WO2023082964A1 - Complexe, procédé de préparation du complexe et dispositif électroluminescent - Google Patents

Complexe, procédé de préparation du complexe et dispositif électroluminescent Download PDF

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WO2023082964A1
WO2023082964A1 PCT/CN2022/126331 CN2022126331W WO2023082964A1 WO 2023082964 A1 WO2023082964 A1 WO 2023082964A1 CN 2022126331 W CN2022126331 W CN 2022126331W WO 2023082964 A1 WO2023082964 A1 WO 2023082964A1
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type semiconductor
semiconductor material
component
black phosphorus
fullerene
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Chinese (zh)
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王劲
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Tcl科技集团股份有限公司
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the application relates to the field of optoelectronic technology, in particular to a compound, a preparation method of the compound and an electroluminescent device.
  • Black phosphorus nanosheets are a highly efficient P-type semiconductor material, which has the advantages of large specific surface area, abundant adsorption sites, high carrier mobility, excellent mechanical strength and thermal conductivity, and its surface has phosphorus atoms carrying lone pairs of electrons.
  • phosphorus atoms serve as highly reactive sites of black phosphorus nanosheets, and the surface of black phosphorus nanosheets can form phosphorus atom-metal atom chemical bond bridging, phosphorus atom-oxygen atom-carbon atom chemical bond bridging, or phosphorus atom-oxygen atom -Silicon atom chemical bond bridging.
  • Phosphorus atoms serve as highly reactive sites of black phosphorus nanosheets, which makes the black phosphorus nanosheets have unsatisfactory chemical stability. Therefore, how to improve the chemical stability of black phosphorus nanosheets is of great significance to the application of black phosphorus nanosheets.
  • the present application provides a compound, a preparation method of the compound and an electroluminescent device, so as to improve the chemical stability of black phosphorus nanosheets.
  • the present application provides a composite, the composite includes a P-type semiconductor material and an N-type semiconductor material, and the P-type semiconductor material is connected to the N-type semiconductor material through a covalent chemical bond;
  • the P Type semiconductor materials include black phosphorus nanosheets;
  • the N-type semiconductor materials include:
  • Component A inorganic nanoparticles
  • Component B one or more of fullerenes and fullerene derivatives.
  • the compound includes: 5% to 80% of N-type semiconductor material and 20% to 95% of P-type semiconductor material.
  • the compound includes: 5% to 40% of N-type semiconductor material and 60% to 95% of P-type semiconductor material.
  • the N-type semiconductor material includes: 80% to 99% of component A, and 1% to 20% of component B.
  • the compound is composed of a P-type semiconductor material and an N-type semiconductor material, and the P-type semiconductor material is connected to the N-type semiconductor material through a covalent chemical bond; the P-type semiconductor material is a black phosphorus nanosheet ;
  • the N-type semiconductor material is composed of component A and component B.
  • the thickness of the black phosphorus nanosheets is 0.5nm to 10nm.
  • the energy level difference between the highest occupied orbital of the P-type semiconductor material and the lowest unoccupied orbital of the N-type semiconductor material is -1.0eV to 1.0eV, and the band gap of the compound is 1.0 eV to 2.5eV.
  • the inorganic nanoparticles are selected from one or more of metal oxide nanoparticles and metal sulfide nanoparticles, and the phosphorus atoms of the black phosphorus nanosheets coordinate with the metal atoms of the inorganic nanoparticles Bond.
  • the inorganic nanoparticles are selected from ZnO, TiO 2 , SnO 2 , Ta 2 O 3 , ZrO 2 , NiO, TiLiO, ZnAlO, ZnMgO, ZnSnO, ZnLiO, InSnO, AlZnO, CdS, ZnS, MoS, WS and at least one of CuS.
  • the fullerene derivative contains an alkyl chain with 10 to 40 carbon atoms, and the alkyl chain contains one or more of nitro groups, aromatic groups, ester groups and fluorine atoms.
  • the fullerene derivative is [60]PCBM or [70]PCBM.
  • the present application provides a method for preparing a complex, the preparation method comprising the following steps:
  • a mixed solution is provided, the mixed solution includes black phosphorus nanosheets and component B, and the component B is one or more of fullerenes and fullerene derivatives;
  • a dispersion comprising component A, the component A is inorganic nanoparticles, mix the black phosphorus nanosheet-fullerene composite material with the dispersion, and react at a second preset temperature to obtain the complex.
  • the first preset temperature is 100°C to 200°C, and the first reaction time is 1h to 12h;
  • the second preset temperature is -15°C to 80°C, and the second reaction time is 0.5h to 24h.
  • the mass ratio of the black phosphorus nanosheets is 1: (0.01 ⁇ 0.10).
  • the black phosphorus nanosheet-fullerene composite in the step of mixing the black phosphorus nanosheet-fullerene composite with the dispersion, the black phosphorus nanosheet-fullerene composite: the mass ratio of the component A It is 1: (0.01 ⁇ 0.64).
  • the present application provides an electroluminescent device, the electroluminescent device comprising:
  • N light-emitting layers are arranged at intervals between the anode and the cathode;
  • N-1 charge generation layers are arranged at intervals between the anode and the cathode, and each of the charge generation layers is respectively arranged between two adjacent light-emitting layers, and N is greater than or equal to 2 positive integer;
  • the material of the charge generation layer includes black phosphorus nanosheets and inorganic nanoparticles; or, the material of the charge generation layer includes a P-type semiconductor material and an N-type semiconductor material, and the P-type semiconductor material and the N-type semiconductor material
  • the semiconductor materials are connected by covalent chemical bonds, the P-type semiconductor materials include black phosphorus nanosheets, the N-type semiconductor materials include component A and component B, the component A is inorganic nanoparticles, and the component B
  • One or more of fullerenes and fullerene derivatives; or, the material of the charge generation layer is prepared by the following method:
  • a mixed solution is provided, the mixed solution includes black phosphorus nanosheets and component B, and the component B is one or more of fullerenes and fullerene derivatives;
  • a dispersion comprising component A, the component A is inorganic nanoparticles, mix the black phosphorus nanosheet-fullerene composite material with the dispersion, and react at a second preset temperature to obtain the complex.
  • the compound includes: 5% to 80% of N-type semiconductor material and 20% to 95% of P-type semiconductor material;
  • the compound includes: 5% to 40% of N-type semiconductor material and 60% to 95% of P-type semiconductor material.
  • the N-type semiconductor material includes: 80% to 99% of component A, and 1% to 20% of component B.
  • the energy level difference between the highest occupied orbital of the P-type semiconductor material and the lowest unoccupied orbital of the N-type semiconductor material is -1.0eV to 1.0eV, and the band gap of the compound is 1.0 eV to 2.5eV.
  • the material of the light-emitting layer is an organic light-emitting material or a quantum dot
  • the organic light-emitting material is selected from diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, blue At least one of the TBPe fluorescent material of colored light, the TTPA fluorescent material of green light, the TBRb fluorescent material of orange light and the DBP fluorescent material of red light
  • the quantum dot is selected from II-VI group compounds, III-V At least one of group compound, IV-VI group compound and I-III-VI group compound, wherein, the II-VI group compound is selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe , HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgS
  • the electroluminescence device also includes an electron transport layer, the electron transport layer is arranged between the cathode and the light-emitting layer, the material of the electron transport layer includes nano-metal oxide, and the nano-metal oxide is selected from At least one of ZnO, TiO 2 , SnO 2 , Ta 2 O 3 , ZrO 2 , NiO, TiLiO, ZnGaO, ZnAlO, ZnMgO, ZnSnO, ZnLiO, InSnO and AlZnO;
  • the electroluminescence device also includes a hole transport layer, the hole transport layer is arranged between the anode and the light-emitting layer, and the material of the hole transport layer is selected from poly(9,9-dioctyl fluorene-CO-N-(4-butylphenyl) diphenylamine), 3-hexyl substituted polythiophene, poly(9-vinylcarbazole), poly[bis(4-phenyl)(4-butylphenyl base)amine], poly(N,N'-bis(4-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine-CO-9,9-dioctylfluorene) , 4,4',4"-tris(carbazol-9-yl)triphenylamine, 4,4'-bis(9-carbazole)biphenyl, N,N'-diphenyl-N,N'- Bis(3-methylpheny
  • the compound of the present application is a bulk heterojunction structure material based on component A, component B and black scale nanosheets, wherein component A is inorganic nanoparticles, and component B is fullerene and/or fullerene Derivatives, component A and component B are used as N-type semiconductor materials, and black scale nanosheets are used as P-type semiconductor materials.
  • Component A is connected to the surface of black phosphorus nanosheets through covalent chemical bonds, thereby effectively passivating black scale nanosheets.
  • the phosphorus atoms on the surface improve the stability of the composite;
  • component B is covalently connected to the edge of the black phosphorus nanosheet through the phosphorus atom-carbon atom chemical bond, which further improves the stability of the composite and improves the photocurrent response of the composite rate.
  • the preparation method of the composite of the present application is to first prepare the black phosphorus nanosheet-fullerene composite material, and then mix the black phosphorus nanosheet-fullerene composite material with a dispersion liquid containing inorganic nanoparticles to obtain the composite, It has the advantages of simple operation, easy control and suitability for industrialized production.
  • the material of the charge generation layer includes a P-type semiconductor material and an N-type semiconductor material
  • the P-type semiconductor material includes black phosphorus nanosheets
  • the N-type semiconductor material includes component A
  • the N-type semiconductor material includes component A and component B
  • the charge generation layer can be a single-layer structure prepared by a solution method, which changes the traditional mode of relying on vacuum deposition to prepare charge generation layers, and is suitable for the preparation of large-scale
  • the electroluminescent device is beneficial to reduce manufacturing cost and working voltage, and avoid damage to the light-emitting layer caused by high temperature.
  • Fig. 1 is a schematic flow chart of a preparation method of a complex provided in an example of the present application.
  • Fig. 2 is a schematic structural diagram of the first electroluminescent device provided in the embodiment of the present application.
  • Fig. 3 is a schematic structural diagram of a second electroluminescent device provided in the embodiment of the present application.
  • Fig. 4 is a schematic structural diagram of a third electroluminescent device provided in the embodiment of the present application.
  • Fig. 5 is a schematic structural diagram of a fourth electroluminescent device provided in the embodiment of the present application.
  • Fig. 6 is a characteristic curve of current density-voltage of the electroluminescent devices of Examples 6 to 8, Comparative Example 1 and Comparative Example 2 in the experimental examples of the present application.
  • Fig. 7 is a characteristic curve of current density-voltage of the electroluminescent devices of Example 9, Example 10, Comparative Example 1 and Comparative Example 2 in the experimental examples of the present application.
  • Fig. 8 is a characteristic curve of current density-voltage of the electroluminescent devices of Examples 11 to 13, Comparative Example 1 and Comparative Example 2 in the experimental examples of the present application.
  • Embodiments of the present application provide a quantum dot light emitting diode device, a manufacturing method thereof, and a display panel. Each will be described in detail below. It should be noted that the description sequence of the following embodiments is not intended to limit the preferred sequence of the embodiments.
  • a description of a range from 1 to 6 should be considered to have specifically disclosed subranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and Single numbers within the stated ranges, eg 1, 2, 3, 4, 5 and 6, apply regardless of the range.
  • a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.
  • the term "and/or” is used to describe the relationship between associated objects, indicating that there may be three relationships, for example, "A and/or B" may indicate three situations: the first situation is that A exists alone ; The second case is the presence of A and B at the same time; the third case is the case of B alone, wherein A and B can be singular or plural respectively.
  • the term "at least one” means one or more, and “multiple” means two or more.
  • the terms “at least one”, “at least one of the following", “one or more” or similar expressions refer to any combination of these items, including single item(s) or plural item(s) random combination.
  • “at least one (one) of a, b, or c” or “at least one (one) of a, b, and c” can be expressed as: a, b, c, a-b (that is, a and b ), a-c, b-c or a-b-c, wherein, a, b and c can be single or multiple respectively.
  • An embodiment of the present application provides a compound, the compound includes a P-type semiconductor material and an N-type semiconductor material, the P-type semiconductor material is connected to the N-type semiconductor material through a covalent chemical bond; the P-type semiconductor material includes black Phosphorus nanosheets; N-type semiconductor materials include component A and component B, wherein component A is inorganic nanoparticles, and component B is fullerene and/or fullerene derivatives.
  • black phosphorus nanosheets is a highly efficient P-type semiconductor material with the advantages of large specific surface area, abundant adsorption sites, high carrier mobility, excellent mechanical strength and thermal conductivity, and its surface has A phosphorus atom carrying a lone pair of electrons. Therefore, the phosphorus atom serves as a highly reactive site of the black phosphorus nanosheet.
  • the surface of the black phosphorus nanosheet can form, for example, a phosphorus atom-metal atom chemical bond bridge, phosphorus atom-oxygen atom-carbon atom Chemical bond bridging or phosphorus atom-oxygen atom-silicon atom chemical bond bridging;
  • black phosphorus nanosheets can be either undoped black phosphorus nanosheets, doped black phosphorus nanosheets, or undoped black phosphorus nanosheets
  • the band gap and carrier mobility of undoped black phosphorus nanosheets can be adjusted by means of surface modification and element doping.
  • Doped black phosphorus nanosheets refers to black phosphorus nanosheets having ions of one or more doping elements in the nanolattice.
  • the doping element of the doped black phosphorus nanosheet is a metal element, and the metal element is selected from Se, Te, Sb, Bi, As, Co, Fe, Mn, Fe, Pt and at least one of Zn.
  • the number of doped metal atoms accounts for no more than 50% of the total number of atoms.
  • the compound of the embodiment of the present application is a bulk heterojunction structure material based on the covalent combination of a P-type semiconductor material and an N-type semiconductor material, which can be used to prepare a charge generation layer of a stacked electroluminescent device, and can be solution-processed into a film , so as to effectively avoid the negative impact of the charge generation layer formed by the traditional vacuum deposition method on the working performance and service life of the stacked electroluminescent device.
  • the single-layer thin film formed by the solution method of the composite can be used as the charge generating layer of the stacked electroluminescent device, which effectively reduces the number and thickness of the film layer of the charge generating layer, and is beneficial to improve the efficiency of the stacked electroluminescent device. performance and prolong the service life of stacked electroluminescent devices.
  • component A is connected to the surface of black phosphorus nanosheets through covalent chemical bonds, thereby effectively passivating the phosphorus atoms on the surface of black phosphorus nanosheets, improving the stability of the composite, and promoting the hole- electronic balance.
  • Component B is covalently linked to the edge of black phosphorus nanosheets through a phosphorus atom-carbon atom chemical bond. Since component B has excellent stability in water, oxygen and air environments, it can further improve the stability of the composite; In addition, component B has an ideal ability to accept electrons, and the electrons excited by light are easily transferred from black phosphorus nanosheets to component B. Therefore, the photogenerated electrons and holes in the composite can be quickly transferred and separated, which is beneficial to improve the complex photocurrent response rate.
  • the compound includes: 5% to 80% of N-type semiconductor material and 20% to 95% of P-type semiconductor material.
  • the compound includes: 5% to 40% of N-type semiconductor material and 60% to 95% of P-type semiconductor material.
  • the compound is used as the charge generation layer material of a laminated electroluminescent device, if the content of the N-type semiconductor material is too small, the protective effect on the P-type semiconductor material will be limited; However, the effect of improving the electron-hole transport imbalance problem of multi-layer electroluminescent devices is limited.
  • the N-type semiconductor material includes: 80% to 99% of component A, and 1% to 20% of component B.
  • component B When the compound is used as the charge generation layer material of the stacked electroluminescent device, the content of component B is too small, the effect of improving the stability of the compound is limited, and the effect of improving the stability of the charge generation layer is limited; If the content of component B is too high, the effect of improving the electron-hole transport imbalance of the stacked electroluminescent device is limited.
  • the thickness of the black phosphorus nanosheets is 0.5 nm to 10 nm.
  • the energy level difference between the highest occupied orbital of the P-type semiconductor material and the lowest unoccupied orbital of the N-type semiconductor material is -1.0eV to 1.0eV
  • the The band gap of the complex is 1.0eV to 2.5eV.
  • the inorganic nanoparticles are selected from metal oxide nanoparticles and/or metal sulfide nanoparticles, and the phosphorus atoms of the black phosphorus nanosheets are coordinated and bonded to the metal atoms of the inorganic nanoparticles .
  • metal oxide nanoparticles can be either undoped metal oxide nanoparticles, doped metal oxide nanoparticles, or undoped metal oxide nanoparticles and Mixture of doped metal oxide nanoparticles.
  • Doped metal oxide nanoparticles means metal oxide nanoparticles having ions of one or more doping elements in the crystal lattice, the doping elements being different from the host metal elements of the metal oxide nanoparticles, doped Heteroelements include but are not limited to one or more of Mg, Al, Ga, Li, In, Sn and Mo, and the doped metal oxide nanoparticles can be, for example, molybdenum-doped zinc oxide (MZO), doped magnesium and Lithium zinc oxide (MLZO), gallium and magnesium doped zinc oxide (MGZO), zinc doped magnesium oxide (ZnMgO), zinc doped tin oxide (ZnSnO), zinc doped lithium oxide (ZnLiO), indium doped oxide One or more of
  • metal sulfide nanoparticles can be either undoped metal sulfide nanoparticles, doped metal sulfide nanoparticles, or undoped metal sulfide nanoparticles and Mixture of doped metal sulfide nanoparticles.
  • Doped metal sulfide nanoparticles means metal sulfide nanoparticles having ions of one or more doping elements in the crystal lattice, the doping elements being different from the host metal elements of the metal oxide nanoparticles, doped Heteroelements include but are not limited to one or more of Mg, Al, Ga, Li, In, Sn, and Mo, and the doped metal sulfide nanoparticles can be, for example, one or more of ZnMgS, AlZnS, and ZnLiS kind.
  • the inorganic nanoparticles are selected from ZnO, TiO 2 , SnO 2 , Ta 2 O 3 , ZrO 2 , NiO, TiLiO, ZnAlO, ZnMgO, ZnSnO, ZnLiO, InSnO, AlZnO, CdS, ZnS, At least one of MoS, WS and CuS.
  • the fullerene derivative comprises an alkyl chain with 10 to 40 carbon atoms, and the alkyl chain comprises at least one of a nitro group, an aromatic group, an ester group and a fluorine atom, To further reduce the lowest unoccupied orbital energy level of the fullerene derivatives, thereby improving the electron accepting ability of the fullerene derivatives, and further improving the photocurrent response rate of the composite.
  • the fullerene derivative is [60]PCBM or [70]PCBM.
  • the embodiment of the present application also provides a preparation method of the complex, as shown in Figure 1, the preparation method includes the following steps:
  • B101 providing a mixed solution, the mixed solution comprising black phosphorus nanosheets and component B, where component B is fullerene and/or fullerene derivatives;
  • the solvents of the mixed solution include but are not limited to acetone, ethanol, methanol, isopropanol, N-methylpyrrolidone, N,N-dimethylformamide, carbon disulfide, cyclohexane, chlorobenzene and at least one of toluene.
  • the mass ratio of black phosphorus nanosheets:component B in the mixed solution is 1:(0.01 ⁇ 0.10).
  • B102 put the mixed solution of B101 at the first preset temperature to react to obtain a solution containing black phosphorus nanosheet-fullerene composite material, remove the solvent of the solution, and obtain a solid black phosphorus nanosheet-fullerene composite Material;
  • B102 What needs to be explained for B102 is that the mixed solution is treated with high temperature hydrothermal method to make component B bonded to the edge of black phosphorus nanosheets.
  • component B is selectively covalently linked to the edge of black phosphorus nanosheets by carbon atom-phosphorus atom chemical bond.
  • the second preset temperature may be, for example, 100° C. to 200° C.
  • the reaction time may be, for example, 1 h to 12 h.
  • Removing the solvent of the solution refers to everything that can remove the solvent in the solution containing the black phosphorus nanosheet-fullerene composite material to obtain one or more separations of the solid black phosphorus nanosheet-fullerene composite material.
  • the solvent of the solution can be removed by drying under reduced pressure.
  • component A is inorganic nanoparticles
  • mixing the black phosphorus nanosheet-fullerene composite material of B102 with the dispersion liquid and reacting at a second preset temperature to obtain Complex.
  • the solvent of the dispersion containing component A includes but not limited to at least one of ethanol, methanol, isopropanol, ethylene glycol methyl ether and acetone.
  • the black phosphorus nanosheet-fullerene composite material the mass ratio of component A is 1: (0.01 ⁇ 0.64).
  • the second preset temperature is -15°C to 80°C. In an embodiment of the present application, the second preset temperature is -5°C to 60°C, and the reaction time is 0.5h to 24h.
  • the preparation method of the complex further includes step B104: adding a precipitating agent to the complex prepared by B103, solid Liquid separation and collection of the liquid phase, removal of the solvent of the liquid phase, to obtain a purified complex.
  • the solid-liquid separation process includes but is not limited to one or more operations in precipitation, centrifugation, decantation, filtration and gravity sedimentation;
  • the precipitant is selected from ethyl acetate, methyl acetate, ethyl formate and methyl formate At least one of the above;
  • removing the solvent in the liquid phase refers to one or more separation and purification processes that can remove the solvent in the liquid phase to obtain a solid compound, for example, the decompression drying method can be used to remove the solvent in the liquid phase. solvent.
  • "adding precipitating agent to the complex prepared by B103" includes the steps of: adding dropwise to the compound prepared by B103 Precipitant until no more precipitation occurs.
  • the embodiment of the present application also provides an electroluminescent device.
  • the electroluminescent device 1 includes an anode 11, a cathode 12, N light-emitting layers and (N-1) charge generation layers, and N is greater than A positive integer equal to 2; N light-emitting layers are arranged at intervals between the anode 11 and the cathode 12; (N-1) charge generation layers are arranged at intervals between the anode 11 and the cathode 12, and each charge generation layer is respectively arranged on the phase Adjacent to the two light-emitting layers; wherein, the material of the charge generation layer includes black phosphorus nanosheets and inorganic nanoparticles, or the material of the charge generation layer includes any one of the compounds described in the embodiments of this application or this application The composite that any one of the preparation methods described in the examples makes.
  • the material of the charge generation layer includes 20% to 95% of black phosphorus nanosheets and 5% to 80% of inorganic nanoparticles.
  • the material of the charge generation layer includes 60% to 95% of black phosphorus nanosheets and 5% to 40% of inorganic nanoparticles.
  • the material of the charge generation layer is prepared by the following method:
  • B201 providing a first solution containing black phosphorus nanosheets and a second solution containing inorganic nanoparticles, mixing the first solution and the second solution to obtain a mixture;
  • the solvent of the first solution includes but is not limited to at least one of acetone, ethanol, methanol, isopropanol, N-methylpyrrolidone and N,N-dimethylformamide
  • the first concentration of black phosphorus nanosheets in the solution may be, for example, 5 mg/mL to 100 mg/mL.
  • the solvent of the second solution includes but is not limited to at least one of ethanol, methanol, isopropanol, ethylene glycol methyl ether and acetone, and the concentration of inorganic nanoparticles in the second solution can be, for example, 5 mg/mL to 60 mg/mL .
  • the mass ratio of black phosphorus nanosheets:inorganic nanoparticles in the mixture is 1:(0.02 ⁇ 0.7).
  • the preset temperature is -15°C to 80°C.
  • the preset temperature is -5°C to 60°C, and the reaction time is 0.5h to 24h.
  • the reaction product of B202 includes black phosphorus nanosheets, inorganic nanoparticles and impurities, and the purified charge generation layer material can be obtained by purifying the reaction product of B202.
  • the purification process includes but is not limited to solid-liquid Separation process, solid-liquid separation process includes but not limited to one or more operations in sedimentation, centrifugation, decantation, filtration and gravity sedimentation.
  • B203 includes the steps of: adding a precipitating agent to the reaction product of B202, separating the solid from the liquid and collecting the liquid phase, removing the solvent of the liquid phase, and obtaining a purified charge generation layer material.
  • the precipitant is selected from at least one of ethyl acetate, methyl acetate, ethyl formate and methyl formate, in an embodiment of the application, in order to control the amount of the precipitant to reduce the difficulty of subsequent separation and purification,
  • the precipitating agent was added dropwise to the reaction product of B202 until no more precipitation occurred.
  • Removing the solvent in the liquid phase refers to one or more separation and purification procedures that can remove the solvent in the liquid phase to obtain a solid charge generation layer material. For example, the solvent in the liquid phase can be removed by drying under reduced pressure.
  • the N light-emitting layers respectively correspond to the first light-emitting layer 13-1 to the Nth light-emitting layer 13-N, and (N-1) charges
  • the generation layers correspond to the first charge generation layer 14-1 to the (N-1)th charge generation layer 14-(N-1), the first light-emitting layer 13-1 is close to the anode 11, and the N-th light-emitting layer 13-N is close to Cathode 12, the first charge generation layer 14-1 is arranged between the first light emitting layer 13-1 and the second light emitting layer 13-2, the second charge generation layer 14-2 is arranged between the second light emitting layer 13-2 and the second light emitting layer Between the three light-emitting layers 13-3, and so on, the (N-1)th charge generation layer 14-(N-1) is arranged between the (N-1)-th light-emitting layer 13-(N-1) and the N-th light-e
  • the materials of the anode 11 and the cathode 12 can be common materials in the field, for example: the materials of the anode 11 and the cathode 12 include but are not limited to one or more of metals, carbon materials and metal oxides
  • the metal can be one or more of Al, Ag, Cu, Mo, Au, Ba, Ca and Mg
  • the carbon material can be one or more of graphite, carbon nanotube, graphene and carbon fiber, for example.
  • metal oxides can be doped or non-doped metal oxides, including one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO and AMO, also including doped or non-doped transparent
  • Composite electrodes with metal sandwiched between metal oxides, composite electrodes include but not limited to AZO/Ag/AZO, AZO/Al/AZO, ITO/Ag/ITO, ITO/Al/ITO, ZnO/Ag/ZnO, ZnO /Al/ZnO, TiO 2 /Ag/TiO 2 , TiO 2 /Al/TiO 2 , ZnS/Ag/ZnS, ZnS/Al/ZnS, TiO 2 /Ag/TiO 2 and TiO 2 /Al/TiO 2 one or more.
  • the thickness of the anode can be, for example, 40 nm to 160 nm, and the thickness of the
  • the material of the light-emitting layer includes but is not limited to organic light-emitting materials or quantum dots, and the organic light-emitting materials include but not limited to diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives or At least one of fluorene derivatives, TBPe fluorescent material emitting blue light, TTPA fluorescent material emitting green light, TBRb fluorescent material emitting orange light and DBP fluorescent material emitting red light.
  • Quantum dots can be at least one of red quantum dots, green quantum dots and blue quantum dots, quantum dots are selected from II-VI group compounds, III-V group compounds, IV-VI group compounds and I-III-VI group compounds At least one of the group I-VI compounds selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe , HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSe
  • the electroluminescent device further includes an electron transport layer, the electron transport layer is arranged between the cathode and the light-emitting layer, and the material of the electron transport layer includes a nano-metal oxide, and the nano-metal oxide is selected from ZnO, At least one of TiO 2 , SnO 2 , Ta 2 O 3 , ZrO 2 , NiO, TiLiO, ZnGaO, ZnAlO, ZnMgO, ZnSnO, ZnLiO, InSnO, and AlZnO; and/or, the electroluminescent device further includes a hole transport layer, the hole transport layer is arranged between the anode and the light-emitting layer, and the material of the hole transport layer is selected from poly(9,9-dioctylfluorene-CO-N-(4-butylphenyl)diphenylamine) ( TFB for short, CAS No.
  • TFB poly(9,9-dioc
  • the material of the hole transport layer can also be selected from inorganic materials with hole transport capabilities, including but not limited to NiO, WO3 , MoO3 and at least one of CuO.
  • the thickness of the hole transport layer 15 may be, for example, 10 nm to 50 nm.
  • the thickness of the electron transport layer 16 may be, for example, 10 nm to 60 nm.
  • the electroluminescent device may also include other layer structures, for example, the electroluminescent device may also include a hole injection layer, for example, the hole injection layer is arranged between the hole transport layer and the anode, and the hole injection layer Materials include but are not limited to 3,4-ethylenedioxythiophene monomer (PEDOT), styrene sulfonate (PSS), copper phthalocyanine (CuPc), 2,3,5,6-tetrafluoro-7,7 ',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexa One or more of azatriphenylene (HATCN), transition metal oxides and transition metal chalcogenides, wherein the transition metal oxides can be NiO x , MoO x , WO x , CrO x and CuO One or more, the metal chalc
  • the preparation method of each layer structure in the electroluminescence device includes but not limited to solution method and deposition method.
  • the solution method includes but not limited to spin coating, coating, inkjet printing, scraping coating, dipping and pulling, soaking, spraying, rolling coating or casting.
  • a drying process needs to be added.
  • the drying process includes all A process in which a wet film obtains higher energy and is transformed into a dry film.
  • the drying process can be, for example, heat treatment, standing to dry naturally, etc.; wherein, "heat treatment” can be a constant temperature heat treatment, or a non-constant temperature heat treatment (for example, the temperature is gradient format change).
  • Deposition methods include chemical methods and physical methods. Chemical methods include but are not limited to chemical vapor deposition, continuous ion layer adsorption and reaction methods, anodic oxidation, electrolytic deposition or co-precipitation methods. Physical methods include but are not limited to thermal evaporation. Coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion coating method, physical vapor deposition method, atomic layer deposition method or pulsed laser deposition method.
  • the material of the charge generation layer includes a P-type semiconductor material and an N-type semiconductor material
  • the P-type semiconductor material includes black phosphorus nanosheets
  • the N-type semiconductor material includes inorganic nanoparticles or N-type semiconductor materials.
  • the materials include fullerene and/or fullerene derivatives and inorganic nanoparticles, which can effectively improve the stability of the charge generation layer and at the same time improve the photocurrent response rate of the charge generation layer, and can efficiently charge the charge generation layer without doubling the voltage.
  • the light-emitting layer injects electrons and holes, thereby significantly improving the luminous brightness and current efficiency of the electroluminescent device.
  • the charge generation layer can be a single-layer structure prepared by the solution method, which changes the traditional mode of relying on the vacuum deposition method to prepare the charge generation layer, and is suitable for the preparation of large-sized electroluminescent devices, which is conducive to reducing manufacturing costs and operating voltages , and avoid high temperature damage to the light-emitting layer.
  • An embodiment of the present application further provides a display device, the display device comprising any one of the electroluminescent devices described in the embodiments of the present application.
  • the display device can be any electronic product with a display function, including but not limited to smart phones, tablet computers, notebook computers, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, vehicle displays, televisions Or an e-book reader, wherein the smart wearable device may be, for example, a smart bracelet, a smart watch, a virtual reality (Virtual Reality, VR) helmet, and the like.
  • the composite consists of 32% ZnO nanoparticles (6nm particle size), 8% fullerene and 60% black phosphorus nanosheets .
  • the preparation method of described complex comprises the steps:
  • step S1.2 Place the mixed solution in step S1.1 at 150°C for 4 hours to react, and the obtained reaction product is a black phosphorus nanosheet-fullerene composite solution, and dry under reduced pressure (at a pressure of -0.1MPa) to remove the black phosphorus A solvent in the nanosheet-fullerene composite solution to obtain a solid black phosphorus nanosheet-fullerene composite material;
  • ZnO nanoparticles (particle diameter is 6nm) is dissolved in ethanol to obtain the dispersion liquid that concentration is 20mg/mL, get the black phosphorus nanosheet-fullerene composite material that 1.36g step S1.2 makes and 16.2mL of the dispersion were mixed, placed at 0°C and stirred for 8 hours to obtain a reaction product containing the complex;
  • step S1.4 At room temperature, add ethyl acetate dropwise to the reaction product in step S1.3, and stir fully at the same time, stop adding ethyl acetate until no white precipitate occurs, let it settle for 5 hours naturally, filter to remove the precipitate and remove
  • the liquid phase was collected, dried under reduced pressure (at a pressure of -0.1 MPa) to remove the solvent of the liquid phase, and a purified compound was obtained.
  • the composite consists of 21% ZnO nanoparticles (particle size is 6nm), 4% fullerene and 75% black phosphorus nanosheets .
  • the preparation method of described complex comprises the steps:
  • step S2.2 Place the mixed solution in step S2.1 at 150°C for 4 hours to react, and the obtained reaction product is a black phosphorus nanosheet-fullerene composite solution, and dry under reduced pressure (at a pressure of -0.1MPa) to remove the black phosphorus A solvent in the nanosheet-fullerene composite solution to obtain a solid black phosphorus nanosheet-fullerene composite material;
  • step S2.4 At room temperature, add ethyl acetate dropwise to the reaction product in step S2.3, and stir fully at the same time, stop adding ethyl acetate until no white precipitate occurs, let it settle for 5 hours naturally, filter to remove the precipitate and remove
  • the liquid phase was collected, dried under reduced pressure (at a pressure of -0.1 MPa) to remove the solvent of the liquid phase, and a purified compound was obtained.
  • the composite is composed of 4.95% ZnO nanoparticles (particle size is 6nm), 0.05% fullerene and 95% black phosphorus nanosheets .
  • the preparation method of described complex comprises the steps:
  • step S3.2 Place the mixed solution in step S3.1 at 150°C for 4 hours to react, and the obtained reaction product is a black phosphorus nanosheet-fullerene composite solution, and dry under reduced pressure (at a pressure of -0.1MPa) to remove the black phosphorus A solvent in the nanosheet-fullerene composite solution to obtain a solid black phosphorus nanosheet-fullerene composite material;
  • step S3.4 At room temperature, add ethyl acetate dropwise to the reaction product in step S3.3, and stir fully at the same time, stop adding ethyl acetate until no white precipitate occurs, let it settle for 5 hours naturally, remove the precipitate by filtration and remove The liquid phase was collected, dried under reduced pressure (at a pressure of -0.1 MPa) to remove the solvent of the liquid phase, and a purified compound was obtained.
  • This example provides a composite and a preparation method thereof. Compared with the composite of Example 1, the only difference of the composite of this example is that fullerene is replaced by [60]PCBM.
  • This example provides a composite and a preparation method thereof. Compared with the composite of Example 1, the only difference of the composite of this example is that fullerene is replaced by [70]PCBM.
  • the embodiment of the present application provides an electroluminescent device and its preparation method. As shown in FIG. 13-1, the first charge generation layer 14-1, the second light emitting layer 13-2, the electron transport layer 16 and the cathode 12.
  • each layer structure in the electroluminescent device 1 is as follows:
  • the material of the substrate 10 is glass with a thickness of 0.55mm;
  • the material of the anode 11 is ITO, and the thickness is 50nm;
  • the material of the cathode 12 is silver, and the thickness is 100nm;
  • the material of the first light-emitting layer 13-1 is CdSe/ZnS, and the thickness is 15nm;
  • the material of the first light-emitting layer 13-2 is CdSe/ZnS, and the thickness is 15nm;
  • the material of the first charge generation layer 14-1 is the composite prepared in Example 1, and the thickness is 30 nm;
  • the hole transport layer 15 is made of TFB with a thickness of 30nm;
  • the electron transport layer 16 is made of zinc oxide nanoparticles with a particle size of 6 nm and a thickness of 40 nm.
  • ITO substrate After cleaning and drying the ITO substrate, treat it with ultraviolet and ozone for 15 minutes to serve as anode and substrate;
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device in Embodiment 6, the only difference between the electroluminescent device in this embodiment is that the material of the charge generation layer is replaced with the one in Embodiment 2. The compound produced.
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device of Embodiment 6, the only difference between the electroluminescent device of this embodiment is that the material of the charge generation layer is replaced by the material of Embodiment 3. The compound produced.
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device of Embodiment 6, the only difference between the electroluminescent device of this embodiment is that the material of the charge generation layer is replaced by the material of Embodiment 4. The compound produced.
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device of Embodiment 6, the only difference between the electroluminescent device of this embodiment is that the material of the charge generation layer is replaced by the material of Embodiment 5. The compound produced.
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device in Embodiment 6, the only difference of the electroluminescent device in this embodiment is that the material of the charge generation layer is replaced by "by weight Percentage calculation, the composite is composed of 50% ZnO nanoparticles (particle size is 6nm) and 50% black phosphorus nanosheets".
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • step S11.2 placing the mixture in step S11.1 at 0° C. for 5 h and stirring to react to obtain a reaction product comprising black phosphorus nanosheet-ZnO nanoparticle composite material;
  • step S11.3 At room temperature, add ethyl acetate dropwise to the reaction product in step S11.2, and stir thoroughly at the same time, stop adding ethyl acetate until no white precipitate is produced, let it settle for 5 hours, remove the precipitate by filtration and remove The liquid phase is collected, dried under reduced pressure (the pressure is -0.1 MPa) to remove the solvent of the liquid phase, and a purified charge generation layer material is obtained.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device in Embodiment 6, the only difference of the electroluminescent device in this embodiment is that the material of the charge generation layer is replaced by "by weight Calculated in percentage, the composite is composed of 10% ZnO nanoparticles (particle size is 6nm) and 90% black phosphorus nanosheets".
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • step S12.2 placing the mixture in step S12.1 at 0° C. for 5 h and stirring to react to obtain a reaction product comprising black phosphorus nanosheet-ZnO nanoparticle composite material;
  • step S12.3 At room temperature, add ethyl acetate dropwise to the reaction product in step S12.2, and stir fully at the same time, stop adding ethyl acetate until no white precipitate occurs, let it settle for 5 hours naturally, remove the precipitate by filtration and remove The liquid phase is collected, dried under reduced pressure (the pressure is -0.1 MPa) to remove the solvent of the liquid phase, and a purified charge generation layer material is obtained.
  • This embodiment provides an electroluminescent device. Compared with the electroluminescent device in Embodiment 6, the only difference of the electroluminescent device in this embodiment is that the material of the charge generation layer is replaced by "by weight Calculated in percentage, the composite is composed of 40% ZnO nanoparticles (particle size is 6nm) and 60% black phosphorus nanosheets".
  • the preparation method of the electroluminescent device of this embodiment is carried out with reference to Example 6.
  • step S13.2 placing the mixture in step S13.1 at 0° C. for 5 h to react, and obtaining a reaction product comprising black phosphorus nanosheet-ZnO nanoparticle composite material;
  • step S13.3 At room temperature, add ethyl acetate dropwise to the reaction product in step S13.2, and stir fully at the same time, stop adding ethyl acetate until no white precipitate occurs, let it settle for 5 hours naturally, remove the precipitate by filtration and remove The liquid phase is collected, dried under reduced pressure (the pressure is -0.1 MPa) to remove the solvent of the liquid phase, and a purified charge generation layer material is obtained.
  • This comparative example provides an electroluminescent device and a preparation method thereof. Compared with the electroluminescent device of Example 9, the difference between the electroluminescent device of this comparative example is that the structural composition of the charge generation layer is different.
  • the charge generation layer is composed of the first sub-film and the second sub-film stacked, the material of the first sub-film is tris(8-hydroxyquinoline)aluminum (Alq 3 ), the first sub-film The thickness of the film is 30nm; the material of the second sub-film is molybdenum trioxide (MoO 3 ), and the thickness of the second sub-film is 25nm, wherein the first sub-film is close to the first light-emitting layer, and the second sub-film is close to the second light-emitting layer layer.
  • step S9.4 is replaced with "Using the vacuum evaporation method on the side of the first light-emitting layer away from the hole transport layer to depositing to form a first sub-film and a second sub-film”.
  • This comparative example provides an electroluminescent device and its preparation method. Compared with the electroluminescent device of Example 6, the difference between the electroluminescent device of this comparative example is that the material of the charge generation layer is replaced It is the black phosphorus nanosheet-fullerene composite material prepared in step S1.2 in Example 1.
  • step S6.4 replaces the black phosphorus nanosheet-fullerene composite material in ethanol to obtain a concentration of 30mg/mL black phosphorus nanosheet-fullerene composite solution, inkjet printing the composite solution on the side of the first light-emitting layer away from the hole transport layer in step 6.3 under a nitrogen atmosphere at normal temperature and pressure, Then place it at 150°C for constant temperature heat treatment for 30 minutes to obtain a charge generation layer.”
  • the electroluminescent device of embodiment 6 to embodiment 13 and the electroluminescent device of comparative example 1 and comparative example 2 are carried out performance detection, and the project of performance test is: the voltage (U@ 1000nit, V) and the maximum current efficiency (Cd/A), among them, the performance parameters of the electroluminescent device are detected by the optoelectronic instrument composed of CS-2000 and Keithley source meter, and the performance test results are shown in the following table 1: Table 1 The performance testing results of the electroluminescent devices of Example 6 to Example 13 and Comparative Example 1 and Comparative Example 2
  • the photoelectric performance of the electroluminescent devices of Example 6 to Example 13 has obvious advantages, indicating that the use of this
  • the compound of the application example is used as the material of the charge generation layer, which is beneficial to reduce the operating voltage of the electroluminescent device, and can efficiently inject electrons and holes into the light-emitting layer, thereby significantly improving the current efficiency of the electroluminescent device and effectively improving the efficiency of the electroluminescent device.
  • Comparative Example 2 uses black phosphorus nanosheet-fullerene composite material as the material of the charge generation layer.
  • the stability of the black phosphorus nanosheet-fullerene composite is not as good as the composite of the embodiment of the present application; further, The electron mobility of fullerene is lower than that of black phosphorus nanosheets, and fullerenes are distributed on the edge of black phosphorus nanosheets, which may cause hole-electron imbalance in black phosphorus nanosheets-fullerene composites Therefore, the overall performance of the electroluminescent device of Comparative Example 2 is not as good as that of the electroluminescent devices of Examples 6 to 13.

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Abstract

La présente demande divulgue un complexe, un procédé de préparation du complexe et un dispositif électroluminescent. Le complexe comprend : un matériau semi-conducteur de type P et un matériau semi-conducteur de type N qui sont liés de manière covalente. Le matériau semi-conducteur de type P comprend des nanofeuillets de phosphore noir, et le matériau semi-conducteur de type N comprend un composant A et un composant B. Le composant A comprend des nanoparticules inorganiques, le composant B comprend un ou plusieurs éléments parmi un fullerène et des dérivés de fullerène, et le complexe peut être utilisé pour préparer une couche de génération de charge d'un dispositif électroluminescent.
PCT/CN2022/126331 2021-11-15 2022-10-20 Complexe, procédé de préparation du complexe et dispositif électroluminescent WO2023082964A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012038841A (ja) * 2010-08-05 2012-02-23 Japan Aviation Electronics Industry Ltd 光電変換素子および太陽電池
CN109817731A (zh) * 2019-02-02 2019-05-28 京东方科技集团股份有限公司 一种光电二极管及其制作方法、电子设备
CN111303485A (zh) * 2020-04-03 2020-06-19 北京石墨烯技术研究院有限公司 复合填料、聚四氟乙烯基复合材料及制备方法和制成品

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012038841A (ja) * 2010-08-05 2012-02-23 Japan Aviation Electronics Industry Ltd 光電変換素子および太陽電池
CN109817731A (zh) * 2019-02-02 2019-05-28 京东方科技集团股份有限公司 一种光电二极管及其制作方法、电子设备
CN111303485A (zh) * 2020-04-03 2020-06-19 北京石墨烯技术研究院有限公司 复合填料、聚四氟乙烯基复合材料及制备方法和制成品

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