Patent Application
20240196741
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0138624, filed on Oct. 25, 2022, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
One or more embodiments relate to an organic compound, an opto-electronic device including the same, an electronic apparatus including the opto-electronic device, and an electronic device including the electronic apparatus.
Opto-electronic devices are devices that convert light energy or a light signal into electrical energy or an electrical signal. Examples of opto-electronic devices include a photovoltaic cell or a solar cell that converts light energy into electrical energy, a photodetector or a light sensor that detects light energy and converts the detected light energy into an electrical signal, and/or the like.
Electronic apparatuses including opto-electronic devices and organic light-emitting devices have been developed. As an example, light emitted from an organic light-emitting device may be reflected by an object (e.g., a finger of a user) in contact with an electronic apparatus, and then incident on an opto-electronic device. As the opto-electronic device detects incident light energy and converts the detected incident light energy into an electrical signal, it may be utilized to recognize that the object is in contact with the electronic apparatus. The opto-electronic device may be utilized as a fingerprint recognition sensor and/or the like.
Aspects according to one or more embodiments are directed toward an organic compound having a relatively small molecular weight and improved light absorption efficiency for green light, and an opto-electronic device having relatively high heat resistance characteristics and high photoelectric characteristics with respect to green light by including the organic compound. In addition, aspects according to one or more embodiments are directed toward a high-quality electronic apparatus and a high-quality electronic device, each including the opto-electronic device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, an opto-electronic device includes a first electrode, a second electrode facing the first electrode, a photoactive layer between the first electrode and the second electrode, and an organic compound represented by Formula 1:
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, or a C1-C60 alkoxy group, or
According to one or more embodiments, an electronic apparatus includes the opto-electronic device.
According to one or more embodiments, an electronic device includes the electronic apparatus.
According to one or more embodiments, an organic compound is represented by Formula 1.
The above and other aspects, features, and enhancements of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, 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 below, by referring to the drawings, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c”, “at least one selected from a, b, and c”, “at least one selected from the group consisting of a, b, and c”, “at least one from among a, b, and c”, “at least one of a to c”, etc., 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.
According to one or more embodiments of the present disclosure, an opto-electronic device includes a first electrode, a second electrode facing the first electrode, a photoactive layer arranged between the first electrode and the second electrode, and an organic compound represented by Formula 1. Formula 1 will be described in more detail below.
In an embodiment, the first electrode may be an anode. The second electrode may be a cathode. The photoactive layer may be to absorb light to generate excitons. The excitons may be separated into electrons and holes. As the electrons and holes are generated, current may flow (e.g., an electrical current may be generated).
In an embodiment, the photoactive layer may include the organic compound.
The organic compound may be to absorb light to generate electrons and holes, and may serve as an electron donor. The organic compound may be referred to as an electron donating compound.
In an embodiment, the opto-electronic device may further include an electron accepting compound. The electron accepting compound may serve as an electron acceptor. For example, the electron accepting compound may be fullerene, or may be represented by one of Formulae 4-1 to 4-4:
In an embodiment, the electron accepting compound may be fullerene. For example, the electron accepting compound may be fullerene 60 or fullerene 70:
In an embodiment, the electron accepting compound may be one of Compounds N1 to N36:
In an embodiment, the photoactive layer may include the organic compound and the electron accepting compound.
In an embodiment, the opto-electronic device may further include a hole transport region arranged between the first electrode and the photoactive layer and an electron transport region arranged between the photoactive layer and the second electrode. Holes generated by the photoactive layer may move to the first electrode through the hole transport region. Electrons generated by the photoactive layer may move to the second electrode through the electron transport region.
In an embodiment, the photoactive layer may include a first layer adjacent to the hole transport region and a second layer adjacent to the electron transport region.
In an embodiment, the first layer may include the organic compound. For example, the first layer may not include (e.g., may exclude) the electron accepting compound.
In an embodiment, the second layer may include the electron accepting compound. The electron accepting compound may be fullerene. For example, the second layer may not include (e.g., may exclude) the organic compound.
For example, the first layer may be referred to as a p-type or kind photoactive layer or an electron donor layer. The second layer may be referred to as an n-type or kind photoactive layer or an electron acceptor layer.
In an embodiment, the photoactive layer may further include a third layer arranged between the first layer and the second layer. The third layer may include (e.g., both) the organic compound and the electron accepting compound.
According to one or more embodiments of the present disclosure, an electronic apparatus includes the opto-electronic device.
In an embodiment, the electronic apparatus may further include a light-emitting device adjacent to the opto-electronic device. The light-emitting device may not overlap the opto-electronic device.
For example, light emitted by the light-emitting device may be extracted (e.g., emitted) to the outside of the electronic apparatus. The light may be reflected by an external object to be incident into the electronic apparatus. The opto-electronic device may be to absorb the incident light. For example, the opto-electronic device may be utilized as a sensor that recognizes an object outside the electronic apparatus.
In an embodiment, the light-emitting device may include a first electrode, a second electrode facing the first electrode, and an emission layer arranged between the first electrode and the second electrode. In an embodiment, the first electrode of the light-emitting device may be a portion of the first electrode of the opto-electronic device. In one or more embodiments, the first electrode of the light-emitting device may be apart from the first electrode of the opto-electronic device, but may include the same material as the first electrode of the opto-electronic device. In an embodiment, the second electrode of the light-emitting device may be a portion of the second electrode of the opto-electronic device. In one or more embodiments, the second electrode of the light-emitting device may be apart from the second electrode of the opto-electronic device, but may include the same material as the second electrode of the opto-electronic device. The emission layer may include a dopant and a host, and may be to emit light.
In an embodiment, the opto-electronic device may further include a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof. The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof. For example, the emission auxiliary layer may generate a resonance phenomenon by light interference, and the buffer layer may control injection of electrons and prevent or reduce loss of holes.
For example, the first electrode, the hole transport region, the electron transport region, and the second electrode included in the opto-electronic device may be substantially identical to or different from the first electrode, the hole transport region, the electron transport region, and the second electrode included in the light-emitting device, respectively. For example, a portion of the opto-electronic device may extend (e.g., laterally or in a plan view) to constitute a portion of the light-emitting device.
In an embodiment, the electronic apparatus may further include a thin-film transistor, a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof, and the thin-film transistor may be electrically connected to the first electrode.
According to one or more embodiments of the present disclosure, an electronic device includes the electronic apparatus. The electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and/or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual or augmented-reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and/or a signboard.
