Aromatic amine derivative and organic electroluminescent element using same

Abstract

An aromatic amine derivative represented by the following formula (1): wherein at least one of R 1 to R 8 is a group other than a hydrogen atom, Ar 1 to Ar 4 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

1 . An organic electroluminescence device comprising a cathode, an anode, and one or more organic thin film layers comprising an emitting layer therebetween,
 wherein at least one layer of the organic thin film layers comprises an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (10):   
       
         
           
           
               
               
           
         
         wherein R 1  to R 8  are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, 
         at least one of R 1  to R 5  is a group other than a hydrogen atom, and 
         Ar 1  to Ar 4  are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, at least one of Ar 1  to Ar 4  is an aryl group substituted with one or more substituents selected from a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group, 
         provided that, when at least one of Ar 1  to Ar 4  is a p-fluorophenyl group, at least one of Ar 1  to Ar 4  which are not a p-fluorophenyl group is an aryl group other than a p-fluorophenyl group which is substituted with one or more substituents selected from a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group and a carbonyl group, 
       
       
         
           
           
               
               
           
         
         wherein Ar 11  and Ar 12  are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and 
         R 101  to R 108  are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. 
       
     
     
         2 . The organic electroluminescence device according to  claim 1 , wherein the emitting layer comprises the aromatic amine derivative represented by the formula (1) and the anthracene derivative represented by the formula (10). 
     
     
         3 . The organic electroluminescence device according to  claim 1 , wherein the aromatic amine derivative represented by the formula (1) is represented by the following formula (2): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 8 , Ar 2  and Ar 4  are the same as those in the formula (1),
 R 11  to R 20  are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group, and 
 at least one of R 11  to R 15  is a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group, and at least one of R 16  to R 20  is a cyano group, a fluorine atom, a halogenated alkyl group, a nitro group or a carbonyl group 
 
     
     
         4 . The organic electroluminescence device according to  claim 3 , wherein one of R 11  to R 15  is a cyano group, and the remaining R 11  to R 15  are hydrogen atoms, and
 one of R 16  to R 20  is a cyano group, and the remaining R 16  to R 20  are hydrogen atoms.   
     
     
         5 . The organic electroluminescence device according to  claim 4 , wherein R 1 , R 3 , R 4 , R 5 , R 7  and R 5  are hydrogen atoms 
     
     
         6 . The organic electroluminescence device according to  claim 5 , wherein R 2  and R 6  are independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms. 
     
     
         7 . The organic electroluminescence device according to  claim 1 , wherein Ar 1  to Ar 4  are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar 1  to Ar 4  is an aryl group having one or more cyano groups. 
     
     
         8 . The organic electroluminescence device according to  claim 1 , wherein in the formula (10), Ar 11  and Ar 12  are independently a substituted or unsubstituted fused aromatic ring group having 10 to 30 ring carbon atoms. 
     
     
         9 . The organic electroluminescence device according to  claim 1 , wherein in the formula (10), Ar 11  is a substituted or unsubstituted phenyl group, and Ar 12  is a substituted or unsubstituted fused aromatic ring group having 10 to 30 ring carbon atoms. 
     
     
         10 . The organic electroluminescence device according to  claim 9 , wherein the anthracene derivative is represented by the following formula (10-4); 
       
         
           
           
               
               
           
         
       
       wherein R 101  to R 108  are the same as those in formula (10),
 R 111  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, 
 b is an integer of 0 to 7, and plural R 111 s may be the same or different when b is an integer of 2 or more, and 
 Ar 6  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or Ar 6  may form a ring with the benzene ring to which Ar 6  bonds. 
 
     
     
         11 . The organic electroluminescence device according to  claim 9 , wherein the anthracene derivative is represented by the following formula (10-5): 
       
         
           
           
               
               
           
         
         wherein R 101  to R 108  are the same as those in formula (10), 
         R 111  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, 
         b is an integer of 0 to 7, and plural R 111 s may be the same or different when b is an integer of 2 or more, and 
         Ar 7  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or Ar 7  may form a ring with the benzene ring to which Ar 7  bonds. 
       
     
     
         12 . The organic electroluminescence device according to  claim 1 , wherein the anthracene derivative is represented by the following formula (10-6): 
       
         
           
           
               
               
           
         
       
       wherein R 101  to R 108  are the same as those in the formula (10),
 Ar 8  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or Ar 8  may form a ring with the benzene ring to which Ar 8  bonds, and 
 Ar 9  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 
 
     
     
         13 . The organic electroluminescence device according to  claim 1 , wherein the anthracene derivative is represented by the following formula (10-7): 
       
         
           
           
               
               
           
         
       
       wherein R 101  to R 108  and Ar 12  are the same as those in the formula (10),
 L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, 
 R 121  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and 
 n is an integer of 0 to 11, and plural R 121 s may be the same or different when n is an integer of 2 or more. 
 
     
     
         14 . The organic electroluminescence device according to  claim 1 , wherein the anthracene derivative is represented by the following formula (10-8): 
       
         
           
           
               
               
           
         
       
       wherein R 101  to R 108  and Ar 12  are the same as those in the formula (10),
 L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 
 X 11  is an oxygen atom, a sulfur atom, or —NR— wherein R is the same as in R 101  to R 108 , 
 R 121  is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and 
 m is an integer of 0 to 7, and plural R 121 s may be the same or different when m is an integer of 2 or more. 
 
     
     
         15 . The organic electroluminescence device according to  claim 1 , wherein the anthracene derivative is represented by the following formula (10-9): 
       
         
           
           
               
               
           
         
         wherein R 101  to R 108  and Ar 12  are the same as those in the formula (10). 
       
     
     
         16 . The organic electroluminescence device according to  claim 1 , wherein the anthracene derivative is represented by the following formula (10-10): 
       
         
           
           
               
               
           
         
       
       wherein R 101  to R 108  and Ar 12  are the same as those in the formula (10). 
     
     
         17 . The organic electroluminescence device according to  claim 1 , wherein in the formula (10), Ar 11  and Ar 12  are independently a group formed by 1 to 4 hydrocarbon aromatic rings which may be substituted, and  R 101 to R 108  are independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a silyl group or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms.