Heterocyclic compound and organic electroluminescence device including the same

Patent metadata

Field	Value
Publication number	US-10844059-B2
Application number	US-201715805012-A
Country	US
Kind code	B2
Filing date	Nov 6, 2017
Priority date	Nov 17, 2016
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

A heterocyclic compound may be represented by Formula 1. The heterocyclic compound may be included in an organic electroluminescence device. The organic electroluminescence device including the heterocyclic compound according to an embodiment of the present disclosure may attain high emission efficiency and a low driving voltage effect.

where X is O, S, NR 10 , CR 11 R 12 or SiR 13 R 14 .

First claim

What is claimed is:

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

wherein in Formula 1,
X is O, S, NR 10 , CR 11 R 12 or SiR 13 R 14 ,
R 1 to R 4 , R 6 , R 7 , and R 10 to R 14 are each independently selected from hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,
R 5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,
R 8 and R 9 are each hydrogen, and
m and n are each independently an integer of 0 to 4.

2. The heterocyclic compound of claim 1 , wherein Formula 1 is represented by the following Formula 2:

wherein in Formula 2,
definitions for X, R 2 , R 5 , R 8 , R 9 , n and m are the same as those in Formula 1.

3. The heterocyclic compound of claim 2 , wherein at least one of R 2 or R 5 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuranyl group.

4. The heterocyclic compound of claim 1 , wherein R 5 is represented by the following Formula 3:

wherein in Formula 3,
Y is O, S, NR 21 , CR 22 R 23 or SiR 24 R 25 ,
R 15 to R 25 are each independently selected from hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,
R 22 and R 24 each independently optionally form a ring by combining with R 23 and R 25 , respectively,
r is an integer of 0 to 3, and
p and q are each independently an integer of 0 to 4.

5. The heterocyclic compound of claim 4 , wherein X and Y are the same as each other.

6. The heterocyclic compound of claim 1 , wherein X is CR 11 R 12 , and
R 11 and R 12 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, wherein R 11 and R 12 optionally form a ring by combining with each other.

7. The heterocyclic compound of claim 1 , wherein X is O.

8. The heterocyclic compound of claim 1 , wherein X is S.

9. The heterocyclic compound of claim 1 , wherein X is SiR 13 R 14 , and
R 13 and R 14 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, wherein R 13 and R 14 optionally form a ring by combining with each other.

10. The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Formula 1 is any one selected from the group consisting of Compounds 2, 3, 5 to 24, 26, 27, and 29 to 32, collectively denoted as Compound Group 1:

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;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the hole transport region comprises a heterocyclic compound represented by the following Formula 1:

wherein in Formula 1,
X is O, S, NR 10 , CR 11 R 12 or SiR 13 R 14 ,
R 1 to R 4 , R 6 , R 7 , and R 10 to R 14 are each independently selected from hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,
R 8 and R 9 are each hydrogen,
R 11 and R 13 each independently optionally form a ring by combining with R 12 and R 14 , respectively, and
m and n are each independently an integer of 0 to 4.

12. The organic electroluminescence device of claim 11 , wherein the hole transport region comprises:
a hole injection layer on the first electrode; and
a hole transport layer on the hole injection layer, and
the hole transport layer comprises the heterocyclic compound represented by Formula 1.

13. The organic electroluminescence device of claim 11 , wherein Formula 1 is represented by the following Formula 2:

wherein in Formula 2,
definitions for X, R 2 , R 5 , R 8 , R 9 , n and m are the same as in Formula 1.

14. The organic electroluminescence device of claim 11 , wherein at least one of R 2 or R 5 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuranyl group.

15. The organic electroluminescence device of claim 11 , wherein R 5 is represented by the following Formula 3:

wherein in Formula 3,
Y is O, S, NR 21 , CR 22 R 23 or SiR 24 R 25 ,
R 15 to R 25 are each independently selected from hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,
R 22 and R 24 each independently optionally form a ring by combining with R 23 and R 25 , respectively,
r is an integer of 0 to 3, and
p and q are each independently an integer of 0 to 4.

16. The organic electroluminescence device of claim 11 , wherein X is CR 11 R 12 , and
R 11 and R 12 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon at

Assignees

• Samsung Display Co Ltd

Inventors

• Itoi Hiroaki

Classifications

• C07D513/06

  Peri-condensed systems · CPC title

• C07D498/06

  Peri-condensed systems · CPC title

• C07D471/06 Primary

  Peri-condensed systems · CPC title

• H10K85/656

  comprising two or more different heteroatoms per ring (H10K85/652 takes precedence) · CPC title

• H10K50/15

  Hole transporting layers · CPC title