Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11844266-B2
Application number	US-202016750214-A
Country	US
Kind code	B2
Filing date	Jan 23, 2020
Priority date	Jan 31, 2019
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

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

M, X 1 to X 4 , X 11 , ring CY 2 to ring CY 4 , T 1 , T 2 , R 1 to R 4 , and a1 to a4 in Formula 1 are the same as described in the present specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,
M is a transition metal,
X 1 is C, and X 2 to X 4 are each independently C or N,
a bond between X 1 and M is a coordinate bond,
one of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two bonds are covalent bonds,
X 11 is O, S, or N(R 1a ),
a group represented by

is a group represented by one of Formulae CY1-5 to CY1-15,

wherein, in Formulae CY1-5 to CY1-15,
R 11 to R 14 are each independently an unsubstituted or substituted C 1 -C 60 alkyl group or an unsubstituted or substituted C 3 -C 10 cycloalkyl group,
* indicates a binding site to M in Formula 1, and *′ indicates a binding site to ring CY 2 in Formula 1,
ring CY 2 to ring CY 4 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 is a single bond, a double bond, *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5 ) (R 6 )—*′, *—Si(R 5 )(R 6 )—*′, *—Ge(R 5 )(R 6 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5 )═C(R 6 )—*′, *—C(═S)—*′, or *—C≡C—*′,
T 2 is a single bond, a double bond, *—N(R 7 )—*′, *—B(R 7 )—*′, *—P(R 7 )—*′, *—C(R 7 ) (R 8 )—*′, *—Si(R 7 )(R 8 )—*′, *—Ge(R 7 )(R 8 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 7 )═*′, *═C(R 7 )—*′, *—C(R 7 )═C(R 8 )—*′, *—C(═S)—*′, or *C≡C—*′,
R 1a , R 1 to R 8 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 7 -C 60 alkylaryl 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 alkyl 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 ),
a1 is an integer from 1 to 4,
a2 to a4 are each independently an integer from 0 to 20,
at least one of R 1 in the number of a1 is each independently an unsubstituted or substituted C 1 -C 60 alkyl group or an unsubstituted or substituted C 3 -C 10 cycloalkyl group,
two or more of a plurality of R 1 (s) are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 2 (s) are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 3 (s) are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 4 (s) are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
two or more of R 1a and R 1 to R 8 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 10a is the same as described in connection with R 2 ,
* and *′ each indicate a binding site to a neighboring atom,
a substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -Coo 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 with C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted, a C 7 -C 60 alkylaryl 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 alkylheteroaryl 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 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, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD 3 , -CD 2 H, -CDH 2 , —CF 3 , —CF 2

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Min Minsik
• Kim Sangmo
• Kang Hosuk
• Kim Wook
• Nam Sungho
• Bae Hyejin
• Son Jhunmo
• Jung Yongsik
• Chwae Jun

Classifications

• H10K85/346 Primary

  comprising platinum · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title