Organic light emitting device

Patent metadata

Field	Value
Publication number	US-12501823-B2
Application number	US-202218039780-A
Country	US
Kind code	B2
Filing date	Feb 28, 2022
Priority date	Mar 8, 2021
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

Provided is an organic light-emitting device comprising: a light emitting layer comprising a compound of the following Chemical Formula 1, and one or more of an electron transport layer, an electron injection layer, or an electron transport and injection layer that comprises at least one of a compound of the following Chemical Formula 2 and a compound of the following Chemical Formula 3:

wherein Ar 2 and Ar 3 are each independently a substituent of Chemical Formula 4,

where X 1 to X 5 are each independently N or C(R 8 ), wherein at least two of X 1 to X 5 are N, and the other substituents are as defined in the specification. The organic light emitting device including the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 or 3 had significantly superior efficiency and lifespan.

First claim

The invention claimed is:

1 . An organic light emitting device, comprising:
an anode; a hole transport layer; a light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer comprises a compound of the following Chemical Formula 1, and the electron transport layer, the electron injection layer, or the electron transport and injection layer comprises at least one compound of the following Chemical Formula 2 and Chemical Formula 3:

wherein in Chemical Formula 1:
Z is O or S;
L 1 is a direct bond or a substituted or unsubstituted C 6-60 arylene;
Ar 1 is a substituted or unsubstituted C 6-60 aryl;
R 1 to R 3 are each independently hydrogen, deuterium, or a substituted or unsubstituted C 6-60 aryl, or two adjacent substituents thereof are combined to form a benzene ring;
n is an integer of 0 to 8;
m is an integer of 0 to 4; and
o is an integer of 0 to 3;

wherein in Chemical Formula 2 or 3:
R 4 to R 7 are each independently hydrogen or deuterium;
p1 to p4 are an integer of 1 to 4;
L 2 and L 3 are each independently a direct bond or a substituted or unsubstituted C 6-60 arylene; and
Ar 2 and Ar 3 are each independently a substituent of Chemical Formula 4:

wherein in Chemical Formula 4:
X 1 to X 5 are each independently N or C(R 8 ), wherein at least two of X 1 to X 5 are N; and
each R 8 is independently hydrogen, deuterium, a substituted or unsubstituted C 1-20 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or two adjacent R 8 s combine to form a benzene ring.

2 . The organic light emitting device of claim 1 , wherein L 1 is a direct bond, phenylene, biphenylene, or naphthylene, and the phenylene, biphenylene, or naphthylene is each independently unsubstituted or substituted with deuterium.

3 . The organic light emitting device of claim 1 , wherein Ar 1 is phenyl, biphenylyl, naphthyl, or phenanthrenyl, and the phenyl, biphenylyl, naphthyl, or phenanthrenyl is each independently unsubstituted or substituted with deuterium.

4 . The organic light emitting device of claim 1 , wherein R 1 to R 3 are each independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof combine to form a benzene ring, and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

5 . The organic light emitting device of claim 1 , wherein:
each R 1 is independently hydrogen or deuterium; each R 2 or R 3 is independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof combine to form a benzene ring, and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

6 . The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 contains at least one deuterium.

7 . The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 is any one compound selected from the group consisting of the following compounds:

Assignees

• Lg Chemical Ltd

Inventors

• Heo Dong Uk
• Han Miyeon
• Lee Jae Tak
• Yoon Jung Min
• Yun Heekyung
• Park Hoyoon
• Hong Sung Kil

Classifications

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title