Phosphorescent materials

• US 9,076,973 B2
• Filed: 08/16/2013
• Issued: 07/07/2015
• Est. Priority Date: 09/03/2008
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Alleyne, Bert, Kwong, Raymond C., Fiordeliso, James, Weaver, Michael S., Ansari, Nasrin, DeAngelis, Alan, Rayabarapu, Dinesh, Adamovich, Vadim
• Primary Examiner(s): Ho, Anthony
• Application Number:
  US13/968,551
• Publication Number:
  US 20140021449A1
• Time in Patent Office: 690 Days
• Field of Search: 257/40, 257/E51.001
• 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 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1066 with sulfur
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• 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 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

Claims

1. A compound comprising a ligand L having the structure:

2. The compound of claim 1, wherein only one of R₁, R₂, and the R_a substituents is not hydrogen.

3. The compound of claim 1, wherein only one of R₁, R₂, and the R_a substituents is alkyl.

4. The compound of claim 1, wherein only one of R₁, R₂, and the R_a substituents is ethyl.

5. The compound of claim 1, wherein only one of R₁, R₂, and the R_a substituents is methyl.

6. The compound of claim 1, wherein the compound has the structure:

7. The compound of claim 6, wherein the metal M is Ir.

8. The compound of claim 6, wherein only one of R₁, R₂, and the R_a substituents adjacent to C is not hydrogen.

9. The compound of claim 6, wherein only one of R₁, R₂, and the R_a substituents adjacent to C is alkyl.

10. The compound of claim 6, wherein only one of R₁, R₂, and the R_a substituents adjacent to C is ethyl.

11. The compound of claim 6, wherein only one of R₁, R₂, and the R_a substituents adjacent to C is methyl.

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

13. The compound of claim 12, wherein R is an alkyl.

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

15. The compound of claim 9, wherein the alkyl is on the pyridine ring.

16. The compound of claim 9, wherein the alkyl is para to the nitrogen of the pyridine ring.

17. An organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer further comprising a compound having the formula;

18. A heteroleptic complex having the formula Ir(L_A-B)₂(L_C-D),

wherein L_A-B is

19. The compound of claim 18, wherein L_C-D is selected from the group consisting of:

20. The compound of claim 18, wherein the compound is: