Patent Application
20240431195
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0078354, filed on Jun. 19, 2023, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the entire content of which is incorporated by reference herein.
The present subject matter relates to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices (OLEDs) are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is arranged between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged 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. The excitons may transition from an excited state to a ground state, thereby generating light.
Provided are an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the detailed description that follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments herein.
According to an aspect, provided is an organometallic compound represented by Formula 1:
M1(L1)n1(L2)n2 Formula 1
wherein, in Formula 1,
wherein, in Formulae 1A, 1B, and 2,
According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one of the organometallic compound.
At least one of the organometallic compounds may be included in the emission layer of the organic layer, and the at least one of the organometallic compounds included in the emission layer may act as a dopant.
According to another aspect, an electronic apparatus includes the organic light-emitting device.
The above and other aspects, features, and advantages of certain exemplary embodiments will be more apparent from the following detailed description taken in conjunction with the FIGURE, which is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.
Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the detailed descriptions set forth herein. Accordingly, the exemplary embodiments are merely described in further detail below, and by referring to the FIGURE, to explain certain aspects and features. 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.
The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” 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.
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 of the present embodiments.
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.
It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with 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.
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 general inventive concept 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.
“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%, 5% of the stated value.
As used herein, an “energy level” (e.g., a highest occupied molecular orbital (HOMO) energy level or a triplet (T1) energy level) is expressed as an absolute value from a vacuum level. In addition, when the energy level is referred to as being “deep,” “high,” or “large,” the energy level has a large absolute value based on “0 electron Volts (eV)” of the vacuum level, and when the energy level is referred to as being “shallow,” “low,” or “small,” the energy level has a small absolute value based on “0 eV” of the vacuum level.
An aspect provides an organometallic compound represented by Formula 1:
M1(L1)n1(L2)n2. Formula 1
In Formula 1, M1 is a transition metal.
For example, M1 may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements.
In one or more embodiments, M1 may be iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In one or more embodiments, M1 may be iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).
In one or more embodiments, M1 may be iridium (Ir).
In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.
In one or more embodiments, a sum of n1 and n2 may be 2 or 3.
In one or more embodiments, M1 may be iridium (Ir), and the sum of n1 and n2 may be 3.
In one or more embodiments, M1 may be platinum (Pt), and the sum of n1 and n2 may be 2.
In Formula 1, L1 is a ligand represented by Formula 1A:
In Formula 1A, X1 is C or N, and X2 is C or N.
In one or more embodiments, X1 may be N, and X2 may be C.
In Formula 1A, ring CY1 and ring CY2 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, ring CY1 and ring CY2 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring group in which two or more first rings are condensed with each other, iv) a condensed ring group in which two or more second rings are condensed with each other, or v) a condensed ring group in which at least one first ring is condensed with at least one second ring,
In one or more embodiments, ring CY1 and ring CY2 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene 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 benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.
In one or more embodiments,
In one or more embodiments, a group represented by
in Formula 1A may be a group represented by one of Formulae CY(1)-1 to CY(1)-16:
In Formulae CY(1)-1 to CY(1)-16,
In one or more embodiments, a group represented by
in Formula 1A may be a group represented by one of Formulae CY(2)-1 to CY(2)-16:
In Formulae CY(2)-1 to CY(CY(2)-16,
In one or more embodiments, L1 is a ligand represented by Formula 1A-1:
In Formula 1A-1,
In one or more embodiments, in Formula 1A-1, at least one of R11 to R14 or R21 to R24 may be a C1-C10 alkyl group unsubstituted or substituted with at least one deuterium (e.g., —CD3, —CD2H, —CDH2, or the like).
For example, i) one or two of R11 to R14 may each independently be a C1-C10 alkyl group unsubstituted or substituted with at least one deuterium, ii) one of R21 to R24 may be a C1-C10 alkyl group unsubstituted or substituted with at least one deuterium, or iii) one of R11 to R14 or one of R21 to R24 may each be a C1-C10 alkyl group unsubstituted or substituted with at least one deuterium.
In Formula 1, L2 is a ligand represented by Formula 1B:
In Formula 1B, X3 is C or N.
In one or more embodiments, X3 may be N, and X4 may be C.
In Formula 1B, ring CY3 is (i) a 5-membered carbocyclic group, (ii) a 5-membered heterocyclic group, (iii) a 5-membered carbocyclic group to which a C5-C30 carbocyclic group is condensed, or a 5-membered carbocyclic group to which a C1-C30 heterocyclic group is condensed, or (iv) a 5-membered heterocyclic group to which a C5-C30 carbocyclic group is condensed, or a 5-membered heterocyclic group to which a C1-C30 heterocyclic group is condensed.
In one or more embodiments, ring CY3 may be i) a first ring, ii) a condensed ring group in which two or more first rings are condensed with each other, or iii) a condensed ring group in which at least one first ring is condensed with at least one second ring,
In one or more embodiments, ring CY3 may be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.
For example, ring CY3 may be an imidazole group or a benzimidazole group.
In one or more embodiments, a group represented by
in Formula 1B may be a group represented by one of Formulae CY(3)-1 to CY(3)-3:
In Formulae CY(3)-1 to CY(3)-3,
In one or more embodiments, a group represented by
in Formula 1B may be a group represented by one of Formulae CY(3A)-1 to CY(3A)-16:
In Formulae CY(3A)-1 to CY(3A)-16,
In one or more embodiments, in Formulae CY(3A)-1 to CY(3A)-16, X31 may be N(R31a), and R31a may be a C6-C60 aryl group or a C1-C30 heteroaryl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C1-C20 alkyl group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), or a combination thereof, and
In Formula 1B, ring CY41 is a 6-membered carbocyclic group or a 6-membered heterocyclic group.
In one or more embodiments, ring CY41 may be a benzene group or a pyridine group.
In Formula 1B, X43 is C(R43) or N, X44 is C(R44) or N, X45 is C(R45) or N, X46 is C(R46) or N, X47 is C(R47) or N, and X48 is C(R48) or N, with the proviso that i) X45 is C(R45), X46 is C(R46), and R45 and R46 are bonded to each other to form a group represented by Formula 2, ii) X46 is C(R46), X47 is C(R47), and R46 and R47 are bonded to each other to form a group represented by Formula 2, or iii) X47 is C(R47), X48 is C(R48), and R47 and R48 are bonded to each other to form a group represented by Formula 2:
Ring CY42 in Formula 1B and ring CY5 in Formula 2 are condensed with each other.
In Formula 2, indicates a single bond or a double bond.
It should be understood that, by the proviso above, the moiety represented by in Formula 2 may correspond to (i) a bond between X45 and X46 in Formula 1B, (ii) a bond between X46 and X47 in Formula 1B, or (iii) a bond between X47 and X48 in Formula 1B, wherein ring CY42 in Formula 1B and ring CY5 in Formula 2 are condensed with each other.
In Formula 1B, Y1 is O, S, Se, C(R61)(R62), or N(R63).
In Formula 2, Y2 is O, S, Se, C(R64)(R65), or N(R66).
In one or more embodiments, Y1 and Y2 may be identical to each other.
In one or more embodiments, Y1 and Y2 may be different from each other.
In Formula 2, X51 is C(R51) or N, X52 is C(R52) or N, X53 is C(R53) or N, and X54 is C(R54) or N.
In one or more embodiments, L2 may be a ligand represented by Formula 1B-1:
In Formula 1B-1,
In one or more embodiments, L2 may be a ligand represented by one of Formulae 1B(1)-1 to 1B(1)-6:
In Formulae 1B(1)-1 to 1B(1)-6,
In one or more embodiments, L2 may be a ligand represented by one of Formulae 1B(2)-1 to 1B(2)-6:
In Formulae 1B(2)-1 to 1B(2)-6,
In one or more embodiments, in Formulae 1B(2)-1 to 1B(2)-6, R31 may be a C6-C30 aryl group or a C1-C30 heteroaryl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C1-C20 alkyl group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), or a combination thereof, and
In Formulae 1A, 1B, and 2, R1 to R4, R43 to R48, R51 to R54, and R61 to R66 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl 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 C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(Q8)(Q9), or —P(═O)(Q8)(Q9).
In one or more embodiments, R1 to R4, R43 to R48, R51 to R54, and R61 to R66 may each independently be:
In one or more embodiments, R1 to R4, R43 to R48, R51 to R54, and R61 to R66 may each independently be:
In Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-134, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph” indicates a phenyl group, “TMS” indicates a trimethylsilyl group, and “TMG” indicates a trimethylgermyl group.
In Formula 1A, neighboring two or more of a plurality of R1 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 1A, neighboring two or more of a plurality of R2 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 1B, neighboring two or more of a plurality of R3 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 1B, neighboring two or more of R43 to R48 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 2, neighboring two or more of R51 to R54 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 1A, b1 to b3 are each independently an integer from 1 to 10.
In Formula 1B, b4 is an integer from 1 to 4.
In Formulae 1A and 1B, * and *′ each indicate a binding site to M1.
In one or more embodiments, the organometallic compound may be represented by at least one of Compounds 1 to 30:
In one or more embodiments, the organometallic compound may be electrically neutral.
The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 described above, and includes a ligand having the structure represented by Formula 1B. Due to this structure, the organometallic compound represented by Formula 1 may have excellent luminescence characteristics, and in particular, may have such characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.
In addition, the organometallic compound represented by Formula 1 may have excellent electrical mobility. Thus, an electronic device, for example, an organic light-emitting device, including at least one of the organometallic compounds represented by Formula 1 may exhibit a low driving voltage, high efficiency, and a long lifespan.
A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a singlet (S1) energy level, and a triplet (T1) energy level of selected organometallic compounds represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimized at the B3LYP level, and results thereof are shown in Table 1. The energy levels are expressed in electron volts (eV).
From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has such electrical characteristics suitable for use as a dopant for an electronic device, for example, an organic light-emitting device.
In one or more embodiments, a maximum emission wavelength (emission peak wavelength, λmax) of an emission peak of an emission spectrum or electroluminescence (EL) spectrum of the organometallic compound may be about 490 nanometers (nm) to about 550 nm.
Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art and by referring to Synthesis Examples provided below.
Accordingly, the organometallic compound represented by Formula 1 may be suitable for use as a dopant in an organic layer, for example, an emission layer, of an organic light-emitting device. Thus, another aspect provides an organic light-emitting device including a first electrode; a second electrode; and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one of the organometallic compounds represented by Formula 1.
The organic light-emitting device may have an excellent driving voltage, an excellent maximum external quantum efficiency, and excellent lifespan characteristics due to the inclusion of the organic layer including at least one of the organometallic compounds represented by Formula 1 as described herein.
The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, at least one of the organometallic compounds 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. When the emission layer further includes a host, an amount of the host in the emission layer may be greater than an amount of the at least one organometallic compound represented by Formula 1 in the emission layer, based on weight.
In one or more embodiments, the emission layer may emit a green light. For example, the emission layer may emit a green light having a maximum emission wavelength of about 490 nm to about 550 nm.
The expression “(an organic layer) includes at least one organometallic compound represented by Formula 1” or ““(an organic layer) includes at least one of the organometallic compounds represented by Formula 1” as used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
For example, the organic layer may include, as the at least one organometallic compound represented by Formula 1, only Compound 1. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the at least one organometallic compound represented by Formula 1, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in an identical layer (e.g., both Compound 1 and Compound 2 may be present 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; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode and the emission layer, and an electron transport region arranged between the emission layer and the second electrode, wherein 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 arranged 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.
