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

Patent metadata

Field	Value
Publication number	US-12101994-B2
Application number	US-202016835818-A
Country	US
Kind code	B2
Filing date	Mar 31, 2020
Priority date	Apr 17, 2019
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

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:

wherein, in Formula 1, R 1 to R 9 , R 21 to R 23 , and A 1 to A 7 are each independently the same as described herein.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1A:

wherein, in Formula 1A,
R 1 to R 9 , and A 1 to A 6 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 6 -C 60 cycloalkenyl group, a substituted or unsubstituted C 7 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 arylalkyl 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 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 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
R 21 is
a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group; or
a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each substituted with 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 a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, or any combination thereof;
R 23 is 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 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group;
R 31 is hydrogen or deuterium,
A 7 is
hydrogen, deuterium, an unsubstituted C 1 -C 20 alkyl group, or an unsubstituted C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each substituted with deuterium, an unsubstituted C 1 -C 10 alkyl group, an unsubstituted cyclopentyl group, an unsubstituted cyclohexyl group, an unsubstituted cycloheptyl group, an unsubstituted cyclooctyl group, an unsubstituted adamantyl group, an unsubstituted norbornenyl group, an unsubstituted cyclopentenyl group, an unsubstituted cyclohexenyl group, an unsubstituted cycloheptenyl group, an unsubstituted bicyclo [1.1.1]pentyl group, an unsubstituted bicyclo [2.1.1]hexyl group, an unsubstituted bicyclo[2.2.1]heptyl group, an unsubstituted bicyclo [2.2.2]octyl group, an unsubstituted phenyl group, an unsubstituted (C 1 -C 20 alkyl)phenyl group, an unsubstituted biphenyl group, or an unsubstituted terphenyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo [1.1.1]pentyl group, a bicyclo [2.1.1]hexyl group, a bicyclo [2.2.1]heptyl group, a bicyclo [2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, an unsubstituted C 1 -C 20 alkyl group, an unsubstituted C 1 -C 20 alkoxy group, an unsubstituted cyclopentyl group, an unsubstituted cyclohexyl group, an unsubstituted cycloheptyl group, an unsubstituted cyclooctyl group, an unsubstituted adamantyl group, an unsubstituted norbornenyl group, an unsubstituted cyclopentenyl group, an unsubstituted cyclohexenyl group, an unsubstituted cycloheptenyl group, an unsubstituted bicyclo [1.1.1]pentyl group, an unsubstituted bicyclo [2.1.1]hexyl group, an unsubstituted bicyclo [2.2.1]heptyl group, an unsubstituted bicyclo [2.2.2]octyl group, an unsubstituted phenyl group, an unsubstituted (C 1 -C 20 alkyl)phenyl group, an unsubstituted biphenyl group, or an unsubstituted a terphenyl group; or
—Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 );
CY 1 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group,
CY 1 and R 21 are not linked to form a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,
CY 1 and R 23 are not linked to form a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,
two or more of R 1 to R 9 are optionally linked to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 2 -C 60 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of A 1 to A 7 are not optionally linked to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one Ria or a C 2 -C 60 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1a is the same as defined in connection with R 7 ,
a substituent of 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 7 -C 60 arylalkyl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio 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 , —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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each substituted with 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 arylalkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 hetero

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jiyoun
• Kwak Yoonhyun
• Koo Hyun
• Kim Soyeon
• Sim Myungsun
• Cho Yongsuk
• Choi Jongwon
• Kravchuk Dmitry

Classifications

• H10K71/40

  Thermal treatment, e.g. annealing in the presence of a solvent vapour · CPC title

• H10K85/342 Primary

  comprising iridium · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2102/351

  Thickness · CPC title

• H10K2101/10

  Triplet emission · CPC title