JP7271850B2 - 有機金属前駆体化合物 - Google Patents
有機金属前駆体化合物 Download PDFInfo
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- JP7271850B2 JP7271850B2 JP2021183735A JP2021183735A JP7271850B2 JP 7271850 B2 JP7271850 B2 JP 7271850B2 JP 2021183735 A JP2021183735 A JP 2021183735A JP 2021183735 A JP2021183735 A JP 2021183735A JP 7271850 B2 JP7271850 B2 JP 7271850B2
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- 150000001875 compounds Chemical class 0.000 title claims description 81
- 239000002243 precursor Substances 0.000 title claims description 77
- 125000002524 organometallic group Chemical group 0.000 title claims description 64
- 239000010409 thin film Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 238000000231 atomic layer deposition Methods 0.000 claims description 22
- 239000010408 film Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229910000449 hafnium oxide Inorganic materials 0.000 claims description 7
- RQJBPBBHDSYDRW-UHFFFAOYSA-N CC(C)O[Hf](C1(C)C=CC=C1)(N(C)C)N(C)C Chemical compound CC(C)O[Hf](C1(C)C=CC=C1)(N(C)C)N(C)C RQJBPBBHDSYDRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052735 hafnium Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- JIGXARPLYFNBCG-UHFFFAOYSA-N C1(C=CC=C1)[Hf](N(C)C)(N(C)C)N(C)C Chemical compound C1(C=CC=C1)[Hf](N(C)C)(N(C)C)N(C)C JIGXARPLYFNBCG-UHFFFAOYSA-N 0.000 claims description 4
- -1 bis(dimethylamino)(iso-propoxy)(methylcyclopentadienyl)hafnium oxide Chemical compound 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000005121 nitriding Methods 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 238000000277 atomic layer chemical vapour deposition Methods 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910021481 rutherfordium Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 description 16
- 238000000151 deposition Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000008021 deposition Effects 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- 239000002184 metal Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000005229 chemical vapour deposition Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000012495 reaction gas Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002363 hafnium compounds Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000005240 physical vapour deposition Methods 0.000 description 4
- 238000000427 thin-film deposition Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005137 deposition process Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- DCPPOHMFYUOVGH-UHFFFAOYSA-N CN(C)[Zr](C1C=CC=C1)(N(C)C)N(C)C Chemical compound CN(C)[Zr](C1C=CC=C1)(N(C)C)N(C)C DCPPOHMFYUOVGH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910008328 ZrNx Inorganic materials 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 1
- INIGCWGJTZDVRY-UHFFFAOYSA-N hafnium zirconium Chemical compound [Zr].[Hf] INIGCWGJTZDVRY-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 0.000 description 1
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- C07F17/00—Metallocenes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- 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
- C23C16/02—Pretreatment of the material to be coated
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- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/301—AIII BV compounds, where A is Al, Ga, In or Tl and B is N, P, As, Sb or Bi
- C23C16/303—Nitrides
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- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
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- C23C16/448—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 generating reactive gas streams, e.g. by evaporation or sublimation of precursor materials
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- 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
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- 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]
- C23C16/45527—Atomic layer deposition [ALD] characterized by the ALD cycle, e.g. different flows or temperatures during half-reactions, unusual pulsing sequence, use of precursor mixtures or auxiliary reactants or activations
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- C23C16/45525—Atomic layer deposition [ALD]
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Description
R1、R2、R3、R4、及びR5は、それぞれ独立して、水素、炭素数1~5のアルキル基、炭素数1~5のアルコキシ基及び炭素数6~12のフェニル基の中から選択され、
Mは、周期表上で4族に属する金属元素の中から選択され、
R6、R7及びR8は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択され、
X1は、それぞれ独立して、下記化2aまたは2bで表される有機基の中から選択され、
R9、R10及びR11は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択され得る。
本発明の特徴によれば、前記化1において、Mは、Ti、Zr、Hf及びRfの中から選択され得るが、これに制限されるものではない。
以下においては、図1を参照して、本発明の一実施例に係る有機金属前駆体化合物及びそれを用いた薄膜の製造方法について説明する。
R1、R2、R3、R4、及びR5は、それぞれ独立して、水素、炭素数1~5のアルキル基、炭素数1~5のアルコキシ基及び炭素数6~12のフェニル基の中から選択され得るが、これに制限されるものではない。
Mは、周期表上で4族に属する金属元素の中から選択され得るが、これに制限されるものではなく、多様な金属元素をいずれも含むことができる。
R6、R7及びR8は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択され得るが、これに制限されるものではない。
R9、R10及びR11は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択され得るが、これに制限されるものではない。
R1、R2、R3、R4、R5、R6及びR7は、それぞれ独立して、水素及び炭素数1~5のアルキル基の中から選択され得るが、これに制限されるものではない。
以下においては、図2から図4を参照して、本発明の一実施例に係る特性を説明する。
R1、R2、R3、R4、R5、R6及びR7は、それぞれ独立して、水素及び炭素数1~5のアルキル基の中から選択され得るが、これに制限されるものではない。
Claims (9)
- 下記化1で表される、有機金属前駆体化合物であって、
R1、R2、R3、R4、及びR5は、それぞれ独立して、水素、炭素数1~5のアルキル基、および炭素数1~5のアルコキシ基の中から選択され、
Mは、周期表上で4族に属する金属元素の中から選択され、
R6、R7及びR8は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択され、
X1は、それぞれ独立して、下記化2aまたは2bで表される有機基の中から選択され、
R9、R10及びR11は、それぞれ独立して、水素、炭素数1~5の線状のアルキル基及び炭素数3~5の分枝状アルキル基の中から選択される、有機金属前駆体化合物。 - 前記化1において、Mは、Ti、Zr、Hf及びRfの中から選択される、請求項1に記載の有機金属前駆体化合物。
- 請求項1から3のいずれか一項に記載の有機金属前駆体化合物を反応器に導入するステップを含む、薄膜の製造方法。
- 前記薄膜の製造方法は、
原子層蒸着(Atomic Layer Deposition)または化学気相蒸着(Chemical Vapor Deposition)である、請求項4に記載の薄膜の製造方法。 - 前記薄膜の製造方法は、
酸化剤、窒化剤及び還元剤の少なくとも一つを導入するステップをさらに含む、請求項4に記載の薄膜の製造方法。 - 前記薄膜は、
ビス(ジメチルアミノ)(iso-プロポキシ)(メチルシクロペンタジエニル)ハフニウム酸化物(HfOx)膜である、請求項4に記載の薄膜の製造方法。 - 前記ビス(ジメチルアミノ)(iso-プロポキシ)(メチルシクロペンタジエニル)ハフニウムは、
(シクロペンタジエニル)トリス(ジメチルアミノ)ハフニウムよりGPC(Growth Per Cycle)値が0.2ずつ低い水準である、請求項7に記載の薄膜の製造方法。 - 前記薄膜の製造方法は、
前記有機金属前駆体化合物を基板上に移送するステップをさらに含み、
前記移送は、
蒸気圧を利用して揮発移送方法、直接液体注入方法(Direct Liquid Injection)及び液体移送方法(Liquid Delivery System)の少なくとも一つによって遂行される、請求項4に記載の薄膜の製造方法。
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