KR102029071B1 - Group 13 metal precursor, composition for depositing thin film comprising the same, and a process for producing the thin film using the composition - Google Patents
Group 13 metal precursor, composition for depositing thin film comprising the same, and a process for producing the thin film using the composition Download PDFInfo
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- 229910021482 group 13 metal Inorganic materials 0.000 title claims abstract description 56
- 239000002243 precursor Substances 0.000 title claims abstract description 41
- 239000010409 thin film Substances 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 title claims description 11
- 238000000151 deposition Methods 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 238000000427 thin-film deposition Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052738 indium Inorganic materials 0.000 claims description 7
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 238000000231 atomic layer deposition Methods 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052733 gallium Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000005229 chemical vapour deposition Methods 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- -1 tert-butyl ( tert-butyl) group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 239000007788 liquid Substances 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000004767 nitrides Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- BCEIDMOIGXJROC-UHFFFAOYSA-N CC(C(C)(N)C)NC Chemical compound CC(C(C)(N)C)NC BCEIDMOIGXJROC-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- MIKNSPXOIZYKIT-UHFFFAOYSA-N 2-methylbutane-2,3-diamine Chemical compound CC(N)C(C)(C)N MIKNSPXOIZYKIT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021617 Indium monochloride Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 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
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance 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
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- 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
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- 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
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- 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
- C23C16/06—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 metallic material
- C23C16/18—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 metallic material from metallo-organic compounds
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- 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
- C23C16/44—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 method of coating
- C23C16/455—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 method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
- C23C16/45523—Pulsed gas flow or change of composition over time
- C23C16/45525—Atomic layer deposition [ALD]
- C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD
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Abstract
본 발명의 13족 금속 전구체, 이의 제조방법 및 이를 이용하여 박막의 제조방법을 제공하는 것으로, 본 발명의 13족 금속 전구체는 상온에서 액체로 존재함으로써 취급이 용이하며, 휘발성 및 열안정성이 높아 이를 이용하여 쉽게 양질의 13족 금속 함유 박막을 제공할 수 있다.To provide a Group 13 metal precursor of the present invention, a method of manufacturing the same and a method for manufacturing a thin film using the same, Group 13 metal precursor of the present invention is a liquid at room temperature, easy to handle, high volatility and thermal stability It is possible to easily provide a high quality Group 13 metal-containing thin film.
Description
본 발명은 13족 금속 전구체, 이를 포함하는 박막증착용 조성물 및 이를 이용하는 박막의 제조방법에 관한 것으로, 보다 상세하게는 13족 금속을 포함하는 박막증착의 전구체로 유용한 13족 금속 전구체, 이를 포함하는 박막증착용 조성물 및 이를 이용하는 박막의 제조방법에 관한 것이다.The present invention relates to a Group 13 metal precursor, a composition for thin film deposition including the same, and a method for manufacturing a thin film using the same, and more particularly, to a Group 13 metal precursor useful as a precursor for thin film deposition including a Group 13 metal, It relates to a thin film deposition composition and a method for producing a thin film using the same.
최근 액정 표시 장치, 유기 발광 다이오드 등의 박막형 디스플레이 등의 전자 소자에 대한 수요가 증가함에 따라 양질의 전자 소자에 대한 요구도 급증하고 있다.Recently, as the demand for electronic devices such as liquid crystal displays and thin film displays such as organic light emitting diodes increases, the demand for high quality electronic devices also increases rapidly.
그동안 디스플레이 구동 소자로 실리콘이 가장 많이 사용되었으나, 산화물 반도체의 등장으로 실리콘을 대체하고자 하는 연구가 진행되고 있다.While silicon has been used most often as a display driving device, researches to replace silicon with the advent of oxide semiconductors are being conducted.
일례로 산화물 반도체는 새로운 박막트랜지스터 재료로서 에너지 밴드갭이 넓고 광투과도가 우수하여 박막트랜지스터에서 활성 영역의 채널층으로 이용하는데 큰 관심을 받고 있으며, 기존의 실리콘이 가지고 있는 특성적인 단점인 균일도와 이동도 향상에 대해 미래의 재료로써 많은 연구가 진행되고 있다.For example, oxide semiconductor is a new thin film transistor material, which has wide energy band gap and excellent light transmittance, so it is attracting much attention as a channel layer of active region in thin film transistor, and uniformity and movement, which are characteristic disadvantages of conventional silicon, A lot of research is being carried out as a future material for the improvement of the degree.
13족 금속산화물은 투명 산화물 반도체 소재로 사용 가능하며 전극, 전도성 코팅재료 등으로 응용이 가능하다.The Group 13 metal oxide can be used as a transparent oxide semiconductor material and can be applied as an electrode, a conductive coating material, and the like.
특히 13족 금속 중 인듐은 전기 도금을 통한 인듐 코팅 분야에 있어 마모에 대한 저항력이 뛰어난 점과 알루미늄 전선에 접촉 시 저항이 낮다는 특성 때문에 유용하게 활용되고 있으며 산화 인듐 증착에 사용되어온 전구체로서 Me3In가 널리 사용되고 있다. In particular, indium of Group 13 metal may be useful to utilize because there Resistant this point, the resistance when in contact with the aluminum wire is low superior to the wear characteristics to indium coatings by electroplating Me 3 as a precursor, which has been used in the indium oxide deposition In is widely used.
그러나 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 민감하다며 고체인 단점이 있다.However, InCl 3 may have chlorine contamination during thin film deposition and requires an oxygen source from the outside. Trialkylindium (III) such as Me 3 In or Et 3 In is highly volatile but highly resistant to oxygen and moisture. There is a disadvantage of being solid.
따라서 한국등록특허 제10-1629696호에 상기와 같은 단점을 해결하고자 할로겐을 함유하지 않아 오염을 방지할 수 있는 인듐 전구체를 제공하고 있다.Therefore, in order to solve the above disadvantages in Korea Patent Registration No. 10-1629696 it does not contain a halogen to provide an indium precursor that can prevent contamination.
그러나 여전히 휘발성 및 열안정성이 높고 다양한 박막에 적용이 가능한 13족 금속 전구체에 대한 연구가 요구된다.However, there is still a need for research on Group 13 metal precursors that are highly volatile and thermally stable and applicable to various thin films.
본 발명은 휘발성 및 열안정성이 높아 양질의 13족 금속박막의 전구체로 사용가능한 13족 금속 전구체를 제공한다.The present invention provides a Group 13 metal precursor that can be used as a precursor of a Group 13 metal thin film having high volatility and thermal stability.
또한 본 발명은 본 발명의 13족 금속 전구체를 포함하는 박막증착용 조성물을 제공한다.In another aspect, the present invention provides a composition for thin film deposition comprising a Group 13 metal precursor of the present invention.
또한 본 발명은 본 발명의 박막증착용 조성물을 이용하는 박막의 제조방법 및 본 발명의 13족 금속 전구체를 이용하여 제조된 박막을 제공한다.In another aspect, the present invention provides a method for producing a thin film using the composition for thin film deposition of the present invention and a thin film prepared using the Group 13 metal precursor of the present invention.
본 발명은 13족 금속 박막증착에 유용한 13족 금속 전구체를 제공하는 것으로, 본 발명의 13족 금속 전구체는 하기 화학식 1로 표시된다.The present invention provides a Group 13 metal precursor useful for Group 13 metal thin film deposition, the Group 13 metal precursor of the present invention is represented by the following formula (1).
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1,
M은 13족 금속이며;M is a Group 13 metal;
R1 및 R2는 서로 독립적으로 C1 내지 C4의 선형 또는 분지형 알킬이고, R3 내지 R7은 서로 독립적으로 C1 내지 C10의 선형 또는 분지형 알킬이며;R 1 and R 2 are independently of each other C1 to C4 linear or branched alkyl, and R 3 to R 7 are independently of each other C1 to C10 linear or branched alkyl;
A는 -(CR11R12)n-이며, R11 및 R12는 서로 독립적으로 수소 또는 (C1-C5)알킬이며;A is-(CR 11 R 12 ) n- , R 11 and R 12 independently of one another are hydrogen or (C 1 -C 5) alkyl;
n은 0 내지 5의 정수이다.]n is an integer of 0 to 5.]
바람직하게 본 발명의 상기 화학식 1에서 M은 알루미늄, 인듐 또는 갈륨일 수 있다.Preferably M in the formula 1 of the present invention may be aluminum, indium or gallium.
본 발명이 상기 화학식 1에서 R1 및 R2는 각각 독립적으로 (C1-C4)알킬이고, R3 내지 R7은 각각 독립적으로 (C1-C10)알킬이며, R11 및 R12는 수소일 수 있으며; 바람직하게는 R1 내지 R7은 서로 독립적으로 (C1-C4)알킬이며, R11 및 R12는 수소이며, n은 1일 수 있으며; 보다 바람직하게는 R1 내지 R4는 메틸이며, R5 내지 R7은 (C1-C3)알킬이며, R11 및 R12는 수소이며, n은 1일 수 있다.In the present invention, in Formula 1, R 1 and R 2 are each independently (C1-C4) alkyl, R 3 to R 7 are each independently (C1-C10) alkyl, R 11 and R 12 may be hydrogen; Preferably R 1 to R 7 are independently of each other (C1-C4) alkyl, R 11 and R 12 is hydrogen and n can be 1; More preferably R 1 to R 4 are methyl, R 5 to R 7 are (C 1 -C 3) alkyl, R 11 and R 12 is hydrogen and n may be 1.
또한 본 발명은 본 발명의 13족 금속 전구체를 포함하는 박막증착용 조성물 및 본 발명의 13족 금속 전구체를 이용하여 13족 금속 함유 박막을 성장시키는 방법 및 이로부터 제조된 13족 함유 박막을 제공한다.The present invention also provides a composition for thin film deposition comprising the Group 13 metal precursor of the present invention, a method for growing a Group 13 metal-containing thin film using the Group 13 metal precursor of the present invention, and a Group 13-containing thin film prepared therefrom. .
본 발명의 13족 금속 전구체는 상온에서 액체로 존재하여 보관 및 취급이 용이할 뿐만 아니라 열안정성 및 휘발성이 우수하여 양질의 박막을 제조할 수 있다.The Group 13 metal precursor of the present invention is a liquid at room temperature, not only easy to store and handle, but also excellent in thermal stability and volatility, thereby producing a thin film of good quality.
또한 본 발명의 13족 금속 전구체는 다양한 박막, 13족 금속산화물 박막 뿐만 아니라 특히 13족 금속질화물 박막을 균일하고 순도 높은 박막을 제조할 수 있다.In addition, the Group 13 metal precursor of the present invention can prepare a thin film of uniform and high purity, as well as various thin films, Group 13 metal oxide thin film, in particular Group 13 metal nitride thin film.
따라서 본 발명의 13족 금속 전구체를 포함하는 박막증착용 조성물은 본 발명의 13족 금속 전구체를 사용함으로써 용이하게 양질의 박막을 제조할 수 있다.Therefore, the thin film deposition composition containing the Group 13 metal precursor of the present invention can be easily produced a high quality thin film by using the Group 13 metal precursor of the present invention.
도 1은 본 발명의 실시예 2에서 제조된 알루미늄 전구체의 TG 분석 결과를 나타낸 도면이다.1 is a view showing the results of TG analysis of the aluminum precursor prepared in Example 2 of the present invention.
본 발명은 열안정성 및 휘발성이 높아 다양한 13족 금속박막의 증착의 선구물질로 유용하게 사용가능한 13족 금속 전구체를 제공하는 것으로, 본 발명의 13족 금속 전구체는 하기 화학식 1로 표시된다.The present invention provides a Group 13 metal precursor that can be usefully used as a precursor for the deposition of various Group 13 metal thin films having high thermal stability and volatility, and the Group 13 metal precursor of the present invention is represented by the following Chemical Formula 1.
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1,
M은 13족 금속이며;M is a Group 13 metal;
R1 및 R2는 서로 독립적으로 C1 내지 C4의 선형 또는 분지형 알킬이고, R3 내지 R7은 서로 독립적으로 C1 내지 C10의 선형 또는 분지형 알킬이며;R 1 and R 2 are independently of each other C1 to C4 linear or branched alkyl, and R 3 to R 7 are independently of each other C1 to C10 linear or branched alkyl;
A는 -(CR11R12)n-이며, R11 및 R12는 서로 독립적으로 수소 또는 (C1-C5)알킬이며;A is-(CR 11 R 12 ) n- , R 11 and R 12 independently of one another are hydrogen or (C 1 -C 5) alkyl;
n은 0 내지 5의 정수이다.]n is an integer of 0 to 5.]
본 발명의 상기 화학식 1에서 M은 13족 금속이며 모두 가능하며, 일례로 붕소(B), 알루미늄(Al), 갈륨(Ga), 인듐(In), 탈륨(Tl) 또는 니호늄(Nh)일 수 있으며, 바람직하게는 알루미늄, 인듐 또는 갈륨일 수 있다.In Formula 1 of the present invention, M is a Group 13 metal, and all are possible, for example, boron (B), aluminum (Al), gallium (Ga), indium (In), thallium (Tl), or nihonium (Nh) yl. And preferably aluminum, indium or gallium.
본 발명이 상기 화학식 1에서 R1 및 R2는 각각 독립적으로 (C1-C4)알킬이고, R3 내지 R7은 각각 독립적으로 (C1-C10)알킬이며, R11 및 R12는 수소일 수 있으며; 바람직하게는 R1 내지 R7은 서로 독립적으로 (C1-C4)알킬이며, R11 및 R12는 수소이며, n은 1일 수 있으며; 보다 바람직하게는 R1 내지 R4는 메틸이며, R5 내지 R7은 (C1-C3)알킬이며, R11 및 R12는 수소이며, n은 1일 수 있다.In the present invention, in Formula 1, R 1 and R 2 are each independently (C1-C4) alkyl, R 3 to R 7 are each independently (C1-C10) alkyl, R 11 and R 12 may be hydrogen; Preferably R 1 to R 7 are independently of each other (C1-C4) alkyl, R 11 and R 12 is hydrogen and n can be 1; More preferably R 1 to R 4 are methyl, R 5 to R 7 are (C 1 -C 3) alkyl, R 11 and R 12 is hydrogen and n may be 1.
본 발명에 기재된 '알킬'은 직쇄 또는 분지쇄를 모두 포함한다.'Alkyl' as described herein includes both straight and branched chains.
바람직하게는 본 발명의 상기 화학식 1에서 상기 R1 내지 R7은 서로 독립적으로 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(iso-propyl), 부틸(butyl), 이소부틸(iso-butyl) 또는 tert-부틸(tert-butyl)일 수 있다.Preferably, in Formula 1 of the present invention, R 1 to R 7 are independently of each other methyl, ethyl, propyl, isopropyl, butyl, isobutyl (iso-butyl) or tert-butyl.
본 발명의 13족 금속 전구체는 일례로 하기 화학식 2와 화학식 3 또는 하기 화학식 4를 반응시켜 제조될 수 있으나, 당업자가 인식할 수 있는 범위내에서 가능한 방법이라면 모두 가능하다.The Group 13 metal precursor of the present invention may be prepared by reacting the following Chemical Formula 2 with Chemical Formula 3 or Chemical Formula 4 as an example, but any method may be possible within a range that can be recognized by those skilled in the art.
[화학식 2][Formula 2]
M(R1)(R2)(Ra)M (R 1 ) (R 2 ) (R a )
[화학식 3][Formula 3]
[화학식 4][Formula 4]
(상기 화학식 2 및 3에서, M, R1 내지 R7, A는 상기 화학식 1과 동일하며, Ra는 상기 화학식 R1 및 R2의 정의와 동일하며, M1은 알칼리금속이다.) (In Formulas 2 and 3, M, R 1 to R 7 , A are the same as in Formula 1, R a is the same as defined in Formulas R 1 and R 2 , M 1 is an alkali metal.)
본 발명의 일 실시예에 따른 상기 화학식 1의 제조방법에서 반응은 질소 또는 비활성 기체하에서 수행될 수 있으며, 상온(10 내지 35 ℃)에서 8시간 내지 24시간동안 수행될 수 있다.In the preparation method of Chemical Formula 1 according to an embodiment of the present invention, the reaction may be performed under nitrogen or an inert gas, and may be performed at room temperature (10 to 35 ° C.) for 8 hours to 24 hours.
또한 본 발명은 본 발명의 박막증착용 조성물 및 본 발명의 13족 금속 전구체를 이용하는 박막의 제조방법을 제공한다.The present invention also provides a composition for thin film deposition of the present invention and a method for producing a thin film using the Group 13 metal precursor of the present invention.
본 발명의 13족 금속 박막은 통상적인 방법으로 제조될 수 있으며, 일례로 유기금속 화학기상 증착법(MOCVD), 원자층 증착법(ALD) 공정, 저압 기상 증착법(LPCVD), 플라즈마 강화 기상 증착법 (PECVD) 또는 플라즈마 강화 원자층 증착법(PEALD)등을 들 수 있다.The Group 13 metal thin film of the present invention may be manufactured by a conventional method, for example, organometallic chemical vapor deposition (MOCVD), atomic layer deposition (ALD) process, low pressure vapor deposition (LPCVD), plasma enhanced vapor deposition (PECVD) Or plasma enhanced atomic layer deposition (PEALD).
본 발명의 13족 금속 박막은 본 발명의 13족 금속 전구체를 이용하여 제조되며, 한정이 있는 것은 아니나 일례로 13족 금속질화막, 13족 금속산화막, 13족 금속탄소질화막, 규소-13족 금속질화막일 수 있으며, 바람직하게 13족 금속질화막일 수 있다.The Group 13 metal thin film of the present invention is manufactured by using the Group 13 metal precursor of the present invention, but is not limited to, for example, Group 13 metal nitride film, Group 13 metal oxide film, Group 13 metal carbon nitride film, silicon-group 13 metal nitride film It may be, preferably a group 13 metal nitride film.
본 발명의 13족 금속 박막의 제조방법은 높은 휘발성과 높은 열적 안정성을 가지는 본 발명의 13족 금속 전구체를 사용하여 제조됨으로써 제조된 13족 금속 박막은 물리적, 전기적, 화학적 특성이 매우 우수하다.The Group 13 metal thin film manufacturing method of the present invention is manufactured by using the Group 13 metal precursor of the present invention having high volatility and high thermal stability is very excellent in physical, electrical, and chemical properties.
본 발명의 13족 금속 박막의 제조방법에서 본 발명의 13족 금속 전구체의 주입온도는 25 내지 120 ℃일 수 있으며, 본 발명의 13족 금속 전구체의 높은 휘발성으로 인해 13족 금속이 증착될 기판의 온도는 100 내지 450 ℃, 챔버내부 압력은 0.1 내지 10 torr일 수 있다.In the manufacturing method of the Group 13 metal thin film of the present invention, the injection temperature of the Group 13 metal precursor of the present invention may be 25 to 120 ℃, due to the high volatility of the Group 13 metal precursor of the present invention of the substrate to be deposited The temperature may be 100 to 450 ° C., and the internal pressure of the chamber may be 0.1 to 10 torr.
본 발명의 13족 금속 박막의 제조방법에서 사용되는 반응가스는 한정이 있는 것은 아니나, 수소(H2), 히드라진(N2H4), 오존(O3), 산소(O2), 물(H2O), 암모니아(NH3), 질소(N2), 실란(SiH4), 보란(BH3), 디보란(B2H6) 및 포스핀(PH3)에서 선택되는 하나 또는 하나이상의 혼합기체일 수 있다.The reaction gas used in the manufacturing method of the Group 13 metal thin film of the present invention is not limited, but hydrogen (H 2 ), hydrazine (N 2 H 4 ), ozone (O 3 ), oxygen (O 2 ), water ( One or one selected from H 2 O), ammonia (NH 3 ), nitrogen (N 2 ), silane (SiH 4 ), borane (BH 3 ), diborane (B 2 H 6 ) and phosphine (PH 3 ) It may be a mixed gas.
아래에 실시 예를 통하여 본 발명을 더 구체적으로 설명한다. 이에 앞서, 본 명세서 및 청구범위에 사용된 용어나 단어는 통상적이거나 사전적인 의미로 한정해서 해석되어서는 아니 되며, 발명자는 그 자신의 발명을 가장 최선의 방법으로 설명하기 위해 용어의 개념을 적절하게 정의할 수 있다는 원칙에 입각하여 본 발명의 기술적 사상에 부합하는 의미와 개념으로 해석되어야만 한다. 따라서, 본 명세서에 기재된 실시 예와 도면에 도시된 구성은 본 발명의 가장 바람직한 일 실시예에 불과할 뿐이고 본 발명의 기술적인 사상을 모두 대변하는 것은 아니므로, 본 출원시점에 있어서 이들은 대체할 수 있는 다양한 균등물과 변형 예들이 있음을 이해하여야 한다.The present invention will be described in more detail with reference to the following examples. Prior to this, terms or words used in the present specification and claims should not be construed as being limited to the common or dictionary meanings, and the inventors should properly explain the concept of terms in order to best explain their own invention. Based on the principle that can be defined, it should be interpreted as meaning and concept corresponding to the technical idea of the present invention. Therefore, the embodiments described in the specification and the drawings shown in the drawings are only one of the most preferred embodiments of the present invention and do not represent all of the technical spirit of the present invention, they can be replaced at the time of the present application It should be understood that there are various equivalents and variations.
[실시예 1] Al(CH3)2(tmpda) (tmpda: N2-methyl-N1,N1,2-dimethylpropan-1,2-diamine)의 합성Example 1 Synthesis of Al (CH 3 ) 2 (tmpda) (tmpda: N 2 -methyl-N 1 , N 1 , 2-dimethylpropan-1,2-diamine)
둥근 플라스크에 Trimethylaluminum (0.28 g, 3.83 mmol)을 Toluene(20mL)에 용해시킨 후, 저온(0 ℃)에서 tmpda (0.50 g, 3.83 mmol) 넣고, 상온으로 온도를 올린 후 상온에서 12시간동안 교반시켰다. 반응물을 여과하여 얻은 용액을 감압 하에서 부산물을 제거 하였으며, 표제 화합물인 노란색 액체 화합물 (0.46 g, 수율 64%)을 얻었다. (정제온도: 75 ℃/0.05 mmHg) Trimethylaluminum (0.28 g, 3.83 mmol) was dissolved in Toluene (20 mL) in a round flask, tmpda (0.50 g, 3.83 mmol) was added at low temperature (0 ° C.), the temperature was raised to room temperature, and the mixture was stirred at room temperature for 12 hours. . The reaction product was filtered to remove the by-products under reduced pressure, to obtain a yellow liquid compound (0.46 g, 64% yield) as the title compound. (Purification temperature: 75 ℃ / 0.05 mmHg)
1H NMR (C6D6, 300 MHz): δ -0.55 (s, 6H), 1.05 (s, 6H), 1.84 (s, 6H), 2.11 (s, 2H), 2.69 (s, 3H). 1 H NMR (C 6 D 6 , 300 MHz): δ -0.55 (s, 6H), 1.05 (s, 6H), 1.84 (s, 6H), 2.11 (s, 2H), 2.69 (s, 3H).
[실시예 2] Al(CH3)2(etmpda) (etmpda: N2-ethyl-N1,N1,2-trimethylpropan-1,2-diamine)의 합성Example 2 Synthesis of Al (CH 3 ) 2 (etmpda) (etmpda: N 2 -ethyl-N 1 , N 1 , 2-trimethylpropan-1,2-diamine)
둥근 플라스크에 Trimethylaluminum (1.00 g, 13.8 mmol)을 Toluene(50)mL에 용해시킨 후, 저온(0℃)에서 etmpda (2.00 g, 13.8 mmol) 넣고, 상온으로 온도를 올린 후 상온에서 12시간동안 교반시켰다. 반응물을 여과하여 얻은 용액을 감압 하에서 부산물을 제거 하였으며, 표제 화합물인 노란색 액체 화합물 (2.13 g, 수율 77 %)을 얻었다. (정제온도: 70 ℃/0.05 mmHg) In a round flask, Trimethylaluminum (1.00 g, 13.8 mmol) was dissolved in Toluene (50) mL, and then etmpda (2.00 g, 13.8 mmol) was added at low temperature (0 ° C.), raised to room temperature and stirred at room temperature for 12 hours. I was. The reaction product was filtered to remove the by-products under reduced pressure to obtain the title compound yellow liquid compound (2.13 g, yield 77%). (Purification temperature: 70 ℃ / 0.05 mmHg)
1H NMR (C6D6, 300 MHz): δ -0.48 (s, 6H), 1.07 (s, 6H), 1.43 (t, 3H), 1.82 (s, 6H), 2.09 (s, 2H), 3.00 (q, 2H). 1 H NMR (C 6 D 6 , 300 MHz): δ -0.48 (s, 6H), 1.07 (s, 6H), 1.43 (t, 3H), 1.82 (s, 6H), 2.09 (s, 2H), 3.00 (q, 2 H).
13C NMR (C6D6, 300 MHz): δ -7.6 (2C, Al(CH3)2), 19.0 (1C, N(CH2 CH3)), 28.9 (2C, C(CH3)2), 38.0 (1C, C(CH3)2), 47.1 (2C, CH2N(CH3)2), 54.5 (1C, N(CH2CH3)), 73.6 (1C, CH2N(CH3)2). 13 C NMR (C 6 D 6 , 300 MHz): δ -7.6 (2C, Al ( C H 3 ) 2 ), 19.0 (1C, N (CH 2 C H 3 )), 28.9 (2C, C ( C H 3 ) 2 ), 38.0 (1C, C (CH 3 ) 2 ), 47.1 (2C, CH 2 N ( C H 3 ) 2 ), 54.5 (1C, N ( C H 2 CH 3 )), 73.6 (1C, C H 2 N (CH 3 ) 2 ).
실시예 2에서 제조된 알루미늄 전구체의 TG 분석 결과를 도 1에 나타내었으며, 도 1에 서 보이는 바와 같이 실시예 2의 알루미늄 전구체는 80 ℃ 부근에서 질량 감소가 일어나기 시작하고 242 ℃에서 87% 이상의 질량 감소가 일어나는 것을 알 수 있으며, 이로서 제조된 알루미늄 전구체가 열적 안정성이 높은 것을 알 수 있다.The TG analysis of the aluminum precursor prepared in Example 2 is shown in FIG. 1, and as shown in FIG. 1, the aluminum precursor of Example 2 began to lose mass at about 80 ° C. and a mass of at least 87% at 242 ° C. It can be seen that a decrease occurs, whereby the aluminum precursor produced has a high thermal stability.
[실시예 3] Ga(CH3)2(etmpda) (etmpda: N2-ethyl-N1,N1,2-trimethylpropan-1,2-diamine)의 합성Example 3 Synthesis of Ga (CH 3 ) 2 (etmpda) (etmpda: N 2 -ethyl-N 1 , N 1 , 2-trimethylpropan-1,2-diamine)
둥근 플라스크에 Trimethylaluminum (0.79 g, 6.93 mmol)을 Toluene(50)mL에 용해시킨 후, 저온(0℃)에서 etmpda (1.0 g, 6.93 mmol) 넣고, 상온으로 온도를 올린 후 상온에서 12시간동안 교반시켰다. 반응물을 여과하여 얻은 용액을 감압 하에서 부산물을 제거 하였으며, 표제 화합물인 노란색 액체 화합물 (0.97g, 수율 58 %)을 얻었다. (정제온도: 80 ℃/ 0.05 mmHg) In a round flask, Trimethylaluminum (0.79 g, 6.93 mmol) was dissolved in Toluene (50) mL, and then etmpda (1.0 g, 6.93 mmol) was added at low temperature (0 ° C.), raised to room temperature and stirred at room temperature for 12 hours. I was. The reaction product was filtered to remove the by-products under reduced pressure, and the title compound was obtained as a yellow liquid compound (0.97 g, yield 58%). (Purification temperature: 80 ℃ / 0.05 mmHg)
1H NMR (C6D6, 300 MHz): δ -0.14 (s, 6H), 1.11 (s, 6H), 1.36 (t, 3H), 1.80 (s, 6H), 2.08 (s, 2H), 3.07 (q, 2H). 1 H NMR (C 6 D 6 , 300 MHz): δ -0.14 (s, 6H), 1.11 (s, 6H), 1.36 (t, 3H), 1.80 (s, 6H), 2.08 (s, 2H), 3.07 (q, 2 H).
[실시예 4] In(CH3)2(etmpda) (etmpda : N2-ethyl-N1,N1,2-trimethylpropan-1,2-diamine)의 합성Example 4 Synthesis of In (CH 3 ) 2 (etmpda) (etmpda: N 2 -ethyl-N 1 , N 1 , 2-trimethylpropan-1,2-diamine)
삼각 플라스크에 In(CH3)2Cl (0.95g, 5.26 mmol)을 THF(50)mL에 용해시킨 후, Li(etmpda) (0.79 g, 5.26 mmol) 넣어 상온에서 12시간동안 교반시켰다. 반응물을 여과하여 얻은 용액을 감압 하에서 부산물을 제거하였고 hexane으로 추출한 후, hexane을 제거하여 건조시켜 옅은 노란색 액체 화합물 (0.95g, 수율 63 %)을 얻었다. (정제온도: 75 ℃/0.05 mmHg) In (CH 3 ) 2 Cl (0.95 g, 5.26 mmol) was dissolved in THF (50) mL in an Erlenmeyer flask, and Li (etmpda) (0.79 g, 5.26 mmol) was added thereto and stirred at room temperature for 12 hours. The reaction product was filtered to remove the by-products under reduced pressure, extracted with hexane, hexane was removed and dried to give a pale yellow liquid compound (0.95g, 63% yield). (Purification temperature: 75 ℃ / 0.05 mmHg)
1H NMR (C6D6, 300 MHz): δ -0.07 (s, 6H), 1.16 (s, 6H), 1.30 (t, 3H), 1.83 (s, 6H), 2.09 (s, 2H), 3.20 (q, 2H). 1 H NMR (C 6 D 6 , 300 MHz): δ -0.07 (s, 6H), 1.16 (s, 6H), 1.30 (t, 3H), 1.83 (s, 6H), 2.09 (s, 2H), 3.20 (q, 2 H).
13C NMR (C6D6, 300 MHz): δ-5.9 (2C, In(CH3)2), 20.7 (1C, N(CH2 CH3)), 28.7 (2C, C(CH3)2), 41.3 (1C, N(CH2CH3)), 48.9 (2C, CH2N(CH3)2), 57.9 (1C, C(CH3)2), 76.3 (1C, CH2N(CH3)2). 13 C NMR (C 6 D 6 , 300 MHz): δ-5.9 (2C, In ( C H 3 ) 2 ), 20.7 (1C, N (CH 2 C H 3 )), 28.7 (2C, C ( C H 3 ) 2 ), 41.3 (1C, N ( C H 2 CH 3 )), 48.9 (2C, CH 2 N ( C H 3 ) 2 ), 57.9 (1C, C (CH 3 ) 2 ), 76.3 (1C, C H 2 N (CH 3 ) 2 ).
실험예 1. 망간 전구체 물질의 분석Experimental Example 1. Analysis of Manganese Precursor Material
상기 실시예 2의 Al(CH3)2(etmpda)의 열적 안정성 및 휘발성과 분해 온도를 알아보기 위해, 열무게 분석(thermogravimetric analysis, TGA)법을 이용하였다. 상기 TGA 방법은 생성물을 10 ℃/분의 속도로 900 ℃까지 가온 시키면서, 1.5 bar/분의 압력으로 아르곤 가스를 주입하였다. In order to determine the thermal stability, volatility and decomposition temperature of Al (CH 3 ) 2 (etmpda) of Example 2, thermogravimetric analysis (TGA) was used. The TGA method injected argon gas at a pressure of 1.5 bar / minute while warming the product to 900 ° C. at a rate of 10 ° C./min.
실시예 2의 Al(CH3)2(etmpda)은 80 ℃ 근처에서 질량 감소가 일어나기 시작하고, 200 ℃에서 87% 이상의 질량 감소가 일어나는 것을 관찰하였다[도 1].Al (CH 3 ) 2 (etmpda) of Example 2 observed that mass reduction began to occur around 80 ° C., and mass loss of 87% or more occurred at 200 ° C. [FIG. 1].
또한 상기 TGA 데이터로 본 발명의 화합물의 휘발성 정도가 양호하다는 것을 알 수 있었다. In addition, the TGA data showed that the degree of volatility of the compound of the present invention was good.
Claims (7)
[화학식 1]
(상기 화학식 1에서,
M은 알루미늄, 인듐 또는 갈륨이며;
R1 및 R2는 각각 독립적으로 C1 내지 C4의 선형 또는 분지형 알킬이고,
R3 내지 R7은 각각 독립적으로 (C1-C4)알킬이며;
A는 -(C(R11R12)n-이며, R11 및 R12는 서로 독립적으로 수소 또는 (C1-C5)알킬이며;
n은 0 내지 5의 정수이다.]Group 13 metal precursor represented by the following formula (1).
[Formula 1]
(In Formula 1,
M is aluminum, indium or gallium;
R 1 and R 2 are each independently C 1 to C 4 linear or branched alkyl,
R 3 to R 7 are each independently (C 1 -C 4) alkyl;
A is-(C (R 11 R 12 ) n- , R 11 and R 12 independently of one another are hydrogen or (C 1 -C 5) alkyl;
n is an integer of 0 to 5.]
상기 화학식 1에서 R11 및 R12는 수소이며; n은 1 내지 2인 13족 금속 전구체.The method of claim 1,
In Formula 1 R 11 And R 12 is hydrogen; n is a group 13 metal precursor of 1 to 2.
상기 R1 내지 R7은 서로 독립적으로 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(iso-propyl), 부틸(butyl), 이소부틸(iso-butyl) 또는 tert-부틸(tert-butyl)인 13족 금속 전구체.The method of claim 1,
R 1 to R 7 are independently of each other methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl ( tert-butyl) group 13 metal precursor.
상기 박막은 성장 공정이 화학기상증착법(CVD) 또는 원자층증착법(ALD)에 의해 수행되는 것인 방법.The method of claim 5,
Wherein said thin film is grown by chemical vapor deposition (CVD) or atomic layer deposition (ALD).
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