Emitters based on octahedral metal complexes
Iridium, rhodium, and platinum complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters have the following structure:
1. A compound of Formula V:
wherein:
M is Ir(III), Rh(III) or Pt(IV),
each of L 1 is independently a substituted or unsubstituted structure selected from the group consisting of
L 3 is a substituted or unsubstituted structure selected from the group consisting of
each of L 2 and L 4 is independently substituted or unsubstituted phenyl,
each of V 1 and V 3 is coordinated with M and is independently N or C,
each of V 2 and V 4 is coordinated with M and is C,
each of F 1 , F 2 , F 3 , and F 4 is independently present or absent, wherein at least one of F 1 , F 2 , F 3 , and F 4 is present, and each F 1 , F 2 , F 3 , and F 4 present is a fluorescent luminophore, and
each of R a , R b , R c , and R d is independently present or absent, and if present each R a , R b , R c , and R d independently represents mono-, di-, or tri-substitutions, and wherein each R a , R b , R c , and R d present is independently deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, 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 compound of claim 1 , wherein the compound has a neutral charge.
3. The compound of claim 1 , wherein each of
is independently one of the following structures:
and
is one of the following structures:
wherein R is 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 compound of claim 1 , wherein each of F 1 , F 2 , F 3 , and F 4 , if present, is independently one of the following structures:
1 Aromatic Hydrocarbons and Their Derivatives
2 Arylethylene, Arylacetylene and Their Derivatives
3 Heterocyclic Compounds and Their Derivatives
4 Other fluorescent luminophors
wherein:
each of R 1 , R 2 , R 3 , R 4 , R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , R 81 , R 91 , and R 101 , if present, is a mono-, di-, tri-, or tetra-substitution, valency permitting, and each R 1 , R 2 , R 3 , R 4 , R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , R 81 , R 91 , and R 101 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,
each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o , and Y p , if present, is independently C, N or B,
each of U a and U b , if present, is independently CH 2 , CR 1 R 2 , C═O, CH 2 , SiR 1 R 2 , GeH 2 , GeR 1 R 2 , NH, NR 3 , PH, PR 3 , R 3 P═O, AsR 3 , R 3 As═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR 3 , R 3 Bi═O, BiH, or BiR 3 , and
each of W, W a , and W b , if present, is independently CH, CR 1 , SiR 1 , GeH, GeR 1 , N, P, B, Bi, or Bi═O.
5. The compound of claim 1 , wherein the compound is one of the following structures
6. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter.
7. An emitter comprising the compound of claim 1 , wherein the emitter is a phosphorescent emitter.
8. An emitter comprising the compound of claim 1 , wherein the emitter is a delayed fluorescent emitter.
9. A device comprising a compound of claim 1 .
10. The device of claim 9 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings.
11. The device of claim 9 , wherein the device is an organic light emitting diode.
12. The compound of claim 1 , wherein polymeric comprises polyalkylene, polyester, or polyether.
13. The compound of claim 12 , 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.
14. The compound of claim 1 , wherein each of L 1 is independently a substituted or unsubstituted structure selected from the group consisting of
and
L 3 is a substituted or unsubstituted structure selected from the group consisting of