WO2014035203A1 - Styryl-based compound, coloring material comprising the styryl-based compound, photosensitive resin composition comprising the coloring material, photoresist material prepared from the photosensitive resin composition, color filter comprising the photoresist material, and display device comprising the color filter - Google Patents

Styryl-based compound, coloring material comprising the styryl-based compound, photosensitive resin composition comprising the coloring material, photoresist material prepared from the photosensitive resin composition, color filter comprising the photoresist material, and display device comprising the color filter Download PDF

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Publication number
WO2014035203A1
WO2014035203A1 PCT/KR2013/007864 KR2013007864W WO2014035203A1 WO 2014035203 A1 WO2014035203 A1 WO 2014035203A1 KR 2013007864 W KR2013007864 W KR 2013007864W WO 2014035203 A1 WO2014035203 A1 WO 2014035203A1
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group
substituted
unsubstituted
carbon atoms
styryl
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PCT/KR2013/007864
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French (fr)
Korean (ko)
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박종호
김한수
김성현
조창호
김선화
류장현
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주식회사 엘지화학
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Priority to JP2015527399A priority Critical patent/JP2015532667A/en
Priority to CN201380056895.4A priority patent/CN104768925B/en
Publication of WO2014035203A1 publication Critical patent/WO2014035203A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • 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
    • G03F7/0041—Photosensitive materials providing an etching agent upon exposure
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2014—Contact or film exposure of light sensitive plates such as lithographic plates or circuit boards, e.g. in a vacuum frame
    • G03F7/2016—Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing
    • G03F7/202—Masking pattern being obtained by thermal means, e.g. laser ablation

Definitions

  • the present specification relates to a styryl-based compound, a color material including the styryl-based compound, a photosensitive resin composition including the same, a photosensitive material prepared from the photosensitive resin composition, a color filter including the same, and a display device including the color filter. .
  • LED or OLED device which emits self light, instead of driving or liquid crystal, is being used instead of a conventional CCFL.
  • LED or OLED when LED or OLED is used as a light source, light of red, green, and blue is emitted by itself, and thus no separate color filter is required.
  • color filters are generally used to improve the color purity of light emitted from LED or OLED light sources to achieve high color reproducibility.
  • a color filter is necessary for color separation.
  • the color purity can be increased to improve the color reproduction and luminance.
  • the present specification is to provide a styryl-based compound, a color material including the styryl-based compound, a photosensitive resin composition comprising the same, a photosensitive material prepared from the photosensitive resin composition, a color filter including the same, and a display device including the color filter. do.
  • a styryl-based compound represented by Formula 1 is provided.
  • n is an integer from 1 to 3
  • n 1 to 4
  • X is NR or O
  • R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; And a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms,
  • L 1 is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; A substituted or unsubstituted 7 to 50 aralkyl group; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
  • R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms,
  • R 4 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
  • R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted acryloyl group having 3 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted acrylate group; Substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms; Or a substituted or un
  • a color material including the styryl compound is provided.
  • a photosensitive resin composition containing the color material.
  • a photosensitive material prepared from the photosensitive resin composition is provided.
  • a color filter including the photosensitive material is provided.
  • a display device including the color filter is provided.
  • the colorant according to one embodiment of the present specification has excellent heat resistance and / or solubility in organic solvents.
  • the photosensitive resin composition according to an exemplary embodiment of the present specification may obtain an absorption and transmission spectrum suitable for a light source to be applied, thereby achieving higher color reproducibility, higher brightness, and high contrast ratio.
  • the photosensitive resin composition which concerns on one Embodiment of this specification has high crosslinking degree, and is excellent in heat resistance. Therefore, the photosensitive resin composition which concerns on one Embodiment of this specification has little change of the color by heat processing.
  • 1 is a diagram showing absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7.
  • FIG. 2 is a diagram showing transmission spectra of Chemical Formulas 1-1, 1-3, and 1-7.
  • FIG. 2 is a diagram showing transmission spectra of Chemical Formulas 1-1, 1-3, and 1-7.
  • FIG. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 2.
  • FIG. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 2.
  • the present specification provides a styryl compound represented by Chemical Formula 1.
  • the styryl compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2.
  • n, m, R1 to R4, X and L1 are the same as defined above,
  • R6 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group containing at least one of N, O and S atoms.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  • R1 and R2 which are substituents of an amine are substituted or unsubstituted aryl groups having 6 to 40 carbon atoms; Or in the case of a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, the styryl-based compound including the same has a high molecular weight and excellent heat resistance.
  • R4 is a nitrile group; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms
  • L1 is a halogen group, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylamine group, alkylamine group, carbazole group, fluorenyl group, acryloyl group, acrylate group, nitrile group And a straight or branched chain alkylene group having 1 to 10 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group including one or more of N, O and S atoms.
  • R5 is hydrogen; Hydrogen; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms
  • substituted or unsubstituted is deuterium; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Silyl groups; Aryl alkenyl group; Aryl group; Aryloxy group; Alkyl thioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Boron group; Alkylamine group; Aralkyl amine groups; Arylamine group; Heteroaryl group; Carbazole groups; Acryloyl group; Acrylate group; Ether group; Fluorenyl group; Nitrile group; Nitro group; Hydroxyl group; It means that it is substituted with one or more substituents selected from the group consisting of a cyano group and a heterocyclic group containing one or more of N, O, S or P atoms or has no substituent.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl groups.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 25. Specific examples include, but are not limited to, alkenyl groups in which aryl groups such as stylbenyl and styrenyl groups are substituted.
  • the alkoxy group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 25.
  • a cycloalkyl group is not specifically limited, It is preferable that it is C3-C20, A cyclopentyl group and a cyclohexyl group are especially preferable.
  • the acryloyl group is not particularly limited, but preferably has 3 to 40 carbon atoms, especially methyl acrylate, ethyl acrylate, methacrylate, 3- (acryloyloxy) propyl methacrylate, or the like. There is, but is not limited to these.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example Etc.
  • the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example Etc.
  • the aralkyl group specifically has an aryl portion having 6 to 49 carbon atoms and an alkyl portion having 1 to 44 carbon atoms.
  • Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, ⁇ -methylbenzyl group, ⁇ , ⁇ -dimethylbenzyl Group, ⁇ , ⁇ -methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, ⁇ , ⁇ -ditrifluoromethylbenzyl group , p-methoxybenzyl group, m-methoxybenzyl group, ⁇ -phenoxybenzyl group, ⁇ -benzyl groupoxybenzyl group, nap
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 40 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C40.
  • the polycyclic aryl group may be naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is preferably 2-40 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.
  • an alkylene group means that there are two bonding positions in an alkane.
  • the alkylene group may be straight, branched or cyclic.
  • carbon number of an alkylene group is not specifically limited, It is preferable that it is C1-C6.
  • n 1
  • Formula X is O.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  • R1 is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
  • R1 is a substituted or unsubstituted methyl group.
  • R1 is a methyl group.
  • R1 is a substituted or unsubstituted ethyl group.
  • R1 is an ethyl group.
  • R1 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • R1 is a substituted or unsubstituted phenyl group.
  • R1 is a phenyl group.
  • R1 is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  • R1 is a substituted or unsubstituted benzyl group.
  • R1 is a benzyl group.
  • R2 is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
  • R2 is a substituted or unsubstituted methyl group.
  • R2 is a methyl group.
  • R2 is a substituted or unsubstituted ethyl group.
  • R2 is an ethyl group.
  • R2 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • R2 is a substituted or unsubstituted phenyl group.
  • R2 is a phenyl group.
  • R2 is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  • R2 is a substituted or unsubstituted benzyl group.
  • R2 is a benzyl group.
  • L1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • L1 is a linear or branched ethylene group.
  • L1 is a substituted or unsubstituted linear or branched propylene group.
  • L1 is a substituted or unsubstituted branched propylene group.
  • L1 is a propylene group in which a branched acrylate is substituted.
  • L1 is an isopropylene group in which (meth) acrylate is substituted.
  • R3 of Formula 1 is hydrogen.
  • R4 of the general formula 1 is a nitrile group.
  • R5 of Chemical Formula 1 is a substituted or unsubstituted carbonyl group.
  • R5 of Chemical Formula 1 is a substituted or unsubstituted acryloyl group.
  • R5 of the general formula 1 is an acryloyl group substituted with an alkyl group.
  • R5 of Formula 1 is an acryloyl group substituted with a methyl group.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8, but is not limited thereto.
  • the maximum absorption wavelength ( ⁇ max ) of the styryl compound is 400 nm to 500 nm.
  • the absorption spectrum of the styryl compound is in the range of 350 nm to 500 nm.
  • FIG. 1 is a diagram showing absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7.
  • the maximum absorption wavelength ( ⁇ max) of the styryl compound of one embodiment is 400 to 500 nm.
  • the said photosensitive resin composition expresses green.
  • 2 is a diagram of transmission spectra of 1-1, 1-3, and 1-7.
  • FIG. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 1.
  • FIG. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 1.
  • FIG. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1.
  • FIG. 4 In the wavelength region of 500 nm to 800 nm of the styryl compound of an exemplary embodiment of the present specification, the transmittance may be 90% to 100%.
  • Example 5 is an enlarged view of the transmission spectrum of Example 4 and Comparative Example 2 and the same. As described above, it can be seen that the luminance is increased during green development.
  • the styryl-based compound of Formula 1 may be prepared in a structure including a carbazole group, a cyan group and an acryl group by reacting a cyan group and a compound containing acrylic acid, such as NCCH 2 COOH, to a starting material including a tertiary amine structure. If necessary, an additional acrylic group may be introduced into the acrylic group.
  • the styryl-based compound according to one embodiment of the present specification may be combined with another substituent by light or heat.
  • a color material including the styryl compound is provided.
  • the photosensitive resin composition according to the exemplary embodiment of the present specification includes a colorant including a styryl system represented by Chemical Formula 1.
  • Colorant according to an exemplary embodiment of the present specification may be easy to fine-tune the transmission spectrum.
  • the color material is a dye type color material composed of the styryl-based compound alone.
  • the color material is the styryl-based compound; And at least one additional colorant selected from the group consisting of pigments and dyes.
  • the colorant according to one embodiment of the present specification may be used alone or in combination with the styryl compound and the pigment, dyes other than the styryl compound, or a mixture thereof.
  • the color material is a color material of a mixed type of a dye containing the styryl-based compound and a dye not containing the styryl-based compound.
  • the color material is a hybrid type color material of a salt / pigment containing a dye and a pigment containing the styryl-based compound.
  • the color material is a hybrid type color material of a salt / pigment including a dye including the styryl compound and a dye and a pigment not containing the styryl compound.
  • the color filter using the photosensitive resin composition comprising a styryl-based compound according to an exemplary embodiment of the present specification, it is possible to obtain an absorption and transmission spectrum suitable for a light source to be applied using various dyes and pigments, high color reproducibility, High brightness and high contrast ratio can be achieved.
  • Pigment means a powdery coloring material that is insoluble in water and organic solvents.
  • Dye refers to a coloring material that is dissolved in water and an organic solvent, dispersed as a single molecule, and combined and colored with molecules such as fibers.
  • colorant is meant herein a pigment, dye or mixture of pigments and dyes.
  • colorant means a mixture of the styryl compound and / or the colorant.
  • carbon black As black pigment, carbon black, graphite, a metal oxide, etc. can be used.
  • carbon black include cysto 5HIISAF-HS, cysto KH, cysto 3HHAF-HS, cysto NH, cysto 3M, cysto 300HAF-LS, cysto 116HMMAF-HS, cysto 116MAF, cysto FMFEF-HS , Sisto SOFEF, Sisto VGPF, Sisto SVHSRF-HS and Sisto SSRF (Donghae Carbon Co., Ltd.); Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, # 25, # CF9
  • examples of the coloring material that is colored is carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), perylene black (BASF K0084. K0086), cyanine black, linole yellow (CI21090), Linol yellow GRO (CI 21090), benzidine yellow 4T-564D, Victoria pure blue (CI42595), CI PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 202, 214, 215, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I.
  • PIGMENT yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 21
  • PIGMENT VIOLET 1 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc.
  • a white pigment, fluorescent pigment, etc. can also be used.
  • a substance containing zinc as the center metal can be used as the phthalocyanine-based complex compound to be used as a pigment.
  • the color material comprises one or two or more additional coloring materials selected from the group consisting of the styryl compound and a pigment and a dye, and the weight ratio of the coloring material and the styryl compound is 1:99 to 99: 1. In another embodiment, the weight ratio of the coloring material and the styryl compound is 3:97 to 97: 3. In another exemplary embodiment, the weight ratio of the coloring material and the styryl compound is 95: 5 to 5:95. There is an advantage of high transmittance within the above range.
  • the pigment may be PG58 or PY138.
  • the color material is composed of PG58 which is a pigment and the styryl compound.
  • the color material is composed of PG58 and PY138 which are pigments, and the styryl compound.
  • the dye has a solubility of 10% or more with respect to propylene glycol methyl ether acetate (PGMEA).
  • a photosensitive resin composition containing the color material.
  • the photosensitive resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.
  • the binder resin is not particularly limited as long as it can exhibit physical properties such as strength, developability, and the like of the film made of the photosensitive resin composition.
  • the binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
  • Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.
  • unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate
  • aromatic vinyl monomers include styrene, ⁇ -methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro It may be selected from the group consisting of styrene, but is not limited thereto.
  • unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
  • unsaturated imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.
  • acid anhydride examples include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.
  • the monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group.
  • the acid value of the binder resin is 50 to 130 KOH mg / g, the weight average molecular weight is 1,000 to 50,000.
  • the polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.
  • the photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking, and is, for example, from an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more selected.
  • the acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio)
  • biimidazole-based compound 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.
  • the triazine compound is 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionate, ethyl-2- ⁇ 4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate, 2-epoxyethyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio ⁇ acetate, cyclohexyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate,
  • the oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.
  • the solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropano
  • the content of the color material containing a styryl-based compound represented by Formula 1 is 5% by weight to 60% by weight
  • the binder resin The content of is from 1% to 60% by weight
  • the content of the initiator is from 0.1% to 20% by weight
  • the content of the multifunctional monomer is from 0.1% to 50% by weight.
  • the total weight of the solid content means the sum of the total weight of the components excluding the solvent in the photosensitive resin composition.
  • the weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.
  • the photosensitive resin composition is selected from the group consisting of photocrosslinking sensitizers, curing accelerators, adhesion promoters, surfactants, antioxidants, thermal polymerization inhibitors, ultraviolet absorbers, antioxidants, dispersants and leveling agents. It further comprises one or two additives.
  • the amount of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
  • the photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as
  • the curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.
  • methacryloyloxy propyltrimethoxy silane methacryloyloxy propyldimethoxy silane
  • methacryloyloxy propyltriethoxy silane methacryloyloxy propyldimethoxysilane
  • methacryloyl silane coupling agents such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.
  • the surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like.
  • F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.
  • the antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
  • antioxidants include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-t-
  • UV absorber 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.
  • thermal polymerization inhibitor examples include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.
  • the dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment.
  • a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
  • the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.
  • the leveling agent may be polymeric or nonpolymeric.
  • polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides
  • nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.
  • a photosensitive material prepared from the photosensitive resin composition is provided.
  • the photosensitive resin composition of this specification is apply
  • a spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely.
  • some residual solvent can be removed in some cases under reduced pressure.
  • Light sources for curing the photosensitive resin composition according to the present specification include, but are not limited to, mercury vapor arcs, carbon arcs, Xe arcs, etc., which emit light having a wavelength of 250 nm to 450 nm.
  • the photosensitive resin composition according to the present disclosure is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode Photoresist for forming overcoat layer, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photoresist for printed circuit board, photoresist for plasma display panel (PDP), etc.
  • TFT LCD thin film transistor liquid crystal display device
  • TFT LCD thin film transistor liquid crystal display device
  • PDP plasma display panel
  • a color filter including the photosensitive material is provided.
  • the color filter may be manufactured using the photosensitive resin composition including the styryl compound represented by Chemical Formula 1.
  • the color filter may be formed by coating the photosensitive composition on a substrate to form a coating film and exposing, developing and curing the coating film.
  • the photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having high color reproducibility and high luminance and contrast ratio even during the curing process during the manufacture of the color filter. Can be.
  • the substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • the color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
  • the color filter may further include an overcoat layer.
  • a black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast.
  • Chromium can be used as the material of the black matrix.
  • a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used.
  • a resin black matrix by a pigment dispersion method capable of fine processing can be used.
  • the black matrix according to one embodiment of the present specification may use black pigment or black dye as a colorant.
  • black pigment or black dye may be used alone, or carbon black and coloring pigments may be used.
  • coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.
  • a display device including a color filter according to the present specification.
  • the display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor.
  • the liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
  • the display device may have high color reproducibility, high luminance and contrast ratio, and excellent high light blocking characteristics. Due to these characteristics, the display device can be manufactured slim.
  • the display module itself may be manufactured slim, and the display may be maximized.
  • the compound 3a 1.5g (4.407mmol), 3b 0.917g (7.051mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.047g (5.464mmol), dimethylaminopyridine (DMAP) 0.070g (0.573mmol) 0 ⁇ 50 ml of 4 ° C tetrahydrofuran (THF) was added, followed by stirring for 2 hours at room temperature. 150 ml of water was added to the reaction and extracted with 700 ml of methyl chloride (MC).
  • EDC-HCl ethylcarbodiimide hydrochloride
  • DMAP dimethylaminopyridine
  • the compound 4a 1.25g (3.393mmol), 4b 0.706g (5.428mmol) ethylcarbodiimide hydrochloride (EDC-HCl) 0.806g, (4.207mmol), dimethylaminopyridine (DMAP) 0.051g, (0.441mmol) 0 401 ml of tetrahydrofuran (THF) was added to ⁇ 40 ° C., followed by stirring for 2 hours at room temperature for 24 hours. 150 ml of water was added to the reaction and extracted with 600 ml of methyl chloride (MC).
  • EDC-HCl ethylcarbodiimide hydrochloride
  • DMAP dimethylaminopyridine
  • Table 1 shows the results of comparing the color compositions of the green photosensitive resin compositions prepared according to the above Examples and Comparative Examples.
  • Binder resin copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI) 2.0, solids (SC) 25%
  • DPHA Diphenylpentaerythritol hexaacrylate
  • Table 2 shows the results of comparing the color compositions of the green photosensitive resin compositions prepared according to the above Examples and Comparative Examples.
  • Binder resin copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI) 2.0, solids (SC) 25%
  • the photosensitive resin composition is spin coated on a glass of 5 * 5 cm (Corning Co., Ltd.) and prebake at 90 ° C. for about 100 seconds to form a film.
  • the distance between the substrate on which the film was formed and the photo mask was set to 300 ⁇ m, and the exposure amount of 40 mJ / cm 2 was irradiated using an exposure machine (Hoya-shott).
  • the exposed substrate was developed for 60 seconds in a developing solution (KOH, 0.05%), and post-baked at 230 ° C. for 20 minutes to obtain a color pattern.
  • the transmittance spectrum of the visible light region in the range of 380 nm to 780 nm was obtained through a color pattern spectrometer.
  • the tristimulus value (X, Y, Z) value was obtained using the following equation, and the CIE1931 coordinates x, y, and Y were obtained from the following equation. Calculated using.
  • Table 3 shows the color coordinates calculated by the C light source using the green photosensitive resin composition.

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Abstract

The present specification relates to a styryl-based compound, to a coloring material comprising the styryl-based compound, to a photosensitive resin composition comprising the coloring material, to a photoresist material prepared from the photosensitive resin composition, to a color filter comprising the photoresist material, and to a display device comprising the color filter.

Description

스티릴계 화합물, 상기 스티릴계 화합물을 포함하는 색재, 이를 포함하는 감광성 수지 조성물, 상기 감광성 수지 조성물로 제조된 감광재, 상기 감광재를 포함하는 컬러필터 및 상기 컬러필터를 포함하는 디스플레이 장치A styryl-based compound, a color material including the styryl-based compound, a photosensitive resin composition comprising the same, a photosensitive material made of the photosensitive resin composition, a color filter including the photosensitive material, and a display device including the color filter.
본 명세서는 스티릴계 화합물, 상기 스티릴계 화합물을 포함하는 색재, 이를 포함하는 감광성 수지 조성물, 상기 감광성 수지 조성물로 제조된 감광재, 이를 포함하는 컬러필터 및 상기 컬러필터를 포함하는 디스플레이 장치에 관한 것이다. The present specification relates to a styryl-based compound, a color material including the styryl-based compound, a photosensitive resin composition including the same, a photosensitive material prepared from the photosensitive resin composition, a color filter including the same, and a display device including the color filter. .
본 명세서는 2012년 8월 31일에 한국특허청에 제출된 한국 특허출원 제 10-2012-0096343호의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다. 또한, 본 명세서는 2013년 1월 2일에 한국 특허청에 제출된 한국 특허출원 제 10-2013-0000370 호의 출원일의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다.This specification claims the benefit of Korean Patent Application No. 10-2012-0096343, filed with the Korea Intellectual Property Office on August 31, 2012, the contents of which are incorporated in full herein. In addition, this specification claims the benefit of the filing date of Korean Patent Application No. 10-2013-0000370 filed with the Korea Intellectual Property Office on January 2, 2013, the contents are all incorporated herein.
최근 액정 디스플레이(LCD)의 광원으로 기존 CCFL 대신 구동도 액정도 아닌 자체 발광을 하는 LED 또는 OLED 소자가 많이 이용되고 있다. 일반적으로 LED 또는 OLED 를 광원으로 이용하게 되면 자체로 적색, 녹색, 청색의 광이 나오기 때문에 별도의 컬러필터를 필요로 하지 않는다. Recently, as a light source of a liquid crystal display (LCD), an LED or an OLED device which emits self light, instead of driving or liquid crystal, is being used instead of a conventional CCFL. In general, when LED or OLED is used as a light source, light of red, green, and blue is emitted by itself, and thus no separate color filter is required.
그러나, 일반적으로 LED 또는 OLED 광원으로부터 나오는 광의 색순도를 향상시켜 높은 색 재현율을 달성하기 위하여 컬러필터를 사용한다. 특히 OLED 광원을 이용하여 백색광을 만들어 내는 경우에는 컬러의 구분을 위하여 반드시 컬러필터가 필요하다. However, color filters are generally used to improve the color purity of light emitted from LED or OLED light sources to achieve high color reproducibility. In particular, in the case of producing white light using an OLED light source, a color filter is necessary for color separation.
광원에서 나오는 스펙트럼과 컬러필터의 흡수 및 투과스펙트럼이 적절한 조합이 되어야만 색순도를 높여 색재현 및 휘도를 향상시킬 수 있다. Only when the spectrum from the light source and the absorption and transmission spectrum of the color filter are properly combined, the color purity can be increased to improve the color reproduction and luminance.
본 명세서는 스티릴계 화합물, 상기 스티릴계 화합물을 포함하는 색재, 이를 포함하는 감광성 수지 조성물, 상기 감광성 수지 조성물로 제조된 감광재, 이를 포함하는 컬러필터 및 상기 컬러필터를 포함하는 디스플레이 장치를 제공하고자 한다. The present specification is to provide a styryl-based compound, a color material including the styryl-based compound, a photosensitive resin composition comprising the same, a photosensitive material prepared from the photosensitive resin composition, a color filter including the same, and a display device including the color filter. do.
본 명세서의 일 실시상태에 있어서, 하기 화학식 1로 표시되는 스티릴계 화합물을 제공한다. In one embodiment of the present specification, a styryl-based compound represented by Formula 1 is provided.
[화학식 1][Formula 1]
Figure PCTKR2013007864-appb-I000001
Figure PCTKR2013007864-appb-I000001
화학식 1에 있어서, In Chemical Formula 1,
n은 1 내지 3의 정수이고, n is an integer from 1 to 3,
m은 1 내지 4의 정수이며, m is an integer from 1 to 4,
X는 NR 또는 O이고, X is NR or O,
R은 수소; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로 알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 및 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기로 이루어진 군에서 선택되며,R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; And a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms,
L1은 직접결합; 또는 탄소수 1 내지 10의 치환 또는 비치환된 알킬렌기이며, L 1 is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 7 내지 50의 아르알킬기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이고,R1 and R2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; A substituted or unsubstituted 7 to 50 aralkyl group; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
R3는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기이며, R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms,
R4는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이고,R 4 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
R5는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 탄소수 3 내지 40의 아크릴로일기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 아크릴레이트기; 치환 또는 비치환된 탄소수 1 내지 40의 카보닐기; 또는 N, O, S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다. R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted acryloyl group having 3 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted acrylate group; Substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing one or more of N, O, S atoms.
본 명세서의 일 실시상태에 있어서, 상기 스티릴계 화합물을 포함하는 색재를 제공한다. In one embodiment of the present specification, a color material including the styryl compound is provided.
본 명세서의 일 실시상태에 있어서, 상기 색재를 포함하는 감광성 수지 조성물을 제공한다. In one embodiment of the present specification, there is provided a photosensitive resin composition containing the color material.
본 명세서의 일 실시상태에 있어서, 상기 감광성 수지 조성물로 제조된 감광재를 제공한다. In an exemplary embodiment of the present specification, a photosensitive material prepared from the photosensitive resin composition is provided.
본 명세서의 일 실시상태에 있어서, 상기 감광재를 포함하는 컬러필터를 제공한다. In one embodiment of the present specification, a color filter including the photosensitive material is provided.
본 명세서의 일 실시상태에 있어서, 상기 컬러필터를 포함하는 디스플레이 장치를 제공한다. In one embodiment of the present specification, a display device including the color filter is provided.
본 명세서의 일 실시상태에 따른 색재는 내열성 및/또는 유기 용매에 대한 용해도가 우수하다. The colorant according to one embodiment of the present specification has excellent heat resistance and / or solubility in organic solvents.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 적용하고자 하는 광원에 적합한 흡수 및 투과 스펙트럼을 얻을 수 있어, 보다 높은 색재현율 및 고휘도, 고명암비 등을 달성할 수 있다. The photosensitive resin composition according to an exemplary embodiment of the present specification may obtain an absorption and transmission spectrum suitable for a light source to be applied, thereby achieving higher color reproducibility, higher brightness, and high contrast ratio.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 가교도가 높아, 내열성이 우수하다. 따라서, 본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 열처리에 의한 색의 변화가 적다.The photosensitive resin composition which concerns on one Embodiment of this specification has high crosslinking degree, and is excellent in heat resistance. Therefore, the photosensitive resin composition which concerns on one Embodiment of this specification has little change of the color by heat processing.
도 1은 화학식 1-1, 1-3, 1-5 및 1-7의 흡수 스펙트럼을 나타낸 도이다.1 is a diagram showing absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7.
도 2는 화학식 1-1, 1-3 및 1-7의 투과 스펙트럼에 대한 도이다. FIG. 2 is a diagram showing transmission spectra of Chemical Formulas 1-1, 1-3, and 1-7. FIG.
도 3은 실시예 3 및 비교예 1의 투과 스펙트럼에 대한 도이다. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1. FIG.
도 4는 실시예 3 및 비교예 1의 투과 스펙트럼을 확대한 도이다. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1. FIG.
도 5는 실시예 4 및 비교예 2의 투과 스펙트럼을 나타낸 도이다. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 2. FIG.
이하 본 명세서를 보다 상세히 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 스티릴계 화합물을 제공한다. The present specification provides a styryl compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 스티릴계 화합물은 하기 화학식 2로 표시된다. In one embodiment of the present specification, the styryl compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
Figure PCTKR2013007864-appb-I000002
Figure PCTKR2013007864-appb-I000002
화학식 2에 있어서, In Chemical Formula 2,
n, m, R1 내지 R4, X 및 L1은 상기에서 정의한 바와 동일하고, n, m, R1 to R4, X and L1 are the same as defined above,
R6는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다. R6 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group containing at least one of N, O and S atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기이다. In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기이다. In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
본 명세서에 있어서, 아민의 치환기인 R1 및 R2가 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기인 경우, 이를 포함하는 스티릴계 화합물은 분자량이 높아 내열성이 우수한 효과가 있다. In the present specification, R1 and R2 which are substituents of an amine are substituted or unsubstituted aryl groups having 6 to 40 carbon atoms; Or in the case of a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, the styryl-based compound including the same has a high molecular weight and excellent heat resistance.
본 명세서의 일 실시상태에 있어서, 상기 R4는 니트릴기; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기이다. In one embodiment of the present specification, R4 is a nitrile group; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms An aryl group having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from; Or a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group including at least one of N, O and S atoms Heterocyclic group containing one or more of N, O and S atoms unsubstituted or substituted with one or more substituents selected from the group.
본 명세서의 일 실시상태에 있어서, L1은 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 아크릴로일기, 아크릴레이트기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 직쇄 또는 분지쇄의 탄소수 1 내지 10의 알킬렌기이다. In one embodiment of the present specification, L1 is a halogen group, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylamine group, alkylamine group, carbazole group, fluorenyl group, acryloyl group, acrylate group, nitrile group And a straight or branched chain alkylene group having 1 to 10 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group including one or more of N, O and S atoms.
본 명세서의 일 실시상태에 있어서, 상기 R5는 수소; 수소; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아크릴레이트기; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 카보닐기; 또는 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아크릴로일기이다. In one embodiment of the present specification, R5 is hydrogen; Hydrogen; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms An acrylate group unsubstituted or substituted with one or more substituents selected from; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms A carbonyl group unsubstituted or substituted with one or more substituents selected from; Or a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group including at least one of N, O and S atoms It is an acryloyl group unsubstituted or substituted with one or more substituents selected from the group.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents are described below, but are not limited thereto.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 알킬기; 알케닐기; 알콕시기; 시클로알킬기; 실릴기; 아릴알케닐기; 아릴기; 아릴옥시기; 알킬티옥시기; 알킬술폭시기; 아릴술폭시기; 붕소기; 알킬아민기; 아랄킬아민기; 아릴아민기; 헤테로아릴기; 카바졸기; 아크릴로일기; 아크릴레이트기; 에테르기; 플루오레닐기; 니트릴기; 니트로기; 히드록시기; 시아노기 및 N, O, S 또는 P 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되었거나 또는 어떠한 치환기도 갖지 않는 것을 의미한다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Silyl groups; Aryl alkenyl group; Aryl group; Aryloxy group; Alkyl thioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Boron group; Alkylamine group; Aralkyl amine groups; Arylamine group; Heteroaryl group; Carbazole groups; Acryloyl group; Acrylate group; Ether group; Fluorenyl group; Nitrile group; Nitro group; Hydroxyl group; It means that it is substituted with one or more substituents selected from the group consisting of a cyano group and a heterocyclic group containing one or more of N, O, S or P atoms or has no substituent.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 25인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, t-부틸기, 펜틸기, 헥실기 및 헵틸기 등이 있으나, 이들에 한정되지 않는다.  In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl groups.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 25인 것이 바람직하다. 구체적인 예로는 스틸베닐기(stylbenyl), 스티레닐기(styrenyl)기 등의 아릴기가 치환된 알케닐기가 바람직하나 이들에 한정되지 않는다. In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 25. Specific examples include, but are not limited to, alkenyl groups in which aryl groups such as stylbenyl and styrenyl groups are substituted.
본 명세서에 있어서, 상기 알콕시기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 25인 것이 바람직하다. In the present specification, the alkoxy group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 25.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 20인 것이 바람직하며, 특히 시클로펜틸기, 시클로헥실기가 바람직하다.In this specification, although a cycloalkyl group is not specifically limited, It is preferable that it is C3-C20, A cyclopentyl group and a cyclohexyl group are especially preferable.
본 명세서에 있어서, 상기 아크릴로일기는 특별히 한정되지 않으나, 탄소수 3 내지 40인 것이 바람직하며, 특히 메틸아크릴레이트, 에틸아크릴레이트, 메타크릴레이트, 3-(아크릴로일옥시) 프로필 메타크릴레이트 등이 있으나, 이들에 한정되지 않는다. In the present specification, the acryloyl group is not particularly limited, but preferably has 3 to 40 carbon atoms, especially methyl acrylate, ethyl acrylate, methacrylate, 3- (acryloyloxy) propyl methacrylate, or the like. There is, but is not limited to these.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는
Figure PCTKR2013007864-appb-I000003
등이 있다. In the present specification, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example
Figure PCTKR2013007864-appb-I000003
Etc.
본 명세서에 있어서, 플루오레닐기는 열린 플루오레닐기의 구조를 포함하며, 여기서 열린 플루오레닐기는 2개의 고리 화합물이 1개의 원자를 통하여 연결된 구조에서 한쪽 고리 화합물이 연결이 끊어진 상태의 구조로서, 예로는
Figure PCTKR2013007864-appb-I000004
등이 있다. In the present specification, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example
Figure PCTKR2013007864-appb-I000004
Etc.
본 명세서에 있어서, 상기 아르알킬기는 구체적으로 아릴부분은 탄소수 6 내지 49이고, 알킬 부분은 탄소수 1 내지 44이다. 구체적인 예로는 벤질기, p-메틸벤질기, m-메틸벤질기, p-에틸벤질기, m-에틸벤질기, 3,5-디메틸벤질기, α-메틸벤질기, α,α-디메틸벤질기, α,α-메틸페닐벤질기, 1-나프틸벤질기, 2-나프틸벤질기, p-플루오르벤질기, 3,5-디플루오르벤질기, α,α-디트리플루오로메틸벤질기, p-메톡시벤질기, m-메톡시벤질기, α-페녹시벤질기, α-벤질기옥시벤질기, 나프틸메틸기, 나프틸에틸기, 나프틸이소프로필기, 피롤릴메틸기, 피롤렐에틸기, 아미노벤질기, 니트로벤질기, 시아노벤질기, 1-히드록시-2-페닐이소프로필기, 1-클로로-2-페닐이소프로필기 등이 있으나, 이에 한정되지 않는다.In the present specification, the aralkyl group specifically has an aryl portion having 6 to 49 carbon atoms and an alkyl portion having 1 to 44 carbon atoms. Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, α-methylbenzyl group, α, α-dimethylbenzyl Group, α, α-methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, α, α-ditrifluoromethylbenzyl group , p-methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyl groupoxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrole Ethyl group, aminobenzyl group, nitrobenzyl group, cyanobenzyl group, 1-hydroxy-2-phenyl isopropyl group, 1-chloro-2-phenyl isopropyl group and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 단환식 아릴기 또는 다환식 아릴기일 수 있다. In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 40인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 40 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 40인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트릴기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C40. Specifically, the polycyclic aryl group may be naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 헤테로고리기는 이종원자로 O, N 또는 S를 포함하는 헤테로 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2-40인 것이 바람직하다. 헤테로 고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 트리아진기, 아크리딜기, 피리다진기, 퀴놀리닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨란기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is preferably 2-40 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.
본 명세서에서 알킬렌기는 알칸(alkane)에 결합위치가 두 개 있는 것을 의미한다. 상기 알킬렌기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알킬렌기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 6인 것이 바람직하다.In the present specification, an alkylene group means that there are two bonding positions in an alkane. The alkylene group may be straight, branched or cyclic. Although carbon number of an alkylene group is not specifically limited, It is preferable that it is C1-C6.
본 명세서의 일 실시상태에 있어서, 상기 n은 1이다. In one embodiment of the present specification, n is 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 X는 O이다. In one embodiment of the present specification, Formula X is O.
본 명세서의 하나의 실시상태에 있어서, R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기이다. In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 탄소수 1내지 25의 알킬기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 메틸기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted methyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 메틸기이다. In one embodiment of the present specification, R1 is a methyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 에틸기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 에틸기이다. In one embodiment of the present specification, R1 is an ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 탄소수 6 내지 40의 아릴기이다.In one embodiment of the present specification, R1 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 페닐기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 페닐기이다. In one embodiment of the present specification, R1 is a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1은 치환 또는 비치환된 벤질기이다. In one embodiment of the present specification, R1 is a substituted or unsubstituted benzyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1은 벤질기이다. In one embodiment of the present specification, R1 is a benzyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 탄소수 1내지 25의 알킬기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 메틸기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted methyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 메틸기이다. In one embodiment of the present specification, R2 is a methyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 에틸기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 에틸기이다. In one embodiment of the present specification, R2 is an ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 탄소수 6 내지 40의 아릴기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 페닐기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 페닐기이다. In one embodiment of the present specification, R2 is a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 벤질기이다. In one embodiment of the present specification, R2 is a substituted or unsubstituted benzyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 벤질기이다. In one embodiment of the present specification, R2 is a benzyl group.
본 명세서의 일 실시상태에 있어서, L1은 탄소수 1 내지 10의 치환 또는 비치환된 알킬렌기이다. In one embodiment of the present specification, L1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
또 하나의 실시상태에 있어서, L1은 직쇄 또는 분지쇄의 에틸렌기이다.In another exemplary embodiment, L1 is a linear or branched ethylene group.
본 명세서의 일 실시상태에 있어서, L1은 치환 또는 비치환된 직쇄 또는 분지쇄의 프로필렌기이다. In one embodiment of the present specification, L1 is a substituted or unsubstituted linear or branched propylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1은 치환 또는 비치환된 분지쇄의 프로필렌기이다. In one embodiment of the present specification, L1 is a substituted or unsubstituted branched propylene group.
또 하나의 실시상태에 있어서, 상기 L1은 분지쇄의 아크릴레이트가 치환된 프로필렌기이다. In another exemplary embodiment, L1 is a propylene group in which a branched acrylate is substituted.
본 명세서의 일 실시상태에 있어서, 상기 L1은 (메트)아크릴레이트가 치환된 이소프로필렌기이다. In one embodiment of the present specification, L1 is an isopropylene group in which (meth) acrylate is substituted.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R3는 수소이다. In one embodiment of the present specification, R3 of Formula 1 is hydrogen.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R4는 니트릴기이다. In one embodiment of the present specification, R4 of the general formula 1 is a nitrile group.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R5는 치환 또는 비치환된 카보닐기이다. In one embodiment of the present specification, R5 of Chemical Formula 1 is a substituted or unsubstituted carbonyl group.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R5는 치환 또는 비치환된 아크릴로일기이다. In one embodiment of the present specification, R5 of Chemical Formula 1 is a substituted or unsubstituted acryloyl group.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R5는 알킬기로 치환된 아크릴로일기이다. In one embodiment of the present specification, R5 of the general formula 1 is an acryloyl group substituted with an alkyl group.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 1의 R5는 메틸기로 치환된 아크릴로일기이다. In one embodiment of the present specification, R5 of Formula 1 is an acryloyl group substituted with a methyl group.
또한, 상기 화학식 1은 하기 화학식 1-1 내지 1-8 중 어느 하나로 표시되나, 이에 한정되는 것은 아니다. In addition, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8, but is not limited thereto.
Figure PCTKR2013007864-appb-I000005
Figure PCTKR2013007864-appb-I000005
본 명세서의 일 실시상태에 있어서, 상기 스티릴계 화합물의 최대 흡수 파장(λmax)는 400 nm 내지 500 nm이다. In one embodiment of the present specification, the maximum absorption wavelength (λ max ) of the styryl compound is 400 nm to 500 nm.
본 명세서의 일 실시상태에 있어서, 상기 스티릴계 화합물의 흡수 스펙트럼의 범위는 350 nm 내지 500 nm이다. In one embodiment of the present specification, the absorption spectrum of the styryl compound is in the range of 350 nm to 500 nm.
도 1은 화학식 1-1, 1-3, 1-5 및 1-7의 흡수 스펙트럼을 나타낸 도이다. 도 1에서 보면 일 실시상태의 스티릴계 화합물의 최대 흡수 파장(λmax)은 400 내지 500 nm 임을 확인 할 수 있다. 이 경우, 상기 감광성 수지 조성물은 녹색을 발현한다.1 is a diagram showing absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7. In Figure 1 it can be seen that the maximum absorption wavelength (λ max) of the styryl compound of one embodiment is 400 to 500 nm. In this case, the said photosensitive resin composition expresses green.
도 2는 1-1, 1-3 및 1-7의 투과 스펙트럼에 대한 도이다. 2 is a diagram of transmission spectra of 1-1, 1-3, and 1-7.
도 3은 실시예 3 및 비교예 1의 투과 스펙트럼에 대한 도이다. 3 is a diagram showing transmission spectra of Example 3 and Comparative Example 1. FIG.
도 4는 실시예 3 및 비교예 1의 투과 스펙트럼을 확대한 도이다. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1. FIG.
도 5는 실시예 4 및 비교예 1의 투과 스펙트럼에 대한 도이다. 5 is a diagram showing transmission spectra of Example 4 and Comparative Example 1. FIG.
또한, 도 4는 실시예 3 및 비교예1의 투과 스펙트럼을 확대한 도이다. 본 명세서의 일 실시상태의 상기 스티릴계 화합물의 500 nm 내지 800 nm 파장 영역에서 투과도가 90 % 내지 100 %일 수 있다. 4 is an enlarged view of transmission spectra of Example 3 and Comparative Example 1. FIG. In the wavelength region of 500 nm to 800 nm of the styryl compound of an exemplary embodiment of the present specification, the transmittance may be 90% to 100%.
도 5는 실시예 4 및 비교예 2의 투과스펙트럼에 대한 도 및 이를 확대한 도이다. 상기와 같이, 녹색 발현시 휘도가 상승하는 것을 확인할 수 있다. 5 is an enlarged view of the transmission spectrum of Example 4 and Comparative Example 2 and the same. As described above, it can be seen that the luminance is increased during green development.
상기 화학식 1의 스티릴계 화합물은 3차 아민 구조를 포함하는 출발물질에 시안기와 아크릴산을 포함하는 화합물, 예컨대 NCCH2COOH를 반응시킴으로써 카바졸기, 시안기 및 아크릴기를 포함하는 구조로 제조될 수 있다. 필요에 따라 아크릴기에 추가의 아크릴기를 도입할 수 있다. The styryl-based compound of Formula 1 may be prepared in a structure including a carbazole group, a cyan group and an acryl group by reacting a cyan group and a compound containing acrylic acid, such as NCCH 2 COOH, to a starting material including a tertiary amine structure. If necessary, an additional acrylic group may be introduced into the acrylic group.
본 명세서의 일 실시상태에 따른 스티릴계 화합물은 광이나 열에 의하여 다른 치환기와 결합할 수 있다. The styryl-based compound according to one embodiment of the present specification may be combined with another substituent by light or heat.
본 명세서의 일 실시상태에 있어서, 상기 스티릴계 화합물을 포함하는 색재를 제공한다. In one embodiment of the present specification, a color material including the styryl compound is provided.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 상기 화학식 1로 표시되는 스티릴계를 포함하는 색재를 포함한다.The photosensitive resin composition according to the exemplary embodiment of the present specification includes a colorant including a styryl system represented by Chemical Formula 1.
기존 안료만을 포함한 안료 타입의 감광성 수지 조성물을 이용한 컬러필터의 경우, 사용되는 광원에 적합한 흡수 및 투과 스펙트럼을 갖는 안료의 수가 제한적이며, 흡수 및 투과 스펙트럼의 미세 조절이 어렵다. In the case of a color filter using a pigment type photosensitive resin composition containing only existing pigments, the number of pigments having an absorption and transmission spectrum suitable for the light source used is limited, and fine control of the absorption and transmission spectrum is difficult.
