3-coordinate copper(I)-carbene complexes

• US 8,580,394 B2
• Filed: 11/17/2010
• Issued: 11/12/2013
• Est. Priority Date: 11/19/2009
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: Universal Display Corporation
• Inventors: Thompson, Mark, Djurovich, Peter, Krylova, Valentina
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US12/948,396
• Publication Number:
  US 20120056529A1
• Time in Patent Office: 1,091 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 1/08 Copper compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/371 Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver

Abstract

Novel phosphorescent trigonal copper carbene complexes are provided. The complex comprise a carbene ligand coordinated to a three coordinate copper atom. The complex may be used in organic light emitting devices. In particular, the complexes may be especially useful in OLEDs used for lighting applications.

Claims

1. A phosphorescent complex comprising a carbene ligand coordinate a three coordinate copper atom, wherein the phosphorescent complex has the formula:

2. The complex of claim 1, wherein each of X₁ and X₂ independently forms a bond with *C;

wherein a first bond is formed between *C and an atom X′

₁ in substituent X₁;

wherein a second bond is formed between *C and an atom X′

₂ in substituent X₂; and

wherein X′

₁ and X′

₂ are independently selected from the group consisting of C, N, O, S and P.

3. The complex of claim 1, wherein the complex has the formula:

4. The complex of claim 3, wherein Y₁-Y₂ is selected from the group consisting of:

5. The complex of claim 3, wherein Y₁-Y₂ is selected from the group consisting of:

6. The complex of claim 1, wherein Y₁-Y₂ is/are an unconjugated, monoanionic ligand containing BY₄⁻

, SO₃Y⁻

, CY₄³¹, SiO₄³¹, OY₂⁻

, or SY₂⁻

, and wherein each Y is independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl.

7. The complex of claim 6, wherein ligand Y₁-Y₂ comprises two monodentate ligands, one of which is BY₄⁻

.

8. The complex of claim 7, wherein ligand Y₁-Y₂ has the formula:

9. The complex of claim 6, wherein Y₁-Y₂ is a bidentate ligand having the formula BY₄⁻

.

10. The complex of claim 9, wherein the ligand Y₁-Y₂ is selected from the group consisting of:

11. The complex of claim 6, wherein Y₁-Y₂ is selected from the group consisting of:

12. The complex of claim 1, wherein the complex comprises two copper (I) centers.

13. The complex of claim 1, wherein the carbene ligand is selected from the group consisting of:

14. The complex of claim 1, wherein the complex is selected from the group consisting of:

15. The complex of claim 1, wherein the complex has the formula:

16. The complex of claim 15, wherein a Cu—

Y₁-Y₂ structure of the complex is selected from the group consisting of;

17. The complex of claim 1, wherein the carbene ligand is bidentate.

18. The complex of claim 17, wherein the complex is selected from the group consisting of:

19. The complex of claim 1, wherein the complex is included in a polymer, a dendritic complex, or a small molecule.

20. A phosphorescent complex selected from the group consisting of:

21. 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, the organic layer further comprising a phosphorescent complex itself comprising a three coordinate copper atom and a carbene ligand, wherein phosphorescent complex has the formula;

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

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