CN1214290C - 在基体上形成平面化薄膜的方法,涂布该薄膜的基体和形成该薄膜的组合物 - Google Patents
在基体上形成平面化薄膜的方法,涂布该薄膜的基体和形成该薄膜的组合物 Download PDFInfo
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Abstract
一种在基体上形成平面化薄膜使它加热时不会冒烟的方法，该方法包括在基体上涂布一种包含一种酚醛清漆树脂、一种表面活性剂和一种任选的有机溶剂的聚合物溶液，然后加热该基体，所述酚醛清漆树脂的重均分子量在约1000-3000原子质量单位之间，它已经过分级而除去了分子量低于约350原子质量单位的分子，所述表面活性剂选自非氟化烃、氟化烃和它们的组合物。
Description
发明背景
发明领域
本发明一般地涉及用于微电子器件如集成电路的酚醛聚合物平面化薄膜，更具体地说，涉及具有高温稳定性的平面化薄膜。再具体的说，本发明涉及的是在基体上形成平面化薄膜的方法、涂布平面化薄膜的基体和在该基体上形成平面化薄膜的组合物。
相关技术描述
酚醛聚合物已广泛用来制造集成电路与其它半导体和微电子器件。特别是，用于半导体结构光刻电路的光刻胶中常含有一个酚醛清漆树脂组分。见，例如，授予Nakayama等人的美国专利5,601,961。
此外，酚醛聚合物也是微电子器件制造中所用平面化薄膜的组分，目的是提供一个较平整的表面。见，例如，美国专利5,276,126及其中的参考文献。随着这类器件上的特征尺寸变得越来越小，平面化薄膜在器件制造工艺中越来越重要。业已发现，低重均分子量酚醛聚合物，即分子量在约200-约2300原子质量单位之间者，在形成平面化薄膜中非常有用，因为它们比分子量较高的聚合物更容易流动。
在形成平面化薄膜的典型工艺中，要配制一种含酚醛聚合物与一种表面活性剂的溶液。将这种含表面活性剂的聚合物溶液用传统的旋转技术涂布在基体上。加热已涂布了聚合物溶液的基体，以蒸发掉存于薄膜材料中的所有残留溶剂并降低薄膜的粘度。粘度降低有利于材料流动和提高薄膜在基体上的流平性。用这种酚醛聚合物配方形成平面化薄膜的困难在于，加热时会看到冒烟。受热挥发的材料在可能形成颗粒，导致所制造器件中的缺陷并可能堵塞真空管道等方面是有害的。
所以希望有一种方法能从酚醛聚合物材料形成平面化薄膜，它既能保留先前材料优良的平面化作用，但在加热时又不会冒烟。
发明概述
按照本发明，提供一种在基体上形成平面化薄膜的方法，该方法包括先在基体表面涂布一种包含一种酚醛清漆树脂与一种表面活性剂的溶液，所述酚醛清漆树脂的重均分子量在约1000-3000原子质量单位之间，以及其中酚醛清漆树脂已经过分级以除去分子量低于约350原子质量单位的分子，所述表面活性剂选自非氟化烃、氟化烃和它们组合物。该方法还包括加热已涂布溶液的基体以形成平面化薄膜。
按照本发明的另一个发明点，提供一种其上已涂布平面化薄膜的基体，所述薄膜包含一种酚醛清漆树脂和一种表面活性剂，所述酚醛清漆树脂的重均分子量在约1000-3000原子质量单位之间，以及其中酚醛清漆树脂已经过分级以除去分子量低于约350原子质量单位的低分子，所述表面活性剂选自非氟化烃、氟化烃和它们组合物。
在本发明的又一个实施方案中，提供一种用来在基体上形成平面化薄膜的组合物，该组合物包含如上所述已经过分级的酚醛清漆树脂、一种选自非氟化烃、氟化烃及它们的组合物的表面活性剂，以及一种任选的有机溶剂。按照本发明的组合物中所用的酚醛清漆树脂，用柱萃取、液-液萃取或超临界流体萃取等萃取技术进行分级，以除去分子量低于约350原子质量单位的级分。
采用按照本发明的组合物来形成平面化薄膜时，在加热带涂层基体的过程中观察不到冒烟。
参考实施方案详述
按照本发明形成平面化薄膜的方法使用一种组合物，它包含一种已经过分级而除去了低分子量组分的酚醛清漆树脂和一种表面活性剂。能用于本发明的酚醛清漆树脂和表面活性剂在题为“用于微电子结构的酚聚合物平面化薄膜”的美国专利申请号08/271,291(标为‘291申请，其也就是美国专利5,858,547)中已有所述，该申请已转让于本申请，包括于此供参考。
如上所述，低分子量酚醛清漆树脂在形成平面化薄膜中特别有用，因为它们倾向于比分子量较高的聚合物更易流动。聚合物的分子量，如本文所用，是指重均分子量，由，例如，凝胶渗透色谱法测定，以聚苯乙烯标定。按照本发明，已经确定，最低分子量级分，即分子量低于约350原子质量单位的酚醛清漆树脂，当含酚醛聚合物配方在形成平面化薄膜的过程中受热时具有热挥发性。因此，除去这个最低分子量级分就能克服带涂层基体加热时冒烟的问题。
酚醛清漆树脂可以市购，也可以从苯酚或其衍生物，如邻-、间-和对甲酚，与甲醛或与其它醛类化合物反应而生成。用甲苯萃取、柱萃取、液-液萃取和超临界萃取之类的萃取技术可以基本上除去最低分子量级分。
在甲苯萃取法中，将固体酚醛树脂与甲苯组合在一起并加热到约75-80℃之间。滗去甲苯，加入第二批甲苯；加热该混合物；再滗去甲苯。留下的固体是最低分子量级分已减少的酚醛聚合物。另一种萃取法，即柱萃取法，是对装填在一根玻璃柱中的已磨成细粉末的聚合物树脂和干硅胶的混合物进行的。先用第一种溶剂混合物，如乙酸乙酯和己烷的混合物，淋洗柱内混合物，直到获得大量萃取了低分子量组分的淋出溶剂。然后用第二种溶剂，如甲醇进行淋洗，从中回收已除去最低分子量级分的酚醛聚合物。
在液-液萃取法中，将酚醛聚合物与两种极性不同的溶剂，例如，乙酸乙酯和己烷，进行组合并用一种超声装置进行混合。混合物料分离成两相；从底层回收除去了最低分子量级分的聚合物。也可以用超临界流体萃取技术。在该方法中，让极性溶剂如乙酸乙酯、乙醇或甲醇和CO2流过萃取容器中的一个酚醛聚合物样品，加热到约60-65℃范围内的温度，加压到约200-300巴。留在容器中的酚醛聚合物已除尽了低分子量组分。
正如所附实施例中详细报告，用上述技术进行萃取使酚醛聚合物具有提高的分子量和更窄的多分散性。多分散性定义为重均分子量与数均分子量之比。例如，对Borden Chemical公司提供的命名为SD-333A的酚醛清漆树脂进行的萃取，使分子量从约900提高到了约1300-1800之间，同时使多分散性从1.5以上降到1.4以下，取决于萃取方法。组成酚醛清漆树脂的分子的分子量分布，可以用凝胶渗透色谱法(GPC)测定。高效液相色谱(HPLC)用来测定除去造成冒烟的低分子量物质的效率。分级使分子量低于约200的分子对HPLC面积百分数的贡献从占总分子量分布的20％以上降到低于约4％，并使分子量低于约350的分子的贡献从30％以上降到约10％以下。此外，分级能提高酚醛聚合物的热稳定性，这一点可以从玻璃化转变温度的提高和加热时重量损失的减少得以证明。
因此，本发明所用的酚醛聚合物是用它们分级后残留物的重均分子量以及分子量低于约350，即最低分子量级分的分数来表征的。最好使用分子量在约900-约2500之间，优选在约1200-2300之间且最低分子量级分少于约22％，优选少于约15％的酚醛聚合物。
分级后的酚醛聚合物可以与一种表面活性剂组合配制成一种形成平面化薄膜的涂布液。如‘291申请中所述，适用于本发明的表面活性剂包括非氟化烃和氟化烃以及它们的混合物。适用的非氟化烃表面活性剂可以由含约5-约50个碳原子，优选含约10-约30个碳原子的有机酸及其酯的烷基化衍生物或它们的组合物组成。适用的氟化烃表面活性剂可由含约5-约50个碳原子，优选含约10-约30个碳原子，且至少有一个碳-氟键的有机酸及其酯的烷基化衍生物以及它们的组合物组成。更具体地说，特定的氟化烃表面活性剂包括含约50-约20个碳原子的氟化脂肪族氧化乙烯加成物、氟化烷基烷氧基化物和胺磺酰、由含约50-约20个碳原子并带酯端基的部分氟化烃链的单体衍生的含氟脂肪族聚酯、由含约5-约20个碳原子并带有酯和酸功能性端基的部分氟化烃链的单体衍生的含氟脂肪族共聚物以及它们的组合物，这类氟化表面活性剂都可从3M公司购得。
有机溶剂可以任选地作为第三组分包括在涂布液中。适用于本发明的溶剂包括脂肪族和芳香族的烃、醇、酮、酯、醚、醚醇、醚酯、醇酯、酮酯、酮醚、酮醇、酰胺、腈类以及它们的组合物。更具体地说，特定的溶剂包括乳酸乙酯、乙酸乙酯、乙酸丙酯、乙酸丁酯以及它们的组合物。
