Organic electroluminescence device and organometallic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11849630-B2
Application number	US-202017074493-A
Country	US
Kind code	B2
Filing date	Oct 19, 2020
Priority date	Mar 4, 2020
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes an organometallic compound represented by Formula 1, and may show high emission efficiency properties.

First claim

What is claimed is:

1. An organic electroluminescence 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,
wherein the emission layer comprises an organometallic compound represented by the following Formula 1:

in Formula 1,
M is a transition metal,
one or two selected from X 1 to X 6 are N, and the remainder are CR 4 ,
if X 1 is N, any one selected from among X 2 to X 6 is N,
R 4 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A 1 to A 3 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 60 carbon atoms for forming a ring, or a substituted or unsubstituted heterocycle of 1 to 60 carbon atoms for forming a ring,
b1 to b3 are each independently an integer of 1 to 4,
R 1 to R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 1 to 10 carbon atoms for forming a ring,
at least one selected from among R 1 to R 3 is a deuterium atom or CD 3 , or at least one selected from among R 1 to R 3 is substituted with a deuterium atom or CD 3 ,
L is a direct linkage, O, S, —CR 11 R 12 —, —CR 13 ═CR 14 —, —C═C—, —C(═O)—, —C(═S)—, —BR 15 —, —NR 16 —, —PR 17 R 18 —, or —GeR 19 R 20 —, and
R 11 to R 20 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

2. The organic electroluminescence device of claim 1 , wherein M is Pt, Pd, Cu, or Os.

3. The organic electroluminescence device of claim 1 , wherein the emission layer emits phosphorescence.

4. The organic electroluminescence device of claim 1 , wherein the emission layer comprises a host and a dopant, and
the dopant comprises the organometallic compound represented by Formula 1.

5. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 2-1 or Formula 2-2:

in Formula 2-1 and Formula 2-2,
A 1 to A 3 , X 1 to X 6 , R 1 to R 3 , and b 1 to b 3 are the same as defined with respect to Formula 1.

6. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 3:

in Formula 3,
R 50 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and
M, L, X 1 to X 6 , R 1 to R 3 , and b 1 to b 3 are the same as defined with respect to Formula 1.

7. The organic electroluminescence device of claim 6 , wherein Formula 3 is represented by the following Formula 3-1:

in Formula 3-1,
any one selected from among X 2 to X 6 is N, and the remainder are CR 4 , and
M, L, R 1 to R 4 , R 50 and b 1 to b 3 are the same as defined with respect to Formula 3.

8. The organic electroluminescence device of claim 6 , wherein Formula 3 is represented by the following Formula 3-2 or Formula 3-3:

in Formula 3-2,
any one selected from among X 2 to X 4 is N, and the remainder are CR 4 , and
R 5 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and
in Formula 3-3,
any one selected from among X 5 and X 6 is N, and the remainder is CR 6 ,
b 4 is an integer of 1 to 4,
R 6 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and
M, L, R 1 to R 4 , b 1 to b 3 , and R 50 are the same as defined with respect to Formula 3.

9. The organic electroluminescence device of claim 6 , wherein R 50 is represented by any one selected from among compounds represented in the following Compound Group R:
Compound Group R

10. The organic electroluminescence device of claim 9 , wherein, if R 50 is Compound R-7 or R-8, R 1 comprises at least one deuterium atom.

11. The organic electroluminescence device of claim 1 , wherein the emission layer comprises at least one selected from among compounds represented in the following Compound Group 1:
Compound Group 1

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Eunyoung
• Ko Soo-Byung
• Kim Sungbum
• Lee Jaesung
• Lee Hyunjung

Classifications

• H10K85/346 Primary

  comprising platinum · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title