Germanium-containing red emitter materials for organic light emitting diode

• US 8,492,006 B2
• Filed: 02/24/2011
• Issued: 07/23/2013
• Est. Priority Date: 02/24/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Xia, Chuanjun
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US13/034,057
• Publication Number:
  US 20120217868A1
• Time in Patent Office: 880 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

Organometallic compounds comprising a germanium-containing substituent are provided. The compounds may be used in organic light emitting devices to provide improved device efficiency, line shape and lifetime. In particular, the compounds comprise a phenylquinoline or phenylisoquinoline ligand having a germanium-containing substituent on the quinoline or isoquinoline portion of the ligand. These compounds may be advantageously used as red emitters in the emissive layer of organic light emitting devices.

Claims

1. A compound having the formula M(L)_x(L₁)_y(L₂)_z:

wherein the ligand L is

2. The compound of claim 1, wherein M is Ir.

3. The compound of claim 1, wherein L₂ is a monoanionic bidentate ligand.

4. The compound of claim 1, wherein L₂ is

5. The compound of claim 1, wherein Ge is directly attached to the fused carbocyclic or heterocyclic ring R.

6. The compound of claim 1, wherein the compound has the formula:

7. The compound of claim 1, wherein the compound has the formula:

8. The compound of claim 1, wherein the compound is homoleptic.

9. The compound of claim 1, wherein the compound is heteroleptic.

10. The compound of claim 1, wherein the compound is selected from the group consisting of:

11. The compound of claim 1, wherein the compound has the formula:

12. The compound of claim 11, wherein each of R′

, R″

, and R′

″

are the same.

13. The compound of claim 11, wherein each of R′

, R″

, and R′

″

is an alkyl group having 3 or less carbon atoms.

14. The compound of claim 11, wherein each of R′

, R″

, and R′

″

is different.

15. A first device, comprising an organic light emitting device further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode;

comprising a compound having the formula M(L)_x(L₁)_y(L₂)_z;

wherein the ligand L is

16. The first device of claim 15, wherein L₂ is

17. The first device of claim 15, wherein Ge is directly attached to the fused carbocyclic or heterocyclic ring R.

18. The first device of claim 15, wherein the compound has the formula:

19. The first device of claim 15, wherein the compound has the formula:

20. The first device of claim 15, wherein the compound is selected from the group consisting of:

21. The first device of claim 15, wherein the first device is a consumer product.

22. The first device of claim 15, wherein the first device is an organic light emitting device.

23. The first device of claim 15, wherein the compound has the formula:

24. The first device of claim 23, wherein each of R′

, R″

, and R′

″

are the same.

25. The first device of claim 23, wherein each of R′

, R″

, and R′

″

is an alkyl group having 3 or less carbon atoms.

26. The first device of claim 23, wherein each of R′

, R″

, and R′

″

is different.

27. The first device of claim 15, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

28. The first device of claim 27, wherein the organic layer further comprises a host.

29. The first device of claim 28, wherein the host is a compound that comprises at least one of the chemical groups selected from the group consisting of:

30. The first device of claim 28, wherein the host is a metal complex.

31. The first device of claim 30, wherein the metal complex is selected from the group consisting of:

32. The first device of claim 30, wherein the host is a metal 8-hydroxyquinolate.