Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12069879-B2
Application number	US-201816161574-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Nov 20, 2017
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes a first material not including an electron transport moiety, a second material including at least one electron transport moiety, a third material having reorganization energy of about 0.4 eV or more, and a light-emitting material, wherein the first material, the second material, the third material, and the light-emitting material are different from one another, and wherein a ratio of a light-emitting component emitted from the light-emitting material to a total of light-emitting components emitted from the emission layer is about 90% or more.

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 emission layer disposed between the first electrode and the second electrode,
wherein the emission layer comprises a first material, a second material, a third material, and a light-emitting material,
the first material does not comprise an electron transport moiety,
the second material comprises at least one electron transport moiety,
the third material has reorganization energy of about 0.4 electron volts or more,
the first material, the second material, the third material, and the light-emitting material are different from one another, and
a ratio of a light-emitting component emitted from the light-emitting material to a total of light-emitting components emitted from the emission layer is about 90% or more,
wherein the second material comprises at least one of a compound represented by Formula E-1(1), a compound represented by Formula E-1(2), and a compound represented by Formula E-1(3):

wherein, in Formulae E-1(1) to E-1(3),
Z 1 to Z 6 are each independently:
hydrogen, deuterium, or a cyano group (CN);
a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one selected from deuterium, a cyano group, an unsubstituted phenyl group, and an unsubstituted biphenyl group,
b1 to b6 are each independently 1, 2, or 3,
at least one of groups Z 1 in the number of b1, groups Z 2 in the number of b2, groups Z 3 in the number of b3, groups Z 4 in the number of b4, groups Z 5 in the number of b5, and groups R 6 in the number of b6 is a cyano group,
X 21 and X 22 are each independently O or S, and
m is 0 or 1,
provided that when the second material comprises a compound represented by Formula E-1(1), then m is 1,
wherein the third material comprises a compound represented by Formula 11:

wherein, in Formula 11,
X 1 is a single bond, N-[(L 4 ) c4 -R 4 ], C(R 5 )(R 6 ), O, or S,
A 1 and A 2 are each independently a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group,
L 3 and L 4 are each independently selected from a single bond, 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,
c3 and c4 are each independently an integer from 1 to 4,
R 1 to R 6 are each independently selected from hydrogen, 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 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 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 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),
a1 and a2 are each independently an integer from 0 to 10,
provided that L 3 is not a dibenzofuranylene group and R 3 is not a substituted triazine 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 divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
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 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 selected from 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 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );
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 monovalent non-aromatic condensed polycyclic group, and a monovalent 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Jongsoo
• Kim Joonghyuk
• Lee Namheon
• Kim Inkoo
• Jeong Daun
• Kim Sunghan
• Sim Myungsun
• Ihn Sooghang

Classifications

• H10K50/805 Primary

  Electrodes · CPC title

• C07D209/82 Primary

  Carbazoles; Hydrogenated carbazoles · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title