본 명세서의 일 실시상태에 따른 색재는 투과 스펙트럼의 미세 조절이 용이할 수 있다. Colorant according to an exemplary embodiment of the present specification may be easy to fine-tune the transmission spectrum.
본 명세서의 일 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물 단독으로 구성된 염료타입의 색재다. In one embodiment of the present specification, the color material is a dye type color material composed of the styryl-based compound alone.
본 명세서의 일 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물; 및 안료 및 염료로 이루어진 군으로부터 선택되는 1 또는 2 이상의 추가의 착색제를 포함한다. In one embodiment of the present specification, the color material is the styryl-based compound; And at least one additional colorant selected from the group consisting of pigments and dyes.
구체적으로 본 명세서의 일 실시상태에 따른 색재는 상기 스티릴계 화합물 단독으로 사용하거나, 상기 스티릴계 화합물과 안료, 상기 스티릴계 화합물 이외의 염료, 또는 이들의 혼합물을 혼합하여 사용할 수 있다. Specifically, the colorant according to one embodiment of the present specification may be used alone or in combination with the styryl compound and the pigment, dyes other than the styryl compound, or a mixture thereof.
구체적으로, 하나의 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물을 포함하는 염료와 상기 스티릴계 화합물을 포함하지 않는 염료의 혼합 타입의 색재다. 또 하나의 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물을 포함하는 염료와 안료를 포함하는 염/안료의 하이브리드 타입의 색재다. 또 하나의 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물을 포함하는 염료, 상기 스티릴계 화합물을 포함하지 않은 염료 및 안료를 포함하는 염/안료의 하이브리드 타입의 색재다. Specifically, in one embodiment, the color material is a color material of a mixed type of a dye containing the styryl-based compound and a dye not containing the styryl-based compound. In another exemplary embodiment, the color material is a hybrid type color material of a salt / pigment containing a dye and a pigment containing the styryl-based compound. In another exemplary embodiment, the color material is a hybrid type color material of a salt / pigment including a dye including the styryl compound and a dye and a pigment not containing the styryl compound.
본 명세서의 일 실시상태에 따른 스티릴계 화합물을 포함하는 감광성 수지 조성물을 이용한 컬러필터의 경우, 다양한 염료 및 안료를 이용하여 적용하고자 하는 광원에 적합한 흡수 및 투과 스펙트럼을 얻을 수 있어, 높은 색재현율, 고휘도 및 고명암비를 달성할 수 있다. In the case of the color filter using the photosensitive resin composition comprising a styryl-based compound according to an exemplary embodiment of the present specification, it is possible to obtain an absorption and transmission spectrum suitable for a light source to be applied using various dyes and pigments, high color reproducibility, High brightness and high contrast ratio can be achieved.
안료(pigment)는 물 및 유기용매에 녹지 않는 분말상의 착색재를 의미한다. Pigment means a powdery coloring material that is insoluble in water and organic solvents.
염료(dye)는 물 및 유기용매에 녹아 단분자로 분산하여 섬유등의 분자와 결합하여 착색되는 착색재를 의미한다.Dye refers to a coloring material that is dissolved in water and an organic solvent, dispersed as a single molecule, and combined and colored with molecules such as fibers.
본 명세서에서의 "착색재"는 안료, 염료 또는 안료와 염료의 혼합물을 의미한다. By "colorant" is meant herein a pigment, dye or mixture of pigments and dyes.
본 명세서에서의 "색재"는 상기 스티릴계 화합물 및/또는 상기 착색재의 혼합물을 의미한다. As used herein, "colorant" means a mixture of the styryl compound and / or the colorant.
흑색 안료로는 카본 블랙, 흑연, 금속 산화물 등을 사용할 수 있다. 카본 블랙의 예로는 시스토 5HIISAF-HS, 시스토 KH, 시스토 3HHAF-HS, 시스토 NH, 시스토 3M, 시스토 300HAF-LS, 시스토 116HMMAF-HS, 시스토 116MAF, 시스토 FMFEF-HS, 시스토 SOFEF, 시스토 VGPF, 시스토 SVHSRF-HS 및 시스토 SSRF(동해카본 ㈜) ; 다이어그램 블랙 II, 다이어그램 블랙 N339, 다이어그램 블랙 SH, 다이어그램 블랙 H, 다이어그램 LH, 다이어그램 HA, 다이어그램 SF, 다이어그램 N550M, 다이어그램 M, 다이어그램 E, 다이어그램 G, 다이어그램 R, 다이어그램 N760M, 다이어그램 LR, #2700, #2600, #2400, #2350, #2300, #2200, #1000, #980, #900, MCF88, #52, #50, #47, #45, #45L, #25, #CF9, #95, #3030, #3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B 및 OIL31B(미쯔비시화학㈜) ; PRINTEX-U, PRINTEX-V, PRINTEX-140U, PRINTEX-140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, PRINTEX-25, PRINTEX-200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, 및 LAMP BLACK-101(대구사㈜); RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN-820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN-2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170(콜롬비아 카본㈜) 또는 이들의 혼합물 등이 있다. 또한, 색깔을 띄는 착색재의 예로는 카민 6B(C.I.12490), 프탈로시아닌 그린(C.I. 74260), 프탈로시아닌 블루(C.I. 74160), 페릴렌 블랙(BASF K0084. K0086), 시아닌 블랙, 리놀옐로우(C.I.21090), 리놀 옐로우GRO(C.I. 21090), 벤지딘 옐로우4T-564D, 빅토리아 퓨어 블루(C.I.42595), C.I. PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 202, 214, 215, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I. PIGMENT GREEN 7, 10, 36, 37, 58; C.I. PIGMENT blue 1, 1:2, 1:3, 2, 2:1, 2:2, 3, 8, 9, 10, 10:1, 11, 12, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 18, 19, 22, 24, 24:1, 53, 56, 56:1, 57, 58, 59, 60, 61, 62, 64; C.I. PIGMENT yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214; C.I. PIGMENT VIOLET 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 등이 있고, 이 밖에 백색 안료, 형광 안료 등도 이용할 수 있다. 안료로 사용되는 프탈로시아닌계 착화합물로는 구리 외에 아연을 중심 금속으로 하는 물질도 사용 가능하다.As black pigment, carbon black, graphite, a metal oxide, etc. can be used. Examples of carbon black include cysto 5HIISAF-HS, cysto KH, cysto 3HHAF-HS, cysto NH, cysto 3M, cysto 300HAF-LS, cysto 116HMMAF-HS, cysto 116MAF, cysto FMFEF-HS , Sisto SOFEF, Sisto VGPF, Sisto SVHSRF-HS and Sisto SSRF (Donghae Carbon Co., Ltd.); Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, # 25, # CF9, # 95, # 3030, # 3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B and OIL31B (Mitsubishi Chemical Corporation); PRINTEX-U, PRINTEX-V, PRINTEX-140U, PRINTEX-140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, PRINTEX-25, PRINTEX- 200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, and LAMP BLACK-101 (Daegu Corporation); RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN- 820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN-2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170 (Colombia Carbon, Inc.) or mixtures thereof. In addition, examples of the coloring material that is colored is carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), perylene black (BASF K0084. K0086), cyanine black, linole yellow (CI21090), Linol yellow GRO (CI 21090), benzidine yellow 4T-564D, Victoria pure blue (CI42595), CI PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 202, 214, 215, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I. PIGMENT GREEN 7, 10, 36, 37, 58; C.I. PIGMENT blue 1, 1: 2, 1: 3, 2, 2: 1, 2: 2, 3, 8, 9, 10, 10: 1, 11, 12, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 18, 19, 22, 24, 24: 1, 53, 56, 56: 1, 57, 58, 59, 60, 61, 62, 64; C.I. PIGMENT yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214; C.I. PIGMENT VIOLET 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc. In addition, a white pigment, fluorescent pigment, etc. can also be used. As the phthalocyanine-based complex compound to be used as a pigment, in addition to copper, a substance containing zinc as the center metal can be used.
본 명세서의 일 실시상태에 있어서, 상기 색재는 상기 스티릴계 화합물과 안료 및 염료로 이루어진 군으로부터 선택되는 1 또는 2 이상의 추가의 착색재를 포함하고, 상기 착색재와 상기 스티릴계 화합물의 중량 비율은 1:99 내지 99:1 이다. 또 하나의 실시상태에 있어서, 상기 착색재와 상기 스티릴계 화합물의 중량비율은 3:97 내지 97:3이다. 또 하나의 실시상태에 있어서, 상기 착색재와 상기 스티릴계 화합물의 중량비율은 95:5 내지 5:95이다. 상기 범위 내에서 투과율이 높은 이점이 있다. In one embodiment of the present specification, the color material comprises one or two or more additional coloring materials selected from the group consisting of the styryl compound and a pigment and a dye, and the weight ratio of the coloring material and the styryl compound is 1:99 to 99: 1. In another embodiment, the weight ratio of the coloring material and the styryl compound is 3:97 to 97: 3. In another exemplary embodiment, the weight ratio of the coloring material and the styryl compound is 95: 5 to 5:95. There is an advantage of high transmittance within the above range.
본 명세서의 일 실시상태에 있어서, 상기 안료는 PG58 또는 PY138 일 수 있다. In one embodiment of the present specification, the pigment may be PG58 or PY138.
본 명세서의 일 실시상태에 있어서, 상기 색재는 안료인 PG58과 상기 스티릴계 화합물로 구성된다. In one embodiment of the present specification, the color material is composed of PG58 which is a pigment and the styryl compound.
본 명세서의 일 실시상태에 있어서, 상기 색재는 안료인 PG58 및 PY138과 상기 스티릴계 화합물로 구성된다. In one embodiment of the present specification, the color material is composed of PG58 and PY138 which are pigments, and the styryl compound.
본 명세서의 일 실시상태에 있어서, 상기 염료는 프로필렌글리콜메틸에테르아세테이트(PGMEA)에 대해서 용해도는 10% 이상이다. In one embodiment of the present specification, the dye has a solubility of 10% or more with respect to propylene glycol methyl ether acetate (PGMEA).
본 명세서의 일 실시상태에 있어서, 상기 색재를 포함하는 감광성 수지 조성물을 제공한다. In one embodiment of the present specification, there is provided a photosensitive resin composition containing the color material.
본 명세서의 일 실시상태에 있어서, 상기 감광성 수지 조성물은 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 더 포함할 수 있다. In one embodiment of the present specification, the photosensitive resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.
상기 바인더 수지는 감광성 수지 조성물로 제조된 막의 강도, 현상성 등의 물성을 나타낼 수 있다면, 특별히 한정하지 않는다. The binder resin is not particularly limited as long as it can exhibit physical properties such as strength, developability, and the like of the film made of the photosensitive resin composition.
상기 바인더 수지는 기계적 강도를 부여하는 다관능성 모노머와 알칼리 용해성을 부여하는 모노머의 공중합 수지를 이용할 수 있으며, 당 기술분야에서 일반적으로 사용하는 바인더를 더 포함할 수 있다. The binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
상기 막의 기계적 강도를 부여하는 다관능성 모노머는 불포화 카르복시산 에스테류; 방향족 비닐류; 불포화 에테르류; 불포화 이미드류; 및 산 무수물 중 어느 하나이상일 수 있다. Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.
상기 불포화 카르복시산 에스테르류의 구체적인 예로는, 벤질(메타)아크릴레이트, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 디메틸아미노에틸(메타)아크릴레이트, 이소부틸(메타)아크릴레이트, t-부틸(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 2-페녹시에틸(메타)아크릴레이트, 테트라히드로퍼프릴(메타)아크릴레이트, 히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시-3-클로로프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메타)아크릴레이트, 글리세롤(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 에톡시디에틸렌글리콜 (메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시트리프로필렌글리콜(메타)아크릴레이트, 폴리(에틸렌 글리콜) 메틸에테르(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메타)아크릴레이트, 글리시딜(메타)아크릴레이트, 테트라플루오로프로필(메타)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필 (메타)아크릴레이트, 옥타플루오로펜틸(메타)아크릴레이트, 헵타데카플루오로데실(메타)아크릴레이트, 트리브로모페닐(메타)아크릴레이트, 메틸 α-히드록시메틸 아크릴레이트, 에틸 α-히드록시메틸 아크릴레이트, 프로필 α-히드록시메틸 아크릴레이트 및 부틸 α-히드록시메틸 아크릴레이트로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate , p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1 , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.
상기 방향족 비닐 단량체류의 구체적인 예로는, 스티렌, α-메틸스티렌, (o,m,p)-비닐 톨루엔, (o,m,p)-메톡시 스티렌, 및 (o,m,p)-클로로 스티렌으로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro It may be selected from the group consisting of styrene, but is not limited thereto.
상기 불포화 에테르류의 구체적인 예로는, 비닐 메틸 에테르, 비닐 에틸 에테르, 및 알릴 글리시딜 에테르로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
상기 불포화 이미드류의 구체적인 예로는, N-페닐 말레이미드, N-(4-클로로페닐) 말레이미드, N-(4-히드록시페닐) 말레이미드, 및 N-시클로헥실 말레이미드로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.
상기 산 무수물로는 무수 말레인산, 무수 메틸 말레인산, 테트라하이드로 프탈산 무수물 등이 있으나, 이들에만 한정되는 것은 아니다.Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.
상기 알칼리 용해성을 부여하는 모노머는 산기를 포함한다면 특별히 한정되지 않으며, 예를 들면, (메타)아크릴산, 크로톤산, 이타콘산, 말레인산, 푸마르산, 모노메틸 말레인산, 5-노보넨-2-카복실산, 모노-2-((메타)아크릴로일옥시)에틸 프탈레이트, 모노-2-((메타)아크릴로일옥시)에틸 숙시네이트, ω-카르복시 폴리카프로락톤 모노(메타)아크릴레이트로 이루어지는 군으로부터 선택되는 1 종 이상을 사용하는 것이 바람직하나, 이들에만 한정되는 것은 아니다.The monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.
본 명세서의 일 실시상태에 있어서, 상기 바인더 수지의 산가는 50 내지 130 KOH mg/g이고, 중량 평균 분자량은 1,000 내지 50,000이다. In one embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg / g, the weight average molecular weight is 1,000 to 50,000.
