CN104109589B - 用于绝缘膜的清洗液以及清洗绝缘膜的方法 - Google Patents

用于绝缘膜的清洗液以及清洗绝缘膜的方法 Download PDF

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CN104109589B
CN104109589B CN201310567460.8A CN201310567460A CN104109589B CN 104109589 B CN104109589 B CN 104109589B CN 201310567460 A CN201310567460 A CN 201310567460A CN 104109589 B CN104109589 B CN 104109589B
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cleaning solution
insulating layer
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CN104109589A (zh
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裵镇希
李汉松
任浣熙
金古恩
郭泽秀
金补宣
金相均
罗隆熙
朴银秀
徐珍雨
宋炫知
赵娟振
韩权愚
黄丙奎
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Cheil Industries Inc
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Abstract

本发明提供了用于绝缘膜的清洗液以及清洗绝缘膜的方法。公开了包含由以下化学式1表示的溶剂的用于绝缘层的清洗液、以及利用所述清洗液清洗绝缘层的方法。在化学式1中，R1和Ra至Re与在详细描述中所定义的相同。[化学式1]

Description

用于绝缘膜的清洗液以及清洗绝缘膜的方法
本申请要求于2013年4月18日在韩国知识产权局提交的韩国专利申请号10-2013-0043079的优先权和权益，将其全部内容以引用方式结合于本文中。
技术领域
披露了用于绝缘层的清洗液（冲洗液，漂洗液，rinse liquid）以及清洗绝缘层的方法。
背景技术
随着半导体技术日益发达，对形成具有改善性能并集成更小半导体芯片的高度集成且更快的半导体存储单元存在持续的研究。在这些半导体存储单元中，例如，可以使用DRAM（动态随机存取存储器）。DRAM能够自由输入和输出信息，并可以实现大容量。
DRAM可以包括，例如，多个单元，其包括一个MOS晶体管（MOS晶体管）和一个电容器。电容器可以包括两个电极和设置在其间的介电层。电容器可以具有不同的容量，其取决于，例如，介电常数、介电层的厚度、电极的面积等。
随着半导体芯片的尺寸减小，也可以减小其中的电容器的尺寸。然而，更小的电容器需要足够的存储容量。通过例如增加垂直面积来代替降低水平面积以增加总有效面积，电容器可以实现更大容量。在这里，需要这样的绝缘材料，其具有间隙填充特性以填充在图案之间的窄间隙而没有真空空间。
这种绝缘材料可以通过施加含硅氮化合物如聚硅氮烷并使其固化而包括二氧化硅。二氧化硅可以在电子器件如半导体装置或显示器件中用作，例如，用于电容器的介电层、层间绝缘层、平坦化层、钝化膜、分离绝缘体等。
另一方面，当含硅氮化合物如聚硅氮烷用来在基底（衬底，基板，substrate）上形成薄膜时，在不期待形成薄膜处形成的含硅氮化合物或其残留在基底的侧面或后面的残留物需要被除去，并且在这里可以使用用于绝缘层的清洗液。
发明内容
一个实施方式提供了用于绝缘层的清洗液，其有效地清洗绝缘层的残留物而不会对绝缘层的特性具有影响。
另一个实施方式提供了利用用于绝缘层的清洗液来清洗绝缘层的方法。
根据一个实施方式，提供了一种用于绝缘层的清洗液，其包含由以下化学式1表示的溶剂。
[化学式1]
