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

Patent metadata

Field	Value
Publication number	US-11512105-B2
Application number	US-202016840871-A
Country	US
Kind code	B2
Filing date	Apr 6, 2020
Priority date	Apr 16, 2019
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

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(L1)n1(L2)n2,  Formula 1wherein, in Formula 1, M, L1, L2, n1, and n2 are each independently the same as described herein.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2 ,  Formula 1

wherein, in Formula 1,
M is Ir or Os, and the sum of n1 and n2 is 3 or 4; or
M is Pt, and the sum of n1 and n2 is 2,
L 1 is a ligand represented by Formula 2,
n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more Li are identical to or different from each other,
L 2 is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,
n2 is 0, 1, 2, 3, or 4, wherein, when n2 is 2 or more, two or more L 2 are identical to or different from each other, and
L 1 and L 2 are different from each other:

wherein, in Formula 2,
X 1 is C or N
X 21 is C or N,
a group represented by

in Formula 2 is 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, or an imidazopyrimidinyl group, each unsubstituted or substituted with R 1 in the number of a1,
a group represented by

in Formula 2 is a group represented by one of Formulae CY21-1 to CY21-25:

wherein, in Formulae CY21-1 to CY21-25,
X 21 is C or N,

X 22 is C(R 22 )(R 23 ), N(R 22 ), O, S, or Si(R 22 )(R 23 ),
R 21 to R 29 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 2 -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 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 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropoly cyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ) or —P(Q 8 )(Q 9 ),
a26 is an integer from 0 to 6,
a24 is an integer from 0 to 4,
a23 is an integer from 0 to 3,
a22 is an integer from 0 to 2,
*″ indicates a binding site to a carbon atom of a neighboring 6-membered ring in Formula 2, and
* indicates a binding site to M in Formula 1,

X 2 and X 3 are each independently O, S, Se, or C(R 2 ), wherein one of X 2 or X 3 is O, S, or Se,
X 4 is N or C(R 4 ),
X 5 is N or C(R 5 ),
R 1 , R 2 , R 4 , and R 5 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 2 -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 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 heteroarylalkyl 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 ), —P(═O)(Q 8 )(Q 9 ) or —P(Q 8 )(Q 9 ),
a1 is an integer from 0 to 20,
ring CY 1 and R 2 are not linked to each other, and R 1 and R 2 are not linked to each other,
b11 is 0, wherein, when b11 is 0, a group represented by *-(L 11 ) b11 -*′ is a single bond, two or more of a plurality of neighboring R 21 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a groups or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a group,
R 10a is the same as defined in connection with R 21 ,
* and *′ each indicate a binding site to M in Formula 1,
a substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 2 -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 2 -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 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 ,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Kum Hee
• Kwak Seungyeon
• Kwak Yoonhyun
• Kwon Ohyun
• Jeon Aram
• Choi Whail
• Hwang Kyuyoung
• Choi Byoungki
• Choi Hyeonho

Classifications

• C09K2211/185

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

• G01N33/00

  Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00 · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07D329/00

  Heterocyclic compounds containing rings having oxygen and selenium or oxygen and tellurium atoms as the only ring hetero atoms · CPC title