WO2019015345A1 - 配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管 - Google Patents

配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管 Download PDF

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WO2019015345A1
WO2019015345A1 PCT/CN2018/079221 CN2018079221W WO2019015345A1 WO 2019015345 A1 WO2019015345 A1 WO 2019015345A1 CN 2018079221 W CN2018079221 W CN 2018079221W WO 2019015345 A1 WO2019015345 A1 WO 2019015345A1
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ligand
quantum dot
group
modified quantum
modified
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French (fr)
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张振琦
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京东方科技集团股份有限公司
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Priority to US16/305,712 priority patent/US11453820B2/en
Priority to EP18807546.9A priority patent/EP3656832B1/en
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    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
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    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/56—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing sulfur
    • C09K11/562—Chalcogenides
    • C09K11/565—Chalcogenides with zinc cadmium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
    • C09K11/883—Chalcogenides with zinc or cadmium
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Definitions

  • the present disclosure relates to a ligand-modified quantum dot composition, a ligand-modified quantum dot layer, a preparation method thereof, and a quantum dot light-emitting diode.
  • the OLED light-emitting layer is an organic material, which has problems such as easy oxidation, short life, wide luminescence spectrum, and complicated synthesis.
  • quantum dot materials have gradually emerged, their luminescence spectra are narrower than organic materials, their stability is better than that of organic materials, and the synthesis cost is lower than that of organic materials, and has been applied to electroluminescent devices, so QD-LED has also become A strong contender for OLED technology.
  • Embodiments of the present disclosure provide a ligand-modified quantum dot composition
  • a ligand-modified quantum dot composition comprising a quantum dot and a ligand modifier adsorbed on the surface of the quantum dot, wherein the ligand modifier has the structural formula: segment A-segment B
  • the ligand modifier is adsorbed on the surface of the quantum dot by the segment A, and the segment B is a long chain of chains that can be broken. .
  • the ligand-modified quantum dot composition is an ink
  • the quantum dot composition has a viscosity of 8-15 cP
  • the ligand-modified quantum dot composition has a surface tension of 20-40 mN/m.
  • cP is a unit of viscosity centipoise
  • 1 centipoise (1 cP) 1 mPas s (1 mPa.s).
  • the quantum dots include any one or more of a group III-V quantum dot, a group IV quantum dot, a II-VI quantum dot, a core-shell quantum dot, and an alloy quantum dot.
  • the quantum dots include CdS, CdSe, CdTe, ZnSe, InP, PbS, CuInS 2 , ZnO, CsPbCl 3 , CsPbBr 3 , CsPhI 3 , CdS/ZnS, CdSe/ZnS, ZnSe, InP/ZnS Any one or more of PbS/ZnS, InAs, InGaAs, InGaN, GaNk, ZnTe, Si, Ge, and C.
  • the segment A includes any one or more of the following groups: amino, thiol, hydroxy, polyamino, polythiol, polyhydroxy, phosphorus, oxyphosphorus, organophosphorus, thioether .
  • the segment B comprises an R1 group, an R2 group, an R3 group, which are sequentially linked one after the other, wherein the R1 group is attached to the segment A, and the R2 group is cleavable.
  • the R2 group comprises a group that is photodegraded or thermally degraded.
  • the chemical bond between the R2 group and the R1 group is broken under heat or illumination.
  • the chemical bond between the R2 group and the R1 group is broken under heat or illumination, and the chemical bond between the R2 group and the R3 group is broken.
  • the chemical bond in the R2 group itself is broken under heat or illumination.
  • the R1 group includes any one or more of the following groups: an aromatic group, an ethyl group, a butyl group, a cyclohexyl group, a methoxy group, a methylamino fatty chain; A cyclohexyl alicyclic compound.
  • the R3 group includes any one or more of the following groups: an aromatic group, and an ethyl, butyl, cyclohexyl, methoxy, methylamino fatty chain; epoxy Propane-based, cyclohexyl alicyclic compound.
  • the aromatic group includes any one or more of the following groups: phenyl, alkylphenyl, thienyl, pyrimidinyl, anilino, naphthalene, phenoxy.
  • the embodiment of the present disclosure further provides a method for preparing a ligand-modified quantum dot composition, comprising the steps of:
  • Adding a second ligand modifier to the first ligand-modified quantum dot wherein the second ligand modifier has the structural formula: segment A-segment B, and the segment B is chain-breakable a long molecular chain, the second ligand modifying agent being displaced with the first ligand such that the segment A of the second ligand modifying agent is adsorbed on the surface of the quantum dot to obtain a second ligand-modified quantum dot;
  • the second ligand modified quantum dot is separated from the first ligand.
  • the first ligand modifying agent comprises oleic acid and the solvent comprises octadecene.
  • the present disclosure also provides a method for preparing a ligand-modified quantum dot layer, comprising the steps of:
  • the step of forming a ligand-modified quantum dot layer further comprises the step of adding a radical scavenger.
  • the radical scavenger comprises any one or more of the following groups: alcohol, water, phenol, thiol.
  • the method further includes the step of heating to separate the chain scission from the ligand-modified quantum dot layer.
  • FIG. 1 is a schematic structural view of a ligand-modified quantum dot composition according to an embodiment of the present disclosure
  • FIGS. 2 and 3 are schematic diagrams showing the structure of a ligand-modified quantum dot composition according to another embodiment of the present disclosure
  • FIG. 4 and FIG. 5 are schematic diagrams showing a reaction process of a segment B according to another embodiment of the present disclosure.
  • FIG. 6 is a flow chart of a method for preparing a ligand-modified quantum dot composition according to still another embodiment of the present disclosure
  • FIG. 7 is a flow chart of a method for preparing a ligand-modified quantum dot layer according to still another embodiment of the present disclosure.
  • Quantum dot materials are inorganic nanoparticles that require an outer layer to modify the organic ligand to improve stability and solubility.
  • Quantum dot materials which usually have short-chain ligands, form a denser film when forming a light-emitting layer film, and have a higher carrier transport rate.
  • short-chain ligands may reduce solubility, while short-chain ligands make quantum dot materials more interactive, easier to coagulate and cannot be preserved. Therefore, the current mainstream quantum dot material ligands are still long-chain ligands such as oleic acid oleylamine.
  • the quantum dots are not dense enough when the long-chain ligand-modified quantum dots are formed, and the carrier transport efficiency is low.
  • the present invention proposes a ligand-modified quantum dot composition and a ligand for the problem that the existing short-chain ligand makes the quantum dot material difficult to store and the long-chain ligand-modified quantum dot carrier has low transmission efficiency.
  • Embodiments of the present disclosure provide a ligand-modified quantum dot composition, as shown in FIG. 1, which includes a quantum dot 1 and a ligand modifier 2 adsorbed on the surface of the quantum dot.
  • the ligand modifier 2 contains a long molecular chain group, and at least a part of the long chain chain can be broken under certain conditions.
  • the ligand modifier 2 has the structural formula: segment A-segment B. Segment A is used to adsorb to the surface of the quantum dot, and segment B is a long chain of chains that can be broken.
  • the segment B in the ligand modifier of the quantum dot composition of the embodiment of the present disclosure is a chain segment that can be broken, that is, the segment B is a longer molecular chain, so that the composition has good solubility and stability, and thus
  • the ligand-modified quantum dot composition is present in the form of a solution or ink.
  • segment B itself is not very stable, and it can be broken under certain conditions.
  • the group in the segment B can be broken by heating or illumination, so that the ligand modifier becomes a short molecular chain ligand, thereby making the quantum dots densely packed and improving carrier transport performance.
  • the mass ratio of quantum dots to ligand modifiers is from about 5% to 300%.
  • the ligand modifier has the structural formula: segment A-segment B, segment A is used for adsorption on the surface of the quantum dot, and segment B is a long chain of chains that can be broken.
  • segment B includes an R1 group, an R2 group, and an R3 group which are sequentially connected one by one.
  • the R1 group is attached to segment A, which can be cleaved.
  • the R2 group can be broken in two ways.
  • the first one is shown in Figure 2, the chemical bond between the R1 group and the R2 group is broken. In this case, usually the chemical bond between the R2 group and the R3 group is also broken at the same time.
  • the second see Figure 3, is the chemical bond disconnection in R2 itself.
  • R2 is cleaved to R2a, R2b, R2c, wherein R2a is attached to R1, R2c is attached to R3, and R2b is released as a gas.
  • the manner in which the R1 group and the R2 group are divided can be selected according to different long molecular chains, and the specific substance thereof can be changed as needed.
  • the above three specific forms are given in the embodiments of the present disclosure. It will be appreciated that it is also possible to have other chain cleavable groups.
  • the quantum dot includes any one or more of a group III-V quantum dot, a group IV quantum dot, a II-VI quantum dot, a core-shell quantum dot, and an alloy quantum dot. Specifically, it may be CdS, CdSe, CdTe, ZnSe, InP, PbS, CuInS 2 , ZnO, CsPbCl 3 , CsPbBr 3 , CsPhI 3 , CdS/ZnS, CdSe/ZnS, ZnSe, InP/ZnS, PbS/ZnS, InAs Any one or more of InGaAs, InGaN, GaNk, ZnTe, Si, Ge, and C.
  • the existing quantum dots can be used as the luminescent material in the embodiments of the present disclosure, which may be a single quantum dot or a composite of two or more quantum dots.
  • the specific choice of quantum dots can be selected according to the desired luminescent color, etc., and will not be mentioned here.
  • segment A includes any one or more of the following groups: amino, thiol, hydroxy, polyamino, polyfluorenyl, polyhydroxy, phosphorus, oxyphosphorus, organophosphorus, thioether.
  • the segment A contains a group which is easily complexed with a quantum dot, such as an amino group, a thiol group, a hydroxyl group, a polyamino group, a polyfluorenyl group, a polyhydroxy group, a phosphorus, a phosphorus phosphide, an organic phosphorus, a thioether or the like.
  • a quantum dot such as an amino group, a thiol group, a hydroxyl group, a polyamino group, a polyfluorenyl group, a polyhydroxy group, a phosphorus, a phosphorus phosphide, an organic phosphorus, a thioether or the like.
  • the R1 group includes any one or more of the following groups: an aromatic group, an ethyl group, a butyl group, a cyclohexyl group, a methoxy group, a methylamino fatty chain, an propylene oxide group, a cyclohexyl group.
  • the R3 group includes any one or more of the following groups: an aromatic group, and an ethyl group, a butyl group, a cyclohexylmethoxy group, a methylamino group, an aliphatic chain propylene oxide group, a cyclohexyl alicyclic compound. .
  • the aromatic group includes any one or more of the following groups: phenyl, alkylphenyl, thienyl, pyrimidine, anilino, naphthalene, phenoxy.
  • the ligand-modified quantum dot composition is an ink
  • the viscosity of the quantum dot composition is 8-15 cP
  • the surface tension of the ligand-modified quantum dot composition is 20-40 mN/m.
  • Embodiments of the present disclosure provide a method of preparing a ligand-modified quantum dot composition. As described in Figure 6, the method includes the steps of:
  • the quantum dot is prepared by using a long molecular chain ligand (ie, the first ligand) as a complex, and the preparation method is simple and the process is mature. Since the complexing force of the existing long molecular chain ligand (for example, oleic acid) and the quantum dot is relatively weak, the first ligand is replaced by the second ligand in step S2. It can be understood that the combining force of the second ligand with the quantum dots is stronger than that of the first ligand.
  • a long molecular chain ligand for example, oleic acid
  • the first ligand modifying agent is oleic acid and the solvent is octadecene.
  • the following is a description of specific steps for preparing ligand-modified green CdSe/ZnS alloy quantum dots as an example:
  • Embodiments of the present disclosure provide a method for preparing a ligand-modified quantum dot layer, as described in FIG. 7, comprising the following steps.
  • the above-described ligand-modified quantum dot composition is formed on a substrate.
  • a substrate having a Hole Injection Layer (HIL) and a Hole Transport Layer (HTL).
  • HIL Hole Injection Layer
  • HTL Hole Transport Layer
  • the method further includes the step of heating to separate the chain scission from the ligand-modified quantum dot layer. That is to say, the temperature is further increased by heating, so that the group removed on the long molecular chain volatilizes with the solvent, leaving a closely packed quantum dot film to obtain a quantum dot light-emitting layer.
  • step (2) also includes the step of adding a radical scavenger.
  • the radical scavenger comprises any one or more of the following groups: alcohol, water, phenol, thiol. That is, the radical generated after the cleavage reacts with the radical scavenger to obtain a quantum dot having a short-chain ligand.
  • Embodiments of the present disclosure provide a quantum dot light emitting diode comprising a ligand-modified quantum dot composition prepared by the method of the above embodiments.
  • the specific raw materials of the ligand modifier can be selected as needed, and the specific amount of the ligand modifier can be adjusted according to actual conditions.
  • the ligand-modified quantum dot composition, the ligand-modified quantum dot layer, the preparation method thereof and the quantum dot light-emitting diode of the present disclosure are suitable for various quantum dot light-emitting diodes and display devices and a preparation method thereof.
  • the display device may be any product or component having a display function, such as an electronic paper, an OLED panel, a mobile phone, a tablet computer, a television, a display, a notebook computer, a digital photo frame, a navigator, and the like.
  • the segment B in the ligand modifying agent of the ligand-modified quantum dot composition of the present disclosure is a chain segment that can be broken, that is, the segment B is a longer molecular chain, so that the material has good solubility and stability, so
  • the ligand-modified quantum dot composition exists in the form of a solution or ink; however, the segment B itself is not very stable, and it can be broken under certain conditions.
  • the group in the segment B can be broken by heating or illumination, so that the ligand modifier becomes a short molecular chain ligand, thereby making the quantum dots densely packed and improving carrier transport performance.

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Abstract

本公开提供一种配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管。配体修饰量子点组合物中配体修饰剂的链段B为可断链的链段，即链段B是较长的分子链，使得材料具有良好的溶解度和稳定性，配体修饰量子点组合物以溶液或墨水等形式存在。链段B本身不是十分稳定，可在一定条件下断链。在具体应用中，可以通过加热或光照使链段B中的基团断裂，使得配体修饰剂变成短分子链配体，从而使得量子点堆积致密，提高载流子传输性能。 (图5)

Description

配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管
相关专利申请
本申请主张于2017年7月17日提交的中国专利申请No.201710580198.9的优先权，其全部内容通过引用结合于此。
技术领域
本公开涉及一种配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管。
背景技术
目前，OLED处于大规模产业化的发展阶段，有逐步替代LCD成为主流显示技术的趋势。但是OLED发光层为有机材料，具有易氧化，寿命短，发光光谱较宽，合成复杂等问题。近年来量子点材料逐渐兴起，其发光光谱较有机材料更窄，稳定性较有机材料更好，同时合成成本较有机材料更低，并且已经应用于电致发光器件中，因此QD-LED也成为了OLED技术的有力竞争者。
发明内容
本公开实施例提供一种配体修饰量子点组合物，包括量子点以及吸附于所述量子点表面的配体修饰剂，其中所述配体修饰剂的结构式为：链段A-链段B，所述配体修饰剂以链段A吸附于量子点表面，并且所述链段B为可断链的长分子链。。
在一实施例中，所述配体修饰量子点组合物为墨水，所述量子点组合物的粘度为8-15cP，并且所述配体修饰量子点组合物的表面张力为20-40mN/m。此处，cP为粘度单位厘泊，1厘泊(1cP)＝1毫帕斯卡·秒·(1mpa.s)。
在一实施例中，所述量子点包括III-V族量子点、IV族量子点、II-VI族量子点、核壳型量子点、合金量子点中的任意一种或几种。
在一实施例中，所述量子点包括CdS、CdSe、CdTe、ZnSe、InP、PbS、CuInS 2、ZnO、CsPbCl 3、CsPbBr 3、CsPhI 3、CdS/ZnS、CdSe/ZnS、 ZnSe、InP/ZnS、PbS/ZnS、InAs、InGaAs、InGaN、GaNk、ZnTe、Si、Ge、C中的任意一种或几种。
在一实施例中，所述链段A中包括以下基团中的任意一种或几种：氨基、巯基、羟基、多氨基、多巯基、多羟基、磷、氧磷、有机磷、硫醚。
在一实施例中，所述链段B包括依次逐一连接的R1基团、R2基团、R3基团，其中R1基团与链段A连接，并且所述R2基团可断裂。
在一实施例中，R2基团包括光降解或热降解的基团。
在一实施例中，在加热或光照下，R2基团与R1基团之间的化学键断开。
在一实施例中，在加热或光照下，R2基团与R1基团之间的化学键断开，并且R2基团与R3基团之间的化学键断开。
在一实施例中，在加热或光照下，R2基团自身中的化学键断开。
在一实施例中，R2包括以下基团中的任意一种或几种：偶氮基团(-N＝N-)、过氧基团(-O-O-)、过氧化二酰基团
Figure PCTCN2018079221-appb-000001
在一实施例中，所述R1基团包括以下基团中的任意一种或几种：芳香基团、乙基、丁基、环己基、甲氧基、甲胺基脂肪链；环氧丙烷基、环己基脂环族化合物。
在一实施例中，所述R3基团包括以下基团中的任意一种或几种：芳香基团，及乙基、丁基、环己基、甲氧基、甲胺基脂肪链；环氧丙烷基、环己基脂环族化合物。
在一实施例中，所述芳香基团包括以下基团中的任意一种或几种：苯基、烷基苯基、噻吩基、嘧啶基、苯胺基、萘、苯氧基。
本公开实施例还提供一种配体修饰量子点组合物的制备方法，包括步骤：
在溶剂中第一配体修饰剂存在的条件下合成第一配体修饰的量子点；
向上述第一配体修饰的量子点中加入第二配体修饰剂，其中所述第二配体修饰剂的结构式为：链段A-链段B，所述链段B为可断链的长分子链，所述第二配体修饰剂与第一配体置换，以使第二配体修饰 剂的链段A吸附于所述量子点表面得到第二配体修饰的量子点；以及
将第二配体修饰的量子点与所述第一配体分离。
在一实施例中，所述第一配体修饰剂包括油酸，并且所述溶剂包括十八烯。
本公开还提供一种配体修饰量子点层的制备方法，包括步骤：
在基板上形成上述的配体修饰量子点组合物；以及
加热或光照以使配体修饰剂链段B断链后形成配体修饰量子点层。
在一实施例中，形成配体修饰量子点层的步骤还包括加入自由基捕捉剂的步骤。
在一实施例中，所述自由基捕捉剂包括以下基团中的任意一种或几种：醇、水、酚、硫醇。
在一实施例中，在形成配体修饰量子点层的步骤之后，该方法还包括加热以使断链从所述配体修饰量子点层中分离出去的步骤。
附图说明
图1为本公开的一实施例的配体修饰量子点组合物的结构示意图；
图2、图3为本公开的另一实施例的配体修饰量子点组合物的结构示意图；
图4、图5为本公开的另一实施例的链段B反应过程示意图；
图6为本公开的又一实施例的配体修饰量子点组合物的制备方法流程图；
图7为本公开的再一实施例的配体修饰量子点层的制备方法流程图；以及
图8为本公开的又一实施例的含偶氮(-N＝N-)的第二配体分解示意图。
具体实施方式
为使本领域技术人员更好地理解本公开的技术方案，下面结合附图和具体实施方式对本公开作进一步详细描述。
附图中出现的附图标记为：1、量子点；2、配体修饰剂。
发明人发现现有QD-LED中至少存在如下问题。量子点材料为无机纳米粒子，需要外层修饰有机配体来提高稳定性及溶解度。通常具 有短链配体的量子点材料形成发光层薄膜时排列更紧密，且载流子传输率更高。但是短链的配体可能会降低溶解度，同时短链配体使量子点材料相互作用力更强，更容易聚沉，无法保存。因此目前主流的量子点材料配体仍为油酸油胺等长链配体。但长链配体修饰的量子点成膜时量子点不够致密，载流子传输效率较低。
本公开针对现有的短链配体使量子点材料难保存，长链配体修饰的量子点载流子传输效率低的问题，发明人提出了一种配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管。
本公开实施例提供一种配体修饰量子点组合物，如图1所示，其包括量子点1以及吸附于所述量子点表面的配体修饰剂2。该配体修饰剂2含有长分子链的基团，并且该长分子链中的至少部分基团在一定的条件下可以发生断链。具体的，所述配体修饰剂2的结构式为：链段A-链段B。链段A用于吸附于量子点表面，并且链段B为可断链的长分子链。
本公开实施例的量子点组合物的配体修饰剂中的链段B为可断链的链段，即链段B是较长的分子链，使得组合物具有良好的溶解度和稳定性，因此配体修饰量子点组合物以溶液或墨水等形式存在。然而链段B本身不是十分稳定，其可在一定条件下断链。在具体应用中，可以通过加热或光照的方式使链段B中的基团断裂，使得配体修饰剂变成短分子链配体，从而使得量子点堆积致密，提高载流子传输性能。
在示例性实施例中，量子点与配体修饰剂的质量比为大约5％-300％。如图2、图3所示，所述配体修饰剂的结构式为：链段A-链段B，链段A用于吸附于量子点表面，并且链段B为可断链的长分子链。具体的，所述链段B包括依次逐一连接的R1基团、R2基团、R3基团。R1基团与链段A连接，所述R2基团可断裂。
具体的，R2基团断裂可以有两种方式。第一种参见图2，R1基团与R2基团之间的化学键断开。这种情况下，通常R2基团与R3基团之间的化学键也同时断开。第二种参见图3，是R2自身中的化学键断开。例如，R2断裂为R2a、R2b、R2c，其中R2a与R1连接，R2c与R3连接，R2b以气体形式释放。
例如，R2包括光降解或热降解的基团。具体的，包括以下基团中的任意一种或几种：偶氮基团(-N＝N-)、过氧基团(-O-O-)、 过氧化二酰
Figure PCTCN2018079221-appb-000002
具体的，当R2基团以第一种形式断裂时，参见图4，由上至下分别为基团(-N＝N-)、过氧基团(-O-O-)。
当R2基团以第二种形式断裂时，参见图5，由上至下分别为偶氮基团(-N＝N-)、过氧基团(-O-O-)、过氧化二酰
Figure PCTCN2018079221-appb-000003
也就是说，R1基团与R2基团的划分方式可以根据不同长分子链进行选择，并且其具体物质可以根据需要进行改变。本公开实施例中给出了以上三种具体形式。可以理解的是，含有其它可断链的基团也是可行的。
作为一种可选实施方案，所述量子点包括III-V族量子点、IV族量子点、II-VI族量子点、核壳型量子点、合金量子点中的任意一种或几种。具体的，可以是CdS、CdSe、CdTe、ZnSe、InP、PbS、CuInS 2、ZnO、CsPbCl 3、CsPbBr 3、CsPhI 3、CdS/ZnS、CdSe/ZnS、ZnSe、InP/ZnS、PbS/ZnS、InAs、InGaAs、InGaN、GaNk、ZnTe、Si、Ge、C中的任意一种或几种。
也就是说，目前已有的量子点均可用于本公开实施例中作为发光材料，其可以是单一的一种量子点，也可以是两种或多种量子点复合的。量子点的具体选择可以根据所需的发光颜色等进行选择，在此不再一一例举。
例如，所述链段A包括以下基团中的任意一种或几种：氨基、巯基、羟基、多氨基、多巯基、多羟基、磷、氧磷、有机磷、硫醚。
也就是说，链段A中含有易于与量子点配合的基团，例如氨基、巯基、羟基、多氨基、多巯基、多羟基、磷、氧磷、有机磷、硫醚等。
例如，所述R1基团包括以下基团中的任意一种或几种：芳香基团、乙基、丁基、环己基、甲氧基、甲胺基脂肪链、环氧丙烷基、环己基脂环族化合物。R3基团包括以下基团中的任意一种或几种：芳香基团，及乙基、丁基、环己基甲氧基、甲胺基、脂肪链环氧丙烷基、环己基脂环族化合物。
又例如，所述芳香基团包括以下基团中的任意一种或几种：苯基、烷基苯基、噻吩基、嘧啶、苯胺基、萘、苯氧基基。
例如，所述配体修饰量子点组合物为墨水，所述量子点组合物的粘度为8-15cP，并且所述配体修饰量子点组合物的表面张力为20-40mN/m。
本公开实施例提供一种配体修饰量子点组合物的制备方法。如图6所述，该方法包括步骤：
S1、在溶剂中第一配体修饰剂存在的条件下合成第一配体修饰的量子点；
S2、向上述第一配体修饰的量子点中加入第二配体修饰剂，所述第二配体修饰剂与第一配体置换，以使第二配体修饰剂的基团A吸附于所述量子点表面得到第二配体修饰的量子点；其中所述第二配体修饰剂的结构式为：A-B，所述基团B为可断链的长分子链；以及
S3、将第二配体修饰的量子点与所述第一配体分离。
需要说明的是，在此采用长分子链配体(即第一配体)作为配合物制备量子点，这样的制备方法较简单，工艺较成熟。由于现有的长分子链配体(例如油酸)与量子点的配合力相对较弱，因此在步骤S2中采用第二配体将第一配体置换出来。可以理解的是，第二配体与量子点的配合力相对于第一配体要强。
作为示例，所述第一配体修饰剂为油酸，所述溶剂为十八烯。以下以制备配体修饰的绿色CdSe/ZnS合金量子点为例进行具体步骤的说明：
