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

Patent metadata

Field	Value
Publication number	US-11569460-B2
Application number	US-201816176330-A
Country	US
Kind code	B2
Filing date	Oct 31, 2018
Priority date	Nov 8, 2017
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2 (L 3 ) n3   Formula 1
wherein M, L 1 , L 2 , L 3 , n1, n2, and n3 are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by

wherein, in Formula 1A(1),
M is a transition metal,
X 1 and X 2 are each independently N or C,
X 5 is selected from a covalent or coordinate bond, O, S, B(R′), N(R′), P(R′), (C′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′, R″), N(R′)(R″), and P(R′)(R″); when X 5 is a covalent or coordinate bond, X 1 and M are directly bound to each other,
X 4 is bound to M via a coordinate bond,
two bonds selected from a bond between M and X 5 or X 1 , a bond between X 2 and M, and a bond between X 3 and M are each a covalent bond, while the remaining bond is a coordinate bond,
X 3 and Y 12 are each independently N or C,
X 4 is O or S,
ring CY 1 to ring CY 4 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 and T 2 are each independently selected from a single bond, a double bond, *—N(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)—*′, or *—C≡C—*′, wherein * and *′ each indicate a binding site to an adjacent atom,
R 1 to R 6 , R′ and R 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 heteroaryl 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 arylthio 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 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 )
a1 to a4 are each independently an integer from 0 to 20,
two adjacent groups selected from a plurality of R 1 groups are optionally linked to form a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, wherein the C 5 -C 30 carbocyclic group and the C 1 -C 30 heterocyclic group are each unsubstituted or substituted with at least one R 10a ,
two adjacent groups selected from a plurality of R 2 groups are optionally linked to form a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, wherein the C 5 -C 30 carbocyclic group and the C 1 -C 30 heterocyclic group are each unsubstituted or substituted with at least one R 10a ,
two adjacent groups selected from a plurality of R 3 are optionally linked to form a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, wherein the C 5 -C 30 carbocyclic group and the C 1 -C 30 heterocyclic group are each unsubstituted or substituted with at least one R 10a ,
at least two adjacent groups selected from R 1 , R 2 , R 3 , R 5 , R 6 , R′, and R″ are optionally linked to form a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, wherein the C 5 -C 30 carbocyclic group and the C 1 -C 30 heterocyclic group are each unsubstituted or substituted with at least one R 10a ,
R 10a is 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 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 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 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 ),
Y 11 is selected from N and C, and
wherein in Formula 1A(1) when Y 12 is C, then Y 11 is C.

2. The organometallic compound of claim 1 , wherein M is Pt, Pd, or Au.

3. The organometallic compound of claim 1 , wherein
ring CY 3 is selected from i) a first ring, ii) a second ring, iii) a condensed ring in which two or more second rings are condensed, and iv) a condensed ring in which at least one first ring and at least one second ring are condensed,
the first ring is selected from a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group, and
the second ring is selected from an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group.

4. The organometallic compound of claim 1 , wherein R 3 R 4 , and R 10a are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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, —SF 5 , 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, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino 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 C 1 -C 10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an

Assignees

• Samsung Electronics Co Ltd

Inventors

• Cho Yongsuk
• Kwon Ohyun
• Kwak Yoonhyun
• Kim Sungjun
• Baik Chul
• Lee Kum Hee
• Lee Sunghun
• Jeon Aram
• Choi Jongwon

Classifications

• H01L51/0085

  Electricity · mapped topic

• C09K2211/185

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

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/5016

  Electricity · mapped topic