JP3832267B2 - Method for producing photoresist liquid product with reduced number of fine particles - Google Patents
Method for producing photoresist liquid product with reduced number of fine particles Download PDFInfo
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- JP3832267B2 JP3832267B2 JP2001115091A JP2001115091A JP3832267B2 JP 3832267 B2 JP3832267 B2 JP 3832267B2 JP 2001115091 A JP2001115091 A JP 2001115091A JP 2001115091 A JP2001115091 A JP 2001115091A JP 3832267 B2 JP3832267 B2 JP 3832267B2
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Description
【０００１】
【発明の属する技術分野】
本発明は微粒子数の低減されたフォトレジスト液製品の製造方法に関し、詳しくは、紫外線、遠紫外線、電子線、Ｘ線等の放射線によって作用するリソグラフィに適したフォトレジスト液製品を製造する方法に関するものである。
【０００２】
【従来の技術】
微粒子数が低減されたフォトレジスト液製品は、従来、フッ素系樹脂製及びポリオレフィン製のフィルターから選ばれる１種以上のフィルターにより、原料フォトレジスト液を濾過して製造されていた。
【０００３】
【発明が解決しようとする課題】
しかしながら、上記フィルターは繰り返し濾過操作に使用すると、フィルターに捕捉された微粒子により目詰まりしてしまい、事実上使い捨てになるため、従来の製造方法は、結果的にコストがかさむものであった。
【０００４】
【課題を解決するための手段】
本発明者は、コストがかさまないフォトレジスト液製品の製造方法を提供すべく鋭意検討した結果、一回以上原料フォトレジスト液の濾過に使用されたフッ素系樹脂製及びポリオレフィン製のフィルターから選ばれる１種以上のフィルターを、他の有機溶媒を含んでいてもよいＮ−メチルピロリドンを用いて濾過時の方向とは逆向きに洗浄し、この逆洗浄されたフィルターにより前記の原料フォトレジスト液を濾過すると、上記課題を解決できることを見出して、本発明を完成するに至った。
【０００５】
即ち、本発明は、フッ素系樹脂製製及びポリオレフィン製のフィルターから選ばれる１種以上のフィルターにより、原料フォトレジスト液を濾過してフォトレジスト液製品を製造する方法であって、一回以上原料フォトレジスト液の濾過に使用された上記１種以上のフィルターを、他の有機溶媒を含んでいてもよいＮ−メチルピロリドンを用いて濾過時の方向とは逆向きに洗浄し、この逆洗浄されたフィルターにより前記の原料フォトレジスト液を濾過することを特徴とする微粒子数の低減されたフォトレジスト液製品の製造方法を提供するものである。
以下、本発明を詳細に説明する。
【０００６】
【発明の実施の形態】
本発明において用いられる原料フォトレジスト液は、上記リソグラフィに適用できるものであればよいが、好ましくは、上記フォトレジスト液中の樹脂成分又は感光剤成分が、Ｎ−メチルピロリドンの希薄濃度溶液中において、容易に溶解又は分解するものを挙げることができる。このような感光剤成分としては、例えば、ｏ−ベンゾキノンジアジドスルホン酸エステル、ｏ−ベンゾキノンジアジドスルホン酸アミド、ｏ−ナフトキノンジアジドスルホン酸エステルやｏ−ナフトキノンジアジドスルホン酸アミドのようなキノンジアジドスルホン酸エステル及びキノンジアジドスルホン酸アミド等が挙げられる。
【０００７】
本発明において用いられる他の有機溶媒としては、Ｎ−メチルピロリドンと混和するものであればよいが、好ましくは、例えば、原料フォトレジスト液中に含まれる溶媒が挙げられる。このような原料フォトレジスト液中に含まれる溶媒としては、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、アセトン、メチルイソブチルケトン、２−ヘプタノン、シクロヘキサノン、γ−ブチロラクトン、乳酸エチル、酢酸ブチル、酢酸アミル、ピルビン酸エチル、ジエチレングリコールジメチルエーテル、メチルセロソルブアセテート及びエチルセロソルブアセテート等が例示される。
原料フォトレジスト液中の樹脂成分としては、アルカリ可溶性樹脂が好ましい。
又、アルカリ可溶性樹脂としては、例えば、ポジ型フォトレジストに用いられるノボラック樹脂が好ましい。
【０００８】
本発明は、一回以上原料フォトレジスト液の濾過に使用された上記フィルターを、他の有機溶媒を含んでいてもよいＮ−メチルピロリドンを用いて濾過時の方向とは逆向きに洗浄し、この逆洗浄されたフィルターにより前記の原料フォトレジスト液を濾過することを特徴とするものであるが、原料フォトレジスト液を、一旦、フッ素系樹脂製のフィルターに通過させ、その後、ポリオレフィン製のフィルターに通過させる方法が好ましい。
本発明において用いられるフッ素系樹脂製フィルターとしては、ポリテトラフルオロエチレン製のものがこのましい。又、ポリオレフィン製のフィルターとしては、ポリエチレン製のものが好ましい。
本発明において、逆洗浄後に再使用するフィルターとしては、ポリエチレン製のフィルターが好ましい。
フィルターの逆洗浄の際には、原料フォトレジスト液に含まれる感光剤成分が、Ｎ−メチルピロリドン溶液中において、1〜500ｐｐｍの範囲の希薄濃度になることが好ましい。例えば、ｏ−ベンゾキノンジアジドスルホン酸エステル、ｏ−ベンゾキノンジアジドスルホン酸アミド、ｏ−ナフトキノンジアジドスルホン酸エステルやｏ−ナフトキノンジアジドスルホン酸アミド等のポジ型フォトレジストに用いられる感光剤成分は、比較的、フォトレジスト液中の微粒子数の増加原因となりやすいが、フィルターに残存している感光剤成分が上記濃度範囲でＮ−メチルピロリドンにより分解されやすいので、効率的な逆洗浄を行うことが可能になる。
【０００９】
本発明で好ましく用いられるポリテトラフルオロエチレン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0.01〜１μｍ程度のものが使用される。又、本発明で好ましく用いられるポリエチレン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。
【００１０】
【実施例】
以下、実施例等により、本発明を更に詳細に説明する。
【００１１】
参考例１
図１に記載の装置［配管における太線及び矢印は、液の流れ方向を示す。］を用いて、ポリエチレン製のフィルターＳＨ４Ｍ２２８Ｊ３［孔径０．２μｍ、日本ミリポア（株）製］の逆洗浄を行った。
上記ポリエチレン製フィルターは、原料フォトレジスト液を一回濾過して、住友化学工業（株）製ＰＦＩ−３２Ａ６［アルカリ可溶性ノボラック樹脂、キノンジアジドスルホン酸エステル系感光剤及び２−ヘプタノンからなるポジ型フォトレジスト液製品］を得たときに使用したものである。又、図１記載の釜（１）内には、アルカリ可溶性ノボラック樹脂、キノンジアジドスルホン酸エステル系感光剤及び２−ヘプタノン等を混合することにより調製された上記ＰＦＩ−３２Ａ６（原料フォトレジスト液）の残液が溜まっている。
【００１２】
上記原料フォトレジストの残液が溜まった釜（１）からフィルターハウジング（２）内までのバルブや配管、並びに、フィルターハウジング（２）からフィルターハウジング（３）内までのバルブや配管を、２−ヘプタノン、Ｎ−メチルピロリドン及び２−ヘプタノンを用いて、この順に逆洗浄した。
最初の２−ヘプタノンによる洗浄（以下、粗洗浄という）は３回行い、それぞれ順に、２−ヘプタノンを１４．１ｋｇ、７．４ｋｇ及び８．４ｋｇ使用した。２番目のＮ−メチルピロリドンによる洗浄（以下、ＮＭＰ洗浄という）は２回行い、それぞれ順に、ＮＭＰを５．４ｋｇ及び７ｋｇ使用した。３番目の２−ヘプタノンによる洗浄（以下、置換洗浄という）は７回行い、それぞれ順に、２−ヘプタノンを５ｋｇ、６．２ｋｇ、６ｋｇ、７．２ｋｇ、６ｋｇ、８ｋｇ及び７ｋｇ使用した。
２回目の粗洗浄後に得られた液中の感光剤濃度は０．４ｐｐｍであり、３回目の粗洗浄後に得られた液中には、感光剤は検出されなかった。又、１回目の置換洗浄後に得られた液中のＮＭＰ濃度は２８０７ｐｐｍであり、４回目の置換洗浄後に得られた液中のＮＭＰ濃度は９３ｐｐｍであり、７回目の置換洗浄後に得られた液中のＮＭＰ濃度は２９ｐｐｍであった。なお、フィルターハウジング（２）は、溶媒由来の微粒子のカットを主目的として設けている。
【００１３】
参考例２
ポリエチレン製のフィルターＳＨ４Ｍ２２８Ｊ３（購入直後の新品を２−ヘプタノンで湿潤させたもの）と、参考例１で得た逆洗浄後のポリエチレン製フィルターＳＨ４Ｍ２２８Ｊ３（以下、再使用品という）とを、図２記載のフィルターハウジング（３）内にそれぞれ別個に装着し、図２記載の装置を用いて以下に記すテストを行った。
【００１４】
＜粒子除去性能に影響するフィルター微細孔構造の損壊有無の確認試験＞
フィルターハウジング（３）の側部に設けたバルブ（５）から窒素ガスを導入し、バルブ（６）を調節することにより、上記装着したフィルターを一定時間加圧後、拡散通過ガス量を捕集して、フィルター微細孔構造の損壊有無を試験した。窒素圧１５０ｋＰａにおいても、再使用品の拡散通過ガス量は、新品フィルターの拡散通過ガス量以下であり、フィルターの微細孔構造の損壊がないことが確認された。
【００１５】
参考例３
参考例１で得たポリエチレン製フィルターＳＨ４Ｍ２２８Ｊ３（再使用品）を上記ＰＦＩ−３２Ａ６（フォトレジスト液製品）に浸漬し、前記ＰＦＩ−３２Ａ６製品（フィルターの浸漬はなし）を対照として、０．２μｍ径以上の微粒子数の変化を経時的に試験して、表１の結果を得た。
【００１６】
表１のとおり、室温以上の温度では、微粒子数の増加は認められなかった。このことから、参考例１で得た再使用ポリエチレン製フィルターは２−ヘプタノンに対する耐性に優れており、このフィルターをフォトレジスト液の濾過に使用しても、微粒子数増加の原因にならないことが判る。
【００１８】
実施例１
図３記載の装置［参考例１で得たポリエチレン製フィルターＳＨ４Ｍ２２８Ｊ３（再使用品）をフィルターハウジング（３）内に装着している。又、フィルターハウジング（２）は、原料レジストを構成する溶媒由来の微粒子のカットを主目的として設けている。なお、配管における太線及び矢印は、液の流れ方向を示す］を用い、参考例１で使用した原料フォトレジスト液を、窒素ガス加圧によるワンパス方式で濾過した結果、０．２μｍ径以上の微粒子数の少ないフォトレジスト製品が得られた。
なお、本例では窒素ガス加圧によるワンパス方式で濾過したが、ポンプを用いて循環方式で濾過しても、ワンパス方式と同様、微粒子数の少ないフォトレジスト製品が得られる。
【００１９】
【発明の効果】
本発明によれば、フォトレジスト製品を工業的有利に製造することができる。
【図面の簡単な説明】
【図１】参考例１で用いた装置
【図２】参考例２で用いた装置
【図３】実施例１で用いた装置
【符号の説明】
１・・釜、２・・フィルターハウジング、３・・フィルターハウジング、４・・逆洗浄入口部、５・・開閉用バルブ、６・・圧力調節用バルブ[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a photoresist liquid product having a reduced number of fine particles, and more particularly, to a method for producing a photoresist liquid product suitable for lithography that acts by radiation such as ultraviolet rays, far ultraviolet rays, electron beams, and X-rays. Is.
[0002]
[Prior art]
Conventionally, a photoresist liquid product with a reduced number of fine particles has been produced by filtering a raw material photoresist liquid through one or more filters selected from a fluororesin filter and a polyolefin filter.
[0003]
[Problems to be solved by the invention]
However, when the filter is repeatedly used for filtration operations, the filter is clogged with fine particles trapped in the filter and becomes practically disposable. As a result, the conventional manufacturing method is costly.
[0004]
[Means for Solving the Problems]
As a result of intensive studies to provide a method for producing a photoresist liquid product that does not cost much, the present inventor has selected from fluororesin-made and polyolefin-made filters that have been used for filtering the raw photoresist liquid more than once. One or more types of filters are washed with N-methylpyrrolidone which may contain other organic solvents in a direction opposite to the direction of filtration, and the raw photoresist solution is obtained by the backwashed filter. As a result, it was found that the above-mentioned problems could be solved by filtering, and the present invention was completed.
[0005]
That is, the present invention is a method for producing a photoresist liquid product by filtering a raw material photoresist solution with one or more types of filters selected from fluororesin-made and polyolefin-made filters. The one or more filters used for the filtration of the photoresist solution are washed with N-methylpyrrolidone, which may contain other organic solvents, in the direction opposite to the direction of filtration, and this back washing is performed. And providing a method for producing a photoresist liquid product with a reduced number of fine particles, wherein the raw material photoresist liquid is filtered with a filter.
Hereinafter, the present invention will be described in detail.
[0006]
DETAILED DESCRIPTION OF THE INVENTION
The raw material photoresist solution used in the present invention may be any material that can be applied to the lithography. Preferably, the resin component or the photosensitive agent component in the photoresist solution is in a dilute solution of N-methylpyrrolidone. And those that dissolve or decompose easily. Examples of such a photosensitizer component include o-benzoquinone diazide sulfonic acid ester, o-benzoquinone diazide sulfonic acid amide, o-naphthoquinone diazide sulfonic acid ester, and quinone diazide sulfonic acid ester such as o-naphthoquinone diazide sulfonic acid amide, and And quinonediazide sulfonic acid amide.
[0007]
The other organic solvent used in the present invention is not particularly limited as long as it is miscible with N-methylpyrrolidone, and preferably includes, for example, a solvent contained in the raw material photoresist solution. Solvents contained in such a raw material photoresist solution include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, acetone, methyl isobutyl ketone, 2-heptanone, cyclohexanone, γ-butyrolactone, ethyl lactate, butyl acetate, Examples include amyl acetate, ethyl pyruvate, diethylene glycol dimethyl ether, methyl cellosolve acetate and ethyl cellosolve acetate.
The resin component in the raw material photoresist solution is preferably an alkali-soluble resin.
As the alkali-soluble resin, for example, a novolak resin used for a positive photoresist is preferable.
[0008]
In the present invention, the filter used for filtering the raw material photoresist solution at least once is washed with N-methylpyrrolidone which may contain another organic solvent in a direction opposite to the direction during filtration, The raw photoresist solution is filtered by the back-washed filter. The raw photoresist solution is once passed through a filter made of a fluororesin, and then a polyolefin filter. The method of passing through is preferable.
The fluororesin filter used in the present invention is preferably a polytetrafluoroethylene filter. The polyolefin filter is preferably a polyethylene filter.
In the present invention, a polyethylene filter is preferable as a filter to be reused after backwashing.
In the backwashing of the filter, it is preferable that the photosensitive agent component contained in the raw material photoresist solution has a dilute concentration in the range of 1 to 500 ppm in the N-methylpyrrolidone solution. For example, photosensitizer components used in positive photoresists such as o-benzoquinone diazide sulfonic acid ester, o-benzoquinone diazide sulfonic acid amide, o-naphthoquinone diazide sulfonic acid ester and o-naphthoquinone diazide sulfonic acid amide are relatively Although it tends to cause an increase in the number of fine particles in the photoresist solution, the photosensitizer component remaining on the filter is easily decomposed by N-methylpyrrolidone within the above concentration range, so that efficient back cleaning can be performed. .
[0009]
Examples of the filter made of polytetrafluoroethylene preferably used in the present invention include ABD1UFD3E [manufactured by Nippon Pole Co., Ltd.], ABD1UFT3EN [manufactured by Nippon Pole Co., Ltd.] and the like. A pore diameter of about 0.01 to 1 μm is usually used. Examples of the polyethylene filter preferably used in the present invention include SH4M228J3 [manufactured by Nippon Millipore Co., Ltd.], CS09XFE [manufactured by Mitsubishi Kasei Co., Ltd.], CS20XFE [manufactured by Mitsubishi Kasei Co., Ltd.], and the like. . The pore diameter is usually about 0.01 to 0.2 μm.
[0010]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples and the like.
[0011]
Reference example 1
The apparatus shown in FIG. 1 [thick lines and arrows in the piping indicate the flow direction of the liquid. ] Was used to back-wash polyethylene filter SH4M228J3 [pore size 0.2 μm, manufactured by Nippon Millipore Corporation].
The polyethylene filter is obtained by filtering the raw material photoresist solution once to produce a positive photoresist comprising PFI-32A6 [alkali-soluble novolak resin, quinonediazide sulfonate photosensitizer and 2-heptanone, manufactured by Sumitomo Chemical Co., Ltd. Used when the liquid product is obtained. Further, in the pot (1) shown in FIG. 1, the PFI-32A6 (raw material photoresist solution) prepared by mixing an alkali-soluble novolak resin, a quinonediazide sulfonate ester photosensitizer, 2-heptanone, and the like. Residual liquid has accumulated.
[0012]
Valves and piping from the pot (1) where the residual liquid of the raw material photoresist is accumulated to the filter housing (2), and valves and piping from the filter housing (2) to the filter housing (3) Back washing was performed in this order using heptanone, N-methylpyrrolidone and 2-heptanone.
The first washing with 2-heptanone (hereinafter referred to as rough washing) was performed three times, and 14.1 kg, 7.4 kg and 8.4 kg of 2-heptanone were used in this order. The second washing with N-methylpyrrolidone (hereinafter referred to as NMP washing) was performed twice, and 5.4 kg and 7 kg of NMP were used in this order, respectively. The third washing with 2-heptanone (hereinafter referred to as displacement washing) was performed 7 times, and 2-heptanone was used in order of 5 kg, 6.2 kg, 6 kg, 7.2 kg, 6 kg, 8 kg and 7 kg, respectively.
The concentration of the photosensitive agent in the solution obtained after the second rough cleaning was 0.4 ppm, and no photosensitive agent was detected in the solution obtained after the third rough cleaning. The NMP concentration in the liquid obtained after the first substitution cleaning was 2807 ppm, and the NMP concentration in the liquid obtained after the fourth substitution washing was 93 ppm, and the liquid obtained after the seventh substitution washing. The NMP concentration therein was 29 ppm. The filter housing (2) is provided mainly for cutting fine particles derived from the solvent.
[0013]
Reference example 2
FIG. 2 shows a polyethylene filter SH4M228J3 (a new product immediately after purchase was wetted with 2-heptanone) and a polyethylene filter SH4M228J3 (hereinafter referred to as a reusable product) obtained in Reference Example 1 after backwashing. Each of the filter housings (3) was mounted separately, and the following test was performed using the apparatus shown in FIG.
[0014]
<Confirmation test of filter micropore structure that affects particle removal performance>
Nitrogen gas is introduced from a valve (5) provided on the side of the filter housing (3), and the valve (6) is adjusted to pressurize the attached filter for a certain period of time, and then collect the amount of diffusion gas passing through Then, the presence or absence of breakage of the filter micropore structure was tested. Even at a nitrogen pressure of 150 kPa, it was confirmed that the amount of diffusion pass gas of the reused product was not more than the amount of diffusion pass gas of the new filter, and the fine pore structure of the filter was not damaged.
[0015]
Reference example 3
The polyethylene filter SH4M228J3 (reused product) obtained in Reference Example 1 is immersed in the above PFI-32A6 (photoresist solution product), and the PFI-32A6 product (without filter immersion) as a control is 0.2 μm or more in diameter. The change in the number of fine particles was tested over time, and the results in Table 1 were obtained.
[0016]
As shown in Table 1, no increase in the number of fine particles was observed at temperatures above room temperature. From this, it can be seen that the reused polyethylene filter obtained in Reference Example 1 is excellent in resistance to 2-heptanone, and even if this filter is used for filtration of a photoresist solution, it does not cause an increase in the number of fine particles. .
[0018]
Example 1
The apparatus shown in FIG. 3 [the polyethylene filter SH4M228J3 (reuse product) obtained in Reference Example 1 is mounted in the filter housing (3). The filter housing (2) is provided mainly for cutting fine particles derived from the solvent constituting the raw material resist. In addition, as a result of filtering the raw material photoresist solution used in Reference Example 1 by a one-pass method using nitrogen gas pressurization, fine particles having a diameter of 0.2 μm or more are used. A few photoresist products were obtained.
In this example, filtration is performed by a one-pass method using nitrogen gas pressurization. However, even if filtration is performed by a circulation method using a pump, a photoresist product with a small number of fine particles can be obtained as in the one-pass method.
[0019]
【The invention's effect】
According to the present invention, a photoresist product can be produced industrially advantageously.
[Brief description of the drawings]
FIG. 1 shows an apparatus used in Reference Example 1. FIG. 2 shows an apparatus used in Reference Example 2. FIG. 3 shows an apparatus used in Example 1.
1 .... Kan, 2 .... Filter housing, 3 .... Filter housing, 4 .... Backwash inlet, 5 .... Open / close valve, 6 .... Pressure adjustment valve
Claims (10)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001115091A JP3832267B2 (en) | 2001-04-13 | 2001-04-13 | Method for producing photoresist liquid product with reduced number of fine particles |
| US10/117,248 US7264912B2 (en) | 2001-04-13 | 2002-04-08 | Method of producing photoresist |
| KR1020020019381A KR20020092170A (en) | 2001-04-13 | 2002-04-10 | Process for preparation of photoresist |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001115091A JP3832267B2 (en) | 2001-04-13 | 2001-04-13 | Method for producing photoresist liquid product with reduced number of fine particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002311600A JP2002311600A (en) | 2002-10-23 |
| JP3832267B2 true JP3832267B2 (en) | 2006-10-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001115091A Expired - Fee Related JP3832267B2 (en) | 2001-04-13 | 2001-04-13 | Method for producing photoresist liquid product with reduced number of fine particles |
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| Country | Link |
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| JP (1) | JP3832267B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107413202A (en) * | 2017-05-11 | 2017-12-01 | 江苏博大环保股份有限公司 | A kind of efficient supermicro filtration membrane degreasing cleaning agent |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101109808B1 (en) | 2005-05-13 | 2012-02-15 | 제이에스알 가부시끼가이샤 | Process for producing radiation-sensitive resin composition |
| WO2011121960A1 (en) * | 2010-03-31 | 2011-10-06 | 住友ベークライト株式会社 | Method for producing positive photosensitive resin composition, positive photosensitive resin composition, and filter |
-
2001
- 2001-04-13 JP JP2001115091A patent/JP3832267B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107413202A (en) * | 2017-05-11 | 2017-12-01 | 江苏博大环保股份有限公司 | A kind of efficient supermicro filtration membrane degreasing cleaning agent |
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| JP2002311600A (en) | 2002-10-23 |
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