WO2024130481A1 - Procédé de production d'un composé d'halogénure métallique - Google Patents

Procédé de production d'un composé d'halogénure métallique Download PDF

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WO2024130481A1
WO2024130481A1 PCT/CN2022/139974 CN2022139974W WO2024130481A1 WO 2024130481 A1 WO2024130481 A1 WO 2024130481A1 CN 2022139974 W CN2022139974 W CN 2022139974W WO 2024130481 A1 WO2024130481 A1 WO 2024130481A1
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metal halide
halide compound
precursor
producing
solution
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PCT/CN2022/139974
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English (en)
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Meng Li
Takuo Hayashi
Jianjun Yuan
Xiao-han HAO
Wei Zhao
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Dic Corporation
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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
    • C09K11/66—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing germanium, tin or lead

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  • the present invention relates to a method for producing a metal halide compound.
  • metal halide compounds have attracted attentions from the viewpoint of a plurality of applications.
  • the emission wavelength of PeQDs can be controlled by the proportion of the halogen elements and the control of a particle size is easy as compared to InP quantum dots and the like. Therefore, PeQDs are advantageous from the viewpoint of productivity.
  • the metal halide compounds are useful and a method for efficiently producing the metal halide has been required.
  • NPL 1 and NPL 2 have described methods for obtaining metal halide compounds by dissolving a metal precursor into a polar solvent such as DMSO and DMF and adding the resultant solution into a poor solvent (a non-polar solvent such as toluene) .
  • a polar solvent such as DMSO and DMF
  • a non-polar solvent such as toluene
  • NPL 3 has described a method for obtaining metal halide compounds by dissolving a metal precursor into a hydrohalic acid.
  • PTL 1 has described a method for producing a crystalline A/M/X material including a step of a) bringing an aqueous solution including a precursor of A and an aqueous solvent into contact with an organic solution including a precursor of M and an organic solvent, and a step of b) forming a precipitate when the aqueous solution and the organic solution are contacted.
  • NPL 1 Adv. Funct. Mater. 2016, 26, 2435-2445
  • NPL 2 J. Am. Chem. Soc. 2014, 136, 850-853
  • NPL 3 ACIE 2020, 59, 21414-21418
  • the present invention is made in view of the above problems and an object of the present invention is to provide a method for producing a metal halide compound that improves process safety and provides the desired composition can be provided.
  • the present invention adopts the following constitution.
  • step (b) comprises
  • A is one or more selected from the group consisting of alkali metal ions and ammonium cations.
  • B is one or more selected from the group consisting of Cu + , Ag + , Au + , Li + , Na + , K + , Tl + , Mn 2+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Mg 2+ , Ca 2+ , Sr 2+ , Pd 2+ , Cd 2+ , Ge 2+ , Sn 2+ , Pb 2+ , Eu 2+ , yb 2+ , Fe 3+ , Co 3+ , Cr 3+ , Ga 3+ , Sb 3+ , Bi 3+ , In 3+ , Sc 3+ , y 3+ , La 3+ , Ce 3+ , Sm 3+ , Eu 3+ , Gd 3+ , Lu 3+ , Nd 3+ , Er 3+ , Pr 3+
  • X is one or more halogen anions selected from the group consisting of F - , Cl - , Br - , and I - .
  • a method for producing a metal halide compound that improves process safety and provides the desired composition can be provided.
  • FIG. 1 is a SEM photograph of Cs 3 Sb 2 Br 9 obtained in Example 2.
  • FIG. 2 is an emission spectrum and an absorption spectrum of Cs 3 Cu 2 Cl 5 obtained in Example 3.
  • FIG. 3A is a SEM photograph of Cs 3 Sb 2 Br 9 obtained in Example 14.
  • FIG. 3B is a SEM photograph of Cs 3 Sb 2 Br 9 obtained in Example 14.
  • FIG. 4 is a SEM photograph of Cs 3 CeCl 6 obtained in Example 16.
  • FIG. 5 is a SEM photograph of Cs 3 CeCl 6 obtained in Example 18.
  • FIG. 6 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 20.
  • FIG. 7 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 21.
  • FIG. 8 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 22.
  • FIG. 9 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 23.
  • the method of producing the metal halide compound according to the present embodiment is a method for producing a metal halide compound represented by General Formula (1) including a step (a) of mixing a precursor of A and an alcohol to obtain an organic solution A, and
  • c is a number of 1 to 18.
  • A may be substituted with one or more substituents selected from alkali metal cations, amines, C 1-6 alkylamines, imines, C 1-6 alkylimines, C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, and C 6-12 aryl.
  • substituents selected from the group consisting of C 1-10 alkylammonium, C 2- 10 alkenylammonium, C 1-10 alkyliminium, C 3-10 cycloalkylammonium, and C 3-10 cycloalkylimiium are preferable.
  • One or more substituents selected from the group consisting of alkali metal ions and ammonium ions are more preferable and Cs + , Rb + , methylammonium, formamidinium, and Li + are further preferable.
  • B is preferably one or more cations selected from the group consisting of Cu + , Ag + , Au + , Li + , Na + , K + , Tl + , Mn 2+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Mg 2+ , Ca 2+ , Sr 2+ , Pd 2+ , Cd 2+ , Ge 2+ , Sn 2+ , Pb 2+ , Eu 2+ , yb 2+ , Fe 3+ , Co 3+ , Cr 3+ , Ga 3+ , Sb 3+ , Bi 3+ , In 3+ , Sc 3+ , y 3+ , La 3+ , Ce 3+ , Sm 3+ , Eu 3+ , Gd 3+ , Lu 3+ , Nd 3+ , Er 3+ , Pr 3+ , Tb 3+ , Dy 3+ , Tm 3+ , Ho 3+ , Cu
  • X is preferably one or more ions selected from the group consisting of F - , Cl - , Br - , and I - and more preferably one or more ions selected from the group consisting of Cl - and Br - .
  • the precursor of A and the alcohol are mixed to obtain an organic solution A.
  • the precursor of A is a compound including one or more monovalent cations A (hereinafter, also simply referred to as "A cation" ) in the compound represented by Formula (1) .
  • a cation monovalent cations A
  • [A] contains one kind of the A cation
  • one kind of the precursor of A is usually used and this precursor of A is generally formed of this A cation together with one or more counterions.
  • [A] contains two or more of the A cations
  • Each precursor of A can contain one or more of the A cations in two or more of the A cations existing in [A] .
  • each precursor of A contains one kind or two kinds of the A cations.
  • Each precursor of A preferably contains one kind of the A cation. This is because such precursors are generally commercially available in high purity.
  • the precursor of A is preferably a halide salt from the viewpoint of solubility into the alcohol and is more preferably a compound formed of the A cation and one or more halide anions selected from F - , Cl - , Br - , and I - .
  • the precursor of A include CsCl, CsBr, LiCl, LiBr, methylammonium chloride, formamidinium chloride, methylammonium bromide, and formamidinium bromide.
  • the alcohol is not particularly limited. Aliphatic alcohols are preferable from the viewpoint of the solubility of the precursor of A. Methanol, ethanol, propanol, isopropyl alcohol, 1-butanol, and tert-butyl alcohol are more preferable and methanol is further preferable.
  • the organic solution A includes preferably 40%by mass or less, more preferably 30%by mass or less, and further preferably 20%by mass or less of water relative to 100%by mass of the total amount of the organic solution A.
  • the content of water in the organic solution A within the above preferable range allows the dissolution or decomposition of the target metal halide compound to be likely to be prevented.
  • the step (a) can be performed under mild conditions such as room temperature.
  • the treatment time of the step (a) time is not particularly limited. One minute to 3 hours are preferable and 5 minutes to 1 hour is further preferable.
  • a surfactant may be mixed with the organic solution A.
  • surfactant examples include oleic acid, trimethylstearylammonium chloride, didodecyldimethylammonium chloride, methyltrioctylammonium chloride, trimethyl-n-octylammonium chloride, oleylamine, n-octylammonium bromide, and oleylammonium bromide.
  • the organic solution A obtained at the step (a) is brought into contact with the precursor of B to obtain the metal halide compound represented by Formula (1) .
  • step (b) is preferably any one of the following steps (b1) to (b3) .
  • Step (b1) Including a step (b1-1) of bringing the organic solution A into contact with the precursor of B to obtain a suspension liquid;
  • Step (b2) Including a step (b2-1) of bringing the organic solution A into contact with the precursor of B to obtain a solution;
  • Step (b3) Including a step (b3-1) of bringing the organic solution A into contact with the precursor of B to obtain a solution, and a step (b3-2) of drying the solution obtained at the step (b3-1) under reduced pressure to obtain the precipitate of the metal halide compound represented by Formula (1) .
  • Step (b1) Step (b1-1)
  • the method for bringing the organic solution A into contact with the precursor of B is not particularly limited.
  • the organic solution A is added to the precursor of B or the precursor of B is added to the organic solution A.
  • the step (b1-1) can be performed under mild conditions such as room temperature.
  • the treatment time of step (b1-1) time is not particularly limited. One minute to 3 hours are preferable and 5 minutes to 1 hour is further preferable.
  • the precursor of B is a compound containing one or more monovalent to hexavalent metal cations B (hereinafter simply referred to as a "B metal cation") in the compound represented by Formula (1) .
  • B metal cation a compound containing one or more monovalent to hexavalent metal cations B (hereinafter simply referred to as a "B metal cation") in the compound represented by Formula (1) .
  • [B] contains one kind of the B cation
  • one kind of the precursor of B is usually used and this precursor of B is generally formed of this B cation together with one or more counterions.
  • [B] contains two or more of the B cations
  • Each precursor of B can contain one or more of the B metal cations among two or more of the B metal cations existing in [B] .
  • each precursor of B contains one kind or two kinds of the B cations.
  • Each precursor of B preferably contains one kind of the B cation. This is because such precursors are generally commercially
  • the precursor of B is preferably a halide salt and a compound formed of a B metal cation and one or more halide anions selected from F - , Cl - , Br - , and I - .
  • the precursor of B of the halide salt allows the target metal halide compound to be easily obtained.
  • salts other than the halide salt for example, acetate salts
  • other salts for example, acetate salts
  • use of the halide salt as the precursor of B allows byproduct formation to be prevented.
  • the form of the precursor of B is not particularly limited and may be a solid or a solution.
  • the precursor of B is not limited to compounds that easily dissolve in methanol and thus the precursor of B is preferably a solid.
  • the precursors of B include ZnCl 2 , ZnBr 2 , FeCl 2 , FeCl 3 , CoCl 2 , ZrCl 4 , SbCl 3 , SbBr 3 , InCl 3 , YCl 3 , AgAc, BiBr 3 , CeCl 3 , LaCl 3 , TeCl 4 , NaCl, CuCl, PrCl 3 , SmCl 3 , HoCl 3 , ErCl 3 , EuCl 3 ⁇ 6H 2 O, GdCl 3 ⁇ 6H 2 O, NdCl 3 , TbCl 3 ⁇ 6H 2 O, DyCl 3 ⁇ 6H 2 O, TmCl 3 ⁇ 6H 2 O, LuCl 3 ⁇ 6H 2 O, HoCl 3 ⁇ 6H 2 O, ErCl 3 ⁇ 6H 2 O, NdCl 3 ⁇ 6H 2 O, SmCl 3 ⁇ 6H 2 O
  • the method of purifying the suspension liquid obtained at the step (b1-1) is not particularly limited and known purification methods can be employed.
  • the suspension liquid is purified by centrifugation to obtain a precipitate and the precipitate is further dried under reduced pressure to obtain the metal halide compound represented by Formula (1) .
  • Step (b2) Step (b2-1)
  • the method for bringing the organic solution A into contact with the precursor of B is not particularly limited.
  • the organic solution A is added to the precursor of B or the precursor of B is added to the organic solution A.
  • the step (b2-1) can be performed under mild conditions such as room temperature.
  • the treatment time of step (b2-1) time is not particularly limited. One minute to 3 hours are preferable and 5 minutes to 1 hour is further preferable.
  • the precursor of B is the same as the precursor of B at the step (b1-1) .
  • the metal halide compound represented by Formula (1) can be precipitated and obtained.
  • the poor solvent to be added is not particularly limited.
  • examples of the poor solvent include alcohol solvents such as ethanol and isopropyl alcohol.
  • Step (b3) Step (b3-1)
  • the method for bringing the organic solution A into contact with the precursor of B is not particularly limited.
  • the organic solution A is added to the precursor of B or the precursor of B is added to the organic solution A.
  • the step (b3-1) can be performed under mild conditions such as room temperature.
  • the treatment time of step (b3-1) time is not particularly limited. One minute to 3 hours are preferable and 5 minutes to 1 hour is further preferable.
  • the metal halide compound represented by Formula (1) can be obtained by drying the solution obtained at the step (b3-1) under reduced pressure.
  • the treatment temperature for drying under reduced pressure is not particularly limited and is preferably 20°C to 120°C and further preferably 60°C to 100°C.
  • the method for producing the metal halide compound according to the present embodiment described above allows the reaction of the precursor compounds to be performed under mild conditions such as room temperature.
  • the method for producing the metal halide compound according to the present embodiment allows the metal halide compound having the desired composition to be obtained without using strong acids such as hydrohalic acid.
  • the method of producing the metal halide compound according to the present embodiment allows the safety of the process to be improved as compared to conventional production methods and the metal halide compound having the desired composition to be simply provided.
  • a metal halide compound having a perovskite structure can also be obtained. Therefore, the metal halide compound obtained by the production method according to the present embodiment can be applied to UV-curable inkjet-inks including quantum dots for light conversion layers.
  • the shape of the metal halide compound particles can be controlled. Therefore, the metal halide compound obtained by the production method according to the present embodiment can be applied to effect pigments.
  • metal halide compounds in which the A cation in Formula (1) is Li + can also be obtained. Therefore, the metal halide compound obtained by the production method according to the present embodiment can be applied to solid electrolytes for lithium ion batteries.
  • the metal halide compound obtained by the production method according to the present embodiment can also be applied to photocatalysts.
  • a sample powder was filled into a sample holder for measurement having a depth of 0.5 mm and set in a wide-angle X-ray diffraction (XRD) apparatus (MiniFlex II, manufactured by Rigaku Corporation) .
  • the measurement was performed under conditions of Cu/K ⁇ ray, 40 kV/40 mA, a scan speed of 5°/min, and a scan range of 10° to 70° or a scan range of 10° to 90°.
  • Epsilon 1 X-ray fluorescence analyzer manufactured by Malvern Panalytical Ltd. . , approximately 70 mg of the sample powder was placed on a filter paper, covered with a PP film, and subjected to XRF (X-ray fluorescence) analysis under the following conditions.
  • the sample powder was photographed with a scanning electron microscope (JSM7900-F, manufactured by JEOL Ltd. ) .
  • the photoluminescence quantum yield (PLQY) of approximately 100 mg of the sample powder was measured by an absolute PL quantum yield measuring apparatus Quantaurus-QY ⁇ C11347-11 (Hamamatsu Photonics K.K. ) under the following conditions.
  • This solution was added to zinc bromide (0.1125 g, 0.5 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (3,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°Cfor 3 hours to obtain a solid.
  • the result of the XRD analysis indicates that the obtained solid was Cs 2 ZnBr 4 .
  • FIG. 1 is a SEM photograph of Cs 3 Sb 2 Br 9 obtained in Example 2.
  • the magnification of the SEM photograph in FIG. 1 is 10,000 times, the measurement condition is 3.0 keV, and the scale bar indicates 1 ⁇ m.
  • This solution was added to copper (I) chloride (0.099 g, 1.0 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (3,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 3 Cu 2 Cl 5 .
  • the emission spectrum and absorption spectrum of the obtained solid are illustrated in FIG. 2.
  • the maximum emission wavelength at an excitation wavelength of 300 nm is 528 nm.
  • This solution was added to neodymium chloride hexahydrate (0.1793 g, 0.5 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (3,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 3 NdCl 6 .
  • the reaction was performed in accordance with Example 4 except that neodymium chloride hexahydrate was replaced by gadolinium chloride hexahydrate (0.1859 g, 0.5 mmol) to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 3 GdCl 6 .
  • This solution was added to samarium chloride (0.1925 g, 0.75 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (5,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 NaSmCl 6 .
  • This solution was added to erbium chloride (0.2052 g, 0.75 mmol) and stirred at 40°C for 30 min to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (5,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 NaErCl 6 .
  • Cesium bromide (0.1064 g, 0.5 mmol) , silver acetate (0.0417 g, 0.25 mmol) , and methanol (5.5 mL) were mixed to obtain a solution.
  • This solution was added to bismuth bromide (0.1122 g, 0.25 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (5,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 2 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 AgBiBr 6 .
  • This solution was added to a mixture of zinc chloride (0.0273 g, 0.2 mmol) and zinc bromide (0.0676 g, 0.3 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (3,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°Cfor 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 Zn (Cl 0.7 Br 0.3 ) 4 .
  • This solution was added to zirconium chloride (0.1165 g, 0.5 mmol) to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (5,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°C for 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 ZrCl 6 .
  • Zirconium chloride (0.1165 g, 0.5 mmol) was added to this solution to obtain a suspension liquid.
  • the suspension liquid was purified by centrifugation (5,000 rpm, 5 min) and the resultant precipitate was dried under reduced pressure at 60°Cfor 3 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 ZrCl 6 .
  • FIG. 3A and FIG. 3B are SEM photographs of Cs 3 Sb 2 Br 9 obtained in Example 14.
  • the magnification of the SEM photograph in FIG. 3A is 10,000 times, the measurement condition is 3.0 keV, and the scale bar indicates 1 ⁇ m.
  • the magnification of the SEM photograph in FIG. 3B is 5,000 times, the measurement condition is 3.0 keV, and the scale bar indicates 1 ⁇ m.
  • the solution B was added dropwise to the solution A to obtain a suspension liquid, and thereafter the resultant suspension liquid was reacted by heating at 40°C for 30 minutes.
  • the reaction solution was allowed to stand to cool to room temperature and thereafter purified by centrifugation (5,000 rpm, 5 min) .
  • the resultant precipitate was dried under reduced pressure at 60°C for 2 hours to obtain a solid.
  • the results of the XRD analysis and the XRF analysis indicate that the obtained solid was Cs 2 NaYCl 6 .
  • FIG. 4 is a SEM photograph of Cs 3 CeCl 6 obtained in Example 16. The magnification of the SEM photograph in FIG. 4 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.
  • FIG. 5 is a SEM photograph of Cs 3 CeCl 6 obtained in Example 18. The magnification of the SEM photograph in FIG. 5 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.
  • Lithium chloride (0.0763 g, 1.8 mmol) and methanol (2 mL) were mixed to obtain a solution.
  • FIG. 6 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 20.
  • the magnification of the SEM photograph in FIG. 6 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.
  • FIG. 7 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 21.
  • the magnification of the SEM photograph in FIG. 7 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.
  • FIG. 8 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 22.
  • the magnification of the SEM photograph in FIG. 8 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.
  • FIG. 9 is a SEM photograph of Cs 3 Bi 2 Br 9 obtained in Example 23.
  • the magnification of the SEM photograph in FIG. 9 is 5,000 times, the measurement condition is 5.0 keV, and the scale bar indicates 1 ⁇ m.

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Abstract

L'invention concerne un procédé de production d'un composé d'halogénure métallique représenté par la formule générale (1) : [A] a[B] b[X] c (1) [dans la formule (1), A représente un ou plusieurs cations monovalents ; B représente un ou plusieurs cations métalliques monovalents à hexavalents ; X représente un ou plusieurs anions halogènes ; a est un nombre de 1 à 6 ; b est un nombre de 1 à 6 ; et c est un nombre de 1 à 18], le procédé comprenant : une étape (a) consistant à mélanger un précurseur de A et un alcool pour obtenir une solution organique A ; et une étape (b) consistant à mettre en contact la solution organique A avec un précurseur de B pour obtenir le composé d'halogénure métallique représenté par la formule (1).
PCT/CN2022/139974 2022-12-19 2022-12-19 Procédé de production d'un composé d'halogénure métallique WO2024130481A1 (fr)

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CN112739798A (zh) * 2018-07-13 2021-04-30 牛津大学科技创新有限公司 A/m/x材料的制备方法
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CN107805779A (zh) * 2017-10-10 2018-03-16 东南大学 一种激光溅射法制备CsPbBr3薄膜的方法
CN112739798A (zh) * 2018-07-13 2021-04-30 牛津大学科技创新有限公司 A/m/x材料的制备方法
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