KR101629696B1 - Novel indium derivatives, its preparation method and the thin film using the same - Google Patents
Novel indium derivatives, its preparation method and the thin film using the same Download PDFInfo
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- 239000010409 thin film Substances 0.000 title claims abstract description 27
- 150000002471 indium Chemical class 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 229910052738 indium Inorganic materials 0.000 claims abstract description 48
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000002243 precursor Substances 0.000 claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000000231 atomic layer deposition Methods 0.000 claims description 6
- 238000005229 chemical vapour deposition Methods 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000002411 thermogravimetry Methods 0.000 description 9
- 239000003446 ligand Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 6
- 238000011109 contamination Methods 0.000 description 6
- 150000002472 indium compounds Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KTSFMFGEAAANTF-UHFFFAOYSA-N [Cu].[Se].[Se].[In] Chemical compound [Cu].[Se].[Se].[In] KTSFMFGEAAANTF-UHFFFAOYSA-N 0.000 description 3
- -1 indium alkoxide Chemical class 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021617 Indium monochloride Inorganic materials 0.000 description 1
- BGVIOMZXEIPKTI-UHFFFAOYSA-N [In].[Cs] Chemical compound [In].[Cs] BGVIOMZXEIPKTI-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 1
- RJMMFJHMVBOLGY-UHFFFAOYSA-N indium(3+) Chemical compound [In+3] RJMMFJHMVBOLGY-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- ATKFKPHZVBDUTR-UHFFFAOYSA-N sodium;1-(dimethylamino)-2-methylpropan-2-olate Chemical compound CN(C)CC(C)(C)O[Na] ATKFKPHZVBDUTR-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/305—Sulfides, selenides, or tellurides
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
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- Organic Chemistry (AREA)
Abstract
본 발명은 신규한 인듐 전구체, 이의 제조 방법 및 이를 이용한 박막에 관한 것으로, 열적 안정성 및 휘발성이 우수하고, 다루기 용이한 인듐 3가의 신규한 인듐 전구체 및 이의 제조 방법, 그리고 이를 이용한 고순도의 인듐 함유 박막에 관한 것이다.The present invention relates to a novel indium precursor, a method for producing the same, a thin film using the same, a novel indium trivalent indium precursor excellent in thermal stability and volatility and easy to handle, a method for producing the same, and a high purity indium- .
Description
본 발명은 신규한 인듐 전구체, 이의 제조방법 및 이를 이용한 박막에 관한 것으로, 보다 구체적으로는 열적 안정성과 휘발성이 개선되고 낮은 온도에서 쉽게 양질의 인듐을 포함한 박막의 제조가 가능한 인듐 전구체 및 이의 제조 방법, 그리고 이를 이용한 인듐을 포함한 박막을 제조하는 방법에 관한 것이다.The present invention relates to a novel indium precursor, a method for producing the same, and a thin film using the indium precursor. More specifically, the present invention relates to an indium precursor capable of easily producing a thin film containing indium at a low temperature with improved thermal stability and volatility, And a method for producing a thin film containing indium using the same.
인듐은 전기 도금을 통한 인듐 코팅 분야에 있어 마모에 대한 저항력이 뛰어난 점과 알루미늄 전선에 접촉 시 저항이 낮다는 특성 때문에 유용하게 활용되고 있으며 유럽 지역에 있어 나트륨 가스램프(sodium vapor lamp)의 내부 코팅 재료로 산화 인듐이 이용되기도 한다. 또한 산화 인듐과 산화 주석-인듐 필름은 유리나 세라믹의 전도성을 띤 코팅 재료와 전자 발광 패널(electroluminescent pannels)에도 이용된다. 또한 산화 인듐은 열 절연체(heat insulator)로서 이용될 수 있고 태양 전지나 반도체 산업에도 응용될 수 있다. 또한 광전극 물질(photoelectrode material), 액정 표시 장치(liquid crystal display) 또는 광기전 장치(photovoltaic device) 등에도 이용 가능하다.Indium is used effectively because of its excellent resistance to abrasion in the field of indium plating through electroplating and its low resistance in contact with aluminum wires. Inside the coating of sodium vapor lamp in Europe Indium oxide may be used as the material. In addition, indium oxide and tin oxide-indium films are also used in coating materials for electroconductivity of glass or ceramics and electroluminescent panels. In addition, indium oxide can be used as a heat insulator and can be applied to solar cells and the semiconductor industry. It can also be used for photoelectrode materials, liquid crystal displays or photovoltaic devices.
산화 인듐 증착에 사용되어온 전구체로서 InCl3는 박막 증착 시에 염소 오염이 있을 수 있고 외부로부터 산소 원을 필요로 하는 단점이 있으며, Me3In나 Et3In 등의 트리알킬인듐(III)은 휘발성이 좋으나 산소와 수분에 매우 민감하다는 단점이 있다. As a precursor used for indium oxide deposition, InCl 3 may have chlorine contamination during thin film deposition and requires an oxygen source from the outside, and trialkyl indium (III) such as Me 3 In or Et 3 In is volatile But it is very sensitive to oxygen and moisture.
또한 [In(OC2H4OMe)3]m, [In(OC2H4NMe2)3]m 등의 인듐 알콕사이드는 휘발성도 없고 공기 중에서 불안정하여 사용에 어려움이 많은 것으로 알려져 있다. 또 다른 전구체로 In(thd)3 (여기서 thd는 2,2,6,6-테트라메틸-3,5-헵타디오네이트이다)와 In(acac)3 (여기서 acac는 아세틸아세토네이트이다)와 같은 베타디케토네이트 리간드를 이용한 화합물이 있다. 그러나 이들 베타 디케토네이트 리간드를 이용한 화합물을 이용하여 인듐을 포함하는 재료를 만드는 경우 산소와 탄소의 오염으로 인하여 이를 이용한 박막의 성질을 저하시키는 단점을 가진다. It is also known that indium alkoxide such as [In (OC 2 H 4 OMe) 3 ] m and [In (OC 2 H 4 NMe 2 ) 3 ] m are not volatile and are unstable in air and thus are difficult to use. Other precursors include In (thd) 3 (where thd is 2,2,6,6-tetramethyl-3,5-heptadionate) and In (acac) 3 (where acac is acetylacetonate) Beta-diketonate ligand. However, when a material containing indium is formed by using a compound using these betad diketonate ligands, it has disadvantages in that it deteriorates the properties of the thin film due to contamination of oxygen and carbon.
또 다른 전구체로 [Et2InOHEt2InNH2], [ i Pr2InOH i Pr2InNH2]와 같은 물과 InR3 (여기서 R은 Et 또는 iPr) 유도체의 알케인 제거 반응을 이용한 화합물이 있다. 그러나 이 인듐 화합물은 암모니아를 첨가해 줌으로써 인듐 옥사이드 박막을 고온에서 증착할 수 있다. 또한 단순한 알콕사이드 리간드 대신에 두 자리 리간드를 사용하여 금속의 배위 자리를 포화시키는 방법이 알려져 있다. 또한 두 자리 리간드 중에서도 아미노 알콕사이드 계통이 알콕시 알콕사이드보다 더 유용하다고 알려져 있다.As another precursor, compounds such as [Et 2 InOHEt 2 InNH 2 ], [ i Pr 2 InOH i Pr 2 InNH 2 ] and compounds using an alkane elimination reaction of water and InR 3 (where R is Et or i Pr) . However, this indium compound can be deposited at high temperature by adding ammonia to the indium oxide thin film. It is also known to use a bidentate ligand instead of a simple alkoxide ligand to saturate the coordination site of the metal. Also among the bidentate ligands, the amino alkoxide system is known to be more useful than the alkoxy alkoxide.
일반적으로 진공 공정으로 박막을 제조하기 위해서 해당 전구체가 높은 휘발성을 가져야 하고, 용액 공정을 이용하여 나노 물질을 제조하기 위해서는 전구체가 공기 중에서 안정하고 다루기 쉬워야 한다. Generally, in order to prepare a thin film by a vacuum process, the precursor must have high volatility, and in order to produce a nanomaterial using a solution process, the precursor should be stable in air and easy to handle.
이에 최근에는 인듐 화합물이 다른 금속과 함께 사용되어 인듐-갈륨-아연 산화물 (indium-gallium-zinc oxide, IGZO)와 같은 투명전자소자나 구리-인듐-갈륨 셀레나이드 (copper indium gallium selenide, CIGS)와 같은 무기태양전지소재를 제작하기 위한 전구체로 많이 연구하고 있다. 미국 등록 특허 제 6,127,202호는 나노입자 합성 단계에서 Cu-In-O, Cu-(In,Ga) -O(이하 CI, CIG 산화물) 산화물 전구체를 합성한 뒤 이를 이용하여 다시 CIS 및 CIGS 광흡수층을 제조하는 방법을 보고하였다. 이러한 전착법은 전구체 합성 공정 같은 추가 공정 없이 CIGS 박막을 제조할 수 있어 공정을 단순화할 수 있다는 장점을 가지나, 계면활성제 등과 같은 유기 화합물을 추가로 첨가하기 때문에 유기물에 의한 박막의 오염을 피할 수 없다는 것이 단점으로 지적되고 있다. Recently, indium compounds have been used with other metals to form transparent electronic devices such as indium-gallium-zinc oxide (IGZO), copper indium gallium selenide (CIGS) We are studying as a precursor for making inorganic solar cell materials. US Patent No. 6,127,202 discloses a method of synthesizing an oxide precursor of Cu-In-O and Cu- (In, Ga) -O (hereinafter referred to as CI, CIG oxide) . This electrodeposition method has the advantage of simplifying the process because it can produce the CIGS thin film without any additional process such as the precursor synthesis process. However, since an organic compound such as a surfactant is additionally added, contamination of the thin film by the organic material can not be avoided It is pointed out as a disadvantage.
이상과 같이 종래에 알려진 인듐 3가 화합물은 박막을 진공 공정에서 요구하는 충분하지 못한 휘발성, 제조된 막에 생기는 할로겐(halogen) 오염 및 용액 공정에서 필요로 하는 공기 중에서 안정하고 적절한 온도에서 분해가 일어나지 않는 문제점을 가지고 있다. As described above, the conventionally known indium trivalent compounds have a problem that insufficient volatility required for a vacuum process in a thin film, halogen contamination in a produced film, and decomposition at a stable and suitable temperature in the air required in a solution process I have a problem.
이에 본 발명자들은 상기와 같은 문제점을 해결하기 위하여, 화합물 자체에 할로겐을 함유하지 않고, 휘발성이 우수한 인듐 3가의 신규한 인듐 전구체, 이의 제조 방법 및 이를 이용한 박막을 제공하고자 본 발명을 완성하였다.Accordingly, the present inventors have completed the present invention to provide a novel indium trivalent indium precursor which does not contain a halogen in the compound itself and has excellent volatility, a process for producing the same, and a thin film using the same.
본 발명의 목적은 새로운 전자 주개 리간드가 배위되도록 함으로써, 열적 안정성과 휘발성이 개선되어 양질의 인듐을 포함한 박막의 제조가 가능한 우수한 신규의 인듐 전구체 및 이의 제조 방법을 제공하는 것이다.An object of the present invention is to provide a novel novel indium precursor which is capable of producing a thin film containing indium of high quality by improving the thermal stability and volatility by allowing a new electron donating ligand to be coordinated, and a process for producing the same.
본 발명은 하기 화학식1로 표시되는 인듐 전구체를 포함한다.The present invention includes an indium precursor represented by the following general formula (1).
[화학식1][Chemical Formula 1]
[상기 화학식1에 있어서, [In the formula 1,
상기 R1 내지 R6은 각각 독립적으로 C1-C10의 선형 또는 분지형 알킬기이고; Each of R 1 to R 6 is independently a C1-C10 linear or branched alkyl group;
상기 n은 1 내지 3의 정수이며; N is an integer of 1 to 3;
상기 a는 1 내지 2이다.]Wherein a is 1 to 2. "
본 발명의 일실시예에 따른 상기 인듐 전구체는 상기 R1 내지 R6이 각각 독립적으로 C1-C5의 선형 또는 분지형 알킬일 수 있다.In the indium precursor according to an embodiment of the present invention, R 1 to R 6 may each independently be a linear or branched alkyl of C 1 -C 5.
본 발명은 하기 화학식2로 표시되는 화합물과 하기 화학식3으로 표시되는 화합물을 반응하여 하기 화학식1로 표시되는 화합물을 제조하는 단계; 를 포함하는 하기 화학식1로 표시되는 인듐 전구체의 제조방법을 제공한다.The present invention relates to a process for preparing a compound represented by the following general formula (1) by reacting a compound represented by the following general formula (2) and a compound represented by the following general formula (3) Wherein the indium precursor is represented by the following general formula (1).
[화학식2](2)
In(R1)(R2)X1 In (R 1 ) (R 2 ) X 1
[화학식3](3)
[화학식1][Chemical Formula 1]
[상기 화학식1 내지 화학식3에 있어서, [In the above Chemical Formulas 1 to 3,
상기 R1 내지 R6은 각각 독립적으로 C1-C10의 선형 또는 분지형 알킬기이고;Each of R 1 to R 6 is independently a C1-C10 linear or branched alkyl group;
상기 X1은 할로겐이며;X < 1 > is halogen;
상기 M은 Li, Na 또는 K이고;M is Li, Na or K;
상기 n은 1 내지 3의 정수이며;N is an integer of 1 to 3;
상기 a는 1 내지 2이다.]Wherein a is 1 to 2. "
본 발명은 상기 화학식1로 표시되는 인듐 전구체를 이용한 인듐 함유 박막의 제조 방법을 제공한다.The present invention provides a process for preparing an indium-containing thin film using the indium precursor represented by the above formula (1).
본 발명의 일실시예에 따른, 상기 인듐 함유 박막은 화학기상증착법(CVD) 또는 원자층증착법(ALD)을 사용하는 공정에 바람직하게 적용될 수 있다.According to an embodiment of the present invention, the indium-containing thin film can be preferably applied to a process using chemical vapor deposition (CVD) or atomic layer deposition (ALD).
본 발명에 따른 상기 인듐 전구체는 다루기 쉽고, 보관이 용이하다는 장점을 가진다. The indium precursor according to the present invention has an advantage that it is easy to handle and easy to store.
또한 상기 인듐 전구체는 할로겐을 함유하고 있지 않아 이에 의한 오염을 일으키지 않을 뿐 아니라, 열적 안정성과 휘발성이 우수하여, 낮은 온도에서도 용이하게 박막을 제조할 수 있어 경제적으로 고순도의 인듐 함유 박막을 제조할 수 있다는 장점을 가진다.In addition, since the indium precursor does not contain halogen and does not cause contamination by this, the thin film can be easily manufactured even at a low temperature because of its excellent thermal stability and volatility, so that an indium-containing thin film of high purity can be produced economically .
도1은 [In(CH3)2(dmamp)]2의 열중량 분석(TGA) 결과 도면이다.
도2는 [In(CH3)2(dmamp)]2의 결정구조(X-ray structure)이다.
도3은 [In(CH3)2(dmamb)]2의 열중량 분석(TGA) 결과 도면이다.
도4는 [In(CH3)2(dmamb)]2의 결정구조(X-ray structure)이다.
도5는 [In(CH3)2(dmaeb)]2의 열중량 분석(TGA) 결과 도면이다.
도6은 [In(CH3)2(dmaeb)]2의 결정구조(X-ray structure)이다.1 is a thermogravimetric analysis (TGA) result of [In (CH 3 ) 2 (dmamp)] 2 .
2 is an X-ray structure of [In (CH 3 ) 2 (dmamp)] 2 .
3 is a thermogravimetric analysis (TGA) result of [In (CH 3 ) 2 (dmamb)] 2 .
4 is an X-ray structure of [In (CH 3 ) 2 (dmamb)] 2 .
5 is a thermogravimetric analysis (TGA) result of [In (CH 3 ) 2 (dmaeb)] 2 .
6 is an X-ray structure of [In (CH 3 ) 2 (dmaeb)] 2 .
본 발명에 따른 인듐 전구체, 이의 제조 방법 및 이를 이용한 박막에 대하여 이하 상술하나, 이때 사용되는 기술 용어 및 과학 용어에 있어서 다른 정의가 없다면, 이 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 통상적으로 이해하고 있는 의미를 가지며, 하기의 설명에서 본 발명의 요지를 불필요하게 흐릴 수 있는 공지 기능 및 구성에 대한 설명은 생략한다.
INDUSTRIAL APPLICABILITY The indium precursor according to the present invention, a method for producing the same, and a thin film using the same will be described in detail below. Unless otherwise defined in technical terms and scientific terms used herein, In the following description, well-known functions and constructions are not described in order to avoid unnecessary obscuration of the present invention.
본 발명은 하기 화학식1로 표시되는 인듐 전구체를 제공한다.The present invention provides an indium precursor represented by the following general formula (1).
