Near-infrared light-emitting diode and device including near-infrared light-emitting diode

Patent metadata

Field	Value
Publication number	US-11963437-B2
Application number	US-201916718062-A
Country	US
Kind code	B2
Filing date	Dec 17, 2019
Priority date	Jan 17, 2019
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

Provided are a near-infrared light-emitting diode including an osmium (Os)-containing organometallic compound and a device including the near-infrared light-emitting diode. The near-infrared light-emitting diode includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, where the organic layer includes a near-infrared light-emitting layer, the near-infrared light-emitting layer includes the osmium (Os)-containing organometallic compound.

First claim

What is claimed is:

1. A near-infrared light-emitting diode comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode,
wherein the organic layer comprises a near-infrared light-emitting layer, the near-infrared light-emitting layer comprises an osmium (Os)-containing organometallic compound, and the osmium (Os)-containing organometallic compound is configured to emit near-infrared light,
wherein the osmium (Os)-containing organometallic compound is represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2   Formula 1

wherein, in Formula 1,
M is Os,
L 1 is selected from ligands represented by Formula 1-1:

n1 is an integer from 1 to 4; and when n1 is 2 or greater, at least two L 1 (s) are identical to or different from each other,
L 2 is an organic ligand,
n2 is an integer from 0 to 4; and when n2 is 2 or greater, at least two L 2 (s) are identical to or different from each other,
i) at least two selected from L 1 (s) in the number of n1, ii) at least two selected from L 2 (s) in the number of n2, or iii) at least one selected from Li (s) in the number of n1 and at least one selected from L 2 (s) in the number of n2 are optionally bound via a single bond, a double bond, *═N—*′, *—N═*′, *═C[(L 3 ) a3 -(R 3 )]—*′, *—C[(L 3 ) a3 -(R 3 )]=*′, *—N[(L 3 ) a3 -(R 3 )]—*′, *—B(R 3 )—*′, *—P(R 3 )—*′, *—C(R 3 )(R 4 )—*′, *—Si(R 3 )(R 4 )—*′, *—Ge(R 3 )(R 4 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 3 )═*′, *═C(R 3 )—*′, *—C(R 3 )═C(R 4 )—*′, *—C(═S)—*′, or *—C≡C—*′ to form a tridentate ligand, a tetradentate ligand, a pentadentate ligand, or a hexadentate ligand, and * and *′ each indicate a binding site to an adjacent atom,
wherein, in Formula 1-1,
ring A 1 and ring A 2 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
Z 31 and Z 32 are each independently a covalent bond, a coordinate bond, O, S, C(R 7 )(R 8 ), Si(R 7 )(R 8 ), N(R 7 ), P(R 7 ), C(R 7 )(R 8 )(R 9 ), Si(R 7 )(R 8 )(R 9 ), N(R 7 )(R 8 ), or P(R 7 )(R 8 ),
X 1 and X 2 are each independently C or N,
ring A 1 and T 1 ; and T 1 and ring A 2 are each independently bound via a single bond or a double bond,
T 1 is a single bond, a double bond, *═N—*′, *—N═*′, *═C[(L 5 ) a5 -(R 5 )]—*′, *—C[(L 5 ) a5 -(R 5 )]═*′, *—N[(L 5 ) a5 -(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—*′, wherein * and *′ each indicate a binding site to an adjacent atom,
L 3 and L 5 are each independently a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10 , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10 ,
a3 and a5 are each independently an integer from 1 to 5,
R 1 to R 10 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O) 2 (Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
two adjacent groups selected from R 1 to R 10 are optionally bound 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 defined the same as R 10 ,
b1 and b2 are each independently an integer from 0 to 10,
* 1 and * 2 each indicate a binding site to M in Formula 1,
a bond between M and Z 31 or X 1 in Formula 1-1 and a bond between M and Z 32 or X 2 in Formula 1-1 are each independently a covalent bond or a coordinate bond, and
at least one 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 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -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 is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O) 2 (Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, a biphenyl group, and a terphenyl group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 het

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Myeongsuk
• Kang Sunwoo
• Ko Soobyung
• Ye Jimyoung
• Yoo Byeongwook
• Cho Illhun

Classifications

• H10K85/348 Primary

  comprising osmium · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title