# US 9,520,564 B2 · Photoelectric conversion material, method for producing the same, and organic photovoltaic cell containing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,520,564 B2 - Document ID: US9520564B2 - Status: Granted - Kind: B2 - Application number: 14/445,332 - Filed: 2014-07-29 - Published: 2015-02-05 - Granted: 2016-12-13 - Earliest claimed: 2013-08-02 - Assignees: Honda Motor Co., Ltd. - Applicants: Honda Motor Co., Ltd. - Inventors: Kazuhiro Miura; Takahiro Miyazaki; Tadahiro Shiba - Web page: https://patentgrep.com/patent/US9520564B2 ## CPC - C09J 175/04: Polyurethanes - C08G 61/10: only aromatic carbon atoms, e.g. polyphenylenes - H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains - H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene} - H10K 85/151: {Copolymers} - C08G 2101/00: Manufacture of cellular products - C08G 2261/12: Copolymers - C08G 2261/228: Polymers, i.e. more than 10 repeat units - C08G 2261/312: Non-condensed aromatic systems, e.g. benzene - C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene - C08G 2261/46: Diels-Alder reactions - C08G 2261/91: Photovoltaic applications - H10K 30/50: Photovoltaic [PV] devices - H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene} - H10K 85/215: {comprising substituents, e.g. PCBM} - Y02E 10/549: Organic PV cells - Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract A bulk heterojunction-type organic photovoltaic cell, i.e., BHJ solar cell, has a photoelectric conversion layer containing a mixture of a donor domain and an acceptor domain. The donor domain contains a polymer as a donor (photoelectric conversion material), and the polymer is obtained by reaction of a polyphenylene represented by the following general formula (1). For example, the acceptor domain contains phenyl-C61-butyric acid methyl ester (PCBM) as an acceptor. At least one of R1 to R6 in the general formula (1) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group. ## Claims ### Claim 1 A photoelectric conversion material that acts as an electron donor for donating an electron or an electron acceptor for accepting an electron, comprising: a polymer obtained by reaction of a polyphenylene represented by the following general formula (1): wherein at least one of R1 to R6 in the general formula (1) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and n is the polymerization degree and has a value of 2 or more. ### Claim 2 (depends on 1) The photoelectric conversion material according to claim 1, wherein all of R1 to R10 in the general formula (1) are alkoxy groups. ### Claim 3 (depends on 2) The photoelectric conversion material according to claim 2, wherein R1 to R10 in the general formula (1) independently represent an alkoxy group having 1 to 20 carbon atoms. ### Claim 4 (depends on 1) The photoelectric conversion material according to claim 1, wherein the polymer has at least one structural unit selected from graphenes represented by the following general formulae (2) and (3): wherein at least one of R1 to R6 in each of the general formulae (2) and (3) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group. ### Claim 5 (depends on 1) The photoelectric conversion material according to claim 1, wherein the polymer has a polymerization degree of 2 to 1,000. ### Claim 6 (depends on 5) The photoelectric conversion material according to claim 5, wherein the polymer has a molecular weight of 1,500 to 4,000,000. ### Claim 7 A method for producing a photoelectric conversion material that acts as an electron donor for donating an electron or an electron acceptor for accepting an electron, comprising: polymerizing a phenylene derivative to prepare a polyphenylene; and reacting the polyphenylene to prepare a polymer as the photoelectric conversion material, the polyphenylene being represented by the following general formula (1): wherein at least one of R1 to R6 in the general formula (1) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and n is the polymerization degree and has a value of 2 or more. ### Claim 8 (depends on 7) The method according to claim 7, wherein all of R1 to R10 in the general formula (1) are alkoxy groups. ### Claim 9 (depends on 8) The method according to claim 8, wherein R1 to R10 in the general formula (1) independently represent an alkoxy group having 1 to 20 carbon atoms. ### Claim 10 (depends on 7) The method according to claim 7, wherein the polymer has at least one structural unit selected from graphenes represented by the following general formulae (2) and (3): wherein at least one of R1 to R6 in each of the general formulae (2) and (3) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group. ### Claim 11 (depends on 7) The method according to claim 7, wherein the polymer has a polymerization degree of 2 to 1,000. ### Claim 12 An organic photovoltaic cell comprising a photoelectric conversion material that acts as an electron donor for donating an electron or an electron acceptor for accepting an electron, wherein the organic photovoltaic cell has a photoelectric conversion layer, and the photoelectric conversion layer contains, as an electron donor, the photoelectric conversion material containing a polymer obtained by reaction of a polyphenylene represented by the following general formula (1): wherein at least one of R1 to R6 in the general formula (1) is an alkoxy group, and R7 to R10 independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and n is the polymerization degree and has a value of 2 or more. ### Claim 13 (depends on 12) The organic photovoltaic cell according to claim 12, including a bulk heterojunction structure containing the photoelectric conversion layer wherein the photoelectric conversion layer contains a mixture of the electron donor and an electron acceptor for accepting an electron released from the electron donor.