Organic electroluminescent materials and devices

Abstract

A method of making an osmium(II) complex having Formula I, L 1 -Os-L 2 , wherein L 1 and L 2 are independently a biscarbene tridentate ligand, wherein L 1 and L 2 can be same or different is disclosed. The method includes (a) reacting a precursor of ligand L 1 with an osmium precursor to form an intermediate product, wherein the osmium precursor having the formula OsH x (PR 3 ) y , wherein x is an integer from 2 to 6 and y is an integer from 2 to 5, and R is selected from the group consisting of aryl, alkyl and cycloalkyl; and (b) reacting a precursor of ligand L 2 with said intermediate product.

We claim: 
     
         1 . A compound having a structure according to Formula I:
   L 1 -Os-L 2 ;   wherein L 1  and L 2  are different;   wherein L 1  and L 2  are independently selected from ligands having Formula II:   
       
         
           
           
               
               
           
         
         wherein:
 1) for L 1 , Y 1 , Y 2  and Y 3  comprise C and, for L 2 , either (i) Y 1  and Y 3  comprises C and Y 2  is N, or (ii) Y 1  and Y 3  are N, and Y 2  comprises C, or 
 2) for L 1 , Y 1  and Y 3  comprises C and Y 2  is N, and, for L 2 , Y 1  and Y 3  are N, and Y 2  comprises C; 
 
         wherein R 3  and R 4  may represent mono-, or di-substitutions, or no substitution; 
         wherein R 5  may represent mono-, di-, or tri-substitutions, or no substitution; 
         wherein R 1  and R 2  are independently selected from the group consisting of alkyl and cycloalkyl; 
         wherein R 3 , R 4  and R 5  are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; 
         wherein any two adjacent substituents of R 1 , R 2 , R 3 , R 4  and R 5  are optionally joined to condense into a fused ring; and 
         wherein the dash lines show the connection points to osmium. 
       
     
     
         2 . The compound of  claim 1 , wherein, for L 2 , Y 1  and Y 3  comprise C, and Y 2  is N. 
     
     
         3 . The compound of  claim 1 , wherein, for L 2 , Y 1  and Y 3  are N, and Y 2  comprise C. 
     
     
         4 . The compound of  claim 1 , wherein each R 1  and R 2  is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and partially or fully deuterated variants thereof. 
     
     
         5 . The compound of  claim 1 , wherein each R 1  and R 2  is independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof. 
     
     
         6 . The compound of  claim 1 , wherein L 1  and L 2  are independently selected from ligands having Formula III: 
       
         
           
           
               
               
           
         
         wherein each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7  and X 8  independently comprises C or N. 
       
     
     
         7 . The compound of  claim 1 , wherein each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7  and X 8  comprises C. 
     
     
         8 . The compound of  claim 1 , wherein ligand L 1  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 1 , wherein R 5  of L 1  is different from R 5  of L 2 . 
     
     
         10 . The compound of  claim 1 , wherein, for L 1 , Y 1 , Y 2  and Y 3  comprise C, and, for L 2 , Y 1  and Y 3  comprises C and Y 2  is N 
     
     
         11 . The compound of  claim 1 , wherein, for L 1 , Y 1 , Y 2  and Y 3  comprise C, and, for L 2 , Y 1  and Y 3  are N, and Y 2  comprises C. 
     
     
         12 . The compound of  claim 1 , wherein for L 1 , Y 1  and Y 3  comprises C and Y 2  is N, and, for L 2 , Y 1  and Y 3  are N, and Y 2  comprises C. 
     
     
         13 . A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a compound having the structure according Formula I
   L 1 -Os-L 2 ; 
   wherein L 1  and L 2  are different;   wherein L 1  and L 2  are independently selected from ligands having Formula II:   
       
         
           
           
               
               
           
         
         wherein:
 1) for L 1 , Y 1 , Y 2  and Y 3  comprise C and, for L 2 , either (i) Y 1  and Y 3  comprises C and Y 2  is N, or (ii) Y 1  and Y 3  are N, and Y 2  comprises C, or 
 2) for L 1 , Y 1  and Y 3  comprises C and Y 2  is N, and, for L 2 , Y 1  and Y 3  are N, and Y 2  comprises C; 
 wherein R 3  and R 4  may represent mono-, or di-substitutions, or no substitution; 
 wherein R 5  may represent mono-, di-, or tri-substitutions, or no substitution; 
 wherein R 1  and R 2  are independently selected from the group consisting of alkyl and cycloalkyl; 
 wherein R 3 , R 4  and R 5  are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof, 
 wherein any two adjacent substituents of R 1 , R 2 , R 3 , R 4  and R 5  are optionally joined to condense into a fused ring; and 
 wherein the dash lines show the connection points to osmium. 
 
       
     
     
         14 . The first device of  claim 13 , wherein the first device is a consumer product selected from the group consisting of light panels, flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, large area walls, theater or stadium screens, and signs. 
     
     
         15 . The first device of  claim 13 , wherein the first device is an organic light emitting device. 
     
     
         16 . The first device of  claim 13 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant. 
     
     
         17 . The first device of  claim 13 , wherein the organic layer further comprises a host material. 
     
     
         18 . The first device of  claim 17 , wherein the host material comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
 wherein any substituent in the host material is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and C n H 2n —Ar 1 ;   wherein n is from 1 to 10; and   wherein Ar 1  and Ar 2  are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.   
     
     
         19 . The first device of  claim 17 , wherein the host material comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. 
     
     
         20 . The first device of  claim 17 , wherein the host material is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof.