WO2019142955A1 - Composition de résine photosensible colorée, filtre coloré comprenant une matrice noire, espaceur de colonne ou espaceur de colonne noir fabriqué au moyen de celle-ci, et dispositif d'affichage comprenant ledit filtre coloré - Google Patents

Composition de résine photosensible colorée, filtre coloré comprenant une matrice noire, espaceur de colonne ou espaceur de colonne noir fabriqué au moyen de celle-ci, et dispositif d'affichage comprenant ledit filtre coloré Download PDF

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Publication number
WO2019142955A1
WO2019142955A1 PCT/KR2018/000921 KR2018000921W WO2019142955A1 WO 2019142955 A1 WO2019142955 A1 WO 2019142955A1 KR 2018000921 W KR2018000921 W KR 2018000921W WO 2019142955 A1 WO2019142955 A1 WO 2019142955A1
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WO
WIPO (PCT)
Prior art keywords
resin composition
photosensitive resin
colored photosensitive
pigment
black
Prior art date
Application number
PCT/KR2018/000921
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English (en)
Korean (ko)
Inventor
권민정
권영수
안기훈
Original Assignee
동우 화인켐 주식회사
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Application filed by 동우 화인켐 주식회사 filed Critical 동우 화인켐 주식회사
Priority to PCT/KR2018/000921 priority Critical patent/WO2019142955A1/fr
Publication of WO2019142955A1 publication Critical patent/WO2019142955A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G03F7/09—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

Definitions

  • the present invention relates to a colored photosensitive resin composition, a black matrix made using the same, a color filter including a column spacer or a black column spacer, and a display device including the color filter.
  • a color filter can be embedded in a color photographing apparatus of an image sensor such as a complementary metal oxide semiconductor (CMOS), a charge coupled device (CCD), or the like and used to actually obtain a color image.
  • CMOS complementary metal oxide semiconductor
  • CCD charge coupled device
  • the color filter is widely used for a photographing element, a plasma display panel (PDP), a liquid crystal display (LCD), a field emission display (FEL), a light emitting display (LED) and the like.
  • PDP plasma display panel
  • LCD liquid crystal display
  • FEL field emission display
  • LED light emitting display
  • the color filter is prepared by uniformly applying a colored photosensitive resin composition containing a coloring agent corresponding to each color of red, green and blue on a substrate on which a black matrix is pattern-formed by spin coating and then heating and drying (hereinafter, (Hereinafter sometimes referred to as "post-baking") is repeated for each color to form pixels of each color, if necessary, by exposing and developing the resulting coating film .
  • post-baking a method of using a dye instead of the pigment dispersion method, which was conventionally used as a coloring method of a colored photosensitive resin composition, or using a dye and a pigment simultaneously .
  • a colored photosensitive resin composition for a color filter using a dye and a colored photosensitive resin composition for a hybrid type color filter using both a dye and a pigment simultaneously can provide a color filter excellent in transmittance.
  • the sensitivity may be lowered depending on the kind of the ink. Therefore, studies have been actively made to solve the above problems and to prevent the sensitivity of the color filter from deteriorating.
  • Korean Patent Registration No. 10-0529638 discloses a photopolymerizable resin composition containing an N-phenylglycine and a triazine-based compound excellent in adhesion, resolution, surface and internal curability of resolution or pattern as an initiator and the like, It seems to be insufficient for improvement of the formability and optical density.
  • An object of the present invention is to provide a colored photosensitive resin composition which is excellent in optical density and low-temperature reactivity and has improved hardness and thus has excellent reliability such as solvent resistance and chemical resistance.
  • the present invention relates to a colored photosensitive resin composition
  • a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent,
  • the colorant comprises organic black, a blue pigment and a violet pigment
  • the alkali-soluble resin comprises a copolymer of the following general formula (1) or (2).
  • (A) is 3,4-epoxycyclohexylmethyl (meth) acrylate, 4-methacryloyloxyethyl trimellitate anhydride, or (hydroxyethyl) methacrylate,
  • the molar ratio of a monomer and b monomer in the above formula (1) is 2: 8 to 9: 1,
  • the molar ratio of a monomer, b monomer and c monomer in the above formula (2) is 2: 3: 5 to 8: 1: 1.
  • the present invention also provides a color filter comprising a black matrix, a column spacer or a black column spacer made of the colored photosensitive resin composition of the present invention.
  • the present invention provides a display device including the color filter.
  • the colored photosensitive resin composition of the present invention is excellent in optical density and low temperature reactivity, and has an excellent reliability such as solvent resistance and chemical resistance.
  • the color filter and the display device made of the colored photosensitive resin composition of the present invention have an excellent color reproduction effect.
  • the present invention relates to a colored photosensitive resin composition
  • a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent,
  • the colorant comprises organic black, a blue pigment and a violet pigment
  • the alkali-soluble resin comprises a copolymer of the following general formula (1) or (2).
  • (A) is 3,4-epoxycyclohexylmethyl (meth) acrylate, 4-methacryloyloxyethyl trimellitate anhydride, or (hydroxyethyl) methacrylate,
  • the molar ratio of a monomer and b monomer in the above formula (1) is 2: 8 to 9: 1,
  • the molar ratio of a monomer, b monomer and c monomer in the above formula (2) is 2: 3: 5 to 8: 1: 1.
  • the present invention also provides a color filter comprising a black matrix, a column spacer or a black column spacer made of the colored photosensitive resin composition of the present invention.
  • the present invention provides a display device including the color filter.
  • the present invention relates to a colored photosensitive resin composition
  • a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent,
  • the colorant comprises organic black, a blue pigment and a violet pigment
  • the alkali-soluble resin comprises a copolymer of the following general formula (1) or (2).
  • (A) in the above Chemical Formula 1 and / or Chemical Formula 2 is 3,4-epoxycyclohexylmethyl (meth) acrylate, 4-methacryloyloxyethyl trimellitate anhydride, or (hydroxyethyl) methacrylate ,
  • the molar ratio of a monomer and b monomer in the above formula (1) is 2: 8 to 9: 1,
  • the molar ratio of a monomer, b monomer and c monomer in the above formula (2) is 2: 3: 5 to 8: 1: 1.
  • the present invention can improve the optical density of a colored photosensitive resin composition including an organic black pigment, a violet pigment and a blue pigment as a colorant, and includes a copolymer of the above formula (1) or (2) as an alkali-
  • the low-temperature reactivity can be improved and the reliability such as solvent resistance and chemical resistance can be improved through the crosslinking reaction.
  • the colorant used in the present invention is one which is shielding against visible light, and the colorant of the present invention includes an organic black pigment, a violet pigment and a blue pigment.
  • the organic black pigment includes at least one selected from the group consisting of lactam black, aniline black and perylene black, and more specifically 100 CF (Basf).
  • Basf 100 CF
  • the violet pigment serves to improve the optical density (O.D.) by reducing the transmittance in the region of 400 to 600 nm.
  • the content of the organic black pigment can be reduced through the use of the violet pigment, and the reliability of the colored photosensitive resin composition can be improved.
  • the type of the violet pigment is not particularly limited, but C.I. Pigment Violet 19, 23, 29, 31 and 37, and it is preferable to use at least one selected from the group consisting of C.I. It is most preferred to use Pigment Violet 29.
  • the blue pigment is a compound that does not include a center metal. When the center metal is present, it may affect the liquid crystal driving. In the present invention, by using a compound that does not include a center metal as a blue pigment, .
  • the type of the blue pigment is not particularly limited as long as it is a compound that does not include a center metal.
  • Pigment Blue 16, 60, 63 and 66 is preferably used, and C.I. Pigment Blue 60 is most preferably used.
  • the colorant is contained in an amount of 13 to 60% by weight, preferably 25 to 45% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • the colorant is included in an amount of 13 to 50% by weight, the optical density and reliability are excellent.
  • the colorant is a mixture of an organic black pigment, a violet pigment and a blue pigment at a weight ratio of 1: 0.08 to 2.5: 0.2 to 3.3, preferably 1: 0.27 to 1: 0.47 to 2.25 will be.
  • the organic black pigment When the organic black pigment is contained in the above weight ratio, a colored photosensitive resin composition excellent in optical density and reliability can be obtained.
  • the organic black pigment may be contained in an amount of 6 to 25% by weight, and preferably 8 to 15% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • the violet pigment When the violet pigment is contained in the above weight ratio, a colored photosensitive resin composition excellent in optical density and reliability can be obtained.
  • the violet pigment may be contained in an amount of 2 to 15% by weight, preferably 4 to 8% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • the blue pigment When the blue pigment is contained in the above weight ratio, a colored photosensitive resin composition having an excellent optical density can be obtained.
  • the blue pigment may be included in the colored photosensitive resin composition in an amount of 5 to 20% by weight, and preferably 7 to 18% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • the colored photosensitive resin composition of the present invention may contain carbon black as an additional colorant.
  • the colorant may be mixed in a weight ratio of 1: 0.08 to 2.5: 0.2 to 3.3: 0.12 to 1.7 in terms of the weight ratio of the organic black pigment, the violet pigment, the blue pigment and the carbon black. Further, it may preferably be mixed in a weight ratio of 1: 0.27 to 1: 0.47 to 1.88: 0.27 to 0.87.
  • the carbon black may be contained in an amount of 3 to 10% by weight, and preferably 4 to 7% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • the solid content in the colored photosensitive resin composition means the sum of the components from which the solvent has been removed.
  • a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed.
  • a method for uniformly dispersing the particle diameter of the pigment include a method of dispersing the pigment dispersion (a1) by containing the pigment dispersant (a1), and a method of obtaining a pigment dispersion in which the pigment is uniformly dispersed in the solution have.
  • the pigment dispersant is added for deaggregation of the pigment and maintenance of stability.
  • Specific examples of the pigment dispersant include a cationic surfactant, an anionic surfactant, a nonionic surfactant, a positive surfactant, a polyester surfactant, and a polyamine surfactant. , Which may be used alone or in combination of two or more.
  • cationic surfactant examples include amine salts such as stearylamine hydrochloride and lauryltrimethylammonium chloride, and quaternary ammonium salts.
  • anionic surfactant examples include higher alcohol sulfuric acid ester salts such as sodium lauryl alcohol sulfate ester and sodium oleyl alcohol sulfate ester, alkylsulfates such as sodium laurylsulfate and ammonium laurylsulfate, sodium dodecylbenzenesulfonate, And alkylarylsulfonic acid salts such as sodium dodecylnaphthalenesulfonate.
  • higher alcohol sulfuric acid ester salts such as sodium lauryl alcohol sulfate ester and sodium oleyl alcohol sulfate ester
  • alkylsulfates such as sodium laurylsulfate and ammonium laurylsulfate
  • sodium dodecylbenzenesulfonate sodium dodecylbenzenesulfonate
  • alkylarylsulfonic acid salts such as sodium dodecylnaphthalenesulfonate.
  • nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene aryl ethers, polyoxyethylene alkyl aryl ethers, other polyoxyethylene derivatives, oxyethylene / oxypropylene block copolymers, sorbitan fatty acid esters, Polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene fatty acid esters, and polyoxyethylene alkylamines.
  • polyoxyethylene alkyl ethers polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines have.
  • the pigment dispersant preferably includes an acrylate-based dispersant (hereinafter referred to as an acrylate-based dispersant) containing butyl methacrylate (BMA) or N, N-dimethylaminoethyl methacrylate (DMAEMA).
  • BMA butyl methacrylate
  • DMAEMA N, N-dimethylaminoethyl methacrylate
  • Dispersing BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 and the like may be used as the acrylate-based dispersing agent,
  • the rate-based dispersing agents may be used alone or in combination of two or more.
  • the other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer
  • DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, and DISPER BYK-160 available from BYK (Big) Chemie are examples of commercially available pigment dispersants of other resin types.
  • resin-type pigment dispersants may be used alone or in combination of two or more, and may be used in combination with an acrylate-based dispersant.
  • the pigment dispersant is contained in an amount of more than 0 to 1 part by weight, preferably 0.05 to 0.5 part by weight based on 1 part by weight of the colorant. When the pigment dispersant is contained in an amount exceeding 0 to 1 part by weight, the uniformly dispersed pigment can be obtained.
  • the alkali-soluble resin usually makes the unexposed portion of the colored photosensitive resin layer formed using the colored photosensitive resin composition alkali-soluble, and also acts as a binder resin and a dispersing medium for the coloring agent.
  • the alkali-soluble resin is soluble in an alkaline developer used in the development step for the production of a color filter
  • the alkali-soluble resin of the present invention includes a copolymer represented by the following formula (1) or (2).
  • (A) is 3,4-epoxycyclohexylmethyl (meth) acrylate (CYM-M100, manufactured by Daicel), (hydroxy- Methacryloyloxyethy trimellitate anhydride (4-META) and / or 4-methacryloyloxyethyl trimellitate anhydride (HEMA) and / or 4-methacryloyloxyethyl trimellitate anhydride
  • the molar ratio of a monomer and b monomer in the above formula (1) is 2: 8 to 9: 1,
  • the molar ratio of a monomer, b monomer and c monomer in the above formula (2) is 2: 3: 5 to 8: 1: 1.
  • the low temperature reactivity of the colored photosensitive resin composition is improved and the hardness is improved through the crosslinking reaction, Can be improved.
  • the weight average molecular weight of the alkali-soluble resin is 3,000 to 20,000, preferably 5,000 to 15,000.
  • the acid value of the alkali-soluble resin is 50 to 200 mgKOH / g based on the solid content, and the developability against the alkali development in the above range is excellent, the occurrence of the residue can be suppressed and the adhesion of the pattern can be improved.
  • the alkali-soluble resin may be a copolymer of at least one monomer selected from the group consisting of the above-mentioned formulas (1) and (2) and other monomer copolymerizable therewith.
  • the alkali-soluble resin is contained in an amount of 5 to 60% by weight, preferably 20 to 50% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • content of the alkali-soluble resin is within the above-mentioned range, pattern formation is easy and resolution and residual film ratio are improved.
  • the photopolymerizable compound contains an unsaturated bond and forms a colored photosensitive resin layer by proceeding a photoreaction with the photopolymerization initiator, and should be a compound capable of polymerizing under the action of a photopolymerization initiator (D) described later.
  • the functional group of the photopolymerizable compound may be a commonly used (meth) acrylate.
  • the photopolymerizable compound contains 3 to 10 functional groups, preferably 4 to 8 functional groups.
  • trifunctional monomer in the polyfunctional monomer examples include trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate And pentaerythritol tri (meth) acrylate.
  • tetrafunctional monomer in the polyfunctional monomer examples include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, ditrimethylol propane tetraacrylate, ditrimethylol propane tetramethacrylate, dipentaerythritol tetramethacrylate, Tetramethylolmethane tetraacrylate, ethoxylated pentaerythritol tetraacrylate, glycerin tetraacrylate, glycerin tetramethacrylate, and the like.
  • monofunctional monomer in the polyfunctional monomer examples include dipentaerythritol pentaacrylate, dipentaerythritol penta methacrylate, dipentaerythritol monohydroxypentaacrylate, dipentaerythritol monohydroxypentaacrylate, Acrylate and the like.
  • hexafunctional monomer in the polyfunctional monomer examples include dipentaerythritol hexaacrylate, dipentaerythritol hexa methacrylate, and the like.
  • 7 to 10 functional monomer in the polyfunctional monomer include tripentaerythritol octa methacrylate, tripentaerythritol octaacrylate, tetrapentaerythritol hepta methacrylate, and tetrapentaerythritol heptaacrylate. .
  • the photopolymerizable compound is included in the colored photosensitive resin composition of the present invention in an amount of 5 to 50% by weight, preferably 7 to 45% by weight based on the total weight of the solid component.
  • the photopolymerizable compound can improve the strength and flatness of the pixel portion in the range of 5 to 50% by weight.
  • the alkali-soluble resin and the photopolymerizable compound of the present invention are mixed in a weight ratio of 1: 1 to 5: 1, preferably in a weight ratio of 1.2: 1 to 3.7: 1.
  • the alkali-soluble resin and the photopolymerizable compound are mixed at a weight ratio of 1: 1 to 5: 1, the processability is improved, and a colored photosensitive resin composition that can easily form a pattern can be provided.
  • the photopolymerization initiator can be used without limitation as long as it can polymerize the photopolymerizable compound.
  • the photopolymerization initiator is an acetophenone-based compound, a benzoin-based compound, a benzophenone-based compound, Based compound, a triazine-based compound, a non-imidazole-based compound, an oxime-based compound, and a thioxanthone-based compound.
  • acetophenone compound examples include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan- ] Propane-1-one and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoisobutyl ether.
  • benzophenone compound examples include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ' -Tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone.
  • triazine compound examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (Trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- Ethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4 dimethoxyphenyl) ethenyl] -1 , 3,5-triazine, and the like.
  • imidazole compound examples include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'-bis , 3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'- ) Diimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) ) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, or an imidazole compound in which the phenyl group at the 4,4', 5,5 'position is substituted by a carboalkoxy group .
  • it is selected from the group consisting of 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 4 ', 5,5'-tetraphenylbiimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4', 5,5'-tetraphenyl- And the like.
  • oxime compound examples include o-ethoxycarbonyl- ⁇ -oximino-1-phenylpropan-1-one and the like.
  • Commercially available oxime compounds may be OXE01 and OXE02 of BASF.
  • the thioxanthone compound is specifically exemplified by 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro- Santon et al.
  • photopolymerization initiators may be used singly or in combination of two or more.
  • the photopolymerization initiator is contained in an amount of 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the total solid content of the colored photosensitive resin composition.
  • the colored photosensitive resin composition becomes highly sensitive within the range of 0.1 to 40% by weight, and the strength of the pixel portion formed using the colored photosensitive resin composition and the smoothness on the surface of the pixel portion can be improved.
  • a photopolymerization initiator may be used in addition to the photopolymerization initiator.
  • the photopolymerization initiation assistant is a compound used for promoting polymerization of the photopolymerizable compound initiated by the photopolymerization initiator.
  • Examples of the photopolymerization initiation assistant include an amine compound or an alkoxyanthracene compound.
  • the amine compound examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, benzoic acid 2 N, N-dimethyl para-toluidine, 4,4'-bis (dimethylamino) benzphenone (collectively, Michler's ketone), 4,4'-bis (Diethylamino) benzophenone, and 4,4'-bis (ethylmethylamino) benzophenone. Of these, 4,4'-bis (diethylamino) benzophenone is preferable.
  • alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene and 2-ethyl- Diethoxyanthracene and the like.
  • photopolymerization initiators may also be used.
  • Commercially available photopolymerization initiators include trade names " EAB-F " (manufactured by Hodogaya Chemical Industry Co., Ltd.).
  • the photopolymerization initiator When used, it is preferably used in an amount of usually 0 to 10 mol, preferably 0.01 to 5 mol, per 1 mol of the photopolymerization initiator. When the photopolymerization initiator is used in the range of more than 0 to 10 moles, the sensitivity of the colored photosensitive resin composition becomes higher and the productivity of the color filter formed using the colored photosensitive resin composition can be improved.
  • the solvent used in the conventional colored photosensitive resin composition can be used without particular limitation so long as it is effective to dissolve the other components contained in the colored photosensitive resin composition.
  • the solvent may be selected from ethers, acetates, aromatic hydrocarbons, ketones, Alcohols or esters are preferred.
  • ethers examples include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether;
  • diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether.
  • acetates examples include methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3 Methoxy-1-butylacetate, methoxypentyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, methyl 3-methoxypropionate, propylene glycol methyl ether acetate, 3-methoxy- Butyl acetate, 1,2-propylene glycol diacetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, diethylene glycol monobutyl ether Acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethy
  • aromatic hydrocarbons examples include benzene, toluene, xylene, and mesitylene.
  • the ketones include, for example, methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • the alcohols include, for example, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin and 4-hydroxy-4-methyl-2-pentanone.
  • esters examples include ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and? -Butyrolactone.
  • solvents may be used alone or in combination of two or more.
  • the solvent is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C in terms of coating property and drying property, and examples thereof include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 3- Ethyl ethoxypropionate and methyl 3-methoxypropionate.
  • the solvent is contained in an amount of 60 to 90% by weight, preferably 65 to 85% by weight based on the total weight of the colored photosensitive resin composition.
  • a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater) .
  • the colored photosensitive resin composition of the present invention includes other additives according to the needs of those skilled in the art, as long as the objects of the present invention are not impaired, in addition to the above-mentioned components.
  • the additive may specifically include, for example, at least one additive selected from the group consisting of another polymer compound, a thermal initiator, a curing agent, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber and an anti- In the invention, it is preferable to include a thermal initiator as an additive.
  • the other polymer compound examples include a curable resin such as an epoxy resin and a maleimide resin; and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester and polyurethane.
  • a curable resin such as an epoxy resin and a maleimide resin
  • thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester and polyurethane.
  • the thermal initiator causes a curing reaction by heat to maximize the initiation efficiency.
  • the thermal initiator may be a peroxide-based compound.
  • thermal initiator examples include, but are not limited to, tetramethyl butyl peroxyneodecanoate (eg Perocta ND, NOF), bis (4-butylcyclohexyl) peroxydicarbonate (eg Peroyl TCP Perfluoroalkane (ex. Perbutyl ND, manufactured by NOF), dipropyl peroxydicarbonate (ex.
  • tetramethyl butyl peroxyneodecanoate eg Perocta ND, NOF
  • bis (4-butylcyclohexyl) peroxydicarbonate eg Peroyl TCP Perfluoroalkane (ex. Perbutyl ND, manufactured by NOF)
  • dipropyl peroxydicarbonate ex.
  • Peroyl NPP manufactured by NOF Corporation
  • di (2-ethylhexyl) peroxycarbonate butyl peroxyneodecanoate , NOF Corp.
  • diisopropyl peroxy dicarbonate e.g., Peroyl IPP, NOF
  • diethoxyethyl peroxydicarbonate e.g., Peroyl EEP, NOF
  • diethoxy e.g., Peroyl OEP, NOF
  • hexyl peroxydicarbonate e.g., Perhexyl ND, NOF
  • dimethoxybutyl peroxydicarbonate e.g.
  • Perbutyl trimethyl hexanoyl peroxide (e.g., Peroyl 355, NOF), dimethylhydroxybutyl peroxyneodecanoate (ex Luperox 610M75) , Atofina (manufactured by Atofina), amyl peroxyneodecanoate (ex Luperox 546M75, Atofina), butyl peroxyneodecanoate (ex Luperox 10M75, Atofina), t-butyl peroxy (Luperox 546M75, Alofina), t-butyl peroxypivalate, t-amylperoxy-2-ethylhexanoate, lauryl peroxide , Dilauroyl peroxide, didecanoyl peroxide, benzoyl peroxide, dibenzoyl peroxide, 2,2-bis (tert-butylperoxy) butane, 1,1- Butyl peroxy)
  • the content of the thermal initiator it is preferably contained in an amount of 1 to 10% by weight, and more preferably 1 to 5% by weight based on the total solid content of the colored photosensitive resin composition.
  • the curing agent is used for increasing the curing depth and mechanical strength, and specific examples thereof include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound and an oxetane compound.
  • the epoxy compound in the curing agent include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin Alicyclic or aromatic epoxy compounds, butadiene (co) polymeric epoxides and isoprene (co) polymers other than the brominated derivatives, epoxy resins and brominated derivatives of these epoxy resins, glycidyl ester resins, glycidyl amine resins, (Co) polymer epoxides, glycidyl (meth) acrylate (co) polymers, and triglycidyl isocyanurate.
  • oxetane compound in the curing agent include carbonates bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane, and the like.
  • the curing agent may be used together with a curing assistant compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound together with the curing agent.
  • the curing assistant compound includes, for example, polyvalent carboxylic acids, polyvalent carboxylic anhydrides, and acid generators.
  • the polyvalent carboxylic acid anhydrides may be those commercially available as an epoxy resin curing agent.
  • epoxy resin curing agents include commercial products such as ADEKA HARDONA EH-700 (ADEKA INDUSTRIAL CO., LTD.), Trade name (RICACIDO HH) (manufactured by New Japan Chemical Co., Ltd.) Manufactured by Shin-Etsu Chemical Co., Ltd.).
  • the curing agents exemplified above may be used alone or in combination of two or more.
  • the surfactant may be used for further improving the film-forming property of the photosensitive resin composition, and a silicone surfactant or a fluorine surfactant may be preferably used.
  • TS-4440, TSF-4300, TSF-4445, TSF-4446, and TSF-4400 of GE Toshiba Silicones such as DC3PA, DC7PA, SH11PA, SH21PA and SH-8400 from Dow Corning Toray Silicone Co., 4460 and TSF-4452.
  • F-472, F-482 and F-489 (Dainippon Ink and Chemicals, Inc.), BM-1000 and BM-1100 (trade names, (BM Chemie), Proride FC-135 / FC-170C / FC-430 (Sumitomo 3M Co., Ltd.), and the like.
  • the above-exemplified surfactants may be used alone or in combination of two or more.
  • the adhesion promoter is an additive which is used for improving coatability and adhesion to a substrate, and is a silane coupling agent containing a reactive substituent selected from the group consisting of a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, .
  • a silane coupling agent include trimethoxysilylbenzoic acid, ⁇ -methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, ⁇ -isocyanatepropyltriethoxysilane, r- Glycidoxypropyltrimethoxysilane, and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane.
  • antioxidants examples include 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.
  • ultraviolet absorber examples include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.
  • anti-aggregation agent examples include sodium polyacrylate and the like.
  • the additive is contained in an amount of 0.01 to 10% by weight, preferably 0.05 to 2% by weight based on the total weight of the solid content of the colored photosensitive resin composition.
  • a coloring agent may be added to a solvent, followed by addition of the rest of the composition and other additives, followed by stirring.
  • the colorant may be added in the form of a mill base in which a pigment or the like is dissolved or dispersed in advance in a solvent or an alkali-soluble resin.
  • the additive if in solution form, may be added in advance to the solvent along with the colorant.
  • the thus-prepared colored photosensitive resin composition can be preferably used for the production of a display device, preferably a black matrix of a liquid crystal display, a column spacer for maintaining a cell gap, or a black column spacer.
  • the colored photosensitive resin composition of the present invention can be suitably used for producing a black column spacer (black matrix integrated spacer), and the black column spacer does not form a black matrix and a column spacer, Means that the matrix and the column spacer are integrally formed.
  • the present invention also relates to a color filter comprising a black matrix, a column spacer or a black column spacer manufactured using the colored photosensitive resin composition.
  • the present invention relates to a display device including the color filter
  • a glass substrate or a polymer plate is used as the substrate.
  • the glass substrate in particular, soda lime glass, barium or strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass or quartz can be preferably used.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the coating may be performed by a wet coating method using a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater (which may be referred to as a die coater), an ink jet or the like so as to obtain a desired thickness.
  • a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater (which may be referred to as a die coater), an ink jet or the like so as to obtain a desired thickness.
  • Prebaking is performed by heating with an oven, a hot plate or the like.
  • the heating temperature and the heating time in the pre-baking are appropriately selected depending on the solvent to be used, for example, at a temperature of 80 to 150 ° C for 1 to 30 minutes.
  • the exposure performed after the pre-baking is performed by an exposure machine, and exposed through a photomask to expose only the portion corresponding to the pattern.
  • the light to be irradiated may be, for example, visible light, ultraviolet light, X-ray, electron beam, or the like.
  • the alkali development after exposure is performed for the purpose of removing the colored photosensitive resin composition in a portion where the non-exposed portion is not removed, and a desired pattern is formed by this development.
  • the developer suitable for the alkali development for example, an aqueous solution of a carbonate of an alkali metal or an alkaline earth metal may be used.
  • the post-baking is performed in order to enhance the adhesion between the patterned film and the substrate, and is performed by heat treatment at 80 to 220 DEG C for 10 to 120 minutes. Post-baking is performed by using an oven, a hot plate, or the like as in pre-baking.
  • the thickness of the black matrix is preferably 0.2 to 20 ⁇ ⁇ , more preferably 0.5 to 10 ⁇ ⁇ , and particularly preferably 0.8 to 5 ⁇ ⁇ .
  • the film thickness of the column spacer and the black column spacer is preferably 0.1 ⁇ to 8 ⁇ , more preferably 0.1 ⁇ to 6 ⁇ , and particularly preferably 0.1 ⁇ to 4 ⁇ .
  • the black matrix, the column spacer, or the black column spacer made of the colored photosensitive resin composition of the present invention is excellent in physical properties such as optical density, adhesion, electrical insulation and light shielding property, and is excellent in heat resistance and solvent resistance, It is possible to improve the reliability.
  • EDCPA (3,4-epoxytricyclo [5.2.1.0,2,6] decan-9-yl acrylate and 3,4-epoxytricyclo [5.2.1.0,2,6] decan- At a molar ratio of 50:50)
  • CYM-M100 3,4-Epoxycyclohexylmethyl methacrylate
  • a colored dispersion was prepared with the composition shown in Table 2 below.
  • the dispersing resin the alkali-soluble resin of B1 to B6 of Preparation Example 1 was used.
  • the dispersing agent a polymer dispersing agent (DisperBYK-2000) was used, and PGMEA (propylene glycol monomethyl ether acetate) was used as a solvent. The mixture was dispersed in a paint shaker at room temperature for 8 hours. Dispersion was performed using 0.1 mm zirconia beads, and the dispersion was terminated and filtered.
  • a colored dispersion was prepared by the same composition and method as those in Table 2, except that B2 was used instead of B1 as a dispersing resin in Table 2 above.
  • a coloring dispersion was prepared by the same composition and method as in Table 2, except that B3 was used instead of B1 as the dispersing resin in Table 2 above.
  • a colored dispersion was prepared by the same composition and method as in Table 2, except that B4 was used instead of B1 as the dispersing resin in Table 2 above.
  • a colored dispersion was prepared by the same composition and method as in Table 2, except that B5 was used instead of B1 as the dispersing resin in Table 2 above.
  • a colored dispersion was prepared by the same composition and method as in Table 2, except that B6 was used in place of B1 as a dispersing resin in Table 2 above.
  • a colored photosensitive resin composition was prepared by mixing the coloring dispersion prepared in Table 2 with an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, and the content thereof is shown in Table 3 below.
  • the following table is a standard in which the solid content is 20% by weight based on the colored photosensitive resin composition.
  • Examples 1 and 5 are coloring dispersions of Production Example 2.
  • Examples 2 and 6 are Production Example 2.
  • Examples 3 and 7 are Production Example 2.
  • Colored dispersions of Examples 4 and 8 to 12 colored dispersions of Production Example 2 (4) were used
  • Comparative Examples 1 to 7 were colored dispersions of Production Example 2.
  • Comparative Example 8 was Production Example 2 (5)
  • Comparative Example 9 was a colored dispersion of Production Example 2. (6).
  • OBP Organic black pigment (100 CF, available from Basf)
  • V29 C.I. Pigment Violet 29
  • PI-G Green pigment (G58, DIC)
  • Photopolymerizable compound DIPENTAERYTHRITOL HEXAACRYLATE (DPHA) (Nippon Kayaku Co., Ltd.)
  • Photopolymerization initiator 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -ethanone- 1- (O- acetyloxime) (Irgacure OXE-
  • Dispersant DisperBYK-2000
  • a 5 cm x 5 cm glass substrate (Corning) was cleaned with a neutral detergent and water and dried.
  • Each of the colored photosensitive resin compositions prepared in Examples 1 to 12 and Comparative Examples 1 to 9 was spin-coated on the glass substrate so as to have a final film thickness of 3.0 ⁇ ⁇ and prebaked at 80 to 120 ⁇ ⁇ for 1 to 2 minutes The solvent was removed by drying.
  • a coloring substrate coated with the colored photosensitive resin composition on the entire surface without pattern was prepared by baking at 200 to 250 ° C for 10 to 30 minutes.
