Aromatic amine derivative and organic electroluminescence device utilizing the same

Abstract

Provided is a novel aromatic amine derivative with specified structure. Also provided is an organic electroluminescence device having one or more organic thin-film layers including at least a luminescent layer interposed between a cathod and an anode, in which at least one of the organic thin-film layers contains the above aromatic amine derivative alone or as a component of mixture. As a result, there is provided an organic electroluminescence device that has high emission luminance and high heat resistance, excelling in high-temperature storage ability and has long life, and provided an aromatic amine derivative for realizing the organic electroluminescence device.

1 . (canceled) 
     
     
         2 . An aromatic amine derivative represented by formula (1-a), (1-b), or (1-c): 
       
         
           
           
               
               
           
         
       
       in formula (1-a):
 each of Ar 8  to Ar 11  is independently selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar 8  to Ar 11  does not contain a vinyl group; 
 each of R 23  to R 26  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon 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 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group; and 
 an optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 8  to Ar 11  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 40 ring carbon atoms, an amino group substituted by an aryl group having 5 to 40 ring carbon atoms, a cyano group, a nitro group, and a halogen atom; 
 
       in formula (1-b):
 each of Ar 12  to Ar 15  is independently selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar 12  to Ar 15  does not contain a vinyl group; 
 each of R 27  to R 32  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon 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 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group; and 
 an optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 12  to Ar 15  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 40 ring carbon atoms, an amino group substituted by an aryl group having 5 to 40 ring carbon atoms, a cyano group, a nitro group, and a halogen atom; 
 
       in formula (1-c):
 each of Ar 16  to Ar 19  is independently selected from the group consisting of a substituted or unsubstituted aryl group having 5 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, provided that each of Ar 16  to Ar 19  does not contain a vinyl group; 
 each of R 33  to R 40  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon 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 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group; and 
 an optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 16  to Ar 19  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 40 ring carbon atoms, an amino group substituted by an aryl group having 5 to 40 ring carbon atoms, a cyano group, a nitro group, and a halogen atom. 
 
     
     
         3 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-a) wherein:
 the aryl group represented by each of Ar 8  to Ar 11  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted; and   the heterocyclic group represented by each of Ar 8  to Ar 11  is a pyridinyl group optionally substituted.   
     
     
         4 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-b) wherein:
 the aryl group represented by each of Ar 12  to Ar 15  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted; and   the heterocyclic group represented by each of Ar 12  to Ar 15  is a pyridinyl group optionally substituted.   
     
     
         5 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-c) wherein:
 the aryl group represented by each of Ar 16  to Ar 19  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted; and   the heterocyclic group represented by each of Ar 16  to Ar 19  is a pyridinyl group optionally substituted.   
     
     
         6 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-a) wherein each of R 23  to R 26  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted silyl group. 
     
     
         7 . The aromatic amine derivative according to  claim 6 , wherein:
 the aryl group is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted;   the alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a cyclopentyl group, and a cyclohexyl group, each optionally substituted; and   the substituted silyl group is selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group.   
     
     
         8 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-b) wherein each of R 27  to R 32  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted silyl group. 
     
     
         9 . The aromatic amine derivative according to  claim 8 , wherein
 the aryl group is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted;   the alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a cyclopentyl group, and a cyclohexyl group, each optionally substituted; and   the substituted silyl group is selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group.   
     
     
         10 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-c) wherein each of R 33  to R 40  is independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted silyl group. 
     
     
         11 . The aromatic amine derivative according to  claim 10 , wherein:
 the aryl group is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, and a fluorenyl group, each optionally substituted;   the alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a cyclopentyl group, and a cyclohexyl group, each optionally substituted; and   the substituted silyl group is selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyklimethylsilyl group, and a propyldimethylsilyl group.   
     
     
         12 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-a) wherein the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 8  to Ar 11  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms. 
     
     
         13 . The aromatic amine derivative according to  claim 12 , wherein:
 the alkyl group is selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, and a cyclohexyl group; and   the alkoxy group is selected from the group consisting of a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group, a hexyloxy group, a cyclopentoxy group, and a cyclohexyloxy group.   
     
     
         14 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-b) wherein the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 12  to Ar 15  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms. 
     
     
         15 . The aromatic amine derivative according to  claim 14 , wherein:
 the alkyl group is selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, and a cyclohexyl group; and   the alkoxy group is selected from the group consisting of a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group, a hexyloxy group, a cyclopentoxy group, and a cyclohexyloxy group.   
     
     
         16 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-c) wherein the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 16  to Ar 19  is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms. 
     
     
         17 . The aromatic amine derivative according to  claim 16 , wherein:
 the alkyl group is selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, and a cyclohexyl group; and   the alkoxy group is selected from the group consisting of a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group, a hexyloxy group, a cyclopentoxy group, and a cyclohexyloxy group.   
     
     
         18 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-a) wherein:
 each of Ar 8  to Ar 11  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a fluorenyl group, and a pyridinyl group, each optionally substituted;   each of R 23  to R 26  is independently selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, a biphenyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a trimethylsilyl group, and a triethylsilyl group; and   the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 8  to Ar 11  is independently selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an isopropoxy group, a n-propoxy group, a s-butoxy group, and a t-butoxy group.   
     
     
         19 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-b) wherein:
 each of Ar 12  to Ar 15  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a fluorenyl group, and a pyridinyl group, each optionally substituted;   each of R 27  to R 32  is independently selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, a biphenyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a trimethylsilyl group, and a triethylsilyl group; and   the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 12  to Ar 15  s independently selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an isopropoxy group, a n-propoxy group, a s-butoxy group, and a t-butoxy group.   
     
     
         20 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is represented by formula (1-c) wherein:
 each of Ar 16  to Ar 19  is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a fluorenyl group, and a pyridinyl group, each optionally substituted;   each of R 33  to R 40  is independently selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, a biphenyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a trimethylsilyl group, and a triethylsilyl group; and   the optional substituent of the aryl group having 5 to 40 ring carbon atoms and the heterocyclic group having 5 to 40 ring atoms each represented by Ar 16  to Ar 19  is independently selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an isopropoxy group, a n-propoxy group, a s-butoxy group, and a t-butoxy group.   
     
     
         21 . The aromatic amine derivative according to  claim 2 , wherein the aromatic amine derivative is any one of the following compounds: