5-substituted 2 phenylquinoline complexes materials for light emitting diode

• US 9,130,177 B2
• Filed: 01/13/2011
• Issued: 09/08/2015
• Est. Priority Date: 01/13/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, DeAngelis, Alan, Xia, Chuanjun, Adamovich, Vadim
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US13/006,016
• Publication Number:
  US 20120181511A1
• Time in Patent Office: 1,699 Days
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• 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
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Compounds are provided that comprise a ligand having a 5-substituted 2-phenylquinoline. In particular, the 2-phenylquinoline may be substituted with a bulky alkyl at the 5-position. These compounds may be used in organic light emitting devices, in particular as red emitters in the emissive layer of such devices, to provide devices having improved properties.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein each of R₁ and R₃ are a branched alkyl with branching at a position further than the α

position to the carbonyl group.

3. The compound of claim 1, wherein each of R₅, R₆ and R₇ are independently selected from methyl and hydrogen, and at least one of R₅, R₆ and R₇ is methyl.

4. The compound of claim 1, wherein each of R₅ and R₇ are methyl, and R₆ is hydrogen.

5. The compound of claim 1, wherein each of R₅ and R₆ are methyl, and R₇ is hydrogen.

6. The compound of claim 1, wherein each of R₅, R₆ and R₇ are methyl.

7. The compound of claim 1, wherein R₄ is isobutyl.

8. The compound of claim 1, wherein R₄ is isopropyl.

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

10. The compound of claim 1, wherein each of R₁, R₂, R₃, R₅, R₆ and R₇ is independently selected from the group consisting of hydrogen, deuterium, and alkyl.

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

12. The composition of claim 1, wherein the compound is

13. The compound of claim 1, wherein R₄ is t-butyl.

14. 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 comprising a ligand L having the formula;

15. The first device of claim 14, wherein the compound is selected from the group consisting of:

16. The first device of claim 14, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

17. The first device of claim 16, wherein the organic layer further comprises a host.

18. The first device of claim 17, wherein the host is a metal 8-hydroxyquinolate.

19. The first device of claim 18, wherein the host is:

20. The first device of claim 14, wherein the first device is a consumer product.

21. The first device of claim 14, wherein the first device is an organic light emitting device.

22. A compound comprising a ligand L having the formula:

23. The compound of claim 22, wherein R_B is amino.

24. The compound of claim 22, wherein R_B is silyl.

25. The compound of claim 22, wherein the compound has a structure according to Formula III:

26. The compound of claim 22, wherein the compound is selected from the group consisting of: