WO2012067457A2 - 아크릴레이트계 화합물을 포함하는 감광성 조성물 - Google Patents
아크릴레이트계 화합물을 포함하는 감광성 조성물 Download PDFInfo
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- WO2012067457A2 WO2012067457A2 PCT/KR2011/008820 KR2011008820W WO2012067457A2 WO 2012067457 A2 WO2012067457 A2 WO 2012067457A2 KR 2011008820 W KR2011008820 W KR 2011008820W WO 2012067457 A2 WO2012067457 A2 WO 2012067457A2
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- 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
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- 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
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- 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
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- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- 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
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- 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
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- the present invention relates to a photosensitive composition comprising an acrylate compound that can increase the developability of the photosensitive composition.
- the photosensitive composition is used as an essential material in manufacturing the color filter of a liquid crystal display element.
- a color pixel representing a color, a black diaphragm blocking light, an overcoat correcting a step difference between pixels, a column spacer maintaining a cell gap of a liquid crystal display, and the like are all used as photolithography. It consists of a thin film layer of 5 micrometers or less formed using the (photoetching process) method.
- the photosensitive composition used for a column spacer and an overcoat can also be used for the passivation of a thin film transistor layer, the characteristic of a photosensitive composition has a big influence on the productivity and quality of a color filter and a liquid crystal display element.
- Defects may occur after the manufacture of the color filter or after the passivation process of the thin film transistor. This may be due to the adhesion of foreign matter suspended in the air, or the fine damage of the thin film layer during storage or process progress. At this time, if the defective part is minute, it can be locally processed by applying a repair process. If not, the glass substrate having a relatively high unit cost is regenerated by reprocessing the color filter or the thin film transistor substrate. Chemicals used in reprocessing are mostly toxic, so glass should be regenerated at the lowest possible temperatures or shorter processing times.
- the thin film when the thin film is formed softly, the thin film may be easily damaged or may cause a problem such as an afterimage when the liquid crystal display is driven. Therefore, there is a need for the development of a composition capable of producing a thin film that is easy to reprocess while maintaining the strength of the thin film.
- the problem to be solved by the present invention is to provide a photosensitive composition comprising an acrylate-based compound capable of producing a thin film easy to peel without compromising strength.
- the present invention provides a photosensitive composition
- a photosensitive composition comprising a binder resin, a crosslinkable compound, a photopolymerization initiator, an acrylate compound represented by the following Formula 1, and a solvent including an alkali-soluble polymer resin.
- At least one of R 1 to R 4 is represented by the following formula (2), (3), (4) or (5),
- the remainder is selected from the group consisting of hydrogen, a halogen group, an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, and a haloalkyl group of 1 to 5 carbon atoms,
- R 5 , R 6 , R 7 and R 8 are the same as or different from each other, and are each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.
- the present invention provides a developability improving composition
- a developability improving composition comprising an acrylate compound represented by the formula (1).
- the present invention provides a photosensitive material comprising the photosensitive composition.
- the acrylate compound according to the present invention can be more usefully applied to the photosensitive composition by including at least one acrylate group around the adamantyl structure.
- the photosensitive composition according to the present invention has a feature that can shorten the development time during the photolithography process without compromising the strength of the thin film.
- Figure 1 shows the result of observing with an electron scanning microscope whether the pattern is formed after the development using the composition of Example 1.
- FIG. 2 shows the results of observing with an electron scanning microscope whether a pattern is formed after development using the composition of Comparative Example 2.
- the width indicated by the arrow is 5.20 ⁇ m.
- the photosensitive composition according to the present invention is characterized in that it comprises a binder resin containing an alkali-soluble polymer resin, a crosslinkable compound including two or more unsaturated acrylic groups, a photopolymerization initiator, an acrylate compound represented by the formula (1) and a solvent. do.
- the acrylate compound represented by Formula 1 includes at least one acrylate group centered on the adamantyl structure.
- halogen group examples include -F, -Cl, -Br, and -I, but are not limited thereto.
- the alkyl group may be straight or branched chain, carbon number is not particularly limited, but is preferably 1 to 5. Specific examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group and the like, but are not limited thereto.
- the alkoxy group may be one having 1 to 5 carbon atoms, more specifically methoxy, ethoxy, isopropyloxy, and the like, but is not limited thereto.
- the haloalkyl group may have 1 to 5 carbon atoms, and refers to a functional group in which at least one hydrogen of the alkyl group is substituted with a halogen group.
- the developability improving composition according to the present invention is characterized in that it comprises an acrylate compound represented by the formula (1).
- the developability improving composition may be the photosensitive composition described above.
- R 1 and R 2 are each independently represented by Formula 2, Formula 3, Formula 4 or Formula 5, and R 3 and R 4 may be hydrogen, but is not limited thereto.
- Chemical Formula 1 may be represented by any one of the following Chemical Formulas 6 to 13.
- the acrylate compound according to the present invention has a bulky multi-ring shape in which the central structure of the molecule is bulky, so that the molecules in the thin film are more easily separated from each other when the polymer thin film meets the alkali developer and the neutralization reaction proceeds and dissolves. It makes a role.
- the acrylate compound according to the present invention can be more usefully applied to the photosensitive composition by including at least one acrylate group around the adamantyl structure.
- the photosensitive composition according to the present invention has a feature that can shorten the development time during the photolithography process without compromising the strength of the thin film.
- the content of the acrylate compound represented by Chemical Formula 1 is preferably 0.8 to 4% by weight based on the total weight of the photosensitive composition, and more preferably 0.8 to 3.2% by weight. good.
- the content of the acrylate compound represented by Formula 1 is 0.8% by weight or more based on the total weight of the photosensitive composition, an improvement effect in peeling is good, and in the case of 4% by weight or less, there is an effect of preventing the strength of the thin film. .
- the content of the acrylate compound represented by Formula 1 is preferably 5 to 25% by weight based on the weight of the crosslinkable compound, and more preferably 5 to 20% by weight. It is effective.
- the content of the acrylate compound represented by Formula 1 is 5% by weight or more based on the weight of the crosslinkable compound, the improvement effect in peeling is good, and in the case of 25% by weight or less, the effect of preventing the strength inhibition of the thin film There is.
- the photosensitive composition which concerns on this invention has the effect of adjusting a viscosity by including binder resin, and the effect which enables patterning using alkaline developing solution.
- binder resin those generally used in the art such as an alkali-soluble binder resin may be used.
- the acrylic binder resin containing a carboxyl group can be used, More specifically, the thing comprised by copolymerizing the monomer which gives the mechanical strength of a film
- monomers usable for controlling the mechanical strength of the membrane for example, benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acryl Rate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth ) Acrylate, tetrahydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4 -Hydroxybutyl (meth) acrylate, glycerol (
- a monomer which gives alkali solubility it is (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth) acrylo, for example. It is effective to use at least one selected from the group consisting of yloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, and ⁇ -carboxy polycaprolactone mono (meth) acrylate. It is good, but it is not limited to these.
- binder resin what has a weight average molecular weight 3,000-150,000 can be used specifically. If the molecular weight is 3,000 or more, there is an effect of preventing the loss of the pattern during the development process, the viscosity is 150,000 or less has the effect of preventing the problem that the coating becomes difficult.
- the content of the binder resin is preferably 1 to 20% by weight based on the total weight of the photosensitive composition, but is not limited thereto.
- the content of the binder resin is 1% by weight or more, the patterning using the aqueous alkali solution is possible.
- the content is 20% by weight or less, there is an effect of preventing the loss of the pattern during the development process.
- a crosslinkable compound including an ethylenically unsaturated group may be used as the crosslinkable compound, and specifically, a crosslinkable compound including two or more unsaturated acrylic groups, three or more A crosslinkable compound containing an unsaturated acrylic group can be used.
- Ethylene glycol di (meth) acrylate polyethylene glycol di (meth) acrylate having the number of ethylene groups 2 to 14, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri ( Meta) acrylate, pentaerythritol tetra (meth) acrylate, 2-trisacryloyloxymethylethylphthalic acid, propylene glycol di (meth) acrylate with 2 to 14 propylene groups, dipentaerythritol penta (meth) acrylic A mixture of an acidic modification of latex, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate (trade name TO-2348, TO- 2349) compounds
- silica dispersions may be used for these compounds. Examples thereof include Nanocryl XP series (0596, 1045, 21/1364) and Nanopox XP series (0516, 0525) manufactured by Hanse Chemie.
- the content of the crosslinkable compound is preferably 1 to 30% by weight based on the total weight of the photosensitive composition, but is not limited thereto.
