CN101218541B - 用于厚膜成像的光致抗蚀剂组合物 - Google Patents
用于厚膜成像的光致抗蚀剂组合物 Download PDFInfo
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- CN101218541B CN101218541B CN2006800253403A CN200680025340A CN101218541B CN 101218541 B CN101218541 B CN 101218541B CN 2006800253403 A CN2006800253403 A CN 2006800253403A CN 200680025340 A CN200680025340 A CN 200680025340A CN 101218541 B CN101218541 B CN 101218541B
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Abstract
本发明提供可用于使厚膜成像的光敏光致抗蚀剂组合物，它包括在含水碱性显影剂中不溶但在显影之前变得可溶的聚合物，一旦辐照则产生强酸的光致产酸剂和可光漂白的染料。本发明进一步提供使本发明的光致抗蚀剂成像的方法，特别是其中光致抗蚀剂的厚度最多200微米的情况和其中该方法包括单步曝光的情况。
Description
技术领域
本发明涉及特别地可用于使厚膜成像的光敏光致抗蚀剂组合物，它包括成膜的碱不溶性树脂、生产强酸的光致产酸剂、溶剂和可光漂白的染料，所述可光漂白的染料在与光致产酸剂相同的辐射下吸收且优选具有与光致产酸剂类似或比其低速的光漂白。优选地，光致抗蚀剂膜的厚度大于2微米(μm)。本发明进一步提供涂布本发明的光敏组合物并使之成像的方法。
背景技术
光致抗蚀剂组合物用于制造小型化电子组件的微型平版印刷(microlithography)方法，例如用于制造计算机芯片和集成电路。一般地，在这些方法中，首先施加光致抗蚀剂组合物的涂布膜到基底材料，例如制造集成电路所使用的硅片上。然后烘烤涂布的基底，以蒸发在光致抗蚀剂组合物内的任何溶剂并在基底上固定涂层。接下来将烘烤过的基底的涂布表面成像式曝光于辐射线下。
这一辐射曝光引起在涂布表面的曝光区域内的化学转变。可见光、紫外(UV)光、电子束和X射线辐射能是当今在微型平版印刷方法中常用的辐射线类型。在这一成像式曝光之后，用显影剂溶液处理涂布的基底，溶解并除去或者辐射线曝光或者未曝光的基底的涂布表面。
存在两类光致抗蚀剂组合物，即负性工作和正性工作的光致抗蚀剂组合物。当负性工作的光致抗蚀剂组合物成像式曝光于辐射线下时，曝光于辐射线下的抗蚀剂组合物区域不那么可溶于显影剂溶液(例如发生交联反应)，而光致抗蚀剂涂层的未曝光区域保持相对可溶于这一溶液中。因此，用显影剂处理曝光的负性工作的抗蚀剂引起除去光致抗蚀剂涂层的未曝光区域并在涂层内产生负性图像。于是露出光致抗蚀剂组合物在其上沉积的下部基底表面的所需部分。
另一方面，当正性工作的光致抗蚀剂组合物成像式曝光于辐射线下时，曝光于辐射线下的光致抗蚀剂组合物的那些区域更加可溶于显影剂溶液(例如，发生重排反应)，而没有曝光的那些区域保持相对不溶于显影剂溶液。因此，用显影剂处理曝光的正性工作的光致抗蚀剂将引起除去涂层的曝光区域并在光致抗蚀剂涂层内产生正性图像。再次露出下部基底表面的所需部分。
在这一显影操作之后，可用基底蚀刻剂溶液、等离子体气体处理新的部分未受保护的基底，或者使金属或金属复合材料沉积在其中显影期间除去光致抗蚀剂涂层的基底空间内。其中光致抗蚀剂涂层仍然保留的基底区域受到保护。随后，可在汽提操作过程中除去光致抗蚀剂涂层的剩余区域，从而留下构图的基底表面。在一些情况下，希望在显影步骤之后和蚀刻步骤之前，热处理其余的光致抗蚀剂层，以增加它对下部基底的粘合性。
在构图结构的制造，例如晶片级包装中，当互连密度增加时，使用电化学沉积的电连接点。例如，参见Solomon，ElectrochemicallyDeposited Solder Bumps for Wafer-Level Packaging，Packaging/Assembly，Solid State Technology。在晶片级包装中用于再分配的金隆起焊盘、铜柱(copper post)和铜线要求抗蚀剂模具，在高级互连技术中，所述抗蚀剂模具随后被电镀，形成最终的金属结构。与在临界层(critical layer)的IC制造中所使用的光致抗蚀剂相比，抗蚀剂层非常厚。特征尺寸和抗蚀剂厚度二者典型地在2微米-100微米范围内，以便在光致抗蚀剂中必须构图高的长径比(抗蚀剂厚度与线尺寸之比)。
作为微电子机械机器使用而制造的器件也使用非常厚的光致抗蚀剂膜来确定机器的组件。
含可溶可熔酚醛树脂和重氮醌化合物作为光活性化合物的正性作用的光致抗蚀剂是本领域中众所周知的。典型地在酸催化剂，例如草酸存在下，通过缩合甲醛和一种或更多种多取代的酚类，生产可溶可熔酚醛树脂。通常通过使多羟基酚类化合物与重氮萘醌酸或其衍生物反应，获得光活性化合物。可溶可熔酚醛树脂也可与重氮醌反应并与聚合物结合。已发现，基于仅仅可溶可熔酚醛树脂/重氮化物的光致抗蚀剂不具有光敏性或者一些类型的工艺所需的侧壁陡峭度，特别是对于厚膜来说。
本发明的目的是提供使厚至200微米(μm)的膜成像有用的化学放大的光致抗蚀剂，它提供良好的平版印刷性能，尤其是光敏性，高的长径比，垂直的侧壁，在金属和硅基底上改进的粘合性，与电镀溶液和工艺的相容性，降低的抗蚀剂膜致裂性和改进的环境稳定性。本发明的发明人已发现，含聚合物(该聚合物在含水碱性显影剂中不溶，但在显影之前变为可溶)、一旦辐照则产生强酸的光致产酸剂和可光漂白的染料(该染料在与光致产酸剂相同的辐射波长下吸收，和优选与光致产酸剂相比，具有类似或比其低速度的光漂白)的光致抗蚀剂，当成像时，提供所需的平版印刷性能，特别是对于最多200微米(μm)的厚膜来说。
发明内容
本发明涉及一种光致抗蚀剂组合物，它包括在含水碱性显影剂中不溶，但在显影之前成为可溶的聚合物，一旦辐照则产生强酸的光致产酸剂，和在与光致产酸剂相同的辐射下吸收的可光漂白的染料。优选地，该可光漂白的染料具有与光致产酸剂类似或低速度的光漂白。本发明还涉及使这种光致抗蚀剂组合物成像的方法，和以上所述的组合物作为光致抗蚀剂的用途。
具体实施方式
本发明的新型光致抗蚀剂提供可用于使厚膜成像的光敏光致抗蚀剂组合物，它包括在含水碱性显影剂中不溶，但在显影之前成为可溶的聚合物，一旦辐照则产生强酸的光致产酸剂，和可光漂白的染料。可光漂白的染料和光致产酸剂吸收相同的辐射线，所述辐射线是使光致抗蚀剂曝光所使用的辐射线。此外，与光致产酸剂的光解速度相比，可光漂白的染料具有大致类似或比其低速度的光漂白。染料的漂白速度优选没有显著高于光致产酸剂的光解。优选在抗蚀剂剂量清理(clear)时，应当发生不大于95％的染料漂白。抗蚀剂的清理剂量定义为使用给定的工艺条件，全部抗蚀剂厚度完全显影所要求的最小曝光剂量。本发明进一步提供以上所述的组合物作为光致抗蚀剂的用途，尤其用于形成厚至200微米(μm)的膜。本发明进一步提供使本发明的光致抗蚀剂成像的方法，特别是其中光致抗蚀剂厚度大于2微米(μm)的情况，和其中该方法包括单一的曝光步骤的情况。可使厚至200微米(μm)的光致抗蚀剂膜成像。光致抗蚀剂尤其可用于使在要求长宽比大于3的铜基底上的光致抗蚀剂膜成像(长宽比是光致抗蚀剂图案的高度与宽度之比)。
本发明的光致抗蚀剂组合物中的聚合物不溶于含水碱性显影剂中，但在显影之前可溶。典型地，聚合物是通过酸不稳定基团受到保护的含水碱性可溶聚合物。碱可溶的聚合物可以是含衍生于包括羟基或酯基的单体衍生单元的均聚物或共聚物。优选含酚基，例如含羟基苯乙烯单体的聚合物。酚基用酸不稳定基团，例如酯和/或缩醛、叔丁氧基羰基或烷氧基羰基烷基(例如(叔丁氧基羰基)甲基)封端。还优选(烷基)丙烯酸酯，所述(烷基)丙烯酸酯可共聚，以提供酸不稳定的酯基，其实例是丙烯酸叔丁酯、甲基丙烯酸叔丁酯和丙烯酸甲基金刚烷酯。优选羟基苯乙烯和丙烯酸酯的共聚物。该聚合物可进一步包括不具有酸不稳定基团且衍生于可聚合单体，例如苯乙烯、乙酰氧基苯乙烯和甲氧基苯乙烯的共聚单体单元。
可用酸不稳定基团封端的羟基苯乙烯基树脂的实例包括聚(4-羟基苯乙烯)；聚(3-羟基苯乙烯)；聚(2-羟基苯乙烯)；和4-、3-或2-羟基苯乙烯与其他单体的共聚物，尤其二元聚合物和三元聚合物。此处可用的其他单体的实例包括4-、3-或2-乙酰氧基苯乙烯、4-、3-或2-烷氧基苯乙烯、苯乙烯、α-甲基苯乙烯、4-、3-或2-烷基苯乙烯、3-烷基-4-羟基苯乙烯、3，5-二烷基-4-羟基苯乙烯、4-、3-或2-氯苯乙烯、3-氯-4-羟基苯乙烯、3，5-二氯-4-羟基苯乙烯、3-溴-4-羟基苯乙烯、3，5-二溴-4-羟基苯乙烯、乙烯基苄基氯、2-乙烯基萘、乙烯基蒽、乙烯基苯胺、乙烯基苯甲酸、乙烯基苯甲酸酯、N-乙烯基吡咯烷酮、1-乙烯基咪唑、4-或2-乙烯基吡啶、1-乙烯基-2-吡咯烷酮、N-乙烯基内酰胺、9-乙烯基咔唑、苯甲酸乙烯酯、丙烯酸及其衍生物，即丙烯酸甲酯及其衍生物，丙烯酰胺及其衍生物，甲基丙烯酸及其衍生物，即甲基丙烯酸甲酯及其衍生物，甲基丙烯酰胺及其衍生物，丙烯腈、甲基丙烯腈、4-乙烯基苯甲酸及其衍生物，即4-乙烯基苯甲酸酯、4-乙烯基苯氧基乙酸及其衍生物，即4-乙烯基苯氧基乙酸酯、马来酰亚胺及其衍生物、N-羟基马来酰亚胺及其衍生物、马来酸酐、马来酸/富马酸及其衍生物，即马来酸酯/富马酸酯、乙烯基三甲基硅烷、乙烯基三甲氧基硅烷或乙烯基降冰片烯及其衍生物。此处可用的优选的其他单体的另一实例包括异丙烯基苯酚、丙烯基苯酚、聚(4-羟苯基)(甲基)丙烯酸酯、聚(3-羟苯基)(甲基)丙烯酸酯、聚(2-羟苯基)(甲基)丙烯酸酯、N-(4-羟苯基)(甲基)丙烯酰胺、N-(3-羟苯基)(甲基)丙烯酰胺、N-(2-羟苯基)(甲基)丙烯酰胺、N-(4-羟苄基)(甲基)丙烯酰胺、N-(3-羟苄基)(甲基)丙烯酰胺、N-(2-羟苄基)(甲基)丙烯酰胺、3-(2-羟基六氟丙基-2)苯乙烯和4-(2-羟基六氟丙基-2)苯乙烯。
如上所述，对于本发明的光致抗蚀剂来说，通过用酸可解离的保护基保护树脂上的碱可溶的基团，使得羟基苯乙烯基树脂变得碱不溶。可通过任何合适的方法进行保护基的引入，这取决于在树脂上的碱可溶基团，且本领域的普通技术人员可容易地进行。
例如，当在树脂上的碱可溶基团是酚羟基时，通过任何已知的酸不稳定保护基，优选通过一个或更多个保护基(所述保护基将形成酸可解离的C(O)OC、C-O-C或C-O-Si键)部分或全部保护存在于树脂内的酚羟基。此处可用的保护基的实例包括由烷基或环烷基乙烯基醚形成的缩醛或缩酮基，由合适的三甲基甲硅烷基或叔丁基(二甲基)甲硅烷基前体形成的甲硅烷基醚，由甲氧基甲基、甲氧基乙氧基甲基、环丙基甲基、环己基、叔丁基、戊基、4-甲氧基苄基、邻硝基苄基或9-蒽基甲基前体形成的烷基醚，由叔丁氧基羰基前体形成的碳酸叔丁酯，和由乙酸叔丁酯前体形成的羧酸酯。同样有用的是诸如(叔丁氧基羰基)甲基及其(C1-C6)烷基类似物之类的基团。
当在树脂上的碱可溶基团是羧基时，通过酸不稳定的保护基，优选通过一个或更多个保护基(所述保护基将形成酸可解离的C-O-C或C-O-Si键)，部分或全部保护存在于树脂上的羧基。此处可用的保护基的实例包括由含甲基、甲氧基甲基、甲氧基乙氧基甲基、苄氧基甲基、苯甲酰甲基、N-邻苯二甲酰亚胺基甲基、甲硫基甲基、叔丁基、戊基、环戊基、1-甲基环戊基、环己基、1-甲基环己基、2-氧环己基、甲基戊酰基、二苯基甲基、α-甲基苄基、邻硝基苄基、对甲氧基苄基、2，6-二甲氧基苄基、胡椒基、蒽基甲基、三苯基甲基、2-甲基金刚烷基、四氢吡喃基、四氢呋喃基、2-烷基-1，3-
唑啉基、三甲基甲硅烷基或叔丁基二甲基甲硅烷基的前体形成的烷基或环烷基乙烯基醚和酯。
根据本发明，上述树脂可单独或以两种或更多种的混合物形式使用。
尤其优选含衍生于至少一种下述单体的单元的聚合物，所述单体选自取代的羟基苯乙烯、未取代的羟基苯乙烯、取代的丙烯酸烷酯、未取代的丙烯酸酯。丙烯酸酯可含有酸不稳定的基团或者非酸不稳定的基团。该聚合物可进一步包括不具有酸不稳定基团的单元，例如衍生于基于取代或未取代苯乙烯的单体的那些单元，具有侧挂基团的亚乙基，例如环(C5-C10)烷基、金刚烷基、苯基、羧酸等。
本发明的碱不溶性聚合物的重均分子量范围为约2000-约100,000，优选约3000-约50,000，和更优选约5000-约30,000。该聚合物以范围为光致抗蚀剂全部固体重量的约20-约99wt％，优选约85-约98wt％的水平存在于配方内。
尽管可在光致抗蚀剂中使用任何光活性的化合物，但通常一旦辐照，则能产生强酸的化合物，即新型组合物中的光致产酸剂(PAG)选自在所需曝光波长，优选低于370nm，和更优选365nm下吸收的那些。光产生的酸使光致抗蚀剂中碱不溶性聚合物去保护，在曝光区域内得到在碱性显影剂内可溶的聚合物。可使用产生强酸，尤其磺酸的任何PAG。产生酸的光敏化合物的合适实例包括，但不限于，离子光致产酸剂(PAG)，例如重氮盐、碘鎓盐、锍盐，或非离子PAG，例如重氮磺酰基化合物、磺酰氧基酰亚胺、硝基苄基磺酸酯和酰亚胺基磺酸酯，但可使用一旦辐照，则产生酸的任何光敏化合物。通常以在有机溶剂内可溶的形式使用鎓盐，最常见碘鎓盐或锍盐，其实例是二苯基碘鎓三氟甲磺酸盐、二苯基碘鎓九氟丁磺酸盐、三苯基锍三氟甲磺酸盐、三苯基锍九氟丁磺酸盐和类似物。其他有用的鎓盐，例如在2003年5月16日提交的序列号为10/439472、2003年6月30日提交的10/609735、2003年5月16日提交的10/439753和2004年6月8日提交的10/863042的美国专利申请中公开的那些并在此通过参考引入。一旦辐照则形成酸的可使用的其他化合物是三嗪、
唑、二唑、噻唑、取代2-吡喃酮。PAGS，例如在US2002/0061464中所述的那些也是有用的。酚类磺酸酯、三氯甲基三嗪、双磺酰基甲烷、双磺酰基甲烷或双磺酰基重氮甲烷、三苯基锍三(三氟甲磺酰基)甲基化物、三苯基锍双(三氟甲基磺酰)亚胺、二苯基碘鎓三(三氟甲磺酰基)甲基化物、二苯基碘鎓双(三氟甲基磺酰)亚胺、N-羟基萘二甲酰亚胺三氟甲磺酸盐及其同系物也是可能的候选物。
流程式1示出了光活性化合物的一些实例：
流程式1
其中R1-R3独立地为(C1-C8)烷基或(C1-C8)烷氧基取代基，X-是磺酸根抗衡离子，n＝1-20，和R独立地选自(C1-C8)烷基、(C1-C8)烷氧基、苯基、苯乙烯基苯基、(C1-C8)烷氧基-苯乙烯基苯基、呋喃基亚乙基、(C1-C8)烷基取代的呋喃基亚乙基、萘基、(C1-C8)烷基或(C1-C8)烷氧基取代的萘基。
也可使用光活性化合物的混合物。在一个优选的实施方案中，优选碘鎓盐和锍盐作为光活性的化合物，和更优选锍盐作为光活性的化合物。在PAG的另一实施方案中，PAG是三嗪和酰亚胺的混合物。可掺入范围为0.1-10wt％固体，优选0.3-5wt％固体，和更优选0.5-2.5wt％固体的光活性的化合物，优选光致产酸剂。本发明中可用的更多类型的PAGS是三氯甲基三嗪，特别是当用于与其他PAG，例如萘二甲酰亚胺的混合物中时。
本发明的光致抗蚀剂组合物包括碱不溶性聚合物、光致产酸剂和可光漂白的染料。可光漂白的染料优选是在与光致产酸剂相同的辐射下吸收和更优选具有类似或比其低速度的可光漂白的染料。已发现，可通过调节可漂白的染料的类型及其浓度来获得光致抗蚀剂图案的垂直侧壁。优选地，可漂白的染料是多羟基化合物或单羟基酚类化合物的重氮萘醌磺酸酯，该化合物可通过在碱性催化剂存在下，用具有2-7个酚部分的酚类化合物或多羟基化合物酯化1，2-重氮萘醌-5-磺酰氯和/或1，2-重氮萘醌-4-磺酰氯来制备。作为光活性化合物的重氮萘醌及其合成是本领域的技术人员众所周知的。含本发明组分的这些化合物优选是取代的重氮萘醌染料(它在本领域中常规地用于正性光致抗蚀剂配方内)。在例如美国专利号2797213、3106465、3148983、3130047、3201329、3785825和3802885中公开了这种敏化化合物。有用的可光漂白的染料包括，但不限于，通过使酚类化合物，例如羟基二苯甲酮、低聚苯酚、苯酚及其衍生物、可溶可熔酚醛树脂和多取代的多羟基苯基烷烃与(1，2)-重氮萘醌-5-磺酰氯和/或(1，2)-重氮萘醌-4-磺酰氯缩合制备的磺酸酯。在可漂白染料的一个实施方案中，优选单羟基酚类，例如枯基苯酚。在可漂白染料的另一实施方案中，用作可漂白染料主链的每一多羟基化合物分子中的酚部分的数量范围为2-7，和更优选范围为3-5。
多羟基化合物的一些代表性实例是：
(a)多羟基二苯甲酮，例如2，3，4-三羟基二苯甲酮，2，4，4′-三羟基二苯甲酮、2，4，6-三羟基二苯甲酮、2，3，4-三羟基-2′-甲基二苯甲酮、2，3，4，4′-四羟基二苯甲酮、2，2′，4，4′-四羟基二苯甲酮、2，4，6，3′，4′-五羟基二苯甲酮、2，3，4，2′，4′-五羟基二苯甲酮、2，3，4，2′，5′-五羟基二苯甲酮、2，4，6，3′，4′，5′-六羟基二苯甲酮和2，3，4，3′，4′，5′-六羟基二苯甲酮；
(b)多羟苯基烷基酮，例如2，3，4-三羟基苯乙酮、2，3，4-三羟基苯基戊基酮和2，3，4-三羟基苯基己基酮；
(c)双(多羟基苯基)烷烃，例如双(2，3，4-三羟基苯基)甲烷、双(2，4-二羟基苯基)甲烷和双(2，3，4-三羟基苯基)丙烷；
(d)多羟基苯甲酸酯，例如3，4，5-三羟基苯甲酸丙酯、2，3，4-三羟基苯甲酸苯酯和3，4，5-三羟基苯甲酸苯酯；
(e)双(多羟基苯甲酰基)烷烃或双(多羟基苯甲酰基)芳基，例如双(2，3，4-三羟基苯甲酰基)甲烷、双(3-乙酰基-4，5，6-三羟基苯基)甲烷、双(2，3，4-三羟基苯甲酰基)苯和双(2，4，6-三羟基苯甲酰基)苯；
(f)亚烷基二(多羟基苯甲酸酯)，例如乙二醇二(3，5-二羟基苯甲酸酯)和乙二醇二(3，4，5-三羟基苯甲酸酯)；
(g)多羟基联苯，例如2，3，4-联苯三醇、3，4，5-联苯三醇、3，5，3′，5′-联苯四醇、2，4，2′，4′-联苯四醇、2，4，6，3′，5′-联苯五醇、2，4，6，2′，4′，6′-联苯六醇和2，3，4，2′，3′，4′-联苯六醇；
(h)双(多羟基)硫醚，例如4，4′-硫代双(1，3-二羟基)苯；
(i)双(多羟基苯基)醚，例如2，2′，4，4′-四羟基二苯醚；
(j)双(多羟基苯基)亚砜，例如2，2′，4，4′-四羟基二苯基亚砜；
(k)双(多羟基苯基)砜，例如2，2′，4，4′-四羟基二苯基砜；
(l)多羟基三苯甲烷，例如三(4-羟苯基)甲烷、4，4′，4″-三羟基-3，5，3′，5′-四甲基三苯甲烷、4，4′，3″，4″-四羟基-3，5，3′，5′-四甲基三苯甲烷、4，，4′，2″，3″，4″-五羟基-3，5，3′，5′-四甲基三苯甲烷、2，3，4，2′，3′，4′-六羟基-5，5′-二乙酰基三苯甲烷、2，3，4，2′，3′，4′，3″，4″-八羟基-5，5-二乙酰基三苯甲烷和2，4，6，2′，4′，6′-六羟基-5，5′-二丙酰基三苯甲烷；
(m)多羟基螺双茚，例如3，3，3′，3′-四甲基-1，1′-螺双茚-5，6，5′，6′-四醇、3，3，3′，3′-四甲基-1，1′-螺双茚-5，6，7，6′，6′，7′-六醇和3，3，3′，3′-四甲基-1，1′-螺双茚-4，5，6，4′，5′，6′-六醇；
(n)多羟基2-苯并[c]呋喃酮，例如3，3-双(3，4-二羟基苯基)2-苯并[c]呋喃酮、3，3-双(2，3，4-三羟基苯基)2-苯并[c]呋喃酮和3′，4′，5′，6′-四羟基螺(2-苯并[c]呋喃酮-3，9′-占吨)；
(o)在JP No.4-253058中所述的多羟基化合物，例如α′，α″-三(4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3，5-二甲基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3，5-二乙基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3，5-二正丙基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3，5-二异丙基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3，5-二正丁基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3-甲基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(3-甲氧基-4-羟基苯基)-1，3，5-三异丙基苯、α，α′，α″-三(2，4-二羟基苯基)-1，3，5-三异丙基苯、2，4，6-三(3，5-二甲基-4-羟基苯基硫代甲基)-1，3，5-三甲基苯、1-[α-甲基-α-(4″-羟基苯基)乙基]-4-[α，α′-双(4″-羟基苯基)乙基]苯、1-[α-甲基-α-(4′-羟基苯基)乙基]-3-[α，α′-双(4″-羟基苯基)乙基]苯、1-[α-甲基-α-(3′，5′-二甲基-4′-羟基苯基)乙基]苯、1-[α-甲基-α-(3′-甲氧基-4′-羟基苯基)乙基]-4-[α′，α′-双(3′-甲氧基-4′-羟基苯基)乙基]苯和1-[α-甲基-α-(2′，4′-二羟基苯基)乙基]-4-[α，α′-双(4′-羟基苯基)乙基]苯。
重氮萘醌光活性化合物的其他实例包括可溶可熔酚醛树脂与重氮萘醌磺酰氯的缩合产物。可使用这些缩合产物(也称为封端的可溶可熔酚醛树脂)替代多羟基化合物的重氮邻醌或者与其结合使用。许多美国专利公开了这种封端的可溶可熔酚醛树脂。美国专利No.5225311是一个这样的实例。也可使用各种重氮萘醌化合物的混合物。可漂白染料可以以全部固体的最多15wt％，优选范围为全部固体的约0.1％-约10％，更优选全部固体的约0.30-约5％，和甚至更优选全部固体的约0.35％-约2.5％的水平存在于新型的光致抗蚀剂组合物内。
本发明的光致抗蚀剂包括碱不溶性聚合物，光致产酸剂、可光漂白的染料和任选地碱性添加剂。在一些情况下，碱或光活性的碱加入到光致抗蚀剂中，以控制成像的光致抗蚀剂的轮廓并防止表面抑制效果，例如T-top。可添加含量为固体的约0.01wt％-约5wt％，优选最多固体的1wt％，和更优选固体的0.07wt％的碱，优选含氮碱。其具体实例是胺类，例如三乙胺、三乙醇胺、苯胺、乙二胺、吡啶、四烷基氢氧化铵及其盐。光敏碱的实例是氢氧化二苯基碘鎓、氢氧化二烷基碘鎓、氢氧化三烷基锍等。相对于光致产酸剂，可添加含量最多100mol％的碱。尽管使用术语碱添加剂，但除去酸的其他机制(mechanism)也是可能的，例如通过使用挥发性酸(例如CF3CO2 -)或亲核酸(例如Br-)的四烷基铵盐，它们分别通过在曝光后烘烤过程中从膜中挥发出或者通过使亲核部分与酸前体的碳阳离子反应(例如叔丁基碳阳离子与溴化物反应，形成叔丁基溴化物)来除去酸。
流程式2示出了可用作碱的铵衍生物的结构。
流程式2：合适的铵碱的实例
也可使用非挥发性胺添加剂。优选的胺是具有位阻结构的那些，以便阻碍亲核反应性同时维持抗蚀剂配方内的碱度、低挥发性和溶解度，例如质子海绵、1，5-二氮杂双环[4.3.0]-5-壬烯、1，8-二氮杂双环[5.4.0]-7-十一烯、环烷胺或带有胺的聚醚，例如如US6274286中所述。
本发明的光致抗蚀剂可含有其他组分，例如添加剂、表面活性剂、染料、增塑剂和其他辅助的聚合物。表面活性剂典型地是含有氟或硅化合物的化合物/聚合物，它们可辅助形成良好均匀的光致抗蚀剂涂层。可使用一些类型的染料提供不想要光的吸收。特别是对于厚膜来说，可使用增塑剂，以辅助膜的流动性能，例如含有硫或氧的那些。增塑剂的实例是己二酸酯、癸二酸酯和邻苯二甲酸酯。可添加浓度范围为光致抗蚀剂组合物内全部固体重量的0.1-约10wt％的表面活性剂和/或增塑剂。可将辅助聚合物加入到本发明的组合物中，特别优选可溶可熔酚醛树脂，它可由苯酚、甲酚、二-和三甲基取代的-苯酚、多羟基苯、萘酚、多羟基萘酚和其他烷基取代的多羟基苯酚和甲醛、乙醛或苯甲醛的聚合来制备。可添加含量范围为全部固体的约0％-约70％，优选全部固体的约5％-约60％，优选全部固体的约10％-约40％的辅助聚合物。
在生产光致抗蚀剂组合物中，混合光致抗蚀剂中的固体组分与溶解光致抗蚀剂中的固体组分的溶剂或溶剂的混合物。合适的用于光致抗蚀剂的溶剂可包括例如二元醇醚衍生物，例如乙基溶纤剂、甲基溶纤剂、丙二醇单甲醚、二甘醇单甲醚、二甘醇单乙醚、二丙二醇二甲醚、丙二醇正丙醚或二甘醇二甲醚；二元醇醚酯衍生物，例如乙基溶纤剂乙酸酯、甲基溶纤剂乙酸酯或丙二醇单甲醚乙酸酯；羧酸酯，例如乙酸乙酯、乙酸正丁酯和乙酸戊酯；二元酸的羧酸酯，例如草酸二乙酯(diethyloxylate)和丙二酸二乙酯；二元醇的二羧酸酯，例如乙二醇二乙酸酯和丙二醇二乙酸酯；和羟基羧酸酯，例如乳酸甲酯、乳酸乙酯、羟基乙酸乙酯和3-羟基丙酸乙酯；酮酯，例如丙酮酸甲酯或丙酮酸乙酯；烷氧基羧酸酯，例如3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-羟基-2-甲基丙酸乙酯或乙氧基丙酸甲酯；酮衍生物，例如甲乙酮、乙酰基丙酮、环戊酮、环己酮或2-庚酮；酮醚衍生物，例如双丙酮醇甲醚；酮醇衍生物，例如丙酮醇或双丙酮醇；内酯，例如丁内酯；酰胺衍生物，例如二甲基乙酰胺或二甲基甲酰胺、茴香醚及其混合物。
可通过光致抗蚀剂领域中使用的任何常规的方法，其中包括浸涂、喷涂、旋转和旋涂，将所制备的光致抗蚀剂组合物溶液施加到基底上。当旋涂时，可例如相对于固体含量的百分数来调节抗蚀剂溶液，以便考虑到所使用的旋转设备的类型和旋转工艺所要求的时间量来提供所需厚度的涂层。合适的基底包括，但不限于，硅、铜、铝、聚合物树脂、二氧化硅、金属、掺杂的二氧化硅、氮化硅、钽、多晶硅、陶瓷、铝/铜的混合物；砷化镓和其他诸如第III/V族的化合物。
通过所公开的工序生产的光致抗蚀剂涂层尤其适合于施加铜涂布的晶片，正如在生产微型处理器和其他小型化集成电路组件中所使用的。也可使用硅/二氧化硅晶片。基底也可包括各种聚合物树脂，特别是抗反射涂层。基底可具有合适组成的粘合促进层，例如含六烷基二硅氮烷的那种。
然后在基底上涂布光致抗蚀剂组合物溶液，并在热板上，在约70℃-约150℃的温度下处理基底约30秒-约6分钟，或者在对流烘箱内处理约15-约90分钟。选择这一温度处理，以便降低光致抗蚀剂内残留溶剂的浓度，同时不引起光吸收化合物显著的热降解。一般地，人们希望最小化溶剂的浓度，并首先进行这一温度处理，直到基本上所有的溶剂蒸发，并在基底上保留厚度数量级为2-200微米的光致抗蚀剂组合物涂层。可进行多次涂布以实现厚的膜。在优选的实施方案中，温度为约95℃-约135℃。温度和时间的选择取决于使用者希望的光致抗蚀剂的性能，以及所使用的设备，和商业上所需的涂布时间。然后可按照通过使用合适的掩膜、负片、模版(stencil)、模板等产生的任何所需的图案，于光化辐射下曝光涂布的基底，例如波长为约300nm(纳米)-约450nm的紫外线、x-射线、电子束、离子束或激光辐射下。一般地，使用诸如Ultratech、Karl Süss或Perkin Elmer宽带曝光工具之类的设备，使用宽带辐射线，曝光厚的光致抗蚀剂膜，但也可使用436nm和365nm的Steppers。
然后在显影之前或之后，任选对光致抗蚀剂进行曝光后的二次烘烤或者热处理。加热温度范围可以是约90℃-约150℃，更优选约90℃-约130℃。可在热板上进行加热约30秒-约3分钟，更优选约60秒-约2分钟，或者通过对流烘箱加热约30-45分钟。
通过在显影溶液内浸渍或者通过喷洒显影工艺显影，使曝光的光致抗蚀剂涂布的基底显影，以除去图像状曝光的区域。优选例如通过喷氮搅拌，来搅动溶液。允许基底保持在显影剂内，直到所有或基本上所有的光致抗蚀剂涂层从曝光区域中溶解。显影剂包括铵或碱金属氢氧化物的水溶液。一种优选的氢氧化物是四甲基氢氧化铵。其他优选的碱是氢氧化钠或氢氧化钾。诸如表面活性剂之类的添加剂可加入到显影剂中。在从显影溶液中除去涂布的晶片之后，人们可进行任选的显影后的热处理或烘烤，以增加涂层的粘合性和光致抗蚀剂的密度。然后可用金属或金属层涂布成像的基底，形成隆起(bump)，这是本领域众所周知的，或者视需要进一步加工。
为了所有的目的，以上提到的每一篇文献在此通过参考全文引入。下述具体的实施例提供生产和利用本发明组合物的方法的详细说明。然而，这些实施例决不打算为以任何方式限制或限定本发明的范围，且不应当解释为为了实践本发明，提供必须唯一使用的条件、参数或数值。
实施例
实施例1-13
如表1所示配制光致抗蚀剂样品1-13。然后通过从0.2微米-10微米中选择的微孔尺寸的过滤器(这取决于光致抗蚀剂的粘度)，微滤光致抗蚀剂样品。
然后评价光致抗蚀剂样品的平版印刷性能。单独地在硅片上和在铜基底上以合适的旋转速度旋涂每一样品。对于10微米厚的膜来说，在110℃下软烘烤涂布的基底至少120分钟。较厚的膜(40-50微米)需要在110℃下多次烘烤至多7分钟。对于10微米的膜来说和对于大于10微米的膜来说，所使用的曝光工具是ASML I-线分档器，接近式，Suss MA-200校准器。在110℃下曝光后烘烤基底30分钟。在23℃下，使用具有AZ 300MIF显影剂(获自AZ Electronic Materials USACorps.)的puddle显影，显影具有10微米光致抗蚀剂膜的基底60分钟。在23℃下，使用具有AZ
300MIF显影剂(获自AZ
ElectronicMaterials，Somerville，USA Corps.)的puddle显影，4次显影具有40微米光致抗蚀剂膜的基底60分钟。采用扫描电子显微术检验光致抗蚀剂轮廓，以评价光致抗蚀剂的侧壁轮廓、分辨率和基底的清理(clearing)。表1中给出了结果。
相对于不含染料、含有染料或可漂白染料的配方，比较光致抗蚀剂的性能。使用两类基底，硅(Si)和铜(Cu)，和检测两种膜厚度，10微米和40微米。
在所有Cu基底的情况下，就具有陡峭的侧壁和良好的分辨率的轮廓来说，添加可漂白染料到光致抗蚀剂中得到改进的性能，正如在实施例7-13中观察到的。对比例(1和5)显示出用于光致抗蚀剂图案的差的分辨率和曲面或倾斜的侧壁。实施例6表明对于40微米厚的膜来说，光致抗蚀剂不具有最佳的可漂白染料浓度。实施例2和3均没有得到良好的分辨率和垂直的轮廓。
当基底是硅时，可漂白染料在所有情况下(实施例6-13)提供良好的性能。
与硅基底相比，可漂白染料对铜基底具有较大的有益影响。
表1配方和结果
| 实施例 | 聚合物GIJ Novolak | PAG(1)(2) | 碱 | 染料 | 可漂白染料 | LutonalM40 | 溶剂PGMEA/ 环己酮 | ％固体 | 膜厚 | 在Si片上的轮廓 | Cu片上的性能 |
| 1 | 16.48 7.06 | 0.33 | - | - | - | 0.328 | 26.094 - | 47.8 | 10μm和40μm | 翻转的轮廓 | 分辨率差，下凹的轮廓和细线损失：10μm和以下 |
| 2 | 13.516 5.792 | 0.0596 | - | 0.0958 | - | 0.536 | 30 - | 40.0 | 10μm | 垂直的轮廓 | 分辨率差，在线路之间具有残留的抗蚀剂 |
| 3 | 13.827 5.926 | 0.0272 | - | 0.0998 | - | - | 30.12 - | 39.76 | 40μm | 倾斜的轮廓 | 分辨率差且在整个晶片上具有残留的抗蚀剂 |
| 4 | 16.411 7.033 | 0.0327 | - | 0.023 | - | - | 26.5 - | 47 | 40μm | 垂直的轮廓 | 分辨率差，严重的渣滓和残渣 |
| 5 | 24.565 - | 0.174 | - | - | - | 1.306多羟基化合物 | 20.08 3.872 | 52.09 | 52μm | 垂直的轮廓 | 分辨率差(30μm)长宽比1.7 |
| 6 | 25.332 - | 0.1914 | 0.03 | - | 0.0832(2) | 0.408 | 21.364 5.341 | 46.59 | 40μm | 垂直的轮廓 | 分辨率差(20μm)长宽比2.0 |
| 7 | 14.919 6.3938 | 0.1619 | 0.029 | - | 0.1425(2) | 0.3455 | 22.4 5.6015 | 43.985 | 33μm | 垂直的轮廓 | 分辨率好：(10μm)长宽比＞3 |
| 8 | 18.8873 - | 0.1548 | 0.024 | - | 0.2694(2) | 0.3049 | 24.2856 6.0714 | 39.286 | 40μm | 垂直的轮廓 | 分辨率好(10μm)长宽比＞3 |
| 9 | 16.1128 6.905 | 0.1713 | 0.0304 | - | 0.1496(1) | - | 21.304 5.326 | 46.74 | 10μm和40μm | 陡峭的轮廓 | 具有良好分辨率的陡峭轮廓：在40μm膜内10μm，长宽比＞3在10μm膜内4μm |
| 10 | 19.043 - | 0.1692 | 0.0318 | - | 0.1227(1) | 0.2881 | 24.276 6.069 | 39.31 | 10μm | 陡峭的轮廓 | 具有良好分辨率的陡峭轮廓(3μm)长宽比＞3 |
| 11 | 19.0508 - | 0.1693 | 0.0117 | - | 0.1228(1) | 0.2883 | 24.286 6.0714 | 39.286 | 10μm | 陡峭的轮廓 | 具有分辨率的下凹轮廓(4.2μm) |
| 12 | 19.0465 - | 0.16917 | 0.02176 | - | 0.1227(1) | 0.2883 | 24.281 6.0703 | 39.297 | 10μm | 陡峭的轮廓 | 具有良好分辨率的陡峭轮廓(3.2μm) |
| 13 | 13.521 5.795 | 0.16480.1849(2) | 0.1407 | - | 0.0724(2) | 0.3477 | 23.92 5.98 | 40.2 | 10μm | 陡峭的轮廓 | 具有良好分辨率的陡峭轮廓(2.2μm) |
聚合物：GIJ聚合物是羟基苯乙烯、苯乙烯和丙烯酸叔丁酯的三元聚合物(获自Dupont Electronic Technologies，Ingleside，Texas.)
PAG：(1)N-羟基萘二甲酰亚胺三氟甲磺酸盐，(2)2-{2′-(5′-甲基呋喃基)亚乙基}-4，6-双(三氯甲基)-S-三嗪
染料：2，2′，4，4′-四羟基二苯甲酮
可漂白染料：
(1)2，3，4-三羟基二苯甲酮与2，1，4和2，1，5-重氮萘醌磺酰氯的混合物的二酯
(2)四羟基二苯甲酮与2，1，5-重氮萘醌磺酰氯的80％酯
将最多1wt％表面活性剂，APS-437(获自D.H.LitterCo.，565，Taxter Rd.，Elmsford，New York)加入到溶液中。
Claims (20)
1.一种光致抗蚀剂组合物，它包括在含水碱性显影剂中不溶但在显影之前变得可溶的聚合物、一旦辐照则产生强酸的光致产酸剂和在与光致产酸剂相同的辐射线下为吸收性的可光漂白的染料，并且所述光致产酸剂是磺酰氧基酰亚胺，并且所述可光漂白的染料是具有2-7个酚部分的多羟基化合物的1，2-重氮萘醌-5-磺酰基酯和/或1，2-重氮萘醌-4-磺酰基酯。
2.权利要求1的光致抗蚀剂组合物，其中所述染料的漂白速度没有显著高于光致产酸剂的光解。
3.权利要求1或2的光致抗蚀剂组合物，其中所述聚合物已经用酸不稳定基团保护以使其在显影之前可溶于含水碱性显影剂。
4.权利要求1的光致抗蚀剂组合物，其中所述聚合物包括衍生于下述单体的至少一种单元，所述单体选自羟基苯乙烯、苯乙烯、乙酰氧基苯乙烯、甲氧基苯乙烯、用酸不稳定基团封端的丙烯酸酯、用酸不稳定基团封端的甲基丙烯酸酯、用酸不稳定基团封端的羟基苯乙烯及其混合物。
5.权利要求1的光致抗蚀剂组合物，其中一旦辐照，光致产酸剂就产生磺酸。
6.权利要求1的光致抗蚀剂组合物，其中可光漂白的染料是2，3，4-三羟基二苯甲酮与2，1，4-重氮萘醌磺酰氯和2，1，5-重氮萘醌磺酰氯的混合物的二酯，或者是四羟基二苯甲酮与2，1，5-重氮萘醌磺酰氯的80％酯。
7.权利要求1的光致抗蚀剂组合物，其中该组合物进一步包括可溶可熔酚醛树脂。
8.权利要求1的光致抗蚀剂组合物，其中该组合物进一步包括碱。
9.权利要求1的光致抗蚀剂组合物，其中该组合物进一步包括增塑剂。
10.权利要求1的光致抗蚀剂组合物，其中光致产酸剂是具有选自以下结构的磺酰氧基酰亚胺，
其中R1为C1-C8烷基或C1-C8烷氧基，并且n＝1-20。
11.使光致抗蚀剂成像的方法，该方法包括下述步骤：
a)在基底上形成光致抗蚀剂组合物的涂层，所述光致抗蚀剂组合物包括在含水碱性显影剂中不溶但在显影之前变得可溶的聚合物、一旦辐照则产生强酸的光致产酸剂和在与光致产酸剂相同的辐射线下为吸收性的可光漂白的染料，所述光致产酸剂是磺酰氧基酰亚胺，并且所述可光漂白的染料是具有2-7个酚部分的多羟基化合物的1，2-重氮萘醌-5-磺酰基酯和/或1，2-重氮萘醌-4-磺酰基酯，并且所述基底包括铜和所述光致抗蚀剂涂层的膜厚大于2微米而小于200微米；
b)用辐射线成像式曝光光致抗蚀剂涂层；
c)曝光后烘烤光致抗蚀剂涂层；
d)用含水碱性显影剂使光致抗蚀剂涂层显影，形成光致抗蚀剂结构。
12.权利要求11的方法，其中将光致抗蚀剂涂层一步曝光。
13.权利要求11的方法，其中用300nm-450nm的辐射线使光致抗蚀剂成像。
14.权利要求11的方法，其中所述光致抗蚀剂结构具有大于3的长宽比，所述长宽比是光致抗蚀剂图案的高度与宽度之比。
15.权利要求11的方法，其中显影剂是四甲基氢氧化铵的水溶液。
16.权利要求11的方法，其中所述聚合物已经用酸不稳定基团保护以使其在显影之前可溶于含水碱性显影剂。
17.权利要求11的方法，其中所述聚合物包括衍生于下述单体的至少一种单元，所述单体选自羟基苯乙烯、苯乙烯、乙酰氧基苯乙烯、甲氧基苯乙烯、用酸不稳定基团封端的丙烯酸酯、用酸不稳定基团封端的甲基丙烯酸酯、用酸不稳定基团封端的羟基苯乙烯及其混合物。
18.权利要求11的方法，其中一旦辐照，光致产酸剂就产生磺酸。
19.权利要求11的方法，其中光致产酸剂是具有选自以下结构的磺酰氧基酰亚胺，
其中R1为C1-C8烷基或C1-C8烷氧基，并且n＝1-20。
20.使光致抗蚀剂成像的方法，该方法包括下述步骤：
a)在基底上形成权利要求1的光致抗蚀剂组合物的涂层；
b)用辐射线成像式曝光光致抗蚀剂涂层；
c)曝光后烘烤光致抗蚀剂涂层；
d)用含水碱性显影剂使光致抗蚀剂涂层显影，形成光致抗蚀剂结构。
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| Application Number | Priority Date | Filing Date | Title |
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| US11/179,364 US7255970B2 (en) | 2005-07-12 | 2005-07-12 | Photoresist composition for imaging thick films |
| US11/179,364 | 2005-07-12 | ||
| PCT/IB2006/001933 WO2007007176A2 (en) | 2005-07-12 | 2006-07-07 | Photoresist composition for imaging thick films |
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| MY (1) | MY137961A (zh) |
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| US5556734A (en) * | 1993-12-24 | 1996-09-17 | Japan Synthetic Rubber Co., Ltd. | Radiation sensitive resin composition comprising copolymer of isopropenylphenol and T-butyl(meth)acrylate |
| US6627377B1 (en) * | 1997-10-13 | 2003-09-30 | Pi R&D Co., Ltd. | Positive photosensitive poliymide composition |
| CN1564967A (zh) * | 2001-10-05 | 2005-01-12 | 横滨Tlo株式会社 | 反应显影布图方法 |
| WO2005043247A1 (ja) * | 2003-10-31 | 2005-05-12 | Az Electronic Materials (Japan) K.K. | 厚膜および超厚膜対応化学増幅型感光性樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007007176A2 (en) | 2007-01-18 |
| TW200712763A (en) | 2007-04-01 |
| KR20080016971A (ko) | 2008-02-22 |
| US7255970B2 (en) | 2007-08-14 |
| CN101218541A (zh) | 2008-07-09 |
| EP1913444B1 (en) | 2013-01-16 |
| WO2007007176A3 (en) | 2007-03-22 |
| MY137961A (en) | 2009-04-30 |
| KR101304607B1 (ko) | 2013-09-05 |
| US20070015080A1 (en) | 2007-01-18 |
| EP1913444A2 (en) | 2008-04-23 |
| JP5051395B2 (ja) | 2012-10-17 |
| TWI418931B (zh) | 2013-12-11 |
| JP2009501352A (ja) | 2009-01-15 |
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