상기 다관능성 모노머는 광에 의해 포토레지스트상을 형성하는 역할을 하는 모노머로서, 구체적으로는 프로필렌글리콜 메타크릴레이트, 디펜타에리쓰리톨 헥사아크릴레이트, 디펜타에리쓰리톨 아크릴레이트, 네오펜틸글리콜 디아크릴레이트, 6-헥산디올 디아크릴레이트, 1,6-헥산디올 아크릴레이트 테트라에틸렌글리콜 메타크릴레이트, 비스페녹시 에틸알콜 디아크릴레이트, 트리스히드록시에틸이소시아누레이트 트리메타크릴레이트, 트리메틸프로판 트리메타크릴레이트, 디페닐펜타에리스톨리톨 헥사아크릴레이트, 펜타에리 쓰리톨 트리메타 크릴레이트, 펜타에리쓰리톨 테트라메타크릴레이트 및 디펜타에리쓰리톨 헥사메타 크릴레이트로 이루어진 그룹 중에서 선택되는 1종 또는 2종 이상의 혼합물일 수 있다.The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.
상기 광 개시제는 빛에 의해 라디칼을 발생시켜 가교를 촉발하는 개시제이면, 특별히 한정되지 않으나, 예를 들면, 아세토페논계 화합물, 비이미다졸계 화합물, 트리아진계 화합물, 및 옥심계 화합물로 이루어진 군으로부터 선택되는 1종 이상일 수 있다. The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking, and is, for example, from an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more selected.
상기 아세토페논계 화합물은 2-히드록시-2-메틸-1-페닐프로판-1-온, 1-(4-이소프로필페닐)-2-히드록시-2-메틸프로판-1-온, 4-(2-히드록시에톡시)-페닐-(2-히드록시-2-프로필)케톤, 1-히드록시시클로헥실페닐케톤, 벤조인메틸 에테르, 벤조인에틸 에테르, 벤조인이소부틸 에테르, 벤조인부틸 에테르, 2,2-디메톡시-2-페닐아세토페논, 2-메틸-(4-메틸티오)페닐-2-몰폴리노-1-프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온, 2-(4-브로모-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온 또는 2-메틸-1-[4-(메틸티오)페닐]-2-몰폴리노프로판-1-온 등이 있으며, 이에 한정되지 않는다. The acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and the like.
상기 비이미다졸계 화합물로는 2,2-비스(2-클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4',5,5'-테트라키스(3,4,5-트리메톡시페닐)-1,2'-비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4,5,5'-테트라페닐-1,2'-비이미다졸 등이 있으며, 이에 한정되지 않는다. As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.
상기 트리아진계 화합물은 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 1,1,1,3,3,3-헥사플로로이소프로필-3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오네이트, 에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 2-에폭시에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 시클로헥실-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 벤질-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 3-{클로로-4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피온아미드, 2,4-비스(트리클로로메틸)-6-p-메톡시스티릴-s-트리아진, 2,4-비스(트리클로로메틸)-6-(1-p-디메틸아미노페닐)-1,3,-부타디에닐-s-트리아진, 2-트리클로로메틸-4-아미노-6-p-메톡시스티릴-s-트리아진 등이 있으며, 이에 한정되지 않는다. The triazine compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloro Methyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto. .
상기 옥심계 화합물은 1,2-옥타디온,-1-(4-페닐치오)페닐,-2-(o-벤조일옥심)(시바가이기사, 시지아이124), 에타논,-1-(9-에틸)-6-(2-메틸벤조일-3-일)-,1-(O-아세틸옥심)(씨지아이242), N-1919(아데카사) 등이 있으며, 이에 한정되지 않는다. The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.
상기 용매는 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤, 메틸셀로솔브, 에틸셀로솔브, 테트라히드로퓨란, 1,4-디옥산, 에틸렌글리콜 디메틸 에테르, 에틸렌글리콜 디에틸 에테르, 프로필렌글리콜 디메틸 에테르, 프로필렌글리콜 디에틸 에테르, 디에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 메틸 에틸 에테르, 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,1-트리클로로에탄, 1,1,2-트리클로로에탄, 1,1,2-트리클로로에텐, 헥산, 헵탄, 옥탄, 시클로헥산, 벤젠, 톨루엔, 크실렌, 메탄올, 에탄올, 이소프로판올, 프로판올, 부탄올, t-부탄올, 2-에톡시 프로판올, 2-메톡시 프로판올, 3-메톡시 부탄올, 시클로헥사논, 시클로펜타논, 프로필렌글리콜 메틸 에테르 아세테이트, 프로펠렌글리콜 에틸 에테르 아세테이트, 3-메톡시부틸 아세테이트, 에틸 3-에톡시프로피오네이트, 에틸 셀로솔브아세테이트, 메틸 셀로솔브아세테이트, 부틸 아세테이트, 프로필렌글리콜 모노메틸에테르 및 디프로필렌글리콜 모노메틸에테르로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다.The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.
본 명세서의 일 실시상태에 있어서, 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로, 상기 화학식 1로 표시되는 스티릴계 화합물을 포함하는 색재의 함량은 5 중량% 내지 60 중량%이고, 상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이며, 상기 개시제의 함량은 0.1 중량% 내지 20 중량%이며, 상기 다관능성 모노머의 함량은 0.1 중량% 내지 50 중량%이다. In one embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the color material containing a styryl-based compound represented by Formula 1 is 5% by weight to 60% by weight, the binder resin The content of is from 1% to 60% by weight, the content of the initiator is from 0.1% to 20% by weight, the content of the multifunctional monomer is from 0.1% to 50% by weight.
상기 고형분의 총 중량이란, 감광성 수지 조성물에서 용매를 제외한 성분 총 중량의 합을 의미한다. 고형분 및 각 성분의 고형분을 기준으로 한 중량%의 기준은 액체크로마토그래피 또는 가스크로마토그래피 등의 당업계에서 쓰이는 일반적인 분석 수단으로 측정할 수 있다. The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the photosensitive resin composition. The weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.
상기의 수치 범위에서는 고휘도 녹색 컬러 필터를 얻을 수 있다.Within the above numerical range, a high luminance green color filter can be obtained.
본 명세서의 일 실시상태에 있어서, 상기 감광성 수지 조성물은 광가교증감제, 경화촉진제, 밀착촉진제, 계면활성제, 산화방지제, 열중합방지제, 자외선흡수제, 산화방지제, 분산제 및 레벨링제로 이루어진 군으로부터 선택되는 1 또는 2 이상의 첨가제를 추가로 포함한다. In an exemplary embodiment of the present specification, the photosensitive resin composition is selected from the group consisting of photocrosslinking sensitizers, curing accelerators, adhesion promoters, surfactants, antioxidants, thermal polymerization inhibitors, ultraviolet absorbers, antioxidants, dispersants and leveling agents. It further comprises one or two additives.
본 명세서의 일 실시상태에 있어서, 상기 첨가제의 함량은 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로 0.1 중량% 내지 20 중량%이다. In one embodiment of the present specification, the amount of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
상기 광가교증감제는 벤조페논, 4,4-비스(디메틸아미노)벤조페논, 4,4-비스(디에틸아미노)벤조페논, 2,4,6-트리메틸아미노벤조페논, 메틸-o-벤조일벤조에이트, 3,3-디메틸-4-메톡시벤조페논, 3,3,4,4-테트라(t-부틸퍼옥시카보닐)벤조페논 등의 벤조페논계 화합물; 9-플로레논, 2-크로로-9-프로레논, 2-메틸-9-플로레논 등의 플로레논계 화합물; 티옥산톤, 2,4-디에틸 티옥산톤, 2-클로로 티옥산톤, 1-클로로-4-프로필옥시 티옥산톤, 이소프로필티옥산톤, 디이소프로필티옥산톤 등의 티옥산톤계 화합물; 크산톤, 2-메틸크산톤 등의 크산톤계 화합물; 안트라퀴논, 2-메틸 안트라퀴논, 2-에틸 안트라퀴논, t-부틸 안트라퀴논, 2,6-디클로로-9,10- 안트라퀴논 등의 안트라퀴논계 화합물; 9-페닐아크리딘, 1,7-비스(9-아크리디닐)헵탄, 1,5-비스(9-아크리디닐펜탄), 1,3-비스(9-아크리디닐)프로판 등의 아크리딘계 화합물; 벤질, 1,7,7-트리메틸-비시클로[2,2,1]헵탄-2,3-디온, 9,10-펜안트렌퀴논 등의 디카보닐 화합물; 2,4,6-트리메틸벤조일 디페닐포스핀 옥사이드, 비스(2,6-디메톡시벤조일)-2,4,4-트리메틸펜틸 포스핀 옥사이드 등의 포스핀 옥사이드계 화합물; 메틸-4-(디메틸아미노)벤조에이트, 에틸-4-(디메틸아미노)벤조에이트, 2-n-부톡시에틸-4-(디메틸아미노)벤조에이트 등의 벤조에이트계 화합물; 2,5-비스(4-디에틸아미노벤잘)시클로펜타논, 2,6-비스(4-디에틸아미노벤잘)시클로헥사논, 2,6-비스(4-디에틸아미노벤잘)-4-메틸-시클로펜타논 등의 아미노 시너지스트; 3,3-카본닐비닐-7-(디에틸아미노)쿠마린, 3-(2-벤조티아졸일)-7-(디에틸아미노)쿠마린, 3-벤조일-7-(디에틸아미노)쿠마린, 3-벤조일-7-메톡시-쿠마린, 10,10-카르보닐비스[1,1,7,7-테트라메틸-2,3,6,7-테트라히드로-1H,5H,11H-C1]-벤조피라노[6,7,8-ij]-퀴놀리진-11-온 등의 쿠마린계 화합물; 4-디에틸아미노 칼콘, 4-아지드벤잘아세토페논 등의 칼콘 화합물; 2-벤조일메틸렌, 3-메틸-b-나프토티아졸린;으로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.
상기 경화촉진제로는 경화 및 기계적 강도를 높이기 사용되며, 구체적으로 2-머캅토벤조이미다졸, 2-머캅토벤조티아졸, 2-머캅토벤조옥사졸, 2,5-디머캅토-1,3,4-티아디아졸, 2-머캅토-4,6-디메틸아미노피리딘, 펜타에리스리톨-테트라키스(3-머캅토프로피오네이트), 펜타에리스리톨-트리스(3-머캅토프로피오네이트), 펜타에리스리톨-테트라키스(2-머캅토아세테이트), 펜타에리스리톨-트리스(2-머캅토아세테이트), 트리메틸올프로판-트리스(2-머캅토아세테이트), 및 트리메틸올프로판-트리스(3-머캅토프로피오네이트)로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.
본 명세서에서 사용되는 밀착촉진제로는 메타아크릴로일옥시 프로필트리메톡시 실란, 메타아크릴로일옥시 프로필디메톡시 실란, 메타아크릴로일옥시 프로필트리에톡시 실란, 메타아크릴로일옥시 프로필디메톡시실란 등의 메타 아크릴로일 실란 커플링제 중 1종 이상을 선택하여 사용할 수 있고, 알킬 트리메톡시 실란으로서 옥틸트리메톡시 실란, 도데실트리메톡시 실란, 옥타데실트리메톡시 실란 등에서 1종 이상을 선택하여 사용할 수 있다.As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.
상기 계면활성제는 실리콘계 계면활성제 또는 불소계 계면활성제이며, 구체적으로 실리콘계 계면활성제는 BYK-Chemie 사의 BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 등을 사용할 수 있으며, 불소계 계면활성제로는 DIC(DaiNippon Ink & Chemicals) 사의 F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442 등을 사용할 수 있으나, 이에만 한정되는 것은 아니다.The surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.
상기 산화 방지제로는 힌더드 페놀계(Hindered phenol) 산화 방지제, 아민계 산화 방지제, 티오계 산화 방지제 및 포스핀계 산화 방지제로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다. The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
산화 방지제의 구체적인 예로는, 인산, 트리메틸포스페이트 또는 트리에틸포스페이트와 같은 인산계 열안정제; 2,6-디-t-부틸-p-크레졸, 옥타데실-3-(4-하이드록시-3,5-디-t-부틸페닐)프로피오네이트, 테트라비스[메틸렌-3-(3,5-디-t-부틸-4-하이드록시페닐)프로피오네이트]메탄, 1,3,5-트리메틸-2,4,6-트리스(3,5-디-t-부틸-4-하이드록시벤질)벤젠, 3,5-디-t-부틸-4-하이드록시벤질포스파이트 디에틸에스테르, 2,2-티오비스(4-메틸-6-t-부틸페놀), 2,6-g,t-부틸페놀 4,4'-부틸리덴-비스(3-메틸-6-t-부틸페놀), 4,4'-티오비스(3-메틸-6-t-부틸페놀) 또는 비스[3,3-비스-(4'-히드록시-3'-터트-부틸페닐)부탄산]글리콜 에스테르 (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester)와 같은 힌더드 페놀(Hindered phenol)계 1차 산화방지제; 페닐-α-나프틸아민, 페닐-β-나프틸아민, N,N'-디페닐-p-페닐렌디아민 또는 N,N'-디-β-나프틸-p-페닐렌디아민과 같은 아민계 2차 산화방지제; 디라우릴디설파이드, 디라우릴티오프로피오네이트, 디스테아릴티오프로피오네이트, 머캡토벤조티아졸 또는 테트라메틸티우람디설파이드 테트라비스[메틸렌-3-(라우릴티오)프로피오네이트]메탄 등의 Thio계 2차 산화방지제; 또는 트리페닐 포스파이트, 트리스(노닐페닐)포스파이트, 트리이소데실포스파이트, 비스(2,4-디부틸페닐) 펜타에리스톨 디포스파이트(Bis (2,4-ditbutylphenyl)Pentaerythritol Diphosphite 또는 (1,1'-비페닐)-4,4'-디일비스포스포노산 테트라키스 [2,4-비스(1,1-디메틸에틸)페닐]에스테르((1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester)와 같은 포스파이트계 2차 산화방지제를 들 수 있다.Specific examples of the antioxidant include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' Phosphite-based secondary antioxidants such as -diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).
상기 자외선 흡수제로는 2-(3-t-부틸-5-메틸-2-히드록시페닐)-5-클로로-벤조트리아졸, 알콕시 벤조페논 등을 사용할 수 있으나, 이에 한정되지 않고, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다. As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.
상기 열중합방지제로는 예컨대 p-아니솔, 히드로퀴논, 피로카테콜(pyrocatechol), t-부틸카테콜(t-butyl catechol), N-니트로소페닐히드록시아민 암모늄염, N-니트로소페닐히드록시아민 알루미늄염, p-메톡시페놀, 디-t-부틸-p-크레졸, 피로가롤, 벤조퀴논, 4,4-티오비스(3-메틸-6-t-부틸페놀), 2,2-메틸렌비스(4-메틸-6-t-부틸페놀), 2-머캅토이미다졸 및 페노티아진(phenothiazine)으로 이루어진 군으로부터 선택된 1 종 이상을 포함할 수 있으나, 이들로만 한정되는 것은 아니며 당 기술분야에 일반적으로 알려져 있는 것들을 포함할 수 있다.Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.
