Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device

Patent metadata

Field	Value
Publication number	US-12415827-B2
Application number	US-202217692455-A
Country	US
Kind code	B2
Filing date	Mar 11, 2022
Priority date	Mar 23, 2021
Publication date	Sep 16, 2025
Grant date	Sep 16, 2025

Abstract

Provided are an organometallic compound represented by Formula 1, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device:Each substituent in Formula 1 is the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein in Formula 1,
M 1 and M 2 are each independently 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), or thulium (Tm),
A1 to A4 and B1 to B4 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
Y 10 to Y 12 , Y 20 to Y 22 , Y 30 to Y 32 , Y 40 to Y 42 , Y 50 to Y 52 , Y 60 to Y 62 , Y 70 to Y 72 , and Y 80 to Y 82 are each independently C or N,
T 1 and T 2 are each independently a single bond, *—O—*′, *—S—*′, *—C(R 1 )(R 2 )—*′, *—C(R 1 )═*′, *═C(R 1 )—*′, *—C(R 1 )═C(R 2 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 1 )—*′, *—N(R 1 )—*, *—P(R 1 )—*, *—Si(R 1 )(R 2 )—*′, or *—Ge(R 1 )(R 2 )—*′,
L 10 is a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
a10 is 1, 2, 3, 4, or 5,
R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , and R 80 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 20 alkyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 20 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkyl group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryl group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroaryl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroaryloxy group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroarylthio group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 41 )(Q 42 )(Q 43 ), —N(Q 41 )(Q 42 ), —B(Q 41 )(Q 42 ), —C(═O)(Q 41 ), —S(═O) 2 (Q 41 ), or —P(═O)(Q 41 )(Q 42 ),
two neighboring substituents among R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , and R 80 are optionally linked to each other to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
b10, b20, b30, b40, b50, b60, b70, and b80 are each independently 1, 2, 3, 4, 5, 6, 7, or 8,
* and *′ each indicate a binding site to a neighboring atom, and
R 10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 6 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, or a C 1 -C 60 heteroarylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ),
wherein Q 11 to Q 13 , Q 21 to Q 23 , Q 31 to Q 33 , and Q 41 to Q 43 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro 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; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 6 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.

2. The organometallic compound of claim 1 , wherein M 1 and M 2 are each independently Pt or Pd.

3. The organometallic compound of claim 1 , wherein A1 to A4 are each independently:
a 5-membered heterocyclic group, or
a polycyclic C 1 -C 30 heterocyclic group comprising a 5-membered heterocyclic group.

4. The organometallic compound of claim 1 , wherein
A1 and A4 are each independently a group represented by one of Formulae 3-1 to 3-3, and
A2 and A3 are each independently a group represented by one of Formulae 3-4 and 3-5:

wherein in Formulae 3-1 to 3-5,
X 31 to X 39 are each independently C(Z 32 ) or N,
Z 31 and Z 32 are each independently the same as described in connection with R 10 in Formula 1, and
*, *′ and *″ each indicate a binding site to a neighboring atom.

5. The organometallic compound of claim 1 , wherein
a bond between M 1 and Y 10 is a coordinate bond,
a bond between M 1 and Y 20 is a coordinate bond,
a bond between M 2 and Y 30 is a coordinate bond,
a bond between M 2 and Y 40 is a coordinate bond,
a bond between M 1 and Y 50 is a covalent bond,
a bond between M 1 and Y 60 is a covalent bond,
a bond between M 2 and Y 70 is a covalent bond, and
a bond between M 2 and Y 80 is a covalent bond.

6. The organometallic compound of claim 1 , wherein T 1 and T 2 are each independently *—O—*′ or *—S—*′.

7. The organometallic compound of claim 1 , wherein L 10 is a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 2 -C 20 alkenylene group unsubstituted or substituted with at least one R 10a , a C 2 -C 20 alkynylene group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkylene group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkylene group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkenylene group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkenylene group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylene group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroarylene group unsubst

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jaesung
• Shin Sujin
• Lee Eunyoung
• Lee Hyunjung
• HAN Junghoon

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

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

• H10K2101/10

  Triplet emission · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title