Patent Application
20240276874
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0001951, filed on Jan. 5, 2023, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
One or more embodiments of the present disclosure relate to a light-emitting device including an amine-containing compound, an electronic apparatus including the light-emitting device, and the amine-containing compound.
Light-emitting devices (for example, organic light-emitting devices) are self-emissive devices that have relatively wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of brightness, driving voltage, and response speed.
Light-emitting devices may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition and decay from an excited state to a ground state to thus generate light.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device including an amine-containing compound, an electronic apparatus including the light-emitting device, and the amine-containing compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments of the present disclosure, a light-emitting device may include:
According to one or more embodiments of the present disclosure, an electronic apparatus and electronic equipment may each include the light-emitting device.
According to one or more embodiments of the present disclosure, provided is the amine-containing compound represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the present disclosure, and duplicative descriptions thereof may not be provided for conciseness. In this regard, the embodiments of the present disclosure may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments of the present disclosure are merely described, by referring to the drawings, to explain aspects of the present disclosure. As utilized herein, the term “and/or” or “or” may include any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, “at least one of a, b or c”, “at least one selected from a, b, and c”, “at least one selected from among a to c”, etc., may indicate only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof. The “/” utilized herein may be interpreted as “and” or as “or” depending on the situation.
In one or more embodiments of the present disclosure, 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:
In one or more embodiments, R3 may be hydrogen, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, or a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, R3 may be hydrogen.
In one or more embodiments, R3 may be a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, and in some embodiments, R3 may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, or a bicyclo[2.2.2]octyl group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R11 to R16 may each independently be hydrogen, deuterium, —F, a cyano group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, R11 to R16 may each independently be: hydrogen, deuterium, —F, or a cyano group;
In one or more embodiments, R21 to R23 and R31 to R34 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, or a C1-C20 alkyl group;
In some embodiments, R21 to R23 and R31 to R34 may each independently be:
b13 and b15 may each be an integer from 0 to 7, b14 may be an integer from 0 to 8, b16 may be an integer from 0 to 3, b21, b23, and b31 to b34 may each independently be an integer from 0 to 3, and b22 may be an integer from 0 to 6.
In one or more embodiments, R1 may be one selected from groups represented by Formulae 1-1 to 1-12:
In one or more embodiments, L2 may be one selected from groups represented by Formulae 2-1 to 2-17:
In some embodiments, R2 may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, or a bicyclo[2.2.2]octyl group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R2 may be one selected from Formulae 2-A to 2-G:
Any hydrogen in a cyclohexyl group of Formula 2-A may be substituted with R2a other than hydrogen,
Any hydrogen in a norbornanyl group of Formulae 2-B and 2-C may be substituted with R2b other than hydrogen,
Any hydrogen in a bicyclo[2.2.2]octyl group of Formulae 2-D and 2-E may be substituted with R2c other than hydrogen, and
Any hydrogen in an adamantanyl group of Formulae 2-F and 2-G may be substituted with R2d other than hydrogen.
In one or more embodiments, L3 may be one selected from groups represented by Formulae 3-1 to 3-18:
In one or more embodiments, the amine-containing compound represented by Formula 1 may be one selected from Compounds 1 to 375:
The amine-containing compound represented by Formula 1 may reduce intermolecular interaction by including L3, thereby having low packing density and low refractive properties, and a refractive index of the molecule may be changed by varying the substituents of L3.
In some embodiments, by including R1 in the amine-containing compound, π-conjugation of the molecule may be widely extended, and stability of the molecule in a Polaron state may be increased, so that device lifespan and efficiency may be improved, and a glass transition temperature may be greatly increased by increasing the molecular weight. In some embodiments, by changing the type or kind and position of the substituent in R1, the energy level may be varied and tuned, and through such a variation, the hole injection barrier of the ITO and hole transfer layer may be varied. In some embodiments, the exciton generation efficiency inside the emission layer may be increased by controlling the appropriate or suitable energy level between the hole transfer layer and the emission layer.
As a result, an organic electroluminescent device employing the amine-containing compound represented by Formula 1 may have characteristics of high efficiency, low voltage, high luminance, and long lifespan.
Methods of synthesizing the amine-containing compound represented by Formula 1 may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
In one or more embodiments, at least one of the amine-containing compounds represented by Formula 1 may be utilized in a light-emitting device (e.g., an organic light-emitting device). Accordingly, 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 as described herein.
In one or more embodiments,
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or a combination thereof.
In one or more embodiments, the amine-containing compound represented by Formula 1 may be included in the interlayer.
In one or more embodiments, the amine-containing compound represented by Formula 1 may be included in the hole transport region.
In one or more embodiments, the amine-containing compound represented by Formula 1 may be included in the hole transport layer.
In one or more embodiments, the amine-containing compound represented by Formula 1 may be included in the hole transport layer, and the hole transport layer and the emission layer may be in direct contact with each other.
In one or more embodiments, the emission layer may be to emit blue light. For example, the emission layer may be to emit blue light having a maximum emission wavelength in a range of about 400 nanometers (nm) to about 500 nm, about 410 nm to about 490 nm, about 420 nm to about 480 nm, or about 430 nm to about 470 nm.
In one or more embodiments, the emission layer of the light-emitting device may include a dopant and a host.
In one or more embodiments, the electron transport region in the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicone-containing compound, or any combination thereof. In some embodiments, the hole blocking layer may be in a direct contact with the emission layer.
In one or more embodiments, the light-emitting device may include a capping layer located outside the first electrode or the second electrode. In some embodiments, the light-emitting device may further include a capping layer located outside the first electrode or the second electrode, and the amine-containing compound represented by Formula 1 may be included in the capping layer.
In one or more embodiments, the light-emitting device may further include at least one selected from among a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and at least one selected from among the first capping layer and the second capping layer may include the amine-containing compound. The first capping layer and the second capping layer may respectively be understood by referring to the descriptions of the first capping layer and the second capping layer provided herein.
In some embodiments, the light-emitting device may include:
The expression that an “(interlayer and/or a capping layer) includes an amine-containing compound” as utilized herein may be construed as meaning that the “(interlayer and/or the capping layer) may include one amine-containing compound of Formula 1 or two or more different amine-containing compounds of Formula 1”.
For example, in some embodiments, the interlayer and/or the capping layer may include Compound 1 only as the amine-containing compound. In those embodiments, Compound 1 may be included in the hole transport layer or the emission layer of the light-emitting device. In some embodiments, the interlayer may include Compounds 1 and 2 as the amine-containing compounds. In those embodiments, Compounds 1 and 2 may be included in substantially the same layer (for example, both (e.g., simultaneously) Compounds 1 and 2 may be included in the emission layer) or in different layers (for example, Compound 1 may be included in the emission layer, and Compound 2 may be included in the hole transport region).
The term “interlayer” as utilized herein refers to a single layer and/or a plurality of all layers located between a first electrode and a second electrode in a light-emitting device.
According to one or more embodiments, an electronic apparatus may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. In some embodiments, the electronic apparatus may further include a thin-film transistor including a source electrode and drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In some embodiments, the electronic apparatus may further include a color filter, a color-conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. The electronic apparatus may be understood by referring to the description of the electronic apparatus provided herein.
Hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 according to one or more embodiments will be described in more detail with reference to
In
The first electrode 110 may be formed by depositing or sputtering, on the substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, a high work function material that facilitates hole injection may be utilized as a material for the first electrode.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In some embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be utilized as a material for forming the first electrode 110.
The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO.
The interlayer 130 may be on the first electrode 110. The interlayer 130 may include an emission layer.
In one or more embodiments, 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.
In one or more embodiments, the interlayer 130 may further include metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, and/or the like, in addition to one or more suitable organic materials.
In one or more embodiments, the interlayer 130 may include: i) at least two emitting units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer between the at least two emitting units. When the interlayer 130 includes the at least two emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of 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 a combination thereof.
For example, in some embodiments, the hole transport region may have a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein constituent layers of each structure are sequentially stacked on the first electrode 110 in each stated order.
In some embodiments, the hole transport region may include, as an amine-containing compound, a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In some embodiments, Formulae 201 and 202 may each include at least one selected from groups represented by Formulae CY201 to CY217:
In one or more embodiments, in Formulae CY201 to CY217, ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, Formulae 201 and 202 may each include at least one selected from the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R202 may be represented by one selected from Formulae CY204 to CY207.
In one or more embodiments, Formulae 201 and 202 may each not include (e.g., may each exclude) any groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formulae 201 and 202 may each not include (e.g., may each exclude) any groups represented by Formulae CY201 to CY203, and may include at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, Formulae 201 and 202 may each not include (e.g., may each exclude) any groups represented by Formulae CY201 to CY217.
In some embodiments, the hole transport region may include one selected from Compounds HT1 to HT46, 4,4′,4″-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB (NPD)), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated-NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine](TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (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), and polyaniline/poly(4-styrenesulfonate (PANI/PSS), and/or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å (Angstroms) to about 10,000 Å, and in some embodiments, about 100 A to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and in some embodiments, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in some embodiments, 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, excellent or suitable hole transport characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer. The electron blocking layer may prevent or reduce leakage of electrons to the hole transport region from the emission layer. Materials that may be included in the hole transport region may also be included in the emission auxiliary layer and the electron blocking layer.
p-Dopant
In one or more embodiments, the hole transport region may include a charge generating material as well as the aforementioned materials to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed (for example, as a single layer including (e.g., consisting of) the charge generating material) in the hole transport region.
The charge generating material may include, for example, a p-dopant.
In some embodiments, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
In some embodiments, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound containing element EL1 and element EL2, or any combination thereof.
Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/or the like.
Non-limiting examples of the compound containing a cyano group include dipyrazino[2,3-f: 2′,3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), a compound represented by Formula 221, and/or the like:
In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be non-metal, a metalloid, or a combination thereof.
Non-limiting examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), and/or the like); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), and/or the like); a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and/or the like); and/or the like.
Non-limiting examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Non-limiting examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, and/or the like), and/or the like.
For example, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, and/or the like), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, and/or the like), a metal telluride, or any combination thereof.
Non-limiting examples of the metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, or W2O5), a vanadium oxide (e.g., VO, V2O3, VO2, or V2O5), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, or Mo2O5), a rhenium oxide (e.g., ReO3), and/or the like.
Non-limiting examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and/or the like.
Non-limiting examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCI, NaCl, KCl, RbCI, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, Nal, KI, Rbl, Csl, and/or the like.
Non-limiting examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mgl2, Cal2, Srl2, Bal2, and/or the like.
Non-limiting examples of the transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, or Til4), a zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, or Zrl4), a hafnium halide (e.g., HfF4, HfCl4, HfBr4, or Hfl4), a vanadium halide (e.g., VF3, VCl3, VBr3, or Vl3), a niobium halide (e.g., NbF3, NbCl3, NbBr3, or Nbl3), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, or Tal3), a chromium halide (e.g., CrF3, CrCl3, CrBr3, or Crl3), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, or Mol3), a tungsten halide (e.g., WF3, WCl3, WBr3, or Wl3), a manganese halide (e.g., MnF2, MnCl2, MnBr2, or Mnl2), a technetium halide (e.g., TcF2, TcCl2, TcBr2, or Tcl2), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, or Rel2), a ferrous halide (e.g., FeF2, FeCl2, FeBr2, or Fel2), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, or Rul2), an osmium halide (e.g., OsF2, OsCl2, OsBr2, or Osl2), a cobalt halide (e.g., CoF2, COCl2, CoBr2, or COl2), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, or Rhl2), an iridium halide (e.g., IrF2, IrCl2, IrBr2, or Irl2), a nickel halide (e.g., NiF2, NiCl2, NiBr2, or Nil2), a palladium halide (e.g., PdF2, PdCl2, PdBr2, or Pdl2), a platinum halide (e.g., PtF2, PtCl2, PtBr2, or Ptl2), a cuprous halide (e.g., CuF, CuCl, CuBr, or Cul), a silver halide (e.g., AgF, AgCl, AgBr, or Agl), a gold halide (e.g., AuF, AuCI, AuBr, or Aul), and/or the like.
Non-limiting examples of the post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, or Znl2), an indium halide (e.g., Inl3), a tin halide (e.g., Snl2), and/or the like.
Non-limiting examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, Ybl, Ybl2, Ybl3, Sml3, and/or the like.
Non-limiting examples of the metalloid halide may include an antimony halide (e.g., SbCl5) and/or the like.
Non-limiting examples of the metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, or Cs2Te), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, or BaTe), a transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, or Au2Te), a post-transition metal telluride (e.g., ZnTe), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, or LuTe), and/or the like.
When the light-emitting device 10 is a full color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact with each other or may be separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, and/or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer to emit white light (e.g., combined white light).
In one or more embodiments, the emission layer may include a host and a dopant. The dopant may be 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 to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emission layer may further include a first host and a second host, and the first host may be an electron transporting host, and the second host may be a hole transporting host.
In one or more embodiments, the first host may include at least one azine moiety, and the second host may include at least one carbazole moiety.
In one or more embodiments, the first host may include a compound represented by Formula 5:
In one or more embodiments, in Formula 5, ring CY51 to ring CY53 may each independently include i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
In some embodiments, in Formula 5, rings CY51 to CY53 may each independently include a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, in Formula 5, L51 to L53 may each independently include a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.
In one or more embodiments, the first host may include at least one selected from compounds represented by Formulae ETH1 to ETH32:
In one or more embodiments, the second host may include a compound including a group represented by Formula 7:
In one or more embodiments, in Formula 7, ring CY71 and ring CY72 may each independently include i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
In some embodiments, in Formula 7, rings CY71 and CY72 may each independently include a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, the second host may include a compound represented by one selected from Formulae 7-1 to 7-5:
In one or more embodiments,
may be selected from groups represented by Formulae CY71-1(1) to CY71-1(8),
may be selected from groups represented by Formulae CY71-2(1) to CY71-2(8)
may be selected from groups represented by Formulae CY71-3(1) to CY71-3(32),
may be selected from groups represented by Formulae CY71-4(1) to CY71-4(32), and
may be selected from groups represented by Formulae CY71-5(1) to CY71-5(8):
In Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
In one or more embodiments, the second host may include at least one selected from compounds represented by Formulae HTH1 to HTH40.
In a light-emitting device according to one or more embodiments, the first host and the second host may form an exciplex, an organometallic compound and the first host or the organometallic compound and the second host may not form an exciplex.
In some embodiments, the emission layer may include quantum dots.
In some embodiments, 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, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the host may include a compound represented by Formula 301:
In some embodiments, when xb11 in Formula 301 is 2 or greater, at least two Ar301(s) may be bound via a single bond.
In some embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In some embodiments, the host may include an alkaline earth-metal complex, a post-transitional metal complex, or any combination thereof. For example, in some embodiments, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In some embodiments, the host may include one selected from among Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di(carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl) benzene (TCP), and/or any combination thereof:
In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a center 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.
In some embodiments, the phosphorescent dopant may be electrically neutral.
In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
For example, in some embodiments, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) X401 and X402 may each be nitrogen.
In one or more embodiments, when xc1 in Formula 402 is 2 or greater, two ring A401 (s) of at least two L401 (s) may optionally be bound via T402 as a linking group, and/or two ring A402(s) may optionally be bound via T403 as a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be understood by referring to the description of T401 provided herein.
In Formula 401, L402 may be any suitable organic ligand. For example, in some embodiments, L402 may be a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, —CN, a phosphorus-containing group (e.g., a phosphine group or a phosphite group), or any combination thereof.
In one or more embodiments, the phosphorescent dopant may be, for example, one selected from among Compounds PD1 to PD39, and/or any combination thereof:
In one or more embodiments, the fluorescent dopant may include an amine-containing compound represented by Formula 501, a styryl-containing compound, or any combination thereof:
In some embodiments, in Formula 501, Ar501 may include a condensed ring group (e.g., an anthracene group, a chrysene group, or a pyrene group) in which at least three monocyclic groups are condensed.
In some embodiments, xd4 in Formula 501 may be 2.
In some embodiments, the fluorescent dopant may include one selected from among Compounds FD1 to FD37, 4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl (DPVBi), 4,4′-bis[4-(N,N-diphenylamino)styryl]biphenyl (DPAVBi), and/or any combination thereof:
In one or more embodiments, the emission layer may include a delayed fluorescence material.
The delayed fluorescence material described herein may be any suitable compound that may be to emit delayed fluorescence according to a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may serve as a host or a dopant, depending on types (kinds) of other materials included in the emission layer.
In some embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be about 0 eV or greater and about 0.5 eV or less. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is within this range, up-conversion from the triplet state to the singlet state in the delayed fluorescence material may be effectively occurred, thus improving luminescence efficiency and/or the like of the light-emitting device 10.
In some embodiments, the delayed fluorescence material may include: i) a material including at least one electron donor (e.g., a rr electron-rich C3-C60 cyclic group such as a carbazole group and/or the like) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a rr electron-deficient nitrogen-containing C1-C60 cyclic group, and/or the like), ii) a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other and sharing boron (B), and/or iii) the like.
Non-limiting examples of the delayed fluorescence material may include at least one selected from Compounds DF1 to DF14:
In one or more embodiments, the emission layer may include quantum dots.
The term “quantum dot” as utilized herein refers to a crystal of a semiconductor compound and may include any suitable material capable of emitting emission wavelengths of one or more suitable lengths according to the size of the crystal.
The diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
Quantum dots may be synthesized by a wet chemical process, an organic metal chemical vapor deposition process, a molecular beam epitaxy process, or any similar process.
The wet chemical process is a method of growing a quantum dot particle crystal by mixing a precursor material with an organic solvent. When the crystal grows, the organic solvent may naturally serve as a dispersant coordinated on the surface of the quantum dot crystal and control the growth of the crystal. Thus, the wet chemical method may be easier to perform than the vapor deposition process such a metal organic chemical vapor deposition (MOCVD) or a molecular beam epitaxy (MBE) process. Further, the growth of quantum dot particles may be controlled or selected with a lower manufacturing cost.
The quantum dot may include a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element or compound; or any combination thereof.
Non-limiting 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, and/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, and/or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or a combination thereof.
Non-limiting 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, and/or InSb; a ternary compound such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GalnNP, GaInNAs, GalnNSb, GaInPAs, GalnPSb, InAINP, InAINAs, InAINSb, InAIPAs, and/or InAIPSb; or any combination thereof. In some embodiments, the group Ill-V semiconductor compound may further include a group II element. Non-limiting examples of the group III-V semiconductor compound further including the group II element may include InZnP, InGaZnP, InAIZnP, and/or the like.
Non-limiting examples of the III-VI group semiconductor compound may include a binary compound such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and/or the like; a ternary compound such as InGaS3, InGaSe3, and/or the like; or a combination thereof.
Non-limiting examples of the group I—III-VI semiconductor compound may include a ternary compound such as AgInS, AgInS2, CuInS, CulnS2, CuGaO2, AgGaO2, or AgAlO2; or a combination thereof.
Non-limiting examples of the group IV-VI semiconductor compound may include: a binary compound such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quaternary compound such as SnPbSSe, SnPbSeTe, and/or SnPbSTe; or a combination thereof.
The group IV element or compound may be a single element material such as Si and/or Ge; a binary compound such as SiC and/or SiGe; or a combination thereof.
Individual elements included in a multi-element compound, such as a binary compound, a ternary compound, and a quaternary compound, may be present in a particle thereof at a substantially uniform or non-substantially uniform concentration.
The quantum dot may have a single structure in which the concentration of each element included in the quantum dot is substantially uniform or a core-shell double structure. In some embodiments, materials included in the core may be different from materials included in the shell.
The shell of the quantum dot may serve as a protective layer for preventing or reducing chemical denaturation of the core to maintain semiconductor characteristics and/or as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be a monolayer or a multilayer. An interface between the core and the shell may have a concentration gradient where a concentration of elements present in the shell decreases toward the core.
Non-limiting examples of the shell of the quantum dot may include metal, metalloid, or nonmetal oxide, a semiconductor compound, or a combination thereof. Non-limiting examples of the metal, the metalloid, or the nonmetal oxide suitable as a shell may include a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, CO3O4, and/or NiO; a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; or any combination thereof. Non-limiting examples of the semiconductor compound suitable as a shell may include: a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group 1-III-VI semiconductor compound; a group IV-VI semiconductor compound; or any combination thereof. In some embodiments, the semiconductor compound suitable as a shell may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
The quantum dot may have a full width of half maximum (FWHM) of an emission spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of the quantum dot is within this range, color purity or color reproducibility may be improved. In some embodiments, because light emitted through the quantum dots is emitted in all directions, an optical viewing angle may be improved.
In some embodiments, the quantum dot may be a substantially spherical, pyramidal, multi-arm, or cubic nanoparticle, nanotube, nanowire, nanofiber, or nanoplate particle.
By adjusting the size of the quantum dot, the energy band gap of the quantum dot may also be adjusted, thereby obtaining light of one or more suitable wavelengths in a quantum dot emission layer. By utilizing quantum dots of one or more suitable sizes, a light-emitting device that may be to emit light of one or more suitable wavelengths may be realized. In some embodiments, the size of the quantum dot may be selected such that the quantum dot may be to emit red, green, and/or blue light. In some embodiments, the size of the quantum dot may be selected such that the quantum dot may be to emit white light by combining one or more suitable light colors.
The electron transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein constituent layers of each structure are sequentially stacked on the emission layer in each stated order.
In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one rr electron-deficient nitrogen-containing C1-C60 cyclic group.
In some embodiments, the electron transport region may include a compound represented by Formula 601:
For example, in some embodiments, in Formula 601, when xe11 is 2 or greater, two or more of Ar601(s) may be bound to each other via a single bond.
In some embodiments, in Formula 601, Ar601 may be a substituted or unsubstituted anthracene group.
In some embodiments, the electron transport region may include a compound represented by Formula 601-1:
For example, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In one or more embodiments, the electron transport region may include at least one selected from among Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), and/or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, and in some embodiments, 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 a combination thereof, the thicknesses of the buffer layer, the hole blocking layer, and/or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are each within these ranges, excellent or suitable electron transport characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, 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. A metal ion of the alkali metal complex may be a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, or a cesium (Cs) ion. A metal ion of the alkaline earth metal complex may be a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, or a barium (Ba) ion. Each ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may independently be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (LiQ) or Compound ET-D2:
In one or more embodiments, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
The electron injection layer may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of 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 be Li, Na, K, Rb, Cs or any combination thereof. The alkaline earth metal may be Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may be 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 respectively be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), tellurides, or any combination thereof of each of the alkali metal, the alkaline earth metal, and the rare earth metal.
The alkali metal-containing compound may be alkali metal oxides such as Li2O, Cs2O, and/or K2O, alkali metal halides such as LiF, NaF, CsF, KF, Lil, Nal, Csl, and/or KI, or any combination thereof. The alkaline earth-metal-containing compound may include alkaline earth-metal oxides, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), and/or BaxCa1-xO (wherein x is a real number satisfying 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, Ybl3, Scl3, Tbl3, or any combination thereof. In some embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting 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/or Lu2Te3.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may include: i) one of ions of the alkali metal, alkaline earth metal, and rare earth metal described above, respectively, and ii) a ligand bond to the metal ion, e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In some embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
In some embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In some embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a Rbl:Yb co-deposition layer, a LiF:Yb co-deposition layer, and/or the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof may be substantially homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, excellent or suitable electron injection characteristics may be obtained without a substantial increase in driving voltage.
Second electrode 150
The second electrode 150 may be on the interlayer 130. In one or more embodiments, the second electrode 150 may be a cathode that is an electron injection electrode. In those embodiment, a material for forming the second electrode 150 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a combination thereof, each having 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 including two or more layers.
A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
In some embodiments, in the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer to the outside. In some embodiments, in the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the second electrode 150 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer to the outside.
The first capping layer and the second capping layer may improve the external luminescence efficiency based on the principle of constructive interference. Accordingly, the optical extraction efficiency of the light-emitting device 10 may be increased, thus improving the luminescence efficiency of the light-emitting device 10.
The first capping layer and the second capping layer may each include a material having a refractive index of 1.6 or higher (e.g., at 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one selected from among the first capping layer and the second capping layer may (e.g., 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. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In some embodiments, at least one selected from among the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each) independently include an amine group-containing compound.
In some embodiments, at least one selected from among the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each) independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each) independently include at least one selected from among Compounds HT28 to HT33, Compounds CP1 to CP6, β-NPB, and/or any combination thereof:
The amine-containing compound represented by Formula 1 may be included in one or more suitable films. According to one or more embodiments of the present disclosure, a film including the amine-containing compound represented by Formula 1 may be provided. 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 polarizing layer, a quantum dot-containing layer, and/or the like), alight-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).
The light-emitting device may be included in one or more suitable electronic apparatuses. In some embodiments, an electronic apparatus including the light-emitting device may be a light-emitting apparatus or an authentication apparatus.
In one or more embodiments, the electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be disposed on at least one travel direction of light emitted from the light-emitting device. For example, in some embodiments, light emitted from the light-emitting device may be blue light or white light (e.g., combined white light). The light-emitting device may be understood by referring to the descriptions provided herein. In some embodiments, the color conversion layer may include quantum dots. The quantum dot may be, for example, the quantum dot described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the plurality of sub-pixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the plurality of sub-pixel areas.
A pixel-defining film may be located between the plurality of sub-pixel areas to define each sub-pixel area.
The color filter may further include a plurality of color filter areas and light-blocking patterns between the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-blocking patterns between the plurality of color conversion areas.
The plurality of color filter areas (or a plurality of color conversion areas) may include: a first area to emit first color light; a second area to emit second color light; and/or a third area to emit third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. In some embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In some embodiments, the plurality of color filter areas (or the plurality of color conversion areas) may each include quantum dots. In some embodiments, the first area may include red quantum dots to emit red light, the second area may include green quantum dots to emit green light, and the third area may not include (e.g., may exclude) a quantum dot. The quantum dot may be understood by referring to the description of the quantum dot provided herein. The first area, the second area, and/or the third area may each further include an emitter.
In some embodiments, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. In these embodiments, the first-first color light, the second-first color light, and the third-first color light may each have a different maximum emission wavelength. In some embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first light may be blue light.
In one or more embodiments, the electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The active layer may include a crystalline silicon, an amorphous silicon, an organic semiconductor, and/or an oxide semiconductor.
In one or more embodiments, the electronic apparatus may further include an encapsulation unit for sealing the light-emitting device. The encapsulation unit may be located between the color filter and/or the color conversion layer and the light-emitting device. The encapsulation unit may allow light to pass to the outside from the light-emitting device and prevent or reduce the air and moisture to permeate to the light-emitting device at the same time. The encapsulation unit may be a sealing substrate including transparent glass or a plastic substrate. The encapsulation unit may be a thin-film encapsulating layer including at least one of an organic layer and/or an inorganic layer. When the encapsulation unit is a thin-film encapsulating layer, the electronic apparatus may be flexible.
In addition to the color filter and/or the color conversion layer, one or more suitable functional layers may be disposed on the encapsulation unit depending on the utilization of the electronic apparatus. Non-limiting examples of the functional layer may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a resistive touch screen layer, a capacitive touch screen layer, or an infrared beam touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according to biometric information (e.g., a fingertip, a pupil, and/or the like).
The authentication apparatus may further include a biometric information collecting unit, in addition to the light-emitting device described above.
The electronic apparatus may be applicable to one or more suitable displays, an optical source, lighting, a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, or an endoscope display device), a fish finder, one or more suitable measurement devices, gauges (e.g., gauges of an automobile, an airplane, or a ship), and/or a projector.
The electronic apparatus shown in
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and provide a flat surface on the substrate 100.
A thin-film transistor may be on the buffer layer 210. The thin-film transistor may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor and may include a source area, a drain area, and a channel area.
A gate insulating film 230 for insulating the active layer 220 and the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to provide insulation therebetween.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source area and the drain area of the active layer 220, and the source electrode 260 and the drain electrode 270 may be adjacent to (e.g., in contact with) the exposed source area and the exposed drain area of the active layer 220, respectively.
The thin-film transistor may be electrically connected to a light-emitting device to drive the light-emitting device and may be protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device may be on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not fully cover the drain electrode 270 and expose a specific area of the drain electrode 270, and the first electrode 110 may be disposed to connect to the exposed area of the drain electrode 270.
A pixel-defining film 290 may be on the first electrode 110. The pixel-defining film 290 may expose a specific area of the first electrode 110, and the interlayer 130 may be formed in the exposed area of the first electrode 110. The pixel-defining film 290 may be a polyimide or polyacryl organic film. In some embodiments, at least some layers of the interlayer 130 may extend to the upper portion of the pixel-defining film 290 to be located in the form of a common layer.
The second electrode 150 may be 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 unit 300 may be on the capping layer 170. The encapsulation unit 300 may be on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation unit 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including PET, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxy methylene, poly arylate, hexamethyl disiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy resin (e.g., aliphatic glycidyl ether (AGE) and/or the like), or any combination thereof; or a combination of the inorganic film(s) and/or the organic film(s).
The electronic apparatus shown in
The electronic equipment 1 shown in
The non-display area NDA may be an area that may not display an image, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to the display devices arranged in the display area DA may be arranged. In the non-display area NDA, a pad, which is an area to which an electronic device or a printed circuit board may be electrically connected, may be arranged.
The electronic equipment 1 may have different lengths in the x-axis direction and in the y-axis direction. For example, in some embodiments, as shown in
In
The vehicle 1000 may travel on roads or tracks. The vehicle 1000 may move in a set or predetermined direction according to rotation of at least one wheel thereof. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a motorbike, a bicycle, or a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as the remaining parts except for the body. The exterior of the body of the vehicle 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 generating apparatus, a power transmitting apparatus, a traveling apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, front and rear, left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar located between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on a side of the vehicle 1000. In some embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. In some embodiments, the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In some embodiments, the side window glasses 1100 may be spaced apart from each other in the x direction or the −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the −x direction. In other words, an imaginary straight line L connecting the side window glasses 1100 may extend in the x direction or the −x direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed on a front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the body of the vehicle. In some embodiments, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be located outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be located outside the second side window glass 1120.
The cluster 1400 may be located in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning indicator, a seat belt warning indicator, an odometer, a hodometer, an automatic shift selector indicator, a door open warning indicator, an engine oil warning indicator, and/or a low fuel warning indicator.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio apparatus, an air conditioning apparatus, and/or a heater of seats. The center fascia 1500 may be on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 interposed therebetween. In some embodiments, the cluster 1400 may be disposed to correspond to a driver seat, and the passenger seat dashboard 1600 may be disposed to correspond to a passenger seat. In some embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In one or more embodiments, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be inside the vehicle 1000. In some embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be on at least one selected from among the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic EL display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, as the display apparatus 2 according to one or more embodiments, an organic light-emitting display apparatus including the light-emitting device according to one or more embodiments will be described as an example, however, embodiments of the present disclosure may include one or more suitable types (kinds) of the display apparatus.
As shown in
As shown in
As shown in
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a specific region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and/or laser-induced thermal imaging.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C. at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, depending on a material to be included in each layer and the structure of each layer to be formed.
The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group including (e.g., consisting of) carbon atoms only and having 3 to 60 carbon atoms as ring-forming atoms. The term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group having 1 to 60 carbon atoms in addition to a heteroatom as a ring-forming atom other than carbon atoms. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group including (e.g., consisting of) one ring or a polycyclic group in which at least two rings are condensed. For example, the number of ring-forming atoms in the C1-C60 heterocyclic group may be in a range of 3 to 61.
The term “cyclic group” as utilized herein may include the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “rr electron-rich C3-C60 cyclic group” refers to a cyclic group having 3 to 60 carbon atoms and not including *—N═*′ as a ring-forming moiety. The term “rr electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refers to a heterocyclic group having 1 to 60 carbon atoms and *—N═*′ as a ring-forming moiety.
In some embodiments,
The term “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “rr electron-rich C3-C60 cyclic group”, or “rr electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein may be a group condensed with any suitable cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a quadrivalent group, and/or the like), depending on the structure of a formula to which the term is applied. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, and this may be understood by one of ordinary skill in the art, depending on the structure of Formula including the “benzene group”.
Depending on context, in the present disclosure, a divalent group may refer or be a polyvalent group (e.g., trivalent, tetravalent, etc., and not just divalent) per, e.g., the structure of a formula in connection with which of the terms are utilized.
In some embodiments, non-limiting examples of the monovalent C3-C60 carbocyclic group and monovalent C1-C60 heterocyclic group may include a C3-C10 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and non-limiting examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C60 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and/or a tert-decyl group. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as utilized herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group. Non-limiting examples thereof may include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group. Non-limiting examples thereof may include an ethynyl group and/or a propynyl group. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as utilized herein refers to a monovalent group represented by —OA101 (wherein A101 is a C1-C60 alkyl group). Non-limiting examples thereof may include a methoxy group, an ethoxy group, and/or an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon monocyclic group including 3 to 10 carbon atoms. Non-limiting examples of the C3-C10 cycloalkyl group as utilized herein may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl (bicyclo[2.2.1]heptyl) group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and/or a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group including at least one heteroatom other than carbon atoms as a ring-forming atom and having 1 to 10 carbon atoms. Non-limiting examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and/or a tetrahydrothiophenyl group. The term “C1-C60 heterocycloalkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as utilized herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and is not aromatic. Non-limiting examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and/or a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as utilized herein refers to a monovalent cyclic group including at least one heteroatom other than carbon atoms as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and/or a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as utilized herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C6-C60 arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and/or an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each independently include two or more rings, the respective rings may be fused.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system further including at least one heteroatom other than carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system further including at least one heteroatom other than carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and/or a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each independently include two or more rings, the respective rings may be fused.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group that has two or more rings condensed to each other and only carbon atoms (e.g., 8 to 60 carbon atoms) as ring forming atoms, wherein the molecular structure when considered as a whole is non-aromatic. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and/or an indenoanthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group that has two or more rings condensed to each other and at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the molecular structure when considered as a whole is non-aromatic. Non-limiting examples of 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 indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is a C6-C60 aryl group). The term “C6-C60 arylthio group” as utilized herein refers to —SA103 (wherein A103 is a C6-C60 aryl group).
The term “C7-C60 aryl alkyl group” as utilized herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group). The term “C2-C60 heteroaryl alkyl group” as utilized herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as utilized herein may be:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 aryl alkyl group; or a C2-C60 heteroaryl alkyl group.
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
A third-row transition metal as utilized herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
The term “Ph” as utilized herein refers to a phenyl group. The term “Me” as utilized herein refers to a methyl group. The term “Et” as utilized herein refers to an ethyl group. The term “tert-Bu” or “But” as utilized herein refers to a tert-butyl group. The term “OMe” as utilized herein refers to a methoxy group.
The term “biphenyl group” as utilized herein refers to a phenyl group substituted with a phenyl group. In other words, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as utilized herein refers to a phenyl group substituted with a biphenyl group. In other words, the “terphenyl group” may be a substituted phenyl group having a C6-C60 aryl group substituted with a C6-C60 aryl group as a substituent.
The symbols * and *′ as utilized herein, unless defined otherwise, refer to a binding site to an adjacent atom in a corresponding formula or moiety.
In the present disclosure, the x-axis, y-axis, and z-axis are not limited to three axes on an orthogonal coordinates system, and may be interpreted in a broad sense including the orthogonal coordinates system. For example, the x-axis, y-axis, and z-axis may be orthogonal to each other, but the x-axis, y-axis, and z-axis may also refer to different directions that are not orthogonal to each other.
Hereinafter, compounds and a light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical number of molar equivalents of B was utilized in place of A.
4-cyclohexylaniline (1.0 eq.), 2-bromo-9,9-dimethyl-9H-fluorene (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 1-1 was obtained (yield: 85%).
phenylboronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in 2-bromo-4′-chloro-1,1′-biphenyl (1.0 eq.) were dissolved in a solvent having a volumetric ratio of tetrahydrofuran (THF):H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 1-2 was obtained (yield: 85%).
Intermediate Compound 1-1 (1.0 eq.), Intermediate Compound 1-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 1 was obtained (yield: 80%). By fast-atom bombardment mass spectrometry (FAB-MS), mass number m/z=595.32 was observed as a molecular ion peak. Thus, Compound 1 was identified.
phenylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in 2,2′-dibromo-1,1′-biphenyl (1.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 2-1 was obtained (yield: 55%).
Intermediate Compound 1-1 (1.0 eq.), Intermediate Compound 2-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 2 was obtained (yield: 80%). By FAB-MS, mass number m/z=595.32 was observed as a molecular ion peak. Thus, Compound 2 was identified.
[1,1′-biphenyl]-2-ylboronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in 2-bromo-4′-chloro-1,1′-biphenyl (1.0 eq.) were dissolved in a solvent having a volumetric ratio of dioxane:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 3-1 was obtained (yield: 65%).
Intermediate Compound 1-1 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 3 was obtained (yield: 63%). By FAB-MS, mass number m/z=671.36 was observed as a molecular ion peak. Thus, Compound 3 was identified.
1-Bromo-4-cyclohexylbenzene (1.0 eq.), 9,9-dimethyl-9H-fluoren-2-amine (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 5-1 was obtained (yield: 68%).
2-bromo-4′-chloro-1,1′-biphenyl (1.0 eq.), (4-cyclohexylphenyl)boronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (6.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 5-2 was obtained (yield: 65).
Intermediate Compound 5-1 (1.0 eq.), Intermediate Compound 5-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 5 was obtained (yield: 65%). By fast-atom bombardment mass spectrometry (FAB-MS), mass number m/z=677.40 was observed as a molecular ion peak. Thus, Compound 5 was identified.
2-methylphenylboronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in methyl 2-bromo-5-chlorobenzoate (1.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 23-1 was obtained (yield: 85%).
200 mL of THF was added to Intermediate Compound 23-1 (1.0 eq.), followed by cooling to 0° C. Under nitrogen atmosphere, methyl magnesium bromide (4.0 eq.) was added dropwise thereto, followed by stirring for 1 hour. Ammonium chloride aqueous solution was added dropwise thereto for neutralization, extraction was performed with ethyl acetate and water three times (e.g., dissolved in ethyl acetate and washed with water three times), and the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 23-2 was obtained (yield: 78%).
Trifluoromethanesulfonic acid (10 eq.) was slowly added dropwise to Intermediate Compound 23-2 (1.0 eq.) and dichloromethane (DCM) (200 mL), followed by stirring at a temperature of 50° C. Once the mixture was cooled to room temperature and extracted three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 23-3 was obtained (yield: 72%).
4-cyclohexylaniline (1.0 eq.), Intermediate Compound 23-3 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 23-4 was obtained (yield: 85%).
Intermediate Compound 23-4 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 23 was obtained (yield: 63%). By FAB-MS, mass number m/z=685.37 was observed as a molecular ion peak. Thus, Compound 23 was identified.
9,9-dimethyl-9H-fluoren-2-amine (1.0 eq.) was dissolved in DCM, and N-bromosuccinimide (1.0 eq.) was slowly added dropwise thereto at a temperature of 0° C. Once the mixture was warmed to room temperature and washed three times utilizing ethyl acetate and water in which sodium thiosulfate was dissolved, the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 83-1 was obtained (yield: 95%).
Intermediate Compound 83-1 (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in phenylboronic acid (1.2 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 2 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 83-2 was obtained (yield: 85%).
Intermediate Compound 83-2 (1.0 eq.), 1-bromo-4-cyclohexylbenzene (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 83-3 was obtained (yield: 85%).
Intermediate Compound 83-3 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 83 was obtained (yield: 63%). By FAB-MS, mass number m/z=747.39 was observed as a molecular ion peak. Thus, Compound 83 was identified.
9,9-diphenyl-9H-fluoren-2-amine (1.0 eq.), 1-bromo-4-cyclohexylbenzene (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 103-1 was obtained (yield: 87%).
Intermediate Compound 103-1 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 103 was obtained (yield: 63%). By FAB-MS, mass number m/z=795.39 was observed as a molecular ion peak. Thus, Compound 103 was identified.
2-methylphenylboronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in methyl 2-bromo-5-chlorobenzoate (1.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 123-1 was obtained (yield: 85%).
200 mL of THF was added to Intermediate Compound 123-1 (1.0 eq.), followed by cooling to 0° C. Under nitrogen atmosphere, phenyl magnesium bromide (4.0 eq.) was added dropwise thereto, followed by stirring for 1 hour. Ammonium chloride aqueous solution was added dropwise thereto for neutralization, extraction was performed with ethyl acetate and water three times (e.g., dissolved in ethyl acetate and washed with water three times), and the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 123-2 was obtained (yield: 76%).
Trifluoromethanesulfonic acid (10 eq.) was slowly added dropwise to Intermediate Compound 123-2 (1.0 eq.) and DCM (200 mL), followed by stirring at a temperature of 50° C. Once the mixture was cooled to room temperature and extracted three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 123-3 was obtained (yield: 68%).
4-cyclohexylaniline (1.0 eq.), Intermediate Compound 123-3 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 123-4 was obtained (yield: 85%).
Intermediate Compound 123-4 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 123 was obtained (yield: 63%). By FAB-MS, mass number m/z=809.40 was observed as a molecular ion peak. Thus, Compound 123 was identified.
p-tolylboronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) in 1-bromo-4-methylbenzene (1.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 241-1 was obtained (yield: 85%).
Intermediate Compound 241-1 (1.0 eq.) was dissolved in DCM, and Br2 (1.0 eq.) was slowly added thereto under a nitrogen atmosphere and at a temperature of 0° C. After stirring for 4 hours at room temperature, an organic layer resulting from washing three times with ethyl acetate and water was washed with sodium thiosulfate aqueous solution and dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 241-2 was obtained (yield: 85%).
THF was added to Intermediate Compound 241-2 (1.0 eq.), followed by cooling to −78° C. Under nitrogen atmosphere, n-butyl lithium (1.1 eq.) was added dropwise thereto, followed by stirring for 1 hour at room temperature. 2-bromo-9H-fluoren-9-one (1.1 eq.) dissolved in THF was added dropwise thereto at room temperature, followed by stirring for 4 hours. Then, the resulting organic layer washed three times with ethyl acetate and water was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 241-3 was obtained (yield: 67%).
Trifluoromethanesulfonic acid (10 eq.) was slowly added dropwise to Intermediate Compound 241-3 (1.0 eq.) and DCM, followed by stirring at a temperature of 50° C. Once the mixture was cooled to room temperature and extracted three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 241-4 was obtained (yield: 72%).
4-cyclohexylaniline (1.0 eq.), Intermediate Compound 241-4 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 241-5 was obtained (yield: 85%).
Intermediate Compound 241-5 (1.0 eq.), Intermediate Compound 1-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 241 was obtained (yield: 63%). By FAB-MS, mass number m/z=75.37 was observed as a molecular ion peak. Thus, Compound 241 was identified.
1-bromo-4-cyclohexylbenzene (1.0 eq.), (4-aminophenyl)boronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (6.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 265-1 was obtained (yield: 65%).
Intermediate Compound 265-1 (1.0 eq.), 2-bromo-9,9-dimethyl-9H-fluorene (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-1 2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 265-2 was obtained (yield: 68%).
2-bromo-4′-chloro-1,1′-biphenyl (1.0 eq.), (4-cyclohexylphenyl)boronic acid (1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (6.0 eq.) were dissolved in a solvent having a volumetric ratio of THF:H2O of 4:1, followed by stirring under nitrogen atmosphere at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 265-3 was obtained (yield: 65%).
Intermediate Compound 265-2 (1.0 eq.), Intermediate Compound 265-3 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 265 was obtained (yield: 65%). By FAB-MS, mass number m/z=753.43 was observed as a molecular ion peak. Thus, Compound 265 was identified.
Intermediate Compound 265-1 (1.0 eq.), Intermediate Compound 23-3 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 268-1 was obtained (yield: 68%).
Intermediate Compound 268-1 (1.0 eq.), Intermediate Compound 3-1 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 268 was obtained (yield: 80%). By FAB-MS, mass number m/z=761.40 was observed as a molecular ion peak. Thus, Compound 268 was identified.
Intermediate Compound 268-1 (1.0 eq.), Intermediate Compound 5-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 270 was obtained (yield: 80%). By FAB-MS, mass number m/z=767.45 was observed as a molecular ion peak. Thus, Compound 270 was identified.
Intermediate Compound 265-1 (1.0 eq.), 2-bromo-9,9-diphenyl-9H-fluorene (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 291-1 was obtained (yield: 68%).
Intermediate Compound 291-1 (1.0 eq.), Intermediate Compound 1-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Compound 291 was obtained through column chromatography (yield: 80%). By FAB-MS, mass number m/z=795.39 was observed as a molecular ion peak. Thus, Compound 291 was identified.
Intermediate Compound 265-1 (1.0 eq.), Intermediate Compound 123-3 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 296-1 was obtained (yield: 68%).
Intermediate Compound 296-1 (1.0 eq.), Intermediate Compound 1-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Finally, through column chromatography, Compound 268 was obtained (yield: 80%). By FAB-MS, mass number m/z=809.40 was observed as a molecular ion peak. Thus, Compound 296 was identified.
Intermediate Compound 265-1 (1.0 eq.), 2′-bromospiro[benzo[de]anthracene-7,9′-fluorene] (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 100° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Through column chromatography, Intermediate Compound 356-1 was obtained (yield: 68%).
Intermediate Compound 356-1 (1.0 eq.), Intermediate Compound 1-2 (1.2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, followed by stirring under nitrogen atmosphere at a temperature of 110° C. for 1 hour. Once the mixture was cooled and washed three times utilizing ethyl acetate and water (e.g., dissolved in ethyl acetate and washed with water three times), the resulting organic layer was dried utilizing MgSO4 and then dried under reduced pressure. Compound 356 was obtained through column chromatography (yield: 80%). By FAB-MS, mass number m/z=843.39 was observed as a molecular ion peak. Thus, Compound 356 was identified.
Methods of synthesizing compounds other than the compounds synthesized in Synthesis Examples 1 to 15 may be easily understood to those skilled in the art by referring to the synthesis pathways and raw materials described above.
The lowest unoccupied molecular orbital (LUMO) energy level, highest occupied molecular orbital (HOMO) energy level, Bandgap, maximum emission wavelength (λmax), and refractive index of each of the Compounds prepared in the Synthesis Examples were measured as shown in Table 1. The results thereof are shown in Table 2.
As an anode, a 15 Ohms per square centimeter (0/cm2) (1,200 Å) ITO glass substrate (available from Corning Co., Ltd) was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, cleaned with ultraviolet rays for 30 minutes, and then ozone, and was 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. Compound 1 was then 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) as a host material and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) as a dopant material were co-deposited concurrently (e.g., simultaneously) on the hole transport layer at a weight ratio of 98:2 to form an emission layer having a thickness of 300 Å.
Then, 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, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices of Examples 2 to 15 and Comparative Examples 1 to 13 were each manufactured in substantially the same manner as in Example 1, except that Compounds 2, 3, 5, 23, 83, 103, 123, 241, 265, 268, 270, 291, 296, and 351 and Comparative Example Compounds 1 to 13 were respectively utilized instead of Compound 1 in forming a hole transport layer.
An organic light-emitting device of Example 16 was manufactured in substantially the same manner as in Example 1, except that, in forming a hole transport layer, Compound 1 was deposited to a thickness of 100 Å to form a first hole transport layer, HT01 was deposited to a thickness of 100 Å on the first hole transport layer to form a second hole transport layer, Compound 1 was deposited on the second hole transport layer to a thickness of 100 Å to form a third hole transport layer, thereby forming a hole transport layer.
In some embodiments, an organic light-emitting device of Example 17 was manufactured in substantially the same manner as in Example 16, except that Compound 268, HT01, and Compound 268 were respectively utilized for the first hole transport layer, the second hole transport layer, and the third hole transport layer, and an organic light-emitting device of Example 18 was manufactured in substantially the same manner as in Example 16, except that Compound 270, HT01, and Compound 270 were respectively utilized for the first hole transport layer, the second hole transport layer, and the third hole transport layer.
An organic light-emitting device of Comparative Example 14 was manufactured in substantially the same manner as in Example 16, except that Comparative Example Compound 9, HT01, and Comparative Example Compound 9 were respectively utilized for the first hole transport layer, the second hole transport layer, and the third hole transport layer.
The driving voltage (V), current density (mA/cm2), luminance (cd/m2), luminescence efficiency (cd/A), and lifespan (hours) at 1,000 cd/m2 of each of the organic light-emitting devices of Examples 1 to 18 and Comparative Examples 1 to 14 were measured utilizing a Keithley SMU 236 and a PR650 luminance meter. The results thereof are shown in Table 3.
As should be apparent from the foregoing description, when the amine-containing compound represented by Formula 1 is utilized, a light-emitting device and an electron apparatus including the light-emitting device may have a high efficiency and long lifespan.
In the present disclosure, it will be understood that the terms “comprise(s),” “include(s),” or “have/has” specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
Throughout the present disclosure, when a component such as a layer, a film, a region, or a plate is mentioned to be placed “on” another component, it will be understood that it may be directly on another component or that another component may be interposed therebetween. In some embodiments, “directly on” may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, “directly on” may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.
In the present disclosure, although the terms “first,” “second,” “third,” “fourth,” etc., may be utilized herein to describe one or more elements, components, regions, and/or layers, these elements, components, regions, and/or layers should not be limited by these terms. These terms are only utilized to distinguish one component from another component.
As utilized herein, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
In the present disclosure, when particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “diameter” indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
As utilized herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The light-emitting device, the display device, the display apparatus, the electronic apparatus, the electronic equipment, or any other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0001951 | Jan 2023 | KR | national |
