Patent Application
20230397491
This application claims priority to and benefits of Korean Patent Application No. 10-2022-0068502 under 35 U.S.C. § 119, filed on Jun. 3, 2022, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to an amine-containing compound, a light-emitting device including the same, an electronic device including the light-emitting device, and an electronic apparatus including the electronic device.
An organic light-emitting device may have wider viewing angles, higher contrast ratios, and shorter response times, compared to an inorganic light-emitting device. An organic light-emitting device may include a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, which are 11 emission layer through the hole transport region. Electrons injected from the second electrode may move to the emission layer through the electron transport region. Carriers such as the holes and the electrons may combine in the emission layer. The carriers may combine to generate excitons. These excitons transition from an excited state to a ground state to 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 an amine-containing compound with improved hole transport characteristics and a light-emitting device having a low driving voltage, a high luminance, high luminescence efficiency, and a long lifespan by employing the amine-containing compound. Embodiments may include a high-quality electronic apparatus and an electronic device that includes the light-emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the embodiments of the disclosure.
Embodiments provide, an amine-containing compound which may be represented by Formula 1:
In Formula 1,
According to an embodiment, L1 to L3 and Ar1 to Ar4 may each independently be a cyclohexane group, an adamantane group, a norbornane group, a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a spiro-bifluorene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with deuterium, a C1-C20 alkyl group, a cyclohexane group, an adamantane group, a norbornane group, a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a spiro-bifluorene group, a dibenzofuran group, a dibenzothiophene group, or any combination thereof.
According to an embodiment, L1 to L3 may each independently be a group represented by one of Formulae 2-1 to 2-11, which are explained below.
According to an embodiment, Ar1 to Ar4 may each independently be:
a cyclohexane group, an adamantane group, or a norbornane group, each unsubstituted or substituted with at least one R10a; or
a group represented by one of Formulae 3-1 to 3-22, which are explained below.
According to an embodiment, a1 and a2 may each independently be 0, 1, or 2.
According to an embodiment, a3 may be 0 or 1.
According to an embodiment, R1 to R4 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, or a phenyl group.
According to an embodiment, R1 and R2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and
R1 and R2 may be bonded via a single bond, *—O—*′, or *—S—*′.
According to an embodiment, the amine-containing compound may be represented by one of Formulae 1-1 to 1-12, which are explained below.
According to an embodiment, the amine-containing compound may be one of Compounds 1 to 116, which are explained below.
According to embodiments, a light-emitting device 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 an amine-containing compound represented by Formula 1, which is explained herein.
According to an embodiment, 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,
According to an embodiment, the interlayer may include the amine-containing compound.
According to an embodiment, the hole transport region may include the amine-containing compound.
According to an embodiment, the hole transport layer may include the amine-containing compound, and the hole transport layer may directly contact the emission layer.
According to an embodiment, the light-emitting device may further include a capping layer outside the first electrode, wherein the capping layer may include the amine-containing compound.
According to an embodiment, the light-emitting device may further include a first capping layer outside the first electrode and a second capping layer outside the second electrode, wherein the first capping layer or the second capping layer may include the amine-containing compound.
According to embodiments, an electronic device may include the light-emitting device.
According to an embodiment, the electronic device may further include:
According to embodiments, an electronic apparatus may include the electronic device, wherein
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 numbers 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 an amine-containing compound which may be represented by Formula 1.
According to an embodiment, the first electrode may be an anode. The second electrode may be a cathode. The emission layer may include a dopant and a host and may emit light. The dopant and the host are to be described later.
The term “interlayer” as used herein may be a single layer and/or multiple layers located between the first electrode and the second electrode of the light-emitting device.
According to an embodiment, 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. 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 hole transport region may include the hole injection layer on the first electrode and the hole transport layer between the hole injection layer and the emission layer. The hole injection layer may have a single-layer structure or a multi-layer structure. The hole transport layer may have a single-layer structure or a multi-layer structure. For example, the hole transport layer may include a first hole transport layer, a second hole transport layer, and a third hole transport layer, which may be in this stated order from the hole injection layer.
For example, the electron transport region may include the electron transport layer on the emission layer, and the electron injection layer between the electron transport layer and the second electrode.
According to an embodiment, the interlayer may include the amine-containing compound.
According to an embodiment, the hole transport region may include the amine-containing compound.
According to an embodiment, the hole transport layer may include the amine-containing compound, and the hole transport layer may directly contact the emission layer. For example, the amine-containing compound may be included in the third hole transport layer. In another example, the amine-containing compound may be included in the first hole transport layer and the third hole transport layer. In another example, the amine-containing compound may be included in the first to third hole transport layers.
According to an embodiment, the light-emitting device may further include a capping layer outside of the first electrode, and the capping layer may include the amine-containing compound.
According to an embodiment, the light-emitting device may further include a first capping layer outside of the first electrode and a second capping layer outside of the second electrode, and the first capping layer or the second capping layer may include the amine-containing compound. For example, the amine-containing compound may be included in the first capping layer, among the first capping layer, the first electrode, and the interlayer, which may be in this stated order. In another example, the amine-containing compound may be included in the second capping layer, among the interlayer, the second electrode, and the second capping layer, which may be in this stated order. The amine-containing compound may be included in both of the first capping layer and the second capping layer.
Embodiments also provide an electronic device which may include the light-emitting device.
According to an embodiment, the electronic device may further include a thin-film transistor electrically connected to the light-emitting device, and a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. For example, the electronic device may include the light-emitting device, the thin-film transistor, and the color filter. In another example, the electronic device may include the light-emitting device, the thin-film transistor, the color filter, and the color conversion layer.
Embodiments also provide, an electronic apparatus which may include the electronic device. The electronic apparatus may be a flat panel display, a curved display, a computer monitor, a medical monitor, a TV, a billboard, an indoor light, or 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 phone, a cell 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, virtual reality display, an augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Embodiments also provide, the amine-containing compound which may be represented by Formula 1:
In Formula 1,
According to an embodiment, the amine-containing compound may not include a carbazole group.
According to an embodiment, Ar3 and Ar4 may not be hydrogen or deuterium. Examples in which Ar3 and Ar4 may not be hydrogen or deuterium and Comparative Examples in which Ar3 and Ar4 may not be hydrogen or deuterium are to be described later.
According to an embodiment, L1 to L3, and Ar1 to Ar4 may each independently be:
For example, L1 to L3 and Ar1 to Ar4 may not include a carbazole group.
For example, L1 to L3 may each independently be a phenyl group unsubstituted or substituted with at least one R10a, a naphthyl group unsubstituted or substituted with at least one R10a, or a biphenyl group unsubstituted or substituted with at least one R10a.
For example, Ar1 to Ar4 may each independently be a phenyl group unsubstituted or substituted with at least one R10a, a naphthyl group unsubstituted or substituted with at least one R10a, a phenanthrenyl group unsubstituted or substituted with at least one R10a, a fluorenyl group unsubstituted or substituted with at least one R10a, a dibenzofuranyl group unsubstituted or substituted with at least one R10a, a dibenzothiophenyl group unsubstituted or substituted with at least one R10a, a biphenyl group unsubstituted or substituted with at least one R10a, a terphenyl group unsubstituted or substituted with at least one R10a, or a spiro-bifluorenyl group unsubstituted or substituted with at least one R10a.
According to an embodiment, L1 to L3 may each independently be a group represented by one of Formulae 2-1 to 2-11:
In Formulae 2-1 to 2-11,
According to an embodiment, Ar1 to Ar4 may each independently be:
In Formulae 3-1 to 3-22,
According to an embodiment, a1 and a2 may each independently be 0, 1, or 2.
According to an embodiment, a3 may be 0 or 1.
According to an embodiment, R1 to R4 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, or a phenyl group.
According to another embodiment, R1 and R2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and R1 and R2 may be bonded to each other via a single bond, *—O—*′ or *—S—*′.
According to an embodiment, the amine-containing compound may be represented by any one of Formulae 1-1 to 1-12:
In Formulae 1-1 to 1-12,
According to an embodiment, the amine-containing compound may be one of Compounds 1 to 116:
In the amine-containing compound represented by Formula 1, Ar3 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a. A group represented by *-(L3)a3-N[(L1)a1-Ar1][(L2)a2-Ar2] in Formula 1, for example, an amine-containing group, may be bonded to a carbon in the 2-position of a fluorene core. In this manner, the amine-containing compound may have an energy level suitable for the hole transport layer. Moreover, as r-conjugation of the amine-containing compound increases, the amine-containing compound may effectively stabilize the holes. Accordingly, the amine-containing compound represented by Formula 1 may have excellent hole transport characteristics, and the light-emitting device including the amine-containing compound represented by Formula 1 may have a low driving voltage, high luminance, high luminescence efficiency and long lifespan.
[Description of
Hereinafter, a structure of the light-emitting device 10 according to an embodiment of the disclosure and a method of manufacturing the light-emitting device 10 will be described in connection with
[First Electrode 110]
In
The first electrode 110 may be formed by applying a material for forming the first electrode 110 onto the substrate by using a deposition or sputtering method. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combinations thereof.
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.
[Interlayer 130]
The interlayer 130 may be arranged 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, or the like.
The interlayer 130 may include, two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between the two emitting units. When the interlayer 130 includes the two or more emitting units and the at least one charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
[Hole Transport Region in Interlayer 130]
The hole transport region may have: a structure consisting of a single layer consisting of a single material, a structure consisting of a single layer consisting of 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.
For example, 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, wherein the layers of each structure may be stacked from the first electrode 110 in its respective 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 embodiments, each of Formulae 201 and 202 may 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 with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described herein.
In an embodiment, in Formulae CY201 to CY217 ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In embodiments, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY203.
According to another embodiment, 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 a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203.
In embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203, and may include at least one of groups represented by Formulae CY204 to CY217.
In embodiments, each of Formulae 201 and 202 may not include a group represented by one of 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), p-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, a 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, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, a thickness of the hole injection layer may be in a range of 100 Å to about 1,000 Å, and a 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 compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer to improve the light emission efficiency. The electron blocking layer may be a layer that prevents 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 further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge generation material).
The charge-generation material may be, for example, a p-dopant.
