Organic electroluminescence device and polycyclic compound for organic electroluminescence device
An organic electroluminescence device includes: a first electrode; a second electrode disposed on the first electrode; and at least one organic layer disposed between the first electrode and the second electrode. wherein the at least one organic layer includes a polycyclic compound having a core structure including a n,n′-bicarbazole moiety and, outside the core structure, at least one optionally substituted carbazole group, and the substituted or unsubstituted carbazole groups of the core structure substituted at any one among carbon atoms at position n±1 of the n,n′-bicarbazole moiety, and any one among carbon atoms at position n′±1 of the n,n′-bicarbazole moiety, respectively; and n and n′ are, independently from one another, integers of 1 to 4 (where n±1 and n′±1 are not 0).
1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
at least one organic layer disposed between the first electrode and the second electrode;
wherein
the at least one organic layer comprises a polycyclic compound having a core structure including a n,n′-bicarbazole moiety and at least one substituted or unsubstituted carbazole group, and
the substituted or unsubstituted carbazole groups are substituted at any one among carbon atoms at position n±1 of the n,n′-bicarbazole moiety, and any one among carbon atoms at position n′±1 of the n,n′-bicarbazole moiety, respectively; and
n and n′ are, independently from one another, integers of 1, 2, or 4, wherein n+1 and n′+1 are not 0.
2. The organic electroluminescence device of claim 1 , wherein n and n′ are the same; and
the substituted or unsubstituted carbazole groups are substituted at a carbon atom at position n+1 of the n,n′-bicarbazole moiety and a carbon atom at position n′+1 of the n,n′-bicarbazole moiety, respectively, or at a carbon atom at position n−1 of the n,n′-bicarbazole moiety and a carbon atom at position n′−1 of the n,n′-bicarbazole moiety, respectively.
3. The organic electroluminescence device of claim 1 , wherein the polycyclic compound has a symmetrical structure about a connecting group of the n,n′-bicarbazole moiety; and
the connecting group is a group connecting two carbazole groups at carbon at position n and carbon at position n′ of the n,n′-bicarbazole moiety via a direct bond.
4. The organic electroluminescence device of claim 1 , wherein nitrogen at position 9 of the at least one substituted or unsubstituted carbazole group is bonded to the n,n′-bicarbazole moiety.
5. The organic electroluminescence device of claim 1 , wherein an energy level of a highest occupied molecular orbital of the polycyclic compound is from about −5.50 eV to about −5.00 eV.
6. The organic electroluminescence device of claim 1 , wherein a lowest excitation triplet energy level of the polycyclic compound is about 3.00 eV to about 3.20 eV.
7. The organic electroluminescence device of claim 1 , wherein the at least one organic layer comprises:
a hole transport region comprising the polycyclic compound disposed on the first electrode;
an emission layer disposed on the hole transport region; and
an electron transport region disposed between the emission layer and the second electrode.
8. The organic electroluminescence device of claim 7 , wherein the emission layer is configured to emit thermally activated delayed fluorescence.
9. The organic electroluminescence device of claim 7 , wherein the emission layer is configured to emit blue light.
10. The organic electroluminescence device of claim 1 , wherein the polycyclic compound is represented by the following Formula 1:
in Formula 1,
L is a direct linkage;
R 1 to R 4 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m1 to m4 are each, independently from one another, an integer of 1 to 4;
Z 1 to Z 8 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring; and
at least one pair among Z 1 and Z 2 , Z 2 and Z 3 , and Z 3 and Z 4 represented by the following Formula 2-1, and at least one pair among Z 5 and Z 6 , Z 6 and Z 7 , and Z 7 and Z 8 represented by the following Formula 2-2:
in Formulae 2-1 and 2-2,
R 11 , and R 12 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m11 and m12 are each, independently from one another, an integer of 1 to 4; and
Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
wherein
when Z 2 and Z 3 are represented by the Formula 2-1 and Z 6 and Z 7 are represented by the Formula 2-2, then Z 2 is not represented by nitrogen of the Formula 2-1 and Z 6 is not represented by nitrogen of the Formula 2-2.
