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WO2015108240A1 - Composition de résine photosensible pour filtre coloré, et filtre coloré utilisant ladite composition - Google Patents

Composition de résine photosensible pour filtre coloré, et filtre coloré utilisant ladite composition Download PDF

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Publication number
WO2015108240A1
WO2015108240A1 PCT/KR2014/003515 KR2014003515W WO2015108240A1 WO 2015108240 A1 WO2015108240 A1 WO 2015108240A1 KR 2014003515 W KR2014003515 W KR 2014003515W WO 2015108240 A1 WO2015108240 A1 WO 2015108240A1
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WO
WIPO (PCT)
Prior art keywords
pigment
resin composition
photosensitive resin
formula
functional resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2014/003515
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English (en)
Korean (ko)
Inventor
형경희
김남광
이연수
이유진
정지영
최세영
최승집
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Cheil Industries Inc
Original Assignee
Cheil Industries Inc
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Filing date
Publication date
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Priority to CN201480073417.9A priority Critical patent/CN105934712A/zh
Publication of WO2015108240A1 publication Critical patent/WO2015108240A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G03F7/0005—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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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

Definitions

  • the present disclosure relates to a photosensitive resin composition for color filters and a color filter using the same.
  • the color filter is used in a liquid crystal display device, an optical filter of a camera, and the like, and is manufactured by coating a fine region colored with three or more colors on a solid state image pickup device or a transparent substrate.
  • Such colored thin films are usually formed by a pigment dispersion method or the like.
  • the colored photosensitive resin composition used for manufacturing the color filter according to the pigment dispersion method generally consists of a binder resin, a photopolymerization monomer, a photopolymerization initiator, a colorant, a solvent, other additives, and the like.
  • Many pigment dispersions are used as the colorant.
  • a red pigment dispersion in which a red pigment and a yellow pigment are mixed is used to implement a red pixel of a color filter
  • a green pigment dispersion in which a green pigment and a yellow pigment is mixed is used to implement a green pixel of a color filter.
  • color filter manufacturing process is produced in a continuous process capable of mass production.
  • color filters having excellent color characteristics, heat resistance, etc. are required according to high quality specifications, and in particular, attempts to improve pigments, which are colorants, have been continued to improve luminance characteristics.
  • One embodiment is to provide a photosensitive resin composition having excellent transmittance and excellent color characteristics by having high brightness and high contrast ratio.
  • Another embodiment is to provide a color filter using the photosensitive resin composition.
  • One embodiment includes (A) an acrylic binder resin; (B) photopolymerizable monomers; (C) photoinitiator; (D) at least one repeating unit represented by formula 1, at least one repeating unit represented by formula 2, at least one repeating unit represented by formula 3, at least one repeating unit represented by formula 4 Pigment dispersion containing a functional resin and a pigment comprising; And (E) provides a photosensitive resin composition comprising a solvent.
  • R 1 to R 8 are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group
  • L 1 to L 4 are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
  • the functional resin may include a repeating unit represented by Formula 5 below.
  • a, b, c and d are each independently an integer of 1 or more.
  • the weight average molecular weight of the functional resin may be 5,000 g / mol to 30,000 g / mol.
  • the pigment may be a pigment in which the functional resin is adsorbed on the pigment surface.
  • the pigment may comprise an organic pigment, an inorganic pigment, or a combination thereof.
  • the pigment may comprise a green pigment.
  • the pigment may be surface-treated with the functional resin
  • the photosensitive resin composition is 3 to 10% by weight of the acrylic binder resin; 3 wt% to 13 wt% of the photopolymerizable monomer; 0.1 wt% to 3 wt% of the photopolymerization initiator; 2 wt% to 10 wt% of the pigment surface-treated with the functional resin; And the balance of the solvent.
