Patent Application
20230165095
This application is based on and claims priority to Korean Patent Application No. 10-2021-0124268, filed on Sep. 16, 2021, in the Korean Intellectual Property Office, and all benefits under 35 U.S.C. § 119, the content of which is incorporated by reference herein in its entirety.
The present disclosure relates to light-emitting devices and electronic apparatuses including the same.
From among light-emitting devices, organic light-emitting devices (OLEDs) are self-emission devices, which have improved characteristics in terms of viewing angles, response time, luminance, 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 located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located 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 transition from an excited state to a ground state to thereby generate light.
Meanwhile, a light-emitting device including a plurality of color conversion elements (for example, quantum dot color conversion elements) uses a blue-organic light-emitting device substrate or a white-organic light-emitting device substrate as a light source.
Provided are light-emitting devices having high luminescence efficiency and long lifespans, and electronic apparatuses including the same.
Additional aspects will be set forth in part in the description, which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect, a light-emitting device includes:
an organic light-emitting device (OLED) substrate including a structure in which at least one blue emission unit and at least one green emission unit are stacked, wherein the OLED substrate emits blue light and green light; and
a color control unit located in the path of light emitted from the OLED substrate, wherein the color control unit controls a color of the light emitted from the OLED substrate,
wherein the at least one green emission unit includes a first compound and a second compound,
the first compound and the second compound may be different from each other,
the first compound emits first light having a first spectrum, and λP(1) is a first emission peak wavelength (nm) of the first spectrum, as evaluated from a first photoluminescence spectrum measured from a first film including the first compound,
the second compound may emit second light having a second spectrum, and λP(2) is a second emission peak wavelength (nm) of the second spectrum, as evaluated from a second photoluminescence spectrum measured from a second film including the second compound,
an absolute value of the difference between λP(1) and λP(2) is from about 0 nanometer (nm) to about 30 nm, and
λP(1) and λP(2) are each independently from about 500 nm to about 570 nm.
Both the first compound and the second compound may emit a green light.
According to another aspect, a light-emitting device includes:
an organic light-emitting device (OLED) substrate including a structure in which at least one blue emission unit and at least one green emission unit are stacked, wherein the OLED substrate emits blue light and green light; and
a color control unit located in the path of light emitted from the OLED substrate, wherein the color control unit controls a color of the light emitted from the OLED substrate,
wherein the at least one green emission unit includes a first compound and a second compound,
the first compound and the second compound may be different from each other,
the first compound and the second compound may emit a green light,
an absolute value of the difference between λP(1) and λP(2) is from about 0 nanometer (nm) to about 30 nm, and
λP(1) and λP(2) are each independently from about 500 nm to about 570 nm.
According to another aspect, provided is an organic light-emitting device (OLED) substrate including a structure in which at least one blue emission unit and at least one green emission unit are stacked, wherein the OLED substrate emits blue light and green light,
wherein the at least one green emission unit includes a first compound and a second compound,
the first compound and the second compound may be different from each other,
the first compound emits first light having a first spectrum, and λP(1) is a first emission peak wavelength (nm) of the first spectrum, as evaluated from a first photoluminescence spectrum measured from a first film including the first compound,
the second compound may emit second light having a second spectrum, and λP(2) is a second emission peak wavelength (nm) of the second spectrum, as evaluated from a second photoluminescence spectrum measured from a second film including the second compound,
an absolute value of the difference between λP(1) and λP(2) is from about 0 nanometer (nm) to about 30 nm, and
λP(1) and λP(2) are each independently from about 500 nm to about 570 nm.
Both the first compound and the second compound may emit a green light.
According to another aspect, provided is an organic light-emitting device (OLED) substrate including a structure in which at least one blue emission unit and at least one green emission unit are stacked, wherein the OLED substrate emits blue light and green light,
wherein the at least one green emission unit includes a first compound and a second compound,
the first compound and the second compound may be different from each other,
the first compound and the second compound may emit a green light,
an absolute value of the difference between λP(1) and λP(2) is from about 0 nanometer (nm) to about 30 nm, and
λP(1) and λP(2) are each independently from about 500 nm to about 570 nm.
According to another aspect, an electronic apparatus includes the light-emitting device.
The above and other aspects, features, and advantages of one or more exemplary embodiments of the disclosure will be more apparent from the following detailed description taken in conjunction with the accompanying drawings, in which:
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 the specification. 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.
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.
Hereinafter, a light-emitting device according to embodiments will be described in further detail with reference to the accompanying drawings. The width and thickness of the layers or regions shown in the accompanying drawings may be exaggerated for clarity of the specification and convenience of description. The same reference numerals denote the same elements throughout the detailed description.
The light-emitting device of
The number of emission units included in the OLED substrate 1 may be two or more, or for example, 2 to 20, or 2 to 10. In one or more embodiments, the number of emission units included in the OLED substrate 1 may be 2, 3, 4, or 5.
The OLED substrate 1 includes a structure in which at least one blue emission unit and at least one green emission unit are stacked, for example sequentially stacked. In one or more embodiments, in the OLED substrate 1, the at least one blue emission unit and the at least one green emission unit may be connected in series to each other to form a tandem structure. Accordingly, the OLED substrate 1 may have a tandem structure.
Each of the blue emission units may emit a blue light having an emission peak wavelength of about 440 nanometers (nm) to about 500 nm, or about 450 nm to about 480 nm.
Each of the green emission units may emit a green light having an emission peak wavelength of about 500 nm to about 570 nm, or about 510 nm to about 550 nm.
The number of the blue emission units included in the OLED substrate 1 may be the same as or greater than the number of the green emission units. In one or more embodiments, the ratio of the number of the blue emission units to the number of the green emission units may be 1:1 to 10:1, or 1:1 to 5:1.
In one or more embodiments, the number of the blue emission units may be 1, 2, 3, 4, or 5, and the number of the green emission units may be 1, 2, 3, or 4.
In one or more embodiments, the number of the blue emission units may be 1, 2, or 3, and the number of the green emission units may be 1 or 2.
In one or more embodiments, the number of the blue emission units may be 2 or 3, and the number of the green emission units may be 1 or 2. In one or more embodiments, the number of the blue emission units may 3, and the number of the green emission units may be 1.
The stacking order of the at least one blue emission unit and at least one green emission unit may be variously modified. In one or more embodiments, the at least one blue emission unit and the at least one green emission unit may be alternately stacked. In one or more embodiments, the at least one green emission unit (for example, all green emission units) may be located closer to the color control unit 2 than the at least one blue emission unit (for example, all blue emission units).
From the OLED substrate 1, mixed light including blue light and green light is emitted.
The at least one green emission units of the OLED substrate 1 includes of a first compound and a second compound, for example, the first compound and the second compound may be mixed. The first compound and the second compound are different from each other.
In one or more embodiments, the at least one green emission units of the OLED substrate 1 may include a layer including a mixture of the first compound and the second compound.
The layer including the mixture of the first compound and the second compound may be formed by i) a co-deposition process or ii) a soluble process including providing a first solution and a heat treatment. During the co-deposition process, a deposition target material may include a first compound and a second compound, and the first solution may include the first compound and the second compound. Therefore, the “layer including the mixture of the first compound and the second compound” is clearly distinguished from, for example, a double-layer structure in which a layer containing the first compound and a layer containing the second compound are stacked.
The color control unit 2 may include a quantum dot, an inorganic phosphor, an organic fluorescent material, an organic phosphorescent material, or a combination thereof. In one or more embodiments, the color control unit 2 may include a plurality of quantum dots.
The color control unit 2 may include a first color control element for green conversion and a second color control element for red conversion. The first color control element and the second color control element may be patterned for corresponding pixels capable of emitting a different color of light.
The color control unit 2 may include a first color control element for green conversion, a second color control element for red conversion, and a third color control element for blue conversion. The first color control element, the second color control element, and the third color control element may be patterned for corresponding pixels capable of emitting a different color of light.
In one or more embodiments, each of the first color control element and the second color control element may be a color conversion element.
In one or more embodiments, each of the first color control element and the second color control element may be a quantum dot-containing color conversion element.
In one or more embodiments, the third color control element may be a color conversion element or a color filter.
In one or more embodiments, the third color control element may be a quantum dot-containing color conversion element or an absorption type color filter.
In one or more embodiments, the color control unit 2 may include a first color control element including a first quantum dot for green conversion, a second color control element including a second quantum dot for red conversion, and a third color control element for blue conversion.
In one or more embodiments, the color control unit 2 may further include a first color filter located on the first color control element, and a second color filter located on the second color control element.
The light-emitting device may further include a thin-film transistor (TFT) array substrate including a plurality of TFTs (not shown). The plurality of TFTs of the TFT array substrate may be a device for driving pixel (subpixel) regions of the OLED substrate 1. When the light-emitting device is a top-emission type light-emitting device, the TFT array substrate may be located under or below the OLED substrate 1. When the light-emitting device is a bottom-emission type light-emitting device, the TFT array substrate may be located between the OLED substrate 1 and the color control unit 2.
Located between the OLED substrate 1 and the color control unit 2 may be an optical film (for example, a selective reflection film, a capping layer, or the like) that may control the optical characteristics of the light-emitting device in various ways; an encapsulating member to prevent oxygen and/or moisture from external air from reaching the OLED substrate 1; or the like.
In one or more embodiments, a selective reflection film may be additionally located between the OLED substrate 1 and the color control unit 2.
The selective reflection film may be configured to transmit blue light and green light and to reflect red light. The selective reflection film may act to transmit a wavelength band of about 440 nm to about 550 nm and reflect a wavelength band of about 610 nm to about 760 nm. Accordingly, the mixed light including blue light and green light emitted from the OLED substrate 1 may be irradiated to the color control unit 2 through the selective reflection film. In one or more embodiments, red light emitted downward from the second color control element 70b, which will be described later, may be reflected by the selective reflection film and emitted upward. Accordingly, the optical efficiency may be improved by the selective reflection film. When necessary, the selective reflection film may be optionally formed only under the second color control element 70b, which will be described later.
For example, the selective reflection film may be formed in a distributed Bragg reflector (DBR) structure. A DBR structure that passes or reflects only the desired wavelength band may be created by repeatedly stacking two material layers (dielectrics) having different refractive indices and adjusting the thickness and the number of layers to be stacked of the material layers. The DBR structure may be applied to the selective reflection film. For example, a first dielectric layer and a second dielectric layer may be repeatedly stacked, and the reflectance or transmittance of the desired wavelength band may be increased by adjusting the material, the thickness, and the number of layers to be stacked of the material layers. In one or more embodiments, the selective reflection film may have a dichroic mirror structure.
The light-emitting device may not emit white light.
The first compound emits first light having a first spectrum and λP(1) is a first emission peak wavelength (nm) of the first spectrum, and the second compound emits second light having a second spectrum and λP(2) is a second emission peak wavelength (nm) in the second spectrum. The absolute value of the difference between the λP(1) and λP(2) is from 0 nm to about 30 nm, 0 nm to about 25 nm, 0 nm to about 20 nm, 0 nm to about 15 nm, or 0 nm to about 10 nm, and λP(1) and λP(2) are each independently about 500 nm to about 570 nm, or about 500 nm to about 550 nm. In one or more embodiments, each of λP(1) and λP(2) may independently be about 500 nm to about 540 nm, or about 510 nm to about 540 nm.
λP(1) and λP(2) are evaluated from the photoluminescence (PL) spectra measured with respect to the first film and the second film, respectively, and are emission peak wavelengths in the corresponding photoluminescence spectra, respectively. In other words, λP(1) is evaluated from a first photoluminescence spectrum measured from a first film comprising the first compound and is an emission peak wavelengths in the first photoluminescence spectrum, and λP(2) is evaluated from a second photoluminescence spectrum measured from a second film comprising the second compound and is an emission peak wavelengths in the second photoluminescence spectrum.
The term “first film” as used herein refers to a film including the first compound, and the term “second film” as used herein refers to a film including the second compound. The first film and the second film may be manufactured using various methods, for example, a vacuum deposition method, and a coating and heating method. The first film and the second film may further include a compound, for example, a host described herein, other than the first compound and the second compound.
In one or more embodiments, the first compound and the second compound may each be an emitter.
In one or more embodiments, both the first compound and the second compound may emit a green light.
In one or more embodiments, the first compound and the second compound may each be an emitter, and λP(1) and λP(2) may each independently be about 510 nm to about 540 nm.
In one or more embodiments, the first compound may be a sensitizer, and the second compound may be an emitter.
In one or more embodiments, the first compound may be a sensitizer, the second compound may be an emitter, λP(1) may be about 500 nm to about 520 nm, and λP(2) may be about 510 nm to about 540 nm.
In one or more embodiments, the first compound and the second compound may each be a phosphorescent compound.
The phosphorescent compound may be an organometallic compound containing a transition metal (for example, iridium, platinum, osmium, or the like), and may be electrically neutral.
In one or more embodiments, the phosphorescent compound may be a platinum-containing organometallic compound or an iridium-containing organometallic compound. In one or more embodiments, the platinum-containing organometallic compound may be a platinum-containing organometallic compound including platinum and a tetradentate ligand bonded to the platinum. In one or more embodiments, the tetradentate ligand includes a carbon atom and an oxygen atom (or, a sulfur atom), and the platinum-containing organometallic compound may include a chemical bond between the carbon atom of the tetradentate ligand and the platinum, and a chemical bond between the oxygen atom (or, the sulfur atom) of the tetradentate ligand and the platinum.
In one or more embodiments, the first compound may be a phosphorescent compound, and the second compound may be a fluorescent compound.
In one or more embodiments, the first compound and the second compound may each independently be a fluorescent compound.
The fluorescent compound may be a thermally-activated delayed fluorescence (TADF) compound, or a prompt fluorescent compound.
In one or more embodiments, each of the first compound and the second compound may independently be a fluorescent compound, wherein the first compound may be a thermally-activated delayed fluorescence compound, and the second compound may be a prompt fluorescent compound.
The first compound and the second compound may satisfy Condition 1 or Condition 2:
Condition 1
The first compound is a platinum-containing organometallic compound including platinum and a tetradentate ligand bonded to the platinum, and
the second compound is an iridium-containing organometallic compound.
Condition 2
Each of the first compound and the second compound is independently an iridium-containing organometallic compound.
In one or more embodiments, the first compound and the second compound may satisfy Condition 1,
μ(Pt) may be about 0.5 debye to about 5.0 debye,
μ(Pt) may be less than μ(Ir),
μ(Pt) may be an electric dipole moment of the first compound,
μ(Ir) may be an electric dipole moment of the second compound, and
each of μ(Pt) and μ(Ir) may be calculated based on density functional (DFT) theory. Any various programs may be used for the quantum mechanical calculation based on the DFT, and for example, a Gaussian 16 program may be used.
In the case of a mixture of the first compound and the second compound that satisfy Condition 1, aggregation among molecules of the first compound in the mixture, aggregation among molecules of the second compound in the mixture, and/or aggregation among molecules of the first compound and molecules of the second compound in the mixture, may be substantially minimized. Accordingly, without any consideration about intermolecular aggregation, the amounts (for example, weight) of the first compound and the second compound in the mixture may be relatively increased. Accordingly, a layer including the mixture and a light-emitting device including the mixture may have excellent luminescence efficiency and lifespan characteristics. In addition, when an emission unit of a light-emitting device contains a mixture of the first compound and the second compound which satisfy Condition 1, the hole flux in the emission unit is increased due to the mixture, so that an exciton recombination zone in the emission unit may be spaced apart from each of the interface between an emission layer and a hole transport region and the interface between an emission layer and an electron transport region, resulting in improved lifespan characteristics of the light-emitting device.
The platinum-containing organometallic compound includes one platinum atom and may contain no metal(s) other than platinum.
The platinum-containing organometallic compound may contain no ligands other than the tetradentate ligand bound to the platinum.
The tetradentate ligand bound to platinum in the platinum-containing organometallic compounds may have excellent electrical characteristics and structural rigidity. In addition, the platinum-containing organometallic compound having the tetradentate ligand bound to platinum has a planar structure and may have a relatively small dipole moment. Thus, the layer including the platinum-containing organometallic compound or the light-emitting device including the platinum-containing organometallic compound have excellent luminescence efficiency and a long lifespan.
The iridium-containing organometallic compound contains one iridium atom and may contain no metal(s) other than iridium.
In this specification, the terms “electric dipole moment of the first compound” and “electric dipole moment of the second compound” as used herein may refer to “total permanent dipole moment in the molecule of the first compound” and “total permanent dipole moment in the molecule of the second compound”, respectively.
In one or more embodiments, μ(Pt) may be from about 0.5 debye to about 5.0 debye.
In one or more embodiments, μ(Pt) may be from about 0.5 debye to about 3.0 debye, about 1.0 debye to about 3.0 debye, about 1.5 debye to about 3.0 debye, about 1.7 debye to about 3.0 debye, or about 1.7 debye to about 2.7 debye.
In one or more embodiments, μ(Pt) may be from about 2.0 debye to about 5.0 debye, about 3.0 debye to about 5.0 debye, or about 4.0 debye to about 5.0 debye.
In one or more embodiments, μ(Ir) may be from about 4.0 debye to about 9.0 debye, about 4.5 debye to about 7.5 debye, or about 5.0 debye to about 7.0 debye.
In one or more embodiments, μ(Ir)-μ(Pt) may be from about 0.3 debye to about 4.0 debye.
In one or more embodiments, μ(Ir)-μ(Pt) may be from about 2.0 debye to about 4.0 debye or about 2.0 debye to about 3.0 debye.
In one or more embodiments, μ(Ir)-μ(Pt) may be from about 0.3 debye to about 1.0 debye.
In one or more embodiments, in Condition 1,
λP(Pt) may be equal to λP(Ir),
λP(Pt) may be less than λP(Ir),
λP(Pt) may be greater than λP(Ir),
λP(Pt) and λP(Ir) may each be about 510 nm to about 570 nm,
λP(Pt) and λP(Ir) may each be about 510 nm to about 540 nm,
λP(Pt) may be about 510 nm to about 530 nm, and λP(Ir) may be about 520 nm to about 540 nm,
λP(Pt) and λP(Ir) may each be about 540 nm to about 570 nm, or
λP(Pt) may be about 540 nm to about 560 nm, and λP(Ir) may be about 550 nm to about 570 nm,
wherein λP(Pt) is the first emission peak wavelength λP(1) of the first compound, as evaluated from the first photoluminescence spectrum measured from the first film comprising the first compound, and
λP(Ir) is the second emission peak wavelength λP(2) of the second compound, as evaluated from the second photoluminescence spectrum measured from the second film comprising the second compound.
In one or more embodiments, the light emitting device may satisfy Condition 2, and at least one of Equation 1 to Equation 4. Accordingly, a light-emitting device including the first compound and the second compound satisfying Condition 2 may have better luminescence efficiency and long lifespan:
λP(Ir1)>λP(Ir2) Equation 1
PLQY(Ir1)>PLYQ(Ir2) Equation 2
k
r(Ir1)>kr(Ir2) Equation 3
HOR(Ir1)>HOR(Ir2) Equation 4
wherein, in Equation 1,
λP(Ir1) is the first emission peak wavelength λP(1) of the first compound, as evaluated from the first photoluminescence spectrum measured from the first film comprising the first compound, and λP(Ir2) is the second emission peak wavelength λP(2) of the second compound, as evaluated from the second photoluminescence spectrum measured from the second film comprising the second compound.
In relation to Equation 2, PLQY(Ir1) is the first photoluminescence (PL) quantum yield of the first compound, as evaluated from the first PL spectrum measured from the first film comprising the first compound, and PLQY(Ir2) is the second PL quantum yield of the second compound, as evaluated from the second PL spectrum measured from the second film comprising the second compound.
In relation to Equation 3, kr(Ir1) is a first radiative decay rate of the first compound, as evaluated from the first PL spectrum and first time-resolved PL spectra measured from the first film comprising the first compound, and kr(Ir2) is a second radiative decay rate of the second compound, as evaluated from the second PL spectrum and second time-resolved PL spectra measured from the second film comprising the second compound.
In relation to Equation 4, HOR(Ir1) is a first horizontal orientation ratio of the first compound, as evaluated from a first emission intensity with respect to a first angle measured from the first film comprising the first compound, and HOR(Ir2) is a second horizontal orientation ratio of the second compound, as evaluated from a second emission intensity with respect to a second angle measured from the second film comprising the second compound.
The first film and the second film are those described in the present specification.
In one or more embodiments, the light-emitting device including the first compound and the second compound that satisfies Condition 2 may satisfy:
Equation 1,
at least one of Equation 2 to Equation 4, or
Equation 1, and at least one of Equation 2 to Equation 4.
In one or more embodiments, the light-emitting device including the first compound and the second compound that satisfy Condition 2 may further satisfy Equation 5:
HOMO(Ir1)<HOMO(Ir2) Equation 5
wherein, in Equation 5,
HOMO (Ir1) is a first highest occupied molecular orbital (HOMO) energy level of the first compound, as evaluated from a first atmospheric photoelectron spectrum measured from the first film comprising the first compound, and
HOMO (Ir2) is a second highest occupied molecular orbital (HOMO) energy level of the second compound, as evaluated from a second atmospheric photoelectron spectrum measured from the second film comprising the second compound.
Each of HOMO (Ir1) and HOMO (Ir2) may be a negative value measured using an atmospheric photoelectron spectrometer, for example, AC3 manufactured by RIKEN KEIKI Co., Ltd.
Since the light-emitting device including the first compound and the second compound satisfies Condition 2 and satisfies Equation 5, the second compound in the mixture has a shallower HOMO energy level than the first compound, and a relatively greater amount of holes may be trapped in the second compound. As a result, in the case of the light-emitting device including the mixture, without the phenomenon in which the first compound and the second compound are changed into an anionic state due to electrons injected into the mixture and the increase in the driving voltage, holes and electrons may effectively recombine in the first compound and/or the second compound. Accordingly, the light-emitting device may have excellent luminescence efficiency characteristics and excellent lifespan characteristics.
In one or more embodiments, in the light-emitting device including the first compound and the second compound satisfying Condition 2,
|HOMO (Ir1)−HOMO (Ir2)| may be about 0.03 electron volts (eV) to about 0.30 eV, and
|HOMO (Ir1)−HOMO (Ir2)| may be the absolute value of HOMO (Ir1)−HOMO (Ir2).
In one or more embodiments, the platinum-containing organometallic compound in Condition 1 may comprise a chemical bond between a carbon atom of the tetradentate ligand and the platinum, and
a chemical bond between an oxygen atom of the tetradentate ligand and the platinum, and each of the iridium-containing organometallic compounds in Condition 1 and Condition 2 contains a first ligand, a second ligand, and a third ligand,
wherein, in each of the iridium-containing organometallic compounds,
the first ligand, the second ligand, and the third ligand are identical to each other,
the first ligand and the second ligand are identical to each other, and the second ligand and the third ligand are different from each other, or
the first ligand, the second ligand, and the third ligand are different from each other, and
wherein the first ligand, the second ligand, and the third ligand may each be:
a bidentate ligand bonded to the iridium of the iridium-containing organometallic compound via two nitrogen atoms;
a bidentate ligand bonded to the iridium of the iridium-containing organometallic compound via a nitrogen atom and a carbon atom; or
a bidentate ligand bonded to the iridium of the iridium-containing organometallic compound via two carbon atoms.
In one or more embodiments, the platinum-containing organometallic compound may be an organometallic compound represented by Formula 1, and the iridium-containing organometallic compound may be an organometallic compound represented by Formula 2:
M1 in Formula 1 may be platinum (Pt),
M2 in Formula 2 may be iridium (Ir),
L11 in Formula 2 may be a ligand represented by Formula 2-1,
L12 in Formula 2 may be a ligand represented by Formula 2-2,
L13 in Formula 2 may be a ligand represented by Formula 2-1 or 2-2,
L11 and L12 in Formula 2 may be different from each other,
n11, n12 and n13 in Formula 2 may each independently be 0, 1, 2, or 3, and the sum of n11, n12, and n13 may be 3,
X1 to X4 and Y1 to Y4 in Formulae 1, 2-1, and 2-2 may each independently be C or N,
X5 to X8 in Formula 1 may each independently be a chemical bond, *—O—*′, *—S—*′, *—N(R′)—*′, *—C(R′)(R″)—*′, or *—C(═O)—*′, wherein at least one of X5 to X8 may not be a chemical bond,
two of a bond between X5 or X1 and M1, a bond between X6 or X2 and M1, a bond between X7 or X3 and M1, and a bond between X8 or X4 and M1 may each be a coordinate bond, and the other two may each be a covalent bond,
ring CY1 to ring CY4 and ring A1 to ring A4 in Formulae 1, 2-1, and 2-2 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
T11 to T14 in Formula 1 may each independently be a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5a)═*′, *═C(R5a)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
n1 to n4 in Formula 1 may each independently be 0 or 1, and 3 or more of n1 to n4 may each be 1,
when n1 is 0, T11 does not exist, when n2 is 0, T12 does not exist, when n3 is 0, T13 does not exist, when n4 is 0, T14 does not exist,
L1 to L4 and W1 to W4 in Formulae 1, 2-1, and 2-2 may each independently be a single bond, a C1-C20 alkylene group that is unsubstituted or substituted with at least one R10a, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
b1 to b4 in Formula 1 may each independently be an integer of 1 to 10,
R1 to R4, R5a, R5b, R′, R″, and Z1 to Z4 in Formulae 1, 2-1, and 2-2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 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 C1-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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
c1 to c4, a1 to a4, e1 to e4, and d1 to d4 in Formulae 1, 2-1, and 2-2 may each independently be an integer of 0 to 20,
the second compound may not be tris[2-phenylpyridine]iridium,
two or more substituents in at least one of i) two or more of a plurality of R1(s), ii) two or more of a plurality of R2(s), iii) two or more of a plurality of R3(s), iv) two or more of a plurality of R4(s), v) R5a and R5b, vi) two or more of a plurality of Z1(s), vii) two or more of a plurality of Z2(s), viii) two or more of a plurality of Z3(s), ix) two or more of a plurality of Z4(s), x) two or more of R1 to R4, R5a, and R5b, and xi) two or more of Z1 to Z4 may optionally be linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R10a is understood by referring to the description of R1 provided herein,
* and *′ in Formulae 2-1 and 2-2 each indicate a binding site to M2,
* and *′ in X5 to X8 and T11 to T14 each indicate a binding site to an adjacent atom, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted 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:
deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
Platinum (Pt) as M1 in Formula 1 may be replaced by palladium (Pd) or gold (Au). That is, the platinum-containing organometallic compound may be replaced with a palladium-containing or a gold-containing organometallic compound.
In Formula 2, n11 to n13 each indicates the number of L11(s) to the number of L13(s), respectively, and may each independently be 0, 1, 2, or 3, wherein n11+n12+n13 may be 3.
In one or more embodiments, in Formula 2, n11 may be 1, 2, or 3, and n12 and n13 may each independently be 0, 1, or 2.
In one or more embodiments, in Formula 2, n12 may be 1, 2, or 3, and n11 and n13 may each independently be 0, 1, or 2.
In one or more embodiments, n11 may be 1, n12 may be 2, and n13 may be 0.
In one or more embodiments, n11 may be 2, n12 may be 1, and n13 may be 0.
In one or more embodiments, n11 may be 3, and n12 and n13 may each be 0.
In one or more embodiments, n12 may be 3, and n11 and n13 may each be 0.
The iridium-containing organometallic compound represented by Formula 2 may be a heteroleptic complex or a homoleptic complex.
In one or more embodiments, the iridium-containing organometallic compound may be a heteroleptic complex.
In Formulae 1, 2-1, and 2-2, X1 to X4 and Y1 to Y4 may each independently be C or N.
In one or more embodiments, at least one of X1 to X4 in Formula 1 may be C.
In one or more embodiments, X1 in Formula 1 may be C.
In one or more embodiments, in Formula 1, i) X1 and X3 may each be C, and X2 and X4 may each be N, or ii) X1 and X4 may each be C, and X2 and X3 may each be N.
In one or more embodiments, in Formulae 2-1 and 2-2, Y1 and Y3 may each be N, and Y2 and Y4 may each be C.
In Formula 1, X5 to X8 may each independently be a chemical bond, *—O—*′, *—S—*′ *—N(R′)—*′, *—C(R′)(R″)—*′, or *—C(═O)—*′, wherein at least one of X5 to X8 may not be a chemical bond, and * and *′ each indicated a bonding site to an adjacent atom. R′ and R″ may each be the same as described herein.
In one or more embodiments, X5 in Formula 1 may not be a chemical bond.
In one or more embodiments, X5 in Formula 1 may be O or S.
In one or more embodiments, in Formula 1, X5 may be O or S, and X5 to X8 may each be a chemical bond.
In Formula 1, two bonds of a bond between X5 or X1 and M1, a bond between X5 or X2 and M1, a bond between X7 or X3 and M1, and a bond between X8 or X4 and M1 may each be a coordinate bond, and the other two bonds may each be a covalent bond.
In one or more embodiments, a bond between X2 and M in Formula 1 may be a coordinate bond.
In one or more embodiments, in Formula 1, a bond between X5 or X1 and M and a bond between X3 and M may each be a covalent bond, and a bond between X2 and M and a bond between X4 and M may each be a coordinate bond.
In one or more embodiments, the platinum-containing organometallic compound and iridium-containing organometallic compound may each be electrically neutral.
In Formulae 1, 2-1, and 2-2, ring CY1 to ring CY4 and ring A1 to ring A4 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, each of ring CY1, ring CY3, and ring CY4 may not be a benzimidazole group.
For example, in Formulae 1, 2-1, and 2-2, ring CY1 to ring CY4 and ring A1 to A4 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings are condensed with one or more second rings,
wherein the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a piperidine group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one or more embodiments, in Formulae 1, 2-1, and 2-2, ring CY1 to ring CY4 and ring A1 to ring A4 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene 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 benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidinopyrrole group, a pyrimidinopyrazole group, a pyrimidinoimidazole group, a pyrimidinooxazole group, a pyrimidinoisoxazole group, a pyrimidinothiazole group, a pyrimidinoisothiazole group, a pyrimidinooxadiazole group, a pyrimidinothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthoxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthoxadiazole group, a naphthothiadiazole group, a phenanthrenopyrrole group, a phenanthrenopyrazole group, a phenanthrenoimidazole group, a phenanthrenoxazole group, a phenanthrenoisoxazole group, a phenanthrenothiazole group, a phenanthrenoisothiazole group, a phenanthrenoxadiazole group, a phenanthrenothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, a benzene group condensed with a norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.
In one or more embodiments, ring CY1 and ring CY3 in Formula 1 may each independently be:
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, or
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each condensed with at least one of a cyclohexane group, a cyclohexene group, a norbornane group, a piperidine group, or a combination thereof.
In one or more embodiments, ring CY2 in Formula 1 may be:
an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group; or
an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, each condensed with at least one of a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a pyridine group, a pyrimidine group, or a combination thereof.
In one or more embodiments, ring CY4 in Formula 1 may be:
a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group; or
a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group, each condensed with at least one of a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a pyridine group, a pyrimidine group, or a combination thereof.
In Formulae 2-1 and 2-2, ring A1 and ring A3 may be the same as or different from each other.
In one or more embodiments, a Y1-containing monocyclic group in ring A1, a Y2-containing monocyclic group in ring A2, and Y4-containing monocyclic group in ring A4 may each be a 6-membered ring.
In one or more embodiments, a Y3-containing monocyclic group in ring A3 may be a 6-membered ring.
In one or more embodiments, a Y3-containing monocyclic group in ring A3 may be a 5-membered ring.
In one or more embodiments, a Y1-containing monocyclic group in ring A1 may be a 6-membered ring, and a Y3-containing monocyclic group in ring A3 may be a 5-membered ring.
In one or more embodiments, in Formulae 2-1 and 2-2, ring A1 and ring A3 may each independently be i) one of Group A, ii) a polycyclic group in which two or more of Group A are condensed with each other, or iii) a polycyclic group in which at least one of Group A and at least one of Group B are condensed with each other,
wherein Group A may include a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
Group B may include a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, or silole group.
In one or more embodiments, in Formula 2-2, ring A3 may be i) one of Group C, ii) a polycyclic group in which two or more of Group C are condensed with each other, or iii) a polycyclic group in which at least one of Group C and at least one of Group D are condensed with each other,
wherein Group C may include a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, or an isothiazole group, and
Group D may include a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a cyclopentadiene group, a silole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group.
In one or more embodiments, ring A1 in Formula 2-1 may be:
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group; or
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.
In one or more embodiments, ring A3 in Formula 2-2 may be:
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group;
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof; or
an imidazole group, a benzimidazole group, a naphthoimidazole group, a phenanthrenoimidazole group, a pyridoimidazole group, an oxazole group, a benzoxazole group, a naphthooxazole group, a phenanthrenoxazole group, a pyridooxazole group, a thiazole group, a benzothiazole group, a naphthothiazole group, a phenanthrenothiazole group, or a pyridothiazole group.
In one or more embodiments, ring A2 and ring A4 in Formulae 2-1 and 2-2 may be different from each other.
In one or more embodiments, in Formulae 2-1 and 2-2, ring A2 and ring A4 may each independently be i) one of Group E, ii) a polycyclic group in which two or more of Group E are condensed with each other, or iii) a polycyclic group in which at least one of Group E and at least one of Group F are condensed with each other,
wherein Group E may include a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
Group F may include a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, or an isothiazole group.
In one or more embodiments, in Formula 2-1, ring A2 may be a polycyclic group in which two or more of Group E and at least one of Group F are condensed with each other.
In one or more embodiments, in Formula 2-2, ring A4 may be a polycyclic group in which two or more of Group E and at least one of Group F are condensed with each other.
In one or more embodiments, ring A2 in Formula 2-1 may be:
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.
In one or more embodiments, ring A4 in Formula 2-2 may be:
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or a dibenzosilole group; or
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or a dibenzosilole group, each condensed with at least one of a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a cyclohexane group, a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, an isothiazole group, or a combination thereof.
In Formula 1, T11 to T14 may each independently be a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′ *—C(R5a)═*′, *═C(R5a)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, wherein * and *′ each indicates a binding site to an adjacent atom.
In one or more embodiments, T11 and T12 in Formula 1 may be a single bond, and T13 may be a single bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, or *—O*′, wherein * and *′ each indicates a binding site to an adjacent atom.
n1 to n4 in Formula 1 indicate numbers of T11 to T14, respectively, and may each independently be 0 or 1, wherein three or more of n1 to n4 may each be 1. That is, an organometallic compound represented by Formula 1 may have a tetradentate ligand.
In Formula 1, when n1 is 0, T11 does not exist (that is, ring CY1 and ring CY2 are not linked to each other), when n2 is 0, T12 does not exist (that is, ring CY2 and ring CY3 are not linked to each other), when n3 is 0, T13 does not exist (that is, ring CY3 and ring CY4 are not linked to each other), and when n4 is 0, T14 does not exist (that is, ring CY4 and ring CY1 are not linked to each other).
In one or more embodiments, in Formula 1, n1 to n3 may each be 1, and n4 may be 0.
L1 to L4 and W1 to W4 in Formulae 1, 2-1, and 2-2 may each independently be a single bond, a C1-C20 alkylene group that is unsubstituted or substituted with at least one R10a, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, in Formulae 1, 2-1, and 2-2, L1 to L4 and W1 to W4 may each independently be:
a single bond, or
a C1-C20 alkylene group, a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 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 iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 to L4 and W1 to W4 in Formulae 1, 2-1, and 2-2 may each independently be:
a single bond; or
a C1-C20 alkylene group, a benzene group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, in Formulae 1, 2-1, and 2-2, L1 to L4 and W1 to W4 may each independently be:
a single bond; or
a C1-C20 alkylene group, a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.
b1 to b4 in Formula 1 indicate the number of L1(s) to the number of L4(s), respectively, and may each independently be an integer from 1 to 10. When b1 is 2 or more, two or more of L1(s) may be identical to or different from each other, when b2 is 2 or more, two or more of L2(s) may be identical to or different from each other, when b3 is 2 or more, two or more of L3(s) may be identical to or different from each other, and when b4 is 2 or more, two or more of L4(s) may be identical to or different from each other. For example, b1 to b4 may each independently be 1, 2, or 3.
R1 to R4, R5a, R5b, R′, R″, and Z1 to Z4 in Formulae 1, 2-1, and 2-2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 may each be as described herein.
In one or more embodiments, R1 to R4, R5a, R5b, R, R″, and Z1 to Z4 in Formulae 1, 2-1, and 2-2 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
a C1-C20 alkyl group, a C2-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (a bicyclo[2.2.1]heptyl group), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 may each independently be:
deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, —CD2CDH2, —CF3, —CF2H, —CFH2, —CH2CF3, —CH2CF2H, —CH2CFH2, —CHFCH3, —CHFCF2H, —CHFCFH2, —CHFCF3, —CF2CF3, —CF2CF2H, or —CF2CFH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, —F, C1-C10 alkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, in Formulae 1, 2-1, and 2-2, R1 to R4, R5a, R5b, R, R″, and Z1 to Z4 may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated C1-C20 alkoxy group, a fluorinated C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in Formula 2-1, each of e1 and d1 may not be 0, and at least one of a plurality of Z1(s) may be a deuterated C1-C20 alkyl group, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5). Q3 to Q5 are as described in the present specification.
For example, Q3 to Q5 may each independently be:
a C1-C60 alkyl group unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; or
a C1-C60 aryl group unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof.
In one or more embodiments, Q3 to Q5 may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, Q3 to Q5 may be identical to each other.
In one or more embodiments, two or more of Q3 to Q5 may be different from each other.
In one or more embodiments, the iridium-containing organometallic compound may satisfy at least one of Condition 10-1 to Condition 10-8:
Condition 10-1
Each of e1 and d1 in Formula 2-1 is not 0, and at least one Z1 includes deuterium.
Condition 10-2
Each of e2 and d2 in Formula 2-1 is not 0, and at least one Z2 includes deuterium.
Condition 10-3
Each of e3 and d3 in Formula 2-2 is not 0, and at least one Z3 includes deuterium.
Condition 10-4
Each of e4 and d4 in Formula 2-2 is not 0, and at least one Z4 includes deuterium.
Condition 10-5
Each of e1 and d1 in Formula 2-1 is not 0, and at least one Z1 includes a fluoro group.
Condition 10-6
Each of e2 and d2 in Formula 2-1 is not 0, and at least one Z2 includes a fluoro group.
Condition 10-7
Each of e3 and d3 in Formula 2-2 is not 0, and at least one Z3 includes a fluoro group.
Condition 10-8
Each of e4 and d4 in Formula 2-2 is not 0, and at least one Z4 includes a fluoro group.
In one or more embodiments, in Formulae 1, 2-1, and 2-2, R1 to R4, R5a, R5b, R, R″, and Z1 to Z4 may each independently be hydrogen, deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C2-C10 alkenyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-227, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-129, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5) (Q3 to Q5 may each be as described herein):
In Formulae 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is a trimethylgermyl group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 9-701 to 9-710:
The “group in which at least one hydrogen in Formulae 10-1 to 10-129 is substituted with deuterium” and “the group in which at least one hydrogen in Formulae 10-201 to 10-350 is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
The “group in which at least one hydrogen in Formulae 10-1 to 10-129 is substituted with —F” and “the group in which at least one hydrogen in Formulae 10-201 to 10-350 is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-617:
In Formulae 1, 2-1, and 2-2, c1 to c4 indicate the number of R1(s) to the number of R4(s), respectively; a1 to a4 indicate the number of groups represented by *-[(L1)b1-(R1)c1], the number of groups represented by *-[(L2)b2-(R2)c2], the number of groups represented by *-[(L3)b3-(R3)c3], and the number of groups represented by *-[(L4)b4-(R4)c4], respectively; e1 to e4 indicate the number of Z1(s) to the number of Z4(s), respectively; and d1 to d4 indicate the number of a group(s) represented by *—[W1—(Z1)e1], the number of groups represented by *—[W2—(Z2)e2], the number of groups represented by *—[W3—(Z3)e3], and the number of groups represented by *—[W4—(Z4)e4], respectively, and c1 to c4, a1 to a4, e1 to e4, and d1 to d4 may each independently be an integer from 0 to 20. When c1 is 2 or more, two or more R1(s) may be identical to or different from each other, when c2 is 2 or more, two or more R2(s) may be identical to or different from each other, when c3 is 2 or more, two or more R3(s) may be identical to or different from each other, when c4 is 2 or more, two or more R4(s) may be identical to or different from each other, when a1 is 2 or more, two or more groups represented by *-[(L1)b1-(R1)c1] may be identical to or different from each other, when a2 is 2 or more, two or more groups represented by *-[(L2)b2-(R2)c2] may be identical to or different from each other, when a3 is 2 or more, two or more groups represented by *-[(L3)b3-(R3)c3] may be identical to or different from each other, when a4 is 2 or more, two or more groups represented by *-[(L4)b4-(R1)c4] may be identical to or different from each other, when e1 is 2 or more, two or more Z1(s) may be identical to or different from each other, when e2 is 2 or more, two or more Z2(s) may be identical to or different from each other, when e3 is 2 or more, two or more Z3(s) may be identical to or different from each other, when e4 is 2 or more, two or more Z4(s) may be identical to or different from each other, when d1 is 2 or more, two or more groups represented by *—[W1—(Z1)e1] may be identical to or different from each other, when d2 is 2 or more, two or more groups represented by *—[W2—(Z2)e2] may be identical to or different from each other, when d3 is 2 or more, two or more groups represented by *—[W3—(Z3)e3] may be identical to or different from each other, and when d4 is 2 or more, two or more groups represented by *—[W4—(Z4)e1] may be identical to or different from each other. For example, in Formulae 1, 2-1, and 2-2, c1 to c4, a1 to a4, e1 to e4, and d1 to d4 may each independently be 0, 1, 2, or 3.
In one or more embodiments, in Formula 2-1, a case where Y1 is N, ring A1 is a pyridine group, Y2 is C, ring A2 is a benzene group, and each of d1 and d2 is 0 may be excluded.
In Formulae 1, 2-1, and 2-2, two or more substituents in at least one of i) two or more of a plurality of R1(s), ii) two or more of a plurality of R2(s), iii) two or more of a plurality of R3(s), iv) two or more of a plurality of R4(s), v) R5a and R5b, vi) two or more of a plurality of Z1(s), vii) two or more of a plurality of Z2(s), viii) two or more of a plurality of Z3(s), ix) two or more of a plurality of Z4(s), x) two or more of R1 to R4, R5a, and R5b, and xi) two or more of Z1 to Z4 may optionally be linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
R10a may be as described in connection with R1.
The symbols * and *′ as used herein each indicate a binding site to a neighboring atom, unless otherwise stated.
In one or more embodiments, in Formula 1, n1 may not be 0, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY1(1) to CY1(23):
wherein, in Formulae CY1(1) to CY1(23),
X1 is as described above,
X19 may be *—O—*′, *—S—*′, *—Se—*′, *—N(R19a)—*′, *—C(R19a)(R19b)—*′, or *—Si(R19a)(R19b)—*′
R19a and R19b may each be as described in connection with R1,
* indicates a binding site to X5 in Formula 1, and
*′ indicates a binding site to T11 in Formula 1.
In one or more embodiments, in Formula 1, n1 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY1-1 to CY1-18:
wherein, in Formulae CY1-1 to CY1-18,
X1 is as described above,
R11 to R14 may each be the same as described in connection with R1, and each of R11 to R14 may not be hydrogen,
* indicates a binding site to X5 in Formula 1, and
*′ indicates a binding site to T11 in Formula 1.
In one or more embodiments, in Formula 1, n1 and n2 may each be 1, and ring CY2 may be a group represented by Formula CY2A or CY2B:
wherein, in Formulae CY2A and CY2B,
X2 and CY2 may each be as described herein,
Y91 to Y93 may each independently be *—O—*′, *—S—*′, *—N—*′, *—C—*′, or *—Si—*′,
in Formula CY2A, a bond between X2 and Y91, a bond between X2 and Y92, a bond between X2 and Y93, and a bond between Y22 and Y93 may each be a chemical bond,
*′ indicates a binding site to T11 in Formula 1,
* indicates a binding site to M1 in Formula 1, and
*″ indicates a binding site to T12 in Formula 1.
In one or more embodiments, in Formula 1, each of n1 and n2 may not be 0, and a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(21):
wherein, in Formulae CY2(1) to CY2(21),
X2 is as described in the present specification,
X29 may be O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described herein,
R29a and R29b may each be the same as described in connection with R2,
*′ indicates a binding site to T11 in Formula 1,
* indicates a binding site to M1 in Formula 1,
*″ indicates a binding site to T12 in Formula 1.
In one or more embodiments, in Formula 1, each of n1 and n2 may be 1, and a group represented by
may be a group represented by one of Formulae CY2-1 to CY2-16:
wherein, in Formulae CY2-1 to CY2-16,
X2 is the same as described in the present specification,
X29 may be O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described herein,
R21 to R23, R29a, and R29b may each be the same as described in connection with R2, wherein each of R21 to R23 may not be hydrogen,
*′ indicates a binding site to T1 in Formula 1,
* indicates a binding site to M1 in Formula 1,
*″ indicates a binding site to T12 in Formula 1.
In one or more embodiments, in Formula 1,
each of n1 and n2 may be 1,
a group represented by
may be represented by one of Formulae CY2-9 to CY2-16,
X29 in Formulae CY2-9 to CY2-16 may be N-[(L2)b2-(R2)c2],
L2 may be a benzene group unsubstituted or substituted with at least one R10a,
b2 may be 1 or 2,
c2 may be 2, and
a) one of two R2(s) may be a phenyl group unsubstituted or substituted with at least one of deuterium, a C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, or a combination thereof, and b) the other R2 may be a C4-C20alkyl group or a deuterated C1-C20 alkyl group, each unsubstituted or substituted with at least one C3-C10 cycloalkyl group.
In one or more embodiments, in Formula 1, each of n2 and n3 may not be 0, and a group represented by
may be a group represented by one of Formulae CY3(1) to CY3(15):
wherein, in Formulae CY3(1) to CY3(15),
X3 is the same as described in the present specification,
X39 may be O, S, N(Z39a), C(R39a)(R39b), or Si(R39a)(R39b),
R39a and R39b may each be the same as described in connection with R3,
*″ indicates a binding site to T12 in Formula 1,
* indicates a binding site to M1 in Formula 1,
* indicates a binding site to T13 in Formula 1.
In one or more embodiments, in Formula 1, each of n2 and n3 may be 1, and a group represented by
may be a group represented by one of Formulae CY3-1 to CY3-13:
wherein, in Formulae CY3-1 to CY3-31,
X3 is the same as described in the present specification,
X39 may be O, S, N-[(L3)b3-(R3)c3], C(R39a)(R39b), or Si(R39a)(R39b),
L3, b3, R3, and c3 may each be the same as described herein,
R31 to R33, R39a, and R39b may each be the same as described in connection with R3, wherein each of R31 to R33 may not be hydrogen,
*″ indicates a binding site to T12 in Formula 1,
* indicates a binding site to M1 in Formula 1,
*′ indicates a binding site to T13 in Formula 1.
In one or more embodiments, in Formula 1, n3 may not be 0, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY4(1) to CY4(20):
wherein, in Formulae CY4(1) to CY4(20),
X4 is the same as described in the present specification,
X49 may be O, S, N(R49a), C(R49a)(R49b), or Si(R49a)(R49b),
R49a and R49b may each be the same as described in connection with R4,
*′ indicates a binding site to T13 in Formula 1, and
* indicates a binding site to M1 in Formula 1.
In one or more embodiments, in Formula 1, n3 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY4-1 to CY4-16:
wherein, in Formulae CY4-1 to CY4-16,
X4 is the same as described in the present specification,
R41 to R44 may each be the same as described in connection with R4, and each of R41 to R44 may not be hydrogen,
*′ indicates a binding site to T13 in Formula 1, and
* indicates a binding site to M1 in Formula 1.
In one or more embodiments, the platinum-containing organometallic compound may be a compound represented by one of Formulae 1-1 to 1-3:
wherein, in Formulae 1-1 to 1-3,
M1, X1 to X5, T12, and T13 may each be the same as described herein,
X11 may be N or C(R11), X12 may be N or C(R12), X13 may be N or C(R13), and X14 may be N or C(R14),
R11 to R14 may each be the same as described in connection with R1,
two or more of Ru to R14 may optionally be linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
X21 may be N or C(R21), X22 may be N or C(R22), and X23 may be N or C(R23),
X29 may be O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described herein,
R21 to R23, R29a, and R29b may each be the same as described in connection with R2,
two or more of R21 to R23 may optionally be linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
X31 may be N or C(R31), X32 may be N or C(R32), and X33 may be N or C(R33),
R31 to R33 may each be the same as described in connection with R3,
two or more of R31 to R33 may optionally be linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
X41 may be N or C(R41), X42 may be N or C(R42), X43 may be N or C(R43), and X44 may be N or C(R44),
R41 to R44 may each be the same as described in connection with R4, and
two or more of R41 to R44 may optionally be linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments,
Y1 in Formula 2-1 may be N, and
a group represented by
in Formula 2-1 may be a group represented by one of Formulae A1-1 to A1-3:
wherein, in Formulae A1-1 to A1-3,
Z1 to Z14 may each be the same as described in connection with Z1,
R10a may be understood by referring to the description of R10a provided herein, and
a14 may be an integer from 0 to 4,
a18 may be an integer from 0 to 8,
*′ indicates a binding site to M2 in Formula 2, and
*″ indicates a binding site to ring A2.
For example, in Formulae A1-1 to A1-3, Z14 may be a deuterated C1-C20 alkyl group, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).
In one or more embodiments,
Y3 in Formula 2-2 may be N, and
a group represented by
in Formula 2-2 may be a group represented by one of Formulae NR1 to NR48:
wherein, in Formulae NR1 to NR48,
Y39 may be O, S, Se, N—[W3—(Z3)e3], C(Z39a)(Z39b), or Si(Z39a)(Z39b),
W3, Z3, and e3 may each be the same as described herein, and Z39a and Z39b may each be the same as described in connection with Z3,
*′ indicates a binding site to M2 in Formula 2, and
*″ indicates a binding site to ring A4.
In one or more embodiments,
in Formulae 2-1 and 2-2, each of Y2 and Y4 may be C, and
a group represented by
in Formula 2-1 and
a group represented by
in Formula 2-2
may each independently be a group represented by one of Formulae CR1 to CR29:
wherein, in Formulae CR1 to CR29,
Y49 may be 0, S, Se, N—[W2—(Z2)e2], N—[W4—(Z4)e4], C(Z29a)(Z29b), C(Z49a)(Z49b), Si(Z29a)(Z29b), or Si(Z49a)(Z49b),
W2, W4, Z2, Z4, e2, and e4 may each be the same as described herein, Z29a and Z29b may each be the same as described in connection with Z2, and Z49a and Z49b may each be the same as described in connection with Z4,
Y21 to Y24 may each independently be N or C,
ring A40 may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group (for example, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, or a benzoquinazoline group),
* indicates a binding site to M2 in Formula 2, and
*″ indicates a binding site to ring A1 in Formula 2-1 or ring A3 in Formula 2-2.
In one or more embodiments,
a group represented by
in Formulae CR24 to CR29 may be a group represented by one of Formulae CR(1) to CR(13):
wherein, in Formulae CR(1) to CR(13),
Y39 may be the same as described herein in connection with Y49, and
Y31 to Y34 and Y41 to Y48 may each independently be C or N.
In one or more embodiments, the platinum-containing organometallic compound may include at least one deuterium.
In one or more embodiments, the iridium-containing organometallic compound may include at least one deuterium.
For example, the platinum-containing organometallic compound may be a compound of Group 1-1 to Group 1-4:
In one or more embodiments, the iridium-containing organometallic compound may be a compound of Group 2-1 to Group 2-6:
In the present specification, “Ome” is a methoxy group, “TMS” is a trimethylsilyl group, and “TMG” is a trimethylgermyl group.
In one or more embodiments, the iridium-containing organometallic compound may not be a compound of Group B:
R′ and R″ of Group B may each be an alkyl group.
The fluorescent compound
a) may not include a transition metal, and
b) may include i) B(boron), and ii) O, S, N, or a combination thereof.
In one or more embodiments, the fluorescent compound may include at least one 6-membered ring containing at least one nitrogen atom and at least one boron atom.
In one or more embodiments, the fluorescent compound may be a compound represented by Formula 3 or a compound represented by Formula 4:
wherein, in Formulae 3 and 4,
ring A31 to ring A33, ring A41, and ring A42 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
T34 may be O, S, or N—[W34—(Z34)e34],
T35 may be O, S, or N—[W35—(Z35)e35],
T41 and T42 may each independently be N or C,
W31 to W33 are each the same as described in connection with W1 in Formula 2-1,
Z31 to Z35 and Z41 to Z45 are each the same as described in connection with Z1 in Formula 2-1,
e31 to e35 are each the same as described in connection with e1 in Formula 2-1, and
d31 to d33 and d41 to d42 are each the same as described in connection with d1 in Formula 2-1.
For example, ring A31 to ring A33, ring A41 and ring A42 are each the same as described in connection with ring A1 in Formula 2-1.
In one or more embodiments, in relation to Formula 3, ring A31 and A32 may each be a benzene group, and ring A33 may be a benzene group, a quinoline group, or an isoquinoline group.
In one or more embodiments, T34 in Formula 3 may be N—[W34—(Z34)e34].
