# US 8,541,111 B2 · Organic electroluminescent device and display apparatus > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,111 B2 - Document ID: US8541111B2 - Status: Granted - Kind: B2 - Application number: 12/117,544 - Filed: 2008-05-08 - Published: 2008-11-27 - Granted: 2013-09-24 - Earliest claimed: 2007-05-21 - Assignees: Sony Corporation - Applicants: Emiko Kambe; Shigeyuki Matsunami; Yasunori Kijima - Inventors: Emiko Kambe; Shigeyuki Matsunami; Yasunori Kijima - Web page: https://patentgrep.com/patent/US8541111B2 ## CPC - H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons} - H10K 85/623: {containing five rings, e.g. pentacene} - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/14: Carrier transporting layers - H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene} - H10K 85/114: {Poly-phenylenevinylene; Derivatives thereof} - H10K 85/146: {poly N-vinylcarbazol; Derivatives thereof} - H10K 85/30: Coordination compounds - H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene - H10K 85/611: {Charge transfer complexes} - H10K 85/622: {containing four rings, e.g. pyrene} - H10K 85/6565: {Oxadiazole compounds} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract A red light-emitting organic electroluminescent device is provided and includes an anode; a cathode; and an organic layer which includes a light-emitting layer and is interposed between the anode and cathode. The light-emitting layer includes a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound whose mother skeleton has a ring member number of from four to seven. The organic electroluminescent device also includes an electron transport layer containing a benzimidazole derivative provided adjacent to the light-emitting layer. ## Claims ### Claim 1 A red light-emitting organic electroluminescent device comprising: an anode; a cathode; an organic layer which includes a light-emitting layer and is interposed between the anode and cathode, the light-emitting layer including a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound with a mother skeleton having a ring member number of from four to seven; and an electron transport layer including a benzimidazole derivative represented by the following general formula (1) provided adjacent to the light-emitting layer wherein A1 represents a hydrogen atom, a substituted or unsubstituted aryl group having not more than sixty carbon atoms, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms; A2 represents a hydrogen atom, an unsubstituted aryl group having not more than sixty carbon atoms, an unsubstituted heterocyclic group, an unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms; B represents a substituted or unsubstituted arylene group having not more than sixty carbon atoms, a pyridinylene group which may have a substituted or unsubstituted group, a quinolinylene group which may have a substituent or a fluorenylene group which may have a substituent; and Ar represents a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or a substituted or unsubstituted alkoxy group having from one to twenty carbon atoms. ### Claim 2 (depends on 1) The organic electroluminescent device according to claim 1, wherein the mother skeleton of the polycyclic aromatic hydrocarbon compound which configures the host material of the light-emitting layer is selected from the group consisting of pyrene, benzopyrene, chrysene, naphthacene, benzonaphthacene, dibenzonaphthacene, perylene and coronene. ### Claim 3 (depends on 1) The organic electroluminescent device according to claim 1, wherein a compound represented by the following general formula (2) is used as the host material of the light-emitting layer: wherein R1 to R8 each independently represents hydrogen, a halogen, a hydroxyl group, a substituted or unsubstituted carbonyl group having not more than twenty carbon atoms, a substituted or unsubstituted carbonyl ester group having not more than twenty carbon atoms, a substituted or unsubstituted alkyl group having not more than twenty carbon atoms, a substituted or unsubstituted alkenyl group having not more than twenty carbon atoms, a substituted or unsubstituted alkoxyl group having not more than twenty carbon atoms, a cyano group, a nitro group, a substituted or unsubstituted silyl group having not more than thirty carbon atoms, a substituted or unsubstituted aryl group having not more than thirty carbon atoms, a substituted or unsubstituted heterocyclic group having not more than thirty carbon atoms or a substituted or unsubstituted amino group having not more than thirty carbon atoms. ### Claim 4 (depends on 1) The organic electroluminescent device according to claim 1, wherein the electron transport layer has a stack structure including a plurality of layers. ### Claim 5 (depends on 1) The organic electroluminescent device according to claim 1, wherein the electron transport layer has a layer formed by subjecting plural kinds of the benzimidazole derivative to simultaneous vapor deposition. ### Claim 6 A display apparatus comprising: a substrate; and a plural number of red light-emitting organic electroluminescent devices provided on the substrate and including an anode, a cathode, an organic layer which includes a light-emitting layer and is interposed between the anode and cathode, the light-emitting layer including a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound whose mother skeleton has a ring member number of from four to seven; and an electron transport layer containing a benzimidazole derivative represented by the following general formula (1) provided adjacent to the light-emitting layer wherein A1 represents a hydrogen atom, a substituted or unsubstituted aryl group having not more than sixty carbon atoms, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms; A2 represents a hydrogen atom, an unsubstituted aryl group having not more than sixty carbon atoms, an unsubstituted heterocyclic group, an unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms; B represents a substituted or unsubstituted arylene group having not more than sixty carbon atoms, a pyridinylene group which may have a substituted or unsubstituted group, a quinolinylene group which may have a substituent or a fluorenylene group which may have a substituent; and Ar represents a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or a substituted or unsubstituted alkoxy group having from one to twenty carbon atoms. ### Claim 7 (depends on 6) The display apparatus according to claim 6, wherein the organic electroluminescent device is provided as a red light-emitting device in a part of plural pixels. ### Claim 8 (depends on 6) The display apparatus according to claim 6, wherein a blue light-emitting, organic electroluminescent device and a green light-emitting, organic electroluminescent device are provided together with the red light-emitting device on the substrate. ### Claim 9 (depends on 1) The organic electroluminescent device according to claim 1, wherein the guest material is represented by the following formula (106) ### Claim 10 (depends on 1) The organic electroluminescent device according to claim 1, wherein the guest material is represented by the following formula (107) ### Claim 11 (depends on 1) The organic electroluminescent device according to claim 1, wherein the guest material is represented by the following formula (108) ### Claim 12 (depends on 1) The organic electroluminescent device according to claim 1, wherein the guest material is represented by the following formula (109) ### Claim 13 (depends on 1) The organic electroluminescent device according to claim 1, wherein the host material is represented by the following formula (103)