Organic compound, composition, and organic optoelectronic diode
The present invention relates to: an organic compound represented by Chemical Formula 1; a composition for an organic optoelectronic diode containing the organic compound; and an organic optoelectronic diode to which the organic compound or the composition is applied. In Chemical Formula 1, Z, R 1 to R 11 , and n1 to n4 are the same as those defined in the specification.
1. An organic compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.
2. The organic compound of claim 1 , wherein the organic compound is represented by Chemical Formula 1-I:
wherein, in Chemical Formula 1-I,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.
3. The organic compound of claim 1 , wherein the organic compound is represented by one of Chemical Formula 1-B:
wherein, in Chemical Formula 1-B,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.
4. The organic compound of claim 1 , wherein the organic compound is represented by one of Chemical Formulae 2 to 4:
wherein, in Chemical Formulae 2 to 4,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 , R 2 , R 3 , R 4 , R 3a , R 4a , R 3b , R 4b , R 5 , R 6 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring, and
n3 and n4 are independently 0 or 1.
5. The organic compound of claim 4 , wherein the compound represented by Chemical Formula 2 is represented by Chemical Formula 2a or 2b:
wherein, in Chemical Formulae 2a and 2b,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 4 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring, and
n3 and n4 are independently 0 or 1.
6. The organic compound of claim 4 , wherein the compound represented by Chemical Formula 3 is represented by one of Chemical Formulae 3a to 3g:
wherein, in Chemical Formulae 3a to 3g,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 , R 2 , R 3 , R 4 , R 3a , R 4a , R 3b , R 4b , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring, and
n3 and n4 are independently 0 or 1.
7. The organic compound of claim 4 , wherein the compound represented by Chemical Formula 4 is represented by Chemical Formula 4a:
wherein, in Chemical Formula 4a,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 , R 11 , and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring, and
n3 and n4 are independently 0 or 1.
8. The organic compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.
9. An organic compound selected from Group 1:
10. The organic compound of claim 1 , wherein the organic compound is represented by Chemical Formula 1-II:
wherein, in Chemical Formula 1-II,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 , and R 11 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.
11. The organic compound of claim 1 , wherein the organic compound is represented by Chemical Formula 1-A:
wherein, in Chemical Formula 1-A,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.
12. The organic compound of claim 1 , wherein the organic compound is represented by Chemical Formula 1-C:
wherein, in Chemical Formula 1-C,
Z is independently N, C, or CR a ,
at least one of Z's is N,
Ar 1 is a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C3 to C12 nitrogen-containing six-membered ring,
R 1 to R 6 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof,
R 7 to R 10 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C3 to C12 heterocyclic group,
R 1 and R 2 are independently present or linked with each other to form a ring,
R 5 and R 6 are independently present or linked with each other to form a ring,
R 7 and R 8 are independently present or linked with each other to form a ring,
R 9 and R 10 are independently present or linked with each other to form a ring,
n1 is an integer ranging from 1 to 5,
n2 is an integer ranging from 0 to 2, and
n3 and n4 are independently 0 or 1.