  • optical characteristics were measured using a UV-vis (UV-2550, Shimadzu). Optical properties were measured at 400 to 600 nm in the evaluation of the optical characteristics, and in the near-IR region at 700 to 750 nm and 950 nm. The measured values for each wavelength were confirmed.
  • a substrate was prepared in the same manner as in the production of the substrate prepared by the optical property measurement.
  • the substrate was cut into a size of 3 x 3 cm, immersed in NMP solvent, and then heated at 100 DEG C for 60 minutes. After that, only the NMP solvent was extracted, and the degree of dissolution in NMP solvent was measured by UV-vis spectrometer at 300 to 800 nm to confirm the solvent resistance.
  • the evaluation criteria are as follows, and the results are shown in Table 4 below.
  • a glass substrate on which a cured film is coated is prepared in the same manner as in the above-mentioned 1-1, except that a column spacer pattern is formed.
  • the fabricated substrate is measured by SNU (SIS-2000, manufactured by SNU) and the thickness and height of the pattern in the reference state. Thereafter, using a hardness meter (Nano-indenter HM500, Fisher), the pattern is pressed to the point where it is deformed by 1 ⁇ ⁇ .
  • the hardness meter uses a flat indenter and presses at a rate of 2 mN / sec. Holding time is 5 seconds at the point of 1 ⁇ m deformation.
  • the thickness and line width of the pattern were measured using SNU (SIS-2000, SNU), and the thickness of the pattern before and after the change (the thickness of the after-deformation pattern and the percentage of the line width)
  • the elastic recovery rate is measured.
  • the evaluation criteria are as follows, and the results are shown in Table 4 below.
  • Examples 1 to 12 exhibited excellent optical characteristics, reliability, and elastic recovery.
  • Examples 5 to 8, 11 and 12, which further contain carbon black, showed better optical properties at 400 to 600 nm.
  • the colored photosensitive resin compositions of Comparative Examples 8 and 9 which did not use the compounds of the formulas (1) and (2) as the soluble resins were excellent in optical characteristics, but were not excellent in reliability and elastic recovery rate.
  • the colored photosensitive resin composition of the present invention is excellent in optical density and low temperature reactivity, and has an excellent reliability such as solvent resistance and chemical resistance.
  • the color filter and the display device made of the colored photosensitive resin composition of the present invention have an excellent color reproduction effect.

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Abstract

La présente invention concerne une composition de résine photosensible colorée comprenant un colorant contenant un pigment noir organique, un pigment violet, et un pigment bleu, une résine soluble alcaline, un composé photopolymérisable, un initiateur de photopolymérisation, et un solvant. L'invention concerne également un filtre coloré comprenant une matrice noire, un espaceur de colonne ou un espaceur de colonne noir fabriqué au moyen de la composition de résine photosensible colorée, ainsi qu'un dispositif d'affichage comprenant le filtre coloré.
PCT/KR2018/000921 2018-01-19 2018-01-19 Composition de résine photosensible colorée, filtre coloré comprenant une matrice noire, espaceur de colonne ou espaceur de colonne noir fabriqué au moyen de celle-ci, et dispositif d'affichage comprenant ledit filtre coloré WO2019142955A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100066197A (ko) * 2008-12-09 2010-06-17 제일모직주식회사 흑색 감광성 수지 조성물, 및 이를 이용한 차광층 및 칼럼 스페이서
KR20140136408A (ko) * 2012-01-13 2014-11-28 스미또모 가가꾸 가부시키가이샤 착색 경화성 수지 조성물
KR20160079692A (ko) * 2014-12-26 2016-07-06 스미또모 가가꾸 가부시키가이샤 화합물
KR20160119240A (ko) * 2014-04-11 2016-10-12 메르크 파텐트 게엠베하 유기 전계발광 소자용 물질
KR20170078158A (ko) * 2015-12-29 2017-07-07 동우 화인켐 주식회사 착색 감광성 수지 조성물 및 이를 포함하는 컬럼 스페이서

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100066197A (ko) * 2008-12-09 2010-06-17 제일모직주식회사 흑색 감광성 수지 조성물, 및 이를 이용한 차광층 및 칼럼 스페이서
KR20140136408A (ko) * 2012-01-13 2014-11-28 스미또모 가가꾸 가부시키가이샤 착색 경화성 수지 조성물
KR20160119240A (ko) * 2014-04-11 2016-10-12 메르크 파텐트 게엠베하 유기 전계발광 소자용 물질
KR20160079692A (ko) * 2014-12-26 2016-07-06 스미또모 가가꾸 가부시키가이샤 화합물
KR20170078158A (ko) * 2015-12-29 2017-07-07 동우 화인켐 주식회사 착색 감광성 수지 조성물 및 이를 포함하는 컬럼 스페이서

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