Amine-based compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12514114-B2
Application number	US-201916406957-A
Country	US
Kind code	B2
Filing date	May 8, 2019
Priority date	Sep 27, 2018
Publication date	Dec 30, 2025
Grant date	Dec 30, 2025

Abstract

Provided are an amine-based compound represented by Formula 1, and an organic light-emitting device including the same, wherein at least one selected from Ar 1 to Ar 4 is a group represented by Formula 2, in which A 1 and A 2 are each independently a naphthalene group:

When the amine-based compound represented by Formula 1 is applied to the organic light-emitting device, resistance to high-temperature conditions and Joule heating may be increased. Accordingly, the organic light-emitting device including the amine-based compound represented by Formula 1 may have improved durability during storage and driving, as well as a longer lifespan.

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 between the first electrode and the second electrode, the organic layer comprising an emission layer and a hole transport region between the first electrode and the emission layer, wherein the hole transport region comprises at least one amine-based compound represented by Formula 1:

wherein, in Formula 1,
L 1 to L 4 are each independently a substituted or unsubstituted benzene group,
a1 and a4 are each 0,
a2 and a3 are each independently 0 or 1,
-(L 1 ) a1 - is a single bond, -(L 4 ) a4 - is a single bond,
Ar 1 and Ar 4 are each independently selected from groups represented by Formulae 2-1A and 2-1B,
Ar 2 and Ar 3 are each independently a substituted or unsubstituted C 6 -C 60 aryl group, and
Ar 1 and Ar 4 are the same, and
b1 to b4 are each 1, and
in Formulae 2-1A and 2-1B,
R 1 and R 2 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a propyl group, a isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, a phenyl group, and a biphenyl group,
c1 is an integer from 1 to 6,
c2 is an integer from 1 to 5,
at least one substituent of the substituted benzene group and the substituted C 6 -C 60 aryl group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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;
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 amidino group, a hydrazino group, a hydrazono 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, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
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, a biphenyl group, and a terphenyl 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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 hydrazino group, a hydrazono group, 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 aryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to a neighboring atom, and
wherein in Formula 1, a group represented by *-(L 5 ) a5 -* is selected from groups represented by Formulae 4-1 to 4-6:

wherein in Formulae 4-1 to 4-6,
Z 21 and Z 22 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), and —B(Q 31 )(Q 32 ),
d14 is an integer from 1 to 4,
d16 is an integer from 1 to 6,
d18 is an integer from 1 to 8,
Q 31 to Q 33 are each independently selected from hydrogen, deuterium, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to a neighboring atom.

2 . The organic light-emitting device of claim 1 , wherein:
the first electrode is an anode, the second electrode is a cathode, and the organic layer further comprises an electron transport region between the emission layer and second electrode, wherein the hole transport region further comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combi

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Dongjun
• Kim Youngkook
• Kim Jongwoo
• Jeong Eunjae
• Han Sanghyun

Classifications

• H10K50/155

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6574 Primary

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title