Carbene containing metal complexes as OLEDs

• US 7,956,192 B2
• Filed: 08/18/2009
• Issued: 06/07/2011
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation, University of Southern California
• Original Assignee: Universal Display Corporation, University of Southern California
• Inventors: Tsai, Jui-Yi, Barone, Michael S., Tamayo, Arnold, Thompson, Mark E.
• Primary Examiner(s): NAZARIO GONZALEZ, PORFIRIO
• Application Number:
  US12/543,057
• Publication Number:
  US 20090302754A1
• Time in Patent Office: 658 Days
• Field of Search: 556/136, 548/103, 546/4, 546/2, 313/504
• US Class Current: 548/103
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• 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

A process for preparing a compound having the formula L₂IrL′ is provided. The process comprises:

combining

and L′ in the presence of an organic solvent to form a mixture, wherein L is a suitable carbene ligand precursor coordinated to Ir; and L′ is a bidentate ligand or two monodentate ligands, and L is different from L′;

Also provided is a process for preparing a compound having the formula

The process comprises:

• • (a) combining L, a carbene ligand precursor, with an organic solvent;
  • (b) maintaining the mixture of step (a) at a temperature from about 175° C. to less than the boiling point of the organic solvent in (a).

A process for preparing a compound with the formula L₃Ir is also provided. This process comprises combining

and L in the presence of alcohol and a base to form a mixture, wherein L is a bidentate ligand that may form a five-membered chelate ring.

Claims

1. A compound, having the structure:

2. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having the formula;

3. A compound having the formula:

4. The compound of claim 3, wherein L has the structure:

5. The compound of claim 4, wherein L has the structure:

6. The compound of claim 5, wherein L has the structure:

14. The compound of claim 3, wherein the carbene carbon is between two adjacent heteroatoms.

15. The compound of claim 14, wherein the two adjacent heteroatoms are both nitrogen.

16. The compound of claim 15, wherein the carbene ligand includes an imidazole ring, and wherein the carbene carbon and the two adjacent nitrogen atoms are part of the imidazole ring.

7. A process for preparing a compound having the formula

8. The process of claim 7, wherein the temperature at (b) is at least about 185°

C.

9. A process for preparing a compound with the formula L₃Ir, wherein L is a bidentate ligand and L forms a five-membered metal chelate ring, comprising:

(a) combining

10. The process of claim 9, wherein L has the structure:

11. The process of claim 10, wherein L has the structure:

12. The process of claim 11, wherein L has the structure:

13. A compound selected from the group consisting of: