# US 8,771,843 B2 · Fluorene derivative, organic compound, and light-emitting element, light-emitting device, and electronic device using the compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,771,843 B2 - Document ID: US8771843B2 - Status: Granted - Kind: B2 - Application number: 13/218,597 - Filed: 2011-08-26 - Published: 2012-03-01 - Granted: 2014-07-08 - Earliest claimed: 2010-08-27 - Assignees: Semiconductor Energy Laboratory Co., Ltd. - Applicants: Satoshi Seo; Sachiko Kawakami; Harue Osaka - Inventors: Satoshi Seo; Sachiko Kawakami; Harue Osaka - Web page: https://patentgrep.com/patent/US8771843B2 ## CPC - C07D 235/18: with aryl radicals directly attached in position 2 - H10K 85/611: {Charge transfer complexes} - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/13: comprising stacked EL layers within one EL unit - H10K 2101/10: Triplet emission - Y02E 10/549: Organic PV cells - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract To provide a novel organic compound having a bipolar property. To reduce power consumption of a light-emitting element, a light-emitting device, and an electronic device. The organic compound has a fluorene skeleton and a structure in which an electron-accepting unit and a hole-accepting unit are bonded through carbon at the 9-position of the fluorene skeleton. The organic compound has a bipolar property and a large band gap. The use of the organic compound makes it possible to reduce power consumption of a light-emitting element, a light-emitting device, and an electronic device. ## Claims ### Claim 1 An organic compound represented by General Formula (G1): wherein EA is an 1,3-azole group or a phenyl group substituted with an 1,3-azole group, and wherein HA represents a hole-accepting unit. ### Claim 2 (depends on 1) The organic compound according to claim 1, wherein the EA is a phenyl group substituted with an 1,3-azole group. ### Claim 3 (depends on 1) The organic compound according to claim 1, wherein the HA is a phenyl group having a π-electron rich heteroaromatic substituent or a phenyl group substituted with a diarylamino group. ### Claim 4 (depends on 1) The organic compound according to claim 1, wherein the organic compound is an organic semiconductor material. ### Claim 5 (depends on 1) A light-emitting element comprising the organic compound according to claim 1 between a pair of electrodes. ### Claim 6 (depends on 1) A light-emitting element comprising: a light-emitting layer comprising the organic compound according to claim 1 and a phosphorescent compound, between a pair of electrodes. ### Claim 7 (depends on 1) A light-emitting element comprising: a layer comprising the organic compound according to claim 1, between a pair of electrodes; and a light-emitting layer comprising a phosphorescent compound, between the layer and one of the pair of electrodes. ### Claim 8 (depends on 1) A light-emitting element comprising a light-emitting layer comprising the organic compound according to claim 1. ### Claim 9 (depends on 1) A light-emitting device comprising: a light-emitting element comprising the organic compound according to claim 1; and a control circuit configured to control light emission from the light-emitting element. ### Claim 10 (depends on 1) An electronic device comprising: a display portion comprising: a light-emitting element comprising the organic compound according to claim 1; and a control circuit configured to control light emission from the light-emitting element. ### Claim 11 A fluorene derivative represented by General Formula (G2-1): wherein E1 represents an oxygen atom or a nitrogen atom to which a phenyl group or a biphenyl group is bonded, wherein m and n separately represent 0 or 1, wherein α1 and α2 separately represent an arylene group, and wherein Ar1 and Ar2 separately represent any of a phenyl group, a naphthyl group, a phenanthryl group, and a triphenylenyl group. ### Claim 12 (depends on 11) The fluorene derivative according to claim 11, wherein the α1 and the α2 separately represent a phenylene group or a biphenyldiyl group. ### Claim 13 (depends on 11) The fluorene derivative according to claim 11, wherein the E1 represents the nitrogen atom to which a phenyl group is bonded, wherein n represents 1, wherein α1 and α2 separately represent a phenylene group, and wherein Ar1 and Ar2 separately represent a phenyl group. ### Claim 14 (depends on 11) The fluorene derivative according to claim 11, wherein the fluorene derivative is represented by Structural Formula (1) below: ### Claim 15 (depends on 11) A light-emitting element comprising the fluorene derivative according to claim 11 between a pair of electrodes. ### Claim 16 (depends on 11) A light-emitting element comprising: a light-emitting layer comprising the fluorene derivative according to claim 11 and a phosphorescent compound, between a pair of electrodes. ### Claim 17 (depends on 11) A light-emitting element comprising: a layer comprising the fluorene derivative according to claim 11, between a pair of electrodes; and a light-emitting layer comprising a phosphorescent compound, between the layer and one of the pair of electrodes. ### Claim 18 (depends on 11) A light-emitting element comprising a light-emitting layer comprising the fluorene derivative according to claim 11. ### Claim 19 (depends on 11) A light-emitting device comprising: a light-emitting element comprising the fluorene derivative according to claim 11; and a control circuit configured to control light emission from the light-emitting element. ### Claim 20 (depends on 11) An electronic device comprising: a display portion comprising: a light-emitting element comprising the fluorene derivative according to claim 11; and a control circuit configured to control light emission from the light-emitting element. ### Claim 21 A fluorene derivative represented by General Formula (G2-2): wherein E1 represents an oxygen atom or a nitrogen atom to which a phenyl group or a biphenyl group is bonded, and wherein m represents 0 or 1. ### Claim 22 (depends on 21) A light-emitting element comprising the fluorene derivative according to claim 21 between a pair of electrodes. ### Claim 23 (depends on 21) A light-emitting element comprising: a light-emitting layer comprising the fluorene derivative according to claim 21 and a phosphorescent compound, between a pair of electrodes. ### Claim 24 (depends on 21) A light-emitting element comprising: a layer comprising the fluorene derivative according to claim 21, between a pair of electrodes; and a light-emitting layer comprising a phosphorescent compound, between the layer and one of the pair of electrodes. ### Claim 25 (depends on 21) A light-emitting element comprising a light-emitting layer comprising the fluorene derivative according to claim 21. ### Claim 26 (depends on 21) A light-emitting device comprising: a light-emitting element comprising fluorene derivative according to claim 21; and a control circuit configured to control light emission from the light-emitting element. ### Claim 27 (depends on 21) An electronic device comprising: a display portion comprising: a light-emitting element comprising the fluorene derivative according to claim 21; and a control circuit configured to control light emission from the light-emitting element. ### Claim 28 (depends on 2) The organic compound according to claim 2, wherein the EA is a phenyl group substituted with a benzimidazole group. ### Claim 29 (depends on 3) The organic compound according to claim 3, wherein the HA is a diphenylaminophenyl group.