Deuterated compounds for electronic applications
View Patent ↗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.
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 one 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 8 is D.
7. The compound of claim 1 , wherein R 1 through R 8 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 each 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 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 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 one 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.
26. 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 and D;
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 one D.
27. 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 and D;
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 one D.
28. The aryl-substituted anthracene compound of claim 1 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, and aryloxy and which is at least 10% deuterated.