WO2016068203A1 - Composé - Google Patents

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Publication number
WO2016068203A1
WO2016068203A1 PCT/JP2015/080428 JP2015080428W WO2016068203A1 WO 2016068203 A1 WO2016068203 A1 WO 2016068203A1 JP 2015080428 W JP2015080428 W JP 2015080428W WO 2016068203 A1 WO2016068203 A1 WO 2016068203A1
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Prior art keywords
group
carbon atoms
formula
compound
alkyl group
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PCT/JP2015/080428
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English (en)
Japanese (ja)
Inventor
拓麻 藤田
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東友ファインケム株式会社
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Application filed by 東友ファインケム株式会社 filed Critical 東友ファインケム株式会社
Priority to JP2016556602A priority Critical patent/JP6625548B2/ja
Priority to CN201580059099.5A priority patent/CN107109074A/zh
Priority to KR1020177011610A priority patent/KR101970416B1/ko
Publication of WO2016068203A1 publication Critical patent/WO2016068203A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • 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

Definitions

  • the present invention relates to a compound useful as a pigment.
  • Patent Document 1 As a blue dye for a color filter contained in a liquid crystal display device or a solid-state image sensor, Patent Document 1, C.I. I. Acid Blue 90 is described. This acid blue 90 has the chemical structure shown below, and is classified as a preferred dye in Patent Document 1.
  • An object of the present invention is to provide a compound having high absorbance and to provide a colored curable resin composition containing such a compound.
  • the present invention includes the following inventions.
  • [1] A compound represented by formula (AI).
  • R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an SO 3 - group or SO 3 M Represents a group.
  • R 9a and R 10a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
  • R 11a to R 20a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a SO 3 - group or a SO 3 M group.
  • the alkyl group may have an oxygen atom inserted between methylene groups constituting the alkyl group.
  • R 45a and R 46a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • the alkyl group may have an oxygen atom inserted between the methylene groups constituting the alkyl group.
  • M represents a hydrogen ion, a metal ion, or an ammonium ion.
  • R 1a to R 20a , R 45a , R 46a and R 55a satisfy at least one of the requirements (1), (2) and (3) and the requirement (4).
  • At least one of R 1a to R 8a and R 11a to R 20a is a SO 3 — group or a SO 3 M group.
  • At least one of R 9a , R 10a , R 45a , R 46a and R 55a is an aromatic hydrocarbon group having a SO 3 — group or a SO 3 M group as a substituent.
  • At least one of R 9a and R 10a is an aralkyl group having a SO 3 — group or a SO 3 M group as a substituent on the ring.
  • SO 3 (A-I) compound represented by a - number of groups is 1, the number of SO 3 M groups is 0-6. ]
  • a colored curable resin composition comprising a compound represented by the formula (AI) according to [1].
  • a display device including the color filter according to [3].
  • the compound of the present invention has high absorbance. If the colored curable resin composition containing such a compound is used, the usage-amount of a coloring agent can be suppressed.
  • the compound of the present invention is a compound represented by formula (AI) (hereinafter sometimes referred to as compound (AI)).
  • AI formula (AI)
  • the compounds of the present invention include tautomers and salts thereof.
  • R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an SO 3 - group or SO 3 M Represents a group.
  • R 9a and R 10a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
  • R 11a to R 20a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a SO 3 - group or a SO 3 M group.
  • the alkyl group may have an oxygen atom inserted between methylene groups constituting the alkyl group.
  • R 45a and R 46a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • the alkyl group may have an oxygen atom inserted between the methylene groups constituting the alkyl group.
  • M represents a hydrogen ion, a metal ion, or an ammonium ion.
  • R 1a to R 20a , R 45a , R 46a and R 55a satisfy at least one of the requirements (1), (2) and (3) and the requirement (4).
  • At least one of R 1a to R 8a and R 11a to R 20a is a SO 3 — group or a SO 3 M group.
  • At least one of R 9a , R 10a , R 45a , R 46a and R 55a is an aromatic hydrocarbon group having a SO 3 — group or a SO 3 M group as a substituent.
  • At least one of R 9a and R 10a is an aralkyl group having a SO 3 — group or a SO 3 M group as a substituent on the ring.
  • SO 3 (A-I) compound represented by a - number of groups is 1, the number of SO 3 M groups is 0-6. ]
  • the compound of formula (AI) has a valence of zero.
  • the alkyl group represented by R 1a to R 20a may be linear, branched or cyclic.
  • Examples of the linear or branched alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, and a decyl group.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 6 carbon atoms.
  • the cyclic alkyl group represented by R 1a to R 20a may be monocyclic or polycyclic.
  • Examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
  • the cyclic alkyl group preferably has 3 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.
  • alkyl group represented by R 1a to R 20a include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group; isopropyl Groups, sec-butyl groups, tert-butyl groups, isopentyl groups, 1-methylpentyl groups, 2-ethylbutyl groups and the like branched chain alkyl groups; cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, adamantyl groups, etc.
  • examples of the group in which an oxygen atom is inserted between methylene groups constituting the alkyl group include groups represented by the following formulae.
  • * represents a bond.
  • the group having an oxygen atom inserted between the methylene groups constituting the alkyl group is preferably a group having 1 to 10 carbon atoms, more preferably a group having 1 to 6 carbon atoms.
  • the alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group.
  • the number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
  • examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group.
  • examples of the aromatic hydrocarbon group in the aralkyl group include a phenyl group and a naphthyl group.
  • the aralkyl group preferably has 7 to 20 carbon atoms.
  • examples of the substituent in the aromatic hydrocarbon group and the aralkyl group include a halogen atom such as a fluorine atom, a chlorine atom and iodine; and a carbon number such as a methoxy group and an ethoxy group
  • a halogen atom such as a fluorine atom, a chlorine atom and iodine
  • a carbon number such as a methoxy group and an ethoxy group
  • aromatic hydrocarbon group examples include groups represented by the following formulae.
  • * represents a bond.
  • aralkyl group which may be substituted include groups in which a methylene group is bonded to the bond of each specific example of the following aromatic hydrocarbon group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
  • R 1a to R 8a are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a methyl group, from the viewpoint of ease of synthesis. .
  • R 9a to R 10a are each independently an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group or an optionally substituted aralkyl group from the viewpoint of ease of synthesis.
  • At least one of R 11a to R 12a is preferably a halogen atom or an alkyl group having 1 to 10 carbon atoms, and at least one of them is a halogen atom or an alkyl group having 1 to 8 carbon atoms. It is more preferable that at least one of them is a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
  • At least one of R 13a to R 14a is preferably a halogen atom or an alkyl group having 1 to 10 carbon atoms, and at least one of them is a halogen atom or alkyl having 1 to 8 carbon atoms. It is more preferable that at least one of them is a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
  • R 15a to R 20a are each independently preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms from the viewpoint of ease of synthesis, and preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. It is more preferable that it is a hydrogen atom or a methyl group.
  • Examples of the alkyl group for R 45a and R 46a include alkyl groups having 1 to 10 carbon atoms for R 1a to R 20a , respectively.
  • specific examples of the alkyl group having 1 to 10 carbon atoms include groups represented by the following formulae. In the following formula, * represents a bond. Of these, an alkyl group having 1 to 8 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
  • examples of the group in which an oxygen atom is inserted between the methylene groups constituting the alkyl group include groups represented by the following formulae.
  • * represents a bond.
  • the alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group.
  • the number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
  • the group having an oxygen atom inserted between the methylene groups constituting the alkyl group is preferably a group having 1 to 10 carbon atoms, more preferably a group having 1 to 6 carbon atoms.
  • the alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group.
  • the number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
  • examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group.
  • the substituent is a halogen atom such as a fluorine atom, a chlorine atom or iodine; a haloalkyl having 1 to 6 carbon atoms such as a chloromethyl group or a trifluoromethyl group Group: alkoxy group having 1 to 6 carbon atoms such as methoxy group and ethoxy group; hydroxy group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; sulfamoyl group; carbon number such as methylsulfonyl group An alkylsulfonyl group having 1 to 6 carbon atoms; an alkoxycarbonyl group having 1 to 6 carbon atoms such as
  • R 45a and R 46a are each independently preferably an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group, from the viewpoint of ease of synthesis.
  • * represents a bond.
  • Examples of the alkyl group for R 55a include the alkyl groups for R 1a to R 20a , respectively.
  • specific examples of the alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n -Linear alkyl groups such as nonyl and n-decyl groups; branched alkyl groups such as isopropyl, sec-butyl, tert-butyl, isopentyl, 1-methylpentyl and 1-propylbutyl
  • a cyclic alkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group; and the like, for example, a group represented by the al
  • * represents a bond.
  • an alkyl group having 1 to 8 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
  • examples of the group in which an oxygen atom is inserted between the methylene groups constituting the alkyl group include groups represented by the following formulae.
  • * represents a bond.
  • the alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group.
  • the number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
  • examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group, and a phenyl group is preferable.
  • the substituent in the aromatic hydrocarbon group includes a halogen atom such as a fluorine atom, a chlorine atom and iodine; a haloalkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; a methoxy group and an ethoxy group
  • An alkoxy group having 1 to 6 carbon atoms such as a group; a hydroxy group; an alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group; a sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; C 1-6 alkoxy
  • R 55a is preferably an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group, more preferably an alkyl group having 1 to 8 carbon atoms or a halogen atom.
  • examples of metal ions include alkali metal ions such as lithium ions, sodium ions, and potassium ions.
  • the ammonium ion is preferably a quaternary ammonium ion such as a tetraalkylammonium ion. Quaternary ammonium ions are useful when included in a colored curable resin composition.
  • M is preferably a hydrogen ion or an alkali metal ion, more preferably a hydrogen ion from the viewpoint of absorbance.
  • the compound represented by the formula (AI) has 1 SO 3 - group.
  • the number of SO 3 M groups is appropriately set in the range of 0 to 6, more preferably 1 to 3, and still more preferably 1.
  • the SO 3 — group and the SO 3 M group may have a substituent represented by R 1a to R 8a and R 11a to R 20a , or the following (1a) and You may have as a substituent of (2a).
  • (2a) Substituent on the ring in the aralkyl group represented by R 9a and R 10a SO 3 - group and SO 3 M group may be attached to the same aromatic ring are similar, but that are attached to different aromatic rings is large.
  • the compound (AI) is a compound having a valence of 0, that is, electrically neutral.
  • Examples of the compound represented by the formula (AI) include compounds 1 to 90 represented by the formula (AI-1).
  • R 9a to R 20a , R 45a , R 46a and R 55a are as shown in Tables 1 to 6.
  • the compound of the formula (AI-1) is a group represented by R 1a to R 8a , R 11a to R 20a , or any one of (1a) and (2a) as an SO 3 - group and SO 3 H group. At least one of the above.
  • Ph1 to Ph5 are as follows. In the following formula, * represents a bond.
  • compounds 31 to 90 are preferable, and compounds 46 to 60 are more preferable.
  • Compound (AI) can be produced by sulfonation of a compound of formula (A-II) (hereinafter sometimes referred to as compound (A-II)).
  • Examples of compound (A-II) include hydrochloride, phosphate, perchlorate, BF 4 salt, PF 6 salt and the like.
  • R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • R 9a and R 10a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
  • R 11a to R 20a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a halogen atom.
  • the alkyl group may have an oxygen atom inserted between methylene groups constituting the alkyl group.
  • R 45a and R 46a each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
  • the alkyl group may have an oxygen atom inserted between the methylene groups constituting the alkyl group.
  • M 1 represents Cl ⁇ , phosphate ion, perchlorate, BF 4 salt or PF 6 salt.
  • Compound (A-II) can be produced, for example, by reacting a compound represented by formula (BI) with a compound represented by formula (CI). Such a reaction may be performed in the presence of an organic solvent or may be performed in the absence of a solvent.
  • R 1a to R 20a , R 45a , R 46a and R 55a each have the same meaning as described above.
  • Compound (A-II) is produced by reacting a compound represented by formula (B-II) with a compound represented by formula (C-II) and formula (C-III). Can do. Such a reaction may be performed in the presence of an organic solvent or may be performed in the absence of a solvent.
  • R 1a to R 20a , R 45a , R 46a, and R 55a each have the same meaning as described above.
  • the compound represented by the formula (C-II) and the compound represented by the formula (C-III) are preferably the same.
  • the amount of the compound represented by the formula (CI) to be used relative to the compound represented by the formula (BI) is preferably about 1 mol of the compound represented by the formula (BI). Is 0.5 mol or more and 8 mol or less, more preferably 1 mol or more and 3 mol or less.
  • the total amount of the compound represented by the formula (C-II) and the compound represented by the formula (C-III) to the compound represented by the formula (B-II) ) Is preferably 0.5 mol or more and 8 mol or less, and more preferably 1 mol or more and 3 mol or less with respect to 1 mol of the compound represented by).
  • the reaction temperature is preferably 30 ° C. to 180 ° C., more preferably 80 ° C. to 130 ° C.
  • the reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours. Any reaction is preferably carried out in an organic solvent from the viewpoint of yield.
  • Organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitro hydrocarbon solvents such as nitrobenzene; methyl isobutyl Ketone solvents such as ketones; amide solvents such as 1-methyl-2-pyrrolidone; and the like.
  • the amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass with respect to 1 part by mass of the compound represented by the formula (BI) or the formula (B-II). Part to 10 parts by mass.
  • the above reaction is preferably carried out in the presence of a condensing agent from the viewpoint of yield.
  • a condensing agent examples include phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, thionyl chloride and the like.
