Patent Application
20240341187
This application claims priority to and benefits of Korean Patent Application No. 10-2023-0039300 under 35 U.S.C. § 119, filed on Mar. 24, 2023, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to a light-emitting device including a condensed cyclic compound, an electronic apparatus including the light-emitting device, and the condensed cyclic compound.
Light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed.
In a light-emitting device, a first electrode may be located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode may be arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.
It is to be understood that this background of the technology section is, in part, intended to provide useful background for understanding the technology. However, this background of the technology section may also include ideas, concepts, or recognitions that were not part of what was known or appreciated by those skilled in the pertinent art prior to a corresponding effective filing date of the subject matter disclosed herein.
Embodiments include a light-emitting device including a condensed cyclic compound, an electronic apparatus including the light-emitting device, and the condensed cyclic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the embodiments of the disclosure.
According to embodiments, a light-emitting device may include a first electrode,
In Formulae 1 and 2,
In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
In an embodiment, the emission layer may include the condensed cyclic compound represented by Formula 1.
In an embodiment, the emission layer may include a host and a dopant, and the dopant may include the condensed cyclic compound represented by Formula 1.
In an embodiment, the host may include a first host containing at least one electron donating group, and a second host containing at least one electron withdrawing group.
In an embodiment, the emission layer may emit blue light.
Embodiments provide an electronic apparatus which may include the light-emitting device.
In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
Embodiments provide an electronic equipment which may include a light-emitting device.
In an embodiment, the electronic equipment is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Embodiments provide a condensed cyclic compound which may be represented by Formula 1, which is described herein.
In an embodiment, the condensed cyclic compound may include at least one deuterium.
In an embodiment, X1 may be N(R5), and X2 may be N(R6).
In an embodiment, X1 and X2 may be identical to each other, and (R2)a2 and (R3)a3 may be identical to each other.
In an embodiment, the condensed cyclic compound may have a symmetric structure.
In an embodiment, R1 may be a group represented by Formula 2.
In an embodiment, R1 to R6 may each independently be:
In an embodiment, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-5, which are explained below.
In an embodiment, R2, R3, R5, and R6 may each independently be a group represented by one of Formulae 2-1 to 2-11, which are explained below.
In an embodiment, the condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 162, which are explained below.
It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purpose of limitation, and the disclosure is not limited to the embodiments described above.
The above and other aspects and features of the disclosure will be more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:
The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like reference numbers and/or like reference characters refer to like elements throughout.
In the description, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.
In the description, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.
As used herein, the expressions used in the singular such as “a,” “an,” and “the,” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.
In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group of” for the purpose of its meaning and interpretation. For example, “at least one of A and B” may be understood to mean “A, B, or A and B.” When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.
It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.
The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component 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, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within +20%, +10%, or +5% of the stated value.
It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.
Embodiments provide a light-emitting device which may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and a condensed cyclic compound represented by Formula 1:
In Formulae 1 and 2,
In an embodiment, the condensed cyclic compound may include at least one deuterium.
In an embodiment, at least one of R1 and R6 may include deuterium. In an embodiment, at least one of R1 to R6 may be deuterium.
In an embodiment, X1 may be N(R5), and X2 may be N(R6).
In an embodiment, X1 and X2 may be identical to each other. In embodiments, X1 and X2 may be different from each other.
In an embodiment, (R2)a2 and (R3)a3 may be identical to each other. In embodiments, (R2)a2 and (R3)a3 may be different from each other.
In an embodiment, X1 and X2 may be identical to each other, and (R2)a2 and (R3)a3 may be identical to each other.
In an embodiment, the condensed cyclic compound may have a symmetric structure. In embodiments, the condensed cyclic compound may have a symmetric structure with respect to a plane including a dotted line while being perpendicular to a plane including B, X1, and X2.
In an embodiment, R1 may be a group represented by Formula 2. For example, R1 may be a group represented by Formula 2, and R2 and R3 may each not be a group represented by Formula 2.
In an embodiment, R2 or R3 may be a group represented by Formula 2. For example, R2 or R3 may be a group represented by Formula 2, and R1 may not be a group represented by Formula 2.
In an embodiment, R1 to R6 may each independently be:
In an embodiment, R1 to R6 may each independently be:
In an embodiment, R1 to R6 may each independently be:
In an embodiment, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-5:
In Formulae 1-1 to 1-5,
In an embodiment, R2, R3, R5, and R6 may each independently be a group represented by one of Formulae 2-1 to 2-11:
In Formulae 2-1 to 2-11,
In an embodiment, the condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 162:
The condensed cyclic compound includes at least one group represented by Formula 2 as a substituent of a structure represented by Formula 1, and in embodiments, at least one of R1 to R3 may each independently be a group represented by Formula 2. The group represented by Formula 2 does not form a complete resonance structure as in anthracene, and thus, when introduced into the structure represented by Formula 1, the overall resonance tendency may be lowered in comparison to when anthracene is introduced, and the suppression of Dexter energy transfer may be maximized since the group represented by Formula 2 is a bulky substituent, which may result in improved stability of a material.
Thus, the condensed cyclic compound may enhance color purity and driving voltage of a light-emitting device. In a light-emitting device that includes the condensed cyclic compound, energy may be readily transferred from a host, which leads to improved lifespan characteristics.
Methods of synthesizing the condensed cyclic compound represented by Formula 1 may be readily recognized by those of ordinary skill in the art with reference to Synthesis Examples and Examples, which will be described below.
At least one of the condensed cyclic compound represented by Formula 1 may be used in a light-emitting device (for example, an organic light-emitting device). Accordingly, embodiments provide a light-emitting device which may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and the condensed cyclic compound represented by Formula 1 as described herein.
In an embodiment,
In embodiments, the interlayer may include the condensed cyclic compound represented by Formula 1.
In embodiments, the emission layer may include the condensed cyclic compound represented by Formula 1.
In embodiments, the emission layer may include a host and a dopant, and the dopant may include the condensed cyclic compound represented by Formula 1.
In embodiments, the dopant may be a phosphorescent dopant or a delayed fluorescence dopant.
In embodiments, the host may include a first host containing at least one electron donating group, and a second host containing at least one electron withdrawing group.
In embodiments, the emission layer may further include a sensitizer.
In embodiments, the emission layer may include a delayed fluorescence material.
In embodiments, the emission layer may emit blue light.
In embodiments, the condensed cyclic compound represented by Formula 1 may be a delayed fluorescence material.
In embodiments, the condensed cyclic compound included in the emission layer may be an emitter.
In an embodiment, the emission layer may further include a first host and a second host, and the first host may be a hole transporting compound containing at least one electron donating group, and the second host may be an electron transporting compound containing at least one electron withdrawing group.
In an embodiment, the emission layer may further include a third compound, and the third compound may be a metal-containing compound.
In an embodiment, the third compound may serve as a sensitizer, for example, a phosphorescent sensitizer.
In an embodiment, the third compound may not emit light.
The emission layer may further include at least one of an auxiliary dopant and a sensitizer.
In embodiments, the auxiliary dopant and the sensitizer may each independently be an organometallic compound including platinum and a tetradentate ligand bonded to platinum, and the tetradentate ligand may include a carbene moiety chemically bonded to platinum. For example, the auxiliary dopant and/or the sensitizer may include the third compound.
In an embodiment, the first host and the second host may serve as an exciplex host.
In the specification, the term “electron donating group” may refer to any moiety with the ability to provide electrons, and for example, may be a π electron-rich C3-C60 cyclic group or an amine group, but the disclosure is not limited thereto, or the term may refer to a cyclic group that is not a π electron-depleted nitrogen-containing C1-C60 cyclic group.
In the specification, the term “electron withdrawing group” may refer to any moiety with the ability to withdraw electrons. For example, the electron withdrawing group may be, but is not limited to, —F, —CFH2, —CF2H, —CF3, —CN, —NO2, a π electron-depleted nitrogen-containing C1-C60 cyclic group, or any combination thereof.
A light emission path of the light-emitting device according to embodiments of the disclosure may be as follows: the first host and the second host form an exciton (first operation), the energy of the exciton is transferred to the third compound (second operation), and energy is transferred from the third compound to the organometallic compound satisfying Formula 1 (third operation).
In an embodiment, an amount of the third compound may be in a range of about 0 parts by weight to about 50 parts by weight, with respect to a total of 100 parts by weight of the emission layer.
In an embodiment, the first host may include at least one carbazole moiety, and the second host may include at least one azine moiety.
In an embodiment, the first host may be represented by Formula 301-1A or Formula 301-2A:
In Formulae 301-1A and 301-2A,
In an embodiment, the first host may include, but is not limited to, at least one of Compounds HTH1 to HTH56:
In an embodiment, the second host may be represented by Formula 302:
In Formula 302,
In an embodiment, the second host may include, but is not limited to, at least one of Compounds ETH1 to ETH92:
In an embodiment, the third compound may be represented by Formula 401A:
M401(L401)xc1(L402)xc2 [Formula 401A]
In Formulae 401A and 402A to 402D,
In an embodiment, the compound represented by Formula 401A may be a carbene complex.
The term “carbene complex” as used herein may be a complex which includes a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand may be a bond between the metal and a carbon atom of a carbene moiety.
In an embodiment, the sensitizer may include the compound represented by Formula 401A.
In an embodiment, the third compound may be, but is not limited to, one of Compounds PD1 to PD41:
In an embodiment, R301 to R303, R304a to R306a, R304b to R306b, and R311 to R314 in Formulae 301-1A and 301-2A, R321 to R326 in Formula 302, and R401 to R408 in Formulae 401A and 402A to 402D may each independently be:
In embodiments, R301 to R303, R304a to R306a, R304b to R306b, and R311 to R314 in Formulae 301-1A and 301-2A, R321 to R326 in Formula 302, and R401 to R408 in Formulae 401A and 402A to 402D may each independently be:
In Formulae 9-1 to 9-61 and 10-1 to 10-348, * indicates a binding site to a neighboring atom, Ph refers to a phenyl group, and TMS refers to a trimethylsilyl group, and
In embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may contact (e.g., directly contact) the emission layer.
In embodiments, the light-emitting device may include a capping layer arranged outside the first electrode or outside the second electrode.
For example, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, and the condensed cyclic compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer. The first capping layer and the second capping layer may be the same as described herein.
In an embodiment, the light-emitting device may include:
The expression “(an interlayer and/or a capping layer) includes a condensed cyclic compound” as used herein may be construed as “(an interlayer and/or a capping layer) may include one type of condensed cyclic compound represented by Formula 1 or two different types of condensed cyclic compounds represented by Formula 1.”
For example, the interlayer and/or the capping layer may include Compound 1 only as the condensed cyclic compound. In an embodiment, Compound 1 may be present in the emission layer of the light-emitting device. In embodiments, the interlayer may include, as the condensed cyclic compounds, Compound 1 and Compound 2. In an embodiment, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
The term “interlayer” as used herein may be a single layer and/or all layers between the first electrode and the second electrode of the light-emitting device.
According to embodiments, an electronic apparatus may include the light-emitting device as described above. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In embodiments, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic apparatus may be the same as described herein.
According to embodiments, an electronic equipment including the light-emitting device may be provided, in which the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a 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. In embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (AI), 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 structure consisting of a single layer or a structure including multiple layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, and the like.
In embodiments, the interlayer 130 may include at least two emitting units stacked between the first electrode 110 and the second electrode 150 and at least one charge generation layer disposed between the at least two emitting units. When the interlayer 130 includes the emitting units and the at least one charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
In an embodiment, the hole transport region may have a multi-layered 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, in which constituent layers of each structure may be stacked from the first electrode 110 in its respectively stated order, but the structure of the hole transport region is not limited thereto.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In Formulae 201 and 202,
In an embodiment, Formulae 201 and 202 may each include at least one of groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each independently be the same as described in connection with R10a as described herein, rings CY201 to CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described herein.
In an embodiment, in Formulae CY201 to CY217, rings CY201 to CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of groups represented by Formulae CY201 to CY203.
In embodiments, the compound represented by Formula 201 may include at least one of groups represented by Formulae CY201 to CY203 and at least one of groups represented by Formulae CY204 to CY217.
In embodiments, in Formula 201, xa1 may be 1, R201 may be one of groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one of groups represented by Formulae CY204 to CY207.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY203.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY203, and may each independently include at least one of groups represented by Formulae CY204 to CY217.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY217.
In an embodiment, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may serve to increase light-emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron-blocking layer may serve to prevent 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 may include, in addition to the materials as described above, a charge generation material for the improvement of conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge generation material).
The charge generation material may be, for example, a p-dopant.
In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of equal to or less than about-3.5 eV.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
Examples of a quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of a cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
In Formula 221,
In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Examples of a metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or the like); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), 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), or the like); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), or the like); 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), or the like); and the like.
Examples of a metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Examples of a non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, or the like), and the like.
For example, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, or the like), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, or the like), a metal telluride, or any combination thereof.
Examples of a metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, or the like), a vanadium oxide (e.g., VO, V2O3, VO2, V2O5, or the like), a molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, or the like), a rhenium oxide (e.g., ReO3 or the like), and the like.
Examples of a metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and the like.
Examples of an alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
Examples of an alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and the like.
Examples of a transition metal halide may include a titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, or the like), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, or the like), a hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, or the like), a vanadium halide (for example, VF3, VCl3, VBr3, VI3, or the like), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, or the like), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, or the like), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, or the like), a molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, or the like), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, or the like), a manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, or the like), a technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, or the like), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, or the like), an iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, or the like), a ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, or the like), an osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, or the like), a cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, or the like), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, or the like), an iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, or the like), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, or the like), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, or the like), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, or the like), a copper halide (for example, CuF, CuCl, CuBr, CuI, or the like), a silver halide (for example, AgF, AgCl, AgBr, AgI, or the like), a gold halide (for example, AuF, AuCl, AuBr, AuI, or the like), and the like.
Examples of a post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, or the like), an indium halide (e.g., InI3 or the like), a tin halide (e.g., SnI2 or the like), and the like.
Examples of a lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3 SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
Examples of a metalloid halide may include an antimony halide (e.g., SbCl5 or the like) and the like.
Examples of a metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, or the like), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, or the like), a transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, or the like), a post-transition metal telluride (e.g., ZnTe or the like), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, or the like), and the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other, to emit white light. In embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials may be mixed with each other in a single layer, to emit white light.
The emission layer 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 may be in a range of about 0.01 parts by weight to about 15 parts by weight with respect to 100 parts by weight of the host.
In embodiments, the emission layer may include a quantum dot.
In embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or as a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer 15 is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host may further include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 [Formula 301]
In Formula 301,
In an embodiment, in Formula 301, when xb11 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.
In embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In embodiments, the host may include: one of Compounds H1 to H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN); 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN); 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP); 1,3-di-9-carbazolylbenzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
The phosphorescent dopant may include at least one transition metal as a core 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 an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
M(L401)xc1(L402)xc2 [Formula 401]
In Formulae 401 and 402,
For example, in Formula 402, X401 may be nitrogen and X402 may be carbon, or X401 and X402 may each be nitrogen.
In embodiments, in Formula 401, when xc1 is 2 or more, two rings A401 among two or more of L401 may optionally be linked to each other via T402, which is a linking group, or two rings A402 among two or more of L401 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as described in connection with T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, or the like), or any combination thereof.
The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
In an embodiment, in Formula 501, Ar501 may include a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, or the like) in which three or more monocyclic groups are condensed together.
In embodiments, in Formula 501, xd4 may be 2.
In an embodiment, the fluorescent dopant may include: one of Compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:
The emission layer may include a delayed fluorescence material.
In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may serve as a host or as a dopant depending on the types of other materials included in the emission layer.
In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be in a range of 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 above 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.
For example, the delayed fluorescence material may include a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, or a Ir electron-deficient nitrogen-containing C1-C60 cyclic group, and the like), and a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other while sharing boron (B).
Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF14:
The emission layer may include quantum dots.
In the specification, a “quantum dot” may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to a size of the crystal.
The diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any similar process.
The wet chemical process is a method of growing a quantum dot particle crystal by mixing a precursor material with an organic solvent. When the crystal grows, the organic solvent may naturally serve as a dispersant coordinated on the surface of the quantum dot crystal and may control the growth of the crystal. Thus, the wet chemical method may be more readily performed than the vapor deposition process such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE)), and the growth of quantum dot particles may be controlled through a low-cost process.
The quantum dots 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 a Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, 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, or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or the like; or any combination thereof.
Examples of a Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, 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, or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or the like; or any combination thereof. In embodiments, a Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of a Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, or the like; a ternary compound, such as InGaS3, InGaSe3, or the like; or any combination thereof.
Examples of a Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, or the like; or any combination thereof.
Examples of a 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, or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, or the like; or any combination thereof.
Examples of a Group IV element or compound may include: a single element material, such as Si, Ge, or the like; a binary compound, such as SiC, SiGe, or the like; or any combination thereof.
Each element included in a multi-element compound, such as a binary compound, a ternary compound, and a quaternary compound, may be present at a uniform concentration or at a non-uniform concentration in a particle.
In embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. For example, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may serve as a protective layer that prevents chemical denaturation of the core to maintain semiconductor characteristics, and/or may serve as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be single layered or multi-layered. The interface between the core and the shell may have a concentration gradient in which the concentration of a material present in the shell decreases toward the core.
Examples of a material forming the shell of the quantum dot may include a metal oxide, a metalloid oxide, or a non-metal oxide, a semiconductor compound, or any combination thereof. Examples of a metal oxide, a metalloid oxide, or a non-metal oxide may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; or any combination thereof. As described herein, examples of the semiconductor compound 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; or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum of less than or equal to about 45 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be less than or equal to about 40 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be less than or equal to about 30 nm. When the FWHM of the quantum dot is within the above range, color purity or color reproducibility may be improved. Light emitted through the quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
In an embodiment, the quantum dot may be in, for example, a spherical form, a pyramidal form, a multi-arm form, or a cubic form, or the quantum dot may be in the shape of nanoparticles, a nanotube, a nanowire, a nanofiber, or a nanoplate particle.
By adjusting the size of the quantum dot, the energy band gap may be adjusted, and thus, light of various wavelengths may be obtained in the quantum dot emission layer. Thus, by using quantum dots with difference sizes, a light-emitting device that emits light of various wavelengths may be realized. In embodiments, the size of the quantum dot may be selected so that red light, green light, and/or blue light may be emitted. The size of the quantum dot may be configured to emit white light by combination of light of various colors.
The electron transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a structure including multiple layers including different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, a buffer layer/electron transport layer/electron injection layer structure, or the like, in which constituent layers of each structure may be stacked from the emission layer.
The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 [Formula 601]
In Formula 601,
In an embodiment, in Formula 601, when xe11 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.
In embodiments, in Formula 601, Ar601 may be a substituted or unsubstituted anthracene group.
In embodiments, the electron transport region may include a compound represented by Formula 601-1:
In an embodiment, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
The electron transport region may include: one of Compounds ET1 to ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); Alq3; BAlq; TAZ; NTAZ; or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å. For example, the thickness of the electron transport region may be in a range of about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (e.g., the electron transport layer in the electron transport region) may further include, in addition to the materials as described above, 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 the metal ion of an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. Each 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 an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure having multipole layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of each of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include alkali metal oxides such as Li2O, Cs2O, K2O, and the like, alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and the like, or any combination thereof. The alkaline earth metal-containing compound may include alkaline earth metal compounds, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), and the like. The rare earth metal-containing compound may include YbF3, ScF3, SC2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and the like.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may include an alkali metal ion, an alkaline earth metal ion, or a rare earth metal and a ligand bonded to the metal ion, 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 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 above, and may further include an organic material (e.g., a compound represented by Formula 601).
In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (e.g., an alkali metal halide), or the electron injection layer may consist of an alkali metal-containing compound (e.g., an alkali metal halide), and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the interlayer 130 as described above. The second electrode 150 may be a cathode, which is an electron injection electrode. The second electrode 150 may include a material having a low-work function, for example, a metal, an alloy, an electrically conductive compound, or any combination thereof.
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-layered structure or a multi-layered structure.
The light-emitting device 10 may include a first capping layer outside the first electrode 110, and/or a second capping layer outside the second electrode 150. In embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the stated order.
Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may pass through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first capping layer to the outside. Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may pass through the second electrode 150, which may be 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 based on the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, thus improving the luminous efficiency of the light-emitting device 10.
The first capping layer and the second capping layer may each include a material having a refractive index of greater than or equal to about 1.6 (with respect to a wavelength at about 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In embodiments, at least one of the first capping layer and the second capping layer may each independently include: one of Compounds HT28 to HT33; one of Compounds CP1 to CP6; β-NPB; or any combination thereof:
The condensed cyclic compound represented by Formula 1 may be included in various films. According to embodiments, a film including the condensed cyclic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or a light control means)(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-shielding member (for example, a light reflective layer, a light absorbing layer, or the like), a protective member (for example, an insulating layer, a dielectric layer, or the like).
The light-emitting device may be included in various electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light-emitting device. In an embodiment, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, the quantum dot as described herein.
The electronic apparatus may include a first substrate. The first substrate may include subpixels, the color filter may include color filter areas respectively corresponding to the subpixels, and the color conversion layer may include color conversion areas respectively corresponding to the subpixels.
A pixel-defining film may be arranged among the subpixels to define each subpixel.
The color filter may further include color filter areas and light-shielding patterns arranged between the color filter areas, and the color conversion layer may further include color conversion areas and light-shielding patterns arranged between the color conversion areas.
The color filter areas (or the 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, in which the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the color filter areas (or the 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 a quantum dot. The quantum dot may be the same as described herein. The first area, the second area, and/or the third area may each further include a scatterer.
For example, the light-emitting device may a emit first light, the first area may absorb the first light to emit a first-first color light, the second area may absorb the first light to emit a second-first color light, and the third area may absorb the first light to emit a third-first color light. The first-first color light, the second-first color light, and the third-first color light may each have different maximum emission wavelengths from one another. In embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, in which any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
The electronic apparatus may further include an encapsulation unit for encapsulating the light-emitting device. The encapsulation unit may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The encapsulation unit allows light to pass to the outside from the light-emitting device and prevents the air and moisture from permeating into the light-emitting device at the same time. The encapsulation unit may be an encapsulation substrate including a transparent glass substrate or a plastic substrate. The encapsulation unit may be a thin-film encapsulation layer including at least one of an organic layer and an inorganic layer. When the encapsulation unit is a thin film encapsulation layer, the electronic apparatus may be flexible.
In addition to the color filter and/or the color conversion layer, various functional layers may be further disposed on the encapsulation unit depending on the use of the electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarizing layer, and the like. The touch screen layer may be a resistive touch screen layer, a capacitive touch screen layer, or an infrared beam touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual by using biometric information of a living body (e.g., fingertips, a pupil, or the like).
The authentication apparatus may further include a biometric information collector, in addition to the optoelectronic device and the light-emitting device as described above.
The electronic apparatus may be applied to various displays, an optical source, lighting, a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measurement device, a pulse wave measuring device, an electrocardiogram recorder, an ultrasonic diagnostic device, or an endoscope display), a fish finder, various measurement devices, gauges (e.g., gauges of an automobile, an airplane, or a ship), and a projector.
The light-emitting device may be included in various electronic equipment.
For example, the electronic equipment including the light-emitting device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Since the light-emitting device has excellent effects in terms of luminescence efficiency, long lifespan, and the like, the electronic equipment including the light-emitting device may have characteristics such as high luminance, high resolution, and low power consumption.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be arranged on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be arranged on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active 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 active layer 220 from the gate electrode 240 may be arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 140 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 a source region and a drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may respectively contact the exposed portions of the source region and the drain region of the active layer 220.
Such a TFT may be electrically connected to a light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270, may not fully cover the drain electrode 270. The first electrode 110 may be arranged to be electrically connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. Although not shown in
The second electrode 150 may be arranged on the interlayer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation unit 300 may be arranged on the capping layer 170. The encapsulation unit 300 may be arranged on a light-emitting device to protect the light-emitting device from moisture or oxygen. The encapsulation unit 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 (e.g., polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE) or the like), or any combination thereof; or any combination of the inorganic film and the organic film.
The electronic apparatus of
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A display device may implement an image through a two-dimensional array of pixels that are arranged in the display area DA.
The non-display area NDA may be an area that does not display an image, and may entirely surround the display area DA. On the non-display area NDA, a driver for providing electrical signals or power to display devices arranged on the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element, a printing circuit board, or the like may be electrically connected, may be arranged.
In the electronic equipment 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. In an embodiment, as illustrated in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a direction (e.g., a predetermined direction or a selectable direction) according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis that is a portion excluding the body in which mechanical apparatuses necessary for driving are installed. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and 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 the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. Multiple side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400 and the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in the x direction or the −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the −x direction. For example, an imaginary straight line L connecting the side window glasses 1100 may extend in the x direction or the −x direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In an embodiment, multiple side mirrors 1300 may be provided. Any one of the side mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in the 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, 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 buttons for adjusting an audio device, an air conditioning device, and a seat heater may be disposed. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In an embodiment, the cluster 1400 may be arranged to correspond to a driver seat (not shown), and the passenger seat dashboard 1600 may be disposed to correspond to a passenger seat (not shown). In an embodiment, 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 an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, and the like. Hereinafter, as the display device 2 according to an embodiment, an organic light-emitting display apparatus including the light-emitting device according to the disclosure will be described as an example, but various types of display devices as described above may be used in embodiments of the disclosure.
Referring to
Referring to
Referring to
Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a selected region by using various 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 respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region 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 rate of about 0.01 Å/sec to about 100 Å/sec, depending on the material to be included in each layer to be formed and the structure of each layer to be formed.
The term “C3-C60 carbocyclic group” as used herein may be a cyclic group consisting of carbon atoms as the only ring-forming atom and having 3 to 60 carbon atoms. The term “C1-C60 heterocyclic group” as used herein may be a cyclic group that has 1 to 60 carbon atoms and further has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of a C1-C60 heterocyclic group may be from 3 to 61.
The term “cyclic group” as used herein may be a C8-C60 carbocyclic group or a C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used herein may be a cyclic group that has 3 to 60 carbon atoms and may not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein may be a heterocyclic group that has 1 to 60 carbon atoms and may include *—N═*′ as a ring-forming moiety.
In embodiments,
The terms “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, or “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of a monovalent C3-C60 carbocyclic group or a 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 a divalent C3-C60 carbocyclic group or a monovalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as used herein may be a divalent group having a same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at a terminus of the C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and the like. The term “C2-C60 alkenylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at a terminus of the C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and the like. The term “C2-C60 alkynylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein may be a monovalent group represented by —O(A101) (wherein A101 may be a C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
The term “C3-C10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and the like. The term “C3-C10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkyl group.
The term “C5-C10 cycloalkenyl group” as used herein may be a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C3-C10 cycloalkenylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one carbon-carbon double bond in the cyclic structure thereof. Examples of a C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkenylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of a C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the respective rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein may be a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C1-C60 heteroarylene group” as used herein may be a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of a C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the respective rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein may be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of a monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indeno anthracenyl group, and the like. The term “divalent non-aromatic condensed polycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of a monovalent non-aromatic condensed heteropolycyclic group may 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 indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C6-C60 aryloxy group” as used herein may be a group represented by —O(A102) (wherein A102 may be a C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein may be a group represented by —S(A103) (wherein A103 may be a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein may be a group represented by (A104)(A105) (wherein A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as used herein may be a group represented by (A106)(A107) (wherein A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
In the specification, the group “R10a” may be:
In the specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group.
The term “heteroatom” as used herein refers to any atom other than a carbon atom or a hydrogen atom. Examples of a heteroatom may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
In the specification, the third-row transition metal may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
In the specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “tert-Bu” or “But” each refer to a tert-butyl group, and “OMe” refers to a methoxy group.
The term “biphenyl group” as used herein may be “a phenyl group substituted with a phenyl group.” For example, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein may be “a phenyl group substituted with a biphenyl group”. For example, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
The symbols * and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
In the specification, 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.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to the following Synthesis Examples and Examples. The wording “B was used instead of A” used in describing synthesis examples refers to an amount of B that was identical to an amount of A in terms of molar equivalents.
(3,5-dichlorophenyl)boronic acid (1.2 eq), 9-bromo-9,10-dihydroanthracene (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. The reaction solution was cooled, and an organic layer was obtained through extraction while adding 1 L of water and 300 mL of ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 21-1 (yield: 69%).
Intermediate 21-1 (1 eq), 4′,5-di-tert-butyl-[1,1′-biphenyl]-2-amine (2.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 21-2 (yield: 73%).
Intermediate 21-2 (1 eq), 1-bromo-4-iodobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 21-3 (yield: 77%).
