JP2011178988A - 感光性組成物 - Google Patents
感光性組成物 Download PDFInfo
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- JP2011178988A JP2011178988A JP2010289057A JP2010289057A JP2011178988A JP 2011178988 A JP2011178988 A JP 2011178988A JP 2010289057 A JP2010289057 A JP 2010289057A JP 2010289057 A JP2010289057 A JP 2010289057A JP 2011178988 A JP2011178988 A JP 2011178988A
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- 229920000642 polymer Polymers 0.000 claims abstract description 110
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- VDDICZVAQMPRIB-UHFFFAOYSA-N (2-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2C(O)C1(OC(=O)C(=C)C)C3 VDDICZVAQMPRIB-UHFFFAOYSA-N 0.000 claims description 2
- ZEFPSJCRLPUDJQ-UHFFFAOYSA-N (2-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(O)C2(OC(=O)C=C)C3 ZEFPSJCRLPUDJQ-UHFFFAOYSA-N 0.000 claims description 2
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
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- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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Abstract
【解決手段】第1の形態に従って、ポリマーが提供される。ポリマーはポリマー骨格およびポリマー骨格に共有結合したモノマー系光酸発生剤を含む。光酸発生剤は、重合性スルホナートアニオンを有するスルホニウム塩またはヨードニウム塩の1種以上に由来する。
【選択図】なし
Description
本発明は、感光性組成物およびその使用方法に関する。より具体的には、本発明は、化学線、特に、深紫外線(DUV−248nm)、193nmおよび極紫外線(EUV−13.4nm)のような300nm未満の波長、並びに、電子線(e−ビーム)放射線への露光でのフォトスピード(photospeed)を増大させるための分子構造を組み込むポジ型化学増幅フォトレジスト組成物に関する。本感光性組成物には、フォトリソグラフィプロセスにおいて有用な、例えば、半導体製造において、特別な適用性が見いだされる。
さらなる形態においては、Zは、末端CF2、C(F)(CF3)またはC(CF3)2を含む直鎖状または分岐フッ素化アルキル鎖を介してスルホナートアニオンに共有結合されている。さらなる形態においては、ポリマーは、光酸不安定(photoacid−labile)基を含む繰り返し単位をさらに含む。さらなる形態においては、ポリマーは、メタクリル酸2−メチルアダマンタニル、アクリル酸2−メチルアダマンタニル、アクリル酸ヒドロキシアダマンチル、メタクリル酸ヒドロキシアダマンチル、無水マレイン酸、ノルボルネン、3,4−ジヒドロピラン、場合によって置換されたフェニルおよび場合によって置換されたナフチルの1種以上から選択される重合単位をさらに含む。
さらなる形態においては、本発明に従って、ポリマーおよび組成物は、放射線に、例えば、300nm未満、例えば、248nm、193nmおよび13.4nmの活性化放射線、並びに電子線放射線で露光される場合に優れたフォトスピードを提供する。
さらなる形態においては、樹脂構造は、光子の高い断面吸収率を有し、そして光酸化を介して容易に二次電子を生じさせることができる。さらなる形態においては、本発明に従った樹脂構造は、酸拡散を効果的に制御することができ、かつ均一な酸分布および熱処理中の移動を提供することができる。
以下の非限定的な実施例は本発明の例示である。
モノマー系PAG合成:トリフェニルスルホニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートの合成
250mLのジクロロメタンおよび100mLの水の混合物に、19.14g(56.93mmol)の4−(メタクリルオキシ)−2,3,5,6−テトラフルオロベンゼンスルホナートナトリウム塩および17.0g(49.52mmol)のトリフェニルスルホニウムブロミドを添加した。この混合物を室温で36時間攪拌した。有機相が水性相から分けられて、水性相が100mLのジクロロメタンで洗浄された。ジクロロメタン溶液は一緒に集められて、引き続いて、1体積%の水酸化アンモニウム(2×100mL)および脱イオン水(3×100mL)で洗浄された。ジクロロメタン溶液はMgSO4で乾燥させられ、ろ過された。ジクロロメタンは蒸留除去されて、27.0gの純粋なトリフェニルスルホニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートを生じた。精製された物質についてNMR測定が行われ、以下の結果であった:
1HNMR(CDCl3,25℃,ppm):2.06(s,3H,CH3);5.90(s,1H,=CH);6.42(s,1H,=CH);7.68−7.76(m,15H,ArH)。
19FNMR(CDCl3,25℃,ppm):−139.06(m,2F);−154.33(m,2F)。
モノマー系PAG合成:トリ−(4−tert−ブチルフェニル)スルホニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートの合成
100mLのジクロロメタンおよび50mLの水の混合物に、6.0g(17.84mmol)の4−(メタクリルオキシ)−2,3,5,6−テトラフルオロベンゼンスルホナートナトリウム塩および8.0g(15.63mmol)のトリ−(4−tert−ブチルフェニル)スルホニウムブロミドを添加した。この混合物を室温で36時間攪拌した。有機相が水性相から分けられて、水性相が70mLのジクロロメタンで洗浄された。ジクロロメタン溶液は一緒に集められて、引き続いて、1体積%の水酸化アンモニウム(2×70mL)および脱イオン水(5×70mL)で洗浄された。ジクロロメタン溶液はMgSO4で乾燥させられ、ろ過された。ジクロロメタンは蒸留除去されて、11.70gの純粋なトリ−(4−tert−ブチルフェニル)スルホニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートを生じた。精製された物質についてNMR測定が行われ、以下の結果であった:
1HNMR(CDCl3,25℃,ppm):1.33(s,27H,3C(CH3)3);2.06(s,3H,CH3);5.86(s,1H,=CH);6.41(s,1H,=CH);7.69(m,12H,ArH)。
モノマー系PAG合成:ビス−(4−tert−ブチルフェニル)ヨードニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートの合成
100mLのジクロロメタンおよび70mLの水の混合物に、6.4g(19.0mmol)の4−(メタクリルオキシ)−2,3,5,6−テトラフルオロベンゼンスルホナートナトリウム塩および7.5g(16.57mmol)のビス−(4−tert−ブチルフェニル)ヨードニウムアセタートを添加した。この混合物を室温で12時間攪拌した。有機相が水性相から分けられて、水性相が50mLのジクロロメタンで洗浄された。ジクロロメタン溶液は一緒に集められて、引き続いて、1体積%の水酸化アンモニウム(2×50mL)および脱イオン水(5×50mL)で洗浄された。ジクロロメタン溶液はMgSO4で乾燥させられ、ろ過された。ジクロロメタンは蒸留除去されて、11.70gの純粋なビス−(4−tert−ブチルフェニル)ヨードニウム4−(メタクリルオキシ)−2,3,5,8−テトラフルオロベンゼンスルホナートを生じた。精製された物質についてNMR測定が行われ、以下の結果であった:
1HNMR(CDCl3,25℃,ppm):1.30(s,18H,2C(CH3)3);2.09(s,3H,CH3);6.05(s,1H,=CH);6.45(s,1H,=CH);7.56(d,4H,ArH);8.20(d,4H,ArH)。
ポリマー合成
0.039molのバゾ(Vazo登録商標)52低温重合開始剤(イーアイデュポンデネモラスアンドカンパニー)が、70.30g(0.3mol)のメタクリル酸2−メチル−2−アダマンチル、51.05g(0.3mol)の2−メチル−アクリル酸2−オキソ−テトラヒドロ−フラン−3−イルエステル、34.23g(0.15mol)のアクリル酸ヒドロキシナフチルメチル、および22.40g(0.039mol)の実施例1で形成されたPAGの、アセトニトリル:テトラヒドロフラン2:1混合物178g中の溶液に添加された。このモノマーおよび開始剤溶液は10分間脱ガスされた。不活性雰囲気下で、5mLのモノマーおよび開始剤溶液が、80℃に予備加熱された(オイルバス)反応器に導入された。モノマーおよび開始剤混合物の残りは、2時間の期間にわたって80℃で反応器に供給された。この添加の完了後、反応混合物はさらに二時間還流された。この混合物は室温に冷却され、重合溶液は多量のジイソプロピルエーテル中で沈殿させられ、ろ過され、真空下で乾燥された。得られた粗ポリマーは25−30重量%のテトラヒドロフラン(THF)中に溶解され、ジイソプロピルエーテル中で沈殿させられた。次いで、この物質は0.2ミクロンフィルタを用いてろ過され、ろ取物はジイソプロピルエーテルにゆっくりと添加され、THF:ジイソプロピルエーテルの1:10(体積/体積)溶液を得た。沈殿したポリマーがろ過によって単離され、真空下40℃で一晩乾燥させられた。
ポリマー合成
表1に特定されるようなモノマー種類およびモル供給物比を用いたことを除いて、実施例4におけるのと同じ手順を用いて表1に示されたポリマーが製造された。表1に示されたモノマーの構造は表2〜4に提供される。
フォトレジスト製造および処理
実施例4において製造されたポリマー1を4.95g、プロピレングリコールモノメチルエーテルアセタート中のオムノバ(Omnova)PF656界面活性剤の5重量%溶液を0.1g、塩基添加剤(トロジャーズ塩基(Troger’s Base))の1重量%溶液を1.0g、プロピレングリコールメチルエーテルアセタート溶媒を37.91g、および乳酸エチル溶媒を156g混合して一緒にすることにより、ポジ型フォトレジスト組成物が製造された。
レジストは以下のようにリソグラフィ処理された。配合されたレジストはHMDSまたはBARCコートされたシリコンウェハ上にスピンコートされ、130℃で90秒間ソフトベークされた。レジスト層はフォトマスクを通してDUVまたはEUV放射線で露光され、露光された層は約130℃で露光後ベーク(PEB)された。次いで、コーティングされたウェハはアルカリ塩基現像剤(0.26Nの水酸化テトラメチルアンモニウム水溶液)で処理されて、ポジ型レジスト層を現像した。
フォトレジスト製造および処理
表5に特定されるポリマーを使用したことを除いて、実施例26におけるのと同じ手順を使用して、ポジ型フォトレジスト組成物が製造された。各レジストは以下のようにリソグラフィ処理された。有機反射防止コーティング(AR商標19、ロームアンドハースエレクトロニックマテリアルズエルエルシー)を有する200mmシリコンウェハ上にレジストがスピンコートされ、130℃で60秒間ベークされ、70nmの厚みのレジスト膜を形成した。このレジストは193nmのフォトリソグラフィシステムを用いて化学線でパターン状(patternwise)に露光され、130℃90秒間で露光後ベーク(PEB)され、0.26Nの水酸化テトラメチルアンモニウム水溶液で現像されて、レジストパターンを形成した。90nmラインアンドスペースパターン(90nm L:SでのEsize)の頂部および底部において、1:1解像度を提供するのに必要とされる露光線量が表5に示される。
表6に特定されるポリマーを使用したことを除いて、実施例26におけるのと同じ手順を使用して、ポジ型フォトレジスト組成物が製造された。各レジストは以下のようにリソグラフィ処理された。有機反射防止コーティング(AR商標19またはAR商標107、ロームアンドハースエレクトロニックマテリアルズエルエルシー)を有する200mmシリコンウェハ上にレジストがスピンコートされ、130℃で60または90秒間ベークされ、60nmの厚みのレジスト膜を形成した。このレジスト層はEUV放射線(13.5nm波長)でパターン状に露光され、約130℃90秒間で露光後ベークされ、0.26Nの水酸化テトラメチルアンモニウム水溶液で現像されて、レジストパターンを形成した。30nmラインアンドスペースパターン(30nm L:SでのEsize)の頂部および底部において1:1解像度を提供するのに必要とされる露光線量が表6に示される。
Claims (10)
- Zが末端CF2、C(F)(CF3)またはC(CF3)2を含む直鎖状または分岐フッ素化アルキル鎖を介してスルホナートアニオンに共有結合されている、請求項1に記載のポリマー。
- 光酸不安定基を含む繰り返し単位をさらに含む、請求項1に記載のポリマー。
- メタクリル酸2−メチルアダマンタニル、アクリル酸2−メチルアダマンタニル、アクリル酸ヒドロキシアダマンチル、メタクリル酸ヒドロキシアダマンチル、無水マレイン酸、ノルボルネン、3,4−ジヒドロピラン、場合によって置換されたフェニルおよび場合によって置換されたナフチルの1種以上から選択される重合単位をさらに含む、請求項1に記載のポリマー。
- 請求項1のポリマーを含むポジ型フォトレジスト組成物。
- ポリマー骨格に共有結合しているモノマー系光酸発生剤を含まないポリマー骨格;および
光酸不安定基;
を含む第2のポリマーをさらに含む、請求項6に記載のポジ型フォトレジスト組成物。 - (a)パターン形成されるべき1以上の層を基体表面上に有する基体;並びに
(b)パターン形成されるべき1以上の層上の、請求項6のポジ型フォトレジスト組成物の層;
を含む、コーティングされた基体。 - (a)請求項6のポジ型フォトレジスト組成物の層を基体上に適用し;
(b)フォトレジスト組成物層を活性化放射線にパターン状に露光し;並びに
(c)露光されたフォトレジスト組成物層を現像して、レジストレリーフ像を提供する;
ことを含む、電子デバイスを形成する方法。 - 活性化放射線が極紫外線もしくは電子線放射線である、請求項9に記載の方法。
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JP2019038998A (ja) * | 2017-08-22 | 2019-03-14 | 住友化学株式会社 | 樹脂、レジスト組成物及びレジストパターンの製造方法 |
JP7363018B2 (ja) | 2017-08-22 | 2023-10-18 | 住友化学株式会社 | 樹脂、レジスト組成物及びレジストパターンの製造方法 |
Also Published As
Publication number | Publication date |
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TW201136957A (en) | 2011-11-01 |
EP2527380A1 (en) | 2012-11-28 |
EP2341089A1 (en) | 2011-07-06 |
CN102153695B (zh) | 2014-02-26 |
CN102153695A (zh) | 2011-08-17 |
EP2527380B1 (en) | 2013-12-18 |
JP5851688B2 (ja) | 2016-02-03 |
TWI444394B (zh) | 2014-07-11 |
US20110159429A1 (en) | 2011-06-30 |
KR20110079556A (ko) | 2011-07-07 |
EP2341089B1 (en) | 2013-02-13 |
KR101705043B1 (ko) | 2017-02-09 |
US8507176B2 (en) | 2013-08-13 |
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