  • the amount of the condensing agent used is preferably 0.1 parts by weight or more and 20 parts by weight or less, more preferably 1 part by weight of the compound represented by the formula (BI) or formula (B-II). 0.2 parts by mass or more and 5 parts by mass or less.
  • the method for obtaining the compound (A-II) from the reaction mixture is not particularly limited, and various known methods can be employed.
  • the reaction mixture can be mixed with a solvent such as alcohol (for example, methanol) and the precipitated crystals can be collected by filtration.
  • the reaction mixture is preferably added to a solvent such as the alcohol.
  • the temperature at which the reaction mixture is added is preferably ⁇ 100 ° C. or higher and 50 ° C. or lower, more preferably ⁇ 80 ° C. or higher and 0 ° C. or lower. After that, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystals collected by filtration are preferably washed with water and then dried. Moreover, you may refine
  • Examples of methods for producing the compound (BI) and the compound (B-II) include various known methods, for example, the methods described in West German Patent Application P3928243.0.
  • Examples of the method for producing the compound (C-II) and the compound (C-III) include various known methods such as the method described in International Publication No. 2012/053211.
  • the compound (CI) is a compound represented by the formula (C-IV) (hereinafter referred to as the compound (C-IV)) as an alkylating agent or This compound (C-IV) can be produced by reacting with an aralkylating agent.
  • This compound (C-IV) is represented by the formula (CV) (hereinafter referred to as compound (CV)) and the formula (C-VI).
  • the compound can be produced by reacting with a compound (hereinafter referred to as compound (C-VI)).
  • Compound (CI) can also be produced directly from compound (CV) and compound (C-VI) regardless of the types of R 9a and R 10a .
  • R 1a to R 20a are the same as above, R 1B is the same as R 9a and R 10a , R 2B is the same as R 11a and R 13a , and R 3B is R 12a and R 14a .
  • R 4B is the same as R 15a and R 18a
  • R 5B is the same as R 16a and R 19a
  • R 6B is the same as R 17a and R 20a
  • R 7B and R 8B are halogen. Atom
  • alkylating agent known alkylating agents such as alkyl halides and sulfates can be used.
  • alkyl halides are preferable because of their availability, and primary alkyl iodides are particularly preferable because of their ease of synthesis.
  • aralkylating agent benzyl halide or the like can be used.
  • Specific examples of the alkylating agent include methyl iodide, ethyl iodide, normal butyl iodide, ethyl bromide, normal butyl bromide, dimethyl sulfate, diethyl sulfate and the like.
  • Specific examples of the aralkylating agent include benzyl iodide, benzyl bromide and the like.
  • the amount of the alkylating agent or aralkylating agent to be used is preferably 2 to 6 mol, more preferably 2 to 4 mol, per 1 mol of the compound represented by the formula (C-IV). It is.
  • the reaction temperature is preferably 20 ° C to 180 ° C, more preferably 30 ° C to 50 ° C.
  • the reaction time is preferably 10 minutes to 10 hours, more preferably 30 minutes to 2 hours.
  • Organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitro hydrocarbon solvents such as nitrobenzene; methyl isobutyl Ketone solvents such as ketones; amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone; and the like.
  • hydrocarbon solvents such as toluene and xylene
  • halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform
  • alcohol solvents such as methanol, ethanol, isopropanol and butanol
  • nitro hydrocarbon solvents such as nitrobenzene
  • methyl isobutyl Ketone solvents such as ketones
  • amide solvents such as
  • the amount of the organic solvent to be used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (C-IV). is there.
  • the above reaction is preferably carried out in the presence of a basic substance from the viewpoint of yield.
  • a basic substance sodium hydride, LDA, DIBAL, potassium t-butoxy and the like can be mentioned.
  • the amount of the basic substance used is preferably 2 mol or more and 6 mol or less, more preferably 2 mol or more and 4 mol or less, per 1 mol of the compound represented by the formula (C-IV).
  • the method for obtaining the compound (CI) from the reaction mixture is not particularly limited, and various known methods can be employed.
  • the reaction mixture can be mixed with a solvent such as alcohol (for example, methanol) and the precipitated crystals can be collected by filtration.
  • the reaction mixture is preferably added to a solvent such as the alcohol.
  • the temperature at which the reaction mixture is added is preferably ⁇ 100 ° C. or higher and 50 ° C. or lower, more preferably ⁇ 80 ° C. or higher and 0 ° C. or lower. After that, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystals collected by filtration are preferably washed with water and then dried. Moreover, you may refine
  • the compound (C-IV) can be produced by reacting the compound (CV) with the compound (C-VI) as described above.
  • the compound (CI) can also be produced by reacting the compound (CV) and the compound (C-VI) as described above.
  • examples of the halogen atom represented by R 7B and R 8B include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of easy availability of raw materials, a fluorine atom, chlorine Atoms are preferred.
  • the amount of compound (CV) to be used is preferably 2 to 5 mol, more preferably 2 to 3 mol, per 1 mol of compound (C-VI).
  • the reaction temperature is preferably 20 ° C to 180 ° C, more preferably 30 ° C to 50 ° C.
  • the reaction time is preferably 10 minutes to 10 hours, more preferably 30 minutes to 2 hours.
  • Organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitro hydrocarbon solvents such as nitrobenzene; methyl isobutyl Ketone solvents such as ketones; amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone; and the like.
  • hydrocarbon solvents such as toluene and xylene
  • halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform
  • alcohol solvents such as methanol, ethanol, isopropanol, and butanol
  • nitro hydrocarbon solvents such as nitrobenzene
  • methyl isobutyl Ketone solvents such as ketones
  • the amount of the organic solvent to be used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (C-VI). is there.
  • the above reaction is preferably carried out in the presence of a palladium compound, a phosphine compound and a basic substance from the viewpoint of yield.
  • the palladium compound include palladium acetate (II), palladium chloride (II), palladium bromide (II), bis (2,4-pentanedionato) palladium (II), bis (dibenzylideneacetone) palladium (0), And tris (dibenzylideneacetone) dipalladium (0).
  • the amount of the palladium compound to be used is preferably 0.0001 mol or more and 0.5 mol or less, more preferably 0.001 mol or more and 0.1 mol or less, relative to 1 mol of the compound (C-VI). .
  • Examples of the phosphine compound include dppf, Xantphos, BINAP, XPhos, SPhos, MePhos and the like.
  • the amount of the phosphine compound to be used is preferably 0.001 mol or more and 0.5 mol or less, more preferably 0.003 mol or more and 0.1 mol or less, relative to 1 mol of the compound (C-VI). .
  • Examples of the basic compound include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, t-butoxy sodium, t-butoxy potassium and the like.
  • the amount of the basic compound to be used is preferably 1 mol or more and 5 mol or less, more preferably 1 mol or more and 3 mol or less, per 1 mol of compound (C-VI).
  • the method for obtaining the compound (C-IV) from the reaction mixture is not particularly limited, and various known methods can be employed.
  • the reaction mixture can be mixed with a solvent such as alcohol (for example, methanol) and the precipitated crystals can be collected by filtration.
  • the reaction mixture is preferably added to a solvent such as the alcohol.
  • the temperature at which the reaction mixture is added is preferably ⁇ 100 ° C. or higher and 50 ° C. or lower, more preferably ⁇ 80 ° C. or higher and 0 ° C. or lower. After that, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystals collected by filtration are preferably washed with water and then dried. Moreover, you may refine
  • the compound (AI) of the present invention can be applied to a fiber product.
  • the fiber material can be colored by kneading, impregnating or adhering to the fiber material.
  • the compound (AI) of the present invention is contained in the colored curable resin composition as a dye of a colorant (hereinafter sometimes referred to as “colorant (A)”).
  • the colored curable resin composition preferably further contains a resin (B), and more preferably contains a polymerizable compound (C), a polymerization initiator (D), and a solvent (E). It is also preferable to further contain a polymerization initiation assistant (D1), a leveling agent (F) and the like.
  • the compound illustrated as each component can be used individually or in combination of multiple types.
  • a dye containing the compound (AI) of the present invention as an active ingredient may be used alone.
  • other dyes ( A1), pigment (P), or a mixture thereof may be included.
  • Examples of the dye (A1) include oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, and sulfonamides of acid dyes.
  • Dyers ⁇ and Colourists publication
  • known dyes described in dyeing notes color dyeing company.
  • organic solvent-soluble dyes are preferably used.
  • C. I. Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted, and only the number is described), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82 83, 89, 94, 98, 99, 162;
  • Solvent Orange 2 7, 11, 15, 26, 41, 54, 56, 99; C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; I. Solvent dyes,
  • Acid Blue 1 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335; C.
  • Acid Green 1 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc.
  • Acid dyes 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc.
  • xanthene dyes are preferable in classification by chemical structure.
  • a known substance can be used as the xanthene dye.
  • a compound represented by the formula (1) is preferable.
  • R ⁇ 1 > and R ⁇ 2 > represents the phenyl group which may have a substituent each independently.
  • R 3 and R 4 each independently represents a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, —CH 2 — contained in the hydrocarbon group may be replaced by —O—, —CO— or —NR 11 —.
  • R 1 and R 3 may be bonded together to form a ring containing a nitrogen atom together with the nitrogen atom to which they are bonded, and R 2 and R 4 are bonded to each other to form a nitrogen to which they are bonded.
  • R 5 is, -OH, -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO 2 NR 9 R 10
  • R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • m represents an integer of 0 to 4. When m is an integer of 2 or more, the plurality of R 5 may be the same or different.
  • R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
  • Z + represents + N (R 11 ) 4 , Na + or K + .
  • R 9 and R 10 each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and R 9 and R 10 are bonded to each other to form a 3 to 10 member together with a nitrogen atom A nitrogen-containing heterocycle may be formed.
  • R 11 each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms representing R 8 , R 9 , R 10 and R 11 include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl A linear alkyl group having 1 to 20 carbon atoms such as octyl group, nonyl group, nonyl group, decyl group, dodecyl group, hexadecyl group and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group A branched alkyl group having 3 to 20 carbon atoms such as a group, neopentyl group and 2-ethylhexyl group; 3 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclohepty
  • Examples of —CO 2 R 8 include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.
  • Examples of —SO 3 R 8 include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.
  • —SO 2 NR 9 R 10 includes, for example, a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-
  • R 9 and R 10 may be bonded to each other to form a 3- to 10-membered nitrogen-containing heterocycle together with the nitrogen atom.
  • Examples of the heterocyclic ring include the following.
  • Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms representing R 3 and R 4 include those having 1 to 10 carbon atoms.
  • the hydrogen atom contained in the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms representing R 3 and R 4 may be substituted with a halogen atom, and —CH 2 — contained in the saturated hydrocarbon group is It may be replaced by —O—, —CO— or —NR 11 —.
  • halogen atom a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example.
  • saturated hydrocarbon group substituted with a halogen atom include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, and a chlorobutyl group.
  • alkyl group having 1 to 6 carbon atoms representing R 6 and R 7 examples include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, sec-butyl group, tert group -Butyl group, isopentyl group, neopentyl group and the like.
  • Examples of the aralkyl group having 7 to 10 carbon atoms representing R 11 include a benzyl group, a phenylethyl group, and a phenylbutyl group.
  • Z + is + N (R 11 ) 4 , Na + or K + , preferably + N (R 11 ) 4 .
  • the + N (R 11 ) 4 it is preferable that at least two of the four R 11 are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. Further, the total carbon number of the four R 11 is preferably 20 to 80, more preferably 20 to 60.
  • the phenyl group representing R 1 and R 2 may have a substituent.
  • substituents include a halogen atom, -R 8, -OH, -OR 8 , -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 R 8, -SR 8, -SO 2 R 8 , —SO 3 R 8 and —SO 2 NR 9 R 10 may be mentioned.
  • —R 8 is preferable, and a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms is more preferable.
  • the Z +, -SO 3 - - -SO 3 in this case N + (R 11) 4 are preferred.
  • Examples of —OR 8 include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group and icosyloxy group.
  • Examples of —SR 8 include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.
  • Examples of —SO 2 R 8 include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
  • an unsubstituted monovalent saturated hydrocarbon group having 1 to 10 carbon atoms is preferable, a monovalent saturated hydrocarbon group having 1 to 4 carbon atoms is more preferable, and a methyl group and an ethyl group are preferable. Further preferred.
  • R 1 and R 3 may be bonded together to form a ring containing a nitrogen atom together with the nitrogen atom to which they are bonded, and R 2 and R 4 are bonded to each other to form a nitrogen to which they are bonded.
  • a ring containing a nitrogen atom may be formed together with the atom. Examples of the ring containing a nitrogen atom include the following.
  • R 5 -SO 3 H, -SO 3 - Z + and -SO 2 NR 9 R 10 are preferred.
  • R 6 and R 7 are preferably a hydrogen atom, a methyl group or an ethyl group, more preferably a hydrogen atom.
  • m is preferably an integer of 0 to 2, and more preferably 0 or 1.
  • Compound (1) is preferably a compound represented by Formula (2).
  • R 21 , R 22 , R 23 and R 24 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • p and q each independently represents an integer of 0 to 5.
  • the plurality of R 23 may be the same or different, and when q is 2 or more, the plurality of R 24 may be the same or different.
  • Examples of the alkyl group having 1 to 4 carbon atoms representing R 21 , R 22 , R 23 and R 24 include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Groups and the like.
  • R 21 and R 22 are preferably each independently a methyl group or an ethyl group.
  • R 23 and R 24 are preferably methyl groups.
  • p and q are preferably integers of 0 to 2, and more preferably 0 or 1.
  • Compound (1) is preferably a compound represented by Formula (3).
  • R 31 and R 32 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • R 33 and R 34 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Examples of the alkyl group having 1 to 4 carbon atoms representing R 31 , R 32 , R 33 and R 34 are the same as those described above.
  • R 31 and R 32 are preferably each independently a methyl group or an ethyl group.
  • R 33 and R 34 are preferably each independently a hydrogen atom or a methyl group.
  • Examples of the compound (1) include compounds represented by formulas (1-1) to (1-7), respectively.
  • the compound represented by the formula (1-1) is preferable because it is excellent in solubility in an organic solvent.
  • the pigment (P) is not particularly limited, and a known pigment can be used, and examples thereof include pigments classified as pigments by a color index (published by The Society, of Dyers, and Colorists).
  • Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I.
  • Red pigments such as CI 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 CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60; C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; C. I. Green pigments such as CI Pigment Green 7, 36, 58; C. I. Brown pigments such as CI Pigment Brown 23 and 25; C. I. And black pigments such as CI Pigment Black 1 and 7.
  • Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60
  • C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38
  • Green pigments such as CI Pigment Green 7, 36, 58
  • C. I. Brown pigments such as
  • the pigment (P) is preferably a phthalocyanine pigment or a dioxazine pigment, more preferably C.I. I. At least one selected from the group consisting of CI Pigment Blue 15: 6 and CI Pigment Violet 23.
  • the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter are improved.
  • the pigment can be atomized by rosin treatment, surface treatment using a pigment derivative having an acidic group or basic group introduced, graft treatment on the pigment surface with a polymer compound, sulfuric acid atomization method, etc.
  • a treatment, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed.
  • the pigment preferably has a uniform particle size.
  • the pigment can be made into a pigment dispersion in a state where the pigment is uniformly dispersed in the solution by carrying out a dispersion treatment by containing a pigment dispersant.
  • the pigments may be subjected to a dispersion treatment alone, or a plurality of types may be mixed and dispersed.
  • pigment dispersant examples include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specific examples include pigment dispersants such as polyester, polyamine, and acrylic. These pigment dispersants may be used alone or in combination of two or more.
  • the pigment dispersant KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Geneca Corporation), EFKA (registered trademark) (BASF) ), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemie), and the like.
  • the amount used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, with respect to 100 parts by mass of the pigment.
  • the amount of the pigment dispersant used is in the above range, there is a tendency that a pigment dispersion in a uniform dispersion state is obtained.
  • the content of the compound (AI) is preferably 1% by mass or more and 100% by mass or less, more preferably 10% by mass or more and 100% by mass or less, with respect to the total amount of the colorant (A).
  • the content thereof is preferably 0.5% by mass or more and 80% by mass or less, more preferably 40% by mass or more and 90% by mass or less, with respect to the total amount of the colorant (A). It is.
  • the pigment (P) is contained, the content thereof is preferably 35% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 70% by mass or less with respect to the total amount of the colorant (A). More preferably, it is 1 mass% or more and 50 mass% or less.
  • the content of the colorant (A) is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and further preferably 5% by mass with respect to the total amount of the solid content. % To 50% by mass. When the content of the colorant (A) is within the above range, a desired spectral degree can be obtained.
  • total amount of solids refers to the total amount of components excluding the solvent (E) from the colored curable resin composition.
  • the total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.
  • the resin (B) is preferably an alkali-soluble resin (B).
  • the alkali-soluble resin (B) (hereinafter sometimes referred to as “resin (B)”) is derived from at least one monomer (Ba) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. A copolymer containing structural units. Examples of such a resin (B) include the following resins [K1] to [K6].
  • Resin [K1] At least one monomer (Ba) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(Ba)”); A copolymer of a monomer (Bb) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(Bb)”); Resin [K2] (Ba), (Bb), and monomer (Bc) copolymerizable with (Ba) (however, different from (Ba) and (Bb)) (hereinafter referred to as “(Bc)”) In some cases) Resin [K3] Copolymer of (Ba) and (Bc); Resin [K4] Resin obtained by reacting (Bb) with a copolymer of (Ba) and (Bc); Resin [K5] Resin obtained by reacting (Ba) with a copolymer of (
  • (Ba) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methyl
  • (Bb) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
  • (Bb) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
  • (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
  • Examples of (Bb) include a monomer (Bb1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(Bb1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond.
  • a monomer (Bb2) (hereinafter sometimes referred to as “(Bb2)”), a monomer (Bb3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(Bb3)”), etc. Can be mentioned.
  • Examples of (Bb1) include a monomer (Bb1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(Bb1-1)”) And a monomer (Bb1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(Bb1-2)”).
  • (Bb1-1) includes glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -Vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (
  • Examples of (Bb1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) Acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), represented by the formula (BI) And a compound represented by the formula (BII).
  • Vignoxide (registered trademark) 2000 for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation
  • 3,4-epoxycyclohexylmethyl (meth) Acrylate for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation
  • 3,4-epoxycyclohexylmethyl (meth) acrylate
  • R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group represents a hydroxy group May be substituted.
  • X a and X b is a single bond, * - R c -, * - R c -O -, * - represents the R c -S- or * -R c -NH-.
  • R c represents an alkanediyl group having 1 to 6 carbon atoms. * Represents a bond with O.
  • Examples of the alkyl group having 1 to 4 carbon atoms of R a and R b include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
  • Examples of the alkyl group in which the hydrogen atoms of R a and R b are substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxy Examples include propyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like. .
  • R a and R b are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • a hydrogen atom, a methyl group, an ethyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are preferable, and a hydrogen atom and a methyl group are more preferable.
  • alkanediyl group of R c examples include a linear or branched alkanediyl group, and specifically include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4- And linear alkanediyl groups such as diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group; branched alkanediyl groups such as propane-1,2-diyl group.
  • the X a and X b a single bond, * - R c -, or * -R c -O-, more preferably a single bond, or * -R c -O-, and particularly preferably a single bond , Methylene group, ethylene group, * —CH 2 —O— and * —CH 2 CH 2 —O—, more preferably a single bond, * —CH 2 CH 2 —O— (* is O Represents a bond with).
  • Examples of the compound represented by the formula (BI) include compounds represented by any one of the formulas (BI-1) to (BI-15). Among them, formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) or formula (BI-11) to formula (BI-15) A compound represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15) is more preferred.
  • Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15). Among them, formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) to formula (BII-15) A compound represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15) is more preferred.
  • the compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination with a compound represented by formula (BI) and a compound represented by formula (BII). May be.
  • the content ratio of the compound represented by Formula (BI) and the compound represented by Formula (BII) is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, more preferably 20:80 to 80:20.
  • (Bb2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group.
  • (Bb2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, and the like.
  • (Bb3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group.
  • Specific examples of (Bb3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • (Bb) is preferably (Bb1) from the viewpoint that the obtained color filter can have higher reliability such as heat resistance and chemical resistance. Furthermore, (Bb1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.
  • Examples of (Bc) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • (Meth) acrylic acid esters of Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate; Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2 .1] Hept-2
  • styrene vinyl toluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferable.
  • the ratio of the structural unit derived from each is the total structural unit constituting the resin [K1] Structural unit derived from (Ba); 2 to 60 mol% Structural unit derived from (Bb); 40 to 98 mol% It is preferable that Structural unit derived from (Ba); 10-50 mol% Structural unit derived from (Bb); 50-90 mol% It is more preferable that When the ratio of the structural unit of the resin [K1] is in the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter are excellent. Tend.
  • Resin [K1] is, for example, a method described in the document “Experimental Methods for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972) and the document Can be produced with reference to the cited references described in 1.
  • a predetermined amount of (Ba) and (Bb), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, for example, by substituting oxygen with nitrogen to create a deoxygenated atmosphere and stirring, The method of heating and heat retention is mentioned.
  • the polymerization initiator, the solvent, and the like used here are not particularly limited, and those usually used in the field can be used.
  • the polymerization initiator include azo compounds (such as 2,2′-azobisisobutyronitrile and 2,2′-azobis (2,4-dimethylvaleronitrile)) and organic peroxides (such as benzoyl peroxide).
  • the solvent any solvent that dissolves each monomer may be used.
  • the solvent (E) for the colored curable resin composition of the present invention include a solvent described later.
  • the obtained copolymer may use the solution after reaction as it is, a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used.
  • a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used.
  • the solvent contained in the colored curable resin composition of the present invention as a solvent during the polymerization, the solution after the reaction is used as it is for the preparation of the colored curable resin composition of the present invention. Therefore, the manufacturing process of the colored curable resin composition of the present invention can be simplified.
  • Resin [K2] can be produced, for example, in the same manner as the method described as the production method of resin [K1].
  • Resin [K4] obtains a copolymer of (Ba) and (Bc), and (Ba) has a carboxylic acid and / or carboxylic acid anhydride (Ba) having a cyclic ether having 2 to 4 carbon atoms of (Bb) It can manufacture by adding to.
  • a copolymer of (Ba) and (Bc) is produced in the same manner as described for the production method of the resin [K1]. In this case, it is preferable that the ratio of the structural units derived from each is the same as that described for the resin [K3].
  • the carboxylic acid and / or carboxylic anhydride derived from (Ba) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (Bb).
  • a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether for example, tris ( Dimethylaminomethyl) phenol, etc.
  • a polymerization inhibitor eg, hydroquinone, etc.
  • the amount of (Bb) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (Ba). By adjusting the amount of (Bb) used within this range, the storage stability of the colored curable resin composition, the developability when forming the pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting pattern are obtained. And the balance of sensitivity tends to be good.
  • (Bb) used in the resin [K4] is preferably (Bb1) and more preferably (Bb1-1) because the cyclic ether has high reactivity and it is difficult for unreacted (Bb) to remain.
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (Ba), (Bb) and (Bc).
  • the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (Ba), (Bb) and (Bc).
  • reaction conditions such as the charging method of each reagent, the reaction temperature, and the reaction time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization.
  • the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
  • a copolymer of (Bb) and (Bc) is obtained in the same manner as in the production method of the resin [K1] described above.
  • the obtained copolymer may be used as it is after the reaction, or may be a concentrated or diluted solution, or may be solid (powder) by a method such as reprecipitation. You may use what was taken out as.
  • the ratio of the structural units derived from (Bb) and (Bc) is respectively based on the total number of moles of all structural units constituting the copolymer of (Bb) and (Bc).
  • the cyclic ether derived from (Bb) of the copolymer of (Bb) and (Bc) under the same conditions as in the production method of the resin [K4], the carboxylic acid of (Ba) Resin [K5] can be obtained by reacting an acid or carboxylic anhydride.
  • the amount of (Ba) to be reacted with the copolymer of (Bb) and (Bc) is preferably 5 to 80 mol per 100 mol of (Bb).
  • (Bb) used in the resin [K5] is preferably (Bb1), more preferably (Bb1-1), because the cyclic ether has high reactivity and it is difficult for unreacted (Bb) to remain.
  • Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5].
  • Carboxylic anhydride is reacted with a hydroxy group generated by reaction of cyclic ether with carboxylic acid or carboxylic anhydride.
  • the resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride.
  • the resin [K6] is a cyclic ether derived from (Bb) and a carboxylic acid or carboxylic acid of (Ba). It can be produced by reacting a carboxylic acid anhydride with a hydroxy group generated by a reaction with an acid anhydride.
  • Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride, and the like.
  • the amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (Ba) used.
  • the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] Resin such as decyl (meth) acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (Meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3 , 4-epoxytricyclo [5.2.1.0 2,6] decyl (meth) acrylate / (meth) acrylic acid / (
  • the resin (B) is preferably a kind selected from the group consisting of a resin [K1], a resin [K2] and a resin [K3], and more preferably from a group consisting of a resin [K2] and a resin [K3]. It is the kind chosen. When these resins are used, the colored curable resin composition is excellent in developability. Resin [K2] is more preferable from the viewpoint of adhesion between the coloring pattern and the substrate.
  • the polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. .
  • the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
  • the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, still more preferably 70 to 135 mg-KOH / g.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
  • the content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of the solid content.
  • the content of the resin (B) is in the above range, a colored pattern can be formed, and the resolution and remaining film ratio of the colored pattern tend to be improved.
  • the polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.
  • Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone. And the above-mentioned (Ba), (Bb) and (Bc).
  • Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol diester.
  • the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
  • examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( (Meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) ) Is
  • the weight average molecular weight of the polymerizable compound (C) is preferably from 150 to 2,900, more preferably from 250 to 1,500.
  • the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass based on the total amount of the solid content. is there.
  • the content ratio of the resin (B) and the polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80 to 80:20, more preferably on a mass basis. Is from 35:65 to 80:20.
  • the content of the polymerizable compound (C) is within the above range, the remaining film ratio at the time of forming the colored pattern and the chemical resistance of the color filter tend to be improved.
  • the polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.
  • Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.
  • the O-acyloxime compound is a compound having a partial structure represented by the formula (Dd1).
  • * represents a bond.
  • O-acyloxime compound examples include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane.
  • O-acyloxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1 At least one selected from the group consisting of -one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy -1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.
  • the alkylphenone compound is, for example, a compound having a partial structure represented by the formula (Dd2) or a partial structure represented by the formula (Dd3).
  • the benzene ring may have a substituent.
  • Examples of the compound having a partial structure represented by the formula (Dd2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4 -Morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one Etc.
  • Commercial products such as Irgacure 369, 907, 379 (above, manufactured by BASF) may be used.
  • Examples of the compound having a partial structure represented by the formula (Dd3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2 -Hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, ⁇ , ⁇ -diethoxy Examples include acetophenone and benzyl dimethyl ketal.
  • the alkylphenone compound is preferably a compound having a partial structure represented by the formula (Dd2).
  • Examples of the biimidazole compound include a compound represented by the formula (Dd4).
  • R d1 to R d6 each represents an aryl group having 6 to 10 carbon atoms which may have a substituent.
  • Examples of the aryl group having 6 to 10 carbon atoms of R d1 to R d6 include a phenyl group, a toluyl group, a xylyl group, an ethylphenyl group, and a naphthyl group, and a phenyl group is preferable.
  • Examples of the substituent that may be substituted on the aryl group of R d1 to R d6 include a halogen atom and an alkoxy group having 1 to 4 carbon atoms.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example, Preferably it is a chlorine atom.
  • Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, and a methoxy group is preferable.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2′-bis (2,3-dichlorophenyl) -4.
  • triazine compound examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4- Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy Styryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamin
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
  • polymerization initiation assistant D1 (particularly amines) described later.
  • the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium-p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium-p-toluenesulfonate, Onium salts such as acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium-p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium-p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, Examples thereof include nitrobenzyl tosylate and benzoin
  • the polymerization initiator (D) a polymerization initiator that generates an active radical is preferable.
  • the polymerization initiator (D) is selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds. It is a polymerization initiator containing at least one selected, and more preferably a polymerization initiator containing an O-acyloxime compound.
  • the content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass, and more preferably 1 to 30 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass.
  • the polymerization initiation assistant (D1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound that has been polymerized by the polymerization initiator. When the polymerization initiation assistant (D1) is included, it is usually used in combination with the polymerization initiator (D).
  • Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
  • Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylbenzoate Aminobenzoic acid esters such as aminoethyl and 4-dimethylaminobenzoic acid 2-ethylhexyl; N, N-dimethylparatoluidine; 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis ( Alkylaminobenzophenone such as diethylamino) benzophenone and 4,4′-bis (ethylmethylamino) benzophenone; and the like.
  • alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine
  • alkylaminobenzophenone is preferable, and 4,4′-bis (diethylamino).
  • Benzophenone is preferable.
  • Commercial products such as EAB-F (Hodogaya Chemical Co., Ltd.) may be used.
  • alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-di Examples include butoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene.
  • thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.
  • carboxylic acid compound examples include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, Examples thereof include N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
  • the content thereof is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
  • the amount is preferably 1 to 20 parts by mass.
  • a solvent (E) is not specifically limited, The solvent normally used in the said field
  • 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 ester solvents intramolecular Solvent containing -COO- and -O-
  • ketone solvent solvent containing -CO- in the molecule and not containing -COO-
  • alcohol solvent containing OH in the molecule, -O-,- Solvent containing no CO- and -COO-
  • aromatic hydrocarbon solvent amide solvent, dimethyl sulfoxide and the like.
  • Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, ⁇ -butyrolactone, and the like.
  • Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, die Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.
  • ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl acetate Le acetate, propylene glycol monopropyl ether
  • ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone. Etc.
  • Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
  • Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
  • Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
  • solvents may be used alone or in combination of two or more.
  • ethylene glycol monobutyl ether propylene glycol monomethyl ether
  • Propylene glycol monomethyl ether acetate dipropylene glycol Ether acetate, 3-methoxy-1-butanol, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, N- methylpyrrolidone is more preferred.
  • the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition.
  • the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
  • Leveling agent (F) examples include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
  • silicone surfactant examples include a surfactant having a siloxane bond in the molecule.
  • Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH29PA, SH30PA, SH8400 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 are included.
  • fluorosurfactant examples include surfactants having a fluorocarbon chain in the molecule.
  • Florard registered trademark
  • FC430 FC431
  • MegaFac registered trademark
  • F142D F171, F172, F173, F177, F183, F183, F554, R30
  • RS-718-K manufactured by DIC Corporation
  • EFTOP registered trademark
  • EF301 EF301
  • EF303 EF351
  • EF352 manufactured by Mitsubishi Materials Electronic Chemicals
  • Surflon registered trademark
  • SC101 SC105
  • SC105 Asahi Glass Co., Ltd.
  • E5844 Daikin Fine Chemical Laboratory Co., Ltd.
  • silicone surfactant having a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain in the molecule.
  • Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.
  • the content thereof is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002%, based on the total amount of the colored curable resin composition. It is 0.005 mass% or more and 0.07 mass% or less more preferably. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the colored curable resin composition may contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like, if necessary. Good.
  • the colored curable resin composition is, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent used as necessary. It can be prepared by mixing (F), the polymerization initiation assistant (D1) and other components.
  • the pigment in the case of containing the pigment (P) is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment is about 0.2 ⁇ m or less. Under the present circumstances, you may mix
  • the desired colored curable resin composition can be prepared by mixing the remaining components in the pigment dispersion thus obtained so as to have a predetermined concentration. Further, it is preferable to prepare a solution by dissolving the compound (AI) in part or all of the solvent (E) in advance. Further, the solution is preferably filtered with a filter having a pore size of about 0.01 to 1 ⁇ m. The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 ⁇ m.
  • Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Of these, the photolithographic method is preferable.
  • the photolithographic method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed.
  • a colored coating film that is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing during exposure.
  • the colored pattern and the colored coating film thus formed are the color filter of the present invention.
  • the film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application, for example, 0.1 to 30 ⁇ m, preferably 0.1 to 20 ⁇ m, and more preferably 0.5. ⁇ 6 ⁇ m.
  • resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon
  • aluminum, silver, or a silver / copper / palladium alloy thin film is used.
  • another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.
  • Formation of each color pixel by the photolithographic method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied on a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, and a smooth colored composition layer is obtained. Examples of the coating method include spin coating, slit coating, and slit and spin coating.
  • the temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C.
  • the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably performed at a temperature of 20 to 25 ° C. under a pressure of 50 to 150 Pa.
  • the film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.
  • the coloring composition layer is exposed through a photomask for forming a target coloring pattern.
  • the pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
  • the light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Or you may.
  • examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.
  • Use an exposure device such as a mask aligner or a stepper because the entire exposure surface can be illuminated with parallel rays uniformly, or the photomask can be accurately aligned with the substrate on which the colored composition layer is formed. Is preferred.
  • a colored pattern is formed on the substrate by developing the exposed colored composition layer in contact with a developer.
  • a developer for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide is preferable.
  • concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.
  • the developer may contain a surfactant.
  • the developing method may be any of paddle method, dipping method, spray method and the like.
  • the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water.
  • the post bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C.
  • the post-bake time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.
  • a color filter with particularly high brightness can be produced by using a colored curable resin composition using the compound.
  • 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 image sensors.
  • Example 1 The following reaction was performed in a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 32.2 parts of potassium thiocyanate and 160.0 parts of acetone, and then stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of 2-fluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Next, the reaction mixture was ice-cooled, and 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise.
  • 2-fluorobenzoic acid chloride manufactured by Tokyo Chemical Industry Co., Ltd.
