Tetradentate metal complexes containing indoloacridine and its analogues

1. A complex of Formula II:

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 and X 1 is independently present or absent, and each X and X 1 present independently represents CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P═O, AsR 7 , R 7 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, BiR 7 , or a single bond,

each of Y and Y 1 is independently CR 9 , SiR 9 , GeR 9 , N, P, P═O, As, As═O, B, Bi═O, or Bi,

L is a substituted or unsubstituted: 5-membered heteroaryl or 5-membered N-heterocyclic carbene,

each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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 , and R 6 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 7 , R 8 , and R 9 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 2 are C,

V 1 and V 3 are N,

Y and Y 1 are N, and

L is a substituted or unsubstituted 5-membered heteroaryl.

3. The complex of claim 2 , wherein X is a single bond.

4. The complex of claim 3 , wherein X 1 is CR 8 R 9 .

5. The complex of claim 1 , wherein M is Pt or Pd; one of X and X 1 is BR 7 R 8 or AlR 7 R 8 ; and one of V, V 1 , V 2 , and V 3 is C or Si.

6. The complex of claim 1 , wherein M is Pt or Pd; both of X and X 1 are independently BR 7 R 8 or AlR 7 R 8 ; and each of V, V 1 , V 2 , and V 3 is independently N or P.

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

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

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

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

11. The OLED device of claim 10 , wherein the device is a phosphorescent OLED device.

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

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

14. The complex of claim 1 , wherein X and X 1 are both CR 8 R 9 .

15. The complex of claim 14 , wherein R 8 and R 9 are both alkyl.

16. The complex of claim 1 , wherein M is Pt or Pd; X and X 1 are CR 8 R 9 ; and each of V, V 1 , V 2 , and V 3 is independently C or N.

17. The complex of claim 1 , wherein L is a substituted or unsubstituted 5-membered N-heterocyclic carbene.

18. The complex of claim 1 , wherein each of R 1 , R 2 , R 3 ,R 4 , R 5 , and R 6 is hydrogen.

19. The complex of claim 1 , wherein:

V and V 2 are C,

V 1 and V 3 are N,

Y and Y 1 are N, and

L is a substituted or unsubstituted 5-membered N-heterocyclic carbene.