Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12291540-B2
Application number	US-202016831700-A
Country	US
Kind code	B2
Filing date	Mar 26, 2020
Priority date	Mar 29, 2019
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device:

wherein, in Formula 1, Y 2 , ring CY 1 , ring CY 2 , T 1 , T 2 , A 1 to A 7 , a1, and a2 are as defined in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1,

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

in Formula 1 is one of groups represented by Formulae CY1(1)-1 to CY1(1)-64, CY1(6)-2 to CY1(6)-8, and CY1(6)-10 to CY1(6)-16:

wherein, in Formulae CY1(1)-1 to CY1(1)-64, and CY1(6)-2 to CY1(6)-8 and CY1(6)-10 to CY1(6)-16,
indicates a binding site to Ir in Formula 1, and
*″ indicates a binding site to ring CY 2 in Formula 1,
ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 , T 2 and A 1 to A 7 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 1 -C 60 alkylthio 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 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 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 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
T 11 to T 18 are the same as defined in connection with T 1 , provided that each of Ti to T 18 is not hydrogen, T 101 to T 108 in Formulae CY1(1)-1 to CY1(1)-64 each comprises at least one fluoro group (—F) and T 106 and T 107 in Formulae CY1(6)-2 to CY1(6)-8 and CY1(6)-10 to CY1(6)-16 each comprises a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, a fluorinated biphenyl group, or a fluorinated terphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof,
a1 and a2 are each independently an integer of 0 to 20; when al is 2 or greater, two or more T 1 (s) are identical to or different from each other; when a2 is 2 or greater, two or more T 2 (s) are identical to or different from each other; and the sum of a1 and a2 is 1 or greater,
two or more of Ti(s) in the number of a1 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of T 2 ( s ) in the number of a2 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
T 1 and T 2 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of A 1 to A 7 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1a is the same as defined in connection with A 7 ,
a substituent(s) 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 1 -C 60 alkylthio group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -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 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently:
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 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, —C 1 , —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 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 1 -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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof;
a C 3 -C 10 cycloalkyl group, a C 1 -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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jiyoun
• Kim Soyeon
• Cho Yongsuk
• Choi Jongwon
• Kravchuk Dmitry
• Lee Banglin
• Koo Hyun
• Lee Sunghun
• Cho Yuri

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K50/18

  Carrier blocking layers · CPC title