Heterocyclic compound and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-12415823-B2
Application number	US-202017612703-A
Country	US
Kind code	B2
Filing date	Oct 20, 2020
Priority date	Oct 25, 2019
Publication date	Sep 16, 2025
Grant date	Sep 16, 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,
R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group; or 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;
L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
X1 to X3 are the same as or different from each other, and each independently N; or CRa, and at least one thereof is N;
Ra, Ar2 and Ar4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; 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;
R3 to R11 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; and —CN;
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
m is an integer of 1 to 6, and when m is 2 or greater, substituents in the parentheses are the same as or different from each other.

2. The heterocyclic compound of claim 1 , wherein L1 is any one of the following structural formulae:

in the structural formulae,

means a position linked to the substituents of Chemical Formula 1;
R12 is 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; —CN; or —P(═O)RR′; and
R and R′ have the same definitions as in Chemical Formula 1.

3. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 2 to Chemical Formula 4:

in Chemical Formulae 2 to 4,
X1 to X3, R3 to R11, L1, Ar2, Ar4 and m have the same definitions as in Chemical Formula 1.

4. The heterocyclic compound of claim 1 , wherein

of Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-5:

in Chemical Formulae 1-1 to 1-5,

means a position linked to L1 of Chemical Formula 1;
Ar11 to Ar15 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; 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; and
R, R′ and R″ have the same definitions as in Chemical Formula 1.

5. The heterocyclic compound of claim 1 , wherein

of Chemical Formula 1 is represented by the following Chemical Formula 1-6 or 1-7:

in Chemical Formulae 1-6 and 1-7,

means a position linked to L1 of Chemical Formula 1; and
R21 is hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

6. The heterocyclic compound of claim 4 , wherein Ar12 is represented by

and Ar14 is a substituted or unsubstituted C6 to C60 aryl group;
L2 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
Z2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; and
a and b are the same as or different from each other and each an integer of 1 to 6, and when a and b are 2 or greater, substituents in the parentheses are the same as or different from each other.

7. 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
• Heo Yu-Jin
• Jeong Won-Jang

Classifications

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6574

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