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

Patent metadata

Field	Value
Publication number	US-12145950-B2
Application number	US-201816141292-A
Country	US
Kind code	B2
Filing date	Sep 25, 2018
Priority date	Sep 29, 2017
Publication date	Nov 19, 2024
Grant date	Nov 19, 2024

Abstract

Aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound. The organometallic compound, which may act as a dopant in the emission layer is 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, in Formula 1,
M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
X 1 , X 2 , and X 4 are each independently C or N,
X 3 is C,
X 5 is O,
two bonds selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M are each a coordinate bond, and the other thereof is a covalent bond,
a bond between X 5 and M is a covalent bond,
a moiety represented by

is selected from a group represented by Formulae CY1(1) to CY1(16),
a moiety represented by

is selected from a group represented by Formulae CY2(2) to CY2(8),
a moiety represented by

is selected from a group represented by Formulae CY3(2) to CY3(8),
a moiety represented by

is selected from a group represented by Formulae CY4(235) to CY4(8),

T 1 is a single bond,
T 2 is selected from a double bond, *—N[(L 63 ) a63 -(R 63 )]—*′, *—B(R 63 )—*′, *—P(R 63 )—*′, *—Si(R 63 )(R 64 )—*′, *—Ge(R 63 )(R 64 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 63 )═*′, *═C(R 63 )—*′, *—C(R 63 )═C(R 64 )—*′, *—C(═S)—, and *—C≡C—*′, and * and *′ each indicate a binding site to a neighboring atom,
T 3 is a single bond,
L 63 is 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,
a63 is an integer from 1 to 3, wherein, when a63 is two or more, two or more groups L 63 are identical to or different from each other,
X 41 is C(R 41 )(R 42 ), N(R 41 ), O, S, or Si(R 41 )(R 42 ),
R 1a to R 1d are the same as described in connection with R 1 ,
R 2a to R 2c are the same as described in connection with R 2 ,
R 3a to R 3c are the same as described in connection with R 3 ,
R 41 , and R 42 are the same as described in connection with R 4 ,
R 1 to R 4 , R 41 , R 42 , R 63 and R 64 , 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, 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl 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 cycloctyl 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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl 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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl 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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Baik Chul
• Lee Kum Hee
• Cho Yongsuk
• Choi Jongwon
• Kwak Yoonhyun
• Kwon Ohyun
• Kim Sangdong
• Cho Hwayoung

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title