WO2014192973A1 - Composé et composition de résine vulcanisable colorée - Google Patents

Composé et composition de résine vulcanisable colorée Download PDF

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Publication number
WO2014192973A1
WO2014192973A1 PCT/JP2014/064901 JP2014064901W WO2014192973A1 WO 2014192973 A1 WO2014192973 A1 WO 2014192973A1 JP 2014064901 W JP2014064901 W JP 2014064901W WO 2014192973 A1 WO2014192973 A1 WO 2014192973A1
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group
compound
formula
carbon atoms
alkyl group
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Japanese (ja)
Inventor
鈴木　智也
芦田　徹
龍虎 呉
哲郎 赤坂
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to KR1020207027082A priority Critical patent/KR102250530B1/ko
Priority to CN201480030604.9A priority patent/CN105408427A/zh
Priority to KR1020207027072A priority patent/KR102250529B1/ko
Priority to KR1020157035042A priority patent/KR102204232B1/ko
Priority to JP2015519988A priority patent/JP6370778B2/ja
Publication of WO2014192973A1 publication Critical patent/WO2014192973A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
    • C07D311/88—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments

Definitions

  • the present invention relates to a compound useful as a dye and a colored curable resin composition.
  • Dyes are used for color display using reflected light or transmitted light in the fields of, for example, fiber materials, liquid crystal display devices, and ink jets.
  • a dye for example, a sulfoxanthene dye having a xanthene skeleton and represented by the following formula (a) is known (Patent Document 1).
  • Rhodamine B represented by the following formula (b) is also known (Non-Patent Document 1).
  • R 1a , R 2a , R 3a and R 4a each independently represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.
  • R 1a and R 2a may be bonded to each other to form a ring with the nitrogen atom to which they are bonded, and R 3a and R 4a are bonded to each other to form a ring with the nitrogen atom to which they are bonded. May be formed.
  • R 1a , R 2a , R 3a and R 4a are not all the same group.
  • —CH 2 — contained in the alkyl group may be substituted with —O—, —NR b — or —CO—, and the hydrogen atom contained in the alkyl group is a halogen atom, having 6 to 20 carbon atoms.
  • the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 8 carbon atoms, and R b is An alkyl group having 1 to 3 carbon atoms is represented.
  • R 1a , R 2a , R 3a and R 4a are each independently an alkyl group having 1 to 20 carbon atoms, and —CH 2 — contained in the alkyl group is —O— or CO—.
  • the compound according to [1], wherein a hydrogen atom contained in the alkyl group may be substituted with a halogen atom or an aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • At least two of R 1a , R 2a , R 3a and R 4a are alkyl groups having 2 to 20 carbon atoms, and —CH 2 — contained in the alkyl group is —O— or CO—.
  • the hydrogen atom contained in the alkyl group may be substituted with a halogen atom or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the compound according to [1] or [2] .
  • R 1a , R 2a , R 3a and R 4a are each independently an alkyl group having 2 to 20 carbon atoms, and —CH 2 — contained in the alkyl group is substituted with —O—.
  • One of R 1a , R 2a , R 3a and R 4a is a group in which —CH 2 — contained in an alkyl group having 2 to 20 carbon atoms is substituted with —O— ]
  • R 1a and R 2a are each independently an alkyl group having 2 to 6 carbon atoms
  • R 3a and R 4a are each independently an alkyl group having 1 to 6 carbon atoms.
  • R 1b , R 2b and R 3b each independently represents an alkyl group having 1 to 8 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 3 carbon atoms.
  • Ar represents a group represented by formula (i).
  • R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom.
  • M represents an integer of 1 to 5. m. And when R is 2 or more, the plurality of R may be the same or different from each other.
  • Ar is a group represented by the formula (C-0), a group represented by the formula (C-1), or a group represented by the formula (C-2) [9] to [12] The compound in any one of. (* Represents a bond with a nitrogen atom.)
  • [X 1 and X 2 are different from each other and each represent an alkyl group having 1 to 8 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms. The hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 3 carbon atoms.
  • Ar 1 and Ar 2 each independently represent a group represented by formula (i).
  • R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom.
  • M represents an integer of 1 to 5.
  • m represents an integer of 1 to 5.
  • R is 2 or more, the plurality of R may be the same or different from each other.
  • * Represents a bond with a nitrogen atom.
  • a colored curable resin composition comprising the colorant, resin, polymerizable compound, polymerization initiator and solvent according to [19] or [20].
  • the compound of the present invention is excellent in solubility in an organic solvent, and a color filter formed from a colored curable resin composition containing the compound of the present invention can be expected to have higher brightness.
  • the first compound of the present invention is a compound represented by the formula (Ia) (hereinafter sometimes referred to as “compound (Ia)”).
  • the compounds of the present invention include tautomers and stereoisomers thereof.
  • [R 1a , R 2a , R 3a And R 4a Each independently represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.
  • R 1a And R 2a May be bonded to each other to form a ring together with the nitrogen atom to which they are bonded, 3a And R 4a And may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded.
  • R 1a , R 2a , R 3a And R 4a Are not all the same group.
  • —CH contained in the alkyl group 2 -Is -O-, -NR b -Or -CO- may be substituted, and a hydrogen atom contained in the alkyl group may be substituted with a halogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms or -OH, The hydrogen atom contained in the group hydrocarbon group may be substituted with an alkoxy group having 1 to 8 carbon atoms.
  • b Represents an alkyl group having 1 to 3 carbon atoms.
  • R 1a , R 2a , R 3a And R 4a Are not all the same group.
  • alkyl group having 1 to 20 carbon atoms examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, A linear alkyl group having 1 to 20 carbon atoms such as a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group; Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group,
  • R b Represents an alkyl group having 1 to 3 carbon atoms, and examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • R b Represents an alkyl group having 1 to 3 carbon atoms, and examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • Examples of the group substituted with-or -CO- include -CH contained in an alkyl group. 2 -Is preferably a group substituted with -O- or -CO-, and -CH contained in the alkyl group.
  • the hydrogen atom contained in the alkyl group may be substituted with a halogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms or —OH, and the hydrogen atom contained in the aromatic hydrocarbon group has a carbon number It may be substituted with 1 to 8 alkoxy groups.
  • the hydrogen atom contained in the alkyl group is substituted with a halogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms or —OH
  • the hydrogen atom contained in the alkyl group is a halogen atom or 6 to 20 carbon atoms.
  • a group substituted with an aromatic hydrocarbon group is preferred.
  • halogen atom examples include a fluorine atom
  • examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, a tolyl group, an ethylphenyl group, a propylphenyl group, a butylphenyl group, Examples thereof include a pentylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, and a decylphenyl group.
  • alkoxy group having 1 to 8 carbon atoms examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, pentyloxy group, isopentyloxy group, hexyloxy group, heptyloxy Group, octyloxy group and the like.
  • Specific examples of the group in which the hydrogen atom contained in the alkyl group is substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms are as follows. In the following formula, * represents a bond with a nitrogen atom.
  • a group substituted with-or CO-, a hydrogen atom contained in an alkyl group is a halogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms or a group substituted with -OH, and an alkyl group -CH 2 -Is -O-, -NR b
  • Examples of the group substituted with-or -CO- and the hydrogen atom contained in the alkyl group is substituted with a halogen atom, an aromatic hydrocarbon group having 6 to 20 carbon atoms or OH include the following formula (D- Examples thereof include groups represented by 1) to (D-18), (D-31) to (D-45) and (D-50) to (D-57).
  • * represents a bond with a nitrogen atom.
  • Formula (D-2), Formula (D-8), Formula (D-14), Formula (D-17), Formula (D- 42), a group represented by the formula (D-43), a formula (D-45) or a formula (D-56) is preferable, and the formula (D-8), the formula (D-14), and the formula (D-17).
  • a group represented by formula (D-42) or formula (D-45) is more preferred.
  • Examples of the cycloalkyl group having 5 to 10 carbon atoms include cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 2-methylpentyl group, 2-methylhexyl group, 2,5-dimethylpentyl group, 2,6- A dimethylhexyl group etc. are mentioned.
  • R 1a And R 2a Examples of the ring formed together with the nitrogen atom to which they are bonded to each other include a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring.
  • R 3a And R 4a examples of the ring formed together with the nitrogen atom to which they are bonded to each other include a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring.
  • R 1a , R 2a , R 3a And R 4a Are each independently an alkyl group having 1 to 20 carbon atoms, and —CH contained in the alkyl group. 2 - May be substituted with -O- or CO-, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom or an aromatic hydrocarbon group having 6 to 10 carbon atoms. (Ia) is preferred.
  • R 1a , R 2a , R 3a And R 4a At least two of them are alkyl groups having 2 to 20 carbon atoms, and —CH contained in the alkyl group. 2 - May be substituted with -O- or CO-, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom or an aromatic hydrocarbon group having 6 to 10 carbon atoms. (Ia) is preferred.
  • R 1a , R 2a , R 3a And R 4a Are each independently an alkyl group having 2 to 20 carbon atoms, and —CH contained in the alkyl group. 2 -Is preferably Compound (Ia) which may be substituted with -O-.
  • R 1a , R 2a , R 3a And R 4a One of these is —CH contained in an alkyl group having 2 to 20 carbon atoms.
  • 2 Compound (Ia) in which — is a group substituted with —O— is preferable.
  • R 1a And R 2a Are each independently an alkyl group having 2 to 6 carbon atoms;
  • 3a And R 4a Are preferably each independently a compound (Ia) which is an alkyl group having 1 to 6 carbon atoms.
  • R 1a And R 2a are each an ethyl group and R 3a Is —CH contained in an alkyl group having 4 to 15 carbon atoms.
  • 2 Compound (Ia) in which — is a group substituted with —O— is preferable.
  • Specific examples of compound (Ia) include the compounds shown in Table 1. In Table 1, Me is -CH.
  • Compound (Ia) has the formula (IIIa) (Hereinafter sometimes referred to as “compound (IIIa)”) and formula (IVa) [In formula (IVa), R 1a And R 2a Represents the same meaning as above. ] And a compound represented by formula (Va) may be reacted with the compound represented by formula (Va). (Hereinafter sometimes referred to as “compound (Va)”), and the resulting compound (Va) and formula (VIa) [In formula (VIa), R 3a And R 4a Represents the same meaning as above. ] And a compound represented by the formula (hereinafter sometimes referred to as “compound (VIa)”).
  • a compound (Ia) is produced by reacting the obtained compound (VIIa) with the compound (IVa) (hereinafter sometimes referred to as “compound (VIIa)”). You can also. Such a reaction can be carried out in the presence of a solvent.
  • the solvent include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; methanol, ethanol, propanol and isopropanol.
  • Alcohol solvents such as butanol and ethylene glycol; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amides such as 1-methyl-2-pyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide Solvent; water; and the like.
  • the reaction temperature is preferably ⁇ 10 ° C. to 180 ° C., more preferably 0 ° C. to 100 ° C.
  • the reaction time is preferably 1 to 12 hours, more preferably 1 to 8 hours.
  • the amount of compound (IVa) or compound (VIa) to be used is preferably 1 to 30 mol, more preferably 2 to 4 mol, per 1 mol of compound (IIIa).
  • the method for obtaining the target compound (Ia) from the reaction mixture is not particularly limited, and various known techniques can be employed.
  • the reaction mixture can be mixed with an acid (for example, acetic acid, hydrochloric acid, etc.), and the precipitated crystals can be collected by filtration.
  • the acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution.
  • the temperature at which the reaction mixture is added is preferably 0 ° C. or higher and 50 ° C. or lower, more preferably 10 ° C. or higher and 40 ° C. or lower. Further, after adding the reaction mixture to the aqueous acid solution, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the second compound of the present invention is a compound represented by the formula (Ib) (hereinafter sometimes referred to as “compound (Ib)”).
  • the compounds of the present invention also include tautomers thereof.
  • R 1b , R 2b And R 3b Each independently represents an alkyl group having 1 to 8 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms. The hydrogen atom contained in the hydrocarbon group may be substituted with an alkoxy group having 1 to 3 carbon atoms.
  • Ar represents a group represented by formula (i).
  • R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom.
  • M represents an integer of 1 to 5.
  • m when R is 2 or more, the plurality of R may be the same or different from each other.
  • R 1b , R b2 And R 3b Examples of the alkyl group having 1 to 8 carbon atoms represented by: methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n- A linear alkyl group such as an octyl group; Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1- Methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group
  • the hydrogen atom contained in these alkyl groups having 1 to 8 carbon atoms may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms, and examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl Group, naphthyl group, tolyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group and the like.
  • the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms may be substituted with an alkoxy group having 1 to 3 carbon atoms. Examples of the alkoxy group having 1 to 3 carbon atoms include methoxy group and ethoxy group. Group, n-propoxy group, isopropoxy group.
  • Examples of the group in which the hydrogen atom contained in the alkyl group is substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms include the following groups. (* Represents a bond with a nitrogen atom.)
  • Examples of the alkyl group having 1 to 3 carbon atoms represented by R include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • a hydrogen atom contained in the alkyl group having 1 to 3 carbon atoms is a halogen atom.
  • Examples of the group substituted with include the following groups.
  • m represents an integer of 1 to 5, and is preferably 1 or 2 from the viewpoint of obtaining raw materials.
  • Examples of the group represented by the formula (i) include the following groups.
  • Examples of compound (Ib) include the compounds shown in Table 2.
  • Me is -CH.
  • 3 Et is -CH 2 CH 3 Pr is —CH 2 CH 2 CH 3
  • I-Pr is -CH (CH 3 ) 2
  • Bu is -CH 2 CH 2 CH 2 CH 3
  • T-Bu is -C (CH 3 ) 3
  • EtHex is -CH 2 CH (C 2 H 5 ) (CH 2 ) 3 CH 3 Respectively.
  • the numbers beginning with C in the Ar column of Table 2 represent the numbers of the above formulas exemplified as the group represented by the formula (i).
  • the compound (Ib-8), the compound (Ib-36), the compound (Ib-37), the compound (Ib-38), and the compound (Ib-101) are particularly excellent in solubility in an organic solvent. preferable.
  • the manufacturing method of compound (Ib) is demonstrated.
  • the compound of the formula (IIb) A compound represented by formula (hereinafter sometimes referred to as “compound (IIb)”), and formula (IIIb) [In formula (IIIb), R 1b And R 2b Represents the same meaning as above.
  • Examples of the organic solvent in the reaction of compound (IIb) and compound (IIIb) include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol; Nitrated hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidone;
  • the reaction temperature in the reaction of compound (IIb) and compound (IIIb) is preferably 0 ° C. to 100 ° C., more preferably 20 ° C. to 80 ° C.
  • the reaction time is preferably 1 to 12 hours, more preferably 1 to 8 hours.
  • the amount of compound (IIIb) to be used is preferably 1 to 30 mol, more preferably 2 to 20 mol, per 1 mol of compound (IIb).
  • the organic solvent in the reaction of compound (IVb) and compound (Vb) include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol; Nitrated hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidone;
  • the reaction temperature in the reaction of the compound (IVb) and the compound (Vb) is preferably 30 ° C.
  • the reaction time is preferably 1 hour to 24 hours, more preferably 1 hour to 8 hours.
  • the amount of compound (Vb) to be used is preferably 1 to 30 mol, more preferably 2 to 20 mol, per 1 mol of compound (IIIb).
  • the method for obtaining the target compound (Ib) from the reaction mixture is not particularly limited, and various known techniques can be employed.
  • the reaction mixture can be mixed with an acid (for example, acetic acid and the like), and the precipitated crystals can be collected by filtration.
  • the acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution.
  • the temperature at which the reaction mixture is added is preferably 10 ° C. or higher and 50 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower, and further preferably 20 ° C. or higher and 30 ° C. or lower. Further, after adding the reaction mixture to the aqueous acid solution, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystal collected by filtration is preferably washed with water or the like and then dried. Moreover, you may refine
  • the third compound of the present invention is a compound represented by the formula (Ic) (hereinafter sometimes referred to as “compound (Ic)”).
  • the compounds of the present invention also include tautomers thereof.
  • [X 1 And X 2 are different from each other and each represent an alkyl group having 1 to 8 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms. A hydrogen atom contained in the hydrogen group may be substituted with an alkoxy group having 1 to 3 carbon atoms.
  • Ar 1 And Ar 2 Each independently represents a group represented by the formula (i). (R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a halogen atom.
  • M represents an integer of 1 to 5.
  • X 1 And X 2 are different from each other.
  • X 1 And X 2 Examples of the alkyl group having 1 to 8 carbon atoms represented by: methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n- A linear alkyl group such as an octyl group; Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1- Methylhexyl group, 2-methylhexyl group, 3-methylhex
  • the hydrogen atom contained in these alkyl groups having 1 to 8 carbon atoms may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms, and examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl Group, naphthyl group, tolyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group and the like.
  • the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms may be substituted with an alkoxy group having 1 to 3 carbon atoms. Examples of the alkoxy group having 1 to 3 carbon atoms include methoxy group and ethoxy group. Group, n-propoxy group, isopropoxy group.
  • Examples of the group in which the hydrogen atom contained in the alkyl group is substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms include the following groups. (* Represents a bond with a nitrogen atom.)
  • X 1 And X 2 Are different from each other and are more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group or a 2-ethylhexyl group.
  • Examples of the alkyl group having 1 to 3 carbon atoms represented by R include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • a hydrogen atom contained in the alkyl group having 1 to 3 carbon atoms is a halogen atom.
  • the group substituted with include the following groups.
  • m represents an integer of 1 to 5, and is preferably 1 or 2 from the viewpoint of obtaining raw materials.
  • Examples of the group represented by the formula (i) include the following groups. Among these, a group represented by the formula (C-0), a group represented by the formula (C-1), or a group represented by the formula (C-2) is preferable.
  • Ar 1 And Ar 2 are preferably the same group. (* Represents a bond with a nitrogen atom.)
  • Examples of the compound (Ic) include compounds shown in Table 3. In Table 2, Me is -CH.
  • compound (Ic-140) is preferred.
  • the manufacturing method of compound (Ic) is demonstrated.
  • the compound of the formula (IIc) A compound represented by formula (hereinafter sometimes referred to as “compound (IIc)”), and formula (IIIc) [In the formula (IIIc), X 1 , R and m each have the same meaning as described above. ] And a compound represented by the formula (IVc) (hereinafter, may be referred to as “compound (IIIc)”) in an organic solvent.
  • Examples of the organic solvent in the reaction of compound (IIc) with compound (IIIc) include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol A nitrated hydrocarbon solvent such as nitrobenzene; a ketone solvent such as methyl isobutyl ketone; an amide solvent such as 1-methyl-2-pyrrolidone; and the like.
  • the reaction temperature in the reaction between the compound (IIc) and the compound (IIIc) is preferably 0 ° C. to 100 ° C., more preferably 20 ° C. to 80 ° C.
  • the reaction time is preferably 1 to 12 hours, more preferably 1 to 8 hours.
  • the amount of compound (IIIc) to be used is preferably 1 to 30 mol, more preferably 2 to 20 mol, per 1 mol of compound (IIc).
  • the organic solvent in the reaction of compound (IVc) with compound (Vc) include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol A nitrated hydrocarbon solvent such as nitrobenzene; a ketone solvent such as methyl isobutyl ketone; an amide solvent such as 1-methyl-2-pyrrolidone; and the like.
  • the reaction temperature in the reaction of the compound (IVc) and the compound (Vc) is preferably 30 ° C. to 180 ° C., more preferably 20 ° C. to 130 ° C.
  • the reaction time is preferably 1 hour to 24 hours, more preferably 1 hour to 8 hours.
  • the amount of compound (Vc) to be used is preferably 1 to 30 mol, more preferably 2 to 20 mol, per 1 mol of compound (IIIc).
  • the method for obtaining the target compound (Ic) from the reaction mixture is not particularly limited, and various known techniques can be employed.
  • the reaction mixture can be mixed with an acid (for example, acetic acid and the like), and the precipitated crystals can be collected by filtration.
  • the acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution.
  • the temperature at which the reaction mixture is added is preferably 10 ° C. or higher and 50 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower, and further preferably 20 ° C. or higher and 30 ° C. or lower.
  • After adding the reaction mixture to the aqueous acid solution it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystal collected by filtration is preferably washed with water or the like and then dried. Moreover, you may refine
  • Compound (Ia), Compound (Ib), and Compound (Ic) are useful as dyes and exhibit high solubility in organic solvents. Therefore, it is particularly useful as a dye used for a color filter of a display device such as a liquid crystal display device.
  • the content of the compound (I) contained in the colored curable resin composition forming the color filter is preferably 0.025% by mass or more and 48% by mass or less, and 0.08% by mass with respect to the total solid content.
  • the content is more preferably 42% by mass or less and further preferably 0.1% by mass or more and 30% by mass or less.
  • the “total amount of solid content” in this specification refers to an amount obtained by removing the content of the solvent from the total amount of 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 colored curable resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E). Furthermore, a leveling agent (F) may be included.
  • the colorant (A) contains the compound (I), preferably further contains the pigment (A1), and may further contain a dye (A2) different from the compound (I).
  • the content of the compound (I) is 0.5 mass relative to the total amount of the colorant (A). % To 80% by mass is preferable, 1% to 70% by mass is more preferable, and 1% to 50% by mass is more preferable.
  • the pigment (A1) is not particularly limited, and a known pigment can be used, and examples thereof include compounds classified as pigments in the color index (published by The Society of Dyers and Colorists). Examples of the pigment include C.I. I.
  • Pigment Yellow 1 (hereinafter, CI Pigment Yellow is omitted and only the number is described) 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc .;
  • Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
  • Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60, 80
  • 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
  • pigments may be used alone or in combination of two or more.
  • examples of the pigment include C.I. I. Yellow pigments such as CI Pigment Yellow 138, 139 and 150; I. Red pigments such as C.I. Pigment Red 177, 242, and 254; I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and the like, and C.I. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, and 38 are preferable.
  • the transmission spectrum of the color filter using the colored curable resin composition of the present invention can be easily optimized, and the light resistance and chemical resistance of the color filter are improved.
  • the pigment (A1) is optionally treated with rosin, surface treatment using a pigment derivative having an acidic group or basic group introduced, grafting onto the pigment surface with a polymer compound, sulfuric acid atomization method, etc. May be subjected to the atomization treatment by, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, or the like.
  • the pigment (A1) preferably has a uniform particle size.
  • pigment dispersant examples include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more.
  • KP manufactured by Shin-Etsu Chemical Co., Ltd.
  • Floren manufactured by Kyoeisha Chemical Co., Ltd.
  • Solsperse manufactured by Geneca Co., Ltd.
  • EFKA manufactured by BASF
  • Ajispur Ajinomoto Fine (Techno Co., Ltd.
  • Disperbyk Bic Chemie
  • the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less with respect to the pigment (A1).
  • the amount of the pigment dispersant used is within the above range, a pigment dispersion having a uniform dispersion state tends to be obtained.
  • the colorant (A) contains the pigment (A1)
  • the content of the pigment (A1) is preferably 20% by mass or more and 99.5% by mass or less, and 30% by mass with respect to the total amount of the colorant (A). More preferred is 99% by mass or less.
  • the dye (A2) include oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, sulfonamide derivatives of acid dyes, and the like, for example, color index (The Society). of Dyers and Colorists) and known dyes described in Dyeing Notes (Color Dyeing).
  • azo dye cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline And dyes and nitro dyes.
  • organic solvent-soluble dyes are preferred. Specifically, C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162; C. I. Solvent Red 45, 49, 125, 130, 218; C. I.
  • Solvent dyes C.I. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; C.
  • 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 C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; C. I.
  • Direct dyes C. I. C. such as Disperse Yellow 54, 76
  • Disperse dyes C. I. Basic Red 1, 10; C. I. Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68; C. I. C. such as Basic Green 1;
  • 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 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.
  • 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 (a) 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 (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), and having 2 to 4 carbon atoms A copolymer of a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”); Resin [K2] (a) and (b), monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”) In some cases) Resin [K3] Copolymer of (a) and (c); Resin [K4] A resin obtained by reacting (b) with a copolymer of (a) and (c); Resin [K5] A resin obtained by reacting (a) with a copolymer of (b) and (c); Resin [K
  • (a) 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-methylbic
  • (B) 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.
  • (B) 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 (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond.
  • Monomer (b2) (hereinafter sometimes referred to as “(b2)”), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”), etc.
  • (b1) for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”)
  • a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).
  • 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 (glycidyl (meth
  • Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), a compound represented by Formula (VI) and Formula (VII) The compound etc. which are represented by these are mentioned.
  • R a And R b Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.
  • X a And X b Is a single bond, -R c -, * -R c -O-, * -R c -S- or * -R c -NH- is represented.
  • 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 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 a hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy Examples include a -1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
  • R a And R b As for, Preferably a hydrogen atom, a methyl group, a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group is mentioned, More preferably, a hydrogen atom and a methyl group are mentioned.
  • alkanediyl group having 1 to 6 carbon atoms include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, and pentane-1,5. -A diyl group, a hexane-1, 6-diyl group, etc. are mentioned.
  • X a And X b are preferably a single bond, a methylene group, an ethylene group, or * -CH. 2 -O- and * -CH 2 CH 2 -O-, more preferably a single bond, * -CH 2 CH 2 -O- is mentioned (* represents a bond with O).
  • Examples of the compound represented by the formula (VI) include compounds represented by any one of the formulas (VI-1) to (VI-15). Among them, formula (VI-1), formula (VI-3), formula (VI-5), formula (VI-7), formula (VI-9) or formula (VI-11) to formula (VI-15) A compound represented by formula (VI-1), formula (VI-7), formula (VI-9) or formula (VI-15) is more preferred.
  • Examples of the compound represented by the formula (VII) include compounds represented by any one of the formulas (VII-1) to (VII-15). Among them, formula (VII-1), formula (VII-3), formula (VII-5), formula (VII-7), formula (VII-9) or formula (VII-11) to formula (VII-15) A compound represented by formula (VII-1), formula (VII-7), formula (VII-9) or formula (VII-15) is more preferred.
  • the compound represented by formula (VI) and the compound represented by formula (VII) may be used alone or in combination with the compound represented by formula (VI) and the compound represented by formula (VII). May be.
  • the content ratio of the compound represented by formula (VI) and the compound represented by formula (VII) is preferably 5:95 to 95: 5, more preferably 10:90 to 5 on a molar basis.
  • (B2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group.
  • (B2) 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.
  • (B3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group.
  • Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance.
  • (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.
  • Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • Decen-8-yl (meth) acrylate (in this technical field, it is called "dicyclopentenyl (meth) acrylate” as a common name), dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) (Meth) acrylic acid esters such as acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate; 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
  • styrene vinyltoluene
  • benzyl (meth) acrylate tricyclo [5.2.1.0] from the viewpoint of copolymerization reactivity and heat resistance.
  • decan-8-yl (meth) acrylate N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo [2.2.1] hept-2-ene.
  • the ratio of the structural unit derived from each is the total structural unit constituting the resin [K1] Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (b); 40 to 98 mol% It is preferable that Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (b); 50 to 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.
  • the resin [K1] is, for example, a method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., First Edition, First Edition, issued March 1, 1972) Can be produced with reference to the cited references described in 1. Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel and, for example, oxygen is replaced with nitrogen to form a deoxygenated atmosphere and heated while stirring. And a method of keeping warm.
  • 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 examples include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.).
  • the solvent any solvent that dissolves each monomer may be used.
  • the solvent (E) for the colored curable resin composition of the present invention examples 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.
  • 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 (a) and (c), and (b) has a carboxylic acid and / or carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms. It can manufacture by adding to. First, a copolymer of (a) and (c) is produced in the same manner as described in the method for producing 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]. Next, the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms which (b) has.
  • the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (for example, tris ( Dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) are placed in a flask and reacted, for example, at 60-130 ° C. for 1-10 hours to produce resin [K4]. it can.
  • the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a).
  • the storage stability of the colored curable resin composition, the developability when forming the pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting pattern are improved.
  • (b1) is preferable as (b) used for the resin [K4], and (b1-1) is more preferable.
  • 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 (a), (b) and (c).
  • 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 (a), (b) and (c).
  • the reaction conditions such as the charging method, reaction temperature, and 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.
  • Resin [K5] obtains a copolymer of (b) and (c) as a first step in the same manner as in the method for producing 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 (b) and (c) is respectively based on the total number of moles of all the structural units constituting the copolymer.
  • Resin [K5] can be obtained by reacting the product.
  • the amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K5], and (b1-1) is more preferable.
  • 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.
  • Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 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 (a) 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 ] Resins such as decyl (meth) acrylate / ( (me
  • 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 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, and N-vinylpyrrolidone.
  • Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di (Meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate, and the like.
  • a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds.
  • polymerizable compounds examples 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) ) Isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipenta
  • dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.
  • 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 with respect to the total amount of the solid content. is there.
  • the content ratio of the resin (B) to the polymerizable compound (C) is on a mass basis, preferably 20:80 to 80:20, more preferably. Is 35:65 to 80:20.
  • 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-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.
  • the O-acyl oxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * represents a bond.
  • Examples of the O-acyloxime compound 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 -on-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 (d2) or a partial structure represented by the formula (d3).
  • the benzene ring may have a substituent.
  • Examples of the compound having a partial structure represented by the formula (d2) 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.
  • Examples of the compound having a partial structure represented by the formula (d3) 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 (d2).
  • the biimidazole compound is, for example, a compound represented by the formula (d5).
  • R 13 ⁇ R 18 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 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 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.
  • 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 (
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • polymerization initiator (D) 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 pheny
  • the polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds, and more preferably. Is a polymerization initiator containing an O-acyloxime compound.
  • the content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass, 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 triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 2-dimethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4′-bis (Ethylmethylamino) benzophenone and the like can be mentioned, among which 4,4′-bis (diethylamino) benzophenone is preferable.
  • 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, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.
  • 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
  • an ester solvent (a solvent containing —COO— in the molecule and not containing —O—), an ether solvent (a solvent containing —O— in the molecule and not containing —COO—), an ether ester solvent (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-,- A solvent not containing CO- and -COO-), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide and the like.
  • ester solvents 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, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the
  • 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 ether Acetate, propylene glycol monopropyl ether acetate,
  • ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
  • Etc. examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
  • the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
  • amide solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like. These solvents may be used alone or in combination of two or more. Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3- Methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N, N-dimethylformamide, N-methylpyrrolidone and the like are preferable, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, di Propylene glycol methyl ether acetate, ethyl
  • 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 solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
  • the leveling agent (F) 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.
  • Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan GK) .
  • fluorosurfactant examples include surfactants having a fluorocarbon chain in the molecule.
  • Florard (registered trademark) FC430, FC431 manufactured by Sumitomo 3M Co., Ltd.
  • MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, F183, F554, R30, RS-718-K manufactured by DIC Corporation
  • Ftop registered trademark
  • EF301 EF303
  • EF351, EF352 manufactured by Mitsubishi Materials Electronic Chemicals
  • Surflon registered trademark
  • S381, S382 SC101, SC105 (Asahi Glass Co., Ltd.) and E5844 (Daikin Fine Chemical Laboratory Co., Ltd.).
  • silicone-based surfactant having a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.
  • the leveling agent (F) is contained, 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 not less than 0.1% by mass and more preferably not more than 0.005% by mass and not more than 0.07% by mass.
  • the colored curable resin composition of the present invention includes additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc., if necessary. May be included.
  • ⁇ Method for producing colored curable resin composition> The colored curable resin composition of the present invention is used as necessary, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E).
  • a leveling agent (F), a polymerization initiation assistant (D1), and other components can be mixed.
  • the pigment (A1) is included, the pigment 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 size 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. It is preferable to prepare a solution by dissolving Compound (I) in part or all of the solvent (E) in advance.
  • 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.
  • ⁇ Color filter manufacturing method> 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 and developed through a photomask.
  • 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
  • an aluminum, silver, silver / copper / palladium alloy thin film or the like 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.
  • 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.
  • the coating method include spin coating, slit coating, and slit and spin coating.
  • the temperature for performing heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. Further, 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, and 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.
  • 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.
  • a colored pattern is formed on the substrate by developing the exposed colored composition layer in contact with a developer. By the development, the unexposed portion of the colored composition layer is dissolved in the developer and removed.
  • the 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.
  • post-bake the obtained colored pattern 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.
  • Example 1a 50.0 parts of the compound represented by the formula (IIIa) and 350 parts of isopropyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) are mixed at room temperature, and diethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) 18.1 parts is mixed with the mixture. Was added dropwise at a temperature not exceeding 20 ° C. and stirred at 20 ° C.
  • the reaction mixture was cooled to room temperature, washed twice with 98 parts of 10% hydrochloric acid, twice with 98 parts of 10% saline and twice with 98 parts of ion-exchanged water, and then the chloroform was distilled off and dried. 1.2 parts of the compound represented by Ia-69) were obtained. The yield was 41%.
  • the reaction solution was cooled to room temperature and then charged into 73 parts of saturated brine.
  • the obtained precipitate was obtained as a residue of suction filtration, washed 3 times with 20 parts of 10% brine, then washed with 20 parts of ion-exchanged water and dried, and then compound 6.4 represented by the formula (Ia-100) Got a part.
  • the yield was 59%.
  • the obtained precipitate was obtained as a residue of suction filtration, washed 3 times with 30 parts of 10% brine, then washed with 30 parts of ion-exchanged water and dried, and then compound 6.4 represented by the formula (Ia-101) Got a part.
  • the yield was 59%.
  • Example 1b A solution obtained by mixing 40 parts of compound (IIb) and 146 parts of diethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) as compound (IIIb) in the presence of 100 parts of 1-methyl-2-pyrrolidone under light-shielding conditions. Was stirred at 30 ° C. for 3 hours.
  • the obtained reaction solution was cooled to room temperature, then added to a mixed solution of 400 parts of water and 20 parts of 35% hydrochloric acid and stirred at room temperature for 1 hour, whereby crystals were deposited.
  • the precipitated crystals were obtained as a suction filtration residue and dried to obtain 40 parts of a compound represented by the formula (Ib-37A).
  • 44.1 parts of the compound represented by the formula (Ib-37A) and 27.1 parts of N-methyl-ortho-toluidine manufactured by Tokyo Chemical Industry Co., Ltd.
  • Example 1c 20 parts of compound (IIc) and 14 parts of N-ethyl-ortho-toluidine (manufactured by Wako Pure Chemical Industries, Ltd.) as compound (IIIc) in the presence of 50 parts of 1-methyl-2-pyrrolidone under light-shielding conditions The resulting solution was stirred at 30 ° C. for 3 hours. The obtained reaction solution was cooled to room temperature, then added to a mixed solution of 400 parts of water and 20 parts of 35% hydrochloric acid and stirred at room temperature for 1 hour, whereby crystals were deposited. The precipitated crystals were obtained as a suction filtration residue and dried to obtain 25 parts of a compound represented by the formula (Ic-132A).
  • the temperature was maintained at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer (resin (B-1)) having a solid content of 43.5%.
  • the weight average molecular weight of the obtained resin (B-1) was 8000, the molecular weight distribution was 1.98, and the acid value in terms of solid content was 53 mg-KOH / g.
  • the polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
  • HLC-8120GPC manufactured by Tosoh Corporation
  • TSK-GELG2000HXL Column temperature: 40 ° C
  • Solvent THF Flow rate: 1.0 mL / min
  • Test liquid solid content concentration 0.001 to 0.01% by mass Injection volume: 50 ⁇ L Detector; RI Reference material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation)
  • Mw / Mn number average molecular weight ratio
  • Pigment Blue 15 6 30.1 parts; 13 parts acrylic pigment dispersant; Alkali-soluble resin (B): 53 parts of resin (B-1) (in terms of solid content); Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 10 parts; Solvent (E): 700 parts of propylene glycol monomethyl ether acetate; Solvent (E): 80 parts of propylene glycol monomethyl ether; In addition, the coloring agent composition (a) is obtained by mixing 0.1 part of a leveling agent (F): Megafac (registered trademark) F55
  • Colorant (A) 2.5 parts of the compound represented by formula (Ib-37), formula (Ib-8), formula (Ib-36), formula (Ib-38) or formula (Ib-101); C. I.
  • Pigment Blue 15 6 30.1 parts; 13 parts acrylic pigment dispersant; Alkali-soluble resin (B): 50 parts of resin (B-1) (in terms of solid content); Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 10 parts; Solvent (E): 720 parts of propylene glycol monomethyl ether acetate; Solvent (E): 80 parts of propylene glycol monomethyl ether; In addition, 0.1 part of a leveling agent (F): Megafac (registered trademark) F554 (manufactured by DIC
  • Colorant (A) represented by formula (Ic-132), formula (Ic-1), formula (Ic-7), formula (Ic-134), formula (Ic-138) or formula (Ic-140) 2.6 parts of a compound; C. I.
  • Pigment Blue 15 6 30.1 parts; 13 parts acrylic pigment dispersant; Alkali-soluble resin (B): 53 parts of resin (B-1) (in terms of solid content); Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts; Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 10 parts; Solvent (E): 700 parts of propylene glycol monomethyl ether acetate; Solvent (E): 80 parts of propylene glycol monomethyl ether; In addition, leveling agent (F): 0.1 part of MegaFac (registered trademark) F554 (manufactured by DIC Corporation) is
  • a colored curable composition (a), (b) or (c) is applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then pre-baked at 100 ° C. for 3 minutes. A composition layer is obtained. After cooling, the distance between the glass substrate on which the composition layer is formed and the photomask made of quartz glass is set to 100 ⁇ m, and using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), the atmospheric pressure is 150 mJ / cm 2. Light is irradiated with an exposure amount (365 nm reference). A photomask having a 100 ⁇ m line and space pattern is used.
  • the coating film was immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C. for 80 seconds, washed with water, and 220 ° C. in an oven. And bake for 20 minutes to obtain a pattern.
  • the compound of the present invention is excellent in solubility in an organic solvent.
  • the color filter formed from the colored curable resin composition containing the compound of the present invention can be expected to have higher brightness.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Optics & Photonics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Molecular Biology (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optical Filters (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Materials For Photolithography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un composé de formule (Ia) utilisé comme composé pour un colorant. (Ia) [R1a, R2a, R3a et R4a sont chacun indépendamment un groupe alkyle contenant 1 à 20 atomes de carbone ou un groupe cycloalkyle contenant 5 à 10 atomes de carbone, à condition que R1a, R2a, R3a et R4a ne soient pas tous le même groupe.]
PCT/JP2014/064901 2013-05-31 2014-05-29 Composé et composition de résine vulcanisable colorée Ceased WO2014192973A1 (fr)

Priority Applications (5)

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KR1020207027082A KR102250530B1 (ko) 2013-05-31 2014-05-29 화합물 및 착색 경화성 수지 조성물
CN201480030604.9A CN105408427A (zh) 2013-05-31 2014-05-29 化合物和着色固化性树脂组合物
KR1020207027072A KR102250529B1 (ko) 2013-05-31 2014-05-29 화합물 및 착색 경화성 수지 조성물
KR1020157035042A KR102204232B1 (ko) 2013-05-31 2014-05-29 화합물 및 착색 경화성 수지 조성물
JP2015519988A JP6370778B2 (ja) 2013-05-31 2014-05-29 化合物及び着色硬化性樹脂組成物

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JP2021073487A (ja) * 2016-12-19 2021-05-13 株式会社Ｄｎｐファインケミカル カラーフィルタ用着色樹脂組成物、色材分散液、カラーフィルタ、及び表示装置
JP2021080434A (ja) * 2019-11-18 2021-05-27 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
JP2021162854A (ja) * 2020-03-31 2021-10-11 住友化学株式会社 ネガ型レジスト組成物
JP2021176960A (ja) * 2016-06-20 2021-11-11 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 化合物及び着色硬化性樹脂組成物
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JP7143432B2 (ja) * 2018-10-11 2022-09-28 富士フイルム株式会社 着色組成物、膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子及び画像表示装置

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JP2017149848A (ja) * 2016-02-24 2017-08-31 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 化合物および着色硬化性樹脂組成物
JP2021176960A (ja) * 2016-06-20 2021-11-11 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 化合物及び着色硬化性樹脂組成物
JP7101295B2 (ja) 2016-06-20 2022-07-14 東友ファインケム株式会社 化合物及び着色硬化性樹脂組成物
KR102328826B1 (ko) 2016-11-07 2021-11-19 동우 화인켐 주식회사 화합물, 상기 화합물 수지를 포함하는 착색 수지 조성물, 상기 착색 수지 조성물로 형성되는 컬러 필터 및 상기 컬러 필터를 포함하는 표시 장치
JP2018076403A (ja) * 2016-11-07 2018-05-17 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 化合物
JP2018076402A (ja) * 2016-11-07 2018-05-17 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 化合物
KR20180051396A (ko) * 2016-11-07 2018-05-16 동우 화인켐 주식회사 화합물, 상기 화합물 수지를 포함하는 착색 수지 조성물, 상기 착색 수지 조성물로 형성되는 컬러 필터 및 상기 컬러 필터를 포함하는 표시 장치
JP2018100323A (ja) * 2016-12-19 2018-06-28 株式会社Ｄｎｐファインケミカル 色素
JP2021073487A (ja) * 2016-12-19 2021-05-13 株式会社Ｄｎｐファインケミカル カラーフィルタ用着色樹脂組成物、色材分散液、カラーフィルタ、及び表示装置
JP2021080434A (ja) * 2019-11-18 2021-05-27 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
JP7590144B2 (ja) 2019-11-18 2024-11-26 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
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JP7706329B2 (ja) 2021-10-15 2025-07-11 富士フイルム株式会社 蛍光性化合物及びこれを用いた蛍光標識生体物質

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JP6370778B2 (ja) 2018-08-08
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TW201823226A (zh) 2018-07-01
KR20160015251A (ko) 2016-02-12
CN106967037A (zh) 2017-07-21
KR102250530B1 (ko) 2021-05-11
JPWO2014192973A1 (ja) 2017-02-23
KR20200111285A (ko) 2020-09-28
KR102204232B1 (ko) 2021-01-19
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TWI644905B (zh) 2018-12-21
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