Compound for organic photoelectric device, organic photoelectric device including the same, and display device including the same

Abstract

A compound for an organic photoelectric device, an organic photoelectric device including the same, and a display device including the same the compound being represented by the following Chemical Formula 1:

1 . A compound for an organic photoelectric device, the compound being represented by the following Chemical Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         A 1  to A 5  are each independently selected from the group of CR 1  to CR 5  and N, provided that three or less of A 1  to A 5  are N, 
         R 1  to R 5  are each independently selected from the group of hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, an ester, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted arylamine, a substituted or unsubstituted heteroarylamine, a substituted or unsubstituted heterocycle, a substituted or unsubstituted amino, BR 6 R 7 , and SiR 6 R 7 R 8 , 
         R 6  to R 8  are each independently selected from the group of a substituted or unsubstituted alkyl and a substituted or unsubstituted aryl, 
         when only one of A 1  to A 5  is N, the remaining four of A 1  to A 5  are respectively selected from the group of CR 1  to CR 5 , provided that at least two of R 1  to R 5  are not hydrogen, 
         when A 1  to A 5  are respectively CR 1  to CR 5 , at least two of R 1  to R 5  are not hydrogen, 
         Z is selected from the group of O, S, Se, and NR″, 
         U and D are each independently selected from the group of CR′ and N, provided that when Z is O, S, or Se, U is N, 
         R′ and R″ are each independently selected from the group of hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, an ester, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted arylamine, a substituted or unsubstituted heteroarylamine, a substituted or unsubstituted heterocycle, a substituted or unsubstituted amino, BR 6 R 7 , and SiR 6 R 7 R 3 , 
         E is selected from the group of hydrogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, a substituted or unsubstituted alkyl, a substituted or unsubstituted fluoroalkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocycle, and SO 2 R 9 , 
         R 9  is selected from the group of a nitrile, a cyano, a nitro, an amide, a carbonyl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, and a substituted or unsubstituted heterocycle, 
         L is selected from the group of a substituted or unsubstituted arylene and a substituted or unsubstituted heteroarylene, and 
         n is 0 or 1. 
       
     
     
         2 . The compound as claimed in  claim 1 , wherein the compound has an asymmetric structure such that upper and lower substituents are different from each other with respect to an axis including A 3 . 
     
     
         3 . The compound as claimed in  claim 1 , wherein:
 A 1  and A 5  are different from each other, and   A 2  and A 4  are different from each other.   
     
     
         4 . The compound as claimed in  claim 1 , wherein, in Chemical Formula 1, R 1 , R 1 ′, and R 1 ″ are each independently a substituted or unsubstituted C6 to C40 aryl. 
     
     
         5 . The compound as claimed in  claim 1 , wherein, in Chemical Formula 1, R 1 , R 1 ′, and R 1 ″ are each independently an arylamine, the arylamine including one of a diphenyl amine, a dinaphthyl amine, a dibiphenyl amine, a phenyl naphthyl amine, a phenyl diphenyl amine, a ditolyl amine, a phenyl tolyl amine, a carbazolyl, and a triphenyl amine. 
     
     
         6 . The compound as claimed in  claim 1 , wherein, in Chemical Formula 1, R 1 , R 1 ′, and R 1 ″ are each independently a substituted or unsubstituted heterocycle, the substituted or unsubstituted heterocycle including one of a thiophenyl, a furanyl, a pyrrolyl, an imidazolyl, a thiazolyl, an oxazolyl, an oxadiazolyl, a triazolyl, a pyridinyl, a pyridazinyl, a quinolinyl, an isoquinolinine, an acridyl, an imidazopyridinyl, and an imidazopyrimidinyl. 
     
     
         7 . The compound as claimed in  claim 1 , wherein, in Chemical Formula 1, R 1 , R 1 ′, and R 1 ″ are each independently a substituted imidazolyl or a substituted triazolyl, the substituent thereof:
 being linked to nitrogen (N) of the imidazolyl or triazolyl, and 
 including one of a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aryl, and a substituted or unsubstituted heterocycle. 
 
     
     
         8 . The compound as claimed in  claim 1 , wherein, in Chemical Formula 1:
 one of R 1 , R 1 ′, and R 1 ″ is substituted with a substituent, the substituent including one of an amine-substituted alkyl, an amine-substituted cycloalkyl, an amine-substituted aryl, and an amine-substituted heterocycle, and   another of R 1 , R 1 ′, and R 1 ″ is substituted with a substituent, the substituent including one of a nitrile, a nitrile, a nitro, an amide, a carbonyl, and a heterocycle.   
     
     
         9 . A compound for an organic photoelectric device, the compound being represented by the following Chemical Formula 112: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 112, 
         A 1  to A 12  are each independently selected from the group of CR 1  to CR 12  and N, provided that at least one of A 7  to A 12  is N, and R 1  to R 6  adjacent to each other optionally form a fused ring, and R 7  to R 12  adjacent to each other optionally form a fused ring, 
         X is selected from the group of O, S, Se, and NR 13 , and Y is CR 14  or N, provided that when X is selected from the group of O, S, and Se, Y is N, 
         L is a substituted or unsubstituted C6 to C50 arylene, 
         a is 0 or 1, provided that when a is 0, A 1  to A 6  are each independently CR 1  to CR 6 , and when a is 1, at least one of A 1  to A 6  is N, 
         b and c are each independently an integer of 1 to 3, and 
         R 1  to R 14  are each independently selected from the group of hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, an ester, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a substituted or unsubstituted arylene, a substituted or unsubstituted arylamine, a substituted or unsubstituted heteroarylamine, a substituted or unsubstituted heterocycle, a substituted or unsubstituted amino, BRR′, or SiRR′R″, wherein R, R′ and R″ are the same or different, and each independently a substituted or unsubstituted alkyl, or a substituted or unsubstituted aryl. 
       
     
     
         10 . The compound as claimed in  claim 9 , wherein in Chemical Formula 112:
 one of R 7  to R 12  is substituted with a substituent selected from the group of an amine-substituted alkyl, an amine-substituted cycloalkyl, an amine substituted aryl, and an amine-substituted heterocycle, and   one of R 1  to R 6  is substituted with a substituent selected from the group of a nitrile, a nitro, an amide, a carbonyl, and a substituted or unsubstituted heterocycle.   
     
     
         11 . The compound as claimed in  claim 9 , wherein the compound is represented by the following Chemical Formula 113: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 113, 
         A 2 , A 4  to A 12  and A 7 ′ to A 12 ′ are each independently selected from the group of CR 2 , CR 4  to CR 12 , CR 7 ′ to CR 12 ′ and N, provided at least one of A 7  to A 12  is N, and at least one of A 7 ′ to A 12 ′ is N, wherein R 4  to R 6  adjacent to each other optionally form a fused ring, R 7  to R 12  adjacent to each other optionally form a fused ring, and R 7 ′ to R 12 ′ adjacent to each other optionally form a fused ring, 
         X is selected from the group of O, S, Se, and NR 13 , and Y is CR 14  or N, provided that when X is selected from the group of O, S, and Se, Y is N, 
         L and L′ are each independently a substituted or unsubstituted C6 to C50 arylene, 
         a and a′ are each independently 0 or 1, provided that when a and a′ are each independently 0, A 2 , A 4  to A 6  are each independently CR 2  and CR 4  to CR 6 , and when a and a′ are each independently 1, at least one of A, and A 4  to A 6  is N, 
         b and b′ are each independently an integer of 1 to 3, and 
         R 2 , R 4  to R 14 , and R 7 ′ to R 12 ′ are each independently hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, an ester, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a substituted or unsubstituted arylene, a substituted or unsubstituted arylamine, a substituted or unsubstituted heteroarylamine, a substituted or unsubstituted heterocycle, a substituted or unsubstituted amino, BRR′, or SiRR′R″, wherein R, R′ and R″ are the same or different, and each independently a substituted or unsubstituted alkyl, or a substituted or unsubstituted aryl. 
       
     
     
         12 . The compound as claimed in  claim 9 , wherein, in Chemical Formula 112, R 1  to R 14  are each independently an arylamine, the arylamine including one of a diphenyl amine, a dinaphthyl amine, a dibiphenyl amine, a phenyl naphthyl amine, a phenyl diphenyl amine, a ditolyl amine, a phenyl tolyl amine, a carbazolyl, and a triphenyl amine. 
     
     
         13 . The compound as claimed in  claim 9 , wherein, in Chemical Formula 112, R 1  to R 14  are each independently a substituted or unsubstituted heterocycle, the substituted or unsubstituted heterocycle including one of a thiophenyl, a furanyl, a pyrrolyl, an imidazolyl, a thiazolyl, an oxazolyl, an oxadiazolyl, a triazolyl, a pyridinyl, a pyridazinyl, a quinolinyl, an isoquinolinine, an acridyl, an imidazopyridinyl, and an imidazopyrimidinyl. 
     
     
         14 . An organic photoelectric device, comprising:
 an anode,   a cathode, and   at least one organic thin layer between the anode and cathode,   wherein the at least one organic thin layer includes the compound as claimed in  claim 1 .   
     
     
         15 . The organic photoelectric device as claimed in  claim 14 , wherein the compound is a host material or a charge transport material. 
     
     
         16 . The organic photoelectric device as claimed in  claim 14 , wherein the at least one organic thin layer includes one of an emission layer, an electron transport layer (ETL), an electron injection layer (EIL), a hole transport layer (HTL), a hole injection layer (HIL), and a hole blocking layer. 
     
     
         17 . The organic photoelectric device as claimed in  claim 14 , wherein the at least one organic thin layer further includes a reducing dopant. 
     
     
         18 . The organic photoelectric device as claimed in  claim 17 , wherein the reducing dopant includes one of an alkaline metal, an alkaline earth metal, a rare earth element metal, an oxide of an alkaline metal, a halide of an alkaline metal, an organic complex of an alkaline metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an organic complex of an alkaline earth metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an organic complex of an alkaline earth metal, an oxide of a rare earth element metal, a halide of a rare earth element metal, and an organic complex of a rare earth element metal. 
     
     
         19 . A display device comprising an organic photoelectric device as claimed in  claim 14 . 
     
     
         20 . An organic photoelectric device, comprising:
 an anode,   a cathode, and   at least one organic thin layer between the anode and cathode,   wherein the at least one organic thin layer includes the compound as claimed in  claim 9 .