KR100830529B1 - 고순도 하프늄아미드의 제조방법 - Google Patents
고순도 하프늄아미드의 제조방법 Download PDFInfo
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- KR100830529B1 KR100830529B1 KR1020070015350A KR20070015350A KR100830529B1 KR 100830529 B1 KR100830529 B1 KR 100830529B1 KR 1020070015350 A KR1020070015350 A KR 1020070015350A KR 20070015350 A KR20070015350 A KR 20070015350A KR 100830529 B1 KR100830529 B1 KR 100830529B1
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- hafnium
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- distillate
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- 229910052735 hafnium Inorganic materials 0.000 title claims abstract description 149
- -1 hafnium amide Chemical class 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims description 21
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 113
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 111
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 61
- 238000004821 distillation Methods 0.000 claims description 32
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 14
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- MLWPJXZKQOPTKZ-UHFFFAOYSA-N benzenesulfonyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1 MLWPJXZKQOPTKZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 239000011521 glass Substances 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000009616 inductively coupled plasma Methods 0.000 description 16
- 238000004611 spectroscopical analysis Methods 0.000 description 16
- 238000004255 ion exchange chromatography Methods 0.000 description 14
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 11
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- GOVWJRDDHRBJRW-UHFFFAOYSA-N diethylazanide;zirconium(4+) Chemical compound [Zr+4].CC[N-]CC.CC[N-]CC.CC[N-]CC.CC[N-]CC GOVWJRDDHRBJRW-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 2
- YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- RHIUIXSTQSQFAX-UHFFFAOYSA-N lithium ethyl(methyl)azanide Chemical compound [Li+].CC[N-]C RHIUIXSTQSQFAX-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
- (a) 카르보닐기 또는 술포닐기를 함유하며, 화학식 A(OyXOnRf)m으로 표시되는 화합물을, 화학식 Hf[N(R1)(R2)]4로 표시되고, 지르코늄 성분을 불순물로 함유하는 미정제된(crude) 하프늄아미드에 첨가하는 단계; 및(b) 상기 (a)의 단계의 생성물을 감압 하에서 증류하여, 상기 미정제된(crude) 하프늄아미드로부터 상기 지르코늄 성분을 제거하는 단계;로 이루어진 고순도 하프늄아미드의 제조방법.상기 화학식 A(OyXOnRf)m에서, A는 수소원자, 산소원자 또는 하프늄원자이며,상기 A가 수소원자 또는 산소원자일 때, X는 탄소원자 또는 황원자이고,상기 A가 하프늄원자일 때, X는 황원자이고,상기 A 및 X가 각각 수소원자 및 탄소원자일 때, m, n 및 y 각각은 1이고,상기 A 및 X가 각각 수소원자 및 황원자일 때, m, n 및 y 각각은 1, 2 및 1이고,상기 A가 산소원자이고, 상기 X가 탄소원자일 때, m, n 및 y 각각은 2, 1 및 0이고,상기 A가 산소원자이고, 상기 X가 황원자일 때, m, n 및 y 각각은 2, 2 및 0이고,상기 A가 하프늄원자일 때, m, n 및 y 각각은 4, 2 및 1이고,상기 A가 수소원자 또는 산소원자일 때, Rf는 C1 내지 C12의 알킬기, C1 내지 C12의 퍼플루오로알킬기, C6 내지 C12의 아릴기 또는 C4 내지 C12의 헤테로아릴기이고,상기 A가 하프늄원자일 때, Rf는 C1 내지 C12의 퍼플루오로알킬기이고,상기 화학식 Hf[N(R1)(R2)]4에서, 상기 R1 및 R2는 각각 독립적으로 메틸기 또는 에틸기이다.
- 제 1 항에 있어서,(c) 화학식 Li(NR3R4)으로 표시되는 상기에서, R3 및 R4가 독립적으로 메틸기 또는 에틸기를 나타내는 리튬알킬아미드를, 단계 (b)에서 수득된 증류물에 첨가하는 단계; 및(d) 단계 (c)의 생성물을 감압 하에서 증류하는 단계;를 더 포함하여 이루어지는 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 단계 (a)의 화합물을 단계 (b)의 생성물에 첨가하는 단계를 반복 수행하는 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 미정제된 하프늄아미드가 테트라키스(디에틸아미도)하프늄인 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 단계 (a)의 화합물이 아세트산, 트리플루오로아세트산, 벤조산, 메탄술폰산, 트리플루오로메탄술폰산, 벤젠술폰산, 아세트산무수물, 트리플루오로아세트산무수물, 벤조산무수물, 메탄술폰산무수물, 트리플루오로메탄술폰산무수물, 벤젠술폰산무수물 및 하프늄 트리플루오로메탄술포네이토로 이루어지는 군으로부터 선택되는 하나인 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 단계 (a)의 화합물이 트리플루오로메탄술폰산, 하프늄 트리플루오로메탄술포네이토, 트리플루오로메탄술폰산무수물, 트리플루오로아세트산, 메탄술폰산, 벤젠술폰산 및 메탄술폰산무수물로 이루어지는 군으로부터 선택되는 하나인 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 단계 (a)의 화합물이 트리플루오로메탄술폰산인 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 1 항에 있어서,상기 단계 (b)의 증류가 0.01 내지 0.60㎪의 압력 하에서 수행되는 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 2 항에 있어서,상기 단계 (c)의 리튬알킬아미드에서, 화학식 R3R4로 표시되는 알킬 치환체가 상기 단계 (a)의 하프늄아미드에서 화학식 (R1)(R2)로 표시되는 알킬 치환체와 동일한 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
- 제 2 항에 있어서,상기 단계 (d)의 증류가 0.01 내지 0.60㎪의 압력 하에서 수행되는 것을 특징으로 하는 상기 고순도 하프늄아미드의 제조방법.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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JP2006042934 | 2006-02-20 | ||
JPJP-P-2006-00042934 | 2006-02-20 | ||
JP2006312847 | 2006-11-20 | ||
JPJP-P-2006-00312847 | 2006-11-20 | ||
JP2007002547 | 2007-01-10 | ||
JPJP-P-2007-00002547 | 2007-01-10 |
Publications (2)
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KR20070083182A KR20070083182A (ko) | 2007-08-23 |
KR100830529B1 true KR100830529B1 (ko) | 2008-05-22 |
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KR1020070015350A KR100830529B1 (ko) | 2006-02-20 | 2007-02-14 | 고순도 하프늄아미드의 제조방법 |
Country Status (4)
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US (1) | US7319158B2 (ko) |
JP (1) | JP4770744B2 (ko) |
KR (1) | KR100830529B1 (ko) |
TW (1) | TWI329113B (ko) |
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JP5088232B2 (ja) * | 2007-06-26 | 2012-12-05 | セントラル硝子株式会社 | ハフニウム錯体の製造方法 |
JP5401950B2 (ja) | 2008-12-02 | 2014-01-29 | セントラル硝子株式会社 | ハフニウムアミド錯体の製造方法及びハフニウム含有酸化膜 |
Citations (3)
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JP2004250431A (ja) * | 2003-01-27 | 2004-09-09 | Mitsubishi Materials Corp | 有機金属化合物及びその合成方法並びに該化合物を含む溶液原料、金属含有薄膜 |
JP2005263771A (ja) * | 2004-02-18 | 2005-09-29 | Shinko Kagaku Kogyo Kk | 高純度テトラキス(ジアルキルアミノ)ハフニウムの製造法 |
JP2007051042A (ja) * | 2005-08-19 | 2007-03-01 | Tri Chemical Laboratory Inc | ハフニウム化合物の製造方法、Zr不純物が50ppm以下のハフニウム化合物、及びハフニウム系膜の成膜方法 |
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JP3698163B1 (ja) * | 2003-09-19 | 2005-09-21 | 三菱マテリアル株式会社 | ハフニウム含有膜形成材料及び該材料から作製されたハフニウム含有薄膜の製造方法 |
US20060062910A1 (en) * | 2004-03-01 | 2006-03-23 | Meiere Scott H | Low zirconium, hafnium-containing compositions, processes for the preparation thereof and methods of use thereof |
JP4562169B2 (ja) * | 2004-04-12 | 2010-10-13 | 株式会社高純度化学研究所 | Hf系酸化物ゲート絶縁膜のプリカーサーの精製方法 |
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JP2004250431A (ja) * | 2003-01-27 | 2004-09-09 | Mitsubishi Materials Corp | 有機金属化合物及びその合成方法並びに該化合物を含む溶液原料、金属含有薄膜 |
JP2005263771A (ja) * | 2004-02-18 | 2005-09-29 | Shinko Kagaku Kogyo Kk | 高純度テトラキス(ジアルキルアミノ)ハフニウムの製造法 |
JP2007051042A (ja) * | 2005-08-19 | 2007-03-01 | Tri Chemical Laboratory Inc | ハフニウム化合物の製造方法、Zr不純物が50ppm以下のハフニウム化合物、及びハフニウム系膜の成膜方法 |
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JP2008189550A (ja) | 2008-08-21 |
US20070197809A1 (en) | 2007-08-23 |
TW200745145A (en) | 2007-12-16 |
JP4770744B2 (ja) | 2011-09-14 |
KR20070083182A (ko) | 2007-08-23 |
TWI329113B (en) | 2010-08-21 |
US7319158B2 (en) | 2008-01-15 |
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