Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials

• US 9,005,772 B2
• Filed: 02/23/2011
• Issued: 04/14/2015
• Est. Priority Date: 02/23/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Elshenawy, Zeinab
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US13/033,287
• Publication Number:
  US 20120212126A1
• Time in Patent Office: 1,511 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 1/005 without C-Metal linkages
• CPC Class Codes: C07F 1/08 Copper compounds
• CPC Class Codes: C07F 1/12 Gold compounds
• CPC Class Codes: C07F 13/00 Compounds containing elements of Groups 7 or 17 of the Periodic Table
• CPC Class Codes: C07F 15/002 Osmium compounds
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C07F 3/003 without C-Metal linkages
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: C07F 5/069 without C-aluminium linkages
• CPC Class Codes: C07F 7/0805 comprising only Si, C or H atoms
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 9/5022 Aromatic phosphines (P-C aromatic linkage)
• CPC Class Codes: C07F 9/5045 Complexes or chelates of phosphines with metallic compounds or metals
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• 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 50/12 : comprising dopants
• CPC Class Codes: H10K 50/15 : Hole transporting layers
• CPC Class Codes: H10K 50/16 : Electron transporting layers
• CPC Class Codes: H10K 50/17 : Carrier injection layers
• CPC Class Codes: H10K 50/171 : Electron injection layers
• CPC Class Codes: H10K 50/18 : Carrier blocking layers
• CPC Class Codes: H10K 50/81 : Anodes
• CPC Class Codes: H10K 50/82 : Cathodes
• CPC Class Codes: H10K 50/844 : Encapsulations
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/348 : comprising osmium
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

Compounds are provided that comprise a heterocyclic carbene ligand. In particular, an oxazole or a thioazole carbene are used in place of the traditional imidazole carbene. These compounds may be used in OLEDs to provide devices having improved properties, such as stability and color-tuning. Additionally, a novel methodology to synthesize heterocyclic carbene metal complexes is provided.

Claims

1. A compound comprising a ligand having the structure:

2. The compound of claim 1, wherein A is benzene.

3. The compound of claim 1, wherein the ligand L has the formula:

4. The compound of claim 1, wherein the ligand L has the formula:

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

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

24. The compound of claim 1, wherein R_A represents a mono substitution of the A ring at a position ortho to the A ring carbon that coordinates to Os.

7. A first device comprising an organic light emitting device 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 structure;

8. The first device of claim 7, wherein A is benzene.

9. The first device of claim 7, wherein the ligand L has the formula:

10. The first device of claim 7, wherein the ligand L has the formula:

11. The first device of claim 7, wherein the compound is selected from the group consisting of:

12. The first device of claim 7, wherein the compound is selected from the group consisting of:

13. The first device of claim 7, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

14. The first device of claim 13, wherein the organic layer further comprises a host.

15. The first device of claim 14, wherein the host is a compound that comprises at least one of the chemical groups selected from the group consisting of:

16. The first device of claim 14, wherein the host is a metal complex.

17. The first device of claim 16, wherein the metal complex is selected from the group consisting of:

18. The first device of claim 7, wherein the first device is a consumer product.

25. The first device of claim 7, wherein R_A represents a mono substitution of the A ring at a position ortho to the A ring carbon that coordinates to Os.

19. A process for making a carbene metal complex, comprising:

reacting a copper chloride carbene complex with an osmium precursor to yield the carbene metal complex comprising a ligand L having the structure;

20. The process of claim 19, further comprising reacting a carbene salt with copper-t-butoxide to yield a copper chloride carbene complex, prior to reacting the copper chloride carbene complex with the osmium precursor.

21. The process of claim 19, wherein the osmium precursor is OsCl₂(DMSO)₄.

22. The process of claim 19, wherein X is S.

23. The process of claim 19, wherein X is O.