In one or more embodiments, T34 in Formula 3 may be N—[W34—(Z34)e34], and Z34 and ring A31 and/or Z34 and Z31 may be bonded to each other via a single bond, or a linking group including O, S, N, B, C, or a combination thereof.
In one or more embodiments, T35 in Formula 3 may be N—[W35—(Z35)e35].
In one or more embodiments, T35 in Formula 3 may be N—[W35—(Z35)e35], and Z35 and ring A32 and/or Z35 and Z32 may be bonded to each other via a single bond or a linking group including O, S, N, B, C, or a combination thereof.
In one or more embodiments, ring A41 and ring A42 in Formula 4 may each be pyrrolyl. For example, T41 and T42 may each be N.
For example, the fluorescent compound may be a compound of Group 3 or Group 4:
A weight ratio of the first compound to the second compound included in the mixture including the first compound and the second compound may be about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60.
The OLED substrate of
A color control unit 2 may be located above the second electrode 50. That is, the green second emission unit 32G of
The first electrode 10 may be anode, which is a hole injection electrode, and the second electrode 50 may be a cathode, which is an electron injection electrode. Alternatively, the first electrode 10 may be a cathode, which is an electron injection electrode, and the second electrode 50 may be an anode, which is a hole injection electrode.
A thin-film transistor (TFT) array substrate including a plurality of TFT (not shown) may be provided under the first electrode 10, and an OLED substrate 1 may be provided on the TFT array substrate.
The first electrode 10 may be formed by, for example, applying a material for forming the first electrode 10 onto the substrate by using a deposition or sputtering method. The first electrode 10 may be an anode. The material for forming the first electrode 10 may include materials with a high work function to facilitate hole injection. The first electrode 10 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 10 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 10 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 10 may have a single-layered structure or a multi-layered structure including a plurality of layers. For example, the first electrode 10 may have a three-layered structure of ITO/Ag/ITO.
The first electrode 10 may be a patterned element corresponding to each subpixel area and electrically connected to each TFT element of the TFT array substrate (not shown).
The blue first emission unit 31B may include a blue luminescent compound (i.e., a blue light-emitting compound).
The blue luminescent compound may include a blue phosphorescent compound, and a blue fluorescent compound (thermal activated delayed fluorescence (TADF) compound and/or prompt fluorescent compound).
In one or more embodiments, the blue luminescent compound may be an iridium-containing organometallic compound or a platinum-containing organometallic compound. The iridium-containing organometallic compound may include a ligand having a carbene moiety, and the carbon of the carbene moiety of the ligand and the iridium of the iridium-containing organometallic compound may be connected by a chemical bond.
In one or more embodiments, the blue luminescent compound may be a fluorescent compound including at least one boron (B) atom and at least one nitrogen (N) atom. In one or more embodiments, the blue luminescent compound may include a C6-C60 polycyclic group in which a 6-membered ring containing boron atom and a nitrogen atom as ring-forming atoms and a cyclic group are condensed with each other.
The green second emission unit 32G may include a mixture of the first compound and the second compound as described herein.
The second electrode 50 may be the cathode. A material for forming the second electrode 50 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like may be used as the material for forming the second electrode 50.
The second electrode 50 may be an unpatterned common electrode, or may be patterned with a plurality of electrode elements.
A protective layer (not shown) may additionally be located on the second electrode 50. In one or more embodiments, the protective layer may include a transparent insulating material.
Referring to
The OLED substrate of
The OLED substrate may include two blue emission units and one green emission unit, as illustrated in
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate may include three blue emission units and one green emission unit, as illustrated in
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate may include four blue emission units and one green emission unit, as illustrated in
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate may include two blue emission units and two green emission units, as illustrated in
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate may include three blue emission units and two green emission units, as illustrated in
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrate of
The OLED substrates of
The OLED substrate of
Each of the first electrode 10, the blue first emission unit 31B, the blue second emission unit 32B, the blue third emission unit 33B, the green fourth emission unit 34G, and the second electrode 50 of
The first charge generation layer 61 may supply charges to the blue first emission unit 31B and/or the blue second emission unit 32B, and the second charge generation layer 62 may supply charges to the blue second emission unit 32B and/or the blue third emission unit 33B, and the third charge generation layer 63 may supply charges to the blue third emission unit 33B and/or the green fourth emission unit 34G. Accordingly, the three blue emission units 31B, 32B, and 33B and one green emission unit 34G may emit light effectively.
The electron transport region 40 may transfer electrons injected from the second electrode 50 to the green fourth emission unit 34G. In one or more embodiments, the electron transport region 40 may include a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The OLED substrate of
The blue first emission unit 31B may include a first hole transport region HTL 1 and a blue first emission layer EML 1B, the blue second emission unit 32B may include a second hole transport region HTL 2 and a blue second emission layer EML 2B, the blue third emission unit 33B may include a third hole transport region HTL 3 and a blue third emission layer EML 3B, and the green fourth emission unit 34G may include a fourth hole transport region HTL 4 and a green fourth emission layer EML 4G.
The first hole transport region HTL 1, the second hole transport region HTL 2, the third hole transport region HTL 3, and the fourth hole transport region HTL 4 may transfer holes to the blue first emission layer EML 1B, the blue second emission layer EML 2B, the blue third emission layer EML 3B, and the green fourth emission layer EML 4G, respectively. Each of the first hole transport region HTL 1, the second hole transport region HTL 2, the third hole transport region HTL 3, and the fourth hole transport region HTL 4 may include a hole injection layer, a hole transport layer, an electron-blocking layer, a buffer layer, or a combination thereof.
The blue first emission layer EML 1B, the blue second emission layer EML 2B, and the blue third emission layer EML 3B may include the blue luminescent compound as described above, and the green fourth emission layer EML 4G may include a mixture of the first compound and the second compound as described herein.
The green fourth emission layer EML 4G may include a host in addition to the mixture of the first compound and the second compound. The host may include a hole-transporting host, an electron-transporting host, a bipolar host, or a combination thereof.
In one or more embodiments, the green fourth emission layer EML 4G may be formed by i) co-depositing a first compound, a second compound, and a host or ii) a soluble process in which a solution including a first compound, a second compound, and a host is provided, and heat treatment is performed.
Although not shown, the OLED substrate of
The light-emitting device of
The OLED substrate 100 may be the same as described above (for example, with reference to
The color control unit 200 may include a first color control element 70a including a first quantum dot (green light emitting quantum dot (G-QD)) for green conversion, a second color control element 70b including a second quantum dot (red light emitting quantum dot (R-QD)) for red conversion, and a third color control element 75c for blue expression. The color control element is not limited to including a quantum dot. In one or more embodiments, an inorganic material, an organic material, or a combination thereof that absorbs blue light or/and green light and converts the same to green light or red light, may be used as the color control element. In one or more embodiments, the color control unit 200 may further include a first color filter 80a located on the first color control element 70a and a second color filter 80b located on the second color control element 70b.
The first color control element 70a may be a green-QD-containing layer, and may convert light generated from the OLED substrate 100 into green light G. The second color control element 70b may be a red-QD containing layer and may convert light generated from the OLED substrate 100 to red light R. Accordingly, the first color control element 70a may be referred to as a first color conversion element, and the second color control element 70b may be referred to as a second color conversion element. The color conversion element may include a resin material, a plurality of quantum dots, and a light scattering agent. The resin material may include, for example, a photoresist (PR) material. In one or more embodiments, the third color control element 75c may be a color filter that optionally allows the blue (B) wavelength region of the light generated from the OLED substrate 100 to pass therethrough. In other words, the third color control element 75c may be a blue-color filter (C/F or CF). In this case, the third color control element 75c may be an absorption type color filter including a specific pigment(s) or quantum dot(s). The absorption type color filter may absorb light of wavelength band except light of the target wavelength band.
The first color filter 80a may cut the remaining blue region wavelength of the light that has passed through the first color control element 70a. The second color filter 80b may cut the remaining blue and green regions wavelength of the light that has passed through the second color control element 70b. The first color filter 80a may be referred to as a blue-cut filter, and the second color filter 80b may be referred to as a blue and green-cut filter. Accordingly, color-controlling/filtering characteristics may be improved by the first color filter 80a and the second color filter 80b. Although not illustrated, a separate optical film may be additionally located on the third color control element 75c. Full colors of RGB may be realized by using the color control unit 200. Herein, the arrangement order or arrangement method of the RGB subpixels is an example, and may be variously changed.
The first quantum dot that may be included in the first color control element 70a may be green-QD, and the second quantum dot that may be included in the second color control element 70b may be red-QD. A quantum dot refers to a semiconductor particle of a small sphere of nanometer (nm) size or a similar shape, and may have a size (diameter) of about several nm to several tens of nm. A quantum dot may have a monolithic structure or a core-shell structure, and in the case of a core-shell structure, the quantum dot may have a single shell structure or a multi-shell structure. For example, a quantum dot may have a core portion (center) including a first semiconductor and a shell portion including a second semiconductor. Here, a material for the core portion (center) may be cadmium selenide (CdSe), cadmium telluride (CdTe), or cadmium sulfide (CdS), and a material for the shell portion may be zinc sulfide (ZnS). Also, a non-cadmium-based quantum dot (QD) may be used. That is, various materials not including cadmium (Cd) may be applied to the quantum dot. However, the materials specifically presented here are exemplary, and other various materials may be applied to the quantum dot. For example, the quantum dot may include at least one of a group Il-VI semiconductor, a group Ill-V semiconductor, a group IV-VI semiconductor, a group IV semiconductor, or combination thereof.
