Material for organic electroluminescent element, and organic electroluminescent element

Abstract

A material for an organic electroluminescence device including at least one of compounds shown by the following formula (Ia), (Ib), (IIa), (IIb), (III), (IVa) or (IVb):

1 - 21 . (canceled) 
     
     
         22 . A compound shown by the following formula (Ia) or (Ib): 
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 1  to R 6  may be bonded to form a substituted aromatic ring, a heterocyclic ring, or a substituted heterocyclic ring, 
         and the substituent of the aromatic ring and heterocyclic ring is a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring. 
       
     
     
         23 . A compound shown by the following formula (IIa) or (IIb): 
       
         
           
           
               
               
           
         
       
       wherein R 7  to R 14 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and
 adjacent groups of R 7  to R 14  may be bonded to form a substituted aromatic ring, or a substituted heterocyclic ring, and the substituent thereof is selected from a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group and a heterocyclic ring. 
 
     
     
         24 . A compound shown by the following formula (IVa) or (IVb): 
       
         
           
           
               
               
           
         
       
       wherein R 30  to R 45 , which may be the same or different, are a hydrogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 30  to R 37  may be bonded to form an aromatic ring or a heterocylic ring, and the aromatic ring or the heterocyclic ring may have a substituent;
 providing that the compound shown by the formula (IVa) or the compound shown by the formula (IVb) contains 6 or more fluorine atoms in its structure. 
 
     
     
         25 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, wherein
 the organic thin film layer is a stack composed of a hole-injecting layer, a hole-transporting layer, an emitting layer and an electron-transporting layer being stacked sequentially from the anode, and   the hole-injecting layer comprises at least one of compounds shown by the following formula (Ia) or (Ib):   
       
         
           
           
               
               
           
         
         wherein R 1  to R 6 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 1  to R 6  may be bonded to form an aromatic ring or a heterocyclic ring, and the aromatic ring or the heterocyclic ring may have a substituent, 
         and the substituent is a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring. 
       
     
     
         26 . The organic electroluminescence device according to  claim 25 , wherein the hole-injecting layer further comprises a phenylenediamine compound shown by the following formula (V): 
       
         
           
           
               
               
           
         
       
       wherein R 61  to R 66 , which may be the same or different, are a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group, an aryl group or a heterocyclic ring, or may form a naphthalene skeleton, a carbazole skeleton or a fluorene skeleton with a phenyl group bonding to R 61  to R 66 ; and
 n is 1 or 2. 
 
     
     
         27 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, wherein
 the organic thin film layer is a stack composed of a hole-injecting layer, a hole-transporting layer, an emitting layer and an electron-transporting layer being stacked sequentially from the anode, and   the hole-injecting layer comprises at least one of compounds shown by the following formula (IIa) or (IIb):   
       
         
           
           
               
               
           
         
       
       wherein R 7  to R 14 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 7  to R 14  may be bonded to form a substituted aromatic ring, a heterocyclic ring, or a substituted heterocyclic ring. 
     
     
         28 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, wherein
 the organic thin film layer is a stack composed of a hole-injecting layer, a hole-transporting layer, an emitting layer and an electron-transporting layer being stacked sequentially from the anode, and   the hole-injecting layer comprises at least one of compounds shown by the following formula (IVa) or (IVb):   
       
         
           
           
               
               
           
         
       
       wherein R 30  to R 45 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 30  to R 37  may be bonded to form an aromatic ring or a heterocylic ring, and the aromatic ring or the heterocyclic ring may have a substituent;
 providing that the compound shown by the formula (IVa) or the compound shown by the formula (IVb) contains 6 or more fluorine atoms in its structure. 
 
     
     
         29 . A compound shown by the following formula (Ia) or (Ib): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 6 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 1  to R 6  may be bonded to form an aromatic ring or a heterocyclic ring, and the aromatic ring or the heterocyclic ring may have a substituent;
 providing that at least one of R 1  to R 6  is a fluorine atom, a fluoroalkyl group or a cyano group. 
 
     
     
         30 . A compound shown by the following formula (IIa) or (IIb): 
       
         
           
           
               
               
           
         
       
       wherein R 7  to R 14 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 7  to R 14  may be bonded to form an aromatic ring or a heterocyclic ring, and the aromatic ring or the heterocyclic ring may have a substituent;
 providing that at least one of R 7  to R 14  is a fluoroalkyl group or a cyano group. 
 
     
     
         31 . The device according to  claim 25  wherein adjacent groups of R 1  to R 6  may be bonded to form a substituted aromatic ring, a heterocyclic ring, or a substituted heterocyclic ring,
 and the substituent of the aromatic ring and heterocyclic ring is a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring. 
 
     
     
         32 . The device according to  claim 25  wherein at least one of R 1  to R 6  is a fluorine atom, a fluoroalkyl group or a cyano group. 
     
     
         33 . The device according to  claim 27  wherein adjacent groups of R 7  to R 14  may be bonded to form a substituted aromatic ring, or a substituted heterocyclic ring, and the substituent thereof is selected from a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group and a heterocyclic ring. 
     
     
         34 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, wherein
 the organic thin film layer is a stack composed of a hole-injecting layer, a hole-transporting layer, an emitting layer and an electron-transporting layer being stacked sequentially from the anode, and   the hole-injecting layer comprises at least one of compounds shown by the following formula (IIa) or (IIb):   
       
         
           
           
               
               
           
         
       
       wherein R 7  to R 14 , which may be the same or different, are a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a fluoroalkyl group, an alkoxy group, an aryloxy group or a heterocyclic ring; and adjacent groups of R 7  to R 14  may be bonded to form an aromatic ring or a heterocyclic ring, and the aromatic ring or the heterocyclic ring may have a substituent;
 providing that at least one of R 7  to R 14  is a fluorine atom, a fluoroalkyl group or a cyano group. 
 
     
     
         35 . The device according to  claim 34  wherein at least one of R 7  to R 14  is a fluoroalkyl group or a cyano group. 
     
     
         36 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer between the anode and the cathode, wherein
 the organic thin film layer is a stack composed of a hole-injecting layer, a hole-transporting layer, an emitting layer and an electron-transporting layer being stacked sequentially from the anode, and   the hole-injecting layer comprises the compound Formula IVa or IVb according to  claim 24 .