CN112592277A - 由二环己基甲酮合成的可降解型树脂单体及其制备方法 - Google Patents
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Abstract
本发明属于可降解型光刻胶树脂单体，公开了一种由二环己基甲酮合成的可降解型树脂单体及其制备方法，树脂单体的结构式如下：
其中R为烷基或杂烷基。其制备方法为，原料Ⅰ的羟基经保护，得到中间体Ⅱ；原料Ⅰ包括以下结构通式
Description
技术领域
本发明涉及可降解型光刻胶树脂单体技术领域，特别涉及一种由二环己基甲酮合成的可降解型树脂单体及其制备方法。
背景技术
光刻材料(特指光刻胶)，又称光致抗蚀剂，是光刻技术中涉及的最关键的功能性化学材料，主要成分是树脂、光致产酸剂、以及相应的添加剂和溶剂，这类材料具有光(包括可见光、紫外线、电子束等)化学敏感性，经光化学反应，本身在显影液中的溶解性发生变化。
光刻胶中所使用的树脂是由多种树脂单体共聚而成的聚合物，其中酸敏树脂单体是实现曝光前后树脂在显影液中溶解差异的重要组成部分，常见的酸敏树脂单体只有一个酸敏基团，其聚合物树脂为线性，曝光区域和未曝光区域的溶解度差异是通过酸敏基团曝光后脱保护形成的，线性聚合物主链并不会断开。因此，现有光刻胶由于酸敏树脂单体的特定结构，存在光刻图案分辨率较低的问题。
发明内容
本发明要解决的技术问题是克服现有技术的缺陷，提供一种由二环己基甲酮合成的可降解型树脂单体及其制备方法。
为了解决上述技术问题，本发明提供了如下的技术方案：
本发明一种由二环己基甲酮合成的可降解型树脂单体，所述树脂单体结构通式如下：
进一步地，所述树脂单体包括以下结构：
上述可降解型树脂单体的制备方法，包括以下合成步骤：
S1，原料Ⅰ的羟基经保护，得到中间体Ⅱ；所述原料Ⅰ包括以下结构通式
R为烷基或杂烷基。
S2，二环己基甲酮在所述中间体Ⅱ与金属形成的格氏试剂的条件下，经还原得到含有一个羟基的中间体Ⅲ；
S3，所述中间体Ⅲ经脱保护，得到含有两个羟基的中间体Ⅳ；
S4，所述中间体Ⅳ与丙烯酸类化合物经酯化反应，得到树脂单体Ⅴ。
进一步地，S1中，所述原料Ⅰ的羟基经苄基或硅醚基的保护，得到中间体Ⅱ。
合成路线:
进一步地，S1中，所述原料Ⅰ的羟基经苄基或硅醚基的保护，得到中间体Ⅱ。
进一步地，所述原料Ⅰ具体包括以下结构：
与现有技术相比，本发明的有益效果如下：
(1)树脂单体上还含有叔丁基结构，在曝光时，树脂上的光致产酸剂基团会产生磺酸，在酸的作用下，叔丁基结构会断开，导致聚合主链断开，产生小的片段，改善光刻图形的边缘粗糙度，提高光刻胶的分辨率，同时形成具有良好碱溶行的羟基，有利于显影过程中的溶解，增加曝光后在光刻胶在显影液中溶解速度，增大光刻胶的对比度。
(2)二环己基甲酮的环状结构也在很大程度上增加了光刻胶耐刻蚀性，树脂单体的多酯基结构也增加了其在脂溶性溶剂中的溶解性，方便旋涂均匀。
(3)本发明的合成路线简单，操作方便。
具体实施方式
应当理解，此处所描述的优选实施例仅用于说明和解释本发明，并不用于限定本发明。
实施例1
化合物1-2的制备：
将叔丁基二甲基氯硅烷(13g，86.3mmol)溶于四氢呋喃(50g)中，然后在0℃氮气保护下，将上述混合液滴加到含有2-溴乙醇1-1(10g，80.0mmol)、三乙胺(10g，98.8mmol)和4-二甲氨基吡啶(1g，8.2mmol)的四氢呋喃(100g)溶液中，搅拌3小时。产生的悬浮液经过滤得到滤液，将滤液浓缩，经减压蒸馏提纯，得到化合物1-2(15.5g，64.8mmol，摩尔收率81.0％)。
化合物1-3的制备：
将化合物1-2(13g，54.3mmol)溶于乙醚(100g)中，在氮气保护下，将上述混合液滴加到含有镁(1.3g,54.2mmol)的乙醚(30g)中，在25℃下，搅拌1小时。然后将二环己基甲酮(10g，51.5mmol)溶于乙醚(80g)中，滴入上述混合液中，搅拌3小时。将反应液淬灭，然后过滤，滤液用乙酸乙酯萃取，将得到有机层合并，并用盐水洗涤，无水硫酸钠干燥，浓缩得到粗产品。将粗产物用乙酸乙酯和己烷重结晶，得到化合物1-3(15g，42.3mmol，摩尔收率82.2％)。
化合物1-4的制备：
在25℃氮气保护下，将1mol/L的四丁基氟化铵四氢呋喃溶液(46mL，46mmol)滴加到含有化合物1-3(15g，42.3mmol)的四氢呋喃(100g)溶液中，搅拌3小时。反应液用饱和氯化铵溶液淬灭，加入乙酸乙酯萃取，合并有机相进行浓缩，得到粗产品，粗产品经硅胶柱纯化得到化合物1-4(9g，37.4mmol，摩尔收率88.5％)。
树脂单体1-5的制备：
将化合物1-4(9g，37.4mmol)，三乙胺(8g，79.1mmol)溶于二氯甲烷(150g)中，然后在0℃，氮气保护下将甲基丙烯酰氯(8g，76.5mmol)滴加到上述混合液中搅拌30分钟，然后在室温下继续搅拌4小时。加饱和碳酸氢钠溶液，萃取，浓缩萃取液，得到粗产品，粗产品经柱层析纯化，得到树脂单体1-5(12g，31.9mmol，摩尔收率85.1％)。
实施例2
化合物2-2的制备：
将叔丁基二甲基氯硅烷(10g，66.3mmol)溶于四氢呋喃(50g)中，然后在0℃氮气保护下，将上述混合液滴加到含有3-溴甲基-3-羟甲基-1-氧杂环丁烷1-1(10g，55.2mmol)、三乙胺(8g，79.1mmol)和4-二甲氨基吡啶(1g，8.2mmol)的四氢呋喃(100g)溶液中中，搅拌3小时。产生的悬浮液经过滤得到滤液，将滤液浓缩，经减压蒸馏提纯，得到化合物2-2(13g，44.0mmol，摩尔收率79.7％)。
化合物2-3的制备：
将化合物2-2(13g，44.0mmol)溶于乙醚(100g)中，在氮气保护下，将上述混合液滴加到含有镁(1.2g,50mmol)的乙醚(30g)中，在25℃下，搅拌1小时。然后将二环己基甲酮(8g，41.2mmol)溶于乙醚(80g)中，滴入上述混合液中，搅拌3小时。将反应液淬灭，然后过滤，滤液用乙酸乙酯萃取，将得到有机层合并，并用盐水洗涤，无水硫酸钠干燥，浓缩得到粗产品。将粗产物用乙酸乙酯和己烷重结晶，得到化合物2-3(12.5g，30.4mmol，摩尔收率73.9％)。
化合物2-4的制备：
在25℃氮气保护下，将1mol/L的四丁基氟化铵四氢呋喃溶液(32mL，32mmol)滴加到含有化合物2-3(12.5g，30.4mmol)的四氢呋喃(100g)溶液中，搅拌3小时。反应液用饱和氯化铵溶液淬灭，加入乙酸乙酯萃取，合并有机相进行浓缩，得到粗产品，粗产品经硅胶柱纯化得到化合物2-4(8g，27.0mmol，摩尔收率88.7％)。
树脂单体2-5的制备：
将化合物2-4(8g，27.0mmol)，三乙胺(6g，59.3mmol)溶于二氯甲烷(150g)中，然后在0℃，氮气保护下将甲基丙烯酰氯(6g，57.4mmol)滴加到上述混合液中搅拌30分钟，然后在室温下继续搅拌4小时。加饱和碳酸氢钠溶液，萃取，浓缩萃取液，得到粗产品，粗产品经柱层析纯化，得到树脂单体2-5(10g，23.1mmol，摩尔收率85.7％)。
最后应说明的是：以上所述仅为本发明的优选实施例而已，并不用于限制本发明，尽管参照前述实施例对本发明进行了详细的说明，对于本领域的技术人员来说，其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换。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 (5)
1.一种由二环己基甲酮合成的可降解型树脂单体，其特征在于，所述树脂单体结构通式如下：
2.根据权利要求1所述的由二环己基甲酮合成的可降解型树脂单体，其特征在于，所述树脂单体包括以下结构：
3.由二环己基甲酮合成的可降解型树脂单体的制备方法，其特征在于，包括以下合成步骤：
S1，原料Ⅰ的羟基经保护，得到中间体Ⅱ；
S2，二环己基甲酮在所述中间体Ⅱ与金属形成的格氏试剂的条件下，经还原得到含有一个羟基的中间体Ⅲ；
S3，所述中间体Ⅲ经脱保护，得到含有两个羟基的中间体Ⅳ；
S4，所述中间体Ⅳ与丙烯酸类化合物经酯化反应，得到树脂单体Ⅴ；
合成路线为：树脂单体的合成路线具体为：
4.根据权利要求3所述的由二环己基甲酮合成的可降解型树脂单体的制备方法，其特征在于，S1中，所述原料Ⅰ的羟基经苄基或硅醚基的保护，得到中间体Ⅱ。
5.根据权利要求3所述的由二环己基甲酮合成的可降解型树脂单体的制备方法，其特征在于，所述原料Ⅰ具体包括以下结构：
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