在化学式1中，
R1是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、或它们的组合，以及
Ra至Re各自独立地是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、羟基基团、卤素原子、或它们的组合。
溶剂可以包括苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸异丙酯、苯甲酸丁酯、苯甲酸苄酯或它们的组合。
溶剂可以包括单一溶剂或两种或更多种的混合物。
用于绝缘层的清洗液可以进一步包括辅助溶剂，其在正常压力下具有约100℃至约300℃的沸点。
辅助溶剂可以包括醚、萘满（1,2,3,4-四氢化萘）、乙酸酯、苯、萘、酮、腈、链烷烃、它们的衍生物或它们的组合。
辅助溶剂可以包括乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丁醚、三乙二醇二甲醚、乙基萘满（乙基-1,2,3,4-四氢化萘，ethyl tetralin）、二甲基萘满（二甲基-1,2,3,4-四氢化萘，dimethyl tetralin）、三甲基萘满、四甲基萘满、乙酸苄酯、1,2-二甲基萘、1-甲基萘、苯乙酮、己二腈、苄基乙基醚、丁基苯、环己基苯、二苄醚、苊烯（acenaphthylene）、1-萘基乙腈、二苯醚、乙二醇醚（二醇醚，glycolether）、链烷烃、或它们的组合。
在正常压力下，链烷烃和它的衍生物可以具有约190℃至约220℃的沸点。
基于清洗液的总量，辅助溶剂可以以大于约0wt%并且小于或等于约99wt%的量被包括。
在1ml清洗液中，用于绝缘层的清洗液可以包括约50个或更少的大于或等于约0.5μm的颗粒。
在1ml清洗液中，用于绝缘层的清洗液可以包括约200个或更少的大于或等于约0.2μm的颗粒。
用于绝缘层的清洗液可以具有小于或等于约150ppm的含湿量（水分含量，含水量，moisture content）。
用于绝缘层的清洗液可以用于清洗聚硅氮烷或聚硅氧氮烷（聚硅氧硅氮烷，polysiloxazane）。
根据另一个实施方式，清洗绝缘层的方法包括在基底上施加绝缘层，以及在绝缘层上将用于绝缘层的清洗液提供到绝缘层的前部、后部（rear part）、边缘部（edge part）、或它们的组合。
附图说明
图1是示出了用于评估在绝缘层的末端处的附聚程度以及根据实施例1至8清洗的绝缘层的残留膜的参考（reference）的示意图。
具体实施方式
本发明的示例性实施方式将在下文中详细描述，并且可以由本领域技术人员容易进行。然而，可以以许多不同的形式来具体实施此披露内容，而不应看作是限于本文陈述的示例性实施方式。
如在本文中所使用的，当没有另外提供定义时，术语“取代的”是指用下述至少一种取代基取代，代替化合物中的氢原子，所述取代基选自卤素原子（F、Br、Cl、或I）、羟基基团、烷氧基基团、硝基基团、氰基基团、氨基基团、叠氮基团、脒基基团、肼基基团、亚肼基基团、羰基基团、氨基甲酰基团、硫羟基团（硫醇基团）、酯基团、羧基基团或其盐、磺酸基团或其盐、磷酸或其盐、C1至C20烷基基团、C2至C20烯基基团、C2至C20炔基基团、C6至C30芳基基团、C7至C30芳烷基基团、C1至C4烷氧基基团、C1至C20杂烷基基团、C3至C20杂芳烷基基团、C3至C30环烷基基团、C3至C15环烯基基团、C6至C15环炔基基团、C3至C30杂环烷基基团、以及它们的组合。
如在本文中所使用的，当没有另外提供定义时，前缀“杂”可以指包括选自N、O、S、和P中的1至3个杂原子。
在下文中，描述了根据一个实施方式的用于绝缘层的清洗液。
根据一个实施方式的用于绝缘层的清洗液包括由以下化学式1表示的溶剂。
[化学式1]
在化学式1中，
R1是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、或它们的组合。