- the photopolymerization initiator is, for example, 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-meth Oxystyryl) -6-triazine, 2,4-trichloromethyl- (piflonil) -6-triazine, 2,4-trichloromethyl- (3 ', 4'-dimethoxyphenyl) -6 -Triazine, 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propanoic acid, 2,4-trichloromethyl- (4'-ethyl ratio Triazine-based compounds such as phenyl) -6-triazine and 2,4-trichloromethyl- (4'-methylbiphenyl) -6-triazine; 2,2'-bis (2-chloroph
- the content of the photoinitiator is preferably 0.1 to 5% by weight based on the total weight of the photosensitive composition, but is not limited thereto.
- the solvent is, for example, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, 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, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-meth It may include, but is not limited to, one or more selected from the group consisting of methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl
- the content of the solvent is preferably 45 to 95% by weight based on the total weight of the photosensitive composition, but is not limited thereto.
- the photosensitive composition according to the present invention may further include at least one selected from the group consisting of colorants, curing accelerators, thermal polymerization inhibitors, surfactants, photosensitizers, plasticizers, adhesion promoters, fillers and adhesion aids, depending on the use. can do.
- one or more pigments, dyes or mixtures thereof may be used.
- a metal oxide such as carbon black, graphite, titanium black, or the like may 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
- examples of the colorant to be colored are 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.
- a white pigment, a fluorescent pigment, etc. can also be used.
- a substance containing zinc as the center metal may be used.
- the curing accelerator for example, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mer Capto-4,6-dimethylaminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), penta Erythritol tris (2-mercaptoacetate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), and trimethyl It may include one or more selected from the group consisting of all ethane tris (3-mercaptopropionate), but is not limited to these may include those generally
- thermal polymerization inhibitor examples include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy It may include one or more selected from the group consisting of amine aluminum salts and phenothiazines, but is not limited thereto and may include those generally known in the art.
- the surfactant, photosensitizer, plasticizer, adhesion promoter, filler and the like can also be used for all compounds that can be included in the conventional photosensitive resin composition.
- the content of the colorant is preferably 1 to 20% by weight based on the total weight of the photosensitive composition, and the other additives are preferably 0.01 to 5% by weight based on the total weight of the photosensitive composition. It is not limited only to this.
- the transparent photosensitive composition according to the present invention is used in roll coaters, curtain coaters, spin coaters, spin coaters, slot die coaters, various printing, deposition, etc., metal, paper, glass plastic substrates It can be applied on a support such as. Moreover, after apply
- Light sources for curing the transparent photosensitive composition of the present invention include, but are not limited to, mercury vapor arcs, carbon arcs, Xe arcs, and the like, which emit light having a wavelength of 250 to 450 nm, for example.
- the thin film strength is 0.21 GPa or more, specifically 0.24 GPa or more. As long as the film strength is 0.21 GPa or more, the effect of the thin film can be obtained. The film is more excellent as long as it is 0.24 GPa or more. Therefore, when forming a thin film with the photosensitive composition of this invention, there exists an effect which peels easily, without reducing thin film strength.
- the substrate includes, for example, a support such as a metal, paper, glass plastic substrate, and the like, but is not limited thereto.
- the photosensitive composition according to the present invention is a photosensitive composition for photoacryl, a photosensitive composition for a touch panel protective material, a photosensitive composition for a TFT LCD color filter, a black matrix photosensitive composition for a TFT LCD or an organic light emitting diode, a photosensitive composition for an overcoat layer, a photosensitive composition for a column spacer.
- the composition may be selected from the group consisting of a photosensitive composition for a photocurable paint, a photosensitive composition for a photocurable ink, a photocurable adhesive photosensitive composition, a photosensitive composition for a printing plate, and a photosensitive composition for a printed circuit board, but is not limited thereto.
- the photosensitive composition according to the present invention is a photoacryl photosensitive material, a photosensitive material for a touch panel protective material, a pigment dispersion type photosensitive material for manufacturing a TFT LCD color filter, a photosensitive material for forming a black matrix of a TFT LCD or an organic light emitting diode (OLED), LCD Or it may be used as a photosensitive material selected from the group consisting of a photosensitive material for forming an overcoat layer of OLED, a column spacer photosensitive material, a printing plate, a photosensitive material for a printed circuit board and a transparent photosensitive material. Moreover, it can also be used for PDP manufacture, the partition material for OLED, the partition material for LED lighting, etc., and the use is not specifically limited.
- the following photosensitive compositions were prepared. 8 parts by weight of a binder BzMA / MAA made of alkali-soluble resin (molar ratio: 70/30, Mw: 24,000), 16 parts by weight of a compound of dipentaerythritol hexaacrylate as a crosslinking compound, Irgacure 369 (manufactured by Ciba-Geigy as a photopolymerization initiator 1 part by weight of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one) and 0.8 part by weight of the acrylate compound represented by the formula (6) 5%), PGMEA, an organic solvent, was added so that the total amount was 100 parts by weight, and a solution mixed for 3 hours using a shaker was obtained by using a 5 micron filter.
- PGMEA an organic solvent
- Example 2 The same procedure as in Example 1 was repeated except that 1.6 parts by weight (10% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 in Example 1. .
- Example 2 The same procedure as in Example 1 was repeated except that 2.4 parts by weight (15% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 in Example 1. .
- Example 2 The same procedure as in Example 1 was performed except that 3.2 parts by weight (20% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 in Example 1. .
- Example 2 The same procedure as in Example 1 was performed except that 4.0 parts by weight (25% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (7) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (7) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (7) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (7) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by Formula 7 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (8) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (8) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (8) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (8) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 2 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by Formula 8 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (9) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (9) was used instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (9) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (9) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 In Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by the formula (9) was used instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (10) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (10) was used instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (10) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (10) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by Formula 10 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (11) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Except for using the acrylate compound represented by the formula (11) 1.6 parts by weight (10% of the crosslinkable compound) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 And proceeded in the same manner as in Example 1.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (11) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (11) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by Formula 11 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (12) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (12) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (12) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Except for using the acrylate compound represented by the formula (12) 3.2 parts by weight (20% of the crosslinkable compound) instead of 0.8 parts by weight (5% of the crosslinkable compound) represented by the formula (6) in Example 1 And proceeded in the same manner as in Example 1.
- Example 1 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by the formula (12) was used instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (13) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 1.6 parts by weight (10% of the crosslinkable compound) of the acrylate compound represented by the formula (13) was used instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 2.4 parts by weight (15% of the crosslinkable compound) of the acrylate compound represented by the formula (13) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 3.2 parts by weight (20% of the crosslinkable compound) of the acrylate compound represented by the formula (13) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 2 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 4.0 parts by weight (25% of the crosslinkable compound) of the acrylate compound represented by Formula 13 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 The procedure was the same as in Example 1 except that 0.5 parts by weight (3% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 in Example 1. .
- Example 1 The procedure was the same as in Example 1 except that 5.0 parts by weight (31% of the crosslinkable compound) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 in Example 1. .
- Example 1 0.5 parts by weight (3% of the crosslinkable compound) of the acrylate compound represented by the formula (7) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 7 Instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by Formula 7 was used. It proceeded in the same manner as in Example 1 except that.
- the acrylate compound represented by the formula (8) 0.5 parts by weight (3% of the crosslinkable compound) instead of 0.8 parts by weight (5% of the crosslinkable compound) represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by the formula (8) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 1 0.5 parts by weight (3% of the crosslinkable compound) of the acrylate compound represented by the formula (9) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by Formula 9 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 An example of using 0.5 parts by weight of the acrylate compound represented by Formula 10 instead of 0.8 parts by weight of the acrylate compound represented by Formula 6 (5% of the crosslinkable compound) in Example 1 (3% of the crosslinkable compound) It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by Formula 10 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.5 parts by weight (3% of the crosslinkable compound) of the acrylate compound represented by the formula (11) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 Instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by Formula 11 was used. It proceeded in the same manner as in Example 1 except for.
- Example 1 0.5 parts by weight (3% of the crosslinkable compound) of the acrylate compound represented by the formula (12) instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6) in Example 1 It proceeded in the same manner as in Example 1 except for.
- Example 1 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by the formula (12) was used instead of 0.8 part by weight (5% of the crosslinkable compound) of the acrylate compound represented by the formula (6). It proceeded in the same manner as in Example 1 except for.
- Example 2 Instead of 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by Formula 6 in Example 1, 5.0 parts by weight (31% of the crosslinkable compound) of the acrylate compound represented by Formula 13 was used. It proceeded in the same manner as in Example 1 except for.
- Example 2 The same procedure as in Example 1 was carried out except that 0.8 parts by weight (5% of the crosslinkable compound) of the acrylate compound represented by Chemical Formula 6 was not used.
- Example 1 is the same as in Example 1, except that 8 parts by weight of the binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin is not used.
- Example 6 8 parts by weight of a binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin was used.
- Example 11 is the same as in Example 11, except that 8 parts by weight of the binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin is not used.
- Example 16 Except that in Example 16, 8 parts by weight of the binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin is not the same as in Example 16.
- Example 21 is the same as Example 21, except that 8 parts by weight of the binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin is not used.
- Example 26 Except that in Example 26, 8 parts by weight of a binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of an alkali-soluble resin is not used, and is the same as Example 26.
- Example 31 Except that in Example 31, 8 parts by weight of a binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of alkali-soluble resin was not used, and was the same as Example 31.
- Example 36 Except that in Example 36, 8 parts by weight of a binder BzMA / MAA (molar ratio: 70/30, Mw: 24,000) made of alkali-soluble resin was not used, and was the same as Example 36.
- a photosensitive composition obtained in the above Examples and Comparative Examples to form a uniform thin film by spin coating, slit coating, dip coating or doctor blading method to perform a prebaking process for 100 seconds at 100 °C
- the solvent was volatilized.
- the thickness of the dried thin film was about 4 microns. It was then exposed under a high pressure mercury lamp using a photo mask consisting of lines with a width of 5 microns spacing from 5 to 50 microns.
- the exposed substrate was developed by spray method in 0.04% aqueous KOH solution at a temperature of 25 ° C., then washed with pure water and dried by air blowing. After the treatment for 30 minutes in an oven holding 210 °C to form a final thin film.
- Comparative Example 1 is a case where no acrylate compound is used as an experiment. In comparison with this, it can be seen that in Examples 1 to 56, the peeling time is shortened depending on the content of the acrylate compound. This phenomenon can be considered to have a bulky characteristic of the adamantyl structure located in the center of the acrylate compound to facilitate the penetration of the stripping solution in the thin film. In addition, it can be seen that when the input amount is 25% or less, specifically 20% or less, based on the crosslinking agent, the strength of the thin film is not significantly affected.
- Comparative Examples 2-9 are the case where a binder is not used by the experiment used as a reference
- the viscosity was adjusted to 11-20 cSt to form a thin film.
- the viscosity was only 2.5 cSt, and it was difficult to control the viscosity to form a thin film.
- the acrylate compound according to the present invention can be more usefully applied to the photosensitive composition by including at least one acrylate group around the adamantyl structure.
- the photosensitive composition according to the present invention has a feature that can shorten the development time during the photolithography process without compromising the strength of the thin film.
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Abstract
Description
Claims (16)
- 알칼리 가용성 고분자 수지를 포함하는 바인더 수지, 가교성 화합물, 광중합 개시제, 하기 화학식 1로 표시되는 아크릴레이트계 화합물 및 용매를 포함하는 것을 특징으로 하는 감광성 조성물:[화학식 1]상기 화학식 1에서,R1 내지 R4 중 적어도 하나는 하기 화학식 2, 화학식 3, 화학식 4 또는 화학식 5로 표시되고,나머지는 수소, 할로겐기, 탄소수 1 내지 5의 알킬기, 탄소수 1 내지 5의 알콕시기 및 탄소수 1 내지 5의 할로알킬기로 이루어진 군으로부터 선택되며,[화학식 2][화학식 3][화학식 4][화학식 5]상기 화학식 2 내지 화학식 5에서,R5, R6, R7 및 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 또는 탄소수 1 내지 5의 알킬기이다.
