Patent Application
20240292743
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0016264, filed on Feb. 7, 2023, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
One or more aspects of embodiments of the present disclosure relate to a light-emitting device including a heterocyclic compound, an electronic apparatus including the light-emitting device, and the heterocyclic compound.
Organic light-emitting devices are a class of light-emitting devices that are self-emissive devices having wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and response speed, compared to devices in the art.
In an example, an organic light-emitting device may have a structure in which a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed (e.g., stacked) on (e.g., above) the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in the emission layer to produce excitons. The excitons may transition (i.e., relax) from an excited state to a ground state, thus generating light.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device including a novel heterocyclic compound, an electronic apparatus including the light-emitting device, and the heterocyclic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, a light-emitting device includes
L1 to L5 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R1 or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R1,
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, electronic equipment includes the light-emitting device.
According to one or more embodiments, the present disclosure is directed toward the heterocyclic compound represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the above and other aspects, features, and advantages of certain embodiments of the present disclosure are incorporated in and constitute a part of this specification. The drawings illustrate example embodiments and, together with the following description taken in conjunction with the accompanying drawings, serve to make the principles of the present disclosure more apparent. In the drawings:
Reference will now be made in more detail to embodiments of the present disclosure, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and duplicative descriptions thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described, by referring to the drawings, to explain aspects of the present description.
As utilized herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “one of,” 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, throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.
The terminology used herein is for the purpose of describing embodiments and is not intended to limit the embodiments described herein. Unless otherwise defined, all chemical names, technical and scientific terms, and terms defined in common dictionaries should be interpreted as having meanings consistent with the context of the related art, and should not be interpreted in an ideal or overly formal sense. It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element.
As used herein, singular forms such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “comprise,” “comprises,” “comprising,” “has,” “have,” “having,” “include,” “includes,” and/or “including,” when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
As used herein, the term “and/or” includes any, and all, combination(s) of one or more of the associated listed items.
The term “may” will be understood to refer to “one or more embodiments of the present disclosure,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments of the present disclosure,” each including a corresponding listed item.
It will be understood that when an element is referred to as being “on,” “connected to,” or “on” another element, it may be directly on, connected, or coupled to the other element or one or more intervening elements may also be present. When an element is referred to as being “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present.
Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper,” “bottom,” “top,” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the drawings. For example, if the device in the drawings is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” or “over” the other elements or features. Thus, the term “below” may encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure pertains. It is also to be understood that terms defined in commonly used dictionaries should be interpreted as having meanings consistent with meanings in the context of the related art, unless expressly defined herein, and should not be interpreted in an ideal or overly formal sense.
In this context, “consisting essentially of” means that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.
Further, in this specification, the phrase “on a plane,” or “plan view,” means viewing a target portion from the top, and the phrase “on a cross-section” means viewing a cross-section formed by vertically cutting a target portion from the side.
A light-emitting device (for example, an organic light-emitting device) may include: a first electrode; a second electrode facing the first electrode; an interlayer arranged between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1.
Hereinafter, the heterocyclic compound represented by Formula 1 will be described in more detail.
One or more embodiments of the present disclosure include a heterocyclic compound represented by Formula 1:
In one or more embodiments, L1 to L5 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R1.
In one or more embodiments, L1 to L5 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, or a chrysene group, each unsubstituted or substituted with at least one R1.
In one or more embodiments, L1 to L5 may each independently be a group represented by one selected from among Formulae 3-1 to 3-13:
In Formulae 3-1 to 3-13,
In one or more embodiments, n1 may be 1 or 2.
In one or more embodiments, a group represented by
may be a group represented by one selected from among Formulae L1-1 to L1-22:
In Formulae L1-1 to L1-22,
In one or more embodiments, R2 to R5 may each independently be a group represented by Formula 2-1 or 2-2, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, R2 to R5 may each independently be: a group represented by Formula 2-1 or 2-2; or a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilolyl group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R2 to R5 may each independently be a group represented by one selected from among Formulae 4-1 to 4-12:
In Formulae 4-1 to 4-12,
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be one selected from among Compounds 1 to 170:
Due to the inclusion of a core in which two triazine moieties are connected to each other via a linker, the heterocyclic compound represented by Formula 1 according to the disclosure may have excellent or suitable electron transport capability and stability.
In some embodiments, in the heterocyclic compound represented by Formula 1, at least one selected from among R1 to R5 includes an adamantyl group so that the refractive index may be reduced.
Accordingly, a light-emitting device including the heterocyclic compound may exhibit excellent or suitable performance in terms of driving voltage, emission peak, current efficiency, and device stability.
Synthesis methods of the heterocyclic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided.
At least one heterocyclic compound represented by Formula 1 may be utilized in a light-emitting device (for example, an organic light-emitting device). Accordingly, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; an interlayer arranged between the first electrode and the second electrode and including an emission layer; and the heterocyclic compound represented by Formula 1.
In one or more embodiments,
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included between the first electrode and the second electrode of the light-emitting device.
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, the electron injection layer, or the electron transport layer of the light-emitting device.
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included in the interlayer of the light-emitting device, for example, in the emission layer of the interlayer.
In one or more embodiments, the light-emitting device may include a capping layer arranged outside the first electrode or outside the second electrode.
For example, the light-emitting device may further include at least one of a first capping layer arranged outside (e.g., on or on an outer side of) the first electrode or a second capping layer arranged outside (e.g., on or on an outer side of) the second electrode, and at least one of the first capping layer or the second capping layer may include the heterocyclic compound represented by Formula 1. Details of the first capping layer and/or the second capping layer may be as described herein.
In one or more embodiments, the light-emitting device may include:
The expression “(an interlayer and/or a capping layer) includes at least one heterocyclic compound” as utilized herein may include a case in which “(an interlayer and/or a capping layer) includes identical heterocyclic compounds represented by Formula 1” and/or a case in which “(an interlayer and/or a capping layer) includes two or more different heterocyclic compounds represented by Formula 1”.
The term “interlayer” as utilized herein refers to a single layer and/or all layers between the first electrode and the second electrode of the light-emitting device.
Another aspect of the disclosure provides an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In one or more embodiments, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. Details of the electronic apparatus may be as described herein.
Hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work-function material that facilitates injection of holes. The “term “high work-function material” as utilized herein refers to a substance (e.g., a metal or metal alloy) that requires a relatively high amount of energy to emit electrons from its surface.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In 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 any combination thereof.
The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer 130 is arranged on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region arranged between the first electrode 110 and the emission layer, and an electron transport region arranged between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, and/or the like.
In one or more embodiments, the interlayer 130 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 130 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 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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
For example, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure. In one or more embodiments, constituent layers of each structure are stacked sequentially from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, and/or any combination thereof:
In Formulae 201 and 202,
For example, each of Formulae 201 and 202 may include at least one selected from among groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each be defined as in connection with 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 among the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from among the groups represented by Formulae CY201 to CY203 and at least one selected from among 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 among the groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one selected from among 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) the (e.g., any) 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) the (e.g., any) groups represented by Formulae CY201 to CY203, and may include at least one of 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) the (e.g., any) groups represented by Formulae CY201 to CY217.
For example, the hole transport region may include one selected from among Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β—NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/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 any combination thereof:
The thickness of the hole transport region may be in a range of about 50 angstrom (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 any combination thereof, the 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 the 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 the ranges described above, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer. In one or more embodiments, the electron blocking layer may block or reduce the 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
The hole transport region may further include, in addition to the materials described above, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of less than or equal to −3.5 eV.
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 any combination thereof.
Examples of the quinone derivative are TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound are 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 any combination thereof, and element EL2 may be non-metal, metalloid, or any combination thereof.
Examples of the metal are: 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.
Examples of the metalloid are silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Examples of the non-metal are oxygen (O), halogen (for example, F, Cl, Br, I, etc.), and/or the like.
Examples of the compound including element EL1 and element EL2 are metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, metal iodide, etc.), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, metalloid iodide, etc.), metal telluride, or any combination thereof.
Examples of the metal oxide are tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (for example, ReO3, etc.), and/or the like.
Examples of the metal halide are alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and/or the like.
Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.
Examples of the alkaline earth metal halide are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and/or the like.
Examples of the transition metal halide are titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), copper halide (for example, CuF, CuCl, CuBr, Cul, etc.), silver halide (for example, AgF, AgCl, AgBr, Agl, etc.), gold halide (for example, AuF, AuCI, AuBr, Aul, etc.), and/or the like.
Examples of the post-transition metal halide are zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (for example, InI3, etc.), tin halide (for example, SnI2, etc.), and/or the like.
Examples of the lanthanide metal halide are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and/or the like.
Examples of the metalloid halide are antimony halide (for example, SbCl5, etc.) and/or the like.
Examples of the metal telluride are alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, TaTe3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, CuzTe, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal telluride (for example, ZnTe, etc.), lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and/or the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other, to emit white light. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer, to emit white light.
The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
The 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.
The 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 is within the ranges described above, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host may further include a compound represented by Formula 301:
In Formula 301,
For example, when xb11 in Formula 301 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.
In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In Formulae 301-1 and 301-2,
In one or more embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include: one selected from among Compounds H1 to H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN); 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN); 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP); 1,3-di-9-carbazolylbenzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); and/or any combination thereof:
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In Formulae 401 and 402,
For example, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A401(s) among two or more of L401 may optionally be linked to each other via T402, which is a linking group, and two ring A402(s) among two or more of L401 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be defined as in connection with T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, at least one selected from among Compounds PD1 to PD39, and/or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
For example, the fluorescent dopant may include a compound represented by Formula 501:
In Formula 501,
For example, 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 with each other.
In one or more embodiments, xd4 in Formula 501 may be 2.
For example, the fluorescent dopant may include: at least one selected from among Compounds FD1 to FD37; DPVBi; DPAVBi; and/or any combination thereof:
The emission layer may include a delayed fluorescence material.
In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may 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 greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the range described above, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be enhanced or improved.
For example, 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, etc., such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, etc.), 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 the like.
Examples of the delayed fluorescence material may include at least one selected from among Compounds DF1 to DF14:
The emission layer may include a quantum dot.
The term “quantum dot” as utilized herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.
The diameter of the quantum dot may be, for example, in a range of about 1 nanometer (nm) to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Examples of the Group II-VI semiconductor compound are: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and/or the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and/or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and/or the like; or any combination thereof.
Examples of the Group III-V semiconductor compound are: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and/or the like; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element are InZnP, InGaZnP, InAlZnP, and/or the like.
Examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and/or the like; a ternary compound, such as InGaS3, InGaSe3, and/or the like; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound are: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, and/or the like; or any combination thereof.
Examples of the Group IV-VI semiconductor compound are: 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 any combination thereof.
Examples of the Group IV element or compound are: a single element compound, such as Si, Ge, and/or the like; a binary compound, such as SiC, SiGe, and/or the like; or any combination thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.
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, 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.
Examples of the shell of the quantum dot are an oxide of metal, metalloid, or non-metal, a semiconductor compound, or a combination thereof. Examples of the oxide of metal, metalloid, or non-metal are: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, and/or the like; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, and/or the like; or any combination thereof. Examples of the semiconductor compound are: as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. Examples of the semiconductor compound are CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
The quantum dot may have a full width at half maximum (FWHM) of the emission wavelength spectrum of less than or equal to about 45 nm, less than or equal to about 40 nm, or for example, less than or equal to about 30 nm. When the FWHM of the quantum dot is within these ranges, the quantum dot may have enhanced or improved color purity and/or enhanced 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, (e.g., the viewing angle of the light-emitting device may be enhanced or improved).
In some embodiments, the quantum dot(s) may be in the form of spherical, pyramidal, multi-arm, and/or cubic nanoparticles, nanotubes, nanowires, nanofibers, and/or nanoplate particles.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dots may be selected to emit red light, green light, and/or blue light. In some embodiments, the size of the quantum dots may be configured to emit white light by combination of light of one or more suitable colors.
The electron transport region 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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein constituent layers of each structure are sequentially stacked from the emission layer.
The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
For example, the electron transport region may include a compound represented by Formula 601:
In Formula 601,
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601 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, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include: at least one selected from among of Compounds ET1 to ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); Alq3; BAlq; TAZ; NTAZ; and/or any combination thereof:
The 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 any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within the ranges described above, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may 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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (for example, fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include: alkali metal oxide, such as Li2O, Cs2O, K2O, and/or the like; alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and/or the like; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x 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, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride are 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) at least one selected from among ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In 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):
For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
The 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 described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the interlayer 130 having a structure as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work-function, may be utilized. The term “low work-function material” as utilized herein refers to a substance (e.g., a metal or metal alloy) that requires a relatively small, or low, amount of energy to emit electrons from its surface.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a 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. For example, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the emission layer of the interlayer 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. Light generated in the emission layer of the interlayer 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 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be enhanced or improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of greater than or equal to 1.6 (at 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one selected from among the first capping layer or the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from among the first capping layer or the second capping layer may each independently include an amine group-containing compound.
For example, at least one selected from among the first capping layer and/or the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one selected from among the first capping layer and/or the second capping layer may each independently include: one selected from among Compounds HT28 to HT33; Compounds CP1 to CP6; β-NPB; and/or any combination thereof:
The heterocyclic compound represented by Formula 1 may be included in one or more suitable films. Accordingly, another aspect of the disclosure provides a film including the heterocyclic compound represented by Formula 1. The film may be, for example, an optical member (or a light control member or component) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, and/or the like), a light blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, etc.), and/or the like.
The light-emitting device may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. Details of the light-emitting device may be as described herein. In one or more embodiments, the color conversion layer may include a quantum dot. 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 emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In one or more embodiments, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may be quantum dot free, e.g., not include (e.g., may exclude) a (e.g., any) quantum dot. Details of the quantum dot may be as described herein. The first area, the second area, and/or the third area may each further include a scatter.
For example, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In one or more embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
One or more 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 utilize of the electronic apparatus. 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 described above, a biometric information collector.
The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting device may be included in one or more suitable electronic equipment.
For example, the electronic equipment including the light-emitting device may be at least one selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, 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 portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and/or a signboard.
The light-emitting device may have excellent or suitable luminescence efficiency and long lifespan, and thus, the electronic equipment including the light-emitting device may have characteristics such as high luminance, high resolution, and low power consumption.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be arranged on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
The TFT may be arranged on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be arranged on the activation layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 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 arranged on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be arranged in contact with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT may be electrically connected to a light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270, 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 arranged 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 one or more 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(s).
The second electrode 150 may be arranged 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 arranged on the capping layer 170. The encapsulation portion 300 may be arranged on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide (ITO), indium zinc oxide (IZO), or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film(s) and the organic film(s).
The light-emitting apparatus of
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A display apparatus 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 and/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 device 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. For example, as shown in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set, certain, or predetermined direction according to rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover apparatus, a bicycle, and a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis 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 apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, front and rear wheels, left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be spaced apart from each other in the x-direction or the −x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-direction or the −x-direction. In other words, an imaginary straight line L connecting the side window glasses 1100 to each other may extend in the x-direction or the −x-direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-direction or the −x-direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the body. In one or more embodiments, 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, a turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, a hodometer, an automatic shift selector indicator lamp, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning lamp.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio apparatus, an air conditioning apparatus, and a heater of a seat are arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In one or more embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be arranged to correspond to a passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In one or more embodiments, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic light-emitting display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, as the display apparatus 2 according to one or more embodiments of the disclosure, an organic light-emitting display apparatus including the light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display apparatuses as described above may be utilized in embodiments of the disclosure.
Referring to
Referring to
Referring to
Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a suitable 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, the emission layer, and respective layers included in the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition 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 consisting of carbon only as a ring-forming atom and having 3 to 60 carbon atoms, and 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 consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C1-C60 heterocyclic group may be from 3 to 61.
The term “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, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic 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 terms “the cyclic group, the C3-C60 carbocyclic group, the C1-C60 heterocyclic group, the π electron-rich C3-C60 cyclic group, or the π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is utilized. For example, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understand by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of the monovalent C5-C60 carbocyclic group and monovalent C1-C60 heterocyclic group are 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, and examples of the divalent C5-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a 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 1 to 60 carbon atoms, and examples thereof are 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, a tert-decyl group, and/or the like. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having 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 the C2-C60 alkyl group, and examples thereof are 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 the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are 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 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 the C1-C60 alkyl group), and examples thereof are 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 examples thereof are 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 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 examples thereof are 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 the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as utilized herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof are 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 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 carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group are 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 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, and 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. Examples of the C6-C60 aryl group are 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 C6-C60 aryl group and the C6-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. Examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, and/or the like. 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. Examples of the monovalent non-aromatic condensed polycyclic group are 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 the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (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. Examples of the monovalent non-aromatic condensed heteropolycyclic group are a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, and/or the like. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein refers to —SA103 (wherein A103 is the C6-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), and 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 specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group.
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
In the specification, the third-row transition metal may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
The term “Ph” as utilized herein refers to a phenyl group, the term “Me” as utilized herein refers to a methyl group, the term “Et” as utilized herein refers to an ethyl group, the term “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and the term “OMe” as utilized herein refers to a methoxy group.
The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group”. In other words, the “terphenyl group” is 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 specification, the x-axis, y-axis, and z-axis are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.
Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
The materials (4-(adamantan-1-yl)phenyl)boronic acid (30.0 g, 117.1 mmol), 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (35.4 g, 117.1 mmol), Pd(PPh3)4 (4.1 g, 3.5 mmol), and K2CO3 (48.6 g, 351.4 mmol) were added to 500 mL of toluene, 75 mL of ethanol, and 75 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (47.0 g, 98.4 mmol, yield: 84%).
Mass: [(M+H)+]: 479
The materials (4-(adamantan-1-yl)phenyl)boronic acid (30.0 g, 117.1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (39.7 g, 175.7 mmol), Pd(PPh3)4 (4.1 g, 3.5 mmol), and K2CO3 (48.6 g, 351.4 mmol) were added to 300 mL of THF and 90 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-chloro-6-phenyl-1,3,5-triazine (33.0 g, 82.0 mmol, yield: 70%).
Mass: [(M+H)+]: 403
Dibenzo[b,d]furan-3-ylboronic acid (30.0 g, 141.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (48.0 g, 212.3 mmol), Pd(PPh3)4 (4.9 g, 4.2 mmol), and K2CO3 (58.7 g, 424.5 mmol) were added to 300 mL of THF and 90 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (32.9 g, 92.0 mmol, yield: 65%).
Mass: [(M+H)+]: 359
The materials (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (30.0 g, 126.0 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (42.7 g, 189.0 mmol), Pd(PPh3)4 (4.4 g, 3.8 mmol), and K2CO3 (52.2 g, 378.0 mmol) were added to 300 mL of THF and 90 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (34.8 g, 90.7 mmol, yield: 72%).
Mass: [(M+H)+]: 385
The materials (4′-cyano-[1,1′-biphenyl]-4-yl)boronic acid (30.0 g, 134.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (45.6 g, 201.8 mmol), Pd(PPh3)4 (4.7 g, 4.0 mmol), and K2CO3 (55.8 g, 403.5 mmol) were added to 300 mL of THF and 90 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 4′-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-carbonitrile (36.2 g, 98.2 mmol, yield: 73%).
Mass: [(M+H)+]: 370
The materials [1,1′-biphenyl]-4-ylboronic acid (30.0 g, 151.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (51.4 g, 227.2 mmol), Pd(PPh3)4 (5.3 g, 4.5 mmol), and K2CO3 (62.8 g, 454.5 mmol) were added to 300 mL of THF and 90 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (33.3 g, 97.0 mmol, yield: 64%).
Mass: [(M+H)+]: 345
The materials [1,1′-biphenyl]-2-ylboronic acid (30.0 g, 151.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (51.4 g, 227.2 mmol), Pd(PPh3)4 (5.3 g, 4.5 mmol), and K2CO3 (62.8 g, 454.5 mmol) were added to 300 mL of THF and 90 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (32.8 g, 95.4 mmol, yield: 63%).
Mass: [(M+H)+]: 345
Naphthalen-2-ylboronic acid (30.0 g, 174.4 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (59.1 g, 261.6 mmol), Pd(PPh3)4 (6.0 g, 5.2 mmol), and K2CO3 (72.3 g, 523.3 mmol) were added to 300 mL of THF and 90 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (42.1 g, 132.6 mmol, yield: 76%).
Mass: [(M+H)+]: 319
The materials (4-(pyridin-3-yl)phenyl)boronic acid (30.0 g, 150.7 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (51.1 g, 226.1 mmol), Pd(PPh3)4 (5.2 g, 4.5 mmol), and K2CO3 (62.5 g, 452.2 mmol) were added to 300 mL of THF and 90 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine (36.9 g, 107.0 mmol, yield: 71%).
Mass: [(M+H)+]: 346
The materials (4-(adamantan-1-yl)phenyl)boronic acid (30.0 g, 117.1 mmol), 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (35.4 g, 117.1 mmol), Pd(PPh3)4 (4.1 g, 3.5 mmol), and K2CO3 (48.6 g, 351.4 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (44.8 g, 93.7 mmol, yield: 80%).
Mass: [(M+H)+]: 479
The materials (3-(adamantan-1-yl)phenyl)boronic acid (30.0 g, 117.1 mmol), 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (35.4 g, 117.1 mmol), Pd(PPh3)4 (4.1 g, 3.5 mmol), and K2CO3 (48.6 g, 351.4 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(3-(adamantan-1-yl)phenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (45.9 g, 96.0 mmol, yield: 82%).
Mass: [(M+H)+]: 479
The materials 2-(4-(adamantan-1-yl)phenyl)-4-chloro-6-phenyl-1,3,5-triazine (30.0 g, 74.6 mmol), (2-chlorophenyl)boronic acid (11.7 g, 74.6 mmol), Pd(PPh3)4 (2.6 g, 2.2 mmol), and K2CO3 (30.9 g, 223.9 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (31.0 g, 64.9 mmol, yield: 87%).
Mass: [(M+H)+]: 479
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (2-chlorophenyl)boronic acid (17.5 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (33.1 g, 96.4 mmol, yield: 86%).
Mass: [(M+H)+]: 345
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (3-chlorophenyl)boronic acid (17.5 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (32.0 g, 93.0 mmol, yield: 83%).
Mass: [(M+H)+]: 345
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (5-chloro-[1,1′-biphenyl]-3-yl)boronic acid (26.0 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(5-chloro-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (38.6 g, 91.9 mmol, yield: 82%).
Mass: [(M+H)+]: 421
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (3-chloronaphthalen-1-yl)boronic acid (23.1 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(3-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (35.8 g, 90.8 mmol, yield: 81%).
Mass: [(M+H)+]: 395
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (6-chloronaphthalen-2-yl)boronic acid (23.1 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 mL of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(6-chloronaphthalen-2-yl)-4,6-diphenyl-1,3,5-triazine (34.9 g, 88.5 mmol, yield: 79%).
Mass: [(M+H)+]: 395
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (2-chloronaphthalen-1-yl)boronic acid (23.1 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours.
After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (33.1 g, 84.0 mmol, yield: 75%).
Mass: [(M+H)+]: 395
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (1-chloronaphthalen-2-yl)boronic acid (23.1 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (46.5 g, 336.2 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(1-chloronaphthalen-2-yl)-4,6-diphenyl-1,3,5-triazine (35.8 g, 90.8 mmol, yield: 81%).
Mass: [(M+H)+]: 395
The materials 2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.1 mmol), (5-chloronaphthalen-2-yl)boronic acid (23.1 g, 112.1 mmol), Pd(PPh3)4 (3.9 g, 3.4 mmol), and K2CO3 (3.9 g, 3.4 mmol) were added to 300 mL of toluene, 45 mL of ethanol, and 45 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(5-chloronaphthalen-2-yl)-4,6-diphenyl-1,3,5-triazine (37.5 g, 95.2 mmol, yield: 85%).
Mass: [(M+H)+]: 395
A01 synthesized by the method of Preparation Example 1 (20.0 g, 41.8 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (19.8 g, 34.7 mmol, yield: 83%).
Mass: [(M+H)+]: 571
A10 synthesized by the method of Preparation Example 10 (20.0 g, 41.8 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) were added to 200 ml of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (19.5 g, 34.3 mmol, yield: 82%).
Mass: [(M+H)+]:571
A11 synthesized by the method of Preparation Example 11 (20.0 g, 41.8 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2-(3-(adamantan-1-yl)phenyl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (19.3 g, 33.9 mmol, yield: 81%).
Mass: [(M+H)+]: 571
A12 synthesized by the method of Preparation Example 12 (20.0 g, 41.8 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) were added to 200 ml of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2-(3-(adamantan-1-yl)phenyl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (18.8 g, 33.1 mmol, yield: 79%).
Mass: [(M+H)+]:571
A15 synthesized by the method of Preparation Example 15 (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-1,3,5-triazine (19.5 g, 38.1 mmol, yield: 80%).
Mass: [(M+H)+]: 512
A16 synthesized by the method of Preparation Example 16 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)-1,3,5-triazine (20.2 g, 41.6 mmol, yield: 82%).
Mass: [(M+H)+]: 486
A17 synthesized by the method of Preparation Example 17 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1,3,5-triazine (21.0 g, 43.2 mmol, yield: 85%).
Mass: [(M+H)+]: 486
A18 synthesized by the method of Preparation Example 18 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) were added to 200 mL of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)-1,3,5-triazine (21.2 g, 43.7 mmol, yield: 86%).
Mass: [(M+H)+]: 486
A19 synthesized by the method of Preparation Example 19 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) were added to 200 ml of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1,3,5-triazine (21.7 g, 44.7 mmol, yield: 88%).
Mass: [(M+H)+]: 486
A20 synthesized by the method of Preparation Example 20 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) were added to 200 ml of 1,4-dioxane, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the reaction solution was filtered, concentrated to remove the solvent therefrom, and then purified by column chromatography to thereby obtain 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1,3,5-triazine (20.5 g, 42.1 mmol, yield: 83%).
Mass: [(M+H)+]: 486
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (12.4 g, 18.4 mmol, yield: 70%).
Mass: [(M+H)+]: 676
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (12.3 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 1,3-bis(4-(4-(adamantan-1yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)benzene (21.7 g, 26.9 mmol, yield: 72%).
Mass: [(M+H)+]: 810
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A03 synthesized by the method of Preparation Example 3 (9.4 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (16.5 g, 21.6 mmol, yield: 82%).
Mass: [(M+H)+]: 766
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A04 synthesized by the method of Preparation Example 4 (10.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3-(4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (16.9 g, 21.3 mmol, yield: 81%).
Mass: [(M+H)+]: 792
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A05 synthesized by the method of Preparation Example 5 (9.7 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 4′-(4-(3-(4-(4-(adamantan-1-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-carbonitrile (15.5 g, 20.0 mmol, yield: 76%).
Mass: [(M+H)+]: 777
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A06 synthesized by the method of Preparation Example 6 (9.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-([1,1′-biphenyl]-4-yl)-4-(3-(4-(4-(adamantan-1-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (14.8 g, 19.8 mmol, yield: 75%).
Mass: [(M+H)+]: 752
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A07 synthesized by the method of Preparation Example 7 (9.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-([1,1′-biphenyl]-2-yl)-4-(3-(4-(4-(adamantan-1-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.8 g, 21.1 mmol, yield: 80%).
Mass: [(M+H)+]: 752
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A08 synthesized by the method of Preparation Example 8 (8.4 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.8 g, 21.9 mmol, yield: 83%).
Mass: [(M+H)+]: 726
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A09 synthesized by the method of Preparation Example 9 (9.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-phenyl-6-(3-(4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazin-2-yl)phenyl)-1,3,5-triazine (16.2 g, 21.6 mmol, yield: 82%).
Mass: [(M+H)+]: 753
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (12.3 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 mL of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 1,2-bis(4-(4-(adamantan-1yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)benzene (25.4 g, 31.3 mmol, yield: 84%).
Mass: [(M+H)+]: 810
B02 synthesized by the method of Preparation Example 22 (15.0 g, 26.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.1 g, 22.4 mmol, yield: 85%).
Mass: [(M+H)+]: 676
B03 synthesized by the method of Preparation Example 23 (15.0 g, 26.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(3-(adamantan-1-yl)phenyl)-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.3 g, 22.6 mmol, yield: 86%).
Mass: [(M+H)+]: 676
B04 synthesized by the method of Preparation Example 24 (15.0 g, 26.3 mmol), A13 synthesized by the method of Preparation Example 13 (9.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(2′-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (15.8 g, 21.1 mmol, yield: 80%).
Mass: [(M+H)+]: 752
B01 synthesized by the method of Preparation Example 21 (15.0 g, 26.3 mmol), A14 synthesized by the method of Preparation Example 14 (9.1 g, 26.3 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), Xphos (0.8 g, 1.6 mmol), and Cs2CO3 (17.2 g, 52.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(3′-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine (15.6 g, 20.8 mmol, yield: 79%).
Mass: [(M+H)+]: 752
B05 synthesized by the method of Preparation Example 25 (15.0 g, 29.3 mmol), A02 synthesized by the method of Preparation Example 2 (11.8 g, 29.3 mmol), Pd(OAc)2 (0.2 g, 0.9 mmol), Xphos (0.8 g, 1.8 mmol), and Cs2CO3 (19.1 g, 58.7 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 mL of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine (17.2 g, 22.9 mmol, yield: 78%).
Mass: [(M+H)+]: 752
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), B06 synthesized by the method of Preparation Example 26 (18.1 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 mL of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalen-2-yl)-6-phenyl-1,3,5-triazine (20.8 g, 28.7 mmol, yield: 77%).
Mass: [(M+H)+]: 726
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), B07 synthesized by the method of Preparation Example 27 (18.1 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(6-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalen-2-yl)-6-phenyl-1,3,5-triazine (20.8 g, 28.7 mmol, yield: 77%).
Mass: [(M+H)+]: 726
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), B08 synthesized by the method of Preparation Example 28 (18.1 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 mL of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(1-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalen-2-yl)-6-phenyl-1,3,5-triazine (20.6 g, 28.4 mmol, yield: 76%).
Mass: [(M+H)+]: 726
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), B09 synthesized by the method of Preparation Example 29 (18.1 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalen-1-yl)-6-phenyl-1,3,5-triazine (21.4 g, 29.5 mmol, yield: 79%).
Mass: [(M+H)+]: 726
A02 synthesized by the method of Preparation Example 2 (15.0 g, 37.3 mmol), B10 synthesized by the method of Preparation Example 30 (18.1 g, 37.3 mmol), Pd(OAc)2 (0.3 g, 1.1 mmol), Xphos (1.1 g, 2.2 mmol), and Cs2CO3 (24.3 g, 74.6 mmol) were added to 180 mL of toluene, 30 mL of EtOH, and 30 ml of water, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, an extraction process was performed on the reaction solution by utilizing methylene chloride, and an organic layer extracted therefrom was dried utilizing magnesium sulfate, concentrated, and then purified by column chromatography to thereby obtain 2-(4-(adamantan-1-yl)phenyl)-4-(6-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalen-1-yl)-6-phenyl-1,3,5-triazine (21.6 g, 29.9 mmol, yield: 80%).
Mass: [(M+H)+]: 726
After Compound 001 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a commonly suitable method, a blue organic electroluminescent device was manufactured as follows.
First, a glass substrate with a 1,200 angstrom (Å)-thick indium tin oxide (ITO) thin-film coated thereon was cleaned by ultrasonication utilizing distilled water. After cleaning with distilled water, ultrasonic cleaning was performed on the substrate by utilizing a solvent such as isopropyl alcohol, acetone, methanol, and/or the like, and the substrate was dried and transferred to a ultraviolet (UV) ozone cleaner (Powersonic 405, Hwashin Tech Co., Ltd.). Then, the substrate was cleaned for 5 minutes by utilizing UV and transferred to a vacuum deposition apparatus.
Compound A and Compound B were co-deposited on the ITO transparent electrode prepared as described above at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and Compound A was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,400 Å. Then, Compound C was deposited on the hole transport layer to form a hole transport auxiliary layer having a thickness of 50 Å, and Compound D and Compound E were co-deposited thereon at a weight ratio of 98:2 to form an emission layer having a thickness of 200 Å. Then, Compound F was deposited on the emission layer to form an electron transport auxiliary layer having a thickness of 50 Å, and Compound 001 and Compound G were co-deposited thereon at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. Then, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic electroluminescent device.
The structures of Compounds A to G utilized herein are as follows.
Blue organic electroluminescent devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 1 were each respectively utilized instead of Compound 001, which was utilized as an electron transport layer material in Example 1.
From Table 1, it was confirmed that the organic electroluminescent devices of Examples 1 to 20 exhibited enhanced or superior performance in terms of driving voltage, emission peak, and current efficiency, compared to the organic electroluminescent devices of Comparative Examples 1 to 10.
According to the one or more embodiments, by including a heterocyclic compound represented by Formula 1, a light-emitting device may exhibit excellent or suitable performance in terms of driving voltage, emission peak, current efficiency, and device stability. In this regard, high-quality electronic apparatuses and electronic equipment may be manufactured by utilizing the light-emitting device.
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 |
|---|---|---|---|
| 10-2023-0016264 | Feb 2023 | KR | national |
