Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12096680-B2
Application number	US-201815868386-A
Country	US
Kind code	B2
Filing date	Jan 11, 2018
Priority date	Jul 14, 2017
Publication date	Sep 17, 2024
Grant date	Sep 17, 2024

Abstract

An organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the emission layer includes an organometallic compound of Formula 1. The organometallic compound of Formula 1 may be a phosphorescent dopant:

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,
M 11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
A 11 to A 14 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
Y 11 to Y 14 are each independently N or C,
Z 11 is N or B,
Ar 1 is a group represented by one selected from Formulae 40A, 40B, 41A, and 41B, wherein Ar 1 is bonded to Z 11 at least at X 41 or X 48 position:

and
wherein the Formulae 40A, 40B, 41A and 41B,
L 41 is selected from *—O—*′, *—S—*′, *—C(R 43 )(R 44 )−*′, *—B(R 43 )—*′, and *N(R 43 )—′,
provided that when L 41 is *—C(R 43 )(R 44 )—*′, or *—N(R 43 )—*′, R 43 and R 44 are not a phenyl group,
a41 is selected rom 1,2, and 3 ,
X 41 to X 48 are each independently C or N, and at least one of X 41 and X 48 is C, wherein when X 41 or X 48 correspond to a position at which Ar 1 is bonded to Z 11 , then the corresponding X 41 or X 48 is C,
R 41 to R 44 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted 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 group, a substituted or unsubstituted C 1 -C 10 heterocyloalkyl 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
wherein when a plurality of adjacent R 41 are linked, and/or when a plurality of adjacent R 42 are linked, the plurality of adjacent R 41 and the plurality of adjacent R 42 each independently form a group selected from:
a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group; and
a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine 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 hydrazino group, a hydrazono 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 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
provided that in Formulae 40B and 41B, at least two R 41 or at least two R 42 are linked,
b41 and b42 are each independently selected from 1, 2, 3, and 4, and
one selected from R 41 and R 42 is a binding site to Formula 1,
T11 to T14 are each independently selected from a single bond, O, and S,
L 11 to L 13 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 15 )(R 16 )—*′, *—C(R 15 )=*′, *=C(R 15 )—*′, *—C(R 15 )═C(R 16 )—*′, *—C(═O)—*′, *—C(=S)—*′, *—C═C—*′, *—B(R 15 )—*′, *—N(R 15 )—*′, *—P(R 15 )—*′, *—Si(R 15 )(R 16 )—*′, *—P(R 15 )(R 16 )—* ′, and *—Ge(R 15 )(R 16 )—*′, and
a11 to a13 are each independently selected from 0, 1, 2, and 3, and
wherein when a11 is 0, A 11 and A 12 are not linked to each other; when a12 is 0, A 12 and A 13 are not linked to each other; and when a13 is 0, A 13 and A 14 are not linked to each other,
R 11 to R 16 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
provided that, when Y 12 is N, R 12 is not —Si(Q 1 )(Q 2 )(Q 3 ), and
when Y 13 is N, R 13 is not —Si(Q 1 )(Q 2 )(Q 3 ),
R 15 and R 11 , R 15 and R 12 , R 15 and R 13 , and R 15 and R 14 are each independently optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, R 15 and R 16 are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
b11 to b14 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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 C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
and *′ each indicate a binding site to a neighboring atom.

2. The organometallic compound of claim 1 , wherein M 11 is selected from Pt, Pd, Cu, Ag, and Au.

3. The organometallic compound of claim 1 , wherein
A 11 to A 14 are each independently selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indeno pyridine group, an indolopyridine grou

Assignees

• Samsung Display Co Ltd

Inventors

• Jeon Mina
• Ko Soobyung
• Kim Sungbum
• Ahn Heechoon
• Jun Mieun
• Kim Youngkook
• Hwang Seokhwan

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/00

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title

• H10K85/346 Primary

  comprising platinum · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title