Patent Application
20240334812
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0037531, filed on Mar. 22, 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 an organic compound, and a light-emitting device and an electronic apparatus including the organic compound.
A light-emitting device may include a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed. Holes injected from the first electrode may move to the emission layer through the hole transport region. Electrons injected from the second electrode may move to the emission layer through an electron injection layer in the electron transport region. Carriers such as holes and electrons may combine in the emission layer to produce excitons. As excitons move/relax from an excited state to a ground state, light may be generated (to, e.g., display an image).
One or more aspects of embodiments of the present disclosure are directed toward an organic compound that emits blue light, and a light-emitting device and an electronic apparatus, each including the organic compound to obtain a lowered driving voltage and improved external quantum efficiency.
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 includes:
According to one or more embodiments of the present disclosure, an electronic apparatus includes the light-emitting device.
According to one or more embodiments of the present disclosure, electronic equipment includes the light-emitting device.
According to one or more embodiments of the present disclosure, provided is the organic 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.
According to one or more embodiments, a light-emitting device may include:
In one or more embodiments, the interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
In one or more embodiments, the interlayer may include the organic compound. For example, in one or more embodiments, the emission layer may include the organic compound.
In one or more embodiments, the electron transport region may include the organic compound. For example, in some embodiments, the electron transport layer may include the organic compound.
In one or more embodiments, the emission layer of the interlayer of the light-emitting device may include a dopant and a host, and the host may include the organic compound. For example, in some embodiments, the organic compound may act as a host. The emission layer may be to emit red light, green light, blue light, and/or white light (e.g., combined white light). For example, in some embodiments, the emission layer may be to emit blue light. The blue light may have, for example, a maximum emission wavelength in a range of about 400 nm to about 490 nm.
In one or more embodiments, the emission layer of the interlayer of the light-emitting device may include a dopant and a host, the host may include the organic compound, and the dopant may be to emit blue light. In some embodiments, the dopant may include a transition metal and m ligand(s), m may be an integer from 1 to 6, m ligand(s) may be identical to or different from each other, at least one of the m ligand(s) may be bound to the transition metal via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordinate bond. For example, in one or more embodiments, at least one of the m ligand(s) may be a carbene ligand (e.g., Ir(pmp)3 and/or the like). The transition metal may be, for example, iridium, platinum, osmium, palladium, rhodium, or gold. The emission layer and the dopant may be the same as described elsewhere in the present disclosure.
In one or more embodiments, the light-emitting device may include a capping layer located outside (e.g., on) the first electrode or outside (e.g., on) the second electrode.
In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside (e.g., on) the first electrode or a second capping layer located outside (e.g., on) the second electrode, and the organic compound represented by Formula 1 may be included in at least one of the first capping layer or the second capping layer. The first capping layer and/or the second capping layer may each be the same as described herein.
In one or more embodiments, the light-emitting device may further include:
The wording “interlayer and/or capping layer includes an organic compound” as utilized herein may be understood as “interlayer and/or capping layer may include one kind of organic compound represented by Formula 1 or two or more different kinds of organic compounds, each represented by Formula 1.”
In one or more embodiments, the interlayer and/or the capping layer may include Compound 1 only as the organic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the organic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in substantially the same layer (for example, all of Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
The term “interlayer” as utilized herein refers to a single layer and/or all of a plurality of layers between the first electrode and the second electrode of the light-emitting device.
In one or more embodiments, the light-emitting device may further include:
For example, in some embodiments, each of the organic compound and the second compound may act as a host. The third compound may act as a dopant. The fourth compound may act as a fluorescent emitter.
In one or more embodiments, the emission layer may include the organic compound and the third compound, and a weight of the organic compound in the emission layer may be greater than a weight of the third compound.
In one or more embodiments, the third compound may further include a tetradentate ligand bonded to platinum, and the tetradentate ligand may include a carbene.
In one or more embodiments, the tetradentate ligand includes a benzimidazole group, and the number of benzimidazole groups in the tetradentate ligand may be one.
In one or more embodiments, the fourth compound may not contain a transition metal.
In one or more embodiments, the fourth compound is a thermally activated delayed fluorescence emitter including at least one 6-membered ring including at least one nitrogen (N) and at least one boron (B).
In one or more embodiments, the fourth compound may be an instantaneous (prompt) fluorescence emitter including at least one 5-membered ring or 6-membered ring including at least one B (boron).
In one or more embodiments, the interlayer may be to emit blue light.
In one or more embodiments, a maximum emission wavelength (or, emission peak wavelength) of the interlayer may be about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about or 450 nm to about 460 nm. For example, in some embodiments, the emission layer including the organic compound may be to emit blue light. For example, in some embodiments, the blue light may be deep blue light.
In one or more embodiments, the CIEx value of the blue light (for example, bottom emission CIEx from a bottom emission organic light-emitting device) may be about 0.125 to about 0.140 or about 0.130 to about 0.140.
In one or more embodiments, the CIEy value (for example, bottom emission CIEy from a bottom emission organic light-emitting device) of the blue light may be about 0.110 to about 0.200 or about 0.115 to about 0.160.
According to one or more embodiments, provided is an electronic apparatus including the light-emitting device.
In one or more embodiments, the electronic apparatus may further include:
For example, in some embodiments, the electronic apparatus may be a display apparatus.
According to one or more embodiments, an electronic equipment may include the light-emitting device, wherein
One or more embodiments of the present disclosure provide an organic compound represented by Formula 1:
For example, in one or more embodiments, the organic compound represented by Formula 1 may be distinctly different from Compound C:
In one or more embodiments, the organic compound may have a highest occupied molecular orbital (HOMO) energy level of about −5.6 eV to about −5.45 eV. For example, in some embodiments, the HOMO energy level of the organic compound may be about −5.6 eV to about −5.50 eV, −5.6 eV to about −5.55 eV, −5.55 eV to about −5.45 eV, or −5.50 eV to about −5.45 eV.
The HOMO energy level of each of the organic compound, the second compound, the third compound, and the fourth compound may have a negative value, and is actually measured according to a suitable method, for example, according to the method described in Evaluation Example 1 of the present disclosure. For example, the HOMO energy level may be evaluated through cyclic voltammetry analysis of the organic compound.
In one or more embodiments, the organic compound may have a lowest excitation triplet (T1) energy level of about 2.75 eV to about 3.0 eV. For example, in some embodiments, the T1 energy level of the organic compound may be about 2.75 eV to about 2.95 eV, about 2.75 eV to about 2.90 eV, about 2.75 eV to about 2.85 eV, about 2.75 eV to about 2.80 eV, about 2.80 eV to about 3.0 eV, about 2.85 eV to about 3.0 eV, about 2.90 eV to about 3.0 eV, or about 2.95 eV to about 3.0 eV.
In one or more embodiments, Ar1 and Ar2 may each independently not include a pyridine group, a pyrimidine group, a triazine group, and/or a cinnoline group.
In one or more embodiments, Ar1 and Ar2 may each independently include: hydrogen; deuterium; a phenyl group unsubstituted or substituted with deuterium; a carbazolyl group unsubstituted or substituted with deuterium; or —Si(Q1)(Q2)(Q3).
For example, in one or more embodiments, i) Ar1 may be —Si(Q1)(Q2)(Q3) and Ar2 may be a phenyl group unsubstituted or substituted with deuterium, a carbazolyl group unsubstituted or substituted with deuterium, hydrogen, or deuterium, ii) Ar1 may be a phenyl group unsubstituted or substituted with deuterium, a carbazolyl group unsubstituted or substituted with deuterium, hydrogen, or deuterium, and Ar2 may be —Si(Q1)(Q2)(Q3), or iii) Ar1 and Ar2 may each be —Si(Q1)(Q2)(Q3).
In one or more embodiments, the organic compound may be represented by any one selected from among Formulae 1-1 to 1-7:
In one or more embodiments, L1 and L2 may each independently be a benzene group unsubstituted or substituted with at least one R10a, a naphthalene group unsubstituted or substituted with at least one R10a, a fluorene group unsubstituted or substituted with at least one R10a, a carbazole group unsubstituted or substituted with at least one R10a, a dibenzofuran group unsubstituted or substituted with at least one R10a, or a dibenzothiophene group unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 and L2 may each independently be represented by one selected from among Formulae 2-1 to 2-7:
In one or more embodiments, i) a2 may be 0, or ii) each of a1 and a2 may be 1. For example, in some embodiments, i) a1 and a2 may each be 0, ii) a1 may be 1 and a2 may be 0, iii) a1 may be 2 and a2 may be 0, or iv) a1 and a2 may each be 1.
In one or more embodiments, when c3 is 2, two R3(s) may not be connected to each other to form a ring. The structure in which two R3(s) are connected to each other to form a ring, may be understood by referring to Compound B:
Therefore, the organic compound represented by Formula 1 is clearly different from Compound B.
In one or more embodiments, Q1 to Q3 may each independently be a phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with a first substituent,
In one or more embodiments, Q1 to Q3 may each independently be:
In one or more embodiments, at least one of Ar1 or Ar2 may be —Si(Q1)(Q2)(Q3), and Q1 to Q3 may be identical to each other.
In one or more embodiments, each of Ar1 to Ar2 may be an unsubstituted or substituted triphenylsilyl group (—Si(Ph)(Ph)(Ph)).
In one or more embodiments, R2 to R5 may each independently be:
In one or more embodiments, at least one selected from among R2 to R5 may be deuterium.
In one or more embodiments, the organic compound may be one selected from among Compounds 1 to 132:
The organic compound represented by Formula 1 includes a triphenylene moiety, and at least one of Ani or Ar2 is —Si(Q1)(Q2)(Q3), so that the glass transition temperature and thermal stability of the organic compound may be improved. —Si(Q1)(Q2)(Q3) is a bulky group that causes steric hindrance. Accordingly, intermolecular interactions are suppressed or reduced and the formation of exciplex with dopants is suppressed or reduced. Also, interatomic dihedral angles are increased, and the increase in conjugation is suppressed or reduced, thereby allowing the organic compound to have a high triplet energy. As a result, the organic compound may be applicable as a host in light-emitting devices that emit blue light (phosphorescence and/or delayed fluorescence).
A triphenylene moiety included in the organic compound represented by Formula 1 has hydrogen (i.e., c3 is less than 2, c4 is less than 4, or c5 is less than 4), and/or may be substituted with deuterium (i.e., R3 to R5 are each deuterium). Accordingly, an increase in conjugation is suppressed or reduced, and a high triplet energy level may be obtained. As a result, the maximum quantum efficiency of a light-emitting device utilizing the organic compound may be improved.
Hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 will be described in more detail with reference to
In
The first electrode 110 may be formed by providing a material for the first electrode 110 on the substrate utilizing a deposition method or a sputtering method. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or a combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or a combination thereof.
The first electrode 110 may have a single-layer structure including (e.g., consisting of) a single layer or a multi-layer structure including multiple layers. For example, in some embodiments, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
An interlayer may be disposed on the first electrode 110. The interlayer may include the hole-transporting region 120, the emission layer 130, and the electron transport region 140.
The interlayer may include one or more suitable organic materials, metal-containing compounds such as organometallic compounds, and inorganic materials such as quantum dots.
In one or more embodiments, the interlayer may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emitting units. When the interlayer includes the two or more emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region 120 may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
The hole transport region 120 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 one or more embodiments, the hole transport region 120 may have a multi-layer structure, for example, a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron-blocking layer structure, wherein constituent layers of each structure are stacked sequentially from the first electrode 110 in each stated order.
In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof:
For example, in some embodiments, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each be the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a.
In one or more embodiments, in Formulae CY201 to CY217, ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one 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 one selected from the groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one selected from the groups represented by Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude any of) the groups represented by Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude any of) the 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, each of Formulae 201 and 202 may not include (e.g., may exclude any of) the groups represented by Formulae CY201 to CY217.
For example, in one or more embodiments, the hole transport region may include at least 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)), p-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), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and/or a combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer increases light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the emission layer. The electron-blocking layer prevents or reduce leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron-blocking layer.
p-Dopant
In one or more embodiments, the hole transport region 120 may further include, in addition to the aforementioned materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be substantially uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer including (e.g., consisting of) a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, in some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be about −3.5 eV or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or a combination thereof.
Non-limiting examples of the quinone derivative may be tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/or the like.
Non-limiting examples of the cyano group-containing compound may be 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 Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
Non-limiting examples of the metal may be an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); and/or the like.
Non-limiting examples of the metalloid may be silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Non-limiting examples of the non-metal may be oxygen (O), a halogen (for example, F, Cl, Br, I, etc.), and/or the like.
Non-limiting examples of the compound including element EL1 and element EL2 may be metal oxides, metal halides (for example, metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (for example, metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or combinations thereof.
Non-limiting examples of the metal oxide may be tungsten oxides (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (for example, MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (for example, ReO3, etc.), and/or the like.
Non-limiting examples of the metal halide may be alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and/or the like.
Non-limiting examples of the alkali metal halide may be LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, Nal, Kl, Rbl, Csl, and/or the like.
Non-limiting examples of the alkaline earth metal halide may be 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 be titanium halides (for example, TiF4, TiCl4, TiBr4, Til4, etc.), zirconium halides (for example, ZrF4, ZrCl4, ZrBr4, Zrl4, etc.), hafnium halides (for example, HfF4, HfCl4, HfBr4, Hfl4, etc.), vanadium halides (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halides (for example, NbF3, NbCl3, NbBr3, Nbl3, etc.), tantalum halides (for example, TaF3, TaCl3, TaBr3, Tal3, etc.), chromium halides (for example, CrF3, CrO3, CrBr3, Crl3, etc.), molybdenum halides (for example, MoF3, MoCl3, MoBr3, Mol3, etc.), tungsten halides (for example, WF3, WCl3, WBr3, Wl3, etc.), manganese halides (for example, MnF2, MnCl2, MnBr2, Mnl2, etc.), technetium halides (for example, TcF2, TcCl2, TcBr2, Tcl2, etc.), rhenium halides (for example, ReF2, ReCl2, ReBr2, Rel2, etc.), ferrous halides (for example, FeF2, FeCl2, FeBr2, Fel2, etc.), ruthenium halides (for example, RuF2, RuCl2, RuBr2, Rul2, etc.), osmium halides (for example, OsF2, OsCl2, OsBr2, Osl2, etc.), cobalt halides (for example, CoF2, CoCl2, CoBr2, Col2, etc.), rhodium halides (for example, RhF2, RhCl2, RhBr2, Rhl2, etc.), iridium halides (for example, IrF2, IrCl2, IrBr2, Irl2, etc.), nickel halides (for example, NiF2, NiCl2, NiBr2, Nil2, etc.), palladium halides (for example, PdF2, PdCl2, PdBr2, Pdl2, etc.), platinum halides (for example, PtF2, PtCl2, PtBr2, Ptl2, etc.), cuprous halides (for example, CuF, CuCl, CuBr, Cul, etc.), silver halides (for example, AgF, AgCl, AgBr, Agl, etc.), gold halides (for example, AuF, AuCl, AuBr, Aul, etc.), and/or the like.
Non-limiting examples of the post-transition metal halide may be zinc halides (for example, ZnF2, ZnCl2, ZnBr2, Znl2, etc.), indium halides (for example, Ink3, etc.), tin halides (for example, Snl2, etc.), and/or the like.
Non-limiting examples of the lanthanide metal halide may be 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 be antimony halides (for example, SbCl5, etc.) and/or the like.
Non-limiting examples of the metal telluride may be alkali metal tellurides (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (for example, ZnTe, etc.), and/or lanthanide metal tellurides (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
Emission layer 130
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 of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other, to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer, to emit white light (e.g., combined white light).
In one or more embodiments, the emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or a combination thereof.
An amount of the dopant in the emission layer may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emission layer may include a quantum dot.
In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer 130.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer 130 is within these ranges, excellent or suitable 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:
[Ar301]xb11-[(L301)xb1-R301]xb21, Formula 301
For example, in some embodiments, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or a combination thereof:
In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or a combination thereof. In one or more embodiments, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.
In one or more embodiments, the host may include: at least one selected from 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(9H-carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl) benzene (TCP); and/or a combination thereof:
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a combination thereof.
In some embodiments, the phosphorescent dopant may be electrically neutral.
For example, in one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
M(L401)xc1(L402)xc2 Formula 401
In Formulae 401 and 402,
For example, in some embodiments, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A401 (s) among two or more of L401(s) may optionally be linked to each other via T402, which is a linking group, and/or two ring A402(s) among two or more of L401(s) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as defined in T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or a combination thereof.
In one or more embodiments, the phosphorescent dopant may include, for example, one selected from Compounds PD1 to PD39, and/or a combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or a combination thereof.
For example, in one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:
In Formula 501,
In one or more embodiments, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed together.
In one or more embodiments, xd4 in Formula 501 may be 2.
In one or more embodiments, the fluorescent dopant may include: at least one selected from 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 a combination thereof:
In one or more embodiments, the emission layer may include a delayed fluorescence material.
In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may act as a host or a dopant depending on the type or kind of other materials included in the emission layer.
In one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be at least 0 eV and not more than 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is satisfied within the range above, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the light-emitting device 10 may have improved luminescence efficiency.
For example, in one or more embodiments, the delayed fluorescence material may include: i) a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group and/or the like, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 heterocyclic group, and/or the like), ii) a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other while 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.
Quantum dots utilized herein refer to crystals of semiconductor compounds. Quantum dots may be to emit light of one or more suitable emission wavelengths depending on the size of the crystal. Quantum dots may be to emit light of one or more suitable emission wavelengths by adjusting the ratio of elements constituting the quantum dots.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or a process that is similar thereto.
The wet chemical process is a method including mixing a precursor material of a quantum dot with an organic solvent and then growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or a combination thereof.
Non-limiting examples of the Group II-VI semiconductor compound may be: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and/or the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and/or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and/or the like; or a combination thereof.
Non-limiting examples of the Group III-V semiconductor compound may be: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GalnNSb, GaInPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and/or the like; or a 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 be InZnP, InGaZnP, InAlZnP, and/or the like.
Non-limiting examples of the Group III-VI semiconductor compound may be: a binary compound, such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and/or the like; a ternary compound, such as InGaS3, InGaSe3, and/or the like; or a combination thereof.
Non-limiting examples of the I-III-VI group semiconductor compound may be a ternary compound, such as AgInS, AgInS2, AgInSe2, AgGaS, AgGaS2, AgGaSe2, CuInS, CulnS2, CulnSe2, CuGaS2, CuGaSe2, CuGaO2, AgGaO2, AgAlO2, and/or the like; a quaternary compound, such as AgInGaS2 and/or AgInGaSe2; or a combination thereof.
Non-limiting examples of the Group IV-VI semiconductor compound may be: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or a combination thereof.
Non-limiting examples of the Group IV element or compound may be: a single element, such as Si, Ge, and/or the like; a binary compound, such as SiC, SiGe, and/or the like; or a combination thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle. For example, the formulae refers to the type or kind of elements included in a compound, and the ratio of elements in the compound may vary. For example, AgInGaS2 may refer to AgInxGa1-xS2 (x is a real number between 0 and 1).
In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, in some embodiments, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
Non-limiting examples of the shell of the quantum dot may be an oxide of metal, or non-metal, a semiconductor compound, and a combination thereof. Non-limiting examples of the oxide of metal or non-metal may be 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; and/or a combination thereof. Non-limiting examples of the semiconductor compound may be, as described herein, Group Ill-VI semiconductor compounds; Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group Ill-VI semiconductor compounds; Group 1-Ill-VI semiconductor compounds; Group IV-VI semiconductor compounds; and/or a combination thereof. For example, the semiconductor compound suitable as a shell may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaS, GaSe, AgGaS, AgGaS2, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AIAs, AIP, AISb, or a combination thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle. For example, the formulae refers to the type or kind of elements included in a compound, and the ratio of elements in the compound may vary.
The quantum dot may have a full width of half maximum (FWHM) of the emission spectrum of not more than about 45 nm, not more than about 40 nm, or for example, not more than about 30 nm. When the FWHM of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. In some embodiments, because light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In some embodiments, the quantum dot may be in the form of one or more of spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, cubic nanoparticles (nano-cubes), nanotubes, nanowires, nanofibers, and/or nanoplate particles (nanoplates).
Because the energy band gap of the quantum dot may be controlled or selected by adjusting the size of the quantum dot or the ratio of elements in the quantum dot compound, light of one or more suitable wavelengths may be obtained from a quantum dot emission layer. Therefore, by utilizing quantum dots as described above (utilizing quantum dots of different sizes or having different element ratios in quantum dot compounds), a light-emitting device emitting light of one or more suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dot and/or the ratio of elements in the quantum dot compound may be adjusted to enable emission of red, green, and/or blue light. In some embodiments, the quantum dots may be configured to emit white light by combination of light of one or more suitable colors.
The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple different materials, or iii) a multi-layer structure including multiple layers including different materials.
The electron transport region may include a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, in one or more embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole-blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein constituent layers of each structure are sequentially stacked from the emission layer in each stated order.
In one or more embodiments, the electron transport region (for example, the buffer layer, the hole-blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
For example, in one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21. Formula 601
In Formula 601,
In one or more embodiments, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group unsubstituted or substituted with at least one R10a.
In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
In Formula 601-1,
For example, in some embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In one or more embodiments, the electron transport region may include: at least one selected from 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 (BAIq); 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 a combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, or a combination thereof, a thickness of the buffer layer, the hole-blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole-blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting 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 a combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or a combination thereof.
For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
In one or more embodiments, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple different materials, or iii) a multi-layer structure including multiple layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a 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 (for example, fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or a combination thereof.
Non-limiting examples of the alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, K2O, and/or the like; alkali metal halides, such as LiF, NaF, CsF, KF, Lil, Nal, Csl, Kl, and/or the like; or combinations thereof. Non-limiting examples of the alkaline earth metal-containing compound may include alkaline earth metal compounds, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, Ybl3, Scl3, Tbl3, or a combination thereof. In one or more embodiments, the rare earth metal-containing compound may include one or more lanthanide metal tellurides. Non-limiting examples of the lanthanide metal telluride may be LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and/or the like.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, one of ions of the alkaline earth metal, and one of ions of the rare earth metal, respectively, and ii) a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a 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 a combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, alkali metal halide), or ii) a) an alkali metal-containing compound (for example, alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or a combination thereof. For example, in some embodiments, the electron injection layer may be a Kl:Yb co-deposited layer, an Rbl:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or a combination thereof may be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be disposed above (e.g., on) the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or a combination thereof, each having a low-work function, may be utilized.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.
A first capping layer may be arranged outside (e.g., on) the first electrode 110, and/or a second capping layer may be arranged outside (e.g., on) the second electrode 150. In one or more embodiments, the light-emitting device 10 may have a structure in which a first capping layer, the first electrode 110, the interlayer, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer, the second electrode 150, and a second capping layer are sequentially stacked in the stated order, or a structure in which a first capping layer, the first electrode 110, the interlayer, the second electrode 150, and a second capping layer are sequentially stacked in the stated order.
In some embodiments, light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110 which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. In some embodiments, light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of at least about 1.2 (e.g., at 470 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 a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or a 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 an amine group-containing compound.
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 a compound represented by Formula 201, a compound represented by Formula 202, or a 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 Compounds HT28 to HT33; Compounds CP1 to CP6; p-NPB; and/or a combination thereof:
The electronic apparatus may further include a film. The film may be, for example, an optical member (or a light control member) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), and/or a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
The light-emitting device may be included in one or more suitable electronic apparatuses. For example, in one or more embodiments, the electronic apparatus including the light-emitting device may be a display apparatus, an authentication apparatus, and/or the like.
In one or more embodiments, the electronic apparatus (for example, display apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one travel direction of light emitted from the light-emitting device. For example, in some embodiments, the light emitted from the light-emitting device may be blue light or white light (e.g., combined white light). Details on the light-emitting device may be referred 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 as described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be arranged among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns arranged among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area configured to emit first color light, a second area configured to emit second color light, and/or a third area configured to emit third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, in one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, in one or more embodiments, the plurality of color filter areas (or the plurality of color conversion areas) may 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 dot to emit green light, and the third area may not include a quantum dot (e.g., may exclude any quantum dots). Details on the quantum dot may be referred to the descriptions provided herein. The first area, the second area, and/or the third area may each further include a scatter.
For example, in one or more embodiments, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. Here, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. 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 color 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 as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation 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 activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
In one or more embodiments, the electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
Various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic apparatus. Non-limiting examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.). The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
The electronic apparatus may be applied to one or more of displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting device may be included in one or more suitable electronic equipment.
For example, the electronic equipment including the light-emitting device may be at least of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, or a signboard.
Because the light-emitting device of the present disclosure has excellent or suitable color conversion efficiency and long lifespan, the electronic equipment including the light-emitting device may have high luminance, high resolution, and low power consumption.
The electronic apparatus of
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 may provide a flat surface on the substrate 100.
A TFT may be on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be on the activation 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 arranged between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate from one another.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be arranged in contact with the exposed portions of the source region and the drain region of the activation layer 220, respectively.
The TFT may be electrically connected to the light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device may be provided 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 be arranged to expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic-based organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form 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 portion 300 may be on the capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or a combination thereof; or a combination of the inorganic films and the organic films.
The electronic apparatus of
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A electronic device of the electronic equipment 1 may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.
The non-display area NDA is an area that does not display an image, and may entirely surround the display area DA. On the non-display area NDA, a driver for providing electrical signals or power to display devices arranged on the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board may be electrically connected, may be arranged.
In the electronic equipment 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. In some embodiments, as shown in
Referring to
In one or more embodiments, the vehicle 1000 may travel on a road or a track. 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 prime mover device, 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 other parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheel, left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on 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. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be spaced apart from each other in the x-direction or the −x-direction. For example, in some embodiments, 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, in some embodiments, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one embodiment, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and/or a heater of a seat are disposed. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In some embodiments, the cluster 1400 may be arranged 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 device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In some embodiments, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, or the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to one or more embodiments of the present disclosure, an organic light-emitting display device including the light-emitting device according to the present disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described above may be utilized in embodiments of the present disclosure.
Referring to
Referring to
Referring to
Respective layers included in the hole transport region 120, the emission layer 130, and respective layers included in the electron transport region 140 may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When respective layers included in the hole transport region 120, the emission layer 130, and respective layers included in the electron transport region 140 are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group including (e.g., consisting of) carbon only as a ring-forming atom and having 3 to 60 carbon atoms. The term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group including (e.g., consisting of) one (e.g., only one) ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C1-C60 heterocyclic group may be from 3 to 61.
The “cyclic group” as utilized herein may include both (e.g., simultaneously) the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety.
The term “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.
For example,
The π electron-rich C3-C60 cyclic group may be i) Group T1, ii) a condensed cyclic group in which at least two of Group T1 are condensed with each other, iii) Group T3, iv) a condensed cyclic group in which at least two of Group T3 are condensed with each other, or v) a condensed cyclic group in which at least one of Group T3 and at least one of Group T1 are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, and/or the like).
The π electron-deficient nitrogen-containing C1-C60 heterocyclic group may be i) Group T4, ii) a condensed cyclic group in which at least two of Group T4 are condensed with each other, iii) a condensed cyclic group in which at least one of Group T4 and at least one of Group T1 are condensed with each other, iv) a condensed cyclic group in which at least one of Group T4 and at least one of Group T3 are condensed with each other, or v) a condensed cyclic group in which at least one of Group T4, at least one of Group T1, and at least one of Group T3 are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like).
Group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group.
Group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group.
Group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group.
Group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
The term “cyclic group,” “C3-C60 carbocyclic group,” “C1-C60 heterocyclic group,” “π electron-rich C3-C60 cyclic group,” or “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein may refer to a monovalent or polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, or the like) that is condensed with (e.g., combined together with) a cyclic group according to the structure of a formula for which the corresponding term is utilized.
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.
For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Non-limiting examples of the monovalent C3-C60 carbocyclic group and monovalent C1-C60 heterocyclic group may be a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
Non-limiting examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may be a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and non-limiting examples thereof may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group.
The term “C1-C60 alkylene group” as 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 monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of a C2-C60 alkyl group, and non-limiting examples thereof may be an ethenyl group, a propenyl group, a butenyl group, and/or the like.
The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having 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 a C2-C60 alkyl group, and non-limiting examples thereof may be an ethynyl group, a propynyl group, and/or the like.
The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having 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), and non-limiting examples thereof may be a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof 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 (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like.
The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having 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 of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and non-limiting examples thereof may be a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like.
The term “C1-C10 heterocycloalkylene group” as utilized herein refers to a divalent group having 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 three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof may be a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like.
The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having 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 of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one double bond in the cyclic structure thereof. Non-limiting examples of the C1-C10 heterocycloalkenyl group may be a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like.
The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having 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 of 6 to 60 carbon atoms.
The term “C6-C60 arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.
Non-limiting examples of the C6-C60 aryl group may be a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and/or the like.
When the C1-C60 aryl group and the C1-C60 arylene group each include two or more rings, the rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms.
The term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms.
Non-limiting examples of the C1-C60 heteroaryl group may be a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group.
When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may be an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indeno anthracenyl group, and/or the like.
The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure as a whole. 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 described above.
The term “C6-C60 aryloxy group” as utilized herein indicates —OA102 (wherein A102 is a C1-C60 aryl group).
The term “C6-C60 arylthio group” as utilized herein indicates —SA103 (wherein A103 is a C1-C60 aryl group).
The term “C7-C60 arylalkyl group” as utilized herein refers to —A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group).
The term “C2-C60 heteroarylalkyl group” as utilized herein refers to —A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as utilized herein may be:
In the present disclosure, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be:
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may be O, S, N, P, Si, B, Ge, Se, and a combination thereof.
In the present disclosure, the transition metal may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
“D” utilized herein may refer to hydrogen or deuterium (an isotope of hydrogen), “Ph” utilized herein may refer to a phenyl group, “Me” utilized herein may refer to a methyl group, “Et” utilized herein may refer to an ethyl group, “tert-Bu,” “tBu,” or “But” utilized herein may refer to a tert-butyl group, and “OMe” utilized herein may refer to a methoxy group.
The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In some embodiments, 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 some embodiments, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
* and *′ as utilized herein, unless defined otherwise, each refer to a binding site to a neighboring 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 in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.
Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to the following Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
For example, Compound 1 may be synthesized by Reaction Scheme 1, and embodiments of the present disclosure are not limited thereto.
2-(5-bromo-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number=2764707-59-5) and chlorotriphenylsilane (CAS number=76-86-8) was reacted with n-BuLi to obtain Intermediate 1-1. Intermediate 1-1 of liquid chromatography mass spectrometry (LC-MS) was measured and the following M+1 peak value was found.
C30H30BNO4Si: M+1 508.21
Intermediate 1-1 and 1-bromotriphenylene (CAS number=74897-21-5) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 1-2. Intermediate 1-2 was measured by LC-MS and the following M+1 peak value was found.
C42H29NO2Si: M+1 608.20
Intermediate 1-2 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 1-3. Intermediate 1-3 was measured by LC-MS and the following M+1 peak value was found.
C42H29NSi: M+1 576.23
1.1 g of bromobenzene (CAS number=108-86-1), 4 g of Intermediate 1-3, 1 g of sodium tert-butoxide, 0.25 g of tris(dibenzylideneacetone)dipalladium(0), and 0.23 mL of tri(tert-butyl) phosphine, and 35 mL of toluene were added to a reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.7 g (yield: 82%) of Compound 1. Compound 1 was identified by LC-MS and 1H-NMR.
For example, Compound 17 may be synthesized by Reaction Scheme 2, and embodiments of the present disclosure are not limited thereto.
2-(4-bromo-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number=1344738-63-1) and chlorotriphenylsilane (CAS number=76-86-8) was reacted with n-BuLi to obtain Intermediate 17-1. Intermediate 17-1 was measured by LC-MS and the following M+1 peak value was found.
C30H30BNO4Si: M+1 508.21
Intermediate 17-1 and 1-bromotriphenylene (CAS number=74897-21-5) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 17-2. Intermediate 17-2 was measured by LC-MS and the following M+1 peak value was found.
C42H29NO2Si: M+1 608.20
Intermediate 17-2 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 17-3. Intermediate 17-3 was measured by LC-MS and the following M+1 peak value was found.
C42H29NSi: M+1 576.22
3 g of 3-bromo-9-phenylcarbazole (CAS number=1153-85-1), 5.2 g of Intermediate 17-3, 1.3 g of sodium tert-butoxide, 0.33 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 mL of tri(tert-butyl) phosphine, and 45 mL of toluene were added to the reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 5.6 g (yield: 76%) of Compound 17. Compound 17 was confirmed by LC-MS and 1H-NMR.
For example, Compound 28 may be synthesized by Reaction Scheme 3, and embodiments of the present disclosure are not limited thereto.
1-bromotriphenylene (CAS number=74897-21-5) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane (CAS number=190788-59-1) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 28-1. Intermediate 28-1 was measured by LC-MS and the following M+1 peak value was found.
C24H15NO2: M+1 350.13
Intermediate 28-1 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 28-2. Intermediate 28-2 was measured by LC-MS and the following M+1 peak value was found.
C24H15N: M+1 318.11
4 g of (4-bromophenyl)triphenylsilane (CAS number=18737-40-1), 3.1 g of Intermediate 28-2, 1.4 g of sodium tert-butoxide, 0.35 g of tris(dibenzylideneacetone)dipalladium(0), 0.31 mL of tri(tert-butyl) phosphine, and 50 mL of toluene were added to the reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 5.2 g (yield: 88%) of Compound 28. Compound 28 was confirmed by LC-MS and 1H-NMR.
For example, Compound 35 may be synthesized by Reaction Scheme 4, but embodiments of the present disclosure are not limited thereto.
2-(5-bromo-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number=2764707-59-5) and carbazole (CAS number=86-74-8) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 35-1. Intermediate 35-1 was measured by LC-MS and the following M+1 peak value was found.
C24H23BN2O4: M+1 415.18
Intermediate 35-1 and 1-bromotriphenylene (CAS number=74897-21-5) were reacted under Pd catalyst conditions to obtain Intermediate 35-2. Intermediate 35-2 was measured by LC-MS and the following M+1 peak value was found.
C36H22N2O2: M+1 515.18
Intermediate 35-2 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 35-3. Intermediate 35-3 was measured by LC-MS and the following M+1 peak value was found.
C36H22N2: M+1 483.18
4 g of (3-bromophenyl)triphenylsilane (CAS number=185626-73-7), 4.65 g of Intermediate 35-3, 1.4 g of sodium tert-butoxide, 0.35 g of tris(dibenzylideneacetone)dipalladium(0), 0.31 mL of tri(tert-butyl) phosphine, and 50 mL of toluene were added to the reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 5.5 g (yield: 70%) of Compound 35. Compound 35 was confirmed by LC-MS and 1H-NMR.
For example, Compound 99 may be synthesized by Reaction Scheme 5, and embodiments of the present disclosure are not limited thereto.
Iodobenzene (CAS number=591-50-4) and 7-bromo-9H-carbazole-1,2,3,4,5,6,8-d7 (CAS number=2650519-97-2) were reacted with each other in the presence of Cu catalyst to obtain Intermediate 99-1. Intermediate 99-1 was measured by LC-MS and the following M+1 peak value was found.
C18H5D7BrN: M+1 329.08
6-bromo-9H-carbazole-1,2,3,4,5,7,8-d7 (CAS number=2764814-81-3), tosyl chloride (CAS number=98-59-9), and potassium hydroxide were reacted with each other in an acetone solvent to obtain Intermediate 99-2. Intermediate 99-2 was measured by LC-MS and the following M+1 peak value was found.
C19H7D7BrNO2S: M+1 407.09
Intermediate 99-2 and Intermediate 17-3 were reacted with each other in the presence of Cu catalyst to obtain Intermediate 99-3. Intermediate 99-3 was measured by LC-MS and the following M+1 peak value was found.
C61H35D7N2O2SSi: M+1 902.33
Intermediate 99-3 was reacted with sodium hydroxide to obtain Intermediate 99-4. Intermediate 99-4 was measured by LC-MS and the following M+1 peak value was found.
C54H29D7N2Si: M+1 748.33
3 g of Intermediate 99-1, 6.8 g of Intermediate 99-4, 1.3 g of sodium tert-butoxide, 0.33 g of tris(dibenzylideneacetone)dipalladium (0), 0.3 mL of tri(tert-butyl) phosphine, and 45 mL of toluene were added to a reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 6.1 g (yield: 68%) of Compound 99. Compound 99 was confirmed by LC-MS and 1H-NMR.
For example, Compound 101 may be synthesized by Reaction Scheme 6, and embodiments of the present disclosure are not limited thereto.
Intermediate 101-1 was obtained by reacting 1,3-dibromobenzene (CAS number=108-36-1) and diphenyldichlorosilane (CAS number=80-10-4) with n-BuLi. Intermediate 101-1 was measured by LC-MS and the following M+1 peak value was found.
C24H18Br2Si: M+1 492.95
Intermediate 101-1 and phenyl-d5-boronic acid (CAS number=215527-70-1) were reacted with each other in the presence of Pd catalyst to obtain Intermediate 101-2. Intermediate 101-2 of liquid chromatography mass spectrometry (LC-MS) was measured and the following M+1 peak value was found.
C30H18D5BrSi: M+1 496.11
3 g of Intermediate 101-2, 2 g of Intermediate 28-2, 0.9 g of sodium tert-butoxide, 0.22 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 mL of tri(tert-butyl) phosphine, and 30 mL of toluene were added to a reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.2 g (yield: 74%) of Compound 101. Compound 101 was confirmed by LC-MS and 1H-NMR.
For example, Compound 112 may be synthesized by Reaction Scheme 7, and embodiments of the present disclosure are not limited thereto.
2-(4-bromo-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number=1344738-63-1) and carbazole-1,2,3,4,5,6,7,8-d8 (CAS number=38537-24-5) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 112-1. Intermediate 112-1 was measured by LC-MS and the following M+1 peak value was found.
C24H15D8BN2O4: M+1 423.24
Intermediate 112-1 and 1-bromotriphenylene (CAS number=74897-21-5) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 112-2. Intermediate 112-2 was measured by LC-MS and the following M+1 peak value was found.
C36H14D8N2O2: M+1 523.22
Intermediate 112-2 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 112-3. Intermediate 112-3 was measured by LC-MS and the following M+1 peak value was found.
C36H14D8N2: M+1 491.22
2 g of Intermediate 101-2, 2 g of Intermediate 112-3, 0.58 g of sodium tert-butoxide, 0.15 g of tris(dibenzylideneacetone)dipalladium(0), 0.13 mL of tri(tert-butyl) phosphine, and 20 mL of toluene were added to a reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 2.5 g (yield: 70%) of Compound 112. Compound 112 was confirmed by LC-MS and 1H-NMR.
For example, Compound 132 may be synthesized by Reaction Scheme 8, and embodiments of the present disclosure are not limited thereto.
2-(4-bromo-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number=1344738-63-1) and 9H-3,9′-bicarbazole-1,1′,2,2′,3′,4,4′,5,5′,6,6′,7,7′,8,8′-d15 (CAS number=2778147-33-2) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 132-1. Intermediate 132-1 was measured by LC-MS and the following M+1 peak value was found.
C36H15D15BN3O4: M+1 595.34
Intermediate 132-1 and 1-bromotriphenylene (CAS number=74897-21-5) were reacted with each other in the presence of a Pd catalyst to obtain Intermediate 132-2. Intermediate 132-2 was measured by LC-MS and the following M+1 peak value was found.
C48H14D15N3O2: M+1 695.33
Intermediate 132-2 and triphenylphosphine (CAS number=603-35-0) were reacted with each other in a dichlorobenzene solvent to obtain Intermediate 132-3. Intermediate 132-3 was measured by LC-MS and the following M+1 peak value was found.
C48H14D15N3: M+1 663.34
3 g of (4-bromophenyl)triphenylsilane (CAS number=18737-40-1), 4.8 g of Intermediate 132-3, 1.04 g of sodium tert-butoxide, 0.26 g of tris(dibenzylideneacetone)dipalladium(0), 0.24 mL of tri(tert-butyl) phosphine, and 35 mL of toluene were added to the reaction vessel and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with ethylacetate, the collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 5.5 g (yield: 77%) of Compound 132. Compound 132 was confirmed by LC-MS and 1H-NMR.
The HOMO energy level and T1 energy level of each of the compounds listed in Table 2 were measured utilizing the method described in Table 1. Results thereof are shown in Table 2. HOMO energy levels are negative values.
As an anode, a Corning 15 Ω/cm2 (1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.
HATCN was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 100 Å. BCFN was vacuum-deposited on the hole injection layer to form a first hole transport layer having a thickness of 600 Å. SiCzCz was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 Å.
SiTrzCz2 as a first host, Compound 1 as a second host, and PtON-TBBI as a phosphorescent dopant were concurrently (e.g., simultaneously) co-deposited on the second hole transport layer in a weight ratio of 60:27:13 to form an emission layer having a thickness of 350 Å.
mSiTrz was vacuum-deposited on the emission layer to form an electron transport layer having a thickness of 50 Å. mSiTrz and LiQ were concurrently (e.g., simultaneously) co-deposited on the first electron transport layer in a weight ratio of 1:1 to form a second electron transport layer having a thickness of 350 Å. LiF was vacuum-deposited on the second electron transport layer to form an electron injection layer having a thickness of 15 Å.
Al was vacuum-deposited on the electron injection layer to form an LiF/Al electrode having a thickness of 80 Å.
Light-emitting devices were each manufactured utilizing the same method as in Example 1, except that each of the compounds listed in Table 3 was respectively utilized instead of Compound 1 when forming the emission layer.
In order to evaluate the characteristics of each the light-emitting devices manufactured according to Example 1 to 8 and Comparative Example 1 to 4, the driving voltage and external quantum efficiency thereof were measured, and maximum quantum efficiency thereof was calculated. Results thereof are shown in Table 3.
Driving voltage, current density, and maximum quantum efficiency were evaluated at a current density of 10 mA/cm2. The driving voltage and the current density of each of the organic light-emitting devices was measured utilizing a source meter (Keithley Instrument Inc., 2400 series), and the maximum quantum efficiency of each of the organic electroluminescent devices was measured utilizing the external quantum efficiency measurement apparatus 09920-2-12 of Hamamatsu Photonics Inc.
In evaluating the maximum quantum efficiency, the luminance/current density was measured utilizing a luminance meter that had been calibrated for wavelength sensitivity, and the measurements were converted into the maximum quantum efficiency by assuming an angular luminance distribution (Lambertian) which introduced a perfect reflecting diffuser.
From Table 3, it can be confirmed that each of the light-emitting devices according to Examples 1 to 8 is a blue organic light-emitting device having a lower driving voltage and/or higher maximum quantum efficiency than the light-emitting devices according to Comparative Examples 1 to 4.
The organic compound represented by Formula 1 contains at least one —Si(Q1)(Q2)(Q3). As a result, the glass transition temperature and thermal stability are improved, the increase in conjugation is suppressed or reduced, and high triplet energy levels may be obtained. Accordingly, the maximum quantum efficiency of a light-emitting device utilizing the organic compound may be improved.
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,” 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”.
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 the present disclosure is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend the disclosure, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
In the present disclosure, when particles are spherical, “size” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “size” 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.
The light-emitting device, the light-emitting apparatus, the display device, 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 |
|---|---|---|---|
| 10-2023-0037531 | Mar 2023 | KR | national |
