Tetradentate metal complexes with carbon group bridging ligands
Platinum, palladium, and gold complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters having one of the following structures:
1. A compound of Formula VI:
wherein:
M is Pt, Pd, or Au,
A is C, Si, or Ge,
each of L 1 and L 4 is a substituted or unsubstituted pyridyl group,
each of L 2 and L 3 is a substituted or unsubstituted phenyl group,
each of V 1 and V 4 is coordinated with M and is independently N or C,
each of V 2 and V 3 is coordinated with M and is C,
each of Y 1 and Y 2 is independently CH, CR, SiH, SiR, N, P, P═O, As, or As═O,
R La and R Lb are covalently bonded to form a fused ring, wherein the fused ring formed by R La and R Lb is substituted by one or more of 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, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof,
each of R a , R b , R c , R d , R e , and R f is independently present or absent, and if present each of R b , R c , R e and R f independently represents mono-, di-, or tri-substitutions, each of R a and R d independently represents mono-, di-, tri-, or tetra-substitutions, and each of R a , R b , R c , R d , R e and R f is independently 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
R is independently R is 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, monarylamino, 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 compound of claim 1 , wherein the compound has a neutral charge.
3. The compound of claim 1 , wherein
is one of the following structures:
wherein:
each R 1 and R 2 present, valency permitting, is independently 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, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof,
Z is CH 2 , CR x R y C═O, SiR x R y , GeH 2 , GeR x R y , NH, NR z , PH, PR z , R z P═O, AsR z , R z As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR z , R z Bi═O, BiH, or BiR z , 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, monarylamino, 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 compound of claim 1 , wherein each of
is independently one of the following structures:
5. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter.
6. An emitter comprising the compound of claim 1 , wherein the emitter is a phosphorescent emitter.
7. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent emitter.
8. A device comprising the compound of claim 1 .
9. The device of claim 8 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings.
10. The device of claim 8 , wherein the device is an organic light emitting diode.
11. The compound of claim 1 , wherein:
A is C or Si.
12. The compound of claim 1 , wherein Y 1 and Y 2 are N.
13. The compound of claim 1 , wherein A is C.
14. A compound selected from one of the following structures:
15. A compound selected from one of the following structures: