Patent Application
20250194410
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0180100, filed on Dec. 12, 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 light-emitting device including a heterocyclic compound, an electronic apparatus and electronic equipment that include the light-emitting device and the heterocyclic compound.
From among light-emitting devices, self-emissive devices have relatively wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and 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. Carriers, such as the holes and electrons, recombine in the emission layer to produce excitons. These excitons transition 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 light-emitting device including a heterocyclic compound, an electronic apparatus and electronic equipment that include the light-emitting device and the heterocyclic compound.
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 light-emitting device includes
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, electronic equipment includes the light-emitting device.
According to one or more embodiments, provided is the heterocyclic 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 one or more 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, one or more embodiments are merely described in more detail, 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,” “selected from,” and “selected from among,” 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.
Because the disclosure may have diverse modified embodiments, the embodiments are illustrated in the drawings and are described in the detailed description. An aspect and a characteristic of the disclosure, and a method of accomplishing these will be apparent if (e.g., when) referring to one or more embodiments described with reference to the drawings. The disclosure may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Hereinafter, embodiments of the disclosure will be described in more detail with reference to the accompanying drawings. The same or corresponding components will be denoted by the same reference numerals, and thus redundant description thereof will not be provided.
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,” and/or the like may be utilized herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only utilized to distinguish one component from another. 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. An expression utilized in the singular forms such as “a,” “an,” and “the” are intended to encompass the expression of the plural forms as well, unless it has a clearly different meaning in the context.
It will be further understood that the terms “comprises,” “comprising,” “comprise,” “has,” “have,” “having,” “include,” “includes,” and/or “including,” as utilized herein specify the presence of stated features or elements, but do not preclude the presence or addition of one or more other features or elements.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
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.
In the following embodiments, if (e.g., when) one or more components such as layers, films, regions, plates, and/or the like are said to be “connected to,” or “on” another component, this may include not only a case in which other components are “immediately on” the layers, films, regions, or plates, but also a case in which other components may be placed therebetween. Sizes of elements in the drawings may be exaggerated for convenience of explanation. In other words, because sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.
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” indicates that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.
Further, in this specification, the phrase “on a plane,” or “plan view,” indicates viewing a target portion from the top, and the phrase “on a cross-section” indicates viewing a cross-section formed by vertically cutting a target portion from the side.
The term “interlayer” as utilized herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.
An aspect of the disclosure provides a light-emitting device including:
In one or more embodiments,
In one or more embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or a (e.g., any suitable) combination thereof. For example, the hole blocking layer may directly contact the emission layer.
In one or more embodiments, the heterocyclic compound may be included in the interlayer.
In one or more embodiments, the heterocyclic compound may be included in the emission layer.
In one or more embodiments, the emission layer may further include a transition metal-containing compound, a delayed fluorescence compound, or a (e.g., any suitable) combination thereof. In the emission layer, the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may be different from each other.
In one or more embodiments, the emission layer may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group. In the emission layer, the second compound may be different from the heterocyclic compound.
In one or more embodiments, the emission layer may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound. In the emission layer, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may be different from each other.
In one or more embodiments, the emission layer may further include a luminescent material.
In one or more embodiments, the luminescent material may include a transition metal-containing compound, a delayed fluorescence compound, or a (e.g., any suitable) combination thereof. In the luminescent material, the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may be different from each other.
In one or more embodiments, the luminescent material may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group. In the luminescent material, the second compound may be different from the heterocyclic compound.
In one or more embodiments, the luminescent material may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound. In the luminescent material, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may be different from each other.
In one or more embodiments, the transition metal-containing compound may include platinum (Pt).
In one or more embodiments, the transition metal-containing compound may include platinum (Pt) and a tetradentate ligand bonded to the platinum, and the platinum and one of carbon atoms of the tetradentate ligand may be bonded to each other via a coordinate bond.
In one or more embodiments, the transition metal-containing compound may be a carbene-containing compound.
In one or more embodiments, the transition metal-containing compound may be a compound represented by Formula 3:
In one or more embodiments, the delayed fluorescence compound may be a compound including at least one cyclic group including both (e.g., simultaneously) boron (B) and nitrogen (N) as ring-forming atoms. The delayed fluorescence compound may serve to improve the color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device.
In one or more embodiments, the delayed fluorescence compound may be a compound in which a difference between a triplet energy level (electron volt (eV)) and a singlet energy level (eV) is at least 0 eV but not more than (i.e., at most) 0.5 eV (or at least 0 eV but not more than (i.e., at most) 0.3 eV).
In one or more embodiments, the delayed fluorescence compound may be a C8-C60 polycyclic group-containing compound including two or more cyclic groups condensed to each other while sharing boron (B).
In one or more embodiments, the delayed fluorescence 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 delayed fluorescence compound may include at least one compound represented by Formula 502, at least one compound represented by Formula 503, or a (e.g., any suitable) combination thereof:
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 a (e.g., any suitable) combination thereof.
In one or more embodiments, the second compound may include a compound represented by Formula 2:
b51 to b53 may each independently be an integer from 1 to 5,
Details on the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may each independently be as described herein.
In one or more embodiments, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound, or a (e.g., any suitable) combination thereof, may include at least one deuterium.
In one or more embodiments, the heterocyclic compound may include at least one deuterium.
In one or more embodiments, the transition metal-containing compound, the delayed fluorescence compound, and the second compound, or a (e.g., any suitable) combination thereof, may include at least one deuterium.
In one or more embodiments, the heterocyclic compound may include at least one silicon.
In one or more embodiments, the second compound may include at least one silicon.
In one or more embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the transition metal-containing compound, in addition to the heterocyclic compound. At least one of (e.g., selected from among) the heterocyclic compound and the transition metal-containing compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the delayed fluorescence compound, in addition to the heterocyclic compound, and at least one of (e.g., selected from among) the heterocyclic compound and the delayed fluorescence compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the transition metal-containing compound and the delayed fluorescence compound, in addition to the heterocyclic compound, and at least one of (e.g., selected from among) the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the second compound, in addition to the heterocyclic compound, and at least one of (e.g., selected from among) the heterocyclic compound and the second compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound, and at least one of (e.g., selected from among) the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may include at least one deuterium.
In one or more embodiments, the heterocyclic compound and the second compound may form (or provide) an exciplex. The heterocyclic compound and the second compound may include at least one deuterium.
In one or more embodiments, the emission layer of the light-emitting device may include: i) the heterocyclic compound and the second compound; and/or ii) the transition metal-containing compound or the delayed fluorescence compound.
In one or more embodiments, the emission layer may include a host and a dopant, and the heterocyclic compound may be included in the host. For example, the heterocyclic compound may act as a host.
In one or more embodiments, the emission layer may be to emit blue light.
The blue light may have a maximum emission wavelength in a range of, for example, about 430 nanometer (nm) to about 480 nm.
In one or more embodiments, the light emitted from the emission layer may have a maximum emission wavelength in a range of about 400 nm to about 500 nm, about 410 nm to about 490 nm, about 420 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
In one or more embodiments, the light-emitting device may satisfy at least one of (e.g., selected from among) Conditions 1 to 4:
lowest unoccupied molecular orbital (LUMO) energy level (eV) of heterocyclic compound>LUMO energy level (eV) of transition metal-containing compound; Condition 1
LUMO energy level (eV) of transition metal-containing compound>LUMO energy level (eV) of second compound; Condition 2
highest occupied molecular orbital (HOMO) energy level (eV) of transition metal-containing compound>HOMO energy level (eV) of heterocyclic compound; and Condition 3
HOMO energy level (eV) of heterocyclic compound>HOMO energy level (eV) of second compound. Condition 4
Each of the HOMO energy level and LUMO energy level of each of (e.g., selected from among) the heterocyclic compound, the second compound, and the transition metal-containing compound may be a negative value, and may be measured according to a suitable method.
In one or more embodiments, the absolute value of a difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the second compound may be at least 0.1 eV but not more than (i.e., at most) 1.0 eV, or the absolute value of a difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the heterocyclic compound may be at least 0.1 eV but not more than (i.e., at most) 1.0 eV, and the absolute value of a difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., at least 0.2 eV but not more than (i.e., at most) 1.25 eV) or the absolute value of a difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the heterocyclic compound may be 1.25 eV or less (e.g., at least 0.2 eV but not more than (i.e., at most) 1.25 eV).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described herein, a balance between holes and electrons 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 heterocyclic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a transition metal-containing compound, and the emission layer may be to emit phosphorescence or fluorescence emitted from the transition metal-containing compound. For example, according to the first embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may be a dopant or an emitter. For example, the transition metal-containing compound may be a phosphorescent dopant or a phosphorescence emitter.
The phosphorescence or fluorescence emitted from the transition metal-containing compound may be blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may serve to improve luminescence efficiency from the transition metal-containing compound by effectively transferring energy to the transition metal-containing compound, which is a dopant or an emitter.
The auxiliary dopant may be different from each of (e.g., selected from among) the transition metal-containing compound and the heterocyclic compound.
In one or more embodiments, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including both (e.g., simultaneously) boron (B) and nitrogen (N) as ring-forming atoms.
The emission layer may further include at least one host that is different from the heterocyclic compound, the transition metal-containing compound, and the auxiliary dopant. For example, the emission layer may further include a second compound as a host.
According to the second embodiment, the heterocyclic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a transition metal-containing compound and a dopant, and the heterocyclic compound, the transition metal-containing compound, 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. For example, according to the second embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may not serve as a dopant, but may serve as an auxiliary dopant that transfers energy to a dopant (or emitter).
In one or more embodiments, in the second embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may serve as an emitter, and, also as an auxiliary dopant that transfers energy to a dopant (or emitter).
In one or more embodiments, the phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
The dopant (or emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the transition metal-containing compound) or any fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or a (e.g., any suitable) combination thereof).
The emission layer may further include at least one host that is different from the heterocyclic compound, the transition metal-containing compound, and the dopant (or emitter). For example, the emission layer may further include a second compound as a host.
The blue light in the first embodiment and the second embodiment may be blue light having a maximum emission wavelength in a range of about 400 nm to about 500 nm, about 410 nm to about 490 nm, about 420 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
The auxiliary dopant in the first embodiment may include, for example, the delayed fluorescence compound represented by Formula 502 or Formula 503.
The host in the first embodiment and the second embodiment may further include a (e.g., any suitable) host material (e.g., a compound represented by Formula 301, a compound represented by 301-1, a compound represented by Formula 301-2, or a (e.g., any suitable) 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 (e.g., selected form among) a first capping layer arranged outside (e.g., and on) the first electrode and a second capping layer arranged outside (e.g., and on) the second electrode, and the heterocyclic compound represented by Formula 1 may be included in at least one of (e.g., selected form among) the first capping layer and the second capping layer. More details on the first capping layer and/or the second capping layer may each independently be as described herein.
In one or more embodiments, the light-emitting device may include:
The expression “(an interlayer and/or a capping layer) includes a heterocyclic compound represented by Formula 1” as utilized herein may include a case in which “(an interlayer and/or a capping layer) includes substantially identical heterocyclic compounds represented by Formula 1” and a case in which “(an interlayer and/or a capping layer) includes two or more different heterocyclic compounds represented by Formula 1.”
In one or more embodiments, the interlayer and/or the capping layer may include, as the heterocyclic compound, Compound 1 only. 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 heterocyclic compound, Compounds 1 and 2. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., both (e.g., simultaneously) Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
The term “interlayer” as utilized herein refers to a single layer and/or each (e.g., any or all) of multiple layers arranged between the first electrode and the second electrode of the light-emitting device.
Another aspect of the disclosure provides an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus 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. The electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a (e.g., any suitable) combination thereof. More details on the electronic apparatus may each independently be as described herein.
Another aspect of the disclosure provides electronic equipment including the light-emitting device.
For example, the electronic equipment may be at least one of (e.g., 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 mobile phone, a tablet, 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/or a signboard.
Another aspect of the disclosure provides the heterocyclic compound represented by Formula 1. Details on Formula 1 may each independently be as described herein.
Synthesis methods of the heterocyclic 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, R1 and R2 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 C1-C60 alkylthio 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, —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).
In Formula 1, a1 and a2 indicate the number of R1 and the number of R2, respectively, and may each independently be an integer from 1 to 7. When a1 is 2 or more, two or more of R1 may be substantially identical to or different from each other, and if (e.g., when) a2 is 2 or more, two or more of R2 may be substantially identical to or different from each other.
In one or more embodiments, R1 and R2 may each independently be:
In one or more embodiments, R1 and R2 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 (e.g., any one selected from among) Formulae 9-1 to 9-19, a group represented by one of (e.g., any one selected from among) Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2):
In one or more embodiments, R1 and R2 may each independently be:
In one or more embodiments, R2 may not be a (e.g., may exclude) a C3-C20 cycloalkyl group unsubstituted or substituted with at least one R10a.
In one or more embodiments, R2 may be:
In one or more embodiments, R2 may be:
In Formula 1, Z1 may be a C3-C20 cycloalkyl group unsubstituted or substituted with at least one R10a.
In one or more embodiments, Z1 may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, or a norbornanyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoisoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzosilolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —O(Q31), —S(Q31), —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or a (e.g., any suitable) combination thereof.
In one or more embodiments, Z1 may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, or a norbornanyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C1 alkylphenyl group, a naphthyl group, or a (e.g., any suitable) combination thereof.
In one or more embodiments, Z1 may be of (e.g., may be selected from among) groups represented by Formulae Z(1) to Z(11):
In Formula 1, L1 may be 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.
In Formula 1, n1 indicates the number of L1, and may be an integer from 1 to 3. When n1 is 2 or more, two or more of L1 may be substantially identical to or different from each other.
In one or more embodiments, L1 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phthalazine group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasiline group, a dibenzothiasiline group, a dibenzodihydroazasiline group, a dibenzodihydrodihydrodisiline group, a dibenzodihydrosiline group, a dibenzodioxine group, a dibenzooxathiine group, a dibenzooxazine group, a dibenzopyran group, a dibenzodithiine group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 may be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, or a phthalazine group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 may be a group represented by one of (e.g., any one selected from among) Formulae L(1) to L(24):
In one or more embodiments, n1 may be 1.
In Formula 1, Ar1 to Ar3 may each independently be 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.
In one or more embodiments, Ar1 to Ar3 may each independently be:
In one or more embodiments, Ar1 to Ar3 may each independently be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a triazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group, each unsubstituted or substituted with deuterium, a cyano group, —CD3, —CD2H, —CDH2, a C1-C20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a triazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or a (e.g., any suitable) combination thereof.
In one or more embodiments, Ar1 to Ar3 may each independently be a group represented by one of (e.g., any one selected from among) Formulae 10-1 to 10-246:
In one or more embodiments, the heterocyclic compound represented by Formula 1 may include one C1-C20 cycloalkyl group.
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be represented by Formula 1-1:
Unless defined otherwise, for example, in the description of Formula 1, R10a may be:
Unless defined otherwise, for example, in the description of Formula 1, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a 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 a (e.g., any suitable) combination thereof.
The heterocyclic compound represented by Formula 1 includes Z1, which is a C1-C20 cycloalkyl group, in a bicarbazole moiety, and thus has improved hole transporting ability. Accordingly, if (e.g., when) the heterocyclic compound is applied to a light-emitting device, a decrease in driving voltage may be obtained. In one or more embodiments, in the heterocyclic compound represented by Formula 1, due to the inclusion of Z1 and *—Si(Ar1)(Ar2)(Ar3), which include (e.g., consist of) sp3 hybrid orbitals, conjugation expansion may be suppressed or reduced, and thus, relatively high triplet energy may be obtained. Accordingly, if (e.g., when) the heterocyclic compound is utilized in a light-emitting device, high luminescence efficiency may be exhibited. Also, due to the increase in bulkiness of molecules, interaction with a dopant compound may be suppressed or reduced, and thus, formation of exciplexes with the dopant compound may be suppressed or reduced. Therefore, due to the utilization of the heterocyclic compound, an electronic device (e.g., an organic light-emitting device) having a low driving voltage and high efficiency may be implemented.
In Formula 2, b51 to b53 indicate the number of L51 to the number of 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 substantially identical to or different from each other, if (e.g., when) b52 is 2 or more, two or more of L52 may be substantially identical to or different from each other, and if (e.g., when) b53 is 2 or more, two or more of L53 may be substantially 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 of L51, a bond between two or more of L52, a bond between two or more of L53, 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), X56 may be N or C(R56), and at least one of X54 to X56 may be N. R54 to R56 are each as described herein. For example, two or three of X54 to X56 may each be N.
In Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may each not be a phenyl group.
In one or more embodiments, in Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may be substantially identical to each other.
In one or more embodiments, in Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 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, in Formula 2, R51 and R52 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 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, —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,
In one or more embodiments,
In one or more embodiments, in Formula 2, R51 to R56 may each independently be:
In Formula 3, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
In one or more embodiments, M may be Pt.
In Formula 3, X901 to X904 may each independently be C or N.
In one or more embodiments, X901 may be C. For example, in Formula 3, X901 may be C, and C may be carbon of a carbene moiety.
In one or more embodiments, in Formula 3, X901 may be N.
In one or more embodiments, X902 and X903 may each be C, and X904 may be N.
In Formula 3, i) a bond between X901 and M may be a coordinate bond, ii) one of a bond between X902 and M, a bond between X903 and M, and a bond between X904 and M may be a coordinate bond, and the other two may each be a covalent bond.
In one or more embodiments, a bond between X901 and M and a bond between X904 and M may each be a coordinate bond, and a bond between X902 and M and a bond between X903 and M may each be a covalent bond.
In one or more embodiments, X901 may be C, and a bond between X901 and M may be a coordinate bond.
In Formula 3, ring CY901 to ring CY004 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, ring CY901 may be a nitrogen-containing C1-C60 heterocyclic group.
In Formula 3, ring CY901 may be i) an X901-containing 5-membered ring, ii) an X901-containing 5-membered ring in which at least one 6-membered ring is condensed, or iii) an X901-containing 6-membered ring. In one or more embodiments, in Formula 3, ring CY901 may be i) an X901-containing 5-membered ring or ii) an X901-containing 5-membered ring in which at least one 6-membered ring is condensed. For example, ring CY901 may include a 5-membered ring bonded to M in Formula 3 via X901. In this regard, the X901-containing 5-membered ring may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and the X901-containing 6-membered ring and the 6-membered ring which may be optionally condensed to the X901-containing 5-membered ring may each independently be a benzene group, a pyridine group, or a pyrimidine group.
In one or more embodiments, ring CY901 may be an X901-containing 5-membered ring, and the X901-containing 5-membered ring may be an imidazole group or a triazole group.
In one or more embodiments, ring CY901 may be an X901-containing 5-membered ring in which at least one 6-membered ring is condensed, and the X901-containing 5-membered ring in which the at least one 6-membered ring is condensed may be a benzimidazole group or an imidazopyridine group.
In one or more embodiments, ring CY901 may be an imidazole group, a triazole group, a benzimidazole group, or an imidazopyridine group.
In one or more embodiments, X901 may be C, and ring CY901 may be an imidazole group, a triazole group, a benzimidazole group, a naphthoimidazol group, or an imidazopyridine group.
In one or more embodiments, ring CY902 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, or an azadinaphthosilole group.
In one or more embodiments, ring CY902 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In Formula 3, ring CY903 may be: a C2-C8 monocyclic group; or a C4-C20 polycyclic group in which two or three C2-C8 monocyclic groups are condensed with each other.
In one or more embodiments, in Formula 3, ring CY903 may be: a C4-C6 monocyclic group; or a C4-C8 polycyclic group in which two or three C4-C6 monocyclic groups are condensed with each other.
The term “C2-C8 monocyclic group” as utilized herein refers to a non-condensed cyclic group. For example, the C2-C8 monocyclic group may be a cyclopentadiene group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a cycloheptadiene group, or a cyclooctadiene group.
In one or more embodiments, ring CY903 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.
In Formula 3, ring CY904 may be a nitrogen-containing C1-C60 heterocyclic group.
In one or more embodiments, ring CY904 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a benzopyrazole group, a benzimidazole group, or a benzothiazole group.
In Formula 3, L901 to L903 may each independently be a single bond, *—C(R1a)(R1b)—*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom.
R1a and R1b are each as described herein.
In one or more embodiments, L901 and L903 may each be a single bond, and L902 may be *—C(R1a)(R1b)—*′, *—B(R1a)—*′,*—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, or *—S—*′.
In one or more embodiments, L902 may be *—O—*′ or *—S—*′.
In Formula 3, n901 to n903 indicate the number of L901 to the number of L903, respectively, and may each independently be an integer from 1 to 5. When each of n901 to n903 is 2 or more, each of: two or more of L901; two or more of L902; and two or more of L903 may be substantially identical to or different from each other.
In one or more embodiments, n902 may be 1.
In Formula 3, R901 to R904, R1a, and R1b 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, —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).
R10a, Q1, Q2, and Q3 are each as described herein.
In one or more embodiments, R901 to R904, R1a, and R1b may each independently be:
Q1 to Q3 and Q31 to Q33 are each as described herein.
In one or more embodiments, R901 to R904, R1a, and R1b may each independently be:
In Formula 3, a901 to a904 indicate the number of R901 to the number of R904, respectively, and may each independently be an integer from 1 to 10. When each of a901 to a904 is 2 or more, each of: two or more of R901; two or more of R902; two or more of R903; and two or more of R904 may be substantially identical to or different from each other.
In Formulae 502 and 503,
In Formulae 502 and 503, a501 to a504 indicate the number of R501 to the number of R504, respectively, and may each independently be an integer from 0 to 20. When a501 is 2 or more, two or more of R501 may be substantially identical to or different from each other, if (e.g., when) a502 is 2 or more, two or more of R502 may be substantially identical to or different from each other, if (e.g., when) a503 is 2 or more, two or more of R503 may be substantially identical to or different from each other, and if (e.g., when) a504 is 2 or more, two or more of R504 may be substantially identical to or different from each other. a501 to a504 may each independently be an integer from 0 to 8.
R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b utilized herein 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 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 are each as described herein.
In one or more embodiments, in Formulae 502 and 503, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b may each independently be:
In one or more embodiments, R10a utilized herein may be:
In one or more embodiments, i) R51 to R56 in Formula 2, ii) R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 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 (e.g., any one selected from among) Formulae 9-1 to 9-19, a group represented by one of (e.g., any one selected from among) Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2) (wherein Q1 to Q3 are each as described herein):
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be one of (e.g., any one selected from among) Compounds 1 to 174:
Hereinafter, the 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 (or providing) the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming (or providing) 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 semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, if (e.g., when) the first electrode 110 is a transmissive electrode, a material for forming (or providing) 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, if (e.g., when) the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming (or providing) 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 is arranged on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region arranged between the first electrode 110 and the emission layer, and an electron transport region arranged 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 a quantum dot, and/or the like.
In one or more embodiments, the interlayer 130 may include i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emitting units. When the interlayer 130 includes the two or more 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 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.
In one or more embodiments, 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 constituent layers of each structure are stacked sequentially 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:
In one or more embodiments, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) groups represented by Formulae CY201 to CY217:
In one or more embodiments, in Formulae CY201 to CY217, ring CY201 to ring CY204 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 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.
In one or more embodiments, the hole transport region may include: at least one (e.g., one or more) 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″-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 the ranges described herein, 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 materials described herein, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly (substantially uniformly) or non-uniformly (substantially non-uniformly) dispersed in the hole transport region (e.g., in the form (or provide) of a single layer including (e.g., consisting of) a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In one or more embodiments, 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 are TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound are 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 are: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); a 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); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), and/or the like); a 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), thull(Tm), ytterbium (Yb), lutetium (Lu), and/or the like); and/or the like.
Examples of the metalloid are silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Examples of the non-metal are oxygen (O), halogen (e.g., F, Cl, Br, I, and/or the like), and/or the like.
Examples of the compound including element EL1 and element EL2 are 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 are 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 are 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 are LiF, NaF, KF, RbF, CsF, LiCl, 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 are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and/or the like.
Examples of the transition metal halide are titanium halide (e.g., TiF4, TiC4, TiBr4, TiI4, and/or the like), zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, and/or the like), hafnium halide (e.g., HfF4, HfCl4, HfBr4, HfI4, and/or the like), vanadium halide (e.g., VF3, VCl3, VBr3, VI3, and/or the like), niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, and/or the like), tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, and/or the like), chromium halide (e.g., CrF3, CrO3, CrBr3, CrI3, and/or the like), molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, and/or the like), tungsten halide (e.g., WF3, WCl3, WBr3, WI3, and/or the like), manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, and/or the like), technetium halide (e.g., TcF2, TcCl2, TcBr2, Tcl2, and/or the like), rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, and/or the like), iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, and/or the like), ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, and/or the like), osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, and/or the like), cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, and/or the like), rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, and/or the like), iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, and/or the like), nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, and/or the like), palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, and/or the like), platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, and/or the like), copper halide (e.g., CuF, CuCl, CuBr, CuI, and/or the like), silver halide (e.g., AgF, AgCl, AgBr, AgI, and/or the like), gold halide (e.g., AuF, AuCl, AuBr, AuI, and/or the like), and/or the like.
Examples of the post-transition metal halide are zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, and/or the like), indium halide (e.g., InI3, and/or the like), tin halide (e.g., SnI2, and/or the like), and/or the like.
Examples of the lanthanide metal halide are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and/or the like.
Examples of the metalloid halide are antimony halide (e.g., SbCl5, and/or the like) and/or the like.
Examples of the metal telluride are 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 subpixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of 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 of 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.
The emission layer may further include an auxiliary dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
An amount of the dopant 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 a quantum dot.
In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer.
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 the ranges described herein, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 Formula 301
In one or more embodiments, if (e.g., 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 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. For example, the host may include a Be complex (e.g., Compound H55), a Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include: at least one of (e.g., one or more selected from among) Compounds H1 to H128; 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-carbazolylbenzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
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.
In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In one or more embodiments, 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, if (e.g., when) xc1 in Formula 401 is 2 or more, two of ring A401 among two or more of L401 may optionally be linked to each other via T402, which is a linking group, and two of ring A402 among two or more of L401 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 are each 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, a —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, and/or the like), or any combination thereof.
The phosphorescent dopant may include, for example, one of (e.g., one or more selected from qamong) Compounds PD1 to PD39, or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In one or more embodiments, the fluorescent dopant may include at least one compound represented by Formula 501:
In one or more embodiments, 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 with each other.
In one or more embodiments, xd4 in Formula 501 may be 2.
In one or more embodiments, the fluorescent dopant may include: at least one (e.g., one or more) selected from among Compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:
The emission layer may include a delayed fluorescence material.
The delayed fluorescence material described herein may be of (e.g., may be selected from among) compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may act as a host or a dopant depending on the type or kind of other materials included in the emission layer.
In one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be at least 0 eV but not more than 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is within the range described herein, up-conversion from the triplet state to the singlet state of the delayed fluorescence material may effectively occur, and thus, the light-emitting device 10 may have improved luminescence efficiency.
In one or more embodiments, the delayed fluorescence material may include i) a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group, and/or the like) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, and/or the like), ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B), and/or the like.
Examples of the delayed fluorescence material may include at least one of (e.g., one or more selected from among) Compounds DF1 to DF14:
The emission layer may include a quantum do”.
The term “quantum dot” as utilized herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.
A diameter of the quantum dot may be, for example, in a range of about 1 nanometer (nm) to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Examples of the Group II-VI semiconductor compound are: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and/or the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and/or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and/or the like; or any combination thereof.
Examples of the Group III-V semiconductor compound are: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and/or the like; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element are InZnP, InGaZnP, InAlZnP, and/or the like.
Examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and/or the like; a ternary compound, such as InGaS3, InGaSe3, and/or the like; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound are: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, and/or the like; or any combination thereof.
Examples of the Group IV-VI semiconductor compound are: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or any combination thereof.
Examples of the Group IV element or compound are: a single element compound, such as Si, Ge, and/or the like; a binary compound, such as SiC, SiGe, and/or the like; or any combination thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.
In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer which prevents chemical denaturation of the core to maintain semiconductor characteristics, and/or as a charging layer which imparts electrophoretic characteristics to the quantum dot. The shell may be single-layered or multi-layered. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
Examples of the shell of the quantum dot are an oxide of metal, metalloid, or non-metal, a semiconductor compound, and/or a (e.g., any suitable) combination thereof. Examples of the oxide of metal, metalloid, or non-metal are: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, and/or the like; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, and/or the like; or any combination thereof. Examples of the semiconductor compound are: as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. Examples of the semiconductor compound are CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or for example, about 30 nm or less. When the FWHM of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. In one or more embodiments, because light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In one or more embodiments, the quantum dot may be in the form (or provide) of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, a nanoplate particle, and/or the like.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. For example, the size of the quantum dot may be selected to emit red light, green light, and/or blue light. In one or more embodiments, the size of the quantum dot may be configured to emit white light by combination of light of one or more suitable colors.
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 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.
In one or more embodiments, 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 constituent layers of each structure are sequentially stacked from the emission layer.
The electron transport region (e.g., the buffer layer, the hole blocking layer, the electron control layer, or the 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 cyclic group.
In one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
In one or more embodiments, if (e.g., 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:
In one or more embodiments, 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 of (e.g., one or more selected from among) Compounds ET1 to ET45; 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:
A 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 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 thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within the ranges described herein, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (e.g., the electron transport layer in the electron transport region) may further include, in addition to the materials described herein, 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 alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In one or more embodiments, 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 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 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, iodides, and/or the like), 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: alkali metal oxides, 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 compound, 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 are 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 of (e.g., selected from among) 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, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, 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., a 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., alkali metal halide), ii) a) an alkali metal-containing compound (e.g., 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 RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, 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 may be uniformly (substantially uniformly) or non-uniformly (substantially non-uniformly) dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described herein, 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 a structure as described herein. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming (or providing) 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 lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (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. For example, 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 aspect of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that 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 of (e.g., 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 of (e.g., 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 of (e.g., selected from among) the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one of (e.g., selected from among) the first capping layer and the second capping layer may each independently include at least one of (e.g., selected from among) Compounds HT28 to HT33, at least one of (e.g., selected from among) Compounds CP1 to CP6, β-NPB, or any combination thereof:
The heterocyclic compound represented by Formula 1 may be included in one or more suitable films. Accordingly, another aspect of the disclosure provides a film including the heterocyclic compound represented by Formula 1. The film may be, for example, an optical member (or a light control component) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, and/or the like), a light blocking member (e.g., a light reflective layer, a light absorbing layer, and/or the like), a protective member (e.g., an insulating layer, a dielectric layer, and/or the like), and/or the like.
The light-emitting device may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. Details on the light-emitting device may each independently be as described herein. In one or more embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, the quantum dot as described herein.
The electronic apparatus 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 layer 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 arranged among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.
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. 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. For example, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include (e.g., may exclude) a quantum dot. Details on the quantum dot may each independently be as described herein. The first area, the second area, and/or the third area may each further include a scatter.
In one or more embodiments, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described herein. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode or the drain electrode may be electrically connected to any one of the first electrode or 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 apparatus 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 apparatus 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 utilize of the electronic apparatus. Examples of the functional layers are 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 apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., a mobile personal computer), 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 device may be included in one or more suitable electronic equipment.
In one or more embodiments, the electronic equipment including the light-emitting device may be one 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 mobile phone, a tablet, 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, or a (e.g., any suitable) combination thereof.
The light-emitting device may have excellent or suitable luminescence efficiency and long lifespan, and thus, the electronic equipment including the light-emitting device may have characteristics such as high luminance, high resolution, and low power consumption.
The light-emitting apparatus 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 may 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 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. A 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, not 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 an 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 one or more 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 (or provide) of a common layer.
The second electrode 150 may be arranged on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be arranged on the capping layer 170. The encapsulation portion 300 may be arranged on a light-emitting device to protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx, where 0<x<1.8), silicon oxide (SiOx, where 0<x≤2), 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 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 equipment 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 equipment 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 the 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 wheels, 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 (e.g., spaced apart or separated) 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 (e.g., spaced apart or separated) from each other in the x-direction or the −x-direction. For example, 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 the 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 (e.g., selected from among) 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 arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced and/or apart (e.g., spaced apart or separated) 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 arranged 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 light-emitting display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to one or more embodiments of the disclosure, an organic light-emitting display device including the light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described herein may be utilized in embodiments of the disclosure.
Referring to
Referring to
Referring to
In one or more embodiments, the display device 2 arranged on the passenger seat dashboard 1600 may display an image related to information displayed on the cluster 1400 and/or information displayed on the center fascia 1500. In one or more embodiments, the display device 2 arranged on the passenger seat dashboard 1600 may display information different from information displayed on the cluster 1400 and/or information displayed on the center fascia 1500.
The 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 the 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 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 including (e.g., consisting of) carbon only as a ring-forming atom and having 3 to 60 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 including (e.g., 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 “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 cyclic 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 cyclic 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 monovalent C1-C60 heterocyclic group are a C3-C1 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, and examples of the divalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may include 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 substituted or unsubstituted 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 examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and/or the like. 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 are 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 are 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 are 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 are 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-C10 cycloalkyl group.
The term “C1-C10 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 examples thereof are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like. The term “C1-C10 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 has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof are 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 having at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C1 heterocycloalkenyl group are 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 are 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 are 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 (e.g., having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are 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.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (e.g., 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 condensed heteropolycyclic group are a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl 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 indenocarbazolyl 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, a benzothienodibenzothiophenyl group, and/or the like. 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 “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein refers to —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 are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
The term “third-row transition metal” as utilized herein includes 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.” For example, 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.” For example, 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.
The x-axis, y-axis, and z-axis as utilized herein are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.
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, the electronic apparatus, the electronic device, 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 the electronic apparatus, 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 the electronic apparatus 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 apparatus 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 one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples indicates that a substantially identical molar equivalent of B was utilized in place of A.
Compound 15 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 1.
1,4-dibromobenzene (CAS number=106-37-6) and 4-bromo-1,1′-biphenyl (CAS number=29558-77-8) were each allowed for a reaction with n-BuLi, and then allowed for a reaction with dichlorodiphenylsilane (CAS number=80-10-4), so as to obtain Intermediate 15-1. In relation to Intermediate 15-1, the following M+1 peak value was confirmed by liquid chromatography mass spectrometry (LC-MS).
C30H23BrSi: M+1 491.08
2-bromo-9H-carbazole (CAS number=3652-90-2) and cyclohexylboronic acid (CAS number=4441-56-9) were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 15-2. In relation to Intermediate 15-2, the following M+1 peak value was confirmed by LC-MS.
C18H19N: M+1 250.14
2-bromo-9H-carbazole (CAS number=3652-90-2), potassium hydroxide, and 4-toluenesulfonyl chloride (CAS number=98-59-9) were allowed for a reaction, so as to obtain Intermediate 15-3. In relation to Intermediate 15-3, the following M+1 peak value was confirmed by LC-MS.
C19H14BrNO2S: M+1 399.99
Intermediate 15-3 and Intermediate 15-2 were allowed for a reaction in the presence of a Cu catalyst, so as to obtain Intermediate 15-4. In relation to Intermediate 15-4, the following M+1 peak value was confirmed by LC-MS.
C37H32N2O2S: M+1 569.23
Intermediate 15-4 and sodium hydroxide were allowed for a reaction, so as to obtain Intermediate 15-5. In relation to Intermediate 15-5, the following M+1 peak value was confirmed by LC-MS.
C30H26N2: M+1 415.21
4 g of Intermediate 15-1, 3.7 g of Intermediate 15-5, 1.2 g of sodium tert-butoxide, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.26 mL of tri-tert-butylphosphine, and 40 mL of toluene were added to a reaction vessel, and refluxed for 24 hours. After completion of the reaction, an aqueous extraction process was performed on the reaction solution by utilizing ethyl acetate, and an organic layer collected therefrom was dried by utilizing magnesium sulfate. A residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, so as to obtain 5.5 g (yield: 82%) of Compound 15. Compound 15 was confirmed by LC-MS and 1H-NMR.
Compound 27 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 2.
