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WO2014035203A1 - Composé à base de styryle, substance colorante comprenant le composé à base de styryle, composition de résine photosensible comprenant la substance colorante, substance de photorésine préparée à partir de la composition de résine photosensible, filtre coloré comprenant la substance de photorésine, et dispositif d'affichage comprenant le filtre coloré - Google Patents

Composé à base de styryle, substance colorante comprenant le composé à base de styryle, composition de résine photosensible comprenant la substance colorante, substance de photorésine préparée à partir de la composition de résine photosensible, filtre coloré comprenant la substance de photorésine, et dispositif d'affichage comprenant le filtre coloré 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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Prior art keywords
group
substituted
unsubstituted
carbon atoms
styryl
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PCT/KR2013/007864
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English (en)
Korean (ko)
Inventor
박종호
김한수
김성현
조창호
김선화
류장현
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LG Chem Ltd
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LG Chem Ltd
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Priority to CN201380056895.4A priority Critical patent/CN104768925B/zh
Priority to JP2015527399A priority patent/JP2015532667A/ja
Publication of WO2014035203A1 publication Critical patent/WO2014035203A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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

La présente invention concerne un composé à base de styryle, une substance colorante comprenant le composé à base de styryle, une composition de résine photosensible comprenant la substance colorante, une substance de photorésine préparée à partir de la composition de résine photosensible, un filtre coloré comprenant la substance de photorésine, et un dispositif d'affichage comprenant le filtre coloré.
PCT/KR2013/007864 2012-08-31 2013-08-30 Composé à base de styryle, substance colorante comprenant le composé à base de styryle, composition de résine photosensible comprenant la substance colorante, substance de photorésine préparée à partir de la composition de résine photosensible, filtre coloré comprenant la substance de photorésine, et dispositif d'affichage comprenant le filtre coloré Ceased WO2014035203A1 (fr)

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CN201380056895.4A CN104768925B (zh) 2012-08-31 2013-08-30 基于苯乙烯基的化合物及其在着色材料、光敏树脂、光阻材料、滤色器和显示器件的应用
JP2015527399A JP2015532667A (ja) 2012-08-31 2013-08-30 スチリル系化合物、前記スチリル系化合物を含む色材、これを含む感光性樹脂組成物、前記感光性樹脂組成物で製造された感光材、これを含むカラーフィルタおよび前記カラーフィルタを含むディスプレイ装置

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JP2015532667A (ja) 2015-11-12
KR101538848B1 (ko) 2015-07-23

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