Patent Application
20210347798
This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0053393, filed on May 4, 2020, in the Korean Intellectual Property Office, the content of which is incorporated herein in its entirety by reference.
Embodiments relate to an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the same.
Organic light-emitting devices are self-emission devices, which have improved characteristics in terms of viewing angle, response times, brightness, driving voltage, and response speed, and produce full-color images.
One example of an organic light-emitting device may include an anode, a cathode, and an organic layer located between the anode and the cathode and including 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.
Meanwhile, luminescent compounds, for example, phosphorescent compounds, may be used for monitoring, sensing, and detecting biological materials such as various cells and proteins.
Embodiments relate to an organometallic compound, an organic light-emitting device including the same, 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 of the disclosure.
According to an aspect, provided is an organometallic compound represented by Formula 1.
In Formula 1,
According to an aspect, provided is an organic light-emitting device including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organometallic compound represented by Formula 1.
According to an aspect, provided is a diagnostic composition including at least one organometallic compound represented by Formula 1.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with
FIGURE, which is a schematic cross-sectional 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. 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 organometallic compound is represented by Formula 1 below:
In Formula 1, M1 may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium(Ge), zirconium (Zr), ruthenium(Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
In an embodiment, M1 may be Pd, Pt, or Au.
In an embodiment, M1 in Formula 1 may be Pt or Pd.
In an embodiment, M1 in Formula 1 may be Pt.
In Formula 1, A2 and A3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In an embodiment, A2 and A3 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole 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, a tetrazole 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, an indazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a benzotriazole group, a diazaindene group, a triazaindene group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, the
moiety in Formula 1 may be a group represented by any one of Formulae A1-1 to A1-9 below:
In Formulae A1-1 to A1-9,
In an embodiment, the
moiety in Formula 1 may be a group represented by any one of Formulae A4-1 to A4-8 below:
In Formulae A4-1 to A4-8,
In Formula 1, X20 and X30 are each independently C or N.
In an embodiment, X20 and X30 in Formula 1 may each be C.
In Formula 1, L10, L20, L30, and L40 each independently indicate a chemical bond.
In an embodiment, L10, L20, L30, and L40 may each independently indicate a coordinate bond or a covalent bond.
In an embodiment, two of L10, L20, L30, and L40 may indicate a covalent bond, and the other two may indicate a coordinate bond. Thus, the organometallic compound represented by Formula 1 may be electrically neutral.
In an embodiment, L10 and L40 may each indicate a coordinate bond, and Lzo and Lao may each indicate a covalent bond.
In Formula 1, T1 and T2 are each independently a single bond, *—N[(L5)a5-(R5)b5]—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R5)—*′, *—Si(R5)(R5)—*′, *—Ge(R5)(R5)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)═C(R6)—*′, *—C(═S)—*′, or *—C≡C—*′.
In an embodiment, T1 and T2 may each independently a single bond, a single bond, *—N[(L5)a5-(R5)b5]—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—O—*′, or *—S—*′.
In an embodiment, T1 may be *—N[(L5)a5-(R5)b5]—*′, and T2 may be *—O—*′ or *—S—*′.
In Formula 1, n1 and n2 are each independently an integer from 1 to 3.
When n1 is 2 or more, two or more of T1(s) are identical to or different from each other, and when n2 is 2 or more, two or more of T2(s) are identical to or different from each other.
In an embodiment, n1 and n2 may each independently be 1 or 2. For example, n1 and n2 may each be 1.
In Formula 1, is *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*′, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, *—Ge(R7)(R8)—*′, *—S—*′, *—Se—*′, *—O—*′, or *—P(═O)(R7)—*′.
In an embodiment, may be *—N(R7)—*′, *—B(R7)—*′, *—C(R7)(R8)—*′, *—S—*′, or *—O—*′.
In an embodiment, may be *—N(R7)—*′, *—S—*′, or *—O—*′.
In an embodiment, L8 may be a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group, and
a5 may be an integer from 1 to 3, wherein when a5 is 2 or more, two or more of L5(s) may be identical to or different from each other.
In an embodiment, L5 may 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
In Formula 1, R1 to R8, R11, R12, R20, R30, and R41 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted 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), —B(Q6)(Q7), or —P(═O)(Q8)(Q9), and
In Formula 1, b20 and b30 are each independently an integer from 1 to 10, wherein when b20 is 2 or more, two or more of R20(s) are identical to or different from each other, and when b30 is 2 or more, two or more of R30(s) are identical to or different from each other.
In an embodiment, R1 to R8, R11, R12, R20, R30, and R41 may each independently be:
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 phenyl 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 benzoquinolinol 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl 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, or an imidazopyrimidinyl group;
In an embodiment, R1 to R8, R11, R12, R20, R30, and R41 may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by Formulae 9-1 to 9-19, or a group represented by Formulae 10-1 to 10-194:
In Formulae 9-1 to 9-19 and 10-1 to 10-194, * indicates a binding site to a neighboring atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.
In Formula 1, neighboring two or more among R1 to R8, R11, R12, R20, R30, and R41 may optionally be linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, neighboring two or more among R1 to R8, R11, R12, R20, R30, and R41 may optionally be linked to each other via a single bond, a double bond, or a first linking group 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 (for example, a fluorene group, a xanthene group, an acridine group, or the like, each unsubstituted or substituted with at least one R10a). R10a is the same as described in connection with R1.
The first linking group may be *—N(R9)—*′, *—B(R9)—*′, *—P(R9)—*′, *—C(R9)(R10)—*′, *—Si (R9)(R10)—*′, *—Ge(R9)(R10)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R9)═*′, *═C(R9)—*′, *—C(R9)═C(R10)—*′, *—C(═S)—*′, or *—C≡C—*′, R9 and R10 are the same as described in connection with R1, and * and *′ each indicate a binding site to a neighboring atom.
In an embodiment, the organometallic compound represented by Formula 1 may have an asymmetric structure.
In an embodiment, the organometallic compound represented by Formula 1 may be represented by any one Formulae 11-1 to 11-12 below:
In Formulae 11-1 to 11-12,
R11 to R18, R21 to R26, R31 to R33, and R41 to R47 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted 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), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, the organometallic compound may be one of Compounds 1 to 240:
The organometallic compound represented by Formula 1 may satisfy a structure of Formula 1 described above, a ligand includes a carbene ring and a pyridine ring, and a pentagonal ring is directly condensed to the pyridine ring as described in Formula 1, and thus, as compared to another compound having a similar structure, the organometallic compound represented by Formula 1 may have a lower singlet energy level and a similar triplet energy level. Accordingly, the organometallic compound represented by Formula 1 may have improved photochemical stability and may be suitable for deep blue emission, and an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1, may have excellent luminescence efficiency and excellent color purity.
For example, with respect to Compounds 1 to 12 and Comparative Compound A, a highest occupied molecular orbital (HOMO), a lowest unoccupied molecular orbital (LUMO), a triplet (T1) energy level, a singlet (S1) energy level, and a spin density were evaluated using DFT method of Gaussian program (involving structure optimization at B3LYP/6-31G(d,p) level), and the results thereof are shown in Table 1.
From Table 1, it is confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use as a material for an emission layer of an electronic device, for example, an organic light-emitting device.
In addition, the organometallic compound represented by Formula 1 may have a higher spin density compared to Comparative Compound. Accordingly, metal to ligand charge transfer (MLCT) may occur, resulting in improved efficiency and improved lifespan of 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.
Accordingly, the organometallic compound represented by Formula 1 is suitable for use as a material of an organic light-emitting device, for example, a material for an emission layer in an organic layer of the organic light-emitting device. Thus, according to an aspect, provided is an organic light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes 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 efficiency, high power, high quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.
In an embodiment, in the organic light-emitting device, 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, 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.
In an embodiment, the organometallic compound represented by Formula 1 may be included in the emission layer.
The organometallic compound included in the emission layer may act as an emitter. For example, an emission layer including the organometallic compound represented by Formula 1 may emit phosphorescent light generated by the transfer of the triplet excitons of the organometallic compound into the ground state.
In an embodiment, the emission layer including the organometallic compound represented by Formula 1 may further include a host. The host may be any host, and details of the host may be the same as described in the present specification. The amount of the host in the emission layer may be greater than the amount of the organometallic compound represented by Formula 1.
In an embodiment, the emission layer may include a host and a dopant, the host may be any host, and the dopant may include the organometallic compound represented by Formula 1. The emission layer may emit phosphorescent light generated by the transfer of triplet excitons of the organometallic compound, which acts as a dopant, to the ground state.
In an embodiment, when the emission layer further includes a host, the amount of the host may be greater than the amount of the organometallic compound.
In an embodiment, the emission layer may include a host and a dopant, the host may be any host, the dopant may include the organometallic compound represented by Formula 1, and the emission layer may further include a fluorescent dopant. The emission layer may emit fluorescent light that is generated by the transfer of the triplet excitons of the organometallic compound to the fluorescent dopant and then transition thereof.
In an embodiment, the emission layer may emit blue light having a maximum emission wavelength of about 430 nm to about 480 nm.
The expression “(an organic layer) includes at least one organometallic compound” 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 in the emission layer of the organic light-emitting device. In an embodiment, 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 term “organic layer” 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.
FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, a 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 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 located under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art 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.
In an embodiment, 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 materials 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 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In an embodiment, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), 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, but the structure of the first electrode 11 is not limited thereto.
The organic layer 15 is located 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 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 an embodiment, 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, wherein, for each structure, each layer is sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, 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 torr 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 at least one of 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/dodecyl benzenesulfonic 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 any combination thereof:
In Formula 201, Ar101 to Ar102 may each independently be:
In Formula 201, xa and xb may each independently be an integer from 0 to 5 or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be:
In Formula 201, R109 may be:
In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but embodiments of the present disclosure are not limited thereto:
In Formula 201A, R101, R111, R112, and R109 may be understood by referring to the description provided herein.
For example, 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 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, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 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 one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. 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; and 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.
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 an 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 material that is used to form the emission layer.
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 and materials for a host to be explained later. 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.
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 at least one of TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or any combination thereof:
In an embodiment, the host may further include a compound represented by Formula 301 below.
In Formula 301, Ar111 and Ar112 may each independently be:
Ar113 to Ar116 in Formula 301 may each independently be:
In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, for example, 0, 1, or 2.
In Formula 301, Ar113 and Ar116 may each independently be:
In an embodiment, the host may include a compound represented by Formula 302 below:
Details of Ar122 to Ar125 in Formula 302 are 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).
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 an embodiment, due to the emission layer having 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 about 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 luminescence characteristics may be obtained without a substantial increase in driving voltage.
Then, an electron transport region may be located 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, and 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, at least one of BCP, Bphen, BAlq, or any 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 excellent hole blocking characteristics without a substantial increase in driving voltage.
The electron transport layer may further include at least one of BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof.
In an embodiment, the electron transport layer may include at least one of Compounds 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.
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 (lithium quinolate, LiQ) or ET-D2:
The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.
The electron injection layer may include at least one LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, 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 located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, 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 the material for forming the second electrode 19. In an embodiment, 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 FIGURE, but embodiments of the present disclosure are not limited thereto.
According to an aspect, provided is a diagnostic composition including at least one organometallic compound represented by Formula 1.
The organometallic compound represented by Formula 1 provides high luminescence 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 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” used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C2-C60 alkenyl group” as used herein has a structure including at least one carbon-carbon double bond in the middle or at the terminus 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 has a structure including at least one carbon-carbon triple bond in the middle or at the terminus 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 group having 3 to 10 carbon atoms, and 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 monocyclic group having at least one heteroatom of N, O, P, Si, B, Se, Ge, Te, and S as a ring-forming atom and 1 to 10 carbon atoms, and 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 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 hetero atom of N, O, P, Si, B, Se, Ge, Te, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include 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. 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 two or more rings may be fused to each other. The C7-C60 alkylaryl group refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom of N, O, P, Si, B, Se, Ge, Te, 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 carbocyclic aromatic system that has at least one heteroatom of N, O, P, B, Se, Ge, Te, and S as a ring-forming atom, and 1 to 60 carbon atoms. 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 C2-C60 alkylheteroaryl group refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as 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 non-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 1 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 non-aromaticity in its entire molecular structure. 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 “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom of N, O, P, Si, B, Se, Ge, Te, and S other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
At least one 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 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 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 alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
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.
3-fluorobenzofuro[3,2-c]pyridine (7.80 g, 41.70 mmol), 2-methoxy-9H-carbazole (9.86 g, 50.04 mmol), and potassium carbonate (11.50 g, 83.40 mmol) were mixed with 160 ml of dimethylsulfoxide (DMSO), and stirred at 150° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and subjected to filtration, followed by concentration under reduced pressure. The obtained product was filtered using isopropyl alcohol to thereby obtain Intermediate (A) (11.80 g, 32.38 mmol, yield=78%).
LC-Mass (calculated: 364.12 g/mol, found: M+1=365 g/mol).
Intermediate (A) (11.80 g, 32.38 mmol) and pyridine hydrochloride (Py-HCl) (37.40 g, 323.80 mmol) were mixed, and stirred at 180° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and methylene chloride (MC) was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was filtered using EA to thereby obtain Intermediate (B) (8.8 g, 25.12 mmol, yield=78%).
LC-Mass (calculated: 350.11 g/mol, found: M+1=351 g/mol).
Benzimidazole (20.0 g, 169.29 mmol), 1,3-dibromobenzene (47.9 g, 203.15 mmol), copper (I) iodide (6.45 g, 33.86 mmol), 1,10-phenanthroline (9.15 g, 50.79 mmol), and cesium carbonate (110.3 g, 338.58 mmol) were mixed with 340 ml of dimethylformamide (DMF), and stirred at 150° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and EA. The organic layer was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Intermediate (C) (21.8 g, 79.82 mmol, yield=47%).
LC-Mass (calculated: 271.00 g/mol, found: M+1=272 g/mol).
Intermediate (C) (5.46 g, 20 mmol), Intermediate (B) (8.41 g, 24 mmol), copper (I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and potassium phosphate tribasic (12.7 g, 60 mmol) were mixed with 133 ml of DMSO, and stirred at 120° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and EA. The organic layer was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Intermediate (D) (7.05 g, 13 mmol, yield=65%).
LC-Mass (calculated: 542.17 g/mol, found: M+1=543 g/mol).
Intermediate (D) (5.0 g, 9.22 mmol) and methyl iodide (3.92 g, 27.65 mmol) were mixed with 46 ml of toluene, and stirred at 60° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then the residue obtained by concentration under reduced pressure was subjected to silica gel column chromatography to thereby obtain Intermediate (E) (5.24 g, 7.65 mmol, yield=83%).
Intermediate (E) (5.24 g, 7.65 mmol), Pt(COD)Cl2 (3.15 g, 8.42 mmol), and sodium acetate (1.88 g, 22.95 mmol) were mixed with 383 ml of benzonitrile, and stirred at 180° C. for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Compound 1 (3.15 g, 4.21 mmol, yield=55%).
LC-Mass (calculated: 749.14 g/mol, found: M+1=750 g/mol).
Benzimidazole (20.0 g, 169.29 mmol), 1,3-dibromo-5-(tert-butyl)benzene (59.3 g, 203.15 mmol), copper(I) iodide (6.45 g, 33.86 mmol), 1,10-phenanthroline (9.15 g, 50.79 mmol), and cesium carbonate (110.3 g, 338.58 mmol) were mixed with 340 ml of DMF, and stirred at 150° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and EA. The organic layer was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was subject to silica gel column chromatography to thereby obtain Intermediate (F) (26.8 g, 81.26 mmol, yield=48%).
LC-Mass (calculated: 328.06 g/mol, found: M+1=329 g/mol).
Intermediate (F) (6.58 g, 20 mmol), Intermediate (B) (8.41 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and potassium phosphate tribasic (12.7 g, 60 mmol) were mixed with 133 ml of DMSO, and stirred at 120° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and EA. The organic layer was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Intermediate (G) (7.54 g, 12.6 mmol, yield=63%).
LC-Mass (calculated: 598.24 g/mol, found: M+1=599 g/mol).
Intermediate (G) (5.0 g, 8.35 mmol) and methyl iodide (3.56 g, 25.05 mmol) were mixed with 42 ml of toluene, and stirred at 60° C. for 12 hours. After the reaction is completed, the mixture was cooled to room temperature, and then the product obtained by concentration under reduced pressure was subjected to silica gel column chromatography to thereby obtain Intermediate (H) (5.13 g, 6.93 mmol, yield=83%).
Intermediate (H) (5.13 g, 6.93 mmol), Pt(COD)Cl2(2.85 g, 7.62 mmol), and sodium acetate (1.71 g, 20.79 mmol) were mixed with 347 ml of benzonitrile, and stirred at 180° C. for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Compound 2 (3.63 g, 4.50 mmol, yield=65%).
LC-Mass (calculated: 805.20 g/mol, found: M+1=806 g/mol).
Intermediate (D) (4.0 g, 7.37 mmol), diphenyliodonium triflate (4.76 g, 11.06 mmol), and copper(II) acetate (0.13 g, 0.74 mmol) were mixed with 74 ml of DMF, and stirred at 180° C. for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, and then an organic layer extracted by using NH4Cl and EA. The organic layer was dried over MgSO4 and subjected to filtration, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Intermediate (I) (4.82 g, 6.26 mmol, yield=85%).
Intermediate (I) (4.82 g, 6.26 mmol), Pt(COD)Cl2 (2.58 g, 6.89 mmol), and sodium acetate (1.54 g, 18.78 mmol) were mixed with 313 ml of benzonitrile, and stirred at 180° C. for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Compound 3 (2.85 g, 3.51 mmol, yield=56%).
LC-Mass (calculated: 811.16 g/mol, found: M+1=806 g/mol).
Intermediate (G) (5.0 g, 8.35 mmol) and methyl iodide-d3 (3.63 g, 25.05 mmol) were mixed with 42 ml of toluene, and stirred at 60° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and then the product obtained by concentration under reduced pressure was subjected to silica gel column chromatography to thereby obtain Intermediate (J) (5.22 g, 7.01 mmol, yield=84%).
Intermediate (J) (5.22 g, 7.01 mmol), Pt(COD)Cl2 (2.89 g, 7.71 mmol), and sodium acetate (1.73 g, 21.03 mmol) were mixed with 350 ml of benzonitrile, and stirred at 180° C. for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, followed by concentration under reduced pressure. The obtained product was subjected to silica gel column chromatography to thereby obtain Compound 110 (3.97 g, 4.91 mmol, yield=70%).
LC-Mass (calculated: 809.23 g/mol, found: M+1=810 g/mol).
An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated in acetone isopropyl alcohol and pure water for 15 minutes each, and then washed by exposure to UV ozone for 30 minutes.
Then, m-MTDATA was deposited on an ITO electrode (anode) of the glass substrate at a deposition speed of 1 Å/sec to form a hole injection layer having a thickness of 600 Å, and then, α-NPD (NPB) was deposited on the hole injection layer at a deposition speed of 1 Å/sec to form a hole transport layer having a thickness of 250 Å.
Compound 1 (dopant) and CBP (host) were co-deposited on the hole transport layer at a deposition speed of 0.1 Å/sec and a deposition speed of 1 Å/sec, respectively, to form an emission layer having a thickness of 400 Å.
BAlq was deposited on the emission layer at a deposition speed of 1 Å/sec to form a hole blocking layer having a thickness of 50 Å, and Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then, Al was vacuum-deposited on the electron injection layer to form a second electrode (cathode) having a thickness of 1,200 Å, thereby completing manufacturing of an organic light-emitting device having a structure of ITO/m-MTDATA (600 Å)/α-NPD (250 Å)/CBP+Compound 1 (10%) (400 Å)/BAlq (50 Å)/Alq3 (300 Å)/LiF (10 Å)/Al (1,200 Å).
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 2 were each used instead of Compound 1 as a dopant in forming an emission layer.
Photoluminescence quantum efficiency (PLQY) and external quantum efficiency (EQE) for each of the organic light-emitting device manufactured according to Examples 1 to 3 and Comparative Example 1 were evaluated as relative values with respect to PLQY and EQE of Comparative Example 1, and the results thereof are shown in Table 2. As evaluation apparatuses, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used.
From Table 2, it can be seen that the organic light-emitting devices of Examples 1 to 3 have excellent PLQY and EQE, and have improved characteristics in terms of PLQY and EQE compared to the organic light-emitting device of Comparative Example 1.
An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, a weight ratio of Compound CBP, which was used as a host, was 88.5%, and a weight ratio of Compound 110 and Compound FD, which were used as dopants, was 10%: 1.5%.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compound FD was used for use as a dopant in forming an emission layer.
With respect to each of the organic light-emitting devices manufactured according to Example 4 and Comparative Example 2, driving voltage, PLQY, EQE, and a maximum emission wavelength were evaluated, and the results thereof are shown in Table 3. As evaluation apparatuses, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used.
From Table 3, it can be seen that the organic light-emitting device of Example 4 has a lower driving voltage and significantly improved EQE, compared to the organic light-emitting device of Comparative Example 2.
The organometallic compound has excellent photochemical stability, and an organic light-emitting device including the organometallic compound has improved efficiency. In addition, the organometallic compound has excellent phosphorescent luminescent characteristics, and thus, when used, a diagnostic composition having a high diagnostic efficiency may be provided.
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 |
|---|---|---|---|
| 10-2020-0053393 | May 2020 | KR | national |
