JP2012208325A - Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same - Google Patents
Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same Download PDFInfo
- Publication number
- JP2012208325A JP2012208325A JP2011074064A JP2011074064A JP2012208325A JP 2012208325 A JP2012208325 A JP 2012208325A JP 2011074064 A JP2011074064 A JP 2011074064A JP 2011074064 A JP2011074064 A JP 2011074064A JP 2012208325 A JP2012208325 A JP 2012208325A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- quaternary ammonium
- same
- eda
- developer
- 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.)
- Pending
Links
Landscapes
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
本発明は、第四級アンモニウム化合物、その製造法及びそれを含むフォトレジストの現像液に関するものである。 The present invention relates to a quaternary ammonium compound, a process for producing the same, and a photoresist developer containing the quaternary ammonium compound.
半導体デバイスやフラットパネルディスプレイの製造工程では、微細加工するために、フォトレジストを使用する。フォトレジストは、マスクをとおして所定のパターンに露光した後、アルカリ系現像液で不要な部分を溶解除去される。この現像液として、金属イオンを忌避する半導体デバイス、フラットパネルディスプレイの製造工程では、金属イオンを含まない有機系塩基として、広く水酸化テトラメチルアンモニウム（以下ＴＭＡＨ）水溶液が使用されている（例えば特許文献１，２参照）。ＴＭＡＨは塩基性が強く、安定であり、工業的に入手が容易である優れた化合物ではあるが、近年、その毒性ため、代替物質が求められている。 In the manufacturing process of semiconductor devices and flat panel displays, a photoresist is used for fine processing. The photoresist is exposed to a predetermined pattern through a mask, and then unnecessary portions are dissolved and removed with an alkaline developer. As this developer, in the manufacturing process of semiconductor devices and flat panel displays that avoid metal ions, tetramethylammonium hydroxide (hereinafter referred to as TMAH) aqueous solution is widely used as an organic base that does not contain metal ions (for example, patents). References 1 and 2). TMAH is an excellent compound that has strong basicity, is stable, and is easily available industrially, but in recent years, an alternative substance has been demanded because of its toxicity.
一方、有機系塩基としては、種々の化合物が提案されている。例えば、トリメチルアダマンチルアンモニウム、テトラエチルアンモニウム、（２−ジメチルアミノエチル）エチルジメチルアンモニウムなどが挙げられる（例えば特許文献３参照）。しかし、これらの第四級アンモニウム塩は塩基性が弱いため、フォトレジストの現像液と使用するには適さず、主にゼオライト製造、ポリウレタン製造などに使用されている。 On the other hand, various compounds have been proposed as organic bases. For example, trimethyladamantyl ammonium, tetraethylammonium, (2-dimethylaminoethyl) ethyldimethylammonium, etc. are mentioned (for example, refer patent document 3). However, since these quaternary ammonium salts are weakly basic, they are not suitable for use as a photoresist developer, and are mainly used for zeolite production, polyurethane production, and the like.
以上のように従来知られている化合物は、いずれも十分なものとは言えず、工業的な実用化を図るために更なる検討が要望されていた。すなわち、塩基性の高い第四級アンモニウム化合物の開発が望まれていた。 As described above, none of the conventionally known compounds can be said to be sufficient, and further studies have been demanded for industrial practical use. That is, development of a highly basic quaternary ammonium compound has been desired.
本発明は、上記した背景技術に鑑みてなされたものであり、その目的は、強塩基性の第四級アンモニウム化合物、その製造方法及びそれを使用した現像液組成物を提供することにある。 The present invention has been made in view of the background art described above, and an object thereof is to provide a strongly basic quaternary ammonium compound, a method for producing the same, and a developer composition using the same.
本発明者らは、第四級アンモニウム化合物について鋭意検討した結果、（ＣＨ３）３ＮＣＨ２ＣＨ２Ｎ（ＣＨ３）３・（ＯＨ）２で表される化合物が、強塩基性を示し、上記した課題を解決できることを見出し、本発明を完成させるに至った。 As a result of intensive studies on quaternary ammonium compounds, the present inventors have shown that a compound represented by (CH 3 ) 3 NCH 2 CH 2 N (CH 3 ) 3. (OH) 2 exhibits strong basicity. The present inventors have found that the above problems can be solved, and have completed the present invention.
