JP3052449B2 - Method for reducing metal in resist - Google Patents
Method for reducing metal in resistInfo
- Publication number
- JP3052449B2 JP3052449B2 JP3176550A JP17655091A JP3052449B2 JP 3052449 B2 JP3052449 B2 JP 3052449B2 JP 3176550 A JP3176550 A JP 3176550A JP 17655091 A JP17655091 A JP 17655091A JP 3052449 B2 JP3052449 B2 JP 3052449B2
- Authority
- JP
- Japan
- Prior art keywords
- resist
- water
- solution
- aqueous solution
- organic solvent
- 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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- Photosensitive Polymer And Photoresist Processing (AREA)
- Extraction Or Liquid Replacement (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、レジスト中に不純物と
して含まれる金属イオンの含有量を低減する方法に関す
るものである。The present invention relates to a method for reducing the content of metal ions contained as impurities in a resist.
【０００２】[0002]
【従来の技術】キノンジアジド基を有する化合物とノボ
ラック樹脂などのアルカリ可溶性樹脂を含む組成物は、
３００〜５００nmの波長の光照射により、キノンジアジ
ド基が分解してカルボキシル基を生じ、アルカリ不溶の
状態からアルカリ可溶の状態に変わることを利用して、
ポジ型レジストとして用いられている。このようなポジ
型レジストは、ネガ型レジストに比べ解像力が著しく優
れるという特徴を有し、集積回路（ＩＣ）や大規模集積
回路（ＬＳＩ）などの製作に利用されている。2. Description of the Related Art A composition containing a compound having a quinonediazide group and an alkali-soluble resin such as a novolak resin is
Utilizing that the quinonediazide group is decomposed to generate a carboxyl group by light irradiation at a wavelength of 300 to 500 nm, and changes from an alkali-insoluble state to an alkali-soluble state,
It is used as a positive resist. Such a positive resist has a feature that resolving power is remarkably superior to that of a negative resist, and is used for manufacturing an integrated circuit (IC), a large-scale integrated circuit (LSI), and the like.
【０００３】[0003]
【発明が解決しようとする課題】より微細化されたＩＣ
やＬＳＩの加工に用いるポジ型レジストには、感度、残
膜率、解像度、パターン形成、プロセス上の各種マージ
ンなどといった基本性能のほか、特に金属含有量が歩留
まり向上のために重要な性能項目となっている。すなわ
ち、金属含有量の多いレジストを用いた場合には、描か
れたパターン中に金属が残存し、半導体の電気特性を低
下させることから、レジスト中の金属含有量の低減が業
界の大きな課題となっている。SUMMARY OF THE INVENTION Finer ICs
In addition to basic performance such as sensitivity, residual film rate, resolution, pattern formation, and various process margins, positive resists used in the processing of LSIs and LSIs are particularly important in terms of metal content, which is important for improving the yield. Has become. That is, when a resist having a high metal content is used, the metal remains in the drawn pattern and the electrical characteristics of the semiconductor deteriorate, so that reducing the metal content in the resist is a major issue in the industry. Has become.
【０００４】ところが、現在市販されているレジストの
金属含有量は、決して半導体メーカーを満足させるレベ
ルでなく、レジスト中に含まれる金属が半導体製造上の
大きな問題点となっている。本発明の目的は、レジスト
に含まれる金属を低減化する方法を提供することにあ
る。However, the metal content of currently marketed resists is not at a level that satisfies semiconductor manufacturers at all, and the metals contained in the resists are a major problem in semiconductor manufacturing. An object of the present invention is to provide a method for reducing a metal contained in a resist.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、上記のよ
うな従来技術の欠点を克服し、レジスト中に含まれる金
属を効果的に低減する方法を見出すべく鋭意研究を行っ
た結果、本発明を完成するに至った。Means for Solving the Problems The present inventors have made intensive studies to overcome the above-mentioned drawbacks of the prior art and to find a method for effectively reducing the metal contained in the resist. The present invention has been completed.
【０００６】すなわち本発明は、レジストを、２０℃に
おける水に対する溶解度が１００ｇ／１００cc以下であ
る有機溶媒に溶解し、その溶液を水または酸性水溶液と
接触させて液々抽出することにより、レジスト中の金属
を低減化する方法を提供するものである。That is, the present invention is to dissolve a resist in an organic solvent having a solubility in water of not more than 100 g / 100 cc at 20 ° C., and contact the solution with water or an acidic aqueous solution to extract the resist. And a method for reducing the amount of metal.
【０００７】以下、本発明を詳細に説明する。本発明で
処理対象となるレジストは、キノンジアジド基を有する
化合物のような感光性物質および、ノボラック樹脂のよ
うなアルカリ可溶性樹脂を、両者に溶解性を有する溶媒
に溶解させたものであり、もちろんレジスト用の各種添
加剤を含有していてもよい。通常、市販されているレジ
ストをそのまま処理対象とすることができるが、感光性
物質、アルカリ可溶性樹脂および溶媒を配合して製造し
たレジストを処理することも、もちろん可能である。Hereinafter, the present invention will be described in detail. The resist to be treated in the present invention is a photosensitive substance such as a compound having a quinonediazide group, and an alkali-soluble resin such as a novolak resin, which is dissolved in a solvent having a solubility in both. May contain various additives. Usually, a commercially available resist can be used as it is, but it is of course possible to treat a resist prepared by mixing a photosensitive substance, an alkali-soluble resin and a solvent.
【０００８】本発明では、このようなレジストを有機溶
媒に溶解する。ここで用いる有機溶媒は、２０℃におけ
る水に対する溶解度が１００ｇ／１００cc以下のもの、
すなわち、２０℃の水１００ccに溶ける最大量が１００
ｇ以下のものである。もちろん、実質的に水に溶解しな
いものであってもよい。好ましくは、２０℃における水
に対する溶解度が３０ｇ／１００cc以下であるもの、さ
らに好ましくは、２０ｇ／１００cc以下であるものが用
いられる。In the present invention, such a resist is dissolved in an organic solvent. The organic solvent used here has a solubility in water at 20 ° C. of 100 g / 100 cc or less.
That is, the maximum amount that can be dissolved in 100 cc of water at 20 ° C. is 100
g or less. Of course, it may not substantially dissolve in water. Preferably, those having a solubility in water at 20 ° C. of 30 g / 100 cc or less, more preferably 20 g / 100 cc or less, are used.
【０００９】２０℃における水に対する溶解度が１００
ｇ／１００cc以下である有機溶媒の具体例としては、酢
酸エチル、酢酸ｎ−ブチル、酢酸イソアミルのごとき酢
酸エステル類、メチルエチルケトン、メチルイソブチル
ケトン、シクロヘキサノン、２−ヘプタノン、２−ペン
タノンのごときケトン類、エチレングリコールモノエチ
ルエーテルアセテート、エチレングリコールモノブチル
エーテルアセテート、プロピレングリコールモノメチル
エーテルアセテートのごときグリコールエーテルアセテ
ート類、トルエン、キシレンのごとき芳香族炭化水素類
などが挙げられる。これらのなかでも、トルエン、２−
ヘプタノン、２−ペンタノン、メチルイソブチルケト
ン、酢酸エチルなどが好ましい。The solubility in water at 20 ° C. is 100
Specific examples of the organic solvent having a g / 100 cc or less include acetic esters such as ethyl acetate, n-butyl acetate and isoamyl acetate; ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone and 2-pentanone; Glycol ether acetates such as ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, and propylene glycol monomethyl ether acetate; and aromatic hydrocarbons such as toluene and xylene. Among these, toluene, 2-
Heptanone, 2-pentanone, methyl isobutyl ketone, ethyl acetate and the like are preferred.
【００１０】これらの溶媒は、それぞれ単独で用いるこ
ともできるし、また２種以上を混合して用いることもで
きる。混合溶媒とする場合の具体例としては、エチレン
グリコールモノエチルエーテルアセテートとトルエン、
エチレングリコールモノエチルエーテルアセテートと酢
酸エチルなどが挙げられる。These solvents can be used alone or in combination of two or more. Specific examples when the mixed solvent is used, ethylene glycol monoethyl ether acetate and toluene,
Examples include ethylene glycol monoethyl ether acetate and ethyl acetate.
【００１１】レジストを有機溶媒に溶解する際の有機溶
媒の使用量は特に限定されるものでないが、有機溶媒を
あまり多く用いると、全体の液量が多くなって操作上の
問題を生ずることがあり、また有機溶媒の量があまり少
ないと、水または酸性水溶液で処理したあとの水層との
分離が悪くなるなどの問題を生ずることがある。好適な
有機溶媒の使用量は、処理対象のレジスト（感光性物
質、アルカリ可溶性樹脂および溶媒を含む）の総重量に
対して、２０〜３００重量％程度であり、より好ましく
は５０〜２００重量％程度、さらに好ましくは５０〜１
００重量％程度である。The amount of the organic solvent used for dissolving the resist in the organic solvent is not particularly limited. However, if too much organic solvent is used, the total amount of the solution may increase, which may cause operational problems. In addition, if the amount of the organic solvent is too small, problems such as poor separation from an aqueous layer after treatment with water or an acidic aqueous solution may occur. A suitable amount of the organic solvent is about 20 to 300% by weight, more preferably 50 to 200% by weight, based on the total weight of the resist to be treated (including the photosensitive substance, the alkali-soluble resin and the solvent). Degree, more preferably 50-1
It is about 00% by weight.
【００１２】こうして有機溶媒に溶解したレジスト溶液
は、次に水または酸性水溶液と接触処理され、液々抽出
される。この際、レジスト溶液に水または酸性水溶液を
添加してもよいし、あるいは水または酸性水溶液にレジ
スト溶液を添加してもよい。用いる水または酸性水溶液
は、本発明の目的に沿って金属含有量の少ないもの、例
えばイオン交換水などが望ましい。例えば、イオン交換
水をそのまま用いるとか、あるいは金属含有量の少ない
水に酸を加えて弱酸性としたものを用いるといった方法
が好ましい。The resist solution thus dissolved in the organic solvent is then subjected to a contact treatment with water or an acidic aqueous solution to extract the liquid. At this time, water or an acidic aqueous solution may be added to the resist solution, or a resist solution may be added to the water or acidic aqueous solution. For the purpose of the present invention, the water or acidic aqueous solution used is preferably one having a low metal content, for example, ion-exchanged water. For example, it is preferable to use ion-exchanged water as it is, or to use a weakly acidic solution obtained by adding an acid to water having a low metal content.
【００１３】水または酸性水溶液の使用量に特別な制限
はないが、その量があまりに少ないと、金属除去のため
の抽出回数を多くする必要があり、また水または酸性水
溶液の量があまりに多いと、全体の液量が多くなって操
作上の問題を生ずることがある。水または酸性水溶液の
好適な使用量は、有機溶媒に溶解したレジスト溶液の総
重量に対して、１０〜２００重量％程度であり、より好
ましくは２０〜１００重量％程度である。There is no particular limitation on the amount of water or acidic aqueous solution. However, if the amount is too small, it is necessary to increase the number of extractions for removing metals, and if the amount of water or acidic aqueous solution is too large, In some cases, the total amount of liquid may increase, causing operational problems. A suitable use amount of water or an acidic aqueous solution is about 10 to 200% by weight, more preferably about 20 to 100% by weight, based on the total weight of the resist solution dissolved in the organic solvent.
【００１４】抽出に用いる液体は水だけであってもよい
が、酸性水溶液、特に蓚酸の水溶液が適当である。この
水溶液のｐＨは、約５以下であるのが好ましい。また、
水溶液の酸性度があまり大きくなるとレジスト性能に影
響が出てくることから、通常はｐＨ０以上程度の酸性水
溶液が好ましい。より好適なｐＨ範囲は０〜４程度であ
り、さらに好ましくはｐＨ１〜３程度である。The liquid used for the extraction may be water alone, but an acidic aqueous solution, particularly an aqueous solution of oxalic acid, is suitable. The pH of the aqueous solution is preferably about 5 or less. Also,
If the acidity of the aqueous solution becomes too large, the resist performance will be affected. Therefore, an acidic aqueous solution having a pH of about 0 or more is usually preferable. A more preferable pH range is about 0 to 4, and further more preferably about pH 1 to 3.
【００１５】抽出処理は通常、前記レジスト溶液と抽出
剤である水または酸性水溶液とを、２０°〜５０℃程
度、好ましくは３０°〜４５℃程度の温度で、撹拌等に
よりよく混合させたあと、静置することによって行われ
る。これにより、レジスト溶液に含まれていた金属イオ
ンが水層に移行する。そして得られる混合物は、レジス
ト溶液層と水層の二層に分かれるので、デカンテーショ
ンなどにより両層を分離する。In the extraction treatment, usually, the resist solution is mixed well with water or an acidic aqueous solution as an extractant at a temperature of about 20 ° to 50 ° C., preferably about 30 ° to 45 ° C. by stirring or the like. This is done by standing still. As a result, metal ions contained in the resist solution move to the aqueous layer. The resulting mixture is separated into two layers, a resist solution layer and an aqueous layer, and the two layers are separated by decantation or the like.
【００１６】このような処理により、レジスト溶液中の
金属含有量を低減することができるが、得られるレジス
ト溶液層についてさらに、水または酸性水溶液の投入、
撹拌による混合、静置、分液という操作を数回繰り返し
て、金属含有量を一層低減するのが望ましい。酸性水溶
液を用いた場合には、一回の処理でも相当量の金属を除
去することができるが、特に、蓚酸水溶液を用いて抽出
処理した後、さらに水を用いて数回抽出処理を行い、酸
を除去しておくのが望ましい。したがって好ましい態様
として、液々抽出を複数回行い、そのうちの少なくとも
最初の一回は蓚酸水溶液を用いて行い、少なくとも最後
の一回は水を用いて行う方法が挙げられる。もちろんこ
の場合も、抽出に用いる水は、金属含有量の少ないもの
であるのが好ましい。By such treatment, the metal content in the resist solution can be reduced. However, the resulting resist solution layer is further charged with water or an acidic aqueous solution.
It is desirable to repeat the operations of mixing, standing, and liquid separation by stirring several times to further reduce the metal content. In the case of using an acidic aqueous solution, a considerable amount of metal can be removed in a single treatment.However, in particular, after an extraction treatment using an oxalic acid aqueous solution, an extraction treatment is further performed several times using water, It is desirable to remove the acid. Therefore, as a preferred embodiment, there is a method in which the liquid-liquid extraction is performed a plurality of times, at least the first of which is performed using an aqueous oxalic acid solution, and the at least one of which is performed using water. Of course, also in this case, it is preferable that the water used for the extraction has a low metal content.
【００１７】こうして得られるレジスト溶液は、そのあ
と必要によりレジスト溶媒を加え、減圧蒸留などの操作
を施して、残っている水ならびに最初に加えた２０℃に
おける水に対する溶解度が１００ｇ／１００cc以下であ
る有機溶媒を除去することにより、金属含有量の低減さ
れたレジストとすることができる。この際必要により加
えられるレジスト溶媒としては、例えば、エチレングリ
コールモノエチルエーテルアセテート、プロピレングリ
コールモノメチルエーテルアセテートのようなグリコー
ルエーテルエステル類、その他、特開平 2-220056 号公
報に記載される溶媒、蒸発速度の異なる２種またはそれ
以上の混合溶媒（特願平 3-138899 号に記載されてい
る）などが挙げられる。The resist solution thus obtained is added with a resist solvent, if necessary, and subjected to an operation such as distillation under reduced pressure, so that the solubility in the remaining water and the initially added water at 20 ° C. is 100 g / 100 cc or less. By removing the organic solvent, a resist with reduced metal content can be obtained. In this case, the resist solvent optionally added includes, for example, glycol ether esters such as ethylene glycol monoethyl ether acetate and propylene glycol monomethyl ether acetate, and other solvents described in JP-A-2-220056; And mixed solvents of two or more (described in Japanese Patent Application No. 3-138899).
【００１８】本発明によって処理したレジストは、処理
前のものに比べ、金属含有量が大幅に低減されたものと
なる。The resist treated according to the present invention has a significantly reduced metal content as compared with the resist before the treatment.
【００１９】[0019]
【実施例】以下、実施例を示して本発明をさらに具体的
に説明するが、本発明はこれらの実施例によってなんら
制限されるものでない。EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
【００２０】実施例１（参考） ３リットル容量の四つ口フラスコ（底抜き型）に、キノ
ンジアジド化合物およびノボラック樹脂をエチレングリ
コールモノエチルエーテルアセテートに溶解させた市販
のレジストであるＰＦＸ−１５（住友化学工業社製、商
品名）を 1,000ｇ仕込み、２３〜２７℃に温度調整した
あと、 エチレングリコールモノエチルエーテルアセテ
ート（２０℃における水に対する溶解度が約２３ｇ／１
００cc）２００ｇおよびトルエン（２０℃における水に
対する溶解度が１ｇ／１００cc未満）５５５ｇを加え、
同温度で３０分間撹拌した。次いでイオン交換水７０７
ｇを仕込み、４０℃まで昇温し、３８〜４２℃の温度範
囲で３０分間撹拌したあと静置した。これにより、レジ
スト溶液層と水層とに分かれたので、下層の水層を分離
した。 得られたレジスト溶液層に、再度イオン交換水
４００ｇを仕込み、３８〜４２℃の温度範囲で３０分間
撹拌後、静置し、水層を分離した。イオン交換水４００
ｇの仕込みから水層分離までの操作を、このあとさらに
４回繰り返した。Example 1 (Reference) A commercially available resist, PFX-15 (Sumitomo), in which a quinonediazide compound and a novolak resin were dissolved in ethylene glycol monoethyl ether acetate, was placed in a three-liter four-neck flask (bottom open type). After charging 1,000 g of Chemical Industry Co., Ltd., and adjusting the temperature to 23 to 27 ° C., ethylene glycol monoethyl ether acetate (the solubility in water at 20 ° C. was about 23 g / 1)
200 cc) and 555 g of toluene (solubility in water at 20 ° C. of less than 1 g / 100 cc) were added,
The mixture was stirred at the same temperature for 30 minutes. Next, ion-exchanged water 707
g, the mixture was heated to 40 ° C, stirred for 30 minutes in a temperature range of 38 to 42 ° C, and allowed to stand. As a result, a resist solution layer and an aqueous layer were separated, and the lower aqueous layer was separated. 400 g of ion-exchanged water was again charged into the obtained resist solution layer, stirred for 30 minutes in a temperature range of 38 to 42 ° C., and allowed to stand to separate an aqueous layer. Ion exchange water 400
The operation from charging g to separation of the aqueous layer was repeated four more times.
【００２１】次にレジスト溶液層を、減圧度５０Torr、
外部バス温度５０℃の条件にて蒸留し、水、トルエンお
よびエチレングリコールモノエチルエーテルアセテート
を合計 737.6ｇ流出させたあと、２５℃まで冷却し、レ
ジスト溶液層の全体が 1,000ｇとなるように、エチレン
グリコールモノエチルエーテルアセテートを９４ｇ加え
た。Next, the resist solution layer is depressurized at a pressure of 50 Torr.
Distillation was carried out under the condition of an external bath temperature of 50 ° C., and after a total of 737.6 g of water, toluene and ethylene glycol monoethyl ether acetate were discharged, the solution was cooled to 25 ° C. so that the entire resist solution layer became 1,000 g. 94 g of ethylene glycol monoethyl ether acetate was added.
【００２２】実施例２ 実施例１におけるイオン交換水７０７ｇを仕込む代わり
に、蓚酸５ｇとイオン交換水７０９ｇを混合した酸性水
溶液（ｐＨ 1.8）を仕込んだ以外は実施例１と同様に処
理して、レジストを得た。Example 2 The procedure of Example 1 was repeated, except that an acidic aqueous solution (pH 1.8) obtained by mixing 5 g of oxalic acid and 709 g of ion-exchanged water was used instead of 707 g of ion-exchanged water in Example 1. A resist was obtained.
【００２３】処理前のレジスト（ＰＦＸ−１５）ならび
に、実施例１および２で得られたそれぞれのレジストに
ついて、灰化炎光光度法によりナトリウム含有量を測定
し、また灰化フレームレス原子吸光光度法によりその他
の金属の含有量を測定した。測定結果は、 ppb単位で表
１に示した。The sodium content of the untreated resist (PFX-15) and each of the resists obtained in Examples 1 and 2 were measured by incineration flame photometry. The content of other metals was measured by the method. The measurement results are shown in Table 1 in ppb units.
【００２４】[0024]
【表１】 [Table 1]
【００２５】[0025]
【発明の効果】本発明に従って、レジストを特定の有機
溶媒に溶解し、それを水または酸性水溶液で処理するこ
とにより、レジスト中に不純物として含まれる金属を効
果的に低減することができる。こうして金属含有量を少
なくしたレジストを用いることにより、高性能の半導体
集積回路を製作することができる。According to the present invention, by dissolving a resist in a specific organic solvent and treating it with water or an acidic aqueous solution, metals contained as impurities in the resist can be effectively reduced. By using a resist having a reduced metal content in this manner, a high-performance semiconductor integrated circuit can be manufactured.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−236030（ＪＰ，Ａ) 特開 平１−228560（ＪＰ，Ａ) 特開 昭63−126502（ＪＰ，Ａ) 特開 昭63−6026（ＪＰ，Ａ) 特開 平２−273641（ＪＰ，Ａ) 特開 昭62−45301（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) G03F 7/26 B01D 11/04 G03F 7/022 ──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-63-236030 (JP, A) JP-A-1-228560 (JP, A) JP-A-63-126502 (JP, A) JP-A 63-236502 6026 (JP, A) JP-A-2-273641 (JP, A) JP-A-62-45301 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) G03F 7/26 B01D 11 / 04 G03F 7/022
Claims (2)
解度が１００ｇ／１００cc以下である有機溶媒に溶解
し、その溶液を蓚酸の水溶液と接触させて液々抽出する
ことを特徴とするレジストの金属低減化方法。1. A method for reducing a metal in a resist, comprising: dissolving a resist in an organic solvent having a solubility in water at 20 ° C. of 100 g / 100 cc or less, and contacting the solution with an aqueous solution of oxalic acid to extract the liquid. Method.
得られるレジスト溶液を水と接触させて液々抽出を行う
請求項１記載の方法。2. After liquid-liquid extraction using an aqueous solution of oxalic acid,
The method according to claim 1, wherein the obtained resist solution is brought into contact with water to perform liquid-liquid extraction .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3176550A JP3052449B2 (en) | 1991-07-17 | 1991-07-17 | Method for reducing metal in resist |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3176550A JP3052449B2 (en) | 1991-07-17 | 1991-07-17 | Method for reducing metal in resist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0519463A JPH0519463A (en) | 1993-01-29 |
| JP3052449B2 true JP3052449B2 (en) | 2000-06-12 |
Family
ID=16015546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3176550A Expired - Fee Related JP3052449B2 (en) | 1991-07-17 | 1991-07-17 | Method for reducing metal in resist |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3052449B2 (en) |
Cited By (1)
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| EP3075728A1 (en) * | 2013-11-29 | 2016-10-05 | Mitsubishi Gas Chemical Company, Inc. | Purification method for compound or resin |
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| CN107428646B (en) * | 2015-03-30 | 2021-03-02 | 三菱瓦斯化学株式会社 | Compounds, resins, and methods for their purification, and uses thereof |
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| TW201714865A (en) * | 2015-09-04 | 2017-05-01 | 三菱瓦斯化學股份有限公司 | Method for purifying compound |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0659364B2 (en) * | 1985-08-23 | 1994-08-10 | 株式会社日立製作所 | Ion treatment equipment for radioactive organic solvents |
| JPH0680119B2 (en) * | 1986-06-27 | 1994-10-12 | 日本ゼオン株式会社 | Purification method of novolak resin |
| JPH0737486B2 (en) * | 1986-11-18 | 1995-04-26 | 日本ゼオン株式会社 | Method for purifying polymer for semiconductor substrate coating material |
| JP2560266B2 (en) * | 1987-03-25 | 1996-12-04 | 日本合成ゴム株式会社 | Radiation-sensitive resin composition |
| JPH01228560A (en) * | 1988-03-08 | 1989-09-12 | Hitachi Chem Co Ltd | Manufacture of solution containing decreased impure metallic components |
| JP2676902B2 (en) * | 1989-04-13 | 1997-11-17 | 住友化学工業株式会社 | Triphenylmethane derivative and process for producing the same |
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1991
- 1991-07-17 JP JP3176550A patent/JP3052449B2/en not_active Expired - Fee Related
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|---|---|---|---|---|
| EP3075728A1 (en) * | 2013-11-29 | 2016-10-05 | Mitsubishi Gas Chemical Company, Inc. | Purification method for compound or resin |
| EP3075728A4 (en) * | 2013-11-29 | 2017-05-03 | Mitsubishi Gas Chemical Company, Inc. | Purification method for compound or resin |
| US9920024B2 (en) | 2013-11-29 | 2018-03-20 | Mitsubishi Gas Chemical Company, Inc. | Method for purifying compound or resin |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0519463A (en) | 1993-01-29 |
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