SYNTHESIS OF CYCLOMETALLATED PLATINUM(II) COMPLEXES

• US 20130172561A1
• Filed: 12/20/2012
• Published: 07/04/2013
• Est. Priority Date: 01/03/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kottas, Gregg, Yeager, Walter, Tsai, Jui-Yi
• Granted Patent: US 8,987,451 B2
• Time in Patent Office: Days
• US Class Current: 546/4
• CPC Class Codes: C07F 15/006 Palladium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds

Abstract

A single-step method of making tetradentate platinum or palladium complexes is disclosed. The method advantageously allows the formation of a platinum or palladium complex in a single step, even with sterically hindered ligands, without the use of highly reactive intermediates. The compounds made by the disclosed method are useful in OLED applications.

Claims

1. A method of preparing a metal complex comprising:

(a) combining at least one ligand L with a metal precursor to form a mixture;

wherein the ligand L is at least bidentate;

wherein the metal precursor is a Pt or Pd compound containing at least one bidentate ligand L′

;

wherein no halogen is directly connected to the Pt or Pd;

(b) reacting the mixture for a sufficient time to form a reaction product;

wherein the reaction product has at least two atoms from ligand L bonded to the Pt or Pd, wherein ligand L has at least one anionic carbon donor bonded to Pt or Pd;

(c) recovering the reaction product from the mixture.

2. The method of claim 1, wherein ligand L has the formula:

3. The method of claim 2, wherein ligand L has the formula:

4. The method of claim 2, wherein the ligand L has the formula:

5. The method of claim 2, wherein the ligand L has the formula:

6. The method of claim 2, wherein the ligand L has the formula:

7. The method of claim 2, wherein rings A, B, C, and D are independently selected from the group consisting of benzene, pyridine, imidazole, and pyrazole.

8. The method of claim 2, wherein at least one of ring A, B, C, and D is benzene.

9. The method of claim 2, wherein two of Z₁, Z₂, Z₃ and Z₄ are CH, and two of Z₁, Z₂, Z₃ and Z₄ are N.

10. The method of claim 1, wherein the metal precursor is Pt compound.

11. The method of claim 2, wherein the ligand L has the formula selected from:

12. The method of claim 1, wherein ligand L′

has the formula;

13. The method of claim 12, wherein X₁ and X₂ are independently selected from the group consisting of O and S.

14. The method of claim 12, wherein X₁ and X₂ are O.

15. The method of claim 14, wherein ligand L′

has the formula;

16. The method of claim 15, wherein R_x, R_y, and R_z are independently selected from the group consisting of alkyl, hydrogen, deuterium, and combinations thereof.

17. The method of claim 16, wherein R_z is hydrogen or deuterium, and R_x and R_y are independently selected from the group consisting of methyl, CH(CH₃)₂, and CH₂CH(CH₃)₂.

18. The method of claim 17, wherein R_x and R_y are methyl.

19. The method of claim 1, wherein the reaction time is at least 30 hours.