Method for synthesizing anthracene derivative and anthracene derivative, light emitting element, light emitting device, electronic device

Abstract

It is an object to provide a novel method for synthesizing an anthracene derivative with the small number of steps. It is another object to provide a novel anthracene derivative. It is further another object to provide a light-emitting element, a light-emitting device, and an electronic device, each using the anthracene derivative. A method for synthesizing an anthracene derivative represented by a general formula (1) is provided by coupling a 9-arylanthracene derivative having an active site at a 10-position with a 9-arylcarbazole derivative having an active site in an aryl group using metal, a metal compound, or a metal catalyst.

1 . A method for synthesizing an anthracene derivative represented by a general formula (1) comprising the steps of: 
 coupling a 9-arylanthracene derivative having a first active site at a 10-position with a 9-arylcarbazole derivative having a second active site in an aryl group, by using metal or a metal compound,                          wherein each of R 1  to R 8  in the formula represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms,    wherein Ar 1  in the formula represents an aryl group having 6 to 25 carbon atoms,    wherein Ar 2  in the formula represents an arylene group having 6 to 25 carbon atoms, and    wherein each of A 1  and A 2  in the formula represents hydrogen, an aryl group having 6 to 25 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.    
     
     
         2 . A method for synthesizing an anthracene derivative represented by a general formula (1) comprising the steps of: 
 coupling an anthracene derivative represented by a general formula (2) with a carbazole derivative represented by a general formula (3), by using metal or a metal compound,                          wherein each of R 1  to R 8  in the formula represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms,    wherein Ar 1  in the formula represents an aryl group having 6 to 25 carbon atoms,    wherein Ar 2  in the formula represents an arylene group having 6 to 25 carbon atoms,    wherein each of A 1  and A 2  in the formula represents hydrogen, an aryl group having 6 to 25 carbon atoms, or an alkyl group having 1 to 4 carbon atoms, and    wherein X 3  in the formula represents a first active site, and    wherein X 6  in the formula represents a second active site.    
     
     
         3 . The method according to  claim 1  or  2 , wherein the metal or the metal compound is used as a catalyst.  
     
     
         4 . The method according to  claim 1  or  2 , wherein the metal is copper or iron.  
     
     
         5 . The method according to  claim 1  or  2 , wherein the metal compound is copper iodide.  
     
     
         6 . The method according to  claim 4 , wherein the catalyst is a palladium catalyst or a nickel catalyst.  
     
     
         7 . The method according to  claim 1  or  2 , 
 wherein the first active sites is halogen, and    wherein the second active site is boronic acid or organoboron.    
     
     
         8 . The method for synthesizing an anthracene derivative represented by a general formula (1) comprising the steps of: 
 coupling 9-aryl-10-anthracene halide with (carbazol-9-yl)arylboronic acid using a metal catalyst,                          wherein each of R 1  to R 8  in the formula represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms,    wherein Ar 1  in the formula represents an aryl group having 6 to 25 carbon atoms,    wherein Ar 2  in the formula represents an arylene group having 6 to 25 carbon atoms, and    wherein each of A 1  and A 2  in the formula represents hydrogen, an aryl group having 6 to 25 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.    
     
     
         9 . The method according to  claim 8 , wherein the metal catalyst is a palladium catalyst.  
     
     
         10 . An anthracene derivative represented by a structural formula (43).  
       
         
           
           
               
               
           
         
       
     
     
         11 . An anthracene derivative represented by a structural formula (16).  
       
         
           
           
               
               
           
         
       
     
     
         12 . A light-emitting element comprising the anthracene derivative according to  claim 10  or  11  between a pair of electrodes.  
     
     
         13 . A light-emitting element comprising a light-emitting layer between a pair of electrodes, 
 wherein the light-emitting layer includes the anthracene derivative according to  claim 10  or  11 .    
     
     
         14 . A light-emitting element comprising a light-emitting layer between a pair of electrodes, 
 wherein the light-emitting layer includes the anthracene derivative according to  claim 10  or  11 , and    wherein the anthracene derivative emits light.    
     
     
         15 . A light-emitting device comprising: 
 the light-emitting element according to  claim 13;  and    a controller for controlling light emission of the light-emitting element.    
     
     
         16 . An electronic device comprising a display portion, 
 wherein the display portion is provided with a light-emitting element according to  claim 10  or  11  and a controller for controlling light emission of the light-emitting element.