  • the organic layer was washed with 200 parts of 1N hydrochloric acid, then with 200 parts of tap water, and finally with 200 parts of saturated saline. An appropriate amount of bowsho was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer.
  • the obtained organic layer was evaporated using an evaporator to obtain a pale yellow liquid.
  • the resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried at 60 ° C. under reduced pressure to obtain 49.9 parts of a compound represented by the formula (BI-2). Yield 51%.
  • the following reaction was performed in a nitrogen atmosphere. After introducing 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N, N-dimethylformamide into a flask equipped with a condenser and a stirrer, the mixed solution was ice-cooled. Under ice cooling, 5.7 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little over 30 minutes, and the mixture was stirred for 1 hour while warming to room temperature. 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little to the reaction solution and stirred at room temperature for 24 hours.
  • the reaction solution was added little by little to 200 parts of ice water, and then allowed to stand at room temperature for 15 hours. When the water was removed by decantation, a viscous solid was obtained as a residue. After adding 60 parts of methanol to this viscous solid, the mixture was stirred at room temperature for 15 hours. The precipitated solid was filtered off and purified by column chromatography. The purified pale yellow solid was dried at 60 ° C. under reduced pressure to obtain 9.8 parts of a compound represented by the formula (CI-2). Yield 53%.
  • reaction solution was poured into 140.0 parts of toluene, and then stirred for 30 minutes.
  • —SO 3 ⁇ and “—SO 3 H” each represent a bond to a carbon atom in at least one of the six phenyl rings.
  • the absorbance of the compound of Example 1 (AI-2) is the same as that of Comparative Example 1. I. Compared to the absorbance of Acid Blue 90, it is 0.3 larger (concentration: 0.028 g / L).
  • Example 2 The following reaction was performed in a nitrogen atmosphere. After putting 24.2 parts of N-ethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 240 parts of N, N-dimethylformamide into a flask equipped with a condenser and a stirrer, the mixed solution was ice-cooled. After adding 8.0 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) little by little over 30 minutes under ice cooling, the mixture was stirred for 1 hour while warming to room temperature.
  • N-ethylaniline manufactured by Tokyo Chemical Industry Co., Ltd.
  • 60% sodium hydride manufactured by Tokyo Chemical Industry Co., Ltd.
  • —SO 3 ⁇ and “—SO 3 H” each represent a bond to a carbon atom in at least one of the six phenyl rings.
  • Example 3 The following reaction was performed in a nitrogen atmosphere. After putting 28.9 parts of potassium thiocyanate and 160.0 parts of acetone in a flask equipped with a condenser and a stirrer, the mixture was stirred at room temperature for 30 minutes. Next, 50.0 parts of 2,6-difluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Subsequently, after cooling the reaction mixture with ice, 36.4 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise.
  • 2,6-difluorobenzoic acid chloride manufactured by Tokyo Chemical Industry Co., Ltd.
  • the organic layer was washed with 200 parts of 1N hydrochloric acid, then with 200 parts of tap water, and finally with 200 parts of saturated saline. An appropriate amount of bowsho was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer.
  • the obtained organic layer was evaporated using an evaporator to obtain a pale yellow liquid.
  • the resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried at 60 ° C. under reduced pressure to obtain 25.2 parts of a compound represented by the formula (BI-3). Yield 27%.
  • —SO 3 ⁇ and “—SO 3 H” each represent a bond to a carbon atom in at least one of the six phenyl rings.
  • the compound of the present invention has high absorbance.
  • the amount used can be reduced.

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

Abstract

La présente invention aborde le problème consistant à proposer un composé présentant une absorbance élevée. La présente invention se rapporte à un composé représenté par la formule (A-1). Dans la formule, R1a à R8a représentent un atome d'hydrogène, un groupe alkyle, un groupe SO3 - ou un groupe SO3M; R9a et R10a représentent un atome d'hydrogène, un groupe alkyle, un groupe hydrocarboné aromatique ou un groupe aralkyle; R11a à R20a représentent un atome d'hydrogène, un groupe alkyle, un atome d'halogène, un groupe SO3 - ou un groupe SO3M; R45a et R46a représentent un atome d'hydrogène, un groupe alkyle ou un groupe hydrocarboné aromatique; et R55a représente un atome d'hydrogène, un groupe alkyle ou un groupe hydrocarboné aromatique.
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CN107422600A (zh) * 2016-05-23 2017-12-01 东友精细化工有限公司 盐及着色固化性树脂组合物
CN107698536A (zh) * 2016-08-08 2018-02-16 东友精细化工有限公司 化合物、着色组合物、纤维材料、滤色器和显示装置
JP2018081210A (ja) * 2016-11-16 2018-05-24 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色硬化性樹脂組成物
KR20180055727A (ko) * 2016-11-16 2018-05-25 동우 화인켐 주식회사 착색 조성물, 착색 경화성 수지 조성물, 컬러 필터 및 표시 장치
JP2018127596A (ja) * 2016-08-08 2018-08-16 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 化合物
CN109426075A (zh) * 2017-08-23 2019-03-05 东友精细化工有限公司 着色固化性树脂组合物、滤色器和显示装置

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KR102110484B1 (ko) * 2016-05-19 2020-05-13 동우 화인켐 주식회사 염 및 착색 경화성 수지 조성물
CN107422600A (zh) * 2016-05-23 2017-12-01 东友精细化工有限公司 盐及着色固化性树脂组合物
CN107422600B (zh) * 2016-05-23 2021-06-15 东友精细化工有限公司 盐及着色固化性树脂组合物
JP2018127596A (ja) * 2016-08-08 2018-08-16 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 化合物
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JP7075724B2 (ja) 2016-08-08 2022-05-26 東友ファインケム株式会社 化合物、着色組成物、繊維材料、カラーフィルタ、及び表示装置
KR20180055727A (ko) * 2016-11-16 2018-05-25 동우 화인켐 주식회사 착색 조성물, 착색 경화성 수지 조성물, 컬러 필터 및 표시 장치
JP2018083933A (ja) * 2016-11-16 2018-05-31 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色組成物、着色硬化性樹脂組成物、カラーフィルタ及び液晶表示装置
CN108073038A (zh) * 2016-11-16 2018-05-25 东友精细化工有限公司 着色固化性树脂组合物、由着色固化性树脂组合物形成的滤色器和包含滤色器的显示装置
KR102334086B1 (ko) * 2016-11-16 2021-12-02 동우 화인켐 주식회사 착색 조성물, 착색 경화성 수지 조성물, 컬러 필터 및 표시 장치
CN108073038B (zh) * 2016-11-16 2022-04-01 东友精细化工有限公司 着色固化性树脂组合物、由着色固化性树脂组合物形成的滤色器和包含滤色器的显示装置
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JP2018081210A (ja) * 2016-11-16 2018-05-24 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色硬化性樹脂組成物
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