Organometallic compound, organic light-emitting device including organometallic compound, and diagnostic composition including organometallic compound

Patent metadata

Field	Value
Publication number	US-11807654-B2
Application number	US-202016744481-A
Country	US
Kind code	B2
Filing date	Jan 16, 2020
Priority date	May 10, 2019
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

An organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound:

M 11 (L 11 ) n11 (L 12 ) n12   Formula 1
wherein, in Formula 1, M 11 is a first-row transition metal, a second-row transition metal, or a third-row transition metal, L 11 is a ligand represented by Formula 1-1, L 12 is a monodentate ligand or a bidentate ligand, n11 is 1, and n12 is 0, 1, or 2:

wherein, in Formula 1-1,
Y 11 , A 11 , T 11 k11, k12, k13, b11, E 11 to E 13 and R 11 to R 17 are described in the specification, and *1 to *4 each independently indicate a binding site to M 11 .

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 a first-row transition metal, a second-row transition metal, or a third-row transition metal,
L 11 is a ligand represented by Formula 1-1,
L 12 is a monodentate ligand or a bidentate ligand,
n11 is 1, and
n12 is 0, 1, or 2:

wherein, in Formula 1-1,
Y 11 is C or N,
A 11 is of Formulae 2-2 to 2-20, 2-22 to 2-36 and 2-38 to 2-47:

wherein, in Formulae 2-2 to 2-20, 2-22 to 2-36 and 2-38 to 2-47,
X 24 is N or C(R 24 ), X 25 is N or C(R 25 ), X 26 is N or C(R 26 ), X 27 is N or C(R 27 ),
b21 is an integer from 1 to 8,
*4 indicates a binding site to M 11 , and
* indicates a binding site to an adjacent atom,
T 11 is C(R 16 )(R 17 ), Si(R 16 )(R 17 ), O, S, B(R 16 ), or N(R 16 ),
k11 is 0, 1, 2, or 3,
k12 is 0, 1, or 2,
k13 is 0, 1, 2, 3, or 4,
the sum of k11 to k13 is 1 or greater,
E 11 to E 13 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl 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 2 -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-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 two adjacent groups of E 11 to E 13 are optionally bound to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
R 11 to R 17 , R 21 , and R 24 to R 27 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 2 -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-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 two adjacent groups R 12 to R 15 are optionally bound to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
R 22 and R 23 are each independently hydrogen,
b11 is 1, 2, 3, 4, 5, 6, 7, or 8,
wherein 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 substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, or a C 6 -C 60 aryl group, or a C 6 -C 60 aryl group substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, or a C 6 -C 60 aryl group, and
*1 to *4 each independently indicate a binding site to M 11 .

2. The organometallic compound of claim 1 , wherein a moiety represented by

is represented by any one of Formulae 3-1 to 3-8:

wherein, in Formulae 3-1 to 3-8,
E 11a , E 11b , and E 11c are each understood by referring to the description of E 11 in Formula 1-1,
*1 indicates a binding site to M 11 , and
* and *′ each indicate a binding site to an adjacent atom.

3. The organometallic compound of claim 2 , wherein a moiety represented by

is represented by any one of Formulae 3-1 to 3-4.

4. The organometallic compound of claim 1 , wherein a moiety represented by

is represented by any one of Formulae 4-1 to 4-42:

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Bae Hyejin
• Sotoyama Wataru
• Kim Sangmo
• Kim Wook
• Kim Jongsoo
• Kim Joonghyuk
• Min Minsik
• Son Jhunmo
• Lee Hasup
• Jung Yongsik

Classifications

• C07F15/0086 Primary

  Platinum compounds · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K2101/10

  Triplet emission · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title