JP2881969B2 - Radiation-sensitive resist and pattern forming method - Google Patents
Radiation-sensitive resist and pattern forming methodInfo
- Publication number
- JP2881969B2 JP2881969B2 JP2146803A JP14680390A JP2881969B2 JP 2881969 B2 JP2881969 B2 JP 2881969B2 JP 2146803 A JP2146803 A JP 2146803A JP 14680390 A JP14680390 A JP 14680390A JP 2881969 B2 JP2881969 B2 JP 2881969B2
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- Prior art keywords
- radiation
- resist
- acrylate
- ester
- pattern
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Description
【発明の詳細な説明】 〔概要〕 放射線用レジストに関し、 優れたエッチング耐性を示すと共に放射線、特に遠紫
外光に対して透明性に優れたレジストを実用化すること
を目的とし、 エステル部にアダマンタン骨格を有するアクリル酸エ
ステルまたはα置換アクリル酸エステルの重合体か、或
いは該エステルの共重合体からなる放射線感光材料を用
いてレジストを形成し、該レジストを塗布した被処理基
板に放射線を選択露光した後に現像し、レジストパター
ンを形成することを特徴とするパターン形成方法を構成
する。DETAILED DESCRIPTION OF THE INVENTION [Summary] Regarding a radiation resist, an object of the present invention is to provide a resist which exhibits excellent etching resistance and has excellent transparency to radiation, particularly to far ultraviolet light, and has an adamantane in an ester portion. A resist is formed using a radiation-sensitive material composed of a polymer of an acrylate or an α-substituted acrylate having a skeleton, or a copolymer of the ester, and selectively exposing the substrate to which the resist is coated with radiation to a treatment target And then developing to form a resist pattern.
本発明は放射線感光材料とパターン形成方法に関す
る。The present invention relates to a radiation-sensitive material and a pattern forming method.
半導体集積回路は集積化が進んでLSIやVLSIが実用化
されており、これと共に配線パターンの最小線幅はサブ
ミクロン（Sub−micron）に及んでいるが更に微細化の
傾向にある。The integration of semiconductor integrated circuits is progressing, and LSIs and VLSIs are being put to practical use. At the same time, the minimum line width of a wiring pattern is in the sub-micron range, but there is a tendency for further miniaturization.
こゝで、微細パターンの形成には薄膜を形成した被処
理基板上にレジストを被覆し、選択露光を行った後に現
像してレジストパターンを作り、これをマスクとしてド
ライエッチングを行い、その後にレジストを溶解除去す
ることにより薄膜パターンを得る写真蝕刻技術の使用が
必須である。Here, in order to form a fine pattern, a resist is coated on a substrate to be processed on which a thin film has been formed, developed after selective exposure, a resist pattern is formed, dry etching is performed using this as a mask, and then the resist is etched. It is indispensable to use a photolithography technique for obtaining a thin film pattern by dissolving and removing the film.
この写真蝕刻技術に使用する光源として、当初は紫外
線が使用されていたが、波長による制限からサブミクロ
ン幅の解像は不可能であり、これに代わって波長の短い
遠紫外線や電子線,X線などを光源としてサブミクロン幅
の解像が行われるようになった。Ultraviolet light was initially used as the light source for this photolithography technology, but resolution at submicron widths was impossible due to wavelength limitations. Resolution of submicron width has been performed using a line as a light source.
本発明はこれら放射線用レジスト材料に関するもので
ある。The present invention relates to these resist materials for radiation.
レジストとして従来はフェノール樹脂をベースとする
ものが数多く開発されてきた。Conventionally, many resists based on phenolic resins have been developed.
然し、これらの材料は芳香族環を含むために光の吸収
が大きく、そのため微細化に対応できるだけのパターン
精度は得られない。However, since these materials contain an aromatic ring, they absorb a large amount of light, so that a pattern precision that can cope with miniaturization cannot be obtained.
一方、吸収の少ない樹脂としてポリメチルメタクリレ
ート（略称PMMA）やポリメチルイソプロピルケトン（略
称PMIPK）などが検討されているが、芳香族環を含んで
いないために充分なエッチング耐性をもっていない。On the other hand, polymethyl methacrylate (abbreviation: PMMA) and polymethyl isopropyl ketone (abbreviation: PMIPK) have been studied as resins having low absorption, but they do not have sufficient etching resistance because they do not contain an aromatic ring.
これらのことから、透明性に優れ、且つ充分なエッチ
ング耐性を備えたレジストは実用化されていない。For these reasons, a resist excellent in transparency and having sufficient etching resistance has not been put to practical use.
以上記したようにサブミクロンの微細パターンを現像
するには遠紫外光に対して透明性が優れ、且つ、充分な
エッチング耐性をもつ感光材料が必要であり、この両方
の特性を兼ね備えた放射用感光材料を実用化することが
課題である。As described above, in order to develop a submicron fine pattern, a photosensitive material having excellent transparency to far ultraviolet light and sufficient etching resistance is required, and a radiation material having both of these characteristics is required. The task is to put the photosensitive material into practical use.
上記の課題は、エステル部にアダマンタン骨格を有す
るアクリル酸エステルまたはα置換アクリル酸エステル
の重合体か、或いは該エステルの共重合体からなり、ド
ライエッチング用のマスクとして用いられる放射線感光
レジストと、エステル部にアダマンタン骨格を有するア
クリル酸エステルまたはα置換アクリル酸エステルの重
合体か、或いは該エステルの共重合体からなる放射線感
光材料を用いてレジストを形成し、該レジストを塗布し
た被処理基板に放射線を選択露光した後に現像し、ドラ
イエッチングに用いるレジストパターンを形成するパタ
ーン形成方法とによって解決することができる。The above-mentioned problem is caused by a radiation-sensitive resist used as a mask for dry etching, comprising a polymer of an acrylate or an α-substituted acrylate having an adamantane skeleton in an ester portion, or a copolymer of the ester, A resist is formed using a radiation-sensitive material composed of an acrylate or an α-substituted acrylate having an adamantane skeleton in its portion, or a copolymer of the ester, and the radiation is applied to the substrate to which the resist is applied. Is developed after selective exposure to light, and a pattern forming method for forming a resist pattern used for dry etching.
本発明は遠紫外光に対して透明性が優れ、且つ、充分
なエッチング耐性をもつ感光材料として、アダマンタン
骨格を有するアクリル酸エステルまたはα置換アクリル
酸エステルの重合体か、或いはこのエステルの共重合体
からなる材料を用いるものである。The present invention provides, as a photosensitive material having excellent transparency to far ultraviolet light and sufficient etching resistance, a polymer of an acrylate or an α-substituted acrylate having an adamantane skeleton, or a copolymer of this ester. A material made of united material is used.
すなわち、第１図の（１）式で構造を示すアダマンタ
ン（C10H16）は椅子型構造のシクロヘキサン環を構成単
位としており化学的に非常に安定な化合物として知ら
れ、医薬品への用途開発が試みられている。In other words, adamantane (C 10 H 16 ), whose structure is represented by the formula (1) in FIG. 1, has a chair-shaped cyclohexane ring as a structural unit and is known as a very chemically stable compound. Have been tried.
発明者はアダマンタン骨格を分子中に含むポリマーは
芳香族環がないにも拘らず優れたエッチング耐性を示
し、また遠紫外光に対して吸収が少ない点に着目した。The inventor has noted that a polymer containing an adamantane skeleton in a molecule exhibits excellent etching resistance despite the absence of an aromatic ring, and has low absorption for far ultraviolet light.
そこで、この特徴を活かし、エステル部にアダマンタ
ン骨格を有するアクリル酸エステルまたはα置換アクリ
ル酸エステルの重合体か、或いはこのエステルの共重合
体を感光材料として使用するものである。Therefore, taking advantage of this feature, a polymer of an acrylate ester or an α-substituted acrylate ester having an adamantane skeleton in the ester portion, or a copolymer of this ester is used as a photosensitive material.
このような感光材料は優れたエッチング耐性をもつと
共に透明性に優れているため、精度よくサブミクロパタ
ーンを形成することができる。Since such a photosensitive material has excellent etching resistance and excellent transparency, a submicro pattern can be formed with high accuracy.
実施例1: 第１図の（２）式に構造式を示すアダマンチルメタク
リレート4.4gとベンゼン5.0gに反応開始剤としてアゾイ
ソブルロニトリル（略称AIBN）0.5モル％を加え、70℃
で約８時間重合した後、メタノールで再沈精製を行った
結果、重量平均分子量18万，分散度1.6のポリマーが得
られた。Example 1: 0.5 mol% of azoisobuluronitrile (abbreviation: AIBN) as a reaction initiator was added to 4.4 g of adamantyl methacrylate having the structural formula shown in the formula (2) of FIG.
After polymerizing for about 8 hours, reprecipitation purification was performed with methanol. As a result, a polymer having a weight average molecular weight of 180,000 and a dispersity of 1.6 was obtained.
これをキシレン溶液とした後、石英基板上に1.0μｍ
厚に被覆し、遠紫外光（248nm）に対する透明性を調べ
た結果、透過率は97％であって、PMMAと同等であった。After making this a xylene solution, 1.0 μm
As a result of examining the transparency to far ultraviolet light (248 nm), the transmittance was 97%, which was equivalent to that of PMMA.
なお、PMMAの透過率は98％またはフェノールノボラッ
ク樹脂の透過率は30％である。The transmittance of PMMA is 98% or the transmittance of phenol novolak resin is 30%.
更に、四弗化炭素ガス（CF4）によるエッチングレー
トをPMMAと比較した結果、PMMAのエッチンレートが1330
Å／分であるのに対しポリアダマンチルメタクリレート
は860Å／分と優れていた。Further, as a result of comparing the etching rate by carbon tetrafluoride gas (CF 4 ) with that of PMMA, the etching rate of PMMA was 1330.
Polyadamantyl methacrylate was excellent at 860 l / min, whereas l / min.
なお、エッチング条件は、CF4の流量は20sccm,真空度
は１×10-3torr,μ波の出力は1KW,高周波電力は100Wで
ある。The etching conditions were as follows: the flow rate of CF 4 was 20 sccm, the degree of vacuum was 1 × 10 −3 torr, the output of the microwave was 1 KW, and the high frequency power was 100 W.
次に、得られたアダマンチルメタクリレートポリマー
に架橋剤として第１図の（３）式に構造式を示す4,4′
−ジアジドジフェニルメチレンを20重量％添加してキシ
レン溶液とし、Si基板上に0.5μｍの厚さに塗布した
後、100℃で30分間プリベークした。Next, the obtained adamantyl methacrylate polymer is used as a crosslinking agent in the formula (4), 4,4 ′ of which
20% by weight of diazidediphenylmethylene was added to form a xylene solution, which was applied on a Si substrate to a thickness of 0.5 μm and then prebaked at 100 ° C. for 30 minutes.
その後、キセノン・水銀（Xe−Hg）ランプにより30秒
間露光した後、キシレンで60秒間現像してパターニング
特性を調べた。Then, after exposing with a xenon-mercury (Xe-Hg) lamp for 30 seconds, development was performed with xylene for 60 seconds, and patterning characteristics were examined.
その結果、0.6μｍのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a 0.6 μm line and space pattern could be resolved.
比較例1: フェノールノボラック樹脂をベースにしたｇ線（436n
m）用レジストを用い、実施例１と同様な実験を行った
が、得られたレジストパターンの断面形状はテーパー状
となった。Comparative Example 1: g-line based on phenol novolak resin (436n
The same experiment as in Example 1 was performed using the resist for m), but the cross-sectional shape of the obtained resist pattern was tapered.
実施例2: 実施例１のアダマンチルメタクレートの代わりに第１
図の（４）式に構造式を示すジメチルアダマンタンアク
リレートを用いて同様な実験を行った結果、同様な結果
が得られた。Example 2: Instead of the adamantyl methacrylate of Example 1, the first
A similar experiment was performed using dimethyl adamantane acrylate having the structural formula shown in Formula (4) in the figure, and similar results were obtained.
実施例3: 実施例１において架橋剤として4,4′−ジアジドフェ
ニルメチレンの代わりに第１図の（５）式に構造式を示
す4,4′−ジアジドフェニルスルホンを用いても同様な
結果を得ることができた。Example 3: In the same manner as in Example 1, 4,4'-diazidophenylsulfone represented by the formula (5) in FIG. 1 was used in place of 4,4'-diazidophenylmethylene as a crosslinking agent. Results were obtained.
実施例4: AIBNを重合開始剤とし、アダマンチルメタクリレート
とメタクリル酸とを1,4−ジオキサン中で80℃,8時間重
合させた後、ヘキサンを用いて再沈精製を行った結果、
重量平均分子量２万，分散度2.0,組成比が7:3の共重合
体が得られた。Example 4: AIBN was used as a polymerization initiator, adamantyl methacrylate and methacrylic acid were polymerized in 1,4-dioxane at 80 ° C. for 8 hours, and reprecipitation purification was performed using hexane.
A copolymer having a weight average molecular weight of 20,000, a dispersity of 2.0, and a composition ratio of 7: 3 was obtained.
このポリマーに架橋剤として4,4′−ジアジドフェニ
ルメチレンを30重量％加えてシクロヘキサン溶液とし、
Si基板上に0.5μｍの厚さに塗布した後、100℃,30分間
プリベークを行った。30% by weight of 4,4'-diazidophenylmethylene as a crosslinking agent was added to this polymer to form a cyclohexane solution,
After coating on a Si substrate to a thickness of 0.5 μm, prebaking was performed at 100 ° C. for 30 minutes.
その後、Xe−Hgランプにより30秒間露光したのち、ア
ルカリ現像を行った。Thereafter, after exposure with a Xe-Hg lamp for 30 seconds, alkali development was performed.
その結果、0.5μｍのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a 0.5 μm line and space pattern could be resolved.
なお、エッチング耐性はポリアダマンチルメタクリレ
ートの場合と同様であった。The etching resistance was similar to that of polyadamantyl methacrylate.
実施例5: 実施例４と同様な方法によりアダマンチルメタクリレ
ートとメタクリル酸ｔ−ブチルを共重合した結果、重量
平均分子量1.2万，分散度1.5,組成比が6:4の共重合体が
得られた。Example 5: As a result of copolymerizing adamantyl methacrylate and t-butyl methacrylate in the same manner as in Example 4, a copolymer having a weight average molecular weight of 12,000, a dispersity of 1.5, and a composition ratio of 6: 4 was obtained. .
このポリマーに酸発生剤であり、第１図の（６）式に
構造式を示すトリフェニルスルホニウムヘキサフロロホ
スフェートを５重量％加えてシクロヘキサン溶液とし、
Si基板上に1.0μｍの厚さに塗布した後、90℃,30分間プ
リベークを行った。To this polymer is added an acid generator, 5% by weight of triphenylsulfonium hexafluorophosphate represented by the formula (6) in FIG. 1 to form a cyclohexane solution,
After coating on a Si substrate to a thickness of 1.0 μm, prebaking was performed at 90 ° C. for 30 minutes.
その後、Xe−Hgランプにより５秒間露光したのち、11
0℃で20分のベークを行った後、アルカリ現像を行っ
た。Then, after exposing for 5 seconds by Xe-Hg lamp,
After baking at 0 ° C. for 20 minutes, alkali development was performed.
その結果、0.5μｍのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a 0.5 μm line and space pattern could be resolved.
なお、エッチング耐性はポリアダマンタンチルメタク
リレートの場合と同様であり、また樹脂の透明性がPMMA
と同様であった。The etching resistance is the same as that of polyadamantantyl methacrylate, and the transparency of the resin is PMMA.
Was similar to
実施例6: 実施例５において、酸発生剤として第１図の（７）式
に構造式を示すジフェニルアイオードヘキサフロロホス
フェートを用いても同様な結果が得られた。Example 6: In Example 5, similar results were obtained by using diphenyliodohexafluorophosphate represented by the formula (7) in FIG. 1 as the acid generator.
実施例7: 実施例４においてアダマンチルメタクリレートの代わ
りにアダマンチルアクリレートを用いた場合も同様な結
果を得ることができた。Example 7: A similar result was obtained when adamantyl acrylate was used instead of adamantyl methacrylate in Example 4.
実施例8: 実施例１と同様の溶液重合により、重量平均分子量1.
2万，分散度1.5,組成比が6:4の共重合体が得られた。Example 8: By the same solution polymerization as in Example 1, the weight average molecular weight was 1.
A copolymer having a molecular weight of 20,000, a dispersity of 1.5, and a composition ratio of 6: 4 was obtained.
この重合体に第１図の（８）式に構造式を示す４−
４′−ジアドカルコンを７重量％添加してキシレン溶液
とした。The polymer has the structural formula shown in Formula (8) of FIG.
7% by weight of 4'-diadchalcone was added to obtain a xylene solution.
この溶液をSi基板上に1.0μｍの厚さに塗布した後、N
2気流中で200℃,1時間のプリベークを行い、熱架橋させ
て不溶化した後、加速電圧20KVの電子線露光装置で露光
した。After applying this solution to a thickness of 1.0 μm on a Si substrate,
Pre-baking was performed at 200 ° C. for 1 hour in two airflows to thermally crosslink and insolubilize, and then exposed with an electron beam exposure apparatus at an acceleration voltage of 20 KV.
この後、キシレンで現像した結果、64μC/cm2の露光
量で0.8μｍのライン・アンド・スペースパターンを解
像することができた。Thereafter, as a result of development with xylene, a 0.8 μm line and space pattern could be resolved with an exposure amount of 64 μC / cm 2 .
なお、同様な実験をPMMAを用いて行い、エッチング耐
性を比較した結果、PMMAの1.5倍であった。A similar experiment was performed using PMMA, and as a result of comparing the etching resistance, it was 1.5 times that of PMMA.
実施例9: 実施例５において現像液としてアルカリ現像液の代わ
りにキシレンを用いることにより、0.8μｍのライン・
アンド・スペースのネガパターンを得ることができた。Example 9: A 0.8 μm line was obtained by using xylene instead of the alkali developer as the developer in Example 5.
A negative pattern of AND space was obtained.
本発明によれば、電離放射線に対し、透明性が高く、
且つ充分なエッチング耐性をもつレジストパターンを得
ることができ、これによりサブミクロン・パターンを得
ることができる。According to the present invention, high transparency to ionizing radiation,
In addition, a resist pattern having sufficient etching resistance can be obtained, whereby a submicron pattern can be obtained.
第１図は本発明の実施において使用した有機化合物の構
造式である。FIG. 1 is a structural formula of an organic compound used in the practice of the present invention.
Claims (2)
クリル酸エステルまたはα置換アクリル酸エステルの重
合体か、或いは該エステルの共重合体からなり、ドライ
エッチング用のマスクとして用いられることを特徴とす
る放射線感光レジスト。1. A radiation comprising a polymer of an acrylate or an α-substituted acrylate having an adamantane skeleton in an ester portion, or a copolymer of the ester, and used as a mask for dry etching. Photosensitive resist.
クリル酸エステルまたはα置換アクリル酸エステルの重
合体か、或いは該エステルの共重合体からなる放射線感
光材料を用いてレジストを形成し、該レジストを塗布し
た被処理基板に放射線を選択露光した後に現像し、ドラ
イエッチングに用いるレジストパターンを形成すること
を特徴とするパターン形成方法。2. A resist is formed by using a radiation-sensitive material comprising a polymer of an acrylate or an α-substituted acrylate having an adamantane skeleton in an ester portion, or a copolymer of the ester, and coating the resist. A selective exposure of radiation to the processed substrate, followed by development to form a resist pattern used for dry etching.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2146803A JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2146803A JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0439665A JPH0439665A (en) | 1992-02-10 |
| JP2881969B2 true JP2881969B2 (en) | 1999-04-12 |
Family
ID=15415885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2146803A Expired - Lifetime JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
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| Country | Link |
|---|---|
| JP (1) | JP2881969B2 (en) |
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|---|---|---|---|---|
| US6953651B2 (en) | 2001-01-19 | 2005-10-11 | Sumitomo Chemical Company, Limited | Chemical amplifying type positive resist composition |
| US6982140B2 (en) | 2001-12-03 | 2006-01-03 | Tokyo Ohka Kogyo., Ltd. | Positive resist composition and method of forming resist pattern |
| US7074543B2 (en) | 2001-12-03 | 2006-07-11 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method of forming resist pattern from the same |
| KR100711691B1 (en) | 2003-03-07 | 2007-05-02 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Alicyclic Methacrylate Having Oxygen Substituent Group on ?-Methyl |
| US7544460B2 (en) | 2003-07-09 | 2009-06-09 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, multilayer body, and method for forming resist pattern |
| US7781144B2 (en) | 2005-05-17 | 2010-08-24 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and resist pattern forming method |
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