Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11678498-B2
Application number	US-201715459258-A
Country	US
Kind code	B2
Filing date	Mar 15, 2017
Priority date	Apr 7, 2016
Publication date	Jun 13, 2023
Grant date	Jun 13, 2023

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, the emission layer including a first compound and a second compound; a hole transport region between the first electrode and the emission layer; and an electron transport region, the electron transport region including a buffer layer between the emission layer and the second electrode, the buffer layer including a third compound, and an electron transport layer between the buffer layer and the second electrode, the electron transport layer including a fourth compound, wherein, in the emission layer, the first compound is a phosphorescent host and the second compound is a phosphorescent dopant, wherein the first compound and the third compound are different from each other, wherein the first compound and the third compound each independently include both an electron transport group and a hole transport group.

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, the emission layer including a first compound and a second compound;
a hole transport region between the first electrode and the emission layer; and
an electron transport region, the electron transport region including:
a buffer layer between the emission layer and the second electrode, the buffer layer including a third compound, and
an electron transport layer between the buffer layer and the second electrode, the electron transport layer including a fourth compound,

wherein, in the emission layer, the first compound is a phosphorescent host and the second compound is a phosphorescent dopant,
wherein the first compound and the third compound are different from each other,
wherein the first compound and the third compound each independently include both an electron transport group and a hole transport group, and
wherein the first compound is represented by Formula 1-1, and the third compound is represented by Formula 1-2:
HT 1 -(L 11 ) a11 -ET 1   <Formula 1-1>

HT 2 -(L 12 ) a12 -ET 2   <Formula 1-2>

wherein, in Formulae 1-1 and 1-2:
HT 1 and HT 2 are a hole transport group,
ET 1 and ET 2 are an electron transport group, and
HT 1 is a group represented by one of Formulae 2-1 to 2-4,
HT 2 is a group represented by one of Formulae 2-1 or 2-2,

wherein, in Formulae 1-1, 1-2, and 2-1 to 2-4,
ring A 1 , ring A 2 , and ring A 3 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
wherein, in Formula 1-1, when HT 1 is a group represented by Formula 2-1,
in Formula 2-1 of HT 1 , ring A 1 is a group represented by one of Formulae 2A to 2C and 2I, and ring A 2 is a group represented by one of Formulae 2E to 2H,
in Formula 2-1 of HT 2 , ring A 1 is a group represented by one of Formulae 2B, 2C, 2E to 2H, 2J to 2N, and ring A 2 is a group represented by one of Formulae 2A to 2C, 2E to 2N,
in Formula 2-2 of HT 2 , ring A 1 is a C5-C60 carbocyclic group;

wherein, in Formulae 2E to 2H,
X 1 is selected from O, S, N(R 11 ), and Si(R 11 )(R 12 ), and
R 11 and R 12 are defined the same as R 1 of Formulae 2-1 to 2-4,
ET 1 and ET 2 are each independently a C 1 -C 60 heterocyclic group having at least one *═N—*′ moiety as a ring-forming moiety,
L 11 , L 12 , and L 1 to L 3 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 and a12 are each independently an integer of 0 to 5,
wherein, in Formula 1-1, when HT 1 is a group represented by Formula 2-1, ring A 1 in Formula 2-1 is a group represented by Formula 2A, ring A 2 in Formula 2-1 is a group represented by Formula 2E, and X 1 in Formula 2E is selected from O, S, and Si(R 11 )(R 12 ),
a1 to a3 are each independently an integer of 0 to 3,
R 1 to R 3 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 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 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
b1 to b3 are each independently an integer of 1 to 3,
c1 to c3 are each independently an integer of 0 to 5,
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 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl 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 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

Assignees

• Samsung Display Co Ltd

Inventors

• Cho Hwan-Hee
• Kim Myeong-Suk
• Kim Sung-Wook
• 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

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K50/166

  comprising a multilayered structure · CPC title

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title