IP Library Granted Patent US 10,686,139
Granted Patent B2
US 10,686,139 · App. 15/378,084 · Granted Jun 16, 2020

Nitrogen-containing compound and organic electroluminescence device including the same

Inventors: Hiromi Nakano (Yokohama, JP); Shuri Sato (Yokohama, JP); Yoshimasa Fujita (Yokohama, JP); Nobutaka Akashi (Yokohama, JP); Takuma Yasuda (Fukuoka, JP); Inseob Park (Fukuoka, JP)
Assignees: Samsung Display Co., Ltd.; Kyushu University, National University Corporation
H01L51/0067C07D401/10C07D401/14C07D403/14C07D491/107C09K11/06H01L51/0071H01L51/0072C09K2211/1007C09K2211/1044H01L51/5016H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 10,686,139
App. No.
15/378,084
Granted
Jun 16, 2020
Kind
B2
Abstract

A nitrogen-containing compound and an organic electroluminescence device including the same, the nitrogen-containing compound being represented by the following Formula 1:

Claims (60)

1. A nitrogen-containing compound represented by the following Formula 1:

wherein, in Formula 1,

X 1 to X 6 are each independently CR 1 or N, provided that one or two of X 1 to X 6 are N and the others are CR 1 ,

each R 1 is independently a bond to L, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 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,

L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

n is 1 or 2, and

when only one of X 1 to X 6 is N, Du is a group represented by one selected from the following Formulae 8 to 9 and 13 to 16, and

when only two of X 1 to X 6 are N, Du is a group represented by one selected from the following Formulae 7 to 9 and 12 to 16,

wherein, in Formulae 7 to 9 and 12 to 16,

represents a bonding site with L of Formula 1.

2. The nitrogen-containing compound as claimed in claim 1 , wherein L is a substituted or unsubstituted phenylene group.

3. The nitrogen-containing compound as claimed in claim 1 , wherein the nitrogen-containing compound represented by Formula 1 is represented by the following Formula 3:

wherein, in Formula 3, L, Du, R 1 , and n are defined the same as those of Formula 1.

4. The nitrogen-containing compound as claimed in claim 1 , wherein the nitrogen-containing compound represented by Formula 1 is represented by the following Formula 4:

wherein, in Formula 4, L, Du, R 1 , and n are defined the same as those of Formula 1.

5. The nitrogen-containing compound as claimed in claim 1 , wherein the nitrogen-containing compound represented by Formula 1 is represented by the following Formula 5:

wherein, in Formula 5, L, Du, R 1 , and n are defined the same as those of Formula 1.

6. A nitrogen-containing compound, wherein the nitrogen-containing compound is one of the following Compounds:

7. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the emission layer includes a host and a dopant, the dopant being included in an amount less than that of the host and being a nitrogen-containing compound represented by the following Formula 1:

wherein, in Formula 1,

X 1 to X 6 are each independently CR 1 or N provided that one or two of X 1 to X 6 are N and the others are CR 1 ,

each R 1 is independently a bond to L, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 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,

L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

n is 1 or 2, and

Du is a group represented by one selected from the following Formulae 7-9 and 12-16, when only one of X 1 to X 6 is N, Du is a group represented by the following Formulae 8 to 9 and 13 to 16, and

when only two of X 1 to X 6 are N, Du is a group represented by one selected from the following Formulae 7 to 9 and 12 to 16,

wherein, in Formulae 7-9 and 12-16,

represents a bonding site with L of Formula 1, or

the nitrogen-containing compound is represented by the following Formula 5:

wherein, in Formula 5, L, Du, R 1 , and n are defined the same as those of Formula 1.

8. The organic electroluminescence device as claimed in claim 7 , wherein an absolute value of a difference between a singlet energy level and a triplet energy level of the nitrogen-containing compound represented by Formula 1 or a triplet energy level of the nitrogen-containing compound represented by Formula 5 is about 0.2 eV or less.

9. The organic electroluminescence device as claimed in claim 7 , wherein L is a substituted or unsubstituted phenylene group.

10. The organic electroluminescence device as claimed in claim 7 , wherein the nitrogen-containing compound represented by Formula 1 is represented by the following Formula 3:

wherein, in Formula 3, L, Du, R 1 , and n are defined the same as those of Formula 1.

11. The organic electroluminescence device as claimed in claim 7 , wherein the nitrogen-containing compound represented by Formula 1 is represented by the following Formula 4:

wherein, in Formula 4, L, Du, R 1 , and n are defined the same as those of Formula 1.

12. The organic electroluminescence device as claimed in claim 7 , wherein the nitrogen-containing compound is represented by the following Formula 6:

wherein, in Formula 6,

R 12 is a hydrogen atom, or substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and

X 1 to X 6 are defined the same as those of Formula 1.

13. The organic electroluminescence device as claimed in claim 7 , wherein the nitrogen-containing compound represented by Formula 1 is one of the following Compounds:

14. The organic electroluminescence device as claimed in claim 7 , wherein:

the hole transport region includes a hole injection layer and a hole transport layer, and

the electron transport region includes an electron injection layer and an electron transport layer.

15. A nitrogen-containing compound represented by one of the following Compounds 53, 55, 61, 66, 67, 69, 70, or 71:

16. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the emission layer includes the nitrogen-containing compound as claimed in claim 15 .

17. The organic electroluminescence device as claimed in claim 16 , wherein an absolute value of a difference between a singlet energy level and a triplet energy level of the nitrogen-containing compound is about 0.2 eV or less.

18. The organic electroluminescence device as claimed in claim 16 , wherein the nitrogen containing compound is a dopant in the emission layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2016
From: NAKANO, HIROMI; SATO, SHURI; FUJITA, YOSHIMASA; AKASHI, NOBUTAKA; YASUDA, TAKUMA; PARK, INSEOB
To: SAMSUNG DISPLAY CO., LTD.; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION
Reel/Frame 040729/0041 →
Priority Claims (1)
KR 10-2016-0065045 · May 26, 2016 · national
Continuity (1)
Related Publication 20170346017A1 · Nov 30, 2017