Light emitting device and polycyclic compound for light emitting device
A polycyclic compound of an embodiment is represented by Formula 1, which is defined in the disclosure. A light emitting device of an embodiment includes a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes the polycyclic compound represented by Formula 1, and the light emitting device may show improved device characteristics.
1. A light emitting device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
an emission layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by Formula 1,
wherein the light emitting device has an external quantum efficiency in a range of about 20% to about 30%:
wherein in Formula 1,
W 1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group,
Q 1 is NR 16 , O, or S, and
R 1 to R 16 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, or a group represented by Formula 2 is bonded to adjacent groups of R 1 to R 16 :
wherein in Formula 2,
Q 2 and Q 3 are each independently NR 23 , O, or S,
m1 is an integer from 1 to 3,
m2 is an integer from 1 to 4,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, and
indicates a binding site to a neighboring atom.
2. A light emitting device, comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region and comprising a polycyclic compound represented by Formula 1;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region:
wherein in Formula 1,
W 1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group,
Q 1 is NR 16 , O, or S,
R 2 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms,
R 12 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, and
R 1 , R 3 to R 11 , and R 13 to R 16 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, or a group represented by Formula 2 is bonded to adjacent groups of R 4 to R 11 :
wherein in Formula 2,
Q 2 and Q 3 are each independently NR 23 , O, or S,
m1 is an integer from 1 to 3,
m2 is an integer from 1 to 4,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms,
indicates a binding site to a neighboring atom, and
the polycyclic compound does not include an alkyl group substituted with a deuterium atom.
3. The light emitting device of claim 2 , wherein Formula 1 is represented by one of Formula 1-A1 to Formula 1-A4:
wherein in Formula 1-A1 to Formula 1-A4,
m31 is an integer from 1 to 8,
m32 is an integer from 1 to 7,
R 31 to R 33 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, and
Q 1 and R 1 to R 15 are the same as defined in connection with Formula 1.
4. The light emitting device of claim 2 , wherein Formula 1 is represented by Formula 1-B1 or Formula 1-B2:
wherein in Formula 1-B1 and Formula 1-B2,
Q 1 to Q 3 , R 1 to R 15 , m1, m2, R 21 , R 22 , and W 1 are the same as defined in connection with Formula 1 and Formula 2.
5. The light emitting device of claim 4 , wherein at least one of Q 1 to Q 3 is O or S.
6. The light emitting device of claim 4 , wherein Formula 1-B1 is represented by one of Formula 1-B1-1 to Formula 1-B1-4:
wherein in Formula 1-B1-1 to Formula 1-B1-4,
m41 is an integer from 1 to 8,
m42 is an integer from 1 to 7,
R 41 to R 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms,
Q 1 to Q 3 , R 1 to R 7 , R 12 to R 15 , m1, m2, R 21 and R 22 are the same as defined in connection with Formula 1 and Formula 2.
7. The light emitting device of claim 4 , wherein Formula 1-B2 is represented by one of Formula 1-B2-1 to Formula 1-B2-4:
wherein in Formula 1-B2-1 to Formula 1-B2-4,
m41 is an integer from 1 to 8,
m42 is an integer from 1 to 7,
R 41 to R 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms,
Q 1 to Q 3 , R 1 to R 3 , R 8 to R 15 , m1, m2, R 21 and R 22 are the same as defined in connection with Formula 1 and Formula 2.
8. The light emitting device of claim 2 , wherein Formula 1 is represented by one of Formula 1-C1 to Formula 1-C3:
wherein in Formula 1-C1 to Formula 1-C3,
W 1 and R 1 to R 16 are the same as defined in connection with Formula 1.
9. The light emitting device of claim 2 , further comprising a capping layer disposed on the second electrode, wherein a refractive index of the capping layer is equal to or greater than about 1.6.
10. The light emitting device of claim 2 , wherein the hole transport region comprises an amine compound represented by Formula H-1:
wherein in Formula H-1,
a and b are each independently an integer from 0 to 10,
L 1 and L 2 are each independently a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
Ar 3 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms.
11. The light emitting device of claim 2 , wherein the emission layer comprises at least one polycyclic compound selected from Compound Group 1:
wherein in the compounds of Compound Group 1,
Ph is a phenyl group,
Mes is a mesityl group, and
D is a deuterium atom.
12. A polycyclic compound represented by Formula 1:
wherein in Formula 1,
W 1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group,
Q 1 is NR 16 , O, or S,
R 2 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms,
R 12 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, and
R 1 , R 3 to R 11 , and R 13 to R 16 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, or a group represented by Formula 2 is bonded to adjacent groups of R 4 to R 11 :
wherein in Formula 2,
Q 2 and Q 3 are each independently NR 23 , O, or S,
m1 is an integer from 1 to 3,
m2 is an integer from 1 to 4,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms,
indicates a binding site to a neighboring atom, and
the polycyclic compound does not include an alkyl group substituted with a deuterium atom.
13. The polycyclic compound of claim 12 , wherein Formula 1 is represented by one of Formula 1-A1 to Formula 1-A4:
wherein in Formula 1-A1 to Formula 1-A4,
m31 is an integer from 1 to 8,
m32 is an integer from 1 to 7,
R 31 to R 33 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, and
Q 1 and R 1 to R 15 are the same as defined in connection with Formula 1.
14. The polycyclic compound of claim 13 , wherein R 32 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, or an unsubstituted anthracenyl group.
15. The polycyclic compound of claim 12 , wherein Formula 1 is represented by Formula 1-B1 or Formula 1-B2:
wherein in Formula 1-B1 and Formula 1-B2,
Q 1 to Q 3 , R 1 to R 15 , m1, m2, R 21 , R 22 , and Wi are the same as defined in connection with Formula 1 and Formula 2.
16. The polycyclic compound of claim 15 , wherein Formula 1-B1 is represented by one of Formula 1-B1-1 to Formula 1-B1-4:
wherein in Formula 1-B1-1 to Formula 1-B1-4,
m41 is an integer from 1 to 8,
m42 is an integer from 1 to 7,
R 41 to R 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, 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 20 ring-forming carbon atoms,
Q 1 to Q 3 , R 1 to R 7 , R 12 to R 15 , m1, m2, R 21 and R 22 are the same as defined in connection with Formula 1 and Formula 2.
17. The polycyclic compound of claim 15 , wherein Formula 1-B2 is represented by one of Formula 1-B2-1 to Formula 1-B2-4:
wherein in Formula 1-B2-1 to Formula 1-B2-4,
m41 is an integer from 1 to 8,
m42 is an integer from 1 to 7,
R 41 to R 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms,
Q 1 to Q 3 , R 1 to R 3 , R 8 to R 15 , m1, m2, R 21 and R 22 are the same as defined in connection with Formula 1 and Formula 2.
18. The polycyclic compound of claim 12 , wherein R 2 is represented by one of R 2-1 to R 2-5 :
wherein in R 2-1 ,
m11 and m12 are each independently an integer from 0 to 5,
R 51 and R 52 are each independently a methyl group, a phenyl group, a carbazole group, or a dibenzofuran group, and
wherein in R 2-1 to R 2-5 ,
indicates a binding site to a neighboring atom.
19. The polycyclic compound of claim 12 , wherein the polycyclic compound represented by Formula 1 is a material emitting thermally activated delayed fluorescence.
20. The polycyclic compound of claim 12 , wherein the polycyclic compound is selected from Compound Group 1:
wherein in the compounds of Compound Group 1,
Ph is a phenyl group,
Mes is a mesityl group, and
D is a deuterium atom.