CN1249525C - 负作用水性光刻胶组合物 - Google Patents
负作用水性光刻胶组合物 Download PDFInfo
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- CN1249525C CN1249525C CNB028188969A CN02818896A CN1249525C CN 1249525 C CN1249525 C CN 1249525C CN B028188969 A CNB028188969 A CN B028188969A CN 02818896 A CN02818896 A CN 02818896A CN 1249525 C CN1249525 C CN 1249525C
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Abstract
本发明涉及一种包含聚乙烯醇缩醛聚合物，水溶性光活性化合物，和交联剂的新型负性的水性光刻胶组合物。所述水溶性光活性化合物优选锍盐。本发明还涉及由该新型光刻胶组合物形成反像的方法。
Description
发明领域
本发明涉及一种对260nm以下波长(深紫外线)尤其敏感的水性负性光刻胶组合物，以及一种使这种光刻胶成像的方法。
发明背景
光刻胶组合物用于缩微平版印刷法(microlithographicprocesses)中，这些印刷法用于例如在制造计算机芯片与集成电路过程中制备微型化电子元件。在这些方法中，一般先将一种光刻胶组合物的薄膜涂覆到一种衬底材料上，例如用于制造集成电路的硅片。然后烘烤经涂覆过的衬底，以蒸发掉光刻胶组合物中的溶剂并将涂层固定到衬底上。接着将衬底的烘干的涂覆表面成像曝光于成像用辐射。
该辐射曝光导致涂覆表面的曝光区域发生化学转变。目前，可见光，紫外线(UV)，电子束和X-射线辐射能是缩微平版印刷法中常用的成像用幅射类型。成像曝光后，用显影剂溶液处理经涂覆过的衬底，以溶解并除去衬底的涂覆表面的辐射曝光或未曝光区域。
有两种类型的光刻胶组合物，负作用型与正作用型。当负作用光刻胶组合物成像曝光于辐射时，曝光于辐射下的光刻胶组合物的区域变得不溶于显影剂溶液中(例如发生交联反应)，而光刻胶涂层的未曝光区域相对而言仍溶于该溶液。因此，用显影剂处理被曝光的负作用光刻胶导致除去光刻胶涂层的未曝光区域，并在涂层中形成反像，从而露出在其上面沉积光刻胶组合物的位于下方的衬底表面的需要部分。对正作用光刻胶而言，显像剂将被曝光部分除掉。在制造器件过程中，有时希望采用负作用光刻胶以在衬底上形成图像。
现有技术中已知有使用负作用的酸敏光刻胶组合物。这样的现有技术光刻胶组合物中绝大多数使用交联剂，其与聚合物粘结剂树脂反应，以生成包含较高分子量聚合物的不溶性膜。传统的负性光刻胶用有机溶剂浇铸，并使用水性碱显影剂显影。但由于环境问题日益受到关注，能用如水或水为主的安全溶剂进行涂覆的负性光刻胶是非常理想的。因此，半导体工业需要负性的水性的光刻胶。此外，集成电路微型化的趋势已经导致能够在越来越短的波长下吸收的光刻胶的开发。目前，优选能够被260纳米(nm)以下光波长的称为深紫外(DUV)成像的光刻胶。因此，更希望有负性的水性的260nm以下敏感的光刻胶。
水性负性光刻胶通常含有聚合物、光活性化合物和交联剂，其中，所有固体组分都可溶于水或水为主的溶剂。此外，对于必须在260nm以下波长下具有光活性的光刻胶，所述聚合物和交联剂在成像波长下应该基本上是非吸收性的，由于聚合物是光刻胶膜的主要部分，这一点对聚合物尤为关键。带有极微量芳族官能度的聚合物对于在260nm以下成像是理想的，而无芳族官能度的聚合物对于在200nm以下成像是特别理想的。所需的光活性化合物基本上为水溶性的，并在曝光波长下产生吸收以生成酸。基于水溶性的并经历有效光化学转变的锍盐衍生物的光活性化合物特别合适。与此类似，需要的交联剂是基本上溶于水的且在酸存在下是非常有效的交联剂。
Harvard等以前曾公开了水性负性光刻胶的例子(Macromolecules1999，32，86-94和Chem.Mater.1999，11，719-725)。Harvard等(Chem.Mater.1999，11，719-725)所描述的光刻胶组合物基于聚乙烯醇、(2，4-二羟基苯基)二甲基锍三氟甲磺酸盐(triflate)和六甲氧基甲基三聚氰胺的水溶液。
