WO2013089483A1 - 금속 도핑된 결정성 철인산염, 이의 제조 방법 및 이로부터 제조된 리튬 복합금속인산화물 - Google Patents
금속 도핑된 결정성 철인산염, 이의 제조 방법 및 이로부터 제조된 리튬 복합금속인산화물 Download PDFInfo
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- WO2013089483A1 WO2013089483A1 PCT/KR2012/010911 KR2012010911W WO2013089483A1 WO 2013089483 A1 WO2013089483 A1 WO 2013089483A1 KR 2012010911 W KR2012010911 W KR 2012010911W WO 2013089483 A1 WO2013089483 A1 WO 2013089483A1
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- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
- H01M4/5825—Oxygenated metallic salts or polyanionic structures, e.g. borates, phosphates, silicates, olivines
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
- C01B25/37—Phosphates of heavy metals
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
- C01B25/37—Phosphates of heavy metals
- C01B25/375—Phosphates of heavy metals of iron
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
- C01B25/45—Phosphates containing plural metal, or metal and ammonium
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G37/00—Compounds of chromium
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G49/00—Compounds of iron
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
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- C—CHEMISTRY; METALLURGY
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- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/50—Solid solutions
- C01P2002/52—Solid solutions containing elements as dopants
- C01P2002/54—Solid solutions containing elements as dopants one element only
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
- C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/03—Particle morphology depicted by an image obtained by SEM
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to a metal-doped crystalline iron phosphate, a method for preparing the same, and an olivine-structured lithium composite metal phosphate prepared therefrom, and more particularly, to an olivine-structured lithium composite metal phosphate used as a cathode active material for a lithium secondary battery.
- a metal-doped crystal is used as a precursor of (LiMFePO 4, below LMFP) St. iron phosphate (MFePO 4, below MFP) and its production method.
- the olivine structure-type LMFP which is generally used as a cathode active material for lithium secondary batteries, has been produced in a heterometal-doped LMFP (LiMFePO 4 ) by solid phase mixing of dissimilar metals.
- the solid phase raw material is present in the manufacturing process of the LMFP, to prepare the nano-sized LMFP particles, fine raw materials or grinding of the raw materials must be performed, and the control of the particle shape and size is more limited than that of the liquid phase method.
- a solid solution such as LiFe 1-x M x PO 4 may not be formed properly, and may exist as phase separation into LiFePO 4 and LiMPO 4 .
- the present inventors doped metal when preparing crystalline iron phosphate used as a precursor of LMFP, that is, inducing metal doping while preparing crystalline iron phosphate by adding a small amount of dissimilar metal in the process of crystallizing amorphous iron phosphate.
- the present invention has been found to produce LMFP from the crystalline iron phosphate can be increased efficiency and lower the process cost than the solid phase mixing of dissimilar metals.
- an object of the present invention is to provide a metal-doped crystalline iron phosphate which is a precursor material capable of efficiently preparing olivine structured LMFP used as a cathode active material for lithium secondary batteries.
- Another object of the present invention is to provide a method for preparing metal-doped crystalline iron phosphate which is a precursor material capable of efficiently preparing olivine structured LMFP used as a cathode active material for lithium secondary batteries.
- Another object of the present invention is to provide an olivine structured LMFP which is used as a cathode active material for lithium secondary batteries manufactured by using metal-doped crystalline iron phosphate as a precursor.
- the present invention provides a metal doped crystalline iron phosphate having the following formula (I) doped with a dissimilar metal while crystallizing the amorphous iron phosphate:
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga and Mg.
- the molar ratio of [Fe] and [M] is 1-x: x, wherein x is 0.01 to 0.05.
- the crystal structure of the metal doped crystalline iron phosphate includes metastronite 1.
- the present invention comprises the steps of forming amorphous iron phosphate; Mixing dissimilar metal salts with amorphous iron phosphate; And crystallizing the amorphous iron phosphate mixed with the dissimilar metal salts.
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga and Mg.
- the molar ratio of [Fe] and [M] is 1-x: x, where x is 0.01 to 0.05.
- the dissimilar metal salt is selected from the group consisting of the following structure, MX 3 (wherein M is Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, and Mg, X preferably has an anion including halogen).
- the amorphous iron phosphate is mixed in the liquid phase with the dissimilar metal salt aqueous solution in the form of a slurry.
- the present invention is an olivine structure type LMFP used as a positive electrode active material for lithium secondary batteries of formula (II) prepared by using a metal-doped crystalline iron phosphate having the formula (I) as a precursor Provides:
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, and Mg.
- Metal-doped crystalline iron phosphate prepared by inducing metal doping in the preparation of crystalline iron phosphate used as a precursor of LMFP has the following effects.
- olivine-structured LMFP with metal-doped crystalline iron phosphate may be more efficient and reduce process costs than the method of producing a mixed mixture of dissimilar metals.
- the metal composition of the metal doped iron phosphate or LMFP can be variously prepared without phase separation.
- FIG. 1 is a diffraction pattern of X-doped chromium-doped crystalline iron phosphate (CrFePO 4 ) according to an embodiment of the present invention.
- Figure 2 is an image showing the SEM results of the chromium doped iron phosphate in accordance with an embodiment of the present invention.
- Figure 3 is an image showing the SEM results of aluminum doped iron phosphate (AlFePO 4 ) according to another embodiment of the present invention.
- LiCrFePO 4 is a diffraction pattern of XRD of LiCrFePO 4 prepared using chromium-doped crystalline iron phosphate (CrFePO 4 ) as a precursor according to another embodiment of the present invention.
- Fig 5 is a SEM image showing a result of synthesis by LiCrFePO 4 CrFePO 4 according to another embodiment of the present invention.
- Figure 6 is a SEM image showing a result of synthesis by LiAlFePO 4 AlFePO 4 according to another embodiment of the present invention.
- the invention is a metal doped crystalline iron phosphate (MFP) having the following formula (I) doped with a dissimilar metal while crystallizing amorphous iron phosphate.
- MFP metal doped crystalline iron phosphate
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga and Mg.
- amorphous iron phosphate (amorphous FePO 4 ) is crystallized to crystalline iron phosphate is used as a precursor of LMFP used as a cathode active material of a lithium secondary battery.
- a small amount of dissimilar metal is added to the crystallization step of iron phosphate, that is, a metal doped crystalline iron phosphate (MFP) is obtained by inducing metal doping while preparing crystalline iron phosphate, thereby producing the metal doped crystalline iron.
- MFP metal doped crystalline iron phosphate
- LMFP may be more efficient and reduce process costs than solid phase mixing of dissimilar metals.
- Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, or Mg may be used, and preferably chromium, aluminum or Vanadium can be used.
- the molar ratio of [Fe] and [M] may be mixed so that 1-x: x, where x is in the range of 0.01 to 0.05.
- the crystal structure of the crystalline metal-doped iron phosphate includes metastronite 1.
- the present invention comprises the steps of forming amorphous iron phosphate; Mixing dissimilar metal salts with amorphous iron phosphate; And crystallizing the amorphous iron phosphate mixed with the dissimilar metal salts.
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, and Mg.
- Forming the amorphous iron phosphate may be prepared according to methods generally used in the art.
- the raw material may be prepared by mixing FeCl 3 with (NH 4 ) 2 HPO 4 or NH 4 H 2 PO 4 in a liquid state, followed by reaction.
- the [Fe]: [P] molar ratio may be in the range of 1: 0.9 to 1, and the volume ratio of the solid to the solvent is preferably 5 to 15%.
- the pH of the reactants it is preferable to adjust the pH of the reactants to 4 to 7, it can be reacted by stirring for 10 to 300 minutes at a temperature of 25 to 70 °C.
- the reactant is preferably washed 2 to 5 times using a reduced pressure filter or centrifuse and then dried.
- the dissimilar metal In the step of mixing the dissimilar metal with the amorphous iron phosphate, it is mixed before the crystallization of the amorphous iron phosphate to induce doping of the dissimilar metal.
- metals added to induce doping include Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, and Mg, preferably chromium or aluminum, or Vanadium can be used.
- the molar ratio of [Fe] and [M] may be mixed to be 1-x: x, where x is in the range of 0.01 to 0.05.
- the dissimilar metal salt is selected from the group consisting of the following structure, MX 3 (wherein M is Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, and Mg); , X is an anion including a halogen).
- the amorphous iron phosphate may be mixed in a liquid form with a heterogeneous metal salt aqueous solution in a slurry form to be uniformly mixed.
- the step of crystallizing the amorphous iron phosphate mixed with the dissimilar metal salt it is crystallized by heating under strong acid.
- the pH is adjusted by adding something such as phosphoric acid or hydrochloric acid in the range of 1 to 3 and heating with stirring for 1 to 6 hours at 90 to 100 ° C.
- the reaction is terminated when the color of the reactant becomes bright.
- the reactant is preferably washed 2 to 5 times using a reduced pressure filter or centrifuse and then dried.
- the crystal structure of the iron phosphate hydrate has a structure of styrene, metastronzite 1, and metastronzide 2, when the pH is 3-4 in the crystallization step Strainite, metastronzite 1 when pH 1-2 is produced, and metastranzite 2 when pH 0-1 is produced. Depending on the pH, a mixture of strontite or metastronite 2 may be produced.
- the metal-doped crystalline iron phosphate obtained through the above process may be used as a precursor to prepare the olivine structured LMFP used as a cathode active material for lithium secondary batteries.
- the present invention provides an olivine structured LMFP using a metal doped crystalline iron phosphate having the following formula (I) as a cathode active material for a lithium secondary battery of the following formula (II) prepared from a precursor: to be.
- M is selected from the group consisting of Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga and Mg.
- LiOH, Li 2 CO 3 or LiCl may be used as a raw material including Li, and sucrose, glucose, escorbic acid or oleic acid may be used as the carbon coating raw material, but the present invention is limited thereto. It is not.
- the heat treatment is preferably performed for 4 to 12 hours at a temperature of 500 to 800 ° C. in a 1 to 5% H 2 / N 2 mixed gas atmosphere.
- FeCl 3 and (NH 4 ) 2 HPO 4 were taken to have a [Fe]: [P] molar ratio of 1: 1, mixed in pure water, and mixed to form a slurry. At this time, the ratio of the solid content to the solvent was 10%. Subsequently, ammonia water (NH 4 OH) was added to the mixed slurry to adjust the pH to 4.5. The pH adjusted slurry was then stirred at 60 ° C. for 15 minutes. The reaction slurry was then washed three times using a reduced pressure filter. The washed cake was dried in a 90 ° C. oven to synthesize amorphous iron phosphate hydrate.
- NH 4 OH ammonia water
- PrCl 3 chromium trichloride
- the chromium-doped crystalline iron phosphate hydrate was observed by XRD (D / Max-2500VK / PC by Rikagu, CuKa radiation, speed 4 ° min -1 ), and its diffraction pattern is shown in FIG. 1, and SEM (JEOL Corporation) JSM-7400F, 20 kV) and observed the particle shape thereof is shown in Figure 2 the results.
- FeCl 3 and (NH 4 ) 2 HPO 4 were taken to have a [Fe]: [P] molar ratio of 1: 0.95, mixed in pure water, and mixed to form a slurry. At this time, the ratio of the solid content to the solvent was 10%. Subsequently, ammonia water (NH 4 OH) was added to the mixed slurry to adjust the pH to 4.5. The pH adjusted slurry was then stirred at 60 ° C. for 15 minutes. The reaction slurry was then washed three times using a reduced pressure filter. The washed cake was dried in a 90 ° C. oven to synthesize amorphous iron phosphate hydrate.
- NH 4 OH ammonia water
- Phosphoric acid (H 3 PO 4 ) was added to the slurry to adjust the pH to 2. The pH adjusted slurry was then stirred at 95 ° C. for 3 hours. The reaction was terminated when the color of the slurry became bright. The reaction slurry was then washed three times using a reduced pressure filter, and the washed cake was dried in an oven at 90 ° C. to synthesize aluminum doped crystalline iron phosphate hydrate.
- the aluminum-doped crystalline iron phosphate was photographed by SEM to observe its particle shape, and the results are shown in FIG. 3.
- Chromium doped crystalline iron phosphate hydrate (crystalline CrFePO 4 2H 2 LiCrFePO using O) 4 Synthesis of
- Example 2 15 g of chromium doped crystalline iron phosphate hydrate prepared in Example 1 was dry mixed with 3.3 g of Li raw material and 1.2 g of carbon coated raw material. The mixed powder was heat-treated at 650 ° C. for 8 hours in a 3% H 2 / N 2 mixed gas atmosphere to synthesize LiCrFePO 4 .
- the synthesized LiCrFePO 4 was observed with XRD, and the diffraction pattern thereof is shown in FIG. 4, and the result was shown in FIG. 5 by SEM.
- Fig. 4 from the XRD diffraction pattern of the synthesized LiCrFePO 4, it can be seen that forms a crystalline olivine (olivine) structure.
- the particles have a nano size.
- Example 2 15 g of aluminum-doped crystalline iron phosphate hydrate prepared in Example 2 was dry mixed with 3.3 g of Li raw material and 1.2 g of carbon coated raw material. The mixed powder was heat-treated at 650 ° C. for 8 hours in a 3% H 2 / N 2 mixed gas atmosphere to synthesize LiAlFePO 4 .
- the synthesized LiAlFePO 4 was taken by SEM to observe its particle shape, and the results are shown in FIG. 6.
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Claims (8)
- 비결정 철인산염을 결정화시키면서 이종 금속을 도핑시킨 하기 식 (I)을 갖는 금속 도핑된 결정성 철인산염:식 IMFePO4여기서, M은 Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga 및 Mg으로 이루어진 군으로부터 선택됨.
- 제1항에 있어서.상기 금속 도핑된 결정성 철인산염의 결정구조는 메타스트렌자이트 1를 포함하는 것인 금속 도핑된 결정성 철인산염.
- 제1항에 있어서.상기 [Fe]와 [M]의 몰비는 1-x:x 이고, 여기서 x는 0.01 내지 0.05인 금속 도핑된 결정성 철인산염.
- 비결정성 철인산염을 형성하는 단계;비결정성 철인산염에 이종 금속염을 혼합시키는 단계; 및이종 금속염이 혼합된 비결정성 철인산염을 결정화시키는 단계를 포함하는 하기 식 I의 금속 도핑된 결정성 철인산염의 제조방법:식 IMFePO4여기서, M은 Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga 및 Mg로 이루어진 군으로부터 선택됨.
- 제4항에 있어서,상기 비결정성 철인산염과 이종 금속염을 혼합시켜 결정화시키는 단계에서 Fe와 M의 몰비는 1-x:x 이고, 여기서 x는 0.01 내지 0.05인 금속 도핑된 결정성 철인산염의 제조방법.
- 제4항에 있어서,상기 이종 금속염은 MX3(여기서, M은 Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, 및 Mg로 이루어진 군으로부터 선택되고, X는 할로겐을 포함한 음이온) 구조를 갖는 것인 금속 도핑된 결정성 철인산염의 제조방법.
