Amine-based compound and organic light-emitting diode including the same

Patent metadata

Field	Value
Publication number	US-9882143-B2
Application number	US-201514876742-A
Country	US
Kind code	B2
Filing date	Oct 6, 2015
Priority date	Feb 7, 2012
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

An amine-based compound and an organic light-emitting diode including the amine-based compound.

First claim

What is claimed is:

1. An amine-based compound represented by Formula 1 below:

wherein, in Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl group or a substituted or unsubstituted C 2 -C 60 heteroaryl group;
X 1 is a substituted or unsubstituted C 6 -C 60 arylene group or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
m is an integer from 1 to 5; and
at least one substituent of each of the substituted C 6 -C 60 aryl group, the substituted C 2 -C 60 heteroaryl group, the substituted C 6 -C 60 arylene group, and the substituted C 2 -C 60 heteroarylene group is one of a deuterium atom; —F; —Cl; —Br; —I; —CN; a hydroxyl group; —NO 2 ; an amino group; an amidino group; hydrazine; hydrazone; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid or a salt thereof; a tri(C 6 -C 60 aryl)silyl group; a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group; a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 2 -C 60 alkenyl group and a C 2 -C 60 alkynyl group that is substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof; a C 3 -C 60 cycloalkyl group, a C 3 -C 60 cycloalkenyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, a C 6 -C 60 aralkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthiol group; a C 3 -C 60 cycloalkyl group, a C 3 -C 60 cycloalkenyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, a C 6 -C 60 aralkyl group, a C 6 -C 60 aryloxy group, and a C 6 -C 60 arylthiol group that is substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 1 -C 60 alkyl group substituted with at least one fluorine (F), a C 1 -C 60 alkoxy group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group,
wherein at least one of Ar 1 and Ar 2 is a C 6 -C 60 aryl group substituted with at least one electron withdrawing group selected from the group consisting of —F; —CN; —NO 2 ; a C 1 -C 60 alkyl group substituted with at least one —F; a C 2 -C 60 heteroaryl group; and a C 2 -C 60 heteroaryl group substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 1 -C 60 alkyl group substituted with at least one —F, a C 1 -C 60 alkoxy group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group.

2. The amine-based compound of claim 1 , wherein the at least one electron withdrawing group is selected from the group consisting of: —F; —CN; —NO 2 ; a C 1 -C 20 alkyl group substituted with at least one —F; a C 2 -C 20 heteroaryl group including a ring-forming N atom; and a C 2 -C 20 heteroaryl group that includes a ring-forming N atom and is substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkyl group substituted with at least one —F, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, and a C 2 -C 20 heteroaryl group.

3. The amine-based compound of claim 1 , wherein the at least one electron withdrawing group is selected from the group consisting of —F; —CN; a C 1 -C 20 alkyl group substituted with at least one —F; a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a benzoimidazolyl group, an indolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, an indolizinyl group, a quinazolinyl group, a cinnolinyl group, an indazolyl group, a carbazolyl group, a phenazinyl group, a phenanthridinyl group, a triazinyl group, a pyridazinyl group, a triazoly group, and a tetrazoly; and a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an imidazopyridinyl group, imidazopyrimidinyl, pyridinyl, pyrazinyl, pyrimidinyl, benzoimidazolyl, indolyl, purinyl, quinolinyl, isoquinolinyl, phthalazinyl, indolizinyl, quinazolinyl, cinolinyl, indazolyl, carbazolyl, phenazinyl, phenanthridinyl, triazinyl, pyridazinyl, triazolyl, and a tetrazolyl group that is substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkyl group substituted with at least one —F, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group and a carbazolyl group.

4. The amine-based compound of claim 1 , wherein the at least one electron withdrawing group in Formula 1 is selected from the group consisting of: —F; —CN; a C 1 -C 20 alkyl group substituted with at least one —F; a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a triazinyl group, and a benzoimidazolyl group; and a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a triazinyl group, a benzoimidazolyl group, and a carbazolyl group that are substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkyl group substituted with at least one —F, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group, and a carbazolyl group.

5. The amine-based compound of claim 1 , wherein the at least one electron withdrawing group is selected from the group consisting of —F; —CN; —CH 2 F; —CHF 2 ; —CF 3 ; and groups represented by Formulae 2(1) to 2(14) below:

wherein, in Formulae 2(1) to 2(14), Z 11 to Z 18 are each independently a hydrogen atom, a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkyl group substituted with at least one —F, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group, or a carbazolyl grou

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Youngkook
• Hwang Seokhwan
• Jung Hyejin
• Lim Jino
• Han Sanghyun
• Jeong Eunjae
• Kim Sooyon
• Park Junha
• Lee Eunyoung
• Lee Jonghyuk

Classifications

• C07C217/92 Primary

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• H01L51/0081

  Electricity · mapped topic