Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues
Tetradentate and octahedral metal complexes suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.
1. A complex of Formula AIX or Formula AX:
wherein:
M is Pt or Pd,
each of V 1 , V 2 , V 3 , and V 4 is coordinated with M;
V 1 and V 4 are N,
V 2 and V 3 are C,
L 1 and L 4 are each independently substituted or unsubstituted pyridine,
L 2 and L 3 are each independently substituted or unsubstituted phenyl,
each of A 1 , A 2 , A 3 , and A 4 is independently a single bond, CR 1 R 2 , SiR 1 R 2 , NR 3 , O, or BR 3 ,
each of X 1 , X 2 , and X 3 is independently CR 1 or N,
each of R a , R b , R c , and R d is independently present or absent, and if present each of R a , R b , R c , and R d is independently a mono-, di-, or tri-substitution as valency permits, and each of R a , R b , R c , and R d 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, and
each of R x , R y , and R z 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 and
each of R 1 , R 2 and R 3 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 the complex has a neutral charge.
3. A complex represented by one of the following chemical structures:
wherein each of R, R 1 , R 2 , R 3 , and R 4 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.
4. The complex of claim 1 , wherein
is one of the following structures:
wherein each of R 1 , R 2 , R 3 and R 4 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.
5. The complex of claim 1 , wherein each of
is:
6. The complex of claim 1 , wherein each of
is:
7. The complex of claim 1 , wherein each of
is:
8. The complex of claim 1 , wherein each of
is independently one of the following structures:
wherein each of R, R 1 , and R 2 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.
9. An emitter comprising the complex of claim 3 .
10. An emitter comprising the complex of claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter.
11. An emitter comprising the complex of claim 1 , wherein the emitter is a phosphorescent emitter.
12. An emitter comprising the complex of claim 1 , wherein the emitter is a delayed fluorescent emitter.
13. The complex of claim 1 , wherein polymeric comprises polyalkylene, polyester, or polyether.
14. The complex of claim 13 , wherein polymeric comprises —(CH 2 O) n —CH 3 , —(CH 2 CH 2 O) n —CH 3 , —[CH 2 CH(CH 3 )] n —CH 3 , —[CH 2 CH(COOCH 3 )] n —CH 3 , —[CH 2 CH(COO CH 2 CH 3 )] n —CH 3 , or —[CH 2 CH(COO t Bu)] n —CH 3 , where n is an integer.
15. A device comprising a complex of claim 1 .