11. The organic electroluminescence device of claim 10 , wherein Formula 1 has a symmetrical structure about L.
12. The organic electroluminescence device of claim 10 , wherein a compound of Formula 1 is represented by one or more compounds of the following Formulae 1-3 to 1-6:
in Formulae 1-3 to 1-6,
R 41 to R 46 , R 51 to R 56 , R 61 to R 66 , and R 71 to R 76 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m41 to m46, m51 to m56, m61 to m66, and m71 to m76 are each, independently from one another, an integer of 1 to 4; and
Ar 31 , Ar 32 , Ar 41 , Ar 42 , Ar 51 , Ar 52 , Ar 61 , and Ar 62 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
13. The organic electroluminescence device of claim 10 , wherein R 1 to R 4 are the same, and Ar 1 and Ar 2 are the same.
14. The organic electroluminescence device of claim 10 , wherein the polycyclic compound comprises at least one compound from the following Compound Group 1:
15. An organic electroluminescence device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
at least one organic layer disposed between the first electrode and the second electrode;
wherein the organic layer comprises a polycyclic compound represented by the following Formula 1:
in Formula 1,
L is a direct linkage;
R 1 to R 4 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m1 to m4 are each, independently from one another, an integer of 1 to 4;
Z 1 to Z 8 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring; and
at least one pair among Z 1 and Z 2 , Z 2 and Z 3 , and Z 3 and Z 4 is represented by the following Formula 2-1, and at least one pair among Z 5 and Z 6 , Z 6 and Z 7 , and Z 7 and Z 8 is represented by the following Formula 2-2:
in Formulae 2-1 and 2-2,
R 11 , and R 12 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m11 and m12 are each, independently from one another, an integer of 1 to 4; and
Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
wherein
when Z 2 and Z 3 are represented by the Formula 2-1 and Z 6 and Z 7 are represented by the Formula 2-2, then Z 2 is not represented by nitrogen of the Formula 2-1 and Z 6 is not represented by nitrogen of the Formula 2-2.
16. The organic electroluminescence device of claim 15 , wherein Formula 1 has a symmetrical structure about L.
17. The organic electroluminescence device of claim 15 , wherein a compound of Formula 1 is represented by one or more compounds of the following Formulae 1-3 to 1-6:
in Formulae 1-3 to 1-6,
R 41 to R 46 , R 51 to R 56 , R 61 to R 66 , and R 71 to R 76 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m41 to m46, m51 to m56, m61 to m66, and m71 to m76 are each, independently from one another, an integer of 1 to 4; and
Ar 31 , Ar 32 , Ar 41 , Ar 42 , Ar 51 , Ar 52 , Ar 61 , and Ar 62 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
18. The organic electroluminescence device of claim 15 , wherein R 1 to R 4 are the same, and Ar 1 and Ar 2 are the same.
19. A polycyclic compound represented by the following Formula 1:
in Formula 1,
L is a direct linkage;
R 1 to R 4 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m1 to m4 are each, independently from one another, an integer of 1 to 4;
Z 1 to Z 8 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring; and
at least one pair among Z 1 and Z 2 , Z 2 and Z 3 , and Z 3 and Z 4 is represented by the following Formula 2-1, and at least one pair among Z 5 and Z 6 , Z 6 and Z 7 , and Z 7 and Z 8 is represented by the following Formula 2-2:
in Formulae 2-1 and 2-2,
R 11 , and R 12 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring;
m11 and m12 are each, independently from one another, an integer of 1 to 4; and
Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
wherein
when Z 2 and Z 3 are represented by the Formula 2-1 and Z 6 and Z 7 are represented by the Formula 2-2, then Z 2 is not represented by nitrogen of the Formula 2-1 and Z 6 is not represented by nitrogen of the Formula 2-2.
20. The polycyclic compound of claim 19 , wherein Formula 1 has a symmetrical structure about L.
21. The polycyclic compound of claim 19 , wherein a compound of Formula 1 is represented by one or more compounds of the following Formulae 1-3 to 1-6:
in Formulae 1-3 to 1-6,
R 41 to R 46 , R 51 to R 56 , R 61 to R 66 , and R 71 to R 76 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,
m41 to m46, m51 to m56, m61 to m66, and m71 to m76 are each, independently from one another, an integer of 1 to 4, and
Ar 31 , Ar 32 , Ar 41 , Ar 42 , Ar 51 , Ar 52 , Ar 61 , and Ar 62 are each, independently from one another, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
22. The polycyclic compound of claim 19 , wherein R 1 to R 4 are the same, and Ar 1 and Ar 2 are the same.
23. The polycyclic compound of claim 19 , wherein a compound of Formula 1 comprises at least one compound from Compound Group 1: