JP4006937B2 - Method for producing photoresist composition with reduced amount of fine particles - Google Patents
Method for producing photoresist composition with reduced amount of fine particles Download PDFInfo
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- JP4006937B2 JP4006937B2 JP2000288264A JP2000288264A JP4006937B2 JP 4006937 B2 JP4006937 B2 JP 4006937B2 JP 2000288264 A JP2000288264 A JP 2000288264A JP 2000288264 A JP2000288264 A JP 2000288264A JP 4006937 B2 JP4006937 B2 JP 4006937B2
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Description
【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。
【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ＩＣ、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。
【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。
【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ポリテトラフルオ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造法を提供するものである。但し、前記ポリテトラフルオロエチレン製のフィルターが複数のポリテトラフルオロエチレン製のフィルターを積層することによって構成され、かつ、前記複数のポリテトラフルオロエチレン製のフィルターのうち、少なくとも一つのポリテトラフルオロエチレン製のフィルターが他のポリテトラフルオロエチレン製のフィルターと異なる孔径を有する場合を除く。
【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。
【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。
【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、ＰＥ製またはナイロン製のフィルターが使用される。
【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−２０型）により行った。
【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。
【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、ＣＷＵＶ０Ｓ１Ｓ３；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。
【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０．０９μｍ、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。
【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。
【００１３】
【表１】
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。
【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。
【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。
【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。
【００１８】
【発明の効果】
本発明によれば、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、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。
【００１９】
【図面の簡単な説明】
【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。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a photoresist composition suitable for lithography or the like that operates by high energy radiation such as ultraviolet rays, far ultraviolet rays (including excimer lasers, etc.), electron beams, X-rays, or synchrotron radiation. .
[0002]
[Prior art, problems to be solved by the invention]
Photoresist compositions are used as pattern forming materials for fine precision processing in the manufacturing process of ICs, LSIs, etc. used in computers, etc. With the high integration of LSIs, the design rules for integrated circuits are also increasing. The size is reduced from 0.35 μm to 0.15 μm. In addition to basic performance (resolution, sensitivity, profile, coatability, etc.), the photoresist composition used for such microfabrication has few fine particles that cannot be visually observed, and even after long-term storage. It is required that the fine particles do not increase remarkably (in other words, have good storage stability). This requirement is that when there are many fine particles in the photoresist composition, etching the substrate through the resist pattern formed from the photoresist composition often causes pinholes in the portion of the substrate covered by the resist pattern. This is because the yield at the time of manufacturing an integrated circuit deteriorates.
[0003]
On the other hand, in order to remove fine particles in the photoresist composition, filtration using a filter is performed, but when only a filter made of polyethylene (hereinafter abbreviated as PE) is used as the filter, fine particles are used. Although it can be temporarily reduced, fine particles may increase remarkably by storage, and when only a filter made of polytetrafluoroethylene (hereinafter abbreviated as PTFE) is used, fine particles even immediately after production. There has been a problem that is not sufficiently reduced.
[0004]
[Means for Solving the Problems]
In view of such circumstances, the present inventors have conducted extensive studies to produce a photoresist composition with reduced fine particles not only immediately after production but also after storage. As a result, PTFE made of PTFE was used as a filter. The inventors have found that the object can be achieved by using both a filter and a filter made of PE, thereby completing the present invention.
That is, the present invention provides a manufacturing method of the photoresist composition a reduced photoresist composition of the fine particle amount, characterized in that passing the filter made of polytetrafluoroethylene filter made of polyethylene It is. However, the polytetrafluoroethylene filter is configured by stacking a plurality of polytetrafluoroethylene filters, and at least one of the plurality of polytetrafluoroethylene filters is selected. Except when the filter made of the filter has a different pore size from other polytetrafluoroethylene filters.
[0005]
DETAILED DESCRIPTION OF THE INVENTION
The photoresist composition used in the present invention is generally obtained by dissolving a photosensitive or non-photosensitive binder resin in an organic solvent. When the binder resin is non-photosensitive, other photosensitive resins are used. It will also contain compounds, and of course may contain other necessary additives.
For example, a positive photoresist composition for g-line or i-line using a novolak resin as a binder and an o-quinonediazide compound as a photosensitizer, and a g-line or i-line using a novolac resin as a binder and an azide compound as a photosensitizer. Negative photoresist composition, excimer laser with vinylphenol or (meth) acrylic resin having a group that can be cleaved by the action of acid as binder and acid generator that generates acid upon exposure as photosensitive compound Positive photoresist composition, novolak, polyvinylphenol, or (meth) acrylic alkali-soluble resin as binder, acid generator as photosensitive compound, and negative photoresist composition containing no crosslinking, novolak Resins and alkyl-substituted polysulfones are used as photosensitive binders. Include electron beam photoresist composition, with respect to any of these photoresist compositions may be applied to the method of the present invention.
[0006]
The present invention is characterized in that the photoresist composition as described above is passed through both a PTFE filter and a PE filter, and after passing through a PTFE filter, It is preferable to pass through a PE filter.
Here, examples of the PTFE filter include ABD1UFD3E (manufactured by Nippon Pole Co., Ltd.), ABD1UFT3EN (manufactured by Nippon Pole Co., Ltd.), and the like. The pore diameter is usually about 0.01 to 1.0 μm.
Examples of the PE filter include SH4M228J3 (Nippon Millipore Corporation), CS09XFE (Mitsubishi Kasei Co., Ltd.), CS20XFE (Mitsubishi Kasei Co., Ltd.), and the like. The pore diameter is usually about 0.01 to 0.2 μm.
[0007]
In passing the photoresist composition through such a filter, a pre-filtered composition can be used, thereby preventing the filter from being clogged as described above. The pore size of the filter used for prefiltration is usually larger than the pore size of the filter as described above. As a preferable filter used for the prefiltration, a filter made of PTFE, PE or nylon having a pore diameter of about 0.1 to 10 μm is usually used.
[0008]
【Example】
EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated in more detail, this invention is not limited at all by these Examples. In Examples and Comparative Examples, fine particle measurement was performed with an automatic fine particle measuring instrument (KL-20 type) manufactured by Rion Co., Ltd.
[0009]
Example 1
Sumiresist PFI-38A4 (positive photoresist composition, hereinafter abbreviated as “resist A”) made of novolak resin, photosensitive material, solvent, etc., is made of PE filter (pore size 0.2 μm, CWUG0 1PLT; manufactured by Nihon Millipore) ). Next, this was passed through a PE filter (pore size 0.1 μm, CWUV01PLT; manufactured by Nippon Millipore Corp.), and then passed through a PTFE filter (pore size 0.05 μm, DFA1UFDESW44; manufactured by Nippon Pol Co., Ltd.). The operation was carried out under nitrogen pressure of 30 kPa, and the number of fine particles of 0.2 μm or more was measured and the results are shown in Table 1. Also, this was stored at 23 ° C. for a long time, The number of fine particles was measured, and the results (number per ml) are shown in Table 1.
[0010]
Comparative Example 1
In Example 1, instead of the PTFE filter, a PE filter (pore size 0.1 μm, CWUV0S1S3; manufactured by Nippon Millipore Co., Ltd.) was used. The measurement results of the fine particles are shown in Table 1.
[0011]
Example 2
Sumiresist EH-900B2 (positive photoresist composition, hereinafter abbreviated as “resist B”) made of novolak resin, photosensitive material, solvent, etc., is made of PE filter (pore size 0.2 μm, CWUG0 1PLT; manufactured by Nihon Millipore Corporation) ). Next, this was passed through a PE filter (pore size 0.1 μm, CWUV01PLT; manufactured by Nippon Millipore Corp.), and then a PTFE filter (pore size 0.1 μm, FVWP14250; manufactured by Nihon Millipore Corp.), then The filter was passed through a PE filter (pore size 0.09 μm, CS09XFE; manufactured by Mitsubishi Kasei Co., Ltd.) The operation was performed under a nitrogen pressure of 30 kPa, and the number of fine particles of 0.2 μm or more was measured. The results are shown in Table 1.
[0012]
Comparative Example 2
In Example 2, it implemented based on Example 1 except not using the filter made from PTFE. The measurement results of the fine particles are shown in Table 1.
[0013]
[Table 1]
Example 3
Sumiresist PFI-26A9 (positive photoresist composition, hereinafter abbreviated as “resist C”) made of novolak resin, photosensitive material, solvent, etc., PTFE filter (pore size 0.1 μm, AB1FT3EJ; manufactured by Nippon Pole Co., Ltd.) And prefiltered. Next, this was passed through a PTFE filter (pore size 0.05 μm, AB1FD3EJ; manufactured by Nippon Pole Co., Ltd.) and then passed through a PE filter (pore size 0.1 μm, CWUV01PLT; manufactured by Nihon Millipore Corp.). . The operation was carried out under nitrogen pressure of 50 kPa, and a glass bottle having a capacity of 1 gallon was continuously filled. The results of the number of filled particles and the number of particles of 0.2 μm or more / ml are shown in FIG.
[0015]
Example 4
In Example 3, it carried out based on Example 3 except having replaced the filter made from PE with the filter made from PE (pore diameter 0.2micrometer, CS 20XFE; Mitsubishi Kasei Co., Ltd. product). The results are shown in FIG.
[0016]
Comparative Example 3
In Example 3, except that the PE filter was replaced with a PTFE filter (pore size 0.05 μm, ABD1UFD3EJ; manufactured by Nippon Pole Co., Ltd.), the results were shown in FIG. .
[0017]
As is clear 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 particles / ml, but the PE filter and the PTFE filter were not used. In the case of the combined Example 3 and Example 4, it can be reduced to 50 pieces / ml or less.
[0018]
【The invention's effect】
According to the present invention, by using both a PTFE filter and a PE filter as a filter and allowing the photoresist composition to pass therethrough, not only immediately after production but also after storing it. In addition, a photoresist composition with reduced fine particles can be produced.
[0019]
[Brief description of the drawings]
FIG. 1 is a graph showing changes in the number of filled particles and the number of fine particles in continuous filtration of a photoresist composition.
Claims (4)
Priority Applications (1)
| 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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| 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 JP2002099076A (en) | 2002-04-05 |
| JP4006937B2 true JP4006937B2 (en) | 2007-11-14 |
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4637967B2 (en) * | 2002-12-19 | 2011-02-23 | 東京応化工業株式会社 | Method for producing photoresist composition |
| JP4637476B2 (en) | 2002-12-19 | 2011-02-23 | 東京応化工業株式会社 | Method for producing photoresist composition |
| JP4222850B2 (en) * | 2003-02-10 | 2009-02-12 | Ｓｐａｎｓｉｏｎ Ｊａｐａｎ株式会社 | Radiation-sensitive resin composition, method for producing the same, and method for producing a semiconductor device using the same |
| JP4786238B2 (en) * | 2005-07-19 | 2011-10-05 | 東京応化工業株式会社 | Resist composition manufacturing method, filtration apparatus, resist composition coating apparatus |
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| JP6461668B2 (en) * | 2014-08-11 | 2019-01-30 | 東京応化工業株式会社 | Filtration material, filtration filter, production method of filtration material, and filtration method |
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| JP6819621B2 (en) * | 2018-01-25 | 2021-01-27 | 信越半導体株式会社 | Work cutting method and wire saw |
| CN114008525A (en) * | 2019-05-22 | 2022-02-01 | 东京应化工业株式会社 | Method for producing purified product of resist composition, method for forming resist pattern, and purified product of resist composition |
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