Intermediate 27-1 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-2, except that 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (CAS number=2650519-97-2) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2). In relation to Intermediate 27-1, the following M+1 peak value was confirmed by LC-MS.
C18H12D7N: M+1 257.18
(3-bromophenyl)triphenylsilane (CAS number=185626-73-7) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS number=38537-24-5) were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 27-2. In relation to Intermediate 27-2, the following M+1 peak value was confirmed by LC-MS.
C36H19D8NSi: M+1 510.24
Intermediate 27-2 and N-bromosuccinimide were allowed for a reaction, so as to obtain Intermediate 27-3. In relation to Intermediate 27-3, the following M+1 peak value was confirmed by LC-MS.
C36H19D7BrNSi: M+1 587.13
Substantially the same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 27-1 and Intermediate 27-3 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 4.8 g (yield: 75%) of Compound 27 was obtained. Compound 27 was confirmed by LC-MS and 1H-NMR.
Compound 28 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 3.
9-(2-bromophenyl)-9H-carbazole (CAS number=902518-11-0) was allowed for a reaction with n-BuLi, and then allowed for a reaction with trimethyl borate (CAS number=121-43-7), so as to obtain Intermediate 28-1. In relation to Intermediate 28-1, the following M+1 peak value was confirmed by LC-MS.
C18H14BNO2: M+1 288.10
(3-bromophenyl)triphenylsilane (CAS number=185626-73-7) and Intermediate 28-1 were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 28-2. In relation to Intermediate 28-2, the following M+1 peak value was confirmed by LC-MS.
C42H31NSi: M+1 578.23
Intermediate 28-2 and N-bromosuccinimide were allowed for a reaction, so as to obtain Intermediate 28-3. In relation to Intermediate 28-3, the following M+1 peak value was confirmed by LC-MS.
C42H30BrNSi: M+1 656.13
Substantially the same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 28-3 and Intermediate 15-2 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 4 g of (yield: 80%) of Compound 28 was obtained. Compound 28 was confirmed by LC-MS and 1H-NMR.
Compound 64 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 4.
1,4-dibromo benzene-2,3,5,6-d4 (CAS number=4165-56-4) was allowed for a reaction with n-BuLi, and then allowed for a reaction with chlorotriphenylsilane (CAS number=76-86-8), so as to obtain Intermediate 64-1. In relation to Intermediate 64-1, the following M+1 peak value was confirmed by LC-MS.
C24H15D4BrSi: M+1 419.06
Intermediate 64-2 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-2, except that 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (CAS number=2764814-81-3) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2). In relation to Intermediate 64-2, the following M+1 peak value was confirmed by LC-MS.
C18H12D7N: M+1 257.19
Intermediate 64-3 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-3, except that 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (CAS number=2650519-97-2) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2). In relation to Intermediate 64-3, the following M+1 peak value was confirmed by LC-MS.
C19H7D7BrNO2S: M+1 407.04
Intermediate 64-4 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-4, except that Intermediate 64-2 and Intermediate 64-3 were utilized instead of Intermediate 15-2 and Intermediate 15-3. In relation to Intermediate 64-4, the following M+1 peak value was confirmed by LC-MS.
C37H18D14N2O2S: M+1 583.32
Intermediate 64-5 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-5, except that Intermediate 64-4 was utilized instead of Intermediate 15-4. In relation to Intermediate 64-5, the following M+1 peak value was confirmed by LC-MS.
C30H12D14N2: M+1 429.32
The same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 64-1 and Intermediate 64-5 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 7.1 g (yield: 78%) of Compound 64 was obtained. Compound 64 was confirmed by LC-MS and 1H-NMR.
Compound 86 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 5.
Intermediate 86-1 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-2, except that 3-bromo-9H-carbazole (CAS number=1592-95-6) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2).
In relation to Intermediate 86-1, the following M+1 peak value was confirmed by LC-MS.
C18H19N: M+1 250.16
Intermediate 86-2 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-3, except that 4-bromo-9H-carbazole (CAS number=3652-89-9) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2). In relation to Intermediate 86-2, the following M+1 peak value was confirmed by LC-MS.
C19H14BrNO2S: M+1 399.99
Intermediate 86-3 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-4, except that Intermediate 86-1 and Intermediate 86-2 were utilized instead of Intermediate 15-2 and Intermediate 15-3. In relation to Intermediate 86-3, the following M+1 peak value was confirmed by LC-MS.
C37H32N2O2S: M+1 569.22
Intermediate 86-4 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-5, except that Intermediate 86-3 was utilized instead of Intermediate 15-4. In relation to Intermediate 86-4, the following M+1 peak value was confirmed by LC-MS.
C30H26N2: M+1 415.23
Substantially the same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 86-4 was utilized instead of Intermediate 15-5. 5.8 g (yield: 77%) of Compound 86 was obtained. Compound 86 was confirmed by LC-MS and 1H-NMR.
Compound 142 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 6.
Intermediate 142-1 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-2, except that 4-bromo-9H-carbazole (CAS number=3652-89-9) was utilized instead of 2-bromo-9H-carbazole (CAS number=3652-90-2). In relation to Intermediate 142-1, the following M+1 peak value was confirmed by LC-MS.
C18H19N: M+1 250.16
Intermediate 142-2 was obtained in substantially the same manner as utilized to synthesize Intermediate 27-2, except that (4-bromophenyl)triphenylsilane (CAS number=18737-40-1) was utilized instead of (3-bromophenyl)triphenylsilane (CAS number=185626-73-7). In relation to Intermediate 142-2, the following M+1 peak value was confirmed by LC-MS.
Intermediate 142-2 and N-bromosuccinimide were allowed for a reaction, so as to obtain Intermediate 142-3. In relation to Intermediate 142-3, the following M+1 peak value was confirmed by LC-MS.
C36H19D7BrNSi: M+1 587.16
Substantially the same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 142-1 and Intermediate 142-3 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 3.9 g (yield: 75%) of Compound 142 was obtained. Compound 142 was confirmed by LC-MS and 1H-NMR.
Compound 157 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 7.
Intermediate 157-1 was obtained in substantially the same manner as utilized to synthesize Intermediate 142-2, except that 9H-carbazole (CAS number=86-74-8) was utilized instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS number=38537-24-5). In relation to Intermediate 157-1, the following M+1 peak value was confirmed by LC-MS.
