CN108977191A - A kind of quantum dot surface ligand exchange processes - Google Patents
A kind of quantum dot surface ligand exchange processes Download PDFInfo
- Publication number
- CN108977191A CN108977191A CN201710399235.6A CN201710399235A CN108977191A CN 108977191 A CN108977191 A CN 108977191A CN 201710399235 A CN201710399235 A CN 201710399235A CN 108977191 A CN108977191 A CN 108977191A
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- Prior art keywords
- ligand
- quantum dot
- proton
- acid
- deprotonation
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- 238000010537 deprotonation reaction Methods 0.000 claims abstract description 56
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- 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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- 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
- C09K11/54—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing zinc or cadmium
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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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- Chemical & Material Sciences (AREA)
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Abstract
A kind of method that the present invention discloses quantum dot surface ligand exchange, wherein comprising steps of pre-processing using proton-removed agent to ligand containing proton, obtain deprotonation ligand；Pre-configured first wife's body quantum dot solution is mixed with the deprotonation ligand, after stirring the predetermined time at room temperature, ligand exchange reaction occurs, the quantum dot that surface is the deprotonation ligand is obtained after cleaning；Quantum dot ligand exchange processes reaction rate provided by the invention is fast, easy to operate, and the cation of deprotonation ligand and quantum dot surface after exchange is firmly combined, and the quantum dot colloidal solution stability after exchange is strong, dissolubility is good, luminous efficiency is high.
Description
Technical field
The present invention relates to technology of quantum dots field more particularly to a kind of quantum dot surface ligand exchange processes.
Background technique
Fluorescence semiconductor is nanocrystalline, also known as quantum dot, and compared with conventional fluorescent dye molecule, quantum dot has many uniquenesses
Luminescent properties, such as: resistance to photobleaching, broadband excitation, the features such as transmitting band gap is adjustable, therefore be widely used in photoelectric device
And the fields such as biomedicine.
Preparing the most common method of quantum dot at present is that heat injection is negative at high temperature using metal-organic cation predecessor
The reaction of ion predecessor generates quantum dot, and the organic matter introduced in zwitterion predecessor includes tri octyl phosphine, tributylphosphine, oil
Acid, stearic acid, oleyl amine etc., the introducing of these organic matters are adjustable the crystal growth rate, crystal morphology, crystalline size of quantum dot
Distribution.In addition, these organic matters can reduce surface defect as the surface end-capping reagent of quantum dot to improve quantum dot light emitting effect
Rate.But surface ligand be above-mentioned organic matter quantum dot there are the following problems:
First is that electronic structure is suitable and how the ligand of binding ability difference is combined by force with quantum dot: the functional group of ligand, chain length
Etc. factors determine the electronic structure of itself, to influence the surface electronic hole wave functions and quantum dot film layer of quantum dot
Electronic transmission performance.Such as, when amino ligands are in conjunction with CdSe quantum dot surface, the shell structurre of quantum dot can be directly served as
The luminous efficiency of quantum dot is improved, does not need the inorganic shell structurre of regrowth.In addition CdSe quantum dot surface ligand is 3- mercapto
When base propionic acid, surface electronic wave function is mobile to quantum dot surface, and surface electronic wave function is inside when surface ligand is alanine
Core is mobile, and and TiO2The electron-transport efficiency ratio of interface is free of 3 ~ 4 times high when alanine ligand.However, part electronics knot
The suitable ligand of structure and quantum dot binding ability are weak, are not easy to replace original ligand in conjunction with quantum dot, therefore how to make this kind
Ligand is effectively in conjunction with quantum dot, however it remains biggish challenge.
Second is that the stability of colloidal solution is poor: quantum dot colloidal solution, which is placed short time (a couple of days) particle agglomeration and generated, to sink
It forms sediment, this is because ligand organic matter and quantum dot surface ion binding capacity are weak, ligand occurs in the short time and falls off.For this
A problem has researcher to propose to generate the reaction later period in quantum dot, and long chain mercaptans ligand is added and is stirred to improve quantum dot
Stability.Mercaptan ligand and quantum dot binding ability are strong, when in conjunction with quantum dot surface, can be-SH or mercaptides,
In-SH not can effectively solve the problem of ligand falls off.And mercaptides sloughs proton, with quantum dot surface cation binding ability
It is more stronger than-SH, the stability of quantum dot colloidal solution can be made to be increased to the several months or more.Therefore, if mercaptan can be made to slough proton shape
At mercaptides, then the stability of quantum dot solution can be improved.
Third is that be mostly oil-soluble using quantum dot prepared by hot injection method, largely limiting its application property: surface
Ligand is that the quantum dot of tri octyl phosphine, tributylphosphine, oleic acid, stearic acid, oleyl amine etc. can only be dissolved in nonpolar solvent, as chloroform,
Toluene, octane, n-hexane etc. will be such that quantum dot generation mutually converts to make quantum dot be dissolved in polar solvent by ligand exchange.
For phase conversion process, researchers propose for water soluble ligand such as mercaptan acid to be added in quantum dot solution and stir, and replace original
Ligand obtains water/alcohol-soluble ligand.This ligand exchange processes are needed by long agitation, or are aided with Ultrasonic Heating mistake
Journey, and exchange rate is low, solubility is not high in water/alcoholic solution after mutually converting, and stability of solution is poor.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of quantum dot surface ligand exchange sides
Method, it is intended to solve that existing quantum dot surface is insecure with ligand binding, and quantum dot colloidal solution stability and dispersibility are poor
The problem of.
Technical scheme is as follows:
A kind of method of quantum dot surface ligand exchange, wherein comprising steps of
A, ligand containing proton is pre-processed using proton-removed agent, obtains deprotonation ligand；
B, pre-configured first wife's body quantum dot solution is mixed with the deprotonation ligand, stirs the predetermined time at room temperature
Afterwards, ligand exchange reaction occurs, the quantum dot that surface is the deprotonation ligand is obtained after cleaning.
The method of the quantum dot surface ligand exchange, wherein the step A is specifically included:
Proton-removed agent is added in the solution of the ligand containing proton, stirs 15-120min at room temperature, deprotonation ligand solution is made.
The method of the quantum dot surface ligand exchange, wherein in the step A, proton-removed agent and ligand containing proton
Molar ratio be 1:1-6.
The method of the quantum dot surface ligand exchange, wherein the step B further include:
After the completion of ligand exchange reaction, 10-30min is stood, after being eventually adding ethyl acetate centrifugation 2-4 times, obtaining surface is
The quantum dot of deprotonation ligand.
The method of the quantum dot surface ligand exchange, wherein first wife's body in the step B is tri octyl phosphine, three
One of octyl phosphine oxide, tributylphosphine, tributylphosphine oxide, oleic acid, stearic acid, oleyl amine.
The method of the quantum dot surface ligand exchange, wherein in the step B, first wife's body quantum dot with go
Proton ligand and molar ratio be 1:1-8.
The method of the quantum dot surface ligand exchange, wherein the proton-removed agent be organic base, inorganic base, carboxylic acid,
One of acyl chlorides or sulfonic acid chloride.
The method of the quantum dot surface ligand exchange, wherein the ligand containing proton is that C atomicity is less than or equal to
One of 18 carboxylic acid, thiol ligand containing proton or amine containing proton.The method of the quantum dot surface ligand exchange,
In, the thiol ligand containing proton is one of mercaptan, two mercaptan, mercaptan acid, mercaptoalcohol or mercapto-amine.
The method of the quantum dot surface ligand exchange, wherein the amine containing proton is alkylamine, mercapto-amine, amino
One of acid or amide.
The utility model has the advantages that the present invention provides a kind of method of quantum dot ligand exchange, wherein will first contain special functional group (carboxylic
Base, sulfydryl or amino) ligand pre-processed with proton-removed agent, obtain deprotonation ligand；Then by the deprotonation ligand
It is mixed with first wife's body quantum dot solution, carries out ligand exchange reaction, the quantum that surface is deprotonation ligand is obtained after cleaning
Point；Quantum dot ligand exchange processes reaction rate provided by the invention is fast, the deprotonation ligand and quantum dot surface after exchange
Cation is firmly combined, and the quantum dot colloidal solution stability after exchange is strong and dissolubility is fabulous.
Detailed description of the invention
Fig. 1 is a kind of flow chart of the method preferred embodiment of quantum dot surface ligand exchange of the present invention.
Fig. 2 is the launching light spectrogram in the embodiment of the present invention 1 before and after quantum dot ligand exchange.
Fig. 3 is the map that the relative luminous intensity in the embodiment of the present invention 1 before and after quantum dot ligand exchange changes over time.
Fig. 4 is not have in the embodiment of the present invention 3/pre-processed ligand to solution after quantum dot ligand exchange with proton-removed agent
Absorption curve schematic diagram.
Specific embodiment
The present invention provides a kind of method of quantum dot surface ligand exchange, to make the purpose of the present invention, technical solution and effect
Fruit is clearer, clear, and the present invention is described in more detail below.It should be appreciated that specific embodiment described herein is only
To explain the present invention, it is not intended to limit the present invention.
Referring to Fig. 1, Fig. 1 is a kind of flow chart of the method preferred embodiment of quantum dot surface ligand exchange of the present invention,
As shown in the figure, wherein comprising steps of
S10, ligand containing proton is pre-processed using proton-removed agent, obtains deprotonation ligand；
S20, pre-configured first wife's body quantum dot solution is mixed with the deprotonation ligand, stirs the predetermined time at room temperature
Afterwards, ligand exchange reaction occurs, the quantum dot colloidal solution that surface is the deprotonation ligand is made.
Specifically, in the present invention, the ligand containing proton is preferably carboxylic acid of the C atomicity less than or equal to 18, contains
Proton thiol ligand or amine containing proton, these three ligands containing proton are respectively provided with-COOH(carboxyl) ,-SH(sulfydryl) ,-NH2(ammonia
Base) these three functional groups, when by three kinds of ligands containing proton directly as quantum dot surface ligand when, each ligand function
Group-COOH ,-SH ,-NH2In H be in free state, at this time functional group and quantum dot with coordinate bond in conjunction with correspondingly generate-COO
(H)-R ,-S (H)-R ,-NH (H) R, wherein R is quantum dot surface cation；And-COO- ,-S- ,-NH are easy to and free state
H in conjunction with, thus with quantum dot surface cation be detached from generate carboxylic acid, mercaptan, amine；It is this directly to contain proton ligand and amount
Son point combines the quantum dot colloidal solution stability generated very poor, and ligand is extremely insecure in conjunction with quantum dot.
Insecure, the problem of the quantum dot colloidal solution stability difference of generation, this hair for solution quantum dot and ligand binding
The bright preparatory H for using proton-removed agent to handle the ligand containing proton, removing in ligand containing proton, obtains deprotonation and matches
Body；
Specifically, the step S10 specifically: the proton-removed agent is added in ligand solution containing proton and is reacted, it is described
The molar ratio of proton-removed agent and the ligand containing proton is 1:1-6, preferably 1:2；Further, to the ligand solution containing proton with it is described
After proton-removed agent mixing, 15-120min is stirred at room temperature, after being then allowed to stand 10-30min, deprotonation is made after fully reacting
Ligand solution.
Further, when the ligand containing proton is oil-soluble ligand, proton-removed agent is complete with the ligand reaction containing proton
Quan Hou, solution generate split-phase, at this time should remove water phase, obtain the oil-phase solution containing deprotonation ligand by liquid separation.Water phase
Presence will affect oil-soluble deprotonation ligand and first wife's body quantum dot ligand exchange reaction occur, cause to exchange the amount after ligand
Son point luminous efficiency reduces.
Further, in the step S20, by pre-configured first wife's body quantum dot solution and the deprotonation ligand
After stirring the predetermined time at room temperature, ligand exchange reaction occurs for mixing, and the amount that surface is the deprotonation ligand is obtained after cleaning
Sub- point.
In particular it is necessary to be pre-configured with first wife's body quantum dot solution, first wife's body is tri octyl phosphine, trioctylphosphine oxidation
One of phosphine, tributylphosphine, tributylphosphine oxide, oleic acid, stearic acid, oleyl amine；These surfaces of first wife's body as quantum dot
End-capping reagent can reduce quantum dot surface defect to improve the luminous efficiency of quantum dot, however these first wife's bodies are deposited with quantum dot
In the various problems such as binding ability is weak, the quantum dot colloidal solution stability difference that is formed and dissolubility are poor；
Specifically, the present invention mixes pre-configured first wife's body quantum dot solution with the deprotonation ligand, the first wife
Body quantum dot and deprotonation ligand and molar ratio be 1:1-8, preferably 1:2；It is lasting to stir during ligand exchange reaction
15-120min；Specifically, it is anti-that ligand exchange occurs after first wife's body quantum dot solution is mixed with the deprotonation ligand
It answers, lasting stirring can accelerate to react and make reaction more evenly.After the completion of ligand exchange reaction, 10-30min is stood, finally
After being added ethyl acetate centrifugation 2-4 times, the quantum dot that surface is deprotonation ligand is obtained, due to lacking the H of free state in solution
With ligand binding, so that quantum dot ligand is not easily to fall off, stability is stronger.
Quantum dot ligand exchange processes reaction rate provided by the invention is fast, the deprotonation ligand after exchange and quantum dot table
The cation in face is firmly combined, and the quantum dot colloidal solution stability after exchange is strong, dissolubility is good and luminous efficiency is high.
Further, in the present invention, the ligand containing proton is carboxylic acid of the C atomicity less than or equal to 18, mercapto containing proton
One of ylidene ligands or amine containing proton；
Specifically, the C atomicity less than or equal to 18 carboxylic acid be valeric acid, penetenoic acid, caproic acid, hexenoic acid, n-nonanoic acid, capric acid,
Undecyl acid, undecenoic acid, dodecyl acid, lauroleic acid, myristyl acid, tetradecenoic acid, cetyl acid, hexadecylene
One of acid, octadecenic acid or Eighteen alkyl acid etc., but not limited to this；
Specifically, the thiol ligand containing proton is one of mercaptan, two mercaptan, mercaptan acid, mercaptoalcohol or mercapto-amine, but not
It is limited to this；
Wherein, the mercaptan is hexyl mercaptan, spicy thioalcohol, nonyl mercaptan, decyl mercaptan, undecyl mercaptan, lauryl mercaptan, 13 mercaptan, ten
One of four mercaptan, 16 mercaptan or stearylmercaptan etc., but not limited to this；Two mercaptan is 1,2- dithioglycol, 1,3-
Pungent two mercaptan of dimercaptopropane, 1,4- succinimide mercaptans, 1,5- pentane disulfide thioalcohol, 1,6- ethanthiol, 1,8- or two mercaptan of the 1,10- last of the ten Heavenly stems etc.
One of, but not limited to this；
The mercaptoalcohol is 2 mercapto ethanol, 3- sulfydryl -1- propyl alcohol, 4- sulfydryl-n-butyl alcohol, 5- sulfydryl -1- amylalcohol, 6- sulfydryl -
One of 1- hexanol, 8- sulfydryl -1- octanol etc., but not limited to this；
The mercaptan acid is 2- thioacetic acid, 3- mercaptopropionic acid, 4- mercaptobutyric acid, dimercaptosuccinic acid, 6- mercaptohexanoic acid, 4- sulfydryl
One of benzoic acid or cysteine etc., but not limited to this；
The mercapto-amine is 2-MEA, 3- mercaptopropylamine, 4- sulfydryl butylamine, 5- sulfydryl amylamine, 6- sulfydryl hexylamine, 2- ammonia
One of base -3- mercaptopropionic acid, 2- aminothiophenol or mercaptoundecylamine etc., but not limited to this.
Specifically, the amine containing proton is one of alkylamine, mercapto-amine, amino acid or amide, but not limited to this:
Wherein, the alkylamine is methylamine, dimethylamine, ethamine, Methylethyl amine, ethylenediamine, propylamine, butylamine, three-level butylamine, penta
Amine, n-hexylamine, cyclohexylamine, methylhexyl amine, heptyl amice, two heptyl amices, octylame, two n-octyl amines, nonyl amine, 4- octyl aniline, N, N '-two
Methyl-1,8- octamethylenediamine, bis- (2- ethylhexyl) amine, aniline, benzene methanamine, open-chain crown ether, N- toluidines, lauryl amine, 14
One of amine, cetylamine, octadecylamine or octadecenyl amine etc., but not limited to this；
The mercapto-amine be the mercapto-amine include 2-MEA, 3- mercaptopropylamine, 4- sulfydryl butylamine, 5- sulfydryl amylamine,
One of 6- sulfydryl hexylamine, 2- amino-3-mercaptopropionic acid, 2- aminothiophenol or mercaptoundecylamine etc., but not limited to this；
The amino acid is glycine, alanine, valine, leucine, isoleucine, cysteine, phenylalanine, paddy ammonia
One of acid, asparagine or lysine etc., but not limited to this；
The amide is formamide, acetamide, propionamide, butyramide, pentanamide, caproamide, asparagine, picolinamide, water
One of poplar amide or 2-TETRAHYDROFUROYL amine etc., but not limited to this；
Further, in the present invention, the proton-removed agent is one in organic base, inorganic base, carboxylic acid, acyl chlorides or sulfonic acid chloride
Kind；
Wherein, the organic base is tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropylammonium hydroxide, tetrabutyl hydrogen-oxygen
Change ammonium, four pentyl ammonium hydroxide, four hexyl ammonium hydroxide, four octyl ammonium hydroxide, methyl triethylammonium hydroxide, trimethylbenzene
One of base ammonium hydroxide, cetyltrimethylammonium hydroxide or hydroxide hexamethonium etc., but not limited to this；
The carboxylic acid is formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, octanoic acid, sourer, benzoic acid, phenylacetic acid, phenyl third
One of acid, phenylbutyric acid, phenylpentanoic acid, phenyl caproic acid or phenylalanine etc., but not limited to this；
The inorganic base is sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, aluminium hydroxide, indium hydroxide or hydroxide
One of ammonium etc., but not limited to this；
The acyl chlorides is chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, 2- chlorpromazine chloride, 3- chlorpromazine chloride, 4- neoprene
Acyl chlorides, 1- butyl sulfochlorides, 1- hexadecane sulfonic acid chloride, 1- perfluorooctane sulfonyl chlorine, 1,7- pimeloyl chloride, three formyl of 1,3,5- benzene
One of chlorine, 4- chlorobenzoyl chloride, 5-Chlorovaleryl Chloride, 6- chlorine caproyl chloride or 2- chloropyridine -4- formyl chloride etc., but be not limited to
This；
The sulfonic acid chloride is methylsufonyl chloride, ethyl chloride, sulfonyl propyl chlorine, butyl sulfochlorides, amyl sulfonic acid chloride, hexyl sulphur
Acyl chlorides, perfluorooctane sulfonyl chlorine, hexadecane sulfonic acid chloride, 2- chloroethene alkanesulphonyl chlorides, benzene sulfonyl chloride or to one of benzene sulfonyl chloride etc., but
It is without being limited thereto.
Further, the quantum dot is CdSe, CdS, ZnSe, ZnS, PbSe, PbS, CdTe, Cd1-xZnxS、Cd1- xZnxSe、CdSeyS1-y、Cd1-xZnxSeyS1-y、PbSeXS1-X、ZnXCd1-XTe、CdSe/ ZnS、CdS/ ZnS、Cd1-xZnxSe/
ZnS、Cd1-xZnxS/ ZnS、CdSe/CdS/ZnS、CdSe/ZnSe/ZnS、CdS/Cd1-xZnxS/CdyZn1-yS/ZnS、CdSe/
Cd1-xZnxSe/CdyZn1-ySe /ZnSe、InP、InP/ZnS、ZnO、MgO、CeO2、NiO、TiO2、CaF2、NaYF4Or NaCdF4
Any one in, but not limited to this luminescent quantum dot.
A kind of method of quantum dot surface ligand exchange of the present invention is further explained below by specific embodiment
It is bright:
Embodiment 1
1, surface ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 8mmol tetramethylammonium hydroxide to be dissolved in chloroform, 8 mmol spicy thioalcohols is then added, 30 min are stirred at room temperature, so
After stand 15 min, solution generates split-phase, and liquid separation obtains chloroform phase, it is molten to obtain the processed spicy thioalcohol of tetramethylammonium hydroxide
Liquid.
3, ligand exchange processes:
The quantum dot that the surface ligand is octadecenic acid is made into the chloroformic solution of 10mg/ml, above-mentioned tetramethyl is then added
30 min are stirred at room temperature in the processed spicy thioalcohol solution of ammonium hydroxide, stand 15min, and ethyl acetate is added and is centrifuged 2 times,
Obtain the quantum dot that surface ligand is deprotonation spicy thioalcohol.
Further, Fig. 2 is the launching light spectrogram in embodiment 1 before and after quantum dot ligand exchange, as shown in Figure 2, quantum dot
Its luminous intensity increases after ligand exchange；It, can effectively and quantum dot surface after explanation is handled ligand with proton-removed agent
Cation combines, and surface defect is reduced, to improve luminous efficiency.
Further, Fig. 3 is the figure that the relative luminous intensity in embodiment 1 before and after quantum dot ligand exchange changes over time
Spectrum, from the figure 3, it may be seen that it is small that the luminous intensity of quantum dot changes over time reduction degree after ligand exchange；This same explanation spends matter
, can be not easily to fall off effectively in conjunction with quantum dot surface cation after sub- agent handles ligand, surface defect is reduced, thus
Improve luminous efficiency.
Embodiment 2
1, surface ligand is the preparation of stearic ZnO quantum dot:
1), the preparation of zinc stearate precursor liquid: take 2mmol zinc stearate that 30 ml ODE Ar exhaust 30 at 130 DEG C is added
Min, solution become colorless and transparent, obtain zinc stearate precursor liquid；
2), the preparation of long-chain alcohol precursor liquid: taking 10 mmol ODA to be dissolved in 12.6 ml ODE, 30 min be vented at 130 DEG C,
Solution is colorless and transparent, then is warming up to 200 DEG C for molten, obtains long-chain alcohol precursor liquid；
3), the preparation of ZnO quantum dot: being warming up to 270 DEG C for zinc stearate solution, then once quickly infuses long-chain alcoholic solution
Enter in zinc stearate solution, reaction maintains 250 DEG C of 4 min of holding.Then solution is cooled to room temperature, cleans 2 times, is sunk
Starch is dried in vacuo 24 h at room temperature, obtains dry ZnO crystal；
2, the deprotonation of ligand containing proton:
It takes 4 mmol tetraethyl ammonium hydroxides to be added and contains 8 mmol 1, in the hexane solution of 2- dithioglycol, at room temperature
30min is stirred, 15 min is then allowed to stand, takes n-hexane phase, it is molten to obtain processed 1, the 2- dithioglycol of tetraethyl ammonium hydroxide
Liquid；
3, ligand exchange processes:
Taking 100mg surface ligand is that stearic quantum dot is added in 10ml n-hexane, is uniformly mixed, above-mentioned tetrem is then added
30 min are stirred at room temperature in processed 1, the 2- dithioglycol solution of base ammonium hydroxide, stand 15min, lower layer is obtained by extraction
Liquid is added ethyl acetate and is centrifuged 2 times, obtains the quantum dot that surface ligand is deprotonation dithioglycol.
Embodiment 3
1, ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 8 mmol tetramethylammonium hydroxide to be added in the hexane solution containing 16 mmol 2 mercapto ethanols, stirs at room temperature
15 min are mixed, 15 min are then allowed to stand, obtain the processed 2 mercapto ethanol solution of tetramethylammonium hydroxide.
3, ligand exchange processes:
The quantum dot that the surface ligand is octadecenic acid is made into the hexane solution of 10mg/ml, above-mentioned tetramethyl is then added
The processed 2 mercapto ethanol solution of base ammonium hydroxide descends 15 min of heating stirring at room temperature, stands 15min, is obtained by extraction
Lower liquid is added ethyl acetate and is centrifuged 2 times, obtains the quantum dot that surface ligand is deprotonation mercaptoethanol.
Further, Fig. 4 be without/with proton-removed agent ligand is pre-processed it is bent to the absorption of solution after quantum dot ligand exchange
Line；As shown in figure 4, the quantum dot for not having to wherein obtain after proton-removed agent pre-processes ligand is difficult to dissolve in ethanol,
A large amount of precipitatings are arranged at solution bottom, and the quantum dot obtained after being pre-processed with proton-removed agent to ligand is completely dissolved in ethanol,
Solution is transparent.The stillness of night of two parts of solution is taken to carry out uv-visible absorption spectra test, if not carrying out as seen from the figure to ligand
Deprotonation processing does not have then the band edge of ZnO to absorb in quantum dot solution absorption curve.And after carrying out deprotonation processing to ligand,
Solution has the band edge absorption peak of ZnO.After illustrating deprotonation ligand to ligand pretreatment, the dissolution of quantum dot can effectively improve
Property.
Embodiment 4
1, ligand be octadecenic acid, tri octyl phosphine quantum dot preparation:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-TOP precursor liquid: by 0.2 mmol selenium powder, 0.6 mmol sulphur powder is dissolved in the tri octyl phosphine of 2mL,
Obtain selenizing tri octyl phosphine-trioctylphosphine sulfide presoma；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected selenizing tri octyl phosphine-trioctylphosphine sulfide
Presoma, reaction maintain 8 min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；So
Chloroform is added afterwards and acetone is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is tri octyl phosphine and precipitates.
2, the deprotonation of ligand containing proton:
It takes 4 mmol tetramethylammonium hydroxide to be added in the hexane solution containing 4mmol lauroleic acid, is stirred at room temperature
30min is then allowed to stand 15 min, removes supernatant liquid, obtains the processed lauroleic acid solution of tetramethylammonium hydroxide.
3, ligand exchange processes:
It takes the quantum dot that 100mg surface ligand is tri octyl phosphine to be added in 10ml n-hexane, is uniformly mixed, is then added above-mentioned four
The processed lauroleic acid solution of ammonium hydroxide, is stirred at room temperature 30 min, stands 15min, be added ethyl acetate from
The heart 2 times, obtain the quantum dot that surface ligand is deprotonation lauroleic acid.
Embodiment 5
1, surface ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 4 mmol ammonium hydroxide to be added in the aqueous solution containing 4mmol caproic acid, 30min is stirred at room temperature, is then allowed to stand 15
Min obtains the processed caproic acid solution of ammonium hydroxide.
3, ligand exchange processes:
It takes the quantum dot that 100mg surface ligand is octadecenic acid to be added in 10ml n-hexane, is uniformly mixed, above-mentioned hydrogen is then added
30 min are stirred at room temperature in the processed caproic acid solution of amine-oxides, stand 15min, and lower liquid is obtained by extraction, and acetic acid is added
Ethyl ester is centrifuged 2 times, obtains the quantum dot that surface ligand is deprotonation caproic acid.
Embodiment 6
1, surface ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 4 mmol propionyl chlorides, 4 mmol octylames to be added in chloroformic solution, 30min is stirred at room temperature, obtain propionyl chloride processing
The octylame solution crossed.
3, ligand exchange processes:
The quantum dot that surface ligand is octadecenic acid is made into the chloroformic solution of 10mg/ml, above-mentioned propionyl chloride processing is then added
60 min are stirred at room temperature in the octylame solution crossed, and stand 15 min, and ethyl acetate is added and is centrifuged 2 times, obtaining surface ligand is
The quantum dot of deprotonation octylame.
Embodiment 7
1, surface ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 4 mmol benzene sulfonyl chlorides, 4 mmol that phenylalanine is added to enter in aqueous solution, 30min is stirred at room temperature, obtains benzene sulfonyl
The processed Phe solution of chlorine.
3, ligand exchange processes:
The quantum dot that surface ligand is octadecenic acid is made into the chloroformic solution of 10mg/ml, is then added at above-mentioned benzene sulfonyl chloride
60 min are stirred at room temperature in the Phe solution managed, and stand 15 min, and ethyl acetate is added and is centrifuged 2 times, obtains surface
Ligand is the quantum dot of deprotonation phenylalanine.
Embodiment 8
1, surface ligand is the preparation of the quantum dot of octadecenic acid:
1) 0.8mmolCdO, 8mmol zinc acetate and 15 ml oleic acid and 20 ml1- ten, cadmium oleate-zinc precursor liquid preparation: are taken
Eight alkene are heated to 150 DEG C of exhaust 1h under an ar atmosphere, it is molten to form transparent cadmium oleate-zinc precursor in 100mL three-necked flask
Liquid；
2), the preparation of Se-S-ODE precursor liquid: 0.8 mmol Se and 8 mmol S is taken to be dissolved in 6 mL1- octadecylenes at 140 DEG C molten
In liquid, Se-S-ODE precursor liquid is formed；
3) cadmium oleate-zinc precursor liquid, is heated slowly to 300 DEG C, is once rapidly injected Se-S-ODE precursor liquid, reaction maintains 8
min.Then temperature is reduced to 100 DEG C, ethyl acetate cleaning is added, centrifugation obtains sediment；Then chloroform and acetone is added
It is centrifuged repeatedly 2 times, obtains the quantum dot that surface ligand is octadecenic acid and precipitate.
2, the deprotonation of ligand containing proton:
It takes 4 mmol benzene sulfonyl chlorides, 4 mmol aniline to be added in aqueous solution, 30min is stirred at room temperature, obtains at benzene sulfonyl chloride
The aniline solution managed.
3, ligand exchange processes:
The quantum dot that surface ligand is octadecenic acid is made into the chloroformic solution of 10mg/ml, is then added at above-mentioned benzene sulfonyl chloride
60 min are stirred at room temperature in the aniline solution managed, and stand 15 min, and ethyl acetate is added and is centrifuged 2 times, obtains surface ligand
For the quantum dot of deprotonation aniline.
In conclusion the present invention provides a kind of method of quantum dot ligand exchange, wherein will first contain special functional group (carboxylic
Base, sulfydryl or amino) ligand pre-processed with proton-removed agent, obtain deprotonation ligand；Then by the deprotonation ligand
It is mixed with first wife's body quantum dot solution, carries out ligand exchange reaction, obtain the quantum dot colloid that surface is deprotonation ligand
Solution；Quantum dot ligand exchange processes reaction rate provided by the invention is fast, easy to operate, the deprotonation ligand after exchange and amount
The cation on son point surface is firmly combined, and the quantum dot colloidal solution stability after exchange is strong, dissolubility is good, luminous efficiency is high.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of method of quantum dot surface ligand exchange, which is characterized in that comprising steps of
A, ligand containing proton is pre-processed using proton-removed agent, obtains deprotonation ligand；
B, pre-configured first wife's body quantum dot solution is mixed with the deprotonation ligand, stirs the predetermined time at room temperature
Afterwards, ligand exchange reaction occurs, the quantum dot that surface is the deprotonation ligand is obtained after cleaning.
2. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that the step A is specifically wrapped
It includes:
Proton-removed agent is added in the solution of the ligand containing proton, stirs 15-120min at room temperature, deprotonation ligand solution is made.
3. according to the method for quantum dot surface ligand exchange described in right 1, which is characterized in that in the step A, proton-removed agent
Molar ratio with the ligand containing proton is 1:1-6.
4. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that also wrapped in the step B
It includes:
After the completion of ligand exchange reaction, 10-30min is stood, after being eventually adding ethyl acetate centrifugation 2-4 times, obtaining surface is
The quantum dot of deprotonation ligand.
5. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that the original in the step B
Ligand is one of tri octyl phosphine, trioctyl phosphine oxide, tributylphosphine, tributylphosphine oxide, oleic acid, stearic acid, oleyl amine.
6. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that described in the step B
First wife's body quantum dot and deprotonation ligand and molar ratio be 1:1-8.
7. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that the proton-removed agent is to have
One of machine alkali, inorganic base, carboxylic acid, acyl chlorides or sulfonic acid chloride.
8. the method for quantum dot surface ligand exchange according to claim 1, which is characterized in that the ligand containing proton is
C atomicity is less than or equal to 18 one of carboxylic acid, thiol ligand containing proton or amine containing proton.
9. the method for quantum dot surface ligand exchange according to claim 7, which is characterized in that the sulfydryl containing proton is matched
Body is one of mercaptan, two mercaptan, mercaptan acid, mercaptoalcohol or mercapto-amine.
10. the method for quantum dot surface ligand exchange according to claim 7, which is characterized in that the amine containing proton is
One of alkylamine, mercapto-amine, amino acid or amide.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710399235.6A CN108977191A (en) | 2017-05-31 | 2017-05-31 | A kind of quantum dot surface ligand exchange processes |
| PCT/CN2018/079531 WO2018219019A1 (en) | 2017-05-31 | 2018-03-20 | Quantum dot surface ligand exchange method |
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| CN110330517A (en) * | 2019-05-22 | 2019-10-15 | 纳晶科技股份有限公司 | Alcohol-soluble quantum dot and preparation method thereof, quantum dot film, quantum dot optoelectronic devices |
| CN110643351A (en) * | 2018-12-14 | 2020-01-03 | 马鞍山微晶光电材料有限公司 | Quantum dot modifier |
| CN111378435A (en) * | 2018-12-29 | 2020-07-07 | Tcl集团股份有限公司 | Preparation method of quantum dot film |
| CN111378433A (en) * | 2018-12-29 | 2020-07-07 | Tcl集团股份有限公司 | Quantum dot ligand exchange method |
| CN111378432A (en) * | 2018-12-29 | 2020-07-07 | Tcl集团股份有限公司 | Quantum dot post-treatment method and ligand exchange method |
| CN111378449A (en) * | 2018-12-27 | 2020-07-07 | Tcl集团股份有限公司 | Post-processing method of quantum dots |
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| CN114621750A (en) * | 2022-04-20 | 2022-06-14 | 广东欧迪明光电科技股份有限公司 | Method for regulating and controlling quantum dot energy level based on phenyl mercaptan ligand |
| 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 |
| CN115109583A (en) * | 2022-06-15 | 2022-09-27 | 广州光达创新科技有限公司 | Colloidal quantum dot material, preparation method thereof and application thereof in colloidal quantum dot light detector and array |
| CN115109467A (en) * | 2022-05-27 | 2022-09-27 | 北京理工大学 | Method for regulating and controlling infrared colloid quantum dot band transport by normal-temperature miscible ligand exchange and application |
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