Aromatic amine derivative and organic electroluminescent device using same

Abstract

Disclosed is an organic electroluminescence device in which an organic thin film which is composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. Since at least one layer of the organic thin film contains a novel aromatic amine derivative, which has an asymmetric structure wherein two different amine units are bonded through a linking group, by itself or as a component of a mixture, molecules are hardly crystallized, thereby improving the production yield of the organic electroluminescence device. This organic electroluminescence device has a long life.

1 . An organic electroluminescence device comprising an organic thin film layer comprising of one or more layers comprising at least a hole transporting layer and a light emitting layer, the organic thin film layer being interposed between a cathode and an anode, wherein the hole transporting layer comprises an aromatic amine derivative represented by the following general formula (1), and the light emitting layer comprises the arylamine compound represented by the following general formula (B):
   A-L-B  (1)
   where:
 L represents a linking group composed of a substituted or unsubstituted arylene group having 5 to 50 ring atoms, or a linking group obtained by bonding multiple substituted or unsubstituted arylene groups each having 5 to 50 ring atoms through a single bond, an oxygen atom, a sulfur atom, a nitrogen atom, or a saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 20 ring carbon atoms; 
 A represents a diarylamino group represented by the following general formula (2); and 
 B represents a diarylamino group represented by the following general formula (3) provided that A and B are not identical to each other: 
   
       
         
           
           
               
               
           
         
         
           where Ar 1  to Ar 4  each independently represent a substituted or unsubstituted aryl group having 5 to 50 ring atoms provided that three or more of Ar 1  to Ar 4  represent aryl groups different from one another: 
         
       
       
         
           
           
               
               
           
         
         
           In the general formula (B), Ar 11  to Ar 13  each represent an aryl group which has 5 to 40 ring carbon atoms and which may be substituted, and q′ represents an integer of 1 to 4. 
         
       
     
     
         2 . The organic electroluminescence device of  claim 1 , wherein the light emitting layer further comprises the asymmetric anthracene represented by the following general formula (i), (ii) or (iv): 
       
         
           
           
               
               
           
         
         where:
 Ar represents a substituted or unsubstituted fused aromatic group having 10 to 50 ring carbon atoms; 
 Ar′ represents a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms; 
 X represents a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group. 
 a, b, and c each represent an integer of 0 to 4; and 
 n represents an integer of 1 to 3. In addition, when n represents 2 or more, anthracene nuclei in [ ] may be identical to or different from each other: 
 
       
       
         
           
           
               
               
           
         
         where:
 Ar 1  and Ar 2  each independently represent a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms. m and n each represent an integer of 1 to 4; provided that Ar 1  and Ar 2  are not identical to each other when m=n=1 and positions at which Ar 1  and Ar 2  are bound to a benzene ring are bilaterally symmetric, and m and n represent different integers when m or n represents an integer of 2 to 4; and 
 R 1  to R 10  each independently represent a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group: 
 
       
       
         
           
           
               
               
           
         
         where:
 A 1  and A 2  each independently represent a substituted or unsubstituted fused aromatic ring group having 10 to 20 ring carbon atoms; 
 Ar 1  and Ar 2  each independently represent a hydrogen atom, or a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms; 
 R 1  to R 10  each independently represent a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; and 
 the number of each of Ar 1 , Ar 2 , R 9 , and R 10  may be two or more, and adjacent groups may form a saturated or unsaturated cyclic structure; 
 provided that the case where groups symmetric with respect to the X-Y axis shown on central anthracene in the general formula (iv) bind to 9- and 10-positions of the anthracene does not occur. 
 
       
     
     
         3 . The organic electroluminescence device of  claim 1 , wherein the Ar 3  and Ar 4  in the general formula (3) each independently represent a group represented by the following general formula (5): 
       
         
           
           
               
               
           
         
         where Ar 6  represents a substituted or unsubstituted aryl group having 5 to 50 ring atoms. 
       
     
     
         4 . The organic electroluminescence device of  claim 1 , wherein a total number of the ring atoms of the aryl groups represented by Ar 1  to Ar 4  in the general formulae (2) and (3) is 45 to 72. 
     
     
         5 . The organic electroluminescence device of  claim 1 , wherein the aromatic amine derivative is the following compound H1: