# US 10,873,032 B2 · Organic photoelectric conversion element, two-dimensional sensor, image sensor, and imaging apparatus > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,873,032 B2 - Document ID: US10873032B2 - Status: Granted - Kind: B2 - Application number: 16/114,686 - Filed: 2018-08-28 - Published: 2019-01-10 - Granted: 2020-12-22 - Earliest claimed: 2016-03-03 - Assignees: Canon Kabushiki Kaisha - Applicants: Canon Kabushiki Kaisha - Inventors: Hirokazu Miyashita; Yosuke Nishide; Naoki Yamada; Jun Kamatani - Web page: https://patentgrep.com/patent/US10873032B2 ## CPC - C07C 211/61: with at least one of the condensed ring systems formed by three or more rings - C07C 255/42: the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms - H04N 25/79: Arrangements of circuitry being divided between different or multiple substrates, chips or circuit boards, e.g. stacked image sensors - H10K 85/211: {Fullerenes, e.g. C60} - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - C07C 2602/08: the other ring being five-membered, e.g. indane - H10K 39/32: Organic image sensors - H10K 85/215: {comprising substituents, e.g. PCBM} - H10K 85/622: {containing four rings, e.g. pyrene} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/655: {comprising only sulfur as heteroatom} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - Y02E 10/549: Organic PV cells - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - H04N: PICTORIAL COMMUNICATION, e.g. TELEVISION - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract Provided is an organic photoelectric conversion element including: an electron-collecting electrode; a hole-collecting electrode; and a photoelectric converter, which is arranged between the electron-collecting electrode and the hole-collecting electrode, wherein the photoelectric converter includes at least a first organic compound layer, and wherein the first organic compound layer contains a compound represented by the following general formula [1]. ## Claims ### Claim 1 An organic photoelectric conversion element comprising: an anode; a cathode; and a photoelectric converter, which is arranged between the anode and the cathode, wherein the photoelectric converter includes at least a first organic compound layer, and wherein the first organic compound layer contains a compound represented by general formula [1]: wherein, in the formula [1]: Ar1 and Ar2 each represent an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar1 and Ar2 may each further have a substituent selected from a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, a phenyl group, a tolyl group, a xylyl group, a mesityl group, and a cumenyl group, and when Ar1 and Ar2 each represent an aromatic hydrocarbon group having 6 to 18 carbon atoms or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar1 and Ar2 may be bonded to each other via any one of a single bond, and a methylene group and an ethylene group each of which may have an alkyl group to form a ring structure; Ar3 represents a fused polycyclic aromatic hydrocarbon group formed by fusion of 4 or 5 six-membered rings, excluding an acene group and a 2,7-pyrene group, Ar3 may further have a fluorine atom, a cyano group, a methyl group, or a tert-butyl group, and when Ar2 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar2 and Ar3 may be bonded to each other via any one of a single bond, and a methylene group and an ethylene group each of which may have an alkyl group to form a ring structure; and Q represents a substituent selected from a group of substituents represented by general formulae [2a] to [2e]: wherein, in the formulae [2a] to [2e], R1 to R27 each represents a substituent selected from a hydrogen atom, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or a cyano group, and * represents a bonding site with Ar3. ### Claim 2 (depends on 1) The organic photoelectric conversion element according to claim 1, wherein the Ar3 represents a pyrenediyl group, a benzopyrenediyl group, a triphenylenediyl group, a perylenediyl group, or a chrysenediyl group. ### Claim 3 (depends on 1) The organic photoelectric conversion element according to claim 1, wherein, in at least one of the Ar1 and the Ar2, the aromatic hydrocarbon group comprises a phenyl group or a naphthyl group, and the heteroaromatic ring group comprises a pyridyl group, a benzothienyl group, or a benzofuranyl group. ### Claim 4 (depends on 1) The organic photoelectric conversion element according to claim 1, wherein the Q represents a substituent selected from the formulae [2a] to [2c]. ### Claim 5 (depends on 1) The organic photoelectric conversion element according to claim 1, wherein the first organic compound layer further contains a fullerene derivative. ### Claim 6 (depends on 1) The organic photoelectric conversion element according to claim 1, further comprising a second organic compound layer, which is arranged between the cathode and the photoelectric converter. ### Claim 7 (depends on 1) The organic photoelectric conversion element according to claim 1, further comprising a third organic compound layer, which is arranged between the anode and the photoelectric converter. ### Claim 8 (depends on 1) A light area sensor comprising a plurality of the organic photoelectric conversion elements of claim 1, wherein the plurality of the organic photoelectric conversion elements are two-dimensionally arranged in an in-plane direction. ### Claim 9 (depends on 1) An organic photoelectric conversion apparatus comprising a plurality of organic photoelectric conversion elements configured to receive light beams having different wavelengths, wherein at least one organic photoelectric conversion element of the plurality of organic photoelectric conversion elements comprises the organic photoelectric conversion element of claim 1, and wherein the plurality organic photoelectric conversion elements are laminated. ### Claim 10 (depends on 9) A light area sensor comprising a plurality of the organic photoelectric conversion apparatus of claim 9, wherein the plurality of the photoelectric conversion apparatus are two-dimensionally arranged in an in-plane direction. ### Claim 11 (depends on 10) An imaging element, which is the light area sensor of claim 10, comprising: a plurality of organic photoelectric conversion elements; and a transistor connected to each of the plurality of organic photoelectric conversion elements, wherein the plurality of organic photoelectric conversion elements each serve as a light-receiving pixel, and wherein at least one of the plurality of organic photoelectric conversion elements comprises: an anode; a cathode; and a photoelectric converter, which is arranged between the anode and the cathode, wherein the photoelectric converter includes at least a first organic compound layer, and wherein the first organic compound layer contains a compound represented by general formula [1]: wherein, in the formula [1]: Ar1 and Ar2 each represent an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar1 and Ar2 may each further have a substituent selected from a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, a phenyl group, a tolyl group, a xylyl group, a mesityl group, and a cumenyl group, and when Ar1 and Ar2 each represent an aromatic hydrocarbon group having 6 to 18 carbon atoms or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar1 and Ar2 may be bonded to each other via any one of a single bond, and a methylene group and an ethylene group each of which may have an alkyl group to form a ring structure; Ar3 represents a fused polycyclic aromatic hydrocarbon group formed by fusion of 4 or 5 six-membered rings, excluding an acene group and a 2,7-pyrene group, Ar3 may further have a fluorine atom, a cyano group, a methyl group, or a tert-butyl group, and when Ar2 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a heteroaromatic ring group having 3 to 15 carbon atoms, Ar2 and Ar3 may be bonded to each other via any one of a single bond, and a methylene group and an ethylene group each of which may have an alkyl group to form a ring structure; and Q represents a substituent selected from a group of substituents represented by general formulae [2a] to [2e]: wherein, in the formulae [2a] to [2e], R1 to R27 each represents a substituent selected from a hydrogen atom, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or a cyano group, and * represents a bonding site with Ar3. ### Claim 12 (depends on 11) The imaging element according to claim 11, further comprising one of a color filter and an optical filter, which corresponds to the light-receiving pixel. ### Claim 13 (depends on 12) The imaging element according to claim 12, wherein the imaging element comprises the optical filter, and the optical filter comprises any one of a low-pass filter configured to transmit light having a wavelength equal to or longer than an infrared wavelength and a long-pass filter configured to transmit light having a wavelength equal to or shorter than an ultraviolet wavelength. ### Claim 14 (depends on 11) The imaging element according to claim 11, further comprising an optical member, which is arranged so as to correspond to each of a plurality of the light-receiving pixels. ### Claim 15 (depends on 11) An imaging apparatus comprising: an imaging optical system; and an imaging element configured to receive light that has passed the imaging optical system, wherein the imaging element comprises the imaging element of claim 11. ### Claim 16 (depends on 11) An imaging apparatus comprising: a joining portion capable of being joined to an imaging optical system; and the imaging element of claim 11. ### Claim 17 (depends on 15) The imaging apparatus according to claim 15, wherein the imaging apparatus comprises one of a digital camera and a digital still camera. ### Claim 18 (depends on 15) The imaging apparatus according to claim 15, further comprising a receiving unit configured to receive a signal from an outside, wherein the signal comprises a signal configured to control at least one of an imaging range of the imaging apparatus, a start of imaging thereof, and an end of the imaging. ### Claim 19 (depends on 15) The imaging apparatus according to claim 15, further comprising a transmitting unit configured to transmit an acquired image to an outside. ### Claim 20 An organic compound represented any one of formulae A1, A2, A5, A8, A9, A13, A14, A16, and A19-A24: ### Claim 21 (depends on 20) An organic photoelectric conversion element comprising: anode; cathode; and a photoelectric converter, which is arranged between the anode and the cathode, wherein the photoelectric converter includes at least a first organic compound layer, and wherein the first organic compound layer contains the organic compound according to claim 20.