US 5,648,196中也公开了二甲基多羟基苯锍盐，但这里所述聚合物含有芳族官能度。Sakamizu等评价了含有芳族聚合物和水溶性锍盐的光刻胶(ACS Symposium Series，614，124-36，1995)。Harvard等在Macromolecules 1999，32，86-94中描述了一种双组分水溶性光刻胶，其采用(4-甲氧基苯基)二甲基锍三氟甲磺酸盐将含有糖官能度的聚甲基丙烯酸酯缩醛转移。
US 5,858,620公开了一种用于采用聚乙烯醇缩醛或聚乙烯醇缩醛与交联剂的混合物的非光敏性水溶液涂覆被成像的光刻胶图案，并加热该溶液以在光刻胶图案上形成交联的涂层的方法。该方法旨在缩小衬底上开放空间的尺寸。
本发明涉及一种包含聚乙烯醇缩醛聚合物、水溶性光活性化合物和交联剂的新型负性的水性光刻胶组合物。本发明还涉及一种从所述新型光刻胶组合物形成反像的方法。
发明概述
本发明涉及一种新型负性的水性光刻胶组合物，所述组合物包含含有至少一种结构(1)单元的聚合物，
其中，R1表示氢或(C1-C4)烷基，n＝1～4；和水溶性光活性化合物；交联剂；和溶剂组合物。优选的光活性化合物的结构为(2)，
其中，R2独立地表示氢、烷基、-O(烷基)、-(烷基)OH、羟基苯基或多羟基苯基，R3和R4独立地表示(C1-C4)烷基，m＝1～3，和X-是一种阴离子。所述光刻胶组合物的溶剂优选为水或水和(C1-C4)烷基醇的混合物。
本发明进一步涉及一种使用本发明的光刻胶组合物形成反像的方法。
发明详述
本发明涉及一种新型负性作用的光刻胶组合物，其可用水或主要是水浇铸，并优选在260nm以下波长下敏感。所述光刻胶组合物包含水溶性聚合物、水溶性光活性化合物和水溶性交联剂。本发明还涉及一种从所述新型光刻胶组合物形成反像的方法。用于使该光刻胶成像的波长优选为254nm、248nm、193nm和157nm。整个本申请中，水溶性材料是指溶于只是水或主要含有水并含有较少量与水混溶的溶剂的混合物的那些水溶性材料，该与水混溶的溶剂例如有低级(C1-C4)烷基醇。
本发明的水溶性聚合物在光生酸与交联剂的存在下能够交联。所述聚合物含有至少一种结构(1)单元，
其中，R1表示氢或(C1-C4)烷基，且n＝1～4。
本发明所述聚合物一般指聚乙烯醇缩醛聚合物，其中结构(1)中的R1可以是氢、甲基、乙基、丙基或丁基。缩醛单元的聚合物骨架可以包含1～4个原子的碳链，优选n的值为1。可以使用含有乙烯醇缩醛单元与任何其他非芳族单体单元的共聚物，条件是所述聚合物基本溶于水。非芳族共单体的例子有：乙烯醇、乙酸乙烯酯、丙烯酰胺和乙烯基吡咯烷酮，但不限于此。一种制备聚乙烯醇缩醛的方法是通过聚乙烯醇与醛反应。视缩醛化程度而定，聚合物中可能存在游离亚甲基醇单元。所述乙烯醇缩醛单体的摩尔百分数可以为10mol％～100mol％，优选15mol％～50mol％。所述聚合物的重均分子量可以为500～15,000。
本发明所述光活性化合物是基本为水溶性，并在暴露于具有450nm以下波长的紫外线下时产生酸的那些光活性化合物。所述光活性化合物的例子有水溶性鎓盐和重氮盐。具有结构(2)的水溶性光活性化合物特别可用于成像。
其中，R2表示氢、(C1-C4)烷基、-O(烷基)、-(烷基)OH、羟基苯基或多羟基苯基，R3和R4独立地表示(C1-C4)烷基，m＝1～4，且X-是阴离子，例如多氟烷基磺酸盐。本申请中，烷基一般指含1～4个碳原子的碳链，其例子有：甲基、乙基、丙基和丁基。已经发现，当R是羟基时，无需曝光，光活性化合物室温即能引发光刻胶组合物中产生交联，并因此降低组合物的存放稳定性。光刻胶组合物具有足够的存放稳定性很重要，以使得保持一致的平版印刷性能。锍盐优选的实施方案中，R2是氢，R3和R4都是甲基，X是三氟甲磺酸根。
可用于本发明的交联剂为水溶性的并在光生酸的存在下能使聚合物交联的交联剂。所述交联剂的例子有：三聚氰胺树脂、尿素树脂和甘脲。特别是，可以使用下列交联剂：甲氧基羟甲基三聚氰胺树脂，甲氧基羟甲基脲树脂，和Cymel树脂。
本发明的固体组分一般溶于水或含有醇的水中。溶剂主要是水，优选去离子水。可以向水中加入一定量的可与水混溶的低级(C1-C4)烷基醇，例如乙醇或异丙醇，以形成一种可溶解固体组分的溶剂混合物。典型的溶剂混合物可以为水与醇的混合物，其中醇的比例为20wt％～1wt％。
可以向光刻胶组合物中加入其他添加剂，以改善工作性能，例如涂层均匀性与存放稳定性。这样的添加剂的例子有碱、无条痕(striation free)添加剂、表面活性剂和染料。
本发明的典型光刻胶组合物可以含有基于光刻胶组合物总重量最高为约50wt％的固体。以光刻胶组合物中固体总量计，所述固体可以包含1wt％～20wt％光酸生成剂，40wt％～95wt％酚醛树脂粘结剂，和5wt％～40wt％交联剂。
所制备的光刻胶溶液可以通过光刻胶领域中使用的任何常规方法涂覆到衬底上，这些方法包括浸涂、喷涂、涡转涂装和旋涂。例如旋涂时，在给定所用旋涂设备的类型和旋涂过程所用时间量的条件下，为提供所需厚度的涂层，可以调节光刻胶溶液的固体料量的百分比。合适的衬底包括硅、铝、聚合物树脂、有机薄膜、二氧化硅、掺杂二氧化硅、氮化硅、钽、铜、多晶硅、陶瓷、铝/铜混合物；砷化镓和其他诸如此类的第III/V族的化合物。
然后将所述的光刻胶组合物溶液涂覆到衬底上并将衬底热处理。选择该热处理，以便在不引起光敏组分明显热降解的同时，降低光刻胶中残留溶剂的浓度。通常，希望将溶剂浓度减到最小，并且该第一次热处理进行到基本上所有溶剂都已蒸发掉，衬底上留下约1微米厚度的光刻胶组合物的薄涂层为止。所述热处理进行到溶剂排除速率的变化变得相当小为止。温度与时间的选择取决于用户所需的光刻胶性能，以及所用设备和商业上期望的涂装次数。随后，涂覆过的衬底可以任何想要的通过使用合适的掩模，负片、镂花模板和样板等产生的图案曝光于光化辐射。然后在显影前将光刻胶进行曝光后的第二次烘烤或热处理。最优化烘烤温度和时间以使光刻胶薄膜中产生适当的交联量。典型的温度范围是100℃～200℃，时间可以为30s～30min。
通常通过在水或碱性显影溶液中进行浸渍或喷雾显影，将已曝光的经负性作用光刻胶涂覆过的衬底显影，以除去未曝光的区域。优选将所述溶液搅拌，例如通过氮气搅动进行。衬底可以保留在显影剂中，直到光刻胶涂层全部或基本全部从未曝光区域溶解下来。所述的显影剂可以是水，水和(C1-C4)烷基醇的混合物，或水和表面活性剂的混合物。优选的混合物是水和异丙醇的混合物。显影剂可以包括铵或碱金属氢氧化物的水溶液。优选的氢氧化物为氢氧化四甲铵。在从显影溶液中取出经涂覆的膜片后，可以进行非必要的显影后热处理或烘烤，以增加涂层的粘合力和提高对蚀刻溶液及其他物质的耐化学性。所述显影后热处理可以包括在涂层软化点以下在烘箱中烘烤该涂层与衬底。
以下的具体实施例将就本发明组合物的制备和使用方法作出详细的解释。但这些实施例无论如何并不意于限制或限定本发明的范围，也不应被认为是在提供为实施本发明所必须唯一使用的条件、参数或数值。
实施例
合成实施例1
(4-甲氧基苯基)二甲基锍三氟甲磺酸盐的合成
将42.2g AgCF3SO3和25.0g 1-甲氧基-4-甲硫基苯溶于500ml四氢呋喃中。在搅拌的同时，滴加入23.5g CH3I。添加完成后，将混合物搅拌12小时；将生成的AgI过滤掉。若滤液仍混浊，则可将溶液静置至少12小时直至澄清为止，或可以加入氯化钠来沉淀未反应的Ag+。然后再过滤。任一种处理后，滤液都应是澄清的。搅拌下将滤液滴加入4倍比例的醚中。将产物过滤并随后用醚彻底洗涤。将产物重新溶于CH2Cl2中，并滤掉残渣。然后将产物在50℃下真空干燥，并用1H NMR分析。NMR结果为：(丙酮-d 6)：δ8.05(d，2H)，7.22(d，2H)，3.91(s，3H)和3.41ppm(s，6H)。
光刻胶实施例1
通过将0.05g在合成实施例1中合成的水溶性光活性化合物加入99.95g R200溶液(从Clariant Corp.，Electronic MaterialsBusiness Unit，Somerville，NJ 08876获得)中，制备水性负性光刻胶溶液。R200是聚乙烯醇缩醛和亚乙基脲树脂(交联剂)在水/异丙醇为94/6 wt％的溶液中的混合物。
光刻胶实施例2
将0.081g 0.4956％的氢氧化四丁铵(TBAH)水溶液加入40.124g光刻胶实施例1所得物中。
光刻胶实施例3
将0.6045g 0.4956％的氢氧化四丁铵(TBAH)水溶液加入148.85g R200和0.15g在合成实施例1中合成的水溶性光活性化合物中。
光刻胶实施例4
将0.30g 0.4956％的氢氧化四丁铵(TBAH)水溶液加入149.925g R200和0.075g在合成实施例1中合成的水溶性光活性化合物中。
平板印刷实施例1
将光刻胶实施例1和2制备的溶液涂覆到6”HMDS打底的硅片上，然后在70℃下轻烘烤60s以得到0.48微米(μm)厚的薄膜。将涂覆过的硅片在ASML DUV分档器上用248nm波长的光曝光。从5mJ/cm2开始，以能量增量为1mJ/cm2成像出一个dose-to-clear(DTC)图案。照明模式设定在常规值，NA为0.57和外σ为0.75。曝光后，膜片在130℃下烘烤70s。
然后将膜片浸渍在AZR2显影剂(水与异丙醇的混合物)中，其从Clariant Corp.，Electronic Materials Business Unit，Somerville，NJ 08876获得。16.2s内清除未曝光区的所有薄膜。在该步骤后，用去离子水冲洗60s并将薄膜干燥。未曝光区上没有残留光刻胶涂层，在用光刻胶实施例1和光刻胶实施例2制备的溶液涂覆过的膜片上能清楚观察到已曝光的10×10 DTC图案，得到清晰的正方形图案的光刻胶图像。
通过Nanospec薄膜厚度测量工具测定光刻胶薄膜厚度与照射剂量的函数关系，绘制为对比曲线，如图1所示。
平版印刷实施例2
将光刻胶实施例3和4制备的溶液涂覆到硅片上以得到0.48μm+/-0.1μm的厚度。膜片在ISA 0.60 NA 193nm微型分档器上曝光，然后以接触模式于热板上在130℃下再烘70s。将膜片浸渍在AZR2显影剂中16.5s。在该步骤后，用去离子水冲洗60s并进行干燥。通过Nanospec薄膜厚度测量工具测定光刻胶薄膜厚度与照射剂量的函数关系，图2和3中分别绘制光刻胶实施例3和4的对比曲线。
Claims (13)
1.一种负性的水性光刻胶组合物，该组合物包含：
(a)含有至少一种结构(1)单元的聚合物，
其中R1表示氢或(C1-C4)烷基，n＝1～4；
(b)水溶性光活性化合物，该光活性化合物具有结构(2)，
其中，R2表示氢、烷基、-O(烷基)、-(烷基)OH、羟基苯基或多羟基苯基，R3和R4独立地表示(C1-C4)烷基，m＝1～3，和X-是阴离子；
(c)交联剂；和
(d)溶剂组合物。
2.根据权利要求1的光刻胶组合物，其中溶剂组合物是水或水与(C1-C4)烷基醇的混合物。
3.根据权利要求1的光刻胶组合物，其中聚合物含有另外的非芳族单元。
4.根据权利要求3的光刻胶组合物，其中非芳族单元选自乙烯醇、乙烯基吡咯烷酮、乙酸乙烯酯和亚甲基醇。
5.根据权利要求1的光刻胶组合物，其中聚合物包含至少10mol％结构1单元。
6.根据权利要求1的光刻胶组合物，其中n＝1，R1选自甲基、乙基、丙基和丁基。
7.根据权利要求1的光刻胶组合物，其中光活性化合物是(4-甲氧基苯基)二甲基锍三氟甲磺酸盐。
8.根据权利要求1的光刻胶组合物，其中交联剂选自三聚氰胺树脂、尿素树脂和甘脲。
9.根据权利要求2的光刻胶组合物，其中醇是异丙醇。
10.一种使负性光刻胶成像的方法，其包括以下步骤：(a)由权利要求1的光刻胶组合物在衬底上形成光刻胶涂层；(b)成像曝光该光刻胶涂层；(c)曝光后烘烤该光刻胶涂层；和(d)用显影剂使该光刻胶涂层显影。
11.根据权利要求10的方法，其中成像曝光的波长在260nm以下。
12.根据权利要求10的方法，其中显影剂选自水，水和(C1-C4)烷基醇的混合物，水和表面活性剂的混合物，和碱的水溶液。
13.根据权利要求12的方法，其中醇是异丙醇。
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| CNB028188969A Expired - Fee Related CN1249525C (zh) | 2001-09-28 | 2002-09-07 | 负作用水性光刻胶组合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6800415B2 (zh) |
| EP (1) | EP1433028A1 (zh) |
| JP (1) | JP4136934B2 (zh) |
| KR (1) | KR100880699B1 (zh) |
| CN (1) | CN1249525C (zh) |
| MY (1) | MY129900A (zh) |
| TW (1) | TW591335B (zh) |
| WO (1) | WO2003029900A1 (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235348B2 (en) * | 2003-05-22 | 2007-06-26 | Taiwan Semiconductor Manufacturing Co., Ltd. | Water soluble negative tone photoresist |
| US7678527B2 (en) * | 2003-10-16 | 2010-03-16 | Intel Corporation | Methods and compositions for providing photoresist with improved properties for contacting liquids |
| US7033735B2 (en) * | 2003-11-17 | 2006-04-25 | Taiwan Semiconductor Manufacturing Co., Ltd. | Water soluble negative tone photoresist |
| US20050148679A1 (en) * | 2003-12-29 | 2005-07-07 | Chingfan Chiu | Aryl sulfonium salt, polymerizable composition and polymerization method of the same |
| KR100680426B1 (ko) * | 2004-12-30 | 2007-02-08 | 주식회사 하이닉스반도체 | 포토레지스트 패턴 코팅용 수용성 조성물 및 이를 이용한미세패턴 형성 방법 |
| US7238624B2 (en) * | 2005-03-01 | 2007-07-03 | Taiwan Semiconductor Manufacturing Company, Ltd. | System and method for manufacturing semiconductor devices using a vacuum chamber |
| KR100745901B1 (ko) * | 2005-05-19 | 2007-08-02 | 주식회사 하이닉스반도체 | 포토레지스트 패턴 코팅용 조성물 및 이를 이용한 미세패턴형성 방법 |
| KR20080057562A (ko) * | 2006-12-20 | 2008-06-25 | 주식회사 하이닉스반도체 | 반도체 소자의 미세 패턴 형성 방법 |
| EP2138531B1 (en) * | 2007-04-11 | 2014-10-29 | Sekisui Chemical Co., Ltd. | Method for production of crosslinked polyvinyl acetal resin, and crosslinked polyvinyl acetal resin |
| JP5236103B1 (ja) * | 2012-07-13 | 2013-07-17 | 株式会社ジェイ・エム・シー | 臓器モデルの製造方法、臓器モデル製造用の型、及び臓器モデル |
| CN103529648A (zh) * | 2013-09-26 | 2014-01-22 | 刘超 | 负型感光材料 |
| WO2018212943A1 (en) * | 2017-05-16 | 2018-11-22 | Applied Materials, Inc. | Wire grid polarizer manufacturing methods using frequency doubling interference lithography |
| US10274847B2 (en) * | 2017-09-19 | 2019-04-30 | Taiwan Semiconductor Manufacturing Co., Ltd. | Humidity control in EUV lithography |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3711263A1 (de) | 1987-04-03 | 1988-10-13 | Hoechst Ag | Lichtempfindliches gemisch, daraus hergestelltes lichtempfindliches kopiermaterial und verfahren zur herstellung von druckformen |
| US5691101A (en) * | 1994-03-15 | 1997-11-25 | Kabushiki Kaisha Toshiba | Photosensitive composition |
| JPH07253668A (ja) * | 1994-03-15 | 1995-10-03 | Toshiba Corp | 水溶性感光性組成物 |
| US5536616A (en) | 1994-09-21 | 1996-07-16 | Cornell Research Foundation, Inc. | Photoresists containing water soluble sugar crosslinking agents |
| US5648196A (en) | 1995-07-14 | 1997-07-15 | Cornell Research Foundation, Inc. | Water-soluble photoinitiators |
| JPH09127693A (ja) * | 1995-11-07 | 1997-05-16 | Kansai Paint Co Ltd | 水系感光性着色組成物及びカラーフィルタの製造方法 |
| TW329539B (en) | 1996-07-05 | 1998-04-11 | Mitsubishi Electric Corp | The semiconductor device and its manufacturing method |
| US5998092A (en) | 1998-05-27 | 1999-12-07 | Clariant International, Ltd. | Water soluble negative-working photoresist composition |
| JP2000010280A (ja) | 1998-06-24 | 2000-01-14 | Toyobo Co Ltd | 感光性樹脂組成物および感光性樹脂積層体 |
| JP3950584B2 (ja) | 1999-06-29 | 2007-08-01 | Ａｚエレクトロニックマテリアルズ株式会社 | 水溶性樹脂組成物 |
-
2001
- 2001-09-28 US US09/966,958 patent/US6800415B2/en not_active Expired - Lifetime
-
2002
- 2002-09-07 KR KR1020047004329A patent/KR100880699B1/ko active IP Right Grant
- 2002-09-07 CN CNB028188969A patent/CN1249525C/zh not_active Expired - Fee Related
- 2002-09-07 WO PCT/EP2002/010026 patent/WO2003029900A1/en active Application Filing
- 2002-09-07 JP JP2003533052A patent/JP4136934B2/ja not_active Expired - Fee Related
- 2002-09-07 EP EP02777031A patent/EP1433028A1/en not_active Withdrawn
- 2002-09-11 TW TW091120721A patent/TW591335B/zh not_active IP Right Cessation
- 2002-09-26 MY MYPI20023590A patent/MY129900A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6800415B2 (en) | 2004-10-05 |
| TW591335B (en) | 2004-06-11 |
| US20030077539A1 (en) | 2003-04-24 |
| MY129900A (en) | 2007-05-31 |
| JP2005504362A (ja) | 2005-02-10 |
| CN1559023A (zh) | 2004-12-29 |
| KR100880699B1 (ko) | 2009-02-02 |
| EP1433028A1 (en) | 2004-06-30 |
| WO2003029900A1 (en) | 2003-04-10 |
| JP4136934B2 (ja) | 2008-08-20 |
| KR20040044987A (ko) | 2004-05-31 |
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