Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-9755158-B2
Application number	US-201514706532-A
Country	US
Kind code	B2
Filing date	May 7, 2015
Priority date	Nov 13, 2014
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

An organic light-emitting device including a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; and an electron transport region between the second electrode and the emission layer, wherein the electron transport region includes at least one first compound represented by the following Formula 1, at least one second compound represented by the following Formula 2, and at least one third compound represented by the following Formula 30:

First claim

What is claimed is:

1. An organic light-emitting device, comprising:
a first electrode;
a second electrode facing the first electrode;
an emission layer between the first electrode and the second electrode; and
an electron transport region between the second electrode and the emission layer,
wherein the electron transport region includes:
at least one first compound represented by the following Formula 1,
at least one second compound represented by the following Formula 2, and
at least one third compound represented by the following Formula 30:

wherein, in Formula 30, R 34 to R 43 are each independently selected from a group represented by the following Formula 50, a group represented by the following Formula 51, 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 60 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), and —B(Q 4 )(Q 5 );
wherein at least one of R 34 to R 38 is a group represented by Formula 50, and at least one of R 39 to R 43 is a group represented by Formula 51;

wherein, in Formulae 1, 2, 30, 50, and 51,
X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, and at least one of X 31 to X 33 is N;
X 55 is C(R 55 ) or N, X 56 is C(R 56 ) or N, X 57 is C(R 57 ) or N, X 58 is C(R 58 ) or N, at least one of X 55 and X 56 in Formula 50 is N, and at least one of X 57 and X 58 in Formula 51 is N;
L 11 to L 13 , L 21 to L 23 , and L 31 to L 33 are each independently selected from 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 divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
a11 to a13, a21 to a23, and a31 to a33 are each independently an integer selected from 0 to 3;
Ar 11 is a substituted or unsubstituted C 1 -C 60 heteroaryl group including one nitrogen atom;
Ar 21 is a substituted or unsubstituted C 1 -C 60 heteroaryl group including at least two nitrogen atoms;
Ar 12 , Ar 22 , and Ar 31 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
R 11 to R 14 , R 21 to R 24 , R 31 to R 33 , and R 51 to R 58 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 60 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), and —B(Q 4 )(Q 5 );
b11, b13, b21, b23, c2, and c4 are each independently an integer selected from 0 to 4,
b12, b14, b22, b24, c1, and c3 are each independently an integer selected from 0 to 3;
* is a binding site to a neighboring atom;
at least one substituent of the substituted C 3 -C 10 cycloalkylene group, substituted C 1 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 1 -C 10 heterocycloalkenylene group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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,

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Donghyun
• Kim Mikyung
• Naijo Tsuyoshi
• Bae Sungsoo

Classifications

• H01L51/5072

  Electricity · mapped topic

• H01L51/0054

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/5096

  Electricity · mapped topic

• H01L2251/301

  Electricity · mapped topic