Deuterated compounds for electronic applications

Patent metadata

Field	Value
Publication number	US-9577199-B2
Application number	US-201414509757-A
Country	US
Kind code	B2
Filing date	Oct 8, 2014
Priority date	Feb 27, 2009
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

This invention relates to deuterated aryl-anthracene compounds that are useful in electronic applications. It also relates to electronic devices in which the active layer includes such a deuterated compound.

First claim

What is claimed is:

1. An aryl-substituted anthracene compound having Formula I:

wherein:
R 1 through R 8 are the same or different at each occurrence and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, siloxane, and silyl;
Ar 1 and Ar 2 are the same or different and are selected from the group consisting of aryl groups; and
Ar 3 and Ar 4 are the same or different and are selected from the group consisting of H, D, and aryl groups;

wherein the compound has at least eight D.

2. The compound of claim 1 which is at least 10% deuterated.

3. The compound of claim 1 which is at least 50% deuterated.

4. The compound of claim 1 which is 100% deuterated.

5. The compound of claim 1 wherein the at least one D is on a substituent group on an aryl ring.

6. The compound of claim 1 wherein at least one of R 1 through R 6 is D.

7. The compound of claim 1 , wherein R 1 through R 6 are selected from H and D.

8. The compound of claim 1 wherein at least one of R 1 through R 8 is selected from alkyl, alkoxy, aryl, aryloxy, siloxane, and silyl, and the remainder of R 1 through R 8 are selected from H and D.

9. The compound of claim 8 wherein R 2 is selected from alkyl and aryl.

10. The compound of claim 1 , wherein at least one of Ar 1 through Ar 4 is a deuterated aryl.

11. The compound of claim 1 , wherein Ar 3 and Ar 4 are selected from D and deuterated aryls.

12. The compound of claim 1 , wherein Ar 1 through Ar 4 are at least 20% deuterated.

13. The compound of claim 1 wherein Ar 1 and Ar 2 are selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, and deuterated derivatives thereof.

14. The compound of claim 5 wherein Ar 3 and Ar 4 are selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenylnaphthylene, naphthylphenylene, deuterated derivatives thereof and a group having Formula II:

where:
R 9 is the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, alkoxy, siloxane and silyl, or adjacent R 9 groups may be joined together to form an aromatic ring; and
m is the same or different at occurrence and is an integer from 1 to 6.

15. The compound of claim 1 wherein Ar 3 and Ar 4 are selected from the group consisting of phenyl, naphthyl, phenylnaphthylene, naphthylphenylene, deuterated derivatives thereof, and a group having Formula III:

where:
R 9 the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, alkoxy, siloxane and silyl, or adjacent R 9 groups may be joined together to form an aromatic ring; and
m is the same or different at each occurrence and is an integer from 1 to 6.

16. The compound of claim 1 wherein at least one of Ar 1 through Ar 4 is a heteroaryl group.

17. The compound of claim 16 wherein the heteroaryl group is selected from carbazole, benzofuran, and dibenzofuran.

18. The compound of claim 1 wherein at least one of R 1 through R 8 is D and at least one of Ar 1 through Ar 4 is a deuterated aryl.

19. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and at least one active layer therebetween, wherein the active layer comprises an aryl-substituted anthracene compound having Formula I:

wherein:
R 1 through R 8 are the same or different at each occurrence and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, siloxane, and silyl;
Ar 1 and Ar 2 are the same or different and are selected from the group consisting of aryl groups; and
Ar 3 and Ar 4 are the same or different and are selected from the group consisting of H, D, and aryl groups;
wherein the compound has at least eight D.

20. The device of claim 19 wherein the active layer is an electroactive layer which further comprises an electroactive dopant compound.

21. The device of claim 19 wherein the active layer is an electroactive layer and consists essentially of a compound having Formula I and an electroactive dopant compound.

22. The device of claim 19 wherein the active layer is an electroactive layer and consists essentially of a compound having Formula I, a second host material, and an electroactive dopant compound.

23. The device of claim 20 wherein the electroluminescent compound is selected from the group consisting of amino-substituted chrysenes and amino-substituted anthracenes.

24. The device of claim 22 further comprising a hole injection layer between the first electrical contact layer and the active layer.

25. The device of claim 24 wherein the hole injection layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.

Assignees

• Du Pont
• E I Du Pont Nemours And Company

Inventors

• Lecloux Daniel David
• Fennimore Adam
• Gao Weiying
• Radu Nora Sabina
• Wu Weishi
• Rostovtsev Vsevolod
• Howard Jr Michael Henry
• Meng Hong
• Shen Yulong
• Merlo Jeffrey A
• Smith Eric Maurice

Classifications

• H01L51/006

  Electricity · mapped topic

• H01L51/5036

  Electricity · mapped topic

• H01L51/0058 Primary

  Electricity · mapped topic

• H01L51/0005

  Electricity · mapped topic

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title