Organic Electroluminescent Element and Manufacturing Method Thereof, and Phosphorus-Containing Organic Compound and Manufacturing Method Thereof

Abstract

An organic electroluminescent element comprising an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the organic compound layers including: a hole-transporting layer made of an organic compound insoluble in alcohols; and an electron-transporting layer formed on the hole-transporting layer by a wet method, the electron-transporting layer being made of a phosphorus-containing organic compound soluble in the alcohols.

1 . An organic electroluminescent element comprising an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the organic compound layers including: a hole-transporting layer made of an organic compound insoluble in alcohols; and an electron-transporting layer formed on the hole-transporting layer by a wet method, the electron-transporting layer being made of a phosphorus-containing organic compound soluble in the alcohols.  
   
   
       2 . The organic electroluminescent element according to  claim 1 , wherein the phosphorus-containing organic compound is a nonionic organic compound.  
   
   
       3 . The organic electroluminescent element according to  claim 1 , wherein the phosphorus-containing organic compound has a molecular weight of 300-5000.  
   
   
       4 . The organic electroluminescent element according to  claim 1 , wherein the phosphorus-containing organic compound is represented by the general formula (1):  
     
       
         
         
             
             
         
       
       wherein Ar 1 -Ar 3 , the same or different from each other, represent an aromatic ring residue optionally containing a substituent.  
     
   
   
       5 . The organic electroluminescent element according to  claim 1 , wherein the phosphorus-containing organic compound is represented by the general formula (2):  
     
       
         
         
             
             
         
       
       wherein Ar 1 -Ar 6 , the same or different from each other, represent an aromatic ring residue optionally containing a substituent; and A 7 -Ar 9 , the same or different from each other, represent an arylene group optionally containing a substituent.  
     
   
   
       6 . The organic electroluminescent element according to  claim 1 , wherein the phosphorus-containing organic compound is represented by the general formula (3):  
     
       
         
         
             
             
         
       
       wherein R 1  or R 2 , the same or different from each other, represents a hydrogen atom, an allyl group, a halogen atom, cyano group, nitro group, amino group, an aryl group or a diarylphosphinyl group, and R 1  and R 2  can form, together with a carbon atom of a benzene ring to which they are linked, a substituted or unsubstituted aromatic ring; and n is 1 or 2.  
     
   
   
       7 . A manufacturing method of an organic electroluminescent element including an anode, a cathode and a plurality of organic compound layers sandwiched between the anode and cathode, the process comprising the steps of: forming a hole-transporting layer using an organic compound insoluble in alcohols; and forming an electron-transporting layer on the hole-transporting layer by a wet method using as an electron transporting layer material a phosphorus-containing organic compound to be dissolved in an alcohol.  
   
   
       8 . The manufacturing method of an organic electroluminescent element according to  claim 7 , wherein the alcohol is a linear or branched C 1 -C 6  aliphatic alcohol.  
   
   
       9 . The manufacturing method of an organic electroluminescent element according to  claim 7 , wherein the phosphorus-containing organic compound is represented by the general formula (1).  
   
   
       10 . The manufacturing method of an organic electroluminescent element according to  claim 7 , wherein the phosphorus-containing organic compound is represented by the general formula (2).  
   
   
       11 . The manufacturing method of an organic electroluminescent element according to  claim 7 , wherein the phosphorus-containing organic compound is represented by the general formula (3).  
   
   
       12 . A phosphorus-containing organic compound as a condensation product of a compound represented by the general formula (4):  
     
       
         
         
             
             
         
       
       wherein Ar 11 , the same or different from each other, represent a phenyl group or naphthyl group optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group or a phenyl group, and either  
       a compound represented by the formula:  
         Ar 12    
       wherein Ar 12  represents benzene substituted with three halogen atoms, or benzene or biphenyl substituted with two halogen atoms  
       or  
       a compound represented by the general formula (5):  
       
         
           
           
               
               
           
         
       
       wherein Ar 13 , the same or different from each other, are a phenyl group or biphenyl group optionally substituted with a halogen atom, at least two of Ar 13  being a phenyl group or biphenyl group substituted with at least one halogen atom.  
     
   
   
       13 . The phosphorus-containing organic compound according to  claim 12 , represented by the subformula (6):  
     
       
         
         
             
             
         
       
       wherein Ar 11  has the same meaning as defined in the general formula (4); and  
       Ar 12 ′ represents a phenylene group or biphenylene group when n=2 and a benzenetriyl group when n=3.  
     
   
   
       14 . The phosphorus-containing organic compound according to  claim 12 , represented by the subformula (7):  
     
       
         
         
             
             
         
       
       wherein Ar 11  has the same meaning as defined in the general formula (4); and Ar 13 ′, the same or different from each other, represent a phenylene group or a biphenylene group.  
     
   
   
       15 . The phosphorus-containing organic compound according to  claim 12 , represented by the subformula (8):  
     
       
         
         
             
             
         
       
       wherein Ar 11  has the same meaning as defined in the general formula (4); Ar 13 ′, the same or different from each other, represent a phenylene group or a biphenylene group; and Ar 13 ′ represents a phenyl group or a biphenyl group.  
     
   
   
       16 . The phosphorus-containing organic compound according to  claim 12 , selected from 
 compounds of the subformula (6):                          compounds of the subformula (7):                                                                                compounds of the subformula (8):                          
   
   
       17 . A phosphorus-containing organic compound having at least three partial structures represented by a diarylphosphine oxide skeleton, the diarylphosphine oxide skeleton represented by either the formula (9):  
     
       
         
         
             
             
         
       
       wherein Ar 11  has the same meaning as defined in the general formula (4) or the formula (10):  
       
         
           
           
               
               
           
         
       
       wherein Ar 13 ′, the same or different from each other, are a phenyl group or a biphenyl group, or a phenylene group or biphenylene group linked to the formula (9).  
     
   
   
       18 . A manufacturing method of a phosphorus-containing organic compound, comprising the step of condensing, in a solvent, in the presence of a condensing catalyst and a base, a compound of the general formula (4):  
     
       
         
         
             
             
         
       
       wherein Ar 11  has the same meaning as defined in the general formula (4), with either a compound of the formula:  
         Ar 12    
       wherein Ar 12  has the same meaning as defined in the above formula Ar 12    
       or  
       a compound of the general formula (5):  
       
         
           
           
               
               
           
         
       
       wherein Ar 13  has the same meaning as defined in the general formula (5).  
     
   
   
       19 . The manufacturing method of a phosphorus-containing organic compound according to  claim 17 , wherein the solvent is dimethyl sulfoxide, the condensing catalyst is palladium acetate or a complex compound of palladium acetate with either 1,3-bis(diphenylphosphino)propane or 1,4-bis(diphenylphosphino)butane, and the base is a trialkylamine, N-ethyldiisopropylamine, or N,N′-dimethylaminopyridine.