Emitters based on octahedral metal complexes

Abstract

Iridium, rhodium, and platinum complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters having the following structures:

What is claimed is: 
     
         1 . A compound of Formula I, Formula II, Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX or Formula X: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein: 
         M is Ir(III), Rh(III) or Pt(IV), 
         each of L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 , if present, is independently substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, carbene, or N-heterocyclic carbene, dione, cyanogen, or phosphine, 
         each of V 1 , V 2 , V 3 , V 4 , V 5 , and V 6 , if present, is coordinated with M and is independently N, C, P, B, or Si, 
         each of X, Y, and Z, 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 , 
         each of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6  is independently present or absent, wherein at least one of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6  is present, and each F 1 , F 2 , F 3 , F 4 , F 5 , and F 6  present is a fluorescent luminophore, 
         each of R a , R b , R c , R d , R e , and R f  is independently present or absent, and if present each R a , R b , R c , R d , R e  and R f  independently represents mono-, di-, or tri-substitutions, and wherein each R a , R b , R c , R d , R e  and R f  present 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 
         each of R 1 , R 2 , and R 3 , if present, 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 compound of  claim 1 , wherein the compound has a neutral charge. 
     
     
         3 . The compound of  claim 1 , wherein each of 
       
         
           
           
               
               
           
         
       
       if present, is independently one of the following structures: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein each of 
       
         
           
           
               
               
           
         
       
       if present, is independently 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. 
       
     
     
         5 . The compound of  claim 1 , wherein each of F 1 , F 2 , F 3 , F 4 , F 5 , and F 6 , 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 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , and R 81 , if present, is a mono-, di-, tri-, or tetra-substitution, valency permitting, and each R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 , and R 81  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 , U b , and U c , 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 a , W b  and W c , if present, is independently CH, CR 1 , SiR 1 , GeH, GeR 1 , N, P, B, Bi, or Bi═O. 
         
       
     
     
         6 . The compound of  claim 1 , wherein each of X, Y, and Z, if present, is independently one of the following structures: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein: 
         x is an integer from 1 to 10, and 
         each of R sl , R tl , R ul , and R vl , if present, 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. 
       
     
     
         7 . The compound of  claim 1 , wherein the compound is selected from any of Structures Ir-1 to Ir-25, Rh-1 to Rh-25, and Pt-1 to Pt-13. 
     
     
         8 . An emitter comprising the compound of  claim 1 , wherein the emitter is a delayed fluorescent and phosphorescent emitter. 
     
     
         9 . An emitter comprising the compound of  claim 1 , wherein the emitter is a phosphorescent emitter. 
     
     
         10 . An emitter comprising the compound of  claim 1 , wherein the emitter is a delayed fluorescent emitter. 
     
     
         11 . A device comprising a compound of  claim 1 . 
     
     
         12 . The device of  claim 11 , wherein the compound is selected to have 100% internal quantum efficiency in the device settings. 
     
     
         13 . The device of  claim 11 , wherein the device is an organic light emitting diode. 
     
     
         14 . The compound of  claim 1 , wherein polymeric comprises polyalkylene, polyester, or polyether. 
     
     
         15 . The compound of  claim 14 , 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(COOCH 2 CH 3 )] n —CH 3 , or —[CH 2 CH(COO t Bu)] n —CH 3 , where n is an integer.