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

Patent metadata

Field	Value
Publication number	US-11832509-B2
Application number	US-202016898744-A
Country	US
Kind code	B2
Filing date	Jun 11, 2020
Priority date	Jun 13, 2019
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

Provided are 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 1 (L 11 ) n11 (L 12 ) n12   <Formula 1>
wherein L 11 in Formula 1 is a ligand represented by Formula 1-1, and the descriptions of other substituents are the same as described in the detailed description of the present application:

First claim

What is claimed is:

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

wherein, in Formula 1,
M 1 is a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements,
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,
*1 to *4 each indicate a binding site to M 1 ;
A 10 is an N-containing heterocyclic group,
A 20 , A 30 , and A 40 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 is a single bond, *—N[(L 1 ) a1 -(R 1 ) b1 ]—*′, *—B(R 1 )—*′, *—P(R 1 )—*′, *—C(R 1 )(R 2 )—*′, *—Si(R 1 )(R 2 )—*′, *—Ge(R 1 )(R 2 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 1 )═C(R 2 )—*′, *—C(═S)—*′, or *—C≡C—*′,
T 2 is a single bond, *—N[(L 2 ) a2 -(R 3 ) b3 ]—*′, *—B(R 3 )—*′, *—P(R 3 )—*′, *—C(R 3 )(R 4 )—*′, *—Si(R 3 )(R 4 )—*′, *—Ge(R 3 )(R 4 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 3 )═C(R 4 )—*′, *—C(═S)—*′, or *—C≡C—*′,
L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C 5 -C 30 carbocyclic group, or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
a1 is an integer from 1 to 3, and when a1 is 2 or more, two or more of L 1 (s) are identical to or different from each other,
a2 is an integer from 1 to 3, and when a2 is 2 or more, two or more of L 2 (s) are identical to or different from each other,
X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N,
X 20 is C or N, X 30 is C or N, X 40 is C or N,
X 21 , X 22 , X 31 , X 32 and X 41 are each independently C or N, and
Ar 1 is a substituted or unsubstituted C 5 -C 30 carbocyclic group, and when Ar 1 is a benzene group, An is represented by one of Formulae Ar1-1 to Ar1-18,

wherein, in Formulae Ar1-1 to Ar1-18,
E 11 to E 15 are each independently a substituted or unsubstituted C 1 -C 60 alkyl 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 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
E 16 and E 17 are each independently a substituted or unsubstituted C 6 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted C 3 -C 10 cycloalkyl group, an unsubstituted C 7 -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 C 6 -C 60 aryl group, an unsubstituted C 7 -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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R 1 to R 4 , Ru, R 12 , R 20 , R 30 , and R 40 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 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 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl 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, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ),
two or more of neighboring R 1 to R 4 , R 20 , R 30 , and R 40 are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b1 and b3 are each independently an integer from 1 to 5,
when b1 is 2 or more, two or more of R 1 (s) are identical to or different from each other, and when b3 is 2 or more, two or more of R 3 (s) are identical to or different from each other,
b20, b30, and b40 are each independently an integer from 1 to 10,
when b20 is 2 or more, two or more R 20 (s) are identical to or different from each other, when b30 is 2 or more, two or more R 30 (s) are identical to or different from each other, and when b40 is 2 or more, two or more R 40 (s) are identical to or different from each other,
* and *′ each indicate a binding site to a neighboring atom,
at least one substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 6 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 1 -C 60 alkylthio group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 7 -C

Assignees

• Samsung Electronics Co Ltd

Inventors

• Bae Hyejin
• Min Minsik
• Kwon Eunsuk
• Kim Sangmo
• Lee Hasup
• Jeon Soonok
• Kim Jongsoo
• Nam Sungho
• Choi Hyeonho

Classifications

• H10K85/346 Primary

  comprising platinum · CPC title

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09B57/10

  Metal complexes of organic compounds not being dyes in uncomplexed form · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title