Phenyl and Fluorenyl Substituted Phenyl-Pyrazole Complexesof Ir

Abstract

The invention provides emissive materials and organic light emitting devices using the emissive materials in an emissive layer disposed between and electrically connected to an anode and a cathode. The emissive materials include compounds with the following structure: wherein at least one of R 8 to R 14 is phenyl or substituted phenyl, and/or at least two of R 8 to R 14 that are adjacent are part of a fluorenyl group. The emissive materials have enhanced electroluminescent efficiency and improved lifetime when incorporated into light emitting devices.

1 .- 20 . (canceled) 
     
     
         21 . A compound, having the structure: 
       
         
           
           
               
               
           
         
         wherein
 M is a metal having an atomic weight greater than 40; 
 (C—N) is a substituted or unsubstituted cyclometallated ligand; 
 each of R 8  through R 14  is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , NO 2 , halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; or 
 any two adjacent substituted positions R 8  through R 14  can form a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the formed 4- to 7-member cyclic group is optionally substituted; 
 at least one of R 8  to R 14 , is selected from substituted or unsubstituted phenyl, substituted or unsubstituted napthyl, or substituted or unsubstituted pyridyl; 
 n has a value of at least 1; and 
 m+n is the maximum number of ligands that may be attached to the metal; 
 provided that when n is 3, none of R 8  to R 14  is a cyano group. 
 
       
     
     
         22 . The compound of  claim 21 , wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag. 
     
     
         23 . The compound of  claim 21 , wherein M is Ir. 
     
     
         24 . The compound of  claim 21 , wherein m has a value of 0. 
     
     
         25 . The compound of  claim 21 , wherein
 m has a value of at least 1; and   a ligand attached to the metal center has a different structure from at least one other ligand.   
     
     
         26 . The device of  claim 26 , wherein at least one ligand functions as a phosphorescent emissive ligand in the compound at room temperature and at least one ligand does not function as a phosphorescent emissive ligand in the compound at room temperature. 
     
     
         27 . The compound of  claim 21 , wherein at least one of R 9 , R 10 , R 13 , and R 14  is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl. 
     
     
         28 . The compound of  claim 21 , wherein the compound has one of the following structures: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         29 . The compound of  claim 21 , wherein the ligands are in facial configuration with respect to the coordinating atoms of the ligands. 
     
     
         30 . The compound of  claim 21 , wherein the ligand 
       
         
           
           
               
               
           
         
       
       and m is 1 or 2. 
     
     
         31 . An organic light emitting device, comprising:
 an anode;   a cathode; and   an emissive layer disposed between the anode and the cathode, the emissive layer comprising a compound having the structure:   
       
         
           
           
               
               
           
         
       
       wherein
 M is a metal having an atomic weight greater than 40; 
 (C—N) is a substituted or unsubstituted cyclometallated ligand; 
 each of R 8  through R 14  is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , NO 2 , halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; or 
 any two adjacent substituted positions R 8  through R 14  can form a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the formed 4- to 7-member cyclic group is optionally substituted; 
 at least one of R 8  to R 14 , is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl; 
 n has a value of at least 1; and 
 m+n is the maximum number of ligands that may be attached to the metal; 
 provided that when n is 3, none of R 8  to R 14  is a cyano group. 
 
     
     
         32 . A compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein 
         M is a metal having an atomic weight greater than 40; 
         (C—N) is a substituted or unsubstituted cyclometallated ligand; 
         each of R 8 , R 9 , R 10 , R 11 , R 12 , and R 14  is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , NO 2 , halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; or 
         any two adjacent substituted positions R 8 , R 9 , R 10 , R 11 , R 12 , and R 14  can form a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the formed 4- to 7-member cyclic group is optionally substituted; 
         X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF 3 , NO 2 , halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, and heterocyclic group 
         n has a value of at least 1; and 
         m+n is the maximum number of ligands that may be attached to the metal; 
         provided that when n is 3, none of R 8 , R 9 , R 10 , R 11 , R 12 , and R 14  is a cyano group. 
       
     
     
         33 . The compound of  claim 32 , wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag. 
     
     
         34 . The compound of  claim 32 , wherein M is Ir. 
     
     
         35 . The compound of  claim 32 , wherein m has a value of 0. 
     
     
         36 . The compound of  claim 32 , wherein
 m has a value of at least 1; and   a ligand attached to the metal center has a different structure from at least one other ligand.   
     
     
         37 . The compound of  claim 36 , wherein at least one ligand functions as a phosphorescent emissive ligand in the compound at room temperature and at least one ligand does not function as a phosphorescent emissive ligand in the compound at room temperature. 
     
     
         38 . The compound of  claim 32 , wherein the ligand 
       
         
           
           
               
               
           
         
       
       is of formula 
       
         
           
           
               
               
           
         
       
       and m is 1 or 2. 
     
     
         39 . An organic light emitting device, comprising:
 an anode;   a cathode; and   an emissive layer disposed between the anode and the cathode, the emissive layer comprising a compound of  claim 32 .