Tetradentate metal complexes containing indoloacridine and its analogues

Patent metadata

Field	Value
Publication number	US-10056564-B2
Application number	US-201715651972-A
Country	US
Kind code	B2
Filing date	Jul 17, 2017
Priority date	Jun 2, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

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

First claim

What is claimed is:

1. A complex of Formula I:

wherein:
M is Pt (II), Pd (II), or Au (III),
each of V, V 1 , V 2 , and V 3 is independently N, C, P, or Si,
each of X, X 1 , X 2 , and X 3 is independently present or absent, and each X, X 1 , X 2 , and X 3 present independently represents a single bond, CR 8 R 9 , C═O, SiR 8 R 9 , GeR 8 R 9 , NR 8 , PR 8 , PR 8 R 9 , R 8 P═O, AsR 8 , R 8 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BR 8 , BR 8 R 9 , AlR 8 , AlR 8 R 9 , R 8 Bi═O, or BiR 8 ,
each of Y, Y 1 and Y 2 is independently CR 10 , SiR 10 , GeR 10 , N, P, P═O, As, As═O, B, Bi═O, or Bi,
L is a substituted or unsubstituted aryl, heteroaryl, or N-heterocyclic carbene,
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 present independently represents deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof, and
each of R 8 , R 9 , and R 10 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

2. The complex of claim 1 , wherein:
V and V 1 are C,
V 2 and V 3 are N,
Y, Y 1 , and Y 2 are N, and
L is a substituted or unsubstituted pyridyl.

3. The complex of claim 2 , wherein:
X is CR 8 R 9 , and
X 1 is a single bond.

4. The complex of claim 1 , wherein M is Pt or Pd; one of X, X 1 , X 2 , and X 3 is BR 8 R 9 or AlR 8 R 9 ; and one of V, V 1 , V 2 , and V 3 is C or Si.

5. The complex of claim 1 , wherein M is Pt or Pd; two of X, X 1 , X 2 , and X 3 are independently BR 8 R 9 or AlR 8 R 9 ; and each of V, V 1 , V 2 , and V 3 is independently N or P.

6. The complex of claim 1 , wherein M is Au; one of X, X 1 , X 2 , and X 3 is BR 8 R 9 or AlR 8 R 9 ; and two of V, V 1 , V 2 , and V 3 are independently C or Si.

7. The complex of claim 1 , wherein M is Au; two of X, X 1 , X 2 , and X 3 are independently BR 8 R 9 or AlR 8 R 9 ; and one of V, V 1 , V 2 , and V 3 is C or Si.

8. The complex of claim 1 , wherein M is Au; three of X, X 1 , X 2 , and X 3 are BR 8 R 9 or AlR 8 R 9 ; and each of V, V 1 , V 2 , and V 3 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, X 1 , and X 2 is independently absent, a single bond or CR 8 R 9 .

16. The complex of claim 15 , wherein R 8 and R 9 are both alkyl.

17. The complex of claim 1 , wherein M is Pt or Pd; and each of V, V 1 , V 2 , and V 3 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 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is independently hydrogen or substituted or unsubstituted alkyl.

20. The complex of claim 1 , wherein Y 2 is a N.

Assignees

• Univ Arizona State

Inventors

• Li Jian

Classifications

• H01L51/0084 Primary

  Electricity · mapped topic

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0087

  Electricity · mapped topic

• H01L51/42

  Electricity · mapped topic