Heterocyclic compound and organic electronic element containing same

Patent metadata

Field	Value
Publication number	US-9882146-B2
Application number	US-201615087847-A
Country	US
Kind code	B2
Filing date	Mar 31, 2016
Priority date	Jul 13, 2012
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

The present disclosure provides a novel compound capable of greatly improving the lifetime, efficiency, electrochemical stability and thermal stability of an organic electronic device, and an organic electronic device including an organic compound layer containing the compound.

First claim

The invention claimed is:

1. A heterocyclic compound represented by the following formula 1:

wherein
n is 2,
X 1 to X 3 are the same or different, and are each independently a N or CH, and two of X 1 to X 3 is a N,
Ar 1 and Ar 2 are the same or different, and are each independently a substituted or unsubstituted aryl group or a heterocyclic group,
L is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted heterocyclic group having a heteroatom selected from O, N, S and P, and
Ar 3 is selected from the group consisting of a substituted or unsubstituted 2,7-naphthyl group, a substituted or unsubstituted 1,2-naphthyl group, a substituted or unsubstituted 1,3-naphthyl group, a substituted or unsubstituted 1,6-naphthyl group, a substituted or unsubstituted 1,7-naphthyl group, a substituted or unsubstituted 1,8-naphthyl group, a substituted or unsubstituted 2,3-naphthyl group, a substituted or unsubstituted 3,6-fluorenyl group and a substituted or unsubstituted 1,8-fluorenyl group,
wherein the term of substituted or unsubstituted means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, a carbazole group, a fluorenyl group, and a heterocyclic group containing at least one heteroatom selected from among N, O, S and P.

2. The heterocyclic compound of claim 1 , wherein Ar 3 is any one selected from among the following structures:

wherein a, c, d and e are each an integer ranging from 1 to 6,
b and b′ are each an integer ranging from 1 to 3,
R1 to R6 are hydrogen,
R′ and R″ are the same or different, and are each independently an unsubstituted alkyl group.

3. The heterocyclic compound of claim 1 , wherein Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted pyridine group,
wherein the term of substituted or unsubstituted means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, a carbazole group, a fluorenyl group, and a heterocyclic group containing at least one heteroatom selected from among N, O, S and P.

4. The heterocyclic compound of claim 1 , wherein L is a direct bond or a substituted or unsubstituted phenylene group.

5. The heterocyclic compound of claim 1 , wherein the compound represented by formula 1 is any one of the following compounds 2-a-1 to 2-a-5, 2-a-8 and 2-a-9:

6. The heterocyclic compound of claim 1 , wherein the compound represented by formula 1 is any one of the following compounds 2-b-1 to 2-b-5, 2-b-8 and 2-b-9:

7. The heterocyclic compound of claim 1 , wherein the compound represented by formula 1 is any one of the following compounds 2-c-1 to 2-c-5, 2-c-8 and 2-c-9:

8. The heterocyclic compound of claim 1 , wherein the compound represented by formula 1 is any one of the following compounds 2-d-1 to 2-d-5, 2-d-8 and 2-d-9:

9. The heterocyclic compound of claim 1 , wherein the compound represented by formula 1 is any one of the following compounds 2-e-1, 2-e-2, 2-e-5 and 2-e-6:

10. An organic electronic device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound of claim 1 .

11. The organic electronic device of claim 10 , wherein the organic electronic device is selected from the group consisting of an organic light-emitting device, an organic solar cell and an organic transistor.

12. The organic electronic device of claim 10 , wherein the organic electronic device is an organic light-emitting device comprising the first electrode, the second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound.

13. The organic electronic device of claim 12 , wherein the organic material layers include a hole-injecting layer or a hole-transporting layer, which comprises the heterocyclic compound.

14. The organic electronic device of claim 12 , wherein the organic material layers include a light-emitting layer comprising the heterocyclic compound as a host.

15. The organic electronic device of claim 12 , wherein the organic material layers include an electron-transporting layer comprising the heterocyclic compound.

16. The organic electronic device of claim 12 , wherein the organic material layers include, in addition to the organic material layers comprising the heterocyclic compound, a hole-injecting layer or a hole-transporting layer, which comprises an arylamino, carbazole or benzcarbazole group.

17. The organic electronic device of claim 12 , wherein the organic material layers comprising the heterocyclic compound comprise the heterocyclic compound as a host, and comprise another organic compound, a metal or a metal compound as a dopant.

18. The organic electronic device of claim 10 , wherein the organic electronic device is an organic solar cell comprising the first electrode, the second electrode and one or more organic material layers, including a photoactive layer, interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound.

19. The organic electronic device of claim 18 , wherein the organic material layers include an electron-transporting layer comprising the heterocyclic compound.

20. The organic electronic device of claim 18 , wherein the organic material layers include a photoactive layer comprising the heterocyclic compound.

21. The organic electronic device of claim 18 , wherein the organic material layers include an electron donor and an electron acceptor, wherein the electron donor or the electron acceptor comprises the heterocyclic compound.

22. The organic electronic device of claim 10 , wherein the organic ele

Assignees

• Lg Chemical Ltd

Inventors

• Lee Sangbin
• Lee Dong Hoon
• Lee Hoyong
• Kim Kongkyeom
• Jang Jungi
• Hong Sung Kil
• Shin Changhwan
• Lee Hyungjin

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C07D213/06

  containing only hydrogen and carbon atoms in addition to the ring nitrogen atom · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title