# US 10,312,452 B2 · Aromatic amine derivative and organic electroluminescence device utilizing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,312,452 B2 - Document ID: US10312452B2 - Status: Granted - Kind: B2 - Application number: 14/269,658 - Filed: 2014-05-05 - Published: 2014-08-28 - Granted: 2019-06-04 - Earliest claimed: 2005-03-18 - Assignees: Idemitsu Kosan Co., Ltd. - Applicants: Makoto Kimura; Chishio Hosokawa; Masakazu Funahashi - Inventors: Makoto Kimura; Chishio Hosokawa; Masakazu Funahashi - Web page: https://patentgrep.com/patent/US10312452B2 ## CPC - C07C 211/58: Naphthylamines; N-substituted derivatives thereof - C07C 211/61: with at least one of the condensed ring systems formed by three or more rings - C07C 217/92: the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring - C09B 57/00: Other synthetic dyes of known constitution - C09B 57/008: {Triarylamine dyes containing no other chromophores} - 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} - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/15: Hole transporting layers - H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene} - H10K 85/115: {Polyfluorene; Derivatives thereof} - H10K 85/324: {comprising aluminium, e.g. Alq3} - H10K 2102/103: {comprising indium oxides, e.g. ITO} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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) - 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 Provided is a novel aromatic amine derivative with specified structure. Also provided is an organic electroluminescence device having one or more organic thin-film layers including at least a luminescent layer interposed between a cathode and an anode, in which at least one of the organic thin-film layers contains the above aromatic amine derivative alone or as a component of mixture. As a result, there is provided an organic electroluminescence device that has high emission luminance and high heat resistance, excelling in high-temperature storage ability and has long life, and provided an aromatic amine derivative for realizing the organic electroluminescence device. ## Claims ### Claim 1 An organic electroluminescence device, comprising: a cathode; an anode; and an organic thin film layer comprising one or more layers, wherein the organic thin film layer comprises a light emitting layer, the organic thin film layer is interposed between the cathode and the anode, the organic thin film layer comprises a hole transporting layer between the anode and the light emitting layer, and the hole transporting layer comprises an aromatic amine compound represented by formula (2-a): wherein: each of Ar20 and Ar21 independently represents a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group; each of R41 to R44 independently represents a hydrogen atom, an unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, an unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group; a leftmost benzene ring is optionally substituted by 1 to 3 substituents selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group; and when the leftmost benzene ring is substituted by 2 or 3 substituents, the 2 or 3 substituents are different from each other. ### Claim 2 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 is independently selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyridinyl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted. ### Claim 3 (depends on 1) The organic electroluminescence device according to claim 1, wherein the aryl group having 5 to 40 ring carbon atoms for Ar20 and Ar21 is optionally substituted by an aryl group, an alkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group, or an alkoxycarbonyl group. ### Claim 4 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of R41 to R44 independently represents a hydrogen atom, an unsubstituted aryl group having 5 to 50 ring carbon atoms or an unsubstituted alkyl group having 1 to 50 carbon atoms. ### Claim 5 (depends on 4) The organic electroluminescence device according to claim 4, wherein the aryl group represented by each of R41 to R44 is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group. ### Claim 6 (depends on 4) The organic electroluminescence device according to claim 4, wherein the alkyl group represented by each of R41 to R44 is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, and a n-octyl group. ### Claim 7 (depends on 1) The organic electroluminescence device according to claim 1, wherein the optional substituent of the leftmost benzene ring is selected from the group consisting of a methyl group, an ethyl group, a t-butyl group, a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. ### Claim 8 (depends on 1) The organic electroluminescence device according to claim 1, wherein the compound is represented by any of formulae (30) to (34): ### Claim 9 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 independently represents a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group. ### Claim 10 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 independently represents a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group. ### Claim 11 (depends on 1) The organic electroluminescence device according to claim 1, wherein the leftmost benzene ring is unsubstituted. ### Claim 12 (depends on 1) The organic electroluminescence device according to claim 1, wherein the leftmost benzene ring is substituted by 1 to 3 substituents selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group. ### Claim 13 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of R41 to R44 independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ### Claim 14 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of R41 to R44 are methyl groups. ### Claim 15 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 independently represents a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group; each of R41 to R44 independently represents a hydrogen atom, an unsubstituted aryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; and the leftmost benzene ring is optionally substituted by a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ### Claim 16 (depends on 1) The organic electroluminescence device according to claim 1, wherein the leftmost benzene ring is optionally substituted by one substituent. ### Claim 17 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 independently represents a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group; each of R41 to R44 independently represents a hydrogen atom, an unsubstituted aryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; and a leftmost benzene ring is optionally substituted by 1 to 3 substituents selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ### Claim 18 (depends on 1) The organic electroluminescence device according to claim 1, wherein each of Ar20 and Ar21 independently represents a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar20 and Ar21 does not contain a vinyl group; each of R41 to R44 independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; and a leftmost benzene ring is unsubstituted. ### Claim 19 (depends on 1) The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is a blue emitting device.