[화학식1][Chemical Formula 1]
[상기 화학식1에 있어서, [In the formula 1,
상기 R1 내지 R6은 각각 독립적으로 C1-C10의 선형 또는 분지형 알킬기이고; Each of R 1 to R 6 is independently a C1-C10 linear or branched alkyl group;
상기 n은 1 내지 3의 정수이며; N is an integer of 1 to 3;
상기 a는 1 내지 2이다.]Wherein a is 1 to 2. "
상기 화학식1로 표시되는 인듐 전구체는 열적 안정성 및 휘발성이 우수하여 이를 이용한 인듐함유 박막의 제조시, 낮은 온도에서 공정 수행이 가능하여 경제적일 뿐 아니라 고순도의 인듐 함유 박막의 제조가 가능하다.The indium precursor represented by the above formula (1) has excellent thermal stability and volatility. Thus, the indium-containing thin film can be processed at a low temperature in the production of the indium-containing thin film.
상기 화학식1로 표시되는 인듐 전구체는 높은 휘발성을 가지기 위한 측면에서 바람직하게는 상기 R1 내지 R6는 각각 독립적으로 (C1-C5)알킬일 수 있다.Indium precursor of the formula (1) may preferably be the above R 1 to R 6 are each independently a (C1-C5) alkyl in the side for has a high volatility.
또한 본 발명은 하기 화학식2로 표시되는 화합물과 하기 화학식3으로 표시되는 화합물을 유기용매 하에서 반응하여 하기 화학식1로 표시되는 화합물을 제조하는 단계를 포함하는 하기 화학식1로 표시되는 인듐 전구체의 제조방법을 제공한다. The present invention also relates to a process for preparing an indium precursor represented by the following general formula (1), comprising the step of reacting a compound represented by the following general formula (2) and a compound represented by the following general formula (3) .
[화학식2](2)
In(R1)(R2)X1 In (R 1 ) (R 2 ) X 1
[화학식3](3)
[화학식1][Chemical Formula 1]
[상기 화학식1 내지 화학식3에 있어서, [In the above Chemical Formulas 1 to 3,
상기 R1 내지 R6은 각각 독립적으로 C1-C10의 선형 또는 분지형 알킬기이고;Each of R 1 to R 6 is independently a C1-C10 linear or branched alkyl group;
상기 X1은 할로겐이며;X < 1 > is halogen;
상기 M은 Li, Na 또는 K이고;M is Li, Na or K;
상기 n은 1 내지 3의 정수이며;N is an integer of 1 to 3;
상기 a는 1 내지 2이다.]Wherein a is 1 to 2. "
상기 화학식1로 표시되는 인듐 전구체의 제조 방법에서 반응용매로 사용한 유기용매는 톨루엔, 메탄올, 에탄올, 벤젠, n-햅탄, 테트라하이드로퓨란(THF), 또는 이들의 혼합용매일 수 있으며, 상기 인듐 전구체의 높은 용해도의 측면에서 테트라하이드로퓨란(THF)이 바람직하나 이에 한정이 있는 것은 아니다.The organic solvent used as the reaction solvent in the process for preparing the indium precursor represented by the above formula (1) may be toluene, methanol, ethanol, benzene, n-heptane, tetrahydrofuran (THF) Tetrahydrofuran (THF) is preferable but not limited in terms of high solubility of the compound.
상기 인듐 전구체는 휘발성이 우수하여 낮은 온도에서 높은 증착율을 가질 수 있으며, 할로겐을 함유하지 않아 이로 인한 박막의 오염의 유발을 막을 수 있다.The indium precursor is excellent in volatility and can have a high deposition rate at a low temperature and can prevent the contamination of the thin film due to the absence of halogen.
본 발명은 상기 인듐 전구체를 이용한 인듐 함유 박막의 제조 방법을 제공한다. 상기 인듐함유 박막은 화학기상증착법(CVD) 또는 원자층증착법(ALD)으로 수행될 수 있다.The present invention provides a method for producing an indium-containing thin film using the indium precursor. The indium-containing thin film may be performed by chemical vapor deposition (CVD) or atomic layer deposition (ALD).
또한 본 발명은 상기 인듐 함유 박막의 제조 방법으로 제조되는 인듐 함유 박막을 제공한다.
The present invention also provides an indium-containing thin film produced by the above-described method for producing an indium-containing thin film.
이하, 본 발명을 하기 실시예에 의해 더욱 구체적으로 설명한다. 그러나 이들 실시예는 본 발명에 대한 이해를 돕기 위한 것일 뿐, 어떤 의미로든 본 발명의 범위가 이들에 의해 제한되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, these embodiments are provided to aid understanding of the present invention, and the scope of the present invention is not limited thereto in any sense.
(실시예1) [In(CH3)2(dmamp)]2의 합성(Example 1) Synthesis of [In (CH 3 ) 2 (dmamp)] 2
삼구 플라스크에 In(CH3)2Cl (1.0 g, 6.25 mmol)을 THF에 용해시킨 후, Na(dmamp)(sodium 1-(dimethylamino)-2-methylpropan-2-olate) (0.87 g, 6.25 mmol) 넣어 상온에서 12 시간 동안 교반하였다. 반응물을 여과하여 얻은 용액을 감압 하에서 용매를 제거하였고, hexane으로 추출한 후, hexane을 감압 농축하여 제거하고, 이를 승화를 통해 순수한 [In(CH3)2(dmamp)]2를 흰색 고체 화합물(0.80 g, 수율 80%)로 얻었다. (승화온도: 80 ℃/0.05 Torr)A three-necked flask In (CH 3) 2 Cl ( 1.0 g, 6.25 mmol) was dissolved in THF, Na (dmamp) (sodium 1- (dimethylamino) -2-methylpropan-2-olate) (0.87 g, 6.25 mmol ) And the mixture was stirred at room temperature for 12 hours. The reaction solution was filtered to remove the solvent under reduced pressure. The solvent was extracted with hexane, and the hexane was concentrated under reduced pressure to remove pure [In (CH 3 ) 2 (dmamp)] 2 via sublimation. g, yield: 80%). (Sublimation temperature: 80 DEG C / 0.05 Torr)
1H NMR (C6D6, 300 MHz): δ 0.05 (s, 6H), 1.24 (s, 6H), 1.91 (s, 6H), 1.92 (s, 2H). 1 H NMR (C 6 D 6 , 300 MHz): δ 0.05 (s, 6H), 1.24 (s, 6H), 1.91 (s, 6H), 1.92 (s, 2H).
Anal. Calcd for C14H34N2O2In2 : C, 36.8; H, 7.72; N, 5.37. Found: C, 36.8; H, 7.80, N; 5.40.Anal. Calcd for C 14 H 34 N 2 O 2 In 2: C, 36.8; H, 7.72; N, 5.37. Found: C, 36.8; H, 7.80, N; 5.40.
녹는점 : 95 ℃
Melting point: 95 ℃
(실시예2) [In(CH3)2(dmamb)]2의 합성(Example 2) Synthesis of [In (CH 3 ) 2 (dmamb)] 2
삼구 플라스크에 In(CH3)2Cl (1.0 g, 6.25 mmol)을 THF에 용해시킨 후, Na(dmamb) (0.87 g, 6.25 mmol) 넣어 상온에서 12 시간 동안 교반하였다. 반응물을 여과하여 얻은 용액을 감압 하에서 용매를 제거하였고, hexane으로 추출한 후, hexane을 감압 농축하여 제거하고, 이를 승화를 통해 순수한 [In(CH3)2(dmamb)]2를 흰색 고체 화합물(0.73 g, 수율 73%)로 얻었다. (승화온도: 80 ℃/0.05 Torr)In (CH 3 ) 2 Cl (1.0 g, 6.25 mmol) was dissolved in THF and then Na (dmamb) (0.87 g, 6.25 mmol) was added to the three-necked flask and stirred at room temperature for 12 hours. The reaction solution was filtered to remove the solvent under reduced pressure. The solvent was extracted with hexane, and the hexane was concentrated under reduced pressure to remove pure [In (CH 3 ) 2 (dmamb)] 2 as a white solid compound g, yield: 73%). (Sublimation temperature: 80 DEG C / 0.05 Torr)
1H NMR (C6D6, 300 MHz): δ 0.04 (s, 6H), 0.82 (t, 3H), 1.64 (m, 2H), 1.74 (m, 1H), 1.91 (s, 6H), 2.14(m, 1H). 1 H NMR (C 6 D 6 , 300 MHz): δ 0.04 (s, 6H), 0.82 (t, 3H), 1.64 (m, 2H), 1.74 (m, 1H), 1.91 (s, 6H), 2.14 (m, 1H).
Anal. Calcd for C18H44N2O2In2 : C, 39.29; H, 8.06; N, 5.09. Found: C, 38.94; H, 8.00, N; 5.01.Anal. Calcd for C 18 H 44 N 2 O 2 In 2 : C, 39.29; H, 8.06; N, 5.09. Found: C, 38.94; H, 8.00, N; 5.01.
녹는점 : 42 ℃
Melting point: 42 ℃
(실시예3) [In(CH3)2(dmaeb)]2의 합성(Example 3) Synthesis of [In (CH 3 ) 2 (dmaeb)] 2
삼구 플라스크에 In(CH3)2Cl (0.39 g, 2.20 mmol)을 THF에 용해시킨 후, Na(dmaeb) (0.37 g, 2.20 mmol) 넣어 상온에서 12 시간 동안 교반하였다. 반응물을 여과하여 얻은 용액을 감압 하에서 용매를 제거하였고, hexane으로 추출한 후, hexane을 감압 농축하여 제거하고, 이를 승화를 통해 순수한 [In(CH3)2(dmaeb)]2를 흰색 고체 화합물(0.25 g, 수율 67%)로 얻었다. (승화온도: 100 ℃/0.05 Torr)In (CH 3 ) 2 Cl (0.39 g, 2.20 mmol) was dissolved in THF and then Na (dmaeb) (0.37 g, 2.20 mmol) was added to the three-necked flask and stirred at room temperature for 12 hours. The reaction mixture was filtered and the solvent was removed under reduced pressure. After extracting with hexane, the hexane was concentrated under reduced pressure to remove pure [In (CH 3 ) 2 (dmaeb)] 2 as a white solid compound g, yield 67%). (Sublimation temperature: 100 DEG C / 0.05 Torr)
1H NMR (C6D6, 300 MHz): δ 0.06 (s, 6H), 0.91 (t, 6H), 1.59 (m, 4H), 1.94 (s, 6H), 2.02 (s, 2H). 1 H NMR (C 6 D 6 , 300 MHz): δ 0.06 (s, 6H), 0.91 (t, 6H), 1.59 (m, 4H), 1.94 (s, 6H), 2.02 (s, 2H).
Anal. Calcd for C20H48N2O2In2 : C, 41.54; H, 8.37; N, 4.84. Found: C, 41.18; H, 8.30, N; 4.56.Anal. Calcd for C 20 H 48 N 2 O 2 In 2: C, 41.54; H, 8.37; N, 4.84. Found: C, 41.18; H, 8.30, N; 4.56.
녹는점 : 135 ℃
Melting point: 135 ℃
인듐 전구체 물질의 분석Analysis of Indium Precursor Materials
상기 인듐 전구체의 열적 안정성 및 휘발성과 분해 온도를 측정하기 위해, 열중량 분석(thermogravimetric analysis, TGA)법을 이용하였다. 상기 TGA 방법은 생성물을 10 ℃/분의 속도로 900 ℃까지 가온시키면서, 1.5 bar/분의 압력으로 아르곤 기체를 주입하였다.Thermogravimetric analysis (TGA) was used to measure the thermal stability, volatility and decomposition temperature of the indium precursor. In the TGA method, argon gas was introduced at a pressure of 1.5 bar / min while warming the product to 900 ° C at a rate of 10 ° C / minute.
상기 실시예 1 내지 3에서 합성한 인듐 전구체 화합물의 그래프를 각각 도 1, 도 3 및 도 5에 도시하였다.The graphs of the indium precursor compounds synthesized in Examples 1 to 3 are shown in Figs. 1, 3 and 5, respectively.
실시예 1에서 수득한 인듐 화합물 [In(CH3)2(dmamp)]2는 110 ℃ 부근에서 질량 감소가 일어나기 시작하고 230 ℃에서 91 % 이상의 질량 감소가 관찰되었다(도 1 참조).The mass reduction of the indium compound [In (CH 3 ) 2 (dmamp)] 2 obtained in Example 1 began to occur at about 110 ° C and a mass decrease of more than 91% was observed at 230 ° C (see FIG.
실시예 2에서 수득한 인듐 화합물 [In(CH3)2(dmamb)]2는 100 ℃ 부근에서 질량 감소가 일어나기 시작하고 250 ℃에서 92 % 이상의 질량 감소가 관찰되었다(도 3 참조). The mass reduction of the indium compound [In (CH 3 ) 2 (dmamb)] 2 obtained in Example 2 began to occur at about 100 ° C and a mass reduction of more than 92% was observed at 250 ° C (see FIG. 3).
