Triarylamine-based compound, method of preparing the same, and organic light emitting device using the triarylamine-based compound

Abstract

A triarylamine-based compound of formula 1, a method of preparing the same, and an organic light emitting device including the triarylamine-based compound of formula 1: where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; R is a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group; n is an integer of 1 through 3; and m is an integer of 1 through 3. The triarylamine-based compound of formula 1 has excellent electrical properties and a great charge transporting capability. An organic light emitting device including an organic layer formed of the triarylamine-based compound has high efficiency, low operating voltage, great luminance, and long lifetime.

1 . A triarylamine-based compound of formula 1:  
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group;  
         each R is independently a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group;  
         n is an integer of 1 through 3; and  
         m is an integer of 1 through 3.  
       
     
     
         2 . The triarylamine-based compound of  claim 1 , wherein each of Ar 1  through Ar 4  is independently selected from the group consisting of a phenyl group, a methylphenyl group, a dimethyl group, a trimethyl group, an ethylphenyl group, an ethylbiphenyl, an o-, m-or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-or p-tolyl group, an o-, m-or p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene) phenyl group, a (N,N′-dimethyl) aminophenyl group, a (N,N′-diphenyl) aminophenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azurenyl group, a heptarenyl group, an acenaphthylrenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl group, a methyl anthryl group, a phenanthrenyl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a lower alkylcarbazolyl group, a biphenyl group, a lower alkyl phenyl group, a lower alkoxy phenyl group, a thiophenyl group, an indolyl group, and a pyridyl group.  
     
     
         3 . The triarylamine-based compound of  claim 1 , wherein each of Ar 1  through Ar 4  is an aryl group having one, two, or three substituents selected from the group consisting of a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, a phenoxy group, a phenyl group, and a halogen atom, wherein the aryl group is a phenyl group or a naphthyl group.  
     
     
         4 . The triarylamine-based compound of  claim 1 , represented by formula 2:  
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are as described in  claim 1 , and R is a C1-C10 alkyl group.  
       
     
     
         5 . The triarylamine-based compound of  claim 4 , wherein each of Ar 1  through Ar 4  is selected from the group consisting of a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 3,5-dimethylphenyl group, a 4-chloro phenyl group, a 3-chlorophenyl group, a 2-chlorophenyl group, a 4-methoxy phenyl group, a 3-methoxyphenyl group, a 2-methoxyphenyl group, a 4-butylphenyl group, a 4-ethylphenyl group, a 3-ethylphenyl group, a 2-ethylphenyl group, a 3,5-diethylphenyl group, a 4-isopropylphenyl group, a 3-isopropylphenyl group, a 2-isopropylphenyl group, a 3,5-diisopropylphenyl group, a 4-bromophenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-octyphenyl group, a 3-octyphenyl group, a 2-octyphenyl group, a 2,4-dioctyl phenyl group, a 2,6-dimethylphenyl group, a 2,4,4-trimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and 
 R is a methyl group.    
     
     
         6 . The triarylamine-based compound of  claim 4 , wherein Ar 1  and Ar 2  are the same and Ar 1  and Ar 2  are selected from the group consisting of a phenyl group, a 4-butylphenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 3,5-diethylphenyl group, a 4-cyanophenyl group, a 4-methoxyphenyl group, a 2,4-dimethylphenyl group, and a 2,4,6-trimethylphenyl group; 
 Ar 3  and Ar 4  are the same and Ar 3  and Ar 4  are selected from the group consisting of a phenyl group, a 4-methoxyphenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and    R is a methyl group.    
     
     
         7 . The triarylamine-based compound of  claim 1 , represented by formula 3:  
       
         
           
           
               
               
           
         
         where each of Ar 1  through Ar 4  is as described in  claim 1 , and R is a C1-C10 alkyl group.  
       
     
     
         8 . The triarylamine-based compound of  claim 7 , wherein Ar 1  through Ar 4  are the same and Ar 1  through Ar 4  are selected from the group consisting of a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 3,5-dimethylphenyl group, a 4-chloro phenyl group, a 3-chlorophenyl group, a 2-chlorophenyl group, a 4-methoxy phenyl group, a 3-methoxyphenyl group, a 2-methoxyphenyl group, a 4-butylphenyl group, a 4-ethylphenyl group, a 3-ethylphenyl group, a 2-ethylphenyl group, a 3,5-diethylphenyl group, a 4-isopropylphenyl group, a 3-isopropylphenyl group, a 2-isopropylphenyl group, a 3,5-diisopropylphenyl group, a 4-bromophenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-octyphenyl group, a 3-octyphenyl group, a 2-octyphenyl group, a 2,4-dioctyl phenyl group, a 2,6-dimethylphenyl group, a 2,4,4-trimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and 
 R is a methyl group.    
     
     
         9 . The triarylamine-based compound of  claim 6 , wherein Ar 1  and Ar 2  are the same and Ar 1  and Ar 2  are selected from the group consisting of a phenyl group, a 4-butylphenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 3,5-diethylphenyl group, a 4-cyanophenyl group, a 4-methoxyphenyl group, a 2,4-dimethylphenyl group, and a 2,4,6-trimethylphenyl group; 
 Ar 3  and Ar 4  are the same and Ar 3  and Ar 4  are selected from the group consisting of a phenyl group, a 4-butylphenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and    R is a methyl group.    
     
     
         10 . The triarylamine-based compound of  claim 1 , represented by formula 4:  
       
         
           
           
               
               
           
         
         where each of Ar 1  through Ar 4  is as described in  claim 1 , and R is a C1-C10 alkyl group.  
       
     
     
         11 . The triarylamine-based compound of  claim 10 , wherein Ar 1  through Ar 4  are the same and Ar 1  through Ar 4  are selected from the group consisting of a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 3,5-dimethylphenyl group, a 4-chloro phenyl group, a 3-chlorophenyl group, a 2-chlorophenyl group, a 4-methoxy phenyl group, a 3-methoxyphenyl group, a 2-methoxyphenyl group, a 4-butylphenyl group, a 4-ethylphenyl group, a 3-ethylphenyl group, a 2-ethylphenyl group, a 3,5-diethylphenyl group, a 4-isopropylphenyl group, a 3-isopropylphenyl group, a 2-isopropylphenyl group, a 3,5-diisopropylphenyl group, a 4-bromophenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-octyphenyl group, a 3-octyphenyl group, a 2-octyphenyl group, a 2,4-dioctyl phenyl group, a 2,6-dimethylphenyl group, a 2,4,4-trimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and 
 R is a methyl group.    
     
     
         12 . The triarylamine-based compound of  claim 10 , wherein Ar 1  and Ar 2  are the same and Ar 1  and Ar 2  are selected from the group consisting of a phenyl group, a 4-butylphenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 3,5-dimethylphenyl group, a 4-cyanophenyl group, a 4-methoxyphenyl group, a 2,4-dimethylphenyl group, and a 2,4,6-trimethylphenyl group; 
 Ar 3  and Ar 4  are the same and Ar 3  and Ar 4  are selected from the group consisting of a phenyl group, a 4-methoxy group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, and a 2-anthracenyl group; and    R is a methyl group.    
     
     
         13 . The triarylamine-based compound of  claim 1 , selected from the group consisting of the compounds represented by formulae below:  
       
         
           
           
               
               
           
         
       
     
     
         14 . An organic light emitting device, comprising: 
 a first electrode;    a second electrode; and    an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a triarylamine-based compound represented by Formula 1:                          where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group;    each R is independently a halogen atom, a cyano group, a substituted or unsubstituted Cl-C30 alkyl group;    n is an integer of 1 through 3; and    m is an integer of 1 through 3.    
     
     
         15 . The organic light emitting device of  claim 14 , wherein the organic layer is at least one selected from the group consisting of a hole injection layer, a hole transport layer, and an emission layer.  
     
     
         16 . The organic light emitting device of  claim 14 , wherein the organic layer comprises a layer having hole injecting and hole transporting capabilities.  
     
     
         17 . A method of preparing a triarylamine-based compound of formula 1,  
       
         
           
           
               
               
           
         
         the method comprising:  
         reacting compounds of formulae 8 through 10:  
         
           
             
             
                 
                 
             
           
         
           Ar 1 -NH-Ar 2   (9), and 
           Ar 3 -NH-Ar 4   (10), 
         where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group;  
         each R is independently a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group;  
         n is an integer of 1 through 3; and  
         m is an integer of 1 through 3.  
       
     
     
         18 . The method of  claim 17 , wherein the reaction is performed in the presence of tri(dibenzylideneacetone)dipalladium(0) at a reaction temperature of 50 to 150° C.  
     
     
         19 . The method of  claim 17 , wherein the compound of formula 8 is prepared by reacting a compound of formula 11 with butyl lithium and then by reacting the resultant product with copper chloride:  
       
         
           
           
               
               
           
         
         where R is a halogen atom, a cyano group, or a substituted or unsubstituted C1-C30 alkyl group;  
         n is an integer of 1 to 3; and  
         m is an integer of 1 through 3.  
       
     
     
         20 . The method of  claim 19 , wherein the reaction temperature for the preparation of the compound of formula 8 is in the range of −78° C. to 0.