CN111413848A - 一种有机硅改性丙烯酸酯类光刻胶及其制备方法 - Google Patents
一种有机硅改性丙烯酸酯类光刻胶及其制备方法 Download PDFInfo
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Abstract
本发明涉及一种有机硅改性丙烯酸酯类光刻胶及其制备方法，属于胶黏剂技术领域。以质量百分数计算，由以下组份组成：成膜树脂14.2～23.7份，交联剂4.2～7.5份，光引发剂0.8～1.4份，助剂0.06～0.13份，溶剂67.3～80.7份。本发明的光刻胶，利用有机硅对成膜树脂进行改性，增强了其与基材的粘接性，同时也降低了光刻胶的脆性，制备的光刻胶附着力好、分辨率高，在液晶显示屏的制备过程中有着很好的应用前景。
Description
技术领域
本发明涉及一种有机硅改性丙烯酸酯类光刻胶及其制备方法，属于胶黏剂技术领域。
背景技术
光刻胶，又称光致抗蚀剂，是电子行业微细加工技术的关键材料，主要应用于电子工业集成电路、半导体分立器和平板显示器的制作。光刻胶，简言之，就是在光源的激发下，发生化学反应，致使分子结构发生变化，使得其在特定溶液中的溶解度发生变化。在光源激发下，光刻胶在特定溶液中的溶解度增大，称之为正性光刻胶，反之，称之为负性光刻胶。目前，国内生产的光刻胶主要满足中低端市场的需求，高档次的光刻胶主要依赖进口，而高端光刻胶的生产技术主要被韩国、日本所垄断。甲基丙烯酸类光刻胶，是一类传统的光刻胶，它存在着分辨率不高、脆性大、与基材粘附力差等缺点。本发明主要利用有机硅对其改性，解决了传统丙烯酸酯类光刻胶的缺点。
发明内容
本发明目的是提供一种有机硅改性丙烯酸酯类光刻胶及其制备方法。
本发明涉及的有机硅改性丙烯酸酯类光刻胶由如下重量分数的原料组成：
成膜树脂14.2～23.7份
交联剂4.2～7.5份
光引发剂0.8～1.4份
助剂0.06～0.13份
溶剂67.3～80.7份
本发明中的成膜树脂具有如下结构通式(m，n，o，p，q指聚合度)：
成膜树脂是由丙烯酸类单体通过溶液自由基聚合方法制成，单体如下：
具体制备过程如下：(a)在配有机械搅拌和冷凝回流管的反应釜中，加入溶剂(丁酮、异丙醇或乙二醇单甲醚)，甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸苯酯的混合单体，加热至87℃，加入引发剂，反应40分钟；(b)补加溶剂(丁酮、异丙醇或乙二醇单甲醚)，甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸苯酯的混合单体、引发剂，反应3小时；(c)补加溶剂(丁酮、异丙醇或乙二醇单甲醚)、N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺、N-(3-(3-乙氧基硅)-丙基)-丙烯酰胺的混合单体，引发剂，继续反应8小时；(d)停止加热，冷却至室温，后处理得到成膜树脂。
本发明中的有机硅改性剂N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺、N-(3-(3-乙氧基硅)-丙基)-丙烯酰胺，按照如下路线制备：
制备方法如下：(a)将丙烯酸和3-(甲/乙氧基硅)-丙基-1-胺溶于干燥的二氯甲烷中，在冰水浴中搅拌10分钟；(b)将二环己基碳二亚胺(DCC)加入至反应瓶中，在0℃反应3小时；(c)撤去冰水浴，在室温下反应1小时，然后将反应液倒入冰水中，过滤，减压蒸馏除去溶剂，得到N-(3-(3-甲/乙氧基硅)-丙基)-丙烯酰胺。
本发明所述交联剂为官能度为2以上的丙烯酸衍生物单体，两种以上混合使用，具体结构如下：
本发明所述光引发剂为六芳基二咪唑、二苯甲酮和安息香双甲醚的一种或两种混合使用。
本发明所述助剂为氟改性流平剂KMT-1020和硅聚醚改性流平剂ZY-8533中的一种。
本发明所述溶剂为丁酮、异丙醇和乙二醇单甲醚，一种或多种混合使用。
本发明制备的成膜树脂的重均聚分子量Mw.45000。
本发明光刻胶采用接触式曝光法进行曝光，使用SBG-型曝光机(3000W紫外灯)。
本发明的光刻胶的工艺过程：涂胶、前烘、曝光、显影、坚膜、刻蚀、去膜。
本发明的光刻胶，与基材的粘接性好、脆度低、分辨率高。
具体实施实例
实施例1改性剂N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺的制备
称取3.6g丙烯酸和17.9g 3-(甲/乙氧基硅)-丙基-1-胺溶于150mL无水二氯甲烷中，冰水浴中搅拌10分钟；分三次加入30.3g二环己基碳二亚胺，在0℃继续反应3小时；撤去冰水浴，在室温下反应1小时，然后将反应液倒入冰水中，过滤，减压蒸馏除去溶剂，得到N-(3-(3-甲/乙氧基硅)-丙基)-丙烯酰胺。产率：95.3％
实施例2成膜树脂的制备
于配有机械搅拌和冷凝回流管的反应釜中，加入32.1g甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸苯酯的混合单体和60.1g丙酮，加热至87℃，加入0.13g引发剂AIBN，反应40钟；然后加入30.5g甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸苯酯的混合单体和28.4g丁酮，0.15g引发剂AIBN，反应3小时；加入7.3g N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺、30.7g溶剂和0.45g引发剂AIBN，继续反应8小时；停止反应，后处理得到成膜树脂。
实施例3光刻胶的配置
称取19g改性成膜树脂、6.1g交联剂(3.2g 3-光能度单体和2.4g 2-官能度单体)和1.2g光引发剂二苯甲酮，再加入73.2g丁酮，充分溶解，过滤三次后直接使用。然后经涂胶、前烘、曝光、显影、坚膜过程。前烘条件为85℃、17min，曝光时间为11S，显影时间为45S，坚膜条件为105℃，25min的工艺条件下，光刻图像边缘清晰，线条比直，所得图像分辨率高，光刻图形质量好。
以上所述仅为本发明的实施例而已，并不用于限制本发明。本发明可以有各种合适的更改和变化。凡在本发明的精神和原则之内所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (3)
1.一种有机硅改性丙烯酸酯类光刻胶及其制备方法，其特征在于，由如下质量份数的原料组成：
成膜树脂 14.2～23.7份
交联剂 4.2～7.5份
光引发剂 0.8～1.4份
助剂 0.06～0.13份
溶剂 67.3～80.7份
其中，所述成膜树脂是由丙烯酸衍生物单体通过溶液自由基聚合方法制成，具体如下结构通式：
(m，n，o，p，q指聚合度)；
其中，所述交联剂为官能度为2以上的变丙烯酸酸衍生物单体，两种以上混合使用，具体结构如下：
其中，所述光引发剂为六芳基二咪唑、二苯甲酮和安息香双甲醚的一种或两种混合使用；
其中，所述助剂为氟改性流平剂KMT-1020和硅聚醚改性流平剂ZY-8533中的一种；
其中，所述溶剂为丁酮、异丙醇和乙二醇单甲醚，一种或多种混合使用。
2.如权利要求1所述的一种有机硅改性甲基丙烯酸酯类光刻胶中，成膜树脂是由单体
通过溶液自由基聚合方法制成，其特征在于，引入了N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺和N-(3-(3-乙氧基硅)-丙基)-丙烯酰胺为有机硅改性剂，一种或两种混合使用。
3.如权利要求2所述的一种有机硅改性甲基丙烯酸酯类光刻胶中，成膜树脂按照如下方法制备：(a)在配有机械搅拌和冷凝回流管的反应釜中，加入溶剂(丁酮、异丙醇或乙二醇单甲醚)和甲基丙烯酸、甲基丙烯酸甲酯和甲基丙烯酸苯酯的混合单体，加热至87℃，加入引发剂，反应40分钟；(b)补加溶剂(丁酮、异丙醇或乙二醇单甲醚)、甲基丙烯酸、甲基丙烯酸甲酯和甲基丙烯酸苯酯的混合单体、引发剂，反应3小时；(c)补加溶剂(丁酮、异丙醇或乙二醇单甲醚)、N-(3-(3-甲氧基硅)-丙基)-丙烯酰胺和N-(3-(3-乙氧基硅)-丙基)-丙烯酰胺的混合单体、引发剂，继续反应8小时；(d)停止反应并后处理得到成膜树脂。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999340A (zh) * | 2021-10-19 | 2022-02-01 | 江苏集萃光敏电子材料研究所有限公司 | 一种含硅或硫的成膜树脂、光刻胶组合物 |
| CN116987225A (zh) * | 2023-09-27 | 2023-11-03 | 甘肃华隆芯材料科技有限公司 | 一种193nm用光刻胶聚合物及其制备方法和光刻胶组合物 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629358A (en) * | 1991-12-27 | 1997-05-13 | Imperial Chemical Industries Plc | Photocurable resin composition containing acrylate silane and epoxy silane and/or their hydrolysis products |
| JPH11279243A (ja) * | 1998-03-31 | 1999-10-12 | Goo Chem Ind Co Ltd | 紫外線硬化性樹脂及び紫外線硬化性樹脂組成物並びにフォトソルダーレジストインク |
| CN1834785A (zh) * | 2006-04-19 | 2006-09-20 | 苏州华飞微电子材料有限公司 | 含硅193nm负性光刻胶及其成膜树脂 |
| US20060210929A1 (en) * | 2005-03-15 | 2006-09-21 | Canon Kabushiki Kaisha | Photosensitive composition and forming process of structured material using the composition |
| JP2009286980A (ja) * | 2008-06-02 | 2009-12-10 | Nissan Chem Ind Ltd | アルカリ可溶性樹脂及び感光性樹脂組成物 |
| US20100041822A1 (en) * | 2006-08-09 | 2010-02-18 | Wacker Chemie Ag | Crosslinkable reactive silicone organic copolymers and method for the production and use thereof |
-
2019
- 2019-01-05 CN CN201910009726.4A patent/CN111413848B/zh active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629358A (en) * | 1991-12-27 | 1997-05-13 | Imperial Chemical Industries Plc | Photocurable resin composition containing acrylate silane and epoxy silane and/or their hydrolysis products |
| JPH11279243A (ja) * | 1998-03-31 | 1999-10-12 | Goo Chem Ind Co Ltd | 紫外線硬化性樹脂及び紫外線硬化性樹脂組成物並びにフォトソルダーレジストインク |
| US20060210929A1 (en) * | 2005-03-15 | 2006-09-21 | Canon Kabushiki Kaisha | Photosensitive composition and forming process of structured material using the composition |
| CN1834785A (zh) * | 2006-04-19 | 2006-09-20 | 苏州华飞微电子材料有限公司 | 含硅193nm负性光刻胶及其成膜树脂 |
| US20100041822A1 (en) * | 2006-08-09 | 2010-02-18 | Wacker Chemie Ag | Crosslinkable reactive silicone organic copolymers and method for the production and use thereof |
| JP2009286980A (ja) * | 2008-06-02 | 2009-12-10 | Nissan Chem Ind Ltd | アルカリ可溶性樹脂及び感光性樹脂組成物 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999340A (zh) * | 2021-10-19 | 2022-02-01 | 江苏集萃光敏电子材料研究所有限公司 | 一种含硅或硫的成膜树脂、光刻胶组合物 |
| CN116987225A (zh) * | 2023-09-27 | 2023-11-03 | 甘肃华隆芯材料科技有限公司 | 一种193nm用光刻胶聚合物及其制备方法和光刻胶组合物 |
| CN116987225B (zh) * | 2023-09-27 | 2023-12-22 | 甘肃华隆芯材料科技有限公司 | 一种193nm用光刻胶聚合物及其制备方法和光刻胶组合物 |
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