KR20100048020A - Novel strontium aminoalkoxide complexes and process for preparing thereof - Google Patents
Novel strontium aminoalkoxide complexes and process for preparing thereof Download PDFInfo
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- 229910052712 strontium Inorganic materials 0.000 title claims abstract description 37
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 6
- -1 strontium alkoxide compound Chemical class 0.000 claims abstract description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 7
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 claims description 23
- 150000003438 strontium compounds Chemical class 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- 239000002105 nanoparticle Substances 0.000 claims description 6
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000004455 differential thermal analysis Methods 0.000 description 12
- 238000002411 thermogravimetry Methods 0.000 description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000005229 chemical vapour deposition Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WPHDRRPDGCWABO-UHFFFAOYSA-N CN(CC(COCC(CC)(O[Sr])C)(C)C)C Chemical compound CN(CC(COCC(CC)(O[Sr])C)(C)C)C WPHDRRPDGCWABO-UHFFFAOYSA-N 0.000 description 3
- 229910002367 SrTiO Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000015654 memory Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- OLVOYOKLPWWMFN-UHFFFAOYSA-N CC(C)(C(NCCCN(C)C)NCCCN(C)C)O Chemical compound CC(C)(C(NCCCN(C)C)NCCCN(C)C)O OLVOYOKLPWWMFN-UHFFFAOYSA-N 0.000 description 1
- YELDSNLHQPEKCV-UHFFFAOYSA-N CN(CC(COCC(CC)(O)C)(C)C)C Chemical compound CN(CC(COCC(CC)(O)C)(C)C)C YELDSNLHQPEKCV-UHFFFAOYSA-N 0.000 description 1
- CGDHCDFSXHKTCI-UHFFFAOYSA-N COCCNC(C(C)(O)C)NCCOC Chemical compound COCCNC(C(C)(O)C)NCCOC CGDHCDFSXHKTCI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910002370 SrTiO3 Inorganic materials 0.000 description 1
- DCFPCVWMLIEHLH-UHFFFAOYSA-N [H]N[Sr] Chemical compound [H]N[Sr] DCFPCVWMLIEHLH-UHFFFAOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052454 barium strontium titanate Inorganic materials 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical class C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G15/00—Compounds of gallium, indium or thallium
- C01G15/006—Compounds containing, besides gallium, indium, or thallium, two or more other elements, with the exception of oxygen or hydrogen
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G23/00—Compounds of titanium
- C01G23/003—Titanates
- C01G23/006—Alkaline earth titanates
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G35/00—Compounds of tantalum
- C01G35/006—Compounds containing, besides tantalum, two or more other elements, with the exception of oxygen or hydrogen
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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
- C01G49/009—Compounds containing, besides iron, two or more other elements, with the exception of oxygen or hydrogen
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G51/00—Compounds of cobalt
- C01G51/006—Compounds containing, besides cobalt, two or more other elements, with the exception of oxygen or hydrogen
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Abstract
Description
본 발명은 신규의 스트론튬 알콕사이드 화합물에 관한 것으로서, 보다 상세하게는 양질의 스트론튬 산화물 박막과 나노입자, 그리고 SrTiO3, SrBi2Ta2O9, BaxSr1-xTiO3, LaSrCoFe, SrGa2S4:Ce 등과 같은 스트론튬을 포함하는 화합물을 형성하기 위한 전구체로서 열적으로 안정하고 휘발성이 증가된 신규한 스트론튬 알콕사이드 화합물 및 그 제조방법에 관한 것이다. The present invention relates to a novel strontium alkoxide compound, and more particularly to a high quality strontium oxide thin film and nanoparticles, and SrTiO 3 , SrBi 2 Ta 2 O 9 , Ba x Sr 1-x TiO 3 , LaSrCoFe, SrGa 2 S 4 : Ce The present invention relates to a novel strontium alkoxide compound which is thermally stable and has increased volatility as a precursor for forming a compound including strontium, and a method for producing the same.
스트론튬 화합물은 SrTiO3, SrBi2Ta2O9, BaxSr1-xTiO3, LaSrCoFe 등의 형태로 제조되어 산소-이온성 및 전자 전도성 박막 필름(oxygen-ionic and electronic conductive thin film)에 사용되고, SrGa2S4:Ce 등으로 제조되어 박막 필름 전기발광 표시(thin film electroluminescent displays)에 사용되는데, 상기와 같이 스트론튬을 포함하는 이종금속 박막의 제조에 있어서, 상기의 물질을 제조하기 위한 전구체 및 나노 크기의 스트론튬 산화물, 스트론튬을 포함하는 이종금속 입자 제조를 위한 전구체로서 이러한 스트론튬 화합물이 유용하게 사용된다. Strontium compounds are manufactured in the form of SrTiO 3 , SrBi 2 Ta 2 O 9 , Ba x Sr 1-x TiO 3 , LaSrCoFe, etc., and are used for oxygen-ionic and electronic conductive thin films. , SrGa 2 S 4 : Ce and the like, which are used for thin film electroluminescent displays. In the production of a dissimilar metal thin film containing strontium as described above, a precursor for preparing the material and Such strontium compounds are usefully used as precursors for the production of dissimilar metal particles including nano-size strontium oxide and strontium.
또한, 알칼리 토금속(Alkaline earth metal)을 포함하는 산화물로서 페로브스카이트(Perovskite)구조를 갖는 바륨 티타네이트 (BaTiO3), 바륨 스트론튬 티타네이트 ((Ba,Sr)TiO3)는 비휘발 강유전성 메모리(nonvolatile ferroelectric memories), 마이크로파 소자(microwave devices), 동적 램(dynamic random access memories;DRAMs), 다층 축전기(multilayer capacitors), 전기 광학 소자(electro optical device), 액추에이터(actuators), 변환기(transducers), 고유전체(high-k dielectrics), 미세전자기계 시스템(micro-electro-mechanical systems; MEMs)등 다양하게 응용된다 (Zhao, J.; Wang, X.; Chen, R.;Li, L. Materials Letters 2005, 59, 2329; Mao, Y.; Baneriee, S.; Wong, S.S. J. Am. Chem. Soc. 2003, 125, 15718; Gong, D.; Grimes, C.A.; Varghese, O.K; Hu, W.; Singh, R.S.; Chen, Z.; Dickey, D.J. J. Mater. Res. 2001, 16, 3331; Padture, N.P. Wei, X.Z. J. Am. Ceram. 2003, 86, 2215; Phule, P.P.; Risbud, S.H. J. Mater. Sci. 1990, 25, 1169; Hill, N.A. J. Phys. Chem. B 2000, 104, 6694). 또한, SrO는 Si과 SrTiO3 사이의 완충층(buffer layer)으로 잘 알려져 있으며 SrGa2S4:Ce 와 같은 알칼리 토 티오갈레이트(alkaline earth thiogallates)는 전기발광표시(electroluminescent displays)의 인광박막(phosphor thin films)으로 연구되고 있다 (Asaoka, H.; Saiki, K.; Koma, A.; Yamamoto, H. Thin Solid Films 2000, 369, 273; Okamoto, S.; Tanaka, K.; Inoue, Y. Appl. Phys. Lett. 2000, 76, 946; Tanaka, K.; Inoue, Y.; Okamoto, S.; Kobayashi, K. J. Cryst. Gorwth 1995, 150, 1211). In addition, barium titanate (BaTiO 3 ) and barium strontium titanate ((Ba, Sr) TiO 3 ) having a perovskite structure as an oxide containing alkaline earth metal are nonvolatile ferroelectric memory. (nonvolatile ferroelectric memories), microwave devices, dynamic random access memories (DRAMs), multilayer capacitors, electro optical devices, actuators, transducers, Various applications include high-k dielectrics and micro-electro-mechanical systems (MEMs) (Zhao, J .; Wang, X .; Chen, R .; Li, L. Materials Letters 2005 , 59, 2329; Mao, Y .; Baneriee, S .; Wong, SS J. Am. Chem. Soc. 2003 , 125, 15718; Gong, D .; Grimes, CA; Varghese, OK; Hu, W. ; Singh, RS; Chen, Z .; Dickey, DJ J. Mater.Res . 2001 , 16, 3331; Padture, NP Wei, XZ J. Am. Ceram. 2003 , 86, 2215; Phule, PP; Risbud, SH J. Mater. Sci. 1990 , 25, 1169; Hill, NA J. Phys. Chem.
상기에 언급한 물질들을 제조하기 위해 졸-겔(sol-gel), MOD(metal-organic decomposition), PLD(pulsed laser ablation), CVD(chemical vapor deposition) MOCVD(metal-organic chemical vapor deposition) 등과 같은 다양한 방법이 이용되고 있으며, 전구체로는 알콕사이드(alkoxides), 아릴록사이드(aryloxides), 비-디케토네이트(b-diketonates), 메탈로센(metallocenes) , 비스트리메틸실릴아미드( bis(trimethylsilyl)amide), 알킬아미드(alkylamide) 등 다양하게 알려져 있으나 대부분 다이머(dimer) 이상으로 휘발온도가 매우 높아 휘발성 개선을 위해 플루오르화(fluorinated) 화합물이 사용되는데, 이는 박막 내에서 플루오르화 물질(fluoride)의 오염을 일으키는 단점이 있다. ( Paw, W.; Baum, T.H.; Lam, K.-C.; Rheingold, A.L. Inorg. Chem. 2000, 39, 2011; Mizushima, Y.; Hirabayashi, I. J. Mater. Res. 1996, 11, 2698; Shamlian, S.H.; Hitchman, M.L.; Cook, S.L.; Richards. B.C. J. Mater Chem. 1994, 4, 81; Gardiner, R.A.; Brown, D.W.; Kirlin, P.S.; Rheingold, A.L. Chem. mater. 1991, 3, 1053)In order to produce the above-mentioned materials, such as sol-gel, metal-organic decomposition (MOD), pulsed laser ablation (PLD), chemical vapor deposition (CVD) and metal-organic chemical vapor deposition (MOCVD) Various methods are used, and precursors include alkoxides, aryloxides, b-diketonates, metallocenes, and bis (trimethylsilyl) amides. ), Alkylamide, etc., but are widely known. Most of them have a higher volatilization temperature than dimers, so fluorinated compounds are used to improve volatility, which is contaminated with fluoride in the thin film. Has the disadvantage of causing. (Paw, W .; Baum, TH; Lam, K.-C .; Rheingold, AL Inorg. Chem. 2000 , 39, 2011; Mizushima, Y .; Hirabayashi, I. J. Mater. Res. 1996 , 11, 2698; Shamlian, SH; Hitchman, ML; Cook, SL; Richards. BC J. Mater Chem. 1994 , 4, 81; Gardiner, RA; Brown, DW; Kirlin, PS; Rheingold, AL Chem. Mater. 1991 , 3 , 1053)
본 발명자들은 새로운 리간드를 도입하여 스트론튬에 배위할 수 있는 여러 전자 주개 리간드가 배위하도록 함으로서 탄소나 할로겐의 오염을 일으키지 않으며 열적 안정성과 휘발성이 개선될 뿐만 아니라 좀 더 낮은 온도에서도 쉽게 스트론튬 산화물, 그리고 스트론튬을 포함하는 물질을 제조하기 위한 신규의 스트론튬 전구체를 개발하기에 이르렀다. The present inventors have introduced a new ligand to coordinate the various electron donor ligands capable of coordinating to strontium, which does not cause contamination of carbon or halogens, improves thermal stability and volatility, and easily strontium oxide and strontium at lower temperatures. It has led to the development of a new strontium precursor for producing a material comprising.
본 발명의 목적은 양질의 스트론튬 산화물 박막과 나노입자, 그리고 SrTiO3, SrBi2Ta2O9, BaxSr1-xTiO3, LaSrCoFe, SrGa2S4:Ce 등과 같은 스트론튬을 포함하는 화합물을 형성하기 위해 열적으로 안정하고 휘발성이 증가된 신규한 스트론튬 화합물 전구체 및 그 제조방법을 제공하는 데 있다.An object of the present invention is to provide high quality strontium oxide thin films and nanoparticles, and SrTiO 3 , SrBi 2 Ta 2 O 9 , Ba x Sr 1-x TiO 3 , LaSrCoFe, SrGa 2 S 4 : Ce The present invention provides a novel strontium compound precursor that is thermally stable and has increased volatility to form a compound including strontium, and a method of preparing the same.
본 발명은 상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1 로 표시되는 스트론튬 알콕사이드 화합물을 제공한다.The present invention to achieve the above object, the present invention provides a strontium alkoxide compound represented by the following formula (1).
[화학식 1][Formula 1]
Sr[O-CR1R2(CH2)m-A]2 Sr [O-CR 1 R 2 (CH 2 ) m -A] 2
상기 식에서 m은 1 내지 3 중에서 선택되는 정수이고;A는 선형 또는 분지형의 (C1-C20)알콕시기 또는 (C1-C20)알킬아민기이고;R1 및 R2는 서로 독립적으로 수소, 할로겐 또는 선형 또는 분지형의 (C1-C10)알킬기이며;상기 A의 알콕시기 또는 알킬아민기와 R1 및 R2의 알킬기는 서로 독립적으로 할로겐, 산소, 질소, (C1-C20)알콕시기, (C1-C20)알킬아민기 또는 (C1-C20)알킬기로 더 치환될 수 있다.Wherein m is an integer selected from 1 to 3; A is a linear or branched (C 1 -C 20) alkoxy group or (C 1 -C 20) alkylamine group; R 1 and R 2 are independently of each other hydrogen, halogen Or a linear or branched (C 1 -C 10) alkyl group; the alkoxy group or alkylamine group of A and the alkyl groups of R 1 and R 2 are independently of each other a halogen, oxygen, nitrogen, (C 1 -C 20) alkoxy group, (C 1 -C20) alkylamine group or (C1-C20) alkyl group.
또한, 본 발명은 하기 화학식 11 내지 화학식 16에서 선택되는 스트론튬 알콕사이드 화합물을 제공한다.The present invention also provides a strontium alkoxide compound selected from the following formulas (11) to (16).
[화학식 11][Formula 11]
Sr[O-CR1R2(CH2)m-O-B-NR3R4]2 Sr [O-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4 ] 2
[화학식 12][Formula 12]
Sr[O-CR1R2(CH2)m-N-(B-NR3R4)2]2 Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2 ] 2
[화학식 13][Formula 13]
Sr[O-CR1R2(CH2)m-N-(B-OR3)2]2 Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2 ] 2
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
Sr[O-CR1R2(CH2)m-O-B-OR3]2 Sr [O-CR 1 R 2 (CH 2 ) m -OB-OR 3 ] 2
상기 식에서 m은 서로 독립적으로 1 내지 3 중에서 선택되는 정수이고; B는 서로 독립적으로 선형 또는 분지형의 (C2-C10)알킬렌기이고; R1 내지 R5는 서로 독립적으로 수소, 할로겐 또는 선형 또는 분지형의 (C1-C10)알킬기이며; 상기 B의 알 킬렌, R1 내지 R5의 알킬기는 서로 독립적으로 할로겐, 산소, 질소, (C1-C20)알콕시기, (C1-C20)알킬아민기 또는 (C1-C20)알킬기로 더 치환될 수 있다.M is an integer selected from 1 to 3 independently of each other; B is, independently from each other, a linear or branched (C 2 -C 10) alkylene group; R 1 to R 5 independently of one another are hydrogen, halogen or a linear or branched (C 1 -C 10) alkyl group; Alkylene of B, alkyl groups of R 1 to R 5 may be independently substituted with a halogen, oxygen, nitrogen, (C 1 -C 20) alkoxy group, (C 1 -C 20) alkylamine group or (C 1 -C 20) alkyl group independently of one another. Can be.
또한, 본 발명은 상기의 스트론튬 알콕사이드 화합물을 전구체로 사용하여 스트론튬 화합물을 제조하는 방법을 제공한다. The present invention also provides a method for producing a strontium compound using the strontium alkoxide compound as a precursor.
또한, 본 발명은 상기 스트론튬 화합물로 스트론튬 산화물의 박막 또는 스트론튬 산화물의 나노 입자인 것을 특징으로 하는 스트론튬 화합물을 제조하는 방법을 제공한다.The present invention also provides a method for producing a strontium compound, characterized in that the strontium compound is a thin film of strontium oxide or nanoparticles of strontium oxide.
이하, 본 발명을 더욱 상세히 설명한다. Hereinafter, the present invention will be described in more detail.
본 발명은 상기 화학식 11 내지 화학식 16의 스트론튬 화합물은 상기 B가 -(CH2)n-또는 -(CH2)(CR3R4)(CH2)-으로 표시되는 하기 화학식 31 내지 화학식 40으로 표시되는 스트론튬 알콕사이드 화합물을 포함한다.In the present invention, the strontium compound of Formula 11 to Formula 16 is represented by Formula 31 to Formula 40, wherein B is represented by-(CH 2 ) n -or-(CH 2 ) (CR 3 R 4 ) (CH 2 )-. The strontium alkoxide compound represented is included.
[화학식 31][Formula 31]
Sr[OCR1R2(CH2)mN(R5)(CH2)nNR3R4]2 Sr [OCR 1 R 2 (CH 2 ) m N (R 5 ) (CH 2 ) n NR 3 R 4 ] 2
[화학식 32][Formula 32]
Sr[OCR1R2(CH2)mN(R5)(CH2)(CR3R4)(CH2)NR3R4]2 Sr [OCR 1 R 2 (CH 2 ) m N (R 5 ) (CH 2 ) (CR 3 R 4 ) (CH 2 ) NR 3 R 4 ] 2
[화학식 33][Formula 33]
Sr[OCR1R2(CH2)mO(CH2)nNR3R4]2 Sr [OCR 1 R 2 (CH 2 ) m O (CH 2 ) n NR 3 R 4 ] 2
[화학식 34][Formula 34]
Sr[OCR1R2(CH2)mO(CH2)(CR3R4)(CH2)NR3R4]2 Sr [OCR 1 R 2 (CH 2 ) m O (CH 2 ) (CR 3 R 4 ) (CH 2 ) NR 3 R 4 ] 2
[화학식 35][Formula 35]
Sr[OCR1R2(CH2)mN(R5)(CH2)nOR3]2 Sr [OCR 1 R 2 (CH 2 ) m N (R 5 ) (CH 2 ) n OR 3 ] 2
[화학식 36][Formula 36]
Sr[OCR1R2(CH2)mN(R5)(CH2)(CR3R4)(CH2)OR3]2 Sr [OCR 1 R 2 (CH 2 ) m N (R 5 ) (CH 2 ) (CR 3 R 4 ) (CH 2 ) OR 3 ] 2
[화학식 37][Formula 37]
Sr[OCR1R2(CH2)mO(CH2)nOR3]2 Sr [OCR 1 R 2 (CH 2 ) m O (CH 2 ) n OR 3 ] 2
[화학식 38][Formula 38]
Sr[OCR1R2(CH2)mO(CH2)(CR3R4)(CH2)OR3]2 Sr [OCR 1 R 2 (CH 2 ) m O (CH 2 ) (CR 3 R 4 ) (CH 2 ) OR 3 ] 2
[화학식 39][Formula 39]
Sr[OCR1R2(CH2)mN{(CH2)nNR3R4}2]2 Sr [OCR 1 R 2 (CH 2 ) m N {(CH 2 ) n NR 3 R 4 } 2 ] 2
[화학식 40][Formula 40]
Sr[OCR1R2(CH2)mN{(CH2)nOR3}2]2 Sr [OCR 1 R 2 (CH 2 ) m N {(CH 2 ) n OR 3 } 2 ] 2
상기 식에서, m은 서로 독립적으로 1 내지 3 중에서 선택되는 정수이고; n은 서로 독립적으로 2 내지 4 중에서 선택되는 정수이고; R1 내지 R5는 서로 독립적으로 수소, 할로겐 또는 선형 또는 분지형의 (C1-C5)알킬기이며; 상기 R1 내지 R5의 알킬기는 서로 독립적으로 불소, 산소, 질소 또는 (C1-C5)알킬기로 더 치환될 수 있다. 더욱 구체적으로는 R1 및 R2는 서로 독립적으로 할로겐, 불소, 산소, 질소로 치환되거나 치환되지 않은 선형 또는 분지형의 (C1-C5)알킬기이며; R3 내지 R5는 서로 독립적으로 수소 또는 불소로 치환되거나 치환되지 않은 선형 또는 분지형의 (C1-C5)알킬기이다.Wherein m is an integer selected from 1 to 3 independently of each other; n is an integer selected from 2 to 4 independently of each other; R 1 to R 5 are each independently hydrogen, halogen or a linear or branched (C 1 -C 5) alkyl group; The alkyl groups of R 1 to R 5 may be further substituted independently of each other with a fluorine, oxygen, nitrogen or (C 1 -C 5) alkyl group. More specifically, R 1 and R 2 are each independently a linear or branched (C 1 -C 5) alkyl group substituted or unsubstituted with halogen, fluorine, oxygen, nitrogen; R 3 to R 5 are each independently a linear or branched (C 1 -C 5) alkyl group substituted or unsubstituted with hydrogen or fluorine.
특히 상기 화학식 31 내지 화학식 40에서 m이 1 또는 2이고 n이 2 또는 3인 스트론튬 알콕사이드 화합물이 바람직하며, 구체적으로는 상기 화학식 31 내지 화학식 40에서 R1 및 R2는 서로 독립적으로 CH3, CF3, C2H5, CH(CH3)2 및 C(CH3)3로부터 선택되며, R3 내지 R5는 서로 독립적으로 수소, CH3, CF3, C2H5, CH(CH3)2 및 C(CH3)3로부터 선택되는 스트론튬 알콕사이드 화합물이 예시된다.In particular, a strontium alkoxide compound having m of 1 or 2 and n of 2 or 3 in Formulas 31 to 40 is preferable. Specifically, in Formulas 31 to 40, R 1 and R 2 independently of each other are CH 3 , CF 3 , C 2 H 5 , CH (CH 3 ) 2 and C (CH 3 ) 3 , R 3 to R 5 are independently of each other hydrogen, CH 3 , CF 3 , C 2 H 5 , CH (CH 3 ) a strontium alkoxide compound selected from 2 and C (CH 3) 3 and the like.
본 발명에 따른 화학식 1에 포함되는 화학식 11 내지 화학식 13은 스트론튬 알콕사이드 화합물은 반응식 1 내지 반응식 9에 기재된 바와 같이 하기 화학식 51 내지 화학식 53에서 선택된 아미노스트론튬 화합물과 하기 화학식 71 내지 화학식 73에서 선택된 아미노 알코올 2 당량과 반응시켜 제조된다.Formula 11 to Formula 13 according to the present invention is a strontium alkoxide compound is an amino strontium compound selected from Formula 51 to Formula 53 and amino alcohol selected from Formula 71 to Formula 73 as described in Schemes 1 to 9 Prepared by reaction with 2 equivalents.
[반응식 1]Scheme 1
Sr[NR6 2]2 + 2 HO-CR1R2(CH2)m-O-B-NR3R4 Sr [NR 6 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4
→ Sr[O-CR1R2(CH2)m-O-B-NR3R4]2 + 2 NR6 2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4 ] 2 + 2 NR 6 2 H
[반응식 2]Scheme 2
Sr[NR6 2]2 + 2 HO-CR1R2(CH2)m-N-(B-NR3R4)2 Sr [NR 6 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2
→ Sr[O-CR1R2(CH2)m-N-(B-NR3R4)2]2 + 2 NR6 2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2 ] 2 + 2 NR 6 2 H
[반응식 3]Scheme 3
Sr[NR6 2]2 + 2 HO-CR1R2(CH2)m-N-(B-OR3)2 Sr [NR 6 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2
→ Sr[O-CR1R2(CH2)m-N-(B-OR3)2]2 + 2 NR6 2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2 ] 2 + 2 NR 6 2 H
[반응식 4]Scheme 4
[반응식 5]Scheme 5
[반응식 6]Scheme 6
Sr[NR6 2]2 + HO-CR1R2(CH2)m-O-B-OR3 Sr [NR 6 2 ] 2 + HO-CR 1 R 2 (CH 2 ) m -OB-OR 3
→ Sr[O-CR1R2(CH2)m-O-B-OR3]2 + 2 NR6 2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -OB-OR 3 ] 2 + 2 NR 6 2 H
[반응식 7]Scheme 7
Sr[N(SiR7 3)2]2 + 2 HO-CR1R2(CH2)m-O-B-NR3R4 Sr [N (SiR 7 3 ) 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4
→ Sr[O-CR1R2(CH2)m-O-B-NR3R4]2 + 2 N(SiR7 3)2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4 ] 2 + 2 N (SiR 7 3 ) 2 H
[반응식 8]
Sr[N(SiR7 3)2]2 + 2 HO-CR1R2(CH2)m-N-(B-NR3R4)2 Sr [N (SiR 7 3 ) 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2
→ Sr[O-CR1R2(CH2)m-N-(B-NR3R4)2]2 + 2 N(SiR7 3)2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2 ] 2 + 2 N (SiR 7 3 ) 2 H
[반응식 9]Scheme 9
Sr[N(SiR7 3)2]2 + 2 HO-CR1R2(CH2)m-N-(B-OR3)2 Sr [N (SiR 7 3 ) 2 ] 2 + 2 HO-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2
→ Sr[O-CR1R2(CH2)m-N-(B-OR3)2]2 + 2 N(SiR7 3)2H ¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2 ] 2 + 2 N (SiR 7 3 ) 2 H
[반응식 10]
[반응식 11]Scheme 11
[반응식 12]Scheme 12
Sr[N(SiR7 3)2]2 + 2HO-CR1R2(CH2)m-O-B-OR3 Sr [N (SiR 7 3 ) 2 ] 2 + 2HO-CR 1 R 2 (CH 2 ) m -OB-OR 3
→ Sr[O-CR1R2(CH2)m-O-B-OR3]2 + 2 N(SiR7 3)2H¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -OB-OR 3 ] 2 + 2 N (SiR 7 3 ) 2 H
[반응식 13]Scheme 13
→ Sr[O-CR1R2(CH2)m-O-B-NR3R4]2 + 2 NH2(CH2)pNH2 ¡Æ Sr [O-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4 ] 2 + 2 NH 2 (CH 2 ) p NH 2
[반응식 14][Reaction Scheme 14]
→ Sr[O-CR1R2(CH2)m-N-(B-NR3R4)2]2 + 2 NH2(CH2)pNH2 → Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2 ] 2 + 2 NH 2 (CH 2 ) p NH 2
[반응식 15]Scheme 15
→ Sr[O-CR1R2(CH2)m-N-(B-OR3)2]2 + 2 NH2(CH2)pNH2 → Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2 ] 2 + 2 NH 2 (CH 2 ) p NH 2
[반응식 16][Reaction Scheme 16]
[반응식 17]Scheme 17
[반응식 18]Scheme 18
[화학식 11][Formula 11]
Sr[O-CR1R2(CH2)m-O-B-NR3R4]2 Sr [O-CR 1 R 2 (CH 2 ) m -OB-NR 3 R 4 ] 2
[화학식 12][Formula 12]
Sr[O-CR1R2(CH2)m-N-(B-NR3R4)2]2 Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-NR 3 R 4 ) 2 ] 2
[화학식 13][Formula 13]
Sr[O-CR1R2(CH2)m-N-(B-OR3)2]2 Sr [O-CR 1 R 2 (CH 2 ) m -N- (B-OR 3 ) 2 ] 2
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
Sr[O-CR1R2(CH2)m-O-B-OR3]2 Sr [O-CR 1 R 2 (CH 2 ) m -OB-OR 3 ] 2
[화학식 51][Formula 51]
Sr[NR6 2]2 Sr [NR 6 2 ] 2
[화학식 52][Formula 52]
Sr[N(SiR7 3)2]2 Sr [N (SiR 7 3 ) 2 ] 2
[화학식 53][Formula 53]
[화학식 71](71)
HO-CR1R2(CH2)m-O-B-NR1R2 HO-CR 1 R 2 (CH 2 ) m -OB-NR 1 R 2
[화학식 72](72)
HO-CR1R2(CH2)m-N-(B-NR1R2)2 HO-CR 1 R 2 (CH 2 ) m -N- (B-NR 1 R 2 ) 2
[화학식 73](73)
HO-CR1R2(CH2)m-N-(B-OR1)2 HO-CR 1 R 2 (CH 2 ) m -N- (B-OR 1 ) 2
[화학식 74]≪ EMI ID =
[화학식 75](75)
[화학식 76][Formula 76]
HO-CR1R2(CH2)m-O-B-OR3 HO-CR 1 R 2 (CH 2 ) m -OB-OR 3
상기 화학식 11 내지 화학식 16, 화학식 51 내지 화학식 53 및 화학식 71 내지 화학식 76에서, 상기 식에서 m은 서로 독립적으로 1 내지 3 중에서 선택되는 정수이고; p는 독립적으로 2 내지 10 중에서 선택된 정수이고; B는 서로 독립적으로 선형 또는 분지형의 (C2-C10)알킬렌기이고; R1 내지 R5는 서로 독립적으로 수소, 할로겐 또는 선형 또는 분지형의 (C1-C10)알킬기이며; 상기 B의 알킬렌, R1 내지 R7의 알킬기는 서로 독립적으로 할로겐, 산소, 질소, (C1-C20)알콕시기, (C1-C20)알킬아민기 또는 (C1-C20)알킬기로 더 치환될 수 있다.In Formulas 11 to 16, 51 to 53, and 71 to 76, m is an integer selected from 1 to 3 independently from each other; p is an integer independently selected from 2 to 10; B is, independently from each other, a linear or branched (C 2 -C 10) alkylene group; R 1 to R 5 independently of one another are hydrogen, halogen or a linear or branched (C 1 -C 10) alkyl group; The alkylene of B, alkyl groups of R 1 to R 7 may be independently substituted with a halogen, oxygen, nitrogen, (C 1 -C 20) alkoxy group, (C 1 -C 20) alkylamine group or (C 1 -C 20) alkyl group independently of one another. Can be.
본 발명에 따른 스트론튬 알콕사이드 화합물의 제조방법에서 반응 용매는 특별히 한정되지는 않고 탄화수소 용매이면 가능하며, 특히 에테르, n-헥산, n-햅탄, 벤젠, 톨루엔 또는 테트라하이드로퓨란(THF), 또는 이들의 혼합 용매가 바람직하다.In the method for preparing a strontium alkoxide compound according to the present invention, the reaction solvent is not particularly limited, and may be a hydrocarbon solvent, and in particular, ether, n-hexane, n-haptan, benzene, toluene or tetrahydrofuran (THF), or their Mixed solvents are preferred.
반응온 도는 상온 내지 70℃에서 수행되나, 특별히 가온하지 않고 상온에서 2내지 10 시간이면 반응이 완료된다.The reaction temperature is carried out at room temperature to 70 ℃, but the reaction is completed in 2 to 10 hours at room temperature without special heating.
반응 생성물인 화학식 1의 화합물은 핵자기 공명 분광법 (nuclear magnetic resonance spectroscopy, NMR), 푸리에 변환 적외선 분광법 (Fourier transform infrared spectroscopy, FTIR), 원소 분석법 (elemental analysis, EA)을 이용하여 확인하였다. 이와 같이 제조된 유기 스트론튬 화합물인 알콕시 스트론튬 화합물은 상온에서 연한 핑크색의 점성이 있는 액체이며 휘발성이 뛰어나다.The reaction product compound of Formula 1 was identified using nuclear magnetic resonance spectroscopy (NMR), Fourier transform infrared spectroscopy (FTIR), elemental analysis (EA). The alkoxy strontium compound, which is the organic strontium compound thus prepared, is a pale pink viscous liquid at room temperature and has excellent volatility.
상기의 알콕시 스트론튬 화합물을 이용하여 스트론튬 산화물 나노 물질, 스트론튬을 포함하는 이종금속 물질을 제조할 수 있을 뿐만 아니라 금속 유기물 화학 증착법(metal organic chemical vapor deposition, MOCVD)을 통하여 스트론튬 산화물 박막 및 스트론튬을 포함하는 이종금속 박막을 제조할 수 있는 장점이 있다.The alkoxy strontium compound may be used to prepare a strontium oxide nanomaterial and a dissimilar metal material including strontium, as well as a strontium oxide thin film and strontium through metal organic chemical vapor deposition (MOCVD). There is an advantage that can produce a dissimilar metal thin film.
한편, 상기 제조된 스트론튬 알콕사이드 화합물을 전구체로 사용하여 대한민국 특허발명 제666759호에 개시된 방법으로 입자의 크기 및 형상을 제어하여 박막 또는 나노 입자 형태의 스트론튬 화합물이 제조될 수 있다.Meanwhile, the strontium compound in the form of a thin film or a nanoparticle may be prepared by controlling the size and shape of the particle by the method disclosed in Korean Patent Invention No. 666759 using the prepared strontium alkoxide compound as a precursor.
본 발명에 따른 스트론튬 화합물은 높은 휘발성 및 열적 안정성을 나타냄으로써 금속 막의 우수한 질을 요구하는 금속 유기물 화학 증착법(MOCVD) 또는 스트론튬 산화물 나노 입자, 그리고 스트론튬을 포함하는 화합물을 생성할 수 있는 전구체로서 유용하게 사용할 수 있는 효과가 있다.The strontium compound according to the present invention exhibits high volatility and thermal stability, and thus is useful as a precursor capable of producing a compound containing metal organic chemical vapor deposition (MOCVD) or strontium oxide nanoparticles, and strontium, which requires excellent quality of a metal film. There is an effect that can be used.
본 발명은 하기의 실시 예에 의하여 보다 더 잘 이해될 수 있으며, 하기의 실시 예는 본 발명의 예시 목적을 위한 것이며 첨부된 특허 청구범위에 의하여 한정되는 보호 범위를 제한하고자 하는 것은 아니다.The invention can be better understood by the following examples, which are intended for the purpose of illustration of the invention and are not intended to limit the scope of protection defined by the appended claims.
모든 실험은 장갑 상자 또는 슐렝크 관(Schlenk line)을 이용하여 비활성 아르곤 또는 질소 분위기에서 다음과 같이 수행되었다.All experiments were performed in an inert argon or nitrogen atmosphere using a glove box or Schlenk line as follows.
실시예 1Example 1
[1-(3-(디메틸아미노)-2,2-디메틸프로폭시)-2-메틸-2-부톡시]스트론튬 [Sr(ddmb)2] 합성 I [1- (3- (dimethylamino) -2,2-dimethylpropoxy) -2-methyl-2-butoxy] strontium [Sr (ddmb) 2 ] Synthesis I
→ Sr[OC(CH3)(C2H5)CH2OCH2C(CH3)2CH2N(CH3)2]2 + 2 NH2CH2CH2NH2 → Sr [OC (CH 3 ) (C 2 H 5 ) CH 2 OCH 2 C (CH 3 ) 2 CH 2 N (CH 3 ) 2 ] 2 + 2 NH 2 CH 2 CH 2 NH 2
50 mL 슐렝크 플라스크에 
실시예 2 Example 2
[1-(3-(디메틸아미노)-2,2-디메틸프로폭시)-2-메틸-2-부톡시]스트론튬 [Sr(ddmb)2] 합성 II [1- (3- (dimethylamino) -2,2-dimethylpropoxy) -2-methyl-2-butoxy] strontium [Sr (ddmb) 2 ] Synthesis II
Sr[N{Si(CH3)3}2]2 + 2 HOC(CH3)(C2H5)CH2OCH2C(CH3)2CH2N(CH3)2 Sr [N {Si (CH 3 ) 3 } 2 ] 2 + 2 HOC (CH 3 ) (C 2 H 5 ) CH 2 OCH 2 C (CH 3 ) 2 CH 2 N (CH 3 ) 2
→ Sr[OC(CH3)(C2H5)CH2OCH2C(CH3)2CH2N(CH3)2]2 + 2 HN{Si(CH3)3}2 ¡Æ Sr [OC (CH 3 ) (C 2 H 5 ) CH 2 OCH 2 C (CH 3 ) 2 CH 2 N (CH 3 ) 2 ] 2 + 2 HN {Si (CH 3 ) 3 } 2
50 mL 슐렝크 플라스크에 Sr[N{Si(CH3)3}2]2 (Sr(btsa)2, 0.82 g, 2 mmol) 을 넣고 디에틸 에테르(diethyl ether) (15 mL)를 첨가하여 녹인 후 1-(3-(디메틸아미노)-2,2-디메틸프로폭시)-2-메틸-2-부탄올 (ddmbH, 0.87 g, 4 mmol)을 천천히 첨가해 준다. 혼합 용액을 5 시간 동안 교반하고 여과하여 여액을 진공 건조하여 끈적이는 액체 화합물을 얻었다.Sr [N {Si (CH 3 ) 3 } 2 ] 2 (Sr (btsa) 2 , 0.82 g, 2 mmol) was added to a 50 mL Schlenk flask, which was dissolved by adding diethyl ether (15 mL). Then 1- (3- (dimethylamino) -2,2-dimethylpropoxy) -2-methyl-2-butanol (ddmbH, 0.87 g, 4 mmol) is added slowly. The mixed solution was stirred for 5 hours and filtered to vacuum dry the filtrate to give a sticky liquid compound.
본 발명의 실시예 1에서 합성한 스트론튬 화합물들의 열적 안정성 및 휘발성 그리고 분해 온도는 열무게 분석법/시차 열 분석법 (Thermogravimetric analysis/differential thermal analysis, TGA/DTA)을 이용하여 분석하였다. 도 2에 나타낸 바와 같이 [1-(3-(디메틸아미노)-2,2-디메틸프로폭시)-2-메틸-2-부톡시]스트론튬 [Sr(ddmb)2] 화합물의 경우에 있어서는 90 내지 220 ℃ 사이와 320 내지 410 ℃ 사이에서 두 번에 거쳐 급격한 질량 감소가 일어나고 최종 잔유량은 18.6%이다. The thermal stability, volatility, and decomposition temperature of the strontium compounds synthesized in Example 1 of the present invention were analyzed using thermogravimetric analysis / differential thermal analysis (TGA / DTA). As shown in Fig. 2, in the case of the compound [1- (3- (dimethylamino) -2,2-dimethylpropoxy) -2-methyl-2-butoxy] strontium [Sr (ddmb) 2 ] There are two rapid mass reductions between 220 ° C. and between 320 and 410 ° C. and the final residue is 18.6%.
실시예 3 Example 3
[1-(비스(2-메톡시에틸아미노)-2-메틸-2-프로폭시]스트론튬 [Sr(bmmp)2] 합성 Synthesis of [1- (bis (2-methoxyethylamino) -2-methyl-2-propoxy] strontium [Sr (bmmp) 2 ]
→ Sr[OC(CH3)2CH2N(CH2CH2OCH3)2]2 + 2 NH2CH2CH2NH2 → Sr [OC (CH 3 ) 2 CH 2 N (CH 2 CH 2 OCH 3 ) 2 ] 2 + 2 NH 2 CH 2 CH 2 NH 2
50 mL 슐렝크 플라스크에 
원소 분석 C20H44N2O6Sr {계산치 (실측치)}: C, 48.41 (50.07); H, 8.94 (9.32); N, 5.65 (5.82).Elemental Analysis C 20 H 44 N 2 O 6 Sr {calculated (calculated)}: C, 48.41 (50.07); H, 8.94 (9.32); N, 5.65 (5.82).
본 발명의 실시예 3에서 합성한 스트론튬 화합물들의 열적 안정성 및 휘발성 그리고 분해 온도는 열무게 분석법/시차 열 분석법 (Thermogravimetric analysis/differential thermal analysis, TGA/DTA)을 이용하여 분석하였다. 도 5 에 나타낸 바와 같이 [1-(비스(2-메톡시에틸아미노)-2-메틸-2-프로폭시]스트론튬 [Sr(bmmp)2] 화합물의 경우에 있어서는 120 내지 270 ℃ 사이의 비교적 넓은 범위에서 단일 단계로 질량 감소가 일어나고 최종 잔유량은 13.5%이다. The thermal stability, volatility and decomposition temperature of the strontium compounds synthesized in Example 3 of the present invention were analyzed using Thermogravimetric analysis / differential thermal analysis (TGA / DTA). As shown in FIG. 5, in the case of the [1- (bis (2-methoxyethylamino) -2-methyl-2-propoxy] strontium [Sr (bmmp) 2 ] compound, a relatively wide range between 120 and 270 ° C Mass reduction occurs in a single step in the range and the final residual volume is 13.5%.
실시예 4 Example 4
[1-(비스(3-디메틸아미노프로필아미노)-2-메틸-2-프로폭시]스트론튬 [Sr(bdmp)2] 합성 Synthesis of [1- (bis (3-dimethylaminopropylamino) -2-methyl-2-propoxy] strontium [Sr (bdmp) 2 ]
→ Sr[OC(CH3)2CH2N{CH2CH2CH2N(CH3)2}2]2 + 2 NH2CH2CH2NH2 → Sr [OC (CH 3 ) 2 CH 2 N {CH 2 CH 2 CH 2 N (CH 3 ) 2 } 2 ] 2 + 2 NH 2 CH 2 CH 2 NH 2
50 mL 슐렝크 플라스크에 
원소 분석 C28H64N6O2Sr {계산치 (실측치)}: C, 55.64 (56.24); H, 10.67 (12.70); N, 13.90 (13.84).Elemental Analysis C 28 H 64 N 6 O 2 Sr {calculated (calculated)}: C, 55.64 (56.24); H, 10.67 (12.70); N, 13.90 (13.84).
본 발명의 실시예 3에서 합성한 스트론튬 화합물들의 열적 안정성 및 휘발성 그리고 분해 온도는 열무게 분석법/시차 열 분석법 (Thermogravimetric analysis/differential thermal analysis, TGA/DTA)을 이용하여 분석하였다. 도 8에 나타낸 바와 같이 [1-(비스(3-디메틸아미노프로필아미노)-2-메틸-2-프로폭시]스트론튬 [Sr(bdmp)2] 화합물의 경우에 있어서는 120 내지 280 ℃ 사이의 비교적 많은 질량 감소가 일어나고 이어서 340 내지 370 사이에서 적은 양의 질량 감소가 일어나는데 최종 잔유량은 14.6%이다. The thermal stability, volatility and decomposition temperature of the strontium compounds synthesized in Example 3 of the present invention were analyzed using Thermogravimetric analysis / differential thermal analysis (TGA / DTA). As shown in FIG. 8, in the case of the [1- (bis (3-dimethylaminopropylamino) -2-methyl-2-propoxy] strontium [Sr (bdmp) 2 ] compound, a relatively large amount between 120 and 280 ° C. Mass loss occurs followed by a small amount of mass loss between 340 and 370 with a final residual amount of 14.6%.
도 1은 실시예 1에서 제조한 Sr(ddmb)2 화합물의 푸리에 변환 적외선 분광 (FTIR) 분석 결과이다.1 is a result of Fourier transform infrared spectroscopy (FTIR) analysis of the Sr (ddmb) 2 compound prepared in Example 1. FIG.
도 2는 실시예 1에서 제조한 Sr(ddmb)2 화합물의 열중량 분석(TGA) 및 시차 열 분석(DTA) 결과를 나타내는 그래프이다.Figure 2 is a graph showing the results of thermogravimetric analysis (TGA) and differential thermal analysis (DTA) of the Sr (ddmb) 2 compound prepared in Example 1.
도 3은 실시예 3에서 제조한 Sr(bmmp)2 화합물의 수소 핵자기 공명 분광(1H NMR) 분석 결과이다.3 is a hydrogen nuclear magnetic resonance spectroscopy ( 1 H NMR) analysis of the Sr (bmmp) 2 compound prepared in Example 3.
도 4는 실시예 3에서 제조한 Sr(bmmp)2 화합물의 푸리에 변환 적외선 분광 (FTIR) 분석 결과이다.4 is a Fourier transform infrared spectroscopy (FTIR) analysis result of the Sr (bmmp) 2 compound prepared in Example 3. FIG.
도 5는 실시예 3에서 제조한 Sr(bmmp)2 화합물의 열중량 분석(TGA) 및 시차 열 분석(DTA) 결과를 나타내는 그래프이다.FIG. 5 is a graph showing the results of thermogravimetric analysis (TGA) and differential thermal analysis (DTA) of the Sr (bmmp) 2 compound prepared in Example 3. FIG.
도 6은 실시예 4에서 제조한 Sr(bdmp)2 화합물의 수소 핵자기 공명 분광(1H NMR) 분석 결과이다.6 shows hydrogen nuclear magnetic resonance spectroscopy ( 1 H NMR) analysis results of Sr (bdmp) 2 compound prepared in Example 4. FIG.
도 7은 실시예 4에서 제조한 Sr(bdmp)2 화합물의 푸리에 변환 적외선 분광 (FTIR) 분석 결과이다.7 shows Fourier transform infrared spectroscopy (FTIR) analysis results of the Sr (bdmp) 2 compound prepared in Example 4. FIG.
도 8은 실시예 4에서 제조한 Sr(bdmp)2 화합물의 열중량 분석(TGA) 및 시차 열 분석(DTA) 결과를 나타내는 그래프이다.8 is a graph showing the results of thermogravimetric analysis (TGA) and differential thermal analysis (DTA) of the Sr (bdmp) 2 compound prepared in Example 4. FIG.
Claims (9)
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