すなわち、本発明は、以下に示すとおりの化合物、その製造法、及びそれを含む現像液組成物に関するものである。
［１］（ＣＨ３）３ＮＣＨ２ＣＨ２Ｎ（ＣＨ３）３・（ＯＨ）２で示される第４級アンモニウム化合物。
［２］ハロゲン化メチル、硫酸ジメチル又は炭酸ジメチル並びにＮ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミンとを反応させ、強塩基で処理することを特徴とする（ＣＨ３）３ＮＣＨ２ＣＨ２Ｎ（ＣＨ３）３・（ＯＨ）２の製造法。
［３］ハロゲン化メチルが臭化メチル又は沃化メチルである上記［２］の製造法。
［４］強塩基がアルカリ金属水酸化物、イオン交換樹脂から選ばれる少なくとも一種である上記［２］又は［３］のいずれかに記載の製造法。
［５］上記［１］の化合物及び水を含んでなるフォトレジスト現像液用組成物。
［６］上記［１］の化合物の濃度が、０．５重量％〜５重量％である上記［５］に記載の組成物。
That is, this invention relates to the compound as shown below, its manufacturing method, and the developing solution composition containing it.
[1] (CH 3) 3 NCH 2 CH 2 N (CH 3) 3 · (OH) quaternary ammonium compounds represented by 2.
[2] Methyl halide, dimethyl sulfate or dimethyl carbonate and N, N, N ′, N′-tetramethylethylenediamine are reacted and treated with a strong base (CH 3 ) 3 NCH 2 CH 2 A method for producing N (CH 3 ) 3. (OH) 2 .
[3] The production method of the above [2], wherein the methyl halide is methyl bromide or methyl iodide.
[4] The production method according to any one of the above [2] or [3], wherein the strong base is at least one selected from alkali metal hydroxides and ion exchange resins.
[5] A composition for a photoresist developer, comprising the compound of [1] above and water.
[6] The composition according to [5] above, wherein the concentration of the compound of [1] is 0.5% by weight to 5% by weight.
本発明は以下に示す効果を奏する。
本発明の化合物は、工業的に入手可能な原料から容易に製造することが可能で、強塩基性を発現することができる。しかも、フォトレジストを安全に効率的に現像することができる。
The present invention has the following effects.
The compound of the present invention can be easily produced from industrially available raw materials and can exhibit strong basicity. Moreover, the photoresist can be developed safely and efficiently.
以下に、本発明をさらに詳細に説明する。 The present invention is described in further detail below.
本発明の化合物は、エチレンジアミンをメチル化し、第四級アンモニム水酸化物にした化合物、すなわち（ＣＨ３）３ＮＣＨ２ＣＨ２Ｎ（ＣＨ３）３・（ＯＨ）２で示される第四級アンモニウム化合物である（以下ＥＤＡ四級塩と称する）。 The compound of the present invention is a compound in which ethylenediamine is methylated to form a quaternary ammonium hydroxide, ie, a quaternary ammonium represented by (CH 3 ) 3 NCH 2 CH 2 N (CH 3 ) 3. (OH) 2 Compound (hereinafter referred to as EDA quaternary salt).
具体的には下記構造式である。 Specifically, it is the following structural formula.
本発明の化合物は、水に溶解すると強塩基性を示す常温で固体の化合物である。ＥＤＡ四級塩の製造方法としては、例えばハロゲン化メチル、硫酸ジメチル又は炭酸ジメチル並びにＮ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミンとを反応させ、強塩基で処理することにより製造できる。用いるハロゲン化メチルとしては、例えば臭化メチル、沃化メチル等が挙げられ、これらのいずれも使用することができる。 The compound of the present invention is a solid compound at room temperature that exhibits strong basicity when dissolved in water. As a method for producing an EDA quaternary salt, for example, it can be produced by reacting methyl halide, dimethyl sulfate or dimethyl carbonate and N, N, N ′, N′-tetramethylethylenediamine and treating with a strong base. Examples of the methyl halide to be used include methyl bromide and methyl iodide, and any of these can be used.
ハロゲン化メチル、硫酸ジメチル又は炭酸ジメチルを使用してメチル化すると、生成した第四級アンモニウム塩のアニオンが、臭化物イオン、沃化物イオン、メチル硫酸イオン、硫酸イオン、メチル炭酸イオン、炭酸イオンになっているため、目的とする水酸化物イオンにするには、強塩基でイオン交換しなければならない。強塩基としては、例えば水酸化ナトリウム、水酸化カリウム、水酸化バリウム等が挙げられる。 When methylated using methyl halide, dimethyl sulfate or dimethyl carbonate, the anion of the quaternary ammonium salt formed becomes bromide ion, iodide ion, methyl sulfate ion, sulfate ion, methyl carbonate ion, carbonate ion. Therefore, in order to obtain the target hydroxide ion, it must be ion-exchanged with a strong base. Examples of the strong base include sodium hydroxide, potassium hydroxide, barium hydroxide and the like.
イオン交換の方法も一般に知られている方法を使用することができ、例えば電気分解法、金属水酸化物で処理する方法、イオン交換樹脂で処理する方法を用いることができる。いずれの方法でもＥＤＡ四級塩を得ることができ、その中でも特殊な設備を必要としない、金属水酸化物で処理する方法、イオン交換樹脂で処理する方法が好ましい。 As the ion exchange method, a generally known method can be used. For example, an electrolysis method, a method of treating with a metal hydroxide, or a method of treating with an ion exchange resin can be used. In any method, an EDA quaternary salt can be obtained. Among them, a method of treating with a metal hydroxide and a method of treating with an ion exchange resin, which do not require special equipment, are preferable.
イオン交換樹脂としては塩基性イオン交換樹脂を使用することができ、特に強塩基性イオン交換樹脂が好ましい。強塩基性イオン交換樹脂としては工業的に流通しているものを使用することができ、イオン形としてはＯＨ形のものが使用できる。 As the ion exchange resin, a basic ion exchange resin can be used, and a strong basic ion exchange resin is particularly preferable. As the strongly basic ion exchange resin, those commercially available can be used, and those in the OH form can be used as the ion form.
ＥＤＡ四級塩は、水を含んでなる組成物とすると、広く使用されているＴＭＡＨと同様、フォトレジストの現像液として使用することができる。現像液として使用するのに必要なＥＤＡ四級塩の濃度は、現像時間及びフォトレジストの膨潤の観点から０．５〜５重量％であることが好ましい。 The EDA quaternary salt can be used as a developer for a photoresist as in the case of a widely used TMAH, when it is a composition comprising water. The concentration of the EDA quaternary salt required for use as a developer is preferably 0.5 to 5% by weight from the viewpoint of development time and photoresist swelling.
本発明のフォトレジスト現像液組成物には、界面活性剤、有機溶媒、キレート剤などを適宜添加してもよい。また、他の第四級アンモニウム塩、例えばＴＭＡＨ，コリン、テトラエチルアンモニウム水酸化物などを添加することもできる。 A surfactant, an organic solvent, a chelating agent, and the like may be appropriately added to the photoresist developer composition of the present invention. Further, other quaternary ammonium salts such as TMAH, choline, tetraethylammonium hydroxide and the like can be added.
以下、実施例により本発明を具体的に説明するが、本発明はこれらの実施例により何ら限定して解釈されるものではない。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not construed as being limited to these examples.
実施例１ ＥＤＡ四級塩の合成
Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン１ｇ、沃化メチル２．５ｇをテトラヒドロフラン５ｇに加え、室温で１時間撹拌した後、５０度で１時間撹拌した。析出したＥＤＡ四級塩の沃化物にエタノール５０ｇを加え、さらに水酸化ナトリウムを０．６８ｇ添加した。析出した沃化ナトリウムを除き、水を加えた後エタノールを減圧で留去し、ＥＤＡ四級塩１．４ｇを含有する水溶液を得た。
Example 1 Synthesis of EDA quaternary salt 1 g of N, N, N ′, N′-tetramethylethylenediamine and 2.5 g of methyl iodide were added to 5 g of tetrahydrofuran, stirred at room temperature for 1 hour, and then stirred at 50 ° C. for 1 hour. did. To the precipitated EDA quaternary salt iodide, 50 g of ethanol was added, and 0.68 g of sodium hydroxide was further added. The precipitated sodium iodide was removed, water was added, and then ethanol was distilled off under reduced pressure to obtain an aqueous solution containing 1.4 g of EDA quaternary salt.
ＥＤＡ四級塩の１Ｈ−ＮＭＲ（Ｄ２Ｏ） δ ２．６ｐｐｍ（ｓ，４Ｈ，ＣＨ２），３．２ｐｐｍ（ｓ，１８Ｈ，ＣＨ３）。 1 H-NMR (D 2 O) δ of EDA quaternary salt 2.6 ppm (s, 4 H, CH 2 ), 3.2 ppm (s, 18 H, CH 3 ).
実施例２ ＥＤＡ四級塩の合成
Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン１ｇ、臭化メチル１．７ｇをテトラヒドロフラン５ｇに加え、室温で１時間撹拌した後、１時間加熱還流した。析出したＥＤＡ四級塩の臭化物にエタノール５０ｇを加え、さらに水酸化カリウムを０．９６ｇ添加した。析出した臭化カリウムを除き、水を加えた後エタノールを減圧で留去し、ＥＤＡ四級塩１．１ｇを含有する水溶液を得た。
Example 2 Synthesis of EDA Quaternary Salt 1 g of N, N, N ′, N′-tetramethylethylenediamine and 1.7 g of methyl bromide were added to 5 g of tetrahydrofuran, and the mixture was stirred at room temperature for 1 hour and then heated to reflux for 1 hour. 50 g of ethanol was added to the precipitated bromide of EDA quaternary salt, and 0.96 g of potassium hydroxide was further added. After removing the precipitated potassium bromide, water was added and ethanol was distilled off under reduced pressure to obtain an aqueous solution containing 1.1 g of EDA quaternary salt.
実施例３ ＥＤＡ四級塩の合成
Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン１ｇ、硫酸ジメチル２．２ｇをテトラヒドロフラン５ｇに加え、室温で１時間撹拌した後、５０度で１時間撹拌した。析出したＥＤＡ四級塩の硫酸塩にエタノール５０ｇを加え、さらに水酸化ナトリウムを０．６８ｇ添加した。析出した硫酸ナトリウムを除き、水を加えた後エタノールを減圧で留去し、ＥＤＡ四級塩１．４ｇを含有する水溶液を得た。
Example 3 Synthesis of EDA quaternary salt 1 g of N, N, N ′, N′-tetramethylethylenediamine and 2.2 g of dimethyl sulfate were added to 5 g of tetrahydrofuran, and the mixture was stirred at room temperature for 1 hour and then stirred at 50 ° C. for 1 hour. . 50 g of ethanol was added to the precipitated EDA quaternary sulfate, and 0.68 g of sodium hydroxide was further added. After removing the precipitated sodium sulfate, water was added and ethanol was distilled off under reduced pressure to obtain an aqueous solution containing 1.4 g of EDA quaternary salt.
実施例４ ＥＤＡ四級塩の合成
Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン１ｇ、炭酸ジメチル２０ｇを耐圧ガラス管に入れ、８０度で３時間加熱した。減圧で溶媒を留去した後、固体状になったＥＤＡ四級塩の炭酸塩を水に溶解した。この水溶液に強塩基性イオン交換樹脂（三菱化学（株）製、ダイヤイオンＳＡ１０Ａ（ＯＨ形））を添加し、室温で８時間撹拌した。イオン交換樹脂を除き、ＥＤＡ四級塩の水溶液を得た。
Example 4 Synthesis of EDA quaternary salt 1 g of N, N, N ′, N′-tetramethylethylenediamine and 20 g of dimethyl carbonate were placed in a pressure-resistant glass tube and heated at 80 ° C. for 3 hours. After distilling off the solvent under reduced pressure, the solid EDA quaternary carbonate was dissolved in water. To this aqueous solution, a strongly basic ion exchange resin (Diaion SA10A (OH form), manufactured by Mitsubishi Chemical Corporation) was added and stirred at room temperature for 8 hours. An aqueous solution of EDA quaternary salt was obtained by removing the ion exchange resin.
実施例５ 現像液の評価
実施例１で合成したＥＤＡ四級塩を水で希釈し、５％ＥＤＡ四級塩水溶液とした。
Example 5 Evaluation of Developer The EDA quaternary salt synthesized in Example 1 was diluted with water to obtain a 5% EDA quaternary salt aqueous solution.
ノボラック樹脂系フォトレジストをシリコンウエハ上に塗布し、乾燥させて、厚さ２．２μｍのフォトレジスト層にした。これを１００℃に加熱し、マスク基板をとおして露光した。 A novolac resin-based photoresist was applied onto a silicon wafer and dried to form a 2.2 μm thick photoresist layer. This was heated to 100 ° C. and exposed through a mask substrate.
この露光フォトレジスト膜を前述の５％ＥＤＡ四級塩水溶液に室温で２分浸漬し、現像した。この現像処理の後、純水で２分間洗浄し、ＳＥＭで基板を観察し、レジストパターンが形成されているのを確認した。 This exposed photoresist film was immersed in the aforementioned 5% EDA quaternary salt aqueous solution at room temperature for 2 minutes and developed. After this development treatment, the substrate was washed with pure water for 2 minutes, and the substrate was observed with an SEM to confirm that a resist pattern was formed.
実施例６ 現像液の評価
実施例５で使用した現像液をさらに水で希釈し、０．５％ＥＤＡ四級塩水溶液とした。現像時間を１０分とした以外は実施例５と同じ方法でフォトレジストを現像したところ、レジストパターンが形成されているのを確認した。
Example 6 Evaluation of Developer The developer used in Example 5 was further diluted with water to obtain a 0.5% EDA quaternary salt aqueous solution. When the photoresist was developed by the same method as in Example 5 except that the development time was 10 minutes, it was confirmed that a resist pattern was formed.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011074064A JP2012208325A (en) | 2011-03-30 | 2011-03-30 | Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011074064A JP2012208325A (en) | 2011-03-30 | 2011-03-30 | Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2012208325A true JP2012208325A (en) | 2012-10-25 |
Family
ID=47188116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011074064A Pending JP2012208325A (en) | 2011-03-30 | 2011-03-30 | Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2012208325A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015098398A1 (en) * | 2013-12-26 | 2015-07-02 | 富士フイルム株式会社 | Pattern formation method, method for producing electronic device, electronic device, and aqueous developing solution |
| US20160195813A1 (en) * | 2015-01-05 | 2016-07-07 | Shin-Etsu Chemical Co., Ltd. | Developer and patterning process using the same |
| CN108970535A (en) * | 2018-06-25 | 2018-12-11 | 江南大学 | A kind of dimeric surfactant vermiculate glues and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004102019A (en) * | 2002-09-11 | 2004-04-02 | Fuji Photo Film Co Ltd | Positive type resist composition |
| JP2006517508A (en) * | 2003-02-14 | 2006-07-27 | コンセホ・スペリオール・デ・インベスティガシオネス・シエンティフィカス | Porous crystalline material (zeolite ITQ-24), process for producing the crystalline material, and use of the crystalline material in the catalytic conversion of organic compounds |
| JP2008536312A (en) * | 2005-04-08 | 2008-09-04 | サッチェム， インコーポレイテッド | Selective wet etching of metal nitride |
| CN101830811A (en) * | 2010-02-23 | 2010-09-15 | 江苏扬农化工集团有限公司 | Preparation method of 4-aminodiphenylamine |
-
2011
- 2011-03-30 JP JP2011074064A patent/JP2012208325A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004102019A (en) * | 2002-09-11 | 2004-04-02 | Fuji Photo Film Co Ltd | Positive type resist composition |
| JP2006517508A (en) * | 2003-02-14 | 2006-07-27 | コンセホ・スペリオール・デ・インベスティガシオネス・シエンティフィカス | Porous crystalline material (zeolite ITQ-24), process for producing the crystalline material, and use of the crystalline material in the catalytic conversion of organic compounds |
| JP2008536312A (en) * | 2005-04-08 | 2008-09-04 | サッチェム， インコーポレイテッド | Selective wet etching of metal nitride |
| CN101830811A (en) * | 2010-02-23 | 2010-09-15 | 江苏扬农化工集团有限公司 | Preparation method of 4-aminodiphenylamine |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015098398A1 (en) * | 2013-12-26 | 2015-07-02 | 富士フイルム株式会社 | Pattern formation method, method for producing electronic device, electronic device, and aqueous developing solution |
| JP2015125321A (en) * | 2013-12-26 | 2015-07-06 | 富士フイルム株式会社 | Pattern formation method, method for manufacturing electronic device, electronic device, and aqueous developing solution |
| US20160195813A1 (en) * | 2015-01-05 | 2016-07-07 | Shin-Etsu Chemical Co., Ltd. | Developer and patterning process using the same |
| JP2016126182A (en) * | 2015-01-05 | 2016-07-11 | 信越化学工業株式会社 | Developer and pattern forming method using the same |
| US9645498B2 (en) * | 2015-01-05 | 2017-05-09 | Shin-Etsu Chemical Co., Ltd. | Developer and patterning process using the same |
| CN108970535A (en) * | 2018-06-25 | 2018-12-11 | 江南大学 | A kind of dimeric surfactant vermiculate glues and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103717562B (en) | Cyclic compound, its manufacture method, compositions and corrosion-resisting pattern forming method | |
| JP2015055844A5 (en) | ||
| JP4594808B2 (en) | PHOTORESIST COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE USING THE SAME OR SEMICONDUCTOR ELEMENT MANUFACTURING METHOD | |
| JPWO2005097725A1 (en) | Calix resorcinarene compound, photoresist substrate and composition thereof | |
| JP2007277219A (en) | Sulfonium salt | |
| JP2008191413A (en) | Photosensitive composition | |
| JP5116311B2 (en) | Sulfonium salt | |
| JP5842778B2 (en) | Pattern formation method | |
| JP5317609B2 (en) | Photosensitive compound, photosensitive composition, and pattern forming method | |
| JP2012208325A (en) | Quaternary ammonium compound, method of manufacturing the same, and developer composition containing the same | |
| JP2014097969A5 (en) | ||
| TW200301409A (en) | Developing solution for photoresist | |
| KR102069041B1 (en) | Novel sulfonium salt, method for producing the same, and photoacid generator | |
| JP5116310B2 (en) | Sulfonium salt | |
| JP2013023407A (en) | Composition for forming metal oxide film | |
| CN1809791A (en) | Developer composition for resists and method for formation of resist pattern | |
| JP4012866B2 (en) | Quaternary ammonium base type semiconductor surface treatment agent and method for producing the same | |
| JP4554193B2 (en) | Method for producing and purifying hydroxylamine stabilizer | |
| JP2013028743A (en) | Silsesquioxane compound, method for producing the same, and resist material | |
| JP5172378B2 (en) | Photosensitive composition and pattern forming method using the same | |
| JP2016023165A (en) | Method for producing trimethyladamantylammonium hydroxide | |
| CN103946204B (en) | Cyclic compound, its manufacture method, radiation-sensitive composition and corrosion-resisting pattern forming method | |
| JP4206718B2 (en) | Method for producing photosensitive polyamide resin composition | |
| JPWO2022059448A5 (en) | ||
| US7045655B2 (en) | Preparation and purification of hydroxylamine stabilizers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140227 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141128 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20150414 |