Heterocyclic compound and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-12448370-B2
Application number	US-202017784423-A
Country	US
Kind code	B2
Filing date	Dec 18, 2020
Priority date	Feb 21, 2020
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

Provided is a heterocyclic compound of Chemical Formula 1:wherein:A1 is Chemical Formula 1-1:Y1 and Y2 are hydrogen or deuterium, or directly bonded to each other, or linked through —C(R31)(R32)-, —Si(R33)(R34)-, —N(R35)-, —O—, or —S—;any one of R11 to R26 is linked to L1, and of the remaining, one is linked to L4 of Chemical Formula 1, and the others are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted: alkyl, aryl, or heteroaryl group;at least two of X1 to X3 are N, and the other is CH;R1 is a substituted or unsubstituted alkyl group;L1 to L4 are each independently a direct bond or a substituted or unsubstituted arylene or heteroarylene group; andAr1 to Ar3 are each independently a substituted or unsubstituted alkyl, aryl, or heteroaryl group; and an organic light-emitting device including the same.

First claim

The invention claimed is:

1. A heterocyclic compound of Chemical Formula 1:

wherein in Chemical Formula 1:
at least two of X1 to X3 are N, and the other is CH;
R1 is a substituted or unsubstituted alkyl group;
L1 to L4 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
n1 to n4 are an integer from 0 to 4;
Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
m1 is an integer from 0 to 3;
when n1 to n4 and m1 are each 2 or higher, substituents in the parenthesis are the same as or different from each other;
A1 is Chemical Formula 1-1,

wherein in Chemical Formula 1-1:
Y1 and Y2 are each hydrogen or deuterium, or are directly bonded to each other, or are linked to each other through —C(R31)(R32)-, —Si(R33)(R34)-, —N(R35)-, —O—, or —S—;
any one of R11 to R26 is linked to L1 of Chemical Formula 1, and of the remaining, one is linked to L4 of Chemical Formula 1, and the others are the same as or different from each other, and are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; and
R31 to R35 are the same as or different from each other, and are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

2. The heterocyclic compound of claim 1 , wherein Chemical Formula 1-1 is any one of the following Chemical Formulae A11 to A13:

wherein in Chemical Formulae A11 to A13, the definitions of R11 to R26 are the same as those defined in Chemical Formula 1-1;
Y1 and Y2 are each hydrogen or deuterium;
G1 is C(R31)(R32), Si(R33)(R34), N(R35), O; or S; and
R31 to R35 are the same as or different from each other, and are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

3. The heterocyclic compound of claim 1 , wherein A1 is a divalent group selected from among the following structures:

wherein in the structures:
G1 is C(R31)(R32), Si(R33)(R34), N(R35), O, or S, R31 to R35 are the same as or different from each other, and are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
the structures are unsubstituted or substituted with deuterium, a cyano group, an alkyl group, an aryl group, or a heteroaryl group; and

 is a position which is linked to L1 or L4 of Chemical Formula 1.

4. The heterocyclic compound of claim 1 , wherein L1 to L4 are the same as or different from each other, and are each independently selected from a direct bond or the following structures:

5. The heterocyclic compound of claim 1 , wherein;
R1 is a C1-C6 alkyl group;
L1 to L4 are the same as or different from each other, and are each independently a direct bond or a C6-C20 arylene group;
Ar1 to Ar3 are the same as or different from each other, and are each independently a C1-C6 alkyl group or a C6-C20 aryl group;
Y1 and Y2 are each hydrogen or deuterium, or are directly bonded to each other, or are linked to each other through —O— or —S—; and
the others among R11 to R26 which are not linked to L1 and L4 of Chemical Formula 1 are the same as or different from each other, and are each independently hydrogen or deuterium.

6. The heterocyclic compound of claim 1 , wherein the heterocyclic compound of Chemical Formula 1 is any one compound selected from among the following compounds:

Assignees

• Lg Chemical Ltd

Inventors

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

Classifications

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · 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