Compound, material for organic electroluminescence devices, organic electroluminescence device, and electronic device

Abstract

a compound represented by formula (A):wherein Ar, R1 to R7, R11 to R14, R21 to R24, R31 to R34, *1, and R41 to R48 are as defined in the description provides organic electroluminescence devices with improved device performance.

1 . A compound represented by formula (A): 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group; 
 R 1  to R 7  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms; 
 R 11  to R 14  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms; 
 R 21  to R 24  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms; 
 R 31  to R 34  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms; 
 R 41  to R 48  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms, provided that one selected from R 47  and R 48  is a single bond bonded to *1; 
 an optional substituent for the phenyl group, the biphenylyl group, the naphthyl group, and the phenanthryl group is independently a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms; 
 adjacent two selected from R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  not the single bond bonded to *1 are not bonded to each other thereby failing to form a ring structure; and 
 if the phenyl group, the biphenylyl group, the naphthyl group, or the phenanthryl group has adjacent two optional substituents, the adjacent two optional substituents are not bonded to each other thereby failing to form a ring. 
 
     
     
         2 . The compound according to  claim 1 , wherein the halogen atom for the optional substituent of Ar and the halogen atom for R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  not the single bond bonded to *1 are each independently selected from an iodine atom, a bromine atom, a chlorine atom, and a fluorine atom. 
     
     
         3 . The compound according to  claim 1 , wherein the alkyl group having 1 to 10 carbon atoms for the optional substituent of Ar and the alkyl group having 1 to 10 carbon atoms for R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  not the single bond bonded to *1 are each independently selected from a methyl group, an ethyl group, a n-propyl group, a sec-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, and a t-butyl group. 
     
     
         4 . The compound according to  claim 1 , wherein the cycloalkyl group having 3 to 6 ring carbon atoms for the optional substituent of Ar and the cycloalkyl group having 3 to 6 ring carbon atoms for R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  not the single bond bonded to *1 are each independently selected from a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. 
     
     
         5 . The compound according to  claim 1 , wherein the compound is represented by formula (1) or (11): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  are as defined in formula (A). 
     
     
         6 . The compound according to  claim 1 , wherein the compound is represented bv formula (2) or (12): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  are as defined in formula (A); and 
 R 51  to R 55  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms. 
 
     
     
         7 . The compound according to  claim 1 , wherein the compound is represented by formula (4) or (14): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  are as defined in formula (A); and 
 one selected from R 71  and R 72  is a single bond bonded to *b, and the other of R 71  and R 72  and R 73  to R 78  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms. 
 
     
     
         8 . The compound according to  claim 7 , wherein formula (4) is represented by formula (4a) or (4b): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 47  are as defined in formula (A); and 
 R 71  to R 7  and R 73  to R 78  are as defined in formula (4). 
 
     
     
         9 . The compound according to  claim 7 , wherein formula (14) is represented by formula (14a) or (14b): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , R 41  to R 46 , and R 48  are as defined in formula (A); and 
 R 71  to R 72  and R 73  to R 78  are as defined in formula (14). 
 
     
     
         10 . The compound according to  claim 1 , wherein the compound is represented by formula (5) or (15): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  are as defined in formula (A); and 
 one selected from R 81  to R 90  is a single bond bonded to *c, and the others of R 81  to R 90  are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 6 ring carbon atoms. 
 
     
     
         11 . The compound according to  claim 10 , wherein formula (5) is represented by any of formulae (5a) to (5e): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 47  are as defined in formula (A); and 
 R 81  to R 90  are as defined in formula (5). 
 
     
     
         12 . The compound according to  claim 10 , wherein formula (15) is represented by any of formulae (15a) to (15e): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein:
 R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , R 41  to R 46 , and R 48  are as defined in formula (A); and 
 R 81  to R 90  are as defined in formula (15). 
 
     
     
         13 . The compound according to  claim 1 , wherein R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , and R 41  to R 48  not the single bond bonded to *1 are all hydrogen atoms. 
     
     
         14 . The compound according to  claim 6 , wherein R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , R 41  to R 48 , and R 51  to R 55  are all hydrogen atoms. 
     
     
         15 . The compound according to  claim 7 , wherein R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , R 41  to R 48 , R 71  or R 72  not the single bond bonded to *b, and R 73  to R 78  are all hydrogen atoms. 
     
     
         16 . The compound according to  claim 10 , wherein R 1  to R 7 , R 11  to R 14 , R 21  to R 24 , R 31  to R 34 , R 41  to R 48 , and R 81  to R 90  not the single bond bonded to *c are all hydrogen atoms. 
     
     
         17 . The compound according to  claim 1 , wherein the compound is represented by any of the following formulae: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         18 . A material for organic electroluminescence device, comprising the compound according to  claim 1 . 
     
     
         19 . An organic electroluminescence device comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein:
 the organic layer comprises a light emitting layer; and   at least one laver of the organic laver comprises the compound according to  claim 1 .   
     
     
         20 . The organic electroluminescence device according to  claim 19 , wherein:
 the organic layer comprises a hole transporting region between the anode and the light emitting layer; and   the hole transporting region comprises the compound.   
     
     
         21 . The organic electroluminescence device according to  claim 20 , wherein:
 the hole transporting region comprises a first hole transporting layer on anode side and a second hole transporting layer on cathode side; and   the first hole transporting layer, the second hole transporting layer, or both thereof comprise the compound.   
     
     
         22 . The organic electroluminescence device according to  claim 21 , wherein the first hole transporting layer comprises the compound. 
     
     
         23 . The organic electroluminescence device according to  claim 21 , wherein the second hole transporting layer comprises the compound. 
     
     
         24 . The organic electroluminescence device according to  claim 19 , wherein the light emitting layer comprises a fluorescent dopant material. 
     
     
         25 . The organic electroluminescence device according to  claim 19 , wherein the light emitting layer comprises a phosphorescent dopant material. 
     
     
         26 . An electronic device comprising the organic electroluminescence device according to  claim 19 . 
     
     
         27 . The compound according to  claim 1 , wherein Ar is a phenyl group, a biphenylyl group, a napthyl group or a phenanthryl group, each having a phenyl substitutent. 
     
     
         28 . The compound according to  claim 1 , wherein Ar is an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, or an unsubstituted phenanthryl group.