Organometallic compound, organic light-emitting device including the organometallic compound, and apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12201016-B2
Application number	US-201916669208-A
Country	US
Kind code	B2
Filing date	Oct 30, 2019
Priority date	Mar 13, 2019
Publication date	Jan 14, 2025
Grant date	Jan 14, 2025

Abstract

Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic light-emitting device. The organometallic compound is represented by Formula 1:

M 11 (L 11 ) n11 (L 12 ) n12   <Formula 1>

In Formula 1, L 11 is a ligand represented by Formula 1-1, which is explained in the specification:

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:
M 11 (L 11 ) n11 (L 12 ) n12 ,  <Formula 1>

wherein, in Formula 1,
M 11 is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal of the Periodic Table of Elements,
L 11 is a ligand represented by Formula 1-1,
L 12 is selected from a monodentate ligand and a bidentate ligand,
n11 is 1, and
n12 is selected from 0, 1, and 2:

wherein, in Formula 1-1,
X 11 to X 13 are each a single bond,
Y 11 , Y 12 , and Y 13 are each C,
Y 14 is N,
T 11 to T 14 are each a single bond,
ring A 12 , ring A 13 , and ring A 15 to ring A 20 are each a benzene group,
R 11 to R 20 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 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 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 ), and —P(═S)(Q 1 )(Q 2 ),
b11 is 3,
b12 and b13 are each independently an integer from 1 to 3,
b14 is 4,
b15 to b20 are each independently an integer from 1 to 4,
Q 1 to Q 3 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 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group, and a C 1 -C 60 heteroaryl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group,
*1 to *4 each indicate a binding site to M 11 ,
a group represented by

 is a group represented by Formula 3-11, and
a group represented by

 is represented by Formula 3-41:

wherein in Formulae 3-11 and 3-41,
R 11a , R 11b , and R 11c are each independently the same as defined in connection with R 1 in Formula 1-1, and R 11a , R 11b , and R 11c do not bond to each other to form a fused ring, and
R 14a , R 14b , R 14c , and R 14d are each independently the same as defined in connection with R 14 in Formula 1-1, and
wherein in Formulae 1-1, 3-11, and 3-41,
* and *′ each indicate a binding site to a neighboring atom.

2. The organometallic compound of claim 1 , wherein
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).

3. The organometallic compound of claim 1 , wherein
a group represented by

 is a group represented by Formula 3-21, and
a group represented by

 is a group represented by Formula 3-31

wherein, in Formulae 3-21 and 3-31,
*, *′, and *″ each indicate a binding site to a neighboring atom,
R 12a , R 12b , and R 12c are each independently the same as defined in connection with R 12 in Formula 1-1, and
R 13a , R 13b , and R 13c are each independently the same as defined in connection with R 13 in Formula 1-1.

4. The organometallic compound of claim 1 , wherein
R 11 to R 20 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenyl group, and a terphenyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jaesung
• Ko Soobyung
• Kim Sungbum
• Kim Haejin
• Shin Sujin
• Ahn Eunsoo
• Lee Eunyoung
• Lee Hyunjung
• Jeon Mina
• HAN Junghoon

Classifications

• H10K50/858

  comprising refractive means, e.g. lenses · CPC title

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K85/346 Primary

  comprising platinum · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/10

  Triplet emission · CPC title