Because quantum dots are very small in size, quantum dots may exhibit a quantum confinement effect. When a particle is very small, electrons in the particle form a discontinuous energy state by the outer wall of the particle. As the size of the space inside the particle is small, the energy state of the electrons is relatively high, and the energy band gap increases. This effect is called as the quantum confinement effect. According to such a quantum confinement effect, when light such as ultraviolet rays or visible rays is incident on a quantum dot, light of various wavelengths may be generated. The wavelength of light generated from a quantum dot may be determined by the size, material, and/or structure of the particle (quantum dot). Specifically, when light with a wavelength greater than the energy band width is incident on the quantum dot, the quantum dot may be excited by absorbing the energy of the light and may transit to a ground state while emitting light of a specific wavelength. In this case, as the size of the quantum dot (or, the core portion of the quantum dot) is smaller, light of a relatively short wavelength, for example, bluish light or greenish light may be generated, and as the size of the quantum dot (or, the core portion of the quantum dot) is larger, light of a relatively long wavelength, for example, reddish light may be generated. Therefore, light of various colors may be realized according to the size of the quantum dot (or the core portion of the quantum dot). Quantum dot particles that may emit greenish light may be referred to as green light quantum dot particles, and quantum dot particles that may emit reddish light may be referred to as red light quantum dot particles. For example, green light quantum dot particles (or the core portion thereof) may be particles having a particle width (diameter) of about 2 nm to about 3 nm, and red light quantum dot particles (or the core portion thereof) may be particles having a particle width (diameter) of about 5 nm to about 6 nm. The emission wavelength may be controlled not only by the size (diameter) of the quantum dot but also by the material and structure.
Since the first color control element 70a may be regarded as a kind of color filter that converts colors using quantum dots, the first color control element 70a may be referred to as a “first QD color filter”. Similarly, the second color control element 70b may be referred to as a “second QD color filter”.
The first color filter 80a and the second color filter 80b of a cut-off filter type may be formed in, for example, a distributed Bragg reflector (DBR) structure. A DBR structure that passes or reflects only the desired wavelength band may be created by repeatedly stacking two material layers (dielectrics) having different refractive indices and adjusting the thickness and the number of layers to be stacked of the material layers. The DBR structure may be applied to the first color filter 80a and the second color filter 80b. For example, a SiO2 layer and a TiO2 layer may be repeatedly stacked under λ/4 condition (here, “A” represents a wavelength of light), and the thickness and the number of layers to be stacked may be controlled to increase a reflectance and a transmittance of a desired wavelength band. As the DBR structure is well known, the detailed descriptions thereof are omitted herein. In addition, at least one of the first color filter 80a and the second color filter 80b may have a structure other than the DBR structure, for example, a high-contrast grating (HCG) structure.
The light-emitting device of
The OLED substrate 100 may be the same as described above (for example, with reference to
The color control unit 201 of
The light scattering element 71c may include a resin material and a light scattering agent. In this embodiment, the resin material may include a photoresist (PR) material. The light scattering agent may include, for example, titanium oxide (TiO2). The first color control element 70a and the second color control element 70b may each include a light scattering agent. Accordingly, by positioning the light scattering element 71c under the third color control element 75c, the impression of colors may be balanced. In other words, change in visibility in a RGB region may be reduced.
The light-emitting device of
The OLED substrate 100 may be the same as described above (for example, with reference to
The color control unit 202 of
The third color control element 70c may convert the light generated from the OLED substrate 100 into blue light B. Accordingly, the third color control element 70c may be referred to as a third color conversion element. The third color control element 70c may include a resin material, quantum dots, and a light scattering agent. The third color filter 80c may cut the remaining green region wavelength of the light that has passed through the third color control element 70c. That is, the third color filter 80c may be a green-cut filter.
The light-emitting device of
The OLED substrate 100 may be the same as described above (for example, with reference to
The color control unit 203 of
An absorption-type green-color filter (G-C/F) may be used as the first color filter 75a, and an absorption-type red-color filter (R-C/F) may be used as the second color filter 75b. The green-color filter 75a may selectively transmit light in the green wavelength region and absorb light in the other wavelength region. Similarly, the red-color filter 75b may selectively transmit light in the red wavelength region and absorb light in the other wavelength region. The color control unit 203 of the present embodiment uses absorption type color filters 75a, 75b, and 75c respectively for the R-subpixel, G-subpixel and B-subpixel regions. In this embodiment, the third color control element 70c containing the blue-QD in
In one or more embodiments, the light-emitting device may further include a fourth sub-pixel, in addition to a R-sub-pixel (first sub-pixel), a G-sub-pixel (second sub-pixel), and a B-sub-pixel (third sub-pixel). The fourth sub-pixel may be configured to exhibit a color (a fourth color) other than R, G, and B. The other color (fourth color) may be, for example, cyan (C). Embodiments of the light-emitting device further including the fourth sub-pixel area are illustrated in
Referring to
Referring to
Referring to
Referring to
In the embodiments illustrated in
Referring to
Referring to
Referring to
OLED substrates A, B, C, 1 and 2, each having the structure illustrated in
From Table 1, It can be seen that the luminescence efficiency and lifespan characteristics of OLED substrate 1 are improved compared to the luminescence efficiency and lifespan (at high luminance) of OLED substrates A and B, and the luminescence efficiency and lifespan characteristics of OLED substrate 2 are improved compared to the luminescence efficiency and lifespan characteristics of OLED substrates A and C.
Subsequently, Light Emitting Device 1 having the structure illustrated in
i) a green-QD containing color conversion element and a red-QD containing color conversion element that can provide the PL quantum yield according to the wavelength illustrated in
ii) three absorption type color filters showing the transmittance according to the wavelength of the absorption type red-color filter (CF-Red), the absorption type green-color filter (CF-Green), and the absorption type blue-color filter (CF-Blue), respectively as three absorption type color filters 75a, 75b, and 75c, respectively; and
iii) the color control unit 203 including the light scattering element that can provide the spectral radiance difference illustrated in
The light-emitting devices according to the embodiments described above may be applicable to various electronic apparatuses such as display apparatus. For example, the light emitting devices may be usefully applied to small-sized electronic devices such as portable devices and wearable devices, and medium- to large-sized electronic devices such as home appliances.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof. For example, Formula 9-33 is a branched C alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
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 examples thereof are a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
The term “C1-C6 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 examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and the term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
Examples of the C3-C10 cycloalkyl group are a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms, and the term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C7-C60 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 that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms, and the term “C1-C6 heteroarylene group” as used herein refers to a divalent group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a carbocyclic aromatic system having 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The 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 indicates —OA102 (wherein A102 indicates the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 indicates the C6-C60 aryl group).
The term “C1-C6 heteroaryloxy group” as used herein indicates —OA102, (wherein A102, indicates the C1-C60 heteroaryl group), and the term “C1-C6 heteroarylthio group” as used herein indicates —SA103 (wherein A103, indicates the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.
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, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
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. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a)” used herein are an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, and a fluorene group (each unsubstituted or substituted with at least one R10a).
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. The “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a)” may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R10a).
Examples of the “C5-C30 carbocyclic group” and the “C1-C30 heterocyclic group” as used herein are i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
wherein the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
The terms “fluorinated C1-C60 alkyl group (or a fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group,” and “fluorinated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group (that is, a fluorinated methyl group)” includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or, a fluorinated C1-C20 alkyl group, or the like)”, “the fluorinated C3-C10 cycloalkyl group”, “the fluorinated C1-C10 heterocycloalkyl group”, or “the fluorinated a phenyl group” may be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen atoms included therein are not substituted with a fluoro group.
The terms “deuterated C1-C60 alkyl group (or a deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group (that is, the deuterated methyl group)” may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C1-C60 alkyl group (or, the deuterated C1-C20 alkyl group or the like)”, “the deuterated C3-C10 cycloalkyl group”, “the deuterated C1-C10 heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein are substituted with deuterium, or ii) a partially deuterated C1-C60 alkyl group (or, a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein are not substituted with deuterium.
The term “(C1-C20 alkyl) ‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group.
The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzothiophene 5,5-dioxide group,” in which, in each group, at least one carbon selected from ring-forming carbons is substituted with nitrogen.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted 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:
deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof.
In the present specification, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 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 C1-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 described herein may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2, or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
Although detailed features are specifically described in the above description, the detailed description should be construed as exemplary embodiments rather than limiting the scope of subject matter. For example, those of ordinary skill in the art may understand that the configuration of the OLED substrate, the color control unit, and the light-emitting device including the same described with reference to
The light-emitting device described above has high luminescence efficiency and long lifespan. Accordingly, an electronic apparatus including the same can be a high-quality electronic apparatus.
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 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 |
|---|---|---|---|
| 10-2021-0124268 | Sep 2021 | KR | national |
