JP2002099076A - Method of manufacturing photoresist composition with reduced amount of fine particles - Google Patents
Method of manufacturing photoresist composition with reduced amount of fine particlesInfo
- Publication number
- JP2002099076A JP2002099076A JP2000288264A JP2000288264A JP2002099076A JP 2002099076 A JP2002099076 A JP 2002099076A JP 2000288264 A JP2000288264 A JP 2000288264A JP 2000288264 A JP2000288264 A JP 2000288264A JP 2002099076 A JP2002099076 A JP 2002099076A
- Authority
- JP
- Japan
- Prior art keywords
- filter
- photoresist composition
- fine particles
- pore size
- ptfe
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
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- Filtering Materials (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、紫外線、遠紫外線
（エキシマーレーザー等を含む）、電子線、Ｘ線または
放射光のような高エネルギーの放射線によって作用する
リソグラフィなどに適したフォトレジスト組成物の製造
法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photoresist composition suitable for lithography and the like, which is acted on by high-energy radiation such as ultraviolet rays, far ultraviolet rays (including excimer lasers, etc.), electron beams, X-rays or radiation. The method relates to a method for producing the same.
【０００２】[0002]
【従来の技術、発明が解決しようとする課題】フォトレ
ジスト組成物は、電子計算機などに使用されているＩ
Ｃ、ＬＳＩ等の製造工程における微細精密加工のパター
ン形成材料として用いられており、 ＬＳＩ等の高集積
化に伴い、集積回路のデザインルールも０．３５μｍか
ら０．１５μｍへ微細化している。このような微細加工
に用いられるフォトレジスト組成物には、基本的性能
（解像度、感度、プロファ イル、塗布性等）以外に、
目視では観察しえない微細粒子が少ないこと、および長
期保存後も微細粒子が顕著に増加しないこと（換言すれ
ば良好な保存安定性を有すること）が要求されている。
そして、この要求は、フォトレジスト組成物中に微細粒
子が多い場合、該フォトレジスト組成物から形成された
レジストパターンを介して基板をエッチングすると、し
ばしば、レジストパターンにより覆われた基板部分にピ
ンホールが発生し、集積回路作製時の歩留りが悪化する
ことに由来している。2. Description of the Related Art Photoresist compositions are used in electronic computers and the like.
It is used as a pattern forming material for fine precision processing in the manufacturing process of C, LSI and the like. With the increase in integration of LSI and the like, the design rule of an integrated circuit is also reduced from 0.35 μm to 0.15 μm. In addition to basic performance (resolution, sensitivity, profile, coatability, etc.), photoresist compositions used for such microfabrication include:
It is required that the number of fine particles that cannot be visually observed is small, and that the fine particles do not significantly increase even after long-term storage (in other words, that they have good storage stability).
And this requirement is that when there are many fine particles in the photoresist composition, when the substrate is etched through the resist pattern formed from the photoresist composition, often a pinhole is formed in the substrate portion covered by the resist pattern. Is caused, and the yield at the time of manufacturing an integrated circuit is deteriorated.
【０００３】一方、フォトレジスト組成物中の微細粒子
を除くため、フィルターを用いた濾過が行われている
が、フィルターとしてポリエチレン(以下、ＰＥと略称
する)製のもののみを用いた場合は、微細粒子を一時的
には低減できるものの、保存により微細粒子が顕著に増
加する場合があり、またポリテトラフルオロエチレン
(以下、ＰＴＦＥと略称する)製のフィルターのみを用い
た場合は、製造直後においても微細粒子が十分低減され
ないという問題があった。On the other hand, in order to remove fine particles in the photoresist composition, filtration using a filter is performed. When only a filter made of polyethylene (hereinafter, abbreviated as PE) is used as a filter, Although the fine particles can be temporarily reduced, the fine particles may increase significantly upon storage.
When only a filter made of PTFE (hereinafter abbreviated as PTFE) is used, there is a problem that fine particles are not sufficiently reduced even immediately after the production.
【０００４】[0004]
【課題を解決するための手段】本発明者等は、かかる状
況に鑑み、製造直後のみならず保存後いおいても微細粒
子が低減されたフォトレジスト組成物を製造すべく、鋭
意検討を重ねた結果、フィルターとして、ＰＴＦＥ製の
フィルターとＰＥ製のフィルターの両者を用いることに
より、目的を達成し得ることを見出し、本発明を完成し
た。すなわち本発明は、フォトレジスト組成物をＰＴＦ
Ｅ製のフィルターとＰＥ製のフィルターとを通過させる
ことを特徴とする微細粒子量の低減されたフォトレジス
ト組成物の製造法を提供するものである。In view of such circumstances, the present inventors have made intensive studies to produce a photoresist composition having reduced fine particles not only immediately after production but also after storage. As a result, it was found that the object could be achieved by using both a PTFE filter and a PE filter as the filter, and completed the present invention. That is, the present invention provides a photoresist composition comprising PTF
An object of the present invention is to provide a method for producing a photoresist composition having a reduced amount of fine particles, characterized by passing through a filter made of E and a filter made of PE.
【０００５】[0005]
【発明の実施の形態】本発明に使用されるフォトレジス
ト組成物は、一般に、感光性または非感光性のバインダ
ー樹脂が有機溶剤に溶解されたものであり、バインダー
樹脂が非感光性の場合には、他の感光性の化合物も含有
することになり、もちろん、その他に必要な添加物を含
有することもある。例えば、ノボラック樹脂をバインダ
ーとし、ｏ−キノンジアジド化合物を感光剤とするｇ線
またはｉ線用ポジ型フォトレジスト組成物組成物、ノボ
ラック樹脂をバインダーとし、アジド化合物を感光剤と
するｇ線またはｉ線用ネガ型フォトレジスト組成物、酸
の作用により解裂する基を有するビニルフェノール系ま
たは（メタ）アクリル系の樹脂をバインダーとし、露光
により酸を発生する酸発生剤を感光性化合物とするエキ
シマレーザー用ポジ型フォトレジスト組成物、ノボラッ
ク系、ポリビニルフェノール系または（メタ）アクリル
系のアルカリ可溶性樹脂をバインダーとし酸発生剤を感
光性化合物とし、さらに架橋剤を含有するネガ型フォト
レジスト組成物、ノボラック樹脂やアルキル置換ポリス
ルホンなどを感光性のバインダーとする電子線用フォト
レジスト組成物などがあり、これらいずれのフォトレジ
スト組成物に対しても、本発明の方法を適用しうる。DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The photoresist composition used in the present invention generally comprises a photosensitive or non-photosensitive binder resin dissolved in an organic solvent. Will also contain other photosensitive compounds and, of course, may contain other necessary additives. For example, a positive photoresist composition composition for g-line or i-line using a novolak resin as a binder and an o-quinonediazide compound as a photosensitizer, a g-line or i-line using a novolak resin as a binder and an azide compound as a photosensitizer Excimer laser with negative photoresist composition for use, vinylphenol or (meth) acrylic resin having a group that can be cleaved by the action of an acid as a binder, and an acid generator that generates an acid upon exposure as a photosensitive compound Positive photoresist composition, novolak-based, polyvinylphenol-based or (meth) acrylic-based alkali-soluble resin as binder, acid generator as photosensitive compound, and negative photoresist composition further containing a crosslinking agent, novolak Use a resin or alkyl-substituted polysulfone as the photosensitive binder. Include electron beam photoresist composition, with respect to any of these photoresist compositions may be applied to the method of the present invention.
