Organic electroluminescent device, an azepine compound, and a method for making the same

Abstract

An organic electroluminescent device having a pair of electrodes, and at least one organic layer interposed between the pair of electrodes, with the organic layer containing at least one compound represented by formula (1): wherein L 11 , L 13 , and L 14 each independently represent an o-arylene group, an o-heteroarylene group, or a vinylene group; L 12 represents an o-arylene group, an o-heteroarylene group, a vinylene group, or an ethylene group; and L 15 represents a trivalent or higher aromatic ring or a trivalent or higher aromatic heterocyclic ring; and a compound represented by formula (2): wherein L 21 , L 22 , L 23 , L 24 , and L 25 each independently represent a group necessary for forming an aromatic ring or a group necessary for forming an aromatic heterocyclic ring; and a method for producing a compound represented by formula (2).

1 . An organic electroluminescent device comprising a pair of electrodes, and at least one organic layer interposed between the pair of electrodes, with the at least one organic layer containing at least one compound represented by formula (1): 
     
       
         
         
             
             
         
       
       wherein L 11 , L 13 , and L 14  each independently represent an o-arylene group, an o-heteroarylene group, or a vinylene group; L 12  represents an o-arylene group, an o-heteroarylene group, a vinylene group, or an ethylene group; and L 15  represents a trivalent or higher aromatic ring or a trivalent or higher aromatic heterocyclic ring. 
     
   
   
       2 . The organic electroluminescent device as claimed in  claim 1 , wherein the compound represented by formula (1) is a compound represented by formula (2): 
     
       
         
         
             
             
         
       
       wherein L 21 , L 22 , L 23 , L 24 , and L 25  each independently represent a group necessary for forming an aromatic ring or a group necessary for forming an aromatic heterocyclic ring. 
     
   
   
       3 . The organic electroluminescent device as claimed in  claim 1 , wherein the compound represented by formula (1) is contained in a hole-transporting layer or a luminescent layer. 
   
   
       4 . A compound represented by formula (2): 
     
       
         
         
             
             
         
       
       wherein L 21 , L 22 , L 23 , L 24 , and L 25  each independently represent a group necessary for forming an aromatic ring or a group necessary for forming an aromatic heterocyclic ring. 
     
   
   
       5 . The compound as claimed in  claim 4 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a ring selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a pyrrole ring, and a carbazole ring. 
   
   
       6 . The compound as claimed in  claim 5 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a benzene ring or a pyridine ring. 
   
   
       7 . The compound as claimed in  claim 6 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a benzene ring. 
   
   
       8 . A method for producing a compound represented by formula (5), which comprises reacting a compound represented by formula (3) with a compound represented by formula (4): 
     
       
         
         
             
             
         
       
       wherein L 3 , L 41 , and L 42  each independently represent a group necessary for forming an aromatic ring or a group necessary for forming an aromatic heterocyclic ring; X, Y, and Z each independently represent a hydrogen atom or a group that splits off in the reaction, and at least one of Y and Z is the group that splits off in the reaction; and R represents a hydrogen atom or a substituent. 
     
   
   
       9 . The method as claimed in  claim 8 , wherein each of L 3 , L 41 , and L 42  forms a ring selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a pyrrole ring, and a carbazole ring. 
   
   
       10 . The method as claimed in  claim 9 , wherein each of L 3 , L 41 , and L 42  forms a ring selected from the group consisting of a benzene ring, and a pyridine ring. 
   
   
       11 . The method as claimed in  claim 8 , wherein the group that splits off in the reaction is selected from the group consisting of a halogen atom, a sulfonyl group, a trifluoromethyl group, and a trifluorobutyl group. 
   
   
       12 . The method as claimed in  claim 8 , wherein R represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. 
   
   
       13 . A method for producing a compound represented by formula (2) as claimed in  claim 4 , which comprises
 reacting a compound represented by formula (3a) with a compound represented by formula (4a):   
     
       
         
         
             
             
         
       
       wherein L 21 , L 22 , L 23 , L 24 , and L 25  each independently represent a group necessary for forming an aromatic ring or a group necessary for forming an aromatic heterocyclic ring; 
       X, Y, and Z each independently represent a hydrogen atom or a group that splits off in the reaction, and at least one of Y and Z is the group that splits off in the reaction. 
     
   
   
       14 . The method as claimed in  claim 13 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a ring selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a pyrrole ring, and a carbazole ring. 
   
   
       15 . The method as claimed in  claim 14 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a benzene ring or a pyridine ring. 
   
   
       16 . The method as claimed in  claim 13 , wherein the group that splits off in the reaction is selected from the group consisting of a halogen atom, a sulfonyl group, a trifluoromethyl group, and a trifluorobutyl group. 
   
   
       17 . The organic electroluminescent device as claimed in  claim 2 , wherein each of L 21 , L 22 , L 23 , L 24 , and L 25  forms a ring selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a pyrrole ring, and a carbazole ring.