Novel compound, organic electroluminescence device and electronic apparatus

Abstract

A compound having structures represented by the following formulas (1) or (2): wherein in the formulas (1) and (2), at least one of R 1 to R 8 is a deuterium atom.

1 . A compound represented by the following formula (1): 
       
         
           
           
               
               
           
         
         wherein in the formula (1), 
         R 1  to R 8  and R 11  to R 14  are independently 
         a hydrogen atom, 
         a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 
         a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
         a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; 
         R 15  to R 16  and R 18  are hydrogen atoms; 
         at least one of R 1  to R 8  is a deuterium atom; 
         two or more adjacent groups of R 1  to R 4 , two or more adjacent groups of R 5  to R 8  and two or more adjacent groups of R 11  to R 14  do not form a ring; 
         L 1  and L 2  are independently 
         a single bond, 
         a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or 
         a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; 
         Ar is 
         a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
         a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 
       
     
     
         2 . The compound according to  claim 1 , wherein Ar is a group represented by the following formula (a2): 
       
         
           
           
               
               
           
         
         wherein in the formula (a2), 
         is a single bond bonding to L 1 ; 
         R 21  is 
         a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 
         a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
         a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; 
         m1 is an integer of 0 to 4; 
         m2 is an integer of 0 to 5; 
         when each of m1 to m2 is 2 or more, the plural R 21 s may be the same or different; and 
         when each of m1 to m2 is 2 or more, adjacent plural R 21 s are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring. 
       
     
     
         3 . The compound according to  claim 1 , wherein Ar is p-biphenyl group, m-biphenyl group, or o-biphenyl group. 
     
     
         4 . The compound according to  claim 1 , wherein at least one of R 11  to R 16  and R 18  is a deuterium atom. 
     
     
         5 . The compound according to  claim 1 , wherein all of R 11  to R 16  and R 18  are deuterium atoms. 
     
     
         6 . The compound according to  claim 1 , wherein
 all hydrogen atoms possessed by Ar are protium atoms;   all hydrogen atoms possessed by L 1  and L 2  in the case when L 1  and L 2  are a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms are protium atoms; and   all of R 11  to R 16  and R 18  which are hydrogen atoms are protium atoms.   
     
     
         7 . The compound according to  claim 1 , wherein L 2  is a single bond. 
     
     
         8 . The compound according to  claim 1 , wherein at least one hydrogen atom possessed by -L 1 -Ar is a deuterium atom. 
     
     
         9 . The compound according to  claim 1 , wherein all hydrogen atoms possessed by -L 1 -Ar are deuterium atoms. 
     
     
         10 . The compound according to  claim 1 , wherein L 1  is a single bond. 
     
     
         11 . The compound according to  claim 1 , wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by each of the following formulas: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         12 . The compound according to  claim 1 , wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by each of the following formulas: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         13 . The compound according to  claim 1 , wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by each of the following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         14 . A composition comprising the compound according to  claim 1 , wherein the content ratio of a protium compound having the same structure as formula (1) except that only protium atoms are contained as hydrogen atoms to the total of the compound represented by formula (1) and the protium compound is 99 mol % or less. 
     
     
         15 . The composition according to  claim 14 , wherein the content ratio of the compound represented by formula (1) to the total of the compound represented by the formula (1) and the protium compound is 30 mol % or more. 
     
     
         16 . An organic electroluminesoence device comprising:
 a cathode,   an anode, and   one or two or more organic layer disposed between the cathode and the anode,   wherein at least one organic layer is an emitting layer, and   at least one layer of the emitting layer comprises   the compound according to  claim 1  or   the composition comprising the compound represented by the formula (1) and a protium compound having the same structure as formula (1) except that only protium atoms are contained as hydrogen atoms, wherein the content ratio of the protium compound to the total of the compound represented by formula (1) and the protium compound is 99 mol % or less.   
     
     
         17 . The organic electroluminescence device according to  claim 16 , wherein in the formula (1),
 all hydrogen atoms possessed by Ar are protium atoms;   all hydrogen atoms possessed by L 1  and L 2  in the case when L 1  and L 2  are a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms are protium atoms; and   all of R 11  to R 16  and R 18  which are hydrogen atoms are protium atoms.   
     
     
         18 . The organic electroluminescence device according to  claim 16 , wherein in the formula (1),
 at least one hydrogen atom possessed by -L 1 -Ar is a deuterium atom;   all hydrogen atoms possessed by L 2  in the case when L 2  is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms are protium atoms; and   all of R 11  to R 16  and R 18  which are hydrogen atoms are protium atoms.   
     
     
         19 . The organic electroluminescence device according to  claim 16 , wherein in the formula (1),
 all hydrogen atoms possessed by -L 1 -Ar are protium atoms; and   at least one of R 11  to R 16  and R 18  which are hydrogen atoms and hydrogen atoms possessed by L 2  is a deuterium atom.   
     
     
         20 . The organic electroluminescence device according to  claim 16 , wherein in the formula (1),
 at least one hydrogen atom possessed by -L 1 -Ar is a protium atom; and   at least one of R 11  to R 16  and R 18  which are hydrogen atoms and hydrogen atoms possessed by L 2  is a deuterium atom.   
     
     
         21 . The organic electroluminescence device according to  claim 16 , wherein the emitting layer further comprises a compound represented by the following formula (41): 
       
         
           
           
               
               
           
         
         wherein, in the formula (41), 
         a ring, b ring and c ring are independently 
         a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or 
         a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms; 
         R 401  and R 402  are independently bonded to the a ring, the b ring or the c ring to form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring; 
         R 401  and R 402  that do not form the substituted or unsubstituted heterocyclic ring are independently 
         a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 
         a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, 
         a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, 
         a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 
         a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 
         a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; 
       
     
     
         22 . The organic electroluminescence device according to  claim 16 , comprising a hole-transporting layer between the anode and the emitting layer, wherein the hole-transporting layer comprises the following compound HT-2.