According to one or more embodiments of the present disclosure, an organic compound is represented by Formula 1:
For example, when Z1 is N, Z1 and Ar1 may be bonded to each other via a single bond. When Z2 is N, Z2 and Ar1 may be bonded to each other via a single bond. When Z1 is N, Ar1 may be a C3-C20 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C20 heterocyclic group unsubstituted or substituted with at least one R10a. For example, when Z1 is N, Ar1 may not be a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, and Z1 and Ar1 may be bonded to each other via a single bond.
In an embodiment, when Z1 is N, a ring formed by bonding between Z1 and Ar1 may be a 5-membered ring.
In an embodiment, when Z1 is N, Formula 2 may be represented by Formula 2-1:
In an embodiment, Formula 2 may be represented by one of Formulae 2a, 2b, or 2c:
In an embodiment, i) b2 may be 1, b3 may be 0, and b4 may be 0; ii) b2 may be 0, b3 may be 1, and b4 may be 0; or iii) b2 may be 1, b3 may be 0, and b4 may be 1.
In an embodiment, Ar1 may be: a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclohexyl group, a phenyl group, a naphthyl group, or a thiophenyl group; or a cyclohexyl group, a phenyl group, a naphthyl group, or a thiophenyl group, each substituted with at least one selected from the group consisting of —F, —Cl, and a cyano group.
In an embodiment, Formula 1 may be represented by one of Formulae 3-1 to 3-3:
In an embodiment, L1 may be a single bond.
In an embodiment, a molecular weight of the organic compound may be about 1,000 or less. For example, the molecular weight of the organic compound may be about 600 or less. In one embodiment, the molecular weight of the organic compound may be in a range of about 400 to about 560.
In an embodiment, at least one of Ar2 to Ar4 may include a thiophene group.
For example, the thiophene group may include thiophene, 2,3-dihydrothiophene, and/or 2,3-dihydrobenzothiophene.
In an embodiment, Ar3 and Ar4 may each independently be a benzene group, a naphthalene group, a thiophene group, a pyrrole group, a furan group, an indole group, a benzothiophene group, a benzofuran group, a quinoline group, or an isoquinoline group.
For example, the furan group may include furan, 2,3-dihydrofuran, benzofuran, and/or 2,3-dihyrobenzofuran.
In an embodiment, i) T2 may be *—C(T21)(T22)-*′ or *—Si(T21)(T22)-*′, and T21 and T22 may be linked to each other via a single bond; ii) T3 may be *—C(T31)(T32)-*′ or *—Si(T31)(T32)-*′, and T31 and T32 may be linked to each other via a single bond; or iii) T4 may be *—C(T41)(T42)-*′ or *—Si(T41)(T42)-*′, and T41 and T42 may be linked to each other via a single bond.
In an embodiment, a highest occupied molecular orbital (HOMO) level of the organic compound may be in a range of about −6.0 eV to about −5.3 eV.
In an embodiment, a lowest unoccupied molecular orbital (LUMO) level of the organic compound may be in a range of about −3.0 eV to about −2.4 eV.
In an embodiment, a maximum absorption wavelength of the organic compound may be in a range of about 400 nm to about 550 nm. In one embodiment, the maximum absorption wavelength of the organic compound may be in a range of about 420 nm to about 535 nm.
In an embodiment, the organic compound may be one of Compounds 1 to 96:
Because the organic compound has a molecular weight of about 1,000 or less, a deposition temperature for forming the organic compound may be relatively low. Thus, the organic compound may have excellent or suitable heat resistance characteristics.
The organic compound represented by Formula 1 may include only one Ar11 (e.g., only one group) represented by Formula 2. Ar11 represented by Formula 2 may not be directly bonded to N of Formula 1, and may be bonded to L1 or Ar2. In some embodiments, at least one of b2 to b4 in Formula 1 may be 1 or 2. In one embodiment, each of b2 to b4 in Formula 1 may not be 0. As a result, a twist angle within a molecule may be reduced so that relatively more (e.g., many) molecules may be included in a unit thickness, and thus, an opto-electronic device including the organic compound may have higher (e.g., high) light absorption efficiency for green wavelength light.
Hereinafter, the structures of the opto-electronic device 30 and the light-emitting device 10 according to embodiments and methods of manufacturing the opto-electronic device 30 and the light-emitting device 10 will be described in more detail 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 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 an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The hole transport region 120 may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The hole transport region 120 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 120 may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein constituting layers of each structure are stacked sequentially from the first electrode 110 in the respective stated order.
The hole transport region 120 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
For example, each of Formulae 201 and 202 may include at least one of the groups represented by Formulae CY201 to CY217:
In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 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 of the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one of groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203, and may include at least one 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) any of the groups represented by Formulae CY201 to CY217.
For example, the hole transport region 120 may include at least one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region 120 may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region 120 includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region 120, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer 130, and the electron blocking layer may block or reduce the flow (e.g., leakage) of electrons from the emission layer 130 to the hole transport region 120. Materials that may be included in the hole transport region 120 may be included in the emission auxiliary layer and the electron blocking layer.
p-Dopant
The hole transport region 120 may further include, in addition to the materials described above, a charge-generation material for improving conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region 120 (e.g., in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, a LUMO energy level of the p-dopant may be −3.5 eV or less.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and/or the like:
In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); and/or the like.
Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, etc.), and/or the like.
Examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
Examples of the metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), a rhenium oxide (e.g., ReO3, etc.), and/or the like.
Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and/or the like.
Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, NaI, KI, RbI, CsI, and/or the like.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mg12, Cal2, Srl2, Bal2, and/or the like.
Examples of the transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), a vanadium halide (e.g., VF3, VCl3, VBr3, VI3, etc.), a niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (e.g., CrF3, CrO3, CrBr3, CrI3, etc.), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), a manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, Rhl2, etc.), an iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and/or the like.
Examples of the post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (e.g., Ink3, etc.), a tin halide (e.g., SnI2, etc.), and/or the like.
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, Sm13, and/or the like.
Examples of the metalloid halide may include antimony halide (e.g., SbCl5, etc.) and/or the like.
Examples of the metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (e.g., ZnTe, etc.), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and/or the like.
The light-emitting device 10 may include the emission layer 130 arranged on the hole transport region 120.
The emission layer 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 an embodiment, the emission layer 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 arranged between the two or more emitting units. When the emission layer 130 includes the two or more emitting units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer 130 may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In an embodiment, the emission layer 130 may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other to emit white light. In one or more embodiments, the emission layer 130 may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
The emission layer 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
An amount of the dopant in the emission layer 130 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 an embodiment, the emission layer 130 may include a quantum dot.
In an embodiment, the emission layer 130 may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or a dopant in the emission layer 130.
A thickness of the emission layer 130 may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer 130 is within these ranges, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 Formula 301
For example, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include one of Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di(carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
The phosphorescent dopant may include at least one transition metal as a 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:
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 an embodiment, when xc1 in Formula 401 is 2 or more, two ring A401(s) in two or more of L401(s) may optionally be linked to each other via T402, which is a linking group, and/or two ring A402(s) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as defined herein in connection with T401.
L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, at least one of Compounds PD1 to PD39 or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
For example, the fluorescent dopant may include a compound represented by Formula 501:
For example, Ar501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed with each other.
In an embodiment, xd4 in Formula 501 may be 2.
For example, the fluorescent dopant may include at least one of Compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
The emission layer 130 may include a delayed fluorescence material.
In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer 130 may serve as a host or a dopant depending on the type or kind of other materials included in the emission layer 130.
In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be 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 above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
For example, the delayed fluorescence material may include i) a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, etc.), and/or ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).
Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF14:
The emission layer 130 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.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected through a process with a lower cost, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) and/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 may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.
Examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and/or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GalnNSb, GaInPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; or any combination thereof. In an embodiment, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and/or the like.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and/or InTe; a ternary compound, such as InGaS3 and/or InGaSes; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CulnS2, CuGaO2, AgGaO2, and/or AgAlO2; a quaternary compound, such as AgInGaS and/or AgInGaS2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, and/or SnPbSTe; or any combination thereof.
The Group IV element or compound may include: a single element, such as Si and/or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and/or the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.
In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or 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 or reduces 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. An 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 may include an oxide of metal, metalloid, or non-metal, a semiconductor compound, or any combination thereof.
Examples of the oxide of metal, metalloid, or non-metal may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; or any combination thereof. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, or, about 30 nm or less, and within these ranges, color purity or color reproducibility may be improved. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the viewing angle of light may be improved.
In some embodiments, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
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 an emission layer including the quantum dot. 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 embodiment, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by combining light of one or more suitable colors.
The opto-electronic device 30 may include the photoactive layer 135 arranged on the hole transport region 120. The photoactive layer 135 may be arranged between the hole transport region 120 and the electron transport region 140. In an embodiment, the photoactive layer 135 may be arranged between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. In one or more embodiments, the photoactive layer 135 may be arranged between the emission auxiliary layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
The photoactive layer 135 may include the organic compound and the electron accepting compound. In one embodiment, the organic compound and the electron accepting compound may be mixed and included in the photoactive layer 135. For example, the photoactive layer 135 may be a single layer including the organic compound and the electron accepting compound.
The photoactive layer 135 may be to absorb light incident to the electronic apparatus to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In one embodiment, the organic compound included in the photoactive layer 135 may serve as a donor for supplying electrons, and the electron accepting compound included in the photoactive layer 135 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 30 including the photoactive layer 135 may serve as a photosensor. For example, the opto-electronic device 30 may serve as a fingerprint recognition sensor, which will be described in more detail with reference to
The electron transport region 140 may be arranged on the emission layer 130 of the light-emitting device 10 and on the photoactive layer 135 of the opto-electronic device 30. The electron transport region 140 may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron transport region 140 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 140 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 constituting layers of each structure are stacked sequentially from the emission layer 130 in the respective stated order.
The electron transport region 140 (e.g., the buffer layer, the hole blocking layer, the electron control layer, and/or the electron transport layer in the electron transport region 140) 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 140 may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In an embodiment, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In one or more embodiments, the electron transport region 140 may include a compound represented by 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 140 may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
A thickness of the electron transport region 140 may be from about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region 140 includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region 140 are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region 140 (e.g., the electron transport layer in the electron transport region 140) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, and/or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, and/or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex and/or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, 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 140 may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
The electron injection layer may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof.
The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include one or more oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), and/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 an alkali metal oxide, such as Li2O, Cs2O, and/or K2O, an alkali metal halide, such as LiF, NaF, CsF, KF, Lil, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound (e.g., oxide), such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying the condition of 0<x<1), and/or BaxCa1-xO (wherein x is a real number satisfying the condition of 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and/or the like.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand linked to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
The electron injection layer may 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 (e.g., a compound represented by Formula 601).
In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a 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, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for 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 second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be arranged outside the first electrode 110, and/or a second capping layer may be arranged outside the second electrode 150. In one embodiment, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the emission layer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the emission layer 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 emission layer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the emission layer 130 of the light-emitting device 10 may be extracted (e.g., emitted) toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, or light generated in the emission layer 130 of the light-emitting device 10 may be extracted (e.g., emitted) 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 luminescence efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (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 of 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 an embodiment, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.
For example, at least one of the first capping layer 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 of the first capping layer or the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
A film may be, for example, an optical member (or a light control member) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.), a protection member (e.g. an insulating layer, a dielectric layer, etc.), and/or the like.
The opto-electronic device 31 shown in
The opto-electronic device 31 may include the photoactive layer 135 arranged between the hole transport region 120 and the electron transport region 140.
In an embodiment, the photoactive layer 135 may be arranged between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. In one or more embodiments, the photoactive layer 135 may be arranged between the emission auxiliary layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
The photoactive layer 135 may include a first layer 131 adjacent to the hole transport region 120 and a second layer 132 adjacent to the electron transport region 140. In an embodiment, the first layer 131 may be in direct contact with the second layer 132.
In an embodiment, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. In one or more embodiments, the first layer 131 may be in direct contact with the emission auxiliary layer arranged on the hole transport layer.
In an embodiment, the second layer 132 may be in direct contact with the buffer layer included in the electron transport region 140.
The first layer 131 may include the organic compound. For example, the first layer 131 may not include (e.g., may exclude) the electron accepting compound.
The second layer 132 may include the electron accepting compound. For example, the second layer 132 may not include (e.g., may exclude) the organic compound.
For example, the photoactive layer 135 may have a multi-layered structure divided into the first layer 131 including the organic compound and the second layer 132 including the electron accepting compound.
The photoactive layer 135 may be to absorb incident light to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In one embodiment, the organic compound included in the first layer 131 may serve as a donor for supplying electrons, and the electron accepting compound included in the second layer 132 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 31 including the photoactive layer 135 may serve as a photosensor. For example, the opto-electronic device 31 may serve as a fingerprint recognition sensor, which will be described with reference to
The opto-electronic device 32 shown in
The opto-electronic device 32 may include the photoactive layer 135 arranged between the hole transport region 120 and the electron transport region 140. In an embodiment, the photoactive layer 135 may be arranged between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. In one or more embodiments, the photoactive layer 135 may be arranged between the emission auxiliary layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
The photoactive layer 135 may include the first layer 131 adjacent to the hole transport region 120, the second layer 132 adjacent to the electron transport region 140, and a third layer 133 arranged between the first layer 131 and the second layer 132. In an embodiment, the third layer 133 may be in direct contact with the first layer 131 and/or the second layer 132.
In an embodiment, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. In one or more embodiments, the first layer 131 may be in direct contact with the emission auxiliary layer arranged on the hole transport layer.
In an embodiment, the second layer 132 may be in direct contact with the buffer layer included in the electron transport region 140.
The first layer 131 may include the organic compound. For example, the first layer 131 may not include (e.g., may exclude) the electron accepting compound.
The second layer 132 may include the electron accepting compound. For example, the second layer 132 may not include (e.g., may exclude) the organic compound.
The third layer 133 may include (e.g., both) the organic compound and the electron accepting compound. For example, the organic compound and the electron accepting compound may be mixed and included in the third layer 133.
For example, the photoactive layer 135 may have a multi-layered structure divided into the first layer 131 including (e.g., only) the organic compound, the third layer 133 including both (e.g., simultaneously) the organic compound and the electron accepting compound, and the second layer 132 including (e.g., only) the electron accepting compound.
The photoactive layer 135 may be to absorb incident light to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In one embodiment, the organic compound included in each of the first layer 131 and the third layer 133 may serve as a donor for supplying electrons, and the electron accepting compound included in each of the second layer 132 and the third layer 133 may serve as an acceptor for receiving electrons. Accordingly, the opto-electronic device 32 including the photoactive layer 135 may serve as a photosensor. For example, the opto-electronic device 32 may serve as a fingerprint recognition sensor, which will be described with reference to
The light-emitting device 10 and the opto-electronic device 30, 31, and/or 32 may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device 10 and the opto-electronic device 30, 31, and/or 32, 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 direction in which light emitted from the light-emitting device 10 travels. For example, the light emitted from the light-emitting device 10 may be blue light or white light. Details on the light-emitting device 10 may be as described above. In an embodiment, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a 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 plurality of subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the plurality of subpixel areas.
A pixel defining layer may be arranged among the plurality of 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 plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the plurality of color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area emitting a first color light, a second area emitting a second color light, and/or a third area emitting a third color light, and 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 embodiment, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include (e.g., may exclude) a quantum dot. Details on the quantum dot may be as described herein. The first area, the second area, and/or the third area may each further include a scatterer.
For example, the light-emitting device 10 may be to emit a first light, the first area may be to absorb the first light to emit a first-first color light, the second area may be to absorb the first light to emit a second-first color light, and the third area may be to absorb the first light to emit a 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 embodiment, 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 opto-electronic device(s) 30, 31, and/or 32 and the light-emitting device 10 as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, and the source electrode or the drain electrode may be electrically connected to the first electrode 110 or the second electrode 150 of the light-emitting device 10.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The active 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 opto-electronic device 30, 31, and/or 32 and the light-emitting device 10. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device 10. The sealing portion may allow light from the light-emitting device 10 to be extracted (e.g., emitted) to the outside, and may concurrently (e.g., simultaneously) prevent or reduce ambient air and/or moisture from penetrating into the opto-electronic device(s) 30, 31, and/or 32 and the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
Various suitable 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 usage of the electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a 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 (e.g., fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the opto-electronic device(s) 30, 31, and/or 32 and the light-emitting device 10 as described above, a biometric information collector.
The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., 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 (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The opto-electronic device(s) 30, 31, and/or 32 may be included in one or more suitable electronic devices.
For example, the electronic device including the opto-electronic device 30, 31, and/or 32 may be at least one of flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lightings, signal lights, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, three-dimensional (3D) displays, virtual or augmented-reality displays, vehicles, video walls including multiple displays tiled together, theater or stadium screens, phototherapy devices, and signboards.
Because the opto-electronic device(s) 30, 31, and/or 32 has excellent or suitable photoelectric characteristics, the electronic device including the opto-electronic device(s) 30, 31, and/or 32 may serve as an optical sensor, such as a fingerprint recognition sensor.
The electronic apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, and/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 thin-film transistor TFT may be arranged on the buffer layer 210. The thin-film transistor TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor, such as silicon and/or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be 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 active layer 220, and the source electrode 260 and the drain electrode 270 may be in contact with the exposed portions of the source region and the drain region of the active layer 220.
The light-emitting device 10 and the opto-electronic device 30 may be arranged on the thin-film transistor TFT.
The thin-film transistor TFT electrically connected to the light-emitting device 10 may be to transmit an electrical signal for driving the light-emitting device 10. The thin-film transistor TFT electrically connected to the opto-electronic device 30 may be to transmit an electrical signal generated by the opto-electronic device 30. The thin-film transistor TFT may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device 10 and the opto-electronic device 30 may be provided on the passivation layer 280.
The light-emitting device 10 may include the first electrode 110, the hole transport region 120, the emission layer 130, the electron transport region 140, and the second electrode 150. The opto-electronic device 30 may include the first electrode 110, the hole transport region 120, the photoactive layer 135, the electron transport region 140, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may expose certain regions of the source electrode 260 and the drain electrode 270 without completely covering the source electrode 260 and the drain electrode 270, and the first electrode 110 may be connected to the exposed regions of the source electrode 260 and 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. The pixel defining layer 290 may be a polyimide or polyacrylic organic film.
The hole transport region 120 may be arranged on the pixel defining layer 290. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the opto-electronic device 30 may be integrally formed as a single body. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
Each of the emission layer 130 and the photoactive layer 135 may be arranged on the hole transport region 120. Each of the emission layer 130 and the photoactive layer 135 may overlap the certain region of the first electrode 110 that is exposed by the pixel defining layer 290.
The electron transport region 140 may be arranged on the emission layer 130 and the photoactive layer 135. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the opto-electronic device 30 may be integrally formed as a single body. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the opto-electronic device 30 may be integrally formed as a single body. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the opto-electronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed substantially at the same time.
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 the light-emitting device 10 and the opto-electronic device 30 to protect the light-emitting device 10 and the opto-electronic device 30 from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film and the organic film.
The light-emitting device 10 may be to emit light L1, L2, and L3. For example, the light L1, L2, and L3 may each be green light.
The light L3 from among the lights L1, L2, and L3 that have been emitted may be incident on an object 600 outside the electronic apparatus. For example, the object 600 may be a finger of a user of the electronic apparatus. A light L3′ reflected by the object 600 may be incident on the opto-electronic device 30.
The photoactive layer 135 may be to absorb the incident light L3′ to form excitons. The excitons may generate holes and electrons. For example, the photoactive layer 135 may be to absorb light to generate an electrical signal. In one embodiment, the organic compound included in the photoactive layer 135 may serve as a donor for supplying electrons, and the electron accepting compound included in the photoactive layer 135 may serve as an acceptor for receiving electrons. For example, the opto-electronic device 30 may detect energy of the light L3′ and convert the detected energy into an electrical signal. Accordingly, the opto-electronic device 30 may recognize the object 600 that has come into contact with (or approached) the electronic apparatus. Accordingly, the opto-electronic device 30 including the photoactive layer 135 may serve as an optical sensor (e.g., a fingerprint recognition sensor).
The electronic apparatus of
The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic device 1 may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.
The non-display area NDA is an area in which an image is not displayed, and may be around (e.g., entirely surround) the display area DA. A driver for providing electrical signals and/or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element and/or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
The electronic device 1 may have different lengths in the x-axis direction and in the y-axis direction. For example, as shown in
Referring to
The vehicle 1000 may travel on a road and/or a track. The vehicle 1000 may move in a certain 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/or a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as the remaining parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, and/or a pillar provided at a boundary between doors. The chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a 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 an embodiment, 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 an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be 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 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 the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a view of the rear of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the body. In an embodiment, a plurality of side mirrors 1300 may be provided. One of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in 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 transmission selection lever indicator, 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 apart from the cluster 1400 with the center fascia 1500 therebetween. In an embodiment, 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 an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In an embodiment, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In an embodiment, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, or the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic electroluminescent (EL) display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, as the display apparatus 2 according to an embodiment, an organic light-emitting display apparatus including the light-emitting device according to an embodiment will be described as an example, but one or more suitable types (kinds) of display apparatuses as described above may be utilized in embodiments.
Referring to
Referring to
Referring to
Respective layers included in the hole transport region 120, the emission layer 130, the photoactive layer 135, and respective layers included in the electron transport region 140 may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When respective layers included in the hole transport region 120, the emission layer 130, the photoactive layer 135, and respective layers included in the electron transport region 140 are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed. Because the organic compound, in which a first moiety represented by Formula 1 and a second moiety represented by Formula 2 are bonded to each other, has excellent or suitable heat resistance characteristics, when the first layer 131 included in the photoactive layer 135 is formed utilizing the organic compound by vacuum deposition, the first layer 131 may be easily formed without defects.
The term “C3-C60 carbocyclic group” as used herein refers to a cyclic group consisting of only carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms, and the term “C1-C60 heterocyclic group” as used herein refers to a cyclic group that has, in addition to 1 to 60 carbon atoms, 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 3 to 61.
The term “cyclic group” as used herein may include the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used 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 used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.
For example,
The term “cyclic group,” “C3-C60 carbocyclic group,” “C1-C60 heterocyclic group,” “π electron-rich C3-C60 cyclic group,” or “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein each refers to a group condensed with any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are used. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may include a C3-C1 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C1 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 C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C1 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C1 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and/or the like. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle and/or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and/or the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle and/or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and/or the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C1 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group that has, in addition to 1 to 10 carbon atoms, at least one heteroatom as a ring-forming atom, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C1 cycloalkenyl group” as used 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 may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-Cia heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has, in addition to 1 to 10 carbon atoms, at least one heteroatom as a ring-forming atom, and at least one double bond in the ring thereof. Examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C1-Cia heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C6a arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a fluorenyl group, and/or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that includes, in addition to 1 to 60 carbon atoms, at least one heteroatom, as ring-forming atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that includes, in addition to 1 to 60 carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiofuranyl group, and/or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed with each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, an adamantyl group, and/or the like. The term polyvalent (e.g., divalent) non-aromatic condensed polycyclic group” as used herein refers to a polyvalent (e.g., divalent) group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more rings condensed with each other, at least one heteroatom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an 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 benzonaphtho silolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, an azaadamantyl group, and/or the like. The term “polyvalent (e.g., divalent) non-aromatic condensed heteropolycyclic group” as utilized herein refers to a polyvalent (e.g., divalent) group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein refers to a monovalent group represented by —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein refers to a monovalent group represented by —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein refers to a monovalent group represented by -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 used herein refers to a monovalent group represented by -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as used herein refers to:
Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group.
The term “heteroatom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “tert-Bu” or “But” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
The term “biphenyl group” as used 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 used 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 used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
The x-axis, y-axis, and z-axis as used herein 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 be orthogonal to each other, but the x-axis, y-axis, and z-axis may also refer to different directions that are not orthogonal to each other.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
3.00 g (10.83 mmol) of Intermediate A1 was dissolved in 10 mL of 40% aqueous methylamine, and then, the mixture was stirred at 50° C. for 6 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered, and then, the obtained solid was extracted three times utilizing 50 mL of water and 50 mL of dichloromethane. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 2.83 g (yield of 90%) of Intermediate A2 (6-bromo-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione). Intermediate A2 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): δ 8.54 (m, 1H), 8.48 (m, 1H), 8.29 (d, 1H), 8.24 (d, 1H), 7.98 (m, 1H), 3.05 (s, 3H)
C13H8BrNO2: calc. 290.12, found 288.97.
2.00 g (6.89 mmol) of Intermediate A2, 2.63 g (10.34 mmol, 1.5 eq) of bis(pinacolato)diborane, 0.30 g (0.34 mmol, 0.05 eq) of PdCl2(dppf)2, and 2.03 g (20.68 mmol, 3 eq) of CH3COOK were dissolved in 60 mL of dimethyl sulfoxide (DMSO), and then, the mixture was stirred at 80° C. for 12 hours. After cooling the reaction solution to room temperature, an extraction process was performed thereon three times utilizing 50 mL of water and 50 mL of dichloromethane. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.63 g (yield of 70%) of Intermediate A3. Intermediate A3 (2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): δ 8.50 (m, 1H), 8.49 (d, 1H), 8.37 (m, 1H), 7.87 (m, 1H), 7.86 (d, 1H), 3.05 (s, 3H), 1.20 (s, 12H)
C19H20BNO4: calc. 337.18, found 337.15.
In a nitrogen atmosphere, 0.85 g (0.93 mmol, 0.1 eq) of Pd2(dba)3 and 0.27 g (0.93 mmol, 0.1 eq) of [(t-Bu)3PH]BF4 were added to 80 mL of toluene. Successively, 2.67 g (27.8 mmol, 3 eq) of NaOC(CH3)3 and 3.00 g (9.26 mmol) of 3,3′-dibromo-2,2′-bithiophene were added thereto. After 5 minutes, 1.12 g (12.04 mmol, 1.3 eq) of aniline was added thereto, and the mixture was stirred at 120° C. for 6 hours. After cooling the reaction solution to room temperature, an extraction process was performed thereon three times utilizing 50 mL of water and 50 mL of diethyl ether. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.30 g (yield of 55%) of Intermediate B2 (4-phenyl-4H-dithieno[3,2-b:2′,3′-d]pyrrole). Intermediate B2 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): δ 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.31 (d, 2H), 7.12 (d, 2H)
C14H9NS2, calc. 255.35, found 255.02.
1.00 g (3.92 mmol, 1 eq) of Intermediate B2 was dissolved in 90 mL of dochloromethane, and then, 0.77 g (4.31 mmol, 1.1 eq) of N-bromosuccinimide was stirred at room temperature for 6 hours. 60 mL of water was added to the reaction solution, and an extraction process was performed thereon three times utilizing 60 mL of dichloromethane. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.08 g (yield of 80%) of Intermediate B3 (2-bromo-4-phenyl-4H-dithieno[3,2-b:2′,3′-d]pyrrole). Intermediate B3 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): δ 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.31 (d, 1H), 7.12 (d, 1H), 6.91 (s, 1H)
C14H8BrNS2: calc. 334.25, found 332.93.
1.01 g (3.00 mmol, 1 eq) of Intermediate A3, 1.0 g (3.00 mmol, 1 eq) of Intermediate B3, 0.70 g (0.6 mmol, 0.2 eq) of Pd(PPh3)4, and 1.03 g (17.92 mmol, 2.5 eq) of K2CO3 were dissolved in 60 mL of a mixed solution of toluene/H2O (volume ratio of 2/1), and then, the mixture was stirred at 100° C. for 12 hours. After cooling the reaction solution to room temperature, 60 mL of water was added thereto, and an extraction process was performed thereon three times utilizing 60 mL of dichloromethane. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 0.97 g (yield of 70%) of Compound 3 (2-methyl-6-(4-phenyl-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione). Compound 3 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): δ 9.22 (m, 1H), 8.68 (d, 1H), 8.50 (m, 1H), 8.23 (d, 1H), 7.87 (m, 1H), 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.31 (d, 1H), 7.12 (d, 1H), 7.10 (s, 1H) 3.05 (s, 3H)
C27H16N2O2S2: calc. 464.56, found 464.07.
1.00 g (5.58 mmol, 1 eq) of Intermediate C1 (4H-dithieno[3,2-b:2′,3′-d]pyrrole), 0.64 g (3.35 mmol, 0.6 eq) of copper(I) Iodide, 1.27 g (11.16 mmol, 2 eq) of trans-1,2-cyclohexanediamine, and 11.84 g (55.78 mmol, 10 eq) of tripotassium phosphate were dissolved in 100 mL of dioxane. 1.82 g (38.9 mmol, 2 eq) of 2-bromothiophene was added thereto, and the mixture was heated under reflux for 30 hours. After cooling the reaction solution to room temperature, 60 mL of water was added thereto, and an extraction process was performed thereon three times utilizing 60 mL of dichloromethane. The obtained organic layer was dried utilizing MgSO4, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.02 g (yield of 70%) of Intermediate C2 (4-(thiophen-2-yl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole). Intermediate C2 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 7.54 (m, 1H), 7.31 (d, 2H), 7.12 (d, 2H), 7.10 (m, 1H), 6.99 (m, 1H)
C12H7NS3: calc. 261.38, found 260.97.
Intermediate C3 (2-bromo-4-(thiophen-2-yl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole) was synthesized in substantially the same manner as utilized to synthesize Intermediate B3, except that Intermediate C2 was utilized instead of Intermediate B2 in the synthesis of Intermediate B3 in Synthesis Example 1. Intermediate C3 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 7.54 (m, 1H), 7.31 (d, 1H), 7.12 (d, 1H), 7.10 (m, 1H), 6.99 (m, 1H), 6.91 (s, 1H)
C12H6BrNS3: calc. 340.27, found 340.88.
Compound 6 (2-methyl-6-(4-(thiophen-2-yl)-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 3, except that Intermediate C3 was utilized instead of Intermediate B3 in the synthesis of Compound 3 in Synthesis Example 1. Compound 6 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.22 (m, 1H), 8.68 (d, 1H), 8.50 (m, 1H), 8.23 (d, 1H), 7.87 (m, 1H), 7.54 (m, 1H), 7.31 (d, 1H), 7.12 (d, 1H), 7.10 (m, 2H), 6.99 (m, 1H), 3.05 (s, 3H)
C25H14N2O2S3: calc. 470.58, found 470.02.
Intermediate D2 (9-phenyl-9H-carbazole) was synthesized in substantially the same manner as utilized to synthesize Intermediate C2, except that, in the synthesis of Intermediate C2 in Synthesis Example 2, Intermediate D1 (9H-carbazole) was utilized instead of Intermediate C1, and iodobenzene was utilized instead of 2-bromothiophene. Intermediate D2 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 2H), 7.94 (m, 2H), 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.35 (m, 2H), 7.16 (m, 2H)
C18H13N: calc. 243.31, found 243.10.
Intermediate D3 (3-bromo-9-phenyl-9H-carbazole) was synthesized in substantially the same manner as utilized to synthesize Intermediate B3, except that Intermediate D2 was utilized instead of Intermediate B2 in the synthesis of Intermediate B3 in Synthesis Example 1. Intermediate D3 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 1H), 8.05 (s, 1H), 7.94 (m, 1H), 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.47 (d, 1H), 7.42 (d, 1H), 7.35 (m, 1H), 7.16 (m, 1H)
C18H12BrN, calc. 322.21, found 321.02.
Compound 14 (2-methyl-6-(9-phenyl-9H-carbazol-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 3, except that Intermediate D3 was utilized instead of Intermediate B3 in the synthesis of Compound 3 in Synthesis Example 1. Compound 14 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.20 (m, 1H), 8.55 (m, 1H), 8.45 (d, 1H), 8.37 (m, 1H), 7.99 (d, 1H), 7.94 (m, 1H), 7.89 (s, 1H), 7.80 (m, 1H), 7.78 (d, 1H), 7.77 (d, 1H), 7.62 (m, 2H), 7.58 (m, 1H), 7.50 (m, 2H), 7.35 (m, 1H), 7.16 (m, 1H), 3.05 (s, 3H)
C31H20N2O2, calc. 452.51, found 452.15.
Compound 13 (6-(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 14, except that 9,9-dimethyl-9,10-dihydroacridine was utilized instead of Intermediate D1 in the synthesis of Compound 14 in Synthesis Example 3. Compound 13 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.20 (m, 1H), 8.45 (d, 1H), 8.37 (m, 1H), 7.80 (m, 1H), 7.78 (d, 1H), 7.76 (s, 1H), 7.45 (d, 1H), 7.36 (d, 1H), 7.24 (m, 2H), 7.19 (m, 1H), 7.17 (m, 1H), 7.14 (m, 1H), 7.08 (m, 2H), 7.00 (m, 1H), 6.95 (m, 1H), 3.05 (s, 3H), 1.69 (s, 6H)
C32H22N2O2S: calc. 494.59, found 494.20.
Intermediate E2 (1-bromo-9-(thiophen-2-yl)-9H-carbazole) was synthesized in substantially the same manner as utilized to synthesize Intermediate C2, except that, in the synthesis of Intermediate C2 in Synthesis Example 2, Intermediate E1 (1-bromo-9H-carbazole) was utilized instead of Intermediate C1, and 2-iodothiophene was utilized instead of 2-bromothiophene. Intermediate E2 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 1H), 8.13 (m, 1H), 7.94 (m, 1H), 7.54 (m, 1H), 7.42 (m, 1H), 7.35 (m, 1H), 7.18 (d, 1H), 7.16 (m, 1H), 7.10 (m, 1H), 6.99 (m, 1H),
3.0 g (9.14 mmol) of Intermediate E2 was dissolved in 60 mL of dehydrated diethyl ether. A solution of 2.5 M (5.5 mL, 13.71 mmol, 1.5 eq) of n-BuLi in hexane was added dropwise thereto at −50° C., and the mixture was stirred at room temperature for 1 hour. 0.58 g (10.97 mmol, 1.2 eq) of dehydrated acetone was added thereto at −50° C., and the mixture was stirred at room temperature for 2 hours. The organic layer extracted from dehydrated diethyl ether was washed utilizing an aqueous sodium chloride solution, and then dried by adding MgSO4. 1.83 g (yield of 65%) of Intermediate E3 (2-(9-(thiophen-2-yl)-9H-carbazol-1-yl)propan-2-ol) was obtained, and the next step was performed immediately without a separate purification process. Intermediate E3 thus produced was identified by MS/FAB.
C19H17NOS, calc. 307.41, found 307.10.
2.0 g (6.51 mmol) of Intermediate E3 was dissolved in 50 mL of dichloromethane. 2.31 g (16.26 mmol, 2.5 eq) of a boron trifluoride-ethyl ether complex was added dropwise thereto at 0° C., and the mixture was stirred for 2 hours. The organic layer extracted from dichloromethane was washed utilizing an aqueous sodium chloride solution, and then dried by adding MgSO4. The obtained product was separated and purified by silica gel column chromatography to obtain 4.09 g (yield of 85%) of Intermediate E4 (4,4-dimethyl-4H-thieno[3′,2′:5,6]pyrido[3,2,1-jk]carbazole). Intermediate E4 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 1H), 8.09 (m, 1H), 7.94 (m, 1H), 7.53 (d, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 7.16 (m, 1H), 7.07 (m, 1H), 7.02 (d, 1H), 1.69 (s, 6H)
C19H15NS: calc. 289.40, found 289.09.
Intermediate E5 (2-bromo-4,4-dimethyl-4H-thieno[3′,2′:5,6]pyrido[3,2,1-jk]carbazole) was synthesized in substantially the same manner as utilized to synthesize Intermediate B3, except that Intermediate E4 was utilized instead of Intermediate B2 in the synthesis of Intermediate B3 in Synthesis Example 1. Intermediate E5 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 1H), 8.09 (m, 1H), 7.94 (m, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 7.16 (m, 1H), 7.07 (m, 1H), 7.00 (s, 1H), 1.69 (s, 6H)
C19H14BrNS: calc. 368.29, found 369.00.
Compound 37 was synthesized in substantially the same manner as utilized to synthesize Compound 3, except that Intermediate E5 was utilized instead of Intermediate B3 in the synthesis of Compound 3 in Synthesis Example 1. Compound 37 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.22 (m, 1H), 8.68 (m, 1H), 8.55 (m, 1H), 8.50 (d, 1H), 8.23 (d, 1H), 8.09 (m, 1H), 7.94 (m, 1H), 7.87 (m, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 7.16 (m, 1H), 7.07 (m, 1H), 7.05 (s, 1H), 3.05 (s, 3H), 1.69 (s, 6H)
C32H22N2O2S: calc. 498.60, found 498.14.
Compound 42 (2-methyl-6-(4,4,8,8-tetramethyl-4H,8H-thieno[3′,2′:5,6]pyrido[3,2,1-de]acridin-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 37, except that 9,9-dimethyl-9,10-dihydroacridine was utilized instead of Intermediate E1 in the synthesis of Intermediate E2 in Synthesis Example 5. Compound 42 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.22 (m, 1H), 8.68 (m, 1H), 8.50 (d, 1H), 8.23 (d, 1H), 7.87 (m, 1H), 7.14 (m, 1H), 7.19 (m, 1H), 7.17 (m, 2H), 7.04 (m, 2H), 6.95 (m, 1H), 6.60 (s, 1H), 3.05 (s, 3H), 1.69 (s, 12H),
Compound 55 (6-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-10-yl)-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 37, except that iodobenzene was utilized instead of 2-iodothiophene in the synthesis of Intermediate E2 in Synthesis Example 5. Compound 55 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.55 (m, 1H), 8.09 (m, 1H), 7.94 (m, 2H), 7.91 (d, 1H), 7.81 (d, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 7.16 (m, 1H), 7.07 (s, 1H), 1.69 (s, 6H), 9.22 (m, 1H), 8.45 (d, 1H), 8.37 (m, 1H), 7.80 (m, 1H), 7.78 (d, 1H), 3.05 (s, 3H)
C34H24N2O2: calc. 492.58, found 492.18.
