Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11667659-B2
Application number	US-201916389289-A
Country	US
Kind code	B2
Filing date	Apr 19, 2019
Priority date	Apr 20, 2018
Publication date	Jun 6, 2023
Grant date	Jun 6, 2023

Abstract

An organometallic compound includes a hexadentate ligand bonded to a metal atom (M1). An energy level (E3MC) of a 3MC state (triplet metal centered state) of the organometallic compound is higher than an energy level (E3MLCT) of a 3MLCT state (triplet metal-to-ligand charge transfer state) of the organometallic compound.

First claim

What is claimed is:

1. An organic light-emitting device, comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode and including an emission layer,
wherein the organic layer includes an organometallic compound,
wherein the organometallic compound includes a hexadentate ligand bonded to a metal atom (M 1 ), and an energy level (E 3Mc ) of a 3 MC (triplet metal centered state) of the organometallic compound is higher than an energy level (E 3MLCT ) of a 3 MLCT (triplet metal-to-ligand charge transfer state) of the organometallic compound, and
wherein the organometallic compound is represented by Formula 1:

wherein, in Formulae 1, 2A, and 2B,
M 1 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 1 to A 6 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
L 1 to L 6 are each independently selected from a single bond, *—O—*′, *—C(R 1 )(R 2 )—*′, *—C(R 1 )═*′, *═C(R 1 )—*′, *—C(R 1 )═C(R 2 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C *′, *—N(R 1 )—*′, *—P(R 1 )—* 1 , *—Si(R 1 )(R 2 )—*′, *—P(R 1 )(R 2 )—*′, and *—Ge(R 1 )(R 2 )—*′,
a1, a3, and a5 are each independently selected from 1, 2, and 3,
a2, a4, and a6 are each independently selected from 0, 1, 2, and 3,
when a2 is 0, A 2 and A 3 are not linked,
when a4 is 0, A 4 and A 5 are not linked,
when a6 is 0, A 6 and A 1 are not linked,
Y 1 to Y 6 are each C,
T 1 to T 6 are each independently selected from a single bond, *—O—*′, and *—S—*′,
A 1 , A 3 , and A 5 are linked via a clipping linker represented by Formula 2A, or 2B,
X 1 is linked to X 10 in Formula 2A, or 2B,
X 2 is linked to X 20 in Formula 2A, or 2B,
X 3 is linked to X 30 in Formula 2A, or 2B,
Y 10 , Y 20 , and Y 30 , are each independently N or C(R 3 ), and when Y 10 , Y 20 , and Y 30 are each C(R 3 ), A 1 , A 3 , and A 5 is a 5-membered heterocyclic group; or a C 1 -C 60 condensed heteropolycyclic group including a 5-membered heterocyclic group,
Y 40 is N,
L 10 , L 20 , and L 30 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 4 )(R 5 )—*′, *—C(R 4 )═*′, *═C(R 4 )—*′, *—C(R 4 )═C(R 5 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 4 )—*′, *—N(R 4 )—*′, *—P(R 4 )—*′, *—Si(R 4 )(R 5 )—*′, *—P(R 4 )(R 5 )—*′, and *—Ge(R 4 )(R 5 )—*′,
a10, a20, and a30 are each independently selected from 0, 1, 2, 3, 4, and 5,
R 1 to R 5 , R 20 , R 30 , R 40 , R 50 , and R 60 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 hetero aryloxy group, a substituted or unsubstituted C 1 -C 60 hetero arylthio 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 ),
R 10 is 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, an 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 hetero aryloxy group, a substituted or unsubstituted C 1 -C 60 hetero arylthio 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 ),
when A 1 , A 3 , and A 5 are linked via a clipping linker represented by Formula 2B, R 30 and R 50 are each independently selected from —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, and Rio is selected from —F, —Cl, —Br, —I, a cyano group, an unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group,
R 1 and R 20 , R 1 and R 30 , R 1 and R 40 , R 1 and R 50 , or R 1 and R 60 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,
R 1 and R 10 are optionally linked to form an unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
b10, b20, b30, b40, b50, and b60 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
*and *′each indicate a binding site to a neighboring atom,
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, 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 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, 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 deuteri

Assignees

• Samsung Display Co Ltd

Inventors

• Kang Sunwoo
• Ko Soobyung
• Kim Taekyung
• Jeon Sangho
• Cho Youngmi

Classifications

• H10K85/371 Primary

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• C09K2211/185

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

• H10K85/342

  comprising iridium · CPC title

• H10K85/348

  comprising osmium · CPC title

• H10K85/346

  comprising platinum · CPC title