Organic electroluminescence device and organometallic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11626564-B2
Application number	US-202016938702-A
Country	US
Kind code	B2
Filing date	Jul 24, 2020
Priority date	Oct 21, 2019
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

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.

First claim

What is claimed is:

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:

Assignees

• Samsung Display Co Ltd

Inventors

• Kang Sunwoo
• Choi Sunmi

Classifications

• H10K85/346 Primary

  comprising platinum · CPC title

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title