Tetradentate metal complexes containing indoloacridine and its analogues
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.
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.