CN108292095A - 具有高介电常数的光可成像薄膜 - Google Patents
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Abstract
一种用于制备光可成像膜的制剂;所述制剂包含:(a)包含甲酚酚醛树脂和重氮萘醌抑制剂的正性光致抗蚀剂;和(b)官能化的氧化锆纳米粒子。
Description
技术领域
本发明涉及一种具有高介电常数的可光可成像薄膜。
背景技术
高介电常数薄膜对于如嵌入式电容器、TFT钝化层和栅极电介质的应用而言具有高度吸引力以便进一步使微电子部件小型化。用于获得光可成像的高介电常数薄膜的一种方法是将高介电常数纳米粒子并入光致抗蚀剂中。US7630043公开了基于含有具有如羧酸的碱溶性单元的丙烯酸聚合物和介电常数高于4的细粒子的正性光致抗蚀剂的复合薄膜。然而,此参考文献没有公开用于本发明的粘结剂。
发明内容
本发明提供了用于制备光可成像膜的制剂;所述制剂包含:(a)包含甲酚酚醛树脂和重氮萘醌抑制剂的正性光致抗蚀剂;和(b)官能化的氧化锆纳米粒子。
具体实施方式
除非另有规定,否则百分比是按重量百分比(wt%)计并且温度是以℃为单位。除非另有规定,否则操作在室温(20-25℃)下进行。术语“纳米粒子”是指直径是1到100nm的粒子;即至少90%粒子在指定尺寸范围内,并且粒度分布的最大峰高在所述范围内。纳米粒子的平均直径优选是75nm或更小;优选50nm或更小;优选25nm或更小;优选10nm或更小;优选7nm或更小。纳米粒子的平均直径优选是0.3nm或更大;优选1 nm或更大。粒径通过动态光散射(DLS)来测定。通过宽度参数BP=(N75-N25)表征的氧化锆粒子的直径分布的宽度优选是4nm或更小;更优选3nm或更小;更优选2nm或更小。通过BP=(N75-N25)表征的氧化锆粒子的直径分布的宽度优选是0.01或更大。如下考虑商W是有用的:
W=(N75-N25)/Dm
其中Dm是数均直径。W优选是1.0或更小;更优选0.8或更小;更优选0.6或更小;更优选0.5或更小;更优选0.4或更小。W优选是0.05或更大。
官能化的纳米粒子优选包含氧化锆和一种或多种配体,优选具有烷基、杂烷基(例如聚(环氧乙烷))或具有极性官能团的芳基的配体;优选羧酸、醇、三氯硅烷、三烷氧基硅烷或混合的氯/烷氧基硅烷;优选羧酸。据信极性官能团键合到纳米粒子的表面。配体优选具有一个到二十五个非氢原子、优选一个到二十个、优选三个到十二个。配体优选包含碳、氢和选自由氧、硫、氮和硅组成的组的额外元素。烷基优选是C1-C18、优选C2-C12、优选C3-C8。芳基优选是C6-C12。烷基或芳基可以用异氰酸酯基、巯基、环氧丙氧基或(甲基)丙烯酰氧基进一步官能化。烷氧基优选是C1-C4,优选甲基或乙基。在有机硅烷中,一些合适的化合物是烷基三烷氧基硅烷、烷氧基(聚亚烷基氧基)烷基三烷氧基硅烷、经取代烷基三烷氧基硅烷、苯基三烷氧基硅烷和其混合物。例如,一些合适的有机硅烷是正丙基三甲氧基硅烷、正丙基三乙氧基硅烷、正辛基三甲氧基硅烷、正辛基三乙氧基硅烷、苯基三甲氧基硅烷、2-[甲氧基(聚亚乙氧基)丙基]-三甲氧基硅烷、甲氧基(三亚乙氧基)丙基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、3-巯基丙基三甲氧基硅烷、3-(甲基丙烯酰氧基)丙基三甲氧基硅烷、3-异氰酸基丙基三乙氧基硅烷、3-异氰酸基丙基三甲氧基硅烷、环氧丙氧基丙基三甲氧基硅烷和其混合物。
在有机醇中,优选是具有式R100H的醇或醇的混合物,其中R10是脂族基团、经芳族取代烷基、芳族基团或烷基烷氧基。更优选的有机醇是乙醇、丙醇、丁醇、己醇、庚醇、辛醇、十二烷醇、十八烷醇、苯甲醇、苯酚、油醇、三甘醇单甲醚和其混合物。在有机羧酸中,优选是具有式R11COOH的羧酸,其中R11是脂族基团、芳族基团、聚烷氧基或其混合物。在其中R11是脂族基团的有机羧酸中,优选的脂族基团是甲基、丙基、辛基、油基和其混合物。在其中R11是芳族基团的有机羧酸中,优选的芳族基团是C6H5。R11优选是聚烷氧基。当R11是聚烷氧基时,R11是线性串列的烷氧基单元,其中每个单元中的烷基可以与其它单元中的烷基相同或不同。在其中R11是聚烷氧基的有机羧酸中,优选的烷氧基单元是甲氧基、乙氧基和其组合。官能化的纳米粒子描述于例如US2013/0221279中。
制剂中的官能化的纳米粒子的量(以整个制剂的固体重量计算)优选是50到95wt%;优选至少60wt%、优选至少70wt%、优选至少80wt%、优选至少90wt%;优选不大于90wt%。
重氮萘醌抑制剂提供对紫外光的敏感度。在曝露于紫外光之后,重氮萘醌抑制剂抑制光致抗蚀剂膜的溶解。重氮萘醌抑制剂可以由具有一个或多个磺酰氯取代基并允许与芳醇物种(例如枯基苯酚、1,2,3-三羟基二苯甲酮、对甲酚三聚体或甲酚酚醛树脂本身)反应的重氮萘醌制成。
甲酚酚醛树脂的环氧官能度优选是2到10、优选至少3;优选不大于8、优选不大于6。甲酚酚醛树脂优选包含甲酚、甲醛和表氯醇的聚合单元。
膜厚度优选是至少50nm、优选至少100nm、优选至少500nm、优选至少1000nm;优选不大于3000nm、优选不大于2000nm、优选不大于1500nm。优选将制剂涂布到标准硅晶片或氧化铟锡(ITO)涂布的载玻片上。
实例
1.1材料
粒度分布范围在2到13nm的Pixelligent PN氧化锆(ZrO2)官能化的纳米粒子是从Pixelligent Inc.购买的。这些纳米粒子是通过溶剂热合成法与基于锆醇盐的前体合成的。所用的潜在性基于锆醇盐的前体可以包括异丙氧基锆(IV)异丙醇、乙氧基锆(IV)、正丙氧基锆(IV)和正丁氧基锆(IV)。本发明的上下文中所描述的不同的潜在性封盖剂(cappingagent)可以通过盖帽交换方法添加到纳米粒子中。正性宽带g线和i线可能性SPR-220光致抗蚀剂购自MicroChem。显影剂MF-26A(2.38wt%氢氧化四甲铵)由陶氏电子材料集团(theDow Electronic Materials group)提供。所用正性光致抗蚀剂SPR-220的组成总结于表1中。
表1.正性光致抗蚀剂SPR-220的组成。
组分 | 百分比 |
乳酸乙酯 | 30-50 |
苯甲醚 | 15-25 |
重氮光活性化合物 | 1-10 |
甲酚酚醛树脂 | 14-40 |
甲酚 | 0.01-0.99 |
2-甲基丁基乙酸酯 | 1-5 |
乙酸正戊酯 | 2-7 |
有机硅氧烷表面活性剂 | 0.01-0.1 |
1.2薄膜制备
制备含有不同比率的与正性光致抗蚀剂SPR-220混合的Pixelligent PA(Pix-PA)和Pixelligent PN(Pix-PB)型纳米粒子(均基于官能化的氧化锆纳米粒子)的溶液。将所获溶液搅拌过夜,并进一步在ITO涂布的玻璃(<15Ω/sq)上加工成薄膜,以及通过旋转涂布机以1500rpm的旋转速度加工2分钟成硅晶片。
1.3介电常数表征
在ITO沉积的纳米粒子-光致抗蚀剂薄膜上以的速率沉积直径是3mm的50nm厚金电极。使ITO与鳄鱼夹接触,并且使金电极与细金线接触。使用Novocontrol Alpha-A阻抗分析仪在1.15MHz下测量每个样品的电容,并且通过方程式1测定介电常数,并且C是电容,εr是介电常数,ε0是真空介电常数,A是电极面积且d是光致抗蚀剂的厚度。在四个不同的位置测量每个膜以确定标准偏差。
C=εr ε0.A/d 方程式1
1.4光可成像性(整片曝露(Flood exposure))
光可成像条件在表2总结为时间以获得小于10%保留膜。使膜在115℃下经受软烤5分钟。随后通过使用Oriel Research弧光灯源使其曝露于UV照射,所述弧光灯源容纳配有设计用于350到450主光谱范围内的高反射性和偏振不敏感性的双色束转向镜的1000W汞灯。所用显影剂是基于氢氧化四甲铵的MF-26A。在后烘烤后,将经涂布晶片浸入含有MF-26A的培养皿中6分钟。通过M-2000Woollam光谱椭偏仪测定每次浸渍时间后的膜厚度。
表2.光可成像条件。
UV曝露 | 保持时间 | 在115℃下后烘烤 |
380mJ/cm2 | 35min | 2min |
2.结果
2.1介电常数结果
表3列出了随并入光致抗蚀剂中的纳米粒子的重量百分比变化的在1.15MHz下测量的由不同量的与SPR-220正性光致抗蚀剂混合的Pixelligent PA(Pix-PA)和Pixelligent PN(Pix-PN)型纳米粒子制成的几个薄膜的介电常数。对于存在于给定薄膜中的89.1wt%纳米粒子,所获得的基于Pixelligent PA型纳米粒子的薄膜的介电常数高达8.88,而对于存在于给定薄膜中的81.23wt%纳米粒子,基于Pixelligent PN型纳米粒子的薄膜的介电常数高达8.46两种结果都显著地高于基础SPR-220光致抗蚀剂的介电常数以及陶氏客户所要求的介电常数CTQ。
表3.随并入光致抗蚀剂中的纳米粒子的重量百分比变化的在1.15MHz下测量的SPR-220-纳米粒子薄膜的介电常数。
2.2复合薄膜的光可成像性
表4显示经历表3中详述的曝露条件前后的SPR-220-纳米粒子薄膜的厚度以及显影剂MF-26A(2.38wt%TMAH)中的6min浸泡时间。含有Pix PN型纳米粒子的膜在6分钟后完全移除,不管存在于膜中的纳米粒子的浓度如何。在含有Pix-PA纳米粒子的薄膜的情况下,只有含有最大量纳米粒子的薄膜几乎完全被移除。当与含有这种类型的纳米粒子的其它膜的厚度(>3000nm)相比时,这可以归属于这种膜的较低厚度( )。含有Pix PA和Pix PN纳米粒子的薄膜的可移除性之间的差异可以通过连接到两种类型的纳米粒子上的不同配体来解释,并且配体连接到在UV曝露下潜在地更强烈交联的Pix PA型纳米粒子。
表4.经历曝露和显影条件前后的SPR-220纳米粒子薄膜的厚度。
Claims (7)
1.一种用于制备光可成像膜的制剂;所述制剂包含:(a)包含甲酚酚醛树脂和重氮萘醌抑制剂的正性光致抗蚀剂;和
(b)官能化的氧化锆纳米粒子。
2.根据权利要求1所述的制剂,其中所述官能化的氧化锆纳米粒子的平均直径是0.3nm到50nm。
3.根据权利要求2所述的制剂,其中所述官能化的氧化锆纳米粒子包含具有羧酸、醇、三氯硅烷、三烷氧基硅烷或混合的氯/烷氧基硅烷官能团的配体。
4.根据权利要求3所述的制剂,其中所述配体具有一个到二十个非氢原子。
5.根据权利要求4所述的制剂,其中所述甲酚酚醛树脂的环氧官能度是2到10。
6.根据权利要求5所述的制剂,其中所述制剂中的官能化的纳米粒子的量以整个制剂的固体重量计算是50到95wt%。
7.根据权利要求6所述的制剂,其中所述甲酚酚醛树脂包含甲酚、甲醛和表氯醇的聚合单元。
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WO2005088396A1 (ja) * | 2004-03-12 | 2005-09-22 | Toray Industries, Inc. | ポジ型感光性樹脂組成物、それを用いたレリーフパターン、及び固体撮像素子 |
US8179622B2 (en) * | 2005-12-22 | 2012-05-15 | Fujifilm Corporation | Photosensitive transfer material, member for display device, process for producing the member, black matrix, color filter, process for producing the color filter, substrate for display device, and display device |
JP4818839B2 (ja) | 2006-07-19 | 2011-11-16 | 株式会社 日立ディスプレイズ | 液晶表示装置及びその製造方法 |
JP5423802B2 (ja) * | 2009-09-29 | 2014-02-19 | 東レ株式会社 | ポジ型感光性樹脂組成物、それを用いた硬化膜および光学デバイス |
WO2012058271A2 (en) | 2010-10-27 | 2012-05-03 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
-
2016
- 2016-11-21 TW TW105138147A patent/TW201741765A/zh unknown
- 2016-12-07 WO PCT/US2016/065226 patent/WO2017105937A1/en active Application Filing
- 2016-12-07 KR KR1020187018077A patent/KR20180095543A/ko unknown
- 2016-12-07 CN CN201680070732.5A patent/CN108292095A/zh not_active Withdrawn
- 2016-12-07 EP EP16820410.5A patent/EP3391146A1/en not_active Withdrawn
- 2016-12-07 US US15/781,722 patent/US20180356726A1/en not_active Abandoned
- 2016-12-07 JP JP2018527084A patent/JP2019502151A/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108780277A (zh) * | 2016-03-24 | 2018-11-09 | 陶氏环球技术有限责任公司 | 具有高介电常数的光可成像薄膜 |
Also Published As
Publication number | Publication date |
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KR20180095543A (ko) | 2018-08-27 |
JP2019502151A (ja) | 2019-01-24 |
EP3391146A1 (en) | 2018-10-24 |
US20180356726A1 (en) | 2018-12-13 |
TW201741765A (zh) | 2017-12-01 |
WO2017105937A1 (en) | 2017-06-22 |
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