For example, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be equal to or less than about −3.5 eV.
In embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.
Examples of the cyano group-containing compound may include HAT-CN, and a compound represented by Formula 221:
In Formula 221,
In the compound including 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 the metal may include an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); 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), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
Examples of the compound including element EL1 and element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, or a metal iodide), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or any combination thereof.
Examples of the metal oxide may include a tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and a rhenium oxide (for example, ReO3, etc.).
Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.
Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
Examples of the transition metal halide may include a titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), a vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), a molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), a manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide may include a zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (for example, InI3, etc.), and a tin halide (for example, SnI2, etc.).
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
An example of the metalloid halide may be an antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[Emission Layer in Interlayer 130]
In case that 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 are 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.
An amount of the dopant in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
In embodiments, the emission layer may include a quantum dot.
The emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, a 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 is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Host
In embodiments, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21. [Formula 301]
In Formula 301,
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 Formula 301-1 and 301-2,
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:
[Phosphorescent Dopant]
In embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In Formulae 401 and 402,
For example, in Formula 402, X401 may be nitrogen, and X402 may be carbon, or each of X401 and X402 may be nitrogen.
In another example, when xc1 in Formula 401 is 2 or more, two ring A401(s) in two or more of L401(s) may optionally be linked to each other via T402, which may be a linking group, and two ring A402(s) may optionally be linked to each other via T403, which may be a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as described herein with respect to T401.
The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:
[Fluorescent Dopant]
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In embodiments, the fluorescent dopant may include a compound represented by Formula 501:
In Formula 501,
In an embodiment in Formula 501, Ar501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) 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 fluorescent light 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 type of other materials included in the emission layer.
According to an embodiment, a difference between a triplet energy level of the delayed fluorescence material and a singlet energy level of the delayed fluorescence material may be greater than or equal to about 0 eV and less than or equal 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 satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
For example, the delayed fluorescence material may include: a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group and the like, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, and the like), a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other while sharing boron (B), and the like.
Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF14:
[Quantum Dot]
The emission layer may include a quantum dot.
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 the size of the crystal.
A diameter of the quantum dots may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled through a process which costs lower, and may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, a Group IV element or compound, or any combination thereof.
Examples of the Group II-VI semiconductor compound may include a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
Examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. The 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, etc.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3, or InGaSe3; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
The Group IV element or compound may include: a single element, material such as Si or Ge; a binary compound, such as SiC or SiGe; 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 in a particle at a uniform concentration or at a non-uniform concentration.
In embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot may be uniform, or the quantum dot may have a core-shell structure. For example, when the quantum dot has a core-shell structure, 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 degeneration 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 a single layer or a multi-layer. An interface between the core and the shell may have a concentration gradient in which the concentration of a material that is present in the shell decreases toward the core.
Examples of 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 the metal oxide, the metalloid oxide, or the 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. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. 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.
A full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be equal to or less than about 45 nm. For example, the FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 40 nm. For example, the FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 30 nm. Within these ranges, color purity or color reproducibility may be increased. Light emitted through the quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
The quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In embodiments, the size of the quantum dot may be selected to emit red, green and/or blue light. The size of the quantum dot may be configured to emit white light by combination of light of various colors.
[Electron Transport Region in Interlayer 130]
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-transporting region may include a buffer layer, a hole-blocking layer, an electron control layer, an electron-transporting layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole-blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the constituting layers of each structure may be stacked from an emission layer in its respective stated order, but the structure of the electron transport region is not limited thereto.
In an embodiment, the electron transport region (for example, the buffer layer, the hole-blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
For example, the electron transport region 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(s) may be linked to each other via a single bond.
In embodiments, Ar601 in Formula 601 may be an anthracene group unsubstituted or substituted with at least one R10a.
In embodiments, the electron transport region may include a compound represented by Formula 601-1:
In Formula 601-1,
In an embodiment, in Formula 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 from 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, a thickness of the buffer layer, the hole-blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1000 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, 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, 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 (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials 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. The metal ion of an 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. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, 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 consisting of different materials, or a structure including multiple 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 (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x may be a real number satisfying the condition of 0<x<1), BaxCa1-xO (wherein x may be a real number satisfying the condition of 0<x<1), or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In 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, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and, as 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 herein. In embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In embodiments, the electron injection layer may consist of: an alkali metal-containing compound (for example, an alkali metal halide); or an alkali metal-containing compound (for example, 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, or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly 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, a 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 the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[Second Electrode 150]
The second electrode 150 may be arranged on the interlayer 130. The second electrode 150 may be a cathode which is an electron injection electrode. A material for forming the second electrode 150 may include a metal, an alloy, an electrically conductive compound, or any combination thereof, each of which has a low work function.
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.
[Capping Layer]
The light-emitting device 10 may include a first capping layer located outside the first electrode 110, and/or a second capping layer located outside the second electrode 150. For example, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this 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 this 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 this stated order.
For example, light generated by the emission layer in the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and the first capping layer. For example, light generated by the emission layer in the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may each increase external emission efficiency according to the principle of constructive interference.
Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
The first capping layer and the second capping layer may each include a material having a refractive index of equal to or greater than about 1.6 (with respect to a wavelength of 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 carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. Optionally, the carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In embodiments, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
For example, 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, p-NPB, or any combination thereof:
[Film]
The film may be, for example, an optical member (or, a light-controlling member) (e.g., a color filter, a color-conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light-absorbing layer, a polarization layer, a quantum dot-containing layer, or the like), a light-blocking member (e.g., a light reflection layer or a light-absorbing layer), or a protection member (e.g., an insulating layer or a dielectric material layer).
[Electronic Device]
The light-emitting device may be included in various electronic devices. For example, the electronic device including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
The electronic device (for example, 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 located in at least one direction in which light emitted from the light-emitting device travels. For example, 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 embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
The electronic device 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 located among the subpixels to define each subpixel.
The color filter may further include color filter areas and light-shielding patterns located between the color filter areas, and the color conversion layer may further include color conversion areas and light-shielding patterns located between the color conversion areas.
The color filter areas (or 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. The first-color light, the second-color light, and/or the third-color light may have different maximum luminescence 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. The first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include 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 include a scatter.
For example, the light-emitting device may emit first light, the first area may absorb the first light to emit first-first color light, the second area may absorb the first light to emit second-first color light, and the third area may absorb the first light to emit third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. 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 device may further include a thin-film transistor, in addition to the light-emitting device as described herein. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein one of the source electrode and the drain electrode may be electrically connected to 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, or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and simultaneously prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
Various functional layers may be further included on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic device. The functional layers may include a touch screen layer, a polarization layer, and the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. An authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device as described herein, a biometric information collector.
The electronic device may be applied to various displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
[Electronic Apparatus]
The light-emitting device may be included in various electronic apparatuses.
For example, the electronic apparatus including the light-emitting device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a TV, 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 phone, a cell phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays, a virtual reality display, an augmented reality display, vehicles, a video wall including multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, and a signboard.
As the light-emitting device has the characteristics of excellent light emission efficiency, long lifespan, etc., the electronic apparatus including the light-emitting device may have the characteristics of high luminance, high resolution, low power consumption, etc.
[Description of
The electronic device of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent infiltration impurities through the substrate 100. The buffer layer 210 may provide a flat surface on the substrate 100.
A TFT may be located on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor, such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor. The activation layer 220 may include a source region, a drain region, and a channel region.
The gate insulating film 230 may be on the activation layer 220. The gate insulating film 230 may insulate the activation layer 220 from the gate electrode 240.
The gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220. The source electrode 260 and the drain electrode 270 may be in contact with the exposed source region and the drain region of the activation layer 220.
The TFT may be electrically connected to the light-emitting device to drive the light-emitting device. The TFT may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may not entirely cover the drain electrode 270. The passivation layer 280 may be arranged to expose a certain region of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed drain electrode 270.
A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110. The interlayer 130 may be formed in the exposed region. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in
The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
The electronic device of
[Description of
The electronic apparatus 1 may be an apparatus displaying a video or a still image and examples of the electronic apparatus may include not only portable electronic apparatuses, such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation device, an ultra-mobile PC, etc.; various products including a television, a laptop, a monitor, a signboard, internet of things (IOT); or a part thereof. In an embodiment, the electronic apparatus 1 may be a wearable device such as a smart watch, a watch phone, a glasses-type display, a head mounted display (HMD), or a part thereof. However, embodiments are not limited thereto. For example, the electronic apparatus 1 may be a dashboard of a vehicle, a center information display (CID) provided at a center fascia or on a dashboard of a vehicle, a room mirror display functioning as a side mirror of a vehicle, a display provided at a backseat entertainment system or at a back of a front seat of a vehicle, a head up display (HUD) arranged at the front of a vehicle or projected on a front window of a vehicle, or a computer generated hologram augmented reality HUD (CGH AR HUD).
The electronic apparatus 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic apparatus 1 may implement an image through an array of pixels arranged in a two-dimensional (2D) manner in the display area DA.
The non-display area NDA may not display an image and entirely surround the display area DA. A driver, etc. to provide an electrical signal or power to display elements and the like (for example, pixels) arranged in the display area DA may be provided in the non-display area NDA. A pad to which an electronic device or a printed circuit board, etc. may be electrically connected in the non-display area NDA.
A length of the electronic apparatus 1 in the x axis may be different from a length of the electronic apparatus 1 in the y axis. In an embodiment, as illustrated in
[Description of
With reference to
The vehicle 1000 may drive on a road or a railroad. The vehicle 1000 may move in a certain direction according to the rotation of at least one wheel. For example, the vehicle 1000 may be a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a motor bicycle, a bicycle, or a train driving on a railroad.
The vehicle 1000 may include a body including an interior and an exterior, and a chassis, which may be a remaining part of the vehicle 1000, excluding the body, while including a mechanism required for driving. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, and a pillar provided at a boundary between doors. The chassis of the vehicle 1000 may include a power generator, a power transfer unit, a driving system, a steering system, a brake system, a suspension system, a transmission, a fuel supply system, front, rear, left, and right wheels, etc.
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 apparatus 2.
The side window glass 1100 and the front window glass 1200 may be divided by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be arranged on the side of the vehicle 1000.
In an embodiment, the side window glass 1100 may be arranged at a door of the vehicle 1000. There may be multiple side window glasses 1100 which 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. 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 arranged apart from each other in the x direction or −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be arranged apart from each other in the x direction or −x direction. A virtual line L connecting the side window glasses 1100 to each other may extend in the x direction or −x direction. For example, a virtual line L connecting the first side window glass 1110 with the second side window glass 1120 to each other may extend in the x direction or −x direction.
The front window glass 1200 may be one 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 arranged at the exterior of the body. In an embodiment, there may be multiple side mirrors 1300. Any one of the side mirrors 1300 may be arranged outside of the first side window glass 1110. Another of the side mirrors 1300 may be arranged outside of the second side window glass 1120.
The cluster 1400 may be placed in front of a steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant temperature sensor, a fuel gage, a turn indicator, a high beam sign light, a warning light, a seatbelt warning light, an odometer, a trechometer, an automatic transmission selector lever sign light, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel in which buttons may be provided for controlling an audio device, an air conditioning system, and a seat heater. The center fascia 1500 may be arranged on one side of the center fascia 1500.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400, with the center fascia 1500 therebetween. In an embodiment, the cluster 1400 may be arranged in correspondence with a driver seat (not shown), and the passenger seat dashboard 1600 may be arranged in correspondence with 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 apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In an embodiment, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged in at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display, an inorganic light-emitting display, a quantum dot display, etc. Although an organic light-emitting display apparatus including the light-emitting device according to embodiments is described hereinafter as the display apparatus 2, various types of display apparatuses described herein may be used in the embodiments, but embodiments are not limited thereto.
With reference to
With reference to
With reference to
[Manufacturing Method]
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 certain region by using suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
When layers constituting the hole transport region, an emission layer, and layers constituting 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 speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as used herein may be a cyclic group that includes only carbon as ring-forming atoms and consists of 3 to 60 carbon atoms. The term “C1-C60 carbocyclic group” as used herein may be a cyclic group that includes hetero atoms as a ring-forming atom, in addition to carbon, and consists of 1 to 60 carbon atoms. 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 C1-C60 heterocyclic group may have 3 to 61 ring-forming atoms.
The term “cyclic group” as used herein may include the C3-C60 carbocyclic group, or the C1-C60 heterocyclic group.
The term “r electron-rich C3-C60 cyclic group” used herein may be a cyclic group that may not include *—N=*′ as a ring-forming moiety and consists of 3 to 60 carbon atoms. The term “π electron-deficient nitrogen-containing C1-C60 cyclic group” used herein may be a heterocyclic group that includes *—N=*′ as a ring-forming moiety and consists of 1 to 60 carbon atoms.
In embodiments,
The C1-C60 heterocyclic group may be a T2 group, a cyclic group in which at least two T2 groups are condensed with each other, or a cyclic group in which at least one T2 group and at least one T1 group are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or the like.)
The π electron-rich C3-C60 cyclic group may be a T1 group, a cyclic group in which at least two T1 groups are condensed with each other, a T3 group, a cyclic group in which at least two T3 groups are condensed with each other, or a cyclic group in which at least one T3 group and at least one T1 group are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, or the like.)
The π electron-deficient nitrogen-containing C1-C60 cyclic group may be a T4 group, a cyclic group in which at least two T4 groups are condensed with each other, a cyclic group in which at least one T4 group and at least one T1 group are condensed with each other, a cyclic group in which at least one T4 group and at least one T3 group are condensed with each other, or a cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and the like.)
The T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group.
The T2 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group.
The T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group.
The T4 group may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
The terms “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 (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term may be used. For example, the “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 and 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-C10heterocycloalkenyl 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 and a divalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group with 1 to 60 carbon atoms. For example, a C1-C60 alkyl group 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, or 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. For example, a C2-C60 alkenyl group may include an ethenyl group, a prophenyl group, a butenyl group, etc.
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 the terminus of the C2-C60 alkyl group. For example, a C2-C60 alkynyl group may include an ethynyl group, a propynyl group, etc.
The term “C2-C60 alkynylene group” as used herein refers to 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 having the formula of —O(A101) (where A101 may be the C1-C60 alkyl group). For example, a C1-C60 alkoxy group may include a methoxy group, an ethoxy group, an isopropyloxy group, etc.
The term “C3-C10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group with 3 to 10 carbon atoms. The C3-C10 cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, or 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 that includes, in addition to carbon atoms, at least one hetero atom as a ring-forming atom, and consists of 1 to 10 carbon atoms. For example, the C1-C10 heterocycloalkyl group may include a 1,2,3,4-oxatriazolidinyl, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc.
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 “C3-C10 cycloalkenyl group” as used herein may be a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, but no aromaticity. For example, the C3-C10 cycloalkenyl group may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, etc.
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. For example, the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, etc.
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” used herein may be a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. For example, the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, etc.
The term “C6-C60 arylene group” used herein may be a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms.
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” used herein may further include at least one hetero atom as a ring-forming atom, in addition to carbon atoms and refers to a monovalent group having a heterocyclic aromatic system with 1 to 60 carbon atoms. For example, the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, etc.
The term “C1-C60 heteroarylene group” used herein may further include at least one hetero atom as a ring-forming atom, in addition to carbon atoms and refers to a divalent group having a heterocyclic aromatic system with 1 to 60 carbon atoms.
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 (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. For example, the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, etc.
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 (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. For example, the 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 indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, and the like.
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” used herein may be a group represented by —O(A102) (wherein A102 may be the C6-C60 aryl group.)
The term “C6-C60 arylthio group” used herein may be a group represented by —S(A103) (wherein A103 may be the C6-C60 aryl group.)
The term “C7-C60 arylalkyl group” 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.)
The term “C2-C60 heteroarylalkyl group” used herein may be a group represented by -(A106)(A107) (here, A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group.)
The group “R10a” as used herein may be:
The groups Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 as used herein may each independently be: hydrogen; deuterium; —F; —CI; —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 may be any atom other than a carbon atom or a hydrogen atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the terms “tert-Bu” or “But” as used herein each refer to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
The term “biphenyl group” as used herein may be a “phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. 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.
The x axis, the y axis, and the z axis used herein are not limited to three axis on an orthogonal coordinates system, and may be interpreted in a broad sense encompassing the foregoing. For example, the x axis, the y axis, and the z axis may be perpendicular to each other, or respectively indicate different directions not perpendicular 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 means that an identical molar equivalent of B was used in place of A.
1.98 g (10.0 mmol) of 2-biphenylboronic acid, 3.41 g (10.0 mmol) of methyl 5-bromo-2-iodobenzoate, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 2.57 g (yield: 70%) of Intermediate 12-1. The resulting compound was identified by LC-MS. C20H15BrO2: M+ 366.0
After 3.66 g (10 mmol) of Intermediate 12-1 was dissolved in THF (20 ml) in a flask, methylmagnesium bromide (8.4 ml, 3.0 M in diethyl ether) was slowly added into the flask, and stirred at a temperature of 0° C. for 2 hours. An extraction process was performed three times on the reaction solution using 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried by using magnesium sulfate, and the residue obtained by evaporating a solvent was separated and purified by silica gel column chromatography to obtain 2.20 g of Intermediate 12-2 (yield: 60%). The resulting compound was identified by LC-MS. C21H19BrO: M+ 366.0
3.66 g (10 mmol) of Intermediate 12-2 was dissolved in 20 ml of acetic acid/HCl (4/1), and stirred at a temperature of 60° C. for 6 hours. After the reaction solution was cooled to room temperature, 10 g of sodium hydroxide was dissolved in 20 ml of water and added to the reaction solution, and an extraction process was performed thereon three times using 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried by using magnesium sulfate, and the residue obtained by evaporating a solvent was separated and purified by silica gel column chromatography to obtain 2.61 g of Intermediate 12-3 (yield: 75%). The resulting compound was identified by LC-MS. C21H17Br: M+ 348.0
3.48 g (10 mmol) of Intermediate 12-3, 1.90 g (10 mmol) of CuI, and 10 ml of aqueous ammonia were dissolved in 20 ml of DMF, and stirred at a temperature of 130° C. for 8 hours in a seal tube. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried by using magnesium sulfate, and the residue obtained by evaporating a solvent was separated and purified by silica gel column chromatography to obtain 2.14 g of Intermediate 12-4 (yield: 75%). The resulting compound was identified by LC-MS. C21H19N: M+ 285.1
After 2.85 g (10 mmol) of Intermediate 12-4 was dissolved in 20 mL of DCM, N-bromosuccinimide (1.78 g, in DCM) was added thereto at a temperature of 0° C. The resultant was stirred for 5 hours at room temperature, and, 3 g of Na2S2O3 was dissolved in water and added thereto, followed by three times of washing using DCM (30 ml). The DCM layer obtained by the washing was dried using MgSO4 and dried under reduced pressure to obtain a product, which was separated and purified by silica gel column chromatography, to thereby obtain 2.91 g (yield: 80%) of Intermediate 12-5. The resulting compound was identified by LC-MS. C21H18BrN: M+ 363.0
3.63 g (10.0 mmol) of Intermediate 12-5, 1.46 g (12.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 ml of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 2.53 g (yield: 70%) of Intermediate 12-6. The resulting compound was identified by LC-MS. C27H23N: M+ 361.1
4.33 g (12.0 mmol) of Intermediate 12-6, 1.11 ml (10 mmol) of iodobenzene, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) (Pd2dba3), 0.24 g (1 mmol) of P(t-Bu)3, and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 40 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 2.84 g (yield: 65%) of Intermediate 12-7. The resulting compound was identified by LC-MS. C33H27N: M+ 437.2
4.37 g (10.0 mmol) of Intermediate 12-7, 2.83 g (10 mmol) of 2-(4-bromophenyl)naphthalene, 0.46 g (0.5 mmol) of Pd2dba3, 0.24 g (1 mmol) of P(t-Bu)3, and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 40 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.48 g (yield: 70%) of Compound 12. The resulting compound was identified by MS/FAB and 1H NMR.
