Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12371611-B2
Application number	US-202117193089-A
Country	US
Kind code	B2
Filing date	Mar 5, 2021
Priority date	Apr 16, 2020
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

Provided is an organic light-emitting device including an emission layer that includes a sensitizer, a fluorescent emitter, and a host.

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 sensitizer, a fluorescent emitter, and a host, the sensitizer comprises ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof,
and
the sensitizer and the fluorescent emitter satisfy Inequality 1 below:
| E adia T1 SE)− E vert S1 (FL)|<0.2 eV  Inequality 1

In Inequality 1,
E adia T1 (SE) indicates an adiabatic triplet excitation energy of the sensitizer, and
E vert S1 (FL) indicates a vertical singlet excitation energy of the fluorescent emitter,
wherein the fluorescent emitter is a compound represented by Formula 511:

wherein, in Formula 511,
L 511 to L 514 are each independently 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 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xd11 to xd14 are each independently 1, 2, 3, 4, or 5,
R 511 to R 514 are each independently a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; or
a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one of 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof, and
xe11 to xe14 are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8.

2. The organic light-emitting device of claim 1 , wherein the sensitizer comprises an organometallic compound represented by Formula 101 below:
M 11 (L 11 ) n11 (L 12 ) n12   Formula 101

In Formula 101,
M 11 is Ru, Pd, Re, Os, or Pt;
L 11 is a ligand represented by one of Formulae 1-1 to 1-4 below;
L 12 is a monodentate ligand or a bidentate ligand;
n11 is 1; and
n12 is 0, 1, or 2,
wherein when n12 is 2, then each occurrence of L 12 is the same or different,

wherein, in Formulae 1-1 to 1-4,
A 1 to A 4 are each independently 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 are each independently 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 are each independently 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 C 5 -C 30 carbocyclic group, a substituent of the substituted C 1 -C 30 heterocyclic group, and R 91 to R 94 are each independently 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 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 ), or —P(═S)(Q 1 )(Q 2 ),
* 1 , * 2 , * 3 , and * 4 each indicate a binding site to M 11 , 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 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, a C 6 -C 60 aryl group, or any combination thereof.

3. The organic light-emitting device of claim 1 , wherein
the sensitizer comprises an organometallic compound represented by Formula 111 below:

In Formula 111,
M 11 , Y 11 to Y 14 , and T 1 to T 3 are each the same as described in claim 2 ,
A 11 to A 14 are each independent

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Hasup
• Kim Sangmo
• Kwon Eunsuk
• Kim Jong Soo
• Nam Sungho
• Min Minsik
• Bae Hyejin
• Choi Hyeonho

Classifications

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K50/121 Primary

  for assisting energy transfer, e.g. sensitization · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/346

  comprising platinum · CPC title