Synthesis of Four Coordinated Palladium Complexes and Their Applications in Light Emitting Devices Thereof

Abstract

Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof.

What is claimed is: 
     
         1 . A compound represented by the formula: 
       
         
           
           
               
               
           
         
         wherein each R 1  and R 2  in (R 1 ) 2  and (R 2 ) 2  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         R 3  represents methyl, ethyl, propyl, or butyl; 
         Y 1a  represents O, S, NR 4a , wherein R 4a  represents optionally substituted C 1 -C 4  alkyl; Si(R 4b ) 2 , wherein each R 4b  in (R 4b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 4c ) 2 , wherein each R 4c  in (R 4c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         n is an integer 0 or 1; 
         Y 1b , when present, represents O, S, NR 5a , wherein R 5a  represents optionally substituted C 1 -C 4  alkyl; Si(R 5b ) 2 , wherein each R 5b  in (R 5b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 5c ) 2 , wherein each R 5c  in (R 5c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         each of Y 2a , Y 2b , Y 2c , and Y 2d  independently represents N, NR 6a , or CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , and Y 4d  independently represents N, O, S, NR 6a , CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; or Z(R 6c ) 2 , wherein Z is C or Si, and wherein each R 6c  in (R 6c ) 2  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
       
       wherein m is an integer 1 or 2;
 wherein the open dotted circle 
 
       
         
           
           
               
               
           
         
       
       indicates partial or full unsaturation of the ring with which it is associated;
 provided that if m is 1, each of Y 2a  and Y 2d  is CH and each of Y 2b  and Y 2c  is N, then at least one of Y 4a , Y 4b , Y 3a , or Y 3d  is not N; and 
 provided that if n is 0, m is 2, each of Y 2a  and Y 2d  is CH, and each of Y 2b  and Y 2c  is N, then at least one of Y 3b  or Y 3c  is not N. 
 
     
     
         2 . The compound of  claim 1 , which is represented by the formula: 
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 1 , which is represented by the formula: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , which is represented by the formula: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 1 , which is represented by the formula: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , which is represented by the formula: 
       
         
           
           
               
               
           
         
       
     
     
         7 . An organic light-emitting diode (OLED) comprising, as an emissive material, a compound represented by the formula: 
       
         
           
           
               
               
           
         
         wherein each R 1  and R 2  in (R 1 ) 2  and (R 2 ) 2  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         R 3  represents methyl, ethyl, propyl, or butyl; 
         Y 1a  represents O, S, NR 4a , wherein R 4a  represents optionally substituted C 1 -C 4  alkyl; Si(R 4b ) 2 , wherein each R 4b  in (R 4b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 4c ) 2 , wherein each R 4c  in (R 4c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         n is an integer 0 or 1; 
         Y 1b , when present, represents O, S, NR 5a , wherein R 5a  represents optionally substituted C 1 -C 4  alkyl; Si(R 5b ) 2 , wherein each R 5b  in (R 5b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 5c ) 2 , wherein each R 5c  in (R 5c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         each of Y 2a , Y 2b , Y 2c , and Y 2d  independently represents N, NR 6a , or CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , and Y 4d  independently represents N, O, S, NR 6a , CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; or Z(R 6c ) 2 , wherein Z is C or Si, and wherein each R 6  in (R 6c ) 2  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
       
       wherein m is an integer 1 or 2;
 wherein the open dotted circle 
 
       
         
           
           
               
               
           
         
       
       indicates partial or full unsaturation of the ring with which it is associated;
 provided that if m is 1, each of Y 2a  and Y 2d  is CH and each of Y 2b  and Y 2c  is N, then at least one of Y 4a , Y 4b , Y 3a , or Y 3d  is not N; and 
 
       provided that if n is 0, m is 2, each of Y 2a  and Y 2d  is CH, and each of Y 2b  and Y 2c  is N, then at least one of Y 3b  or Y 3c  is not N. 
     
     
         8 . An organic photovoltaic device comprising, as a donor or acceptor material, a compound represented by the formula: 
       
         
           
           
               
               
           
         
         wherein each R 1  and R 2  in (R 1 ) 2  and (R 2 ) 2  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         R 3  represents methyl, ethyl, propyl, or butyl; 
         Y 1a  represents O, S, NR 4a , wherein R 4a  represents optionally substituted C 1 -C 4  alkyl; Si(R 4b ) 2 , wherein each R 4b  in (R 4b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 4c ) 2 , wherein each R 4c  in (R 4c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         n is an integer 0 or 1; 
         Y 1b , when present, represents O, S, NR 5a , wherein R 5a  represents optionally substituted C 1 -C 4  alkyl; Si(R 5b ) 2 , wherein each R 5b  in (R 5b ) 2  independently represents optionally substituted C 1 -C 4  alkyl; or C(R 5c ) 2 , wherein each R 5c  in (R 5c ) 2  represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
         each of Y 2a , Y 2b , Y 2v , and Y 2d  independently represents N, NR 6a , or CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen, optionally substituted C 1 -C 4  alkyl, halogen, hydroxyl, amino, nitro, or thiol; 
         each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , and Y 4d  independently represents N, O, S, NR 6a , CR 6b , wherein each of R 6a  and R 6b  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; or Z(R 6c ) 2 , wherein Z is C or Si, and wherein each R 6c  in (R 6c ) 2  independently represents hydrogen or optionally substituted C 1 -C 4  alkyl; 
       
       wherein m is an integer 1 or 2;
 wherein the open dotted circle 
 
       
         
           
           
               
               
           
         
       
       indicates partial or full unsaturation of the ring with which it is associated;
 provided that if m is 1, each of Y 2a  and Y 2d  is CH and each of Y 2b  and Y 2c  is N, then at least one of Y 4a , Y 4b , Y 3a , or Y 3d  is not N; and 
 
       provided that if n is 0, m is 2, each of Y 2a  and Y 2d  is CH, and each of Y 2b  and Y 2c  is N, then at least one of Y 3b  or Y 3c  is not N.