优选聚合物溶液含有占溶液总重量的约1-约90％，更优选约10-约50％，非常优选约20-约40％的酚醛聚合物，以及优选约0.01-约5％，更优选约0.1-约1％以及非常优选约0.3-约0.7％的表面活性剂。任选溶剂的存在量可以为约0-约90％，优选约10-约90％，更优选约50-约90％，非常优选约60-约85％。
聚合物溶液可以用任何传统的方法涂布到基体上去，如旋涂法。优选将溶液涂于基体中心，然后使之以约500-约6000rpm，优选约1500-约4000rpm的转速旋转约5-约60秒钟，优选约10-约30秒钟。任选地，再以约400-600rpm的较低速再旋转约1-约5秒钟的短时间，以使溶液在涂布后立即铺展开来。
一般地说，本发明的组合物是涂布在片基上的，例如其表面有电路图、将要加工成集成电路或其它微电子器件的硅片上。
然后用任何传统的方法加热该带涂层基体。优选将基体放在一块热板上从下面加热片基。一般地说，在工业上，这一步是通过一个常用的整体旋转涂布机/热板系统来完成的。一般将带涂层基体在约50℃-约300℃范围内，优选约100-200℃范围内的温度下加热约0.5分钟-约5分钟。或者，也可以用具有同样涂布时间与温度范围的多块热板，即约2-约5块热板，但后一块板的温度较前一块的高。
正如下面的实施例所示，当如前所述将按照本发明的含有已分级酚醛聚合物的配方涂布在基体上并加热以形成平面化薄膜时，没观察到冒烟。
实施例
实施例1-4中分别给出了用甲苯萃取、液-液萃取、柱萃取和超临界液体萃取等方法制备分级酚醛聚合物的实施例。在这些实施例中，使用的酚醛聚合物SD-333A由Borden Chemical公司提供。实施例1-4中所获得的分级酚醛聚合物的表征方法与性能示于实施例5和6中。将原始酚醛聚合物与已分级酚醛聚合物与一种表面活性剂和溶剂配制成涂布液。涂布液的配方与性能示于实施例7。
实施例1
在一个12升圆底烧瓶中，组合进固体块状酚醛聚合物(206.5g)和8升甲苯，并加热到75-80℃，同时搅拌75分钟。固体在55℃以上熔化。滗去甲苯，加进第二批8升甲苯，加热并搅拌75分钟，再滗去甲苯。将留在烧瓶中的固体溶于甲醇，旋转蒸发，直到得到一种绒毛状粉红色固体，然后在45℃真空烘箱内干燥过夜(88.5g)。
实施例2
在一个12升圆底烧瓶中装入酚醛聚合物(182.34g)。在该烧瓶中加入30体积％乙酸乙酯/70体积％己烷的溶剂混合物(10升)，乙酸乙酯为B&J公司的产品，己烷是Fisher Optima级。充分混合后，物料分离成两相，一个深色粘性底层和一个乳白色顶层。分离出含已分级酚醛聚合物的底层，并用旋转蒸发法除去溶剂。产量为49.6g(27.2％)。
实施例3
将已经磨成细粉末的固体酚醛聚合物(300g)与1200g干硅胶混合。将2英寸厚的一层洁净硅胶与30％乙酸乙酯与70％己烷形成的浆料，装在一根大玻璃柱(3 7/8英寸×48英寸)内。再将这种聚合物/硅胶混合物与同种溶剂混合成的浆料装在硅胶之上。用30％乙酸乙酯/70％己烷淋洗柱子，直至收集到15升淋洗溶剂为止。然后用甲醇淋洗柱子，收集3个4升级分。将头两个级分进行旋转蒸发直到获得固体：第一级分(153.4g)，第二级分(7.1g)，加起来总产量为160.5g。
实施例4
将酚醛聚合物(19.3g)装在一个50cm3的样品管内，插入一个Marc SimsDense Gas Management System，即超临界萃取设备中的一个30cm3的萃取容器中，安装好Alltech 426标准型HPLC泵，以便加入溶剂。用CO2(Air Product公司产品，SFC级)以约2g/min的流速清扫萃取容器10分钟并开始加热。然后关闭气流，继续加热，直至操作温度达60-61℃。在加热期间，用乙酸乙酯(B&J产品)起动HPLC泵。萃取容器中的压力为50-250巴。
萃取分两步进行。第一步始于CO2和乙酸乙酯在250巴压力下分别以9.2-9.4g/min和1.0ml/min流动。在有3597g CO2已通过萃取器后，将温度升到62℃。在又有4023g CO2通过了萃取器后，将温度升到64-65℃，在该温度下，使4500g CO2通过反应器。对于第二步，将CO2和乙酸乙酯分别以9.6-9.8g/min和3.0ml/min的流速维持到有2057g CO2已通过该萃取器为止。在整个第二步内，容器温度一直保持在62-63℃。分级酚醛聚合物的产量为11.29g。
实施例5
重均分子量(Mw)和数均分子量(Mn)由凝胶渗透色谱法(GPC)相对于聚苯乙烯进行测定。玻璃化转变温度由差示扫描量热法(DSC)测定。DSC测定步骤包括在250℃预热1分钟，目的是除去残余溶剂，然后以10℃/min的速率从25℃扫描到200℃。热失重由热重分析(TGA)测定，在其中，随温度以10℃/min的速率从30℃升到300℃，记录样品重量。最终的重量差记录在下表1中。
表1树脂材料的表征
| 材料 | Mw | Mn | 多分散性 | Tg(℃) | 失重，％ |
| 未分级 | 936 | 606 | 1.544 | 36.6 | 27.2 |
| 实施例1 | 1436 | 1055 | 1.361 | 72.4 | 15.2 |
| 实施例2 | 1730 | 1246 | 1.388 | 76.4 | 13.9 |
| 实施例3 | 1364 | 1072 | 1.273 | 73.8 | 13.4 |
| 实施例4 | 1301 | 916 | 1.419 | 64.9 | 13.0 |
实施例6
用Hewlett-Packard HPLC 1100型获得的高效液相色谱(HPLC)分析结果示于下表2中。表中给出了对应于特定分子量的峰面积百分数。假设探头对所有分子量的响应都相同。
表2树脂材料的表征--HPLC数据
| 材料 | Mw≈200(面积％) | Mw≈306(面积％) |
| 未分级 | 22.47 | 9.11 |
| 实施例1 | 3.05 | 4.67 |
| 实施例2 | 3.94 | 3.22 |
| 实施例3 | 0.08 | 4.13 |
| 实施例4 | 1.32 | 6.50 |
实施例7
将未分级酚醛聚合物和从实施例1-4b得到的已分级聚合物，与3M公司提供的商品名为FC-430的氟化酯衍生物表面活性剂和乳酸乙酯溶剂进行组合，以形成固体％和溶剂％如表所示的涂布液。将2-4ml溶液分配在4英寸裸露硅片的中心。让硅片以500rpm旋转2秒，然后以4000rpm旋转20秒。将该硅片在200℃热板上焙烘120秒。观察结果如下表3所示。
表3涂料组合物的性能
| 材料 | 固体％ | 溶剂％ | 厚度() | 冒烟观察 |
| 未分级 | 20.35 | 79.45 | 4253 | 最初20秒浓重 |
| 未分级 | 36.82 | 62.98 | 14802 | 最初60秒浓重 |
| 实施例1 | 17.8 | 81.75 | 4323 | 无 |
| 实施例1 | 31.8 | 67.75 | 14523 | 无 |
| 实施例2 | 17.8 | 81.75 | 4261 | 无 |
| 实施例2 | 31.8 | 67.75 | 13977 | 无 |
| 实施例3 | 15.8 | 83.75 | 3875 | 无 |
| 实施例3 | 29.8 | 69.75 | 14785 | 无 |
| 实施例4 | 17.8 | 81.75 | 4136 | 无 |
| 实施例4 | 31.8 | 67.75 | 13550 | 无 |
从表1中报告的玻璃化转变温度的提高和热失重的降低，可以看到，分级提高了酚醛聚合物热稳定性。表3中的结果清楚地证明，采用按照本发明的含有已分级酚醛聚合物的涂料组合物，在带涂层基体加热期间观察不到冒烟现象。
Claims (3)
1.一种在基体上形成平面化薄膜的方法，它包含：
在所述基体表面上涂布一种聚合物溶液，形成一个带涂层基体，所述聚合物溶液包含一种酚醛清漆树脂和一种表面活性剂，所述酚醛清漆树脂的重均分子量在1000-3000原子质量单位之间，以及其中酚醛清漆树脂已经过分级，使分子量低于350原子质量单位的分子减少至小于总分子量分布的22％，所述表面活性剂选自非氟化烃、氟化烃以及它们的组合物；
以及加热上述带涂层基体，以在所述表面上形成一层平面化薄膜，
其中所述带涂层基体在200℃的热板上加热2分钟时不产生看得见的烟，并且所述酚醛清漆树脂的多分散性小于1.4。
2.一种在其上涂布了平面化薄膜的基体，所述薄膜包含一种酚醛清漆树脂和一种表面活性剂，所述酚醛清漆树脂的重均分子量在1000-3000原子质量单位之间，以及其中酚醛清漆树脂已经过分级以除去分子量低于350原子质量单位的分子，所述表面活性剂选自非氟化烃、氟化烃和它们的组合物，其中所述平面化薄膜在加热到200℃保持2分钟时不产生看得见的烟，且其中所述酚醛清漆树脂中分子量低于350原子质量单位的级分少于总分子量分布的22％，其多分散性小于1.4。
3.一种用于形成平面化薄膜的涂料组合物，该涂料组合物包含
1-90重量％的酚醛清漆树脂，该树脂的重均分子量在1000-3000原子质量单位之间，以及其中酚醛清漆树脂已经过分级以除去分子量低于350原子质量单位的分子，其中所述酚醛清漆树脂中分子量低于350原子质量单位的级分少于总分子量分布的22％，其多分散性小于1.4，且其中所述涂布组合物在200℃的热板上加热2分钟时不产生看得见的烟；
0.01-5重量％的一种选自非氟化烃、氟化烃或它们的组合物的表面活性剂；和
10-90重量％的一种有机溶剂。
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| CL2008001614A1 (es) * | 2007-06-05 | 2008-08-08 | Wyeth Corp | Composicion parasiticida veterinaria que comprende un disolvente que no contiene hidroxilo, un estabilizador, amitraz y opcionalmente una lactona macrociclica y miristato de isopropilo; y su uso para tratar o controlar una infestacion o infeccion par |
| US8557877B2 (en) | 2009-06-10 | 2013-10-15 | Honeywell International Inc. | Anti-reflective coatings for optically transparent substrates |
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| US8864898B2 (en) | 2011-05-31 | 2014-10-21 | Honeywell International Inc. | Coating formulations for optical elements |
| US8986921B2 (en) * | 2013-01-15 | 2015-03-24 | International Business Machines Corporation | Lithographic material stack including a metal-compound hard mask |
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| WO2016208518A1 (ja) * | 2015-06-22 | 2016-12-29 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びパターニングされた基板の製造方法 |
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-
1998
- 1998-12-20 US US09/205,006 patent/US6506831B2/en not_active Expired - Fee Related
-
1999
- 1999-12-01 TW TW088120981A patent/TWI235289B/zh not_active IP Right Cessation
- 1999-12-20 KR KR1020017007798A patent/KR20010111483A/ko not_active Application Discontinuation
- 1999-12-20 DE DE69930418T patent/DE69930418D1/de not_active Expired - Lifetime
- 1999-12-20 AU AU25909/00A patent/AU2590900A/en not_active Abandoned
- 1999-12-20 EP EP99968506A patent/EP1141778B1/en not_active Expired - Lifetime
- 1999-12-20 AT AT99968506T patent/ATE320619T1/de not_active IP Right Cessation
- 1999-12-20 JP JP2000590013A patent/JP2003535352A/ja active Pending
- 1999-12-20 CN CNB998162566A patent/CN1214290C/zh not_active Expired - Fee Related
- 1999-12-20 WO PCT/US1999/030296 patent/WO2000038016A1/en not_active Application Discontinuation
-
2000
- 2000-12-12 US US09/735,838 patent/US6506441B2/en not_active Expired - Fee Related
- 2000-12-12 US US09/735,746 patent/US6517951B2/en not_active Expired - Fee Related
-
2002
- 2002-11-18 US US10/299,127 patent/US6723780B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000038016A1 (en) | 2000-06-29 |
| EP1141778B1 (en) | 2006-03-15 |
| US20020012809A1 (en) | 2002-01-31 |
| US20020002265A1 (en) | 2002-01-03 |
| AU2590900A (en) | 2000-07-12 |
| EP1141778A1 (en) | 2001-10-10 |
| TWI235289B (en) | 2005-07-01 |
| US6506831B2 (en) | 2003-01-14 |
| US6517951B2 (en) | 2003-02-11 |
| JP2003535352A (ja) | 2003-11-25 |
| CN1334931A (zh) | 2002-02-06 |
| KR20010111483A (ko) | 2001-12-19 |
| US6723780B2 (en) | 2004-04-20 |
| DE69930418D1 (de) | 2006-05-11 |
| US20030130482A1 (en) | 2003-07-10 |
| US20010000515A1 (en) | 2001-04-26 |
| US6506441B2 (en) | 2003-01-14 |
| ATE320619T1 (de) | 2006-04-15 |
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