Patent Application
20250115632
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0132834, filed on Oct. 5, 2023, in the Korean Intellectual Property Office, the entire content of which is incorporated by reference herein.
One or more aspects of embodiments of the present disclosure relate to a composition, a light-emitting device, electronic equipment including the light-emitting device, and an organometallic compound.
Light-emitting devices are so-called “self-emissive” devices (for example, organic light-emitting devices) that, as compared with other display devices, have relatively wide viewing angles, relatively high contrast ratios, relatively short response times, and/or excellent or suitable characteristics in terms of luminance, driving voltage, and/or response speed.
In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. The holes and electrons then recombine in the emission layer to produce excitons that may transit (i.e., relax) from an excited state to a ground state, to thereby generate light.
One or more aspects of embodiments of the present disclosure are directed toward a composition capable of providing improved color purity, improved luminescence efficiency, and/or improved lifespan.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device having improved color purity, improved luminescence efficiency, and/or improved lifespan, and electronic equipment including the light-emitting device.
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 one or more embodiments, a composition includes
According to one or more embodiments, a light-emitting device includes
According to one or more embodiments, an electronic equipment includes the light-emitting device.
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, provided is the organometallic compound represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the preceding and other aspects, features, and advantages of certain embodiments of the disclosure are incorporated in and constitute a part of this specification. The drawings illustrate example embodiments and, together with the following description taken in conjunction with the accompanying drawings. In the drawings:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification, and duplicative descriptions thereof may not be provided. 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, by referring to the drawings, to explain aspects of the present description. As utilized 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,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.
Unless otherwise defined, all chemical names, technical and scientific terms, and terms defined in common dictionaries should be interpreted as having meanings consistent with the context of the related art, and should not be interpreted in an ideal or overly formal sense. It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element.
As used herein, singular forms such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “comprise,” “comprises,” “comprising,” “has,” “have,” “having,” “include,” “includes,” and/or “including,” when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
As used herein, the term “and/or” includes any, and all, combination(s) of one or more of the associated listed items.
The term “may” will be understood to refer to “one or more embodiments of the present disclosure,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments of the present disclosure,” each including a corresponding listed item.
It will be understood that when an element is referred to as being “on,” “connected to,” or “on” another element, it may be directly on, connected, or coupled to the other element or one or more intervening elements may also be present. When an element is referred to as being “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present.
Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper,” “bottom,” “top,” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the drawings. For example, if the device in the drawings is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” or “over” the other elements or features. Thus, the term “below” may encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
In this context, “consisting essentially of” means that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.
In present disclosure, “not include (or not including) a or any ‘component’”, “exclude (or excluding) a or any ‘component’”, “‘component’-free”, and/or the like refers to that the “component” not being added, selected or utilized as a component in the element/composition, but the “component” of less than a suitable amount may still be included due to other impurities and/or external factors.
Further, in this specification, the phrase “on a plane,” or “plan view,” means viewing a target portion from the top, and the phrase “on a cross-section” means viewing a cross-section formed by vertically cutting a target portion from the side.
An aspect of the disclosure provides a composition including:
In the present specification, the organometallic compound represented by Formula 1 may be referred to as “first compound.”
Detailed on each of Formula 1 and Formula 3 may be referred to as described in the descriptions provided herein.
In one or more embodiments, the composition may be included in a layer, the layer including 1) the organometallic compound and 2) the second compound, the third compound, the fourth compound, or any combination thereof. The layer including the composition may include a mixture including 1) the organometallic compound and 2) the second compound, the third compound, the fourth compound, or any combination thereof. Therefore, the layer including the composition is clearly differentiated (e.g., different) from, for example, a double layer including 1) a first layer including the organometallic compound and 2) a second layer including the second compound, the third compound, the fourth compound, or any combination thereof.
In one or more embodiments, the composition may be prepared to form the layer, which includes 1) the organometallic compound and 2) the second compound, the third compound, the fourth compound, or any combination thereof, by utilizing one or more suitable methods such as a deposition process, a wet process, and/or the like. In one or more embodiments, the composition may be a pre-mixed mixture prepared for utilization in a deposition process (for example, a vacuum deposition process). The pre-mixed mixture may be, for example, charged into a deposition source within a vacuum chamber, and one, or two, or more compound(s) included in the pre-mixed mixture may be then co-deposited.
In one or more embodiments, a weight ratio of the organometallic compound to the second compound in the composition may be in a range of about 10:90 to about 90:10 or about 20:80 to about 80:20.
Another aspect of the disclosure provides a light-emitting device including:
A detailed description of Formula 1 is as described elsewhere herein.
The light-emitting device includes the organometallic compound represented by Formula 1, and thus may have improved color purity, improved luminescence efficiency, and/or improved lifespan characteristics.
In one or more embodiments, the interlayer in the light-emitting device may include the organometallic compound.
In one or more embodiments, the emission layer in the light-emitting device may include the organometallic compound.
In one or more embodiments, the light-emitting device may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof,
wherein the organometallic compound, the second compound, the third compound, and the fourth compound in the light-emitting device may be different from each other:
The second compound to the fourth compound in the composition and the light-emitting device may each be as described elsewhere herein.
In one or more embodiments, the organometallic compound may include at least one deuterium.
In one or more embodiments, the second compound to the fourth compound may each include at least one deuterium.
In one or more embodiments, the second compound may include at least one silicon.
In one or more embodiments, the third compound may include at least one silicon.
In one or more embodiments, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include, in addition to the organometallic compound represented by Formula 1, the second compound and the third compound, wherein at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, in addition to the organometallic compound. At least one of the organometallic compound and the second compound may include at least one deuterium. In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a third compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the second compound.
In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a third compound, in addition to the organometallic compound. At least one of the organometallic compound and the third compound may include at least one deuterium. In one or more embodiments, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the second compound, the fourth compound, or any combination thereof, in addition to the organometallic compound and the third compound.
In one or more embodiments, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the fourth compound in addition to the organometallic compound. At least one of the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound may have roles in improving color purity, luminescence efficiency, and/or lifespan characteristics of the light-emitting device. In one or more embodiments, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the second compound, the third compound, or any combination thereof, in addition to the organometallic compound and the fourth compound.
In one or more embodiments, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the second compound and the third compound, in addition to the organometallic compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, and the third compound may include at least one deuterium.
In one or more embodiments, a highest occupied molecular orbital (HOMO) energy level of the organometallic compound may be in a range of about −5.70 electron volt (eV) to about −5.15 eV or about −5.61 eV to about −5.20 eV.
In one or more embodiments, a lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound may be in a range of about −2.30 eV to about −1.80 eV or about −2.21 eV to about −2.06 eV.
The HOMO and LUMO energy levels may be evaluated by cyclic voltammetry analysis (refer to Evaluation Example 1) for the organometallic compound.
In one or more embodiments, a maximum emission wavelength (or an emission peak wavelength) of an emission spectrum in a film of the organometallic compound may be in a range of about 430 nanometer (nm) to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
In one or more embodiments, a full width at half maximum (FWHM) of an emission spectrum in film of the organometallic compound may be 110 nm or less, for example, in a range of about 10 nm to about 110 nm, about 30 nm to about 110 nm, about 50 nm to about 110 nm, about 61 nm to about 110 nm, about 10 nm to about 90 nm, about 30 nm to about 90 nm, about 50 nm to about 90 nm, about 61 nm to about 90 nm, about 10 nm to about 72 nm, about 30 nm to about 72 nm, about 50 nm to about 72 nm, or about 61 nm to about 72 nm.
In one or more embodiments, a photoluminescence quantum yield (PLQY) in a film of the organometallic compound may be in a range of about 40% to about 99%, about 49% to about 90%, about 49% to about 80%, or about 49% to about 70%.
In one or more embodiments, a decay time of the organometallic compound may be in a range of about 1.80 microsecond (μs) to about 3.00 μs, about 1.90 μs to about 2.70 μs, or about 1.90 μs to about 2.50 μs.
The maximum emission wavelength, FWHM, PLQY, and decay time of the organometallic compound are evaluated for a film including the organometallic compound, and evaluation methods thereof may each independently be as described in connection with, for example, Evaluation Examples 2 and 3.
In one or more embodiments, the emission layer in the light-emitting device may include: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, wherein the emission layer may be to emit blue light.
In one or more embodiments, a maximum emission wavelength of the blue light may be in a range of about 430 nm to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, or about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
In one or more embodiments, a full width at half maximum of the blue light may be 110 nm or less, for example, in a range of about 10 nm to about 110 nm, about 30 nm to about 110 nm, about 50 nm to about 110 nm, about 61 nm to about 110 nm, about 10 nm to about 90 nm, about 30 nm to about 90 nm, about 50 nm to about 90 nm, about 61 nm to about 90 nm, about 10 nm to about 72 nm, about 30 nm to about 72 nm, about 50 nm to about 72 nm, or about 61 nm to about 72 nm.
In one or more embodiments, the blue light may be deep blue light.
In one or more embodiments, a CIEx coordinate (e.g., a CIEx coordinate for bottom emission) of the blue light may be in a range of about 0.125 to about 0.140 or about 0.130 to about 0.140.
In one or more embodiments, a CIEy coordinate (e.g., a CIEy coordinate for bottom emission) of the blue light may be in a range of about 0.100 to about 0.130.
In one or more embodiments, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In one or more embodiments, the third compound may not include (e.g., may exclude) the following compounds:
In one or more embodiments, a difference between a triplet energy level (unit: eV) and a singlet energy level (eV) of the fourth compound may be in a range of about 0 eV or more to about 0.5 eV or less (or about 0 eV or more to about 0.3 eV or less).
In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as ring-forming atoms.
In one or more embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound including two or more cyclic groups that are condensed while sharing B.
In one or more embodiments, the fourth compound may include a condensed ring in which at least one third ring is condensed with at least one fourth ring,
In one or more embodiments, the third compound may not include (e.g., may exclude) a compound represented by Formula 3-1 described herein.
In one or more embodiments, the second compound may include a compound represented by Formula 2:
In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
In one or more embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
In one or more embodiments, the light-emitting device may satisfy at least one of Conditions 1 to 4:
LUMO energy level (eV) of third compound greater than (>) LUMO energy level (eV) of organometallic compound;
LUMO energy level (eV) of organometallic compound greater than (>) LUMO energy level (eV) of second compound;
HOMO energy level (eV) of organometallic compound greater than (>) HOMO energy level (eV) of third compound; and
HOMO energy level (eV) of the third compound greater than (>) HOMO energy level (eV) of the second compound.
Here, each of the HOMO energy level and the LUMO energy level of each of the organometallic compound, the second compound, and the third compound may be a negative value, and may be measured according to a suitable method, for example, a method described in Evaluation Example 1 in the present specification.
In one or more embodiments, an absolute value of a difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the second compound may be in a range of about 0.1 eV or more to about 1.0 eV or less, an absolute value of a difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the third compound may be in a range of about 0.1 eV or more to about 1.0 eV or less, an absolute value of a difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., about 0.2 eV or more to about 1.25 eV or less), and an absolute value of a difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., about 0.2 eV or more to about 1.25 eV or less).
When the relationships between the LUMO energy level and HOMO energy level satisfy the aforementioned conditions, a suitable or excellent balance between holes and electrons each injected into the emission layer may be achieved.
The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to the first embodiment, the emission layer of the interlayer in the light-emitting device may include the organometallic compound, and may further include a host, wherein the organometallic compound and the host may be different from each other, and the emission layer may be to emit phosphorescence or fluorescence emitted from the organometallic compound. For example, according to the first embodiment, the organometallic compound may be a dopant or an emitter. For example, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
Phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may effectively transfer energy to the organometallic compound which serves as a dopant or an emitter, and in this regard, the auxiliary dopant may serve to improve luminescence efficiency of the organometallic compound.
The auxiliary dopant may be different from each of the organometallic compound and the host.
In one or more embodiments, the auxiliary dopant may be a compound emitting delayed fluorescence.
In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including each of B and N as ring-forming atoms.
According to the second embodiment, the emission layer of the interlayer in the light-emitting device may include the organometallic compound, and may further include a host and a dopant, wherein the organometallic compound, the host, and the dopant may be different from each other, and the emission layer may be to emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
In one or more embodiments, the organometallic compound in the second embodiment is not a dopant, and may rather serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In one or more embodiments, the organometallic compound in the second embodiment may serve as an emitter, and may also serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
For example, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
The dopant (or the emitter) in the second embodiment may be a (e.g., any) phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or a (e.g., any) fluorescent dopant material (e.g., a compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).
In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength in a range of about 430 nm to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503.
In one or more embodiments, the host in the first embodiment and the second embodiment may be a (e.g., any) host material (e.g., a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof).
In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
In one or more embodiments, the light-emitting device may further include a capping layer arranged outside (e.g., and on) the first electrode and/or outside (e.g., and on) the second electrode.
In one or more embodiments, the light-emitting device may further include at least one of a first capping layer arranged outside (e.g., and on) the first electrode and/or a second capping layer arranged outside (e.g., and on) the second electrode, wherein at least one of the first capping layer and the second capping layer may include the organometallic compound represented by Formula 1. More details on the first capping layer and/or the second capping layer may be referred to the descriptions provided herein.
In one or more embodiments, the light-emitting device may include:
The wording “(interlayer and/or capping layer) includes an organometallic compound represented by Formula 1” as utilized herein may be understood as “(interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds, each represented by Formula 1.”
In one or more embodiments, the interlayer and/or the capping layer may include Compound 1 only as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in substantially the same layer (for example, both (e.g., simultaneously) Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in an electron transport region).
The term “interlayer” as utilized herein refers to a single layer and/or each (e.g., all) of multiple layers arranged between the first electrode and the second electrode of the light-emitting device.
Another aspect of the disclosure provides electronic equipment including the light-emitting device. The electronic equipment may further include a thin-film transistor. For example, the electronic equipment may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In one or more embodiments, the electronic equipment may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. More details on the electronic equipment may be referred to the descriptions provided herein.
Another aspect provides an electronic apparatus including the light-emitting device.
For example, the electronic apparatus may be at least one selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.
Another aspect of the disclosure provides the organometallic compound represented by Formula 1. Details on Formula 1 may be referred to the descriptions provided herein.
Synthesis methods of the organometallic compound may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided herein.
In Formula 1, each of Ar1 and Ar2 may be a group represented by Formula 1A:
wherein more details on Formula 1A (or descriptions of each of Ar1 and Ar2 in Formula 1) may be referred to the descriptions provided herein.
In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu). For example, M may be Pt.
In Formula 1, L1 may be a monodentate ligand. More details on L1 are provided elsewhere herein.
In Formula 1 and Formula 1A, X1 to X3 and Y1 to Y3 may each independently be C or N. For example, each of X1 to X3 and Y1 to Y3 may be C.
In Formula 1 and Formula 1A, ring CY1 to ring CY3 and ring A1 to ring A4 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, ring CY1 to ring CY3 and ring A1 to ring A4 may each independently be:
In one or more embodiments, ring CY1 may be:
In one or more embodiments, ring CY1 may be an imidazole group, a benzimidazole group, or a pyridoimidazole group.
In one or more embodiments, ring CY2 may be:
In one or more embodiments, ring CY2 may be an imidazole group, a benzimidazole group, a pyridoimidazole group, an oxazole group, a benzoxazole group, a pyridooxazole group, a thiazole group, a benzothiazole group, or a pyridothiazole group.
In one or more embodiments, ring CY3 may be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a naphthalene group, a quinoline group, or an isoquinoline group.
In one or more embodiments, ring A1 to ring A4 may each independently be:
In one or more embodiments, ring A1 to ring A4 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a 1,2,3,4-tetrahydronaphthalene group.
In Formula 1, two of four bonds selected from among a bond between X1 and M, a bond between X2 and M, a bond between X3 and M, and a bond between L1 and M may each be a coordinate bond, and two of four bonds not selected (e.g., the other two) may each be a covalent bond (e.g., two coordinate bonds and two covalent bonds are included in a bond between X1 and M, a bond between X2 and M, a bond between X3 and M, and a bond between L1 and M).
In one or more embodiments, in Formula 1, a bond between X1 and M and a bond between X2 and M may each be a coordinate bond, and a bond between X3 and M and a bond between L1 and M may each be a covalent bond.
In one or more embodiments, in Formula 1, a bond between X1 and M and a bond between X2 and M may each be a coordinate bond, wherein each of X1 and X2 may be C, and C may be carbon of a carbene moiety.
In Formula 1 and Formula 1A, n1 and n2 may each independently be 0 or 1. When n1 in Formula 1 is 0, ring A3 may be directly bonded to Y3 in Formula 1A. n2 may represent the number of Ar2(s) in Formula 1.
In Formula 1 and Formula 1A, R1 to R3 and T1 to T4 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C1-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1 to Q3 may each be as described elsewhere herein.
In one or more embodiments, R1 to R3 and T1 to T4 may each independently be:
The terms “a C1-C60 alkyl group unsubstituted or substituted with at least one deuterium” and “a C1-C20 alkyl group unsubstituted or substituted with at least one deuterium” as utilized herein may each be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with at least one deuterium.
In one or more embodiments, the terms “a C1-C60 alkyl group unsubstituted or substituted with at least one deuterium” and “a C1-C20 alkyl group unsubstituted or substituted with at least one deuterium” as utilized herein may each be —CH3, —CDH2, —CD2H, —CDs, —CH2CH3, —CDHCH3, —CD2CH3, —CH2CDH2, —CDHCDH2, —CD2CDH2, —CH2CD2H, —CDHCD2H, —CD2CD2H, —CH2CD3, —CDHCD3, —CD2CD3, or a group represented by one of Formulae X-1 to X-30:
wherein, in Formulae X-1 to X-30, * indicates a binding site to a neighboring atom.
The term “a deuterated C1-C60 alkyl group”, “a C1-C60 alkyl group substituted with (at least one) deuterium”, “a deuterated C1-C20 alkyl group”, or “a C1-C20 alkyl group substituted with (at least one) deuterium” as utilized herein may refer to a group in which at least one hydrogen in a linear or branched C1-C60 alkyl group (or a linear or branched C1-C20 alkyl group) is substituted with deuterium, and examples thereof may be 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 substituted with at least one deuterium (e.g., —CDH2, —CD2H, —CD3, —CDHCH3, —CD2CH3, —CH2CDH2, —CDHCDH2, —CD2CDH2, —CH2CD2H, —CDHCD2H, —CD2CD2H, —CH2CD3, —CDHCD3, —CD2CD3, or a group represented by one of Formulae X-2 to X-6, X-8 to X-10, X-12 to X-22, and X-24 to X-30).
In Formula 1 and Formula 1A, a1 to a3 and b1 to b4 may each independently be an integer from 0 to 20. a1 to a3 and b1 to b4 indicate the number of R1 to R3 and the number of T1 to T4, respectively. When a1 is 2 or more, two or more of R1 may be identical to or different from each other, when a2 is 2 or more, two or more of R2 may be identical to or different from each other, when a3 is 2 or more, two or more of R3 may be identical to or different from each other, when b1 is 2 or more, two or more of T1 may be identical to or different from each other, when b2 is 2 or more, two or more of T2 may be identical to or different from each other, when b3 is 2 or more, two or more of T3 may be identical to or different from each other, and when b4 is 2 or more, two or more of T4 may be identical to or different from each other.
