WO2020108079A1 - Procédé de préparation d'un point quantique - Google Patents

Procédé de préparation d'un point quantique Download PDF

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WO2020108079A1
WO2020108079A1 PCT/CN2019/109072 CN2019109072W WO2020108079A1 WO 2020108079 A1 WO2020108079 A1 WO 2020108079A1 CN 2019109072 W CN2019109072 W CN 2019109072W WO 2020108079 A1 WO2020108079 A1 WO 2020108079A1
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quantum dots
composite material
oil
pamam dendrimer
initial
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程陆玲
杨一行
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Tcl科技集团股份有限公司
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    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots

Definitions

  • the present disclosure relates to the field of quantum dots, and in particular to a method for preparing quantum dots.
  • quantum dots There are many techniques for preparing quantum dots. No matter what way the quantum dots are prepared, there will be corresponding anion and cation defects on the surface layer, that is, the surface growth is not very good; the anion and cation defects on the surface of the quantum dots will be to a certain extent.
  • the exciton trapping causes quenching.
  • the anion defects on the surface of quantum dots can be compensated and improved by surface ligand modifiers, while the cationic defects on the surface of quantum dots in the prior art mainly use organic metal cation precursors to passivate the surface of quantum dots.
  • the treatment of the technical solution will cause further anion defects on the surface of the quantum dot, so the existing technology needs to be improved.
  • the purpose of the present disclosure is to provide a quantum dot and its preparation method, and quantum dot light-emitting diode, aiming to solve the problem that the prior art cannot effectively remove the cation defects on the surface of the quantum dot.
  • a method for preparing quantum dots which includes the steps of:
  • a composite material including PAMAM dendrimers and metal ions bound in the cavity of the PAMAM dendrimers;
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent to ionize the metal ions in the oil-soluble composite material and combine with the cation vacancies on the surface of the initial quantum dots to obtain the quantum dots.
  • the present disclosure provides a method for preparing quantum dots.
  • PAMAM dendrimers combined with metal ions in the cavity as a passivation precursor, surface passivation treatment of the initial quantum dots can produce fewer surface cation defects Quantum dots.
  • FIG. 1 is a flow chart of a preferred embodiment of a method for preparing quantum dots of the present disclosure.
  • the present disclosure provides a method for preparing quantum dots. To make the objectives, technical solutions, and effects of the present disclosure clearer and more specific, the present disclosure will be described in further detail below. It should be understood that the specific embodiments described herein are only used to explain the present disclosure and are not intended to limit the present disclosure.
  • the present disclosure provides a flow chart of a preferred embodiment of a method for preparing quantum dots. As shown in the figure, the method includes the following steps:
  • PAMAM dendrimers with metal ions incorporated in the cavity are used as precursors for the passivation element, and surface passivation treatment of the initial quantum dots can produce quantum dots with fewer surface cation defects.
  • the mechanism for achieving the above effects is as follows:
  • Quantum dots prepared by conventional oil phase technology usually have more cation vacancies on the surface, and the cation vacancies on the quantum dot surface are prone to coordination effects when they encounter metal ions again in a certain solution environment.
  • the modified oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the metal ions in the oil-soluble composite material are ionized, and the initial quantum dots with cation vacancies on the surface are It is easier to produce chemical coordination when encountering free metal ions, so that free metal ions are bound to the cation vacancies on the surface of the initial quantum dots.
  • the metal ions in the PAMAM dendrimer can be ionized to fill the cation vacancies on the surface of the initial quantum dots, thereby reducing the defect states on the surface of the quantum dots.
  • the method for preparing the composite material includes the steps of: providing a PAMAM dendrimer; adding the PAMAM dendrimer to a metal ion solution, and mixing the N atoms in the PAMAM dendrimer cavity with The metal ions are coordinated and combined to obtain a composite material.
  • the PAMAM (polyamide-amine) dendrimer is obtained by reacting different molecular units A (ethylenediamine) and molecular units B (methyl acrylate), and the PAMAM dendrimer can be obtained by a divergent method Synthesis, the first step is the reaction of ethylenediamine and methyl acrylate to produce carboxylic acid ester. The second step is to react the obtained carboxylic acid ester with excess ethylenediamine. After the above two steps, the first generation of PAMAM can be prepared For dendrimers, repeat the above two steps to obtain higher algebraic PAMAM dendrimers.
  • the general formulas of molecular unit A and molecular unit B contained in PAMAM dendrimers of different algebras are: A(2 n +2 n-1 +...+2 n-3 )+B(2 n+1 +2 n + ....+2 n-1 ), where the value of n is 3-10; in addition, the general formula of the first generation PAMAM dendrimer containing molecular unit A and molecular unit B is A+4B, the second generation PAMAM dendrimer The general formula of the molecule containing molecular unit A and molecular unit B is 5A+8B.
  • the number of metal ions that can be combined by different generations of PAMAM dendrimers is different.
  • the main reason is that different generations of PAMAM dendrimers can coordinate metal ions.
  • the generation of PAMAM dendrimers is from the first generation to In the fourth generation, due to its low density of terminal functional groups (amine groups), it is not easy to be used as a carrier for adsorbing metal ions.
  • the PAMAM dendrimer is selected from the fifth generation PAMAM dendrimer (G5), the sixth generation PAMAM dendrimer (G6), the seventh generation PAMAM dendrimer (G7), and the eighth generation PAMAM One or more of dendrimer (G8), ninth generation PAMAM dendrimer (G9), tenth generation PAMAM dendrimer (G10), etc.
  • the algebra of the PAMAM dendrimer is G5-G10
  • the functional groups and functional groups can form a complete and The closed cavity, so the PAMAM dendrimers of the G5-G10 generation can be used as candidate materials for the coordination with metal ions.
  • the elemental species of the metal ion is selected from the group consisting of Mn, Zn, Cd, Hg, Pb, In, Ag, Mg, Au, Cu, Li, Al, Cd, In, Cs, Ga, and Gd One or more, but not limited to this.
  • the terminal functional groups of the PAMAM dendrimer in the composite material are modified to convert the amine groups in the PAMAM dendrimer into oil-soluble groups
  • the step of obtaining an oil-soluble composite material includes: After the composite material is dissolved in a polar solvent, an end group modifier is added, so that the amine functional group on the PAMAM dendrimer in the composite material reacts with the end group modifier to transform into an oil-soluble group to obtain the oil-soluble property Composite materials.
  • the composite material can be stably stored and dissolved In a polar solvent, a composite material solution is prepared. Adding an excessive amount of end-group modifier to the composite material solution under an inert atmosphere and rapidly stirring can make the amine functional group on the PAMAM dendrimer react with the end-group modifier to transform into oil-soluble groups to prepare oil Soluble composite material.
  • the end group modifier is selected from p-toluenesulfonyl chloride, o-toluenesulfonyl chloride, m-toluenesulfonyl chloride, p-dimethylaminobenzenesulfonyl chloride, o-dimethylbenzenesulfonyl chloride and m-dimethylaminobenzene
  • p-toluenesulfonyl chloride o-toluenesulfonyl chloride, m-toluenesulfonyl chloride, p-dimethylaminobenzenesulfonyl chloride, o-dimethylbenzenesulfonyl chloride and m-dimethylaminobenzene
  • the Dendrimer-NH 2 is a PAMAM dendrimer of the G5-G10 generation. After being modified with end groups, the composite material can be effectively dispersed in a non-polar solvent.
  • the end group modifier is added after dissolving the composite material in a polar solvent under the condition of 20-50°C, so that the amine functional group and the end group on the PAMAM dendrimer in the composite material The modifier reacts to transform into oil-soluble groups to obtain the oil-soluble composite material.
  • the oil-soluble composite material and the initial quantum dots are added to a non-polar solvent according to a predetermined ratio, and mixed to ionize the metal ions in the oil-soluble composite material to the cation vacancies on the surface of the initial quantum dots Coordinate bonding to obtain the quantum dots.
  • the metal ions in the oil-soluble composite material described in this embodiment can efficiently coordinate with the cation vacancy on the surface of the quantum dot, and will not introduce other unnecessary anions to affect the passivation effect of the quantum dot.
  • the amount of PAMAM dendrimers of different generations bound to metal ions is different, so the oil-soluble composite material and the initial quantum
  • the molar mass ratio of points is related to the algebra of PAMAM dendrimers.
  • the PAMAM dendrimer in the composite material is the fifth generation PAMAM dendrimer
  • the molar ratio to the initial quantum dot mass ratio is 1 mmol: (1-100) mg, and the oil-soluble composite material and the initial quantum dot are mixed in a non-polar solvent.
  • the molar ratio of the sixth-generation PAMAM dendrimer to the initial quantum dot mass ratio is 1 mmol: (10-150) mg
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the molar ratio of the seventh-generation PAMAM dendrimer to the initial quantum dot mass ratio is 1 mmol: (50-200) mg
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the molar ratio of the eighth-generation PAMAM dendrimer to the initial quantum dot mass ratio is 1 mmol: (100-250) mg.
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the molar ratio of the ninth-generation PAMAM dendrimer to the initial quantum dot mass ratio is 1 mmol: (150-300) mg,
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the molar ratio of the molar amount of the tenth generation PAMAM dendrimer to the initial quantum dot is 1 mmol: (200-500) mg
  • the oil-soluble composite material and the initial quantum dots are mixed in a non-polar solvent.
  • the PAMAM dendrimer is selected from one or both of the fifth generation PAMAM dendrimer and the sixth generation PAMAM dendrimer. Because the metal ions in the composite material will form a chemical bond with multiple N atoms in the gap of the terminal functional group of the PAMAM dendrimer, this makes the pyrolysis rate of the metal ion in the composite material slower than that of the organometallic precursor More; and the PAMAM dendrimers containing metal ions have larger corresponding viscosities as the algebraic number increases, and the greater the viscosity makes the metal ions and the cation vacancy coordination binding efficiency on the surface of the initial quantum dots decrease.
  • the PAMAM dendrimer is selected from the fifth generation PAMAM dendrimer and the sixth generation PAMAM dendrimer One or two of the molecules.
  • the oil-soluble composite material and quantum dots are added to a non-polar solvent and mixed at 80-300°C to combine the metal ions in the oil-soluble composite material with cation vacancies on the surface of the quantum dots.
  • Get quantum dots When the temperature of the PAMAM dendrimer (oil-soluble composite material) modified with end groups and containing metal ions in a nonpolar solvent is higher than a certain value, the metal ions will leave the dendrimer and enter the nonpolar solvent to participate in other chemical reactions.
  • the temperature range of the metal ions in PAMAM dendrimers of different algebras can be separated from PAMAM dendrimers is 800-300°C. Therefore, in order to ensure that the metal ions in the oil-soluble composite material can coordinately coordinate with the cation vacancy on the surface of the quantum dot, the oil-soluble composite material and the quantum dot are mixed under the condition of 80-300°C.
  • the oil-soluble composite material and the quantum dot are added to a non-polar solvent, wherein the metal ion in the oil-soluble composite material and the cation on the surface of the quantum dot are the same element.
  • the metal ion coordinated to the N atom in the gap of the terminal functional group of the PAMAM dendrimer in the oil-soluble composite material is Zn 2+ .
  • the effect after passivation can effectively reduce the defect on the surface of the quantum dot and improve the fluorescence intensity of the light-emitting quantum dot.
  • the metal ion in the oil-soluble composite material and the cation on the surface of the quantum dot are different elements.
  • the metal ion in the oil-soluble composite material is Zn 2+ .
  • the metal ion in the oil-soluble composite material is different from the cationic element on the surface of the quantum dot, if the band gap of the passivated quantum dot surface layer compound is greater than the band gap of the inner shell layer, it can not only enhance the quantum dot fluorescence intensity It can also improve the stability of quantum dots.
  • the quantum dots are selected from one of single-type quantum dots, core-shell quantum dots, or alloy structure quantum dots.
  • the group III-V single quantum dot is selected from one or more of GaN, GaP, GaAs, InP, InAs, InAsP, GaAsP, InGaP, InGaAs, and InGaAsP.
  • the group II-VI single quantum dot is selected from one or more of CdSe, CdS, CdTe, ZnSe, ZnS, ZnTe, HgSe, HgS, and HgTe.
  • the group III-V and group II-VI alloy structure quantum dots are selected from one or more of InPZnS, InPZnSe, InPZnSeS, InGaPZnSe, InGaPZnS and InGaPZnSeS.
  • the group II-VI core-shell quantum dots are selected from one or more of CdHgTe/CdS, CdTe/CdS, CdSe/ZnS, CdSeS/CdS and ZnSe/ZnS.
  • the present disclosure also provides a quantum dot, which is prepared by the method of the present disclosure.
  • the present disclosure also provides a quantum dot light emitting diode, including a quantum dot light emitting layer, wherein the material of the quantum dot light emitting layer is a quantum dot prepared by the preparation method of the present disclosure.
  • quantum dots with fewer surface defects prepared in the present disclosure can effectively improve the fluorescence intensity of the quantum dot light emitting diode.
  • the quantum dot light-emitting diode includes an anode, a hole transport layer, a quantum dot light-emitting layer, an electron transport layer, and a cathode that are stacked, wherein the material of the quantum dot light-emitting layer is prepared by the preparation method of the present disclosure Quantum dots.
  • the present disclosure is not limited to the quantum dot light-emitting diode of the above structure, and may further include an interface function layer or an interface modification layer, including but not limited to an electron blocking layer, a hole blocking layer, an electrode modification layer, and an isolation protection layer One or more.
