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

Patent metadata

Field	Value
Publication number	US-9923155-B2
Application number	US-201514805691-A
Country	US
Kind code	B2
Filing date	Jul 22, 2015
Priority date	Jul 24, 2014
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

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

First claim

What is claimed is:

1. A complex represented by Formula I:

wherein:
each R 1 is independently

each of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently hydrogen, halogen, hydroxy, nitro, thiol; substituted or unsubstituted: C 1 -C 4 alkyl, alkoxy, aryl, or amino,
or any two of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 on the same ring or adjacent rings are bonded together to form a fused ring system,
X is O, S, S═O, O═S═O, Se, Se═O, O═Se═O, NR 2a , PR 2b , AsR 2c , CR 2d R 2e , SiR 2f R 2g , or BR 2h , wherein X is optionally directly linked to R 10 or R 11 , and
each of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , and R 2h is independently substituted or unsubstituted C 1 -C 4 alkyl or aryl.

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

wherein Ad refers to adamantyl;
Mes refers to mesityl;
Dipp refers to 2,6-diisopropylphenyl;
Cy refers to cyclohexyl.

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 R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 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 K 2 PtCl 4 .

9. The method of claim 7 , wherein the bromine-containing compound is n-Bu 4 NBr.

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 R 2 , R 3 , R 4 , and R 5 are hydrogen.

16. The complex of claim 14 , wherein R 8 and R 9 are hydrogen.

17. The complex of claim 14 , wherein R 1 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:

wherein Np refers to neopentyl.

Assignees

• Univ Arizona State

Inventors

• Li Jian
• Zhu zhi-qiang

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title