# US 10,312,457 B2 · Photoelectric conversion film, photoelectric conversion element 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 10,312,457 B2 - Document ID: US10312457B2 - Status: Granted - Kind: B2 - Application number: 15/645,428 - Filed: 2017-07-10 - Published: 2017-12-28 - Granted: 2019-06-04 - Earliest claimed: 2014-05-13 - Assignees: Sony Semiconductors Solutions Corporation - Applicants: Sony Semiconductor Solutions Corporation - Inventors: Yoshiaki Obana; Yuki Negishi; Yuta Hasegawa; Ichiro Takemura; Osamu Enoki; Hideaki Mogi; Nobuyuki Matsuzawa - Web page: https://patentgrep.com/patent/US10312457B2 ## CPC - C09B 47/00: Porphines; Azaporphines {(non-dyeing compounds C07D487/22)} - C07D 471/04: Ortho-condensed systems - C07F 5/022: {without C-boron linkages} - C09B 48/00: Quinacridones - C09B 67/0033: {Blends of pigments; Mixtured crystals; Solid solutions} - H10K 39/32: Organic image sensors - H10K 85/311: {Phthalocyanine} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions - H10K 39/00: Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00 - Y02E 10/542: Dye sensitized solar cells - Y02E 10/549: Organic PV cells - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract There is provided a photoelectric conversion film including a quinacridone derivative represented by the following General formula and a subphthalocyanine derivative represented by the following General formula. ## Claims ### Claim 1 An imaging device, comprising: a first electrode and a second electrode; and a photoelectric conversion film selectively absorbing light of a specific wavelength and disposed between the first electrode and the second electrode; wherein the photoelectric conversion film includes a first compound and a second compound, and the first compound and the second compound are formed as a bulk hetero mixed film, wherein the first compound is a subphthalocyanine derivative represented by General formula (1): wherein R11 to R16 are each fluorine, wherein the second compound is configured to transport a hole or an electron, wherein X is selected from the group consisting of a halogen, a hydroxy group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group, and wherein the photoelectric conversion film has a microstructure in which one of the first compound or the second compound is in a crystal fine particle state and the other of the first compound or the second compound is in an amorphous state. ### Claim 2 (depends on 1) The imaging device according to claim 1, wherein the first compound is represented by one of the following Formulas: ### Claim 3 (depends on 1) The imaging device according to claim 1, wherein the first compound is represented by one of the following Formulas: ### Claim 4 (depends on 1) The imaging device according to claim 1, further comprising; a third compound to block a hole from being introduced by the first electrode to the photoelectric conversion film. ### Claim 5 (depends on 4) The imaging device according to claim 4, wherein the third compound is fullerene. ### Claim 6 (depends on 1) The imaging device according to claim 1, wherein the first compound absorbs green light having a wavelength band of greater than or equal to approximately 450 nm and less than or equal to approximately 600 nm. ### Claim 7 (depends on 6) The imaging device according to claim 6, further comprising; a semiconductor substrate disposed below the photoelectric conversion film, wherein the semiconductor substrate includes a first photodiode and a second photodiode disposed below the first photodiode, and wherein the first photodiode absorbs blue light, the second photodiode absorbs red light, and the first photodiode and the second photodiode perform photoelectric conversion. ### Claim 8 (depends on 1) The imaging device according to claim 1, wherein the photoelectric conversion film having a microstructure in which the first compound is in a crystal fine particle state and the second compound is in an amorphous state. ### Claim 9 (depends on 1) The imaging device according to claim 1, wherein the photoelectric conversion film having a microstructure in which the second compound is in a crystal fine particle state and the first compound is in an amorphous state. ### Claim 10 An imaging device, comprising: a first electrode and a second electrode; and a photoelectric conversion film selectively absorbing light of a specific wavelength and disposed between the first electrode and the second electrode, wherein the photoelectric conversion film includes a first compound and a second compound, and the first compound and the second compound are formed as a bulk hetero mixed film, wherein the first compound is a subphthalocyanine derivative represented by General formula (2) or (3): wherein the second compound is configured to transport a hole or an electron, wherein X is selected from the group consisting of a halogen, a hydroxy group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group, and wherein the photoelectric conversion film has a microstructure in which one of the first compound or the second compound is in a crystal fine particle state and the other of the first compound or the second compound is in an amorphous state. ### Claim 11 (depends on 10) The imaging device according to claim 10, further comprising; a third compound configured to block a hole from being introduced by the first electrode to the photoelectric conversion film. ### Claim 12 (depends on 11) The imaging device according to claim 11, wherein the third compound is fullerene. ### Claim 13 (depends on 10) The imaging device according to claim 10, wherein the first compound absorbs green light having a wavelength band of greater than or equal to approximately 450 nm and less than or equal to approximately 600 nm. ### Claim 14 (depends on 13) The imaging device according to claim 13, further comprising; a semiconductor substrate disposed below the photoelectric conversion film, wherein the semiconductor substrate includes a first photodiode and a second photodiode disposed below the first photodiode, and wherein the first photodiode absorbs blue light, the second photodiode absorbs red light, and the first photodiode and the second photodiode perform photoelectric conversion. ### Claim 15 An imaging device, comprising: a first electrode; a second electrode; and an organic region including first, second, third, and fourth materials and disposed between the first electrode and the second electrode, the first material blocking a hole introduced from the first electrode to the organic region, the second material blocking an electron introduced from the second electrode to the organic region, the third material including a subphthalocyanine derivative represented by General formula (1): wherein R11 to R16 are each fluorine, performing photoelectric conversion and selectively absorbing light of a specific wavelength, wherein X is selected from the group consisting of a halogen, a hydroxy group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group, wherein the fourth material transports a hole or an electron, wherein the third material and the fourth material are formed as a bulk hetero mixed film, and wherein the bulk hetero mixed film has a microstructure in which one of the third material or the fourth material is in a crystal fine particle state and the other of the third material or the fourth material is in an amorphous state. ### Claim 16 (depends on 15) The imaging device according to claim 15, wherein the third material is represented by one of the following Formulas: ### Claim 17 (depends on 15) The imaging device according to claim 15, wherein the third material is represented by one of the following Formulas: ### Claim 18 (depends on 15) The imaging device according to claim 15, wherein the first material is fullerene. ### Claim 19 (depends on 15) The imaging device according to claim 15, wherein the organic region includes a hole blocking layer, a photoelectric conversion layer, and an electron blocking layer, wherein the photoelectric conversion layer is disposed between the hole blocking layer and the electron blocking layer, and wherein the hole blocking layer includes the first material, the electron blocking layer includes the second material, and the photoelectric conversion layer includes the third and fourth materials. ### Claim 20 (depends on 15) The imaging device according to claim 15, wherein the third material absorbs green light having a wavelength band of greater than or equal to approximately 450 nm and less than or equal to approximately 600 nm. ### Claim 21 (depends on 20) The imaging device according to claim 20, further comprising; a semiconductor substrate disposed below the organic region, wherein the semiconductor substrate includes a first photodiode and a second photodiode disposed below the first photodiode, and wherein the first photodiode absorbs blue light, the second photodiode absorbs red light, and the first photodiode and the second photodiode perform photoelectric conversion. ### Claim 22 (depends on 15) The imaging device according to claim 15, wherein the organic region having a microstructure in which the third material is in a crystal fine particle state and the fourth material is in an amorphous state. ### Claim 23 (depends on 15) The imaging device according to claim 15, wherein the organic region having a microstructure in which the fourth material is in a crystal fine particle state and the third material is in an amorphous state.