S01、将0.6mmol CdO、12mmol ZnO和10mL OA(油酸，即油酸作为第一配体)置于烧瓶中。加热至150℃时用注射器注入45mL溶剂十八烯。氮气保护下加热至310℃，得到澄清的Cd(OA) 2和Zn(OA) 2溶液，并且将温度保持在300℃。将0.6mmol Se和12mmol S溶于12mL TOP(三辛基膦)后注入上述体系。反应10min后，得到CdSe/ZnS合金量子点溶液。
S02、室温下，取12mL上述的CdSe/ZnS合金量子点溶液的粗产品，加入5-20mmol含偶氮(-N＝N-)的第二配体
Figure PCTCN2018079221-appb-000004
然后搅拌12小时，以使第二配体与第一配体置换。
S03、将置换(或称交换)配体后的溶液在12000rpm转速下离心10min，除去不溶物。得到的清液再加入己烷/乙醇(v/v＝1/4)沉淀，离心，重复三次后，得到纯化的含有偶氮(-N＝N-)的第二配体修饰的量子点组合物，溶于12mL氯仿中，得到粘度为8-15cP，表面张力20-40mN/m的量子点墨水。本实施例中第二配体修饰量子点组合物的基团断裂参见图8。
本公开实施例提供一种配体修饰量子点层的制备方法，如图7所述，包括下述步骤。
(1)在基板上形成上述的配体修饰量子点组合物。例如，在具有空穴注入层(Hole Injection Layer，HIL)、空穴传输层(Hole Transport Layer，HTL)的基板上打印结合图6描述的实施例制备的含有偶氮(-N＝N-)第二配体的量子点墨水。
(2)加热至50-200℃或光照(照度为波长为200-400nm，曝光量为50-250mJ/cm 2，照射时间为2-60秒)以使偶氮(-N＝N-)第二配体的量子点墨水中偶氮(-N＝N-)断链，形成厚度为5-30nm的配体修饰量子点层。
具体的，加热过程中可以同时抽真空以促使在偶氮(-N＝N-)配体断裂过程中放出的少量氮气被抽走。
例如，在步骤(2)之后，该方法还包括加热以使断链从所述配体修饰量子点层中分离出去的步骤。也就是说，进一步升高温度加热，使得长分子链上脱去的基团随溶剂一起挥发，留下紧密排列的量子点薄膜，得到量子点发光层。
例如，步骤(2)还包括加入自由基捕捉剂的步骤。作为示例，所述自由基捕捉剂包括以下基团中的任意一种或几种：醇、水、酚、硫醇。也就是说，断裂后生成的自由基与自由基捕获剂反应，得到具有短链配体的量子点。
本公开实施例提供一种量子点发光二极管，包括由上述实施例的方法制备的配体修饰量子点组合物。
显然，上述各实施例的具体实施方式还可进行许多变化。例如：配体修饰剂的具体原料可以根据需要进行选择，配体修饰剂的具体用量可以根据实际情况进行调整。
本公开的配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管适用于各种量子点发光二极管和显示装置及其制备方法。所述显示装置可以为：电子纸、OLED面板、手机、平板电脑、电视机、显示器、笔记本电脑、数码相框、导航仪等任何具有显示功能的产品或部件。
本公开的配体修饰量子点组合物中配体修饰剂中的链段B为可断链的链段，即链段B是较长的分子链，使得材料具有良好的溶解度和稳定性，因此配体修饰量子点组合物以溶液或墨水等形式存在；然而链段B本身不是十分稳定，其可在一定条件下断链。在具体应用中，可以通过加热或光照的方式使链段B中的基团断裂，使得配体修饰剂变成短分子链配体，从而使得量子点堆积致密，提高载流子传输性能。
可以理解的是，以上实施方式仅仅是为了说明本公开的原理而采用的示例性实施方式，然而本公开并不局限于此。对于本领域内的普通技术人员而言，在不脱离本公开的精神和实质的情况下，可以做出各种变型和改进，这些变型和改进也视为本公开的保护范围。

Claims (22)

  1. 一种配体修饰量子点组合物，包括量子点以及吸附于所述量子点表面的配体修饰剂，其中所述配体修饰剂的结构式为：链段A-链段B，所述配体修饰剂以链段A吸附于量子点表面，并且所述链段B为可断链的长分子链。
  2. 根据权利要求1所述的配体修饰量子点组合物，其中所述配体修饰量子点组合物为墨水，所述量子点组合物的粘度为8-15cP，并且所述配体修饰量子点组合物的表面张力为20-40mN/m。
  3. 根据权利要求1所述的配体修饰量子点组合物，其中所述量子点包括III-V族量子点、IV族量子点、II-VI族量子点、核壳型量子点、合金量子点中的任意一种或几种。
  4. 根据权利要求3所述的配体修饰量子点组合物，其中所述量子点包括CdS、CdSe、CdTe、ZnSe、InP、PbS、CuInS 2、ZnO、CsPbCl 3、CsPbBr 3、CsPhI 3、CdS/ZnS、CdSe/ZnS、ZnSe、InP/ZnS、PbS/ZnS、InAs、InGaAs、InGaN、GaNk、ZnTe、Si、Ge、C中的任意一种或几种。
  5. 根据权利要求1所述的配体修饰量子点组合物，其中所述链段A中包括以下基团中的任意一种或几种：氨基、巯基、羟基、多氨基、多巯基、多羟基、磷、氧磷、有机磷、硫醚。
  6. 根据权利要求1所述的配体修饰量子点组合物，其中所述链段B包括依次逐一连接的R1基团、R2基团、R3基团，其中R1基团与链段A连接，并且所述R2基团可断裂。
  7. 根据权利要求6所述的配体修饰量子点组合物，其中所述R2基团包括光降解或热降解的基团。
  8. 根据权利要求7所述的配体修饰量子点组合物，其中在加热或光照下，所述R2基团与所述R1基团之间的化学键断开。
  9. 根据权利要求8所述的配体修饰量子点组合物，其中在加热或光照下，所述R2基团与所述R3基团之间的化学键断开。
  10. 根据权利要求7所述的配体修饰量子点组合物，其中在加热或光照下，所述R2基团自身中的化学键断开。
  11. 根据权利要求6-10中任一项所述的配体修饰量子点组合物，其中所述R2基团包括以下基团中的任意一种或几种：偶氮基团、过氧 基团、过氧化二酰基团。
  12. 根据权利要求6所述的配体修饰量子点组合物，其中所述R1基团包括以下基团中的任意一种或几种：芳香基团、乙基、丁基、环己基、甲氧基、甲胺基脂肪链、环氧丙烷基、环己基脂环族化合物。
  13. 根据权利要求6所述的配体修饰量子点组合物，其中所述R3基团包括以下基团中的任意一种或几种：芳香基团，及乙基、丁基、环己基、甲氧基、甲胺基脂肪链、环氧丙烷基、环己基脂环族化合物。
  14. 根据权利要求12或13所述的配体修饰量子点组合物，其中所述芳香基团包括以下基团中的任意一种或几种：苯基、烷基苯基、噻吩基、嘧啶基、苯胺基、萘、苯氧基。
  15. 一种配体修饰量子点组合物的制备方法，包括步骤：
    在溶剂中第一配体修饰剂存在的条件下合成第一配体修饰的量子点；
    向上述第一配体修饰的量子点中加入第二配体修饰剂，其中所述第二配体修饰剂的结构式为：链段A-链段B，所述链段B为可断链的长分子链，所述第二配体修饰剂与第一配体置换，以使第二配体修饰剂的链段A吸附于所述量子点表面得到第二配体修饰的量子点；以及
    将第二配体修饰的量子点与所述第一配体分离。
  16. 根据权利要求15所述的配体修饰量子点组合物的制备方法，其中所述第一配体修饰剂包括油酸，并且所述溶剂包括十八烯。
  17. 一种配体修饰量子点层的制备方法，包括步骤：
    在基板上形成权利要求1-14中任一项所述的配体修饰量子点组合物；以及
    加热或光照以使配体修饰剂链段B断链后形成配体修饰量子点层。
  18. 根据权利要求17所述的配体修饰量子点层的制备方法，其中形成配体修饰量子点层的步骤还包括加入自由基捕捉剂的步骤。
  19. 根据权利要求18所述的配体修饰量子点层的制备方法，其中所述自由基捕捉剂包括以下基团中的任意一种或几种：醇、水、酚、硫醇。
  20. 根据权利要求17所述的配体修饰量子点层的制备方法，还包括：在形成配体修饰量子点层的步骤之后，加热以使断链从所述配体修饰量子点层中分离出去的步骤。
  21. 一种配体修饰量子点层，包括根据权利要求1-14中任一项所述的配体修饰量子点组合物。
  22. 一种量子点发光二极管，包括根据权利要求1-14中任一项所述的配体修饰量子点组合物。
PCT/CN2018/079221 2017-07-17 2018-03-16 配体修饰量子点组合物、配体修饰量子点层及其制备方法、量子点发光二极管 WO2019015345A1 (zh)

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EP18807546.9A EP3656832B1 (en) 2017-07-17 2018-03-16 Ligand-modified quantum dot composition, ligand-modified quantum dot layer, preparation method therefor, and quantum dot light-emitting diode

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