Method for producting aromatic amino compound

Abstract

A method for producing aromatic amino compound (V): by synthesizing intermediate compound (IV): by the reaction of compound (I): H 2 N—R 1 with a mixture of halogenated aryl compounds (II): Ar 1 -X and (III): Ar 2 -X in the presence of a noble metal catalyst, followed by eliminating the substituent R 1 from the nitrogen atom in compound (IV) under an acidic condition or an alkaline condition or by addition of a reducing agent or an oxidizing agent. (R 1 : a substituent having 2 to 50 carbon atoms; Ar 1 and Ar 2 : a substituted or unsubstituted hydrocarbon group or heterocyclic group having 6 to 50 carbon atoms and the same with or different from each other; and X: a halogen group). The aromatic amino compound useful as the charge transporting material can be produced efficiently at a great yield without using highly toxic raw materials.

1 . A method for producing an aromatic amino compound represented by following general formula (V):  
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each independently represent a substituted or unsubstituted hydrocarbon group or heterocyclic group having 6 to 50 carbon atoms and may represent a same group or different groups, which comprises 
 synthesizing an intermediate compound for an aromatic amino compound which is represented by following general formula (IV):  
                     
 wherein R 1  represents a substituent having 2 to 50 carbon atoms, by reacting an amino compound represented by following general formula (I):  
 H 2 N—R 1   (I)  
 wherein R 1  is as defined above, with a mixture of halogenated aryl compounds represented by following general formulae (II) and (III):  
 Ar 1 -X  (II) Ar 2 -X  (III)  
 wherein Ar 1  and Ar 2  are as defines above, and X represents a halogen group, in a presence of a noble metal catalyst; and  
 eliminating the substituent represented by R 1  from the nitrogen atom in the compound represented by general formula (IV) either under an acidic condition or an alkaline condition or by addition of a reducing agent or an oxidizing agent.  
 
     
     
         2 . A method for producing an aromatic amino compound represented by following general formula (VII):  
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each independently represent a substituted or unsubstituted hydrocarbon group or heterocyclic group having 6 to 50 carbon atoms and may represent a same group or different groups, Ar 3  represents a substituted or unsubstituted aromatic residue group having 6 to 60 carbon atoms, and n represents an integer of 1 to 4, which comprises 
 reacting an intermediate compound for an aromatic amino compound which is represented by following general formula (V):  
                     
 wherein Ar 1  and Ar 2  are as defined above, and X represents a halogen group, with a mixture of halogenated aryl compounds represented by following general formula (VI):  
 Ar 3 -(X) n   (VI)  
 wherein Ar 3 , X and n are as defined above, in a presence of a noble metal catalyst.  
 
     
     
         3 . A method for producing an aromatic amino compound represented by following general formula (X):  
       
         
           
           
               
               
           
         
       
       wherein Ar 1  represents a substituted or unsubstituted hydrocarbon group or heterocyclic group having 6 to 50 carbon atoms, Ar 3  represents a substituted or unsubstituted aromatic residue group having 6 to 60 carbon atoms, and n represents an integer of 1 to 4, which comprises 
 synthesizing an intermediate compound of an aromatic amino compound represented by following general formula (VIII):  
                     
 wherein R 1  represents a substituent having 2 to 50 carbon atoms, and Ar 1  is as defined above, by reacting an amino compound represented by following general formula (I):  
 H 2 N—R 1   (I)  
 wherein R 1  is as defined above, with a halogenated aryl compound represented by following general formula (II):  
 Ar 1 -X  (II)  
 wherein Ar 1  is as defined above and X represents a halogen group, in a presence of a noble metal catalyst;  
 synthesizing another intermediate compound for an aromatic amino compound which is represented by following general formula (IX):  
                     
 wherein R 1 , Ar 1 , Ar 3  and n are as defined above, by reacting the compound represented by general formula (VIII) with a halogenated aryl compound represented by following general formula (VI):  
 Ar 3 -(X) n   (VI)  
 wherein Ar 3 , X and n are as defined above, in a presence of a noble metal catalyst; and  
 eliminating the substituent represented by R 1  from the nitrogen atom in the compound represented by general formula (IX) either under an acidic condition or an alkaline condition or by addition of a reducing agent.  
 
     
     
         4 . A method for producing an aromatic amino compound represented by general formula (VII):  
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each independently represent a substituted or unsubstituted hydrocarbon group or heterocyclic group having 6 to 50 carbon atom and may represent a same group or different groups, Ar 3  represents a substituted or unsubstituted aromatic residue group having 6 to 60 carbon atoms, and n represents an integer of 1 to 4, which comprises 
 reacting a compound represented by following general formula (X):  
                     
 wherein Ar 1 , Ar 3  and n are as defined above, with a halogenated aryl compound represented by following general formula (III):  
 Ar 2 -X  (III)  
 wherein Ar 2  is as defined above, and X represents a halogen group, in a presence of a noble metal catalyst.  
 
     
     
         5 . A method according to any one of  claims 1  to  4 , wherein the substituent represented by R 1  is a substituted or unsubstituted arylalkyl group.  
     
     
         6 . A method according to any one of  claims 1  to  4 , wherein the substituent represented by R 1  has carbonyl group.  
     
     
         7 . A method according to any one of  claims 1  to  4 , wherein Ar 1  and Ar 2  each independently represent a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group.  
     
     
         8 . A method according to any one of  claims 1  to  4 , wherein the aromatic amino compound is a charge transporting material.  
     
     
         9 . A method according to any one of  claims 1  to  4 , wherein the aromatic amino compound is a charge transporting material for organic electroluminescence devices.