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

• US 8,563,737 B2
• Filed: 02/23/2011
• Issued: 10/22/2013
• 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:
  US13/033,160
• Publication Number:
  US 20120215000A1
• Time in Patent Office: 972 Days
• Field of Search: 548/103, 548/108, 548/305.1, 546/4
• 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

Methods of making bis-tridentate carbene complexes of ruthenium and osmium are provided. The use of DMSO solvates of ruthenium(II) and osmium(II) halide salts provides good yields of the corresponding complexes. These materials may be used in OLEDs to provide devices having improved performance.

Claims

1. A method of making a metal complex having the formula I,

Q₁-M-Q₂,

the method comprising:

mixing a salt of formula MX₂L_n with precursors of carbenes Q₁ and Q₂, wherein Q₁ and Q₂ are independently selected from a compound of formula II,

2. The method of claim 1, wherein M is Ru or Os.

3. The method of claim 1, wherein the carbene forming agent is selected from silver(I) oxide and copper(I) alkoxide.

4. The method of claim 3, wherein the copper(I) alkoxide is copper(I) tert-butoxide.

5. The method of claim 2, wherein M is Ru, L is DMSO, and n is 4.

6. The method of claim 5, wherein X is Cl.

7. The method of claim 2, wherein M is Os, L is DMSO, and n is 4.

8. The method of claim 7, wherein X is Cl.

9. The method of claim 2, wherein the solvent comprises a polar solvent.

10. The method of claim 9, wherein the polar solvent comprises an alcohol.

11. The method of claim 10, wherein the alcohol is selected from the group consisting of 2-methoxyethanol, 2-ethoxyethanol, and mixtures thereof.

12. The method of claim 2, wherein precursors of carbenes Q1 and Q2 is independently selected from a compound of formula III:

13. The method of claim 12, wherein the carbene precursor is selected from the group consisting of:

14. The method according to claim 1, wherein L is DMSO.

15. The method according to claim 1, wherein L is THF.

16. The method according to claim 1, wherein L is CH₃CN.