JP3980124B2 - New bissulfonyldiazomethane - Google Patents
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- JP3980124B2 JP3980124B2 JP19895497A JP19895497A JP3980124B2 JP 3980124 B2 JP3980124 B2 JP 3980124B2 JP 19895497 A JP19895497 A JP 19895497A JP 19895497 A JP19895497 A JP 19895497A JP 3980124 B2 JP3980124 B2 JP 3980124B2
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【０００１】
【発明の属する技術分野】
本発明は化学増幅型レジストの酸発生剤として好適な新規ビススルホニルジアゾメタン化合物に関するものである。
【０００２】
【従来の技術】
近年、半導体素子や液晶素子などの製造においては、化学増幅型レジスト組成物が使用されるようになってきた。この化学増幅型レジスト組成物は、放射線の照射により生成した酸の触媒作用を利用したレジストであって、高い感度と解像性を有し、放射線の照射により酸を発生する化合物すなわち酸発生剤の使用量が少なくてよいという利点を有している。
【０００３】
この化学増幅型レジストにはポジ型とネガ型の２つのタイプがあり、これらは、一般に、酸発生剤と、発生する酸の作用によりアルカリ水溶液に対する溶解性が変化する被膜形成成分とを基本成分としている。
【０００４】
前記ポジ型レジストにおいては、被膜形成成分として、通常ｔｅｒｔ‐ブトキシカルボニル基、テトラヒドロピラニル基などの溶解抑制基で水酸基の一部を保護したポリヒドロキシスチレンなどが用いられており、一方、ネガ型レジストにおいては、被膜形成成分として、通常上記溶解抑制基で水酸基の一部を保護したポリヒドロキシスチレン、あるいはポリヒドロキシスチレンやノボラック樹脂などの樹脂成分に、メラミン樹脂や尿素樹脂などの酸架橋性物質を組み合わせたものが用いられている。
【０００５】
ところで、このような酸発生剤として、ある種のジアゾメタン化合物が用いられているが（特開平３−１０３８５４号公報、特開平４−２１０９６０号公報、特開平４−２１７２４９号公報）、これらを用いたレジスト組成物は、露光部と未露光部のコントラストに劣るため、残膜率が低くなるという欠点がある。
【０００６】
【発明が解決しようとする課題】
本発明は、従来のジアゾメタン化合物がもつ欠点を克服し、化学増幅型レジストの酸発生剤として用いた場合、露光部と未露光部のコントラストに優れ、高残膜率を示す新規なビススルホニルジアゾメタンを提供することを目的としてなされたものである。
【０００７】
【課題を解決するための手段】
本発明者らは、化学増幅型レジストの酸発生剤として用いたときに、露光部と未露光部のコントラストに優れ、高残膜率を示す新規なビススルホニルジアゾメタン化合物を開発するために鋭意研究を重ねた結果、２個のテトラヒドロピラニルオキシ基置換脂環式基をもつ化合物が、その目的を達成しうることを見出し、この知見に基づいて本発明をなすに至った。
【０００８】
すなわち、本発明は、一般式
【化２】
で表わされるビススルホニルジアゾメタンを提供するものである。
【０００９】
この一般式（Ｉ）中の脂環式基は、２個のＲが水素原子の場合はシクロヘキシル基であり、２個のＲが一緒になってジメチルメチレン基を形成している場合は、７，７‐ジメチルビシクロ［２．２．１］ヘプチル基である。
この脂環式基に結合しているテトラヒドロピラニルオキシ基は、２‐位置、３‐位置、４‐位置のいずれの位置に結合していてもよい。
【００１０】
【発明の実施の形態】
本発明の化合物の中で前記一般式（Ｉ）中のＲが水素原子であるもの、すなわち脂環式基がシクロヘキシル基である場合は、例えば次に示す反応式に従い、ビス（ヒドロキシシクロヘキシル）スルホニルジアゾメタン又はビス（ヒドロキシシクロヘキシルメチル）スルホニルジアゾメタン（ＩＩ）に、３，４‐ジヒドロ‐２Ｈ‐ピラン（ＩＩＩ）を反応させることにより製造することができる。
【００１１】
【化３】
【００１２】
この反応は、不活性溶媒例えばテトラヒドロフラン、ジオキサンのような環状エーテル中、ｐ‐トルエンスルホン酸ピリジニウムの存在下で行われる。
