Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device
An organic electroluminescence device of an embodiment includes oppositely disposed first electrode and second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one from among the organic layers includes a fused polycyclic compound represented by Formula 1 below, thereby showing improved emission efficiency.
1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode opposite to the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, or a compound of two or more selected from them, a mixture of two or more selected from them, or oxides thereof,
wherein at least one organic layer from among the plurality of organic layers comprises the fused polycyclic compound
wherein in Formula 1,
one selected from X and Y is BR a or P(═O)R b , and an other one selected from X and Y is SiR c R d ,
R a to R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R a to R d are optionally combined with an adjacent group to form a ring, and
R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a boron group, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 11 to R 21 are optionally combined with an adjacent group to form a ring,
with the proviso that when the fused polycyclic compound is represented by Formula 1-3 and X 13 of Formula 1-3 is B, then R 17 of Formula 1-3 is a substituted or unsubstituted amine group, or one of R m in a number of m is a carbazole group, or two adjacent R m s are combined to form a spiro structure in Formula 1-3:
wherein in Formula 1-3, R 11 to R 13 , R 15 to R 21 , R c , and R d are the same as respectively defined in association with Formula 1,
R m is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, or optionally combined with an adjacent group to form a ring,
m is an integer of 0 to 4, and
Ar is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring.
2. The organic electroluminescence device of claim 1 , wherein
the plurality of organic layers comprises:
a hole transport region on the first electrode;
an emission layer on the hole transport region; and
an electron transport region on the emission layer, and
the emission layer comprises the fused polycyclic compound represented by Formula 1.
3. The organic electroluminescence device of claim 2 , wherein the emission layer is to emit delayed fluorescence.
4. The organic electroluminescence device of claim 2 , wherein
the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and
the dopant comprises the fused polycyclic compound represented by Formula 1.
5. The organic electroluminescence device of claim 2 , wherein the emission layer comprises:
a host having a first lowest triplet excitation energy level;
a first dopant having a second lowest triplet excitation energy level lower than the first lowest triplet excitation energy level; and
a second dopant having a third lowest triplet excitation energy level lower than the second lowest triplet excitation energy level, and
the first dopant comprises the fused polycyclic compound represented by Formula 1.
6. The organic electroluminescence device of claim 5 , wherein
the first dopant is a delayed fluorescence dopant, and
the second dopant is a fluorescence dopant.
7. The organic electroluminescence device of claim 1 , wherein
the fused polycyclic compound represented by Formula 1 is represented by any one from among the following Formula 1-1 to Formula 1-3:
wherein in Formula 1-1 to Formula 1-3,
R 1 to R 21 , R c , and R d are the same as respectively defined in association with Formula 1,
X 1 , X 11 , X 12 , and X 13 are each independently B or P(=O),
R n and R m are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R n and R m are optionally combined with an adjacent group to form a ring,
n is an integer of 0 to 5,
m is an integer of 0 to 4,
R aa and R bb are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R aa and R bb are optionally combined with an adjacent group to form a ring, and
Ar is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring,
with the proviso that when the fused polycyclic compound is represented by Formula 1-3 and X 13 of Formula 1-3 is B, then R 17 of Formula 1-3 is a substituted or unsubstituted amine group, or one of R m in a number of m is a carbazole group, or two adjacent R m s are combined to form a spiro structure in Formula 1-3.
8. The organic electroluminescence device of claim 7 , wherein X 1 in Formula 1-1 is P(=O), and n is 0.
9. The organic electroluminescence device of claim 7 , wherein X 11 and X 12 in Formula 1-2 are the same.
10. The organic electroluminescence device of claim 7 , wherein
in Formula 1-2, in case where X 11 and X 12 are each B, R aa and R bb are each independently a substituted or unsubstituted phenyl group, and
in case where X 11 and X 12 are each P(=O), R aa and R bb are each independently an unsubstituted phenyl group.
11. The organic electroluminescence device of claim 1 , wherein R c and R d are each independently an unsubstituted phenyl group.
12. The organic electroluminescence device of claim 1 , wherein the fused polycyclic compound represented by Formula 1 comprises at least one selected from compounds in the following Compound Group 1:
13. A fused polycyclic compound represented by the following Formula 1:
wherein in Formula 1,
one selected from X and Y is BR a or P(═O)R b , and an other one selected from X and Y is SiR c R d ,
R a to R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R a to R d are optionally combined with an adjacent group to form a ring, and
R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a boron group, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R 11 to R 21 are optionally combined with an adjacent group to form a ring,
with the proviso that when the fused polycyclic compound is represented by Formula 1-3 and X 13 of Formula 1-3 is B, then R 17 of Formula 1-3 is a substituted or unsubstituted amine group, or one of R m in a number of m is a carbazole group, or two adjacent R m s are combined to form a spiro structure in Formula 1-3:
wherein in Formula 1-3, R 11 to R 13 , R 15 to R 21 , R c , and R d are the same as respectively defined in association with Formula 1,
R m is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, or optionally combined with an adjacent group to form a ring,
m is an integer of 0 to 4, and
Ar is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring.
14. The fused polycyclic compound of claim 13 , wherein
the fused polycyclic compound represented by Formula 1 has an absolute value of a difference between a lowest singlet excitation energy level (S1) and a lowest triplet excitation energy level (T1) of about 0.1 eV or less.
15. The fused polycyclic compound of claim 13 , wherein
the fused polycyclic compound represented by Formula 1 is represented by any one from among the following Formula 1-1 to Formula 1-3:
wherein in Formula 1-1 to Formula 1-3,
R 1 to R 21 , R c , and R d are the same as respectively defined in association with Formula 1,
X 1 , X 11 , X 12 , and X 13 are each independently B or P(═O),
R n and R m are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R n and R m are optionally combined with an adjacent group to form a ring,
n is an integer of 0 to 5,
m is an integer of 0 to 4,
R aa and R bb are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R aa and R bb are optionally combined with an adjacent group to form a ring, and
Ar is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring,
with the proviso that when the fused polycyclic compound is represented by Formula 1-3 and X 13 of Formula 1-3 is B, then R 17 of Formula 1-3 is a substituted or unsubstituted amine group, or one of R m in a number of m is a carbazole group, or two adjacent R m s are combined to form a spiro structure in Formula 1-3.
16. The fused polycyclic compound of claim 15 , wherein X 1 in Formula 1-1 is P(═O), and n is O.
17. The fused polycyclic compound of claim 15 , wherein X 11 and X 12 in Formula 2 are the same.
18. The fused polycyclic compound of claim 15 , wherein
in Formula 1-2, in case where X 11 and X 12 are each B, R aa and R bb are each independently a substituted or unsubstituted phenyl group, and
in case where X 11 and X 12 are each P(═O), R aa and R bb are each independently an unsubstituted phenyl group.
19. The fused polycyclic compound of claim 13 , wherein R c and R d are each independently an unsubstituted phenyl group.
20. The fused polycyclic compound of claim 13 , wherein the fused polycyclic compound represented by Formula 1 is any one selected from compounds in the following Compound Group 1: