Organic light emitting materials with anionic ligand

Abstract

Emissive phosphorescent organometallic compounds that produce electroluminescence and organic light emitting devices employing such emissive phosphorescent organometallic compounds are provided. More specifically the present invention is directed to novel primarily non-emitting ligands which produce a blue shift in emitted light when associated with a cyclometallated ligand.

1 - 43 . (canceled) 
   
   
       44 . A compound represented by the Formula (I): 
     
       
         
         
             
             
         
       
     
     wherein 
     
       
         
         
             
             
         
       
     
     is a cyclometallated ligand,
 M is a metal with an atomic weight of greater than 40, 
 X and Y are each independently selected from a heteroatom, heteroatom-containing group or heterocycle, 
 Z is a group of the formula JR′ p R″ q  
 wherein J is hydrogen or a metal or a non-metal, R′ and R″ are independently, alkenyl, heteroaryl, hydroxy, alkoxy, aryloxy, amino, alkylamino, arylamino, sulfido, alkylsulfido, arylsulfido, phosphino, alkylphosphino or arylphosphino and p and q are integers between 0 and 2, 
 
 m and n are integers selected from 1 and 2 wherein the sum of n+m is 2 or 3, 
 
     with the proviso that 
     
       
         
         
             
             
         
       
     
     is anionic. 
   
   
       45 . The compound of claim  1 , wherein J is boron. 
   
   
       46 . The compound of claim  1 , wherein J is selected from Al, Ga, In, Zn, Cd, Hg, Cu, Ag and Au. 
   
   
       47 . The compound of claim  1 , wherein the heteroatom-containing group is selected from OR, SR, NR 2  and PR 2 , wherein R is alkyl, aryl, or heteroaryl. 
   
   
       48 . The compound of claim  4 , wherein R is a C 1 -C 6  alkyl, aryl, or heteroaryl. 
   
   
       49 . The compound of claim  1 , wherein X and Y are heterocycles. 
   
   
       50 . The compound of claim  6 , wherein R′ and R″ are heteroaryl. 
   
   
       51 . The compound of claim  7 , wherein R′ and R″ are selected from the group consisting of alkyls, aryls, and pyrazoles and p and q are each 1. 
   
   
       52 . The compound of claim  7 , wherein R′ is pyrazole, R″ is a pyrazole and p and q are each 1. 
   
   
       53 . The compound of claim  7 , wherein X and Y are pyrazoles. 
   
   
       54 . The compound of claim  1 , wherein Z is hydrogen. 
   
   
       55 . The compound of claim  1 , wherein R′ is selected from the group consisting of bidentate alkyl, aryl and carboxyl ligands and chelating coordination ligands, p is equal to 1 and q is equal to 0. 
   
   
       56 . The compound of claim  1 , wherein the heavy metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Ag, and Au. 
   
   
       57 . The compound of claim  13 , wherein the heavy metal is Ir. 
   
   
       58 . The compound of claim  13 , wherein the heavy metal is Pt. 
   
   
       59 . The compound of claim  1 , having the Formula III: 
     
       
         
         
             
             
         
       
     
     wherein each R 11  and R 12  is independently selected from alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , CO 2 R, C(O)R, NR 2 , NO 2 , OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl or a heterocyclic group, and additionally, or alternatively, any two adjacent substituted positions together form, independently, a fused 5- to 6-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the fused 5- to 6-member cyclic group cyclic group may be optionally substituted with one or more of alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , CO 2 R, C(O)R, NR 2 , NO 2 , OR, or halo;
 each R is independently alkyl, aryl, or heteroaryl; and 
 subscript a and b are independently selected from 0, 1, 2, and 3. 
 
   
   
       60 . The compound of claim  1 , having the formula IV: 
     
       
         
         
             
             
         
       
     
   
   
       61 . The compound of claim  1 , having the Formula V: 
     
       
         
         
             
             
         
       
     
     wherein each R 11 , R 12 , R 13 , and R 14  is independently selected alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , CO 2 R, C(O)R, NR 2 , NO 2 , OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl or a heterocyclic group, and additionally, or alternatively, any two adjacent substituted positions together form, independently, a fused 5- to 6-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the fused 5- to 6-member cyclic group cyclic group may be optionally substituted with one or more of alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , CO 2 R, C(O)R, NR 2 , NO 2 , OR, or halo;
 each R is independently alkyl aryl and heteroaryl; and 
 subscript a, b, c, and d are independently selected from 0, 1, 2, and 3. 
 
   
   
       62 . The compound of claim  1  having the formula (II). 
     
       
         
         
             
             
         
       
     
     wherein 
     
       
         
         
             
             
         
       
     
     is a cyclometallated ligand,
 M is a metal with an atomic weight of greater than 40, 
 m is 1 or 2, 
 R a , R b , R c , R′ a , R′ b  and R′ c , if present, are selected from H, alkyl, aryl, heteroaryl, halogen, alkoxy, amino, alkylamino, arylamino, sulfido, alkylsulfido, arylsulfido, phosphino, alkylphosphino or arylphosphino, 
 
     with the proviso that 
     
       
         
         
             
             
         
       
     
     is anionic.