# US 12,216,403 B2 · Positive photosensitive resin composition and display device using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,216,403 B2 - Document ID: US12216403B2 - Status: Granted - Kind: B2 - Application number: 17/767,873 - Filed: 2020-10-08 - Published: 2024-04-11 - Granted: 2025-02-04 - Earliest claimed: 2019-10-11 - Assignees: Donjin Semichem Co., Ltd. - Applicants: Dongjin Semichem Co., Ltd. - Inventors: Kyoungsoon Shin; Hyoc-Min Youn; Tai Hoon Yeo; Dong Myung Kim; Gi Seon Lee; Ah Rum Park; Seok Hyeon Lee - Web page: https://patentgrep.com/patent/US12216403B2 ## CPC - G03F 7/0226: {characterised by the non-macromolecular additives} - G03F 7/00: Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor (using photoresist structures for special production processes, see the relevant places, e.g. B44C, H10P76/00, H05K) - G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence) - G03F 7/0048: {characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents} - G03F 7/022: Quinonediazides (G03F7/075 takes precedence) - G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides} - G03F 7/031: Organic compounds not covered by group G03F7/029 - G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) - G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain} - G03F 7/075: Silicon-containing compounds - G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)} - 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; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) ## Abstract This invention relates to a positive photosensitive resin composition that includes a siloxane copolymer of two kinds of reactive silane compounds with specific structures wherein residual impurities such as unreacted monomers and catalysts are minimized, and a UV absorber including one or more kinds of phenol hydroxyl groups capable of crosslinking and an alkoxy group. Accordingly, the resin composition exhibits excellent performances such as sensitivity, resolution, and degree of planarization, and also has excellent weatherability and UV absorbance, thereby providing excellent panel reliability. ## Claims ### Claim 1 A positive photosensitive resin composition comprising: 100 parts by weight of a siloxane-based copolymer; 5 to 50 parts by weight of a 1,2 quinonediazide compound; 0.1 to 10 parts by weight of one or more kinds of UV absorbers represented by the following Chemical Formula 1; and a solvent included in such an amount that the solid content of the total resin composition becomes 10 to 90 wt %, wherein the siloxane-based copolymer contains an unreacted monomer content less than 10 wt % and a residual catalyst content less than 2,000 ppm: wherein R1 is one or more functional groups selected from the group consisting of hydrogen, a substituted or unsubstituted C1-20 alkyl, a substituted or unsubstituted C3-20 cycloalkyl, a substituted or unsubstituted C2-10 alkenyl, a substituted or unsubstituted C6-18 aryl, a substituted or unsubstituted C7-18 alkylaryl, a substituted or unsubstituted C7-18 arylalkyl, a substituted or unsubstituted C1-20 alkoxy, a substituted or unsubstituted C1-30 acetal, a substituted or unsubstituted C1-30 hemiacetal, a substituted or unsubstituted C1-20 heteroalkyl, a substituted or unsubstituted C3-20 cycloheteroalkyl, a substituted or unsubstituted C2-10 heteroalkenyl, a substituted or unsubstituted C6-18 heteroaryl, a substituted or unsubstituted C7-18 heteroalkylaryl, a substituted or unsubstituted C7-18 heteroarylalkyl, a substituted or unsubstituted C1-20 heteroalkoxy, a substituted or unsubstituted C1-30 heteroacetal, and a substituted or unsubstituted C1-30 heterohemiacetal, and wherein R2 to R5 are each independently one or more functional groups selected from the group consisting of hydrogen, hydroxy, a substituted or unsubstituted C1-20 alkyl, a substituted or unsubstituted C3-20 cycloalkyl, a substituted or unsubstituted C2-10 alkenyl, a substituted or unsubstituted C6-18 aryl, a substituted or unsubstituted C7-18 alkylaryl, a substituted or unsubstituted C7-18 arylalkyl, a substituted or unsubstituted C1-20 alkoxy, a substituted or unsubstituted C1-30 acetal, a substituted or unsubstituted C1-30 hemiacetal, a substituted or unsubstituted C1-20 heteroalkyl, a substituted or unsubstituted C3-20 cycloheteroalkyl, a substituted or unsubstituted C2-10 heteroalkenyl, a substituted or unsubstituted C6-18 heteroaryl, a substituted or unsubstituted C7-18 heteroalkylaryl, a substituted or unsubstituted C7-18 heteroarylalkyl, a substituted or unsubstituted C1-20 heteroalkoxy, a substituted or unsubstituted C1-30 heteroacetal, and a substituted or unsubstituted C1-30 heterohemiacetal. ### Claim 2 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein R1 is a substituted or unsubstituted C1-20 alkyl group, wherein R2 to R4 are each independently or simultaneously one or more functional groups selected from the group consisting of hydrogen and a substituted or unsubstituted C1-20 alkoxy group, and wherein R5 is a hydroxy group. ### Claim 3 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein R1 is one or more functional groups selected from the group consisting of a substituted or unsubstituted C1-20 alkyl, a substituted or unsubstituted C1-30 acetal, and a substituted or unsubstituted C1-30 hemiacetal, and wherein R2 to R5 are each independently or simultaneously a substituted or unsubstituted C1-20 alkyl group. ### Claim 4 (depends on 3) The positive photosensitive resin composition according to claim 3, wherein R1 includes an alkyl group, which is substituted with a hydroxy group or a C1-12 alkyl or alkoxy group, or interrupted by an oxygen atom, a carbonyl group, or an ester group. ### Claim 5 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein R1 is one or more functional groups selected from the group consisting of a substituted or unsubstituted C1-20 alkyl, a substituted or unsubstituted C1-30 acetal, and a substituted or unsubstituted C1-30 hemiacetal, wherein R2 and R3 are each independently hydrogen, and wherein R4 and R5 are each independently or simultaneously one or more functional groups selected from the group consisting of hydrogen, a substituted or unsubstituted C6-18 aryl, a substituted or unsubstituted C7-18 alkylaryl, and a substituted or unsubstituted C7-18 arylalkyl. ### Claim 6 (depends on 5) The positive photosensitive resin composition according to claim 5, wherein R1 includes an alkyl group, which is substituted with a hydroxy group or a C1-12 alkyl or alkoxy group, or interrupted by an oxygen atom, a carbonyl group, or an ester group. ### Claim 7 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein in Chemical Formula 1, R1 is a substituted or unsubstituted C1-20 alkyl group, and wherein R2 to R5 are each independently or simultaneously one or more functional groups selected from the group consisting of hydrogen and a substituted or unsubstituted C1-20 alkyl group. ### Claim 8 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the siloxane-based copolymer is obtained by hydrolysis and condensation polymerization of i) 10 to 90 parts by weight of a silane compound represented by the following Chemical Formula 2, and ii) 10 to 90 parts by weight of a silane compound represented by the following Chemical Formula 3, based on 100 parts by weight of total monomers: (R6)nSi(R7)4-n, [Chemical Formula 2] wherein R6's are identical to or different from one another, and are each independently hydrogen, a C1-10 alkyl, a C2-10 acyl, a C2-10 alkenyl, or a C6-20 aryl, wherein R7's are identical to or different from one another, and are each independently, hydrogen, alkoxy, or chloro, and wherein n is an integer of 1 to 3, Si(OR8)4, [Chemical Formula 3] wherein R8's are identical to or different from one another, and are each independently methyl, ethyl, propyl, isopropyl, or butyl. ### Claim 9 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the siloxane copolymer has a polystyrene-converted weight average molecular weight of 1,000 g/mol to 30,000 g/mol. ### Claim 10 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the 1.2-quinonediazide compound is one or more selected from the group consisting of 1,2-quinonediazide 4-sulfonic acid ester, 1,2-quinonediazide 5-sulfonic acid ester, and 1,2-quinonediazide 6-sulfonic acid ester. ### Claim 11 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the UV absorber is one or more selected from compounds represented by the following Chemical Formulas 4 and 5, Chemical Formula 6-1, Chemical Formula 6-2, and Chemical Formulas 7 to 12: ### Claim 12 (depends on 11) The positive photosensitive resin composition according to claim 11, wherein the UV absorber is a mixture of two kinds, including: a mixture of i) one selected from the group consisting of Chemical Formula 4, Chemical Formula 5, a mixture of Chemical Formula 6-1 and Chemical Formula 6-2, and Chemical Formula 8; and ii) one selected from the group consisting of Chemical Formula 7, Chemical Formula 9, and Chemical Formula 10; or a mixture of iii) one selected from the group consisting of Chemical Formula 9 and Chemical Formula 10; and iv) one selected from the group consisting of Chemical Formula 11 and Chemical Formula 12. ### Claim 13 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the solvent is one or more selected from the group consisting of methanol, ethanol, benzyl alcohol, hexyl alcohol, ethylene glycol methylether acetate, ethylene glycol ethyletheracetate, ethylene glycol methylether propionate, ethylene glycol ethylether propionate, ethylene glycol methylether, ethylene glycol ethylether, diethylene glycol monomethylether, diethylene glycol monoethylether, diethylene glycol dimethylether, diethylene glycol methyl ethylether, propylene glycol methylether acetate, propylene glycol ethylether acetate, propylene glycol propylether acetate, propylene glycol methylether propionate, propylene glycol ethylether propionate, propylene glycol propylether propionate, propylene glycol methylether, propylene glycol ethylether, propylene glycol propylether, propylene glycol butylether, dipropylene glycol dimethylether, dipropylene glycol diethylether, butylene glycol monomethyl ether, butylene glycol monoethylether, dibutylene glycol dimethylether, and dibutylene glycol diethylether. ### Claim 14 (depends on 1) The positive photosensitive resin composition according to claim 1, wherein the UV absorber and the 1,2-quinonediazide compound are included at the weight ratio of 1:1 to 1:20. ### Claim 15 (depends on 1) A cured film comprising a cured body of the positive photosensitive resin composition according to claim 1. ### Claim 16 (depends on 15) The cured film according to claim 15, wherein transmittance at the wavelength of 400 nm, based on the film thickness of 3 μm, is equal to or greater than 80% and less than 95%. ### Claim 17 (depends on 1) A display device comprising a cured body of the positive photosensitive resin composition according to claim 1.