Heterocyclic compound and organic light emitting diode comprising same

Patent metadata

Field	Value
Publication number	US-12338239-B2
Application number	US-202017439955-A
Country	US
Kind code	B2
Filing date	Jun 19, 2020
Priority date	Jun 24, 2019
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

First claim

The invention claimed is:

1. A heterocyclic compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
R 1 is hydrogen; or deuterium,
R 2 to R 5 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring;
A, B and C are a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
Ar 1 to Ar 3 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring;
q, r and s are an integer of 0 to 4;
m, n and p are an integer of 1 to 6;
R, R′ and R″ are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group; and
at least one of Ar 1 to Ar 3 is represented by the following Chemical Formula 1-2,

in Chemical Formula 1-2,
R 21 is a substituted or unsubstituted C6 to C60 aryl group;
L 2 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
b is an integer of 0 to 3;
c is an integer of 1 to 6,
X 1 to X 3 are N; or CR 13 , and at least one thereof is N;
L 1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; and
a is an integer of 0 to 3,
Z 2 is a C10 to C40 tricycle or more aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C40 alkyl group and a C6 to C60 aryl group; or represented by the following Chemical Formula 2-1; or the following Chemical Formula 2-2,

in Chemical Formulae 2-1 and 2-2,
Y is O; or S;
R31 and R32 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
d is an integer of 0 to 7; and
e is an integer of 0 to 8.

2. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 2:

in Chemical Formula 2,
R 1 to R 5 , Ar 1 to Ar 3 , A, m, n, p and q have the same definitions as in Chemical Formula 1.

3. The heterocyclic compound of claim 1 , wherein the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; —SiRR′R″; —P(═O)RR′; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or being unsubstituted, or being substituted with a substituent linking two or more substituents selected from among the substituents illustrated above, or being unsubstituted; and
R, R′ and R″ have the same definitions as in Chemical Formula 1.

4. The heterocyclic compound of claim 1 , wherein R 1 to R 5 are hydrogen.

5. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:

Assignees

• Lt Materials Co Ltd

Inventors

• Lee Gi-Back
• La Hyun-Ju
• Jeong Won-Jang

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/16

  Electron transporting 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