Intermediate 21-3 (1 eq), (4-(tert-butyl)phenyl)boronic acid (2.5 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (2 eq) were added and dissolved in toluene/H2O under a nitrogen atmosphere, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Intermediate 21-4 (yield: 80%).
Intermediate 21-4 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 12 hours. After cooling, triethylamine (5 eq) was added thereto to terminate the reaction, and an organic layer was obtained through extraction with H2O/CH2Cl2, and dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Compound 21 (yield: 30%).
3,5-dichlorophenyl)boronic acid (1.2 eq), 9-bromo-9,10-dihydroanthracene (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction while adding 1 L of water and 300 mL of ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 69-1 (yield: 72%).
Intermediate 69-1 (1 eq), 4,4″-di-tert-butyl-[1,1′,3′,1″-terphenyl]-2′-amine (2.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 69-2 (yield: 69%).
Intermediate 69-2 (1 eq), 3,5-di-tert-butyl-3′-iodo-1,1′-biphenyl (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 69-3 (yield: 72%).
Intermediate 69-3 (1 eq), 4,4″-di-tert-butyl-[1,1′,3′,1″-terphenyl]-2′-amine (2.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Intermediate 69-4 (yield: 67%).
Intermediate 69-4 (1 eq), 1-chloro-3-iodobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Intermediate 69-5 (yield: 71%).
Intermediate 69-5 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 12 hours. After cooling, triethylamine (5 eq) was added thereto to terminate the reaction, and an organic layer was obtained through extraction with H2O/CH2Cl2, and dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and the chromatography to thereby obtain Intermediate 69-6 (yield: 51%).
Intermediate 69-6 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (2.4 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Compound 69 (yield: 62%).
3,5-dichlorophenyl)boronic acid (1.2 eq), 9-bromo-9,10-dihydroanthracene (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction while adding 1 L of water and 300 mL of ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 89-1 (yield: 75%).
Intermediate 89-1 (1 eq), 4,4″,5′-tri-tert-butyl-[1,1′:3′,1″-terphenyl]-2′-amine (2.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 89-2 (yield: 71%).
Intermediate 89-2 (1 eq), 1-bromo-3-iodobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 89-3 (yield: 65%).
Intermediate 89-3 (1 eq), dibenzo[b,d]furan-2-ylboronic acid (2.5 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (2 eq) were dissolved in toluene/H2O as a solvent under a nitrogen atmosphere, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Intermediate 89-4 (yield: 75%).
Intermediate 89-4 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 12 hours. After cooling, triethylamine (5 eq) was added thereto to terminate the reaction, and an organic layer was obtained through extraction with H2O/CH2Cl2, and dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Compound 89 (yield: 51%).
3,5-dichlorophenyl)boronic acid (1.2 eq), 9-bromo-9,10-dihydroanthracene (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction while adding 1 L of water and 300 ml of ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 120-1 (yield: 74%).
Intermediate 120-1 (1 eq), 5′-(tert-butyl)-[1,1′: 3′,1″-terphenyl]-2′-amine (2.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 120-2 (yield: 67%).
Intermediate 120-2 (1 eq), 3-iodochlorobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 120-3 (yield: 66%).
Intermediate 120-3 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 24 hours. After cooling, triethylamine (5 eq.) was added to terminate the reaction, and an organic layer is obtained through extraction with H2O/CH2Cl2, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Intermediate 120-4 (yield: 41%).
Intermediate 120-4 (1 eq), 3,6-di-tert-butyl-9H-carbazole (2.4 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (3 eq) were added and dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction with water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the chromatography to thereby obtain Compound 120 (yield: 81%).
3,5-dichlorophenyl)boronic acid (1.2 eq), 9-bromo-9,10-dihydroanthracene (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an organic layer was obtained through extraction while adding 1 L of water and 300 mL of ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 161-1 (yield: 71%).
Intermediate 161-1 (1 eq), 3,5-di-tert-butylaniline (1.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 161-2 (yield: 53%).
Intermediate 161-2 (1 eq), p-toluidine (1.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 161-3 (yield: 68%).
Intermediate 161-3 (1 eq), iodobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 161-4 (yield: 61%).
Intermediate 161-4 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 24 hours. After cooling, triethylamine (5 eq) was added thereto to terminate the reaction, and an organic layer was obtained through extraction with H2O/CH2Cl2, and dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and recrystallized by silica gel column chromatography to thereby obtain Compound 161 (yield: 43%).
(Phenyl-d5)boronic acid (1.0 eq), 9,10-dibromo-9,10-dihydroanthracene (1.1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, extraction was performed while adding 1 L of water and 300 mL of ethyl acetate, to thereby obtain an organic layer, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 162-1 (yield: 48%).
3,5-dichlorophenyl)boronic acid (1.2 eq), Intermediate 162-1 (1 eq), tris(dibenzylideneacetone)dipalladium(0)(0.05 eq), Pd(PPh3)4 (0.05 eq), and potassium carbonate (1.5 eq) were dissolved in toluene/H2O as a solvent, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, extraction was performed while adding 1 L of water and 300 mL of ethyl acetate, to thereby obtain an organic layer, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to thereby obtain Intermediate 162-2 (yield: 65%).
