Benzofluorene compound, emission materials and organic electroluminescent device

Abstract

Provided is a benzofluorene compound which exhibits excellent performances when applied to an organic electroluminescent device. In the benzofluorene compound, a central five-membered ring in a benzofluorene skeleton is substituted with aryl, and a benzene ring condensed to the five-membered ring is substituted with aryl, diarylamino and the like.

1 . A benzofluorene compound represented by the following Formula (1): 
       
         
           
           
               
               
           
         
         (wherein Ar 1  and Ar 2  are aryl which may be substituted; 
         R 1  and R 2  each are independently hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted or aryl which may be substituted, and at least one of R 1  and R 2  is aryl which may be substituted). 
       
     
     
         2 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are aryl having 6 to 30 carbon atoms which may be substituted;
 R 1  and R 2  each are independently hydrogen, alkyl having 1 to 24 carbon atoms which may be substituted, cycloalkyl having 3 to 12 carbon atoms which may be substituted or aryl having 6 to 30 carbon atoms which may be substituted, and at least one of R 1  and R 2  is aryl having 6 to 30 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms.   
     
     
         3 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are aryl having 6 to 16 carbon atoms which may be substituted;
 R 1  and R 2  are aryl having 6 to 24 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 20 carbon atoms.   
     
     
         4 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are aryl having 6 to 12 carbon atoms which may be substituted;
 R 1  and R 2  are aryl having 6 to 20 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently methyl, ethyl, propyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenylyl or naphthyl.   
     
     
         5 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  each are independently phenyl or biphenylyl; and
 R 1  and R 2  each are independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl or phenanthryl.   
     
     
         6 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are aryl having 6 to 16 carbon atoms which may be substituted;
 one of R 1  and R 2  is hydrogen, and the other is aryl having 6 to 24 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 20 carbon atoms.   
     
     
         7 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are aryl having 6 to 12 carbon atoms which may be substituted;
 one of R 1  and R 2  is hydrogen, and the other is aryl having 6 to 20 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently methyl, ethyl, propyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenylyl or naphthyl.   
     
     
         8 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  each are independently phenyl or biphenylyl; and
 one of R 1  and R 2  is hydrogen, and the other is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl or phenanthryl.   
     
     
         9 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are phenyl;
 R 1  is 4-biphenylyl, and R 2  is 4-biphenylyl.   
     
     
         10 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are phenyl;
 R 1  is 2-naphthyl, and R 2  is 2-naphthyl.   
     
     
         11 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are phenyl;
 R 1  is 4-biphenylyl, and R 2  is 2-naphthyl.   
     
     
         12 . The benzofluorene compound as described in  claim 1 , wherein Ar 1  and Ar 2  are phenyl;
 R 1  is 2-naphthyl, and R 2  is 4-biphenylyl.   
     
     
         13 . A benzofluorene compound represented by the following Formula (1′): 
       
         
           
           
               
               
           
         
         (wherein Ar 1  and Ar 2  are aryl which may be substituted; 
         R 1  is diarylamino having aryl which may be substituted; and 
         R 2  is hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, aryl which may be substituted or diarylamino having aryl which may be substituted). 
       
     
     
         14 . The benzofluorene compound as described in  claim 13 , wherein
 Ar 1  and Ar 2  are aryl having 6 to 30 carbon atoms which may be substituted;   R 1  is diarylamino having aryl having 6 to 30 carbon atoms which may be substituted;   R 2  is hydrogen, alkyl having 1 to 24 carbon atoms which may be substituted, cycloalkyl having 3 to 12 carbon atoms which may be substituted, aryl having 6 to 30 carbon atoms which may be substituted or diarylamino having aryl having 6 to 30 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently alkyl having 1 to 24 carbon atoms, aryl having 6 to 30 carbon atoms or heteroaryl having 2 to 30 carbon atoms.   
     
     
         15 . The benzofluorene compound as described in  claim 13 , wherein
 Ar 1  and Ar 2  are aryl having 6 to 16 carbon atoms which may be substituted;   R 1  is diarylamino having aryl having 6 to 16 carbon atoms which may be substituted;   R 2  is hydrogen, aryl having 6 to 24 carbon atoms which may be substituted or diarylamino having aryl having 6 to 16 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently alkyl having 1 to 12 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 10 carbon atoms.   
     
     
         16 . The benzofluorene compound as described in  claim 13 , wherein
 Ar 1  and Ar 2  are aryl having 6 to 12 carbon atoms which may be substituted;   R 1  is diarylamino having aryl having 6 to 12 carbon atoms which may be substituted;   R 2  is hydrogen, aryl having 6 to 20 carbon atoms which may be substituted or diarylamino having aryl having 6 to 12 carbon atoms which may be substituted; and   substituents in Ar 1 , Ar 2 , R 1  and R 2  each are independently methyl, ethyl, propyl, t-butyl, phenyl, biphenylyl, naphthyl, pyridyl or thienyl.   
     
     
         17 . The benzofluorene compound as described in  claim 13 , wherein
 Ar 1  and Ar 2  each are independently phenyl or biphenylyl;   R 1  is diphenylamino, dibiphenylamino, dinaphthylamino or phenylnaphthylamino; and   R 2  is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, diphenylamino, dibiphenylamino, dinaphthylamino or phenylnaphthylamino.   
     
     
         18 . The benzofluorene compound as described in  claim 13 , wherein
 Ar 1  and Ar 2  are phenyl; and   R 1  and R 2  are diphenylamino.   
     
     
         19 . A material for an emission layer in a light emitting device and which contains the benzofluorene compound as described in  claim 1 . 
     
     
         20 . The material for an emission layer as described in  claim 19 , further containing at least one selected from the group consisting of perylene derivatives, borane derivatives, amine-containing styryl derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, iridium complexes and platinum complexes. 
     
     
         21 . An organic electroluminescent device comprising a pair of electrodes comprising an anode and a cathode and an emission layer which is disposed between a pair of the electrodes and which contains the material for an emission layer as described in  claim 19 . 
     
     
         22 . The organic electroluminescent device as described in  claim 21 , further comprising an electron transport layer and/or an electron injection layer disposed between the cathode and the emission layer, wherein at least one of the electron transport layer and electron injection layer contains at least one selected from the group consisting of quinolinol metal complexes, pyridine derivatives and phenanthroline derivatives. 
     
     
         23 . A display unit comprising the organic electroluminescent device as described in  claim 21 . 
     
     
         24 . A lighting instrument comprising the organic electroluminescent device as described in  claim 21 . 
     
     
         25 . A material for an emission layer in a light emitting device and which contains the benzofluorene compound as described in  claim 13 .