The FIG. is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments will be described with reference to the FIGURE, but embodiments are not limited thereto. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in this stated order.
A substrate may be additionally arranged under the first electrode 11 or on 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 for example, a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance, may be used.
The first electrode 11 may be formed by, for example, depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from 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 one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but embodiments are not limited thereto.
The organic layer 15 may be arranged on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, an electron transport region, or a combination thereof.
The hole transport region may be arranged 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 a hole injection layer or only 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, wherein constituent layers of each structure 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, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like, or a combination thereof.
When the 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 in a range of about 10−8 torr to about 10−3 torr, and a deposition rate in a range of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec, but embodiments are not limited thereto.
When the hole injection layer is formed by spin coating, the coating 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 coating conditions may include a coating speed of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature for removing a solvent after coating of about 80° C. to about 200° C., but embodiments are not limited thereto.
Conditions for forming the hole transport layer and the electron blocking layer may be the same as or similar to the conditions for forming the hole injection layer.
The hole transport region may include, for example, at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′di(1-naphthyl)-N,N′diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′diphenyl-[1,1-biphenyl]-4,4′˜diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′cyclohexylidene bis[N,N-bis(4-methyiphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (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, or a compound represented by Formula 202, but embodiments are not limited thereto:
In Formula 201, Ar101 and Ar102 may each independently be:
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but 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, but embodiments are not limited thereto:
In Formula 201A, R101, R111, R112, and Rios may each be as described herein.
For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one or more of Compounds HT1 to HT20, but embodiments are not limited thereto:
A thickness of the hole transport region may be 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 about 50 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 about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. Without wishing to be bound to theory, 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 materials described above, 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, or a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant include a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), or the like; a metal oxide, such as a tungsten oxide, a molybdenum oxide, or the like; or a cyano group-containing compound, such as Compounds HT-D1 or F12, but 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 depending on a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.
The emission layer may be formed on the hole transport region by using one or more suitable methods, 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 material that is used.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be described below, but embodiments are 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 described in further detail below.
The emission layer may include a host and a dopant, and the dopant may include at least one of the organometallic compounds represented by Formula 1.
The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN) (also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50, or Compound H51, but embodiments are not limited thereto:
In one or more embodiments, the host may include a compound represented by Formula 301:
In Formula 301, Ar111 and Ar112 may each independently be:
In Formula 301, Ar113 to Ar116 may each independently be:
In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and for example, may each independently be 0, 1, or 2.
In Formula 301, Ar113 to Ar116 may each independently be:
In one or more embodiments, the host may include a compound represented by Formula 302:
In Formula 302, Ar122 to Ar125 may each be as described in connection with Ar113 in Formula 301.
In Formula 302, Ar126 and Ar127 may each independently be a C1-C10 alkyl group (e.g., a methyl group, an ethyl group, a propyl group, or the like).
In Formula 302, k and i may each independently be an integer from 0 to 4. For example, k and i may each independently be 0, 1, or 2.
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit a white light, and various modifications are possible.
When the emission layer includes a host and a dopant, an amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host, but embodiments are not limited thereto.
A thickness of the emission layer may be about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. Without wishing to be bound to theory, when the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
Next, an electron transport region may be arranged 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, but embodiments are not limited thereto. The electron transport layer may have a single-layer structure or a multi-layer 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 the same as or similar 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 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), but embodiments are not limited thereto:
A thickness of the hole blocking layer may be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. Without wishing to be bound to theory, when the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxy-quinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but embodiments are not limited thereto:
In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:
A thickness of the electron transport layer may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Without wishing to be bound to theory, when the thickness of the electron transport layer is within these ranges, satisfactory electron transporting characteristics may be obtained 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, but embodiments are not limited thereto:
The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
A thickness of the electron injection layer may be about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. Without wishing to be bound to theory, when the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be arranged 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, the material for forming the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-L1), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19, and various modifications are possible.
Hereinbefore, the organic light-emitting device 10 has been described with reference to the FIGURE, but embodiments are not limited thereto.
Another aspect provides a diagnostic composition including at least one of the organometallic compounds represented by Formula 1.
Since the organometallic compound represented by Formula 1 provides a high luminescence efficiency, the diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have a high diagnostic efficiency.
The diagnostic composition may be used in various applications, such as a diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, or the like, but embodiments are not limited thereto.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, or the like. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, or the like.
The term “C1-C60 alkylthio group” as used herein refers to a monovalent group represented by —SA101 (wherein A101 is the C1-C60 alkyl group).
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond 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, a butenyl group, or the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethynyl group, a propynyl group, or the like. 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 cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, or 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 cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, or the like. 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 cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond in its ring, and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a norbornenyl group, or the like. 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 cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom, 1 to 10 carbon atoms as ring-forming atoms, and at least one double bond in its ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. 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 ring system having 6 to 60 carbon atoms, and the term “C6-C6a arylene group” as used herein refers to a divalent group having a carbocyclic aromatic ring 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, a chrysenyl group, or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C7-C60 aryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C6-C60 aryl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom and having 1 to 60 carbon atoms as ring-forming atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group. The term “C2-C60 heteroaryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C1-C60 heteroaryl group.
The term “C6-C60 aryloxy group” as used herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C1-C60 heteroaryloxy group” as used herein refers to —OA104 (wherein A104 is the C1-C60 heteroaryl group), and the term “C1-C60 heteroarylthio group” as used herein refers to —SA105 (wherein A105 is the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group or the like. 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 (e.g., having 1 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom selected from B, N, O, P, Si, S, Se, or Ge other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or the like. 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 ring 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 ring group having, as a ring-forming atom, at least one heteroatom selected from B, N, O, Si, P, S, Se, or Ge other than 1 to 30 carbon atoms as ring-forming 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 C1-C60 alkylthio 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 alkyl aryl group, the substituted C7-C60 aryl alkyl 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 C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be:
Hereinafter, an organometallic compound represented by Formula 1 and an organic light-emitting device according to one or more embodiments will be described in further detail with reference to Synthesis Examples and Examples. However, embodiments are not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used based on molar equivalence.
2-phenyl-pyridine (5.2 grams (g), 33.2 millimoles (mmol)) and iridium chloride trihydrate (5.2 g, 14.8 mmol) were mixed with 120 milliliters (mL) of ethoxyethanol and 25 mL of deionized (DI) water, and heated and stirred under reflux for 24 hours. Then, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed sufficiently with water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 7.2 g (yield of 91%) of Compound 1A(1).
Compound 1A(1) (1.6 g, 1.2 mmol) was mixed with 45 mL of methylene chloride (MC), and then, silver trifluoromethanesulfonate (AgOTf) (0.6 g, 2.3 mmol) mixed with 15 mL of methanol was added thereto. Afterwards, the mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then filtered through Celite to remove the resulting solid. The solvent was removed from filtrate under a reduced pressure to obtain a solid (Compound 1A), which was used in the next reaction without an additional purification process.
In a nitrogen atmosphere, 2-(benzo[4′,5′]furo[2′,3′:5,6]naphtho[1,2-b]benzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane (1.1 g, 2.54 mmol) and 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole (1.0 g, 2.31 mmol) were dissolved in 45 mL of 1,4-dioxane. Then, potassium carbonate (K2CO3) (0.73 g, 5.82 mmol) was dissolved in 15 mL of DI water and added to the reaction mixture, and a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4) (0.13 g, 0.12 mmol) was added thereto. Afterwards, the reaction mixture was stirred and heated under reflux at 100° C.
After an extraction process was performed thereon, the obtained solid was purified by column chromatography (eluents: MC and hexane) to obtain 1.25 g (yield of 82%) of Compound 1B. The obtained compound was identified by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.
HRMS (MALDI) calculated for C47H36N2O2: m/z: 660.82; found: 661.78.
2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.
2-(benzo[4′,5′]furo[2′,3′:5,6]naphtho[1,2-b]benzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane was synthesized according to the following reaction scheme. The product yield of each step is as described in the scheme.
Compound 1A (1.1 g, 1.6 mmol) and Compound 1B (1.2 g, 1.8 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N,N-dimethylformamide, and stirred and heated under reflux for 24 hours. Then, the temperature was lowered to room temperature.
An extraction process was performed thereon with MC and water, and the water layer was removed therefrom. The resulting organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure. After an extraction process was performed thereon, the obtained solid was purified by column chromatography (eluents: MC and hexane) to obtain 0.90 g (yield of 50%) of Compound 1. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C69H51IrN4O2: m/z: 1160.41; found: 1161.32.
0.84 g (yield of 40%) of Compound 7 was obtained in a similar manner as in the synthesis of Compound 1, except that, in the synthesis of Compound 7 Å, 5-(methyl-d3)-2-phenylpyridine (5.7 g, 33.2 mmol) was used instead of 2-phenyl-pyridine in synthesizing Compound 1A(1). The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C71H49D6IrN4O2: m/z: 1194.50; found: 1195.34.
0.76 g (yield of 37%) of Compound 13 was obtained in a similar manner as in the synthesis of Compound 1, except that, in the synthesis of Compound 13A, 4,5-bis(methyl-d3)-2-phenylpyridine (6.04 g, 31.90 mmol) was used instead of 2-phenyl-pyridine in synthesizing Compound 1A(1). The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C73H47D12IrN4O2: m/z: 1228.59; found: 1229.41.
0.71 g (yield of 34%) of Compound 19 was obtained in a similar manner as in the synthesis of Compound 1, except that, in the synthesis of Compound 19 Å, 5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridine (6.04 g, 31.90 mmol) was used instead of 2-phenyl-pyridine in synthesizing Compound 1A(1). The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C73H47D12IrN4O2: m/z: 1228.59; found: 1229.38.
As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water, each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
Compound HT3 and Compound F12-P-Dopant were co-deposited by vacuum on the anode at 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.
Then, Compound GH3 (host) and Compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form an emission layer having a thickness of 400 Å.
Afterwards, Compound ET3 and Liq-N-Dopant were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, Liq-N-Dopant 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 completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in a similar manner as in Example 1, except that the compounds shown in Table 2 were each used instead of Compound 1 as a dopant in forming an emission layer.
For the organic light-emitting devices (OLEDs) of Examples 1 to 4 and Comparative Examples 1 and 2, the driving voltage (Volts, V), maximum value of external quantum efficiency (Max EQE, %), maximum emission wavelength (λmax, nm), and lifespan (LT97, relative %) were evaluated, 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. The lifespan (LT97) (at 6,000 nit) was a measure of the time taken for the luminance to decline to 97% of the initial luminance of 100%, and the lifespan values are expressed as relative values with respect to Comparative Example 1.
From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had low driving voltages, increased maximum external quantum efficiencies, and long lifespan characteristics.
From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had a lower driving voltage, higher maximum external quantum efficiency, and an improved lifespan, compared to the organic light-emitting devices of Comparative Examples 1 and 2.
As described above, an organometallic compound represented by Formula 1 according to one or more embodiments may have excellent electrical characteristics. Thus, an electronic device, for example, an organic light-emitting device, including at least one of the organometallic compounds represented by Formula 1 may have a low driving voltage, a high external quantum efficiency, and long lifespan characteristics. Accordingly, by using the organometallic compound, a high-quality organic light-emitting device may be realized.
It should be understood that exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the FIGURE, 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 |
|---|---|---|---|
| 10-2023-0078354 | Jun 2023 | KR | national |
