Novel compound and organic electroluminescence device

Abstract

A compound represented by the following formula (1), wherein one or more pairs among R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , and R 18 and R 19 independently form a ring represented by the following formula (2A) or a ring represented by the following formula (2B), or do not form a ring represented by the following formula (2A) and do not form a ring represented by the following formula (2B); and one of R 12 to R 28 is bonded with L 2 .

1 . A compound represented by the following formula (1): 
       
         
           
           
               
               
           
         
         wherein in the formula (1), 
         one or more pairs of adjacent two or more among R 1  to R 11  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         one or more pairs among R 12  and R 13 , R 13  and R 14 , R 14  and R 15 , R 16  and R 17 , R 17  and R 18 , and R 18  and R 19  independently form a ring represented by the following formula (2A), or a ring represented by the following formula (2B), or do not form a ring represented by the following formula (2A) and do not form a ring represented by the following formula (2B): 
       
       
         
           
           
               
               
           
         
         wherein in the formulas (2A) and (2B), 
         one or more pairs of adjacent two or more among R 20  to R 27  form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         wherein in the formulas (1), (2A) and (2B), X 1  and X 2  are independently O, S or C(R 28 ) 2 ; 
         adjacent two R 28  form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         one of R 12  to R 28  is bonded with L 2 ; 
         R 1  to R 11  which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 12  to R 27  which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; 
         R 28 's which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2  are a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; 
         L 1  and L 2  are independently a single bond, a substituted or unsubstituted alkylene group including 1 to 30 carbon atoms, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms; 
         Ar 1  is a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; 
         R 31  to R 37  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and 
         when two or more of each of R 28  and R 31  to R 37  are present, the two or more of each of R 28  and R 31  to R 37  may be the same or different. 
       
     
     
         2 . The compound according to  claim 1 , wherein the compound is represented by the following formula (3): 
       
         
           
           
               
               
           
         
         wherein in the formula (3), R 1  to R 19 , X 1  and Ar 1  are as defined in the formula (1); and 
         L 2  is a single bond. 
       
     
     
         3 . The compound according to  claim 1 , wherein the compound is represented by the following formula (4): 
       
         
           
           
               
               
           
         
         wherein in the formula (4), R 12  to R 19 , X 1  and Ar 1  are as defined in the formula (1); and 
         L 2  is a single bond. 
       
     
     
         4 . The compound according to  claim 1 , wherein the compound is represented by the following formula (4A): 
       
         
           
           
               
               
           
         
         wherein in the formula (4A), R 12  to R 19  and Ar 1  are as defined in the formula (1); and 
         L 2  is a single bond. 
       
     
     
         5 . A compound according to  claim 1 , wherein Ar 1  is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 
     
     
         6 . The compound according to  claim 1 , wherein the compound is represented by the following formula (5): 
       
         
           
           
               
               
           
         
         wherein in the formula (5), R 1  to R 19 , X 1  and L 2  are as defined in the formula (1); 
         one or more pairs among R 12A  and R 13A , R 13A  and R 14A , R 14A  and R 15A , R 16A  and R 17A , R 17A  and R 18A , and R 18A  and R 19A  independently form a ring represented by the following formula (2AA) or a ring represented by the following formula (2BA), or do not form a ring represented by the following formula (2AA) and do not form a ring represented by the following formula (2BA): 
       
       
         
           
           
               
               
           
         
         wherein in the formulas (2AA) and (2BA), 
         one or more pairs of adjacent two or more among R 20A  to R 27A  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         wherein in the formulas (5), (2AA) and (2BA), X 1A  and X 2A  are independently O, S or C(R 28A ) 2 ; adjacent two R 28A 'S form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         one of R 12A  to R 28A  is bonded with L 2A ; 
         R 12A  to R 27A  which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2A  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; 
         R 28A 's which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2 A are a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when two or more R 28A 's are present, the two or more R 28A 's may be the same or different; 
         L 2A  is independently a single bond, a substituted or unsubstituted alkylene group including 1 to 30 carbon atoms, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms; and 
         R 31  to R 37  are as defined in the formula (1). 
       
     
     
         7 . The compound according to  claim 6 , wherein the compound is represented by the following formula (6): 
       
         
           
           
               
               
           
         
         wherein in the formula (6), R 12  to R 19 , X 1 , and L 2  are as defined in the formula (1); and 
         R 12A  to R 19A , X 1A  and L 2A  are as defined in the formula (5). 
       
     
     
         8 . The compound according to  claim 6 , wherein R 12A  to R 27A  which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2A  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 
     
     
         9 . The compound according to  claim 1 , wherein R 12  to R 27  that does not form a substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 
     
     
         10 . The compound according to  claim 1 , wherein the substituent in the case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, a haloalkyl group including 1 to 50 carbon atoms, an alkenyl group including 2 to 50 carbon atoms, an alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 carbon atoms, an alkoxy group including 1 to 50 carbon atoms, an alkylthio group including 1 to 50 carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, an arylthio group including 6 to 50 ring carbon atoms, an aralkyl group including 7 to 50 carbon atoms, —Si(R 41 )(R 42 )(R 43 ), —C(═O)R 44 , —COOR 45 , —S(═O) 2 R 46 , —P(═O)(R 47 )(R 48 ), —Ge(R 49 )(R 50 )(R 51 ), —N(R 52 )(R 53 ), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms, provided that R 41  to R 53  are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a monovalent heterocyclic group including 5 to 50 ring atoms, and provided that, when two or more R 41  to R 53  are present, the two or more R 41  to R 53  may be the same or different. 
     
     
         11 . The compound according to  claim 1 , wherein the substituent in the case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a monovalent heterocyclic group including 5 to 50 ring atoms. 
     
     
         12 . The compound according to  claim 1 , wherein R 14  and R 17  are a t-butyl group. 
     
     
         13 . The compound according to  claim 1 , wherein the compound is a material for an organic electroluminescence device. 
     
     
         14 . A material for an organic electroluminescence device, comprising the compound according to  claim 1 . 
     
     
         15 . An organic electroluminescence device, comprising:
 a cathode;   an anode; and   at least one organic layer disposed between the cathode and the anode,   wherein at least one layer of the at least one organic layer comprises the compound according to  claim 1 .   
     
     
         16 . The organic electroluminescence device according to  claim 15 , wherein at least one layer of the at least one organic layer is an emitting layer. 
     
     
         17 . The organic electroluminescence device according to  claim 16 , wherein the emitting layer further comprises a compound represented by the following formula (10): 
       
         
           
           
               
               
           
         
         wherein in the formula (10), 
         one or more pairs of adjacent two or more among R 101  to R 110  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; 
         R 101  to R 110  which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 121 )(R 122 )(R 123 ), —C(═O)R 124 , —COOR 125 , —N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 carbon atoms, a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, or a group represented by the following formula (31); 
         R 121  to R 127  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; 
         when two or more R 121  to R 127  are present, the two or more R 121  to R 127  may be the same or different; 
         provided that at least one of R 101  to R 110  which do not form the substituted or unsubstituted, saturated or unsaturated ring is a group represented by the following formula (31); and 
         when two or more of groups represented by the following formula (31) are present, the two or more groups represented by the following formula (31) may be the same or different:
   -L 101 -Ar 101   (31)
 
 
         wherein, in the formula (31), 
         L 101  is a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms; and 
         Ar 101  is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 
       
     
     
         18 . The organic electroluminescence device according to  claim 17 , wherein the compound represented by the formula (10) is represented by the following formula (10-1) or (10-2): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-1), R 101  to R 105 , L 101  and Ar 101  are as defined in the formula (10); and 
         wherein in the formula (10-2), R 101 , R 103  to R 105 , L 101  and Ar 101  are as defined in the formula (10). 
       
     
     
         19 . The organic electroluminescence device according to  claim 17 , wherein the compound represented by the formula (10) is represented by the following formula (10-3): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-3), 
         R 101A  to R 108A  are independently a hydrogen atom, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; 
         L 101A  is a single bond, or a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms; 
         two L 101A  may be the same or different; 
         Ar 101A  is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and 
         two Ar 101A  may be the same or different. 
       