また、前記一般式（Ｉ）の同一環中の２個のＲがジメチルメチレン基を形成しているもの、すなわち７，７‐ジメチルビシクロ［２．２．１］ヘプチル基である場合は、次の反応式に従い、対応するヒドロキシ置換脂環式メルカプタン（ＩＶ）とメチレンハライド（Ｖ）とを縮合させて対応するビス（ヒドロキシ置換脂環式チオ）メタン（ＶＩ）を形成させ、これを酸化して対応するビススルホニルメタン（ＶＩＩ）に変換したのち、ジアゾ化して、ビス（ヒドロキシ置換脂環式スルホニル）ジアゾメタン（ＶＩＩＩ）を製造し、これに３，４‐ジヒドロ‐２Ｈ‐ピラン（ＩＩＩ）を反応させることによって得ることができる。
【００１３】
【化４】
【００１４】
この反応において用いるメチレンハライド（Ｖ）の例としては、メチレンクロリド、メチレンブロミド、メチレンヨージドを挙げることができる。
前記反応式においてヒドロキシ置換脂環式メルカプタン（ＩＶ）とメチレンハライドとの縮合は、不活性溶媒例えばエタノール中において、水酸化カリウムのような塩基の存在下で行われる。
【００１５】
次に、このようにして得たビス（ヒドロキシ置換脂環式チオ）メタン（ＶＩ）を酸化して対応するビススルホニルメタン（ＶＩＩ）に変換する反応は、例えばエタノールのような不活性溶媒中、タングステン酸アルカリを触媒として過酸化水素によって行うことができる。
【００１６】
さらに、このようにして変換したビススルホニルメタン（ＶＩＩ）のジアゾ化は、例えば、エタノールのような不活性溶媒中、水酸化カリウムや水酸化ナトリウムのような塩基の存在下でトシルアジドを反応させることによって行われる。そして、最後のビス（ヒドロキシ置換脂環式スルホニル）ジアゾメタン（ＶＩＩＩ）と３，４‐ジヒドロ‐２Ｈ‐ピラン（ＩＩＩ）との反応は、シクロヘキシル基の場合と同様に、ｐ‐トルエンスルホン酸ピリジニウムの存在下で行われる。このようにして得た生成物は、常法に従い再結晶などの手段により精製することができる。
【００１７】
このようにして得られる前記一般式（Ｉ）のビススルホニルジアゾメタン化合物は、文献未載の新規化合物であって、光の照射により酸を発生すると同時に、テトラヒドロピラニルオキシ基が発生した酸により解離する性質を有している。
【００１８】
【実施例】
次に実施例により本発明をさらに詳細に説明する。
【００１９】
実施例１
ビス（２‐ヒドロキシシクロヘキシルスルホニル）ジアゾメタン５ｇ（０．０１４モル）と３，４‐ジヒドロ‐２Ｈ‐ピラン３．５ｇ（０．０４２モル）をジオキサン５０ｇに溶かし、ｐ‐トルエンスルホン酸ピリジニウム０．１ｇを加え、室温で４０時間かきまぜた。次いで、水５０ｇを加え、酢酸エチル３０ｇで抽出後、溶媒を留去し、さらにシリカゲルカラムクロマトグラフィにより分解、精製することにより、式
【化５】
このものの赤外吸収スペクトル及びプロトン核磁気共鳴スペクトルを図１及び図２に示す。
【００２０】
実施例２
水酸化カリウム３０ｇ（０．５３モル）をエタノール３００ｇに溶かし、これにメルカプトイソボルネオール６０ｇ（０．３２モル）を加えた。次いで、メチレンブロミド２８ｇ（０．１６モル）を室温にて３０分にわたって滴下した。この反応混合物をさらに５０℃で３時間かき混ぜたのち、析出した臭化カリウムをろ別し、次いで、希塩酸で中和し、さらにメチレンクロリド５００ｇで抽出、溶媒を留去し、ビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルチオ〕メタン６７ｇを黄色油状物として得た。
次いで、このビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルチオ〕メタン６７ｇ（０．１７モル）をエタノール３００ｇに溶かし、タングステン酸ナトリウム０．６ｇを加えた。これに、３５％過酸化水素水２００ｇ（２．０６モル）を４５℃において３０分にわたって滴下した。この反応混合物をさらに５０℃で２０時間かきまぜた。次いで、水１０００ｇを加え、析出したビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルスルホニル〕メタン５１ｇを白色結晶として得た。
次に、このビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルスルホニル〕メタン２０ｇ（０．０４５モル）とトシルアジド１０ｇ（０．０５１モル）をエタノール８０ｇに溶かし、これに１０％水酸化カリウム水溶液３００ｇ（０．５３モル）を室温で３０分にわたって滴下した。この反応混合物をさらに室温で２時間かきまぜた。次いで、析出した結晶をろ取し、ビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルスルホニル〕ジアゾメタン６．５ｇを得た。
【００２１】
このようにして得たビス〔２‐ヒドロキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルスルホニル〕ジアゾメタン５．０ｇ（０．０１１モル）と３，４‐ジヒドロ‐２Ｈ‐ピラン２．９ｇ（０．０３３モル）をジオキサン５０ｇに溶かし、ｐ‐トルエンスルホン酸ピリジニウム０．１ｇを加え、室温で４０時間かきまぜた。次いで水５０ｇを加え、酢酸エチル３０ｇで抽出後、溶媒を留去し、さらにシリカゲルカラムクロマトグラフィにより分離精製することにより、式
【化６】
【００２２】
参考例
水酸基の水素原子の３９モル％がｔｅｒｔ‐ブチルオキシカルボニル基で置換された重量平均分子量１０，０００のポリヒドロキシスチレンと水酸基の水素原子の３９モル％がエトキシエチル基で置換された重量平均分子量１０，０００のポリヒドロキシスチレンとを重量比３：７の割合で含む樹脂混合物１００重量部に、酸発生剤として実施例１で得たビス［２‐（２‐テトラヒドロピラニル）オキシシクロヘキシルスルホニル］ジアゾメタン７重量部又は実施例２で得たビス〔２‐［２‐テトラヒドロピラニル］オキシ‐７，７‐ジメチルビシクロ［２．２．１］ヘプタニルメチルスルホニル〕ジアゾメタン７重量部とトリエチルアミン０．３重量部とサリチル酸０．２重量部を配合し、プロピレングリコールモノメチルエーテルアセテート４９０重量部に溶解し、この溶液を孔径０．２μｍのメンブランフィルターを通してろ過し、ポジ型レジスト組成物を調製した。
次に、このポジ型レジスト組成物について以下に示す方法で物性を求め、その結果を表１に示す。
なお、比較のために、公知の酸発生剤であるビス（シクロヘキシルスルホニル）ジアゾメタン５重量部を用いたポジ型レジスト組成物についての物性を求め、その結果を表１に併記した。
【００２３】
（１）感度：
試料をスピンナーを用いてシリコンウエーハ上に塗布し、これをホットプレート上で９０℃、９０秒間乾燥して膜厚０．７μｍのレジスト膜を得た。この膜に縮小投影露光装置ＮＳＲ−２００５ＥＸ８Ａ（ニコン社製）を用いて、１ｍＪ／ｃｍ2ずつドーズ量を加え露光したのち、１１０℃、９０秒間のＰＥＢ（ＰＯＳＴ ＥＸＰＯＳＵＲＥ ＢＡＫＥ）を行い、２．３８重量％テトラメチルアンモニウムヒドロキシド水溶液で２３℃にて６０秒間現像し、３０秒間水洗して乾燥したとき、現像後の露光部の膜厚が０となる最小露光時間を感度としてｍＪ／ｃｍ2（エネルギー量）単位で測定した。
【００２４】
（２）解像性：
上記（１）と同様な操作を行い、０．２５μｍのマスクパターンを再現する露光量における限界解像度で示した。
【００２５】
（３）レジストパターン形状：
上記（１）と同様な操作を行い、０．２５μｍの矩形のレジストパターンが得られた場合を○、レジストパターントップがやや細いパターンとなったり、波打ったレジストパターンとなった場合を×として評価した。
【００２６】
（４）引き置き経時安定性：
上記（１）において、露光までの操作を行ったのち、６０分間放置したあと、同様にＰＥＢ処理、現像を行い、０．２５μｍのレジストパターンの断面形状をＳＥＭ（走査型電子顕微鏡）写真により観察し、０．２５μｍのラインアンドスペースが１：１に形成されたものを５、ライン幅（レジストパターン幅）が０．２５μｍより広くなり、スペース幅が０．２５μｍより狭くなったものを３、解像しないものを１とし、それぞれの中間を４，２として評価した。
【００２７】
（５）残膜率：
上記（１）と同様な操作を行い、未露光部の残膜率を現像前膜厚に対する現像後膜厚の割合として求めた。
【００２８】
【表１】
【発明の効果】
本発明化合物は新規化合物であって、これを化学増幅型レジストの酸発生剤として用いると、露光部と未露光部のコントラストに優れるため、残膜率が高くプロファイル形状の優れたパターンを与える。
【図面の簡単な説明】
【図１】 実施例１で得た化合物の赤外吸収スペクトル図。
【図２】 実施例１で得た化合物のプロトン核磁気共鳴スペクトル図。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a suitable new bissulfonyldiazomethane compounds as an acid generator for a chemically amplified resist.
[0002]
[Prior art]
In recent years, chemically amplified resist compositions have been used in the manufacture of semiconductor devices, liquid crystal devices, and the like. This chemically amplified resist composition is a resist that utilizes the catalytic action of an acid generated by radiation irradiation, and has a high sensitivity and resolution, and is a compound that generates an acid upon radiation irradiation, that is, an acid generator. There is an advantage that the amount of use may be small.
[0003]
There are two types of chemically amplified resists, positive type and negative type, which are generally composed of an acid generator and a film forming component whose solubility in an alkaline aqueous solution is changed by the action of the generated acid. It is said.
[0004]
In the positive resist, polyhydroxystyrene or the like in which a part of the hydroxyl group is protected with a dissolution inhibiting group such as a tert-butoxycarbonyl group or a tetrahydropyranyl group is usually used as a film forming component. In resist, as a film-forming component, polyhydroxystyrene in which a part of the hydroxyl group is usually protected with the above-described dissolution inhibiting group, or a resin component such as polyhydroxystyrene or novolac resin, and an acid-crosslinking substance such as melamine resin or urea resin A combination of these is used.
[0005]
By the way, as such an acid generator, a certain kind of diazomethane compound is used (JP-A-3-103854, JP-A-4-210960, JP-A-4-217249), and these are used. However, the resist composition is inferior in contrast between the exposed area and the unexposed area, so that the remaining film ratio is low.
[0006]
[Problems to be solved by the invention]
The present invention overcomes the disadvantages of conventional diazomethane compounds, and is a novel bissulfonyldiazomethane that exhibits excellent contrast between exposed and unexposed areas and exhibits a high residual film ratio when used as an acid generator for chemically amplified resists. It was made for the purpose of providing.
[0007]
[Means for Solving the Problems]
The inventors of the present invention have made extensive studies to develop a novel bissulfonyldiazomethane compound that has excellent contrast between exposed and unexposed areas and exhibits a high residual film ratio when used as an acid generator for chemically amplified resists. As a result, it was found that a compound having two tetrahydropyranyloxy group-substituted alicyclic groups can achieve the object, and based on this finding, the present invention has been made.
[0008]
That is, the present invention has the general formula:
The bissulfonyl diazomethane represented by these is provided.
[0009]
The alicyclic group in the general formula (I) is a cyclohexyl group when two Rs are hydrogen atoms, and when two Rs together form a dimethylmethylene group, 7 , 7-dimethylbicyclo [2.2.1] heptyl group.
The tetrahydropyranyloxy group bonded to this alicyclic group may be bonded to any position of 2-position, 3-position and 4-position.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
In the compound of the present invention, when R in the general formula (I) is a hydrogen atom, that is, the alicyclic group is a cyclohexyl group, for example, according to the following reaction formula, bis (hydroxycyclohexyl) sulfonyl It can be produced by reacting 3,4-dihydro-2H-pyran (III) with diazomethane or bis (hydroxycyclohexylmethyl) sulfonyldiazomethane (II).
[0011]
[Chemical 3]
[0012]
This reaction is carried out in the presence of pyridinium p-toluenesulfonate in a cyclic ether such as tetrahydrofuran or dioxane.
When two Rs in the same ring of the general formula (I) form a dimethylmethylene group, that is, a 7,7-dimethylbicyclo [2.2.1] heptyl group, The corresponding hydroxy-substituted alicyclic mercaptan (IV) and methylene halide (V) are condensed to form the corresponding bis (hydroxy-substituted alicyclic thio) methane (VI), which is oxidized. Is converted to the corresponding bissulfonylmethane (VII) and then diazotized to produce bis (hydroxy-substituted alicyclicsulfonyl) diazomethane (VIII), to which 3,4-dihydro-2H-pyran (III) is added. It can be obtained by reacting.
[0013]
[Formula 4]
[0014]
Examples of methylene halide (V) used in this reaction include methylene chloride, methylene bromide, and methylene iodide.
In the above reaction scheme, the condensation of hydroxy-substituted alicyclic mercaptan (IV) and methylene halide is performed in an inert solvent such as ethanol in the presence of a base such as potassium hydroxide.
[0015]
Next, the reaction of oxidizing the bis (hydroxy-substituted alicyclicthio) methane (VI) thus obtained to the corresponding bissulfonylmethane (VII) is carried out in an inert solvent such as ethanol. It can be carried out with hydrogen peroxide using alkali tungstate as a catalyst.
[0016]
Furthermore, diazotization of bissulfonylmethane (VII) thus converted can be carried out by reacting tosyl azide in the presence of a base such as potassium hydroxide or sodium hydroxide in an inert solvent such as ethanol. Is done by. The final reaction of bis (hydroxy-substituted alicyclicsulfonyl) diazomethane (VIII) with 3,4-dihydro-2H-pyran (III) is similar to that of the cyclohexyl group, with pyridinium p-toluenesulfonate. Done in the presence. The product thus obtained can be purified by means such as recrystallization according to a conventional method.
[0017]
Dissociation bissulfonyldiazomethane compounds of the general formula thus obtained (I) is a novel compound of the mounting un document, at the same time as generating an acid by irradiation of light, by acid tetrahydropyranyloxy group occurs It has the property to do.
[0018]
【Example】
Next, the present invention will be described in more detail with reference to examples.
[0019]
Example 1
Dissolve 5 g (0.014 mol) of bis (2-hydroxycyclohexylsulfonyl) diazomethane and 3.5 g (0.042 mol) of 3,4-dihydro-2H-pyran in 50 g of dioxane, and add 0.1 g of pyridinium p-toluenesulfonate. And stirred for 40 hours at room temperature. Next, 50 g of water was added, and after extraction with 30 g of ethyl acetate, the solvent was distilled off, and further, decomposition and purification by silica gel column chromatography gave the formula:
The infrared absorption spectrum and proton nuclear magnetic resonance spectrum of this product are shown in FIGS.
[0020]
Example 2
30 g (0.53 mol) of potassium hydroxide was dissolved in 300 g of ethanol, and 60 g (0.32 mol) of mercaptoisoborneol was added thereto. Next, 28 g (0.16 mol) of methylene bromide was added dropwise at room temperature over 30 minutes. The reaction mixture was further stirred at 50 ° C. for 3 hours, and the precipitated potassium bromide was filtered off, then neutralized with dilute hydrochloric acid, extracted with 500 g of methylene chloride, the solvent was distilled off, and bis [2-hydroxy There was obtained 67 g of -7,7-dimethylbicyclo [2.2.1] heptanylmethylthio] methane as a yellow oil.
Next, 67 g (0.17 mol) of this bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylthio] methane was dissolved in 300 g of ethanol, and 0.6 g of sodium tungstate was added. To this, 200 g (2.06 mol) of 35% hydrogen peroxide solution was added dropwise at 45 ° C. over 30 minutes. The reaction mixture was further stirred at 50 ° C. for 20 hours. Subsequently, 1000 g of water was added, and 51 g of precipitated bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] methane was obtained as white crystals.
Next, 20 g (0.045 mol) of this bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] methane and 10 g (0.051 mol) tosyl azide are dissolved in 80 g of ethanol. To this, 300 g (0.53 mol) of 10% aqueous potassium hydroxide solution was added dropwise at room temperature over 30 minutes. The reaction mixture was further stirred at room temperature for 2 hours. Next, the precipitated crystals were collected by filtration to obtain 6.5 g of bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane.
[0021]
5.0 g (0.011 mol) of bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane thus obtained and 3,4-dihydro-2H-pyran 2.9 g (0.033 mol) was dissolved in 50 g of dioxane, 0.1 g of pyridinium p-toluenesulfonate was added, and the mixture was stirred at room temperature for 40 hours. Next, 50 g of water was added, and after extraction with 30 g of ethyl acetate, the solvent was distilled off and further purified by silica gel column chromatography to obtain the formula:
[0022]
REFERENCE EXAMPLE A polyhydroxystyrene having a weight average molecular weight of 10,000 in which 39 mol% of the hydrogen atoms of the hydroxyl group are substituted with tert-butyloxycarbonyl groups and a weight average in which 39 mol% of the hydrogen atoms of the hydroxyl groups are substituted with ethoxyethyl groups Bis [2- (2-tetrahydropyranyl) oxycyclohexylsulfonyl obtained in Example 1 as an acid generator was added to 100 parts by weight of a resin mixture containing polyhydroxystyrene having a molecular weight of 10,000 in a weight ratio of 3: 7. 7 parts by weight of diazomethane or 7 parts by weight of bis [2- [2-tetrahydropyranyl] oxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane obtained in Example 2 and
Next, the physical properties of this positive resist composition were determined by the following method, and the results are shown in Table 1.
For comparison, the physical properties of a positive resist composition using 5 parts by weight of bis (cyclohexylsulfonyl) diazomethane, which is a known acid generator, were determined, and the results are also shown in Table 1.
[0023]
(1) Sensitivity:
The sample was applied onto a silicon wafer using a spinner and dried on a hot plate at 90 ° C. for 90 seconds to obtain a resist film having a thickness of 0.7 μm. The film was exposed using a reduced projection exposure apparatus NSR-2005EX8A (Nikon Corporation) with a dose of 1 mJ / cm 2 , and then subjected to PEB (POST EXPOSURE BAKE) at 110 ° C. for 90 seconds, 2.38. When developed with a weight% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 60 seconds, washed with water for 30 seconds and dried, the sensitivity is defined as the minimum exposure time at which the film thickness of the exposed area after development becomes 0 mJ / cm 2 ( Measured in units of energy.
[0024]
(2) Resolution:
The same operation as the above (1) was performed, and the limit resolution at the exposure amount for reproducing the 0.25 μm mask pattern is shown.
[0025]
(3) Resist pattern shape:
When the same operation as in (1) above is performed and a rectangular resist pattern of 0.25 μm is obtained, ○, and when the resist pattern top becomes a slightly thin pattern or a wavy resist pattern, × evaluated.
[0026]
(4) Stability over time:
In the above (1), after performing the operation up to the exposure, after standing for 60 minutes, PEB treatment and development were performed in the same manner, and the cross-sectional shape of the 0.25 μm resist pattern was observed with an SEM (scanning electron microscope) photograph. 5 in which the line and space of 0.25 μm is formed at 1: 1, 3 in which the line width (resist pattern width) is wider than 0.25 μm, and the space width is narrower than 0.25 μm, Evaluation was made with 1 being the unresolved value and 4 and 2 being the middle of each.
[0027]
(5) Residual film rate:
The same operation as in (1) above was performed, and the remaining film ratio of the unexposed area was determined as the ratio of the film thickness after development to the film thickness before development.
[0028]
[Table 1]
【The invention's effect】
The compound of the present invention is a novel compound, and when it is used as an acid generator for a chemically amplified resist, it has an excellent contrast between exposed and unexposed areas, and therefore gives a pattern with a high residual film ratio and an excellent profile shape.
[Brief description of the drawings]
1 is an infrared absorption spectrum of the compound obtained in Example 1. FIG.
2 is a proton nuclear magnetic resonance spectrum of the compound obtained in Example 1. FIG.
Claims (3)
で表わされるビススルホニルジアゾメタン。General formula
Bissulfonyldiazomethane represented by
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19895497A JP3980124B2 (en) | 1997-07-24 | 1997-07-24 | New bissulfonyldiazomethane |
| US09/119,640 US5945517A (en) | 1996-07-24 | 1998-07-21 | Chemical-sensitization photoresist composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19895497A JP3980124B2 (en) | 1997-07-24 | 1997-07-24 | New bissulfonyldiazomethane |
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| JPH1135573A JPH1135573A (en) | 1999-02-09 |
| JP3980124B2 true JP3980124B2 (en) | 2007-09-26 |
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| JP19895497A Expired - Fee Related JP3980124B2 (en) | 1996-07-24 | 1997-07-24 | New bissulfonyldiazomethane |
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Families Citing this family (159)
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