Asymmetric monoanthracene derivative, material for organic electroluminescent device and organic electroluminescent device utilizing the same

Abstract

Provided are an asymmetric monoanthracene derivative having a specific structure, a material for an organic EL device comprising the above asymmetric monoanthracene derivative and an organic EL device in which an organic thin film layer comprising a single layer or plural layers including a luminescent layer is interposed between a cathode and an anode, wherein at least one of the above organic thin film layers contains the asymmetric monoanthracene derivative described above in the form of a single component or a mixed component. Provided are an organic electroluminescent (EL) device having a high luminous efficiency and a long life, an asymmetric monoanthracene derivative which materializes the same and a material for an organic EL device.

1 - 13 . (canceled) 
     
     
         14 . An organic electroluminescent device in which an organic thin film layer comprising a single layer or plural layers including a luminescent layer is interposed between a cathode and an anode, wherein at least one of the above organic thin film layers contains an asymmetric monoanthracene derivative represented by formula (1) and an arylamine compound represented by the following Formula (B): 
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each are independently a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and m and n each are an integer of 1 to 4, provided that when m and n are 1 and the bonding positions of Ar 1  and Ar 2  in the benzene wrings are symmetric in right and left, Ar 1  is not the same as Ar 2  and that when m or n is an integer of 2 to 4, m and n are different integers;
 R 1  to R 8  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 5 to 50 nuclear carbon atoms, a substituted or non-substituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; 
 R 9  and R 10  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 5 to 50 nuclear carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and any groups are not an alkenyl group; and 
 R 1  to R 10 , Ar 1  and Ar 2  are not an anthracenyl group and fluorenyl group, 
 
       
         
           
           
               
               
           
         
       
       wherein in formula (B):
 Ar 6  to Ar 8  each independently represents a substituted or unsubstituted aryl group having 5 to 40 carbon atoms forming the aromatic ring, and q represents an integer of 1 to 4. 
 
     
     
         15 . The organic electroluminescent device as described in  claim 14 , wherein the Formula (1) is the following Formula (2): 
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each are independently a substituted or non-substituted aromatic hydrocarbon rang group having 6 to 50 nuclear carbon atoms, and n is an integer of 1 to 4, provided that when n is 1 and the bonding positions of Ar 1  and Ar 2  in the benzene ring are symmetric in right and left, Ar 1  is not the same as Ar 2 ;
 R 1  to R 8  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon rang group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; 
 R 9  and R 10  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and any groups are not an alkenyl group; and 
 R 1  to R 10 , Ar 1  and Ar 2  are not an anthracenyl group and fluorenyl group. 
 
     
     
         16 . The organic electroluminescent device as described in  claim 14 , wherein the Formula (1) is the following Formula (3): 
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each are independently a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and n is an integer of 1 to 4, provided that when n is 1 and the bonding positions of Ar 1  and Ar 2  in the benzene ring are symmetric in right and left, Ar 1  is not the same as Ar 2 ;
 R 1  to R 8  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; 
 R 9  and R 10  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and any groups are not an alkenyl group; and 
 R 1  to R 10 , Ar 1  and Ar 2  are not an anthracenyl group and fluorenyl group. 
 
     
     
         17 . The organic electroluminescent device as described in  claim 14 , wherein the Formula (1) is the following Formula (4): 
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  each are independently a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and n is an integer of 1 to 4, provided that when n is 1 and the bonding positions of Ar 1  and Ar 2  in the benzene ring are symmetric in right and left, Ar 1  is not the same as Ar 2 ;
 R 1  to R 8  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; 
 R 9  and R 10  each are independently a hydrogen atom, a substituted or non-substituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 nuclear atoms, a substituted or non-substituted arylthio group having 5 to 50 nuclear atoms, a substituted or non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or non-substituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and any groups are not an alkenyl group; and 
 R 1  to R 10 , Ar 1  and Ar 2  are not an anthracenyl group and fluorenyl group. 
 
     
     
         18 . The organic electroluminescent device as described in  claim 14 , wherein in Formula (1), Ar 1  and Ar 2  described above each are independently any of phenyl, 1-naphthyl, 2-naphthyl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyxenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-tolyl, m-tolyl, p-tolyl and p-t-butylphenyl. 
     
     
         19 . The organic electroluminescent device as described in  claim 14 , wherein in Formula (1), Ar 1  and Ar 2  described above each are independently any of phenyl, 1-naphthyl, 2-naphthyl and 9-phenanthryl. 
     
     
         20 . The organic electroluminescent device as described in  claim 14 , wherein the asymmetric monoanthracene derivative represented by formula (1) is a host material.