# US 11,309,511 B2 · Organic electroluminescence device and nitrogen-containing compound for 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 11,309,511 B2 - Document ID: US11309511B2 - Status: Granted - Kind: B2 - Application number: 16/453,516 - Filed: 2019-06-26 - Published: 2020-01-09 - Granted: 2022-04-19 - Earliest claimed: 2018-07-06 - Assignees: Samsung Display Co., Ltd. - Applicants: Samsung Display Co., Ltd. - Inventors: Naoya Sakamoto - Web page: https://patentgrep.com/patent/US11309511B2 ## CPC - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 50/156: {comprising a multilayered structure} - H10K 50/166: {comprising a multilayered structure} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract An organic electroluminescence device includes a first electrode, a hole transport region, an emission layer including a nitrogen-containing compound, an electron transport region, and a second electrode. The nitrogen-containing compound may include a heterocyclic moiety and two carbazole moieties, the heterocyclic moiety may be a substituted pyridine, a substituted pyrimidine, or a substituted 1,3,5-triazine, each of two carbons among carbons of 2-, 4-, and 6-positions of the substituted pyridine, the substituted pyrimidine, or the substituted 1,3,5-triazine may be substituted with a phenylene group, a carbon in an ortho position of each phenylene group may be linked with a nitrogen at a 9-position of one of the carbazole moieties, and the remaining carbon among the carbons of the 2-, 4-, and 6-positions may be substituted with a substituted or unsubstituted aromatic group, and the carbazole moieties may be linked together by a linker. ## Claims ### Claim 1 An organic electroluminescence device, comprising: a first electrode; a hole transport region on the first electrode; an emission layer on the hole transport region, the emission layer including a nitrogen-containing compound; an electron transport region on the emission layer; and a second electrode on the electron transport region, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and oxides thereof, and wherein: the nitrogen-containing compound includes a heterocyclic moiety and two carbazole moieties, the heterocyclic moiety is a substituted pyridine, a substituted pyrimidine, or a substituted 1,3,5-triazine, each of two carbons among carbons of 2-, 4-, and 6-positions of the substituted pyridine, the substituted pyrimidine, or the substituted 1,3,5-triazine is substituted with a phenylene group, a carbon in an ortho position of each phenylene group being linked with a nitrogen at a 9-position of one of the carbazole moieties, and the remaining carbon among the carbons of the 2-, 4-, and 6-positions is substituted with a substituted or unsubstituted aromatic group, and the carbazole moieties are linked together by a linker. ### Claim 2 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the aromatic group is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and the linker is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. ### Claim 3 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the aromatic group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and the linker is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. ### Claim 4 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the heterocyclic moiety is a substituted pyrimidine or a substituted 1,3,5-triazine. ### Claim 5 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the emission layer includes a host and a dopant, and the dopant includes the nitrogen-containing compound. ### Claim 6 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the nitrogen-containing compound is represented by Formula 1: the heterocyclic moiety includes Z1 to Z3, where Z1 to Z3 are each independently C-R7 or N, provided that at least one of Z1 to Z3 are N, the substituted or unsubstituted aromatic group is Ar, and Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, the linker is L, and L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, R1 to R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a, b, e and f are each independently an integer of 0 to 4, and c and d are each independently an integer of 0 to 3. ### Claim 7 (depends on 6) The organic electroluminescence device as claimed in claim 6, wherein Formula 1 is represented by any one of Formulae 1-1 to 1-3: where Z1 to Z3, Ar, L, R1 to R7 and a to f are the same as defined in Formula 1. ### Claim 8 (depends on 6) The organic electroluminescence device as claimed in claim 6, wherein Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and L is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. ### Claim 9 (depends on 6) The organic electroluminescence device as claimed in claim 6, wherein at least two of Z1 to Z3 are N. ### Claim 10 (depends on 1) The organic electroluminescence device as claimed in claim 1, wherein the nitrogen-containing compound is at least one of compounds in Compound Group 1: ### Claim 11 An organic electroluminescence device, comprising: a first electrode; a hole transport region on the first electrode; an emission layer on the hole transport region, the emission layer including a nitrogen-containing compound represented by Formula 1; and an electron transport region on the emission layer, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and oxides thereof, where Z1 to Z3 are each independently C-R7 or N, provided that at least one of Z1 to Z3 are N, Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, R1 to R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a, b, e and f are each independently an integer of 0 to 4, and c and d are each independently an integer of 0 to 3. ### Claim 12 (depends on 11) The organic electroluminescence device as claimed in claim 11, wherein Formula 1 is represented by any one of Formulae 1-1 to 1-3: where Z1 to Z3, Ar, L, R1 to R7 and a to f are the same as defined in Formula 1. ### Claim 13 (depends on 11) The organic electroluminescence device as claimed in claim 11, wherein Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and L is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. ### Claim 14 (depends on 11) The organic electroluminescence device as claimed in claim 11, wherein at least two of Z1 to Z3 are N. ### Claim 15 (depends on 11) The organic electroluminescence device as claimed in claim 11, wherein the nitrogen-containing compound is at least one of compounds in Compound Group 1: ### Claim 16 A nitrogen-containing compound represented by Formula 1: where Z1 to Z3 are each independently C-R7 or N, provided that at least one of Z1 to Z3 are N, Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, R1 to R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a, b, e and f are each independently an integer of 0 to 4, and c and d are each independently an integer of 0 to 3. ### Claim 17 (depends on 16) The nitrogen-containing compound as claimed in claim 16, wherein Formula 1 is represented by any one of Formulae 1-1 to 1-3: where Z1 to Z3, Ar, L, R1 to R7 and a to f are the same as defined in Formula 1. ### Claim 18 (depends on 16) The nitrogen-containing compound as claimed in claim 16, wherein Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and L is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group. ### Claim 19 (depends on 16) The nitrogen-containing compound as claimed in claim 16, wherein at least two of Z1 to Z3 are N. ### Claim 20 (depends on 16) The nitrogen-containing compound as claimed in claim 16, wherein the nitrogen-containing compound is at least one of compounds in Compound Group 1: