Carbene containing metal complexes as OLEDs

• US 20050258742A1
• Filed: 01/10/2005
• Published: 11/24/2005
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation, University of Southern California
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Yui-Yi, Thompson, Mark E., Barone, Michael S., Tamayo, Arnold
• Granted Patent: US 7,598,388 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• 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 process for preparing a compound having the formula L₂IrL′

comprising;

(a) combining

and L′

in the presence of an organic solvent to form a mixture,

wherein L is a carbene ligand coordinated to Ir; and

L′

is a bidentate ligand or two monodentate ligands, and L is different from L′

;

(b) maintaining the mixture for sufficient time to obtain L₂IrL′

;

(c) recovering L₂IrL′

from the mixture.

2. The process of claim 1, wherein L has the structure

3. The process of claim 2, wherein L has the structure:

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

5. A compound, having the structure:

6. 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;

7. A compound having the formula:

8. The compound of claim 7, wherein L has the structure:

9. The compound of claim 8, wherein L has the structure:

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

11. A process for preparing a compound having the formula

12. The process of claim 11, wherein the temperature at (b) is at least about 185°

C.

13. 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

and L in the presence of alcohol and a base to form a mixture;

(b) maintaining the mixture for sufficient time to obtain L₃Ir; and

(c) recovering L₃Ir from the mixture.

14. The process of claim 13, wherein L has the structure:

15. The process of claim 14, wherein L has the structure:

16. The process of claim 15, wherein L has the structure:

17. A compound L₃Ir selected from the group consisting of: