Organic electroluminescent materials and devices

• US 9,359,549 B2
• Filed: 04/06/2010
• Issued: 06/07/2016
• Est. Priority Date: 04/06/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Rayabarapu, Dinesh, Xia, Chuanjun, Kwong, Raymond C., Ma, Bin, Yeager, Walter, Alleyne, Bert
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US13/263,294
• Publication Number:
  US 20120061654A1
• Time in Patent Office: 2,254 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 2211/1033 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: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• 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

Compounds comprising a metal complex having novel ligands are provided. In particular, the compound is an iridium complex comprising novel aza DBX ligands. The compounds may be used in organic light emitting devices, particularly as emitting dopants, providing improved efficiency, low operating voltage, and long lifetime.

Claims

1. A compound having the structure of formula (L)_n(L′

)_3-nIr, wherein n is 1 or 2, ligand L has a structure

2. The compound of claim 1, wherein ligand L′

is

3. The compound of claim 2, wherein the compound is selected from the group consisting of:

4. The compound of claim 1, wherein X is O.

5. The compound of claim 1, wherein X is S.

6. The compound of claim 1, wherein X is CRR′

.

7. The compound of claim 1, wherein X is CO.

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

9. The compound of claim 8, wherein the compound is selected from the group consisting of Compound 1-Compound 12.

10. The compound of claim 8, wherein the compound is selected from the group consisting of Compound 13-Compound 24.

11. The compound of claim 8, wherein the compound is selected from the group consisting of Compound 37-Compound 48.

12. The compound of claim 8, wherein the compound is selected from the group consisting of Compound 49-Compound 60.

13. An organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of formula (L)_n(L′

)_3-nIr, wherein n is 1 or 2, ligand L has a structure

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

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

16. The device of claim 15, wherein the host has the formula:

17. The device of claim 13, wherein the compound is selected from the group consisting of: