# US 11,309,498 B2 · Photoelectric conversion film, solid-state image sensor, and electronic device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,309,498 B2 - Document ID: US11309498B2 - Status: Granted - Kind: B2 - Application number: 17/026,026 - Filed: 2020-09-18 - Published: 2021-01-07 - Granted: 2022-04-19 - Earliest claimed: 2014-06-23 - Assignees: Sony Semiconductor Solutions Corporation - Applicants: Sony Semiconductor Solutions Corporation - Inventors: Osamu Enoki - Web page: https://patentgrep.com/patent/US11309498B2 ## CPC - H04N 25/70: SSIS architectures; Circuits associated therewith - C07F 5/022: {without C-boron linkages} - H04N 25/17: Colour separation based on photon absorption depth, e.g. full colour resolution obtained simultaneously at each pixel location - H10D 86/85: characterised by only passive components - H10K 85/311: {Phthalocyanine} - H10K 85/322: {comprising boron} - H10K 30/211: {comprising multiple junctions, e.g. double heterojunctions} - H10K 39/32: Organic image sensors - H04N: PICTORIAL COMMUNICATION, e.g. TELEVISION - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - H10D: INORGANIC ELECTRIC SEMICONDUCTOR DEVICES - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract [Object] To provide a photoelectric conversion film, a solid-state image sensor, and an electronic device which have an increased imaging characteristic. [Solution] Provided is a photoelectric conversion film including: a subphthalocyanine derivative represented by the following General Formula (1), where, in General Formula (1), X represents any substituent selected from among the group consisting of a halogen, a hydroxy group, a thiol group, an amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl amine group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted alkylthio group and a substituted or unsubstituted arylthio group, R1 to R3 each independently represent a substituted or unsubstituted ring structure, and at least one of R1 to R3 includes at least one hetero atom in the ring structure. ## Claims ### Claim 1 A photoelectric conversion film comprising: a subphthalocyanine derivative represented by General Formula (1), where, in the General Formula (1), X represents any substituent selected from the group consisting of a halogen, a hydroxy group, a thiol group, an amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl amine group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted alkylthio group and a substituted or unsubstituted arylthio group, R1 to R3 each independently represent a substituted or unsubstituted ring structure, and at least one of R1 to R3 includes at least one hetero atom in the ring structure, wherein the photoelectric conversion film comprises a bulk hetero mixed layer, and wherein the photoelectric conversion film is provided in a solid-state image sensor. ### Claim 2 (depends on 1) The photoelectric conversion film according to claim 1, wherein at least one of R1 to R3 has a ring structure comprising a substituent. ### Claim 3 (depends on 2) The photoelectric conversion film according to claim 2, wherein the substituent of R1 to R3 is a halogen. ### Claim 4 (depends on 1) The photoelectric conversion film according to claim 1, wherein R1 to R3 have a ring structure comprising a π-conjugated system structure. ### Claim 5 (depends on 1) The photoelectric conversion film according to claim 1, wherein R1 to R3 have a ring structure comprising 3 or more and 8 or fewer ring constituent atoms. ### Claim 6 (depends on 5) The photoelectric conversion film according to claim 5, wherein R1 to R3 have a ring structure comprising 6 ring constituent atoms. ### Claim 7 (depends on 1) The photoelectric conversion film according to claim 1, wherein the at least one hetero atom included in the ring structure of R1 to R3 is a nitrogen atom. ### Claim 8 (depends on 1) The photoelectric conversion film according to claim 1, wherein X is a halogen. ### Claim 9 (depends on 1) The photoelectric conversion film according to claim 1, wherein the subphthalocyanine derivative is a n-type light electric conversion material. ### Claim 10 (depends on 1) The photoelectric conversion film according to claim 1, wherein the bulk hetero mixed layer comprises the subphthalocyanine derivative. ### Claim 11 A solid-state image sensor comprising: a photoelectric conversion film comprising a subphthalocyanine derivative represented by General Formula (1), where, in the General Formula (1), X represents any substituent selected from the group consisting of a halogen, a hydroxy group, a thiol group, an amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl amine group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted alkylthio group and a substituted or unsubstituted arylthio group, R1 to R3 each independently represent a substituted or unsubstituted ring structure, and at least one of R1 to R3 includes at least one hetero atom in the ring structure, wherein the photoelectric conversion film comprises a bulk hetero mixed layer. ### Claim 12 (depends on 11) The solid-state image sensor according to claim 11, wherein at least one of R1to R3 has a ring structure comprising a substituent. ### Claim 13 (depends on 12) The solid-state image sensor according to claim 12, wherein the substituent of R1 to R3 is a halogen. ### Claim 14 (depends on 11) The solid-state image sensor according to claim 11, wherein R1 to R3 have a ring structure comprising a π-conjugated system structure. ### Claim 15 (depends on 11) The solid-state image sensor according to claim 11, wherein R1 to R3 have a ring structure comprising 3 or more and 8 or fewer ring constituent atoms. ### Claim 16 (depends on 15) The solid-state image sensor according to claim 15, wherein R1 to R3 have a ring structure comprising 6 ring constituent atoms. ### Claim 17 (depends on 11) The solid-state image sensor according to claim 11, wherein the at least one hetero atom included in the ring structure of R1 to R3 is a nitrogen atom. ### Claim 18 (depends on 11) The solid-state image sensor according to claim 11, wherein X is a halogen. ### Claim 19 (depends on 11) The solid-state image sensor according to claim 11, wherein the subphthalocyanine derivative is a n-type light electric conversion material. ### Claim 20 (depends on 11) The solid-state image sensor according to claim 11, wherein the bulk hetero mixed layer comprises the subphthalocyanine derivative. ### Claim 21 (depends on 11) The solid-state image sensor according to claim 11, wherein the photoelectric conversion film absorbs green light having a wavelength of greater than or equal to 450 nm and equal to or less than 600 nm and photoelectrically converts the absorbed green light. ### Claim 22 (depends on 11) The solid-state image sensor according to claim 11, configured as a laminated type solid-state image sensor, comprising: a first chip in which the photoelectric conversion film is formed; and a second chip in which a signal processing circuit configured to process a signal that is obtained by photoelectric conversion by the photoelectric conversion film is formed, the second chip being laminated with the first chip. ### Claim 23 An electronic device, comprising: a solid-state image sensor comprising a photoelectric conversion film comprising a subphthalocyanine derivative represented by General Formula (1); an optical system configured to guide incident light to the solid-state image sensor; and an arithmetic processing circuit configured to perform arithmetic processing of an output signal from the solid-state image sensor, wherein General Formula (1) is: where, X represents any substituent selected from the group consisting of a halogen, a hydroxy group, a thiol group, an amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl amine group, a substituted or unsubstituted aryl amine group, a substituted or unsubstituted alkylthio group, and a substituted or unsubstituted arylthio group, R1 to R3 each independently represent a substituted or unsubstituted ring structure, and at least one of R1 to R3 includes at least one hetero atom in the ring structure, wherein the photoelectric conversion film comprises a bulk hetero mixed layer.