Tetradentate metal complexes containing indoloacridine and its analogues

• US 10,056,564 B2
• Filed: 07/17/2017
• Issued: 08/21/2018
• Est. Priority Date: 06/02/2015
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US15/651,972
• Publication Number:
  US 20180006246A1
• Time in Patent Office: 400 Days
• Field of Search: 546 10, 313504
• CPC Class Codes: C07F 1/12 Gold compounds
• 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 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the 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 30/00 Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20
• 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
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Platinum, palladium, and gold tetradentate metal complexes of Formulas I and II including indoloacridine.

The complexes are suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.

Claims

1. A complex of Formula I:

2. The complex of claim 1, wherein:

V and V¹ are C,

V² and V³ are N,

Y, Y¹, and Y² are N, and

L is a substituted or unsubstituted pyridyl.

3. The complex of claim 2, wherein:

X is CR⁸R⁹, and

X¹ is a single bond.

4. The complex of claim 1, wherein M is Pt or Pd;

one of X, X¹, X², and X³ is BR⁸R⁹ or AlR⁸R⁹; and

one of V, V¹, V², and V³ is C or Si.

5. The complex of claim 1, wherein M is Pt or Pd;

two of X, X¹, X², and X³ are independently BR⁸R⁹ or AlR⁸R⁹; and

each of V, V¹, V², and V³ is independently N or P.

6. The complex of claim 1, wherein M is Au;

one of X, X¹, X², and X³ is BR⁸R⁹ or AlR⁸R⁹; and

two of V, V¹, V², and V³ are independently C or Si.

7. The complex of claim 1, wherein M is Au;

two of X, X¹, X², and X³ are independently BR⁸R⁹ or AlR⁸R⁹; and

one of V, V¹, V², and V³ is C or Si.

8. The complex of claim 1, wherein M is Au;

three of X, X¹, X², and X³ are BR⁸R⁹ or AlR⁸R⁹; and

each of V, V¹, V², and V³ is independently N or P.

9. The complex of claim 1, wherein the complex is:

10. A light emitting device comprising the complex of claim 1.

11. An OLED device comprising the complex of claim 1.

12. The OLED device of claim 11, wherein the device is a phosphorescent OLED device.

13. A photovoltaic device comprising the complex of claim 1.

14. A luminescent display device comprising the complex of claim 1.

15. The complex of claim 1, wherein X, X¹, and X² is independently absent, a single bond or CR⁸R⁹.

16. The complex of claim 15, wherein R⁸ and R⁹ are both alkyl.

17. The complex of claim 1, wherein M is Pt or Pd;

and each of V, V¹, V², and V³ is independently C or N.

18. The complex of claim 1, wherein L is a substituted or unsubstituted heteroaryl.

19. The complex of claim 1, wherein each of R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ is independently hydrogen or substituted or unsubstituted alkyl.

20. The complex of claim 1, wherein Y² is a N.