Organic compound, and organic photoelectric device including the same
Disclosed is an organic compound represented by the following Chemical Formula 1 that easily dissolves in an organic solvent, and that is applicable as a host material of an emission layer of an organic photoelectric device since it emits fluorescence and phosphorescence at a red wavelength through a blue wavelength.
1. An organic compound represented by the following Chemical Formula 1:
wherein, in the above Chemical Formula 1,
X 1 to X 16 are the same or different, and are independently selected from CR′ and N,
Ar 1 is selected from a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C2 to C30 heteroarylene group, provided that when Ar 1 includes a carbazolylene moiety, the carbazolylene moiety is N-bonded with a substituted phenyl,
Ar 2 to Ar 3 are the same or different, and are independently selected from a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C2 to C30 heteroarylene group,
Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
R′ is independently selected from hydrogen, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group.
2. The organic compound of claim 1 , wherein,
Ar 1 is selected from a carbazole N-bonded with a substituted phenyl, a substituted or unsubstituted arylamine, a substituted or unsubstituted phenyl, a substituted or unsubstituted tolyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted stilbene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted diphenyl anthracenyl, a substituted or unsubstituted dinaphthylanthracenyl, a substituted or unsubstituted pentacenyl, a substituted or unsubstituted bromophenyl, a substituted or unsubstituted hydroxyphenyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted azobenzenyl, and a substituted or unsubstituted ferrocenyl,
Ar 2 to Ar 3 are the same or different, and are independently selected from a substituted or unsubstituted carbazole, a substituted or unsubstituted arylamine, a substituted or unsubstituted phenyl, a substituted or unsubstituted tolyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted stilbene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted diphenyl anthracenyl, a substituted or unsubstituted dinaphthylanthracenyl, a substituted or unsubstituted pentacenyl, a substituted or unsubstituted bromophenyl, a substituted or unsubstituted hydroxyphenyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted azobenzenyl, and a substituted or unsubstituted ferrocenyl, and
Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted carbazole, a substituted or unsubstituted arylamine, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted thiophene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted pyridine, a substituted or unsubstituted aryloxadiazole, a substituted or unsubstituted triazole, and a substituted or unsubstituted arylsilane.
3. The organic compound of claim 1 , wherein Ar′ and Ar″ the same or different, and are independently selected from the substituents of the following Chemical Formulae 2 to 31:
wherein, in the above Chemical Formulae 2 to 31,
R 1 to R 76 are the same or different, and are independently selected from a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyl oxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyl oxy group, a substituted or unsubstituted C2 to C20 acyl amino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 aryl thiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
n 1 , n 2 , n 4 , n 6 , n 10 , n 21 , n 26 , n 27 , n 35 , n 39 , n 46 , n 47 , n 49 , n 53 , n 59 , n 61 , and n 62 are the same or different, and are integers ranging from 0 to 5,
n 3 , n 5 , n 7 , n 8 , n 11 , n 12 , n 16 , n 22 , n 23 , n 29 , n 30 , n 31 , n 33 , n 36 , n 37 , n 40 , n 41 to n 44 , n 48 , n 50 to n 52 , n 54 , n 55 , n 57 , n 60 , n 63 , n 65 , n 67 , n 68 , n 69 , n 70 , and n 71 are the same or different, and are integers ranging from 0 to 4,
n 9 , n 13 , n 14 , n 18 , n 19 , n 20 , n 25 , n 28 , n 32 , n 34 , n 38 , n 45 , n 56 , n 58 , and n 66 are the same or different, and are integers ranging from 0 to 3, and
n 15 and n 24 are the same or different, and are integers ranging from 0 to 2.
4. An organic compound represented by the following Chemical Formula 32:
wherein, in the above Chemical Formula 32,
X 1 to X 16 are the same or different, and are independently selected from CR′ and N,
Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
R 5 is selected from a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted C6 aryl group, a substituted or unsubstituted C7 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
R′ is selected from hydrogen, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group.
5. The organic compound of claim 4 , wherein Ar′ and Ar″ are the same or different, and are independently selected from the substituents represented by the following Chemical Formulae B-1 to B-9:
6. An organic compound represented by one of Chemical Formulae selected from the following Chemical Formulae 33, 34, and 37:
wherein, in the above Chemical Formulae 33, 34, and 37,
X 1 to X 16 are the same or different, and are independently selected from CR′ and N,
Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group,
R 5 is selected from a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted C6 aryl group, a substituted or unsubstituted C7 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino gimp, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
R 6 , R 7 and R′ are the same or different, and are independently hydrogen, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
n 5 to n 7 are the same or different, and are independently integers ranging from 0 to 5 and
n 5 ′ is an integer ranging from 1 to 5.
7. The organic compound of claim 6 , wherein Ar′ and Ar″ are the same or different, and are independently selected from the substituents represented by the following Chemical Formulae B-1 to B-9:
8. The organic compound of claim 4 , wherein Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted carbazole, a substituted or unsubstituted arylamine, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted thiophene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted pyridine, a substituted or unsubstituted aryloxadiazole, a substituted or unsubstituted triazole, and a substituted or unsubstituted arylsilane.
9. The organic compound of claim 6 , wherein Ar′ and Ar″ are the same or different, and are independently selected from a substituted or unsubstituted carbazole, a substituted or unsubstituted arylamine, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted thiophene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted pyridine, a substituted or unsubstituted aryloxadiazole, a substituted or unsubstituted triazole, and a substituted or unsubstituted arylsilane.
10. The organic compound of claim 4 , wherein Ar′ and Ar″ are the same or different, and are independently selected from the following Chemical Formulae 2 to 31:
wherein, in the above Chemical Formulae 2 to 31,
R 1 to R 76 are the same or different, and are independently selected from a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyl oxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyl oxy group, a substituted or unsubstituted C2 to C20 acyl amino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 aryl thiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
n 1 , n 2 , n 4 , n 6 , n 10 , n 21 , n 26 , n 27 , n 35 , n 39 , n 46 , n 47 , n 49 , n 53 , n 59 , n 61 , and n 62 are the same or different, and are integers ranging from 0 to 5,
n 3 , n 5 , n 7 , n 8 , n 11 , n 12 , n 16 , n 22 , n 23 , n 29 , n 30 , n 31 , n 33 , n 36 , n 37 , n 40 , n 41 to n 44 , n 48 , n 50 to n 52 , n 54 , n 55 , n 57 , n 60 , n 63 , n 65 , n 67 , n 68 , n 69 , n 70 , and n 71 are the same or different, and are integers ranging from 0 to 4,
n 9 , n 13 , n 14 , n 18 , n 19 , n 20 , n 25 , n 28 , n 32 , n 34 , n 38 , n 45 , n 56 , n 58 , and n 66 are the same or different, and are integers ranging from 0 to 3, and
n 15 and n 24 are the same or different, and are integers ranging from 0 to 2.
11. The organic compound of claim 6 , wherein Ar′ and Ar″ are the same or different, and are independently selected from compounds represented by the following Chemical Formulae 2 to 31:
wherein, in the above Chemical Formulae 2 to 31,
R 1 to R 76 are the same or different, and are independently selected from a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C2 to C20 heterooxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxy carbonyl amino group, a substituted or unsubstituted C7 to C20 acyloxy carbonyl amino group, a substituted or unsubstituted C1 to C20 sulfamoyl amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 hetero cycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C1 to C20 phosphoric acid amide group, and a substituted or unsubstituted C3 to C40 silyl group,
n 1 , n 2 , n 4 , n 6 , n 10 , n 21 , n 26 , n 27 , n 35 , n 39 , n 46 , n 47 , n 49 , n 53 , n 59 , n 61 , and n 62 are the same or different, and are independently integers ranging from 0 to 5,
n 3 , n 5 , n 7 , n 8 , n 11 , n 12 , n 16 , n 22 , n 23 , n 29 , n 30 , n 31 , n 33 , n 36 , n 37 , n 40 , n 41 to n 44 , n 48 , n 50 to n 52 , n 54 , n 55 , n 57 , n 56 , n 60 , n 63 , n 65 , n 67 , n 68 , n 69 , n 70 , and n 71 are the same or different, and are independently integers ranging from 0 to 4,
n 9 , n 13 , n 14 , n 18 , n 19 , n 20 , n 25 , n 28 , n 32 , n 34 , n 38 , n 45 , n 58 , and n 66 are the same or different, and are independently integers ranging from 0 to 3, and
and n 15 and n 24 are the same or different, and are independently integers ranging from 0 to 2.
12. An organic photoelectric device comprising:
an organic layer between a pair of electrodes,
wherein the organic layer includes the organic compound according to claim 1 .
13. The organic photoelectric device of claim 12 , wherein the organic layer is an emission layer.
14. The organic photoelectric device of claim 12 , wherein the organic layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, and combinations thereof.
15. The organic photoelectric device of claim 12 , wherein the organic layer is selected from an electron injection layer (EIL), an electron transport layer (ETL), an electron blocking layer, and combinations thereof.
16. The organic photoelectric device as claimed in claim 12 , wherein the organic layer includes compound CISH-2: