# US 10,312,291 B2 · Photoelectric conversion device and imaging device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,312,291 B2 - Document ID: US10312291B2 - Status: Granted - Kind: B2 - Application number: 15/267,889 - Filed: 2016-09-16 - Published: 2017-04-20 - Granted: 2019-06-04 - Earliest claimed: 2015-10-16 - Assignees: Kabushiki Kaisha Toshiba - Applicants: Kabushiki Kaisha Toshiba - Inventors: Atsushi Wada; Isao Takasu; Satomi Taguchi - Web page: https://patentgrep.com/patent/US10312291B2 ## CPC - C07D 213/06: containing only hydrogen and carbon atoms in addition to the ring nitrogen atom - H10K 30/353: {comprising blocking layers, e.g. exciton blocking layers} - H10K 30/82: Transparent electrodes, e.g. indium tin oxide [ITO] electrodes - H10K 39/32: Organic image sensors - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10F 39/191: {Photoconductor image sensors} - H10K 30/50: Photovoltaic [PV] devices - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 2102/103: {comprising indium oxides, e.g. ITO} - Y02E 10/549: Organic PV cells - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - H10F: INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract According to one embodiment, a photoelectric conversion device includes a first electrode, a second electrode, a photoelectric conversion layer provided between the first electrode and the second electrode, and a first layer provided between the second electrode and the photoelectric conversion layer, the first layer including a phenyl pyridine derivative. The phenyl pyridine derivative is represented by formula (1) below, Rings A, B, C, and D in the formula (1) are pyridine rings. Each of R1 to R11 in the formula (1) is one selected from the group consisting of hydrogen, a straight-chain alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group. ## Claims ### Claim 1 A photoelectric conversion device comprising: a first electrode; a second electrode; a photoelectric conversion layer provided between the first electrode and the second electrode; and a first layer provided between the second electrode and the photoelectric conversion layer, the first layer comprising a phenyl pyridine derivative represented by formula (1), wherein A, B, C, and D in the formula (1) are each a pyridine ring, and each of R1 to R11 in the formula (1) is independently hydrogen, a straight-chain alkyl group, a branched alkyl group, an aryl group, or an electron-withdrawing heteroaryl group. ### Claim 2 (depends on 1) The device according to claim 1, wherein the R1 to R11 are identical to each other. ### Claim 3 (depends on 1) The device according to claim 1, wherein one of the R1 to R11 is different from another one of the R1 to R11. ### Claim 4 (depends on 1) The device according to claim 1, wherein: the phenyl pyridine derivative is represented by formula (2), ### Claim 5 (depends on 1) The device according to claim 1, wherein: the phenyl pyridine derivative is represented by formula (3), ### Claim 6 (depends on 1) The device according to claim 1, wherein: the phenyl pyridine derivative is represented by formula (4), ### Claim 7 (depends on 1) The device according to claim 1, wherein: the phenyl pyridine derivative is represented by formula (5), ### Claim 8 (depends on 1) The device according to claim 1, wherein a potential of the second electrode is higher than a potential of the first electrode. ### Claim 9 (depends on 1) The device according to claim 1, wherein a work function of the second electrode is smaller than a work function of the first electrode. ### Claim 10 (depends on 1) The device according to claim 1, wherein the first electrode comprises at least one oxide of indium, zinc, or tin. ### Claim 11 (depends on 1) The device according to claim 1, wherein the second electrode comprises at least one of aluminum, silver, gold, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, calcium-aluminum alloy, or a compound which comprises an oxide of at least one of indium, zinc, or tin. ### Claim 12 (depends on 1) The device according to claim 1, wherein the photoelectric conversion layer comprises at least one of coumarin, quinacridone, subphthalocyanine, fullerene (C60), perylene, or phthalocyanine. ### Claim 13 (depends on 1) The device according to claim 1, wherein a thickness of the first layer is not less than 3 and not more than 10 nm. ### Claim 14 (depends on 1) The device according to claim 1, further comprising a controller electrically connected to the first electrode and the second electrode, and which increases the potential of the second electrode to be higher than the potential of the first electrode. ### Claim 15 (depends on 1) The device according to claim 1, further comprising a second layer provided between the first electrode and the photoelectric conversion layer. ### Claim 16 (depends on 15) The device according to claim 15, wherein the second layer comprises at least one of N,N′-bis(3-methylphenyl)-N,N′-diphenylbenzidine (TPD), or tris(4-carbazoyl-9-yl-phenyl)amine (TCTA). ### Claim 17 An imaging device comprising a photoelectric conversion device, the photoelectric conversion device comprising: a first electrode; a second electrode; a photoelectric conversion layer provided between the first electrode and the second electrode; and a first layer provided between the second electrode and the photoelectric conversion layer, the first layer comprising a phenyl pyridine derivative represented by formula (1), wherein A, B, C, and D in the formula (1) are each a pyridine ring, and each of R1 to R11 in the formula (1) is independently hydrogen, a straight-chain alkyl group, a branched alkyl group, an aryl group, or an electron-withdrawing heteroaryl group. ### Claim 18 (depends on 17) The device according to claim 17, wherein, a plurality of the photoelectric conversion device are provided, the second electrode of one of the plurality of photoelectric conversion devices is separated along a first direction from the first electrode of the one of the plurality of photoelectric conversion devices, and at least a portion of the plurality of photoelectric conversion devices is juxtaposed along a second direction intersecting with the first direction. ### Claim 19 (depends on 17) The device according to claim 17, further comprising: a photodiode, the second electrode being separated along a first direction from the first electrode, and the photodiode overlapping the photoelectric conversion device in the first direction.