Organic light-emitting devices

Patent metadata

Field	Value
Publication number	US-10326080-B2
Application number	US-201815960254-A
Country	US
Kind code	B2
Filing date	Apr 23, 2018
Priority date	Feb 14, 2014
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer including an emission layer between the first electrode and the second electrode. The emission layer includes at least one compound selected from carbazole-based compounds, and at least one compound selected from heterocyclic compounds as described in the detailed description.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer comprising an emission layer between the first electrode and the second electrode,
wherein the emission layer comprises at least one compound selected from carbazole-based compounds represented by Formula 1, and at least one compound selected from heterocyclic compounds represented by Formulae 10A, 10B 10C, 10D, and 10E:

wherein, in Formulae 1, 10A, 10B, 10C, 10D, and 10E, A 11 to A 14 , A 21 , and A 22 are each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7- naphthyridine, 2,7-naphthyridine, quinoxaline, phthalazine, and quinazoline;
X 11 is O, S, C(R 16 )(R 17 ), Si(R 16 )(R 17 ), P(R 16 ), B(R 16 ), P(═O)(R 16 ), or N(R 16 );
X 21 is N-(L 21 ) a21 -R 21 , and X 22 is O or S; or X 21 is O or S, and X 22 is N-(L 21 ) a21 -R 21 ;
L 11 is selected from:
a C 3 -C 10 cycloalkylene group, a C 3 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 3 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, a C 1 -C 60 heteroarylene group, a divalent nonaromatic condensed polycyclic group, and a divalent nonaromatic condensed heteropolycyclic group; and
a C 3 -C 10 cycloalkylene group, a C 3 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 3 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, a C 2 -C 60 heteroarylene group, a divalent nonaromatic condensed polycyclic group, and a divalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium; —F; —Cl; —Br; —I; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; a monovalent nonaromatic condensed polycyclic group; and a monovalent nonaromatic condensed heteropolycyclic group; except for a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a nitrogen (N)-containing C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
a11 is an integer selected from 0 to 5;
R 11 , R 16 , and R 17 are each independently selected from:
a hydrogen, a C 1 -C 60 alkyl group, 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 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and
a C 1 -C 60 alkyl group, 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 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium; —F; —Cl; —Br; —I; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; a monovalent nonaromatic condensed polycyclic group; and a monovalent nonaromatic condensed heteropolycyclic group; except for a nitrogen (N)-containing C 1 -C 60 heteroaryl group, and a nitrogen (N)-containing C 1 -C 60 heteroaryl group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
L 21 is selected from a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
a21 is an integer selected from 0 to 5;
R 21 is selected from:
a hydrogen, a C 1 -C 60 alkyl group, 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 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and
a C 1 -C 60 alkyl group, 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 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
R 12 to R 15 , and R 22 to R 24 are each independently selected from:
a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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, —F, —Cl, —Br, —I, 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 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
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 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;
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 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C

Assignees

• Samsung Display Co Ltd

Inventors

• Cho Hwan-Hee
• Kim Mi-Kyung
• Lee Jae-Yong
• Kim Dong-Hyun
• Kim Se-Hun
• Chu Chang-Woong

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F13/00

  Compounds containing elements of Groups 7 or 17 of the Periodic Table · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D307/78

  Benzo [b] furans; Hydrogenated benzo [b] furans · CPC title