# US 11,309,494 B2 · Copolymer and organic light emitting device comprising same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,309,494 B2 - Document ID: US11309494B2 - Status: Granted - Kind: B2 - Application number: 16/615,535 - Filed: 2018-10-17 - Published: 2020-06-11 - Granted: 2022-04-19 - Earliest claimed: 2017-10-30 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Yeonhui Yi; Jinseck Kim; Jaesoon Bae; Jaechol Lee; Soyoung Yu; Jae Hak Jeong - Web page: https://patentgrep.com/patent/US11309494B2 ## CPC - C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule - C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers - C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers - H10K 85/115: {Polyfluorene; Derivatives thereof} - H10K 85/151: {Copolymers} - C08G 2261/12: Copolymers - C08G 2261/122: statistical - C08G 2261/1412: Saturated aliphatic units - C08G 2261/1414: Unsaturated aliphatic units - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/148: Side-chains having aromatic units - C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene - C08G 2261/3162: Arylamines - C08G 2261/411: Suzuki reactions - C08G 2261/512: Hole transport - C08G 2261/76: crosslinking - C08G 2261/95: Use in organic luminescent diodes - H10K 50/15: Hole transporting layers - H10K 50/16: Electron transporting layers - H10K 50/17: Carrier injection layers - H10K 50/171: {Electron injection layers} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract The present specification provides a copolymer including a unit of Chemical Formula 1 and a unit of Chemical Formula 2; and an organic light emitting device including the same. ## Claims ### Claim 1 A copolymer comprising: a unit of the following Chemical Formula 1; a unit of the following Chemical Formula 2; and a unit of the following Chemical Formula 3, wherein, in Chemical Formulae 1 and 2, Y1 is O; R1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar6 is a direct bond; Ar7 is a substituted or unsubstituted arylene group; Ar8 and Ar9 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; a is an integer of 0 to 3; b is an integer of 0 or 1; c is an integer of 0 to 10; e is an integer of 1 or 2; and f is an integer of 1 or 2; when a is greater than 1, each of R1 is the same as or different from each other; when e is 2, each of is the same as or different from each other; and when f is 2, each of is the same as or different from each other, wherein, in Chemical Formula 3, R2 and R3 are the same as or different from each other, and each independently an unsubstituted alkyl group; R4 is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group; and d is from 0 to 6; when d is greater than 1, each of R4 is the same as or different from each other. ### Claim 2 (depends on 1) The copolymer of claim 1, comprising one, two or more of units represented by the following Chemical Formula 1-1 or Chemical Formula 1-2: wherein, in Chemical Formulae 1-1 and 1-2, R1 to R4, Ar1 to Ar9, Y1, and a to f have the same definitions as in Chemical Formulae 1 to 3. ### Claim 3 (depends on 1) The copolymer of claim 1, which is any one of the following structures: wherein, in the structural formulae, and p are a molar ratio of each represented unit, and o+p=1, is a molar ratio of 0.05 to 0.95, and p is a molar ratio of 0.05 to 0.95. ### Claim 4 (depends on 1) The copolymer of claim 1, which has a number average molecular weight of 1,000 g/mol to 1,000,000 g/mol. ### Claim 5 (depends on 1) A coating composition comprising the copolymer of claim 1. ### Claim 6 (depends on 5) An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the coating composition of claim 5 or a cured material thereof. ### Claim 7 (depends on 6) The organic light emitting device of claim 6, wherein the organic material layer includes a hole transfer layer, a hole injection layer, or a layer carrying out hole transfer and hole injection at the same time; and the hole transfer layer, the hole injection layer, or the layer carrying out hole transfer and hole injection at the same time includes the coating composition or a cured material thereof. ### Claim 8 (depends on 6) The organic light emitting device of claim 6, wherein the organic material layer includes an electron injection layer, an electron transfer layer, or a layer carrying out electron injection and electron transfer at the same time; and the electron injection layer, the electron transfer layer, or the layer carrying out electron injection and electron transfer at the same time includes the coating composition or a cured material thereof. ### Claim 9 (depends on 5) A method for manufacturing an organic light emitting device comprising: preparing a substrate; forming a cathode or an anode on the substrate; forming one or more organic material layers on the cathode or the anode; and forming an anode or a cathode on the organic material layer, wherein the forming of organic material layers includes forming one or more organic material layers using the coating composition of claim 5. ### Claim 10 (depends on 9) The method for manufacturing an organic light emitting device claim 9, wherein the forming of one or more organic material layers formed using the coating composition includes drying after coating the coating composition. ### Claim 11 (depends on 1) The copolymer of claim 1, wherein R1 and R4 are hydrogen; R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Ar1 to Ar3 are a phenylene group; Ar4 and Ar5 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group; Ar6 is a direct bond; Ar7 is a phenylene group unsubstituted or substituted with a methyl group or F, or a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; and Ar8 and Ar9 are hydrogen. ### Claim 12 (depends on 1) The copolymer of claim 1, which includes a structure represented by represented by the following Chemical Formula 1-3: wherein, in Chemical Formula 1-3, R1 to R4, Ar1 to Ar9, Y1, and a to f have the same definitions as in Chemical Formulae 1 to 3, and p are a molar ratio of each represented unit, and o+p=1, is a molar ratio of 0.05 to 0.95, and p is a molar ratio of 0.05 to 0.95. ### Claim 13 (depends on 1) The copolymer of claim 1, wherein an end group of the copolymer is hydrogen or an alkyl group. ### Claim 14 (depends on 5) The coating composition of claim 5, wherein the copolymer is in a range of 1% by weight to 10% by weight.