     
     
         20 . The organic electroluminescence device according to  claim 17 , wherein the compound represented by the formula (10) is represented by the following formula (10-4): 
       
         
           
           
               
               
           
         
         wherein in formula (10-4), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are independently a hydrogen atom, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; 
         X 11  is O, S, or N(R 61 ); 
         R 61  is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; 
         one of R 62  to R 69  is bonded with L 101 ; 
         one or more pairs of adjacent among R 62  to R 69  which are not bonded with L 101  form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; and 
         R 62  to R 69  which are not bonded with L 101  and do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 
       
     
     
         21 . The organic electroluminescence device according to  claim 20 , wherein the compound represented by the formula (10) is represented by the following formula (10-6): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-6), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are as defined in the formula (10-4); 
         R 66  to R 69  are as defined in the formula (10-4); and 
         X 12  is O or S. 
       
     
     
         22 . The organic electroluminescence device according to  claim 20 , wherein the compound represented by the formula (10) is represented by the following formula (10-7): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-7), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are as defined in the formula (10-4); 
         X 11  is as defined in the formula (10-4); 
         R 62  to R 69  are as defined in the formula (10-4); and 
         provided that one pair among R 66  and R 67 , R 67  and R 68 , and R 68  and R 69  is bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. 
       
     
     
         23 . The organic electroluminescence device according to  claim 20 , wherein the compound represented by the formula (10) is represented by the following formula (10-8): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-8), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are as defined in the formula (10-4); 
         X 12  is O or S; 
         R 66  to R 69  are as defined in the formula (10-4); and 
         provided that one pair among R 66  and R 67 , R 67  and R 68 , and R 68  and R 69  is bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. 
       
     
     
         24 . The organic electroluminescence device according to  claim 22 , wherein one pair among R 66  and R 67 , R 67  and R 68 , and R 68  and R 69  is bonded with each other to form a ring represented by the following formula (10-8-1) or (10-8-2); and
 R 66  to R 69  which do not form the ring represented by the formula (10-8-1) or (10-8-2) do not form a substituted or unsubstituted, saturated or unsaturated ring:   
       
         
           
           
               
               
           
         
         wherein in the formulas (10-8-1) and (10-8-2), 
         two “*” are bonded with one pair among R 66  and R 67 , R 67  and R 68 , and R 68  and R 69 ; 
         R 80  to R 83  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and 
         X 13  is O or S. 
       
     
     
         25 . The organic electroluminescence device according to  claim 20 , wherein the compound represented by the formula (10) is represented by the following formula (10-9): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-9), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are as defined in the formula (10-4); 
         R 66  to R 69  are as defined in the formula (10-4); 
         provided that R 66  and R 67 , R 67  and R 68 , and R 69  and R 67  are not bonded with each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and 
         X 12  is O or S. 
       
     
     
         26 . The organic electroluminescence device according to  claim 17 , wherein the compound represented by the formula (10) is represented by the following formula (10-4A): 
       
         
           
           
               
               
           
         
         wherein in the formula (10-4A), 
         L 101  and Ar 101  are as defined in the formula (10); 
         R 101A  to R 108A  are independently a hydrogen atom, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; 
         X 11  is O, S, or N(R 61 ); 
         R 61  is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; 
         one or more pairs of adjacent two or more among R 62A  to R 69A  may form a substituted or unsubstituted, saturated or unsaturated ring, and the adjacent two among R 62A  to R 69A  form a ring represented by the following formula (10-4A-1); and 
         R 62A  to R 69A  which do not form a substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms: 
       
       
         
           
           
               
               
           
         
         wherein in the formula (10-4A-1), 
         two “*” are bonded with adjacent two among R 62A  to R 69A ; 
         one of R 70  to R 73  is bonded with L 101 ; and 
         R 70  to R 73  which do not bonded with L 101  are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 
       
     
     
         27 . The organic electroluminescence device according to  claim 16 , which further comprises a hole-transporting layer between the anode and the emitting layer. 
     
     
         28 . The organic electroluminescence device according to  claim 16 , which further comprises an electron-transporting layer between the cathode and the emitting layer. 
     
     
         29 . An electronic appliance, wherein the organic electroluminescence device according to  claim 15  is provided.