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

Patent metadata

Field	Value
Publication number	US-12286446-B2
Application number	US-201916559056-A
Country	US
Kind code	B2
Filing date	Sep 3, 2019
Priority date	Sep 5, 2018
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

An organometallic compound represented by Formula 1, an organic light-emitting device including the same, and a diagnostic composition including the organometallic compound:

wherein, Formula 1, R 1 to R 12 and R 21 to R 23 are each independently the same as described in the detailed description of the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,
R 1 to R 9 , R 11 and R 23 are each independently:
hydrogen, deuterium, —F, a cyano group, or a C1-C20 alkyl group;
a C 1 -C 20 alkyl group substituted with deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 10 alkyl 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, a terphenyl group, or any combination thereof;
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, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 10 alkyl 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, a terphenyl group, or any combination thereof; or
—Si (Q 3 ) (Q 4 ) (Q 5 ), or —Ge (Q 3 ) (Q 4 ) (Q 5 ); and
at least one of R 1 to R 5 is each independently:
deuterium, —F, a cyano group, or a C 1 -C 20 alkyl group;
a C 1 -C 20 alkyl group substituted with deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 10 alkyl 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, a terphenyl group, or any combination thereof;
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 (C 1 -C 20 alkyl) phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 10 alkyl 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, a terphenyl group, or any combination thereof;
a phenyl group, unsubstituted or substituted with deuterium, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 10 alkyl 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, a terphenyl group, or any combination thereof; or
—Si (Q 3 ) (Q 4 ) (Q 5 ), or —Ge (Q 3 ) (Q 4 ) (Q 5 );
wherein, Q 3 to Q 5 are each independently:
—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, or—CD 2 CDH 2 ; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C 1 -C 10 alkyl group, a phenyl group, or any combination thereof,
R 10 in Formula 1 is represented by Formula 3, and R 12 in Formula 1 is represented by Formula 4,

wherein, in Formulae 3 and 4,
A 1 to A 6 are each independently:
deuterium; or
a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 60 aryl group, or a C 1 -C 60 heteroaryl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or any combination thereof; and
* indicates a binding site to a neighboring atom,
wherein any two of A 1 to A 3 and any two of A 4 to A 6 are not optionally cyclized to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a group or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a group, and
wherein at least one of A 1 to A 6 is:
a C 3 -C 10 cycloalkyl group, unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or any combination thereof, or
a C 2 -C 20 alkyl group, unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or any combination thereof,
R 21 is a C 2 -C 20 alkyl group, a deuterium-containing C 2 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or a deuterium-containing C 3 -C 10 cycloalkyl group,
R 22 is a C 1 -C 20 alkyl group, a deuterium-containing C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or a deuterium-containing C 3 -C 10 cycloalkyl group,
two or more of R 1 to R 9 are not optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a group or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a group,
R 4 is not optionally linked with R 21 , R 22 , or R 23 to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a group or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a group, and
R 1a is the same as defined in connection with R 1 .

2. The organometallic compound of claim 1 , wherein
R 21 is an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-n

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Jongwon
• Cho Yongsuk
• Kwak Yoonhyun
• Koo Hyun
• Kwon Ohyun
• Kim Soyeon
• Aratani Sukekazu
• Lee Jiyoun
• Im Kyuhyun
• Kravchuk Dmitry

Classifications

• H10K85/649

  Aromatic compounds comprising a hetero atom · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/82

  Cathodes · CPC title

• H10K50/81

  Anodes · CPC title