  • the photosensitive resin composition is malonic acid; 3-amino-1,2-propanediol; Coupling agent containing a vinyl group or a (meth) acryloxy group; Leveling agents; Fluorine-based surfactants; And at least one additive selected from radical polymerization initiators.
  • Pigments surface-treated with the functional resin can be prepared by pulverizing the pigment and mixing the pulverized pigment with the functional resin.
  • Mixing the ground pigment with the functional resin may include adding the ground pigment and the functional resin to a solvent to prepare a solution, and drying the solution.
  • the pulverized pigment and the functional resin may be mixed in a weight ratio of 10: 4 to 10: 2.
  • the mixing may be at a temperature of 20 °C to 70 °C.
  • Another embodiment provides a color filter using the photosensitive resin composition for the color filter.
  • the photosensitive resin composition is excellent in transmittance, and has a high brightness and high contrast ratio, and excellent color characteristics, it can be usefully used in color filters.
  • substituted means that at least one hydrogen atom is a halogen atom (F, Cl, Br, I), hydroxy group, C1 to C20 alkoxy group, nitro group, cyano group, amine group, imino group , Azido groups, amidino groups, hydrazino groups, hydrazono groups, carbonyl groups, carbamyl groups, thiol groups, ester groups, ether groups, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C30 aryl group, C3 to C20 cycloalkyl group, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl group, It means substituted with a substituent of C2 to C20 heterohalogen atom (F, Cl, Br, I),
  • hetero means at least one hetero atom of at least one of N, O, S and P in the ring group unless otherwise specified in the present specification.
  • (meth) acrylate means that both “acrylate” and “methacrylate” are possible
  • (meth) acrylic acid means “acrylic acid” and “methacrylic acid”.
  • Photosensitive resin composition is (A) acrylic binder resin; (B) photopolymerizable monomers; (C) photoinitiator; (D) at least one repeating unit represented by formula 1, at least one repeating unit represented by formula 2, at least one repeating unit represented by formula 3, at least one repeating unit represented by formula 4 Pigment dispersion containing a functional resin and a pigment comprising; And (E) a solvent.
  • the photosensitive resin composition according to the embodiment includes a functional resin and a pigment, for example, by including a pigment surface-treated with the functional resin, thereby suppressing agglomeration between pigments, thereby improving dispersibility of the pigment, and thereby scattering light. By reducing, color characteristics such as transmittance and luminance can be improved.
  • the functional resin includes repeating units represented by the following Chemical Formulas 1 to 4.
  • R 1 to R 8 are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group
  • L 1 to L 4 are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
  • the functional resin may include a repeating unit represented by the following Formula 5.
  • a, b, c and d are each independently an integer of 1 or more.
  • the weight average molecular weight of the functional resin may be 5,000 g / mol to 30,000 g / mol.
  • the functional resin can improve the heat resistance of the pigment surface-treated with such a functional resin by including a ring structure having a large molecular weight.
  • the pigment surface-treated with the functional resin may be a pigment in which the functional resin is adsorbed onto the pigment surface.
  • the pigment in which the functional resin is adsorbed on the surface of the pigment may be prepared by mixing the pigment and the functional resin in a solvent at a weight ratio of 10: 4 to 10: 2, and removing the solvent therefrom.
  • Pigments may include organic pigments, inorganic pigments, or combinations thereof.
  • the pigment may comprise a green pigment.
  • the pigment is used through a process of miniaturization, that is, finely pulverizing the large pigment particles, fine pigments are easy to aggregate with each other, a pigment derivative, etc. are added during pigment dispersion to suppress the aggregation.
  • the pigment derivative it has a structure similar to the pigment, or having a structure capable of adsorbing well on the surface of the pigment physicochemically can suppress aggregation between fine pigments.
  • the added pigment derivative may cause color difference with the pigment to cause a decrease in coloring power or to cause dispersibility deterioration due to cohesion between pigment derivatives.
  • Pigment according to an embodiment surface treatment of the surface of the fine pigment with the functional resin that is, the resin containing the repeating units represented by Formula 1 to Formula 4 after the refinement process is completed, thereby improving the treatment efficiency, Therefore, aggregation between fine pigments can be efficiently suppressed.
  • the functional resin may be physicochemically adsorbed on the surface of the fine pigment to prevent adsorption between the fine pigments, and the dispersant described later may be further adsorbed onto the surface of the fine pigment to which the functional resin is not adsorbed, thereby improving dispersibility of the pigment.
  • fine pigment particles do not aggregate with each other, so that light scattering may be reduced to improve transmittance.
  • Treating the surface of the pigment with the functional resin may include pulverizing the pigment and mixing the pulverized pigment with the functional resin.
  • mixing the ground pigment and the functional resin may include adding the ground pigment and the functional resin to a solvent to prepare a solution, and drying the solution.
  • the pulverized pigment and the functional resin may be mixed in a weight ratio of 10: 4 to 10: 2, the mixing may also be carried out at a temperature of 20 °C to 70 °C.
  • pigments examples include red pigments, blue pigments, green pigments, violet pigments, yellow pigments, cyanine pigments, magenta pigments, and black pigments.
  • red pigment examples include perylene pigments, anthraquinone pigments, dianthraquinone pigments, azo pigments, diazo pigments, quinacridone pigments, anthracene pigments, and the like.
  • specific examples of the red pigment include perylene pigments, quinacridone pigments, naphthol AS, cuminamine pigments, anthraquinones (sudan I, II, III, R), dianthraquinolides, Vis azo, benzopyran, etc. are mentioned.
  • blue pigment examples include metal phthalocyanine pigments, indanthone pigments, and indophenol pigments.
  • Specific examples of the blue pigment include phthalocyanine metal complexes such as copper phthalocyanine, chloro copper phthalocyanine, chloro aluminum phthalocyanine, titanyl phthalocyanine, vanadate phthalocyanine, magnesium phthalocyanine, zinc phthalocyanine, iron phthalocyanine, and cobalt phthalocyanine.
  • Halogenated phthalocyanine pigment dye etc. are mentioned as said green pigment.
  • polychloro bromine phthalocyanine such as polychloro copper phthalocyanine and Green 58, etc. are mentioned.
  • Examples of the violet pigment include dioxazine violet, first violet B, methyl violet, indansrene brilliant violet, and the like.
  • yellow pigment examples include a tetra chloro isoindolinone pigment, a hansa pigment, a benzidine yellow pigment, and an azo pigment.
  • hansa yellow (10G, 5G, 3G, G, GR, A, RN, R), benzidine (G, GR), chrome yellow, permanent yellow (FGL, H10G, HR) etc. are mentioned.
  • cyanine pigments examples include metal-free phthalocyanine and merocyanine.
  • the magenta pigment may include dimethyl quinacridone, thio indigo, and the like.
  • black pigment aniline black, perylene black, titanium black, carbon black, etc. are mentioned.
  • the pigment may further include a dispersant for aiding the dispersion of the pigment.
  • a nonionic dispersant As the dispersant, a nonionic dispersant, an anionic dispersant, a cationic dispersant, or the like may be used.
  • the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, and carboxylic acids. Salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more thereof.
  • Examples of commercially available products of the dispersant include, for example, DISKBY-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc.
  • the dispersant may be included in an amount of 0.01 wt% to 15 wt% based on the total amount of the photosensitive resin composition for color filters.
  • the dispersant is included in the above range, excellent stability, developability and patternability can be obtained by excellent dispersibility of the photosensitive resin composition for color filters.
  • the pigment may be included in the photosensitive resin composition in the form of a dispersion.
  • the solvent for forming the pigment dispersion ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like can be used.
  • the content of the pigment dispersion may be 20% to 40% by weight, such as 30% to 40% by weight based on the total amount of the photosensitive resin composition.
  • the average particle diameter of the pigment may be 5 nm to 150 nm, such as 10 nm to 70 nm. When the average particle diameter of the pigment is within the above range, high contrast ratio can be realized while having excellent heat resistance and light resistance.
  • the pigment surface-treated with the functional resin may be included in an amount of 2 wt% to 10 wt%, such as 5 wt% to 8 wt%, based on the total amount of the photosensitive resin composition.
  • the pigment When used in the above range, it can have a high color and contrast ratio at the same color coordinates while having excellent color characteristics.
  • the photosensitive resin composition according to one embodiment includes an acrylic binder resin.
  • the acrylic binder resin is a copolymer of the first ethylenically unsaturated monomer and the second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.
  • the first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid,, or a combination thereof.
  • the first ethylenically unsaturated monomer may be included in an amount of 5 to 50 wt%, such as 10 to 40 wt%, based on the total amount of the acrylic binder resin.
  • the second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, ⁇ -methylstyrene, vinyltoluene, vinylbenzylmethyl ether, etc .; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds, such as vinyl acetate and a vinyl benzoate; Unsaturated carboxy
  • acrylic binder resin examples include polybenzyl methacrylate, (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like, but are not limited thereto, and these alone or in combination thereof. You may mix and use the above.
  • the weight average molecular weight of the acrylic binder resin may be about 3,000 g / mol to 150,000 g / mol, such as about 5,000 g / mol to 30,000 g / mol.
  • the weight average molecular weight of the acrylic binder resin is within the above range, the physical and chemical properties of the photosensitive resin composition for color filters are excellent, the viscosity is appropriate, and the adhesion with the substrate is excellent in the manufacture of the color filter.
  • the acid value of the acrylic binder resin may be about 50 mgKOH / g to 200 mgKOH / g, such as about 80 mgKOH / g to 150 mgKOH / g.
  • the acid value of the acrylic binder resin is within the above range, the resolution of the pixel pattern is excellent.
  • the acrylic binder resin may be included in an amount of 3 wt% to 15 wt%, such as 5 wt% to 10 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • the acrylic binder resin is included in the above range, it is excellent in sensitivity and developability, and chemical resistance is improved, so that pattern tearing does not occur.
  • a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond may be used.
  • the photopolymerizable monomer may form a pattern having excellent heat resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in the pattern forming process.
  • photopolymerizable monomer examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate , Pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) Acrylate, dipentaerythri
  • Examples of commercially available products of the photopolymerizable monomer are as follows.
  • Examples of the monofunctional ester of (meth) acrylic acid include Aronix M-101 ® , M-111 ® , M-114 ®, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nihon Kayaku Co., Ltd. KAYARAD TC-110S ® , TC-120S ®, etc .; The V-158 ® and V-2311 ® of Osaka Yuki Chemical Co., Ltd. are mentioned.
  • difunctional ester of the (meth) acrylic acid examples include, but are not limited to, Aronix M-210 ® , M-240 ® , M-6200 ®, etc. manufactured by Toagosei Chemical Industries, Ltd .; Nihon Kayaku Co., Ltd. KAYARAD HDDA ® , HX-220 ® , R-604 ®, etc .; And V-260 ® , V-312 ® and V-335 HP ® from Osaka Yuki Kagaku Kogyo Co., Ltd.
  • Examples of the trifunctional ester of (meth) acrylic acid include Aronix M-309 ® , M-400 ® , M-405 ® , M-450 ® , M-450 ® from Toagosei Kagaku Kogyo Co., Ltd.
  • the photopolymerizable monomer may be used by treating with an acid anhydride in order to impart better developability.
  • the photopolymerizable monomer may be included in an amount of 3 wt% to 13 wt%, such as 4 wt% to 10 wt%, based on the total amount of the photosensitive resin composition for the color filter.
  • curing is sufficiently performed at the time of exposure in the pattern forming step to provide excellent reliability and excellent developability to an alkaline developer.
  • the photopolymerization initiator may be an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, an oxime compound, or the like.
  • acetophenone-based compound examples include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, etc. are mentioned.
  • benzophenone-based compound examples include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4,4 '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone and the like.
  • thioxanthone-based compound examples include thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diiso Propyl thioxanthone, etc. are mentioned.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.
  • triazine-based compound examples include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4'- Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-biphenyl 4,6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho1-yl) -4,
  • Examples of the oxime compound include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione and 1- (o-acetyloxime) -1- [9- Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone and the like.
  • the photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, or the like.
  • the photopolymerization initiator may be included in an amount of 0.1 wt% to 3.0 wt%, such as 0.5 wt% to 1.0 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • photopolymerization initiator is included in the above range, photopolymerization occurs sufficiently during exposure in the pattern forming process, and it is possible to prevent a decrease in transmittance due to the unreacted initiator.
  • the solvent may be a material having compatibility with the acrylic binder resin, the photopolymerizable monomer, the photopolymerization initiator, and the pigment surface-treated with the functional resin but not reacting.
  • the solvent is not particularly limited, and specific examples thereof include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates
  • glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycols such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates such as propylene glycol monomethylether acetate and propylene glycol propylether acetate can be used.
  • the solvent may be included in a balance, such as 40 wt% to 90 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • a balance such as 40 wt% to 90 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • the photosensitive resin composition for color filters may include malonic acid, in order to prevent spots and spots upon application, to improve leveling performance, and to prevent generation of residue due to undeveloped; 3-amino-1,2-propanediol; Coupling agent containing a vinyl group or a (meth) acryloxy group; Leveling agents; Fluorine-based surfactants; And at least one additive selected from radical polymerization initiators.
  • the additive can be easily adjusted according to the desired physical properties.
  • the coupling agent may be a silane coupling agent, and examples of the silane coupling agent include trimethoxysilyl benzoic acid, ⁇ -methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, ⁇ -isocyanate propyl triethoxysilane, ⁇ -glycidoxy propyl trimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like. It can be mixed and used.
  • the silane coupling agent may be used in an amount of 0.01 parts by weight to 1 part by weight based on 100 parts by weight of the photosensitive resin composition for color filters.
  • the photosensitive resin composition for color filters may further include a fluorine-based surfactant, if necessary.
  • fluorine-based surfactants examples include F-482, F-484, F-478, F-554, etc. of DIC Corporation, but are not limited thereto.
  • the fluorine-based surfactant is preferably included in an amount of 0.01 wt% to 5 wt%, more preferably 0.1 wt% to 2 wt%, based on the total amount of the photosensitive resin composition. If outside the above range, the spreading property is not uniform in the coating step, it is difficult to form a film of uniform thickness.
  • the photosensitive resin composition according to one embodiment is an alkali developing type that is curable by irradiation of light and developable with an alkaline aqueous solution.
  • the photosensitive resin composition is laminated on a substrate and irradiated with an active line to form a pattern required for a color filter, the reaction is caused by light. Only it can be selectively dissolved.
  • the solution for removing the non-exposed sites is called a developer, and there are two types of developer, an organic solvent type and an alkali developer type. Among them, organic solvent type causes air pollution and is harmful to human body, so it is better to use alkaline developing type in terms of environment. Since the photosensitive resin composition according to the exemplary embodiment may use an alkaline developing type developer, it may be usefully used in terms of environment.
  • According to another embodiment provides a color filter manufactured using the photosensitive resin composition described above.
  • the manufacturing method of the color filter is as follows.
  • the above-mentioned photosensitive resin composition is applied to a thickness of, for example, 0.5 ⁇ to 10 ⁇ to form a resin composition layer.
  • UV, an electron beam, or an X-ray can be used as a light source used for irradiation,
  • UV of 190 nm-450 nm, specifically, 200 nm-400 nm region can be irradiated. It can also be performed using a photoresist mask further at the said irradiation process.
  • the resin composition layer irradiated with the light source is treated with a developer. At this time, the non-exposed part is melt
  • a color filter having a desired pattern By repeating this process in accordance with the required number of colors, a color filter having a desired pattern can be obtained.
  • crack resistance, solvent resistance, and the like can be improved by reheating the image pattern obtained by the development in the above step or by curing by actinic radiation.
  • the pigment, dispersant, and acrylic binder surface-treated with the functional resin according to Preparation Example 1 were dissolved and stirred in a solvent.
  • Dispersant (BYK2102, BYK): 6% by weight
  • Solvent propylene glycol methyl ethyl acetate, sigma-aldrich: 74 wt%
  • a pigment, a dispersant, and an acrylic binder were dissolved and stirred in a solvent with the following composition.
  • Acrylic binder (100S, SMS company): 3% by weight
  • Solvent (propylene glycol methyl ethyl acetate, sigma-aldrich): 78.5 wt%
  • acrylic binder resin polybenzyl methacrylate resin (NPR1520), Miwon Corporation)
  • Example 1 Comparative Example 1 (A) Acrylic Binder Resin 10 10 (B) Acrylic Photopolymerizable Monomer 8 8 (C) photopolymerization initiator 0.7 0.7 (D) Pigment Dispersion (D-1) 35 - (D-2) - 35 (E) solvent 45.8 45.8 (F) Additive (Fluorinated Surfactant) 0.5 0.5 Total 100.00 100.00
  • the photosensitive resin compositions according to Example 1 and Comparative Example 1 were coated on a glass substrate using a coating apparatus (MIKASA Co., Ltd.) so as to have a film thickness of 3.0 ⁇ m to 4.0 ⁇ m, and then dried at 90 ° C. on a hot plate to coat the coating film. Obtained.
  • the obtained coating film was irradiated with light at an exposure dose of 100 mJ / cm 2, and then baked at an oven condition of 230 ° C. for 30 minutes. Transmittance, color coordinates, and luminance were measured using a colorimeter (Otsuka, MCPD 3000), and the results are shown in Table 2 below.
  • Example 1 using the pigment according to the embodiment, it can be seen that the brightness of the photosensitive resin composition compared to Comparative Example 1 has a high transmittance.

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Abstract

La présente invention concerne une composition de résine photosensible et un filtre coloré utilisant ladite composition. La composition comprend : (A) une résine liante acrylique ; (B) un monomère photopolymérisable ; (C) un initiateur de photopolymérisation ; (D) une dispersion pigmentée contenant une résine fonctionnelle et un pigment, la résine fonctionnelle comportant au moins une unité de répétition représentée par la formule chimique 1, au moins une unité de répétition représentée par la formule chimique 2, au moins une unité de répétition représentée par la formule chimique 3 et au moins une unité de répétition représentée par la formule chimique 4 ; et (E) un solvant.
PCT/KR2014/003515 2014-01-17 2014-04-22 Composition de résine photosensible pour filtre coloré, et filtre coloré utilisant ladite composition Ceased WO2015108240A1 (fr)

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KR102731671B1 (ko) * 2021-07-19 2024-11-15 삼성에스디아이 주식회사 안료분산액, 이를 포함하는 감광성 수지 조성물, 감광성 수지막, 컬러필터 및 디스플레이 장치
CN115124889B (zh) * 2022-08-31 2022-11-22 山东凯瑞尔光电科技有限公司 一种用于彩色光刻胶的红色色浆及其制备方法
CN119842129B (zh) * 2024-12-24 2025-10-17 金发科技股份有限公司 一种非极性树脂复合材料及制备方法和应用

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JP2003238837A (ja) * 2002-02-14 2003-08-27 Fuji Photo Film Co Ltd 顔料分散剤、それを含む顔料分散組成物及び着色感光性組成物
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