Compound 56 (2-methyl-6-(5,5,9,9-tetramethyl-5,9-dihydroquinolino[3,2,1-de]acridin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) was synthesized in substantially the same manner as utilized to synthesize Compound 37, except that, in the synthesis of Intermediate E2 in Synthesis Example 5, 9,9-dimethyl-9,10-dihydroacridine was utilized instead of Intermediate D1, and iodobenzene was utilized instead of 2-iodothiophene. Compound 56 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.22 (m, 1H), 8.45 (d, 1H), 8.37 (m, 1H), 7.80 (m, 1H), 7.78 (d, 1H), 7.76 (s, 1H), 7.45 (d, 1H), 7.36 (d, 1H), 7.19 (m, 1H), 7.17 (m, 1H), 7.17 (m, 1H), 7.14 (m, 1H), 7.04 (m, 2H), 6.95 (m, 1H), 1.69 (s, 12H), 3.05 (s, 3H)
C37H30N2O2: calc. 534.66, found 534.23.
Intermediate A4 (4-bromo-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one) was synthesized in substantially the same manner as utilized to synthesize Intermediate A2, except that benzene-1,2-diamine was utilized instead of methylamine in the synthesis of Intermediate A2 in Synthesis Example 1. Intermediate A4 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.38 (m, 1H), 8.31 (m, 1H), 8.23 (d, 1H), 8.17 (m, 1H), 8.07 (d, 1H), 7.57 (m, 1H), 7.54 (m, 1H), 7.24 (m, 1H), 7.21 (m, 1H)
C18H9BrN2O: calc. 349.19, found 347.99.
Intermediate A5 (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one) was synthesized in substantially the same manner as utilized to synthesize Intermediate A3, except that Intermediate A4 was utilized instead of Intermediate A2 in the synthesis of Intermediate A3 in Synthesis Example 1. Intermediate A5 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 8.32 (d, 1H), 8.27 (m, 2H), 8.06 (m, 1H), 7.80 (d, 1H), 7.57 (m, 1H), 7.54 (m, 1H), 7.24 (m, 1H), 7.21 (m, 1H), 1.20 (s, 12H)
C24H21BN2O3: calc. 396.25, found 396.16.
Compound 73 was synthesized in substantially the same manner as utilized to synthesize Compound 37, except that Intermediate A5 was utilized instead of Intermediate A3 in the synthesis of Compound 37 in Synthesis Example 5. Compound 73 thus produced was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.
(500 MHz, CDCl3): 9.12 (m, 1H), 8.55 (m, 1H), 8.51 (d, 1H), 8.27 (m, 1H), 8.17 (d, 1H), 8.09 (m, 1H), 8.06 (m, 1H), 7.94 (m, 1H), 7.57 (m, 1H), 7.54 (m, 1H), 7.45 (m, 1H), 7.35 (m, 1H), 7.24 (m, 1H), 7.21 (m, 1H), 7.16 (m, 1H), 7.07 (m, 1H), 7.05 (s, 1H), 1.69 (s, 6H)
C37H23N3OS: calc. 557.67, found 557.16.
A substrate on which an ITO anode was deposited was prepared to have a size of 50 mm×50 mm×0.7 mm. The substrate was ultrasonically cleaned utilizing isopropyl alcohol and pure water, each for 5 minutes. Subsequently, ultraviolet rays were irradiated onto the substrate for 30 minutes, and the substrate was exposed to ozone to be cleaned. The cleaned substrate was loaded onto a vacuum deposition apparatus. A hole injection layer having a thickness of 600 Å was formed on the ITO substrate by vacuum deposition. A hole transport layer vacuum-deposited to a thickness of 300 Å on the hole injection layer. An auxiliary layer was formed to a thickness of 300 Å on the hole transport layer. Compound 3 and Compound N16 were co-deposited on the auxiliary layer to form a photoactive layer having a thickness of 500 Å. An electron transport layer was formed to a thickness of 300 Å on the photoactive layer by deposition. An electron injection layer was formed to a thickness of 10 Å on the electron transport layer by deposition. Subsequently, Al was vacuum-deposited to a thickness of 3,000 Å to form a LiF/Al cathode, thereby completing the manufacture of an opto-electronic device.
Opto-electronic devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 1 were each utilized instead of Compound 3 in forming the photoactive layer.
The HOMO and LUMO of each of the compounds of Examples and Comparative Examples were measured, and the results are shown in Table 1.
By utilizing cyclic voltammetry (CV) (electrolyte: 0.1 M Bu4NPF6, solvent: dimethylforamide (DMF), electrode: 3-electrode system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)), the potential (V)-current (A) graph of each compound was obtained. The HOMO and LUMO values of each compound were calculated from the oxidation onset and reduction onset of the graph.
The maximum absorption wavelength and intensity were measured utilizing UV-vis spectroscopy.
From Table 1, it was confirmed that i) the compound utilized in each of Examples 1 to 9 had a smaller molecular weight than the compound utilized in each of Comparative Examples 1 and 2, and/or ii) the opto-electronic device of each of Examples 1 to 9 had a higher intensity than the opto-electronic devices of Comparative Examples 1 and 2. Accordingly, it was confirmed that the opto-electronic device of each of Examples 1 to 9 had, as compared with the opto-electronic devices of Comparative Examples 1 and 2, i) excellent or suitable heat resistance characteristics and/or ii) excellent or suitable light absorption efficiency for green light (or light having a wavelength similar to that of green light).
Light was irradiated to the opto-electronic devices manufactured utilizing the compounds of Examples 1 to 9 and Comparative Examples 1 and 2, and the external quantum efficiency according to the wavelength of each device was measured. The external quantum efficiency refers to the ratio of electrical energy generated from energy of the irradiated light.
The maximum external quantum efficiency (EQE) refers to the maximum value from among external quantum efficiencies according to wavelengths. The Δmax EQE refers to the wavelength of the maximum external quantum efficiency (EQE). The maximum external quantum efficiency (EQE) and Amax EQE are shown in Table 2.
From Table 2, it was confirmed that the opto-electronic device of each of Examples 1 to 9 had excellent or suitable photoelectric characteristics compared to the opto-electronic devices of Comparative Examples 1 and 2.
According to the one or more embodiments, the organic compound represented by Formula 1 may have high heat resistance characteristics. An opto-electronic device including the organic compound may have high light absorption efficiency. An electronic apparatus including the opto-electronic device and an electronic device utilizing the electronic apparatus may have improved quality.
The use of “may” when describing embodiments of the inventive concept refers to “one or more embodiments of the inventive concept.”
As utilized herein, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
In the present disclosure, when particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “diameter” indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
As used herein, the term “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” or “approximately,” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Also, any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The electronic apparatus and/or any other relevant devices or components according to embodiments of the present invention described herein may be implemented utilizing any suitable hardware, firmware (e.g. an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the apparatus may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the apparatus may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the apparatus may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0138624 | Oct 2022 | KR | national |