- 제4항에 있어서,상기 비결정성 철인산염은 슬러리 형태로 이종 금속염 수용액과 액상에서 혼합되는 것인 금속 도핑된 결정성 철인산염의 제조방법.
- 제1항 또는 제2항에 따른 하기 식 (I)을 갖는 금속 도핑된 결정성 철인산염을 전구체로 하여 제조된 하기 식 (Ⅱ)의 리튬 2차전지용 양극 활물질로 사용되는 감람석 구조형 LMFP.식 IMFePO4식 IILiMFePO4상기 식 I 및 II에서, M은 Ni, Co, Mn, Cr, Zr, Nb, Cu, V, Ti, Zn, Al, Ga, 및 Mg로 이루어진 군으로부터 선택됨.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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JP2014547105A JP6300417B2 (ja) | 2011-12-16 | 2012-12-14 | 金属ドーピングされた結晶性鉄リン酸塩、その製造方法及びそれから製造されたリチウム複合金属リン酸化物 |
CN201280061307.1A CN104024154B (zh) | 2011-12-16 | 2012-12-14 | 金属掺杂结晶磷酸铁、其制备方法以及由其制备的锂复合金属磷酸盐 |
EP12857999.2A EP2792636B1 (en) | 2011-12-16 | 2012-12-14 | Method for preparing crystalline iron phosphates doped with metal |
CA2854760A CA2854760C (en) | 2011-12-16 | 2012-12-14 | Crystalline iron phosphate doped with metal, method of preparing the same, and lithium composite metal phosphate prepared therefrom |
US14/360,338 US9190665B2 (en) | 2011-12-16 | 2012-12-14 | Crystalline iron phosphate doped with metal, method of preparing the same, and lithium composite metal phosphate prepared therefrom |
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KR10-2011-0136536 | 2011-12-16 | ||
KR1020110136536A KR101893955B1 (ko) | 2011-12-16 | 2011-12-16 | 금속 도핑된 결정성 철인산염, 이의 제조 방법 및 이로부터 제조된 리튬 복합금속인산화물 |
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EP (1) | EP2792636B1 (ko) |
JP (1) | JP6300417B2 (ko) |
KR (1) | KR101893955B1 (ko) |
CN (1) | CN104024154B (ko) |
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KR102062705B1 (ko) | 2013-06-14 | 2020-01-06 | 삼성에스디아이 주식회사 | 리튬 금속인산화물의 제조방법 |
KR102172027B1 (ko) * | 2013-12-30 | 2020-11-02 | 삼성에스디아이 주식회사 | 리튬 전이금속 인산화물의 제조방법 및 그 방법에 의해 제조된 리튬 전이금속 인산화물 |
CN106082328B (zh) * | 2016-06-22 | 2017-10-20 | 西安工业大学 | 一种铁掺杂砷酸镓压电材料及其制备方法 |
CN107601447A (zh) * | 2016-07-12 | 2018-01-19 | 南通亨利锂电新材料有限公司 | 一种复合晶相正磷酸铁及其制备方法 |
CN106185857A (zh) * | 2016-07-18 | 2016-12-07 | 铜陵纳源材料科技有限公司 | 一种电池级磷酸铁及其制备方法 |
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CN104024154B (zh) | 2016-10-26 |
KR20130074806A (ko) | 2013-07-05 |
CN104024154A (zh) | 2014-09-03 |
JP2015506897A (ja) | 2015-03-05 |
EP2792636A1 (en) | 2014-10-22 |
CA2854760C (en) | 2020-07-14 |
KR101893955B1 (ko) | 2018-09-03 |
US20140319413A1 (en) | 2014-10-30 |
US9190665B2 (en) | 2015-11-17 |
JP6300417B2 (ja) | 2018-03-28 |
EP2792636A4 (en) | 2015-11-11 |
EP2792636B1 (en) | 2019-04-17 |
CA2854760A1 (en) | 2013-06-20 |
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