Arylamine-based compound and organic light emitting diode comprising the same

Patent metadata

Field	Value
Publication number	US-9960359-B2
Application number	US-201314061733-A
Country	US
Kind code	B2
Filing date	Oct 23, 2013
Priority date	Jun 3, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

An arylamine-based compound is represented by Formula 1 below. The arylamine-based compound is included in an organic light emitting diode.

First claim

What is claimed is:

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

wherein in Formula 1,
ring A is selected from: benzene, naphthalene, anthracene, fluorene, spiro-fluorene, phenanthrene, triphenylene, chrysene, naphthacene, perylene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, quinoline, isoquinoline, benzoquinoline, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, or benzocarbazole;
(X) n is selected from Formulae 3a to 3n below:

wherein in Formulae 3a to 3n, * is a binding site to the nitrogen atom of a pyrrole ring in Formula 1 and *′ is a binding site to the other nitrogen atom;
each of Ar 1 and Ar 2 is independently selected from: a substituted or unsubstituted C 6 -C 30 aryl group or a substituted or unsubstituted C 2 -C 30 heteroaryl group;
each of R 1 , and R 2 is independently selected from: a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group;
each of R 3 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or an unsubstituted C 2 -C 30 heteroaryl group; and
a is an integer of 0 to 4.

2. The arylamine-based compound of claim 1 , wherein the ring A is selected from: benzene, naphthylene, fluorene, phenanthrene, chrysene, perylene, pyridine, pyrazine, pyrimidine, quinoline, isoquinoline, benzoquinoline, carbazole, phenanthroline, dibenzofuran, or dibenzothiophene.

3. The arylamine-based compound of claim 1 , wherein the ring A is any one of Formulae 2a to 2m below:

wherein in Formulae 2a to 2m,
corresponds to carbon number 4 of a pyrrole ring in Formula 1 and *′ corresponds to carbon number 5 of a pyrrole ring in Formula 1.

4. The arylamine-based compound of claim 1 , wherein each of Ar 1 and Ar 2 is independently selected from:
i) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a benzofuranyl group, a benzothienyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothienyl group, or a dibenzosilolyl group; or
ii) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a benzofuranyl group, a benzothienyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothienyl group, or a dibenzosilolyl group, each substituted with at least one of:
a deuterium atom; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; —Si(Q 3 )(Q 4 )(Q 5 ) wherein each of Q 3 to Q 5 is independently a C 1 -C 10 alkyl group; a C 1 -C 10 alkyl group substituted with at least one of: a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —Si(Q 3 )(Q 4 )(Q 5 ) wherein each of Q 3 to Q 5 is independently a C 1 -C 10 alkyl group; a C 6 -C 16 aryl group; a C 2 -C 16 heteroaryl group; or a C 6 -C 16 aryl group or a C 2 -C 16 heteroaryl group, each substituted with a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, a C 2 -C 16 heteroaryl group, or Si(Q 3 )(Q 4 )(Q 5 ) wherein each of Q 3 to Q 5 is independently a C 1 -C 10 alkyl group.

5. The arylamine-based compound of claim 1 , wherein
each of Ar 1 and Ar 2 is independently selected from:
i) a phenyl group, a naphthyl group, a fluorenyl group, a dibenzothienyl group, or a dibenzosilolyl group; or
ii) a phenyl group, a naphthyl group, a fluorenyl group, a dibenzothienyl group, or a dibenzosilolyl group, each substituted with at least one of: a deuterium atom; a fluorine atom; a cyano group; a nitro group; a methyl group; an ethyl group; an n-propyl group; an iso-propyl group; an n-butyl group; a sec-butyl group; an iso-butyl group; a tert-butyl group; —Si(Q 3 )(Q 4 )(Q 5 ) wherein each of Q 3 to Q 5 is independently a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group; a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group, each substituted with at least one of: a deuterium atom, a fluorine atom, a cyano group, a nitro group, or —Si(Q 3 )(Q 4 )(Q 5 ) wherein each of Q 3 to Q 5 is independently a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, or a tert-butyl group; a phenyl group; a naphthyl group; an anthracenyl group; a fluorenyl group; a benzothienyl group; a dibenzothienyl group; a pyridyl group; a pyrimidyl group; a triazinyl group; a carbazolyl group; or a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a benzothienyl group, a dibenzothienyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, or a carbazolyl group, ea

Assignees

• Samsung Display Co Ltd

Inventors

• Hwang Seok-Hwan
• Kim Young-Kook
• Jung Hye-Jin
• Park Jun-Ha
• Lee Eun-Young
• Lim Jin-O
• Han Sang-Hyun
• Jeong Eun-Jae
• Kim Soo-Yon
• Lee Jong-Hyuk

Classifications

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• H01L51/0059

  Electricity · mapped topic

• C07D487/04

  Ortho-condensed systems · CPC title