  • the quantum dot light emitting diode of the present disclosure may be partially encapsulated, fully encapsulated, or unencapsulated.
  • QLED quantum dot light-emitting diode
  • the QLEDs can be divided into a QLED with a formal structure and a QLED with a flip structure.
  • the QLED of the formal structure includes an anode layered from the bottom up (the anode layered layer is disposed on the substrate), a hole transport layer, a quantum dot light emitting layer, an electron transport layer, and a cathode , wherein the quantum dot light emitting layer material is a quantum dot prepared by the preparation method of the present disclosure.
  • the flip-chip QLED includes a cathode stacked from the bottom up (the cathode stack is disposed on the substrate), an electron transport layer, a quantum dot light emitting layer, a hole transport layer, and An anode, wherein the material of the quantum dot light emitting layer is a quantum dot prepared by the preparation method of the present disclosure.
  • the material of the anode is selected from doped metal oxides; wherein, the doped metal oxides include but are not limited to indium-doped tin oxide (ITO), fluorine-doped tin oxide (FTO), Antimony-doped tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), magnesium-doped zinc oxide (MZO), aluminum-doped magnesium oxide One or more of (AMO).
  • ITO indium-doped tin oxide
  • FTO fluorine-doped tin oxide
  • ATO Antimony-doped tin oxide
  • AZO aluminum-doped zinc oxide
  • GZO gallium-doped zinc oxide
  • IZO indium-doped zinc oxide
  • MZO magnesium-doped zinc oxide
  • AMO aluminum-doped magnesium oxide
  • AMO aluminum-doped magnesium oxide
  • the material of the hole transport layer is selected from organic materials with good hole transport capabilities, such as but not limited to poly(9,9-dioctylfluorene-CO-N-(4- (Butylphenyl) diphenylamine) (TFB), polyvinylcarbazole (PVK), poly(N,N'bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine) ( Poly-TPD), poly(9,9-dioctylfluorene-co-bis-N,N-phenyl-1,4-phenylenediamine) (PFB), 4,4',4”-tri(carb Azole-9-yl) triphenylamine (TCTA), 4,4'-bis(9-carbazole) biphenyl (CBP), N,N'-diphenyl-N,N'-bis(3-methyl Phenyl)-1,1'-biphenyl-4,4'
  • the material of the cathode is selected from one or more of conductive carbon materials, conductive metal oxide materials and metal materials; wherein the conductive carbon materials include but are not limited to doped or undoped carbon nanotubes , One or more of doped or undoped graphene, doped or undoped graphene oxide, C60, graphite, carbon fiber and porous carbon; conductive metal oxide materials include but are not limited to ITO, FTO, ATO And one or more of AZO; metal materials include, but are not limited to, Al, Ag, Cu, Mo, Au, or their alloys; wherein, among the metal materials, their morphologies include but are not limited to dense thin films, nanowires, One or more of nanospheres, nanorods, nanocones and hollow nanospheres.
  • the present disclosure also provides a method for preparing a QLED with a hole-transporting layer in a formal structure, including the following steps:
  • the quantum dot light-emitting layer material is a quantum dot prepared by the preparation method of the present disclosure
  • a cathode is prepared on the electron transport layer to obtain QLED.
  • the present disclosure also provides a method for preparing a flip-chip structured QLED containing a hole transport layer, including the following steps:
  • the quantum dot light-emitting layer material is a quantum dot prepared by the preparation method of the present disclosure
  • An anode was prepared on the hole transport layer to obtain QLED.
  • the preparation method of the above layers may be a chemical method or a physical method, wherein the chemical method includes but is not limited to one of chemical vapor deposition method, continuous ion layer adsorption and reaction method, anodizing method, electrolytic deposition method, co-precipitation method or A variety of; physical methods include but are not limited to physical coating method or solution method, wherein the solution method includes but not limited to spin coating method, printing method, blade coating method, dipping method, dipping method, spraying method, roll coating method, casting Method, slot coating method, strip coating method; physical coating method includes but not limited to thermal evaporation coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion coating method, physical vapor deposition method, One or more of atomic layer deposition and pulsed laser deposition.
  • the chemical method includes but is not limited to one of chemical vapor deposition method, continuous ion layer adsorption and reaction method, anodizing method, electrolytic deposition method, co-pre
  • the present disclosure provides a method for preparing quantum dots.
  • Surface cation defects can be prepared by surface passivating the initial quantum dots by using PAMAM dendrimers combined with metal ions in the cavity as passivation precursors Fewer quantum dots.
  • using the quantum dots as the material of the quantum dot light emitting layer of the quantum dot light emitting diode can effectively increase the fluorescence intensity of the quantum dot light emitting diode.

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  • Luminescent Compositions (AREA)

Abstract

L'invention concerne un procédé de préparation d'un point quantique, comprenant Les étapes suivantes : fourniture d'un matériau composite comprenant un dendrimère PAMAM et un ion métallique combiné à l'intérieur du dendrimère PAMAM ; transformation du groupe amido dans le dendrimère PAMAM dans le matériau composite en un groupe liposoluble pour obtenir un matériau composite liposoluble ; et mélange du matériau composite liposoluble et d'un point quantique initial dans un solvant non polaire, et ionisation de l'ion métallique dans le matériau composite liposoluble, et réalisation d'une liaison de coordonnées sur l'ion métallique ionisé et une vacance cationique sur la surface du point quantique initial pour obtenir le point quantique.
PCT/CN2019/109072 2018-11-28 2019-09-29 Procédé de préparation d'un point quantique WO2020108079A1 (fr)

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CN102703057A (zh) * 2012-05-18 2012-10-03 北京工商大学 一种聚酰胺-胺树形分子包覆的ZnX半导体量子点在指纹显现中的应用
CN106398680A (zh) * 2016-08-30 2017-02-15 Tcl集团股份有限公司 一种油溶性蓝光量子点及其制备方法
CN107359264A (zh) * 2017-08-03 2017-11-17 青岛海信电器股份有限公司 一种qled、制备方法及显示装置

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107936943A (zh) * 2017-12-05 2018-04-20 华南师范大学 一种基于树形分子的量子点荧光强度增强方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102703057A (zh) * 2012-05-18 2012-10-03 北京工商大学 一种聚酰胺-胺树形分子包覆的ZnX半导体量子点在指纹显现中的应用
CN106398680A (zh) * 2016-08-30 2017-02-15 Tcl集团股份有限公司 一种油溶性蓝光量子点及其制备方法
CN107359264A (zh) * 2017-08-03 2017-11-17 青岛海信电器股份有限公司 一种qled、制备方法及显示装置

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