Heterocyclic compound and organic light-emitting element including same

Patent metadata

Field	Value
Publication number	US-11450819-B2
Application number	US-201816484641-A
Country	US
Kind code	B2
Filing date	Apr 13, 2018
Priority date	Apr 13, 2017
Publication date	Sep 20, 2022
Grant date	Sep 20, 2022

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,
G1 is hydrogen; deuterium; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group;
an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
L is a direct bond; or a substituted or unsubstituted arylene group;
Ar1 is any one of the following Chemical Formulae 2-A to 2-E:

wherein, in Chemical Formula 2-A to Chemical Formula 2-E,
X1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, and at least two of X1 to X4 are N;
X9 is N or CR9, X10 is N or CR10, and X11 is O; S; or NR11;
and when X11 is NR11, at least one of X9 and X10 is N, and when X11 is O or S, X9 and X10 are each N;
X32 is N or CR32, X33 is N or CR33, X34 is N or CR34, X35 is N or CR35, and at least two of X32 to X35 are N;
any one of R1 to R8, any one of R9 to R13, any one of R14 to R19, any one of R20 to R31 or any one of R32 to R41 is a site bonding to L of Chemical Formula 1;
the rest of R1 to R13 and R20 to R41 other than the site bonding to L of Chemical Formula 1 are the same as or different from each other, and each independently hydrogen; deuterium; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and
the rest of R14 to R19 other than the site bonding to L of Chemical Formula 1 are the same as or different from each other, and each independently hydrogen; a phenyl group unsubstituted or substituted with a nitrile group; a naphthyl group unsubstituted or substituted with a nitrile group; or a biphenyl group unsubstituted or substituted with a nitrile group; and
n is an integer of 0 to 3, and when n is 2 or greater, G1s are the same as or different from each other.

2. The heterocyclic compound of claim 1 , wherein L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthalene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted quaterphenylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; a substituted or unsubstituted pyrenylene group; a substituted or unsubstituted fluorenylene group; or a substituted or unsubstituted spiro cyclopentane fluorenylene group.

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

wherein,
in Chemical Formula 3-A, any one of R2 and R4 to R8 is a site bonding to L of Chemical Formula 1;
in Chemical Formula 3-B, any one of R2, R3 and R5 to R8 is a site bonding to L of Chemical Formula 1;
in Chemical Formula 3-C, any one of R3 to R8 is a site bonding to L of Chemical Formula 1;
in Chemical Formula 3-D, any one of R1 and R4 to R8 is a site bonding to L of Chemical Formula 1; and
the rest of R1 to R8 other than the site bonding to L of Chemical Formula 1 are the same as or different from each other, and each independently hydrogen; deuterium; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

4. The heterocyclic compound of claim 1 , wherein Chemical Formula 2-B is represented by any one of the following Chemical Formulae 4-A to 4-D:

wherein,
in Chemical Formula 4-A, any one of R10 to R13 is a site bonding to L of Chemical Formula 1;
in Chemical Formulae 4-B and 4-C, R12 or R13 is a site bonding to L of Chemical Formula 1;
in Chemical Formula 4-D, any one of R11 to R13 is a site bonding to L of Chemical Formula 1; and
the rest of R10 to R13 other than the site bonding to L of Chemical Formula 1 are the same as or different from each other, and each independently hydrogen; deuterium; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

5. The heterocyclic compound of claim 1 , wherein Chemical Formula 2-E is represented by any one of the following Chemical Formulae 5-A to 5-G:

Assignees

• Lg Chern Ltd
• Lg Chemical Ltd

Inventors

• Heo Dong Uk
• Lee Dong Hoon
• Huh Jungoh
• Jang Boonjae
• Cha Yongbum
• Han Miyeon
• Yang Junghoon
• Yun Heekyung

Classifications

• H10K85/656

  comprising two or more different heteroatoms per ring (H10K85/652 takes precedence) · CPC title

• H10K85/6572

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

• C07D417/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title