Compound and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-11767324-B2
Application number	US-201916761348-A
Country	US
Kind code	B2
Filing date	Jan 4, 2019
Priority date	Jan 4, 2018
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

Provided is a compound of Chemical Formula 1:wherein:one of A1 and A2 is a substituent of Chemical Formula 2:and the other one is a cyano group;R3 is a substituted or unsubstituted aryl or heteroaryl group;R4 to R7 are each independently a hydrogen, deuterium, halogen, or a substituted or unsubstituted: silyl, alkyl, amine, arylamine, alkylamine, aryl, or heteroaryl group;R1 and R2 are each independently a substituted or unsubstituted aryl or heteroaryl group; and(1) at least one of R1 to R3 is a substituted phenyl group, or a substituted or unsubstituted heteroaryl group or C10 or higher aryl group; or(2) R7 is deuterium and d is 1 or greater,and an organic light-emitting device comprising the same.

First claim

The invention claimed is:

1. A compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
one of A1 and A2 is substituent of the following Chemical Formula 2, and the other one is a cyano group;
R3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group;
R4 to R7 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a is an integer of 0 to 4, and when a is 2 or greater, the R4s are the same as or different from each other;
b is an integer of 0 to 2, and when b is 2, the R5s are the same as or different from each other;
c is an integer of 0 to 4, and when c is 2 or greater, the R6s are the same as or different from each other; and
d is an integer of 0 to 3, and when d is 2 or greater, the R7s are the same as or different from each other;

wherein in Chemical Formula 2:
R1 and R2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and
wherein at least one of R1 and R2 is:
a phenyl group substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other; or
a C 10 to C 20 aryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or unsubstituted or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other; or
a C 2 to C 20 heteroaryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or unsubstituted or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other.

2. A compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
one of A1 and A2 is substituent of the following Chemical Formula 2, and the other one is a cyano group;
R3 is:
a phenyl group substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other; or
a C 10 to C 20 aryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or unsubstituted or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other; or
a C 2 to C 20 heteroaryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group, or unsubstituted or substituted with a substituent in which two or more substituents selected from the group consisting of a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group are linked to each other;
R4 to R7 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a is an integer of 0 to 4, and when a is 2 or greater, the R4s are the same as or different from each other;
b is an integer of 0 to 2, and when b is 2, the R5s are the same as or different from each other;
c is an integer of 0 to 4, and when c is 2 or greater, the R6s are the same as or different from each other; and
d is an integer of 0 to 3, and when d is 2 or greater, the R7s are the same as or different from each other;

wherein:
R1 and R2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and
(1) at least one of R1 and R2 is a substituted phenyl group, a substituted or unsubstituted C 10 or higher aryl group, or a substituted or unsubstituted heteroaryl group; or
(2) R7 is deuterium and dis 1 or greater.

3. The compound of claim 1 , wherein R3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

4. The compound of claim 1 , wherein the substituted or unsubstituted aryl group of R1 and R2 is independently selected from the group consisting of
an unsubstituted phenyl group,
a phenyl group substituted with deuterium, and
a biphenyl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group; and the substituted or unsubstituted heteroaryl group of R1 and R2 is independently selected from the group consisting of
a carbazolyl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group;
a dibenzofuranyl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group; and
a dibenzothiophenyl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C 1 to C 10 alkyl group, a C 6 to C 20 aryl group and a C 2 to C 20 heteroaryl group.

5. The compound of claim 1 , wherein the compound of Chemical Formula 1 comprises at lea

Assignees

• Lg Chemical Ltd
• Univ Sungkyunkwan Res Business Found

Inventors

• Yoon Hongsik
• Lee Jun Yeob
• Lee Ho Jung
• Chun Minseung
• Hong Wanpyo
• Suh Sang Duk
• Kang Yujin

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• H10K85/615

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

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/6574

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