JP4920252B2 - リン含有シラザン組成物、リン含有シリカ質膜、リン含有シリカ質充填材、リン含有シリカ質膜の製造方法及び半導体装置 - Google Patents
リン含有シラザン組成物、リン含有シリカ質膜、リン含有シリカ質充填材、リン含有シリカ質膜の製造方法及び半導体装置 Download PDFInfo
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- JP4920252B2 JP4920252B2 JP2005511815A JP2005511815A JP4920252B2 JP 4920252 B2 JP4920252 B2 JP 4920252B2 JP 2005511815 A JP2005511815 A JP 2005511815A JP 2005511815 A JP2005511815 A JP 2005511815A JP 4920252 B2 JP4920252 B2 JP 4920252B2
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- phosphorus
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- carbon atoms
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- 229910052698 phosphorus Inorganic materials 0.000 title claims description 68
- 239000011574 phosphorus Substances 0.000 title claims description 66
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- 239000000203 mixture Substances 0.000 title claims description 42
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- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims description 42
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 29
- -1 phosphorus compound Chemical class 0.000 claims description 28
- 239000012298 atmosphere Substances 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 25
- 238000000576 coating method Methods 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000010304 firing Methods 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000012528 membrane Substances 0.000 claims description 12
- QJMMCGKXBZVAEI-UHFFFAOYSA-N tris(trimethylsilyl) phosphate Chemical compound C[Si](C)(C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C QJMMCGKXBZVAEI-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052736 halogen Inorganic materials 0.000 claims description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
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Description
−(SiR1(NR2)1.5)−(1)
(上式中、R1及びR2は各々独立に水素原子又は炭素原子数1〜3のアルキル基を表す。ただし、R1とR2が共に水素原子である場合を除く。)
−(SiR1(NR2)1.5)−(1)
(上式中、R1及びR2は各々独立に水素原子又は炭素原子数1〜3のアルキル基を表す。ただし、R1とR2が共に水素原子である場合を除く。)
比誘電率=(キャパシタンス〔pF〕)×(膜厚〔μm〕)/35.4
なお、比誘電率の値は17点の平均値とした。
膜密度〔g/cm3〕ニ(膜重量〔g〕〉/(膜厚〔μm〕)/0.008
内容積5Lのステンレス製タンク反応器に原料供給用のステンレスタンクを装着した。反応器内部を乾燥窒素で置換した後、原料供給用ステンレスタンクにメチルトリクロロシラン780gを入れ、これを窒素によって反応タンクに圧送し導入した。次にピリジン入りの原料供給タンクを反応器に接続し、ピリジン4kgを窒素で同様に圧送した。反応器の圧力を1.0kg/cm2に調整し、反応器内の混合液温が−4℃になるように温度調節を行った。そこに、撹拝しながらアンモニアを吹き込み、反応器の圧力が2.0kg/cm2になった時点でアンモニア供給を停止した。排気ラインを開けて反応器圧力を下げ、引き続き乾燥窒素を液層に1時間吹き込み、余剰のアンモニアを除去した。得られた生成物を加圧濾過器を用いて乾燥窒素雰囲気下で加圧濾渦し、濾液3200mLを得た。エバポレーターを用いてピリジンを留去したところ、約340gのポリメチルシラザンを得た。得られたポリメチルシラザンの数平均分子量をGPC(展開液:CHCl3)により測定したところ、ポリスチレン換算で1800であった。IR(赤外吸収)スペクトルは、波数(cm−1)3350、および1200付近のN−Hに基づく吸収;2900および1250のSi−Cに基づく吸収;1020〜820のSi−N−Siに基づく吸収を示した。
原料としてメチルトリクロロシラン780gの代わりに、メチルトリクロロシラン720g(約4.8モル)とジメチルジクロロシラン65g(約0.5モル)の混合物(メチルトリクロロシラン:ジメチルジクロロシラン=95:10(mo1/mo1))を用いたことを除き、参考例1と同様に合成を行い、約370gのポリメチルシラザンを得た。得られたポリメチルシラザンの数平均分子量をGPC(展開液:CHCl3)により測定したところ、ポリスチレン換算で1400であった。IR(赤外吸収)スペクトルは、波数(cm−1)3350、および1200付近のN−Hに基づく吸収;2900および1250のSi−Cに基づく吸収;1020〜820のSi−N−Siに基づく吸収を示した。
リン酸トリス(トリメチルシリル)を添加しないことを除き、実施例1と同様の溶液を調製した。その溶液を、実施例1と同様に濾過し、塗布し、加熱処理を施すに際し、塗布後の塗膜に、加湿器による50℃80%RHの加湿雰囲気において1時間吸湿させる工程を追加した。その後、実施例1と同様に焼成工程を施して焼成シリカ質膜を調製した。
リン酸トリス(トリメチルシリル)を添加しないことを除き、実施例3と同様の溶液を調製した。その溶液を、実施例3と同様に濾過し、塗布し、加熱処理を施すに際し、塗布後の塗膜に、加湿器による50℃80%RHの加湿雰囲気において1時間吸湿させる工程を追加した。その後、実施例3と同様に焼成工程を施して焼成シリカ質膜を調製した。
リン酸トリス(トリメチルシリル)を添加しないことを除き、実施例1と同様の溶液を調製した。その溶液を、実施例1と同様に濾過し、塗布した後、加湿処理を施さずに直ちに大気雰囲気中で150℃、次に250℃のホットプレート上でそれぞれ3分間加熱した。この膜を乾燥窒素雰囲気中500℃で30分間焼成したところ、焼成中に溶液中のコーティング成分が転化や架橋反応をすることなく飛散したことを示唆する膜ムラが生じ、また膜厚が実施例1の焼成膜の1/3程度しかなかった。IRスペクトルは、実施例1のスペクトルに加えて、波数(cm−1)900〜1000のSi−Nに由来するピークが多く残存していること、並びに波数(cm−1)920および3700付近にブロードなSi−OHに基づく吸収が存在することを示した。得られた膜の比誘電率は、焼成直後には3.85であったが、大気雰囲気中(25℃、相対湿度40%)3時間放置後には4.2を超え、膜の吸湿が進んだことが示唆された。
Claims (12)
- 有機溶媒中にポリアルキルシラザン、ならびに一般式(RO) 3 P=O(式中、Rは同一であっても異なってもよく、それぞれ水素、アンモニウム基、炭素原子数1〜5のアルキル基、炭素原子数6〜10の置換もしくは無置換アリール基、または置換基の炭素原子数が1〜4の三置換型シリル基を表す)で表されるリン酸類及び−R 1 2 P=N−(式中、R 1 は同一であっても異なってもよく、それぞれハロゲン、炭素原子数1〜5のアルコキシ基、または炭素原子数6〜10の置換もしくは無置換フェノキシ基を表す)構造を有するホスファゼンからなる群から選ばれる、少なくとも1種のリン化合物を含むことを特徴とする、リン含有シリカ質膜形成用シラザン組成物。
- 前記リン化合物が、リン酸、リン酸アンモニウム、リン酸トリメチル、リン酸トリエチル、リン酸トリブチル、リン酸トリクレシル、リン酸トリス(トリメチルシリル)、リン酸トリス(2−クロロエチル)、ヘキサクロロシクロホスファゼン、プロポキシホスファゼンオリゴマー、およびフェノキシホスファゼンオリゴマーからなる群から選択される、請求項1に記載の組成物。
- 前記リン化合物がリン酸トリス(トリメチルシリル)であることを特徴とする、請求項2に記載の組成物。
- 前記リン化合物が前記ポリアルキルシラザンに対して5〜100質量%含まれることを特徴とする、請求項1〜3のいずれか一項に記載の組成物。
- 前記ポリアルキルシラザンが、下記一般式(1)で表わされる繰返し単位および、少なくとも下記一般式(2)または下記一般式(3)で表される単位の一種を含む数平均分子量100〜50,000のものであることを特徴とする、請求項1〜4のいずれか一項に記載の組成物。
−(SiR1(NR2)1.5)− (1)
(上式中、R1及びR2は各々独立に水素原子又は炭素原子数1〜3のアルキル基を表す。ただし、R1とR2が共に水素原子である場合を除く。)
- 前記一般式(1)において、R1がメチル基であり且つR2が水素原子であり、前記一般式(2)において、R3及びR4が各々独立に水素原子又はメチル基であり且つR5が水素原子であり、さらに前記一般式(3)において、R7、R8、R9がメチル基であり且つR6が水素原子であることを特徴とする、請求項5に記載の組成物。
- 前記ポリアルキルシラザンが、前記一般式(1)で表される繰返し単位を、前記一般式(1)及び(2)及び(3)で表される単位の総数の50%以上含むことを特徴とする、請求項5又は6に記載の組成物。
- 請求項1〜7のいずれか一項に記載の組成物を基板上に塗布して得られた膜を、温度50〜300℃で予備焼成し、次いで温度300〜700℃の不活性雰囲気中で焼成することを特徴とする、リン含有シリカ質膜の製造方法。
- 請求項8記載の方法により製造された、リンを0.5〜10原子%含有することを特徴とするリン含有シリカ質膜。
- 請求項8記載の方法により製造された、比誘電率が3.5以下であることを特徴とする、リン含有シリカ質膜。
- 請求項1〜7のいずれか一項に記載の組成物を、最深部の幅が0.2μm以下であってその幅に対する深さの比が2以上である溝に充填し、温度50〜300℃で予備焼成し、次いで温度300〜700℃の不活性雰囲気中で焼成することにより得られる、リンを0.5〜10原子%含有することを特徴とするリン含有シリカ質充填材。
- 請求項8に記載の方法により製造されたリン含有シリカ質膜を層間絶縁膜として含むことを特徴とする半導体装置。
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EP3976720A1 (en) * | 2019-05-24 | 2022-04-06 | Merck Patent GmbH | Coating composition with phosphazene catalyst |
US20220267617A1 (en) * | 2021-02-23 | 2022-08-25 | Thor Custom Steel Coatings LLC | Steel Protective Coating Compositions, Methods of Their Manufacture, and Methods of Their Use |
US20230124254A1 (en) * | 2021-02-23 | 2023-04-20 | Thor Custom Steel Coatings LLC | Steel Protective Coating Compositions, Methods of Their Manufacture, and Methods of Their Use |
US20230212425A1 (en) * | 2021-02-23 | 2023-07-06 | Thor Custom Steel Coatings LLC | Steel Protective Coating Compositions, Methods of Their Manufacture, and Methods of Their Use |
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- 2004-06-24 TW TW093118298A patent/TWI326114B/zh not_active IP Right Cessation
- 2004-07-07 EP EP04747118.0A patent/EP1652890B1/en not_active Expired - Fee Related
- 2004-07-07 JP JP2005511815A patent/JP4920252B2/ja not_active Expired - Fee Related
- 2004-07-07 US US10/564,336 patent/US7368491B2/en not_active Expired - Fee Related
- 2004-07-07 CN CNB2004800205379A patent/CN100400599C/zh not_active Expired - Fee Related
- 2004-07-07 WO PCT/JP2004/009649 patent/WO2005007748A1/ja active Application Filing
- 2004-07-07 KR KR1020067001139A patent/KR101086625B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
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KR101086625B1 (ko) | 2011-11-25 |
US7368491B2 (en) | 2008-05-06 |
JPWO2005007748A1 (ja) | 2006-11-30 |
EP1652890A1 (en) | 2006-05-03 |
WO2005007748A1 (ja) | 2005-01-27 |
TW200504878A (en) | 2005-02-01 |
TWI326114B (en) | 2010-06-11 |
CN1823136A (zh) | 2006-08-23 |
EP1652890B1 (en) | 2017-01-11 |
US20060217487A1 (en) | 2006-09-28 |
KR20060066172A (ko) | 2006-06-15 |
CN100400599C (zh) | 2008-07-09 |
EP1652890A4 (en) | 2006-09-13 |
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