Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues

• US 10,020,455 B2
• Filed: 01/07/2015
• Issued: 07/10/2018
• Est. Priority Date: 01/07/2014
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian, Li, Guijie
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/591,188
• Publication Number:
  US 20150194616A1
• Time in Patent Office: 1,280 Days
• Field of Search: 546 2, 313504
• CPC Class Codes: C07F 15/006 Palladium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• 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 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1062 with oxygen
• CPC Class Codes: C09K 2211/1066 with sulfur
• CPC Class Codes: C09K 2211/1077 with oxygen
• CPC Class Codes: C09K 2211/1081 with sulfur
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1096 containing other 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 85/341 : Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/346 : comprising platinum

Abstract

A phosphorescent emitter or delayed fluorescent and phosphorescent emitters represented by Formula 1 or Formula II, where M is platinum or palladium.

Claims

1. A compound of Formula I:

2. The compound of claim 1, wherein the compound has the structure of Formula III or Formula V:

3. The compound of claim 1, wherein the compound has the structure of Formula VII:

4. The compound of claim 1, wherein the compound has the structure of anyone of Formulas A1-A23:

5. The compound of claim 1, wherein the compound has a neutral charge.

6. The compound of claim 4, wherein each of Z, Z¹, and Z² is independently selected from the following:

7. The compound of claim 1, wherein F¹, if present, is covalently bonded to L¹ directly, F², if present, is covalently bonded to L² directly, or a combination thereof.

8. The compound of claim 7, wherein F¹, if present, is covalently bonded to L¹ by a linking atom or linking group, F², if present, is covalently bonded to L² by a linking atom or linking group.

9. The compound of claim 8, wherein each linking atom or linking group is independently selected from the following:

10. An emitter comprising the compound of claim 1, wherein the emitter is a delayed fluorescent and phosphorescent emitter.

11. An emitter comprising the compound claim 1, wherein the emitter is a phosphorescent emitter.

12. An emitter comprising the compound of claim 1, wherein the emitter is a delayed fluorescent emitter.

13. A light-emitting device comprising a compound of claim 1.

14. The light-emitting device of claim 13, wherein the compound demonstrates 100% internal quantum efficiency in the device settings.

15. The light emitting device of claim 13, wherein the device is an organic light emitting diode.

16. A compound represented by one of the following structures:

17. An emitter comprising the compound of claim 16, wherein the emitter is a delayed fluorescent emitter.

18. A light-emitting device comprising a compound of claim 16.

19. The light-emitting device of claim 18, wherein the compound demonstrates 100% internal quantum efficiency in the device settings.

20. A compound represented by one of the following structures: