Aromatic amine derivative and organic electroluminescent device using the same

Abstract

Provided are: an aromatic amine derivative in which a terminal substituent such as a dibenzofuran ring or a dibenzothiophene ring is bonded to a nitrogen atom directly or through an arylene group or the like; an organic electroluminescence device including an organic thin film layer formed of one or more layers including a light emitting layer and interposed between a cathode and an anode in which a layer of the organic thin film layer contains the aromatic amine derivative by itself or as a component of a mixture, and the device has a long lifetime and high luminous efficiency; and an aromatic amine derivative for realizing the device.

1 . An aromatic amine derivative represented by the following general formula (1): 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 0  represents a substituted or unsubstituted, divalent fused aromatic hydrocarbon group having 10 to 50 ring-forming carbon atoms, and 
 Ar 1  to Ar 4  each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, 
 provided that one, two or three of Ar 1  to Ar 4  each represent a group represented by formula (2): 
 
       
         
           
           
               
               
           
         
       
       wherein:
 n represents an integer of 0 to 3, m represents an integer of 0 to 5, 
 X represents oxygen (O), sulfur (S), or selenium (Se), Ar represents a substituted or unsubstituted arylene group having 6 to 60 ring-forming carbon atoms, 
 R represents a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a silyl group, or a carboxyl group, 
 when n or m represents 2 or more, multiple Ar's or multiple R's may be identical to or different from each other, and 
 when multiple R's are present, the multiple R's may be bonded to each other to form a saturated or unsaturated, five- or six-membered cyclic structure that may be substituted, provided that: 
 when n=0, a five-membered ring portion including X in the general formula (2) is free from being directly bonded to N bonded to Ar 0 . 
 
     
     
         2 . The aromatic amine derivative according to  claim 1 , wherein Ar 0  in the general formula (1) represents a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted pyrenylene group, or a substituted or unsubstituted benzoanthracenylene group. 
     
     
         3 . The aromatic amine derivative according to  claim 2 , wherein:
 —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 2- and 6-positions of the naphthylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 9- and 10-positions of the anthracenylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 2- and 6-positions of the anthracenylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 2- and 7-positions of the phenanthrylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 6- and 12-positions of the chrysenylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 1- and 6-positions of the pyrenylene group, respectively,   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 2- and 7-positions of the pyrenylene group, respectively, or   —NAr 1 Ar 2  and —NAr 3 Ar 4  are bonded to 7- and 12-positions of the benzoanthracenylene group, respectively.   
     
     
         4 . The aromatic amine derivative according to  claim 1 , wherein Ar 1  and Ar 3  each represent a group represented by the general formula (2). 
     
     
         5 - 6 . (canceled) 
     
     
         7 . The aromatic amine derivative according to  claim 1 , wherein n in formula (2) represents 0. 
     
     
         8 . The aromatic amine derivative according to  claim 1 , wherein m in formula (2) represents 0. 
     
     
         9 . The aromatic amine derivative according to  claim 1 , wherein x in formula (2) represents an oxygen atom. 
     
     
         10 . (canceled) 
     
     
         11 . The aromatic amine derivative according to  claim 1 , wherein X in formula (2) represents a sulfur atom. 
     
     
         12 . (canceled) 
     
     
         13 . The aromatic amine derivative according to  claim 1 , wherein R in formula (2) represents a silyl group. 
     
     
         14 . The aromatic amine derivative according to  claim 1 , wherein the aromatic amine derivative is a light emitting material for an organic electroluminescence device. 
     
     
         15 . The aromatic amine derivative according to  claim 1 , wherein the aromatic amine derivative is a blue light emitting material for an organic electroluminescence device. 
     
     
         16 . The aromatic amine derivative according to  claim 1 , wherein the aromatic amine derivative is a green light emitting material for an organic electroluminescence device. 
     
     
         17 . The aromatic amine derivative according to  claim 1 , wherein the aromatic amine derivative is a doping material for an organic electroluminescence device. 
     
     
         18 - 22 . (canceled)