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

Patent metadata

Field	Value
Publication number	US-12414459-B2
Application number	US-202418431861-A
Country	US
Kind code	B2
Filing date	Feb 2, 2024
Priority date	Sep 5, 2017
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

An organometallic compound represented by Formula 1:wherein, in Formula 1, groups and variables are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, M in Formula 1 is a transition metal,
X 1 in Formula 1 is nitrogen (N),
X 2 to X 4 in Formula 1 are each independently carbon (C) or N,
in Formula 1, a bond between X 1 and M is a coordinate bond, and one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond while the remaining two bonds are each independently be a covalent bond,
n in Formula 1 is 0 or 1, wherein, when n is 0, CY 1 and CY 4 are not linked each other,
in Formula 1, i) when n is 0, CY 1 is a group represented by one selected from Formulae A1-1 to A1-6; and ii) when n is 1, CY 1 is a group represented by one selected from Formulae A11-1 to A11-4,
in Formulae A1-1 to A1-6 and A11-1 to A11-4,
i) X 11 is *—N[(L 11 ) c11 -(R 11 )]—*′, *—B(R 11 )—*′, *—P(R 11 )—*′, *—C(R 11a )(R 11b )—*′, *—Si(R 11a )(R 11b )—*′, *—Ge(R 11a )(R 11b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 -*′, or *—C(═S)—*′, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, and X 15 is C(R 15 ) or N;
ii) when X 14 is C(R 14 ) and X 15 is C(R 15 ), R 14 and R 15 are not linked each other; and
iii) R 11a and R 11b are optionally linked each other via a second linking group to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formulae A1-1 to A1-6 and A11-1 to A11-4, * may indicate a binding site to M in Formula 1, *′ may indicate a binding site to T 1 in Formula 1, and *″ may indicate a binding site to T 4 in Formula 1,
in Formula 1, CY 2 to CY 4 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group,
provided that when CY 4 is a cyclopentadiene group, a thiophene group, a furan group, a pyrrole group, a pyrazole group, an imidazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, then X 4 is C,
in Formula 1, T 1 to T 4 are each independently selected from a single bond, a double bond, *—N[(L 5 ) c5 -(R 5 )]—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5 )(R 6 )—*′, *—Si(R 5 )(R 6 )—*′, *—Ge(R 5 )(R 6 )—*′, *—S—*′, *—Se—*′, *—O—*, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5 )═C(R 6 )—*′, *—C(═S)—*′, and *—C≡C—*′, wherein R 5 and R 6 are optionally linked each other via a first linking group to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
L 5 and L 11 are each independently selected from a single bond, a substituted or unsubstituted C 5 -C 30 carbocyclic group, and a substituted or unsubstituted C 1 -C 30 heterocyclic group,
c5 and c11 are each independently an integer from 1 to 3, wherein, when c5 is two or more, two or more of groups L 5 are identical to or different from each other, and when c11 is two or more, two or more of groups L 11 are identical to or different from each other,
R 2 to R 6 , R 11 to R 15 , R 11a , and R 11b are each independently selected from 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 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 7 -C 60 arylalkyl 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 C 2 -C 60 heteroaryl alkyl 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 ), and —P(═O)(Q 8 )(Q 9 ),
provided that when CY 1 is a group represented by Formula A1-1, then i) X 11 is O and at least one of X 12 to X 15 is N, or ii) X 11 is *—S—*′ or *—Se—*′, a2 to a4 are each independently an integer from 0 to 20,
in Formula 1, two or more selected from groups R 2 in the number of a2 are optionally linked each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formula 1, two or more selected from groups R 3 in the number of a3 are optionally linked each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formula 1, two or more selected from groups R 4 in the number of a4 are optionally linked each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formula 1, two or more of R 2 to R 4 are optionally linked each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formula 1, one of R 5 and R 6 and one of R 2 to R 4 are optionally linked each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
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 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy 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 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 7 -C 60 alkyl aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 7 -C 60 aryl alkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 alkyl heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the C 2 -C 60 heteroaryl alkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 a

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Jongwon
• Aratani Sukekazu
• Lee Kum Hee
• Lee Banglin
• Choi Hyeonho
• Kwak Seungyeon
• Kwak Yoonhyun
• Kim Sangdong
• Kim Jiwhan
• Baik Chul
• Cho Yongsuk

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1033

  with oxygen · CPC title