- 청구항 1에 있어서, 상기 화학식 1의 R1 및 R2는 각각 독립적으로 상기 화학식 2, 화학식 3, 화학식 4 또는 화학식 5로 표시되고, R3 및 R4는 수소인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 아크릴레이트계 화합물의 함량은 감광성 조성물 총 중량을 기준으로 0.8 ~ 4 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 아크릴레이트계 화합물의 함량은 가교성 화합물의 중량을 기준으로 5 ~ 25 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 바인더 수지는 카르복실기를 함유하는 아크릴계 바인더 수지인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 바인더 수지의 함량은 감광성 조성물 총 중량을 기준으로 1 ~ 20 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 가교성 화합물의 함량은 감광성 조성물 총 중량을 기준으로 1 ~ 30 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 광중합 개시제의 함량은 감광성 조성물 총 중량을 기준으로 0.1 ~ 5 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 용매의 함량은 감광성 조성물 총 중량을 기준으로 45 ~ 95 중량%인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 감광성 조성물은 기재에 적용하여 박막을 형성할 경우 박막 강도가 0.24 GPa 이상인 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 감광성 조성물은 착색제, 경화촉진제, 열중합억제제, 계면활성제, 광증감제, 가소제, 접착촉진제, 충전제 및 접착조제로 이루어진 군으로부터 선택되는 1종 이상을 추가로 포함하는 것을 특징으로 하는 감광성 조성물.
- 청구항 1에 있어서, 상기 감광성 조성물은 포토아크릴용 감광성 조성물, 터치패널 보호재료용 감광성 조성물, 컬러필터용 감광성 조성물, 블랙 매트릭스 감광성 조성물, 오버코트층용 감광성 조성물, 컬럼 스페이서용 감광성 조성물, 광경화성 도료용 감광성 조성물, 광경화성 잉크용 감광성 조성물, 광경화성 접착제 감광성 조성물, 인쇄판용 감광성 조성물 및 인쇄배선반용 감광성 조성물으로 이루어진 군으로부터 선택되는 것을 특징으로 하는 감광성 조성물.
- 청구항 1의 화학식 1로 표시되는 아크릴레이트계 화합물을 포함하는 현상성 개선 조성물.
- 청구항 1 내지 청구항 13 중 어느 한 항의 감광성 조성물을 포함하는 감광재.
- 청구항 15에 있어서, 상기 감광재는 포토아크릴용 감광재, 터치패널 보호재료용 감광재, 컬러필터 제조용 안료분산형 감광재, 블랙 매트릭스 형성용 감광재, 오버코트층 형성용 감광재, 컬럼 스페이서 감광재 및 인쇄배선반용 감광재로 이루어진 군으로부터 선택되는 것을 특징으로 하는 감광재.
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CN201180065403.9A CN103329043B (zh) | 2010-11-19 | 2011-11-17 | 包含丙烯酸酯化合物的光敏组合物 |
US13/988,469 US9034561B2 (en) | 2010-11-19 | 2011-11-17 | Photosensitive composition comprising an acrylate compound |
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KR101690814B1 (ko) * | 2012-05-31 | 2017-01-10 | 주식회사 엘지화학 | 감광성 수지 조성물, 상기 감광성 수지 조성물로 제조된 감광재, 이를 포함하는 컬러필터 및 이를 포함하는 디스플레이 장치 |
JP5846061B2 (ja) * | 2012-07-09 | 2016-01-20 | 信越化学工業株式会社 | パターン形成方法 |
KR101953923B1 (ko) | 2013-07-23 | 2019-05-22 | 동우 화인켐 주식회사 | 열경화성 수지 조성물 및 그 조성물로 형성된 보호막을 구비한 컬러 필터 및 표시 장치 |
WO2016158864A1 (ja) * | 2015-04-01 | 2016-10-06 | 東レ株式会社 | 感光性樹脂組成物、導電性パターンの製造方法、基板、タッチパネル及びディスプレイ |
CN105549325A (zh) * | 2015-12-11 | 2016-05-04 | 阜阳欣奕华材料科技有限公司 | 金刚烷衍生物单体、彩色光阻剂及其制备方法、彩色滤光片 |
WO2018029747A1 (ja) * | 2016-08-08 | 2018-02-15 | 東レ株式会社 | 感光性樹脂組成物、導電性パターンの製造方法、基板、タッチパネル及びディスプレイ |
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- 2011-11-17 US US13/988,469 patent/US9034561B2/en active Active
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WO2012067457A3 (ko) | 2012-09-20 |
KR20120054540A (ko) | 2012-05-30 |
TWI473824B (zh) | 2015-02-21 |
US20130244182A1 (en) | 2013-09-19 |
CN103329043A (zh) | 2013-09-25 |
US9034561B2 (en) | 2015-05-19 |
KR101356869B1 (ko) | 2014-01-28 |
TW201233696A (en) | 2012-08-16 |
CN103329043B (zh) | 2016-06-29 |
JP5688159B2 (ja) | 2015-03-25 |
JP2013543993A (ja) | 2013-12-09 |
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