Benzimidazole compound organic photoelectric device including the same, and display element including the same

Abstract

A benzimidazole compound, an organic photoelectric device, and a display element, the benzimidazole compound being represented by the following Chemical Formula 1:

1 . A benzimidazole compound represented by the following Chemical Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         A is CR″ or N wherein R″ is hydrogen or a C1 to C10 alkyl, Ar 1  to Ar 2  are each independently one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene, 
         x and y are each independently an integer of 0 to 5, provided that 1≦x+y≦5, 
         R is hydrogen or a C1 to C7 alkyl, 
         n is an integer of 0 to 3, 
         R′ is one selected from the group of a substituted or unsubstituted C1 to C50 alkyl and a substituted or unsubstituted C6 to C50 aryl, and 
         m is 1 or 2. 
       
     
     
         2 . The benzimidazole compound as claimed in  claim 1 , wherein R′ in the above Chemical Formula 1 is a substituted or unsubstituted C6 to C50 aryl. 
     
     
         3 . The benzimidazole compound as claimed in  claim 1 , wherein the benzimidazole compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2: 
       
         
           
           
               
               
           
         
         wherein, in the above Chemical Formula 2, 
         A is CR″ or N wherein R″ is hydrogen or a C1 to C10 alkyl, 
         Ar 1  to Ar 2  are each independently one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene, 
         x and y are each independently integers of 0 to 5, provided that 1≦x+y≦5, 
         n is an integer of 0 to 3, 
         R 1 ′ to R 5 ′ are each independently one selected from the group of hydrogen, a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20 acyloxy, a substituted or unsubstituted C2 to C20 heteroaryloxy, a substituted or unsubstituted C7 to C20 aryloxycarbonyl amino, a substituted or unsubstituted C1 to C20 sulfamoyl amino, a substituted or unsubstituted C1 to C20 sulfonyl, a substituted or unsubstituted C1 to C20 alkylthiol, a substituted or unsubstituted C6 to C20 arylthiol, a substituted or unsubstituted C1 to C20 heterocyclothiol, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C1 to C20 phosphoric acid amide, and a substituted or unsubstituted C3 to C40 silyl, and 
         m is 1 or 2. 
       
     
     
         4 . The benzimidazole compound as claimed in  claim 1 , wherein Ar 1  to Ar 2  are each independently one selected from the group of a substituted or unsubstituted C6 to C30 arylamine and a substituted or unsubstituted carbazole. 
     
     
         5 . The benzimidazole compound as claimed in  claim 1 , wherein:
 x≧1,   y≧1,   one of Ar 1  and Ar 2  includes a substituted or unsubstituted C6 to C30 arylamine, and   another of Ar 1  and Ar 2  includes a substituted or unsubstituted carbazole.   
     
     
         6 . The benzimidazole compound as claimed in  claim 1 , wherein Ar 1  to Ar 2  are each independently represented by one of the following Chemical Formulae 3 to 33: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein in the above Chemical Formulae 3 to 33, 
         R 1  to R 76  are each independently one selected from the group of a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20 acyloxy, a substituted or unsubstituted C2 to C20 heteroaryloxy, a substituted or unsubstituted C7 to C20 aryloxycarbonyl amino, a substituted or unsubstituted C1 to C20 sulfamoyl amino, a substituted or unsubstituted C1 to C20 sulfonyl, a substituted or unsubstituted C1 to C20 alkylthiol, a substituted or unsubstituted C6 to C20 arylthiol, a substituted or unsubstituted C1 to C20 heterocyclothiol, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C1 to C20 phosphoric acid amide, and a substituted or unsubstituted C3 to C40 silyl, 
         n 1 , n 2 , n 4 , n 6 , n 10 , n 26 , n 27 , n 35 , n 39 , n 46 , n 47 , n 49 , n 53 , n 59 , n 61 , and n 62  are each independently integers of 0 to 5, 
         n 3 , n 5 , n 7 , n 8 , n 11 , n 12 , n 16 , n 22 , n 23 , n 29 , n 30 , n 31 , n 33 , n 36 , n 37 , n 40 , n 41  to n 44 , n 48 , n 50  to n 52 , n 54 , n 55 , n 57 , n 60 , n 63 , n 65 , and n 67  to n 73  are each independently integers of 0 to 4, 
         n 9 , n 13 , n 14 , n 18 , n 19 , n 20 , n 25 , n 28 , n 32 , n 34 , n 38 , n 45 , n 56 , n 58 , and n 66  are each independently integers of 0 to 3, and 
         n 17  and n 24  are each independently integers of 0 to 2. 
       
     
     
         7 . The benzimidazole compound as claimed in  claim 1 , wherein the benzimidazole compounds is a charge transporting material or a host material in an organic photoelectric device. 
     
     
         8 . The benzimidazole compound as claimed in  claim 1 , wherein the benzimidazole compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulae 34-40: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . An organic photoelectric device, comprising:
 an anode,   a cathode, and   at least one organic thin layer between the anode and cathode, the at least one organic thin layer including the benzimidazole compound as claimed in  claim 1 .   
     
     
         10 . The organic photoelectric device as claimed in  claim 9 , wherein the at least one organic thin layer is an emission layer. 
     
     
         11 . The organic photoelectric device as claimed in  claim 9 , wherein the at least one organic thin layer includes at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer. 
     
     
         12 . A display element comprising the organic photoelectric device as claimed in  claim 9 .