脂肪环“燕尾型”共聚物LB膜的制备及光刻性质
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摘要
本论文以248run KrF紫外光作为光刻光源、Langmuir-Blodgett (LB)膜技术为主要成膜手段,设计合成了一系列具有特殊结构和功能基团的高分子化合物,其中包括作为抗蚀剂成膜组分的两亲性分子长链烷基甲基丙烯酰胺；作为抗蚀剂光敏感组分的烯丙基丙二酸二金刚烷甲酯(DAdMAMA),烯丙基丙二酸二环己基甲酯(DCyMAMA),以及甲基丙烯酸-1-甲酯(AdMMA),甲基丙烯酸环己基甲酯(CyMMA),甲基丙烯酸薄荷基酯(MeMMA)(见图1)；并通过自由基共聚将成膜组分与光敏组分进行聚合,并用红外光谱(FT-IR)、质谱(MS)、紫外光谱(UV)、核磁共振氢谱(1HNMR)、碳谱(13CNMR)、凝胶渗透色谱(GPC)和热重-差示扫描量热法(TG-DSC)对单体及聚合物的结构、组成、分子量和热稳定性进行了表征。研究了其成膜性能及光刻性质,并对光刻机理进行了的探究。
研究表明,甲基丙烯酰胺的烷基链长度及其在共聚物中的含量对成膜性能有较大影响,共聚物中高含量的N-十六烷基甲基丙烯酰胺对系列光敏组分的成膜性能有很大帮助,在水面上能形成紧密排列的Langmuir膜并可转移至不同材质的固体基片上形成均匀的LB多层膜；另一方面,高含量的成膜组分虽然使得共聚物的成膜性能提高,但是光敏组分含量的降低使得共聚物对紫外光的敏感性降低,从而导致在光刻的过程中需要更多的能量才能得到较好的光刻图形。如要制备较高分辨率的光刻图形,共聚物应在保证较高的光敏感性基础上,具有较好的成膜性能。以下几种能够达到上述要求的光致抗蚀剂,包括投料比HDMA: DAdMAMA=8:2的h2a20, HDMA:AdMMA=6:4的hla40, HDMA:DCyMAMA=7：3的h2d30。
以h2a20为例,图2所示为p(HDMA-DAdMAMA)[h2a20]单层膜转移到石英基片上的紫外光谱图,从图中我们可以看出,在0-26层时,紫外吸收强度变化随层数呈现良好的线性关系,之后紫外吸收变化开始变缓,说明26层后LB膜的转移比开始减小,成膜性能下降证明Langmuir膜能够均匀地转移到基片上,说明在38层以下可以制备得到排列有序的多层LB膜。图2石英基片上h2a20LB膜沉积不同层数的紫外吸收图谱(86层,Y型,SP=31mN／m)；插图为LB膜在193nm处吸光度与沉积层数的关系
图3为硅基片上4l层h2a20LB膜AFM图,表面有大小均一,平整突起,说明h2a20能够形成均匀有序的LB膜。图3.硅基片上共聚物h2a20LB膜的原子力显微镜图,(a)为高度图,(b)为3D图
除了具有较好的成膜性能,h2a20LB膜通过248nm光刻工艺能够得到较高分辨率的光刻图形和金属刻蚀模型。研究结果表明,聚合物h2a20具有一定的光敏感性,图4为在31mN／m下的15层h2a20分别在硅基片和镀铬玻璃基片表面的光刻图形(光刻条件：曝光时间为60min,显影条件为丙酮显影5s或TMAH显影20s)。图4左图为硅片上15层ha20LB膜曝光显影后放大500倍的光学显微镜图,右图为镀铬玻璃基片上16层h2a0LB膜曝光显影后放大500倍的光学显微镜图(光刻条件：曝光时间为60min,显影条件为丙酮显影3s或TMAH显影10s)
分别用紫外,红外,凝胶渗透色谱,示差扫描量热法(TG-DSC)对共聚物LB膜的光刻机理进行了初步探索。研究结果表明,在248nm曝光下,h2a20共聚物分子首先发生金刚烷甲基侧链的断裂生成羧酸结构,当曝光时间足够长时,还会发生主链的断裂。
图5推测h2a20的光分解机理
In this paper, a series of new "Swallow tailed" photoresists containing amphipathic molecule N-Alkyl methyl acrylamide as film components and a seris of light sensitive components containing Allyl-malonic acid-diadamantane ester (DAdMAMA), Allyl-malonic acid-cyclohexyl Methyl ester, and Adamantane methyl methacrylate (AdMMA), Cyclohexyl methyl methacrylate (CyMMA), Menthol methyl methacrylate (MeMMA)(Fig1); The composition and molecular weight of these copolymers were characterized by1H NMR and gel permeation chromatography (GPC), respectively. Their properties of film-forming, lithographic performance and lithography mechanisms were also explored. Fig1Polymer structure diagram
The monolayer behavior at air/water interface and Langmuir film transfer ability of copolymers were determined by the length and the mole fraction of alkyl in acrylamide in copolymers. The copolymer containing high mole fraction of hexadecyl group could form condensed monolayer on air/water interface, and could be transferred to different substrates to form homogeneous LB films. Through studying, better photopatterning of copolymers, h2a20(HDMA:DAdMAMA=8:2); h1a40(HDMA:AdMMA=6:4) and h2d30(HDMA:DCyMAMA=7:3), could be obtained.
Take p(HDMA-DAdMAMA)[h2a20] as an example, the linear relationship between the absorbance and the number of deposited layers in Figure2suggested that a regular deposition of the copolymer monolayer took place, resulting in uniform h2a20LB films. We observed that the absorbation was propotion to monolayer deposited from2and26layers, and then slowly increase because of lowing of transfer ratio, indicating that regular multilayers ranging from2to26layers could be formed. Fig2UV absorption of p(HDMA-AdMAMA)[h2a20] LB films (Inset:plots of the absorbance at192nm vs. the numberof LB films deposited).
AFM planar graph and3-D images of15layers of h2a20LB films were measured (Figure3). High orientation and order of the molecules in LB films could be observed, suggesting that a regular deposition of the copolymer monolayer took place.
Figure3AFM planar graph (left) and3-D (right) images of15layers of h2a20LB films on silicon.
Photolithographic properties of these copolymers were also investigated. Photopatterns15layers of h2a20LB films with the resolution of0.75μm could be obtained by deep UV irradiation, followed by development with acetone or TMAH solution (Figure4).
Figure4Optical micrograph of photopatterns of15layers p(HDMA-DAdMAMA)[h2a20] LB films on silicon. Right:Optical micrograph of etched pattern of chrome films on glass substrate.
The photodecomposition mechanism of h2a20LB films irradiated with deep UV light was explored. UV-vis, FT-IR, GPC, TG-DSC were used to explore characteristics of h2a20LB films irradiated. Possibly photodecomposition mechanism of h2a20LB films is shown in Fig5.
Fig5Plausible photodecomposition mechanism of h2a20
研究表明,甲基丙烯酰胺的烷基链长度及其在共聚物中的含量对成膜性能有较大影响,共聚物中高含量的N-十六烷基甲基丙烯酰胺对系列光敏组分的成膜性能有很大帮助,在水面上能形成紧密排列的Langmuir膜并可转移至不同材质的固体基片上形成均匀的LB多层膜；另一方面,高含量的成膜组分虽然使得共聚物的成膜性能提高,但是光敏组分含量的降低使得共聚物对紫外光的敏感性降低,从而导致在光刻的过程中需要更多的能量才能得到较好的光刻图形。如要制备较高分辨率的光刻图形,共聚物应在保证较高的光敏感性基础上,具有较好的成膜性能。以下几种能够达到上述要求的光致抗蚀剂,包括投料比HDMA: DAdMAMA=8:2的h2a20, HDMA:AdMMA=6:4的hla40, HDMA:DCyMAMA=7：3的h2d30。
以h2a20为例,图2所示为p(HDMA-DAdMAMA)[h2a20]单层膜转移到石英基片上的紫外光谱图,从图中我们可以看出,在0-26层时,紫外吸收强度变化随层数呈现良好的线性关系,之后紫外吸收变化开始变缓,说明26层后LB膜的转移比开始减小,成膜性能下降证明Langmuir膜能够均匀地转移到基片上,说明在38层以下可以制备得到排列有序的多层LB膜。图2石英基片上h2a20LB膜沉积不同层数的紫外吸收图谱(86层,Y型,SP=31mN／m)；插图为LB膜在193nm处吸光度与沉积层数的关系
图3为硅基片上4l层h2a20LB膜AFM图,表面有大小均一,平整突起,说明h2a20能够形成均匀有序的LB膜。图3.硅基片上共聚物h2a20LB膜的原子力显微镜图,(a)为高度图,(b)为3D图
除了具有较好的成膜性能,h2a20LB膜通过248nm光刻工艺能够得到较高分辨率的光刻图形和金属刻蚀模型。研究结果表明,聚合物h2a20具有一定的光敏感性,图4为在31mN／m下的15层h2a20分别在硅基片和镀铬玻璃基片表面的光刻图形(光刻条件：曝光时间为60min,显影条件为丙酮显影5s或TMAH显影20s)。图4左图为硅片上15层ha20LB膜曝光显影后放大500倍的光学显微镜图,右图为镀铬玻璃基片上16层h2a0LB膜曝光显影后放大500倍的光学显微镜图(光刻条件：曝光时间为60min,显影条件为丙酮显影3s或TMAH显影10s)
分别用紫外,红外,凝胶渗透色谱,示差扫描量热法(TG-DSC)对共聚物LB膜的光刻机理进行了初步探索。研究结果表明,在248nm曝光下,h2a20共聚物分子首先发生金刚烷甲基侧链的断裂生成羧酸结构,当曝光时间足够长时,还会发生主链的断裂。
图5推测h2a20的光分解机理
In this paper, a series of new "Swallow tailed" photoresists containing amphipathic molecule N-Alkyl methyl acrylamide as film components and a seris of light sensitive components containing Allyl-malonic acid-diadamantane ester (DAdMAMA), Allyl-malonic acid-cyclohexyl Methyl ester, and Adamantane methyl methacrylate (AdMMA), Cyclohexyl methyl methacrylate (CyMMA), Menthol methyl methacrylate (MeMMA)(Fig1); The composition and molecular weight of these copolymers were characterized by1H NMR and gel permeation chromatography (GPC), respectively. Their properties of film-forming, lithographic performance and lithography mechanisms were also explored. Fig1Polymer structure diagram
The monolayer behavior at air/water interface and Langmuir film transfer ability of copolymers were determined by the length and the mole fraction of alkyl in acrylamide in copolymers. The copolymer containing high mole fraction of hexadecyl group could form condensed monolayer on air/water interface, and could be transferred to different substrates to form homogeneous LB films. Through studying, better photopatterning of copolymers, h2a20(HDMA:DAdMAMA=8:2); h1a40(HDMA:AdMMA=6:4) and h2d30(HDMA:DCyMAMA=7:3), could be obtained.
Take p(HDMA-DAdMAMA)[h2a20] as an example, the linear relationship between the absorbance and the number of deposited layers in Figure2suggested that a regular deposition of the copolymer monolayer took place, resulting in uniform h2a20LB films. We observed that the absorbation was propotion to monolayer deposited from2and26layers, and then slowly increase because of lowing of transfer ratio, indicating that regular multilayers ranging from2to26layers could be formed. Fig2UV absorption of p(HDMA-AdMAMA)[h2a20] LB films (Inset:plots of the absorbance at192nm vs. the numberof LB films deposited).
AFM planar graph and3-D images of15layers of h2a20LB films were measured (Figure3). High orientation and order of the molecules in LB films could be observed, suggesting that a regular deposition of the copolymer monolayer took place.
Figure3AFM planar graph (left) and3-D (right) images of15layers of h2a20LB films on silicon.
Photolithographic properties of these copolymers were also investigated. Photopatterns15layers of h2a20LB films with the resolution of0.75μm could be obtained by deep UV irradiation, followed by development with acetone or TMAH solution (Figure4).
Figure4Optical micrograph of photopatterns of15layers p(HDMA-DAdMAMA)[h2a20] LB films on silicon. Right:Optical micrograph of etched pattern of chrome films on glass substrate.
The photodecomposition mechanism of h2a20LB films irradiated with deep UV light was explored. UV-vis, FT-IR, GPC, TG-DSC were used to explore characteristics of h2a20LB films irradiated. Possibly photodecomposition mechanism of h2a20LB films is shown in Fig5.
Fig5Plausible photodecomposition mechanism of h2a20
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