In Formula 1 and Formula 1A, at least two selected from among ring CY1, ring CY2, ring A2, ring A3, R1 to R3, and T1 to T4 may optionally be bonded (e.g., may not be bonded (e.g., are not bonded) or may be bonded (e.g., are bonded)) to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
For example, as in Condition A1 and Condition A2 and Formula 1-5 to Formula 1-10 described, ring CY1 and ring A3 in Formula 1 and Formula 1A may be bonded to each other.
For example, as in Condition B1 and Condition B2 and Formula 1-9 and Formula 1-10 described, ring CY2 and ring A3 in Formula 1 and Formula 1A may be bonded to each other.
Unless otherwise stated herein, * indicates a binding site to a neighboring atom.
In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by one of Formulae CY1-1 to CY1-9:
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by one of Formulae CY2-1 to CY2-9:
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by one of Formulae CY3-1 to CY3-5:
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition A1 or Condition A2:
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition B1 or Condition B2:
In one or more embodiments, L1 in Formula 1 may be a group represented by *-(L11)c1-R4.
For example, 11 may be a single bond, *—C≡C—*′, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, wherein the C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each independently be:
In one or more embodiments, R4, R41, and R42 may each independently be:
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition C1 or Condition C2:
In one or more embodiments, the organometallic compound represented by Formula 1 may have a symmetric structure.
In one or more embodiments, the organometallic compound represented by Formula 1 may have an asymmetric structure.
In one or more embodiments, in Formula 1, ring CY1 and ring CY2 may be different from each other.
In one or more embodiments, in Formula 1, ring CY1 and ring CY2 may be identical to each other.
In one or more embodiments, in Formula 1, n2 may be 0.
In one or more embodiments, in Formula 1, n2 may be 1, and Ar1 and Ar2 may be different from each other.
In one or more embodiments, in Formula 1, n2 may be 1, and Ar1 and Ar2 may be identical to each other.
In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by one of (e.g., one selected from among) Formula 1-1 to Formula 1-10:
All descriptions of Formula 1 and Formula 1A and Ar1 and Ar2 in the present specification may be applied to Formula 1-1 to Formula 1-10.
The organometallic compound may have a tridentate ligand and a monodentate ligand (i.e., Ligand L1) as confirmed from Formula 1, and Ar1 in Formula 1 may be the group represented by Formula 1A. Here, Formula 1A may include ring A2 and ring A3, and may (e.g., optionally) further include ring A4. In this regard, intermolecular interactions of the organometallic compound represented by Formula 1 having a square plane structure and/or interactions between the aforementioned organometallic compound and other compounds may be inhibited, thereby preventing or reducing formation of excimers or exciplexes that may result from such interactions. Furthermore, as the rigidity of the organometallic compound molecule is increased, the PLQY of the organometallic compound may be improved. Accordingly, a light-emitting device including the organometallic compound represented by Formula 1 may have excellent or suitable luminescence efficiency and lifespan characteristics.
In Formula 2, b51 to b53 indicate the number of L51 to L53, respectively, and may each be an integer from 1 to 5. When b51 is 2 or more, two or more of L51 may be identical to or different from each other, when b52 is 2 or more, two or more of L52 may be identical to or different from each other, and when b53 is 2 or more, two or more of L53 may be identical to or different from each other. In one or more embodiments, b51 to b53 may each independently be 1 or 2.
In Formula 2, L51 to L53 may each independently be:
In one or more embodiments, in Formula 2, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between two or more L51(s), a bond between two or more L52(s), a bond between two or more L53(s), a bond between L51 and carbon between X54 and X55 in Formula 2, a bond between L52 and carbon between X54 and X56 in Formula 2, and a bond between L53 and carbon between X55 and X56 in Formula 2 may each be a “carbon-carbon single bond.”
In Formula 2, X54 may be N or C(R54), X55 may be N or C(R55), and X56 may be N or C(R56), wherein at least one of X54 to X56 may be N. R54 to R56 may each be as described elsewhere herein. In one or more embodiments, two or three among X54 to X56 may each be N.
R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in the present specification may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroaryl alkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1 to Q3 may each be as described elsewhere herein.
For example, i) R1 to R3, and T1 to T4 in Formula 1, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be:
For example, in Formula 91,
In one or more embodiments, i) R1 to R3, and T1 to T4 in Formula 1, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2) (wherein more details on Q1 to Q3 may be referred to the descriptions provided herein):
wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-246, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “D” represents a deuterium atom, and “TMS” represents a trimethylsilyl group.
In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 each indicate the number of R71 to R74 and the number of R501 to R504, respectively, and may each independently be an integer from 0 to 20. When a71 is 2 or more, two or more of R71 may be identical to or different from each other, when a72 is 2 or more, two or more of R72 may be identical to or different from each other, when a73 is 2 or more, two or more of R73 may be identical to or different from each other, when a74 is 2 or more, two or more of R74 may be identical to or different from each other, when a501 is 2 or more, two or more of R501 may be identical to or different from each other, when a502 is 2 or more, two or more of R502 may be identical to or different from each other, when a503 is 2 or more, two or more of R503 may be identical to or different from each other, and when a504 is 2 or more, two or more of R504 may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
In Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may not each (e.g., simultaneously) be a phenyl group, (i.e., if *-(L51)b51-R51 is a phenyl group then *-(L52)b52-R52 may not be a phenyl group, and if *-(L52)b52-R52 is a phenyl group then *-(L51)b51-R51 may not be a phenyl group).
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be identical to each other.
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be different from each other.
In one or more embodiments, in Formula 2, b51 and b52 may each be 1, 2, or 3, and L51 and L52 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R51 and R52 in Formula 2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3), and
Q1 to Q3 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In one or more embodiments,
For example,
In Formulae 3-1 to 3-5, L81 to L85 may each independently be:
In one or more embodiments, a group represented by
in Formulae 3-1 and 3-2 may be a group represented by one of Formulae CY71-1(1) to CY71-1(8), and/or
In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from among Compounds 1 to 100:
In Compounds 1 to 100,
respectively.
In one or more embodiments, the second compound may be one selected from among Compounds ETH1 to ETH100:
In one or more embodiments, the third compound may be one selected from among Compounds HTH1 to HTH46:
In one or more embodiments, the fourth compound may be one selected from among Compounds DFD1 to DFD29 and DFD051:
In the compounds herein, Ph represents a phenyl group, and DN indicates substitution with deuterium in the number of N.
Description of
Hereinafter, a structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a transflective electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In ), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a single-layer structure including (e.g., consisting of) a single layer, or a multi-layer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer 130 may be arranged on the first electrode 110. The interlayer 130 may include the emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, and/or the like.
In one or more embodiments, the interlayer 130 may include i) two or more light-emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer arranged between two neighboring light-emitting units. When the interlayer 130 includes the two or more light-emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
For example, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron-blocking layer structure, wherein layers in each structure are sequentially stacked from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
For example, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) groups represented by Formulae CY201 to CY217:
wherein, in Formulae CY201 to CY217, R10b and R10c may each be as described in connection with R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a.
In one or more embodiments, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one of (e.g., selected from among) the groups represented by Formulae CY201 to CY203 and at least one of (e.g., selected from among) the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be one of (e.g., selected from among) the groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one of (e.g., selected from among) the groups represented by Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) the groups represented by Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) the groups represented by Formulae CY201 to CY203, and may include at least one of (e.g., selected from among) the groups represented by Formulae CY204 to CY217.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) the groups represented by Formulae CY201 to CY217.
For example, the hole transport region may include: at least one selected from among Compounds HT1 to HT46; m-MTDATA; TDATA; 2-TNATA; NPB(NPD); β-NPB; TPD; spiro-TPD; spiro-NPB; methylated NPB; TAPC; HMTPD; 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA); polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA); poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS); polyaniline/camphor sulfonic acid (PANI/CSA); polyaniline/poly(4-styrenesulfonate) (PANI/PSS); or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce the leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
p-Dopant
The hole transport region may further include, in addition to the aforementioned materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer including (e.g., consisting of) the charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the p-dopant may have a LUMO energy level of −3.5 electron volt (eV) or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and/or the like:
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or any combination thereof, and element EL2 may be non-metal, metalloid, or any combination thereof.
Examples of the metal may include: alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), and/or the like); post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), and/or the like); lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and/or the like); and/or the like.
Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Examples of the non-metal may include oxygen (O), a halogen (for example, F, Cl, Br, I, and/or the like), and/or the like.
For example, the compound containing element EL1 and element EL2 may include metal oxide, metal halide (e.g., metal fluoride, metal chloride, metal bromide, metal iodide, and/or the like), metalloid halide (e.g., metalloid fluoride, metalloid chloride, metalloid bromide, metalloid iodide, and/or the like), metal telluride, or any combination thereof.
Examples of the metal oxide may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, and/or the like), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, and/or the like), molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, and/or the like), rhenium oxide (e.g., ReO3, and/or the like), and/or the like.
Examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and/or the like.
Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCI, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mg12, Cal2, Srl2, Bal2, and/or the like.
Examples of the transition metal halide may include titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, and/or the like), zirconium halide (e.g., ZrF4, ZrC14, ZrBr4, ZrI4, and/or the like), hafnium halide (e.g., HfF4, HfC14, HfBr4, Hfl4, and/or the like), vanadium halide (e.g., VF3, VCI3, VBrs, V13, and/or the like), niobium halide (e.g., NbF3, NbCIs, NbBrs, Nbl3, and/or the like), tantalum halide (e.g., TaF3, TaCl3, TaBrs, Tal3, and/or the like), chromium halide (e.g., CrF3, Cr03, CrBrs, Cr13, and/or the like), molybdenum halide (e.g., MoF3, MoCI3, MoBrs, Mol3, and/or the like), tungsten halide (e.g., WF3, WCI3, WBrs, WI3, and/or the like), manganese halide (e.g., MnF2, MnCl2, MnBr2, Mnl2, and/or the like), technetium halide (e.g., TcF2, TcCl2, TcBr2, Tc12, and/or the like), rhenium halide (e.g., ReF2, ReCl2, ReBr2, Rel2, and/or the like), ferrous halide (e.g., FeF2, FeCl2, FeBr2, Fel2, and/or the like), ruthenium halide (e.g., RuF2, RuCl2, RuBr2, Rul2, and/or the like), osmium halide (e.g., OsF2, OsC12, OsBr2, Os12, and/or the like), cobalt halide (e.g., CoF2, COC12, CoBr2, C012, and/or the like), rhodium halide (e.g., RhF2, RhCl2, RhBr2, Rhl2, and/or the like), iridium halide (e.g., IrF2, IrCl2, IrBr2, Ir12, and/or the like), nickel halide (e.g., NiF2, NiCl2, NiBr2, Nil2, and/or the like), palladium halide (e.g., PdF2, PdCI2, PdBr2, Pd12, and/or the like), platinum halide (e.g., PtF2, PtCl2, PtBr2, Pt12, and/or the like), cuprous halide (e.g., CuF, CuCl, CuBr, Cul, and/or the like), silver halide (e.g., AgF, AgCI, AgBr, Agl, and/or the like), gold halide (e.g., AuF, AuCI, AuBr, Aul, and/or the like), and/or the like.
Examples of the post-transition metal halide may include zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, Zn12, and/or the like), indium halide (e.g., Ink3, and/or the like), tin halide (e.g., Sn12, and/or the like), and/or the like.
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCI, YbCl2, YbC13, SmC13, YbBr, YbBr2, YbBrs, SmBrs, YbI, YbI2, YbI3, Sm13, and/or the like.
Examples of the metalloid halide may include antimony halide (e.g., SbCl5, and/or the like) and/or the like.
Examples of the metal telluride may include alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, and/or the like), alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, and/or the like), transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, and/or the like), post-transition metal telluride (e.g., ZnTe, and/or the like), lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, and/or the like), and/or the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers among a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other, to emit white light. In one or more embodiments, the emission layer may include two or more materials among a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer, to emit white light.
In one or more embodiments, the emission layer may include a host and a dopant (or an emitter). In one or more embodiments, the emission layer may further include an auxiliary dopant that promotes energy transfer to a dopant (or an emitter), in addition to the host and the dopant (or an emitter). When the emission layer includes the dopant (or an emitter) and the auxiliary dopant, the dopant (or an emitter) and the auxiliary dopant are different from each other.
The organometallic compound represented by Formula 1 in the present specification may serve as the dopant (or an emitter), or may serve as the auxiliary dopant.
An amount (weight) of the dopant (or an emitter) in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emission layer may include the organometallic compound represented by Formula 1. An amount of the organometallic compound in the emission layer may be, based on 100 parts by weight of the emission layer, in a range of about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the host in the emission layer may include the second compound, the third compound, or any combination thereof.
In one or more embodiments, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 Formula 301
For example, when xb11 in Formula 301 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.
In one or more embodiments, the host may include at least one selected from among a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In one or more embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include at least one selected from among Compounds H1 to H130, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di(9-carbazolyl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
The host may have one or more suitable modifications. For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.
The emission layer may include, as a phosphorescent dopant, the organometallic compound represented by Formula 1.
In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
M(L401)xc1(L402)xc2 Formula 401
For example, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A401(s) in two or more of L401(s) may not be linked or may be linked to each other via T402, which is a linking group, or two ring A402(s) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be as described in connection with T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, and/or the like), or any combination thereof.
The phosphorescent dopant may include, for example, at least one selected from among compounds PD1 to PD25, or any combination thereof:
In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include at least one compound represented by Formula 501:
For example, Ar501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, and/or the like) in which three or more monocyclic groups are condensed together.
For example, xd4 in Formula 501 may be 2.
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each include at least one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503.
The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers in each structure are sequentially stacked from the emission layer.
The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
For example, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21. Formula 601
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group unsubstituted or substituted with at least one R10a.
In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include: at least one selected from among Compounds ET1 to ET46; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); Alq3; BAlq; TAZ; NTAZ; or any combination thereof:
Å thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (e.g., an electron transport layer in the electron transport region) may further include, in addition to the aforementioned materials, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (Liq) and/or ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
In one or more embodiments, the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include: an alkali metal oxide, such as Li2O, Cs2O, K2O, and/or the like; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and/or the like; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal oxide, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and/or the like.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one selected from among metal ions of the alkali metal, the alkaline earth metal, and the rare earth metal, and ii) as a ligand bonded to the metal ion(s) (e.g., the selected metal ion(s)), for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described herein. In one or more embodiments, the electron injection layer may further include an organic material (e.g., the compound represented by Formula 601).
In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide), and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an Rbl:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 is arranged on the interlayer 130 having the aforementioned structure. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be utilized.
The second electrode 150 may include Li, Ag, Mg, Al, Al—Li, Ca, Mg—In, Mg—Ag, Yb, Ag—Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.
A first capping layer may be arranged outside (and e.g., on) the first electrode 110, and/or a second capping layer may be arranged outside (and e.g., on) the second electrode 150. In detail, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, and accordingly, the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one selected from among the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include: at least one selected from among Compounds HT28 to HT33; at least one selected from among Compounds CP1 to CP6; β-NPB; or any combination thereof:
The light-emitting device may be included in one or more suitable electronic equipment. For example, the electronic equipment including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic equipment (for example, a light-emitting apparatus) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer, in addition to the light-emitting device. The color filter and/or the color conversion layer may be arranged in at least one direction in which light emitted from the light-emitting device travels. For example, light emitted from the light-emitting device may be blue light, green light, or white light. Details on the light-emitting device may be referred to the descriptions provided herein. In one or more embodiments, the color conversion layer may include quantum dots.
The electronic equipment may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be arranged among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns thereon, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns thereon.
The plurality of color filter areas (or the plurality of color conversion areas) may include: a first area emitting first color light; a second area emitting second color light; and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In particular, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include (e.g., may exclude) quantum dots. Details on the quantum dots may be referred to the descriptions provided herein. Each of the first area, the second area, and/or the third area may further include a scatter.
For example, in the light-emitting device emitting first light, the first area may be to absorb the first light to emit 1-1 color light, the second area may be to absorb the first light to emit 2-1 color light, and the third area may be to absorb the first light to emit 3-1 color light. Here, the 1-1 color light, the 2-1 color light, and the 3-1 color light may have different maximum emission wavelengths from one another. In particular, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 color light may be blue light.
The electronic equipment may further include a thin-film transistor, in addition to the aforementioned light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
The electronic equipment may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic equipment may be flexible.
Various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic equipment. Examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (e.g., fingertips, pupils, and/or the like).
The authentication apparatus may further include, in addition to the light-emitting device as described herein, a biometric information collector.
The electronic equipment may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting equipment of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be arranged on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100, and provide a flat surface on the substrate 100.
A TFT may be arranged on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor, such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be arranged on the activation layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate these electrodes from one another.
The source electrode 260 and the drain electrode 270 may be arranged on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be arranged in contact with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT may be electrically connected to a light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without fully covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic-based organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.
The second electrode 150 may be arranged on the interlayer 130, and a second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be arranged on the second capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic-based resin (e.g., polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), and/or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
The light-emitting apparatus of
The electronic apparatus 1 may include a display area DA and a non-display area NDA outside the display area DA. A display device may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.
The non-display area NDA is an area that does not display an image, and may be around (e.g., entirely surround) the display area DA. On the non-display area NDA, a driver for providing electrical signals or power to display devices arranged on the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board, may be electrically connected may be arranged.
In the electronic apparatus 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. In one or more embodiments, as shown in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be spaced and/or apart from each other in the x-direction or the −x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced and/or apart from each other in the x direction or the −x direction. In other words, an imaginary straight line L connecting the side window glasses 1100 may extend in the x-direction or the −x-direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, a tachograph, an automatic shift selector indicator lamp, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a heater of a seat are provided. The center fascia 1500 may be arranged on one side of the cluster 1400.
A passenger seat dashboard 1600 may be spaced and/or apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In one or more embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be provided to correspond to a passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to one or more embodiments, an organic light-emitting display apparatus including the aforementioned light-emitting device will be described as an example, but one or more suitable types (kinds) of the aforementioned display apparatus may be utilized in embodiments.
Referring to
Referring to
Referring to
Layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a certain region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10-3 torr, and at a deposition speed in a range of about 0.01 angstrom per second (Å/sec) to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group consisting of carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be: a monocyclic group consisting of one ring; or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C1-C60 heterocyclic group may be from 3 to 61.
The term “cyclic group” as utilized herein may include both (e.g., simultaneously) the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.
For example,
The terms “the cyclic group, the C3-C60 carbocyclic group, the C1-C60 heterocyclic group, the π electron-rich C3-C60 cyclic group, or the π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein may refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, and/or the like) according to the structure of a formula for which the corresponding term is utilized. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Depending on context, a divalent group may refer or be a polyvalent group (e.g., trivalent, tetravalent, etc., and not just divalent) per, e.g., the structure of a formula in connection with which of the terms are utilized.
Examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may include 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. Examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group are a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and specific examples thereof may include 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, and a tert-decyl group. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and/or the like. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and/or the like. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as utilized herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C3-C1 cycloalkyl group.
The term “C1-C1 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms, and specific examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like. The term “C1-C1 heterocycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as utilized herein refers to a monovalent cyclic group that 3 to 10 carbon atoms, at least one carbon-carbon double bond in the ring thereof, and no aromaticity, and specific examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as utilized herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and/or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms. The term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms. Examples of the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, and/or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized 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 the entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indeno anthracenyl group, and/or the like. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described herein.
The term “monovalent non-aromatic hetero-condensed polycyclic group” as utilized herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic hetero-condensed polycyclic group are a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 aryloxy group” as utilized herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as utilized herein refers to —A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as utilized herein refers to —A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as utilized herein may be:
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
The term “transition metal” as utilized herein may include Hf, Ta, W, Re, Os, Ir, Pt, Au, and/or the like.
“Ph” as utilized herein refers to a phenyl group, “Me” as utilized herein refers to a methyl group, “Et” as utilized herein refers to an ethyl group, “ter-Bu” or “But” as utilized herein refers to a tert-butyl group, and “OMe” as utilized herein refers to a methoxy group.
The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group.” In other words, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
Unless otherwise specified, * *, and *″ each indicate a binding site to a neighboring atom in the corresponding formula or moiety.
Terms such as “substantially,” “about,” and “approximately” are used as relative terms and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. They may be inclusive of the stated value and an acceptable range of deviation as determined by one of ordinary skill in the art, considering the limitations and error associated with measurement of that quantity. For example, “about” may refer to one or more standard deviations, or ±30%, ±20%, ±10%, ±5% of the stated value.
Numerical ranges disclosed herein include and are intended to disclose all subsumed sub-ranges of the same numerical precision. For example, a range of “1.0 to 10.0” includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicant therefore reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The light emitting device, light emitting element, and/or any other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the light emitting device and/or light emitting element may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the light emitting device and/or light emitting element may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device and/or element may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
2.83 g (12.0 millimole (mmol)) of 1,3-dibromobenzene, 10.09 g (30.0 mmol) of N1-([1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,2-diamine, 1.10 g (1.2 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.99 g (2.4 mmol) of S-Phos, and 5.77 g (60.0 mmol) of sodium tert-butoxide (NaOtBu) were added to a reaction vessel and suspended in 120 milliliter (mL) of toluene. The reaction temperature was raised to 110° C., and the mixture was stirred for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, and an extraction process was performed thereon by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 6.27 g (8.4 mmol) of Intermediate 77-A.
6.27 g (8.4 mmol) of Intermediate 77-A, 75 mL (462.0 mmol) of triethyl orthoformate (CH(OEt)3), and 1.8 mL (20.2 mmol) of HCl 35 wt % solution were added to a reaction vessel, and stirred for 12 hours after raising the reaction temperature to 80° C. After completion of the reaction, the reaction product was cooled to room temperature, and the residue obtained by removing the solvent was recrystallized to obtain 4.62 g (5.5 mmol) of Intermediate 77-B.
4.62 g (5.5 mmol) of Intermediate 77-B, 2.28 g (6.1 mmol) of dichloro(1,5-cyclooctadiene)platinum (Pt(COD)C12), and 1.35 g (16.5 mmol) of sodium acetate (NaOAc) were suspended in 220 mL of dioxane. After raising the reaction temperature to 120° C., the reaction mixture was stirred for 24 hours. After completion of the reaction, the reaction product was cooled to room temperature, and an extraction process was performed thereon by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 1.37 g (1.4 mmol) of Intermediate 77-C.
0.21 g (2.1 mmol) of phenylacetylene and 0.50 g (12.6 mmol) of sodium hydroxide were suspended in 20 mL of methanol and stirred at room temperature for 30 minutes. A solution containing 1.37 g (1.4 mmol) of Intermediate 77-C and 1.4 mL of dichloromethane (DCM) was slowly added dropwise thereto at room temperature, and then stirred at room temperature for 12 hours. After completion of the reaction, an extraction process was performed on the reaction product by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 0.11 g (0.1 mmol) of Compound 77.
2.59 g (11.0 mmol) of 1,3-dibromobenzene, 0.65 g (5.5 mmol) of benzimidazole, 0.10 g (0.6 mmol) of copper iodide, 60 mg (0.6 mmol) of L-proline, and 2.33 g (11.0 mmol) of tripotassium phosphate (K3PO4) were added to a reaction vessel and suspended in 55 mL of dimethylformamide (DMF). The reaction temperature was raised to 160° C., and the mixture was stirred for 24 hours. After completion of the reaction, the reaction product was cooled to room temperature, and an extraction process was performed thereon by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 1.07 g (3.9 mmol) of Intermediate 96-A.
1.07 g (3.9 mmol) of Intermediate 96-A, 2.0 g (5.9 mmol) of N1-([1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,2-diamine, 0.18 g (0.2 mmol) of tris(dibenzylideneacetone)dipalladium, 0.16 g (0.4 mmol) of S-Phos, and 0.75 g (7.8 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 40 mL of toluene. The reaction temperature was raised to 110° C., and the mixture was stirred for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, and an extraction process was performed thereon by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 1.43 g (2.7 mmol) of Intermediate 96-B.
1.43 g (2.7 mmol) of Intermediate 96-B, 24 mL (148.5 mmol) of CH(OEt)3, and 0.28 mL (3.2 mmol) of HCl 35 wt % solution were added to a reaction vessel, and stirred for 12 hours after raising the reaction temperature to 80° C. After completion of the reaction, the reaction product was cooled to room temperature, and the residue obtained by removing the solvent was recrystallized to obtain 1.15 g (2.0 mmol) of Intermediate 96-C.
1.15 g (2.0 mmol) of Intermediate 96-C and 0.57 g (4.0 mmol) of iodomethane (Mel) were added to a reaction vessel and suspended in 20 mL of toluene. After raising the reaction temperature to 80° C., the reaction mixture was stirred for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, the solvent was partially removed, and distilled water was added to the reaction product. The resulting solid was filtered, and the filtrate was then purified by utilizing a recrystallization method to obtain 1.0 g (1.4 mmol) of Intermediate 96-D.
1.0 g (1.4 mmol) of Intermediate 96-D, 0.58 g (1.54 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 0.34 g (4.2 mmol) of sodium acetate were suspended in 55 mL of dioxane. After raising the reaction temperature to 120° C., the reaction mixture was stirred for 24 hours. After completion of the reaction, the reaction product was cooled to room temperature, 20 mL of distilled water was added thereto and an extraction process was performed thereon by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 160 mg (0.20 mmol) of Compound 96.
0.21 g (2.1 mmol) of phenylacetylene and 0.50 g (12.6 mmol) of sodium hydroxide were suspended in 20 mL of methanol and stirred at room temperature for 30 minutes. A solution containing 1.10 g (1.4 mmol) of Compound 96 and 1.4 mL of DCM was slowly added dropwise thereto at room temperature, and then stirred at room temperature for 12 hours. After completion of the reaction, an extraction process was performed on the reaction product by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 0.12 g (0.14 mmol) of Compound 93.
0.10 g (2.1 mmol) of sodium cyanide was suspended in 20 mL of methanol and stirred at room temperature for 30 minutes. A solution containing 1.10 g (1.4 mmol) of Compound 96 and 1.4 mL of DCM was slowly added dropwise thereto at room temperature, and then stirred at room temperature for 12 hours. After completion of the reaction, an extraction process was performed on the reaction product by utilizing ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated by utilizing column chromatography to obtain 0.10 g (0.13 mmol) of Compound 3.
Intermediate 2-A was synthesized in substantially the same manner as in the synthesis of Intermediate 96-A of Synthesis Example 2, except that imidazole was utilized instead of benzimidazole.
Intermediates 2-B, 2-C, 2-D, and 2-E were sequentially synthesized in substantially the same manners as in the synthesis of Intermediate 96-B, Intermediate 96-C, Intermediate 96-D, and Compound 96 of Synthesis Example 2, except that Intermediates 2-A, 2-B, 2-C, and 2-D were utilized instead of Intermediates 96-A, 96-B, 96-C, and 96-D, respectively.
80 mg (0.11 mmol) of Compound 2 was obtained in substantially the same manner as in the synthesis of Compound 3 of Synthesis Example 4, except that Intermediate 2-E was utilized instead of Compound 96.
0.15 g (0.15 mmol) of Compound 31 was obtained in substantially the same manner as in the synthesis of Compound 3 of Synthesis Example 4, except that Intermediate 77-C was utilized instead of Compound 96.
For the compounds synthesized in Synthesis Examples 1 to 6, high-resolution mass spectrum (HR-MS) was measured, and the results are shown in Table 1. Synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 6 may be easily recognized by those skilled in the art by referring to the synthesis paths and source materials.
The HOMO and LUMO energy levels of each of Compounds 77, 93, 96, 2, 3, 31, A, B, and C were evaluated according to methods described in Table 2, and the results are shown in Table 3.
Compound 77 (2 milligram (mg)), Compound ETH2 (10 mg), Compound HTH29 (10 mg), and PMMA in CH2Cl2 (wherein the weight of PMMA was 50 mg) were mixed together, and the resulting product was applied to a quartz substrate by utilizing a spin coater. The quartz substrate was heat-treated in an oven at 80° C., and then cooled to room temperature, to prepare Film 77 having a thickness of 40 nm. Next, Films 93, 96, 2, 3, 31, A, B, and C were prepared in substantially the same manner as in the preparation of Film 77, except that Compounds 93, 96, 2, 3, 31, A, B, and C were each utilized instead of Compound 77.
The emission spectrum for each of Films 77, 93, 96, 2, 3, 31, A, B, and C was measured by utilizing by a Quantaurus-QY absolute PL quantum yield spectrometer (equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere) manufactured by Hamamatsu Company and a PLQY measurement software (by Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, an excitation wavelength was scanned from 320 nanometer (nm) to 380 nm at intervals of 10 nm, and a spectrum measured at the excitation wavelength of 340 nm was taken to obtain a maximum emission wavelength (emission peak wavelength) and full width at half maximum (FWHM) of an organometallic compound included in each film. The results are summarized in Table 4.
Next, photoluminescence quantum yield (PLQY) for each of Films 77, 93, 96, 2, 3, 31, A, B, and C was measured by scanning an excitation wavelength from 300 nm to 380 nm at intervals of 10 nm with a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu Company, and the PLQY measured at the excitation wavelength of 330 nm was taken to obtain PLQY of an organometallic compound included in each film. The results are summarized in Table 4.
Referring to Table 4, it was confirmed that Compounds 77, 93, 96, 2, 3, and 31 each emitted blue light having relatively narrow FWHM while having improved PLQY, compared to Compounds A to C.
A glass substrate (product of Corning Inc.) with a 15 ohm per square centimeter (0/cm2) (1,200 angstrom (A)) ITO formed thereon as an anode was cut to a size of 50 millimeter (mm)×50 mm×0.7 mm, sonicated by utilizing isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred as “NPB”) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
A first compound (Compound 77), a second compound (Compound ETH2), and a third compound (Compound HTH29) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 350 Å. Here, the amount of first compound was 13 wt % per a total weight (100 wt %) of the emission layer, and the weight ratio of the second compound to the third compound was adjusted to 3.5:6.5.
Compound ETH34 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, and ET46 and Liq were vacuum-deposited on the hole blocking layer at a weight ratio of 4:6 to form an electron transport layer having a thickness of 310 Å. Next, Yb was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 15 Å, and then Mg was vacuum-deposited thereon to form a cathode having a thickness of 800 Å, thereby completing manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 5 were each utilized instead of Compound 77 as the first compound in forming an emission layer. In Table 5, the weight in parenthesis indicates the weight of the corresponding compound per 100 wt % of the emission layer.
The driving voltage (V) at 1,000 (candela per square meter (cd/m2)), y color coordinates (CIE(y)), color conversion efficiency (candela per ampere per year (cd/A/y)), maximum emission wavelength (nm), and lifespan (T95) of the organic light-emitting devices of Examples 1 to 6 and Comparative Examples A to C were each measured by utilizing a Keithley SMU 236 meter and a luminance meter PR650, and the results are shown in Table 6. In Table 6, the lifespan (T95) is a measure of the time (hr) expressed as a relative value (%) with respect to Comparative Example A, taken for the luminance to reach 95% of the initial luminance.
Referring to Table 6, it was confirmed that:
Organic light-emitting devices were each prepared in substantially the same manner as in Example 1, except that the first compound, the second compound, the third compound, and the fourth compound and the amounts thereof were changed as shown in Table 7 in forming an emission layer. In Table 7, the weight in parenthesis indicates the weight of the corresponding compound per 100 wt % of the emission layer.
The driving voltage (V) at 1,000 cd/m2, y color coordinates (CIE(y)), color conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) of the organic light-emitting devices of Examples 11 and 12 were measured in substantially the same manner as in Evaluation Example 3, and the results are shown in Table 8. In Table 8, the lifespan (T95) is a measure of the time (hr) expressed as a relative value (%) with respect to Comparative Example A, taken for the luminance to reach 95% of the initial luminance. For comparison, the data of the organic light-emitting device of Comparative Example A were also provided in Table 8.
Referring to Table 8, it was confirmed that the organic light-emitting devices of Examples 11 and 12 each emitted blue light and had excellent or suitable driving voltage, excellent or suitable color conversion efficiency, and excellent or suitable lifespan characteristics compared to the organic light-emitting device of Comparative Example A.
According to the one or more embodiments, an organometallic compound may have excellent or suitable processability and electrical properties, and thus a light-emitting device including the organometallic compound may have improved color purity, improved luminescence efficiency, and improved lifespan.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0132834 | Oct 2023 | KR | national |
