Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues

• US 9,923,155 B2
• Filed: 07/22/2015
• Issued: 03/20/2018
• Est. Priority Date: 07/24/2014
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian, Zhu, Zhi-Qiang
• Primary Examiner(s): Jarrell, Noble E
• Application Number:
  US14/805,691
• Publication Number:
  US 20160028028A1
• Time in Patent Office: 972 Days
• Field of Search: None
• CPC Class Codes: C07F 15/0086 Platinum 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 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/346 comprising platinum

Abstract

Tetradentate platinum complexes of Formulas I and II suitable for phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.

Claims

1. A complex represented by Formula I:

2. The complex of claim 1, having one of the following chemical structures:

3. The complex of claim 1, wherein the complex is a delayed fluorescent and phosphorescent emitter.

4. The complex of claim 1, wherein the complex is a phosphorescent emitter.

5. The complex of claim 1, wherein the complex is a delayed fluorescent emitter.

6. The complex of claim 1, wherein the fused ring system formed by any two of R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ on the same ring or adjacent rings, comprises benzimidazole, benzoxazole, benzothiazole, indazole, quinoline, isoquinoline, or imidazo[1,5-a]pyridine.

7. A method of preparing the complex of claim 1, the method comprising:

combining the ligand with a platinum salt, a bromine-containing compound, and acetic acid to yield a mixture;

heating the mixture; and

cooling the mixture to room temperature.

8. The method of claim 7, wherein the platinum salt is K₂PtCl₄.

9. The method of claim 7, wherein the bromine-containing compound is n-Bu₄NBr.

10. A device comprising the complex of claim 1.

11. The device of claim 10, wherein the device is a light-emitting device.

12. The device of claim 11, wherein the device is an organic light emitting diode.

13. The device of claim 11, wherein the device is a full color display.

14. The complex of claim 1, wherein the complex has the formula:

15. The complex of claim 14, wherein R², R³, R⁴, and R⁵ are hydrogen.

16. The complex of claim 14, wherein R⁸ and R⁹ are hydrogen.

17. The complex of claim 14, wherein R¹ is .

18. A device comprising the complex of claim 14.

19. The device of claim 18, wherein the device is a light-emitting device.

20. The device of claim 19, wherein the device is an organic light emitting diode.

21. A complex, which is selected from: