CN1280321C - 光致抗蚀共聚物 - Google Patents

光致抗蚀共聚物 Download PDF

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CN1280321C
CN1280321C CNB031063527A CN03106352A CN1280321C CN 1280321 C CN1280321 C CN 1280321C CN B031063527 A CNB031063527 A CN B031063527A CN 03106352 A CN03106352 A CN 03106352A CN 1280321 C CN1280321 C CN 1280321C
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norbornylene
carboxylic acid
formula
multipolymer
photoresist
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CN1478800A (zh
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郑载昌
卜喆圭
白基镐
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SK Hynix Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
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    • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
    • C08F232/04—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists

Abstract

一种光致抗蚀剂，包括从双环烯衍生物、马来酸酐和/或碳酸亚乙烯酯制备的共聚物，其中共聚物分子量范围是3000-100000。该光致抗蚀剂可用于使用远紫外光作光源的亚微级平版印刷。除耐刻蚀性和耐热性高以外，该光致抗蚀剂具有良好粘附性并可在TMAH溶液中显影。

Description

光致抗蚀共聚物
本发明涉及制造集成电路。本发明具体涉及提供一种氟化氩(ArF)光致抗蚀树脂及其制备方法，并且具体涉及使用远紫外光(DUV)作光源适合亚微级平版印刷的光致抗蚀共聚物和这种共聚物的制备方法。本发明还提供一种包括这种树脂的光致抗蚀剂。
最近在半导体器件领域流行化学放大光致抗蚀，因为发现它们对DUV光敏感，认识到这种光作光源适于实现半导体器件的高度集成。化学放大光致抗蚀一般有光酸(photoacid)产生剂和具有对酸反应灵敏的化学结构的基体聚合物。
关于这种光致抗蚀的作用机理，当光致抗蚀剂通过掩膜在DUV光源下曝光时，通过光酸产生剂的作用产生光子，然后与基体聚合物的主链或侧链起反应。这种反应通过例如分解、交联或改变极性的方式使共聚物结构转化来增大共聚物在显影溶液中的溶解度。因此，在用显影溶液处理时，在曝光区域的共聚物溶解而未曝光区域的共聚物保持不溶，从而在基体上留下掩膜的形状作为正性图象。与此同时，光平版印刷形成的图形的分辨率一般与光源的波长成正比。所以，波长越短形成的图形越精细。作为致力于寻找适合提高分辨率的光源的结果，开发出了使半导体器件的集成达到1千兆或更高程度的远紫外光。
一般来说，要求光致抗蚀剂有高度的耐刻蚀性和耐热性。另外，用于ArF的光致抗蚀剂应当在2.38％四甲基铵氢氧化物(TMAH)溶液中显影。然而事实上，得到完全令人满意特性的光致抗蚀树脂是困难的。
例如，具有聚甲基丙烯酸甲酯主链的树脂，它对上述短波长的光透明，该树脂是容易合成的。但是在实际应用时由于它耐刻蚀性差和在TMAH中显影差而存在一些问题。在主链引入脂环单体可改良耐刻蚀性。但事实上合成具有由脂环构成主链的树脂是不可能的。
为了解决上述问题，AT&T公司(或贝尔实验室)研究出一种树脂，其主链被降冰片烯、丙烯酸酯和马来酸酐取代，可用以下化学式I表示：
式I中，马来酸酐部分A的使用为的是聚合脂环烯烃基团，而且使得在2.38％TMAH溶液中良好溶解甚至在未曝光时依然如是。这种溶解可以通过增加主链上被叔丁基取代的Y部分的比例而得到抑制。如果这样，起增强与基体粘附性功能的Z部分的比例相对变得较小，这导致从基体如晶片中释放出光致抗蚀剂。结果，这种方法不可能形成好的图形。贝尔实验室建议采用含胆甾醇化合物作为溶解抑制剂的双组份体系。然而，该溶解抑制剂要求加入大量例如约30％(重量)的树脂，使得贝尔实验室的树脂在用于光致抗蚀树脂时在原则上有问题。
因此，本发明的目的在于克服现有技术中的上述缺点，并提供在显影溶液中几乎不溶解、其结构不发生化学变化另外耐蚀刻性、耐热性优越的ArF光致抗蚀树脂。
本发明的一个目的是提供一种光致抗蚀共聚物。
本发明另一个目的是提供所述光致抗蚀共聚物的制备方法。
本发明的又一个目的是提供一种包括光致抗蚀共聚物的光致抗蚀剂。
本发明再一个目的是提供一种光致抗蚀剂的制备方法。
本发明另一个目的是提供一种集成电路器件的制备方法。
本发明再一个目的是提供一种部分完成的半导体器件。
本发明新的光致抗蚀共聚物是由以下物质制备：一种或多种式II的双环烯化合物、式III的马来酸酐和/或式IV的碳酸亚乙烯酯：
(式II)
Figure C0310635200061
其中R代表氢或含有1-10取代或未取代碳原子的直链或支链烷基，且n是1或2，
(式III)
Figure C0310635200062
(式IV)
Figure C0310635200071
式II中优选的R基团选自的组包括氢、2-羟乙基和叔丁基。亦即双环烯的优选实例包括5-降冰片烯-2-羧酸2-羟乙酯、5-降冰片烯-2-羧酸叔丁酯、5-降冰片烯-2-羧酸、双环[2，2，2]辛-5-烯-2羧酸2-羟乙酯、双环[2，2，2]辛-5-烯-2羧酸叔丁酯和/或双环[2，2，2]辛-5-烯-2羧酸。
本发明共聚物的分子量为大约3000-100000。
本发明优选的共聚物之一从以下物质制备：碳酸亚乙烯酯和一种或多种其中R是氢、2-羟乙基和叔丁基且n是1的双环烯。亦即双环烯选自5-降冰片烯-2-羧酸2-羟乙酯、5-降冰片烯-2-羧酸叔丁酯、5-降冰片烯-2-羧酸。
本发明的新共聚物由一种或多种式II的双环烯化合物、式III的马来酸酐或式IV的碳酸亚乙烯酯构成，可按照常规游离基聚合技术使用游离基聚合引发剂来制备。
它们可以通过本体聚合或溶液聚合而得到聚合。关于聚合溶剂，有环己酮、甲乙酮、苯、甲苯、二烷、二甲酰胺、四氢呋喃等，可单独或结合使用。聚合通常在存在引发剂诸如过氧化苯甲酰、偶氮双异丁腈(AIBN)、过氧化乙酰、过氧化月桂酰和过乙酸叔丁酯的情况下进行。
在半导体器件上用于形成正性精细图形的正性光致抗蚀组合物的制备方法是，将本发明新的光致抗蚀共聚物与一种光酸产生剂以常规方式在一种有机溶剂内混和。关于配方，共聚物的量取决于有机溶剂、光酸产生剂和平版印刷的条件，优选所用有机溶剂的重量为大约10-30％。
为制造光致抗蚀剂，首先将本发明共聚物或者以10-30wt％的量溶于环己酮，然后将占抗蚀聚合物重量约0.1-10％作光酸产生剂的一种嗡盐或有机磺酸添加进去。用超细过滤器过滤这种溶液，得到光致抗蚀溶液。
将这种光致抗蚀溶液喷涂到硅晶片上，之后置于烘箱或加热板上于80-150℃烘烤软化1-5分钟。可采用远紫外光或受激发射的激光作光源的分步器进行曝光工艺。此后，使晶片于100-200℃温度进行烘烤后步骤。通过使烘烤后的晶片在2.38％TMAH溶液中浸渍90秒可得到一种正抗蚀的超精细图象。
根据下面实施例可更好了解本发明，所述实施例仅供说明绝非限制本发明。
实施例1
5-降冰片烯-2-羧酸2-羟乙酯的合成
下面式V的双环戊二烯在大约120-170℃裂解，从而得到式VI的环戊二烯。
(式V)
Figure C0310635200081
(式VI)
式VI的环戊二烯和式VII的丙烯酸2-羟乙酯以同样的速率溶于乙醚或四氢呋喃。随后在大约-30℃到60℃反应24小时。利用旋转蒸发器去除溶剂，真空蒸馏残留物得到下面式VIII的5-降冰片烯-2-羧酸2-羟乙酯，它是内外向混和型。
(式VII)
Figure C0310635200092
(式VIII)
Figure C0310635200093
实施例II
5-降冰片烯-2-羧酸叔丁酯的合成
在反应器内首先放入66g环戊二烯，然后与500g四氢呋喃混和，再向反应器内添加128g丙烯酸叔丁酯。然后在-30℃到60℃的温度搅拌反应物进行反应10小时。反应完成后利用旋转蒸发器蒸发溶剂，之后真空蒸馏得到标题化合物，产率90％。
实施例III
共聚物的合成
将实施例I合成的91g 5-降冰片烯-2-羧酸(2-羟)乙酯、实施例II合成的97g 5-降冰片烯-2-羧酸叔丁酯和86g的碳酸亚乙烯酯放入反应器中，之后用氮气吹洗。在50-200个大气压的压力下于65-120℃进行反应6小时。反应完成后旋转蒸发器去除部分溶剂，溶剂的残留物在乙醚中沉淀。过滤沉淀并在真空烘箱中干燥。所得产物可用作光致抗蚀树脂。
实施例IV
共聚物的合成
将实施例I合成的91g 5-降冰片烯-2-羧酸(2-羟)乙酯、实施例II合成的97g 5-降冰片烯-2-羧酸叔丁酯和98g的马来酸酐放入反应器中，之后用氮气吹洗。于65-120℃进行6小时反应。反应完成后采用旋转蒸发器去除部分溶剂，溶剂的残留物在乙醚中沉淀。过滤沉淀并在真空烘箱中干燥。所得产物可用作光致抗蚀树脂。
实施例V
共聚物的合成
将98g的2-羟乙基-双环[2，2，2]辛-5-烯、104g的双环[2，2，2]辛-5-烯-丙烯酸叔丁酯和86g的碳酸亚乙烯酯放入反应器，然后与2升四氢呋喃溶剂混合。之后向反应器加入1.5g的偶氮双异丁腈(AIBN)，再用氮气吹洗反应器。在65℃进行6小时反应。反应完成后用旋转蒸发器去除部分溶剂，并使溶剂的残留物在乙醚中沉淀。过滤沉淀并在真空烘箱中干燥。所得产物可用作光致抗蚀树脂。
实施例VI
共聚物的合成
将98g的2-羟乙基-双环[2，2，2]辛-5-烯、104g的双环[2，2，2]辛-5-烯-丙烯酸叔丁酯和86g的马来酸酐放入反应器，然后与2升四氢呋喃溶剂混合。之后向反应器中加入1.5g的偶氮双异丁腈(AIBN)，再用氮气吹洗反应器。在65℃进行反应6小时。反应完成后用旋转蒸发器去除部分溶剂，溶剂的残留物在乙醚中沉淀。过滤沉淀并在真空烘箱中干燥。所得产物可用作光致抗蚀树脂。
实施例VII
ArF光致抗蚀树脂的合成
聚[5-降冰片烯-2-羧酸2-羟乙酯/5-降冰片烯-2-羧酸叔丁酯/5-降冰片烯2-羧酸/马来酸酐]的合成
将1摩尔下面式IX的马来酸酐、0.05-0.8摩尔的5-降冰片烯-2-羧酸2-羟乙酯、0.5-0.95摩尔的5-降冰片烯-2-羧酸叔丁酯和0.01-0.2摩尔的5-降冰片烯-2-羧酸溶于四氢呋喃或甲苯中。此后溶解在一种溶剂中。自由基间反应的条件是温度大约60-70℃、氮气或氩气气氛、存在0.5-10g的偶氮双异丁腈(AIBN)作引发剂，反应4-24小时。将这种聚合得到的树脂在乙醚或己烷中沉淀并干燥，得到下面式X的聚[5-降冰片烯-2-羧酸2-羟乙酯/5-降冰片烯-2-羧酸叔丁酯/5-降冰片烯2-羧酸/马来酸酐]树脂。
(式IX)
5-降冰片烯-2-                   5-降冰片烯-2-                  马来酸酐        5-降冰片烯
羧酸2-羟乙酯                    羧酸叔丁酯                                     -2-羧酸
(式X)
实施例VIII
光致光刻薄膜的制备和图形的形成
10g的聚[5-降冰片烯酸-2-羧酸2-羟乙酯/5-降冰片烯-2-羧酸叔丁酯/5-降冰片烯2-羧酸/马来酸酐]溶于40g的丙酸3-甲氧基甲酯溶剂中，并添加大约0.02-1g的三氟甲磺酸三苯基锍或三氟甲磺酸二丁基萘基锍或这两种光酸产生剂的混和物。充分搅拌后，使混和物通过0.10μm的过滤器。将这种滤出物涂覆在晶片上并形成图形。当涂层大约0.6μm厚时，得到分辨率0.14μm的纵向L/S图形。
如上所述，由本发明的新共聚物制备的光致抗蚀剂具有优异的耐刻蚀性和耐热性。另外，它可在2.38％TMAH溶液中显影。还显示出良好的粘附性，使得从0.7μm厚度的光致抗蚀涂层能够得到具有令人满意分辨率和聚焦深度的0.15μm L/S图形。结果，例如将5-降冰片烯-2-羧酸2-羟乙酯引入树脂主链使得合成的光致抗蚀剂在粘附性方面是优异的。
本发明以说明的方式进行了详述，应当了解，所用术语完全是用于叙述而不是限制本发明。
根据以上技术完全可能对本发明作许多改良和变化。因此，应当了解，本发明实际上可在待批权利要求书限定范围而不是说明书的具体详述的范围内实施。

Claims (4)

1.一种光致抗蚀共聚物，其包括通过共聚合以下物质得到的重复单元，所述物质包括：
A)式VIII所示的5-降冰片烯-2-羧酸2-羟乙酯；
B)如式III所示的马来酸酐或式IV所示的碳酸亚乙烯酯；
C)除了A)组分以外的式II所示的其它双环烯单体：
Figure C031063520002C1
其中R表示氢或含有1-10个取代或未取代的碳原子的直链或支链烷基；并且n为1或2，
Figure C031063520002C2
其中重复单元中的摩尔比为：(A)∶(B)∶(C)为0.05-0.8∶1∶0.51-1.15。
2.根据权利要求1的光致抗蚀共聚物，其中所述式VIII的单体是从环戊二烯和丙烯酸2-羟乙酯制备的。
3.根据权利要求1的光致抗蚀共聚物，其中所述的共聚物由(A)5-降冰片烯-2-羧酸2-羟乙酯、(C1)5-降冰片烯-2-羧酸叔丁酯、(B)马来酸酐和(C2)5-降冰片烯-2-羧酸进行共聚合来制备的，(式IX)
Figure C031063520003C1
     5-降冰片烯-2-         5-降冰片烯-2-                 马来酸酐           5-降冰片烯-2-羧酸2-羟乙酯          羧酸叔丁酯                                       羧酸
其中(A)∶(C1)∶(B)∶(C2)的相对摩尔比为0.05-0.8∶0.5-0.95∶1∶0.01-0.2。
4.根据权利要求1的光致抗蚀共聚物，其中所述的共聚物包括下式X所示的重复单元：
(式X)
Figure C031063520003C2
其中x、y和z分别代表各单体的摩尔比，X∶Y∶Z为0.05-0.8∶0.5-0.95∶0.01-0.2，以及所述共聚物的分子量为3000-100000。
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IT1297352B1 (it) 1999-09-01
US6132926A (en) 2000-10-17
TW388926B (en) 2000-05-01
KR100265597B1 (ko) 2000-09-15
JP3220745B2 (ja) 2001-10-22
JP4025956B2 (ja) 2007-12-26
NL1007939C2 (nl) 1998-11-17
DE19758244A1 (de) 1998-07-02
CN1983029B (zh) 2012-03-14
JP2002003541A (ja) 2002-01-09
ITTO971150A1 (it) 1999-06-30
CN1478800A (zh) 2004-03-03
GB2320718A9 (en) 1999-08-17
GB2320718A8 (en) 1999-08-17
DE19758244B4 (de) 2014-08-14
FR2757868B1 (fr) 2003-11-14
JP4999499B2 (ja) 2012-08-15
JP2002003542A (ja) 2002-01-09
CN1983029A (zh) 2007-06-20
GB9727474D0 (en) 1998-02-25
GB2320718B (en) 2000-09-13
KR19980063345A (ko) 1998-10-07
JPH10218947A (ja) 1998-08-18
NL1007939A1 (nl) 1998-07-01
GB2320718A (en) 1998-07-01
FR2757868A1 (fr) 1998-07-03

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