Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11539012-B2
Application number	US-202016944248-A
Country	US
Kind code	B2
Filing date	Jul 31, 2020
Priority date	Nov 29, 2019
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

Presented is an organic light-emitting device including a host, a dopant, and a sensitizer.

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 host, a dopant, and a sensitizer,
the sensitizer comprises ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof, and
the dopant and the sensitizer satisfy Conditions 1 and 2 below:
0.2 eV≤Δ E ST ( S )  <Condition 1>

|HOMO( D )−HOMO( S )|<0.5 eV  <Condition 2>

wherein, in Conditions 1 and 2,
ΔE ST (S) is a difference between a lowest excitation singlet energy level and a lowest excitation triplet energy level of the sensitizer,
HOMO(D) is a highest occupied molecular orbital (HOMO) energy level of the dopant, and
HOMO(S) is a HOMO energy level of the sensitizer,
wherein the sensitizer comprises an organometallic compound represented by Formula 101 below:
M 11 (L 11 ) n11 (L 12 ) n12   <Formula 101>

wherein, in Formula 101,
M 11 is ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), or platinum (Pt),
L 11 is a ligand represented by one of Formulae 1-1 to 1-4,
L 12 may be a monodentate ligand or a bidentate ligand,
n11 is 1, and
n12 may be 0, 1, or 2,

wherein, in Formulae 1-1 to 1-4,
A 1 to A 4 may each independently be a substituted or unsubstituted C 5 -C 30 carbocyclic group, a substituted or unsubstituted C 1 -C 30 heterocyclic group, or a non-cyclic group,
Y 11 to Y 14 may each independently be a chemical bond, O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ),
T 1 to T 4 may each independently be a single bond, a double bond, *—N(R 93 )—*′, *—B(R 93 )—*′, *—P(R 93 )—*′, *—C(R 93 )(R 94 )—*′, *—Si(R 93 )(R 94 )—*′, *—Ge(R 93 )(R 94 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 93 )═*′, *═C(R 93 )—*′, *—C(R 93 )═C(R 94 )—*′, *—C(═S)—*′, or *—C≡C—*′,
a substituent of the substituted C 5 -C 30 carbocyclic group, a substituent of the substituted C 1 -C 30 heterocyclic group, and R 91 to R 94 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 1 -C 60 alkylthio 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 ), or —P(═S)(Q 1 )(Q 2 ), wherein each of the substituent of the substituted C 5 -C 30 carbocyclic group and the substituent of the substituted C 1 -C 30 heterocyclic group is not hydrogen,
* 1 , * 2 , * 3 , and * 4 each indicate a binding site to M 11 , and
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 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 substituted or unsubstituted C 1 -C 60 alkylthio 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, and a C 6 -C 60 aryl group, or any combination thereof, or a C 6 -C 60 aryl group that is substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, or a C 6 -C 60 aryl group, or any combination thereof.

2. The organic light-emitting device of claim 1 , wherein the organic light-emitting device further satisfies Condition 1-1 below:
0.2 eV≤Δ E ST ( S )≤0.4 eV  <Condition 1-1>

wherein, in Condition 1-1, ΔE ST (S) is a difference between a lowest excitation singlet energy level and a lowest excitation triplet energy level of the sensitizer.

3. The organic light-emitting device of claim 1 , wherein the sensitizer comprises Pt.

4. The organic light-emitting device of claim 1 , wherein the organic light-emitting device further satisfies Condition 3 below:
T 1 ( S )≥2.63 eV  <Condition 3>

wherein, in Condition 3, T 1 (S) is the lowest triplet excitation energy level of the sensitizer.

5. The organic light-emitting device of claim 1 , wherein the organic light-emitting device further satisfies Condition 4 below:
HOMO( S )≥−6.0 eV  <Condition 4>

wherein, in Condition 4, HOMO(S) is a HOMO energy level of the sensitizer.

6. The organic light-emitting device of claim 1 , wherein the host, the dopant, and the sensitizer further satisfy Condition 6 below:
T 1 ( H )≥ T 1 ( S )≥ S 1 ( D )  <Condition 6>

wherein, in Condition 6,
T 1 (H) is a lowest excitation triplet energy level of the host,
S 1 (D) is a lowest excitation singlet energy level of the dopant, and
T 1 (S) is a lowest excitation triplet energy level of the sensitizer.

7. The organic light-emitting device of claim 1 , wherein, among total emission components emitted from the emission layer, a ratio of emission components emitted from the dopant is 90% or more.

8. The organic light-emitting device of claim 1 , wherein each of the host and the sensitizer does not emit light.

9. The organic light-emitting device of claim 1 , wherein the emission layer consists of the host, the dopant, and the sensitizer.

10. The organic light-emitting device of claim 1 , wherein the host, the dopant, and the sensitizer satisfy Condition 5 below:
T 1 ( H )> T 1 ( S )> S 1 ( D )  <Condition 5>

wherein, in Condition 5,
T 1 (H) is a lowest excitation triplet energy level of the host,
T 1 (S) is a lowest excitation triplet energy level of the sensitizer, and
S 1 (D) is a lowest excitation singlet energy level of the dopant.

11. The organic light-emitting device of claim 1 , wherein the host comprises an amphoteric host, an electron transport host, and/or a hole transport host,
the electron transport host comprises at least one electron transport moiety,
the hole transport host does not comprise an electron transport moiety, and
the electron transport moiety is a cyano group, a π electron-deficien

Assignees

• Samsung Electronics Co Ltd

Inventors

• Jeon Soonok
• Kwon Eunsuk
• Kim Sangmo
• Min Minsik
• Bae Hyejin
• Chung Yeonsook
• Jung Yongsik
• Son Youngmok
• Lee Eunkyung
• Lee Hasup
• Choi Hyeonho

Classifications

• H01L51/5056

  Electricity · mapped topic

• H01L51/0087

  Electricity · mapped topic

• H01L51/5024

  Electricity · mapped topic

• H01L51/5004 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic