Heterocyclic compound, organic light-emitting element comprising same, and composition for organic material layer

Patent metadata

Field	Value
Publication number	US-2025287838-A1
Application number	US-202519218623-A
Country	US
Kind code	A1
Filing date	May 27, 2025
Priority date	Dec 13, 2022
Publication date	Sep 11, 2025
Grant date	—

Abstract

Provided is a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device and a composition for an organic material layer, including the same. The heterocyclic compound can be used as a material for the organic material layer of the organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device. In particular, the compound can be used as a material for a light emitting layer of an organic light emitting device.

First claim

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 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring, m and n are each an integer from 1 to 8, and when m is 2 or higher, R1's are the same as or different from each other, and when n is 2 or higher, R2's are the same as or different from each other,
L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, a is an integer from 1 to 4, and when a is 2 or higher, L1's are the same as or different from each other,
Ar1 is 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 comprising O or S,
b is an integer from 1 to 4, and when b is 2 or higher, Ar1's are the same as or different from each other, and
a deuterium content of

of Chemical Formula 1 is 20% or more and 100% or less.

2 . The heterocyclic compound of claim 1 , wherein

of Chemical Formula 1 is represented by any one of the following Chemical Formulae 4 to 17:

in Chemical Formulae 4 to 17,
R11 and R12 are the same as or different from each other, and are each independently hydrogen or deuterium,
Ar11 to Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
m1 and n1 are an integer from 0 to 8,
m2 and n2 are an integer from 0 to 7,
m3 and n3 are an integer from 0 to 6, and
when m1, m2, m3, n1, n2, and n3 are each 2 or higher, substituents in the parenthesis are the same as or different from each other.

3 . The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by each of the following Structural Formulae A and B, a deuterium content of the following Structural Formula A is 10% or less, and a deuterium content of the following Structural Formula B is 20% or more and 100% or less:

in Structural Formulae A and B, a definition of each substituent is the same as a definition in Chemical Formula 1.

4 . The heterocyclic compound of claim 1 , wherein Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted quinquephenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; or a substituted or unsubstituted spirobifluorenyl group.

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

• Jeong Cheol-Hun
• Park Geon-Yu
• No Young-Seok
• Kim Dong-Jun
• Choi Dae-Hyuk

Classifications

• C07D495/04

  Ortho-condensed systems · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/6574

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