JP2012246531A - 酸化モリブデンを含有する薄膜の製造方法、酸化モリブデンを含有する薄膜の形成用原料及びモリブデンアミド化合物 - Google Patents
酸化モリブデンを含有する薄膜の製造方法、酸化モリブデンを含有する薄膜の形成用原料及びモリブデンアミド化合物 Download PDFInfo
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- JP2012246531A JP2012246531A JP2011118760A JP2011118760A JP2012246531A JP 2012246531 A JP2012246531 A JP 2012246531A JP 2011118760 A JP2011118760 A JP 2011118760A JP 2011118760 A JP2011118760 A JP 2011118760A JP 2012246531 A JP2012246531 A JP 2012246531A
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- Prior art keywords
- thin film
- molybdenum
- molybdenum oxide
- compound
- amide compound
- Prior art date
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- 239000010409 thin film Substances 0.000 title claims abstract description 82
- -1 molybdenum amide compound Chemical class 0.000 title claims abstract description 56
- 229910052750 molybdenum Inorganic materials 0.000 title claims abstract description 50
- 239000011733 molybdenum Substances 0.000 title claims abstract description 50
- 229910000476 molybdenum oxide Inorganic materials 0.000 title claims abstract description 47
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title abstract description 53
- 239000007858 starting material Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 230000008016 vaporization Effects 0.000 claims abstract description 16
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- 239000002994 raw material Substances 0.000 claims description 43
- 239000007789 gas Substances 0.000 claims description 35
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910001868 water Inorganic materials 0.000 claims description 4
- 239000002243 precursor Substances 0.000 abstract description 27
- 230000008569 process Effects 0.000 abstract description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 5
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 38
- 238000000151 deposition Methods 0.000 description 20
- 239000007788 liquid Substances 0.000 description 20
- 230000008021 deposition Effects 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 14
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- 239000010408 film Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
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- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
【解決手段】下記一般式(I)で表される化合物を含有してなる薄膜形成用原料を気化させて得たモリブデンアミド化合物を含有する蒸気を基体上に導入し、さらに酸化性ガスを導入することで分解及び/又は化学反応させて基体上に薄膜を形成する、酸化モリブデンを含有する薄膜の製造方法。式中、R1、R2は炭素数1〜4の直鎖又は分岐状アルキル基を表し、R3はt−ブチル基又はt−アミル基を表し、yは0又は2を表し、xはyが0のときに4であり、yが2のときに2であり、複数存在するR1、R2はそれぞれ同一でもよく、異なっても良い。
【選択図】なし
Description
化合物No.37の製造
乾燥アルゴンガス雰囲気下で、500mL反応フラスコにモリブデン酸ナトリウム0.12モル、1,2−ジメトキシエタン2.52モル、t−アミルアミン0.252モル、トリエチルアミン0.48モル、トリメチルクロロシラン0.96モルを仕込み、系内の温度を80〜82℃にコントロールして12時間攪拌を行った。反応液を0.2μmのフィルターで固形分をろ過した後、溶媒を減圧留去により濃縮することで深緑色スラリー状の反応性中間体を収率95%で得た。引き続き、反応フラスコに反応性中間体0.114モルと脱水処理を行ったトルエン1.12モルを加えて溶解した後、溶液を−20℃にドライアイス―イソプロパノールにより冷却し、ジメチルアミンガス0.48モルを吹き込み、続いて1.6mol/Lノルマルブチルリチウムのヘキサン溶液140mLを滴下して反応させた。反応溶液を徐々に室温へ戻し、引き続き2時間撹拌して反応させた。反応液を0.2μmのフィルターにより固形物をろ過後、溶媒を減圧留去により濃縮し、これからさらに減圧蒸留により195Pa、塔頂温度103〜104℃のフラクションを分取し、目的物である化合物No.37を得た。この精製による回収率は60%であった。得られた橙黄色液体について、以下の分析を行った。
(1)元素分析(金属分析:ICP−AES、塩素分析:TOX)
モリブデン;26.89質量%(理論値27.07%)、Na;1ppm未満、Cl;5ppm未満
(2)1H−NMR(溶媒:重ベンゼン)(ケミカルシフト:多重度:H数)
(1.06:t:3)(1.35:s:6)(1.62:q:2)(3.46:s:6)
(3)TG−DTA
(Ar100ml/min、10℃/min昇温、サンプル量8.836mg)
50質量%減少温度190℃
化合物No.38の製造
乾燥アルゴンガス雰囲気下で、500mL反応フラスコにモリブデン酸ナトリウム0.12モル、1,2−ジメトキシエタン2.52モル、t−アミルアミン0.252モル、トリエチルアミン0.48モル、トリメチルクロロシラン0.96モルを仕込み、系内の温度を80〜82℃にコントロールして12時間攪拌を行った。反応液を0.2μmのフィルターで固形分をろ過した後、溶媒を減圧留去により濃縮することで深緑色スラリー状の反応性中間体を収率95%で得た。引き続き、反応フラスコに反応性中間体0.114モルと脱水処理を行ったトルエン1.12モルを加えて溶解した後、溶液を−20℃にドライアイス―イソプロパノールにより冷却し、エチルメチルアミン0.48モルを滴下、続いて1.6mol/Lノルマルブチルリチウムのヘキサン溶液140mLを滴下して反応させた。反応溶液を徐々に室温へ戻し、引き続き2時間撹拌して反応させた。反応液を0.2μmのフィルターにより固形物をろ過後、溶媒を減圧留去により濃縮し、これからさらに減圧蒸留により40Pa、塔頂温度98〜101℃のフラクションを分取し、目的物である化合物No.38を得た。この精製よる回収率は60%であった。得られた黄色液体について、以下の分析を行った。
(1)元素分析(金属分析:ICP−AES、塩素分析:TOX)
モリブデン;25.31質量%(理論値25.09%)、Na;1ppm未満、Cl;5ppm未満
(2)1H−NMR(溶媒:重ベンゼン)(ケミカルシフト:多重度:H数)
(1.02:t:2)(1.30:s:9)(1.59:q:3)(3.47:s:3)(3.67:q:2)
(3)TG−DTA
(Ar100ml/min、10℃/min昇温、サンプル量12.009mg)
50質量%減少温度209℃
上記製造実施例により得られた新規化合物No.37、38、公知化合物である化合物No.1、2、9、73、74及び以下に示す比較化合物1、2について、目視によって常温常圧における化合物の状態を観察し、固体化合物については微小融点測定装置を用いて融点を測定し、さらに各化合物の沸点を測定した。結果を表1に示す。
MoF6
比較化合物 2
Mo(CO)6
比較化合物2、化合物No.2、及び化合物No.37、38についてオゾン雰囲気下でTG−DTA測定を実施した。測定条件はオゾン4%を添加した酸素2000ml/min、10℃/min昇温で行った。モリブデン化合物とオゾンとの反応性の有無を、オゾンによるモリブデン化合物の酸化分解によって発生する重量減少を伴う発熱ピークの有無によって確認し、さらに反応が十分に終了したと考えられる300℃における残分量を確認した。尚、サンプル量は3.275mg〜8.447mgであった。この結果を表2に示す。
化合物No.2を化学気相成長用原料とし、図1に示す装置を用いて以下の条件及び工程のALD法により、シリコンウエハ上に酸化モリブデン薄膜を製造した。得られた薄膜について、蛍光X線による膜厚測定及びX線光電子分光法による組成比分析、X線回折による組成分析を行った。結果を表3に示す。
(条件)
反応温度(基板温度);240℃、反応性ガス;オゾンガス
(工程)
下記(1)〜(4)からなる一連の工程を1サイクルとして、50サイクル繰り返した。
(1)気化室温度70℃、気化室圧力70Paの条件で気化させた化学気相成長用原料の蒸気を導入し、系圧100Paで20秒間堆積させる。
(2)15秒間のアルゴンパージにより、未反応原料を除去する。
(3)反応性ガスを導入し、系圧力80Paで20秒間反応させる。
(4)15秒間のアルゴンパージにより、未反応原料を除去する。
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PCT/JP2012/062199 WO2012165124A1 (ja) | 2011-05-27 | 2012-05-11 | 酸化モリブデンを含有する薄膜の製造方法、酸化モリブデンを含有する薄膜の形成用原料及びモリブデンアミド化合物 |
CN201280020076.XA CN103562434A (zh) | 2011-05-27 | 2012-05-11 | 含有氧化钼的薄膜的制造方法、含有氧化钼的薄膜的形成用原料以及钼酰胺化合物 |
US14/112,125 US20140141165A1 (en) | 2011-05-27 | 2012-05-11 | Method for manufacturing molybdenum oxide-containing thin film, starting material for forming molybdenum oxide-containing thin film, and molybdenum amide compound |
KR1020137027972A KR101912127B1 (ko) | 2011-05-27 | 2012-05-11 | 산화몰리브덴을 함유하는 박막의 제조방법, 산화몰리브덴을 함유하는 박막의 형성용 원료 및 몰리브덴아미드 화합물 |
TW101118237A TWI546308B (zh) | 2011-05-27 | 2012-05-22 | A method for producing a film containing molybdenum oxide, a raw material for forming a film containing molybdenum oxide, and a compound of molybdenum amide (MOLYBDENUM AMIDE) |
US14/823,293 US9881796B2 (en) | 2011-05-27 | 2015-08-11 | Method for manufacturing molybdenum oxide-containing thin film |
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WO2012165124A1 (ja) | 2012-12-06 |
US20140141165A1 (en) | 2014-05-22 |
KR20140025408A (ko) | 2014-03-04 |
US9881796B2 (en) | 2018-01-30 |
JP5730670B2 (ja) | 2015-06-10 |
KR101912127B1 (ko) | 2018-10-26 |
TWI546308B (zh) | 2016-08-21 |
CN103562434A (zh) | 2014-02-05 |
US20150371859A1 (en) | 2015-12-24 |
TW201307362A (zh) | 2013-02-16 |
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