Aromatic amine derivatives and organic electroluminescent device using same

Abstract

The present invention provides a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer in the above organic thin film layer, particularly a hole injecting layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Use of the aromatic amine derivative described above materialize an organic electroluminescence device which reduces an operating voltage and makes molecules less liable to be crystallized and which enhances a yield in producing the organic EL device and has a long lifetime.

1 : An aromatic amine derivative represented by the following Formula (1):  
       
         
           
           
               
               
           
         
       
       wherein L 1  represents a substituted or non-substituted arylene group having 6 to 50 ring atoms; 
 at least one of Ar 1  to Ar 4  is represented by the following Formula (2):  
                     
 wherein R 1  is a substituted or non-substituted aryl group having 6 to 50 ring atoms, a branched or linear alkyl group having 1 to 50 carbon atoms, a halogen atom or a cyano group;  
 a is an integer of 1 to 3; and  
 L 2  represents a substituted or non-substituted arylene group having 6 to 50 ring atoms;  
 in Formula (1), among Ar 1  to Ar 4 , the groups which are not represented by Formula (2) each are independently a substituted or non-substituted aryl group having 6 to 50 ring atoms;  
 provided that substituents for Ar 1  to Ar 4  are an aryl group having 6 to 50 ring atoms, a branched or linear alkyl group having 1 to 50 carbon atoms, a halogen atom or a cyano group;  
 provided that there is no case in which a is 2 and in which two R 1  form a ring to be turned into a benzothiophenyl group.  
 
     
     
         2 : The aromatic amine derivative as described in  claim 1 , wherein Formula (2) described above is represented by the following Formula (3):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is a substituted or non-substituted aryl group having 6 to 50 ring atoms or a branched or linear alkyl group having 1 to 50 carbon atoms; and 
 L 2  represents a substituted or non-substituted arylene group having 6 to 50 ring atoms.  
 
     
     
         3 : The aromatic amine derivative as described in  claim 1  or  2 , wherein in Formula (1) described above, Ar 1  is represented by Formula (2) described above.  
     
     
         4 : The aromatic amine derivative as described in  claim 1  or  2 , wherein in Formula (1) described above, Ar 1  and Ar 2  are each independently represented by Formula (2) described above.  
     
     
         5 : The aromatic amine derivative as described in  claim 1  or  2 , wherein in Formula (1) described above, Ar 1  and Ar 3  are each independently represented by Formula (2) described above.  
     
     
         6 : The aromatic amine derivative as described in  claim 1  or  2 , wherein in Formula (1) described above, three or more of Ar 1  to Ar 4  are different from each other and wherein the aromatic amine compound is asymmetric.  
     
     
         7 : The aromatic amine derivative as described in  claim 1  or  2 , wherein in Formula (1) described above, three of Ar 1  to Ar 4  are the same and wherein the aromatic amine compound is asymmetric.  
     
     
         8 : The aromatic amine derivative as described in any of  claims 1  to  7 , wherein in Formula (1) described above, among Ar 1  to Ar 4 , the groups which are not represented by Formula (2) each are independently phenyl, biphenylyl, terphenylyl or fluorenyl.  
     
     
         9 : The aromatic amine derivative as described in any of  claims 1  to  8 , wherein in Formula (1) described above, L 1  is biphenylylene, terphenylylene or fluorenylene.  
     
     
         10 : The aromatic amine derivative as described in any of  claims 1  to  9 , wherein in Formula (2) described above, L 2  is phenylene, biphenylylene or fluorenylene.  
     
     
         11 : The aromatic amine derivative as described in any of  claims 1  to  10 , wherein in Formula (2) described above, R 1  is phenyl, naphthyl or phenanthrene.  
     
     
         12 : The aromatic amine derivative as described in any of  claims 1  to  11 , wherein in Formula (1) described above, among Ar 1  to Ar 4 , the groups which are not represented by Formula (2) each are independently phenyl, biphenylyl, terphenylyl or fluorenyl; L 1  is biphenylylene, terphenylylene or fluorenylene; and in Formula (2) described above, L 2  is phenylene, biphenylylene or fluorenylene.  
     
     
         13 : An aromatic amine derivative represented by any of the following Formulas (4) to (6):  
       
         
           
           
               
               
           
         
       
       wherein, L 5  to L 12  each independently represent a substituted or non-substituted arylene group having 6 to 50 ring carbon atoms; 
 at least one of Ar 5  to Ar 9  is represented by (7);  
 at least one of Ar 10  to Ar 5  is represented by (7);  
 at least one of Ar 16  to Ar 21  is represented by (7);  
                     
 wherein, R 1  is a substituted or non-substituted aryl group having 6 to 50 ring atoms, a branched or linear alkyl group having 1 to 50 carbon atoms, a halogen atom or a cyano group;  
 a is an integer of 1 to 3; and  
 L 2  represents a substituted or non-substituted arylene group having 6 to 50 ring atoms;  
 provided that there is no case in which a is 2 and in which two R 1  form a ring to be turned into a benzothiophenyl group;  
 in Formulas (4) to (6), among Ar 5  to Ar 21 , the groups which are not represented by Formula (7) each are independently a substituted or non-substituted aryl group having 6 to 50 ring atoms; provided that substituents for Ar 5  to Ar 21  are an aryl group having 6 to 50 ring atoms, a branched or linear alkyl group having 1 to 50 carbon atoms, a halogen atom or a cyano group;  
 provided that there is no case in which in Formula (5), Ar 11  and Ar 14  are thienylaryl groups at the same time.  
 
     
     
         14 : The aromatic amine derivative as described in  claim 13 , wherein Formula (7) described above is represented by the following Formula (8):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is a substituted or non-substituted aryl group having 6 to 50 ring atoms or a branched or linear alkyl group having 1 to 50 carbon atoms; and 
 L 2  represents a substituted or non-substituted arylene group having 6 to 50 ring atoms.  
 
     
     
         15 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (4) described above, at least one of Ar 5  to Ar 9  is represented by Formula (7).  
     
     
         16 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (4) described above, Ar 5  is represented by Formula (7) described above.  
     
     
         17 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (4) described above, Ar 6  and Ar 8  are each independently represented by Formula (7) described above.  
     
     
         18 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (5) described above, at least one of Ar 10  to Ar 15  is represented by Formula (7).  
     
     
         19 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (5) described above, Ar 10  and Ar 15  are each independently represented by Formula (7) described above.  
     
     
         20 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (5) described above, Ar 11  and Ar 13  are each independently represented by Formula (7) described above.  
     
     
         21 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (6) described above, at least one of Ar 16  to Ar 21  is represented by Formula (7).  
     
     
         22 : The aromatic amine derivative as described in  claim 13  or  14 , wherein in Formula (6) described above, Ar 16 , Ar 18  and Ar 20  are each independently represented by Formula (7) described above.  
     
     
         23 : The aromatic amine derivative as described in any of  claims 13  to  22 , wherein in Formulas (4) to (6) described above, among Ar 5  to Ar 21 , the groups which are not represented by Formula (7) each are independently phenyl, biphenylyl, terphenylyl or fluorenyl.  
     
     
         24 : The aromatic amine derivative as described in any of  claims 13  to  23 , wherein in Formulas (4) to (6) described above, L 5  to L 12  each are independently phenylene, biphenylylene, terphenylylene or fluorenylene.  
     
     
         25 : The aromatic amine derivative as described in any of  claims 13  to  24 , wherein in Formula (7) described above, L 2  is phenylene, biphenylylene or fluorenylene.  
     
     
         26 : The aromatic amine derivative as described in any of  claims 13  to  25 , wherein in Formula (7) described above, R 1  is phenyl, naphthyl or phenanthrene.  
     
     
         27 : The aromatic amine derivative as described in any of  claims 13  to  26 , wherein in Formulas (4) to (6) described above, among Ar 5  to Ar 21 , the groups which are not represented by Formula (7) each are independently phenyl, biphenylyl, terphenylyl or fluorenyl; L 5  to L 12  are each independently phenylene, biphenylylene, terphenylylene or fluorenylene; and L 2  in Formula (7) is phenylene, biphenylylene or fluorenylene.  
     
     
         28 : The aromatic amine derivative as described in any of  claims 1  to  27 , wherein it is a material for an organic electroluminescence device.  
     
     
         29 : The aromatic amine derivative as described in any of  claims 1  to  27 , wherein it is a material for an organic electroluminescence device for vapor deposition.  
     
     
         30 : The aromatic amine derivative as described in any of  claims 1  to  27 , wherein it is a hole transporting material for an organic electroluminescence device.  
     
     
         31 : An organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer in the above organic thin film layer contains the aromatic amine derivative as described in any of  claims 1  to  27  in the form of a single component or a mixed component.  
     
     
         32 : The organic electroluminescence device as described in  claim 31 , wherein the above organic thin film layer comprises a hole transporting layer, and the aromatic amine derivative described above is contained in the above hole transporting layer.  
     
     
         33 : The organic electroluminescence device as described in  claim 31 , wherein the above organic thin film layer comprises plural hole transporting layers, and the aromatic amine derivative described above is contained in the layer which is not brought into direct contact with the light emitting layer.  
     
     
         34 : The organic electroluminescence device as described in  claim 31 , wherein the above organic thin film layer comprises a hole injecting layer, and the aromatic amine derivative described above is contained in the above hole injecting layer.  
     
     
         35 : The organic electroluminescence device as described in  claim 31 , wherein the aromatic amine derivative described above is contained in the hole injecting layer as a main component.  
     
     
         36 : The organic electroluminescence device as described in any of  claims 31  to  35 , wherein a styrylamine compound and/or an arylamine compound are contained in the light emitting layer.  
     
     
         37 : The organic electroluminescence device as described in any of  claims 31  to  36 , wherein the layer brought into contact with the anode among the respective layers constituting the hole injecting layer and the hole transporting layer described above is the layer containing an acceptor material.  
     
     
         38 : The organic electroluminescence device as described in any of  claims 31  to  37 , wherein it emits light of a blue color.