# US 2010/0244673 A1 · Oxadiazole Derivative, and Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device Using Oxadiazole Derivative > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0244673 A1 - Document ID: US20100244673A1 - Status: Published application - Kind: A1 - Application number: 12/750,354 - Filed: 2010-03-30 - Published: 2010-09-30 - Earliest claimed: 2009-03-31 - Assignees: Semiconductor Energy Laboratory Co., Ltd. - Inventors: Hiroko Nomura; Hiroshi Kadoma; Takahiro Ushikubo; Satoko Shitagaki; Sachiko Kawakami; Satoshi Seo - Web page: https://patentgrep.com/patent/US20100244673A1 ## CPC - C07D 271/107: with two aryl or substituted aryl radicals attached in positions 2 and 5 - C07D 413/10: linked by a carbon chain containing aromatic rings - C07D 471/04: Ortho-condensed systems - C09K 11/06: containing organic luminescent materials - H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} - H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded - H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene} - H10K 85/6565: {Oxadiazole compounds} - C09K 2211/1048: with oxygen - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/14: Carrier transporting layers - H10K 50/155: comprising dopants - H10K 50/165: comprising dopants - H10K 50/19: Tandem OLEDs - H10K 59/122: Pixel-defining structures or layers, e.g. banks - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - H10K 2101/10: Triplet emission - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract An object is to provide a novel oxadiazole derivative represented by General Formula (G1) as a substance having a high electron-transport property. In the formula, Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring. When Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring. Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms. When Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring. R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ## Claims ### Claim 1 An oxadiazole derivative represented by General Formula (G1), wherein: Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 2 (depends on 1) The oxadiazole derivative according to claim 1, wherein the oxadiazole derivative is represented by General Formula (G2). ### Claim 3 (depends on 1) The oxadiazole derivative according to claim 1, wherein: the oxadiazole derivative is represented by General Formula (G3); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 4 (depends on 1) The oxadiazole derivative according to claim 1, wherein: the oxadiazole derivative is represented by General Formula (G4); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 5 A light-emitting element using an oxadiazole derivative represented by General Formula (G1), wherein: Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 6 A light-emitting device comprising: a pair of electrodes; and a layer including an oxadiazole derivative represented by General Formula (G1) between the pair of electrodes, wherein: Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 7 (depends on 6) The light-emitting device according to claim 6, wherein the oxadiazole derivative is represented by General Formula (G2). ### Claim 8 (depends on 6) The light-emitting device according to claim 6, wherein: the oxadiazole derivative is represented by General Formula (G3); and R1l to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 9 (depends on 6) The light-emitting device according to claim 6, wherein: the oxadiazole derivative is represented by General Formula (G4); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 10 (depends on 6) The light-emitting device according to claim 6, wherein the layer including the oxadiazole derivative is a light-emitting layer. ### Claim 11 An electronic device comprising a light-emitting device which has a light-emitting element, the light-emitting element comprising: a pair of electrodes; and a layer including an oxadiazole derivative represented by General Formula (G1) between the pair of electrodes, wherein: Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when A1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 12 (depends on 11) The electronic device according to claim 11, wherein the oxadiazole derivative is represented by General Formula (G2). ### Claim 13 (depends on 11) The electronic device according to claim 11, wherein: the oxadiazole derivative is represented by General Formula (G3); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 14 (depends on 11) The electronic device according to claim 11, wherein: the oxadiazole derivative is represented by General Formula (G4); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 15 A lighting device having a light-emitting element, the light-emitting element comprising: a pair of electrodes; and an layer comprising a oxadiazole derivative between the pair of electrodes, wherein: the oxadiazole derivative represented by General Formula (G1); Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 16 (depends on 15) The lighting device according to claim 15, wherein the oxadiazole derivative is represented by General Formula (G2). ### Claim 17 (depends on 15) The lighting device according to claim 15, wherein: the oxadiazole derivative is represented by General Formula (G3); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 18 (depends on 15) The lighting device according to claim 15, wherein: the oxadiazole derivative is represented by General Formula (G4); and R11 to R15 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms in a ring. ### Claim 19 A lighting device using an oxadiazole derivative between a pair of electrodes, wherein: the oxadiazole derivative represented by General Formula (G1); Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and when Ar1 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; Ar2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring or a substituted or unsubstituted heteroaryl group having 4 to 9 carbon atoms, and when Ar2 has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms in a ring; and R1 and R2 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.