【０００６】本発明は、上記の様なフォトレジスト組成
物を、ＰＴＦＥ製のフィルターとＰＥ製のフィルターの
両者に通過させることを特徴とするものであるが、先に
ＰＴＦＥ製のフィルターに通過させた後、ＰＥ製のフィ
ルターに通過させることが好ましい。ここで、ＰＴＦＥ
製のフィルターとしては、例えばＡＢＤ１ＵＦＤ３Ｅ
（日本ポール(株)製)、ＡＢＤ１ＵＦＴ３ＥＮ(日本ポー
ル(株)製)等が挙げられる。孔径は、通常0.01〜1.0μｍ
程度のものが使用される。またＰＥ製のフィルターとし
ては、例えばＳＨ４Ｍ２２８Ｊ３(日本ミリポア(株)
製)、CS09XFE(三菱化成(株)製)、CS20XFE(三菱化成(株)
製)等が挙げられる。孔径は、通常0.01〜0.2μｍ程度の
ものが使用される。The present invention is characterized in that the above-mentioned photoresist composition is passed through both a PTFE filter and a PE filter, but is first passed through a PTFE filter. After that, it is preferable to pass through a PE filter. Here, PTFE
For example, ABD1UFD3E
(Manufactured by Nippon Pall Co., Ltd.) and ABD1UFT3EN (manufactured by Nippon Pall Co., Ltd.). The pore size is usually 0.01-1.0 μm
Some are used. As a PE filter, for example, SH4M228J3 (Nippon Millipore Co., Ltd.)
CS09XFE (Mitsubishi Chemical Co., Ltd.), CS20XFE (Mitsubishi Chemical Co., Ltd.)
Manufactured). The pore size is usually about 0.01 to 0.2 μm.
【０００７】このようなフィルターにフォトレジスト組
成物を通過させるに当たり、予めプレ濾過した組成物を
使用することもでき、これにより前記のようなフィルタ
ーの目詰まりを防止し得る。プレ濾過に使用するフィル
ターの孔径は、通常、前記のようなフィルターの孔径以
上である。プレ濾過に使用する好ましいフィルターとし
ては、通常、孔径が0.1〜10μｍ程度のＰＴＦＥ製、Ｐ
Ｅ製またはナイロン製のフィルターが使用される。In passing the photoresist composition through such a filter, a pre-filtered composition may be used, thereby preventing the filter from being clogged as described above. The pore size of the filter used for the pre-filtration is usually equal to or larger than the pore size of the filter as described above. Preferred filters used for pre-filtration are usually made of PTFE having a pore size of about 0.1 to 10 μm,
E or nylon filters are used.
【０００８】[0008]
【実施例】以下、実施例を示して本発明をさらに詳しく
説明するが、本発明はこれらの実施例によって何ら限定
されるものではない。実施例、比較例において、微細粒
子測定は、リオン（株）製自動微粒子測定器（ＫＬ−２
０型）により行った。EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. In Examples and Comparative Examples, the measurement of fine particles was carried out using an automatic particle meter (KL-2) manufactured by Rion Co., Ltd.
0 type).
【０００９】実施例１ ノボラック樹脂、感光材、溶剤等からなるスミレジスト
ＰＦＩ−３８Ａ４(ポジ型フォトレジスト組成物、以下
レジストＡと略称する)を、ＰＥ製フィルター（孔径
０．２μｍ、ＣＷＵＧ０ １ＰＬＴ；日本ミリポア
（株）製）でプレ濾過した。次にこれをＰＥ製フィルタ
ー（孔径０．１μｍ、ＣＷＵＶ０１ＰＬＴ ；日本ミリ
ポア（株）製）に通過させた後、ＰＴＦＥ製フィルター
（（孔径０．０５μｍ、ＤＦＡ１ＵＦＤＥＳＷ４４；日
本ポ−ル（株）製）に通過させた。操作は、３０ｋＰａ
の窒素加圧下で実施した。このものの0.2μｍ以上の微
細粒子数を測定し、その結果を表１に示した。またこの
ものを２３℃で長時間保存し、微細粒子数を測定し、そ
の結果（ｍｌ当たりの個数）を表１に示した。Example 1 A Sumireresist PFI-38A4 (positive photoresist composition, hereinafter abbreviated as "resist A") comprising a novolak resin, a photosensitive material, a solvent, and the like was applied to a PE filter (pore size 0.2 μm, CWUG01PLT; It was pre-filtered through Nippon Millipore Co., Ltd.). Next, this was passed through a PE filter (pore size: 0.1 μm, CWUV01PLT; manufactured by Nippon Millipore Co., Ltd.), and then passed through a PTFE filter (pore size: 0.05 μm, DFA1UFDESW44; manufactured by Nippon Pol Co., Ltd.). Operation was performed at 30 kPa.
Under nitrogen pressure. The number of fine particles of 0.2 μm or more was measured, and the results are shown in Table 1. This was stored at 23 ° C. for a long time, and the number of fine particles was measured. The result (number per ml) is shown in Table 1.
【００１０】比較例１ 実施例１において、ＰＴＦＥ製フィルターの代わりに、
ＰＥ製フィ ルター（孔径０．１μｍ、ＣＷＵＶ０Ｓ１
Ｓ３；日本ミリポア（株）製）を用いる以外は実施例１
に準拠して実施した。 微細粒子の測定結果を表１に示
した。Comparative Example 1 In Example 1, instead of the PTFE filter,
PE filter (pore size 0.1 μm, CWUV0S1
S3; Example 1 except that Nippon Millipore Co., Ltd. was used.
It was carried out in accordance with. Table 1 shows the measurement results of the fine particles.
【００１１】実施例２ ノボラック樹脂、感光材、溶剤等からなるスミレジスト
ＥＨ−９００Ｂ２(ポジ型フォトレジスト組成物、以下
レジストＢと略称する)を、ＰＥ製フィルター（孔径
０．２μｍ、ＣＷＵＧ０ １ＰＬＴ；日本ミリポア
（株）製）でプレ濾過した。次にこれをＰＥ製フィルタ
ー（孔径０．１μｍ、ＣＷＵＶ０１ＰＬＴ ；日本ミリ
ポア（株）製）に通過させた後、ＰＴＦＥ製フィルター
（（孔径０．１μｍ、ＦＶＷＰ１４２５０；日本ミリポ
ア（株）製）、次にＰＥ製フィルター（孔径０．０９μ
ｍ、ＣＳ０９ＸＦＥ；三菱化成（株）製）を通過させ
た。操作は、３０ｋＰａの窒素加圧下で実施した。この
ものの0.２μｍ以上の微細粒子数を測定し、その結果を
表１に示した。Example 2 Sumiresist EH-900B2 (positive photoresist composition, hereinafter abbreviated as "resist B") comprising a novolak resin, a photosensitive material, a solvent and the like was used as a PE filter (pore size 0.2 μm, CWUG01PLT; It was pre-filtered through Nippon Millipore Co., Ltd.). Next, this was passed through a PE filter (pore size: 0.1 μm, CWUV01PLT; manufactured by Nippon Millipore Co., Ltd.), and then a PTFE filter ((pore size: 0.1 μm, FVWP14250; manufactured by Nippon Millipore Co., Ltd.) PE filter (pore size 0.09μ)
m, CS09XFE; manufactured by Mitsubishi Kasei Corporation). The operation was performed under a nitrogen pressure of 30 kPa. The number of fine particles of 0.2 μm or more was measured, and the results are shown in Table 1.
【００１２】比較例２ 実施例２において、ＰＴＦＥ製フィルターを使用しない
こと以外は実施例１に準拠して実施した。 微細粒子の
測定結果を表１に示した。Comparative Example 2 The procedure of Example 2 was repeated, except that no PTFE filter was used. Table 1 shows the measurement results of the fine particles.
【００１３】[0013]
【表１】 レジスト フィルター 製造直後 保存後 実施例１ Ａ PE−PTFE １３ ２９(70日) 比較例１ Ａ PE−PE ５２ １９０９(21日) 実施例２ Ｂ PE−PTFE−PE ５１ ０(51日) 比較例２ Ｂ PE−PE ８１ ２９８０(51日)[Table 1] Resist filter Immediately after production and after storage Example 1 A PE-PTFE 13 29 (70 days) Comparative Example 1 A PE-PE 52 1909 (21 days) Example 2 B PE-PTFE-PE 510 (51 days) ) Comparative Example 2 B PE-PE 81 2980 (51 days)
【００１４】実施例３ ノボラック樹脂、感光材、溶剤等からなるスミレジスト
ＰＦＩ−２６Ａ９(ポジ型フォトレジスト組成物、以下
レジストＣと略称する)を、ＰＴＦＥ製フィルター（孔
径 ０．１μｍ、ＡＢ１ＦＴ３ＥＪ；日本ポール（株）
製）でプレ濾過した。次にこれをＰＴＦＥ製フィルター
（ 孔径０．０５μｍ、ＡＢ１ＦＤ３ＥＪ；日本ポール
（株）製）に通過させた後、ＰＥ製フィルター（孔径
０．１μｍ、ＣＷＵＶ０１ＰＬＴ；日本ミリポア（株）
製）に通過させた。操作は、５０ｋＰａの窒素加圧下で
実施し、容量１ガロンのガラス瓶に連続して充填し、充
填本数と０．２μｍ以上の粒子数／ｍｌの結果を 図１
に示した。Example 3 Sumiresist PFI-26A9 (positive photoresist composition, hereinafter abbreviated as "resist C") comprising a novolak resin, a photosensitive material, a solvent, etc. was used as a filter made of PTFE (pore size: 0.1 μm, AB1FT3EJ; Japan). Paul Corporation
Pre-filtered). Next, this was passed through a PTFE filter (pore size: 0.05 μm, AB1FD3EJ; manufactured by Nippon Pall Co., Ltd.), and then a PE filter (pore size: 0.1 μm, CWUV01PLT; Japan Millipore Co., Ltd.)
). The operation was performed under a nitrogen pressure of 50 kPa, and the glass bottle having a capacity of 1 gallon was continuously filled.
It was shown to.
【００１５】実施例４ 実施例３において、ＰＥ製フィルターをＰＥ製フィルタ
ー（孔径０．２μｍ、ＣＳ ２０ＸＦＥ；三菱化成
（株）製）に代えた以外は、実施例３に準拠して実施し
た。結果を図１に示した。Example 4 Example 3 was carried out in the same manner as in Example 3, except that the PE filter was replaced by a PE filter (pore size: 0.2 μm, CS 20XFE; manufactured by Mitsubishi Kasei Co., Ltd.). The results are shown in FIG.
【００１６】比較例３ 実施例３において、ＰＥ製フィルターをＰＴＦＥ製フィ
ルター（孔径０．０５μｍ、ＡＢＤ１ＵＦＤ３ＥＪ；日
本ポール（株）製）に代えた以外は、実施例３に準拠し
て実施し、結果を図１に示した。Comparative Example 3 The procedure of Example 3 was repeated, except that the PE filter was replaced by a PTFE filter (pore diameter: 0.05 μm, ABD1UFD3EJ; manufactured by Nippon Pall Co., Ltd.). Is shown in FIG.
【００１７】図１から明らかなように、ＰＥ製フィルタ
ーとＰＴＦＥ製フィルターを組合せていない比較例３の
場合は、微細粒子の数を５０個／ｍｌまで低減できなか
ったが、ＰＥ製フィルターとＰＴＦＥ製フィルターを組
合せた実施例３及び実施例４の場合は、５０個／ｍｌ以
下にまで低減できている。As apparent from FIG. 1, in the case of Comparative Example 3 in which the PE filter and the PTFE filter were not combined, the number of fine particles could not be reduced to 50 / ml, but the PE filter and the PTFE filter were not combined. In the case of Example 3 and Example 4 in which filters made in combination are used, the number can be reduced to 50 / ml or less.
【００１８】[0018]
【発明の効果】本発明によれば、フィルターとして、Ｐ
ＴＦＥ製のフィルターとＰＥ製のフィルターの両者を用
い、これにフォトレジスト組成物を通過せしめることに
より、ることにより、製造直後のみならずこれを保存し
た後においても微細粒子が低減されたフォトレジスト組
成物を製造することができる。According to the present invention, as a filter, P
By using both a filter made of TFE and a filter made of PE and allowing the photoresist composition to pass through, a photoresist having reduced fine particles not only immediately after production but also after storage thereof A composition can be manufactured.
【００１９】[0019]
【図面の簡単な説明】[Brief description of the drawings]
【図１】フォトレジスト組成物の連続濾過における、充
填本数と微細粒子数の推移を示すグラフである。FIG. 1 is a graph showing the transition of the number of fillers and the number of fine particles in continuous filtration of a photoresist composition.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｇ０３Ｆ 7/38 ５０１ Ｇ０３Ｆ 7/38 ５０１ Ｈ０１Ｌ 21/027 Ｈ０１Ｌ 21/30 ５０２Ｒ (72)発明者 花元 幸夫 大阪市此花区春日出中３丁目１番98号 住 友化学工業株式会社内 Ｆターム(参考） 2H025 AB16 BJ10 EA01 2H096 AA25 CA20 DA10 4D006 GA02 KA02 KB14 MA22 MC22 MC22X MC30 MC30X MC54 MC54X PB20 PC80 4D019 AA03 BA13 BB08 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) G03F 7/38 501 G03F 7/38 501 H01L 21/027 H01L 21/30 502R (72) Inventor Yukio Hanamoto No. 3-98 Kasuganaka, Konohana-ku, Osaka Sumitomo Chemical Co., Ltd. F term (reference) 2H025 AB16 BJ10 EA01 2H096 AA25 CA20 DA10 4D006 GA02 KA02 KB14 MA22 MC22 MC22X MC30 MC30X MC54 MC54X PB20 PC80 4D019 AA03 BB08
Claims (4)
ロエチレン製のフィルターとポリエチレン製のフィルタ
ーとを通過させることを特徴とする微細粒子量の低減さ
れたフォトレジスト組成物の製法。1. A method for producing a photoresist composition having a reduced amount of fine particles, wherein the photoresist composition is passed through a filter made of polytetrafluoroethylene and a filter made of polyethylene.
ーを通過させた後、ポリエチレン製のフィルターを通過
させることを特徴とする請求項１記載の製造法。2. The method according to claim 1, wherein the mixture is passed through a filter made of polytetrafluoroethylene and then passed through a filter made of polyethylene.
ーの孔径が0.01〜１μｍであり、ポリエチレン製のフィ
ルターの孔径が0.01〜0.2μｍであることを特徴とする
請求項１又は２に記載の製造法。3. The method according to claim 1, wherein the pore size of the polytetrafluoroethylene filter is 0.01 to 1 μm, and the pore size of the polyethylene filter is 0.01 to 0.2 μm.
μｍのポリテトラフルオロエチレン製、ポリエチレン製
またはナイロン製のフィルターでプレ濾過されたもので
あることを特徴とする請求項１〜３いずれかに記載の製
造法。4. A photoresist composition having a pore size of 0.1 to 10
The process according to any one of claims 1 to 3, wherein the product is pre-filtered with a filter made of polytetrafluoroethylene, polyethylene or nylon having a diameter of μm.
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| JP2000288264A JP4006937B2 (en) | 2000-09-22 | 2000-09-22 | Method for producing photoresist composition with reduced amount of fine particles |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000288264A JP4006937B2 (en) | 2000-09-22 | 2000-09-22 | Method for producing photoresist composition with reduced amount of fine particles |
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| Publication Number | Publication Date |
|---|---|
| JP2002099076A true JP2002099076A (en) | 2002-04-05 |
| JP4006937B2 JP4006937B2 (en) | 2007-11-14 |
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|---|---|---|---|
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