JP2014097969A - オニウム化合物およびその合成方法 - Google Patents
オニウム化合物およびその合成方法 Download PDFInfo
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- JP2014097969A JP2014097969A JP2013190009A JP2013190009A JP2014097969A JP 2014097969 A JP2014097969 A JP 2014097969A JP 2013190009 A JP2013190009 A JP 2013190009A JP 2013190009 A JP2013190009 A JP 2013190009A JP 2014097969 A JP2014097969 A JP 2014097969A
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- KWBKGYABUOLUOU-UHFFFAOYSA-N CCC1(CCCC1)OC(COC(c(cc1)cc([S+](c2c3cccc2)c2ccccc2C3=O)c1OC)=O)=O Chemical compound CCC1(CCCC1)OC(COC(c(cc1)cc([S+](c2c3cccc2)c2ccccc2C3=O)c1OC)=O)=O KWBKGYABUOLUOU-UHFFFAOYSA-N 0.000 description 2
- 0 *=C(CCOC(C(C1)(CC(C2)(C3)C1C2C1)CC31O)=O)C(S(O)(=O)=O)=* Chemical compound *=C(CCOC(C(C1)(CC(C2)(C3)C1C2C1)CC31O)=O)C(S(O)(=O)=O)=* 0.000 description 1
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- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
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Abstract
【解決手段】例えば、10−(5−((2−(1−エチルシクロペンチルオキシ)−2−オキソエトキシ)カルボニル)−2−メトキシフェニル)−9−オキソ−2−(トリフルオロメチル)−4,4a,9,10−テトラヒドロチオキサンチリウムトリフルオロメタンスルホネートをヨウ化ナトリウムで処理して下式でのヨウ化物塩を形成し、さらに、3−ヒドロキシアダマンタン−アセトキシ−1,1,2,2−テトラフルオロブタン−1−スルホン酸ナトリウム塩で処理することで、所望の新規オニウム塩化合物を調整する。
【選択図】なし
Description
(a)スルホネート成分が電子求引性基を含む、当該スルホネート成分を含むオニウム塩化合物を提供し;および
(b)前記オニウム塩化合物をハロゲン化物塩で処理してオニウム化合物の異なる塩を形成すること
を含む方法によって得られうるヨウ化物塩オニウム化合物が提供される。
また、
(a)スルホネート成分が電子求引性基を含む、当該スルホネート成分を含むオニウム塩を提供し;および
(b)前記スルホネート塩をハロゲン化物塩で処理してオニウム化合物のハロゲン化物塩を形成し;および
(c)前記オニウム化合物の前記ハロゲン化物塩を処理して前記オニウム化合物の異なる塩を形成すること
を含む方法によって得られうるさらなるオニウム塩化合物も提供される。
上述のように、本明細書に開示されるオニウム塩化合物は、ポジ型およびネガ型の両方の化学増幅型レジスト組成物をはじめとする、フォトレジスト組成物中の放射線感受性成分として有用である。
開始剤溶液は、65.96gの開始剤(V−65)を66gのアセトニトリル/テトラヒドロフラン(2/1 v/v)に溶解することによって調製された。重合は、水凝縮器およびフラスコ内の反応をモニターするための温度計を装備した2L三口丸底フラスコで行われた。オーバーヘッド撹拌機を用いて内容物を撹拌した。反応器にヒール溶液を入れ、その内容物を75℃に加熱した。シリンジポンプを用いて、フィード溶液および開始剤溶液が4時間にわたって反応器に供給された。次に、内容物をさらに2時間撹拌し、それにより、ヒドロキノン(2.0g)を用いて反応がクエンチされた。内容物を室温まで冷却し、10倍の(重量による)IPE/MeOH 95/5(w/w)で2回沈殿させた。得られたポリマーを、各沈殿工程の後に50℃で24時間真空乾燥させて500gのポリマーを得た。
ポジ型フォトレジスト組成物は、実施例20のポリマーの乳酸エチル中10重量%溶液21.088g、上記実施例1の酸発生剤化合物の乳酸エチル中2重量%溶液18.779g、1,1’,1’’,1’’’−(エタン−1,2−ジイルビス(アザントリイル))テトラプロパン−2−オールの乳酸エチル中0.5重量%溶液1.898g、フッ素化界面活性剤(Omnova PF656)の乳酸エチル中0.5重量%溶液0.422g、47.342gの乳酸エチルおよび29.250gの2−ヒドロキシイソ酪酸メチルエステルを一緒にすることによって調製される。配合したレジストを0.01μm PTFEフィルターに通す。こうして製造したレジストをシリコンウエハ上にスピンコーティングし、ソフトベークしてキャリア溶媒を除去し、フォトマスクを通してEUV放射線に露光する。次に、像形成したレジスト層を110℃で60秒間ベークした後、水性アルカリ組成物で現像する。
ポジ型フォトレジスト組成物は、実施例20のポリマーの乳酸エチル中10重量%溶液21.088g、上記実施例2の酸発生剤化合物の乳酸エチル中2重量%溶液19.522g、1,1’,1’’,1’’’−(エタン−1,2−ジイルビス(アザントリイル))テトラプロパン−2−オールの乳酸エチル中0.5重量%溶液1.898g、フッ素化界面活性剤(Omnova PF656)の乳酸エチル中0.5重量%溶液0.422g、46.342gの乳酸エチルおよび29.150gの2−ヒドロキシイソ酪酸メチルエステルを一緒にすることによって調製される。配合したレジストを0.01μm PTFEフィルターに通す。こうして製造したレジストをシリコンウエハ上にスピンコーティングし、ソフトベークしてキャリア溶媒を除去し、フォトマスクを通してEUV放射線に露光する。次に、像形成したレジスト層を110℃で60秒間ベークした後、水性アルカリ組成物で現像する。
Claims (10)
- (a)スルホネート成分が電子求引性基を含む、当該スルホネート成分を含むオニウム塩化合物を提供し、および
(b)前記オニウム塩化合物をハロゲン化物塩で処理してオニウム化合物の異なる塩を形成する
ことを含む、オニウム塩化合物を製造する方法。 - 前記1以上の電子求引性基が1以上のハロゲン原子を含む、請求項1に記載の方法。
- 前記スルホネート成分がトリフレートである、請求項1に記載の方法。
- R1、R2およびR3の1以上がハロゲンまたはハロゲン化アルキルである、請求項6に記載の方法。
- (i)前記オニウム塩化合物がハロゲン化物塩で処理されて、オニウム化合物のハロゲン化物塩を形成し、および(ii)前記オニウム化合物の前記ハロゲン化物塩がさらに処理されて、前記オニウム化合物の異なる塩を提供する、請求項1から5のいずれか一項に記載の方法。
- 請求項1から6のいずれか一項に記載の前記オニウム化合物の前記異なる塩とポリマーとを混合してフォトレジスト組成物を提供することを含む、フォトレジスト組成物を製造する方法。
- (i)請求項7に従って製造されたフォトレジスト組成物のコーティング層を基体表面上に適用し、(ii)前記フォトレジスト組成物層を活性化放射線に露光し、並びに(iii)前記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、フォトリソグラフィ方法。
- (a)スルホネート成分が電子求引性基を含む、当該スルホネート成分を含むオニウム塩を提供し、
(b)前記スルホネート塩をハロゲン化物塩で処理して、オニウム化合物のハロゲン化物塩を形成し、並びに
(c)前記オニウム化合物の前記ハロゲン化物塩を処理して、前記オニウム化合物の異なる塩を形成すること
を含む方法によって得られるオニウム塩化合物。 - ポリマーおよび請求項9に記載のオニウム塩化合物を含むフォトレジスト。
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