Metal assisted delayed fluorescent emitters for organic light-emitting diodes
Compounds of General Formula I may harvest electrogenerated excitons via metal-assisted delayed fluorescence (MADF). The compounds have utility in light emitting diodes and light emitting devices.
1. A compound represented by General Formula VIII:
wherein:
M represents Pt(II) or (Pd(II);
Y 2a , Y 2b , Y 3a , Y 3b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g , and Y 4h each independently represents C or N;
Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;
A, B, C and D each independently represents C, N, O, or S;
X represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 , or X is not present, wherein when X is not present, no bond exists between L 4 and the ring comprising Z 2 ;
X 1 represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
Y 1 and Y 2 each independently represents 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, wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring;
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 independently represents deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazine; 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, or any two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 represent a covalent bond;
any two R 1 may together form a fused ring, any two R 2 may together form a fused ring, any two R 3 may together form a fused ring, any two R 4 may together form a fused ring, any two R 5 may together form a fused ring, any two R 6 may together form a fused ring, and any R may form a ring with an R 7 bound to the same atom;
L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl;
L 5 is present or absent;
V 1 and V 2 are independently present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 1 is not present, then L 4 is not bound to L 5 ; and when V 2 is not present, then L 6 is not bound to L 5 ;
V 3 is present or absent, wherein V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 3 is not present, then a Y 2a is directly bound to Y 2b ; and
each n is independently an integer, valency permitting.
2. The compound of claim 1 , wherein two additional adjacent groups R 2 together are represented by Formula B:
wherein X 2 represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
Y 5a , Y 5b , Y 5c , Y 5d each independently represents C or N;
R 9 represents 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, or any two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 represent a covalent bond; and
each n is independently an integer, valency permitting.
3. The compound of claim 1 , wherein the compound is represented by General Formula II:
wherein:
M represents Pt(II) or (Pd(II);
Y 1a , Y 1b , Y 1c , Y 1d , Y 2a , Y 2b , Y 3a , Y 3b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g , and Y 4h each independently represents C or N;
Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;
C and D each independently represents C, N, O, or S;
X represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 , or X is not present, wherein when X is not present, no bond exists between L 4 and the ring comprising Z 2 ;
X 1 represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 10 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 3 , R 4 , R 5 , R 6 and R 7 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, or any two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 10 represent a covalent bond;
any two R 1 may together form a fused ring, any two R 2 may together form a fused ring, any two R 3 may together form a fused ring, any two R 4 may together form a fused ring, any two R 5 may together form a fused ring, any two R 6 may together form a fused ring, any two R 10 may together form a fused ring, and any R 8 may form a ring with an R 7 bound to the same atom;
L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl;
L 5 is present or absent;
V 1 and V 2 are independently present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 1 is not present, then L 4 is not bound to L 5 ; and when V 2 is not present, then L 6 is not bound to L 5 ;
V 3 is present or absent, wherein V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 3 is not present, then a Y 2a is directly bound to Y 2b ; and
each n is independently an integer, valency permitting.
4. The compound of claim 2 , wherein the compound is represented by General Formula XIV or General Formula XV,
wherein:
Y 1a , Y 1b , Y 1c , Y 1d , Y 2a , Y 2b , Y 3a , Y 3b , Y 4e , Y 4f , Y 4g , Y 4h , Y 5a , Y 5b , Y 5c , and Y 5d each independently represents C or N;
Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;
C and D each independently represents C, N, O, or S;
X represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 , or X is not present, wherein when X is not present, no bond exists between L 4 and the ring comprising Z 2 ;
X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
each of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 independently represents 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, or any two of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 represent a covalent bond;
any two R 1 may together form a fused ring, any two R 3 may together form a fused ring, any two R 4 may together form a fused ring, any two R 5 may together form a fused ring, any two R 6 may together form a fused ring, any two R 9 may together form a fused ring, any two R 10 may together form a fused ring, and any R 8 may form a ring with an R 7 bound to the same atom;
L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl;
L 5 is present or absent;
V 1 and V 2 are independently present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 7 , R 7 Bi═O, or BiR 7 ; wherein when V 1 is not present, then L 4 is not bound to L 5 ; and when V 2 is not present, then L 6 is not bound to L 5 ;
V 3 is present or absent, wherein V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 3 is not present, then a Y 2a is directly bound to Y 2b ; and
each n is independently an integer, valency permitting.
5. The compound of claim 2 , wherein the compound is
represented by General Formula XVIII or General Formula XIX:
wherein:
Y 2a , Y 2b , Y 3a , Y 3b , Y 4e , Y 4f , Y 4g , Y 4h , Y 5a , Y 5b , Y 5c and Y 5d each independently represents C or N;
Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;
A, B, C and D each independently represents C, N, O, or S;
X represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 , or X is not present, wherein when X is not present, no bond exists between L 4 and the ring comprising Z 2 ;
X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
Y 1 and Y 2 each independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, 10ydrazine; 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; wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring;
each of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, 10ydrazine; 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; or any two of R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 represent a covalent bond;
any two R 1 may together form a fused ring, any two R 3 may together form a fused ring, any two R 4 may together form a fused ring, any two R 5 may together form a fused ring, any two R 6 may together form a fused ring, any two R 9 together form a fused ring and any R 8 may form a ring with an R 7 bound to the same atom;
L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl;
L 5 is present or absent;
V 1 and V 2 are independently present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR, PR 7 , PR 7 R 8 , R 7 P═O, AsR 7 , R 7 As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 1 is not present, then L 4 is not bound to L 5 ; and when V 2 is not present, then L 6 is not bound to L 5 ;
V 3 is present or absent, wherein V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or if valency permits, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ; wherein when V 3 is not present, then a Y 2a is directly bound to Y 2b ; and
each n is independently an integer, valency permitting.
6. The compound of claim 1 , wherein
is represented by one of the following structures:
wherein:
M represents Pt(II) or Pd(II);
Y 1a , Y 1b , Y 1c , Y 1d , Y 3a , Y 3b , Y 4e , Y 4f , Y 4g , Y 4h , Y 5a , Y 5b , Y 5c and Y 5d each independently represents C or N;
X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, 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, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi═O, or BiR 7 ;
each of R 1 , R 6 , R 7 , R 8 , R 9 , and R 10 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 6 , R 9 , and R 10 independently represents 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, or any two of R 1 , R 6 , R 9 , and R 10 represent a covalent bond; any two of R 1 , R 6 , R 9 , and R 10 may together form a fused ring;
each n is independently an integer, valency permitting.
7. The compound of claim 1 , wherein
is represented by one of the following structures:
wherein:
Y 1a , Y 1b , Y 1c , Y 1d , Y 2a , Y 2b , Y 2c , Y 2d , Y 3a , Y 3b and Y 3c each independently represents C or N;
each of R 1 , R 2 , R 3 , R 4 , R 5 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 , R 3 , R 4 , R 5 , R 6 and R 7 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.
8. The compound of claim 1 , wherein
is represented by one of the following structures:
wherein:
Y 1a , Y 1b , Y 1c , Y 1d , Y 1e , Y 1f , and Y 1g each independently represents C or N; each of R 1 and R 2 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each of R 1 and R 2 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 any two of R 1 and R 2 may together join to form a ring;
each of Y 1 , Y 2 , Y 3 and Y 4 is independently absent or present, and each of Y 1 , Y 2 , Y 3 and Y 4 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, 15ydrazine; 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
any two of Y 1 , Y 2 , Y 3 , and Y 4 may together join to form a ring.
9. The compound of claim 1 , wherein the compound is selected from the following structures:
10. An organic light emitting diode comprising the compound of claim 3 .
11. An organic light emitting diode comprising the compound of claim 1 .
12. An organic light emitting diode comprising the compound of claim 4 .
13. An organic light emitting diode comprising the compound of claim 5 .
14. A light emitting device comprising the light emitting diode of claim 10 .
15. A light emitting device comprising the light emitting diode of claim 11 .
16. A light emitting device comprising the light emitting diode of claim 12 .
17. A light emitting device comprising the light emitting diode of claim 13 .