Compound 18 was synthesized in the same manner as in Synthesis Example 1, except that 9-(3-bromophenyl)-9-phenyl-9H-fluorene was used instead of 2-(4-bromophenyl)naphthalene. The resulting compound was identified by MS/FAB and 1H NMR.
4.74 g (10.0 mmol) of 2,2′-dibromo-9,9′-spirobi[fluorene], 1.22 g (10.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 2.59 g (yield: 55%) of Intermediate 20-1. The resulting compound was identified by LC-MS. C31H19Br: M+ 470.0
4.71 g (10.0 mmol) of Intermediate 20-1, 4.38 g (10 mmol) of Intermediate 12-7, 0.46 g (0.5 mmol) of Pd2dba3, 0.24 g (1 mmol) of P(t-Bu)3, and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 40 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 5.80 g (yield: 70%) of Compound 20. The resulting compound was identified by MS/FAB and 1H NMR.
Compound 22 was synthesized in the same manner as in Synthesis Example 1, except that 4″-chloro-3′-phenyl-1,1′:2′,1″-terphenyl was used instead of 2-(4-bromophenyl)naphthalene. The resulting compound was identified by MS/FAB and 1H NMR.
3.61 g (10.0 mmol) of Intermediate 12-6, 4.78 g (20 mmol) of 1-bromo-4-cyclohexylbenzene, 0.92 g (1 mmol) of Pd2dba3, 0.42 g (2 mmol) of P(t-Bu)3, and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 80 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.75 g (yield: 70%) of Compound 37. The resulting compound was identified by MS/FAB and 1H NMR.
3.52 g (10.0 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 1.22 g (10.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 1.74 g (yield: 50%) of Intermediate 44-1. The resulting compound was identified by LC-MS. C21H17Br: M+ 348.0
3.48 g (10 mmol) of Intermediate 44-1, 1.90 g (10 mmol) of CuI, and 10 ml of aqueous ammonia were dissolved in 20 ml of DMF, and stirred at a temperature of 130° C. for 8 hours in a seal tube. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried by using magnesium sulfate, and a residue obtained by evaporating a solvent was separated and purified by silica gel column chromatography to obtain 2.14 g of Intermediate 44-2 (yield: 75%). The resulting compound was identified by LC-MS. C21H19N: M+ 285.1
After 2.85 g (10 mmol) of Intermediate 44-2 was dissolved in 20 mL of DCM, N-bromosuccinimide (1.78 g, in DCM) was added thereto at a temperature of 0° C. The resultant was stirred for 5 hours at room temperature, and, 3 g of Na2S2O3 was dissolved in water and added thereto, followed by three times of washing using DCM (30 ml). The washed DCM layer was dried using MgSO4 and dried under reduced pressure to obtain a product, which was separated and purified by silica gel column chromatography, to thereby obtain 2.91 g (yield: 80%) of Intermediate 44-3. The resulting compound was identified by LC-MS. C21H18BrN: M+ 363.0
3.63 g (10.0 mmol) of Intermediate 44-3, 1.46 g (12.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 ml of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 2.53 g (yield: 70%) of Intermediate 44-4. The resulting compound was identified by LC-MS. C27H23N: M+ 361.1
3.61 g (10.0 mmol) of Intermediate 44-4, 4.66 g (20 mmol) of 4-bromo-1,1′-biphenyl, 0.92 g (1 mmol) of Pd2dba3, 0.42 g (2 mmol) of P(t-Bu)3, and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 80 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.40 g (yield: 66%) of Compound 44. The resulting compound was identified by MS/FAB and 1H NMR.
3.64 g (10.0 mmol) of Intermediate 12-5, 2.38 g (12.0 mmol) of [1,1′-biphenyl]-4-ylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 3.29 g (yield: 75%) of Intermediate 60-1. The resulting compound was identified by LC-MS. C33H27N: M+ 437.2
4.38 g (10.0 mmol) of Intermediate 60-1, 4.66 g (20 mmol) of 4-bromo-1,1′-biphenyl, 0.92 g (1 mmol) of Pd2dba3, 0.42 g (2 mmol) of P(t-Bu)3, and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 80 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.60 g (yield: 62%) of Compound 60. The resulting compound was identified by MS/FAB and 1H NMR.
3.61 g (10 mmol) of Intermediate 12-6, 4.29 g (30 mmol) of CuBr were dissolved in a 48% bromic acid aqueous solution (10 ml), and 2.07 g of NaNO2 (in H2O) was slowly added thereto at 0° C. The resultant was stirred for 5 hours at room temperature, and, 3 g of Na2S2O3 was dissolved in water and added thereto, followed by three times of washing using DCM (30 ml). The washed DCM layer was dried using MgSO4 and dried under reduced pressure to obtain a product, which was separated and purified by silica gel column chromatography, to thereby obtain 2.97 g (yield: 70%) of Intermediate 66-1. The resulting compound was identified by LC-MS. C27H21Br: M+ 424.0
4.25 g (10.0 mmol) of Intermediate 66-1, 1.56 g (10.0 mmol) of (4-chlorophenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of THF/H2O (2/1) mixed solution, and stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and an extraction process was performed three times thereon using 60 mL of water and 60 mL of diethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 3.43 g (yield: 75%) of Intermediate 66-2. The resulting compound was identified by LC-MS. C33H25N: M+ 456.1
4.56 g (10.0 mmol) of Intermediate 66-2, 2.45 g (10 mmol) of N-phenyl-[1,1′-biphenyl]-4-amine, 0.92 g (1 mmol) of Pd2dba3, 0.42 g (2 mmol) of P(t-Bu)3, and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 80 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.66 g (yield: 70%) of Compound 66. The resulting compound was identified by MS/FAB and 1H NMR.
