JPH1135573A - New bissulfonyldiazomethane - Google Patents
New bissulfonyldiazomethaneInfo
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- JPH1135573A JPH1135573A JP9198954A JP19895497A JPH1135573A JP H1135573 A JPH1135573 A JP H1135573A JP 9198954 A JP9198954 A JP 9198954A JP 19895497 A JP19895497 A JP 19895497A JP H1135573 A JPH1135573 A JP H1135573A
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Abstract
Description
【0001】[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スルホニルジアゾメタン化
合物に関するものである。The present invention relates to a novel sulfonyldiazomethane compound suitable as an acid generator for a chemically amplified resist.
【0002】[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。2. Description of the Related Art In recent years, in the production of semiconductor devices and liquid crystal devices, chemically amplified resist compositions have been used. This chemically amplified resist composition is a resist utilizing the catalytic action of an acid generated by irradiation with radiation, and has high sensitivity and resolution, and a compound that generates an acid upon irradiation with radiation, that is, an acid generator. This has the advantage that the amount of used may be small.
【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。[0003] There are two types of chemically amplified resists, a positive type and a negative type. These are generally an acid generator and a film-forming component whose solubility in an aqueous alkali solution changes due to the action of the generated acid. Is the basic component.
【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。In the positive resist, as a film-forming component, polyhydroxystyrene or the like in which a part of hydroxyl groups is protected by a dissolution inhibiting group such as a tert-butoxycarbonyl group or a tetrahydropyranyl group is used. In a negative resist, as a film-forming component, a resin component such as polyhydroxystyrene or a polyhydroxystyrene or a novolak resin in which a part of a hydroxyl group is protected by the above-described dissolution inhibiting group is usually added to an acid such as a melamine resin or a urea resin. A combination of crosslinkable substances is used.
【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。As such an acid generator, certain diazomethane compounds have been used (JP-A-3-103854, JP-A-4-210960, JP-A-4-217249). Resist compositions using these have poor contrast between exposed and unexposed portions, and therefore have the disadvantage that the residual film ratio is low.
【0006】[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。SUMMARY OF THE INVENTION The present invention overcomes the drawbacks of the conventional diazomethane compound and, when used as an acid generator for a chemically amplified resist, provides excellent contrast between exposed and unexposed areas and high residuals. The object of the present invention is to provide a novel bissulfonyldiazomethane having a film ratio.
【0007】[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。DISCLOSURE OF THE INVENTION The present inventors have developed a novel bissulfonyl compound which, when used as an acid generator for a chemically amplified resist, has excellent contrast between exposed and unexposed areas and exhibits a high residual film ratio. As a result of intensive studies to develop a diazomethane compound, they have found that a compound having two tetrahydropyranyloxy-substituted alicyclic groups can achieve the object, and based on this finding, the present invention I've reached the point.
【0008】すなわち、本発明は、一般式That is, the present invention provides a compound represented by the general formula
【化2】 (式中のRはそれぞれ水素原子であるか、又は同一環内
の2個のRでジメチルメチレン基を形成する基であり、
nは0又は1である)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。Embedded image (Wherein R is a hydrogen atom or a group forming a dimethylmethylene group with two Rs in the same ring,
n is 0 or 1).
【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。The alicyclic group in the general formula (I) is a cyclohexyl group when two Rs are hydrogen atoms, and a cyclohexyl group when two Rs together form a dimethylmethylene group. Is a 7,7-dimethylbicyclo [2.2.1] heptyl group. The tetrahydropyranyloxy group bonded to the alicyclic group may be bonded to any of the 2-position, 3-position and 4-position.
【0010】[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。BEST MODE FOR CARRYING OUT THE INVENTION In the compounds of the present invention, when R in the above general formula (I) is a hydrogen atom, that is, when the alicyclic group is a cyclohexyl group, for example, according to the following reaction formula: , Bis (hydroxycyclohexyl) sulfonyldiazomethane or bis (hydroxycyclohexylmethyl) sulfonyldiazomethane (II) with 3,4-dihydro-2H-pyran (III).
【0011】[0011]
【化3】 (式中のnは前記と同じ意味をもつ)Embedded image (N in the formula has the same meaning as described above)
【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。This reaction is carried out in an inert solvent such as a cyclic ether such as tetrahydrofuran or dioxane in the presence of pyridinium p-toluenesulfonate. Further, 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) according to the following reaction formula, which is then oxidized. To give the corresponding bissulfonylmethane (VII), followed by diazotization to produce bis (hydroxy-substituted alicyclic sulfonyl) diazomethane (VIII), to which 3,4-dihydro-
It can be obtained by reacting 2H-pyran (III).
【0013】[0013]
【化4】 (ただし、Xはハロゲン原子、nは前記と同じ意味をも
つ)Embedded image (Where X is a halogen atom and n has the same meaning as described above)
【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(I
V)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。Examples of the methylene halide (V) used in this reaction include methylene chloride, methylene bromide and methylene iodide. In the above reaction formula, the hydroxy-substituted alicyclic mercaptan (I
The condensation of V) with methylene halide is carried out in an inert solvent such as ethanol in the presence of a base such as potassium hydroxide.
【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。Next, the reaction of oxidizing the bis (hydroxy-substituted alicyclic thio) methane (VI) thus obtained into the corresponding bissulfonylmethane (VII) is carried out by an inert reaction such as ethanol. In a solvent, the reaction can be carried out with hydrogen peroxide using alkali tungstate as a catalyst.
【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(VII
I)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。Further, the diazotization of bissulfonylmethane (VII) thus converted can be carried out, for example, by converting tosyl azide in an inert solvent such as ethanol in the presence of a base such as potassium hydroxide or sodium hydroxide. It is performed by reacting. And the last bis (hydroxy-substituted alicyclic sulfonyl) diazomethane (VII
The reaction between I) and 3,4-dihydro-2H-pyran (III) is carried out in the presence of pyridinium p-toluenesulfonate, as in the case of the cyclohexyl group. The product thus obtained can be purified by means such as recrystallization according to a conventional method.
【0017】このようにして得られる前記一般式(I)
の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。The thus obtained general formula (I)
Is a novel compound that has not been published in the literature, and generates an acid upon irradiation with light,
It has the property that the tetrahydropyranyloxy group is dissociated by the generated acid.
【0018】[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。Next, the present invention will be described in more detail by way of examples.
【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Example 1 5 g (0.014 mol) of bis (2-hydroxycyclohexylsulfonyl) diazomethane and 3,4-dihydro-
3.5 g (0.042 mol) of 2H-pyran was dissolved in 50 g of dioxane, and 0.1 g of pyridinium p-toluenesulfonate was added, followed by stirring at room temperature for 40 hours. Then
After adding 50 g of water and extracting with 30 g of ethyl acetate, the solvent was distilled off, and the resulting product was further decomposed and purified by silica gel column chromatography, whereby the formula was obtained.
【化5】 で表わされるビス[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2.0
gを得た。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。Embedded image Bis [2- (2-tetrahydropyranyl) represented by
[Oxycyclohexylsulfonyl] diazomethane 2.0
g was obtained. Its infrared absorption spectrum and proton nuclear magnetic resonance spectrum are shown in FIGS. 1 and 2.
【0020】実施例2 水酸化カリウム30g(0.53モル)をエタノール3
00gに溶かし、これにメルカプトイソボルネオール6
0g(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3
0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。Example 2 30 g (0.53 mol) of potassium hydroxide was added to ethanol 3
00 g, and add mercaptoisoborneol 6
0 g (0.32 mol) were added. Then, 28 g (0.16 mol) of methylene bromide was added dropwise at room temperature over 30 minutes. After further stirring the reaction mixture at 50 ° C. for 3 hours, the precipitated potassium bromide was filtered off, then neutralized with dilute hydrochloric acid, and further 500 g of methylene chloride was added.
, And the solvent is distilled off, and bis [2-hydroxy-7,7
-Dimethylbicyclo [2.2.1] heptanylmethylthio] methane (67 g) was obtained as a yellow oil. Then, 67 g of this bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylthio] methane
(0.17 mol) was dissolved in 300 g of ethanol, and 0.6 g of sodium tungstate was added. In addition, 35
200 g (2.06 mol) of a 20% aqueous hydrogen peroxide solution were added dropwise at 45 ° C. over 30 minutes. The reaction mixture was further stirred at 50 ° C. for 20 hours. Then, 1000 g of water
Was added to obtain 51 g of precipitated bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] methane as white crystals. Next, the bis [2-hydroxy-7,7-dimethylbicyclo [2.
2.1] Heptanylmethylsulfonyl] methane 20g
(0.045 mol) and 10 g of tosyl azide (0.051
Mol) was dissolved in 80 g of ethanol, and 300 g (0.53 mol) of a 10% aqueous potassium hydroxide solution was added at room temperature to 3 g.
It was added dropwise over 0 minutes. The reaction mixture was further stirred at room temperature for 2 hours. Then, the precipitated crystals are collected by filtration,
6.5 g of bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane were obtained.
【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The bis [2-hydroxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane thus obtained, 5.0 g (0.011
Mol) and 2.9 g of 3,4-dihydro-2H-pyran
(0.033 mol) was dissolved in 50 g of dioxane.
0.1 g of pyridinium toluenesulfonate was added, and the mixture was stirred at room temperature for 40 hours. Next, 50 g of water was added, and the mixture was extracted with 30 g of ethyl acetate. The solvent was distilled off, and the residue was separated and purified by silica gel column chromatography to obtain the compound of the formula
【化6】 で表わされるビス〔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1.5gを得
た。Embedded image Bis [2- [2-tetrahydropyranyl] represented by
1.5 g of oxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane was obtained.
【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10,00
0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。REFERENCE EXAMPLE A weight-average molecular weight of 10,000 wherein 39 mol% of hydrogen atoms of a hydroxyl group is substituted by a tert-butyloxycarbonyl group.
Polyhydroxystyrene of 0 and 39 of the hydrogen atom of the hydroxyl group
Mol% of polyhydroxystyrene having a weight average molecular weight of 10,000 substituted by an ethoxyethyl group in a weight ratio of 3:
7 parts by weight of bis [2- (2-tetrahydropyranyl) oxycyclohexylsulfonyl] diazomethane obtained in Example 1 or bis [obtained in Example 2 as an acid generator in 100 parts by weight of the resin mixture containing 7 parts by weight. Compounding 7 parts by weight of 2- [2-tetrahydropyranyl] oxy-7,7-dimethylbicyclo [2.2.1] heptanylmethylsulfonyl] diazomethane, 0.3 part by weight of triethylamine and 0.2 part by weight of salicylic acid Was dissolved in 490 parts by weight of propylene glycol monomethyl ether acetate, and this solution was filtered through a membrane filter having a pore size of 0.2 μm to prepare a positive resist composition. Next, physical properties of the positive resist composition were determined by the following methods, and the results are shown in Table 1. For comparison, bis (cyclohexylsulfonyl), a known acid generator, is used.
Physical properties of the positive resist composition using 5 parts by weight of diazomethane were determined, and the results are shown in Table 1.
【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−2005E
X8A(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PE
B(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。(1) Sensitivity: A sample was applied on a silicon wafer using a spinner, and dried on a hot plate at 90 ° C. for 90 seconds to obtain a 0.7 μm-thick resist film. This film has a reduced projection exposure apparatus NSR-2005E
Exposure was performed using X8A (manufactured by Nikon Corporation) at a dose of 1 mJ / cm 2 , followed by PE at 110 ° C. for 90 seconds.
B (POST EXPOSURE BAKE)
When developed with an aqueous solution of 2.38% by weight of tetramethylammonium hydroxide at 23 ° C. for 60 seconds, washed with water for 30 seconds and dried, the minimum exposure time at which the film thickness of the exposed area after development becomes 0 is defined as mJ / It was measured in cm 2 (energy amount).
【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。(2) Resolution: The same operation as in the above (1) was performed, and the resolution was shown as the limit resolution at the exposure amount for reproducing a mask pattern of 0.25 μm.
【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。(3) Resist pattern shape: (1)
The same operation as that described above was performed, and a case where a 0.25 μm rectangular resist pattern was obtained was evaluated as ○, and a case where the top of the resist pattern became a slightly thin pattern or a wavy resist pattern was evaluated as x.
【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。(4) Stability after pulling out: In the above (1), after performing the operations up to exposure, after standing for 60 minutes, PEB treatment and development were performed in the same manner to give 0.25 μm.
The cross-sectional shape of the resist pattern was observed with a SEM (scanning electron microscope) photograph, and the line and space of 0.25 μm were formed 1: 1, and the line width (resist pattern width) was 0.25 μm. The case where the width became wider and the space width became narrower than 0.25 μm was evaluated as 3, the case where no resolution was obtained was evaluated as 1, and the middle of each was evaluated as 4, 2.
【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。(5) Residual film ratio: The same operation as in the above (1) was performed, and the residual film ratio of the unexposed portion was determined as a ratio of the film thickness after development to the film thickness before development.
【0028】[0028]
【表1】 [Table 1]
【0029】[0029]
【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。The compound of the present invention is a novel compound, and when it is used as an acid generator of a chemically amplified resist, the contrast between exposed and unexposed areas is excellent, so that the residual film ratio is high and the profile shape is excellent. Give the pattern.
【図1】 実施例1で得た化合物の赤外吸収スペクトル
図。FIG. 1 is an infrared absorption spectrum of the compound obtained in Example 1.
【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。FIG. 2 is a proton nuclear magnetic resonance spectrum of the compound obtained in Example 1.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 島巻 利治 大阪府大阪市福島区福島7丁目15−26 ダ イトーケミックス株式会社内 (72)発明者 庫本 伸哉 大阪府大阪市福島区福島7丁目15−26 ダ イトーケミックス株式会社内 (72)発明者 早川 訓男 大阪府大阪市福島区福島7丁目15−26 ダ イトーケミックス株式会社内 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Toshiharu Shimaki 7-15-26 Fukushima-ku, Fukushima-ku, Osaka-shi, Osaka Inside Daitomix Mix Co., Ltd. (72) Inventor Nobuya Kuromoto 7-chome, Fukushima-ku, Osaka-shi, Osaka 15-26 Daitomix Mix Co., Ltd. (72) Inventor Norio Hayakawa 7-fukushima, Fukushima-ku, Osaka-shi, Osaka 15-26 Daitomix Mix Co., Ltd.
Claims (3)
の2個のRでジメチルメチレン基を形成する基であり、
nは0又は1である)で表わされるビススルホニルジア
ゾメタン。1. A compound of the general formula (Wherein R is a hydrogen atom or a group forming a dimethylmethylene group with two Rs in the same ring,
n is 0 or 1).
記載のビススルホニルジアゾメタン。2. The compound according to claim 1, wherein R in the general formula is a hydrogen atom.
The bissulfonyldiazomethane as described.
れぞれジメチルメチレン基を形成する基である請求項1
記載のビススルホニルジアゾメタン。3. The compound according to claim 1, wherein two Rs in the same ring in the general formula each form a dimethylmethylene group.
The bissulfonyldiazomethane as described.
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 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19895497A JP3980124B2 (en) | 1997-07-24 | 1997-07-24 | New bissulfonyldiazomethane |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH1135573A true JPH1135573A (en) | 1999-02-09 |
JP3980124B2 JP3980124B2 (en) | 2007-09-26 |
Family
ID=16399710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP19895497A Expired - Fee Related JP3980124B2 (en) | 1996-07-24 | 1997-07-24 | New bissulfonyldiazomethane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3980124B2 (en) |
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