Luminescence device and polycyclic compound for luminescence device
Provided is a luminescence device including a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the hole transport region may include a polycyclic compound represented by Formula 1, thereby exhibiting a long service life and high efficiency.
1. A luminescence device comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region, wherein
the hole transport region comprises a polycyclic compound represented by Formula 1:
wherein in Formula 1,
X 1 is O or S,
Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, except that Ar 1 is not a heteroaryl group containing two or more nitrogen (N) atoms,
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring,
a is an integer from 0 to 4,
b is an integer from 0 to 3,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, except that L does not include a carbazole group, and
A is a group represented by Formula 2-1 or Formula 2-2, except that L is not a direct linkage when A is a group represented by Formula 2-2:
wherein in Formula 2-1 and Formula 2-2,
Y is N(Ar 3 ), O, or S,
X 2 is O or S,
Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, except that Ar 2 and Ar 3 are each not a heteroaryl group containing two or more nitrogen (N) atoms,
R 3 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,
R 6 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
c and e are each independently an integer from 0 to 3,
d and f are each independently an integer from 0 to 4, and
represents a binding site to a neighboring atom.
2. The luminescence device of claim 1 , wherein the hole transport region comprises:
a hole injection layer disposed on the first electrode; and
a hole transport layer disposed on the hole injection layer, wherein
the hole transport layer comprises the polycyclic compound represented by Formula 1.
3. The luminescence device of claim 1 , wherein the hole transport region comprises:
a hole transport layer disposed on the first electrode; and
an electron blocking layer disposed on the hole transport layer, wherein
the electron blocking layer comprises the polycyclic compound represented by Formula 1.
4. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 3-1 to Formula 3-3:
wherein in Formula 3-1 to Formula 3-3,
R 1 to R 4 , L, Ar 1 , Ar 3 , and a to d are the same as defined in connection with Formulas 1 and 2-1.
5. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 4-1 to Formula 4-3:
wherein in Formula 4-1 to Formula 4-3,
R 1 to R 4 , L, Ar 1 , Ar 3 , and a to d are the same as defined in connection with Formulas 1 and 2-1.
6. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 5-1 to Formula 5-3:
wherein in Formula 5-1 to Formula 5-3,
R 1 , R 2 , R 5 , R 6 , L, Ar 1 , Ar 2 , a, b, e, and f are the same as defined in connection with Formulas 1 and 2-2.
7. The luminescence device of claim 1 , wherein
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 6 to 12 ring-forming carbon atoms,
except that L does not include a carbazole group.
8. The luminescence device of claim 7 , wherein L is a direct linkage or is a group represented by one of L-1 to L-4:
wherein in L-1 to L-4,
X 3 is O or S,
R 8 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
p is an integer from 0 to 4, and
represents a binding site to a neighboring atom.
9. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 6:
wherein in Formula 6,
R 7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
g is an integer from 0 to 5, and
R 1 to R 3 , L, Ar 1 , Y, X 1 , and a to c are the same as defined in connection with Formulas 1 and 2-1.
10. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 7-1 to Formula 7-3:
wherein in Formula 7-1 to Formula 7-3,
R 1 to R 3 , L, Ar 1 , Y, X 1 , and a to c are the same as defined in connection with Formulas 1 and 2-1.
11. The luminescence device of claim 1 , wherein R 1 is a hydrogen atom or a deuterium atom.
12. The luminescence device of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted phenyl group.
13. The luminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is at least one selected from Compound Group 1:
14. A polycyclic compound represented by Formula 1:
wherein in Formula 1,
X 1 is O or S,
Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, except that Ar 1 is not a heteroaryl group containing two or more nitrogen (N) atoms,
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring,
a is an integer from 0 to 4,
b is an integer from 0 to 3,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, except that L does not include a carbazole group, and
A is a group represented by Formula 2-1 or Formula 2-2, except that L is not a direct linkage when A is a group represented by Formula 2-2:
wherein in Formula 2-1 and Formula 2-2,
Y is N(Ar 3 ), O, or S,
X 2 is O or S,
Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, except that Ar 2 and Ar 3 are each not a heteroaryl group containing two or more nitrogen (N) atoms,
R 3 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,
R 6 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
c and e are each independently an integer from 0 to 3,
d and f are each independently an integer from 0 to 4, and
represents a binding site to a neighboring atom.
15. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 3-1 to Formula 3-3:
wherein in Formula 3-1 to Formula 3-3,
R 1 to R 4 , L, Ar 1 , Ar 3 , and a to d are the same as defined in connection with Formulas 1, and 2-1.
16. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 4-1 to Formula 4-3:
wherein in Formula 4-1 to Formula 4-3,
R 1 to R 4 , L, Ar 1 , Ar 3 , and a to d are the same as defined in connection with Formulas 1, and 2-1.
17. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 5-1 to Formula 5-3:
wherein in Formula 5-1 to Formula 5-3,
R 1 , R 2 , R 5 , R 6 , L, Ar 1 , Ar 2 , a, b, e, and f are the same as defined in connection with Formulas 1, and 2-2.
18. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 6:
wherein in Formula 6,
R 7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and
g is an integer from 0 to 5, and
R 1 to R 3 , L, Ar 1 , Y, X 1 , and a to c are the same as defined in connection with Formulas 1, and 2-2.
19. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 7-1 to Formula 7-3:
wherein in Formula 7-1 to Formula 7-3,
R 1 to R 3 , L, Ar 1 , Y, X 1 , and a to c are the same as defined in connection with Formulas 1, and 2-1.
20. The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is at least one selected from Compound Group 1: