Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12520712-B2
Application number	US-201916295955-A
Country	US
Kind code	B2
Filing date	Mar 7, 2019
Priority date	Mar 8, 2018
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer. The organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2:

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 and comprising an emission layer, wherein the organic layer further comprises a first compound represented by Formula 1 and a second compound represented by Formula 2, and the first compound is not 1,3-di-9-carbazolylbenzene (mCP):

wherein, in Formulae 1, 1-1, 1-2, and 1-3,
CY 1 and CY 2 are each independently a group represented by one of Formulae 1-1, 1-2, and 1-3,
m1 and m2 are each independently 0, 1 or 2, wherein a sum of m1 and m2 is 2,
L 1 and L 2 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, a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )-,
b1 is an integer from 0 to 5,
b2 is an integer from 0 to 5,
X 1 to X 4 are each independently selected from a single bond, *—O—*, *—S—*, *—C(R 8 )(R 9 )—*′, *—C(═O)—*′, *—B(R 8 )(R 9 )—*′, *—N(R 8 )—*′, *—P(R 8 )—*′, and *—Si(R 8 )(R 9 )—*′,
rings A 1 to A 6 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,
R 1 to R 9 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
a1 to a7 are each independently an integer from 1 to 8,
wherein in Formula 2,
M 11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
A 11 to A 14 are each independently selected from a C 5 -C 6 carbocyclic group and a C 1 -C 60 heterocyclic group,
Y 11 to Y 14 are each independently N or C,
T 11 to T 14 are each independently selected from a single bond, O, and S,
L 11 to L 13 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 15 )(R 16 )—*′, *—C(R 15 )═**, *=C(R 15 )—*′, *—C(R 15 )=C(R 16 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—**, *—B(R 15 )—*′, *—N(R 15 )—*, *—P(R 15 )—*, *—Si(R 15 )(R 16 )—*′, *—P(═O)(R 15 )(R 16 )—*′, and *—Ge(R 15 )(R 16 )—*′,
b11 to b13 are each independently an integer from 0 to 3,
when b11 is 0, A 11 and A 12 are not linked to each other, when b12 is 0, A 12 and A 13 are not linked to each other, and when b13 is 0, A 13 and A 14 are not linked to each other, and
L 14 to L 16 are each independently selected from *—O—*′, *—S—*′, *—C(═O)—*′, *—C(═S)—*′, *—B(R 17 )—*′, *—N(R 17 )—*′, *—P(R 17 )—*′, *—Si(R 17 )(R 18 )—*′, *—P(═O)(R 17 )(R 18 )—*′, *—Ge(R 17 )(R 18 )—*′, a divalent C 2 -C 20 hydrocarbon group, a divalent C 5 -C 60 carbocyclic group, and a divalent C 1 -C 60 heterocyclic group, or the moiety represented by *-(L 14 ) b14 -(L 16 ) b16 -(L 15 ) b15 -*′ in Formula 2 is represented by one selected from Formulae 3-1 to 3-7:

in Formulae 3-1 to 3-7, * and *′ each indicating a binding site to a neighboring atom, and
wherein in Formula 2,
b14 and b15 are each independently an integer from 1 to 5,
b16 is an integer from 0 to 5,
when b16 is 0, L 16 is a single bond,
R 11 to R 18 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (=Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
R 15 and R 11 ; R 15 and R 12 ; R 15 and R 13 ; or R 15 and R 14 are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a11 to a14 are each independently an integer from 1 to 8,
* and *′ each indicate a binding site to a neighboring atom,
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 -Ceo aryloxy group, the subs

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Sungbum
• Ko Soobyung
• Ahn Heechoon
• Jeon Mina
• Jun Mieun
• HAN Junghoon
• Kim Youngkook
• Hwang Seokhwan

Classifications

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title