실시예 3에서 수득한 인듐 화합물 [In(CH3)2(dmaeb)]2는 90 ℃ 부근에서 질량 감소가 일어나기 시작하고 256 ℃에서 79 % 이상의 질량 감소가 일어나는 것을 관찰하였다(도 5 참조).
The mass of the indium compound [In (CH 3 ) 2 (dmaeb)] 2 obtained in Example 3 started to decrease at about 90 ° C and mass reduction of more than 79% at 256 ° C was observed (see FIG. 5).
또한 상기 실시예1 내지 실시예 3에서 제조된 인듐 화합물의 구체적인 구조를 확인하기 위하여 Bruker SMART APEX II X-ray Diffractometer를 이용하여 X-ray structure를 확인하여, 각각 도 2, 도 4 및 도 6에 나타내었다. 이를 통하여 세 인듐 화합물은 각 리간드들에 있는 산소가 두 인듐 원자에 다리 결합을 하고 있는 이합체 형태임을 확인할 수 있었다.In order to confirm the specific structure of the indium compounds prepared in Examples 1 to 3, the X-ray structure was confirmed using a Bruker SMART APEX II X-ray Diffractometer, and the results are shown in FIGS. 2, 4 and 6 Respectively. As a result, it was confirmed that the cesium indium compound was a dimer type in which oxygen in each ligand was bridged to two indium atoms.
Claims (5)
[화학식1]
[상기 화학식1에 있어서,
상기 R1 내지 R6은 각각 독립적으로 C1-C5의 선형 또는 분지형 알킬기이고;
상기 n은 1 내지 3의 정수이며;
상기 a는 1 내지 2이다.]An indium precursor represented by the following general formula (1)
[Chemical Formula 1]
[In the formula 1,
Each of R 1 to R 6 is independently a C1-C5 linear or branched alkyl group;
N is an integer of 1 to 3;
Wherein a is 1 to 2. "
[화학식2]
In(R1)(R2)X1
[화학식3]
[화학식1]
[상기 화학식1 내지 화학식3에 있어서,
상기 R1 내지 R6은 각각 독립적으로 C1-C10의 선형 또는 분지형 알킬기이고;
상기 X1은 할로겐이며;
상기 M은 Li, Na 또는 K이고;
상기 n은 1 내지 3의 정수이며;
상기 a는 1 내지 2이다.]Reacting a compound represented by Formula 2 and a compound represented by Formula 3 to prepare a compound represented by Formula 1 below; (1). ≪ / RTI >
(2)
In (R 1 ) (R 2 ) X 1
(3)
[Chemical Formula 1]
[In the above Chemical Formulas 1 to 3,
Each of R 1 to R 6 is independently a C1-C10 linear or branched alkyl group;
X < 1 > is halogen;
M is Li, Na or K;
N is an integer of 1 to 3;
Wherein a is 1 to 2. "
상기 인듐 함유 박막은 화학기상증착법(CVD) 또는 원자층증착법(ALD)으로 수행되는 것을 특징으로 하는 인듐 함유 박막의 제조 방법.5. The method of claim 4,
Wherein the indium-containing thin film is performed by chemical vapor deposition (CVD) or atomic layer deposition (ALD).
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| KR102548031B1 (en) * | 2022-11-16 | 2023-06-28 | 한국화학연구원 | Novel Organo-Indium Compounds and Method for forming thin film using the same |
| KR20230117368A (en) | 2020-12-04 | 2023-08-08 | 가부시키가이샤 아데카 | Indium compound, raw material for thin film formation, thin film and manufacturing method thereof |
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| KR20180056949A (en) | 2016-11-21 | 2018-05-30 | 한국화학연구원 | Group 13 metal precursor, composition for depositing thin film comprising the same, and a process for producing the thin film using the composition |
| KR20230117368A (en) | 2020-12-04 | 2023-08-08 | 가부시키가이샤 아데카 | Indium compound, raw material for thin film formation, thin film and manufacturing method thereof |
| KR102548031B1 (en) * | 2022-11-16 | 2023-06-28 | 한국화학연구원 | Novel Organo-Indium Compounds and Method for forming thin film using the same |
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