Ra至Re各自独立地是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、羟基基团、卤素、或它们的组合。
由化学式1表示的溶剂是并不与绝缘材料并且因此与绝缘层的残留物反应的苯甲酸酯溶剂，对绝缘层的特性没有影响。
由化学式1表示的溶剂可以包括例如苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸异丙酯、苯甲酸丁酯、苯甲酸苄酯、或它们的组合，但不限于此。
溶剂可以包括单一溶剂或两种或更多种的混合物。
基于清洗液的总量，溶剂可以以约1至约100wt%的量被包括。
清洗液可以进一步包含在正常压力下具有约100℃至约300℃的沸点的辅助溶剂。清洗液进一步包含沸点在上述范围内的辅助溶剂，因而可以改善因为溶剂在完全溶解薄膜以前蒸发的待除去的残留膜残留的问题。
辅助溶剂可以包括，例如，醚、萘满、乙酸酯、苯、萘、酮、腈、链烷烃、它们的衍生物、或它们的组合，具体地乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丁醚、三乙二醇二甲醚、乙基萘满、二甲基萘满、三甲基萘满、四甲基萘满、乙酸苄酯、1,2-二甲基萘、1-甲基萘、苯乙酮、己二腈、苄基乙基醚、丁基苯、环己基苯、二苄醚、苊烯、1-萘基乙腈、二苯醚、乙二醇醚、链烷烃、或它们的组合。
当链烷烃用作辅助溶剂时，链烷烃可以选自脂族烃、环状脂族烃、或它们的组合，其在正常压力下具有约190℃至约220℃的沸点。沸点在上述范围内的链烷烃可以解决以下问题：薄膜在与基底的边界线处变得凸出（convex）或没有被完全除去。
基于清洗液的总量，辅助溶剂可以以大于约0wt%并且小于或等于约99wt%的量被包括。
在1ml清洗液中，清洗液可以包括约50个或更少的大于或等于约0.5μm的颗粒。当颗粒的数目大于50个时，颗粒残留在绝缘层的表面上，因而，可以劣化绝缘层的特性或影响生产成品率（production yield）和特性，以及可以劣化通过利用绝缘层制造的器件的特性。另外，当颗粒的数目大于50个时，可以进行过滤或蒸馏以减少在上述范围内的颗粒的数目。基于同样的原因，在1ml清洗液中，清洗液可以包括约200个或更少的大于或等于约0.2μm的颗粒。
清洗液可以具有小于或等于约150ppm的含湿量。当清洗液具有在上述范围内的含湿量时，清洗液可以延迟接触清洗液的绝缘材料如聚硅氮烷或聚硅氧氮烷的胶凝作用，防止在旋涂机中废液线路（waste fluid line）的堵塞，并有效地除去附着于器件的绝缘材料。清洗液可以具有在该范围内的小于或等于100ppm的含湿量。
用于绝缘层的清洗液可以用于清洗用于电子器件的绝缘层。
电子器件可以包括，例如半导体装置和显示器件，并且可以是包括绝缘层的任何器件。
绝缘层在电子器件中可以是用于电容器的介电层、层间绝缘层、平坦化层、钝化膜、分离绝缘体等。
清洗液可以用于例如由聚硅氮烷或聚硅氧氮烷形成的绝缘层。
聚硅氮烷可以包括由以下化学式2表示的部分。
[化学式2]
在化学式2中，
R2至R4各自独立地是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、羟基基团、或它们的组合。
聚硅氧氮烷包括由化学式2表示的部分和由以下化学式3表示的部分。
[化学式3]
在化学式3中，
R5至R8独立地是氢、取代或未取代的C1至C30烷基基团、取代或未取代的C3至C30环烷基基团、取代或未取代的C6至C30芳基基团、取代或未取代的C7至C30芳烷基基团、取代或未取代的C1至C30杂烷基基团、取代或未取代的C2至C30杂环烷基基团、取代或未取代的C5至C30杂芳基基团、取代或未取代的C2至C30烯基基团、取代或未取代的C2至C30炔基基团、取代或未取代的烷氧基基团、取代或未取代的羰基基团、羟基基团、或它们的组合。
聚硅氮烷可以是，例如，在末端处用氢帽化（capped）的全氢聚硅氮烷（perhydropolysilazane），或用除了氢以外的官能团取代R2至R4中的至少一个的聚硅氮烷，并且聚硅氧氮烷可以是在末端处用氢帽化的全氢聚硅氧氮烷（perhydropolysiloxazane），或用除了氢以外的官能团取代R5至R8中的至少一个的聚硅氧氮烷。
基于总重量，聚硅氮烷或聚硅氧氮烷可以具有范围从约0.2至约3wt%的氧含量。当氧含量在该范围内时，足够减轻由于结构中的硅-氧-硅（Si-O-Si）键引起的应力，可以防止在热处理期间的收缩，因而，可以防止在填料图案中的裂纹。
聚硅氮烷或聚硅氧氮烷可以具有例如在末端处用氢帽化的结构（-SiH3），并且在本文中，基于Si-H键的总重量，由-SiH3表示的部分可以以约15至约35%的量被包括。当在上述范围内包括该部分时，可以防止SiH3部分分散成SiH4，同时在热处理期间足够发生氧化反应，并可以防止在填料图案中的裂纹。
聚硅氮烷或聚硅氧氮烷可以具有例如约1,000至约30,0000的重均分子量。当平均分子量是在上述范围内时，可以在热处理期间使清洗液中的更少成分蒸发，并且清洗液可以致密地填充尺寸为小于或等于50nm的微间隙，结果改善了间隙填充特性。
聚硅氮烷或聚硅氧氮烷可以包括，例如，小于或等于约1ppm的氯含量。
在下文中，描述根据一个实施方式的清洗绝缘层的方法。
根据一个实施方式的清洗绝缘层的方法包括在基底上施加绝缘层，以及在绝缘层上提供上述用于绝缘层的清洗液。
基底可以是，例如，硅片、金属基底、玻璃基底、和聚合物基底，并可以将导电层、绝缘层、和/或半导体层单独或以多个地（in plural）层压在基底上。
绝缘层可以与如上文描述的相同，并且可以包括，例如，聚硅氮烷、聚硅氧氮烷、或它们的组合。
可以将用于绝缘层的清洗液提供在绝缘层的前部、后部、或边缘部、或它们的组合上，以及另外，一次或依次地进行。此外，可通过例如但并不特别限于喷涂、浸涂、旋涂、狭缝涂布等来提供清洗液。
在绝缘层上提供清洗液可以有效地除去其中在不期待形成的地方上形成的绝缘层或残留在基底的侧面或后面上的绝缘层的残留物。
清洗液可以用来清洗绝缘层，然后可以热处理绝缘层。
在下文中，参照实施例来更详细地说明本发明。然而，这些实施例是示例性的，并且本发明并不限于此。
聚硅氮烷的合成
合成实施例1
用干燥氮气内部置换带有搅拌装置和温度控制器的2L反应器。随后，将1,500g干吡啶注入反应器中并与其充分混合，然后，将反应器保温在20℃下。随后，经1小时将100g二氯硅烷慢慢注入其中。在搅拌混合物的同时，经3小时将70g氨慢慢注入其中。随后，将干燥氮气注入其中，时间为30分钟，然后除去残留在反应器中的氨。
在干燥的氮气氛下，用具有1μm尺寸孔的TEFLON（四氟乙烯）过滤器来过滤获得的白色淤浆相产物（white slurry-phased product），从而获得1,000g过滤溶液。随后，将1,000g干二甲苯加入其中，通过借助于旋转式蒸发器，重复三次从吡啶到二甲苯置换溶剂，将其中的固体含量调节成20%，然后用具有0.03μm尺寸孔的TEFLON（四氟乙烯）过滤器来过滤经调节的产物。
获得的全氢聚硅氮烷包括0.5%的氧含量、0.22的SiH3/SiH（总计）、4,000的重均分子量、以及0.9ppm的氯含量。
在本文中，通过利用FlashEA1112（Thermo Fisher Scientific Inc.）来测量氧含量，通过利用200MHz:AC-200（Bruker Co.）的质子NM来测量SiH3/SiH（总计），以及通过利用GPC；HPLC泵1515、RI检测器2414（Waters Co.）和柱：KF801、KF802、KF803（Shodex）来测量重均分子量。
绝缘层的清洗
实施例1
将按照合成实施例1的全氢聚硅氮烷加入3cc的二正丁基醚溶液中，并搅拌混合物，从而制备全氢聚硅氮烷溶液。随后，以1500rpm持续20秒旋涂全氢聚硅氮烷溶液以在硅片上形成绝缘层。随后，以10ml/分钟持续5秒喷涂包括100wt%苯甲酸甲酯（ZOUPINGMINGXING CHEMICALCo.,Ltd.）的清洗液，从硅片的外周向上为3mm。随后，在150℃下，热处理喷涂液3分钟以形成绝缘层，并清洗绝缘层。
实施例2
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括100wt%苯甲酸乙酯（ZOUPING MINGXING CHEMICAL Co.,Ltd.）来代替100wt%苯甲酸甲酯的清洗液。
实施例3
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括10wt%苯甲酸甲酯和90wt%链烷烃（naphthru200,Kodo Chemical）来代替100wt%苯甲酸甲酯的清洗液。
实施例4
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括20wt%苯甲酸甲酯和80wt%链烷烃来代替100wt%苯甲酸甲酯的清洗液。
实施例5
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括30wt%苯甲酸甲酯和70wt%链烷烃来代替100wt%苯甲酸甲酯的清洗液。
实施例6
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括10wt%苯甲酸乙酯和90wt%链烷烃来代替100wt%苯甲酸甲酯的清洗液。
实施例7
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括20wt%苯甲酸乙酯和80wt%链烷烃来代替100wt%苯甲酸甲酯的清洗液。
实施例8
按照与实施例1相同的方法来清洗绝缘层，不同之处在于：使用包括30wt%苯甲酸乙酯和70wt%链烷烃来代替100wt%苯甲酸甲酯的清洗液。
评估
针对在末端处的附聚程度、残留膜、和清洗液的含湿量，评估了根据实施例1至8清洗的绝缘层。
图1是示出了对于在末端处的附聚程度以及根据实施例1至8清洗的绝缘层的残留膜的参考的示意图。
借助于反射分光光度法厚度测量仪（ST-4000,K-MAC TechnologyCorp.）和电子扫描显微镜（S-4800Type-2,Hitachi Ltd.），通过测量图1的ΔT来评估在绝缘层的末端处的附聚程度，并且通过使用光学显微镜（LV100D,Nikon Co.）来检查膜残留物。
借助于卡尔费休（Karl Fisher）水分测量装置利用氧化/还原反应来测量清洗液的含湿量。
结果提供在表1中。
表1
参照表1，根据实施例1至8有效清洗的绝缘层几乎不显示附聚和残留膜。
虽然已经结合目前被认为是实用的示例性实施方式的内容对本发明进行了描述，但应当理解，本发明并不限于所公开的实施方式，而是相反，旨在覆盖包括在所附权利要求书的精神和范围内的各种更改和等同安排。

Claims (6)

1.一种用于绝缘层的清洗液，包含溶剂，所述溶剂包括苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸异丙酯、苯甲酸丁酯、苯甲酸苄酯、或它们的组合，
其中，所述清洗液具有小于或等于150ppm的含湿量，
所述清洗液进一步包含辅助溶剂，所述辅助溶剂包括在正常压力下具有190℃至220℃的沸点的链烷烃。
2.根据权利要求1所述的用于绝缘层的清洗液，其中，基于所述清洗液的总量，所述辅助溶剂以大于0wt％并且小于或等于99wt％的量被包括。
3.根据权利要求1所述的用于绝缘层的清洗液，其中，在1ml所述清洗液中，所述清洗液包含50个或更少的大于或等于0.5μm的颗粒。
4.根据权利要求1所述的用于绝缘层的清洗液，其中，在1ml所述清洗液中，所述清洗液包含200个或更少的大于或等于0.2μm的颗粒。
5.根据权利要求1所述的用于绝缘层的清洗液，其中，所述绝缘层包含聚硅氮烷、聚硅氧氮烷、或它们的组合。
6.一种清洗绝缘层的方法，包括：
在基底上施加绝缘层，以及
在所述绝缘层上将根据权利要求1所述的用于绝缘层的清洗液提供到绝缘层的前部、后部、边缘部、或它们的组合。
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