Novel compound and organic light emitting device comprising the same

Patent metadata

Field	Value
Publication number	US-2025066321-A1
Application number	US-202318695324-A
Country	US
Kind code	A1
Filing date	Sep 5, 2023
Priority date	Sep 5, 2022
Publication date	Feb 27, 2025
Grant date	—

Abstract

A compound Chemical Formula 1:wherein: each X is independently N, CH, or CD, provided that two or more of X are N, L is a single bond, or a substituted or unsubstituted C6-60 arylene, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-60 aryl, Ar3 and Ar4 are each independently phenyl that is unsubstituted or substituted with at least one deuterium, any one of Ar1 to Ar4 is substituted with cyano, HAr is pyrimidinyl which is unsubstituted or substituted with 1 to 3 substituent groups each independently selected from among deuterium, a substituted or unsubstituted C1-60 alkyl, and a substituted or unsubstituted C6-60 aryl; triazinyl which is substituted with two substituted or unsubstituted C6-60 aryls; or quinazolinyl substituted with one substituted or unsubstituted C6-60 aryl, and the other substituents are as described in the specification, and an organic light emitting device comprising the same.

First claim

1 . A compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
each X is independently N, CH, or CD, with the proviso that two or more of the X are N,
L is a single bond, or a substituted or unsubstituted C 6-60 arylene,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl,
Ar 3 and Ar 4 are each independently phenyl that is unsubstituted or substituted with at least one deuterium,
any one of Ar 1 to Ar 4 is substituted with cyano,
HAr is pyrimidinyl which is unsubstituted or substituted with 1 to 3 substituent groups each independently selected from the group consisting of deuterium, a substituted or unsubstituted C 1-60 alkyl, and a substituted or unsubstituted C 6-60 aryl; triazinyl which is substituted with two substituted or unsubstituted C 6-60 aryls; or quinazolinyl which is substituted with one substituted or unsubstituted C 6-60 aryl,
a and b are each independently an integer from 0 to 4,
n and m are each independently 0 or 1,
with the proviso that n+m is 1,
a+n is an integer from 0 to 4, and
b+m is an integer from 0 to 4.

2 . The compound of claim 1 , wherein:
the compound of Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3:

wherein, in Chemical Formulas 1-1 to 1-3:
X, L, Ar 1 , Ar 2 , Ar 3 , Ar 4 , a, b, n and m are as defined in claim 1 ,
Y is N or CR′, with the proviso that two or more of the Y are N,
R′ is hydrogen, deuterium, a substituted or unsubstituted C 1-60 alkyl, or a substituted or unsubstituted C 6-60 aryl,
R 1 and R 2 are each independently a substituted or unsubstituted C 6-60 aryl, and
c is an integer from 0 to 4.

3 . The compound of claim 1 , wherein:
the compound of Chemical Formula 1 is any one of the following Chemical Formulas 1-4 to 1-9:

wherein, in Chemical Formulas 1-4 to 1-9,
X, L, Ar 1 , Ar 2 , Ar 3 , Ar 4 , HAr, a, and b are as defined in claim 1 .

4 . The compound of claim 1 , wherein:
L is a single bond, phenylene, or biphenyldiyl, wherein the phenylene and biphenyldiyl are unsubstituted or substituted with at least one deuterium.

5 . The compound of claim 1 , wherein:
Ar 1 is phenyl that is unsubstituted or substituted with at least one deuterium.

6 . The compound of claim 1 , wherein:
Ar 2 is phenyl, biphenylyl, or naphthyl, wherein the Ar 2 is unsubstituted or substituted with at least one deuterium.

7 . The compound of claim 1 , wherein:
L is phenylene or biphenyldiyl, wherein the L is unsubstituted or substituted with at least one deuterium, and Ar 2 is phenyl substituted with cyano, or naphthyl substituted with cyano, wherein the Ar 2 is substituted with deuterium or is unsubstituted with deuterium.

8 . The compound of claim 1 , wherein:
L is a single bond, Ar 2 is phenyl or biphenylyl, wherein the Ar 2 is unsubstituted or substituted with at least one deuterium, and Ar 3 is phenyl substituted with cyano, wherein the Ar 3 is substituted with deuterium or is unsubstituted with deuterium.

9 . The compound of claim 2 , wherein:
R′ is hydrogen, deuterium, or methyl that is unsubstituted or substituted with at least one deuterium.

10 . The compound of claim 2 , wherein:
R 1 and R 2 are each independently phenyl, biphenylyl, or naphthyl, wherein the R 1 and R 2 are unsubstituted or substituted with at least one deuterium.

11 . The compound of claim 1 , wherein:
the compound of Chemical Formula 1 is any one compound selected from the group consisting of the following compounds:

12 . An organic light emitting device, comprising: a first electrode; a second electrode that is provided opposite to the first electrode; and one or more organic material layers that are provided between the first electrode and the second electrode, wherein at least one layer of the one or more organic material layers comprises the compound of claim 1 .

13 . An organic light emitting device of claim 12 , wherein:
the organic material layer comprising the compound is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

Assignees

• Lg Chemical Ltd

Inventors

• Heo Dong Uk
• Han Su Jin
• Hong Sung Kil
• Lee Jae Tak
• Yoon Jung Min
• Yun Heekyung

Classifications

• C07B2200/05

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

• C07B59/004

  Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title