C36H27NSi: M+1 502.20
Intermediate 157-1 and N-bromosuccinimide were allowed for a reaction, so as to obtain Intermediate 157-2. In relation to Intermediate 157-2, the following M+1 peak value was confirmed by LC-MS.
C36H25Br2NSi: M+1 658.03
Intermediate 157-2 and (phenyl-d5)boronic acid (CAS number=215527-70-1) were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 157-3. In relation to Intermediate 157-3, the following M+1 peak value was confirmed by LC-MS.
C42H25D5BrNSi: M+1 661.18
The same manner as utilized to synthesize Compound 15 was utilized, except that Intermediate 157-3 and Intermediate 15-2 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 4.4 g (yield: 70%) of Compound 157 was obtained. Compound 157 was confirmed by LC-MS and 1H-NMR.
Compound 167 according to one or more embodiments may be synthesized according to, for example, Reaction Scheme 8.
3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (GAS number=2764814-81-3) and (phenyl-d5)boronic acid (GAS number=215527-70-1) were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 167-1. In relation to Intermediate 167-1, the following M+1 peak value was confirmed by LC-MS.
C18HD12N: M+1 256.19
Intermediate 167-1 and N-bromosuccinimide were allowed for a reaction, so as to obtain Intermediate 167-2. In relation to Intermediate 167-2, the following M+1 peak value was confirmed by LC-MS.
C18HD11BrN: M+1 333.09
Intermediate 167-2 and cyclohexylboronic acid (GAS number=4441-56-9) were allowed for a reaction in the presence of a Pd catalyst, so as to obtain Intermediate 167-3. In relation to Intermediate 167-3, the following M+1 peak value was confirmed by LC-MS.
C24H12D11N: M+1 337.25
Intermediate 167-3 and Intermediate 15-3 were allowed for a reaction in the presence of a Cu catalyst, so as to obtain Intermediate 167-4. In relation to Intermediate 167-4, the following M+1 peak value was confirmed by LC-MS.
C43H25D11N2O2S: M+1 656.31
Intermediate 167-5 was obtained in substantially the same manner as utilized to synthesize Intermediate 15-5, except that Intermediate 167-4 was utilized instead of Intermediate 15-4. In relation to Intermediate 167-5, the following M+1 peak value was confirmed by LC-MS.
C36H19D11N2: M+1 502.33
The same manner as utilized to synthesize Compound 15 was utilized, except that (3-bromophenyl)triphenylsilane (CAS number=185626-73-7) and Intermediate 167-5 were utilized instead of Intermediate 15-1 and Intermediate 15-5. 4.4 g (yield: 73%) of Compound 167 was obtained. Compound 167 was confirmed by LC-MS and 1H-NMR.
1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples are shown in Table 1. Synthesis methods of compounds other than the compounds synthesized in Synthesis Examples may be easily recognized by those skilled in the art by referring to the synthesis paths and source materials.
1H NMR (CDCl3, 500 MHz)
The highest occupied molecular orbital (HOMO) energy level (electron volt (eV)) and lowest unoccupied molecular orbital (LUMO) energy level (eV) of Compounds 15, 27, 28, 64, 86, 142, 157, and 167 were evaluated by utilizing the density functional theory (DFT) method of the Gaussian program, which was structure-optimized at the B3LYP/6-31G(d,p) level, and the results are shown in Table 2.
As an anode, a Corning 15 ohm per square centimeter (Ω/cm2) (1,200 angstrom (Å)) ITO glass substrate was cut to a size of 50 millimeter (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the resultant substrate was mounted on a vacuum deposition apparatus.
After HATCN was vacuum-deposited on the substrate to form (or provide) a hole injection layer having a thickness of 100 Å, BCFN as a first hole transport material was vacuum-deposited thereon to a thickness of 600 Å, and then, SiCzCz as a second hole transport material was vacuum-deposited thereon to a thickness of 50 Å, so as to form (or provide) a hole transport layer.
SiTrzCz2 and Compound 15 as hosts and PtON-TBBI as a phosphorescent dopant were co-deposited at a weight ratio of 60:27:13 on the hole transport layer to form (or provide) an emission layer having a thickness of 350 Å.
Subsequently, mSiTrz was deposited on the emission layer to form (or provide) a first electron transport layer having a thickness of 50 Å, and then, mSiTrz and LiQ (Compound ET-D1) were co-deposited thereon at a ratio of 1:1 to form (or provide) a second electron transport layer having a thickness of 350 Å, so as to form (or provide) an electron transport layer. LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form (or provide) an electron injection layer having a thickness of 15 Å, and then, Al was vacuum-deposited thereon to form (or provide) a LiF/Al electrode having a thickness of 80 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that, in forming (or providing) an emission layer, Compound 15 as a host was changed as shown in Table 3.
To evaluate characteristics of the organic light-emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 to 4, the driving voltage at the current density of 10 milliampere per square centimeter (mA/cm2), current density, and maximum quantum efficiency thereof were measured.
The driving voltage and current density of the organic light-emitting device were measured by utilizing a source meter (Keithley Instrument, 2400 series), and the maximum quantum efficiency was measured by utilizing the external quantum efficiency measurement device C9920-2-12 of Hamamatsu Photonics Inc.
In evaluating the maximum quantum efficiency, the luminance/current density was measured by utilizing a luminance meter that was calibrated for wavelength sensitivity, and the maximum quantum efficiency was converted by assuming an angular luminance distribution (Lambertian) which introduced a perfect reflecting diffuser.
The evaluation results of the characteristics of the organic light-emitting devices are shown in Table 3.
Referring to Table 3, it was confirmed that the organic light-emitting devices according to Examples 1 to 8 had a lower driving voltage and superior maximum quantum efficiency than the organic light-emitting devices according to Comparative Examples 1 to 4.
According to the one or more embodiments, by utilizing a heterocyclic compound of the present disclosure, a light-emitting device having a reduced driving voltage, improved efficiency, and an improved lifespan and a high-quality electronic apparatus including the light-emitting device may be manufactured.
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 one or more 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 |
|---|---|---|---|
| 10-2023-0180100 | Dec 2023 | KR | national |