Compound 70 was synthesized in the same manner as in Synthesis Example 8, except that N-phenylnaphthalen-2-amine was used instead of N-phenyl-[1,1′-biphenyl]-4-amine. The resulting compound was identified by MS/FAB and 1H NMR.
Intermediate 101-1 was synthesized in the same manner as in Synthesis of Intermediate 12-2, except that phenylmagnesium bromide was used instead of methylmagnesium bromide.
Intermediate 101-2 was synthesized in the same manner as in Synthesis of Intermediate 12-3, except that Intermediate 101-1 was used instead of Intermediate 12-2.
Intermediate 101-3 was synthesized in the same manner as in Synthesis of Intermediate 12-4, except that Intermediate 101-2 was used instead of Intermediate 12-3.
Intermediate 101-4 was synthesized in the same manner as in Synthesis of Intermediate 12-5, except that Intermediate 101-3 was used instead of Intermediate 12-4.
Intermediate 101-5 was synthesized in the same manner as in Synthesis of Intermediate 12-6, except that Intermediate 101-4 was used instead of Intermediate 12-5. The resulting compound was identified by LC-MS. C37H27N: M+ 485.2
4.85 g (10.0 mmol) of Intermediate 101-5, 4.66 g (20 mmol) of 4-bromo-1,1′-biphenyl, 0.92 g (1 mmol) of Pd2dba3, 0.42 g (2 mmol) of P(t-Bu)3, and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 80 ml of toluene, and stirred at a temperature of 80° C. for 3 hours. After the reaction solution was cooled to room temperature, 40 ml of water was added thereto, and an extraction process was performed thereon three times using 50 ml of ethyl ether. The collected ethyl ether was dried using MgSO4, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, to thereby obtain 4.74 g (yield: 60%) of Compound 101. The resulting compound was identified by MS/FAB and 1H NMR.
Compound 116 was synthesized in the same manner as in Synthesis Example 6, except that bromobenzene was used instead of 4-bromo-1,1′-biphenyl. The resulting compound was identified by MS/FAB and 1H NMR.
Table 1 below shows MS/FAB and 1H NMR results of a compound prepared according to each Synthesis Example.
1H NMR (CDCl3, 400 MHZ)
As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2 (1,200 Å) ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated using isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and mounted on a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å. 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
9,10-di(naphthalen-2-yl)anthracene (DNA) and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) were vacuum-deposited on the hole transport layer at a weight ratio of 98:2 to form an emission layer having a thickness of 300 Å.
Alq3 was vacuum-deposited on the emission layer to form an electron transport layer having a thickness of 300 Å. LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing manufacture of an organic light-emitting device.
An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that, in forming a hole transport layer, corresponding compounds shown in Table 2 were used instead of NPB.
An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that, when forming a hole transport layer, instead of forming a hole transport layer having a thickness of 300 Å by using NPB, Compound 37 was vacuum-deposited on the hole injection layer to form a first hole transport layer having a thickness of 100 Å, Compound HT3 was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 100 Å, and Compound 37 was vacuum-deposited on the second hole transport layer to form a third hole transport layer having a thickness of 100 Å.
An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that, when forming a hole transport layer, instead of forming a hole transport layer having a thickness of 300 Å by using NPB, Compound 37 was vacuum-deposited on the hole injection layer to form a first hole transport layer having a thickness of 100 Å, Compound 66 was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 100 Å, and Compound 37 was vacuum-deposited on the second hole transport layer to form a third hole transport layer having a thickness of 100 Å.
To evaluate characteristics of each of the organic light-emitting devices manufactured according to Comparative Examples 1 to 6 and Examples 1 to 13, driving voltage, luminance, luminescence efficiency, and lifespan were measured, and results thereof are shown in Table 2.
The driving voltage at the current density of 50 mA/cm2 was measured using a source meter (2400 series, Keithley Instrument Inc.).
Power was supplied from a current-voltage (Kethley SMU 236), and the luminance and the luminescence efficiency were measured by using a luminance meter PR650.
From Table 2, it was confirmed that the organic light-emitting devices according to Examples 1 to 13 had a relatively lower driving voltage, a relatively higher luminance, relatively higher luminescence efficiency, and a relatively longer lifespan than the organic light-emitting devices according to Comparative Examples 1 to 6.
According to embodiments, an amine-containing compound represented by Formula 1 may have excellent hole transport characteristics. A light-emitting device including the amine-containing compound may have a low driving voltage, a high luminance, high efficiency, and a long lifespan. The display quality of an electronic device including the light-emitting device and an electronic apparatus using the electronic device may be improved.
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 purpose 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 as set forth in the claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0068502 | Jun 2022 | KR | national |
