# US 2019/0169097 A1 · Organic electroluminescence device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0169097 A1 - Document ID: US20190169097A1 - Status: Published application - Kind: A1 - Application number: 16/267,714 - Filed: 2019-02-05 - Published: 2019-06-06 - Earliest claimed: 2010-01-15 - Assignees: UDC Ireland Limited - Applicants: Udc Ireland Limited - Inventors: Tetsu Kitamura; Toru Watanabe; Toshihiro Ise - Web page: https://patentgrep.com/patent/US20190169097A1 ## CPC - C07C 15/28: Anthracenes - C07C 15/38: containing four rings - C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system - 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 85/342: {comprising iridium} - H10K 85/346: {comprising platinum} - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C09K 2211/1007: Non-condensed systems - C09K 2211/1011: Condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/171: {Electron injection layers} - H10K 50/854: comprising scattering means - H10K 2101/10: Triplet emission - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 Provided is an organic electroluminescence device including a pair of electrodes composed of an anode and a cathode, a light emitting layer between the electrodes and an organic layer which is adjacent to the light emitting layer between the light emitting layer and the cathode, on a substrate, the light emitting layer contains at least one compound having a carbazole structure and the organic layer adjacent to the light emitting layer contains at least one hydrocarbon compound which is composed only of carbon atoms and hydrogen atoms, has a molecular weight in a range of 400 to 1,200, and contains a condensed polycyclic structure with a total carbon number of 13 to 22. ## Claims ### Claim 1 An organic electroluminescence device, comprising: a pair of electrodes composed of an anode and a cathode; a light emitting layer between the electrodes; and an organic layer which is in contact with the light emitting layer between the light emitting layer and the cathode, on a substrate, wherein the light emitting layer comprises at least one compound represented by the following Formula (1), and the organic layer in contact with to the light emitting layer comprises at least one hydrocarbon compound which is composed only of carbon atoms and hydrogen atoms, has a molecular weight in a range of 400 to 1,200, and contains a condensed polycyclic structure with a total carbon number of 13 to 22: in Formula (1), R1 represents an alkyl group, an aryl group or a silyl group, and may further have a substituent Z, provided that R1 does not represent a carbazolyl group and a perfluoroalkyl group, in the case where R1 is present in plurality, each of a plurality of R1 may be the same or different, a plurality of R1 may be bonded to each other to form an aryl ring which may have substituent Z, each of R2 to R5 independently represents an alkyl group, an aryl group, a silyl group, a cyano group or a fluorine atom, and may further have a substituent Z, in the case where each of R2 to R5 is present in plurality, each of a plurality of R2 to R5 may be the same or different, the substituent Z represents an alkyl group, an alkenyl group, a phenyl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a group formed by combining these groups, and a plurality of the substituents Z may be bonded to each other to form an aryl ring, n1 represents an integer of 0 to 5, each of n2 to n5 independently represents an integer of 0 to 4. ### Claim 2 (depends on 1) The organic electroluminescence device according to claim 1, wherein the compound represented by Formula (1) is a compound represented by Formula (2): in Formula (2), each of R6 and R7 independently represents an alkyl group which may have a substituent Z, an aryl group which may have a substituent Z, a cyano group or a fluorine atom, in the case where each of R6 and R7 is present in plurality, each of a plurality of R6 and each of a plurality of R7 may be the same or different, a plurality of R6 and a plurality of R7 may be bonded to each other to form an aryl ring which may have a substituent Z, each of n6 and n7 independently represents an integer of 0 to 5, each of R8 to R11 independently represents a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group which may have a substituent Z, a silyl group which may have a substituent Z, a cyano group or a fluorine atom, the substituent Z represents an alkyl group, an alkenyl group, a phenyl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a group formed by combining these groups, and a plurality of substituents Z may be bonded to each other to form an aryl ring. ### Claim 3 (depends on 1) The organic electroluminescence device according to claim 1, wherein the hydrocarbon compound is a compound represented by Formula (An-1): in Formula (An-1), each of Ar1 and Ar2 independently represents an aryl group, each of R12 to R19 independently represents a hydrogen atom, an alkyl group or an aryl group, R12 and R13, R13 and R14, R14 and R15, R16 and R17, R17 and R18, and R18 and R19 may be bonded to each other to form a ring. ### Claim 4 (depends on 3) The organic electroluminescence device according to claim 3, wherein the compound represented by Formula (An-1) is a compound represented by the following Formula (An-2): in Formula (An-2), each of Ar1 and Ar2 independently represents an aryl group, each of R13, R14, R17 and R18 independently represents a hydrogen atom, an alkyl group or an aryl group, R13 and R14, and R17 and R18 may be bonded to each other to form a ring. ### Claim 5 (depends on 1) The organic electroluminescence device according to claim 1, wherein the compound represented by Formula (1) is the compound represented by Formula (2), and the hydrocarbon compound is the compound represented by Formula (An-2). ### Claim 6 (depends on 5) The organic electroluminescence device according to claim 5, wherein in formula (An-2), R13, R14, R17 and R18 represent a hydrogen atom. ### Claim 7 (depends on 1) The organic electroluminescence device according to claim 1, wherein the light emitting layer contains at least one phosphorescent light emitting material. ### Claim 8 (depends on 1) The organic electroluminescence device according to claim 1, wherein at least one layer of the light emitting layer, the organic layer in contact with the light emitting layer and other organic layers present between the anode and the cathode is formed by a solution application process. ### Claim 9 (depends on 1) The organic electroluminescence device according to claim 1, wherein the device contains a hole injection layer between the electrodes, and contains an electron accepting dopant in the hole injection layer. ### Claim 10 (depends on 1) The organic electroluminescence device according to claim 1, wherein the device contains an electron injection layer between the electrodes, and contains an electron donating dopant in the electron injection layer. ### Claim 11 (depends on 1) A light emission apparatus using the organic electroluminescence device according to claim 1. ### Claim 12 (depends on 1) A display apparatus using the organic electroluminescence device according to claim 1. ### Claim 13 (depends on 1) An illumination apparatus using the organic electroluminescence device according to claim 1. ### Claim 14 (depends on 1) The organic electroluminescence device according to claim 1, wherein the organic layer has a single layer structure, and the light emitting layer has a single layer structure. ### Claim 15 An organic electroluminescence device, comprising: a pair of electrodes composed of an anode and a cathode; a light emitting layer between the electrodes; and an organic layer which is adjacent to the light emitting layer between the light emitting layer and the cathode, on a substrate, wherein the light emitting layer comprises at least one compound represented by the following Formula (1), and the organic layer adjacent to the light emitting layer comprises at least one hydrocarbon compound which is composed only of carbon atoms and hydrogen atoms represented by Formula (An-1); in Formula (1), R1 represents an alkyl group, an aryl group or a silyl group, and may further have a substituent Z, provided that R1 does not represent a carbazolyl group and a perfluoroalkyl group, in the case where R1 is present in plurality, each of a plurality of R1 may be the same or different, a plurality of R1 may be bonded to each other to form an aryl ring which may have substituent Z, each of R2 to R5 independently represents an alkyl group, an aryl group, a silyl group, a cyano group or a fluorine atom, and may further have a substituent Z, in the case where each of R2 to R5 is present in plurality, each of a plurality of R2 to R5 may be the same or different, the substituent Z represents an alkyl group, an alkenyl group, a phenyl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a group formed by combining these groups, and a plurality of the substituents Z may be bonded to each other to form an aryl ring, n1 represents an integer of 1 to 5, each of n2 to n5 independently represents an integer of 0 to 4 in Formula (An-1), each of Ar1 and Ar2 independently represents an aryl group, each of R12 to R19 independently represents a hydrogen atom, an alkyl group or an aryl group, R12 and R13, R13 and R14, R14 and R15, R16 and R17, R17 and R18, and R18 and R19 may be bonded to each other to form a ring. ### Claim 16 (depends on 15) The organic electroluminescence device according to claim 15, wherein the organic layer has a single layer structure, and the light emitting layer has a single layer structure.