Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic apparatus

Abstract

A compound represented by formula (1): wherein R 1 , R 2 , Ar 1 , and Ar 2 are as defined in the description, realizes an electroluminescence device which is capable of driving at a low voltage and has long lifetime and high efficiency.

1 : A compound represented by formula (1): 
       
         
           
           
               
               
           
         
         wherein one of R 1  and R 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and the other represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group; or 
         both R 1  and R 2  each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; 
         when one or both of R 1  and R 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the aryl group and a benzene ring to which R 1  or R 2  is bonded may be crosslinked; 
         Ar 1  represents a group represented by formula (2) or (3); 
         Ar 2  represents a group selected from the group consisting of a group represented by formula (2), a group represented by formula (3), and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms: 
       
       
         
           
           
               
               
           
         
       
       wherein in formula (2):
 X represents an oxygen atom or a sulfur atom; 
 L 1  represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; 
 y represents 0 or 1, and when y is 0, (L 1 ) 0  represents a single bond; 
 R 3  represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group; and 
 m represents an integer of 0 to 4, when m is an integer of 2 to 4, two to four groups R 3  may be the same or different and may be bonded to each other to form a ring, and when m is 0, (R 3 ) 0  represents a hydrogen atom; 
 
       wherein in formula (3):
 R 5  and R 6  each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 10 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group; 
 L 2  represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; 
 z represents 0 or 1, and when z is 0, (L 2 ) 0  represents a single bond; 
 R 4  represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group; and 
 n represents an integer of 0 to 4, when n is an integer of 2 to 4, two to four groups R 4  may be the same or different and may be bonded to each other to form a ring, and when n is 0, (R 4 ) 0  represents a hydrogen atom. 
 
     
     
         2 : The compound according to  claim 1 , wherein one of R 1  and R 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other represents a hydrogen atom. 
     
     
         3 : The compound according to  claim 1 , wherein the group of formula (1) represented by formula (4): 
       
         
           
           
               
               
           
         
       
       is represented by formula (4a) or (4b): 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  each represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 
     
     
         4 : The compound according to  claim 3 , wherein R 1  and R 2  in formulae (4a) and (4b) each represent a substituted or unsubstituted phenyl group. 
     
     
         5 : The compound according to  claim 3 , wherein the group of formula (1) represented by formula (4) is represented by the following group: 
       
         
           
           
               
               
           
         
       
     
     
         6 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (2), and formula (2) is represented by formulae (2a) or (2b): 
       
         
           
           
               
               
           
         
       
       wherein L 1 , y, X, R 3 , and m are as defined above. 
     
     
         7 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (2), and formula (2) is represented by formula (2a′) or (2b′): 
       
         
           
           
               
               
           
         
       
       wherein L 1 , X, R 3 , and m are as defined above. 
     
     
         8 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (2), and formula (2) is represented by formula (2a″) or (2b″): 
       
         
           
           
               
               
           
         
       
       wherein L 1  and X are as defined above. 
     
     
         9 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (2), and formula (2) is represented by formula (2a″-1) or (2b″-1): 
       
         
           
           
               
               
           
         
       
       wherein X is as defined above. 
     
     
         10 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (2), and formula (2) is represented by any of the following groups: 
       
         
           
           
               
               
           
         
       
       wherein X is as defined above. 
     
     
         11 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (3), and formula (3) is represented by formula (3a): 
       
         
           
           
               
               
           
         
       
       wherein L 2 , z, R 4 , R 5 , R 6 , and n are as defined above. 
     
     
         12 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (3), and formula (3) is represented by formula (3a′): 
       
         
           
           
               
               
           
         
       
       wherein R 4 , R 5 , R 6 , and n are as defined above. 
     
     
         13 : The compound according to  claim 1 , wherein Ar 1  and/or Ar 2  represent a group represented by formula (3), and formula (3) is represented by formula (3a″): 
       
         
           
           
               
               
           
         
       
       wherein R 5  and R 6  are as defined above. 
     
     
         14 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a triphenylenyl group, a bonzophenanthryl group, a phenalenyl group, a fluorenyl group, a pentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, a perylenyl group, a naphthylphenyl group, a phenylnaphthyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-bis(p-methylphenyl)fluorenyl group, a 7-phenyl-9,9-diphenylfluorenyl group, a p-(9,9-diphenylfluorenyl)phenyl group, a 7-phenyl-9,9-dimethylfluorenyl group, a 9,9′-spirobifluorenyl group, a spiro[9H-fluorenyl-9,1′-cyclopentane]group, and a spiro[9H-fluorenyl-9,1′-cyclohexane]group. 
     
     
         15 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a naphthylphenyl group, a 9,9-dimethylfluorene-2-yl group, a 9,9-diphenylfluorene-2-yl group, a 9,9-bis(p-methylphenyl)fluorene-2-yl group, a 7-phenyl-9,9-diphenylfluorene-2-yl group, a p-(9,9-diphenylfluorene-2-yl)phenyl group, and a 9,9′-spirobifluorene-2-yl group. 
     
     
         16 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a naphthylphenyl group, a 9,9-dimethylfluorene-2-yl group, a 9,9-diphenylfluorene-2-yl group, a 9,9-bis(p-methylphenyl)fluorene-2-yl group, a 7-phenyl-9,9-diphenylfluorene-2-yl group, and a p-(9,9-diphenylfluorene-2-yl)phenyl group 
     
     
         17 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a terphenylyl group, a phenyl-substituted terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a triphenylenyl group, a bonzophenanthryl group, a phenalenyl group, a fluorenyl group, a pentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, a perylenyl group, a naphthylphenyl group, a phenylnaphthyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-bis(p-methylphenyl)fluorenyl group, a 7-phenyl-9,9-diphenylfluorenyl group, a p-(9,9-diphenylfluorenyl)phenyl group, a 7-phenyl-9,9-dimethylfluorenyl group, a 9,9′-spirobifluorenyl group, a spiro[9H-fluorenyl-9,1′-cyclopentane]group, and a spiro[9H-fluorenyl-9,1′-cyclohexane]group. 
     
     
         18 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a terphenylyl group, a phenyl-substituted terphenylyl group, a naphthyl group, a naphthylphenyl group, a 9,9-dimethylfluorene-2-yl group, a 9,9-diphenylfluorene-2-yl group, a 9,9-bis(p-methylphenyl)fluorene-2-yl group, a 7-phenyl-9,9-diphenylfluorene-2-yl group, a p-(9,9-diphenylfluorene-2-yl)phenyl group, and a 9,9′-spirobifluorene-2-yl group. 
     
     
         19 : The compound according to  claim 1 , wherein Ar 2  represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted aryl group is selected from the group consisting of a terphenylyl group, a phenyl-substituted terphenylyl group, a naphthyl group, a naphthylphenyl group, a 9,9-dimethylfluorene-2-yl group, a 9,9-diphenylfluorene-2-yl group, a 9,9-bis(p-methylphenyl)fluorene-2-yl group, a 7-phenyl-9,9-diphenylfluorene-2-yl group, and a p-(9,9-diphenylfluorene-2-yl)phenyl group. 
     
     
         20 : The compound according to  claim 1 , wherein formula (1) is represented by formula (1a) or (1b): 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  each represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and Ar 1  and Ar 2  are as defined in formula (1). 
     
     
         21 : The compound according to  claim 1 , wherein formula (1) is represented by any of formulae (1a-1) to (1a-3) and (1b-1) to (1b-3): 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  each represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and L 1 , X, R 3 , R 4 , R 5 , R 6 , Ar 2 , m, and n are as defined in formula (1). 
     
     
         22 : The compound according to  claim 1 , wherein formula (1) is represented by any of formulae (1a-1′) to (1a-3′) and (1b-1′) to (1b-3′): 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  each represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and L 1 , X, R 5 , R 6 , and Ar 2  are as defined in formula (1). 
     
     
         23 : A material comprising the compound according to  claim 1 . 
     
     
         24 : An organic electroluminescence device which comprises an anode, a cathode, and an organic thin film layer between the anode and the cathode, wherein the organic thin film layer comprises a light emitting layer and at least one layer of the organic thin film layer comprises the compound according to  claim 1 . 
     
     
         25 : The organic electroluminescence device according to  claim 24 , wherein the organic electroluminescence device comprises an organic thin film layer between the anode and the light emitting layer and the organic thin film layer comprises the compound. 
     
     
         26 : An electronic equipment which comprises the organic electroluminescence device according to  claim 24 .