Methods of making bis-tridentate carbene complexes of ruthenium and osmium

• US 8,754,232 B2
• Filed: 09/13/2013
• Issued: 06/17/2014
• Est. Priority Date: 02/23/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/026,408
• Publication Number:
  US 20140021453A1
• Time in Patent Office: 277 Days
• Field of Search: 546/10, 548/103, 548/108, 313/498
• US Class Current: 548/103
• CPC Class Codes: C07F 1/005 without C-Metal linkages
• CPC Class Codes: C07F 1/12 Gold compounds
• CPC Class Codes: C07F 13/00 Compounds containing elements of Groups 7 or 17 of the Periodic Table
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0046 Ruthenium compounds
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C07F 19/00 Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
• CPC Class Codes: C07F 3/003 without C-Metal linkages
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: C07F 5/069 without C-aluminium linkages
• CPC Class Codes: C07F 7/0805 comprising only Si, C or H atoms
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 9/5022 Aromatic phosphines (P-C aromatic linkage)
• 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 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen 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 85/344 : comprising ruthenium
• CPC Class Codes: H10K 85/348 : comprising osmium

Abstract

Novel polydentate carbene complexes of ruthenium and formulations containing the same are provided. Organic light emitting device containing the novel polydentate carbene complexes of ruthenium in an emissive layer are also provided. The novel polydentate carbene complexes of ruthenium may be particularly useful in OLEDs to provide devices having improved performance.

Claims

1. A compound selected from the group consisting of:

2. The compound of claim 1, wherein said compound is

3. The compound of claim 1, wherein said compound is

4. The compound of claim 1, wherein said compound is

5. The compound of claim 1, wherein said compound is

6. The compound of claim 1, wherein said compound is

7. The compound of claim 1, wherein said compound is

8. The compound of claim 1, wherein said compound is

9. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer, wherein the emissive layer comprises a compound selected from the group consisting of;

10. The organic light emitting device of claim 9, wherein said compound is

11. The organic light emitting device of claim 9, wherein said compound is

12. The organic light emitting device of claim 9, wherein said compound is

13. The organic light emitting device of claim 9, wherein said compound is

14. The organic light emitting device of claim 9, wherein said compound is

15. The organic light emitting device of claim 9, wherein said compound is

16. The organic light emitting device of claim 9, wherein said compound is

17. A formulation comprising a compound selected from the group consisting of: