Patent Grant
12049473
This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0167138, filed on Dec. 13, 2019, in the Korean Intellectual Property Office, the content 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 same, and a diagnostic composition including the same.
Organic light-emitting devices are self-emission devices, which have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
Meanwhile, luminescent compounds, for example, phosphorescent compounds, may be used for monitoring, sensing, and detecting biological materials such as various cells and proteins.
Aspects of the present disclosure provide 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.
According to an aspect of an embodiment, provided is an organometallic compound represented by Formula 1:
M(LA)n1(LB)n2 Formula 1
According to an aspect of another embodiment, provided is an organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, the organic layer including at least one of the above-described organometallic compound represented by Formula 1.
The organometallic compound in the organic layer may serve as a dopant.
According to an aspect of another embodiment, provided is a diagnostic composition including at least one of the above-described organometallic compound represented by Formula 1.
These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawing in which:
FIGURE is a schematic cross-sectional view of an organic light-emitting device according to an exemplary 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. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present
It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.
“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the FIGURES It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the FIGURES For example, if the device in one of the FIGURES is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the FIGURE Similarly, if the device in one of the FIGURES is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
An aspect of the present disclosure provides an organometallic compound represented by Formula 1.
M(LA)n1(LB)n2 Formula 1
In Formula 1, M may be a transition metal.
In one or more embodiments, M may be a Period 1 transition metal, Period 2 transition metal, or a Period 3 transition metal.
In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
For example, M may be Ir, Pt, Os, or Rh.
In Formula 1, LA may be a ligand represented by Formula 2A, and LB may be a ligand represented by Formula 2B.
In Formula 1, n1, which indicates the number of LA (s) in Formula 1, may be 1, 2 or 3. When n1 is 2 or 3, the two or three LA(s) may be identical to or different from each other.
In Formula 1, n2, which indicates the number of LB(s) in Formula 1, may be 0, 1, 2, or 3. When n2 is 2 or 3, the two or three LB(s) may be identical to or different from each other.
The organometallic compound may be a homoleptic compound including ligand LA only, or a heteroleptic compound including both ligand LA and ligand LB.
In one or more embodiments, the organometallic compound may be a heteroleptic compound including both ligand LA and ligand LB.
In one or more embodiments, in Formula 1, M may be Ir, n1 may be 1, 2 or 3, n2 may be 0, 1 or 2, and the sum of n1 and n2 is 3.
In one or more embodiments, M may be Ir, n1 may be 1, and n2 may be 2.
In one or more embodiments, in Formula 1, M may be Pt, n1 may be 1 or 2, and n2 may be 0 or 1, and the sum of n1 and n2 is 2.
In Formula 2A, X21 may be C(R21), N, a carbon bonded to the A10-containing ring system, or carbon bonded to M, X22 may be C(R22), N, a carbon bonded to the A10-containing ring system, or carbon bonded to M, X23 may be C(R23), N, a carbon bonded to the A10-containing ring system, or a carbon bonded to M, X24 may be C(R24), N, a carbon bonded to the A10-containing ring system, or a carbon bonded to M, one of X21 to X24 may be the carbon bonded to the A10-containing ring system, and one of X21 to X24 adjacent to the carbon bonded to the A10-containing ring system may be the carbon bonded to M.
In one or more embodiments, X21 may be carbon bonded to the A10-containing ring system, X22 may be the carbon bonded to M, X22 may be the carbon bonded to the A10-containing ring system, X23 may be the carbon bonded to M, X23 may be the carbon bonded to the A10-containing ring system, and X24 may be the carbon bonded to M.
In Formula 2A, C21 and C22 may be carbon atoms.
In Formula 2A, a 6-membered ring including X21 to X24, C21, and C22 may be a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, or a pyridazine ring.
In Formula 2A, Z21 may be O, S, Se, or N, Z22 may be C(R25), Z23 may be O, S, Se, or N, a 5-membered ring including Z21 to Z23, C21, and C22 may be an oxazole ring, a thiazole ring, or a selenazole ring.
For example, when Z21 is O, S, or Se, Z22 may be C(R25), and Z23 may be N.
For example, when Z23 is O, S, or Se, Z22 may be C(R25), and Z21 may be N.
In Formula 2B, X30 and X40 may each independently be C or N.
In one or more embodiments, in Formula 2B, X30 may be N, and X40 may be C, or X30 may be C, and X40 may be N.
In one or more embodiments, in Formula 2B, X30 may be N, X40 may be C, a bond between X30 and M may be a coordinate bond, and a bond between X40 and M may be a covalent bond.
In Formulae 2A and 2B, ring A10, ring A30, and ring A40 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, in Formulae 2A and 2B, ring A10, ring A30, and ring A40 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazol group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
As used herein, the terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxide group” refer to hetero rings having the same backbone as, respectively, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group, but at least one of the carbons forming the ring being substituted with nitrogen.
In one or more embodiments, in Formulae 2A and 2B, ring A10, ring A30, and ring A40 may each independently be a benzene group, a naphthalene group, 1,2,3,4-tetrahydroa naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, and an azadibenzosilole group.
In one or more embodiments, in Formula 2B, ring A30 may be a pyridine group, and ring A40 may be a benzene group.
In one or more embodiments, in Formula 2B, ring A40 may be a group represented by Formulae A40-1 to A40-32.
In Formulae A40-1 to A40-32,
In Formulae 2A and 2B, R10, R11, R21 to R25, R30, and R40 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
In Formulae 2A and 2B, c10, c30, and c40 may each independently be an integer 1 to 8. When c10 is 2 or greater, two or more R10(s) may be identical to or different from each other. When c30 is 2 or greater, two or more R30(s) may be identical to or different from each other. When c40 is 2 or greater, two or more R40(s) may be identical to or different from each other.
In one or more embodiments, in Formulae 2A and 2B, R10, R11, R21 to R25, R30, and R40 may each independently be:
For example, in Formulae 2A and 2B, R10, R11, R21 to R25, R30, and R40 may each independently be:
In one or more embodiments, in Formulae 2A and 2B, R10, R11, R21 to R25, R30 and R40 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 9-26, a group represented by Formulae 10-1 to 10-256, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q6)(Q7)(Q8), —B(Q)(Q10), or —P(═O)(Q11)(Q12), but embodiments are not limited thereto:
In Formulae 9-1 to 9-26 and 10-1 to 10-256,
In one or more embodiments, in Formula 2A, R11 and R25 may each independently be:
In one or more embodiments, in Formula 2A, R11 and R25 may each independently be hydrogen, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by Formulae 9-1 to 9-13, a group represented by Formulae 10-1 to 10-12, or a group represented by Formulae 10-17 to 10-134. However, embodiments are not limited thereto.
In one or more embodiments, at least one of R30(s) in number of c30 and R40(s) in number of c40 may be:
In one or more embodiments, ring A30 may be a pyridine group, and at least one of R30(s) in number of c30 may be —Si(Q3)(Q4)(Q5), —Ge(Q6)(Q7)(Q8), or a combination thereof.
In one or more embodiments, in Formula 1, LA may be a ligand represented by Formula 2A-1.
In Formula 2A-1,
In one or more embodiments, in Formula 2A-1, X11 may be C(R101), X12 may be C(R102), X13 may be C(R103), and X14 may be C(R104).
In one or more embodiments, in Formulae 2A and 2A-1, a moiety represented by
may be a group represented by one of Formulae A20-1 to A20-6.
In Formulae A20-1 to A20-6,
In one or more embodiments, in Formulae 2A and 2A-1, a moiety represented by
may be a group represented by one of Formulae A20-11 to A20-28.
In Formulae A20-11 to A20-28,
In one or more embodiments, in Formulae A20-1 to A20-6 and A20-11 to A20-28, X21 may be C(R21), X22 may be C(R22), X23 may be C(R23), and X24 may be C(R24).
In one or more embodiments, in Formulae A20-1 to A20-2 and A20-11 to A20-16, one of X23 and X24 may be N; in Formulae A20-3 to A20-4 and A20-17 to A20-22, one of X13 and X24 may be N; and, in Formulae A20-5 to A20-6 and A20-23 to A20-28, one of X21 and X22 may be N.
In one or more embodiments, in Formula 1, LA may be a ligand represented by one of Formulae 2A-11 to 2A-64.
In Formulae 2A-11 to 2A-64,
In one or more embodiments, in Formula 1, LB may be a ligand represented by Formula 2B-1.
In Formula 2B-1,
In one or more embodiments, in Formula 1, LB may be a ligand represented by one of Formulae 2B-2 to 2B-6.
In Formulae 2B-2 to 2B-6,
In one or more embodiments, in Formulae 2-2 to 2B-6,
In one or more embodiments, in Formula 1, LB may be a ligand represented by Formula 2B-2.
In Formula 2B-2, one of R31 to R34 may be —Si(Q3)(Q4)(Q5) or —Ge(Q6)(Q7)(Q8), and
For example, in Formula 1, LB may be a ligand represented by one of Formulae 2B-21 to 2B-24.
In Formulae 2B-21 to 2B-24,
In one or more embodiments, LB may be represented by one of Formulae L1-1 to L1-396, and LA may be represented by one of Formulae L2-1 to L2-568.
In one or more embodiments, the organometallic compound may be represented by the formula of (LA)Ir(LB)2, wherein LA and LB may each independently a ligand as suggested in Table 1. However, embodiments are not limited thereto.
The energy level of the organometallic compound represented by Formula 1, due to the inclusion of ligand LA represented by Formula 2A, can be easily controlled. Accordingly, the organometallic compound may have a suitable energy level, and thus provide improved device characteristics in terms of driving voltage and efficiency.
The ligand represented by Formula 2A includes a condensed polycyclic ring in which A10 ring is condensed to imidazole, and thus have higher electrical stability due to delocalized electrons, as compared to a ligand including an imidazole monocyclic ring. Accordingly, an electronic device, for example, an organic light-emitting device, including the organometallic compound of Formula 1, may have an improved roll-off ratio.
In addition, the ligand represented by Formula 2A includes a condensed polycyclic ring represented by
and thus has increased structural rigidity, as compared to a ligand not including the condensed polycyclic ring. Accordingly, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved lifespan characteristics.
The ligand represented by Formula 2B may include at least one Si-containing group, Ge-containing group, or a combination thereof. Accordingly, the organometallic compound represented by Formula 1 may be significantly improved in molecular orientation and electron mobility, and thus an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved external quantum efficiency. For example, in Formula 2B, ring A30 may be a pyridine, and at least one Si-containing group, Ge-containing group, or a combination thereof may be introduced onto the pyridine ring. Accordingly, the energy level of the organometallic compound represented by Formula 1 may be easily controlled.
The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, and the triplet (T1) energy level of some compounds of the organometallic compounds represented by Formula 1 were evaluated by using the Gaussian 09 program with molecular structure optimization by density functional theory (DFT) based on B3LYP, and the results are shown in Table 2.
Referring to Table 1, it is confirmed that the organometallic compound represented by Formula 1 have electric characteristics that are suitable for use in an electronic device, for example, as a dopant of an organic light-emitting device.
Methods of synthesizing the organometallic compound represented by Formula 1 can be understood by a person of ordinary skill in the art with reference to the synthesis examples described below.
Accordingly, 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. Therefore, another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer and 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 above-described organometallic compound represented by Formula 1, a low driving voltage, high efficiency, high power, high quantum efficiency, improved lifespan, a low roll-off ratio, and excellent color purity.
The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host). The emission layer may emit, for example, green light or red light.
The expression “(an organic layer) includes at least one of the organometallic compound” as used herein may be construed as that the organic layer includes one organometallic compound belonging to the category of Formula 1, or that the organic layer includes two or more different organometallic compounds belonging to the category of Formula 1.
For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may be only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be in the same layer (For example, both Compound 1 and Compound 2 may be in the 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. In other embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described with reference to FIGURE. The organic light-emitting device 10 may have a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 which are sequentially stacked.
A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used. 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 having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (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. However, embodiments are not limited thereto.
The organic layer 15 may be 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 a combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 to about 10−3 torr, and a deposition rate of about 0.01 Å/sec to about 100 Å/sec. However, the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 rpm to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
Conditions for forming a hole transport layer and an electron blocking layer may be understood with reference to the 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/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, a compound represented by Formula 202, or a combination thereof.
In Formula 201, Ar101 and Ar102 may each independently be:
The designations xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may be 0, 1 or 2. For example, xa may be 1 and xb may be 0. However, embodiments 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 one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A. However, embodiments are not limited thereto.
In Formula 201A, R101, R111, R112, and R109 may be defined the same as those defined herein.
Non-limiting examples of the compound represented by Formula 201 and the compound represented by Formula 202 include Compounds HT1 to HT20.
A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes 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 10000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to the above-described 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. However, embodiments are not limited thereto. Non-limiting examples of the p-dopant may be a quinone derivative such as tetracyanoquinonedimethane (TCNQ) and 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. However, embodiments are not limited thereto.
The hole transport region may further 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 increase efficiency.
An emission layer may be formed on the hole transport region using a method such as 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, though the deposition or coating conditions may vary according to a compound 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 the materials for the hole transport region as described above and materials for a host which will be described later. However, embodiments are not limited thereto. For example, when the hole transport region includes an electron blocking layer, mCP, which will be explained later, may be used as the material for the electron blocking layer.
The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 described above.
The host may include at least one of TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compounds H50, Compound H51, and Compound H52.
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 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 100 parts by weight of the host.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Then, an electron transport region may be disposed on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a 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. However, embodiments are 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. However, embodiments are not limited thereto.
A thickness of the hole blocking layer may be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 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 include at least one of BCP, Bphen, Alq3, Balq, TAZ, NTAZ, or a combination thereof.
In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25. However, embodiments are not limited thereto.
A thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the above-described ranges, 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 Compound ET-D2.
The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19.
The electron injection layer may include at least one LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
A thickness of the electron injection layer may be from about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without substantial increase in driving voltage.
The second electrode 19 is provided 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. 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. To manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device according to an embodiment has been described with reference to FIGURE. However, embodiments are not limited thereto
Another aspect of the present disclosure provides a diagnostic composition including at least one of the organometallic compounds represented by Formula 1.
The organometallic compound represented by Formula 1 may provide high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
The diagnostic composition may have a variety of applications, for example, in 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, for example, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, or 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 a C1-C60 alkyl group), and non-limiting examples thereof may include a methoxy group, an ethoxy group, or an isopropyloxy group.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting 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 non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. 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 1 to 10 carbon atoms and including, as a ring-forming atom, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof and non-limiting examples thereof are 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 having 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof but no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group having 2 to 10 carbon atoms and including, as a ring-forming atom, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof, and at least one double bond in the ring thereof. Non-limiting examples of the C2-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 C2-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having 1 to 6 carbon atoms and including, as a ring-forming atom, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system having 1 to 6 carbon atoms and including, as a ring-forming atom, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof. 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” used herein indicates —OA102 (wherein A102 is a C6-C60 aryl group as described above), and the term “C6-C60 arylthio group” used herein indicates —SA103 (wherein A103 is a C6-C60 aryl group as described above).
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, and only carbon atoms as ring-forming atoms, and in which the whole molecular structure has no aromaticity. 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, and including as ring-forming atoms, in addition to carbon atoms, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof and in which the whole molecular structure has no aromaticity. 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 “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as ring-forming atoms, in addition to 1 to 30 carbon atoms, at least one N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof. 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 C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
As used herein, 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 C2-C10 heterocycloalkenyl group; 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; 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, compounds and organic light-emitting devices according to embodiments will now be described in detail with reference to synthesis examples and examples. However, these examples are only for illustrative purposes and are not intended to limit the scope of the one or more embodiments of the present disclosure. The wording “B was used instead of A” used in describing synthesis examples means that the amount of A used was identical to the amount of B used, in terms of a molar equivalent.
Synthesis of Compound 1412A
2-phenyl-5-(trimethylsilyl)pyridine (7.5 g, 33.1 mmol) and iridium chloride) (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water and stirred under reflux for 24 hours, and then the temperature was cooled down to room temperature. The resulting solid was separated by filtration and washed sufficiently with water, methanol, and then hexane. The washed solid was dried in a vacuum oven to obtain 8.3 g of Compound 1412A (Yield: 82%).
Synthesis of Compound 1412B
After Compound 1412B (1.6 g, 1.2 mmol) was mixed with 45 mL of methylene chloride, AgOTf (0.6 g, 2.3 mmol) was mixed with 15 mL of methanol and added thereto. Subsequently, the mixture was stirred for 18 hours at room temperature while blocking light with aluminum foil. The reaction mixture was filtered through celite and the filtrate was concentrated and used in the next reaction without additional purification.
Synthesis of Compound 1412
Compound 1412B (2.0 g, 2.3 mmol) and 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole (1.5 g, 2.8 mmol) were mixed with 100 mL of 2-ethoxyethanol, and stirred under reflux for 24 hours, and then the temperature was cooled down to room temperature. The resulting mixture was concentrated to obtain a solid product. The obtained solid product was subjected to column chromatography (using methylene chloride (MC) and hexane as eluents) to obtain 1.1 g of Compound 1412 (Yield: 42%). This compound was identified by Mass and HPLC analysis).
HRMS (MALDI) calcd for C64H68IrN5OSi2: m/z: 1171.6 Found: 1171.5.
Synthesis of Compound 1509
Compound 1509 (Yield: 39%) was obtained in the same manner as in the synthesis method of Compound 1412 in Synthesis Example 1, except that 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]thiazole was used instead of 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd C59H61IrN4Si2: m/z: 1187.7 Found: 1187.4.
Synthesis of Compound 1917A
Compound 1917A (Yield: 87%) was obtained in the same manner as in the synthesis method of Compound 1412A in Synthesis Example 1, except that 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine.
Synthesis of Compound 1917B
Compound 1917B was obtained in the same manner as in the synthesis method of Compound 1412B in Synthesis Example 1, except that Compound 1917A was used instead of Compound 1412A. Compound 1917B obtained was used in the next reaction without additional purification.
Synthesis of Compound 1917
Compound 1917 (Yield: 43%) was obtained in the same manner as in the synthesis method of Compound 1412 in Synthesis Example 1, except that Compound 1917B was used instead of 1412B, and 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole was used instead of 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C55H66IrN5OSi2: m/z: 1061.5 Found: 1061.4.
Synthesis of Compound 1980
Compound 1980 (Yield: 39%) was obtained in the same manner as in the synthesis method of Compound 1917 in Synthesis Example 3, except that 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole was used instead of 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C72H84IrN5OSi2: m/z: 1283.9 Found: 1283.6.
Synthesis of Compound 2014
Compound 2014 (Yield: 33%) was obtained in the same manner as in the synthesis method of Compound 1917 in Synthesis Example 3, except that 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]thiazole was used instead of 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C55H66IrN5SSi2: m/z: 1077.6 Found: 1077.4.
Synthesis of Compound 2077
Compound 2077 (Yield: 31%) was obtained in the same manner as in the synthesis method of Compound 1917 in Synthesis Example 3, except that 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]thiazole was used instead of 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C72H84IrN5SSi2: m/z: 1299.9 Found: 1299.6.
Synthesis of Compound 2082
Compound 2082 (Yield: 30%) was obtained in the same manner as in the synthesis method of Compound 1917 in Synthesis Example 3, except that 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-(2,6-dimethylphenyl)benzo[d]thiazole was used instead of 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C76H84IrN5SSi2: m/z: 1348.0 Found: 1347.6.
Synthesis of Compound 3684A
Compound 3684A (Yield: 75%) was obtained in the same manner as in the synthesis method of Compound 1412A in Synthesis Example 1, except that 4-isobutyl-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine.
Synthesis of Compound 3684B
Compound 3684B was obtained in the same manner as in the synthesis method of Compound 1412B in Synthesis Example 1, except that Compound 3684A was used instead of Compound 1412A. Compound 3684B obtained was used in the next reaction without additional purification.
Synthesis of Compound 3684
Compound 3684 (Yield: 41%) was obtained in the same manner as in the synthesis method of Compound 1412 in Synthesis Example 1, except that Compound 3684B was used instead of Compound 1412B. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd C72H84Ge2IrN5O: m/z: 1373.0 Found: 1375.5.
Synthesis of Compound 3781
Compound 3781 (Yield: 39%) was obtained in the same manner as in the synthesis method of Compound 3781 in Synthesis Example 8, except that 2-(tert-butyl)-7-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)benzo[d]thiazole was used instead of 2-(tert-butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)benzo[d]oxazole. This compound was identified by Mass and HPLC analysis.
HRMS (MALDI) calcd for C72H84Ge2IrN5S: m/z: 1389.0 Found: 1391.5.
As an anode, a glass substrate with an ITO pattern thereon was cut to a size of 50 mm×50 mm×0.5 mm and washed by ultrasonication using isopropyl alcohol and pure water for 5 minutes each, and then by ultraviolet irradiation for 30 minutes and exposure to ozone. Then, the resultant glass substrate was loaded into a vacuum deposition apparatus.
Compound HT3 and F6-TCNNQ were vacuum-deposited on the anode in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.
Subsequently, Compound CBP (host) and Compound 15 (dopant) were co-deposited on the hole transport layer in a weight ratio of 95:5 to form an emission layer having a thickness of 400 Å.
Then, Compounds ET3 and ET-D1 were co-deposited on the emission layer in a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby manufacturing an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 3 were used, respectively, instead of Compound 1, as a dopant in forming an emission layer.
The maximum external quantum efficiency (Max EQE), roll-off ratio, and lifespan (LT97) of each of the organic light-emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 and 2 were evaluated. The results are shown in Table 3. This evaluation was performed using a current-voltage meter (Keithley 2400) and a luminescence meter (Minolta Cs-1,000A), and the lifespan (LT97) (at 18000 nit) was evaluated as the amount of time that elapsed until the luminance was reduced to 97% with respect to 100% of the initial luminance. The roll-off ratio was calculated according to Equation 20.
Roll-off ratio={1−(efficiency(at 18000 nit)/maximum luminescence efficiency)}×100% Equation 20
Referring to Table 3, the organic light-emitting devices of Examples 1 to 9 were found to have improved external quantum efficiency and lifespan characteristics, as compared to the organic light-emitting devices of Comparative Examples 1 and 2.
As described above, the organometallic compound according to the one or more embodiments has excellent electric characteristics and thermal stability, and thus an organic light-emitting device using the organometallic compound may have excellent characteristics in terms of driving voltage, emission efficiency, color purity, and/or lifespan. The organometallic compound according to the one or more embodiments also has excellent phospholuminescence characteristics, and thus a diagnostic composition having high diagnostic efficiency may be provided using the organometallic compound.
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 |
|---|---|---|---|
| 10-2019-0167138 | Dec 2019 | KR | national |
| Number | Name | Date | Kind |
|---|---|---|---|
| 9923154 | Oshiyama et al. | Mar 2018 | B2 |
| 20210163517 | Jeon et al. | Jun 2021 | A1 |
| Number | Date | Country |
|---|---|---|
| 2016219490 | Dec 2016 | JP |
| 1020210066627 | Jun 2021 | KR |
| 2012111548 | Aug 2012 | WO |
| 2016056562 | Apr 2016 | WO |
| Entry |
|---|
| English Abstract of JP 2016219490, 2016. |
| Number | Date | Country | |
|---|---|---|---|
| 20210198297 A1 | Jul 2021 | US |
