Patent Application
20190326526
This application claims the benefit of Korean Patent Application Nos. 10-2018-0046990, filed on Apr. 23, 2018, and 10-2019-0046949, filed on Apr. 22, 2019, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference.
One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
Organic light-emitting devices are self-emission devices, which have better characteristics in terms of a viewing angle, a response time, a brightness, a driving voltage, and a 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.
Luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins. An example of the luminescent compounds includes a phosphorescent luminescent compound.
Aspects of the present disclosure provide a novel organometallic compound and an organic light-emitting device and a diagnostic composition including the same.
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:
In Formula 1, R1 to R12 and R19 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 C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), and
The number of carbon atoms included in Formula 2 may be 4 or more,
Another aspect of the present disclosure provides an organic light-emitting device includes: a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes an organometallic compound described above.
The organometallic compound in the emission layer of the organic layer may act as a dopant.
Still another aspect of the present disclosure provides a diagnostic composition including an organometallic compound described above.
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.
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, the singular forms “a,” “an,” and “the” are intended to include the plural forms, including “at least one,” unless the content clearly indicates otherwise. 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.
“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). In an exemplary embodiment, “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. In an exemplary embodiment, 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 organometallic compound according to an embodiment is represented by Formula 1 below:
In Formula 1, R1 to R12 and R19 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 C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Formulae 2 and 3 and Q1 to Q9 are the same as described above.
In an exemplary embodiment, R1 to R12 and R19 may each independently be:
In one embodiment, R1 to R9 and R19 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, or —Si(Q3)(Q4)(Q5). Q3 to Q5 are the same as described in this disclosure.
In one or more embodiments, R1 to R12 and R19 may each independently be:
In one or more embodiments, R1 to R12 and R19 may each independently be:
In Formulae 9-1 to 9-66 and 10-1 to 10-249, * indicates a binding site to a neighboring atom, Ph indicates a phenyl group, and TMS indicates a trimethylsilyl group.
The “groups represented by Formulae 9-1 to 9-66 in which a hydrogen is substituted with deuterium” may refer to, for example, groups represented by Formulae 9-501 to 9-552:
The “groups represented by Formulae 10-1 to 10-249 in which a hydrogen is substituted deuterium” may refer to, for example, groups represented by Formulae 10-501 to 10-510:
At least one of R1 to R6 may each independently be a group represented by Formula 2:
The number of carbon atoms included in Formula 2 may be 4 or more (for example, 4 to 20, 4 to 15 or 4 to 10),
The terms “deuterium-containing C1-C20 alkyl group” and “deuterium-containing C3-C10 cycloalkyl group” as used herein refer to a C1-C20 alkyl group or a C3-C10 cycloalkyl group, each substituted with a deuterium. In an exemplary embodiment, the deuterium-containing methyl group refers to —CDH2, —CD2H, and —CD3.
The term “C1-C20 alkyl group” as used herein refers to, for example, 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, or a tert-decyl group, but embodiments of the present disclosure are not limited thereto.
The term “C3-C10 cycloalkyl group” as used herein refers to, for example, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, or a bicyclo[2.2.2]octyl group, but embodiments of the present disclosure are not limited thereto.
In one embodiment, one of R2 to R5 in Formula 1 may be a group represented by Formula 2.
In one or more embodiments, one of R2 to R5 in Formula 1 may be a group represented by Formula 2, and groups other than the one of R2 to R5 which is the group represented by Formula 2 among R1 to R6 may be hydrogen.
In one or more embodiments, in Formula 1,
In one or more embodiments, at least one of R7 to R9 in Formula 1 may not be hydrogen.
In one or more embodiments, at least one of R7 to R9 in Formula 1 may each independently be, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, or a substituted or unsubstituted C6-C60 aryl group.
In one or more embodiments, at least one of R7 to R9 in Formula 1 may each independently be, a substituted or unsubstituted C2-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, or a substituted or unsubstituted C6-C60 aryl group.
In one or more embodiments, in Formula 1,
In one or more embodiments, R19 in Formula 1 may be hydrogen.
In one or more embodiments, R7 and R9 in Formula 1 may not be hydrogen, and R7 and R9 may be identical to each other.
In one or more embodiments, R7 and R9 in Formula 1 may not be hydrogen, and R7 and R9 may be different from each other.
In one or more embodiments, R7 and R9 in Formula 1 may not be hydrogen, R7 and R9 may be different from each other, and the number of carbon atoms included in R7 may be greater than that of carbon atoms included in R9.
In one or more embodiments, R13 in Formula 2 may be hydrogen or deuterium.
In one or more embodiments, R13 in Formula 2 may be a C1-C20 alkyl group, a deuterium-containing C1-C20 alkyl group, a C3-C10 cycloalkyl group, or a deuterium-containing C3-C10 cycloalkyl group.
In one or more embodiments, R14 and R15 in Formula 2 may be different from each other.
In one or more embodiments, in Formula 2,
In one or more embodiments, in Formula 2, R14 and R15 may each independently be —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, groups represented by Formulae 9-1 to 9-33, groups represented by Formulae 9-1 to 9-33 in which a hydrogen is substituted with deuterium, groups represented by Formulae 10-1 to 10-10, or groups represented by Formulae 10-1 to 10-10 in which a hydrogen is substituted with deuterium, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, a case where R13 to R15 in Formula 2 are identical to each other may be excluded.
In one or more embodiments, R13 to R15 in Formula 2 may be different from each other.
In one or more embodiments, a case where each of R13 to R15 in Formula 2 is a methyl group may be excluded. That is, R13, R14 and R15 in Formula 2 may not be a methyl group, simultaneously.
At least one of R10 and R12 in Formula 1 may be a group represented by Formula 3:
R16 to R18 in Formula 3 may each independently be:
In an exemplary embodiment, R16 to R18 in Formula 3 may each independently be hydrogen or deuterium.
In one embodiment, one or more of R16 to R18 in Formula 3 may not be hydrogen or deuterium. That is, Formula 3 may include 0-2 benzylic protons.
In one embodiment, two or more of R16 to R18 in Formula 3 may not be hydrogen or deuterium. That is, Formula 3 may include 0-1 benzylic protons.
In one embodiment, R16 to R18 in Formula 3 may not be hydrogen or deuterium.
In one embodiment, in Formula 3,
Examples of “the C2-C20 alkyl group or the deuterium-containing C2-C20 alkyl group” may include:
In one or more embodiments, R10 and R12 in Formula 1 may be identical to each other.
In one or more embodiments, R10 and R12 in Formula 1 may be different from each other.
In an exemplary embodiment, in Formula 1, R10 may be an ethyl group, and R12 may be a methyl group, an n-propyl group, or an isopropyl group, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, at least one of R10, R12 and R14 in Formulae 1 and 2 may each independently be a C3-C10 cycloalkyl group, a deuterium-containing C3-C10 cycloalkyl group, or a combination thereof.
Two or more of R1 to R9 and R19 in Formula 1 may optionally be linked to form a C5-C30 carbocyclic group unsubstituted or substituted with R1a, a C2-C30 heterocyclic group unsubstituted or substituted with R1a, or a combination thereof.
In an exemplary embodiment, two or more of R1 to R9 and R19 in Formula 1 may optionally be linked to form a cyclopentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a bicycle-heptane group, a bicycle-octane group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, a phenalene group, a benzofuran group, a benzothiophene group, a benzoselenophene group, an indole group, an indene group, a benzosilole group, an azabenzofuran group, an azabenzothiophene group, an azabenzoselenophene group, an azaindole group, an azaindene group, or an azabenzosilole group, each unsubstituted or substituted with R1a, but embodiments of the present disclosure are not limited thereto.
R1a may be the same as defined in connection with R7.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition 1 to Condition 6:
In one or more embodiments, the organometallic compound may be one of Compounds 1 to 20, but embodiments of the present disclosure are not limited thereto:
In Compounds 1 to 20, TMS is a tri(methyl)silyl group.
Formula 1 has the structure as described herein, wherein at least one of R1 to R6 is each independently a group represented by Formula 2:
The number of carbon atoms included in Formula 2 may be 4 or more, R13 may be hydrogen, deuterium, a C1-C20 alkyl group, a deuterium-containing C1-C20 alkyl group, a C3-C10 cycloalkyl group, or a deuterium-containing C3-C10 cycloalkyl group, R14 and R15 may each independently be a C1-C20 alkyl group, a deuterium-containing C1-C20 alkyl group, a C3-C10 cycloalkyl group, or a deuterium-containing C3-C10 cycloalkyl group, and * indicates a binding site to a neighboring atom.
That is, the group represented by Formula 2 may be an alkyl group having 0-1 benzylic protons or a derivative thereof.
While not wishing to be bound to a specific theory, since the benzylic proton has high chemical reactivity, as compared with protons other than the benzylic protons, the benzylic proton may cause a side reaction due to the generation of intermediates in various forms. However, since at least one of R1 to R6 in Formula 1 can each independently be a group represented by Formula 2 which is an alkyl group having 0-1 benzylic protons or a derivative thereof, the organometallic compound represented by Formula 1 has a stable chemical structure in which the generation of side reactions before and after synthesis is minimized. In addition, interaction between the organometallic compound molecules may be minimized during the driving of an electronic device (for example, an organic light-emitting device) including the organometallic compound represented by a Formula 1. Therefore, the electronic device, for example, the organic light-emitting device, which includes an organometallic compound represented by Formula 1, may have improved driving voltage, improved current density, improved external quantum luminescence efficiency, improved roll off ratio, and improved lifespan.
Furthermore, R13, R14 and R15 in Formula 2 are not a methyl group, simultaneously. That is, a group represented by Formula 2 is not a tert-butyl (t-butyl) group. While not wishing to be bound to a specific theory, a t-butyl group may be cleaved from a quinoline ring of Formula 1 to form a t-butyl radical (or, t-butyl cation), which causes a decrease in lifespan of the electronic device, for example, the organic light-emitting device. However, when a group represented by Formula 2 is not a tert-butyl (t-butyl) group, the lifespan of the electronic device, for example, the organic light-emitting device, which includes an organometallic compound represented by Formula 1, may not be substantially decreased.
Synthesis methods of the organometallic compounds represented by Formula 1 may be understood by one of ordinary skill in the art by referring to Synthesis Examples provided below.
The organometallic compound represented by Formula 1 is 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. Thus, another aspect provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is disposed between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes the 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, improved driving voltage, improved current density, improved external quantum luminescence efficiency, improved roll off ratio, and improved lifespan.
The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. In an exemplary embodiment, 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, in the emission layer, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
In one embodiment, the emission layer may emit red light.
The expression “(an organic layer) includes organometallic compounds” 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.”
In an exemplary embodiment, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may exist in an 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 be present in the same layer (for example, Compound 1 and Compound 2 all may be present 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.
In one embodiment, 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, a buffer 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 between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
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 commonly used in 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 be a material with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive 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, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. In an exemplary embodiment, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
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.
A hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a compound that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. In an exemplary embodiment, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 (angstroms per second) 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. In an exemplary embodiment, 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, β-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 sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or a combination thereof:
Ar101 and 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, a perylenylene group, or a pentacenylene group; or 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, a perylenylene group, or a pentacenylene 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, 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 C1-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 a combination thereof.
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may be 0, 1, or 2. In an exemplary embodiment, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
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, a pentyl group, a hexyl group, and so on), or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);
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 a combination thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl 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, a C1-C100 alkyl group, a C1-C10 alkoxy group, or a combination thereof, but embodiments of the present disclosure are not limited thereto.
R109 in Formula 201 may be:
a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or
a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl 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, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.
In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:
wherein R101, R111, R112, and R109 in Formula 201A may be understood by referring to the description provided herein.
In an exemplary embodiment, the compound represented by Formula 201, and the compound represented by Formula 202 may include compounds HT1 to HT20 illustrated below, but are not limited thereto.
A thickness of the hole transport region may be in a range of about 100 angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, and for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and 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, or a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto.
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.
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.
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 and/or materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. In an exemplary embodiment, 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.
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, Compound H50, Compound H51, or a combination thereof:
In one or more embodiments, the host may further include a compound represented by Formula 301:
Ar111 and Ar112 in Formula 301 may each independently be:
a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or
a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, each substituted with a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.
Ar113 to Ar116 in Formula 301 may each independently be:
a C1-C10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or
a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group, each substituted with a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.
In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.
Ar113 to Ar116 in Formula 301 may each independently be:
a C1-C10 alkyl group, substituted with a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, a phenanthrenyl group, or a fluorenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl 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, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, or a combination thereof; or
but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the host may include a compound represented by Formula 302 below:
Ar122 to Ar125 in Formula 302 may be the same as described in connection with Ar113 in Formula 301.
Ar126 and Ar127 in Formula 302 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
In Formula 302, k and l may each independently be an integer from 0 to 4. In an exemplary embodiment, k and l may be 0, 1, or 2.
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 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, but embodiments of the present disclosure are not limited thereto.
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.
In an exemplary embodiment, 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, but the structure of the electron transport region is not limited thereto. 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 a combination thereof, but embodiments of the present disclosure are not limited thereto:
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.
The electron transport layer may include BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or a combination thereof:
In one or more embodiments, the electron transport layer may include at least one ET1 to ET25, but are not limited thereto:
A thickness of the electron transport layer may be in a range of 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) or ET-D2:
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 a combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a 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, or a combination thereof, which have a relatively low work function. In an exemplary embodiment, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, 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 has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.
Another aspect of the present disclosure provides a diagnostic composition including an 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 non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond for a carbon-carbon single bond anywhere in the chain of the C2-C60 alkyl 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 formed by substituting at least one carbon-carbon triple bond for a carbon-carbon single bond anywhere in the chain of the C2-C60 alkyl 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 or multi-cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl 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 “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-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 “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heteroaromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heteroaromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 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 “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group used herein indicates —SA103 (wherein A103 is the C6-C60 aryl 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 selected from 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 “C2-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S other than 2 to 30 carbon atoms. The C2-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
A substituent of the substituted C5-C30 carbocyclic group, the substituted C2-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 C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-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, the substituted monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof may 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 C1-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), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof.
The 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, 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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one of a C1-C60 alkyl group and 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.
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” as 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.
(17.48 mmol) of a starting material 2-A was mixed with 72 mL of tetrahydrofuran (THF), and the mixture was cooled to a temperature of 0° C. 29 mL of 1M LiAlH4 in THF solution was added dropwise thereto. Then, the mixture was heated to room temperature and refluxed overnight. 1 mL of water was added to a reactant obtained therefrom, 2 mL of 50% NaOH (aq) was added thereto, and ethyl acetate (EA) was added thereto to extract an organic layer therefrom. The extracted organic layer was dried, and column chromatography was performed thereon to obtain 3.0 g (yield of 82%) of Intermediate 2-B.
3 g (19.04 mmol) of Intermediate 2-B, 4.23 g (28.55 mmol) of starting material 2-C, 0.18 g (0.190 mmol) of RuCl2(PPh3)3, and 1.92 g (34.26 mmol) of KOH were mixed with 53 mL of toluene and refluxed overnight at a temperature of 120° C. The result obtained therefrom was cooled to room temperature and washed with water. Then, column chromatography was performed thereon to obtain 4.4 g (yield of 48%) of Intermediate 2-E. The obtained compound was identified by LC-MS analysis.
LC-MS m/z=268.14 (M+H)+.
4.4 g (16.43 mmol) of Intermediate 2-E, 1.81 g (18.08 mmol) of starting material 2-F, 0.37 g (1.64 mmol) of Pd(OAc)2, 6.81 g (49.30 mmol) of K2CO3, and 2.70 g (3.29 mmol) of S-phos were mixed with 154 mL of dioxane and 38 mL of H2O and refluxed overnight at a temperature of 90° C. The result obtained therefrom was cooled to room temperature and washed with water and methylene chloride. Then, column chromatography was performed thereon to obtain 3.8 g (yield of 80%) of Intermediate 2-G. The obtained compound was identified by LC-MS analysis. LC-MS: m/z=288.28 (M+H)+.
1.8 g (6.26 mmol) of Intermediate 2-G was mixed with methanol, and 0.36 g of Pd on carbon was added thereto. A hydrogen gas was bubbled into a reactant obtained therefrom for 6 hours or more. After the reaction was completed, MeOH was removed therefrom, and the reaction product was washed with H2O and methylene chloride. Then, column chromatography was performed thereon to obtain 0.8 g (yield of 44%) of Intermediate 2-H. The obtained compound was identified by LC-MS analysis.
LC-MS: m/z=290.20 (M+H)+.
0.40 g (1.13 mmol) of IrCl3.4H2O, 14 mL of 2-ethoxyethanol, and 4.5 mL of H2O were added to 0.74 g (2.55 mmol) of Intermediate 2-H and refluxed overnight at a temperature of 120° C. A result obtained therefrom was cooled to room temperature, filtered, washed with methanol, and then dried to obtain 0.65 g of Intermediate 2-1.
0.65 g (0.40 mmol) of Intermediate 2-1, 0.74 g (4.04 mmol) of 2,2,6,6-tetramethylheptane-3,5-dione, and 0.56 g (4.04 mmol) of K2CO3 were mixed with 22 mL of 2-ethoxyethanol and stirred overnight at room temperature. A result obtained therefrom was washed with ethyl acetate and H2O. Then, column chromatography was performed thereon to obtain 0.43 g (yield of 57%) of Compound 2. The obtained compound was identified by LC-MS analysis.
LC-MS/z=953.27 (M+H)+.
3.70 g (18.67 mmol) of a starting material 1-A, 2.94 g (19.61 mmol) of a starting material 1-B, 1.08 g (0.93 mmol) of Pd(PPh3)4, and 6.45 g (46.68 mmol) of K2CO3 were mixed with 60 mL of THF and 30 mL of H2O and refluxed overnight at a temperature of 90° C. A result obtained therefrom was cooled to room temperature and washed with water and methylene chloride. Then, column chromatography was performed thereon to obtain 4.00 g (yield of 80%) of Intermediate 1-C. The obtained compound was identified by LC-MS analysis.
LC-MS m/z=268.12 (M+H)+.
4.00 g (14.96 mmol) of Intermediate 1-C, 1.79 g (18.95 mmol) of starting material 1-D, 0.17 g (0.75 mmol) of Pd(OAc)2, 5.17 g (37.40 mmol) of K2CO3, and 0.61 g (1.50 mmol) of S-phos were mixed with 50 mL of THF and 25 mL of H2O and refluxed overnight at a temperature of 90° C. A result obtained therefrom was cooled to room temperature and washed with water and methylene chloride. Then, column chromatography was performed thereon to obtain 2.20 g (yield of 51%) of Intermediate 1-E. The obtained compound was identified by LC-MS analysis.
LC-MS m/z=288.22 (M+H)+
2.20 g (7.60 mmol) of Intermediate 1-E was mixed with methanol, and 0.24 g of Pd on carbon was added thereto. A hydrogen gas was bubbled into a reactant obtained therefrom for 6 hours or more. After the reaction was completed, MeOH was removed therefrom, and the reaction product was washed with H2O and methylene chloride.
Then, column chromatography was performed thereon to obtain 1.55 g (yield of 70%) of Intermediate 1-F. The obtained compound was identified by LC-MS analysis.
LC-MS m/z=290.22 (M+H)+.
0.96 g (2.73 mmol) of IrCl3.4H2O, 10 mL of 2-ethoxyethanol, and 3.5 mL of H2O were added to 1.58 g (5.47 mmol) of Intermediate 1-F and refluxed overnight at a temperature of 120° C. A result obtained therefrom was cooled to room temperature, filtered, washed with methanol, and then dried to obtain 1.35 g of Intermediate 1-G.
1.35 g (0.86 mmol) of Intermediate 1-G, 0.89 g (8.64 mmol) of pentane-2,4-dione, and 0.91 g (8.64 mmol) of Na2CO3 were mixed with 17 mL of 2-ethoxyethanol and refluxed overnight. A result obtained therefrom was washed with ethyl acetate and H2O. Then, column chromatography was performed thereon to obtain 0.50 g (yield of 33%) of Compound 1. The obtained compound was identified by LC-MS analysis.
LC-MS m/z=869.36 (M+H)+.
3.33 g (yield of 89%) of Intermediate 5-B was obtained in the same manner as in Synthesis of Intermediate 2-B in Synthesis Example 1, except that 4.00 g (18.52 mmol) of a starting material 5-A was used instead of the starting material 2-A.
3.09 g (yield of 60%) of Intermediate 5-E was obtained in the same manner as in Synthesis of Intermediate 2-E in Synthesis Example 1, except that 3.33 g (16.48 mmol) of Intermediate 5-B was used instead of Intermediate 2-B, and 3.66 g (24.72 mmol) of starting material 5-C was used instead of starting material 2-C.
2.26 g (yield of 82%) of Intermediate 5-G was obtained in the same manner as in Synthesis of Intermediate 2-G in Synthesis Example 1, except that 3.00 g (9.61 mmol) of Intermediate 5-E was used instead of Intermediate 2-E, and 1.06 g (10.57 mmol) of starting material 5-F was used instead of starting material 2-F. The obtained compound was identified by LC-MS analysis. LC-MS m/z=288.28 (M+H)+.
1.22 g (yield of 55%) of Intermediate 5-H was obtained in the same manner as in Synthesis of Intermediate 2-H in Synthesis Example 1, except that 2.2 g (7.65 mmol) of Intermediate 5-G was used instead of Intermediate 2-G. The obtained compound was identified by LC-MS analysis. LC-MS m/z=290.20 (M+H)+.
1.00 g of Intermediate 5-1 was obtained in the same manner as in Synthesis of Intermediate 2-1, except that 1.22 g (4.22 mmol) of Intermediate 5-H was used instead of Intermediate 2-H.
0.72 g (yield of 55%) of Compound 5 was obtained in the same manner as in Synthesis of Compound 2 of Synthesis Example 1, except that 1.00 g (0.97 mmol) of Intermediate 5-1 was used instead of Intermediate 2-1, and pentane-2,4-dione was used instead of 2,2,6,6-tetramethylheptane-3,5-dione. The obtained compound was identified by LC-MS analysis.
LC-MS: m/z=869.40 (M+H)+.
1.10 g (yield of 65%) of Compound 12 was obtained in the same manner as in Synthesis of Compound 2 of Synthesis Example 1, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione was used instead of 2,2,6,6-tetramethylheptane-3,5-dione.
LC-MS: m/z=1008.61 (M+H)+.
As an anode, a glass substrate, on which ITO/Ag/ITO were deposited to thicknesses 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 cleansed by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate 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 (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å.
Then, CBP (host) and Compound 2 (dopant) were co-deposited on the hole transport layer at a weight ratio of 98:2 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, 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 on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device (which emits red light).
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 1 were each used instead of Compound 2 as a dopant in forming an emission layer.
The driving voltage, current density, external quantum luminescent efficiency (EQE), roll-off ratio, full width at half maximum (FWHM) and peak wavelength of emission peaks in EL spectra, and lifespan (LT97) of the organic light-emitting devices manufactured according to Examples 1 to 4 and Comparative Examples A to F are evaluated, and results thereof are shown in Table 1. A current-voltage meter (KEITHLEY 2400) and a luminance meter (MINOLTA Cs-1000 A) were used as the evaluation apparatuses, and the lifespan (LT97) (at 3,500 nit) indicates the time that lapsed when luminance was 97% of initial luminance (100%). The roll-off ratio was calculated by Equation 20 below.
Roll off ratio={1−(Efficiency (at 3,500 nit)/Maximum luminescent efficiency)}×100% Equation 20
n-Hex in Compound A indicates an n-hexyl group.
Referring to Table 1, it was confirmed that the organic light-emitting devices of Examples 1 to 4 showed improved driving voltage, improved current density, improved external quantum luminescent efficiency, improved roll-off ratio, and improved lifespan characteristics compared to those of the organic light-emitting device of Comparative Examples A to F.
Since the organometallic compound has excellent electric characteristics and thermal stability, an organic light-emitting device including the organometallic compound may have excellent driving voltage, luminescent efficiency, quantum efficiency, roll-off ratio, and lifespan characteristics.
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.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2018-0046990 | Apr 2018 | KR | national |
| 10-2019-0046949 | Apr 2019 | KR | national |
