Organic electroluminescence device and organometallic compound for organic electroluminescence device
The present disclosure relates to an organic electroluminescence device including an organometallic compound represented by Formula 1 or Formula 2 below in an emission layer, to achieve long service life of the organic electroluminescence device.
1. An organic electroluminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises an organometallic compound comprising a metal atom and a ligand linked with the metal atom,
wherein the ligand comprises:
at least one substituted or unsubstituted borazine group directly linked to the metal atom; and
at least one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring group.
2. The organic electroluminescence device of claim 1 ,
wherein the metal atom is a platinum (Pt) atom, an iridium (Ir) atom, a palladium (Pd) atom, or an osmium (Os) atom.
3. The organic electroluminescence device of claim 2 ,
wherein the metal atom is a platinum atom, and the ligand is a tetradentate ligand, or
the metal atom is an iridium atom, and the ligand comprises two tridentate ligands or one hexadentate ligand.
4. The organic electroluminescence device of claim 1 ,
wherein the substituted or unsubstituted aryl group is a substituted or unsubstituted benzene derivative, and
the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted aromatic carbene derivative.
5. The organic electroluminescence device of claim 1 ,
wherein the emission layer is to emit light having a center wavelength of about 420 nm to about 470 nm via phosphorescence luminescence.
6. The organic electroluminescence device of claim 1 ,
wherein the emission layer comprises a host and a dopant, and
the dopant comprises the organometallic compound.
7. The organic electroluminescence device of claim 1 ,
wherein a difference (Δ(T 1 − 3 MC)) between T 1 energy level and 3 MC energy level of the organometallic compound is about 0.3 eV or more.
8. The organic electroluminescence device of claim 1 ,
wherein the organometallic compound is represented by Formula 1 or Formula 2:
wherein, in Formula 1 and Formula 2,
X 1 to X 4 and X 11 to X 16 are each independently a carbon atom or a nitrogen atom,
A1 to A4 and B1 to B6 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring,
at least one selected from A1 to A4, and at least one selected from B1 to B6, are a substituted or unsubstituted borazine group,
R 1 to R 4 and R 11 to R 16 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 1 to R 4 and R 11 to R 16 are optionally combined with an adjacent group to form a ring,
a1 to a4 and a11 to a16 are each independently an integer of 0 to 3,
L 1 to L 3 and L 11 to L 16 are each independently a direct linkage, *—O—*, *—S—*, a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms for forming a ring,
b1 to b3 and b11 to b16 are each independently 0 or 1, and
in Formula 2, B1, B3, and B6 are optionally linked to a linker represented by Formula 2A:
wherein, in Formula 2A,
L 31 is a nitrogen atom, a substituted or unsubstituted trivalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trivalent aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted trivalent heteroaryl group having 1 to 30 carbon atoms for forming a ring, and
c is 0 or 1.
9. The organic electroluminescence device of claim 8 ,
wherein A1 to A4 and B1 to B6 are each independently any one selected from LG1 to LG3:
wherein, in LG1 to LG3,
X 21 and X 22 are each independently CR 24 , or a nitrogen atom,
Y 1 is CR 25 or C—*,
Y 2 is NR 26 or N—,
Y 3 is B or B—*, and
R 21 to R 29 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 21 to R 29 are optionally combined with an adjacent group to form a ring.
10. The organic electroluminescence device of claim 9 ,
wherein Formula 1 is represented by Formula 1-1:
wherein, in Formula 1-1,
A21 and A31 are each independently LG1 or LG3, and at least one selected from A21 and A31 is LG3, and
R 31 to R 36 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 31 to R 36 are optionally combined with an adjacent group to form a ring.
11. The organic electroluminescence device of claim 9 ,
wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
wherein, in Formula 2-1 and Formula 2-2,
B41 to B61 are each independently LG1, LG2, or LG3, and at least one selected from B41 to B61 is LG3,
R 41 to R 45 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 41 to R 45 are optionally combined with an adjacent group to form a ring,
R 51 to R 62 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 51 to R 62 are optionally combined with an adjacent group to form a ring,
L 31 is the same as defined in Formula 2A, and
X 21 and X 22 are the same as defined in LG2.
12. The organic electroluminescence device of claim 1 ,
wherein the emission layer comprises at least one selected from compounds represented by Compound Group 1:
13. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises an organometallic compound represented by Formula 1 or Formula 2:
wherein, in Formula 1 and Formula 2,
X 1 to X 4 and X 11 to X 16 are each independently a carbon atom or a nitrogen atom,
A1 to A4 and B1 to B6 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring,
at least one selected from A1 to A4, and at least one selected from B1 to B6, are a substituted or unsubstituted borazine group,
R 1 to R 4 and Rug to R 16 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 1 to R 4 and Rug to R 16 are optionally combined with an adjacent group to form a ring,
a1 to a4 and a11 to a16 are each independently an integer of 0 to 3,
L 1 to L 3 and L 11 to L 16 are each independently a direct linkage, *—O—*, *—S—*, a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms for forming a ring,
b1 to b3 and b11 to b16 are each independently 0 or 1, and
in Formula 2, B1, B3, and B6 are optionally linked to a linker represented by Formula 2A:
wherein, in Formula 2A,
L 31 is a nitrogen atom, a substituted or unsubstituted trivalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trivalent aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted trivalent heteroaryl group having 1 to 30 carbon atoms for forming a ring, and
c is 0 or 1.
14. The organic electroluminescence device of claim 13 ,
wherein A1 to A4 and B1 to B6 are each independently any one selected from LG1 to LG3:
wherein, in LG1 to LG3,
X 21 and X 22 are each independently CR 24 , or a nitrogen atom,
Y 1 is CR 25 or C—*,
Y 2 is NR 26 or N—,
Y 3 is B or B—*, and
R 21 to R 27 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 21 to R 27 are optionally combined with an adjacent group to form a ring.
15. The organic electroluminescence device of claim 14 ,
wherein Formula 1 is represented by Formula 1-1:
wherein, in Formula 1-1,
A21 and A31 are each independently LG1 or LG3, and at least one selected from A21 and A31 is LG3, and
R 31 to R 36 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 31 to R 36 are optionally combined with an adjacent group to form a ring.
16. The organic electroluminescence device of claim 14 ,
wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
in Formula 2-1 and Formula 2-2
B41 to B61 are each independently LG1, LG2, or LG3, and at least one selected from B41 to B61 is LG3,
R 41 to R 45 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 41 to R 45 are optionally combined with an adjacent group to form a ring,
R 51 to R 62 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 51 to R 62 are optionally combined with an adjacent group to form a ring,
L 31 is the same as defined in Formula 2A, and
X 21 and X 22 are the same as defined in LG2.
17. An organometallic compound represented by Formula 1 or Formula 2:
wherein, in Formula 1 and Formula 2,
X 1 to X 4 and X 11 to X 16 are each independently a carbon atom or a nitrogen atom,
A1 to A4 and B1 to B6 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring,
at least one selected from A1 to A4, and at least one selected from B1 to B6, are a substituted or unsubstituted borazine group,
R 1 to R 4 and Ru to R 16 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 1 to R 4 and Ru to R 16 are optionally combined with an adjacent group to form a ring,
a1 to a4 and a11 to a16 are each independently an integer of 0 to 3,
L 1 to L 3 and L 11 to L 16 are each independently a direct linkage, *—O—*, *—S—*, a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms for forming a ring,
b1 to b3 and b11 to b16 are each independently 0 or 1, and
in Formula 2, B1, B3, and B6 are optionally linked to a linker represented by Formula 2A:
wherein, in Formula 2A,
L 31 is a nitrogen atom, a substituted or unsubstituted trivalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trivalent aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted trivalent heteroaryl group having 1 to 30 carbon atoms for forming a ring, and
c is 0 or 1.
18. The organometallic compound of claim 17 ,
wherein A1 to A4, and B1 to B6 are each independently any one selected from selected from LG1 to LG3:
wherein, in LG1 to LG3,
X 21 and X 22 are each independently CR 24 , or a nitrogen atom,
Y 1 is CR 25 or C—*,
Y 2 is NR 26 or N—,
Y 3 is B or B—*, and
R 21 to R 29 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 21 to R 29 are optionally combined with an adjacent group to form a ring.
19. The organometallic compound of claim 18 ,
wherein Formula 1 is represented by Formula 1-1:
wherein, in Formula 1-1,
A21 and A31 are each independently LG1 or LG3, and at least one selected from A21 and A31 is LG3, and
R 31 to R 36 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 31 to R 36 are optionally combined with an adjacent group to form a ring.
20. The organometallic compound of claim 18 ,
wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
wherein in Formula 2-1 and Formula 2-2,
B41 to B61 are each independently LG1, LG2, or LG3, and at least one selected from B41 to B61 is LG3,
R 41 to R 45 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 41 to R 45 are optionally combined with an adjacent group to form a ring,
R 51 to R 62 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 51 to R 62 are optionally combined with an adjacent group to form a ring,
L 31 is the same as those in Formula 2A, and
X 21 and X 22 are the same as defined in LG2.
21. The organometallic compound of claim 17 ,
wherein a difference (Δ(T 1 − 3 MC)) between T 1 energy level and 3 MC energy level of the organometallic compound is about 0.3 eV or more.
22. The organometallic compound of claim 17 ,
wherein Formula 1 is any one selected from compounds represented by Compound Group 1: