Organic electroluminescence device and phenylenediamine derivative

Abstract

The invention is to provide an organic EL device having a long life time that can reduce the driving voltage of the organic EL device, and to provide a material having a small ionization potential and exhibiting a large hole mobility by using as a layer or a zone. The organic electroluminescence device comprises a pair of electrodes and an organic light emitting layer sandwiched in the electrodes, characterized in that a hole transporting zone provided between the electrodes comprises the phenylenediamine derivative represented by the specific structural formulae, and the phenylenediamine derivative has a hole mobility of 10 −4 cm 2 /V·s or more upon using as a layer or a zone, with the organic light emitting layer containing a charge injection auxiliary.

1 . An organic electroluminescence device comprising a pair of electrodes and an organic light emitting layer sandwiched in said electrodes, 
 characterized in that a hole transporting zone provided between said electrodes comprises a phenylenediamine derivative represented by the general formula (I), the general formula (II) or the general formula (II)′, said phenylenediamine derivative exhibits a hole mobility of 10 −4  cm 2 /V·s on using as a layer or a zone, and said organic light emitting layer contains a charge injection auxiliary.                          (Ar 1  to Ar 6  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atoms, an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. X represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, a substituted or unsubstituted vinyl bond, or an aromatic heterocyclic ring. R 1  and R 2  represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring.)                          (Ar 7  to Ar 12  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. Y represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, an aromatic heterocyclic ring, or a substituted or unsubstituted vinyl bond. R 3  and R 4  represent an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring.)                          (Ar 7  to Ar 12  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. Y represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, an aromatic heterocyclic ring, or a substituted or unsubstituted vinyl bond. R 5  and R 6  represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring.)    
     
     
         2 . An organic electroluminescence device as described in  claim 1 , characterized in that said hole transporting zone is constituted by comprising a hole injection layer containing said phenylenediamine derivative represented by the general formula (I), the general formula (II) or the general formula (II)′.  
     
     
         3 . An organic electroluminescence device as described in  claim 1 , characterized in that said hole transporting zone is constituted by comprising a hole transporting layer containing said phenylenediamine derivative represented by the general formula (I), the general formula (II) or the general formula (II)′.  
     
     
         4 . An organic electroluminescence device as described in one of  claims 1  to  3 , 
 characterized in that at least one of Ar 1  to Ar 6  in the general formula (I), Ar 7  to Ar 12  in (II) and Ar 7  to Ar 12  in (II)′ is a condensed aromatic ring having from 10 to 24 nucleus carbon atoms.  
 
     
     
         5 . A phenylenediamine derivative represented by the general formula (III).  
       
         
           
           
               
               
           
         
       
       (Ar 13  to Ar 18  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. X represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, a substituted or unsubstituted vinyl bond, or an aromatic heterocyclic ring. R 7  and R 8  represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring, provided that at least one of Ar 13  to Ar 16  and X represents an aryl group containing a styryl group, or one of Ar 15 , Ar 18  and a basic skeleton shown by the following chemical formula contains a condensed aromatic ring, an aromatic heterocyclic ring or a substituted or unsubstituted vinyl group.)  
       
         
           
           
               
               
           
         
       
     
     
         6 . A phenylenediamine derivative represented by the general formula (IV) or  
       
         
           
           
               
               
           
         
       
       (Ar 19  to Ar 24  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. Y represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, an aromatic heterocyclic ring, or a substituted or unsubstituted vinyl bond. R 9  and R 10  represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring, provided that at least one of Ar 19  to Ar 24  and Y represents an aryl group containing a styryl group, or one of a basic skeleton shown by the following chemical formula contains a condensed aromatic ring, an aromatic heterocyclic ring or a substituted or unsubstituted vinyl group.)  
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
       
       (Ar 25  to Ar 30  represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group. Y represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, an aromatic heterocyclic ring, or a substituted or unsubstituted vinyl bond. R 11  and R 12  represent an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring.)  
     
     
         7 . An organic electroluminescence device comprising a pair of electrodes and an organic light emitting layer sandwiched in said electrodes, characterized in that a hole transporting zone provided between said electrodes comprises a phenylenediamine derivative represented by the general formula (III), the general formula (IV) or the general formula (V).