상기 분산제는 미리 안료를 표면 처리하는 형태로 안료에 내부 첨가시키는 방법, 또는 안료에 외부 첨가시키는 방법으로 사용할 수 있다. 상기 분산제로는 화합물형, 비이온성, 음이온성 또는 양이온성 분산제를 사용할 수 있으며, 불소계, 에스테르계, 양이온계, 음이온계, 비이온계, 양쪽성 계면활성제 등을 들 수 있다. 이들은 각각 또는 2종 이상을 조합하여 사용될 수 있다. The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
구체적으로 상기 분산제는 폴리알킬렌글리콜 및 이의 에스테르, 폴리옥시알킬렌 다가 알코올, 에스테르알킬렌옥사이드 부가물, 알코올알킬렌옥사이드 부가물, 설폰산 에스테르, 설폰산염, 카르복실산에스테르, 카르복실산염, 알킬아미드알킬렌옥사이드 부가물 및 알킬아민으로 이루어진 그룹으로부터 선택된 1종 이상이 있으나, 이에 한정되는 것은 아니다.Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.
상기 레벨링제로는 폴리머성이거나 비폴리머성일 수 있다. 폴리머성의 레벨링제의 구체적인 예로는 폴리에틸렌이민, 폴리아미드아민, 아민과 에폭사이드의 반응 생성물을 예로 들 수 있고, 비폴리머성의 레벨링제의 구체적인 예로는 비-폴리머 황-함유 및 비-폴리머 질소-함유 화합물을 포함하지만, 이에 한정되지는 않으며, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다.The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.
본 명세서의 일 실시상태에 있어서, 상기 감광성 수지 조성물로 제조된 감광재를 제공한다. In an exemplary embodiment of the present specification, a photosensitive material prepared from the photosensitive resin composition is provided.
더 자세히는, 본 명세서의 감광성 수지 조성물을 기재 위에 적절한 방법으로 도포하여 박막 또는 패턴형태의 감광재를 형성한다.In more detail, the photosensitive resin composition of this specification is apply | coated on a base material by an appropriate method, and the photosensitive material of a thin film or a pattern form is formed.
상기 도포 방법으로는 특별히 제한되지는 않지만 스프레이 법, 롤 코팅법, 스핀 코팅법 등을 사용할 수 있으며, 일반적으로 스핀 코팅법을 널리 사용한다. 또한, 도포막을 형성한 후 경우에 따라서 감압 하에 잔류 용매를 일부 제거할 수 있다.Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.
본 명세서에 따른 감광성 수지 조성물을 경화시키기 위한 광원으로는, 예컨대 파장이 250 nm 내지 450 ㎚의 광을 발산하는 수은 증기 아크(arc), 탄소 아크, Xe 아크 등이 있으나 반드시 이에 국한되지는 않는다.Light sources for curing the photosensitive resin composition according to the present specification include, but are not limited to, mercury vapor arcs, carbon arcs, Xe arcs, etc., which emit light having a wavelength of 250 nm to 450 nm.
본 명세서에 따른 감광성 수지 조성물은 박막 트랜지트터 액정 표시장치(TFT LCD) 컬러필터 제조용 안료분산형 감광재, 박막 트랜지트터 액정 표시장치(TFT LCD) 또는 유기 발광 다이오드의 블랙 매트릭스 형성용 감광재, 오버코트층 형성용 감광재, 컬럼 스페이서 감광재, 광경화형 도료, 광경화성 잉크, 광경화성 접착제, 인쇄판, 인쇄배선반용 감광재, 플라즈마 디스플레이 패널(PDP)용 감광재 등에 사용할 수 있으며, 그 용도에 제한을 특별히 두지는 않는다.The photosensitive resin composition according to the present disclosure is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode Photoresist for forming overcoat layer, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photoresist for printed circuit board, photoresist for plasma display panel (PDP), etc. There is no restriction in particular.
본 명세서의 일 실시상태에 있어서, 상기 감광재를 포함하는 컬러필터를 제공한다. In one embodiment of the present specification, a color filter including the photosensitive material is provided.
상기 컬러필터는 상기 화학식 1로 표시되는 스티릴계 화합물을 포함하는 감광성 수지 조성물을 이용하여, 제조될 수 있다. 상기 감광성 조성물을 기판상에 도포하여 코팅막을 형성하고, 상기 코팅막을 노광, 현상 및 경화를 함으로써 컬러필터를 형성할 수 있다.The color filter may be manufactured using the photosensitive resin composition including the styryl compound represented by Chemical Formula 1. The color filter may be formed by coating the photosensitive composition on a substrate to form a coating film and exposing, developing and curing the coating film.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 내열성이 우수하여, 열처리에 의한 색의 변화가 적어, 컬러 필터의 제조시 경화 과정에 의해서도 색재현율이 높고, 휘도 및 명암비가 높은 컬러필터를 제공할 수 있다. The photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having high color reproducibility and high luminance and contrast ratio even during the curing process during the manufacture of the color filter. Can be.
상기 기판은 유리판, 실리콘 웨이퍼 및 폴리에테르설폰(Polyethersulfone, PES), 폴리카보네이트(Polycarbonate, PC) 등의 플라스틱 기재의 판 등일 수 있으며, 그 종류가 특별히 제한되는 것은 아니다. The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
상기 컬러필터는 적색 패턴, 녹색 패턴, 청색 패턴, 블랙 매트릭스를 포함할 수 있다. The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
또 하나의 실시상태에 있어서, 상기 컬러필터는 오버코트층를 더 포함할 수 있다. In another exemplary embodiment, the color filter may further include an overcoat layer.
컬러필터의 컬러픽셀 사이에는 콘트라스트를 향상시킬 목적으로 블랙 매트릭스라고 불리는 격자상의 흑색패턴을 배치할 수 있다. 블랙 매트릭스의 재료로서 크롬을 사용할 수 있다. 이 경우, 크롬을 유리기판 전체에 증착시키고 에칭 처리에 의해 패턴을 형성하는 방식을 이용할 수 있다. 그러나, 공정상의 고비용, 크롬의 고반사율, 크롬 폐액에 의한 환경오염을 고려하여, 미세가공이 가능한 안료분산법에 의한 레진 블랙 매트릭스를 사용할 수 있다. A black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.
본 명세서의 일 실시상태에 따른 블랙 매트릭스는 색재로서 블랙안료 또는 블랙 염료를 사용할 수 있다. 예컨대, 카본블랙을 단독으로 사용하거나, 카본블랙과 착색안료를 혼합하여 사용할 수 있으며, 이때 차광성이 부족한 착색안료를 혼합하기 때문에 상대적으로 색재의 양이 증가하더라도 막의 강도 또는 기판에 대한 밀착성이 저하되지 않는 장점이 있다. The black matrix according to one embodiment of the present specification may use black pigment or black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.
본 명세서에 따른 컬러필터를 포함하는 디스플레이 장치를 제공한다. Provided is a display device including a color filter according to the present specification.
상기 디스플레이 장치는 플라즈마 디스플레이 패널(Plasma Display Panel, PDP), 발광 다이오드(Light Emitting Diode, LED), 유기 발광 소자(Organic Light Emitting Diode, OLED), 액정 표시 장치(Liquid Crystal Display, LCD), 박막 트랜지스터 액정 표시 장치(Thin FIlm Transistor- Liquid Crystal Display, LCD-TFT) 및 음극선관(Cathode Ray Tube, CRT) 중 어느 하나일 수 있다.The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor. The liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
본 명세서의 일 실시상태에 따른 디스플레이 장치는 색재현율이 높고, 휘도 및 명암비가 높아, 고차광 특성이 우수할 수 있다. 이러한 특성으로 디스플레이 장치를 슬림하게 제작할 수 있다. The display device according to the exemplary embodiment of the present specification may have high color reproducibility, high luminance and contrast ratio, and excellent high light blocking characteristics. Due to these characteristics, the display device can be manufactured slim.
또한, 본 명세서의 일 실시상태에 있어서, 모듈의 상, 하판 합착 부분을 최소한의 면적으로 사용하여, 디스플레이 모듈 자체는 슬림하게 제작하고, 디스플레이는 최대화 할 수 있다. In addition, in an exemplary embodiment of the present specification, by using the upper and lower plate bonding portions of the module with a minimum area, the display module itself may be manufactured slim, and the display may be maximized.
이하, 본 명세서를 실시예를 들어 상세하게 설명한다. 하기 실시예는 본 명세서를 설명하기 위한 것으로, 본 명세서의 범위는 하기의 특허청구범위에 기재된 범위 및 그 치환 및 변경을 포함하며, 실시예의 범위로 한정되지 않는다. Hereinafter, the present specification will be described in detail with reference to Examples. The following examples are provided to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims, their substitutions and changes, and is not limited to the examples.
<제조예><Production example>
(1) 화학식 1-1로 표시되는 화합물의 제조(1) Preparation of the compound represented by Chemical Formula 1-1
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-186
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-186
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-187
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-187
1) 화합물 1b의 제조1) Preparation of Compound 1b
상기 1a 5g(33.51mmol), 시아노아세틱산 3.136g (36.866mmol), 피퍼리딘(piperidine) 0.571g(6.703mmol) 을 에탄올 (EtOH)110ml에 넣고 85℃에서 8시간 교반하였다. 상기 혼합물에 염산(HCl) 1ml를 첨가하여 30분간 교반하고 상온으로 냉각시켜 석출된 고체를 필터하고, 건조하여 상기 화합물 1b 3. 985g(8.43mmol)을 얻었다. (수율 55%)5 g (33.51 mmol) of 1a, 3.136 g (36.866 mmol) of cyanoacetic acid, 0.571 g (6.703 mmol) of piperidine were added to 110 ml of ethanol (EtOH), and the mixture was stirred at 85 ° C. for 8 hours. 1 ml of hydrochloric acid (HCl) was added to the mixture, stirred for 30 minutes, cooled to room temperature, and the precipitated solid was filtered and dried to obtain 3.85 g (8.43 mmol) of the compound 1b. (Yield 55%)
상기 1b의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the 1b is as follows.
1H NMR(500MHz, Acetone-d6, ppm): 8.10(1H, s, CH), 8.03-7.99(2H, d, ArH), 6.87-6.85(2H, d, ArH), 3.14(6H, s CH3) 1 H NMR (500 MHz, Acetone-d6, ppm): 8.10 (1H, s, CH), 8.03-7.99 (2H, d, ArH), 6.87-6.85 (2H, d, ArH), 3.14 (6H, s CH 3 )
2) 화학식 1-1의 제조2) Preparation of Chemical Formula 1-1
상기 화합물 1b 1.5g(6.937mmol), 1c 1.44g(11.098mmol), 에틸카르보디이미드염산염(EDC-HCl)1.648g(6.601mmol), 디메틸아미노피리딘(DMAP) 0.169g(1.387mmol)을 0~4℃ 테트라하이드로퓨란(THF) 40ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고 메틸렌클로라이드(MC) 600ml로 추출하였다. 추출한 유기층의 물을 황화마그네슘(MgSO4)를 통과시켜 제거하고, 용매를 진공 하에서 제거하고, 컬럼(헥산/에틸아세테이트=4/1)으로 정제하여 상기 화학식 1-1로 표시되는 화합물 1.140g(3.468mmol)을 얻었다. 수율(50%)The compound 1b 1.5g (6.937mmol), 1c 1.44g (11.098mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.648g (6.601mmol), dimethylaminopyridine (DMAP) 0.169g (1.387mmol) 0 ~ 40 ml of 4 ° C tetrahydrofuran (THF) was added, followed by stirring for 2 hours at room temperature. 150 ml of water was added to the reaction and extracted with 600 ml of methylene chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfide (MgSO 4 ), the solvent was removed under vacuum, purified by column (hexane / ethyl acetate = 4/1), and 1.140 g of a compound represented by Chemical Formula 1-1 ( 3.468 mmol). Yield (50%)
상기 화학식 1-1의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-1 are as follows.
1H NMR(500MHz, Acetone-d6, ppm): 8.10(1H, s, CH), 8.01-7.99(2H, d, ArH), 6.87-6.85(2H, d, ArH), 6.10(1H, s, CH2), 5.64(1H, s, CH2), 4.55-4.53(2H, m, CH2), 4.46-4.44(2H, m, CH2), 3.16(6H, s CH3), 1.92(3H, s, CH3) 1 H NMR (500 MHz, Acetone-d6, ppm): 8.10 (1H, s, CH), 8.01-7.99 (2H, d, ArH), 6.87-6.85 (2H, d, ArH), 6.10 (1H, s, CH 2 ), 5.64 (1H, s, CH 2 ), 4.55-4.53 (2H, m, CH 2 ), 4.46-4.44 (2H, m, CH 2 ), 3.16 (6H, s CH 3 ), 1.92 (3H , s, CH 3 )
(2)화학식 1-2으로 표시되는 화합물의 제조(2) Preparation of the compound represented by Formula 1-2
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-197
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-197
상기 (1)에서 얻은 화합물 1b 2g(9.249mmol), 1e 3.963g(18.4986mmol), 에틸카르보디이미드염산염(EDC-HCl) 1.7736g(9.246mmol), 디메틸아미노피리딘(DMAP)0.227g (1.859mmol)을 0~4℃ 테트라하이드로퓨란(THF)40ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고, 메틸클로라이드(MC) 600ml로 추출하였다. 추출한 유기층의 물을 황화마그네슘을 통과시켜 제거하고, 용매를 진공하에서 제거하고, 컬럼(헥산/에틸 아세테이트 6/1)으로 정제하여 상기 화학식 1-2로 표시되는 화합물 2.67g(6.474mmol)을 얻었다. 수율(70%)1b 2g (9.249mmol), 1e 3.963g (18.4986mmol) obtained in (1), 1.7736g (9.246mmol) of ethylcarbodiimide hydrochloride (EDC-HCl), 0.227g (1.859mmol) of dimethylaminopyridine (DMAP) ) Was added to 40 ml of tetrahydrofuran (THF) at 0 ° C to 4 ° C, and stirred for 2 hours, followed by stirring at room temperature for 24 hours. 150 ml of water was added to the reaction and extracted with 600 ml of methyl chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfide, the solvent was removed under vacuum, and purified by column (hexane / ethyl acetate 6/1) to obtain 2.67 g (6.474 mmol) of the compound represented by Chemical Formula 1-2. . Yield (70%)
상기 화학식 1-2의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-2 is as follows.
1H NMR(500MHz, Acetone-d6, ppm): 8.09(1H, s, CH), 8.00-7.99(2H, d, ArH), 6.87-6.85(2H, d, ArH), 6.42-6.39(1H, d, CH2), 6.22-6.19(1H, q, CH), 6.11(1H, s, CH2), 5.97-5.95(1H, d, CH2), 5.64(1H, s, CH2), 5.58-5.55(1H, m, CH), 4.60-4.40(4H, m CH2), 3.16(6H, s, CH3), 1.92(3H, s, CH3) 1 H NMR (500 MHz, Acetone-d6, ppm): 8.09 (1H, s, CH), 8.00-7.99 (2H, d, ArH), 6.87-6.85 (2H, d, ArH), 6.42-6.39 (1H, d, CH 2 ), 6.22-6.19 (1H, q, CH), 6.11 (1H, s, CH 2 ), 5.97-5.95 (1H, d, CH 2 ), 5.64 (1H, s, CH 2 ), 5.58 -5.55 (1H, m, CH), 4.60-4.40 (4H, m CH 2 ), 3.16 (6H, s, CH 3 ), 1.92 (3H, s, CH 3 )
(3) 화학식 1-3로 표시되는 화합물의 제조(3) Preparation of the compound represented by Formula 1-3
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-202
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-202
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-204
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-204
1) 화합물 2b의 제조1) Preparation of Compound 2b
상기 2a 5g (28.21mmol), 시아노아세틱산 2.640g(31.03mmol), 피퍼리딘 0.480g, (5.642mmol)을 에탄올 110ml에 넣고, 85℃에서 8시간 교반하였다. 상기 혼합물에 염산 1ml를 첨가하여 30분간 교반하고, 상온으로 냉각시켜 석출된 고체를 필터하고, 건조하여 상기 화합물 2b 4.135g (16.93mmol)을 얻었다. 수율 (60%)5 g (28.21 mmol) of 2a, 2.640 g (31.03 mmol) of cyanoacetic acid, 0.480 g of piperidine, and (5.642 mmol) were added to 110 ml of ethanol and stirred at 85 ° C for 8 hours. 1 ml of hydrochloric acid was added to the mixture, stirred for 30 minutes, cooled to room temperature, and the precipitated solid was filtered and dried to obtain 4.135 g (16.93 mmol) of the compound 2b. Yield (60%)
상기 2b의 1H-NMR을 이용한 측정 결과는 다음과 같다.The measurement results using 1 H-NMR of 2b are as follows.
1H NMR (500MHz, CDCl3, ppm): 8.08(1H, s, CH), 7.96-7.94(2H, d, ArH), 6.69-6.68(2H, ArH), 3.49-3.45(4H, q, CH2), 1.25-1.22(6H, t, CH3) 1 H NMR (500 MHz, CDCl 3 , ppm): 8.08 (1H, s, CH), 7.96-7.94 (2H, d, ArH), 6.69-6.68 (2H, ArH), 3.49-3.45 (4H, q, CH 2 ), 1.25-1.22 (6H, t, CH 3 )
2) 화학식 1-3의 제조2) Preparation of Chemical Formula 1-3
상기 화합물 2b 1.5g (6.14mmol), 2c 1.279g (9.824mmol), 에틸카르보디이미드염산염 (EDC-HCl) 1.450g (7.614mmol), 디메틸아미노피리딘(DMAP) 0.150g(1.228mmol)을 0~4℃ 테트라하이드로퓨란(THF) 40ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고, 메틸클로라이드 (MC) 600ml로 추출하였다. 추출한 유기층의 물을 황산마그네슘을 통과시켜 제거하고, 용매를 진공하에서 제거하고, 컬럼(헥산/에틸아세테이트=4/1)으로 정제하여 상기 화학식 1-3로 표시되는 화합물 1.439g (4.060mmol)을 얻었다. 수율 (66%)The compound 2b 1.5g (6.14mmol), 2c 1.279g (9.824mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.450g (7.614mmol), dimethylaminopyridine (DMAP) 0.150g (1.228mmol) 0 ~ 40 ml of 4 ° C tetrahydrofuran (THF) was added, followed by stirring for 2 hours at room temperature. 150 ml of water was added to the reaction and extracted with 600 ml of methyl chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfate, the solvent was removed under vacuum, and purified by column (hexane / ethyl acetate = 4/1) to obtain 1.439 g (4.060 mmol) of the compound represented by Chemical Formula 1-3. Got it. Yield (66%)
상기 화학식 1-3의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-3 is as follows.
1H NMR(500MHz, CDCl3, ppm): 8.02(1H, s, CH), 7.91-7.89(2H, d, ArH), 6.66-6.64(2H, d, ArH), 6.14(1H, s, CH2), 5.57(1H, s, CH2), 4.51-4.49(2H, m, CH2), 4.43-4.41(2H, m, CH2), 3.45-3.41(4H, q, CH2), 1.93(3H, s, CH3), 1.22-1.19(6H, t, CH3) 1 H NMR (500 MHz, CDCl 3 , ppm): 8.02 (1H, s, CH), 7.91-7.89 (2H, d, ArH), 6.66-6.64 (2H, d, ArH), 6.14 (1H, s, CH) 2 ), 5.57 (1H, s, CH 2 ), 4.51-4.49 (2H, m, CH 2 ), 4.43-4.41 (2H, m, CH 2 ), 3.45-3.41 (4H, q, CH 2 ), 1.93 (3H, s, CH 3 ), 1.22-1.19 (6H, t, CH 3 )
(4) 화학식 1-4로 표시되는 화합물의 제조(4) Preparation of the compound represented by Chemical Formula 1-4
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-214
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-214
상기 (3)에서 얻은 화합물 2b 2g (8.187mmol), 2e 2.055g (9.006mmol), 에틸카르보디이미드염산염(EDC-HCl) 1.736g (9.006mmol), 디메틸아미노피리딘(DMAP) 0.2g (1.637mmol) 을 0~4℃ 테트라하이드로퓨란(THF) 40ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고, 메틸클로라이드 (MC) 600ml로 추출하였다. 추출한 유기층의 물을 황산마그네슘을 통과시켜 제거하고, 용매를 진공하에서 제거하고, 컬럼(헥산/에틸아세테이트=6/1)으로 정제하여 상기 화학식 1-4로 표시되는 화합물 3.102g (6.825mmol)을 얻었다. 수율 (83%)2b 2g (8.187mmol), 2e 2.055g (9.006mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.736g (9.006mmol) obtained in the above (3), 0.2g (1.637mmol) dimethylaminopyridine (DMAP) ) Was added to 40 ml of tetrahydrofuran (THF) at 0 ° C to 4 ° C, and stirred at room temperature for 24 hours after stirring for 2 hours. 150 ml of water was added to the reaction and extracted with 600 ml of methyl chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfate, the solvent was removed under vacuum, and purified by column (hexane / ethyl acetate = 6/1) to obtain 3.102 g (6.825 mmol) of the compound represented by Chemical Formula 1-4. Got it. Yield (83%)
상기 화학식 1-4의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-4 are as follows.
1H NMR(500MHz, CDCl3, ppm): 7.97(1H, s, CH), 7.86-7.84(2H, d, ArH), 6.62-6.60(2H, d, ArH), 6.08(2H, s, CH2), 5.54(2H, s, CH2), 5.48-5.46(1H, m, CH), 4.46-4.33(4H, m, CH2), 3.41-3.37(4H, q, CH2), 1.88(6H, s, CH3), 1.17-1.15(6H, t, CH3) 1 H NMR (500 MHz, CDCl 3 , ppm): 7.97 (1H, s, CH), 7.86-7.84 (2H, d, ArH), 6.62-6.60 (2H, d, ArH), 6.08 (2H, s, CH 2 ), 5.54 (2H, s, CH 2 ), 5.48-5.46 (1H, m, CH), 4.46-4.33 (4H, m, CH 2 ), 3.41-3.37 (4H, q, CH 2 ), 1.88 ( 6H, s, CH 3 ), 1.17-1.15 (6H, t, CH 3 )
(5) 화학식 1-5로 표시되는 화합물의 제조(5) Preparation of the compound represented by Chemical Formula 1-5
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-219
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-219
상기 화합물 3a 1.5g(4.407mmol), 3b 0.917g(7.051mmol), 에틸카르보디이미드염산염(EDC-HCl) 1.047g(5.464mmol), 디메틸아미노피리딘(DMAP) 0.070g (0.573mmol)을 0~4℃ 테트라하이드로퓨란(THF) 50ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고, 메틸클로라이드(MC) 700ml로 추출하였다. 추출한 유기층의 물을 황산마그네슘을 통과시켜 제거하고, 용매를 진공하에서 제거하고, 컬럼(헥산/에틸아세테이트=4/1)으로 정제하여 상기 화학식 1-5로 표시되는 화합물 1.595g (3.526mmol)을 얻었다. 수율 (80%)The compound 3a 1.5g (4.407mmol), 3b 0.917g (7.051mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.047g (5.464mmol), dimethylaminopyridine (DMAP) 0.070g (0.573mmol) 0 ~ 50 ml of 4 ° C tetrahydrofuran (THF) was added, followed by stirring for 2 hours at room temperature. 150 ml of water was added to the reaction and extracted with 700 ml of methyl chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfate, the solvent was removed under vacuum, and purified by column (hexane / ethyl acetate = 4/1) to obtain 1.595 g (3.526 mmol) of the compound represented by Chemical Formula 1-5. Got it. Yield (80%)
상기 화학식 1-5의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-5 are as follows.
1H NMR(500MHz, CDCl3, ppm): 8.14(1H, s, CH), 7.88-7.79(2H, d, ArH), 7.39-7.31(4H, m, ArH), 7.24-7.14(6H, m, ArH), 6.97-6.88(2H, d, ArH), 4.52-4.49(2H, m, CH2), 4.43-4.40(2H, m, CH2), 1.94(3H, s, CH3) 1 H NMR (500 MHz, CDCl 3 , ppm): 8.14 (1H, s, CH), 7.88-7.79 (2H, d, ArH), 7.39-7.31 (4H, m, ArH), 7.24-7.14 (6H, m , ArH), 6.97-6.88 (2H, d, ArH), 4.52-4.49 (2H, m, CH 2 ), 4.43-4.40 (2H, m, CH 2 ), 1.94 (3H, s, CH 3 )
(6) 화학식 1-7로 표시되는 화합물의 제조(6) Preparation of the compound represented by Chemical Formula 1-7
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-224
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-224
상기 화합물 4a 1.25g (3.393mmol), 4b 0.706g(5.428mmol) 에틸카르보디이미드염산염(EDC-HCl) 0.806g, (4.207mmol), 디메틸아미노피리딘(DMAP) 0.051g, (0.441mmol)을 0~4℃테트라하이드로퓨란(THF) 401 ml에 넣고, 2시간 교반 후 상온에서 24시간 교반하였다. 상기 반응물에 물 150ml를 첨가하고, 메틸클로라이드(MC) 600ml로 추출하였다. 추출한 유기층의 물을 황산마그네슘을 통과시켜 제거하고, 용매를 진공하에서 제거하고, 컬럼(헥산/에틸아세테이트=4/1)으로 정제하여 상기 화학식 1-7로 표시되는 화합물 1.197g (2.491mmol)을 얻었다. 수율(73%)The compound 4a 1.25g (3.393mmol), 4b 0.706g (5.428mmol) ethylcarbodiimide hydrochloride (EDC-HCl) 0.806g, (4.207mmol), dimethylaminopyridine (DMAP) 0.051g, (0.441mmol) 0 401 ml of tetrahydrofuran (THF) was added to ˜40 ° C., followed by stirring for 2 hours at room temperature for 24 hours. 150 ml of water was added to the reaction and extracted with 600 ml of methyl chloride (MC). Water of the extracted organic layer was removed by passing through magnesium sulfate, the solvent was removed under vacuum, and purified by column (hexane / ethyl acetate = 4/1) to give 1.197 g (2.491 mmol) of the compound represented by Chemical Formula 1-7. Got it. Yield (73%)
상기 화학식 1-7의 1H-NMR을 이용한 측정 결과는 다음과 같다.Measurement results using the 1 H-NMR of the formula 1-7 are as follows.
1H NMR(500MHz, CDCl3, ppm): 8.03(1H, s, CH), 7.88-7.86(2H, d, ArH), 7.35-7.32(4H, t, ArH), 7.29-7.26(2H, t, ArH), 7.19-7.17(4H, d, ArH), 6.78-6.76(2H, d, ArH), 6.13(1H, s, CH2), 5.57(1H, s, CH2), 4.74(4H, s, CH2), 4.51-4.48(2H, m, CH2), 4.42-4.40(2H, m, CH2), 1.93(3H, s, CH3) 1 H NMR (500 MHz, CDCl 3 , ppm): 8.03 (1H, s, CH), 7.88-7.86 (2H, d, ArH), 7.35-7.32 (4H, t, ArH), 7.29-7.26 (2H, t , ArH), 7.19-7.17 (4H, d, ArH), 6.78-6.76 (2H, d, ArH), 6.13 (1H, s, CH 2 ), 5.57 (1H, s, CH 2 ), 4.74 (4H, s, CH 2 ), 4.51-4.48 (2H, m, CH 2 ), 4.42-4.40 (2H, m, CH 2 ), 1.93 (3H, s, CH 3 )
<실시예 1 내지 3 및 비교예 1> 녹색 감광성 수지 조성물의 컬러 조성 비교<Examples 1-3 and Comparative Example 1> Comparison of the color composition of the green photosensitive resin composition
상기 각 실시예와 비교예에 따라 제조된 녹색 감광성 수지 조성물의 컬러조성을 비교한 결과를 다음 표 1에 나타내었다. Table 1 shows the results of comparing the color compositions of the green photosensitive resin compositions prepared according to the above Examples and Comparative Examples.