Intermediate 162-2 (1 eq), aniline (1.1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butyl phosphine (0.1 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 140° C. for 1 day. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 162-3 (yield: 61%).
Intermediate 162-3 (1 eq), iodobenzene (10 eq), Pd2(dba)3 (0.5 eq), tris-tert-butyl phosphine (1 eq), and sodium tert-butoxide (4 eq) were dissolved in o-xylene under a nitrogen atmosphere, and the reaction solution was stirred at 160° C. for 3 days. After cooling, an organic layer was obtained through extraction while adding water and ethyl acetate, followed by drying with MgSO4 and filtering. The filtrate was decompressed to remove the solvent therefrom, and the obtained reaction product was purified and separated by silica gel column chromatography to thereby obtain Intermediate 162-4 (yield: 59%).
Intermediate 162-4 (1 eq) was dissolved in o-dichlorobenzene under a nitrogen atmosphere, followed by cooling using water-ice, BBr3 (5 eq) was slowly added dropwise thereto, and the reaction solution was stirred at 180° C. for 24 hours. After cooling, triethylamine (5 eq) was added thereto to terminate the reaction, and an organic layer was obtained through extraction with H2O/CH2Cl2, and dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and the chromatography to thereby obtain Compound 162 (yield: 44%).
The results of 1H NMR and high-resolution mass (HR-MS) measurements of the compounds synthesized in Synthesis Examples 1 to 6 are shown in Table 1. Synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 6 may be readily recognized by those of ordinary skill in the art with reference to the synthesis pathways and raw materials.
The LUMO, highest occupied molecular orbital (HOMO), bandgap, maximum emission wavelength (λmax), and metal-to-ligand charge transfer (MLCT) values of each of the compounds of Synthesis Examples were measured using the method described in Table 2, and the results thereof are shown in Table 3.
As an anode, a Corning 15 Ω/cm2 (1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water for 5 minutes each, cleaned by irradiation of ultraviolet rays and exposure to ozone for 30 minutes, and mounted on a vacuum deposition apparatus.
NPD was deposited on an ITO anode formed on the glass substrate to a thickness of 300 Å to form a hole injection layer, and HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 600 Å, and CzSi was deposited on the hole transport layer to form an emission auxiliary layer having a thickness of 100 Å.
A host (HT-2 and ET-2), a dopant (Compound 21), and a sensitizer (PS2) were co-deposited on the hole transport layer in a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å.
TSPO1 was deposited on the emission layer to form a hole blocking layer having a thickness of 200 Å, TPBI was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a LiF/AI electrode (cathode) having a thickness of 3,000 Å.
Organic light-emitting devices of Examples 1-2 to 1-6 and Comparative Examples 1-1 to 1-3 were manufactured in the same manner as in Example 1, except that Compound 69, Compound 89, Compound 120, Compound 161, Compound 162, and Comparative Compounds 1 to 3 for the Comparative Examples were used instead of Compound 21 in forming the emission layer.
Organic light-emitting devices of Examples 2-1 to 2-6 and Comparative Examples 2-1 to 2-3 were manufactured in the same manner as in Example 1, except that the compositions of the host, the dopant, and the sensitizer were adjusted as shown in Table 5 in forming the emission layer.
To evaluate the characteristics of the organic light-emitting devices manufactured according to Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3, the driving voltage at a current density of 10 mA/cm2 and maximum quantum efficiency were measured, and results thereof are shown in Table 4. The driving voltage of each of the organic light-emitting devices was measured using a source meter (Keithley Instrument Inc., 2400 series), and the maximum quantum efficiency thereof was measured using the external quantum efficiency measurement apparatus C9920-2-12 of Hamamatsu Photonics Inc. In evaluating the maximum quantum efficiency, the luminance/current density was measured using a luminance meter that was calibrated for wavelength sensitivity, and the maximum quantum efficiency was converted by assuming an angular luminance distribution (Lambertian) which introduced a perfect reflecting diffuser. To evaluate the lifespan of each device, values obtained by comparing the time taken to reach 50% of the initial luminance in Comparative Example 1 with those of Examples 1 to 6 and Comparative Examples 2 and 3 were calculated.
The characteristics of the organic light-emitting devices manufactured in Examples 2-1 to 2-6 and Comparative Examples 2-1 to 2-3 were measured using the method as described above, and the results thereof are shown in Table 5.
According to the embodiments, by using a condensed cyclic compound, a light-emitting device having high efficiency and long lifespan and a high-quality electronic apparatus including the light-emitting device may be manufactured.
Embodiments have been disclosed herein, and although terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purposes of limitation. In some instances, as would be apparent by one of ordinary skill in the art, features, characteristics, and/or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made without departing from the spirit and scope of the disclosure.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0039300 | Mar 2023 | KR | national |
