US20230371359A1 - Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device - Google Patents

Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device Download PDF

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US20230371359A1
US20230371359A1 US18/348,775 US202318348775A US2023371359A1 US 20230371359 A1 US20230371359 A1 US 20230371359A1 US 202318348775 A US202318348775 A US 202318348775A US 2023371359 A1 US2023371359 A1 US 2023371359A1
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Kyuyoung HWANG
Byungjoon Kang
Seungyeon Kwak
Myungsun SIM
Kum Hee LEE
Aram JEON
Byoungki CHOI
Hyeonho CHOI
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Samsung Electronics Co Ltd
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    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
  • Organic light-emitting devices are self-emission devices, which have better characteristics in terms of a viewing angle, response time, brightness, driving voltage, and response speed, and produce full-color images.
  • an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer.
  • a hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode.
  • Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region.
  • the holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
  • aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1 below:
  • an organic light-emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer including at least one organometallic compound.
  • the organometallic compound may be included in the emission layer of the organic layer and the organometallic compound included in the emission layer may act as a dopant.
  • Another aspect of the present disclosure provides an electronic apparatus including the organic light-emitting device.
  • FIGURE is a schematic view of an organic light-emitting device according to an embodiment.
  • relative terms such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures
  • the exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the FIGURE
  • the exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.
  • “About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ⁇ 30%, 20%, 10% or 5% of the stated value.
  • Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1 below:
  • M in Formula 1 may be a transition metal.
  • M may be a first-row transition metal, a second-row transition metal, or a third-row transition metal, of the Periodic Table of Elements.
  • M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
  • M may be Ir, Pt, Os, or Rh.
  • L 1 in Formula 1 may be a ligand represented by Formula 2A, and n1 in Formula 1 indicates the number of L 1 (s) in Formula 1 and may be 1 or 2. When n1 is two, two L 1 (s) may be identical to or different from each other.
  • L 2 in Formula 1 may be a ligand represented by Formula 2B, and n2 in Formula 1 indicates the number of L 2 (s) in Formula 1 and may be 1 or 2. When n2 is two, two L 2 (s) may be identical to or different from each other:
  • L 1 and L 2 in Formula 1 may be different from each other. That is, the organometallic compound represented by Formula 1 may be a heteroleptic complex.
  • M may be Ir, and the sum of n1 and n2 may be 3; or M may be Pt, and the sum of n1 and n2 may be 2.
  • Y 1 and Y 4 in Formulae 2A and 2B may each independently be C or N.
  • Y 1 in Formula 2A may be N and Y 4 in Formula 2B may be C.
  • X 1 in Formula 2B may be Si or Ge.
  • X 21 in Formula 2A may be O, S, S( ⁇ O), N(Z 29 ), C(Z 29 )(Z 30 ), or Si(Z 29 )(Z 30 ).
  • Z 29 and Z 30 will be understood by referring to a detailed description thereof to be provided later.
  • X 21 in Formula 2A may be O or S.
  • T 1 to T 4 may each independently be C, N, carbon linked to ring CY 1 , or carbon linked to M in Formula 1, wherein one of T 1 to T 4 may be carbon linked to M in Formula 1, and one of the remaining T 1 to T 4 that are not linked to M in Formula 1 may be carbon linked to ring CY 1 , and ii) T 5 to T 8 may each independently be C or N.
  • T 1 in Formula 2B when X 1 in Formula 2B is Si, at least one of the remaining T 1 to T 8 that are not carbon linked to M and ring CY 1 may be N.
  • X 1 in Formula 2B may be Si, and at least one of the remaining T 1 to T 8 that are not carbon linked to M and ring CY 1 in Formula 2A may be N.
  • X 1 in Formula 2B may be Ge, and T 1 to T 8 in Formula 2A may be C.
  • X 1 in Formula 2B may be Ge, and at least one of the remaining T 1 to T 8 that are not carbon linked to M and ring CY 1 in Formula 2A may be N.
  • T 8 in Formula 2A may be N.
  • Ring CY 1 and ring CY 14 in Formulae 2A and 2B may each independently be a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group.
  • ring CY 1 and ring CY 14 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed with each other, iv) a condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other.
  • the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasil
  • the second ring may be an admantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
  • ring CY 1 and ring CY 14 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, 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 thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene
  • ring CY 1 and ring CY 14 may each independently be a benzene group, a naphthalene group, 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.
  • ring CY 1 in Formula 2A may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
  • ring CY 14 in Formula 2B may be a benzene group, a naphthalene group, 1,2,3,4-tetrahydronaphthalene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.
  • R 21 to R 23 may each independently be a C 1 -C 60 alkyl group or a C 6 -C 60 aryl group, each unsubstituted or 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 1 -C 60 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, or any combination thereof.
  • R 21 to R 23 in Formula 2B may each independently be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group
  • R 21 to R 23 may each independently be —CH 3 , —CH 2 CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CD 3 , or —CD 2 CH 3 .
  • R 21 to R 23 in Formula 2B may be identical to each other.
  • At least two of R 21 to R 23 may be different from each other.
  • Z 1 , Z 2 , and R 11 to R 14 in Formulae 2A and 2B may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 alky
  • a1 and b1 indicate the number of Z 1 (s) and the number of R 14 (s), respectively, and may each independently be an integer from 0 to 20.
  • a1 is two or more, two or more Z 1 (s) may be identical to or different from each other, and when b1 is two or more, two or more R 14 (s) may be identical to or different from each other.
  • a1 and b1 may each independently be an integer from 0 to 10.
  • a2 indicates the number of Z 2 (s) and may each independently be an integer from 0 to 6. When a2 is two or more, two or more Z 2 (s) may be identical to or different from each other. For example, a2 may each independently be 0, 1, 2 or 3.
  • Z 1 in Formula 2A may be hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, or a substituted or unsubstituted C 3 -C 10 cycloalkyl group.
  • Z 2 and R 11 to R 14 in Formulae 2A and 2B may each independently be:
  • Q 1 to Q 9 may each independently be:
  • a number of carbon included in R 12 of Formula 2B may be at least two.
  • R 12 in Formula 2B may be:
  • R 12 in Formula 2B may be:
  • the organometallic compound represented by Formula 1 may satisfy at least one of Condition (1) to Condition (3) below:
  • Z 1 is not hydrogen, and a1 is an integer of 1 to 20.
  • R 14 is not hydrogen, and b1 is an integer of 1 to 20.
  • Z 2 is not hydrogen, and a2 is an integer of 1 to 6.
  • the organometallic compound represented by Formula 1 may include at least one deuterium, at least one fluoro group (—F), at least one cyano group (—CN), or any combination thereof.
  • the organometallic compound represented by Formula 1 may include at least one deuterium.
  • the organometallic compound represented by Formula 1 may satisfy at least one of Condition A to Condition I below:
  • Z 1 is not hydrogen
  • a1 is an integer of 1 to 20
  • at least one of Z 1 (s) in the number of a1 includes deuterium.
  • Z 2 is not hydrogen
  • a2 is an integer of 1 to 6
  • at least one of Z 2 (s) in the number of a2 includes deuterium.
  • Z 2 is not hydrogen
  • a2 is an integer of 1 to 6
  • at least one of Z 2 (s) in the number of a2 includes —F.
  • Z 2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z 2 (s) in the number of a2 includes —CN.
  • Z 2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z 2 (s) in the number of a2 is a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
  • At least one of R 21 to R 23 includes deuterium.
  • R 12 includes deuterium.
  • R 14 is not hydrogen
  • b1 is an integer of 1 to 20
  • at least one of R 14 (s) in the number of b1 includes deuterium.
  • R 14 is not hydrogen
  • b1 is an integer of 1 to 20
  • at least one of R 14 (s) in the number of b1 includes —F.
  • Z 2 in Formula 2A may not be hydrogen, a2 may be an integer from 1 to 3, and at least one of Z 2 (s) in number of a2 may each independently be a substituted or unsubstituted C 1 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed polycycl
  • Z 2 in Formula 2A may not be hydrogen, a2 may be an integer from 1 to 3, and at least one of Z 2 (s) in number of a2 may each independently be a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
  • Z 1 in Formula 2A may be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , —OCH 3 , —OCDH 2 , —OCD 2 H, —OCD 3 , —SCH 3 , —SCDH 2 , —SCD 2 H, —SCD 3 , one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae
  • Z 2 and R 11 to R 14 in Formulae 2A and 2B may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , —OCH 3 , —OCDH 2 , —OCD 2 H, —OCD 3 , —SCH 3 , —SCDH 2 , —SCD 2 H, —SCD 3 , one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted
  • R 12 in Formula 2B may be one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-1 to 10-132, one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-201 to 10-353, one of groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted
  • groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium and “groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium” as used herein may be, for example, groups represented by Formulae 9-501 to 9-514 and 9-601 to 9-635:
  • groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F and “groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F” as used herein may be, for example, groups represented by Formulae 9-701 to 9-710:
  • groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium and “groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium” as used herein may be, for example, groups represented by Formulae 10-501 to 10-553:
  • groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F and “groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F” as used herein may be, for example, groups represented by Formulae 10-601 to 10-620:
  • two or more of R 21 to R 23 may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a
  • two or more of a plurality of Z 1 (s) may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a
  • iii) two or more of a plurality of Z 2 (s) may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubsub
  • R 10a may be the same as defined in connection with R 14 in the present specification.
  • Formula 2A may be a group represented by one of Formulae CY1-1 to CY1-28:
  • Formula 2A may be a group represented by one of Formulae CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.
  • Formula 2A may be a group represented by one of Formulae CY2-1 to CY2-6:
  • Formula 2A may be a group represented by one of Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065 and CY2-6001 to CY2-6065:
  • Formula 2B may be a group represented by one of Formulae CY14-1 to CY14-64:
  • Formula 2B may be a group represented by one of Formulae CY14(1) to CY14(63):
  • the organometallic compound may be represented by Formula 1A:
  • T 13 in Formula 1A may be C(Z 13 ) and Z 13 may not be a hydrogen.
  • the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1 or 2.
  • the organometallic compound may be one of Compounds 1 to 1620:
  • OMe indicates a methoxy group.
  • L 1 of the organometallic compound represented by Formula 1 may be a ligand represented by Formula 2A, and n1 which indicates the number of L 1 (s) may be 1 or 2.
  • L 2 of the organometallic compound represented by Formula 1 may be a ligand represented by Formula 2B, and n2 which indicates the number of L 2 (s) may be 1 or 2.
  • L 1 and L 2 are different from each other. That is, the organometallic compound may be a heteroleptic complex essentially including, as ligands linked to metal M, at least one ligand represented by Formula 2A and at least one ligand represented by Formula 2B.
  • a group represented by *—X 1 (R 21 )(R 22 )(R 23 ) in Formula 1 may be linked to the fifth position of a pyridine ring in a ligand represented by Formula 2B (see Formula 2B). Accordingly, the organometallic compound including the ligand represented by Formula 2B may have excellent heat resistance and degradation resistance so that an electronic device, for example, an organic light-emitting device, including the organometallic compound may have high stability and long lifespan in production, storage, and/or operation.
  • an electronic device for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved driving voltage and roll-off ratio.
  • R 21 to R 23 , Z 1 , Z 2 , and R 1 to R 14 do not each include a silicon (Si). Accordingly, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved out-coupling characteristics.
  • R 12 in Formula 2B is not hydrogen nor a methyl group.
  • the organometallic compound represented by Formula 1 may emit light that is shifted toward relatively shorter wavelengths, for example, blue light, green light, or greenish blue light, and an electronic device, for example, an organic light-emitting device, including the organometallic compound may have an excellent out-coupling effect, thereby having high luminescence efficiency.
  • a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a singlet (Si) energy level, and a triplet (T 1 ) energy level of some compounds of the organometallic compound represented by Formula 1 are evaluated by a density functional theory (DFT) of Gaussian program with molecular structure optimization based on B3LYP, and results are shown in Table 1.
  • DFT density functional theory
  • the organometallic compound represented by Formula 1 has such electrical characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
  • Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.
  • the organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer.
  • an organic light-emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.
  • the organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high external quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.
  • the organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device.
  • the organometallic compound represented by Formula 1 may be included in the emission layer.
  • the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
  • the emission layer may emit, for example, green light or blue light.
  • (an organic layer) includes at least one of the organometallic compound” as used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
  • the organic layer may include, as the organometallic compound, only Compound 1.
  • Compound 1 may exist only in the emission layer of the organic light-emitting device.
  • the organic layer may include, as the organometallic compound, Compound 1 and Compound 2.
  • Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).
  • the first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode
  • the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof
  • the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • organic layer refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device.
  • the “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
  • FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment.
  • the organic light-emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.
  • a substrate may be additionally disposed under the first electrode 11 or above the second electrode 19 .
  • the substrate any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate.
  • the first electrode 11 may be an anode.
  • the material for forming the first electrode 11 may include a material(s) with a high work function to facilitate hole injection.
  • the first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode.
  • the material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO).
  • the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
  • metal such as magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
  • the first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers.
  • the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
  • the organic layer 15 is disposed on the first electrode 11 .
  • the organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
  • the hole transport region may be disposed between the first electrode 11 and the emission layer.
  • the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
  • the hole transport region may include only either a hole injection layer or a hole transport layer.
  • the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11 .
  • the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
  • suitable methods for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
  • the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer.
  • the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10 ⁇ 8 to about 10 ⁇ 3 torr, and a deposition rate of about 0.01 ⁇ /sec to about 100 ⁇ /sec.
  • the deposition conditions are not limited thereto.
  • coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer.
  • a coating speed may be from about 2,000 rpm to about 5,000 rpm
  • a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C.
  • the coating conditions are not limited thereto.
  • Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
  • the hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, R-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4′′-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonicacid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:
  • Ar 101 to Ar 102 in Formula 201 may each independently be:
  • xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may be 0, 1 or 2.
  • xa may be 1 and xb may be 0.
  • R 101 to R 108 , R 111 to R 119 , and R 121 to R 124 in Formulae 201 and 202 may each independently be:
  • R 109 in Formula 201 may be:
  • the compound represented by Formula 201 may be represented by Formula 201A below:
  • R 101 , R 111 , R 112 , and R 109 in Formula 201A are the same as described above.
  • the hole transport region may include at least one of compounds HT1 to HT20 illustrated below:
  • a thickness of the hole transport region may be from about 100 ⁇ to about 10,000 ⁇ , for example, about 100 ⁇ to about 1,000 ⁇ .
  • a thickness of the hole injection layer may be in a range of about 100 ⁇ to about 10000 ⁇ , for example, about 100 ⁇ to about 1,000 ⁇
  • a thickness of the hole transport layer may be in a range of about 50 ⁇ to about 2,000 ⁇ , for example about 100 ⁇ to about 1,500 ⁇ .
  • the hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties.
  • the charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
  • the charge-generation material may be, for example, a p-dopant.
  • the p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.
  • Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ) and F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1 below:
  • the hole transport region may include a buffer layer.
  • the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
  • a material for the electron blocking layer may be materials for the hole transport region described above, materials for a host to be explained later, or any combination thereof.
  • the material for the electron blocking layer is not limited thereto.
  • a material for the electron blocking layer may be mCP, which will be explained later.
  • an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like.
  • the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.
  • the emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
  • the host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compounds H50, Compound H51, Compound H52, or any combination thereof:
  • the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer.
  • the emission layer may emit white light.
  • an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
  • a thickness of the emission layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , for example, about 200 ⁇ to about 600 ⁇ . When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
  • an electron transport region may be disposed on the emission layer.
  • the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure.
  • the electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
  • Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
  • the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof:
  • a thickness of the hole blocking layer may be from about 20 ⁇ to about 1,000 ⁇ , for example, about 30 ⁇ to about 600 ⁇ . When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a substantial increase in driving voltage.
  • the electron transport layer may include BCP, Bphen, Alq 3 , BAlq, TAZ, NTAZ, or any combination thereof:
  • the electron transport layer may include at least one of ET1 to ET25:
  • a thickness of the electron transport layer may be from about 100 ⁇ to about 1,000 ⁇ , for example, about 150 ⁇ to about 500 ⁇ . When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
  • the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
  • the metal-containing material may include a Li complex.
  • the Li complex may include, for example, Compound ET-D1 (LiQ), Compound ET-D2, or combination thereof:
  • the electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.
  • the electron injection layer may include LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.
  • a thickness of the electron injection layer may be from about 1 ⁇ to about 100 ⁇ , for example, about 3 ⁇ to about 90 ⁇ . When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without substantial increase in driving voltage.
  • the second electrode 19 is disposed on the organic layer 15 .
  • the second electrode 19 may be a cathode.
  • a material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
  • lithium (Li), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be formed as the material for forming the second electrode 19 .
  • a transmissive electrode formed using ITO or IZO may be used as the second electrode 19 .
  • the organic light-emitting device may be included in an electronic apparatus. Accordingly, provided is an electronic apparatus including the organic light-emitting device.
  • the electronic apparatus may include, for example, a display, an illuminator, and a sensor.
  • Another aspect of the present disclosure provides a diagnostic composition including at least one of the organometallic compound represented by Formula 1.
  • the organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
  • the diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
  • C 1 -C 60 alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms
  • C 1 -C 60 alkylene group refers to a divalent group having the same structure as the C 1 -C 60 alkyl group.
  • Non-limiting examples of the C 1 -C 60 alkyl group, the C 1 -C 20 alkyl group, and/or the C 1 -C 10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group,
  • C 1 -C 60 alkoxy group refers to a monovalent group represented by —OA 101 (wherein A 101 is the C 1 -C 60 alkyl group).
  • a 101 is the C 1 -C 60 alkyl group.
  • Non-limiting examples of the C 1 -C 60 alkoxy group, the C 1 -C 20 alkoxy group, or the C 1 -C 10 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
  • C 2 -C 6 alkenyl group refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C 2 -C 60 alkenyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group.
  • C 2 -C 60 alkenylene group refers to a divalent group having the same structure as the C 2 -C 60 alkenyl group.
  • C 2 -C 60 alkynyl group refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C 2 -C 60 alkynyl group, and examples thereof include an ethynyl group, and a propynyl group.
  • C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
  • C 3 -C 10 cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms
  • C 3 -C 10 cycloalkylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
  • Non-limiting examples of the C 3 -C 10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (a norbornyl group), and a bicyclo[2.2.2]octyl group.
  • C 1 -C 10 heterocycloalkyl group refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms
  • C 1 -C 10 heterocycloalkylene group refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkyl group.
  • Non-limiting examples of the C 1 -C 10 heterocycloalkyl group include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
  • C 3 -C 10 cycloalkenyl group refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
  • C 3 -C 10 cycloalkenylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.
  • C 2 -C 10 heterocycloalkenyl group refers to a monovalent monocyclic group that has at least one N, O, P, Si, B, Ge, Se, S, or any combination thereof as a ring-forming atom, 2 to 10 carbon atoms, and at least one double bond in its ring.
  • Examples of the C 2 -C 10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.
  • C 2 -C 10 heterocycloalkenylene group refers to a divalent group having the same structure as the C 2 -C 10 heterocycloalkenyl group.
  • C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms
  • C 6 -C 60 arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms.
  • Non-limiting examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group.
  • the C 6 -C 60 aryl group and the C 6 -C 60 arylene group each include two or more rings, the rings may be fused to each other.
  • C 7 -C 60 alkylaryl group refers to a C 6 -C 59 arylene group substituted with at least one C 1 -C 54 alkyl group.
  • C 1 -C 6 heteroaryl group refers to a monovalent group having a heterocyclic aromatic system that has at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, in addition to 1 to 60 carbon atoms.
  • C 1 -C 60 heteroarylene group refers to a divalent group having a heterocyclic aromatic system that has at least one heteroatom N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, in addition to 1 to 60 carbon atoms.
  • Non-limiting examples of the C 1 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
  • the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group each include two or more rings, the rings may be fused to each other.
  • C 2 -C 60 alkylheteroaryl group refers to a C 1 -C 59 heteroarylene group substituted with at least one C 1 -C 59 alkyl group.
  • C 6 -C 60 aryloxy group used herein indicates —OA 102 (wherein A 102 is the C 6 -C 60 aryl group), a C 6 -C 60 arylthio group used herein indicates —SA 103 (wherein A 103 is the C 6 -C 60 aryl group), and a C 1 -C 60 alkylthio group used herein indicates —SA 104 (wherein A 104 is the C 1 -C 60 alkyl group).
  • the term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure.
  • Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group.
  • divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
  • the term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure.
  • Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group.
  • divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
  • C 5 -C 30 carbocyclic group refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only.
  • the C 5 -C 30 carbocyclic group may be a monocyclic group or a polycyclic group.
  • C 5 -C 30 carbocyclic group (which is unsubstituted or substituted with at least one R 10a )” may include, for example, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (a norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, and a fluorene group
  • C 1 -C 30 heterocyclic group refers to a saturated or unsaturated cyclic group having, as a ring forming atom, at least one N, O, P, Si, Se, Ge, B, S, or any combination thereof other than 1 to 30 carbon atoms.
  • the C 1 -C 30 heterocyclic group may be a monocyclic group or a polycyclic group.
  • the “C 1 -C 30 heterocyclic group (which is unsubstituted or substituted with at least one R 10a )” may include, for example, a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzo
  • (C 1 -C 20 alkyl)‘X’ group refers to a ‘X’ group substituted with at least one C 1 -C 20 alkyl group.
  • the term “(C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group” as used herein refers to a C 3 -C 10 cycloalkylene group substituted with at least one C 1 -C 20 alkyl group and the term “(C 1 -C 20 alkyl)phenyl group” as used herein refers to a phenylene group substituted with at least one C 1 -C 20 alkyl group.
  • An example of a (C 1 alkyl)phenyl group is a toluyl group.
  • Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; 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 unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; 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
  • Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 may each independently be
  • Compound 125A (1.6 g, 1.0 mmol) was mixed with 45 ml of methylene chloride (MC), and a mixture of AgOTf (Silver trifluoromethanesulfonate) (0.5 g, 2.1 mmol) and 15 ml of methanol was added thereto. Afterwards, the mixed solution was stirred at room temperature for 18 hours while blocking the light with aluminum foil. The resulting solution was then filtered through celite to remove a solid produced therefrom, and the solvent was removed from the filtrate under reduced pressure, and a solid (Compound 125B) produced therefrom was used in the next reaction without additional purification.
  • MC methylene chloride
  • Compound 163B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 163A was used instead of Compound 125A. Compound 163B thus obtained was used in the next reaction without additional purification.
  • Compound 505B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 505A was used instead of Compound 125A. Compound 505B thus obtained was used in the next reaction without additional purification.
  • Compound 526B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 526A was used instead of Compound 125A. Compound 526B thus obtained was used in the next reaction without additional purification.
  • Compound 806B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 806A was used instead of Compound 125A. Compound 806B thus obtained was used in the next reaction without additional purification.
  • Compound 1365B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1365A was used instead of Compound 125A. Compound 1365B thus obtained was used in the next reaction without additional purification.
  • Compound 1497B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1497A was used instead of Compound 125A. Compound 1497B thus obtained was used in the next reaction without additional purification.
  • Compound 1505B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1505A was used instead of Compound 125A. Compound 1505B thus obtained was used in the next reaction without additional purification.
  • a glass substrate on which ITO/Ag/ITO was formed to a thickness of 70 ⁇ /1,000 ⁇ /70 ⁇ was cut to a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then, cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the anode was provided to a vacuum deposition apparatus.
  • 2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 ⁇
  • NPB 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • CBP as a host
  • Compound 125 as a dopant
  • BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 ⁇
  • Alq 3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 ⁇ .
  • LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ⁇
  • Mg and Ag were co-deposited at a weight ratio of 90:10 on the electron injection layer to form a cathode having a thickness of 120 ⁇ , thereby completing the manufacture of an organic light-emitting device.
  • Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds listed in Table 2 below were each used as a dopant instead of Compound 125 in forming an emission layer.
  • the driving voltage, maximum external quantum efficiency (Max EQE) value (%), and lifespan (LT 97 , hr) of the organic light-emitting devices manufactured according to Examples 1 to 12 and Comparative Examples A and B were evaluated, and results thereof are shown in Table 2.
  • a current-voltage meter Kelvin 2400
  • a luminance meter Minolta Cs-1000A
  • the lifespan (LT 97 ) (at 3,500 nit) obtained by evaluating time (hr) that lapsed when luminance was 97% of initial luminance (100%), and was indicated in a relative value (%).
  • the organic light-emitting device manufactured according to Examples 1 to 12 had a comparable value of driving voltage and improved external quantum efficiency and longer lifespan characteristics, as compared with the organic light-emitting device manufactured according to Comparative Examples A and B.
  • the organometallic compound has excellent electronic characteristics and heat resistance, and thus, an electronic device, for example, an organic light-emitting device, including the organometallic compound may have good driving voltage, good external quantum efficiency, and good lifespan characteristics.
  • an electronic device for example, an organic light-emitting device, including the organometallic compound may have good driving voltage, good external quantum efficiency, and good lifespan characteristics.
  • a diagnostic composition including the organometallic compound may be provided with a high diagnosis efficiency.

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Abstract

Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus comprising the organic light-emitting device:M(L1)n1(L2)n2  Formula 1wherein, in Formula 1, M, L1, L2, n1, and n2 are the same as described in the detailed description of the specification.

Description

    CROSS-REFERENCE TO RELATED APPLICATION
  • This is a continuation application of U.S. application Ser. No. 16/808,605, filed on Mar. 4, 2020, which claims priority to and the benefit of Korean Patent Applications No. 10-2019-0026320, filed on Mar. 7, 2019, and 10-2020-0026887, filed on Mar. 4, 2020, in the Korean Intellectual Property Office, the contents of which are incorporated herein in their entirety by reference.
    • BACKGROUND 1. Field
  • One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
    • 2. Description of the Related Art
  • Organic light-emitting devices are self-emission devices, which have better characteristics in terms of a viewing angle, response time, brightness, driving voltage, and response speed, and produce full-color images.
  • In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
    • SUMMARY
  • Aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
  • Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1 below:

  • M(L1)n1(L2)n2.  Formula 1
  • In Formula 1,
      • M may be a transition metal,
      • L1 may be a ligand represented by Formula 2A,
      • L2 may be a ligand represented by Formula 2B,
      • n1 and n2 may each independently be 1 or 2, wherein, when n1 is 2, two L1(s) may be identical to or different from each other and when n2 is 2, two L2(s) may be identical to or different from each other,
      • the sum of n1 and n2 may be 2 or 3, and
      • L1 to L2 may be different from each other:
  • Figure US20230371359A1-20231116-C00001
  • In Formulae 2A and 2B,
      • Y1 and Y4 may each independently be C or N,
      • X1 may be Si or Ge,
      • X21 may be O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30),
      • T1 to T4 may each independently be C, N, carbon linked to ring CY1, or carbon linked to M in Formula 1, wherein one of T1 to T4 may be carbon linked to M in Formula 1, and one of the remaining T1 to T4 that are not linked to M in Formula 1 may be carbon linked to ring CY1,
      • T5 to T8 may each independently be C or N,
      • when X1 is Si, at least one of the remaining T1 to T8 that are not carbon linked to M and ring CY1 may be N,
      • ring CY1 and ring CY14 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
      • R21 to R23 may each independently be a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or any combination thereof,
      • Z1, Z2, and R11 to R14 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9) or —P(Q8)(Q9), wherein R12 is neither hydrogen nor a methyl group,
      • a1 and b1 may each independently be an integer from 0 to 20, wherein, when a1 is 2 or more, two or more Z1(s) may be identical or different, and when b1 is 2 or more, two or more R14(s) may be identical or different,
      • a2 may be an integer from 0 to 6, wherein, when a2 is 2 or more, two or more Z2(s) may be identical to or different from each other,
      • two or more of R21 to R23 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of a plurality of Z1(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of a plurality of Z2(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • R12 and R13 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of a plurality of R14(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of Z1, Z2 and R11 to R14 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • R10a may be the same as defined in connection with R14,
      • * and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1,
      • a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
      • deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
      • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
      • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
      • —N(Q31)(Q32), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39) or —P(Q38)(Q39); or any combination thereof,
      • Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; 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 C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
  • Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer including at least one organometallic compound.
  • The organometallic compound may be included in the emission layer of the organic layer and the organometallic compound included in the emission layer may act as a dopant.
  • Another aspect of the present disclosure provides an electronic apparatus including the organic light-emitting device.
    • BRIEF DESCRIPTION OF THE DRAWING
  • These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.
    •  DETAILED DESCRIPTION
  • Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
  • It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present
  • It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.
  • The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.
  • “Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
  • Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the FIGURE Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.
  • “About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.
  • Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
  • Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1 below:

  • M(L1)n1(L2)n2.  Formula 1
  • M in Formula 1 may be a transition metal.
  • For example, M may be a first-row transition metal, a second-row transition metal, or a third-row transition metal, of the Periodic Table of Elements.
  • For example, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
  • In one or more embodiments, M may be Ir, Pt, Os, or Rh.
  • L1 in Formula 1 may be a ligand represented by Formula 2A, and n1 in Formula 1 indicates the number of L1(s) in Formula 1 and may be 1 or 2. When n1 is two, two L1(s) may be identical to or different from each other.
  • L2 in Formula 1 may be a ligand represented by Formula 2B, and n2 in Formula 1 indicates the number of L2(s) in Formula 1 and may be 1 or 2. When n2 is two, two L2(s) may be identical to or different from each other:
  • Figure US20230371359A1-20231116-C00002
  • Formulae 2A and 2B will be understood by referring to a detailed description thereof to be provided later.
  • L1 and L2 in Formula 1 may be different from each other. That is, the organometallic compound represented by Formula 1 may be a heteroleptic complex.
  • In one or more embodiments, M may be Ir, and the sum of n1 and n2 may be 3; or M may be Pt, and the sum of n1 and n2 may be 2.
  • Y1 and Y4 in Formulae 2A and 2B may each independently be C or N.
  • For example, Y1 in Formula 2A may be N and Y4 in Formula 2B may be C.
  • X1 in Formula 2B may be Si or Ge.
  • X21 in Formula 2A may be O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30). Z29 and Z30 will be understood by referring to a detailed description thereof to be provided later.
  • For example, X21 in Formula 2A may be O or S.
  • In Formula 2A, i) T1 to T4 may each independently be C, N, carbon linked to ring CY1, or carbon linked to M in Formula 1, wherein one of T1 to T4 may be carbon linked to M in Formula 1, and one of the remaining T1 to T4 that are not linked to M in Formula 1 may be carbon linked to ring CY1, and ii) T5 to T8 may each independently be C or N.
  • In Formula 1, when X1 in Formula 2B is Si, at least one of the remaining T1 to T8 that are not carbon linked to M and ring CY1 may be N.
  • In one or more embodiments, X1 in Formula 2B may be Si, and at least one of the remaining T1 to T8 that are not carbon linked to M and ring CY1 in Formula 2A may be N.
  • In one or more embodiments, X1 in Formula 2B may be Ge, and T1 to T8 in Formula 2A may be C.
  • In one or more embodiments, X1 in Formula 2B may be Ge, and at least one of the remaining T1 to T8 that are not carbon linked to M and ring CY1 in Formula 2A may be N.
  • In one or more embodiments, T8 in Formula 2A may be N.
  • Ring CY1 and ring CY14 in Formulae 2A and 2B may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
  • For example, ring CY1 and ring CY14 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed with each other, iv) a condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other.
  • The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group.
  • The second ring may be an admantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
  • In one or more embodiments, in Formulae 2A and 2B, ring CY1 and ring CY14 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, 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 thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an admantane group, a norbornane group, or a norbornene group.
  • In one or more embodiments, ring CY1 and ring CY14 may each independently be a benzene group, a naphthalene group, 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.
  • In one or more embodiments, ring CY1 in Formula 2A may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
  • In one or more embodiments, ring CY14 in Formula 2B may be a benzene group, a naphthalene group, 1,2,3,4-tetrahydronaphthalene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.
  • In Formula 2B, R21 to R23 may each independently be a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or any combination thereof.
  • For example, R21 to R23 in Formula 2B may each independently be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or any combination thereof.
  • In one or more embodiments, R21 to R23 may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, or —CD2CH3.
  • In one or more embodiments, R21 to R23 in Formula 2B may be identical to each other.
  • In one or more embodiments, at least two of R21 to R23 may be different from each other.
  • Z1, Z2, and R11 to R14 in Formulae 2A and 2B may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9) or —P(Q8)(Q9), and R12 may be neither hydrogen nor a methyl group. Q1 to Q9 may be the same as described in this disclosure.
  • In Formulae 2A and 2B, a1 and b1 indicate the number of Z1(s) and the number of R14(s), respectively, and may each independently be an integer from 0 to 20. When a1 is two or more, two or more Z1(s) may be identical to or different from each other, and when b1 is two or more, two or more R14(s) may be identical to or different from each other. For example, a1 and b1 may each independently be an integer from 0 to 10.
  • In Formula 2A, a2 indicates the number of Z2(s) and may each independently be an integer from 0 to 6. When a2 is two or more, two or more Z2(s) may be identical to or different from each other. For example, a2 may each independently be 0, 1, 2 or 3.
  • In one or more embodiments, Z1 in Formula 2A may be hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, or a substituted or unsubstituted C3-C10 cycloalkyl group.
  • In one or more embodiments, in Formula 2A,
      • Z1 may be:
      • hydrogen, deuterium, —F, or a cyano group;
      • a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, or any combination thereof; or
      • a C3-C10 cycloalkyl group or a C1-C10 heterocycloalkyl group, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, or any combination thereof.
  • In one or more embodiments, in Formula 2A,
      • Z1 may be:
      • hydrogen, deuterium, —F, or a cyano group;
      • a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, or a bicyclo[2.2.2]octyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, or any combination thereof.
  • In one or more embodiments, Z2 and R11 to R14 in Formulae 2A and 2B may each independently be:
      • hydrogen, deuterium, —F, —Cl, —Br, —I, 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, —SF5, C1-C20 alkyl group, a C1-C20 alkoxy group or a C1-C20 alkylthio group;
      • a C1-C20 alkyl group, a C1-C20 alkoxy group or a C1-C20 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof,
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof; or
      • —N(Q1)(Q2), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
      • R12 may not be hydrogen nor a methyl group, and
  • Q1 to Q9 may each independently be:
      • —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
      • an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
  • In one or more embodiments, a number of carbon included in R12 of Formula 2B may be at least two.
  • In one or more embodiments, R12 in Formula 2B may be:
      • a C2-C20 alkyl group or a C2-C20 alkoxy group;
      • a methyl group or a methoxy group, each substituted with a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof;
      • a C2-C20 alkyl group or a C2-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C10 alkyl group, a C1-C10 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof;
      • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof; or
      • —N(Q1)(Q2), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
  • In one or more embodiments, R12 in Formula 2B may be:
      • a methyl group or a methoxy group, each substituted with a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
      • a methyl group or a methoxy group, each substituted with i) cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof, and ii) at least one deuterium;
      • a C2-C20 alkyl group or a C2-C20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof.
  • In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition (1) to Condition (3) below:
  • Condition (1)
  • In Formula 2A, Z1 is not hydrogen, and a1 is an integer of 1 to 20.
  • Condition (2)
  • In Formula 2B, R14 is not hydrogen, and b1 is an integer of 1 to 20.
  • Condition (3)
  • In Formula 2A, Z2 is not hydrogen, and a2 is an integer of 1 to 6.
  • In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium, at least one fluoro group (—F), at least one cyano group (—CN), or any combination thereof.
  • In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
  • In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition A to Condition I below:
  • Condition A
  • In Formula 2A, Z1 is not hydrogen, a1 is an integer of 1 to 20, and at least one of Z1(s) in the number of a1 includes deuterium.
  • Condition B
  • In Formula 2A, Z2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z2(s) in the number of a2 includes deuterium.
  • Condition C
  • In Formula 2A, Z2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z2(s) in the number of a2 includes —F.
  • Condition D
  • In Formula 2A, Z2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z2(s) in the number of a2 includes —CN.
  • Condition E
  • In Formula 2A, Z2 is not hydrogen, a2 is an integer of 1 to 6, and at least one of Z2(s) in the number of a2 is a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
  • Condition F
  • In Formula 2B, at least one of R21 to R23 includes deuterium.
  • Condition G
  • In Formula 2B, R12 includes deuterium.
  • Condition H
  • In Formula 2B, R14 is not hydrogen, b1 is an integer of 1 to 20, and at least one of R14(s) in the number of b1 includes deuterium.
  • Condition I
  • In Formula 2B, R14 is not hydrogen, b1 is an integer of 1 to 20, and at least one of R14(s) in the number of b1 includes —F.
  • In one or more embodiments, Z2 in Formula 2A may not be hydrogen, a2 may be an integer from 1 to 3, and at least one of Z2(s) in number of a2 may each independently be a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
  • In one or more embodiments, Z2 in Formula 2A may not be hydrogen, a2 may be an integer from 1 to 3, and at least one of Z2(s) in number of a2 may each independently be a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
  • In one or more embodiments, Z1 in Formula 2A may be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-1 to 10-11, one of groups represented by Formulae 10-1 to 10-11 in which at least one hydrogen is substituted with deuterium, or one of groups represented by Formulae 10-1 to 10-11 in which at least one hydrogen is substituted with —F.
  • In one or more embodiments, Z2 and R11 to R14 in Formulae 2A and 2B may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-1 to 10-132, one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-201 to 10-353, one of groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F, —N(Q1)(Q2), or —Ge(Q3)(Q4)(Q5) (wherein Q1 to Q5 are the same as described above).
  • In one or more embodiments, R12 in Formula 2B may be one of groups represented by Formulae 9-1 to 9-39, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 9-201 to 9-233, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, one of groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-1 to 10-132, one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or one of groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, one of groups represented by Formulae 10-201 to 10-353, one of groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, or one of groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F:
  • Figure US20230371359A1-20231116-C00003
    Figure US20230371359A1-20231116-C00004
    Figure US20230371359A1-20231116-C00005
    Figure US20230371359A1-20231116-C00006
    Figure US20230371359A1-20231116-C00007
    Figure US20230371359A1-20231116-C00008
    Figure US20230371359A1-20231116-C00009
    Figure US20230371359A1-20231116-C00010
    Figure US20230371359A1-20231116-C00011
    Figure US20230371359A1-20231116-C00012
    Figure US20230371359A1-20231116-C00013
    Figure US20230371359A1-20231116-C00014
    Figure US20230371359A1-20231116-C00015
    Figure US20230371359A1-20231116-C00016
    Figure US20230371359A1-20231116-C00017
    Figure US20230371359A1-20231116-C00018
  • Figure US20230371359A1-20231116-C00019
    Figure US20230371359A1-20231116-C00020
    Figure US20230371359A1-20231116-C00021
    Figure US20230371359A1-20231116-C00022
    Figure US20230371359A1-20231116-C00023
    Figure US20230371359A1-20231116-C00024
    Figure US20230371359A1-20231116-C00025
    Figure US20230371359A1-20231116-C00026
    Figure US20230371359A1-20231116-C00027
    Figure US20230371359A1-20231116-C00028
    Figure US20230371359A1-20231116-C00029
    Figure US20230371359A1-20231116-C00030
    Figure US20230371359A1-20231116-C00031
    Figure US20230371359A1-20231116-C00032
    Figure US20230371359A1-20231116-C00033
    Figure US20230371359A1-20231116-C00034
    Figure US20230371359A1-20231116-C00035
    Figure US20230371359A1-20231116-C00036
    Figure US20230371359A1-20231116-C00037
    Figure US20230371359A1-20231116-C00038
    Figure US20230371359A1-20231116-C00039
    Figure US20230371359A1-20231116-C00040
    Figure US20230371359A1-20231116-C00041
    Figure US20230371359A1-20231116-C00042
    Figure US20230371359A1-20231116-C00043
    Figure US20230371359A1-20231116-C00044
    Figure US20230371359A1-20231116-C00045
    Figure US20230371359A1-20231116-C00046
    Figure US20230371359A1-20231116-C00047
    Figure US20230371359A1-20231116-C00048
    Figure US20230371359A1-20231116-C00049
  • In Formulae 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-132 and 10-201 to 10-353,
      • * indicates a binding site to a neighboring atom,
      • Ph indicates a phenyl group,
      • TMS indicates a trimethylsilyl group,
      • TMG indicates a trimethylgermyl group, and
      • OMe indicates a methoxy group.
  • The term “groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and “groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium” as used herein may be, for example, groups represented by Formulae 9-501 to 9-514 and 9-601 to 9-635:
  • Figure US20230371359A1-20231116-C00050
    Figure US20230371359A1-20231116-C00051
    Figure US20230371359A1-20231116-C00052
    Figure US20230371359A1-20231116-C00053
    Figure US20230371359A1-20231116-C00054
    Figure US20230371359A1-20231116-C00055
  • The term “groups represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and “groups represented by Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F” as used herein may be, for example, groups represented by Formulae 9-701 to 9-710:
  • Figure US20230371359A1-20231116-C00056
  • The term “groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium” and “groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium” as used herein may be, for example, groups represented by Formulae 10-501 to 10-553:
  • Figure US20230371359A1-20231116-C00057
    Figure US20230371359A1-20231116-C00058
  • The term “groups represented by Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F” and “groups represented by Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F” as used herein may be, for example, groups represented by Formulae 10-601 to 10-620:
  • Figure US20230371359A1-20231116-C00059
    Figure US20230371359A1-20231116-C00060
  • In Formulae 2A and 2B, i) two or more of R21 to R23 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, ii) two or more of a plurality of Z1(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iii) two or more of a plurality of Z2(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iv) R12 and R13 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, v) two or more of a plurality of R14(s) may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, and vi) two or more of Z1, Z2 and R11 to R14 may optionally be linked to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
  • R10a may be the same as defined in connection with R14 in the present specification.
  • In Formulae 2A and 2B, * and *′ each indicate a binding site to M in Formula 1.
  • In one or more embodiments, the group represented by
  • Figure US20230371359A1-20231116-C00061
  • in Formula 2A may be a group represented by one of Formulae CY1-1 to CY1-28:
  • Figure US20230371359A1-20231116-C00062
    Figure US20230371359A1-20231116-C00063
    Figure US20230371359A1-20231116-C00064
    Figure US20230371359A1-20231116-C00065
  • In Formulae CY1-1 to CY1-28,
      • Z11 to Z14 may each be the same as defined in connection with Z1, provided that each of Z11 to Z14 are not hydrogen,
      • ring CY10a may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
      • R10a may be the same as described above,
      • aa may be an integer from 0 to 10,
      • * indicates a binding site to M in Formula 1, and
      • *′ indicates a binding site to one of T1 to T4 in Formula 2A.
  • In one or more embodiments, the group represented by
  • Figure US20230371359A1-20231116-C00066
  • in Formula 2A may be a group represented by one of Formulae CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.
  • In one or more embodiments, the group represented by
  • Figure US20230371359A1-20231116-C00067
  • in Formula 2A may be a group represented by one of Formulae CY2-1 to CY2-6:
  • Figure US20230371359A1-20231116-C00068
    Figure US20230371359A1-20231116-C00069
  • In Formulae CY2-1 to CY2-6,
      • T1 to T8 may each independently be C or N,
      • X21 may be the same as described above,
      • *″ indicates a binding site to ring CY1 in Formula 2A, and
      • *′ indicates a binding site to M in Formula 1.
  • For example,
      • a) X1 in Formula 2B may be Ge, and each of T1 to T8 in Formulae CY2-1 to CY2-6 may be C, (and/or)
      • b) X1 in Formula 2B may be Si or Ge, and at least one of T3 to T8 (for example, one or two of T3 to T8) in Formulae CY2-1 and CY2-6 may be N, (and/or)
      • c) X1 in Formula 2B may be Si or Ge, and at least one of T1, T2, and T5 to T8 (for example, one or two of T1, T2, and T5 to T8) in Formulae CY2-2 and CY2-5 may be N, (and/or)
      • d) X1 in Formula 2B may be Si or Ge, and at least one of T1 and T4 to T8 (for example, one or two T1 and T4 to T8) in Formulae CY2-3 and CY2-4 may be N.
  • In one or more embodiments,
      • 1) T1 to T8 in Formulae CY2-1 to CY2-6 may be C;
      • 2) one of T3 to T8 in Formula CY2-1 may be N, and the remaining T3 to T8 that are not N in Formula CY2-1 may be C;
      • 3) T3 and T8 in Formula CY2-1 may be N, and T4 to T7 in Formula CY2-1 may be C;
      • 4) T5 and T8 in Formula CY2-1 may be N, and T3 to T8 and T7 in Formula CY2-1 may be C;
      • 5) one of T1, T2 and T8 in Formula CY2-2 may be N, and the remaining T1, T2 and T5 to T8 that are not N in Formula CY2-2 may be C;
      • 6) T1 and T8 in Formula CY2-2 may be N, and T2 and T5 to T7 in Formula CY2-2 may be C;
      • 7) T2 and T8 in Formula CY2-2 may be N, and T1 and T5 to T7 in Formula CY2-2 may be C;
      • 8) one of T1, T4 and T8 in Formulae CY2-3 and CY2-4 may be N, and the remaining T1, T4 and T5 to T8 that are not N in Formulae CY2-3 and CY2-4 may be C;
      • 9) T1 and T8 in Formulae CY2-3 and CY2-4 may be N, and T4 and T5 to T7 in Formulae CY2-3 and CY2-4 may be C;
      • 10) T4 and T8 in Formulae CY2-3 and CY2-4 may be N, and T1 and T5 to T7 in Formulae CY2-3 and CY2-4 may be C;
      • 11) one of T1 and T8 in Formula CY2-5 may be N, and the remaining T1, T2 and T5 to T8 that are not N in Formula CY2-5 may be C;
      • 12) T1 and T8 in Formula CY2-5 may be N, and T2 and T5 to T7 in Formula CY2-5 may be C;
      • 13) one of T4 and T8 in Formula CY2-6 may be N, and the remaining T3 to T8 that are not N in Formula CY2-6 may be C; or
      • 14) T4 and T8 in Formula CY2-6 may be N, and T3 and T5 to T7 in Formula CY2-6 may be C.
  • In one or more embodiments, a group represented by
  • Figure US20230371359A1-20231116-C00070
  • in Formula 2A may be a group represented by one of Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065 and CY2-6001 to CY2-6065:
  • Figure US20230371359A1-20231116-C00071
    Figure US20230371359A1-20231116-C00072
    Figure US20230371359A1-20231116-C00073
    Figure US20230371359A1-20231116-C00074
    Figure US20230371359A1-20231116-C00075
    Figure US20230371359A1-20231116-C00076
    Figure US20230371359A1-20231116-C00077
    Figure US20230371359A1-20231116-C00078
    Figure US20230371359A1-20231116-C00079
    Figure US20230371359A1-20231116-C00080
    Figure US20230371359A1-20231116-C00081
    Figure US20230371359A1-20231116-C00082
    Figure US20230371359A1-20231116-C00083
    Figure US20230371359A1-20231116-C00084
    Figure US20230371359A1-20231116-C00085
    Figure US20230371359A1-20231116-C00086
    Figure US20230371359A1-20231116-C00087
    Figure US20230371359A1-20231116-C00088
    Figure US20230371359A1-20231116-C00089
    Figure US20230371359A1-20231116-C00090
    Figure US20230371359A1-20231116-C00091
    Figure US20230371359A1-20231116-C00092
    Figure US20230371359A1-20231116-C00093
    Figure US20230371359A1-20231116-C00094
    Figure US20230371359A1-20231116-C00095
    Figure US20230371359A1-20231116-C00096
    Figure US20230371359A1-20231116-C00097
    Figure US20230371359A1-20231116-C00098
    Figure US20230371359A1-20231116-C00099
    Figure US20230371359A1-20231116-C00100
    Figure US20230371359A1-20231116-C00101
    Figure US20230371359A1-20231116-C00102
    Figure US20230371359A1-20231116-C00103
  • Figure US20230371359A1-20231116-C00104
    Figure US20230371359A1-20231116-C00105
    Figure US20230371359A1-20231116-C00106
    Figure US20230371359A1-20231116-C00107
    Figure US20230371359A1-20231116-C00108
    Figure US20230371359A1-20231116-C00109
    Figure US20230371359A1-20231116-C00110
    Figure US20230371359A1-20231116-C00111
    Figure US20230371359A1-20231116-C00112
    Figure US20230371359A1-20231116-C00113
    Figure US20230371359A1-20231116-C00114
    Figure US20230371359A1-20231116-C00115
    Figure US20230371359A1-20231116-C00116
    Figure US20230371359A1-20231116-C00117
    Figure US20230371359A1-20231116-C00118
    Figure US20230371359A1-20231116-C00119
    Figure US20230371359A1-20231116-C00120
    Figure US20230371359A1-20231116-C00121
    Figure US20230371359A1-20231116-C00122
    Figure US20230371359A1-20231116-C00123
    Figure US20230371359A1-20231116-C00124
    Figure US20230371359A1-20231116-C00125
    Figure US20230371359A1-20231116-C00126
    Figure US20230371359A1-20231116-C00127
    Figure US20230371359A1-20231116-C00128
    Figure US20230371359A1-20231116-C00129
    Figure US20230371359A1-20231116-C00130
    Figure US20230371359A1-20231116-C00131
    Figure US20230371359A1-20231116-C00132
    Figure US20230371359A1-20231116-C00133
    Figure US20230371359A1-20231116-C00134
    Figure US20230371359A1-20231116-C00135
    Figure US20230371359A1-20231116-C00136
    Figure US20230371359A1-20231116-C00137
    Figure US20230371359A1-20231116-C00138
    Figure US20230371359A1-20231116-C00139
    Figure US20230371359A1-20231116-C00140
    Figure US20230371359A1-20231116-C00141
    Figure US20230371359A1-20231116-C00142
    Figure US20230371359A1-20231116-C00143
    Figure US20230371359A1-20231116-C00144
    Figure US20230371359A1-20231116-C00145
    Figure US20230371359A1-20231116-C00146
    Figure US20230371359A1-20231116-C00147
    Figure US20230371359A1-20231116-C00148
    Figure US20230371359A1-20231116-C00149
    Figure US20230371359A1-20231116-C00150
    Figure US20230371359A1-20231116-C00151
    Figure US20230371359A1-20231116-C00152
    Figure US20230371359A1-20231116-C00153
  • Figure US20230371359A1-20231116-C00154
    Figure US20230371359A1-20231116-C00155
    Figure US20230371359A1-20231116-C00156
    Figure US20230371359A1-20231116-C00157
    Figure US20230371359A1-20231116-C00158
    Figure US20230371359A1-20231116-C00159
    Figure US20230371359A1-20231116-C00160
    Figure US20230371359A1-20231116-C00161
    Figure US20230371359A1-20231116-C00162
    Figure US20230371359A1-20231116-C00163
  • In Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065 and CY2-6001 to CY2-6065,
      • X21 may each be the same as described above,
      • Z21 to Z28 may each be the same as defined in connection with Z2, provided that each of Z21 to Z28 are not hydrogen,
      • *″ indicates a binding site to ring CY1 in Formula 2A, and
      • *′ indicates a binding site to M in Formula 1.
  • In one or more embodiments, a group represented by
  • Figure US20230371359A1-20231116-C00164
  • in Formula 2B may be a group represented by one of Formulae CY14-1 to CY14-64:
  • Figure US20230371359A1-20231116-C00165
    Figure US20230371359A1-20231116-C00166
    Figure US20230371359A1-20231116-C00167
    Figure US20230371359A1-20231116-C00168
    Figure US20230371359A1-20231116-C00169
    Figure US20230371359A1-20231116-C00170
    Figure US20230371359A1-20231116-C00171
    Figure US20230371359A1-20231116-C00172
    Figure US20230371359A1-20231116-C00173
  • In Formulae CY14-1 to CY14-64,
      • R14 may be the same as described above,
      • X14 may be C(R1)(R2), N(R1), O, S, or Si(R1)(R2),
      • R1 to R8 may each be the same as defined in connection with R14 in the present specification,
      • b18 may be an integer from 0 to 8,
      • b16 may be an integer from 0 to 6,
      • b15 may be an integer from 0 to 5,
      • b14 may be an integer from 0 to 4,
      • b13 may be an integer from 0 to 3,
      • b12 may be an integer from 0 to 2,
      • *″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2B, and
      • *′ indicates a binding site to M in Formula 1.
  • In one or more embodiments, a group represented by
  • Figure US20230371359A1-20231116-C00174
  • in Formula 2B may be a group represented by one of Formulae CY14(1) to CY14(63):
  • Figure US20230371359A1-20231116-C00175
    Figure US20230371359A1-20231116-C00176
    Figure US20230371359A1-20231116-C00177
    Figure US20230371359A1-20231116-C00178
    Figure US20230371359A1-20231116-C00179
    Figure US20230371359A1-20231116-C00180
    Figure US20230371359A1-20231116-C00181
  • In Formulae CY14(1) to CY14(63),
      • R14a to R14d may each the same as defined in connection with R14, wherein each of R14a to R14d may not be hydrogen,
      • X14 may be C(R1)(R2), N(R1), O, S or Si(R1)(R2),
      • R1 to R8 may each the same as defined in connection with R14, wherein
      • *″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2B, and
      • *′ indicates a binding site to M in Formula 1.
  • In one or more embodiments, the organometallic compound may be represented by Formula 1A:
  • Figure US20230371359A1-20231116-C00182
  • In Formula 1A,
      • M, n1, n2, X1, X21, R21 to R23, and R1 to R13 may each be the same as described above,
      • T11 may be N or C(Z11), T12 may be N or C(Z12), T13 may be N or C(Z13), and T14 may be N or C(Z14), wherein Z11 to Z14 may each be the same as defined in connection with Z1,
      • T21 may be N, C(Z21), carbon linked to a neighboring 6-membered ring, or carbon linked to M in Formula 1, T22 may be N, C(Z22), carbon linked to a neighboring 6-membered ring, or carbon linked to M in Formula 1, T23 may be N, C(Z23), carbon linked to a neighboring 6-membered ring, or carbon linked to M in Formula 1, T24 may be N, C(Z24), carbon linked to a neighboring 6-membered ring, or carbon linked to M in Formula 1, T25 may be N or C(Z25), T26 may be N or C(Z26), T27 may be N or C(Z27), and T28 may be N or C(Z28), wherein one of T21 to T24 may be carbon linked to M in Formula 1, one of the remaining T21 to T24 that are not linked to M in Formula 1 may be carbon linked to a neighboring 6-membered ring, and Z21 to Z24 may each be the same as defined in connection with Z2,
      • T31 may be N or C(R14a), T32 may be N or C(R14b), T33 may be N or C(R14c), and T24 may be N or C(R14a), wherein R14a to R14d may each be the same as defined in connection with R14,
      • two or more of Z1 to Z14 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of Z21 to Z28 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • R12 and R13 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
      • two or more of R14a to R14d may optionally be linked to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, and
      • R10a may be the same as defined in connection with R14.
  • Descriptions for Formula 1A may refer to descriptions for Formula 1 in this disclosure.
  • For example, T13 in Formula 1A may be C(Z13) and Z13 may not be a hydrogen.
  • In one or more embodiments, the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1 or 2.
  • In one or more embodiments, the organometallic compound may be one of Compounds 1 to 1620:
  • Figure US20230371359A1-20231116-C00183
    Figure US20230371359A1-20231116-C00184
    Figure US20230371359A1-20231116-C00185
    Figure US20230371359A1-20231116-C00186
    Figure US20230371359A1-20231116-C00187
    Figure US20230371359A1-20231116-C00188
    Figure US20230371359A1-20231116-C00189
    Figure US20230371359A1-20231116-C00190
    Figure US20230371359A1-20231116-C00191
    Figure US20230371359A1-20231116-C00192
    Figure US20230371359A1-20231116-C00193
    Figure US20230371359A1-20231116-C00194
    Figure US20230371359A1-20231116-C00195
    Figure US20230371359A1-20231116-C00196
    Figure US20230371359A1-20231116-C00197
    Figure US20230371359A1-20231116-C00198
    Figure US20230371359A1-20231116-C00199
    Figure US20230371359A1-20231116-C00200
    Figure US20230371359A1-20231116-C00201
    Figure US20230371359A1-20231116-C00202
    Figure US20230371359A1-20231116-C00203
    Figure US20230371359A1-20231116-C00204
    Figure US20230371359A1-20231116-C00205
    Figure US20230371359A1-20231116-C00206
    Figure US20230371359A1-20231116-C00207
    Figure US20230371359A1-20231116-C00208
    Figure US20230371359A1-20231116-C00209
    Figure US20230371359A1-20231116-C00210
    Figure US20230371359A1-20231116-C00211
    Figure US20230371359A1-20231116-C00212
    Figure US20230371359A1-20231116-C00213
    Figure US20230371359A1-20231116-C00214
    Figure US20230371359A1-20231116-C00215
    Figure US20230371359A1-20231116-C00216
    Figure US20230371359A1-20231116-C00217
    Figure US20230371359A1-20231116-C00218
    Figure US20230371359A1-20231116-C00219
    Figure US20230371359A1-20231116-C00220
    Figure US20230371359A1-20231116-C00221
    Figure US20230371359A1-20231116-C00222
    Figure US20230371359A1-20231116-C00223
    Figure US20230371359A1-20231116-C00224
    Figure US20230371359A1-20231116-C00225
    Figure US20230371359A1-20231116-C00226
    Figure US20230371359A1-20231116-C00227
    Figure US20230371359A1-20231116-C00228
    Figure US20230371359A1-20231116-C00229
    Figure US20230371359A1-20231116-C00230
    Figure US20230371359A1-20231116-C00231
    Figure US20230371359A1-20231116-C00232
    Figure US20230371359A1-20231116-C00233
    Figure US20230371359A1-20231116-C00234
    Figure US20230371359A1-20231116-C00235
    Figure US20230371359A1-20231116-C00236
    Figure US20230371359A1-20231116-C00237
    Figure US20230371359A1-20231116-C00238
    Figure US20230371359A1-20231116-C00239
    Figure US20230371359A1-20231116-C00240
    Figure US20230371359A1-20231116-C00241
    Figure US20230371359A1-20231116-C00242
    Figure US20230371359A1-20231116-C00243
    Figure US20230371359A1-20231116-C00244
    Figure US20230371359A1-20231116-C00245
    Figure US20230371359A1-20231116-C00246
    Figure US20230371359A1-20231116-C00247
    Figure US20230371359A1-20231116-C00248
    Figure US20230371359A1-20231116-C00249
    Figure US20230371359A1-20231116-C00250
    Figure US20230371359A1-20231116-C00251
    Figure US20230371359A1-20231116-C00252
  • Figure US20230371359A1-20231116-C00253
    Figure US20230371359A1-20231116-C00254
    Figure US20230371359A1-20231116-C00255
    Figure US20230371359A1-20231116-C00256
    Figure US20230371359A1-20231116-C00257
    Figure US20230371359A1-20231116-C00258
    Figure US20230371359A1-20231116-C00259
    Figure US20230371359A1-20231116-C00260
    Figure US20230371359A1-20231116-C00261
    Figure US20230371359A1-20231116-C00262
    Figure US20230371359A1-20231116-C00263
    Figure US20230371359A1-20231116-C00264
    Figure US20230371359A1-20231116-C00265
    Figure US20230371359A1-20231116-C00266
    Figure US20230371359A1-20231116-C00267
    Figure US20230371359A1-20231116-C00268
    Figure US20230371359A1-20231116-C00269
    Figure US20230371359A1-20231116-C00270
    Figure US20230371359A1-20231116-C00271
    Figure US20230371359A1-20231116-C00272
    Figure US20230371359A1-20231116-C00273
    Figure US20230371359A1-20231116-C00274
    Figure US20230371359A1-20231116-C00275
    Figure US20230371359A1-20231116-C00276
    Figure US20230371359A1-20231116-C00277
    Figure US20230371359A1-20231116-C00278
    Figure US20230371359A1-20231116-C00279
    Figure US20230371359A1-20231116-C00280
    Figure US20230371359A1-20231116-C00281
    Figure US20230371359A1-20231116-C00282
    Figure US20230371359A1-20231116-C00283
    Figure US20230371359A1-20231116-C00284
    Figure US20230371359A1-20231116-C00285
    Figure US20230371359A1-20231116-C00286
    Figure US20230371359A1-20231116-C00287
    Figure US20230371359A1-20231116-C00288
    Figure US20230371359A1-20231116-C00289
    Figure US20230371359A1-20231116-C00290
    Figure US20230371359A1-20231116-C00291
    Figure US20230371359A1-20231116-C00292
    Figure US20230371359A1-20231116-C00293
    Figure US20230371359A1-20231116-C00294
    Figure US20230371359A1-20231116-C00295
    Figure US20230371359A1-20231116-C00296
    Figure US20230371359A1-20231116-C00297
    Figure US20230371359A1-20231116-C00298
    Figure US20230371359A1-20231116-C00299
    Figure US20230371359A1-20231116-C00300
    Figure US20230371359A1-20231116-C00301
    Figure US20230371359A1-20231116-C00302
    Figure US20230371359A1-20231116-C00303
    Figure US20230371359A1-20231116-C00304
    Figure US20230371359A1-20231116-C00305
    Figure US20230371359A1-20231116-C00306
    Figure US20230371359A1-20231116-C00307
    Figure US20230371359A1-20231116-C00308
    Figure US20230371359A1-20231116-C00309
    Figure US20230371359A1-20231116-C00310
    Figure US20230371359A1-20231116-C00311
    Figure US20230371359A1-20231116-C00312
    Figure US20230371359A1-20231116-C00313
    Figure US20230371359A1-20231116-C00314
    Figure US20230371359A1-20231116-C00315
    Figure US20230371359A1-20231116-C00316
    Figure US20230371359A1-20231116-C00317
    Figure US20230371359A1-20231116-C00318
    Figure US20230371359A1-20231116-C00319
    Figure US20230371359A1-20231116-C00320
    Figure US20230371359A1-20231116-C00321
    Figure US20230371359A1-20231116-C00322
    Figure US20230371359A1-20231116-C00323
    Figure US20230371359A1-20231116-C00324
    Figure US20230371359A1-20231116-C00325
    Figure US20230371359A1-20231116-C00326
    Figure US20230371359A1-20231116-C00327
    Figure US20230371359A1-20231116-C00328
    Figure US20230371359A1-20231116-C00329
    Figure US20230371359A1-20231116-C00330
    Figure US20230371359A1-20231116-C00331
    Figure US20230371359A1-20231116-C00332
    Figure US20230371359A1-20231116-C00333
  • Figure US20230371359A1-20231116-C00334
    Figure US20230371359A1-20231116-C00335
    Figure US20230371359A1-20231116-C00336
    Figure US20230371359A1-20231116-C00337
    Figure US20230371359A1-20231116-C00338
    Figure US20230371359A1-20231116-C00339
    Figure US20230371359A1-20231116-C00340
    Figure US20230371359A1-20231116-C00341
    Figure US20230371359A1-20231116-C00342
    Figure US20230371359A1-20231116-C00343
    Figure US20230371359A1-20231116-C00344
    Figure US20230371359A1-20231116-C00345
    Figure US20230371359A1-20231116-C00346
    Figure US20230371359A1-20231116-C00347
    Figure US20230371359A1-20231116-C00348
    Figure US20230371359A1-20231116-C00349
    Figure US20230371359A1-20231116-C00350
    Figure US20230371359A1-20231116-C00351
    Figure US20230371359A1-20231116-C00352
    Figure US20230371359A1-20231116-C00353
    Figure US20230371359A1-20231116-C00354
    Figure US20230371359A1-20231116-C00355
    Figure US20230371359A1-20231116-C00356
    Figure US20230371359A1-20231116-C00357
    Figure US20230371359A1-20231116-C00358
    Figure US20230371359A1-20231116-C00359
    Figure US20230371359A1-20231116-C00360
    Figure US20230371359A1-20231116-C00361
    Figure US20230371359A1-20231116-C00362
    Figure US20230371359A1-20231116-C00363
    Figure US20230371359A1-20231116-C00364
    Figure US20230371359A1-20231116-C00365
    Figure US20230371359A1-20231116-C00366
    Figure US20230371359A1-20231116-C00367
    Figure US20230371359A1-20231116-C00368
    Figure US20230371359A1-20231116-C00369
    Figure US20230371359A1-20231116-C00370
    Figure US20230371359A1-20231116-C00371
    Figure US20230371359A1-20231116-C00372
    Figure US20230371359A1-20231116-C00373
    Figure US20230371359A1-20231116-C00374
    Figure US20230371359A1-20231116-C00375
    Figure US20230371359A1-20231116-C00376
    Figure US20230371359A1-20231116-C00377
    Figure US20230371359A1-20231116-C00378
    Figure US20230371359A1-20231116-C00379
    Figure US20230371359A1-20231116-C00380
    Figure US20230371359A1-20231116-C00381
    Figure US20230371359A1-20231116-C00382
    Figure US20230371359A1-20231116-C00383
    Figure US20230371359A1-20231116-C00384
    Figure US20230371359A1-20231116-C00385
    Figure US20230371359A1-20231116-C00386
    Figure US20230371359A1-20231116-C00387
    Figure US20230371359A1-20231116-C00388
    Figure US20230371359A1-20231116-C00389
    Figure US20230371359A1-20231116-C00390
    Figure US20230371359A1-20231116-C00391
    Figure US20230371359A1-20231116-C00392
    Figure US20230371359A1-20231116-C00393
    Figure US20230371359A1-20231116-C00394
    Figure US20230371359A1-20231116-C00395
    Figure US20230371359A1-20231116-C00396
    Figure US20230371359A1-20231116-C00397
    Figure US20230371359A1-20231116-C00398
    Figure US20230371359A1-20231116-C00399
    Figure US20230371359A1-20231116-C00400
    Figure US20230371359A1-20231116-C00401
    Figure US20230371359A1-20231116-C00402
  • Figure US20230371359A1-20231116-C00403
    Figure US20230371359A1-20231116-C00404
    Figure US20230371359A1-20231116-C00405
    Figure US20230371359A1-20231116-C00406
    Figure US20230371359A1-20231116-C00407
    Figure US20230371359A1-20231116-C00408
    Figure US20230371359A1-20231116-C00409
    Figure US20230371359A1-20231116-C00410
    Figure US20230371359A1-20231116-C00411
    Figure US20230371359A1-20231116-C00412
    Figure US20230371359A1-20231116-C00413
    Figure US20230371359A1-20231116-C00414
    Figure US20230371359A1-20231116-C00415
    Figure US20230371359A1-20231116-C00416
    Figure US20230371359A1-20231116-C00417
    Figure US20230371359A1-20231116-C00418
    Figure US20230371359A1-20231116-C00419
    Figure US20230371359A1-20231116-C00420
    Figure US20230371359A1-20231116-C00421
    Figure US20230371359A1-20231116-C00422
    Figure US20230371359A1-20231116-C00423
    Figure US20230371359A1-20231116-C00424
    Figure US20230371359A1-20231116-C00425
    Figure US20230371359A1-20231116-C00426
    Figure US20230371359A1-20231116-C00427
    Figure US20230371359A1-20231116-C00428
    Figure US20230371359A1-20231116-C00429
    Figure US20230371359A1-20231116-C00430
    Figure US20230371359A1-20231116-C00431
    Figure US20230371359A1-20231116-C00432
    Figure US20230371359A1-20231116-C00433
    Figure US20230371359A1-20231116-C00434
    Figure US20230371359A1-20231116-C00435
    Figure US20230371359A1-20231116-C00436
    Figure US20230371359A1-20231116-C00437
    Figure US20230371359A1-20231116-C00438
    Figure US20230371359A1-20231116-C00439
    Figure US20230371359A1-20231116-C00440
    Figure US20230371359A1-20231116-C00441
    Figure US20230371359A1-20231116-C00442
    Figure US20230371359A1-20231116-C00443
    Figure US20230371359A1-20231116-C00444
    Figure US20230371359A1-20231116-C00445
    Figure US20230371359A1-20231116-C00446
    Figure US20230371359A1-20231116-C00447
    Figure US20230371359A1-20231116-C00448
    Figure US20230371359A1-20231116-C00449
    Figure US20230371359A1-20231116-C00450
    Figure US20230371359A1-20231116-C00451
    Figure US20230371359A1-20231116-C00452
    Figure US20230371359A1-20231116-C00453
    Figure US20230371359A1-20231116-C00454
    Figure US20230371359A1-20231116-C00455
    Figure US20230371359A1-20231116-C00456
    Figure US20230371359A1-20231116-C00457
    Figure US20230371359A1-20231116-C00458
    Figure US20230371359A1-20231116-C00459
    Figure US20230371359A1-20231116-C00460
    Figure US20230371359A1-20231116-C00461
    Figure US20230371359A1-20231116-C00462
    Figure US20230371359A1-20231116-C00463
    Figure US20230371359A1-20231116-C00464
    Figure US20230371359A1-20231116-C00465
    Figure US20230371359A1-20231116-C00466
    Figure US20230371359A1-20231116-C00467
    Figure US20230371359A1-20231116-C00468
    Figure US20230371359A1-20231116-C00469
    Figure US20230371359A1-20231116-C00470
    Figure US20230371359A1-20231116-C00471
    Figure US20230371359A1-20231116-C00472
    Figure US20230371359A1-20231116-C00473
    Figure US20230371359A1-20231116-C00474
    Figure US20230371359A1-20231116-C00475
    Figure US20230371359A1-20231116-C00476
    Figure US20230371359A1-20231116-C00477
    Figure US20230371359A1-20231116-C00478
  • Figure US20230371359A1-20231116-C00479
    Figure US20230371359A1-20231116-C00480
    Figure US20230371359A1-20231116-C00481
    Figure US20230371359A1-20231116-C00482
    Figure US20230371359A1-20231116-C00483
    Figure US20230371359A1-20231116-C00484
    Figure US20230371359A1-20231116-C00485
    Figure US20230371359A1-20231116-C00486
    Figure US20230371359A1-20231116-C00487
    Figure US20230371359A1-20231116-C00488
    Figure US20230371359A1-20231116-C00489
    Figure US20230371359A1-20231116-C00490
    Figure US20230371359A1-20231116-C00491
    Figure US20230371359A1-20231116-C00492
    Figure US20230371359A1-20231116-C00493
    Figure US20230371359A1-20231116-C00494
    Figure US20230371359A1-20231116-C00495
    Figure US20230371359A1-20231116-C00496
    Figure US20230371359A1-20231116-C00497
    Figure US20230371359A1-20231116-C00498
    Figure US20230371359A1-20231116-C00499
    Figure US20230371359A1-20231116-C00500
    Figure US20230371359A1-20231116-C00501
    Figure US20230371359A1-20231116-C00502
    Figure US20230371359A1-20231116-C00503
    Figure US20230371359A1-20231116-C00504
    Figure US20230371359A1-20231116-C00505
    Figure US20230371359A1-20231116-C00506
    Figure US20230371359A1-20231116-C00507
    Figure US20230371359A1-20231116-C00508
    Figure US20230371359A1-20231116-C00509
    Figure US20230371359A1-20231116-C00510
    Figure US20230371359A1-20231116-C00511
    Figure US20230371359A1-20231116-C00512
    Figure US20230371359A1-20231116-C00513
    Figure US20230371359A1-20231116-C00514
    Figure US20230371359A1-20231116-C00515
    Figure US20230371359A1-20231116-C00516
    Figure US20230371359A1-20231116-C00517
    Figure US20230371359A1-20231116-C00518
    Figure US20230371359A1-20231116-C00519
    Figure US20230371359A1-20231116-C00520
    Figure US20230371359A1-20231116-C00521
    Figure US20230371359A1-20231116-C00522
    Figure US20230371359A1-20231116-C00523
    Figure US20230371359A1-20231116-C00524
    Figure US20230371359A1-20231116-C00525
    Figure US20230371359A1-20231116-C00526
    Figure US20230371359A1-20231116-C00527
    Figure US20230371359A1-20231116-C00528
    Figure US20230371359A1-20231116-C00529
    Figure US20230371359A1-20231116-C00530
    Figure US20230371359A1-20231116-C00531
    Figure US20230371359A1-20231116-C00532
    Figure US20230371359A1-20231116-C00533
    Figure US20230371359A1-20231116-C00534
    Figure US20230371359A1-20231116-C00535
    Figure US20230371359A1-20231116-C00536
    Figure US20230371359A1-20231116-C00537
    Figure US20230371359A1-20231116-C00538
    Figure US20230371359A1-20231116-C00539
    Figure US20230371359A1-20231116-C00540
    Figure US20230371359A1-20231116-C00541
    Figure US20230371359A1-20231116-C00542
    Figure US20230371359A1-20231116-C00543
    Figure US20230371359A1-20231116-C00544
    Figure US20230371359A1-20231116-C00545
    Figure US20230371359A1-20231116-C00546
    Figure US20230371359A1-20231116-C00547
    Figure US20230371359A1-20231116-C00548
  • Figure US20230371359A1-20231116-C00549
    Figure US20230371359A1-20231116-C00550
    Figure US20230371359A1-20231116-C00551
    Figure US20230371359A1-20231116-C00552
    Figure US20230371359A1-20231116-C00553
    Figure US20230371359A1-20231116-C00554
    Figure US20230371359A1-20231116-C00555
    Figure US20230371359A1-20231116-C00556
    Figure US20230371359A1-20231116-C00557
    Figure US20230371359A1-20231116-C00558
    Figure US20230371359A1-20231116-C00559
    Figure US20230371359A1-20231116-C00560
    Figure US20230371359A1-20231116-C00561
    Figure US20230371359A1-20231116-C00562
    Figure US20230371359A1-20231116-C00563
    Figure US20230371359A1-20231116-C00564
    Figure US20230371359A1-20231116-C00565
    Figure US20230371359A1-20231116-C00566
    Figure US20230371359A1-20231116-C00567
    Figure US20230371359A1-20231116-C00568
    Figure US20230371359A1-20231116-C00569
    Figure US20230371359A1-20231116-C00570
    Figure US20230371359A1-20231116-C00571
    Figure US20230371359A1-20231116-C00572
    Figure US20230371359A1-20231116-C00573
    Figure US20230371359A1-20231116-C00574
    Figure US20230371359A1-20231116-C00575
  • In Compounds 1 to 1620, OMe indicates a methoxy group.
  • L1 of the organometallic compound represented by Formula 1 may be a ligand represented by Formula 2A, and n1 which indicates the number of L1(s) may be 1 or 2. L2 of the organometallic compound represented by Formula 1 may be a ligand represented by Formula 2B, and n2 which indicates the number of L2(s) may be 1 or 2. Here, L1 and L2 are different from each other. That is, the organometallic compound may be a heteroleptic complex essentially including, as ligands linked to metal M, at least one ligand represented by Formula 2A and at least one ligand represented by Formula 2B.
  • A group represented by *—X1(R21)(R22)(R23) in Formula 1 may be linked to the fifth position of a pyridine ring in a ligand represented by Formula 2B (see Formula 2B). Accordingly, the organometallic compound including the ligand represented by Formula 2B may have excellent heat resistance and degradation resistance so that an electronic device, for example, an organic light-emitting device, including the organometallic compound may have high stability and long lifespan in production, storage, and/or operation.
  • Furthermore, when X1 is Si, at least one of T1 to T8 which are not linked to M and ring CY1 in Formula 2A may be N. Accordingly, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved driving voltage and roll-off ratio.
  • In one or more embodiments, in Formulae 2A and 2B, R21 to R23, Z1, Z2, and R1 to R14 do not each include a silicon (Si). Accordingly, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved out-coupling characteristics.
  • In addition, R12 in Formula 2B is not hydrogen nor a methyl group. As such, the organometallic compound represented by Formula 1 may emit light that is shifted toward relatively shorter wavelengths, for example, blue light, green light, or greenish blue light, and an electronic device, for example, an organic light-emitting device, including the organometallic compound may have an excellent out-coupling effect, thereby having high luminescence efficiency.
  • A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a singlet (Si) energy level, and a triplet (T1) energy level of some compounds of the organometallic compound represented by Formula 1 are evaluated by a density functional theory (DFT) of Gaussian program with molecular structure optimization based on B3LYP, and results are shown in Table 1.
  • TABLE 1
    Compound No. HOMO (eV) LUMO (eV) S1 (eV) T1 (eV)
    123 −4.773 −1.203 2.880 2.546
    301 −4.787 −1.314 2.738 2.476
    226 −4.780 −1.208 2.876 2.529
    545 −4.767 −1.196 2.879 2.526
  • Referring to Table 1, it is confirmed that the organometallic compound represented by Formula 1 has such electrical characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
  • Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.
  • Therefore, the organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.
  • The organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high external quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.
  • The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host). The emission layer may emit, for example, green light or blue light.
  • The expression “(an organic layer) includes at least one of the organometallic compound” as used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
  • For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may exist only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).
  • The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
  • For example, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, and the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
  • FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
  • A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material(s) with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
  • The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
  • The organic layer 15 is disposed on the first electrode 11.
  • The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
  • The hole transport region may be disposed between the first electrode 11 and the emission layer.
  • The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
  • The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
  • When the hole transport region includes a hole injection layer (HIL), the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
  • When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 to about 10−3 torr, and a deposition rate of about 0.01 Å/sec to about 100 Å/sec. However, the deposition conditions are not limited thereto.
  • When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 rpm to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
  • Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
  • The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, R-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonicacid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:
  • Figure US20230371359A1-20231116-C00576
    Figure US20230371359A1-20231116-C00577
    Figure US20230371359A1-20231116-C00578
  • Ar101 to Ar102 in Formula 201 may each independently be:
      • a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, or a perylenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.
  • The designations xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may be 0, 1 or 2. For example, xa may be 1 and xb may be 0.
  • R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:
      • hydrogen, deuterium, —F, —Cl, —Br, —I, 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 C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, and the like), or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like);
      • a C1-C10 alkyl group or a C1-C10 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, 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, or any combination thereof;
      • a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, 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 C1-C10 alkyl group, a C1-C10 alkoxy group, or any combination thereof
  • R109 in Formula 201 may be:
      • a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.
  • In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A below:
  • Figure US20230371359A1-20231116-C00579
  • Detailed descriptions of R101, R111, R112, and R109 in Formula 201A are the same as described above.
  • For example, the hole transport region may include at least one of compounds HT1 to HT20 illustrated below:
  • Figure US20230371359A1-20231116-C00580
    Figure US20230371359A1-20231116-C00581
    Figure US20230371359A1-20231116-C00582
    Figure US20230371359A1-20231116-C00583
    Figure US20230371359A1-20231116-C00584
    Figure US20230371359A1-20231116-C00585
  • A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer or combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
  • The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
  • The charge-generation material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ) and F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1 below:
  • Figure US20230371359A1-20231116-C00586
  • The hole transport region may include a buffer layer.
  • Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
  • Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be materials for the hole transport region described above, materials for a host to be explained later, or any combination thereof. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.
  • Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.
  • The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
  • The host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compounds H50, Compound H51, Compound H52, or any combination thereof:
  • Figure US20230371359A1-20231116-C00587
    Figure US20230371359A1-20231116-C00588
  • When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
  • When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
  • A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
  • Then, an electron transport region may be disposed on the emission layer.
  • The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
  • Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
  • When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof:
  • Figure US20230371359A1-20231116-C00589
  • A thickness of the hole blocking layer may be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a substantial increase in driving voltage.
  • The electron transport layer may include BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
  • Figure US20230371359A1-20231116-C00590
  • In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25:
  • Figure US20230371359A1-20231116-C00591
    Figure US20230371359A1-20231116-C00592
    Figure US20230371359A1-20231116-C00593
    Figure US20230371359A1-20231116-C00594
    Figure US20230371359A1-20231116-C00595
    Figure US20230371359A1-20231116-C00596
    Figure US20230371359A1-20231116-C00597
    Figure US20230371359A1-20231116-C00598
  • A thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
  • Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
  • The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ), Compound ET-D2, or combination thereof:
  • Figure US20230371359A1-20231116-C00599
  • The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.
  • The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
  • A thickness of the electron injection layer may be from about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without substantial increase in driving voltage.
  • The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be formed as the material for forming the second electrode 19. To manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
  • Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with the FIGURE.
  • In one or more embodiments, the organic light-emitting device may be included in an electronic apparatus. Accordingly, provided is an electronic apparatus including the organic light-emitting device. The electronic apparatus may include, for example, a display, an illuminator, and a sensor.
  • Another aspect of the present disclosure provides a diagnostic composition including at least one of the organometallic compound represented by Formula 1.
  • The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
  • The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
  • The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
  • Non-limiting examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. For example, Formula 9-33 may be a branched C alkyl group, and may be a tert-butyl group that is substituted with two methyl groups.
  • The term “C1-C60 alkoxy group” used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group). Non-limiting examples of the C1-C60 alkoxy group, the C1-C20 alkoxy group, or the C1-C10 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
  • The term “C2-C6 alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkenyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
  • The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkynyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
  • The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and the term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
  • Non-limiting examples of the C3-C10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (a norbornyl group), and a bicyclo[2.2.2]octyl group.
  • The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and the term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
  • Non-limiting examples of the C1-C10 heterocycloalkyl group include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
  • The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
  • The term “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one N, O, P, Si, B, Ge, Se, S, or any combination thereof as a ring-forming atom, 2 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C2-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C2-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkenyl group.
  • The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
  • The term “C7-C60 alkylaryl group” used herein refers to a C6-C59 arylene group substituted with at least one C1-C54 alkyl group.
  • The term “C1-C6 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has at least one heteroatom N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
  • The term “C2-C60 alkylheteroaryl group” used herein refers to a C1-C59 heteroarylene group substituted with at least one C1-C59 alkyl group.
  • The term “C6-C60 aryloxy group” used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), a C6-C60 arylthio group used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group), and a C1-C60 alkylthio group used herein indicates —SA104 (wherein A104 is the C1-C60 alkyl group).
  • The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
  • The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
  • The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. The term “C5-C30 carbocyclic group (which is unsubstituted or substituted with at least one R10a)” may include, for example, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (a norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, and a fluorene group, each being unsubstituted or substituted with at least one R10a.
  • The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring forming atom, at least one N, O, P, Si, Se, Ge, B, S, or any combination thereof other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. The “C1-C30 heterocyclic group (which is unsubstituted or substituted with at least one R10a)” may include, for example, a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, each being unsubstituted or substituted with at least one R10a.
  • The term “(C1-C20 alkyl)‘X’ group” as used herein refers to a ‘X’ group substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkylene group substituted with at least one C1-C20 alkyl group and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenylene group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group.
  • The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxide group” respectively refer to a heterocyclic group having the same backbone as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group” in which at least one of the carbon atoms constituting the cyclic groups is substituted with a nitrogen.
  • A substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
      • deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
      • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
      • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C0 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
      • —N(Q31)(Q32), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39) or —P(Q38)(Q39); or
      • any combination thereof.
  • In the present specification, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; 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 C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
  • For example, in the present specification, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be
      • —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
      • an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
  • Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.
    • EXAMPLES Synthesis Example 1 (Compound 125) Synthesis of Compound 125A
  • Figure US20230371359A1-20231116-C00600
  • 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (8.0 g, 28.4 mmol) and iridium chloride (4.4 g, 12.6 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water. The mixed solution was stirred under reflux for 24 hours, and the temperature was lowered to room temperature. A solid produced therefrom was separated by filtration, and then, washed thoroughly with water/methanol/hexane in the stated order. The resulting solid was then dried in a vacuum oven, thereby obtaining 7.5 g of Compound 125A (yield of 75%).
    • Synthesis of Compound 125B
  • Figure US20230371359A1-20231116-C00601
  • Compound 125A (1.6 g, 1.0 mmol) was mixed with 45 ml of methylene chloride (MC), and a mixture of AgOTf (Silver trifluoromethanesulfonate) (0.5 g, 2.1 mmol) and 15 ml of methanol was added thereto. Afterwards, the mixed solution was stirred at room temperature for 18 hours while blocking the light with aluminum foil. The resulting solution was then filtered through celite to remove a solid produced therefrom, and the solvent was removed from the filtrate under reduced pressure, and a solid (Compound 125B) produced therefrom was used in the next reaction without additional purification.
    • Synthesis of Compound 125
  • Figure US20230371359A1-20231116-C00602
  • Compound 125B (2.0 g, 2.1 mmol) and 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (0.8 g, 2.4 mmol) were mixed with 40 ml of a mixture of MC and ethanol. The mixed solution was stirred under reflux for 18 hours, and the temperature was lowered down. The resulting solution was filtered, and a solid obtained therefrom was washed thoroughly with ethanol and hexane. The resulting product was subjected to column chromatography under the MC: hexane conditions, thereby obtaining 0.8 g of Compound 125 (yield of 36%). Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C57H67IrN4OSi2: m/z 1072.4483 Found: 1072.4490
    • Synthesis Example 2 (Compound 128)
  • Figure US20230371359A1-20231116-C00603
  • 0.9 g of Compound 128 (yield of 40%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that 8-(4-(cyclopentylmethyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C59H69IrN4OSi2: m/z 1098.4639, Found: 1098.4631
    • Synthesis Example 3 (Compound 163) Synthesis of Compound 163A
  • Figure US20230371359A1-20231116-C00604
  • 6.5 g of Compound 163A (yield of 65%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-(cyclopentylmethyl)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 163B
  • Figure US20230371359A1-20231116-C00605
  • Compound 163B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 163A was used instead of Compound 125A. Compound 163B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 163
  • Figure US20230371359A1-20231116-C00606
  • 0.65 g of Compound 163 (yield of 29%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 163B was used instead of Compound 125B and 8-(4-isopropylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C60H69IrN4OSi2: m/z 1110.4639, Found: 1110.4644
    • Synthesis Example 4 (Compound 365)
  • Figure US20230371359A1-20231116-C00607
  • 0.85 g of Compound 365 (yield of 37%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that 6-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C57H67IrN4OSi2: m/z 1072.4483 Found: 1072.4488
    • Synthesis Example 5 (Compound 505) Synthesis of Compound 505A
  • Figure US20230371359A1-20231116-C00608
  • 7.1 g of Compound 505A (yield of 71%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-isobutyl-D2-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 505B
  • Figure US20230371359A1-20231116-C00609
  • Compound 505B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 505A was used instead of Compound 125A. Compound 505B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 505
  • Figure US20230371359A1-20231116-C00610
  • 0.5 g of Compound 505 (yield of 22%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 505B was used instead of Compound 125B and 8-(4-isobutylpyridin-2-yl-D2)-2-methyl(D3)benzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C57H58D9IrN4OSi2: m/z 1081.5048, Found: 1081.5052
    • Synthesis Example 6 (Compound 526) Synthesis of Compound 526A
  • Figure US20230371359A1-20231116-C00611
  • 6.6 g of Compound 526A (yield of 66%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-neopentyl(D2)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 526B
  • Figure US20230371359A1-20231116-C00612
  • Compound 526B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 526A was used instead of Compound 125A. Compound 526B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 526
  • Figure US20230371359A1-20231116-C00613
  • 1.0 g of Compound 526 (yield of 44%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 526B was used instead of Compound 125B and 2-isopropyl(D)-8-(4-neopentyl(D2)pyridin-2-yl)benzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C62H70D7IrN4OSi2: m/z 1149.5705, Found: 1149.5700
    • Synthesis Example 7 (Compound 676)
  • Figure US20230371359A1-20231116-C00614
  • 0.8 g of Compound 676 (yield of 41%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that 2-phenyl-8-(4-(propan-2-yl-2-d)pyridin-2-yl)benzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C61H66IrN4OSi2: m/z 1121.4545, Found: 1121.4549
    • Synthesis Example 8 (Compound 806) Synthesis of Compound 806A
  • Figure US20230371359A1-20231116-C00615
  • 3.7 g of Compound 806A (yield of 74%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-isobutyl-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 806B
  • Figure US20230371359A1-20231116-C00616
  • Compound 806B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 806A was used instead of Compound 125A. Compound 806B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 806
  • Figure US20230371359A1-20231116-C00617
  • 0.53 g of Compound 806 (yield of 35%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 806B was used instead of Compound 125B and 2-methyl(D3)-8-(4-neopentylpyridin-2-yl)benzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C58H66D3Ge2IrN4O: m/z 1181.3712, Found: 1181.3706
    • Synthesis Example 9 (Compound 865)
  • Figure US20230371359A1-20231116-C00618
  • 0.69 g of Compound 865 (yield of 31%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 806B was used instead of Compound 125B and 2-(dibenzo[b,d]furan-4-yl)-4-isobutylpyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C57H66Ge2IrN3O: m/z 1149.3259, Found: 1149.3251
    • Synthesis Example 10 (Compound 1365) Synthesis of Compound 1365A
  • Figure US20230371359A1-20231116-C00619
  • 4.6 g of Compound 1365A (yield of 62%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-isobutyl(D2)-2-(p-tolyl(D3))-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 1365B
  • Figure US20230371359A1-20231116-C00620
  • Compound 1365B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1365A was used instead of Compound 125A. Compound 1365B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 1365
  • Figure US20230371359A1-20231116-C00621
  • 0.43 g of Compound 1365 (yield of 28%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 1365B was used instead of Compound 125B and 2-(7-methyl(D3)dibenzo[b,d]thiophen-4-yl)-4-neopentyl(D2)pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine. Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C61H59D15Ge2IrN3O: m/z 1236.4598, Found: 1236.4591
    • Synthesis Example 11 (Compound 1497) Synthesis of Compound 1497A
  • Figure US20230371359A1-20231116-C00622
  • 4.2 g of Compound 1497A (yield of 58%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 2-phenyl-4-(propan-2-yl-2-d)-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 1497B
  • Figure US20230371359A1-20231116-C00623
  • Compound 1497B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1497A was used instead of Compound 125A. Compound 1497B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 1497
  • Figure US20230371359A1-20231116-C00624
  • 0.53 g of Compound 1497 (yield of 34%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 1497B was used instead of Compound 125B and 2-(2,6-dimethylphenyl)-8-(4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)pyridin-2-yl)benzofuro[2,3-b]pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C64H66D7Ge2IrN4O: m/z 1261.4277, Found: 1261.4271
    • Synthesis Example 12 (Compound 1505) Synthesis of Compound 1505A
  • Figure US20230371359A1-20231116-C00625
  • 4.3 g of Compound 1505A (yield of 49%) was obtained in the same manner as in the synthesis of Compound 125A according to Synthesis Example 1, except that 4-(2,2-dimethylpropyl-1,1-d2)-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
    • Synthesis of Compound 1505B
  • Figure US20230371359A1-20231116-C00626
  • Compound 1505B was obtained in the same manner as in the synthesis of Compound 125B according to Synthesis Example 1, except that Compound 1505A was used instead of Compound 125A. Compound 1505B thus obtained was used in the next reaction without additional purification.
    • Synthesis of Compound 1505
  • Figure US20230371359A1-20231116-C00627
  • 0.32 g of Compound 1505 (yield of 27%) was obtained in the same manner as in the synthesis of Compound 125 according to Synthesis Example 1, except that Compound 1505B was used instead of Compound 125B and 4-(2-methylpropyl-1,1-d2)-2-(8-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 8-(4-isobutylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine Substances of the compound were identified by the Mass Spectrum and HPLC analysis.
  • HRMS(MALDI) calcd for C65H68D6Ge2IrN3O: m/z 1259.4261, Found: 1259.4255
    • Example 1
  • As an anode, a glass substrate on which ITO/Ag/ITO was formed to a thickness of 70 Å/1,000 Å/70 Å was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then, cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the anode was provided to a vacuum deposition apparatus.
  • 2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å.
  • Next, CBP (as a host) and Compound 125 (as a dopant) were co-deposited at a weight ratio of 98:2 on the hole transport layer to form an emission layer having a thickness of 400 Å.
  • Then, BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, and Alq3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 Å. LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Mg and Ag were co-deposited at a weight ratio of 90:10 on the electron injection layer to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device.
  • Figure US20230371359A1-20231116-C00628
    • Examples 2 to 12 and Comparative Examples A and B
  • Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds listed in Table 2 below were each used as a dopant instead of Compound 125 in forming an emission layer.
    • Evaluation Example 1: Evaluation of Characteristics of Organic Light-Emitting Device
  • The driving voltage, maximum external quantum efficiency (Max EQE) value (%), and lifespan (LT97, hr) of the organic light-emitting devices manufactured according to Examples 1 to 12 and Comparative Examples A and B were evaluated, and results thereof are shown in Table 2. Here, as a device used for the evaluation, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The lifespan (LT97) (at 3,500 nit) obtained by evaluating time (hr) that lapsed when luminance was 97% of initial luminance (100%), and was indicated in a relative value (%).
  • TABLE 2
    LT97
    Compound No. of Driving (relative value, %)
    dopant in emission layer voltage(V) Max EQE(%) (at 3,500 nit)
    Example 1  125 4.43 23.3 100
    Example 2  128 4.41 23.4  87
    Example 3  163 4.42 24.1  93
    Example 4  365 4.16 22.3 110
    Example 5  505 4.43 23.6 130
    Example 6  526 4.47 25.4 150
    Example 7  676 4.33 25.8 180
    Example 8  806 4.45 23.2 120
    Example 9  865 4.10 23.0 100
    Example 10 1365 4.38 22.5 110
    Example 11 1497 4.35 25.1 165
    Example 12 1505 4.48 22.8 170
    Comparative A 4.35 19.8  27
    Example A
    Comparative B 4.23 20.5  43
    Example B
    Figure US20230371359A1-20231116-C00629
         		125
    Figure US20230371359A1-20231116-C00630
         		128
    Figure US20230371359A1-20231116-C00631
         		163
    Figure US20230371359A1-20231116-C00632
         		365
    Figure US20230371359A1-20231116-C00633
         		505
    Figure US20230371359A1-20231116-C00634
         		526
    Figure US20230371359A1-20231116-C00635
         		676
    Figure US20230371359A1-20231116-C00636
         		806
    Figure US20230371359A1-20231116-C00637
         		866
    Figure US20230371359A1-20231116-C00638
         		1366
    Figure US20230371359A1-20231116-C00639
         		1497
    Figure US20230371359A1-20231116-C00640
         		1505
    Figure US20230371359A1-20231116-C00641
         		A
    Figure US20230371359A1-20231116-C00642
         		B
  • Referring to Table 2, it was confirmed that the organic light-emitting device manufactured according to Examples 1 to 12 had a comparable value of driving voltage and improved external quantum efficiency and longer lifespan characteristics, as compared with the organic light-emitting device manufactured according to Comparative Examples A and B.
  • According to the one or more embodiments, the organometallic compound has excellent electronic characteristics and heat resistance, and thus, an electronic device, for example, an organic light-emitting device, including the organometallic compound may have good driving voltage, good external quantum efficiency, and good lifespan characteristics. In addition, since the organometallic compound has excellent phosphorescence characteristics, a diagnostic composition including the organometallic compound may be provided with a high diagnosis efficiency.
  • It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
  • While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims (20)

What is claimed is:
1. An organometallic compound represented by Formula 1:

M(L1)n1(L2)n2  Formula 1
wherein, in Formula 1,
M is a transition metal,
L1 is a ligand represented by Formula 2A,
L2 is a ligand represented by Formula 2B,
n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, two L1(s) are identical to or different from each other and when n2 is 2, two L2(s) are identical to or different from each other,
the sum of n1 and n2 is 2 or 3, and
L1 and L2 are different from each other:
Figure US20230371359A1-20231116-C00643
wherein, in Formulae 2A and 2B,
Y1 and Y4 are each independently C or N,
X1 is Si,
X21 is O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30),
T1 to T4 are each independently C, N, carbon linked to ring CY1, or carbon linked to M in Formula 1, wherein one of T1 to T4 is carbon linked to M in Formula 1, and one of the remaining T1 to T4 that are not linked to M in Formula 1 is carbon linked to ring CY1,
T5 to T8 are each independently C or N,
at least one of the remaining T1 to T8 that are not carbon linked to M and ring CY1 is N,
provided that, when a group represented by
Figure US20230371359A1-20231116-C00644
in Formula 2B is an unsubstituted benzene group, then at least one of the remaining T5 to T8 that are not carbon linked to M and ring CY1 in Formula 2A is N,
ring CY1 and ring CY14 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R21 to R23 are each independently a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C3-C10 cycloalkyl group, a phenyl group or any combination thereof,
Z1, Z2, Z29, Z30, and R11 to R14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), wherein R12 is neither hydrogen nor a methyl group,
a1 and b1 are each independently an integer from 0 to 20, wherein, when a1 is 2 or more, two or more Z1(s) are identical to or different from each other, and when b1 is 2 or more, two or more R14(s) are identical to or different from each other,
a2 is an integer from 0 to 6, wherein, when a2 is 2 or more, two or more Z2(s) are identical to or different from each other,
two or more of R21 to R23 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of Z1(s) are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of Z2(s) are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R12 and R13 are optionally linked to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of R14(s) are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of Z1, Z2 and R11 to R14 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R10a is the same as defined in connection with R14,
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1,
a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof;
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; 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 C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
2. The organometallic compound of claim 1, wherein
M in Formula 1 is Ir, and the sum of n1 and n2 is 3, or
M in Formula 1 is Pt, and the sum of n1 and n2 is 2.
3. The organometallic compound of claim 1, wherein
X21 in Formula 2A is O or S.
4. The organometallic compound of claim 1, wherein
Z1 in Formula 2A is:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, or any combination thereof; or
a C3-C10 cycloalkyl group or a C1-C10 heterocycloalkyl group, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, or any combination thereof.
5. The organometallic compound of claim 1, wherein
a number of carbons included in R12 of Formula 2B is at least two.
6. The organometallic compound of claim 1, wherein
the organometallic compound represented by Formula 1 satisfies at least one of Condition (1) to Condition (3) below:
Condition (1)
In Formula 2 Å, Z1 is not hydrogen, and a1 is an integer of 1 to 20.
Condition (2)
In Formula 2B, R14 is not hydrogen, and b1 is an integer of 1 to 20.
Condition (3)
In Formula 2 Å, Z2 is not hydrogen, and a2 is an integer of 1 to 6.
7. The organometallic compound of claim 1, wherein
the organometallic compound represented by Formula 1 comprises at least one deuterium, at least one fluoro group (—F), at least one cyano group (—CN), or any combination thereof.
8. The organometallic compound of claim 1, wherein
Z2 in Formula 2A is not hydrogen,
a2 is an integer from 1 to 3, and
at least one of Z2(s) in number of a2 is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
9. The organometallic compound of claim 1, wherein
a group represented by
Figure US20230371359A1-20231116-C00645
in Formula 2A is represented by one of Formulae CY1-1 to CY1-28:
Figure US20230371359A1-20231116-C00646
Figure US20230371359A1-20231116-C00647
Figure US20230371359A1-20231116-C00648
Figure US20230371359A1-20231116-C00649
wherein, in Formulae CY1-1 to CY1-28,
Z11 to Z14 are each independently the same as defined in connection with Z1 in claim 1, wherein each of Z11 to Z14 are not hydrogen,
ring CY10a is a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R10a is the same as described in claim 1,
aa is an integer from 0 to 10, and
* indicates a binding site to M in Formula 1, and *″ indicates a binding site to one of T1 to T4 in Formula 2 Å.
10. The organometallic compound of claim 9, wherein
a group represented by
Figure US20230371359A1-20231116-C00650
in Formula 2A is represented by one of Formulae CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.
11. The organometallic compound of claim 1, wherein
a group represented by
Figure US20230371359A1-20231116-C00651
in Formula 2A is represented by one of Formulae CY2-1 to CY2-6:
Figure US20230371359A1-20231116-C00652
wherein, in Formulae CY2-1 to CY2-6,
T1 to T8 are each independently C or N,
X21 is the same as described in claim 1,
*″ indicates a binding site to ring CY1 in Formula 2A, and
*′ indicates a binding site to M in Formula 1.
12. The organometallic compound of claim 11, wherein
a) at least one of T3 to T8 in Formulae CY2-1 and CY2-6 is N,
b) at least one of T1, T2, and T5 to T8 in Formulae CY2-2 and CY2-5 is N,
c) at least one of T1 and T4 to T8 in Formulae CY2-3 and CY2-4 is N.
13. The organometallic compound of claim 11, wherein
1) T1 to T8 in Formulae CY2-1 to CY2-6 are C;
2) one of T3 to T8 in Formula CY2-1 is N, and the remaining T3 to T8 that are not N in Formula CY2-1 are C;
3) T3 and T8 in Formula CY2-1 are N, and T4 to T7 in Formula CY2-1 are C;
4) T6 and T8 in Formula CY2-1 are N, and T3 to T5 and T7 in Formula CY2-1 are C;
5) one of T1, T2 and T8 in Formula CY2-2 is N, and the remaining T1, T2 and T5 to T8 that are not N in Formula CY2-2 are C;
6) T1 and T8 in Formula CY2-2 are N, and T2 and T5 to T7 in Formula CY2-2 are C;
7) T2 and T8 in Formula CY2-2 are N, and T1 and T5 to T7 in Formula CY2-2 are C;
8) one of T1, T4 and T8 in Formulae CY2-3 and CY2-4 is N, and the remaining T1, T4 and T5 to T8 that are not N in Formulae CY2-3 and CY2-4 are C;
9) T1 and T8 in Formulae CY2-3 and CY2-4 are N, and T4 and T5 to T7 in Formulae CY2-3 and CY2-4 are C;
10) T4 and T8 in Formulae CY2-3 and CY2-4 are N, and T1 and T5 to T7 in Formulae CY2-3 and CY2-4 are C;
11) one of T1 and T8 in Formula CY2-5 is N, and the remaining T1, T2 and T5 to T8 that are not N in Formula CY2-5 are C;
12) T1 and T8 in Formula CY2-5 are N, and T2 and T5 to T7 in Formula CY2-5 are C;
13) one of T4 and T8 in Formula CY2-6 is N, and the remaining T3 to T8 that are not N in Formula CY2-6 are C; or
14) T4 and T8 in Formula CY2-6 are N, and T3 and T5 to T7 in Formula CY2-6 are C.
14. The organometallic compound of claim 1, wherein
a group represented by
Figure US20230371359A1-20231116-C00653
in Formula 2A is represented by one of Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065 and CY2-6001 to CY2-6065:
Figure US20230371359A1-20231116-C00654
Figure US20230371359A1-20231116-C00655
Figure US20230371359A1-20231116-C00656
Figure US20230371359A1-20231116-C00657
Figure US20230371359A1-20231116-C00658
Figure US20230371359A1-20231116-C00659
Figure US20230371359A1-20231116-C00660
Figure US20230371359A1-20231116-C00661
Figure US20230371359A1-20231116-C00662
Figure US20230371359A1-20231116-C00663
Figure US20230371359A1-20231116-C00664
Figure US20230371359A1-20231116-C00665
Figure US20230371359A1-20231116-C00666
Figure US20230371359A1-20231116-C00667
Figure US20230371359A1-20231116-C00668
Figure US20230371359A1-20231116-C00669
Figure US20230371359A1-20231116-C00670
Figure US20230371359A1-20231116-C00671
Figure US20230371359A1-20231116-C00672
Figure US20230371359A1-20231116-C00673
Figure US20230371359A1-20231116-C00674
Figure US20230371359A1-20231116-C00675
Figure US20230371359A1-20231116-C00676
Figure US20230371359A1-20231116-C00677
Figure US20230371359A1-20231116-C00678
Figure US20230371359A1-20231116-C00679
Figure US20230371359A1-20231116-C00680
Figure US20230371359A1-20231116-C00681
Figure US20230371359A1-20231116-C00682
Figure US20230371359A1-20231116-C00683
Figure US20230371359A1-20231116-C00684
Figure US20230371359A1-20231116-C00685
Figure US20230371359A1-20231116-C00686
Figure US20230371359A1-20231116-C00687
Figure US20230371359A1-20231116-C00688
Figure US20230371359A1-20231116-C00689
Figure US20230371359A1-20231116-C00690
Figure US20230371359A1-20231116-C00691
Figure US20230371359A1-20231116-C00692
Figure US20230371359A1-20231116-C00693
Figure US20230371359A1-20231116-C00694
Figure US20230371359A1-20231116-C00695
Figure US20230371359A1-20231116-C00696
Figure US20230371359A1-20231116-C00697
Figure US20230371359A1-20231116-C00698
Figure US20230371359A1-20231116-C00699
Figure US20230371359A1-20231116-C00700
Figure US20230371359A1-20231116-C00701
Figure US20230371359A1-20231116-C00702
Figure US20230371359A1-20231116-C00703
Figure US20230371359A1-20231116-C00704
Figure US20230371359A1-20231116-C00705
Figure US20230371359A1-20231116-C00706
Figure US20230371359A1-20231116-C00707
Figure US20230371359A1-20231116-C00708
Figure US20230371359A1-20231116-C00709
Figure US20230371359A1-20231116-C00710
Figure US20230371359A1-20231116-C00711
Figure US20230371359A1-20231116-C00712
Figure US20230371359A1-20231116-C00713
Figure US20230371359A1-20231116-C00714
Figure US20230371359A1-20231116-C00715
Figure US20230371359A1-20231116-C00716
Figure US20230371359A1-20231116-C00717
Figure US20230371359A1-20231116-C00718
Figure US20230371359A1-20231116-C00719
Figure US20230371359A1-20231116-C00720
Figure US20230371359A1-20231116-C00721
Figure US20230371359A1-20231116-C00722
Figure US20230371359A1-20231116-C00723
Figure US20230371359A1-20231116-C00724
Figure US20230371359A1-20231116-C00725
Figure US20230371359A1-20231116-C00726
Figure US20230371359A1-20231116-C00727
Figure US20230371359A1-20231116-C00728
Figure US20230371359A1-20231116-C00729
Figure US20230371359A1-20231116-C00730
Figure US20230371359A1-20231116-C00731
Figure US20230371359A1-20231116-C00732
Figure US20230371359A1-20231116-C00733
Figure US20230371359A1-20231116-C00734
Figure US20230371359A1-20231116-C00735
Figure US20230371359A1-20231116-C00736
Figure US20230371359A1-20231116-C00737
Figure US20230371359A1-20231116-C00738
Figure US20230371359A1-20231116-C00739
Figure US20230371359A1-20231116-C00740
Figure US20230371359A1-20231116-C00741
Figure US20230371359A1-20231116-C00742
Figure US20230371359A1-20231116-C00743
Figure US20230371359A1-20231116-C00744
Figure US20230371359A1-20231116-C00745
Figure US20230371359A1-20231116-C00746
wherein, in Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065 and CY2-6001 to CY2-6065,
X21 is the same as described in claim 1,
Z21 to Z28 are each independently the same as defined in connection with Z2 in claim 1, wherein each of Z21 to Z28 are not hydrogen,
*″ indicates a binding site to ring CY1 in Formula 2 Å, and
*′ indicates a binding site to M in Formula 1.
15. The organometallic compound of claim 1, wherein
a group represented by
Figure US20230371359A1-20231116-C00747
in Formula 2B is represented by one of Formulae CY14(1) to CY14(63):
Figure US20230371359A1-20231116-C00748
Figure US20230371359A1-20231116-C00749
Figure US20230371359A1-20231116-C00750
Figure US20230371359A1-20231116-C00751
Figure US20230371359A1-20231116-C00752
Figure US20230371359A1-20231116-C00753
Figure US20230371359A1-20231116-C00754
wherein, in Formulae CY14(1) to CY14(63),
R14a to R14d are each independently the same as defined in connection with R14 in claim 1 wherein each of R14a to R14d are not hydrogen,
X14 is C(R1)(R2), N(R1), O, S, or Si(R1)(R2),
R1 to R8 are each the same as defined in connection with R14 in claim 1,
*″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2B and
*′ indicates a binding site to M in Formula 1.
16. An organic light-emitting device comprising:
a first electrode,
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises at least one organometallic compound of claim 1.
17. The organic light-emitting device of claim 16, wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
18. The organic light-emitting device of claim 16, wherein
the emission layer comprises the at least one organometallic compound.
19. The organic light-emitting device of claim 18, wherein
the emission layer further comprises a host, and an amount of the host is greater than that of the organometallic compound.
20. An electronic apparatus comprising the organic light-emitting device of claim 16.
US18/348,775 2019-03-07 2023-07-07 Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device Pending US20230371359A1 (en)

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