[규칙 제91조에 의한 정정 01.11.2013]　
표 1
Figure WO-DOC-TABLE-1
 [Revision under Rule 91 01.11.2013]
Table 1
Figure WO-DOC-TABLE-1
1) 중량 비율로 나타냄1) expressed as weight ratio
바인더 수지: 벤질메타크릴레이트(benzyl methacrylate)와 메타크릴산(Methacrylic acid)의 공중합체, 몰비 70:30, 산가는 113 KOH mg/g, GPC로 측정한 중량평균분자량 20,000, 분자량 분포 (PDI) 2.0, 고형분(S.C) 25% Binder resin: copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI) 2.0, solids (SC) 25%
용매: 프로필렌글리콜 모노메틸에테르아세테이트(PGMEA)Solvent: Propylene Glycol Monomethyl Ether Acetate (PGMEA)
광 개시제: I-369(BASF 社)Photoinitiator: I-369 (BASF)
다광능성 모노머: 디페닐펜타에리스톨리톨 헥사아크릴레이트(DPHA)Multiphotonic Monomer: Diphenylpentaerythritol hexaacrylate (DPHA)
<실시예 4 및 비교예 2 > 녹색 감광성 수지 조성물 컬러 조성 비교<Example 4 and Comparative Example 2> Comparison of green photosensitive resin composition color composition
상기 각 실시예와 비교예에 따라 제조된 녹색 감광성 수지 조성물의 컬러조성을 비교한 결과를 다음 표 2에 나타내었다. Table 2 shows the results of comparing the color compositions of the green photosensitive resin compositions prepared according to the above Examples and Comparative Examples.
[규칙 제91조에 의한 정정 01.11.2013]　
표 2
Figure WO-DOC-TABLE-2
 [Revision under Rule 91 01.11.2013]
TABLE 2
Figure WO-DOC-TABLE-2
바인더 수지: 벤질메타크릴레이트(benzyl methacrylate)와 메타크릴산(Methacrylic acid)의 공중합체, 몰비 70:30, 산가는 113 KOH mg/g, GPC로 측정한 중량평균분자량 20,000, 분자량 분포 (PDI) 2.0, 고형분(S.C) 25% Binder resin: copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI) 2.0, solids (SC) 25%
<실시예 5> 휘도(Y) 및 색좌표(Gx, Gy)의 비교Example 5 Comparison of Luminance (Y) and Color Coordinates (Gx, Gy)
감광성 수지 조성물을 5*5cm 의 유리(코닝社) 위에 스핀 코팅(spin coating)을 하고, 90℃에서 약 100초간 전열 처리(prebake)하여 필름을 형성시킨다. 필름을 형성시킨 기판과 포토 마스크(photo mask)와 사이의 간격을 300㎛로 하고, 노광기(Hoya-shott 社)를 이용하여 40mJ/cm2 노광량을 조사하였다. 노광된 기판을 현상액 (KOH, 0.05%)에 60초간 현상하고, 230℃로 20분간 후열 처리(postbake)를 시켜, 컬러 패턴을 얻었다. The photosensitive resin composition is spin coated on a glass of 5 * 5 cm (Corning Co., Ltd.) and prebake at 90 ° C. for about 100 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 300 µm, and the exposure amount of 40 mJ / cm 2 was irradiated using an exposure machine (Hoya-shott). The exposed substrate was developed for 60 seconds in a developing solution (KOH, 0.05%), and post-baked at 230 ° C. for 20 minutes to obtain a color pattern.
컬러 패턴을 분광기를 통하여 380nm 내지 780nm의 범위의 가시광 영역의 투과율 스펙트럼을 얻었다. 얻어진 투과율 스펙트럼과 C 광원 백라이트를 이용하여, 아래의 식을 이용하여 삼자극 값 (tristimulus value) (X, Y, Z)값을 구하였으며, 이로부터 CIE1931 좌표인 x, y, Y를 아래의 식을 이용하여 계산하였다. The transmittance spectrum of the visible light region in the range of 380 nm to 780 nm was obtained through a color pattern spectrometer. Using the obtained transmittance spectrum and C light source backlight, the tristimulus value (X, Y, Z) value was obtained using the following equation, and the CIE1931 coordinates x, y, and Y were obtained from the following equation. Calculated using.
[규칙 제91조에 의한 정정 01.11.2013]　
Figure WO-DOC-242
[Revision under Rule 91 01.11.2013]
Figure WO-DOC-242
S: C 광원S: C light source
R: 녹색 감광성 수지 조성물의 패턴 투과율 스펙트럼R: Pattern transmittance spectrum of green photosensitive resin composition
Figure PCTKR2013007864-appb-I000015
: 등색 함수 (color matching function)
Figure PCTKR2013007864-appb-I000015
Color matching function
하기 표 3에 녹색 감광성 수지 조성물을 이용한 C 광원에서 계산된 색 좌표를 나타내었다. Table 3 shows the color coordinates calculated by the C light source using the green photosensitive resin composition.
[규칙 제91조에 의한 정정 01.11.2013]　
표 3
Figure WO-DOC-TABLE-3
 [Revision under Rule 91 01.11.2013]
TABLE 3
Figure WO-DOC-TABLE-3
상기 표 3에서 알 수 있듯이, 비교예 1보다 휘도면에서 우수한 효과를 나타내었다. 상기 휘도 증가는 450 nm 내지 680 nm에서 비교예에 비하여 투과도가 증가하였기 때문에 유래된다. As can be seen from Table 3, it showed an excellent effect in terms of brightness than Comparative Example 1. The increase in brightness is derived because the transmittance increased from 450 nm to 680 nm compared to the comparative example.
<실시예 6> 용해도 Example 6 Solubility
상기 제조한 각 화합물 1-1 내지 1-5 및 1-7에 대하여 용매 프로필렌글리콜메틸에테르아세테이트(PGMEA)를 기준으로 용해도를 측정하고, 하기의 표 4에 그 결과를 나타내었다. The solubility was measured based on the solvent propylene glycol methyl ether acetate (PGMEA) for each of the prepared compounds 1-1 to 1-5 and 1-7, and the results are shown in Table 4 below.
[규칙 제91조에 의한 정정 01.11.2013]　
표 4
Figure WO-DOC-TABLE-4
 [Revision under Rule 91 01.11.2013]
Table 4
Figure WO-DOC-TABLE-4

Claims (22)

  1. 하기 화학식 1로 표시되는 스티릴계 화합물:Styryl compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2013007864-appb-I000016
    Figure PCTKR2013007864-appb-I000016
    화학식 1에 있어서, In Chemical Formula 1,
    n은 1 내지 3의 정수이고, n is an integer from 1 to 3,
    m은 1 내지 4의 정수이며, m is an integer from 1 to 4,
    X는 NR 또는 O이고, X is NR or O,
    R은 수소; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로 알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 및 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기로 이루어진 군에서 선택되며,R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; And a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms,
    L1은 직접결합; 또는 탄소수 1 내지 10의 치환 또는 비치환된 알킬렌기이며, L 1 is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
    R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 7 내지 50의 아르알킬기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이고,R1 and R2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; A substituted or unsubstituted 7 to 50 aralkyl group; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
    R3는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기이며, R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms,
    R4는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이고,R 4 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group including one or more of N, O and S atoms,
    R5는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 탄소수 3 내지 40의 아크릴로일기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 아크릴레이트기; 치환 또는 비치환된 탄소수 1 내지 40의 카보닐기; 또는 N, O, S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다. R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted acryloyl group having 3 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted acrylate group; Substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing one or more of N, O, S atoms.
  2. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 스티릴계 화합물은 하기 화학식 2로 표시되는 것인 스티릴계 화합물: The styryl compound represented by Formula 1 is a styryl compound represented by Formula 2 below:
    [화학식 2][Formula 2]
    Figure PCTKR2013007864-appb-I000017
    Figure PCTKR2013007864-appb-I000017
    화학식 2에 있어서, In Chemical Formula 2,
    n, m, R1 내지 R4, X 및 L1은 상기에서 정의한 바와 동일하고, n, m, R1 to R4, X and L1 are the same as defined above,
    R6는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 25의 알콕시기; 치환 또는 비치환된 탄소수 2 내지 25의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다. R6 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroring group containing at least one of N, O and S atoms.
  3. 청구항 1에 있어서, The method according to claim 1,
    R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 25의 알킬기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 7 내지 50의 아르알킬기인 것인 스티릴계 화합물.R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.
  4. 청구항 1에 있어서, The method according to claim 1,
    R4는 니트릴기; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기인 것인 스티릴계 화합물.R4 is a nitrile group; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms An aryl group having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from; Or a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group including at least one of N, O and S atoms Styryl-based compound which is a heterocyclic group containing one or more of N, O and S atoms unsubstituted or substituted with one or more substituents selected from the group.
  5. 청구항 1에 있어서, The method according to claim 1,
    L1은 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 아크릴로일기, 아크릴레이트기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 직쇄 또는 분지쇄의 탄소수 1 내지 10의 알킬렌기인 스티릴계 화합물. L 1 represents a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, an acryloyl group, an acrylate group, a nitrile group, and one of N, O, and S atoms. A styryl-based compound which is a straight or branched chain alkylene group having 1 to 10 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of two or more heterocyclic groups.
  6. 청구항 1에 있어서, The method according to claim 1,
    상기 R5는 수소; 수소; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아크릴레이트기; 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 카보닐기; 또는 할로겐기, 알킬기, 알케닐기, 시클로알킬기, 아릴기, 아릴아민기, 알킬아민기, 카바졸기, 플루오레닐기, 니트릴기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환된 아크릴로일기인 것인 스티릴계 화합물. R5 is hydrogen; Hydrogen; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms An acrylate group unsubstituted or substituted with one or more substituents selected from; Group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group containing at least one of N, O and S atoms A carbonyl group unsubstituted or substituted with one or more substituents selected from; Or a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and a heterocyclic group including at least one of N, O and S atoms Styryl-based compound which is an acryloyl group unsubstituted or substituted with one or more substituents selected from the group.
  7. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 스티릴계 화합물은 하기 화학식 1-1 내지 1-8 중 어느 하나로 표시되는 것인 스티릴계 화합물. The styryl compound represented by Formula 1 is represented by any one of the following Formulas 1-1 to 1-8.
    Figure PCTKR2013007864-appb-I000018
    Figure PCTKR2013007864-appb-I000018
  8. 청구항 1에 있어서, The method according to claim 1,
    상기 스티릴계 화합물의 최대 흡수 파장(λmax)는 400 nm 내지 500 nm인 것을 특징으로 하는 스티릴계 화합물.The maximum absorption wavelength (λ max ) of the styryl compound is a styryl compound, characterized in that 400 nm to 500 nm.
  9. 청구항 1에 있어서, The method according to claim 1,
    상기 스티릴계 화합물의 흡수 스펙트럼의 범위는 350 nm 내지 500 nm 인 것을 특징으로 하는 스티릴계 화합물.A styryl compound, characterized in that the absorption spectrum of the styryl compound is in the range of 350 nm to 500 nm.
  10. 청구항 1 내지 9 중 어느 한 항에 따른 스티릴계 화합물을 포함하는 색재. A color material comprising the styryl compound according to any one of claims 1 to 9.
  11. 청구항 10에 있어서, The method according to claim 10,
    상기 색재는 상기 스티릴계 화합물 단독으로 구성된 색재. The color material is a color material composed of the styryl-based compound alone.
  12. 청구항 10에 있어서, The method according to claim 10,
    상기 색재는 상기 스티릴계 화합물; 및The color material is the styryl-based compound; And
    안료 및 염료로 이루어진 군으로부터 선택되는 1 또는 2 이상의 추가의 착색재를 포함하는 것인 색재.A colorant comprising at least one additional colorant selected from the group consisting of pigments and dyes.
  13. 청구항 12에 있어서, The method according to claim 12,
    상기 스티릴계 화합물과 상기 착색재의 중량 비율은 1:99 내지 99: 1인 것인 색재.Color ratio of the styryl-based compound and the coloring material is 1:99 to 99: 1.
  14. 청구항 10의 색재를 포함하는 감광성 수지 조성물.The photosensitive resin composition containing the coloring material of Claim 10.
  15. 청구항 14에 있어서, The method according to claim 14,
    상기 감광성 수지 조성물은 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 더 포함하는 것인 감광성 수지 조성물.The photosensitive resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; And a solvent further comprising a solvent.
  16. 청구항 15에 있어서, The method according to claim 15,
    상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로 Based on the total weight of solids in the photosensitive resin composition
    상기 색재의 함량은 5 중량% 내지 60 중량%이고, The content of the color material is 5% by weight to 60% by weight,
    상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이며, The binder resin content is 1% by weight to 60% by weight,
    상기 개시제의 함량은 0.1 중량% 내지 20 중량%이고, The initiator content is 0.1% to 20% by weight,
    상기 다관능성 모노머의 함량은 0.1 중량% 내지 50 중량%인 것인 감광성 수지 조성물.The content of the multifunctional monomer is 0.1% by weight to 50% by weight of the photosensitive resin composition.
  17. 청구항 15에 있어서, The method according to claim 15,
    광가교증감제, 경화촉진제, 밀착촉진제, 계면활성제, 산화방지제, 열중합방지제, 자외선흡수제, 산화방지제, 분산제 및 레벨링제로 이루어진 군으로부터 선택되는 1 또는 2 이상의 첨가제를 추가로 포함하는 것인 감광성 수지 조성물.A photosensitive resin further comprising one or two or more additives selected from the group consisting of photocrosslinking sensitizers, curing accelerators, adhesion promoters, surfactants, antioxidants, thermal polymerization inhibitors, ultraviolet absorbers, antioxidants, dispersants and leveling agents. Composition.
  18. 청구항 17에 있어서, The method according to claim 17,
    상기 첨가제는 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로 0.1 중량% 내지 20 중량%인 것인 감광성 수지 조성물.The additive is a photosensitive resin composition of 0.1% to 20% by weight based on the total weight of solids in the photosensitive resin composition.
  19. 청구항 14의 감광성 수지 조성물로 제조된 감광재.Photosensitive material prepared from the photosensitive resin composition of claim 14.
  20. 청구항 19의 감광재를 포함하는 컬러필터.A color filter comprising the photosensitive material of claim 19.
  21. 청구항 20에 있어서, The method of claim 20,
    상기 컬러필터는 적색 패턴, 녹색 패턴, 청색 패턴 및 블랙 매트릭스를 포함하는 것인 컬러필터.The color filter includes a red pattern, a green pattern, a blue pattern and a black matrix.
  22. 청구항 21의 컬러필터를 포함하는 디스플레이 장치.A display device comprising the color filter of claim 21.
PCT/KR2013/007864 2012-08-31 2013-08-30 Styryl-based compound, coloring material comprising the styryl-based compound, photosensitive resin composition comprising the coloring material, photoresist material prepared from the photosensitive resin composition, color filter comprising the photoresist material, and display device comprising the color filter WO2014035203A1 (en)

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CN201380056895.4A CN104768925B (en) 2012-08-31 2013-08-30 The compound of styrene-based base and its application in coloured material, photosensitive resin, photoresist, color filter and display device

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