CN110746973A - Particle, preparation method thereof and quantum dot light-emitting diode - Google Patents
Particle, preparation method thereof and quantum dot light-emitting diode Download PDFInfo
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- CN110746973A CN110746973A CN201810818952.2A CN201810818952A CN110746973A CN 110746973 A CN110746973 A CN 110746973A CN 201810818952 A CN201810818952 A CN 201810818952A CN 110746973 A CN110746973 A CN 110746973A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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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- 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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- H—ELECTRICITY
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- 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
Abstract
The invention discloses a particle, a preparation method thereof and a quantum dot light-emitting diode. On the one hand, the solubility of the particles in aqueous solvents is improved by two ligand exchanges; when the prepared quantum dot surface simultaneously contains the long-chain mercapto alcohol ligand and the dihydric thiol ligand is used as a quantum dot light-emitting diode material, the charge transfer performance between the quantum dot and the quantum dot is improved, so that the performance of the quantum dot light-emitting diode is further improved.
Description
Technical Field
The invention relates to the technical field of quantum dots, in particular to particles, a preparation method thereof and a quantum dot light-emitting diode.
Background
Quantum dot light emitting diodes are the main window of the next generation of novel display technology, and quantum dot diode devices aimed at by different quantum dot materials are also different.
The luminescent quantum dots are various in types such as cadmium-containing and cadmium-free quantum dots, and oil-soluble and water-soluble quantum dots exist in the cadmium-containing and cadmium-free quantum dots; there are different device structure designs for these different classes of materials, all aimed at improving the efficiency and stability of the device. For water-soluble quantum dots, there are many devices designed based on water-soluble quantum dots, but the device structure mainly focuses on inversion, and there is also the problem of unbalanced charge injection for inversion, and the solution to these problems is mainly improved from two aspects: firstly, the structure of the quantum dot is improved and designed to meet the energy level of a device to prepare a proper quantum dot material, and secondly, the interface engineering between the surfaces of the quantum dots or layers of the device is improved to balance the mobility of electron holes and the like. The following disadvantages exist for water-soluble quantum dots: 1. the surface defects are more, and the surface capture state is easy to generate; 2. the stability is poor, and the surface ligand of the general water-soluble quantum dot is short, so that the stability is poor for the dissolved oxygen in the solution environment or the oxygen in the environment; 3. the water-soluble quantum dots are easy to cause agglomeration due to large surface potential, so that a device prepared by using the common aqueous phase luminescent quantum dots has poor effect.
Accordingly, the prior art remains to be improved and developed.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide particles, a preparation method thereof and a quantum dot light-emitting diode, and aims to solve the problem that the device prepared by using the water-phase quantum dots is poor in effect due to the fact that the existing water-soluble quantum dots have surface defects, poor stability and easy agglomeration.
The technical scheme of the invention is as follows:
a method of preparing a particle, comprising the steps of:
providing a primary particle comprising a quantum dot, an oil-soluble ligand bound to the surface of the quantum dot;
performing first ligand exchange with the initial particles by using a first ligand to obtain intermediate particles;
performing a second ligand exchange with the intermediate particle using a second ligand to obtain the particle;
wherein the firstThe chemical structural formula of the ligand is HS- (CH)2）n-OH, wherein n is an integer from 18 to 30;
the second ligand is a dihydric thiophenol ligand.
A particle, wherein the particle comprises a quantum dot, a first ligand and a second ligand bound to the surface of the quantum dot;
wherein the chemical structural formula of the first ligand is as follows: HS- (CH)2）n-OH, n being an integer from 18 to 30;
the second ligand is a dihydric thiophenol ligand.
A quantum dot light-emitting diode comprises a quantum dot light-emitting layer, wherein the quantum dot light-emitting layer is made of the particles.
Has the advantages that: according to the preparation method of the particles, the solubility of the particles in an aqueous solvent is improved on the one hand through two times of ligand exchange; when the prepared quantum dot surface simultaneously contains the long-chain mercapto alcohol ligand and the dihydric thiol ligand is used as a quantum dot light-emitting diode material, the charge transfer performance between the quantum dot and the quantum dot is improved, so that the performance of the quantum dot light-emitting diode is further improved.
Drawings
FIG. 1 shows the structural formula of 1, 4-dimercaptothiol.
FIG. 2 shows the structural formula of 4, 4-bis-dimercaptothiol.
FIG. 3 shows the structural formula of 4, 4-trimercaptothiol.
FIG. 4 is a schematic flow chart of preparing CdSe/CdS quantum dots in the embodiment of the present invention.
Detailed Description
The invention provides particles, a preparation method thereof and a quantum dot light-emitting diode, and the invention is further described in detail below in order to make the purpose, technical scheme and effect of the invention clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides a preparation method of particles, which comprises the following steps:
s100, providing initial particles, wherein the initial particles comprise quantum dots and oil-soluble ligands bound to the surfaces of the quantum dots;
s200, performing first ligand exchange on the initial particles by adopting a first ligand to obtain intermediate particles;
s300, performing secondary ligand exchange on the intermediate particles by adopting a second ligand to obtain the particles;
wherein the chemical structural formula of the first ligand is HS- (CH)2）n-OH, n being an integer from 18 to 30;
the second ligand is a short-chain mercapto ligand.
According to the preparation method of the particles provided by the embodiment of the invention, on one hand, the solubility of the particles in an aqueous solvent is improved through two times of ligand exchange; when the prepared quantum dot surface simultaneously contains the long-chain mercapto alcohol ligand and the dihydric thiol ligand is used as a quantum dot light-emitting diode material, the charge transfer performance between the quantum dot and the quantum dot is improved, so that the performance of the quantum dot light-emitting diode is further improved.
In particular, mercaptoalcohols as ligands HS- (CH)2）n-OH, wherein the value of n is an integer of 18-30, the steric hindrance effect of the long-chain mercapto alcohol is greater than that of the short-chain aqueous phase ligand, so that the monodispersity of the particles can be improved, and further, the binary thiophenol ligand is used for ligand exchange of the particles so as to improve the charge transfer performance between the particles in the light emitting layer.
In the present invention, the quantum dots are selected from binary phase quantum dots, ternary phase quantum dots, quaternary phase quantum dots, and the like, and are not limited to one or more of these. By way of example, the binary phase quantum dots are selected from CdS, CdSe, CdTe, ZnSe, ZnTe, or ZnTe, and the like, without being limited thereto; the ternary phase quantum dots are selected from ZnCdS, CuInS, ZnCdSe, ZnSeS or ZnCdTe and the like, but are not limited thereto; the quaternary phase quantum dots are selected from ZnCdSSe, CuInZnS, ZnCdSeS, CuInSeS or ZnCdTeS, etc., but are not limited thereto.
Because the sulfhydryl group has stronger binding capacity with the surface of the quantum dot, the ligand containing sulfhydryl group is more easily exchanged with other ligands on the surface of the quantum dot. Therefore, the kind of the oil-soluble ligand of the present invention is not limited, and may be an oil-soluble ligand having no mercapto substituent, for example, the oil-soluble ligand may be one or more selected from organic acids, organic phosphines, organic amines, organic phosphonic acids, organic phosphine oxides, and the like. Preferably, the oil-soluble ligand is selected from one or more of organic acids, organic phosphines and organic amines.
The initial particles according to the embodiments of the present invention can be prepared by a conventional oil phase method, which is prior art and will not be described herein.
In step S200, the first ligand is a long-chain mercapto alcohol ligand, and the chemical structural formula of the long-chain mercapto alcohol ligand is HS- (CH)2）n-OH, wherein n is an integer from 18 to 30. The specific long-chain mercapto alcohol ligand has good water solubility, and can change the dissolved state of quantum dots from an oil phase to a water phase. The first ligand of the present invention is in a liquid state. The first ligand may be dispersed in a polar solvent, which may be selected from ethanol, methanol, water, or the like, without being limited thereto.
In one embodiment, step S200 specifically includes: mixing a proper amount of first ligand with a certain amount of initial particle solution under an inert gas environment, stirring at 25-80 ℃ for 30-60min, and adding a precipitant and a polar solvent for high-speed centrifugal separation to obtain intermediate particles. The solvent in the primary particle solution may be selected from non-polar solvents such as toluene, n-hexane, chlorobenzene, chloroform, or the like, but is not limited thereto. Preferably, the inert gas is nitrogen or argon, etc. Preferably, the precipitant is selected from one or more of ethyl acetate, ethyl formate, methyl acetate, propyl acetate, and the like, without being limited thereto. Preferably, the polar solvent is selected from one or more of ethanol, methanol, water, and the like, without being limited thereto.
In a preferred embodiment, the first ligand is mixed with the primary particles in a molar to mass ratio of the first ligand to the primary particles of (1-10 mmol): 100 mg.
The purpose of ligand exchange of the initial particles by the first ligand is that the first ligand is a long-chain mercapto alcohol ligand which has good water solubility, can change the dissolution state of the quantum dots from an oil phase to a water phase, and can partially exchange oil-soluble ligands on the surfaces of the quantum dots by controlling the dosage of the first ligand.
In one embodiment, in step S300, the second ligand of the present invention is a dihydric thiol ligand. The binary in the binary thiophenol ligand means that two sulfydryl groups are substituted on a benzene ring, and the benzene ring can be in a structure of one benzene ring or a biphenyl structure. Preferably, the second ligand is selected from one or more of 1, 4-benzenedithiol (BDT, see fig. 1), 4-dimercaptobiphenyl (DBDT, see fig. 2), 4-dimercaptop-terphenyl (TBDT, see fig. 3), and the like, without being limited thereto.
In one embodiment, step S300 specifically includes: and (2) mixing a proper amount of second ligand with the intermediate particles in an inert gas environment, stirring at 25-80 ℃ for 30-60min, and adding a precipitant and a polar solvent for high-speed centrifugal separation to obtain the particles. Preferably, the inert gas is nitrogen or argon, etc. Preferably, the precipitant is selected from one or more of ethyl acetate, ethyl formate, methyl acetate, propyl acetate, and the like, without being limited thereto. Preferably, the polar solvent is selected from one or more of ethanol, methanol, water, and the like, without being limited thereto. The second ligand of the invention has a short carbon chain and is a modifier with good conductivity and hydrophilicity, and the second ligand can further exchange the oil-soluble ligand on the surface of the intermediate particle. The specific long-chain mercapto-alcohol ligand and the specific short-chain mercapto-alcohol ligand are combined on the surface of the quantum dot, and are matched with each other, so that the electron transport performance of the quantum dot is further improved.
In a preferred embodiment, the second ligand is mixed with the intermediate particles in a molar to mass ratio of the second ligand to the intermediate particles of (1-10 mmol): 100 mg. The oil-soluble ligand remaining after the first ligand exchange can be replaced completely or partially by adjusting the amount of the second ligand.
The invention also provides a particle, wherein the particle comprises a quantum dot, a first ligand and a second ligand which are combined on the surface of the quantum dot;
wherein the first ligand has the chemical structural formula: HS- (CH)2）n-OH, wherein n is an integer from 18 to 30;
the second ligand is a dihydric thiophenol ligand.
The invention also provides a quantum dot light-emitting diode which comprises a quantum dot light-emitting layer, wherein the material of the quantum dot light-emitting layer is the particle. The quantum dot light emitting diode is the prior art, and the specific structure thereof is not described herein again.
The present invention will be described in detail below with reference to examples.
Referring to FIG. 4, the preparation of CdSe/CdS quantum dots and quantum dot light-emitting diodes by using CdSe/ZnS quantum dots, 1-mercapto-1-octadecanol and 1, 4-dimercaptothiol (BDT) as examples will be described in detail.
1. Preparation of red oil soluble CdSe/ZnS quantum dots:
1) cadmium oleate Cd (OA)2With zinc oleate Zn (OA)2Preparing a precursor:
0.8mmol of cadmium oxide (CdO) and 6mmol of zinc acetate (Zn (Ac) were taken2Adding 8mL of Oleic Acid (OA) and 15mL of Octadecene (ODE) into a three-neck flask, exhausting gas for 10min at normal temperature, heating to 170 ℃, exhausting gas for 60min, and maintaining at 170 ℃;
2) preparation of selenium (Se) precursor:
weighing 4mmol Se, adding into 4mL Trioctyloxyphosphine (TOP), heating to 170 deg.C for 30min, and cooling to 140 deg.C;
3) preparation of sulfur (S) precursor:
weighing 4mmol S, adding into 6mL Trioctyloxyphosphine (TOP), heating to 170 deg.C for 30min, and cooling to 140 deg.C;
4) and (2) after the temperature of the mixed solution in the step 1) is increased to 300 ℃, quickly injecting 2mL of selenium (Se) precursor into the flask for reaction for 10min, then injecting 2mL of sulfur (S) precursor into the reaction mixed solution for reaction for 30min, finally obtaining red CdSe/ZnS quantum dots, cooling the mixed solution to room temperature, centrifugally separating and cleaning to obtain the red oil-soluble CdSe/ZnS quantum dots, and drying the red oil-soluble CdSe/ZnS quantum dots, wherein the ligand on the surface of the red oil-soluble CdSe/ZnS quantum dots is Oleic Acid (OA).
2. And (2) carrying out ligand exchange on the red oil-soluble CdSe/ZnS quantum dots by using 1-mercapto-1-octadecanol:
1) dispersing 100mg of the prepared red oil soluble CdSe/ZnS quantum dots in 10mL of toluene solution, introducing argon to uniformly disperse the red oil soluble CdSe/ZnS quantum dots, dispersing 2mmol of 1-mercapto-1-octadecanol in 5mL of ethanol solution, adding the mixture into the CdSe/ZnS quantum dot solution, stirring at room temperature for 40min until all the CdSe/ZnS quantum dots are completely dispersed in the ethanol solution, and stopping stirring;
2) and adding 20mL of ethyl acetate precipitator into the mixed solution to centrifugally separate the CdSe/ZnS quantum dots, and drying to obtain the CdSe/ZnS quantum dots with the surfaces containing 1-mercapto-1-octadecanol.
3. The method for modifying the CdSe/ZnS quantum dot with the surface containing 1-mercapto-1-octadecanol by using 1, 4-dimercaptothiol (BDT) comprises the following steps:
1) dispersing 50mg of the CdSe/ZnS quantum dots with the surfaces containing 1-mercapto-1-octadecanol in 5mL of ethanol solution, uniformly stirring in an argon atmosphere to fully disperse the CdSe/ZnS quantum dots, and then adding 1mmol of 1, 4-dimercaptothiol (BDT) into the CdSe/ZnS quantum dots with the surfaces containing 1-mercapto-1-octadecanol and stirring at room temperature for 30 min;
2) adding 20mL of ethyl acetate precipitant into the mixed solution to centrifugally separate and dry the CdSe/ZnS quantum dots to obtain the CdSe/ZnS quantum dots with the surfaces containing 1-mercapto-1-octadecanol and 1, 4-dimercaptothiol (BDT), and preparing into 30mg/mL ethanol solution.
4. Quantum dot light-emitting diode prepared from materials
The preparation process of the inversion quantum dot light-emitting diode comprises the following steps: providing an anode (ITO); and sequentially preparing an electron transport layer, a light-emitting layer, a hole transport layer and a cathode on the anode, wherein the light-emitting layer is made of the CdSe/ZnS quantum dot which is prepared by the method and contains 1-mercapto-1-octadecanol and 1, 4-dimercaptothiol (BDT) on the surface.
In summary, the preparation method of the particles provided by the embodiments of the present invention improves the solubility of the particles in the aqueous solvent through two ligand exchanges; when the prepared quantum dot surface simultaneously contains the long-chain mercapto alcohol ligand and the dihydric thiol ligand is used as a quantum dot light-emitting diode material, the charge transfer performance between the quantum dot and the quantum dot is improved, so that the performance of the quantum dot light-emitting diode is further improved.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (10)
1. A method of making a particle, comprising the steps of:
providing a primary particle comprising a quantum dot, an oil-soluble ligand bound to the surface of the quantum dot;
performing first ligand exchange with the initial particles by using a first ligand to obtain intermediate particles;
performing a second ligand exchange with the intermediate particle using a second ligand to obtain the particle;
wherein the chemical structural formula of the first ligand is HS- (CH)2）n-OH, n being an integer from 18 to 30;
the second ligand is a dihydric thiophenol ligand.
2. The method of making a particle of claim 1 wherein said oil soluble ligand is selected from one or more of the group consisting of organic acids, organic phosphines, organic amines, organic phosphonic acids, and organic phosphine oxides.
3. The method for producing particles according to claim 1, wherein in the step of performing the first ligand exchange with the primary particles using the first ligand, the first ligand is mixed with the primary particles in such a manner that the molar ratio of the first ligand to the primary particles is (1-10 mmol): 100 mg.
4. The method for preparing particles according to claim 1, wherein in the step of performing the first ligand exchange with the primary particles using the first ligands, the temperature of the first ligand exchange is 25 to 80 ℃, and/or the time of the first ligand exchange is 10 to 120 min.
5. A method of producing a particle as claimed in claim 1 wherein the second ligand is selected from one or more of 1, 4-benzenedithiol, 4-dimercaptobiphenyl and 4, 4-dimercaptop-terphenyl.
6. The method for producing particles according to claim 1, wherein in the step of performing the second ligand exchange with the intermediate particles using the second ligand, the second ligand is mixed with the intermediate particles in such a manner that the molar ratio of the second ligand to the intermediate particles is (1-10 mmol): 100 mg.
7. The method for preparing particles according to claim 1, wherein in the step of performing the second ligand exchange with the intermediate particles using the second ligand, the temperature of the second ligand exchange is 25 to 80 ℃, and/or the time of the second ligand exchange is 10 to 120 min.
8. A particle comprising a quantum dot, a first ligand and a second ligand bound to the surface of the quantum dot;
wherein the chemical structural formula of the first ligand is as follows: HS- (CH)2）n-OH, n being an integer from 18 to 30;
the second ligand is a dihydric thiophenol ligand.
9. The particle of claim 8, wherein the second ligand is selected from one or more of 1, 4-dimercaptothiol, 4-bisdimercaptothiol, and 4, 4-trisdimercaptothiol.
10. A quantum dot light emitting diode comprising a quantum dot light emitting layer, wherein the material of the quantum dot light emitting layer is the particle of claim 8 or 9.
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| CN114686206A (en) * | 2020-12-30 | 2022-07-01 | Tcl科技集团股份有限公司 | Composite material and preparation method thereof |
| CN115700270A (en) * | 2021-07-27 | 2023-02-07 | 北京京东方技术开发有限公司 | Quantum dot film and preparation method thereof, photoelectric device, display device and preparation method of quantum dot light-emitting device |
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