Organometallic compound, organic light-emitting device including organometallic compound, and apparatus including organometallic compound

Patent metadata

Field	Value
Publication number	US-12359120-B2
Application number	US-201916714608-A
Country	US
Kind code	B2
Filing date	Dec 13, 2019
Priority date	May 3, 2019
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

Provided are an organometallic compound represented by Formula 1, wherein in L 11 is a ligand represented by Formula 1-1, an organic light-emitting device including the organometallic compound, and an apparatus including the organometallic compound. The organic light-emitting device includes a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the organometallic compound.

M 11 (L 11 ) n11 (L 12 ) n12   Formula 1

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:
M 11 (L 11 ) n11 (L 12 ) n12   Formula 1

wherein, in Formula 1,
M 11 is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal,
L 11 is a ligand represented by Formula 1-1,
L 12 is selected from a monodentate ligand and a bidentate ligand,
n11 is 1, and
n12 is selected from 0, 1, and 2:

wherein, in Formula 1-1,
X 11 and X 12 are each independently N or C, provided that at least one selected from X 11 and X 12 is N,
Y 11 , Y 12 , Y 14 are each independently N or C,
Y 13 is C,
T 11 to T 14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 16 )(R 17 )—*′, *—Si(R 16 )(R 17 )—*′, *—B(R 16 )—*′, *—N(R 16 )—*′, and *—P(R 16 )—*′,
L 11 and L 12 are each independently selected from *—O—*′, *—S—*′, *—C(R 18 )(R 19 )—*′, *—C(R 18 )═*′, *=C(R 18 )—*′, *—C(R 18 )═C(R 19 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 18 )—*′, *—N(R 18 )—*′, *—P(R 18 )—*′, *—Si(R 18 )(R 19 )—*′, *—P(R 18 )(R 19 )*′, and *—Ge(R 18 )(R 19 )—*′, L 13 is selected from *—O—*′, *—S—*′, *—C(R 18 )(R 19 )—*′, *—C(R 18 )═*′, *=C(R 18 )*′, *—C(R 18 )(R 19 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 18 )—*′, *—P(R 18 )—*′, *—Si(R 18 )(R 19 )—*′, *—P(R 18 )(R 19 )—*′, and *—Ge(R 18 )(R 19 )*′,
a11 is selected from 0, 1, 2, and 3,
a12 and a13 are each independently selected from 1, 2, and 3, and when a11 is 0, (L 11 ) a11 is a single bond,
A 13 is a 6-membered N-containing heterocyclic group,
A 15 is an imidazole group,
A 11 is i) a first ring, ii) a condensed ring in which at least two first rings are condensed, or iii) a condensed ring in which at least one first ring and at least one second ring are condensed,
the first ring is selected from a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an oxazole group, a dihydrooxazole group, an isoxazole group, a dihydroisoxazole group, an oxadiazole group, a dihydrooxadiazole group, an isooxadiazole group, a dihydroisooxadiazole group, an oxatriazole group, a dihydrooxatriazole group, an isooxatriazole group, a dihydroisooxatriazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, a dihydroisothiazole group, a thiadiazole group, a dihydrothiadiazole group, an isothiadiazole group, a dihydroisothiadiazole group, a thiatriazole group, a dihydrothiatriazole group, an isothiatriazole group, a dihydroisothiatriazole group, a pyrazole group, a dihydropyrazole group, a triazole group, a dihydrotriazole group, a tetrazole group, a dihydrotetrazole group, an azasilole group, a diazasilole group, and a triazasilole group, and
the second ring is selected from a cyclohexane group, a cyclohexene group, a cyclohexadiene group, an adamantane group, a norbonane group, a norbonenegroup, a benzene group, a pyridine group, a dihydropyridine group, a tetrahydropyridine group, a pyrimidine group, a dihydropyrimidine group, a tetrahydropyrimidine group, a pyrazine group, a dihydropyrazine group, a tetrahydropyrazine group, a pyridazine group, a dihydropyridazine group, a tetrahydropyridazine group, a triazine group, a dihydrotriazine group, a tetrahydrotriazine group, and a triazinane group,
A 12 and A 14 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
R 11 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 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 7 -C 60 alkyl 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 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, —C(Q 1 )(Q 2 )(Q 3 ), —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 ), wherein two adjacent groups selected from R 11 to R 19 are optionally bound to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
R 12 to R 19 are each independently selected from 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 7 -C 60 alkyl 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 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, —C(Q 1 )(Q 2 )(Q 3 ), —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 ), wherein two adjacent groups selected from R 11 to R 19 are optionally bound to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, and
b11 is an integer from 3 to 10,
b12 to b15 are each independently an integer from 1 to 10, and
wherein 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 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 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 C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, a cyano

Assignees

• Samsung Display Co Ltd

Inventors

• Ahn Eunsoo
• Ko Soobyung
• Lee Hyunjung
• Jeon Mina
• Kim Sungbum
• Kim Haejin
• Shin Sujin
• Lee Eunyoung
• Lee Jaesung
• HAN Junghoon

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title