Organic electroluminescence device and polycyclic compound for organic electroluminescence device
An organic electroluminescence device having high light emission efficiency is provided, which includes a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes a polycyclic compound represented by Formula 1:
1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
an emission layer disposed between the first electrode and the second electrode,
wherein the first electrode and the second electrode each independently include at a least one material selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, oxides thereof, compounds thereof, and mixtures thereof;
wherein the emission layer includes a polycyclic compound represented by Formula 1:
wherein in Formula 1,
X 1 is NAr 2 , O, or S,
Y 1 to Y 8 are each independently CM 1 or a carbon atom bonded to a group represented by Formula 2,
each M 1 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
Ar 1 and Ar 2 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,
R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
a, b, c, and d are each independently an integer from 0 to 2,
at least one group represented by Formula 2 is bonded to at least one pair of substituents, the at least one pair of substituents selected from the group consisting of Y 1 and Y 2 , Y 3 and Y 4 , Y 5 and Y 6 , and Y 7 and Y 8 ,
wherein in Formula 2,
each X 2 and each X 3 are independently NAr 3 , O, or S,
each Ar 3 is 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,
each R 6 and each R 7 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
each e is independently an integer from 0 to 3,
each f is independently an integer from 0 to 4, and
* indicates a binding site to a neighboring atom.
2. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 1-1a to 1-1c:
wherein in Formulas 1-1a to 1-1c,
Y 1 to Y 8 , Ar 1 , Ar 2 , and R 1 to R 5 are the same as defined in Formulas 1 and 2.
3. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2:
wherein in Formulas 3-1 and 3-2,
X 21 , X 22 , X 31 , and X 32 are each independently NAr 4 , O, or S,
each Ar 4 is 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,
R 61 , R 62 , R 71 , and R 72 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 carbon atoms, or bonded to an adjacent group to form a ring,
a1 and d1 are each independently an integer from 0 to 2,
b1 and c1 are each independently an integer from 0 to 4,
e1 and e2 are each independently an integer from 0 to 3,
f1 and f2 are each independently an integer from 0 to 4, and
X 1 , Ar 1 , and R 1 to R 5 are the same as defined in Formulas 1 and 2.
4. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 4-1a to 4-1d:
wherein in Formulas 4-1a to 4-1d,
X 21 , X 22 , X 31 , and X 32 are each independently NAr 4 , O, or S,
each Ar 4 is 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,
R 61 , R 62 , R 71 , and R 72 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having ring-forming 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring,
a1, b2, c2, and d1 are each independently an integer from 0 to 2,
a2, b1, c1, and d2 are each independently an integer from 0 to 4,
e1 and e2 are each independently an integer from 0 to 3,
f1 and f2 are each independently an integer from 0 to 4, and
X 1 , Ar 1 , and R 1 to R 5 are the same as defined in Formulas 1 and 2.
5. The organic electroluminescence device of claim 4 , wherein the polycyclic compound represented by Formula 4-1a has a line-symmetrical structure with respect to an imaginary line passing through a central nitrogen atom and R 5 .
6. The organic electroluminescence device of claim 4 , wherein the polycyclic compound represented by Formula 4-1d has a line-symmetrical structure with respect to an imaginary line passing through a central nitrogen atom and R 5 .
7. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 4-2a to 4-2d:
wherein in Formulas 4-2a to 4-2d,
X 21 , X 22 , X 31 , and X 32 are each independently NAr 4 , O, or S,
each Ar 4 is 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,
R 61 , R 62 , R 71 , and R 72 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
e1 and e2 are each independently an integer from 0 to 3,
f1 and f2 are each independently an integer from 0 to 4, and
X 1 and Ar 1 are the same as defined in Formulas 1 and 2.
8. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 5-1 or Formula 5-2:
wherein in Formulas 5-1 and 5-2,
each of X 1 , X 2 , X 3 , Ar 1 , R 6 , R 7 , e, and f are independently the same as defined in Formulas 1 and 2.
9. The organic electroluminescence device of claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group.
10. The organic electroluminescence device of claim 1 , wherein R 6 and R 7 are each independently an unsubstituted methyl group, an unsubstituted isopropyl group, an unsubstituted t-butyl group, a substituted or unsubstituted biphenyl amine group, or an unsubstituted phenyl group.
11. The organic electroluminescence device of claim 1 , wherein the emission layer emits delayed fluorescence.
12. The organic electroluminescence device of claim 1 , wherein the emission layer emits light in a blue wavelength range.
13. The organic electroluminescence device of claim 1 , wherein
the emission layer comprises a first compound and a second compound, and
the first compound includes the polycyclic compound.
14. The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is selected from one of the compounds represented by Compound Group 1:
15. A polycyclic compound represented by Formula 1:
wherein in Formula 1,
X 1 is NAr 2 , O, or S,
Y 1 to Y 8 are each independently CM 1 or a carbon atom bonded to a group represented by Formula 2,
each M 1 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
Ar 1 and Ar 2 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,
R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
a, b, c, and d are each independently an integer of 0 to 2,
at least one group represented by Formula 2 is bonded to at least one pair of substituents, the at least one pair of substituents selected from the group consisting of Y 1 and Y 2 , Y 3 and Y 4 , Y 5 and Y 6 , and Y 7 and Y 8 ,
wherein in Formula 2,
each X 2 and each X 3 are independently NAr 3 , O, or S,
each Ar 3 is 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,
each R 6 and each R 7 are independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
each e is independently an integer from 0 to 3,
each f is independently an integer from 0 to 4, and
* indicates a binding site to a neighboring atom.
16. The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 1-1a to 1-1c:
wherein in Formulas 1-1a to 1-1c,
Y 1 to Y 8 , Ar 1 , Ar 2 , and R 1 to R 5 are the same as defined in Formulas 1 and 2.
17. The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 4-1a to 4-1d:
wherein in Formulas 4-1a to 4-1d,
X 21 , X 22 , X 31 , and X 32 are each independently NAr 4 , O, or S,
each Ar 4 is 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,
R 61 , R 62 , R 71 , and R 72 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having ring-forming 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring,
a1, b2, c2, and d1 are each independently an integer from 0 to 2,
a2, b1, c1, and d2 are each independently an integer from 0 to 4,
e1 and e2 are each independently an integer from 0 to 3,
f1 and f2 are each independently an integer from 0 to 4, and
X 1 , Ar 1 , and R 1 to R 5 are the same as defined in Formulas 1 and 2.
18. The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formulas 4-2a to 4-2d:
wherein in Formulas 4-2a to 4-2d,
X 21 , X 22 , X 31 , and X 32 are each independently NAr 4 , O, or S,
each Ar 4 is 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,
R 61 , R 62 , R 71 , and R 72 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, 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 bonded to an adjacent group to form a ring,
e1 and e2 are each independently an integer from 0 to 3,
f1 and f2 are each independently an integer from 0 to 4, and
X 1 and Ar 1 are the same as defined in Formulas 1 and 2.
19. The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 5-1 or Formula 5-2:
wherein in Formulas 5-1 and 5-2,
each of X 1 , X 2 , X 3 , Ar 1 , R 6 , R 7 , e, and f are independently the same as defined in Formulas 1 and 2.
20. The polycyclic compound of claim 15 , wherein the polycyclic compound represented by Formula 1 is selected from one of the compounds represented by Compound Group 1: