Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12048243-B2
Application number	US-202117239871-A
Country	US
Kind code	B2
Filing date	Apr 26, 2021
Priority date	Apr 27, 2020
Publication date	Jul 23, 2024
Grant date	Jul 23, 2024

Abstract

Provided is an organic light-emitting device including an emission layer including a first compound, a second compound, a third compound, and a fourth compound, each satisfying a certain condition.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emission layer,
the emission layer comprises a first compound, a second compound, a third compound, and a fourth compound, wherein the first compound and the second compound form an exciplex, the exciplex and the third compound satisfy Conditions 1-1 and 1-2, and the fourth compound is represented by Formula 503:
T 1 ( Ex )≤ T 1 ( C 3)< S 1 ( Ex )  Condition 1-1

T 1 ( C 3)− T 1 ( Ex )<0.3 eV  Condition 1-2

wherein, in Conditions 1-1 and 1-2,
T 1 (Ex) is a lowest excited triplet energy level of the exciplex,
T 1 (C3) is a lowest excited triplet energy level of the third compound, and
S 1 (Ex) is a lowest excited singlet energy level of the exciplex,

wherein, in Formula 503,
X 501 is B,
Y 501 to Y 503 are each independently O, S, B(R 505 ), C(R 505 )(R 506 ), or Si(R 505 )(R 506 ),
k501 is 0 or 1, wherein, when k501 is 0, —(Y 501 ) k501 — does not exist,
A 501 to A 503 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
L 501 to L 503 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xd1 to xd3 are each independently 0, 1, 2 or 3,
i)

R 501 to R 506 are each independently 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 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted 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, —C(Q 1 )(Q 2 )(Q 3 ), —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 ), or —P(═S)(Q 1 )(Q 2 ), and R 501 to R 506 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
xd11 and xd12 are each independently an integer from 0 to 10, and
Q 1 to Q 3 are each independently 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 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof, a substituted C 6 -C 60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof.

2. The organic light-emitting device of claim 1 , wherein the exciplex and the third compound further satisfy Condition 1-2-1:
T 1 ( C 3)− T 1 ( Ex )≤0.15 eV.  Condition 1-2-1

3. The organic light-emitting device of claim 1 , wherein the first compound is a hole transporting host,
the second compound is an electron transporting host,
the electron transporting host comprises at least one electron transporting moiety,
the hole transporting host does not comprise an electron transporting moiety, and
the electron transporting moiety is a cyano group, —F, —CFH 2 , —CF 2 H, —CF 3 , a π electron-deficient nitrogen-containing cyclic group, or a group represented by one of the formulae below:

wherein *, *′, and *″ in the formulae above are each a binding site to a neighboring atom.

4. The organic light-emitting device of claim 1 , wherein the third compound is a phosphorescent dopant or a delayed fluorescence dopant, and the third compound does not substantially emit light.

5. The organic light-emitting device of claim 1 , wherein, in Formula 503, and Y 501 to Y 503 are each independently O, S, or N(R 505 ).

6. The organic light-emitting device of claim 1 , wherein the fourth compound is represented by Formula 1:

wherein, in Formula 1,
X 11 is NR 14 or O,
X 12 is NR 15 or O,
X 13 is NR 16 or O,
k11 is 0 or 1, wherein, when k11 is 0, (X 11 ) k11 does not exist,
A 11 to A 13 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
R 11 to R 16 are each independently 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 7 -C 60 alkyl 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 2 -C 60 alkyl 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-ar

Assignees

• Samsung Electronics Co Ltd
• Research & Business Found Sungkyunkwan Univ

Inventors

• Kim Jiwhan
• Lee Kyunghyung
• Lee Junyeob
• Jeon Soonok
• Kwon Eunsuk
• Kim Jong Soo
• Kim Joonghyuk
• Nam Sungho
• Maruyama Yusuke
• Androsov Dmitry
• Lee Hasup
• Ihn Sooghang
• Chung Yeonsook
• Choi Hyeonho

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/322

  comprising boron · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title