Organic compound and organic light emitting diode device including the same

Patent metadata

Field	Value
Publication number	US-9647216-B2
Application number	US-201414340474-A
Country	US
Kind code	B2
Filing date	Jul 24, 2014
Priority date	Feb 25, 2014
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

A novel organic compound and an organic light emitting diode device using the same. The organic compound is represented by Chemical Formula 1:

The organic compounds can provide improved electrical stability, high charge transport capability, a high glass transition temperature and may be capable of preventing crystallization. Also disclosed is an organic light emitting diode device including the compound of Chemical Formula 1 in the organic layer.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:
Chemical Formula 1

wherein
R 1 to R 5 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amine group, a substituted or unsubstituted silyl group, a cyano group, a nitro group, a hydroxy group, a carboxyl group, or a combination thereof,
L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
k is an integer from 0 to 2, l is an integer from 1 to 3, m is an integer from 0 to 2, and n, o, and p are each independently integers from 0 to 4, and o and p are not simultaneously 0.

2. The compound of claim 1 , wherein at least one of R 4 and R 5 is a substituted or unsubstituted C1 to C30 amine group.

3. The compound of claim 1 , wherein at least one of R 4 and R 5 is a C1 to C30 amine group substituted with an aryl group.

4. The compound of claim 1 , wherein m is 0.

5. The compound of claim 1 , wherein R 1 and R 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C1 to C30 amine group.

6. The compound of claim 1 , wherein R 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinolinyl group.

7. The compound of claim 1 , wherein L is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group.

8. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 comprises at least one selected from Compounds 1-52:

9. An organic light emitting diode device comprising
an anode;
a cathode; and
an organic layer between the anode and the cathode, the organic layer comprising a compound represented by Chemical Formula 1:

Chemical Formula 1

wherein
R 1 to R 5 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amine group, a substituted or unsubstituted silyl group, a cyano group, a nitro group, a hydroxy group, a carboxyl group, or a combination thereof,
L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
k is an integer from 0 to 2, l is an integer from 1 to 3, m is an integer from 0 to 2, and n, o, and p are each independently integers from 0 to 4, and o and p are not simultaneously 0.

10. The organic light emitting diode device of claim 9 , wherein the organic layer comprises at least one selected from an electron injection layer (EIL), an electron transport layer (ETL), a hole injection layer (HIL), a hole transport layer (HTL), or an emission layer.

11. The organic light emitting diode device of claim 9 , wherein the organic layer comprises an electron injection layer (EIL) or an electron transport layer (ETL).

12. The organic light emitting diode device of claim 11 , wherein the electron transport layer (ETL) comprises an electron transporting organic material and a metal-containing material.

13. The organic light emitting diode device of claim 12 , wherein the metal-containing material is a Li complex.

14. The organic light emitting diode device of claim 9 , wherein the organic layer comprises an emission layer.

15. The organic light emitting diode device of claim 9 , wherein the compound is a host in the emission layer.

16. The organic light emitting diode device of claim 9 , wherein the organic layer comp

Assignees

• Samsung Display Co Ltd
• Pusan Nat Univ Industry-Univ Coop Found

Inventors

• Kim Jae Hong
• Suh Hong Suk
• Kim Myeong Suk
• Kim Sung Wook
• Lee Moon Jae

Classifications

• H01L51/0085

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic

• H01L51/0081

  Electricity · mapped topic