Patent Application
20250228134
This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0003122, filed on Jan. 8, 2024, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.
One or more aspects of embodiments of the present disclosure relate to an organic compound, a light-emitting device including the same, and an electronic apparatus including the light-emitting device.
Self-emissive devices (for example, organic light-emitting devices and/or the like) among light-emitting 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.
A light-emitting device may include a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, arranged sequentially. Holes injected from the first electrode may move toward the emission layer through the hole transport region. Electrons injected from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may combine in the emission layer to produce excitons that may transition (and/or relax) from an excited state to a ground state, and light may be generated thereby.
One or more aspects of embodiments of the present disclosure are directed toward an organic compound having a high photoluminescence quantum yield, a high molar extinction coefficient, and low delayed fluorescence lifespan, and a light-emitting device including the organic compound as a thermally activated delayed fluorescence (i.e., TADF) material and having high luminescence efficiency and long lifespan.
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 a first electrode, a second electrode opposite to (e.g., facing) the first electrode, and an interlayer arranged between the first electrode and the second electrode and including an emission layer, wherein the interlayer further includes an organic compound represented by Formula 1.
In Formula 1,
According to one or more embodiments, an electronic apparatus includes the light-emitting device and a thin-film transistor electrically connected to the light-emitting device.
According to one or more embodiments, an electronic equipment includes the light-emitting device and may be at least one selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertisement board, an indoor or outdoor lighting and/or signaling light, 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 microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, a sign, and combinations thereof.
According to one or more embodiments, provided is the organic 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, and duplicative descriptions thereof may not be provided the specification. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, one or more embodiments are merely described in more detail, by referring to the drawings, to explain aspects of the present description. An aspect and a characteristic of the disclosure, and a method of accomplishing these will be apparent if referring to one or more embodiments described with reference to the drawings. The same or corresponding components will be denoted by the same reference numerals, and thus redundant description thereof will not be provided.
As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “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.
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 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.
Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
According to one or more embodiments, a light-emitting device includes a first electrode, a second electrode opposite to (e.g., facing) the first electrode, and an interlayer arranged between the first electrode and the second electrode and including an emission layer, wherein the interlayer further includes an organic compound represented by Formula 1:
Because the light-emitting device includes the organic compound, the light-emitting device may have improved luminescence efficiency and improved lifespan characteristics. For example, the organic compound may be included in the emission layer.
In one or more embodiments, the light-emitting device may include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound including a transition metal, or any combination thereof, wherein the organic compound, the second compound, the third compound, and the fourth compound are different from each other:
Formulae 1 and 3 are each as described in the present specification.
In one or more embodiments, the light-emitting device may include a layer (e.g., an interlayer) including 1) the organic compound and 2) the second compound, the third compound, the fourth compound, or any combination thereof. The layer (e.g., interlayer) may include a mixture including 1) the organic compound and 2) the second compound, the third compound, the fourth compound, or any combination thereof. For example, the layer (e.g., interlayer) is clearly distinct from a double layer including (e.g., consisting of) 1) a first layer including the organic compound and 2) a second layer including the second compound, the third compound, the fourth compound, or any combination thereof. For example, the layer (e.g., interlayer) may be the emission layer.
For example, the interlayer (for example, the emission layer) may include i) the organic compound, ii) the organic compound and the second compound, iii) the organic compound and the third compound, iv) the organic compound and the fourth compound, v) the organic compound, the second compound, and the third compound, vi) the organic compound, the second compound, and the fourth compound, vii) the organic compound, the third compound, and the fourth compound, or viii) the organic compound and the second compound to the fourth compound.
In one or more embodiments, the organic compound and the second compound to the fourth compound may each include at least one deuterium.
In one or more embodiments, the second compound and the third compound may each include at least one silicon.
In one or more embodiments, the second compound and the third compound may form an exciplex.
In one or more embodiments, the emission layer may be to emit blue light.
In one or more embodiments, the maximum emission wavelength of the blue light may be about 430 nanometer (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 emission full width at half maximum (FWHM) of the blue light may be 40 nm or less, about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 37 nm, about 10 nm to about 37 nm, about 15 nm to about 37 nm, or about 20 nm to about 37 nm.
In one or more embodiments, the blue light may be deep blue light.
In one or more embodiments, the CIEx coordinate (for example, the top emission CIEx coordinate) of the blue light may be about 0.125 to about 0.140 or about 0.130 to about 0.140.
In one or more embodiments, the CIEy coordinate (for example, the top emission CIEy coordinate) of the blue light may be about 0.120 to about 0.210. For example, the CIEy coordinate may be measured via Evaluation Example 2 as described in more detail herein.
In one or more embodiments, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In one or more embodiments, the second compound may include a compound represented by Formula 2:
In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
In one or more embodiments, the third compound may exclude (e.g., neither be) Compound CBP nor mCBP:
In one or more embodiments, the fourth compound may be a compound including a transition metal and a ligand. The transition metal may be platinum (Pt). The ligand may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, or any combination thereof.
In one or more embodiments, the fourth compound may be represented by Formula 4:
In one or more embodiments, in Formula 4, R42 and R43 may be bonded to each other to form a benzene group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, the light-emitting device may satisfy at least one selected from among Condition 1 to Condition 4:
lowest unoccupied molecular orbital (LUMO) energy level (eV) of third compound>LUMO energy level (eV) of fourth compound; Condition 1
LUMO energy level (eV) of fourth compound>LUMO energy level (eV) of second compound; Condition 2
highest occupied molecular orbital (HOMO) energy level (eV) of fourth compound>HOMO energy level (eV) of third compound; and Condition 3
HOMO energy level (eV) of third compound>HOMO energy level (eV) of second compound. Condition 4
Each of the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of each of the second compound to the fourth 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 second compound and the LUMO energy level of the fourth compound may be about 0.1 electron volt (eV) to about 1.0 eV, and/or the absolute value of a difference between the LUMO energy level of the third compound and the LUMO energy level of the fourth compound may be about 0.1 eV to about 1.0 eV.
In one or more embodiments, the absolute value of a difference between the HOMO energy level of the second compound and the HOMO energy level of the fourth compound may be 1.25 eV or less (for example, about 0.2 eV to about 1.25 eV), and/or the absolute value of a difference between the HOMO energy level of the third compound and the HOMO energy level of the fourth compound may be 1.25 eV or less (for example, about 0.2 eV to about 1.25 eV).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described herein, the balance between holes and electrons injected into the emission layer may be achieved.
In one or more embodiments, the emission layer may include i) a dopant or an emitter (organic compound), ii) at least one host (second compound and/or third compound), and iii) a sensitizer (fourth compound), and the emission layer may be to emit phosphorescence or fluorescence (for example, delayed fluorescence) emitted from the dopant. For example, the sensitizer may not act as the dopant, but instead as an auxiliary dopant that transfers energy to the dopant. As another example, the sensitizer may act as an auxiliary dopant that transfers energy to the dopant and may also act as a dopant that emits light.
The emitted phosphorescence or fluorescence may be blue phosphorescence or blue fluorescence (for example, blue delayed fluorescence). The blue light may have a maximum emission wavelength of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
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.
For example, the light-emitting device may further include at least one selected from 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.
At least one selected from among the first capping layer and the second capping layer may include the organic compound represented by Formula 1.
In one or more embodiments, the light-emitting device may include:
The expression “(interlayer and/or a capping layer) includes an organic compound represented by Formula 1” as used herein may be to refer to that the (interlayer and/or the capping layer) may include one kind of organic compound represented by Formula 1 or two or more different kinds of organic compounds, each represented by Formula 1.
For example, the interlayer and/or the capping layer may include Compound 1 only as the organic compound. Compound 1 may be included in the emission layer of the light-emitting device.
As another example, the interlayer may include, as the organic compound, Compound 1 and Compound 2 as described in more detail herein. Compound 1 and Compound 2 may be included in a substantially identical layer (for example, both (e.g., simultaneously) Compound 1 and Compound 2 may be included in the emission layer), or may be included in different layers (for example, Compound 1 may be included in the emission layer, and Compound 2 may be included in the electron transport region).
The term “interlayer” as used herein refers to a single layer and/or each (e.g., all) of a plurality of layers arranged between the first electrode and the second electrode of the light-emitting device.
According to one or more embodiments, an electronic apparatus includes: the light-emitting device; and a thin-film transistor electrically connected to the light-emitting device. For example, the thin-film transistor may include a source electrode and a drain electrode, and the first electrode of 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 any combination thereof. More details of the electronic apparatus may be referred to the descriptions provided herein.
According to one or more embodiments, an electronic equipment includes the light-emitting device and is at least one selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertisement board, an indoor or outdoor lighting and/or signaling light, 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 microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, a sign, and combinations thereof.
According to one or more embodiments, provided is the organic compound represented by Formula 1. Formula 1 is as described in the present specification.
Synthesis methods of the organic compound may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided herein.
The organic compound may be represented by Formula 1:
An example in which Y1 in Formula 1 is C(Z11)(Z12), wherein Z11 and Z12 are bonded to each other to form a C3-C60 carbocyclic group, may refer to Compound 20:
An example in which Y2 in Formula 1 is N(Z21), wherein Z21 is bonded to ring CY31 via a single bond, may refer to Formula FT2, Compound 5, and/or the like:
An example in which Y2 in Formula 1 is N(Z21), wherein Z21 is bonded to ring CY31 via *—O—*′, may refer to Formula FT2, Compound 8, and/or the like:
An example in which Y2 in Formula 1 is N(Z21), wherein Z21 is bonded to ring CY31 via *—S—*′, and Y3 is N(Z31), wherein Z31 is bonded to ring CY32 via *—S—*′, may refer to Formula FT4, Compound 15, and/or the like:
An example in which Y2 in Formula 1 is N(Z21), wherein Z21 is bonded to ring CY31 via a single bond, and Y3 is N(Z31), wherein Z31 is bonded to ring CY32 via *—Si(T31)(T32)-*′, may refer to Formula FT4, Compound 14, and/or the like:
In one or more embodiments, the organic compound may include at least one nitrogen atom.
In one or more embodiments, in Formula 1, i) X1 may be N(Ar11); ii) X2 may be N(Ar21); or iii) X1 may be N(Ar11), and concurrently X2 may be N(Ar21).
In one or more embodiments, Ar11, Ar12, Ar21, and Ar22 may each independently be a biphenyl group that is unsubstituted or substituted with at least one R10a, a terphenyl group that is unsubstituted or substituted with at least one R10a, a fluorenyl group that is unsubstituted or substituted with at least one R10a, a dibenzofuranyl group that is unsubstituted or substituted with at least one R10a, or a dibenzothiophenyl group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, Ar11, Ar12, Ar21, and Ar22 may each independently be a group represented by any one selected from among Formulae AR1 to AR4:
In one or more embodiments, a group represented by Formula AR1 may be a group represented by any one selected from among Formulae AR11 to AR21:
For example, R10c may be:
In one or more embodiments, i) Y2 may be selected from among O, S, Se, and N(Z21), and Z21 may optionally be bonded to ring CY31 via a single bond, *—O—*, *—S—*′, *—Se—*′, *—C(T21)(T22)-*′, or *—Si(T21)(T22)-*′; ii) Y3 may be selected from among O, S, Se, and N(Z31), and Z31 may optionally be bonded to ring CY32 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T31)(T32)-*′, or *—Si(T31)(T32)-*′; or iii) Y2 may be selected from among O, S, Se, and N(Z21), Y3 may be selected from among O, S, Se, and N(Z31), Z21 may optionally be bonded to ring CY31 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T21)(T22)-*′, or *—Si(T21)(T22)-*′, and Z31 may optionally be bonded to ring CY32 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T31)(T32)-*′, or *—Si(T31)(T32)-*′.
In one or more embodiments, Z21, Z22, Z31, and Z32 may each independently be a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C3-C1 cycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, or a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, ring CY1, ring CY2, and ring CY31 to ring CY33 may each independently be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, or an isoquinoline group. For example, ring CY1, ring CY2, and ring CY31 to ring CY33 may each be a benzene group.
In one or more embodiments, ring CY1, ring CY2, and ring CY31 to ring CY33 may each independently be a 6-membered ring. In one or more embodiments, ring CY1, ring CY2, and ring CY31 to ring CY33 may each independently be a C6 carbocyclic group.
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by any one selected from among Formulae FT1 to FT4:
In one or more embodiments, at least one selected from among Y1 to Y3 in Formula FT1 may be O or S, at least one selected from among Y1, L2, and Y3 in Formula FT2 may be O or S, at least one selected from among Y1, Y2, and L3 in Formula FT3 may be O or S, and at least one selected from among Y1, L2, and L3 in Formula FT4 may be O or S. For example, the organic compound may include at least one O or at least one S.
In one or more embodiments, the organic compound may include at least one deuterium.
In one or more embodiments, R1, R2, and R31 to R33 may each independently be selected from among:
In one or more embodiments, at least one selected from among R31 to R33 may be deuterium.
In one or more embodiments, the organic compound represented by Formula 1 may be represented by Formula 1-1:
In one or more embodiments, a bond between two neighboring atoms selected from among X11 to X14, X21 to X23, Y11 to Y13, Y21 to Y23, and Y31 to Y33 may be a single bond or a double bond.
In one or more embodiments, the organic compound represented by Formula 1 and/or Formula 1-1 may include i) a 6-membered ring formed by X1, X11, X12, B, X14, and X13, ii) a 6-membered ring formed by B, X14, X21, X2, X22, and X23, iii) a 6-membered ring formed by Y1, Y11, Y12, B, Y32, and Y33, iv) a 6-membered ring formed by B, Y12, Y13, Y2, Y21, and Y22, and v) a 6-membered ring formed by B, Y22, Y23, Y3, Y31, and Y32.
In one or more embodiments, ring CY1, ring CY2, and ring CY31 to ring CY33 in Formulae 1 and 1-1 may each be a benzene group.
In one or more embodiments, the organic compound represented by Formula 1 may be represented by Formula 1-2:
In one or more embodiments, the organic compound represented by Formula 1 may be represented by Formula 1-2a, 1-2b, or 1-2c:
The organic compound represented by Formula 1, 1-1, 1-2, 1-2a, 1-2b, or 1-2c includes at least two boron atoms (B) at appropriate or suitable positions and includes at least one heteroatom at an appropriate or suitable position such as X1, X2, and any of Y1 to Y3, and these atoms are connected to each other via a plurality of 6-membered rings, ring CY1, ring CY2, and ring CY31 to ring CY33. In some embodiments, ring CY31 and ring CY32 are bonded to each other via a boron atom (B) and Y1, ring CY32 and ring CY33 are bonded to each other via a boron atom (B) and Y3, and ring CY33 and ring CY31 are bonded to each other via a boron atom (B) and Y2. Therefore, the organic compound may undergo enhancement of a multiple-resonance (MR) aspect and reinforcement of structural rigidity, leading to induction of a distortion aspect. As a result, a local excited state (LE state) and a charge transfer state (CT state) are mixed, and thus, an orbital distribution between a lowest excited singlet state (S1) and a lowest excited triplet state (T1) may be changed. For example, spin-orbit coupling is strengthened, and thus, an inhibitory aspect according to the EI-Sayed rule may be offset, and reverse intersystem crossing (RISC) may be induced. Therefore, the organic compound may concurrently (e.g., simultaneously) have a high photoluminescence quantum yield (PLQY), a high molar extinction coefficient, and low delayed fluorescence lifespan, and the luminescence efficiency and lifespan of a light-emitting device including the organic compound may be improved.
In one or more embodiments, the organic compound may be any one selected from among Compounds 1 to 80:
In one or more embodiments, the second compound may be any one selected from among Compounds ETH1 to ETH100.
In one or more embodiments, the third compound may be any one selected from among Compounds HTH1 to HTH46 and HT-1:
In one or more embodiments, the fourth compound may be any one selected from among Compounds D1 to D10 and PS-1, or may be a compound in which at least one hydrogen included in one of Compounds D1 to D10 and PS-1 is substituted with deuterium:
In the preceding compounds, Ph represents a phenyl group, D represents deuterium, D4 represents substitution with four deuterium atoms, and D5 represents substitution with five deuterium atoms. For example, a group represented by
may be substantially identical to a group represented by
Hereinafter, the structure and manufacturing method of the light-emitting device 10 according to one or more embodiments are described with reference to
In
The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high-work function material that facilitates injection of holes may be used as a material for forming the first electrode 110.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be used as a material for forming the first electrode 110.
The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multilayer structure including a plurality of layers. In one or more embodiments, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer may be arranged above the first electrode 110. The interlayer may include the hole transport region 120, the emission layer 130, and the electron transport region 140.
The interlayer may include one or more suitable organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, and/or the like.
In one or more embodiments, the interlayer may include i) at least two emitting units sequentially stacked between the first electrode 110 and the second electrode 150 and ii) a charge generation layer arranged between the two emitting units. When the interlayer includes the emitting units and the charge generation layer as described herein, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region 120 may have i) a single-layer structure including (e.g., consisting of) a single layer including a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including a plurality of materials that are different from each other, or iii) a multilayer structure including (e.g., consisting of) a plurality of layers including a plurality of materials that are different from each other.
The hole transport region 120 may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
For example, the hole transport region 120 may have a multilayer 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 120 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, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) 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) groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one of (e.g., selected from among) Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of (e.g., selected from among) Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formulae 201 and 202 may each not include groups represented by Formulae CY201 to CY203 and may include at least one selected from among 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) groups represented by Formulae CY201 to CY217.
In one or more embodiments, the hole transport region may include at least one of (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′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), or any combination thereof:
The thickness of the hole transport region 120 may be about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region 120 includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. 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 serve to increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer. The electron blocking layer may serve to prevent or reduce electron leakage 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 120 may further include, in addition to the aforementioned materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly (e.g., substantially uniformly) or non-uniformly (e.g., substantially non-uniformly) dispersed in the hole transport region (for example, in the form of a single layer including (e.g., consisting of) a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the LUMO energy level of the p-dopant may be about −3.5 eV or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including an element EL1 and an element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and/or the like.
In Formula 221,
In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, and/or a (e.g., any suitable) combination thereof, and the element EL2 may be a non-metal, a metalloid, and/or a (e.g., any suitable) combination thereof.
Examples of the metal may include an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); a transition metal (for example, 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 (for example, zinc (Zn), indium (In), tin (Sn), and/or the like); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and/or the like).
Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, and/or the like).
Examples of the compound including the element EL1 and the element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, a metal iodide, and/or the like), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, and/or the like), a metal telluride, or any combination thereof.
Examples of the metal oxide may include a tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, and/or the like), a vanadium oxide (for example, VO, V2O3, VO2, V2O5, and/or the like), a molybdenum oxide (for example, MoO, Mo2O3, MoO2, MoO3, Mo2O5, and/or the like), a rhenium oxide (for example, ReO3, and/or the like), and/or the like.
Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.
Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, Mg12, CaI2, SrI2, and BaI2.
Examples of the transition metal halide may include a titanium halide (for example, TiF4, TiC4, TiBr4, TiI4, and/or the like), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, and/or the like), a hafnium halide (for example, HfF4, HfCl4, HfBr4, Hfl4, and/or the like), a vanadium halide (for example, VF3, VCI3, VBr3, VI3, and/or the like), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, and/or the like), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, and/or the like), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, and/or the like), a molybdenum halide (for example, MoF3, MoClK, MoBr3, MoI3, and/or the like), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, and/or the like), a manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, and/or the like), a technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, and/or the like), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, and/or the like), an Iron(II) halide (for example, FeF2, FeCl2, FeBr2, FeI2, and/or the like), a ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, and/or the like), an osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, and/or the like), a cobalt halide (for example, CoF2, COCl2, CoBr2, CoI2, and/or the like), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, and/or the like), an iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, and/or the like), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, and/or the like), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, and/or the like), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, and/or the like), a Copper(I) halide (for example, CuF, CuCl, CuBr, CuI, and/or the like), a silver halide (for example, AgF, AgCl, AgBr, AgI, and/or the like), and a gold halide (for example, AuF, AuCl, AuBr, AuI, and/or the like).
Examples of the post-transition metal halide may include a zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, and/or the like), an indium halide (for example, Ink3, and/or the like), a tin halide (for example, SnI2, and/or the like), and/or the like.
Examples of the lanthanide metal halide may include 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 may include an antimony halide (for example, SbCl5, and/or the like).
Examples of the metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, and/or the like), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, and/or the like), a transition metal telluride (for example, 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), a post-transition metal telluride (for example, ZnTe, and/or the like), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, and/or the like).
When the light-emitting device 10 is a full-color light-emitting device, the emission layer 130 may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer 130 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 130 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 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
The amount of the dopant in the emission layer 130 may be 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 130 may include a quantum dot.
The emission layer 130 may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer.
The thickness of the emission layer 130 may be 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 (e.g., desired) 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 alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (for example, Compound H55), an 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(carbazol-9-yl)benzene (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:
M(L401)xc1(L402)xc2 Formula 401
For example, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, if (e.g., when) xc1 in Formula 401 is 2 or more, two ring A401 among two or more of L401 may be optionally linked together via T402, which is a linking group, and two ring A402 may be optionally linked together 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 (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, and/or the like), or any combination thereof.
The phosphorescent dopant may include, for example, at least one of (e.g., one or more selected from among) 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.
For example, the fluorescent dopant may include a compound represented by Formula 501:
In one or more embodiments, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, a pyrene group, and/or the like) in which three or more monocyclic groups are condensed together.
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 of (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.
Herein, the delayed fluorescence material 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 the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material may be about 0 eV to about 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 herein range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials 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 (for example, a π electron-rich C3-C60 cyclic group such as a carbazole group) and at least one electron acceptor (for example, 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 including at least two cyclic groups that are condensed with each other while sharing boron (B).
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 130 may include a quantum dot.
The term “quantum dot” as used herein refers to a crystal of a semiconductor compound. Quantum dots may be to emit light of one or more suitable emission wavelengths according to the size of the crystal. Quantum dots may also emit light of one or more suitable emission wavelengths by adjusting the ratio of elements constituting the quantum dots.
The diameter of the quantum dots may be, for example, 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 quantum dot particle crystals. 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 may 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 may include: 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 may include: 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 Ill-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and/or the like.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, Ga2S3, 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 may include: a ternary compound, such as AgInS, AgInS2, AgInSe2, AgGaS, AgGaS2, AgGaSe2, CuInS, CuInS2, CuInSe2, CuGaS2, CuGaSe2, CuGaO2, AgGaO2, AgAlO2, and/or the like; a quaternary compound, such as AgInGaS2, AgInGaSe2, and/or the like; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; 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 may include: a single element, 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 substantially non-uniform concentration in a particle. For example, the preceding formulae refer to types (kinds) of elements included in the compound, wherein the element ratios in the compound may vary. For example, AgInGaS2 may refer to AgInxGa1-xS2 (wherein x is a real number between 0 and 1).
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. In one or more embodiments, 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 a single layer or a multilayer. 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 may be an oxide of a metal or non-metal, a semiconductor compound, and/or a (e.g., any suitable) combination thereof. Examples of the oxide of a metal or non-metal may include: 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 may include: a Group Ill-VI semiconductor compound; a Group II-VI semiconductor compound; a Group Ill-V semiconductor compound; a Group 1-Ill-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof, as described herein. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaS, GaSe, AgGaS, AgGaS2, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
Each element included in a multi-element compound, such as the binary compound and the ternary compound, may be present at a substantially uniform concentration or substantially non-uniform concentration in a particle. For example, the preceding formulae refer to types (kinds) of elements included in the compound, wherein the element ratios in the compound may vary.
The quantum dot may have a full width at half maximum (FWHM) of the emission wavelength spectrum of less than or equal to about 45 nm, less than or equal to about 40 nm, or for example, less than or equal to about 30 nm. When the FWHM of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. In some embodiments, because light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In some embodiments, the quantum dot may be in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.
Because the energy band gap may be controlled or selected by adjusting the size of the quantum dots or the ratio of elements in the quantum dot compound, light of one or more suitable wavelengths may be obtained from the quantum dot-containing emission layer. Therefore, by using the aforementioned quantum dots (using quantum dots of different sizes or having different element ratios in the quantum dot compound), a light-emitting device emitting light of one or more suitable wavelengths may be implemented. For example, the control of the size of the quantum dots or the ratio of elements in the quantum dot compound may be selected to emit red light, green light, and/or blue light. In some embodiments, the size of the quantum dots may be configured to emit white light by combination of light of one or more suitable colors.
The electron transport region 140 may have i) a single-layer structure including (e.g., consisting of) a single layer including a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including a plurality of materials that are different from each other, or iii) a multilayer structure including (e.g., consisting of) a plurality of layers including a plurality of materials that are different from each other.
The electron transport region 140 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 140 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, for each structure, constituting layers are sequentially stacked from the emission layer 130.
The electron transport region 140 (for example, 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.
For example, the electron transport region 140 may include a compound represented by Formula 601.
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
In 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 together via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, the electron transport region 140 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 140 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:
The thickness of the electron transport region 140 may be about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region 140 includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region 140 (for example, an electron transport layer in the electron transport region) may further include, in addition to the aforementioned materials, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
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 140 may include an electron injection layer that facilitates 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-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of materials that are different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of 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 include oxides, halides (for example, 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, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (x is a real number satisfying 0<x<1), or BaxCa1-xO (x is a real number satisfying 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
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) 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, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
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 (for example, 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 (for example, alkali metal halide), ii) a) an alkali metal-containing compound (for example, alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In one or more embodiments, 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, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be uniformly (e.g., substantially uniformly) or non-uniformly (e.g., substantially non-uniformly) dispersed in a matrix including the organic material.
The thickness of the electron injection layer may be 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 range as described herein, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged above the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.
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 multilayer structure including a plurality of layers.
The first capping layer may be arranged outside (and e.g., on) the first electrode 110, and/or the second capping layer may be arranged outside (and e.g., on) the second electrode 150. In one or more embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer, 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, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the emission layer 130 of the light-emitting device 10 may pass through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and through the first capping layer to the outside. Light generated in the emission layer 130 of the light-emitting device 10 may pass through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and through the second capping layer to the outside.
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, such that the luminescence efficiency of the light-emitting device 10 may be increased.
Each of the first capping layer and the second capping layer may include a material having a refractive index of about 1.2 or higher (at 460 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/or 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/or 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/or 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/or the second capping layer may each independently include at least one of (e.g., one or more selected from among) Compounds HT28 to HT33, at least one of (e.g., one or more selected from among) Compounds CP1 to CP6, β-NPB, or any combination thereof:
The electronic apparatus may further include a film. The film may be, for example, an optical member (or a light control component) (for example, 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, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
The light-emitting device 10 may be included in one or more suitable electronic apparatuses. In one or more embodiments, an electronic apparatus including the light-emitting device 10 may be a display apparatus or an authentication apparatus.
The electronic apparatus (for example, a display apparatus) may further include, in addition to the light-emitting device 10, 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 direction in which light emitted from the light-emitting device 10 travels. For example, the light emitted from the light-emitting device 10 may be blue light or white light. A more detailed description of the light-emitting device 10 is provided herein. In one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots 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 film may be arranged among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns 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. In one or more embodiments, 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. In one or more embodiments, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. For example, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include (e.g., may exclude any) quantum dot. A detailed description of the quantum dots is provided herein. The first area, the second area, and/or the third area may each further include a scatterer.
In one or more embodiments, the light-emitting device 10 may be to emit first light, the first area may be to absorb the first light to emit first-1 color light, the second area may be to absorb the first light to emit second-1 color light, and the third area may be to absorb the first light to emit third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device 10. 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 use of the electronic apparatus. Examples of the functional layers may include a touch screen layer and a polarizing layer. 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 using biometric information of a living body (for example, 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 (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, 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 (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting device 10 may be included in one or more suitable electronic equipment.
For example, electronic equipment including the light-emitting device 10 may be at least one of (e.g., one or more selected from among) a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertisement board, an indoor or outdoor lighting and/or signaling light, 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 microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, a sign, and/or a (e.g., any suitable) combination thereof.
Because the light-emitting device 10 has improved luminescence efficiency, improve lifespan, and/or the like, the electronic equipment including the light-emitting device 10 may have high luminance, high resolution, and low power consumption.
The electronic apparatus in
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.
The 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 above the activation layer 220, and the gate electrode 240 may be arranged above the gate insulating film 230.
An interlayer insulating film 250 may be arranged above the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
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, 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 film 290 including an insulating material may be arranged on the first electrode 110. The pixel-defining film 290 may expose a certain region of the first electrode 110, and the interlayer may be formed in the exposed region of the first electrode 110. The pixel-defining film 290 may be a polyimide-based organic film or a polyacrylic organic film. In one or more embodiments, at least some layers of the interlayer may extend to the upper portion of the pixel-defining film 290 and may be arranged in the form of a common layer.
The second electrode 150 may be arranged on the interlayer, and a capping layer 170 may be further 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), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or any combination thereof; and/or a (e.g., any suitable) combination of the inorganic film and the organic film.
The electronic apparatus in
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic equipment 1 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 entirely be around (e.g., 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 printed circuit board, may be electrically connected may be arranged.
In the electronic equipment 1, the length in an x-axis direction and the length in a 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 certain direction according to rotation of at least one wheel. In one or more embodiments, 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 vehicle 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 vehicle body. The exterior of the vehicle 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-view mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 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 an x direction or a −x direction. In one or more embodiments, 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. In one or more embodiments, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 opposite to (e.g., facing) each other.
The side-view mirror 1300 may provide a rear view of the vehicle 1000. The side-view mirror 1300 may be installed on the exterior of the vehicle body. In one or more embodiments, a plurality of side-view mirrors 1300 may be provided. Any one of the plurality of side-view mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side-view 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 apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 opposite to (e.g., facing) each other. The display apparatus 2 may be arranged on at least one selected from among the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, and/or the like. Hereinafter, as the display apparatus 2 according to one or more embodiments, an organic light-emitting display apparatus 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 used in embodiments of the disclosure.
Referring to
Referring to
Referring to
The layers included in the hole transport region 120, the emission layer 130, and the layers included in the electron transport region 140 may be formed in a certain region by using one or more suitable methods such as vacuum deposition, spin coating, casting, a Langmuir-Blodgett (LB) method, ink-jet printing, laser-printing, and laser-induced thermal imaging (LITI).
When the layers included in the hole transport region 120, the emission layer 130, and the layers included in the electron transport region 140 are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed 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 used 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.
The term “C1-C60 heterocyclic group” as used 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. In one or more embodiments, the number of ring-forming atoms of the C1-C60 heterocyclic group may be 3 to 61.
The “cyclic group” as used 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 used herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N=*′ as a ring-forming moiety.
The term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N=*′ as a ring-forming moiety.
In one or more embodiments,
The π electron-rich C3-C60 cyclic group may be i) Group T1, ii) a condensed cyclic group in which two or more of Group T1 are condensed with each other, iii) Group T3, iv) a condensed cyclic group in which two or more of Group T3 are condensed with each other, or v) a condensed cyclic group in which at least one Group T3 and at least one Group T1 are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, and/or the like).
The π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) Group T4, ii) a condensed cyclic group in which two or more of Group T4 are condensed with each other, iii) a condensed cyclic group in which at least one Group T4 and at least one Group T1 are condensed with each other, iv) a condensed cyclic group in which at least one Group T4 and at least one Group T3 are condensed with each other, or v) a condensed cyclic group in which at least one Group T4, at least one Group T1, and at least one Group T3 are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like).
Group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group.
Group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group.
Group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group.
Group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
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 used herein, refer to a monovalent or polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, or the like) that is condensed with (e.g., combined together with) a cyclic group according to the structure of a formula for which the corresponding term is used.
In one or more embodiments, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by those 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 may include a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
Examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group 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 divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group.
The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used 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 include an ethenyl group, a propenyl group, and a butenyl group.
The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a 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 include an ethynyl group and a propynyl group.
The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group that has 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.
The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms, at least one carbon-carbon double bond in the ring thereof, and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms, further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom, and has at least one double bond in the ring thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.
The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.
The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.
Examples of the C6-C60 aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group.
When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has 1 to 60 carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom.
The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has 1 to 60 carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom.
Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, 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, and a naphthyridinyl group.
When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group having two or more rings condensed with each other, only carbon atoms (for example, eight to sixty carbon atoms) as ring-forming atoms, and no aromaticity in its molecular structure if (e.g., when) considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group.
The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more rings condensed with each other, further includes, in addition to carbon atoms (for example, one to sixty carbon atoms), at least one heteroatom as a ring-forming atom, and has no aromaticity in its molecular structure if (e.g., when) considered as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group.
The term “divalent non-aromatic condensed heteropolycyclic group” as used 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 used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group).
The term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein refers to —A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group).
The term “C2-C60 heteroarylalkyl group” as used herein refers to —A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as used herein may be:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl 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.
The term “heteroatom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “transition metal” as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
Throughout the present specification, “D” may represent deuterium, “Ph” may represent a phenyl group, “Me” may represent a methyl group, “Et” may represent an ethyl group, “tert-Bu,” “tBu,” or “But” may represent a tert-butyl group, and “OMe” may represent a methoxy group.
The term “biphenyl group” as used herein refers to “a phenyl group that is 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 used herein refers to “a phenyl group substituted with a biphenyl group.” The term “terphenyl group” as used herein may refer to i) a substituted phenyl group wherein the substituent is a C6-C60 aryl group substituted with a C6-C60 aryl group, and ii) a substituted phenyl group wherein two substituents are present, and each substituent is a C6-C60 aryl group.
* and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
Herein, the x-axis, y-axis, and z-axis 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%, or 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 equipment, 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 or equipment 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 or equipment 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, apparatus, and/or equipment 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, organic compounds according to one or more embodiments and light-emitting devices according to one or more embodiments are described in more detail with reference to the following synthesis examples and examples.
Under an argon atmosphere, N1,N3-di([1,1′:3′,1″-terphenyl]-2′-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 16 mmol), 3-iodo-1,1′-biphenyl-2,2′,3′,4,4′,5,5′,6,6′-d9 (4.7 g, 16 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (P(t-Bu)3, 1.6 mL, 3.8 mmol), and sodium tert-butoxide (Na tBuO, 11.5 g, 120 mmol) were placed in a 2 L flask and then dissolved in 300 mL of o-xylene, and then, the reaction solution was stirred at 140° C. for 2 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from the filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 5-a (white solid, 8.1 g, 65%).
ESI-LCMS for Intermediate 5-a: [M]+: C58H39D9N2. 781.4416.
Under an argon atmosphere, Intermediate 5-a (8.1 g, 10 mmol), 25-bromo-19H-5-oxa-3-thia-1(9,2)-carbazola-2,4(1,3)-dibenzenacyclopentaphane-13,14,15,16,17,18,24,26,44,45,46-d11 (4.7 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 5-b (white solid, 8 g, 70%).
ESI-LCMS for Intermediate 5-b: [M]+: C82H41D20N3OS. 1155.5841
Under an argon atmosphere, Intermediate 5-b (8 g, 7 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 5 (yellow solid, 3.6 g, 45%).
ESI-LCMS for Compound 5: [M]+: C82H37D18B2N3OS. 1169.5434
1H-NMR for Compound 5 (CDCl3): δ=8.22 (m, 4H), 7.43 (t, 2H), 7.32 (m, 12H), 7.12 (m, 8H), 7.01 (s, 2H), 1.32 (s, 27H).
Under an argon atmosphere, Intermediate 5-a (8 g, 10 mmol), 8-bromo-16,18-(epiethane[1,2]diylidene)-20,22-etheno-6,10-(metheno)[1]oxa[5,11]diazacyclotetradecino[5,4-a:11,12-a′]diindole-1,2,3,4,7,9,12,13,14,15,23,24,25,26-d14 (5.2 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 7-b (white solid, 8.8 g, 72%).
ESI-LCMS for Intermediate 7-b: [M]+: C88H41D23N4O. 1215.6524
Under an argon atmosphere, Intermediate 7-b (8 g, 6.5 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 7 (yellow solid, 3 g, 37%).
ESI-LCMS for Compound 7: [M]+: C88H37D21B2N4O. 1229.6107
1H-NMR for Compound 7 (CDCl3): δ=8.17 (m, 4H), 7.47 (t, 2H), 7.24 (m, 12H), 7.05 (m, 8H), 6.88 (s, 2H), 1.38 (s, 27H).
Under an argon atmosphere, N1,N3-di([1,1′:3′,1″-terphenyl]-2′-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 16 mmol), 25-iodo-110H-3,5-dioxa-1(10,2)-phenoxazina-2,4(1,3)-dibenzenacyclopentaphane-13,14,26,44,45,46-d6 (8 g, 16 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 200 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 8-a (white solid, 11 g, 71%).
ESI-LCMS for Intermediate 8-a: [M]+: C70H47D6N3O3. 989.4532
Under an argon atmosphere, Intermediate 8-a (10 g, 10 mmol), 9-(3-iodophenyl-2,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3.9 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 8-b (white solid, 8.2 g, 66%).
ESI-LCMS for Intermediate 8-b: [M]+: C88H46D18N4O3. 1242.6138
Under an argon atmosphere, Intermediate 8-b (8 g, 6.4 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 8 (yellow solid, 2.8 g, 35%).
ESI-LCMS for Compound 8: [M]+: C88H41D17B2N4O3. 1257.5828
1H-NMR for Compound 8 (CDCl3): δ=7.47 (m, 2H), 7.42 (m, 4H), 7.30 (m, 12H), 7.08 (m, 8H), 7.01 (m, 4H), 6.94 (s, 2H), 1.31 (s, 9H).
Under an argon atmosphere, Intermediate 5-a (10 g, 12.8 mmol), 8-iodo-16,18:20,22-diethieno-6,10-(metheno)[1]oxa[5,11]diazacyclotetradecino[5,4-a:11,12-a′]diindole-1,2,3,4,7,9,12,13,14,15,23,24,25,26-d14 (7.4 g, 12.8 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 13-a (white solid, 10 g, 64%).
ESI-LCMS for Intermediate 13-a: [M]+: C88H47D17N4O2. 1225.6113
Under an argon atmosphere, Intermediate 13-a (10 g, 8.2 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 13 (yellow solid, 3.34 g, 33%).
ESI-LCMS for Compound 13: [M]+: C88H41D17B2N4O2. 1241.5811
1H-NMR for Compound 13 (CDCl3): δ=7.45 (m, 2H), 7.40 (m, 4H), 7.27 (m, 12H), 7.06 (m, 8H), 7.00 (m, 4H), 6.98 (s, 2H), 1.28 (s, 9H).
Under an argon atmosphere, N1,N3-di([1,1′:3′,1″-terphenyl]-2′-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 16 mmol), 4-iodo-1,1′-biphenyl-2,3,5,6-d4 (4.5 g, 16 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 200 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 14-a (white solid, 8 g, 64%).
ESI-LCMS for Intermediate 14-a: [M]+: C58H44D4N2. 776.4123
Under an argon atmosphere, Intermediate 14-a (8 g, 10 mmol), 20-iodo-5,5-dimethyl-5H-6,8-(epiethane[1,2]diylidene)-10,12-etheno-18,22-(metheno)benzo[5′,6′][1,4]azasilino[1′,2′:11,12][1]oxa[5,11]diazacyclotetradecino[5,4-a]indole-7,11,13,14,15,16,19,21,25,26,27,28-d12 (6.4 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 14-b (white solid, 8.2 g, 65%).
ESI-LCMS Intermediate 14-b: [M]+: C90H56D14N4OSi. 1264.6214
Under an argon atmosphere, Intermediate 14-b (8 g, 6.3 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 14 (yellow solid, 2.34 g, 29%).
ESI-LCMS for Compound 14: [M]+: C90H52D12B2N4OSi. 1278.4151
1H-NMR for Compound 14 (CDCl3): δ=7.43 (m, 2H), 7.39 (m, 4H), 7.29 (m, 17H), 7.10 (m, 8H), 7.01 (m, 4H), 6.95 (s, 2H), 1.33 (s, 9H).
Under an argon atmosphere, N1,N3-di([1,1′:3′,1″-terphenyl]-2′-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 16 mmol), 9-(3-iodophenyl-2,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.1 g, 16 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 200 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 15-a (white solid, 9.5 g, 68%).
ESI-LCMS for Intermediate 15-a: [M]+: C64H39D12N3. 874.2128
Under an argon atmosphere, Intermediate 15-a (9 g, 10 mmol), 21-iodo-6,8-(epiethane[1,2]diylidene)-10,12-etheno-19,23-(metheno)benzo[5,6][1,4]thiazino[3,4-d]benzo[5,6][1,4]thiazino[4,3-k][1]oxa[5,11]diazacyclotetradecine-20,22,26,27,28,29-d6 (6.4 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 15-b (white solid, 8.2 g, 60%).
ESI-LCMS for Intermediate 15-b: [M]+: C94H49D18N5OS2. 1363.5954
Under an argon atmosphere, Intermediate 15-b (8 g, 5.9 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 15 (yellow solid, 1.9 g, 23%).
ESI-LCMS for Compound 15: [M]+: C94H45D16B2N5OS2. 1377.5514
1H-NMR for Compound 15 (CDCl3): δ=7.41 (m, 2H), 7.36 (m, 8H), 7.25 (m, 17H), 7.07 (m, 8H), 7.00 (m, 4H), 6.90 (s, 2H), 1.35 (s, 9H).
Under an argon atmosphere, Intermediate 5-a (10 g, 12.7 mmol), 3′-([1,1′-biphenyl]-2-yl)-5′-iodospiro[fluorene-9,5′-3-aza-1(9,2)-carbazola-2,4(1,3)-dibenzenacyclopentaphane]-3′,4′,4′,4′,5′,5′,6′,6′,7′,8′-d10 (10 g, 12.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 20-a (white solid, 11.8 g, 65%).
ESI-LCMS for Intermediate 20-a: [M]+: C107H59D19N4. 1437.7477
Under an argon atmosphere, Intermediate 20-a (10 g, 7 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 20 (yellow solid, 2.4 g, 24%).
ESI-LCMS for Compound 20: [M]+: C107H55D17B2N4. 1451.7020
1H-NMR for Compound 20 (CDCl3): δ=8.10 (d, 1H), 7.90 (d, 2H), 7.56 (d, 2H), 7.45 (m, 5H), 7.41 (m, 6H), 7.35 (d, 2H), 7.29 (m, 12H), 7.17 (t, 2H), 7.05 (m, 10H), 7.01 (m, 1H), 6.95 (s, 2H), 6.90 (s, 1H), 1.36 (s, 9H).
Under an argon atmosphere, Intermediate 5-a (10 g, 12.7 mmol), 25-iodo-5,5-dimethyl-14,45-diphenyl-19H-3-oxa-5-sila-1 (9,2)-carbazola-2,4(1,3)-dibenzenacyclopentaphane-13,15,16,17,18,24,26,44,46-d9 (6.8 g, 12.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 37-a (white solid, 11.5 g, 66%).
ESI-LCMS for Intermediate 37-a: [M]+: C104H73D18N3OSi. 1443.8062
Under an argon atmosphere, Intermediate 37-a (10 g, 7 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 37 (yellow solid, 2.2 g, 22%).
ESI-LCMS for Compound 37: [M]+: C104H69D16B2N3OSi. 1457.7781
1H-NMR for Compound 37 (CDCl3): δ=7.41 (s, 4H), 7.35 (m, 22H), 7.09 (m, 8H), 7.03 (s, 2H), 1.36 (s, 9H), 1.23 (s, 18H), 0.66 (s, 6H)
Under an argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (10 g, 22 mmol), 3-iodo-1,1′-biphenyl-2,2′,3′,4,4′,5,5′,6,6′-d9 (6.3 g, 16 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and then dissolved in 300 mL of o-xylene, and then, the reaction solution was stirred at 140° C. for 2 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 45-a (white solid, 10.4 g, 77%).
ESI-LCMS for Intermediate 45-a: [M]+: C40H25D9BrN. 616.2421.
Under an argon atmosphere, Intermediate 45-a (10 g, 16 mmol), dibenzo[b,d]furan-1-amine (3 g, 16 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 45-b (white solid, 8.3 g, 67%).
ESI-LCMS for Intermediate 45-b: [M]+: C56H41D9N2O. 775.4534
Under an argon atmosphere, Intermediate 45-b (8 g, 10 mmol), 6-([1,1′:3′,1″-terphenyl]-2′-yl-4′,5′,6′-d3)-15-bromo-34,56-di-tert-butyl-2,4-dioxa-6-aza-1,3,5(1,3)-tribenzenacyclohexaphane-14,16,35,36,55-d5 (7.3 g, 10 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 45-c (white solid, 9 g, 65%).
ESI-LCMS for Intermediate 45-c: [M]+: C100H72D17N3O3. 1396.8004
Under an argon atmosphere, Intermediate 45-c (9 g, 6.4 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 45 (yellow solid, 3.5 g, 39%).
ESI-LCMS for Compound 45: [M]+: C100H68D15B2N3O3. 1410.7667
1H-NMR for Compound 45 (CDCl3): δ=7.98 (d, 1H), 7.53 (s, 2H), 7.41 (m, 3H), 7.32 (m, 10H), 7.24 (m, 9H), 7.11 (m, 2H), 7.04 (m, 4H), 7.00 (s, 2H), 6.75 (s, 1H), 1.44 (s, 18H), 1.32 (s, 9H), 1.21 (s, 9H)
Under an argon atmosphere, N-([1,1′-biphenyl]-3-yl-d9)-N-(3-bromo-5-(tert-butyl)phenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (10 g, 16 mmol), dibenzo[b,d]thiophen-1-amine (3.2 g, 12.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 48-a (white solid, 9 g, 77%).
ESI-LCMS for Intermediate 48-a: [M]+: C52H33D9N2S. 735.3668
Under an argon atmosphere, Intermediate 48-a (10 g, 12.7 mmol), 4-([1,1′:3′,1″-terphenyl]-2′-yl-4′,5′,6′-d3)-35-iodo-15-isopropyl-2-oxa-6-selena-4-aza-1,3,5(1,3)-tribenzenacyclohexaphane-14,16,34,36,54,55-d6 (9.5 g, 12.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 48-b (white solid, 10.7 g, 60%).
ESI-LCMS for Intermediate 48-b: [M]+: C95H61D18N3OSSe. 1407.6212
Under an argon atmosphere, Intermediate 48-b (109 g, 7.1 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 48 (yellow solid, 1.9 g, 19%).
ESI-LCMS for Compound 48: [M]+: C95H57D16B2N3OSSe. 1421.5517
1H-NMR for Compound 48 (CDCl3): δ=8.45 (d, 1H), 7.93 (d, 1H), 7.59 (i, 5H), 7.41 (s, 2H), 7.36 (m, 16H), 7.21 (s, 1H), 7.06 (i, 8H), 7.00 (s, 2H), 2.88 (m, 1H), 1.33 (s, 9H), 1.21 (s, 18H), 1.12 (s, 6H)
Under an argon atmosphere, N-([1,1′-biphenyl]-3-yl-d9)-N-(3-bromo-5-(tert-butyl)phenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (10 g, 16 mmol), [1,1′:4′,1″-terphenyl]-2′-amine (3.9 g, 12.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 53-a (white solid, 9 g, 67%).
ESI-LCMS for Intermediate 53-a: [M]+: C62H47D9N2. 837.5001
Under an argon atmosphere, Intermediate 53-a (9 g, 10.7 mmol), 4-([1,1′:3′,1″-terphenyl]-2″-yl-4′,5′,6′-d3)-35-iodo-14,55-diphenyl-2-oxa-6-thia-4-aza-1,3,5(1,3)-tribenzenacyclohexaphane-15,16,34,54-d4 (8.7 g, 10.7 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 53-b (white solid, 10.2 g, 63%).
ESI-LCMS Intermediate 53-b: [M]+: C110H71D16N3OS. 1513.7618
Under an argon atmosphere, Intermediate 53-b (10 g, 6.6 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 53 (yellow solid, 2.1 g, 21%).
ESI-LCMS for Compound 53: [M]+: C110H66D15B2NOS. 1528.7271
1H-NMR for Compound 53 (CDCl3): δ=7.92 (d, 1H), 7.75 (d, 2H), 7.51 (m, 8H), 7.41 (s, 2H), 7.36 (m, 25H), 7.08 (m, 6H), 7.01 (s, 2H), 6.91 (d, 1H), 1.32 (s, 9H), 1.24 (s, 9H)
Under an argon atmosphere, Intermediate 5-a (10 g, 13 mmol), 15-iodo-35,55-diphenyl-2,4,6-trithia-1,3,5(1,3)-tribenzenacyclohexaphane-14,16,34,36,54,56-d6 (7.9 g, 13 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 74-a (white solid, 10 g, 61%).
ESI-LCMS for Intermediate 74-a: [M]+: C88H49D17N2S3. 1263.5560
Under an argon atmosphere, Intermediate 74-a (10 g, 7.9 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 74 (yellow solid, 3.5 g, 32%).
ESI-LCMS for Compound 74: [M]+: C88H45D15B2N2S3. 1277.4937
1H-NMR for Compound 74 (CDCl3): δ=8.20 (d, 4H), 7.51 (m, 10H), 7.43 (m, 12H), 7.31 (m, 2H), 7.07 (m, 8H), 1.27 (s, 9H)
Under an argon atmosphere, Intermediate 15-a (10 g, 11 mmol), 6-([1,1′:3′,1″-terphenyl]-2″-yl)-35-bromo-2,4-dioxa-6-aza-1,3,5(1,3)-tribenzenacyclohexaphane-14,15,16,34,36,54,55,56-d8 (6.8 g, 11 mmol), Pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (1.4 g, 15 mmol) were placed in a 1 L flask and then dissolved in 100 mL of xylene, and then, the reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect an organic layer, and then, the organic layer was dried with MgSO4 and filtered. The solvent was removed from filtrate under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing solvents, to obtain Intermediate 80-a (white solid, 11 g, 73%).
ESI-LCMS for Intermediate 80-a: [M]+: C100H54D20N4O2. 1382.7727
Under an argon atmosphere, Intermediate 80-a (11 g, 8 mmol) was placed in a 1 L flask and then dissolved in 200 mL of o-dichlorobenzene, and then, BBr3 (2 equiv.) was added. The reaction solution was stirred at 140° C. for 12 hours. After cooling the mixture, triethylamine was added to terminate the reaction and the solvent was removed under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel by using CH2Cl2 and hexane as developing agents, to obtain Compound 80 (yellow solid, 3 g, 27%).
ESI-LCMS for Compound 80: [M]+: C100H50D18B2N4O2. 1396.6768
1H-NMR for Compound 80 (CDCl3): δ=8.23 (d, 4H), 8.19 (d, 2H), 7.56 (m, 2H), 7.38 (m, 1H), 7.44 (m, 12H), 7.36 (m, 6H), 7.22 (m, 8H), 7.14 (m, 4H), 7.00 (m, 2H), 1.29 (s, 9H) Evaluation Example 1
The highest occupied molecular orbital (HOMO) energy level, absorption wavelength (λabs) in solution, emission wavelength (λemi) in solution, molar extinction coefficient (s), photoluminescence quantum yield (PLQY), and delayed fluorescence lifespan (TD) of each of Compounds 5, 7, 8, 13, 14, 15, 20, 37, 45, 48, 53, 74, and 80 and Comparative Compounds CE1 to CE4, which were synthesized in the preceding synthesis examples, were measured, and results thereof are shown in Table 1.
The HOMO energy level was measured by using the Smart Manager software of the SP2 electrochemical workstation from ZIVE LAB.
The absorption wavelength and molar extinction coefficient in solution was measured by using the Labsolution UV-Vis software in such a state that the UV-1800 UV/Visible Scanning Spectrophotometer from SHIMADZU was equipped with a deuterium/tungsten-halogen light source and a silicon photodiode.
The emission wavelength in solution was measured by using the FluorEssence software in such a state that a xenon light source and a monochromator were mounted on the HORIBA fluoromax+ spectrometer.
PLQY was measured by using PLQY measurement software in which a xenon light source, a monochromator, a photonic multi-channel analyzer, and an integrating sphere were mounted on a Quantaurus-QY Absolute PL quantum yield spectrometer from Hamamatsu.
The delayed fluorescence lifespan was measured at 300 K by using a fluorescence lifespan measurement device (C11367-01) from Hamamatsu.
TD
From Table 1, it was confirmed that each of Compounds 5, 7, 8, 13, 14, 15, 20, 37, 45, 48, 53, 74 and 80, which are represented by Formula 1, had a higher PLQY, a higher molar extinction coefficient, and lower delayed fluorescence lifespan than each of Comparative Compounds CE1 to CE4 that are not represented by Formula 1. Therefore, the compound represented by Formula 1 has high luminescence efficiency and emits prompt delayed fluorescence, and thus, is suitable for use as a thermally activated delayed fluorescence (TADF) material.
As an anode, a glass substrate (product of Corning Inc.) with a 15 ohm per square centimeter (0/cm2) (1,200 angstrom (A)) indium tin oxide (ITO) electrode formed thereon was cut to a size of 50 millimeter (mm)×50 mm×0.7 mm, sonicated by using isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.
NPD was vacuum-deposited on the anode to form a hole injection layer having a thickness of 300 Å. HT6 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å. CzSi was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å.
A host mixture in which ETH2 (second compound) and HT-1 (third compound) were mixed at a ratio of 1:1, PS-1 (fourth compound, sensitizer), and Compound 5 (organic Compound) were vacuum-co-deposited on the electron blocking layer at a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å.
TSPO1 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 200 Å. TPBi was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å. LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then, Al was vacuum-deposited thereon to form a second electrode having a thickness of 3,000 Å, thereby forming an LiF/Al electrode. P4 was vacuum-deposited on the second electrode to form a capping layer having a thickness of 700 Å, thereby completing manufacture of a light-emitting device.
Light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of Compound 5 in forming the emission layer.
The driving voltage, luminescence efficiency, emission wavelength, lifespan, and color purity (CIEy coordinate) of each of the light-emitting devices manufactured in Examples 1 to 13 and Comparative Examples 1 to 4 were each measured at a current density of 10 milliampere per square centimeter (mA/cm2) by using the V7000 OLED IVL Test System (Polaronix), and results thereof are shown in Table 2. Lifespan (T95) in Table 2 is a measure of the time (Hr) taken until the luminance reaches 95% relative to the initial luminance, and is expressed as a relative value based on the lifespan of Comparative Example 1.
From Table 2, it was confirmed that Examples 1 to 13 respectively employing Compounds 5, 7, 8, 13, 14, 15, 20, 37, 45, 48, 53, 74 and 80, which are represented by Formula 1 and have high PLOY values, high molar extinction coefficients, and low delayed fluorescence lifespan characteristics, each had a higher luminescence efficiency and a longer lifespan than Comparative Examples 1 to 4 respectively employing Comparative Compounds CE1 to CE4 that are not represented by Formula 1.
Without being bound by any particular theory, it is believed that the organic compound represented by Formula 1 undergoes enhancement of a multiple-resonance (MR) effect and reinforcement of structural rigidity, leading to induction of a distortion effect. As a result, an local excited state (LE state) and a charge transfer state (CT state) are mixed, and thus, an orbital distribution between a lowest excited singlet state (S1) and a lowest excited triplet state (T1) may be changed. Therefore, spin-orbit coupling is strengthened, and thus, an inhibitory aspect according to the EI-Sayed rule may be offset, and reverse intersystem crossing (RISC) may be induced. For example, the organic compound may concurrently (e.g., simultaneously) have a high photoluminescence quantum yield (PLQY), a high molar extinction coefficient, and low delayed fluorescence lifespan, and the luminescence efficiency and lifespan of a light-emitting device including the organic compound may be improved.
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 |
|---|---|---|---|
| 10-2024-0003122 | Jan 2024 | KR | national |
