Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11800801-B2
Application number	US-202016993615-A
Country	US
Kind code	B2
Filing date	Aug 14, 2020
Priority date	Feb 10, 2020
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, the emission layer comprises a first host and a dopant, the dopant is an organometallic compound including platinum, the organic light-emitting device satisfies a condition of: HOMO(D)−HOMO(Host 1)≥0.2 electron volts, HOMO(D) is a highest occupied molecular orbital (HOMO) energy level of the dopant in electron volts, HOMO(Host 1) is a HOMO) energy level of the first host in electron volts, and HOMO(D) and HOMO(Host 1) are each measured using a photoelectron spectrometer in an ambient atmosphere.

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 disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer,
the emission layer comprises a first host and a dopant,
the dopant is an organometallic compound including platinum,
the organic light-emitting device satisfies a condition of: HOMO(D)−HOMO(Host 1)≥0.2 electron volts,
HOMO(D) is a highest occupied molecular orbital (HOMO) energy level of the dopant in electron volts,
HOMO(Host 1) is a HOMO energy level of the first host in electron volts, and
HOMO(D) and HOMO(Host 1) are each measured using a photoelectron spectrometer in an ambient atmosphere,
wherein the emission layer further comprises a second host,
the first host is a hole transport host,
the second host is an electron transport host comprising an electron transport moiety, and
the electron transport moiety in the second host is a π-electron-deficient nitrogen-containing cyclic group.

2. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of HOMO(D)−HOMO(Host 1)≥0.22 electron volts.

3. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of HOMO(Host1)≤−5.65 electron volts.

4. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of HOMO(Host1)−HOMO(Host2)≥0,
HOMO(Host 2) is a HOMO energy level of the second host in electron volts, and
HOMO(Host 2) is measured using a photoelectron spectrometer in an ambient atmosphere.

5. The organic light-emitting device of claim 4 , wherein the electron transport moiety in the second host is a group represented by one of Formulae 3-1 to 3-3:

wherein, in Formulae 2-1 to 2-3,
X 311 is N or C(R 314 ),
X 312 is O, S, or N(R 319 ),
X 313 is O, S, or N(R 324 ),
R 311 to R 324 are each independently a binding site to a neighboring atom, hydrogen, deuterium, —F —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 7 -C 60 arylalkyl 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 C 2 -C 60 heteroarylalkyl 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 ), or —P(═O)(Q 1 )(Q 2 ),
Q 1 to Q 3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 1 -C 60 alkyl group substituted with at least one of deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl 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 at least one of deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 arylalkyl group, a 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 C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group,
at least one of R 311 to R 313 is a binding site to a neighboring atom,
at least one of R 315 to R 318 is a binding site to a neighboring atom, and
at least one of R 320 to R 323 is a binding site to a neighboring atom.

6. The organic light-emitting device of claim 1 , wherein the first host is a carbazole-containing compound that does not comprise an electron transport moiety.

7. The organic light-emitting device of claim 1 , wherein the first host is a carbazole-containing compound comprising an electron transport moiety, and
the electron transport moiety is a π electron-deficient nitrogen-containing cyclic group.

8. The organic light-emitting device of claim 1 , wherein the first host is a carbazole-containing compound represented by Formula 4:

wherein, in Formula 4,
L 401 to L 402 are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a401 to a402 are each independently an integer from 0 to 5,
R 401 and R 402 are each independently 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R 403 to R 406 are each independently selected from hydrogen, deuterium, —F —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 7 -C 60 arylal

Assignees

• Samsung Electronics Co Ltd

Inventors

• Hong Seokhwan
• Sim Myungsun
• Kwak Seungyeon
• Koo Hyun
• Kim Sangdong
• Baik Chul
• Aratani Sukekazu
• Lee Sunyoung
• Lee Sunghun
• Ishihara Shingo
• Yi Jeoungin
• Cho Yuri
• Koishikawa Yasushi

Classifications

• H10K85/346

  comprising platinum · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/6576 Primary

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