Antiaromatic compounds and organic light-emitting devices comprising the same

Patent metadata

Field	Value
Publication number	US-10790452-B2
Application number	US-201414533028-A
Country	US
Kind code	B2
Filing date	Nov 4, 2014
Priority date	Jun 10, 2014
Publication date	Sep 29, 2020
Grant date	Sep 29, 2020

Abstract

An antiaromatic compound and an organic light-emitting device including the same. The antiaromatic compound is represented by Formula 1:

First claim

What is claimed is:

1. An antiaromatic compound represented by Formula 1:

wherein, in Formula 1,
A 11 and A 12 are each independently selected from a benzene, a naphthalene, a phenanthrene, an anthracene, a triphenylene, a pyrene, a chrysene, a pyrrole, a furan, an imidazole, a pyrazole, a thiazole, an oxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indole, a quinoline, an isoquinoline, a benzoquinoline, a naphthyridine, a quinoxaline, a quinazoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, a benzofuran, a benzothiophene, a benzoxazole, a triazole, a triazine, a dibenzofuran, and a dibenzothiophene;
L 11 and L 12 are each independently a moiety selected from a first group of moieties, the first group of moieties comprising a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted non-aromatic condensed polycyclic group, and a substituted or unsubstituted non-aromatic condensed heteropolycyclic group;
at least one substituent of the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted non-aromatic condensed polycyclic group, and the substituted non-aromatic condensed heteropolycyclic group is selected from:
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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, and C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy 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, a hydrazone, 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 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic group; and
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic 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, a hydrazone, 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 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic group;
a11 and a12 are each independently selected from 0, 1, 2, 3, 4, 5 and 6;
R11 and R12 are each independently a moiety selected from a second group of moieties, the second group of moieties comprising a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group, a substituted or unsubstituted non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), and -P(Q 16 )(Q 17 );
Q 11 to Q 17 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
at least one substituent of the substituted C 6 -C 60 aryl group, the substituted C 1 -C 60 heteroaryl group, the substituted non-aromatic condensed polycyclic group, and the substituted non-aromatic condensed heteropolycyclic group is selected from:
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy 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, a hydrazone, 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 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic group; and
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a non-aromatic condensed polycyclic group, and a non-aromatic condensed heteropolycyclic 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, a hydrazone, 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 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl g

Assignees

• Samsung Display Co Ltd
• Nat Univ Gyeongsang Iacf

Inventors

• Kim Mi-Kyung
• Kim Yun-Hi
• Kwon Soon-Ki
• Chu Chang-Woong

Classifications

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07D245/04 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• C09B3/00

  Dyes with an anthracene nucleus condensed with one or more carbocyclic rings · CPC title