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One-pot synthesis of molecular glass photoresists based on β-cyclodextrin containing a t-butyloxy carbonyl group for i-line lithography

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Abstract

Positive chemically amplified molecular glass with pendant t-butyloxy carbonyl (t-BOC) groups based on β-cyclodextrin (β-CD) was prepared. The β-CD derivatives were obtained from the reaction of β-CD and di-tert-butyl dicarbonate (DBDC) in the presence of 4-dimethylaminopyridine, and the protecting ratio was controlled using various feed amounts of DBDC. Fourier-transform infrared spectroscopy and proton nuclear magnetic resonance were employed to characterize the chemical structure, indicating that the synthesis was successful. Thermal behavior was characterized by thermogravimetric analysis; the results showed that the initial thermal decomposition temperature occurred at approximately 160 °C, which could satisfy the lithography process. Ultraviolet–visible spectrophotometer indicated that the t-BOC-protected β-CD derivatives had low absorbance at 365 nm wavelength. Additionally, X-ray diffraction analysis results showed that the β-CD derivatives had amorphous form, and exhibited excellent film-forming property. The photoresists consisting of different t-BOC protecting groups showed high sensitivity when exposed to 365 nm light and post-baked at 105 °C for 90 s, followed by developing in 2.38 wt% aqueous tetramethylammonium hydroxide solution at room temperature. An enhanced line and space positive patterns with 1 μm resolution were delineated according to digital microscope.

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Acknowledgments

This work was supported by Innovation Foundation of Jiangsu (No. BY2015019-14), the National Science and Technology Major Project of China (No. 2010ZX02304), and the Jiangsu Postgraduate Scientific Research and Innovation Plan Project (No. KYLX_1127).

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Authors and Affiliations

  1. Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China

    Hu Li, Zhen Zhou, Jingcheng Liu, Wenjia Xu, Ren Liu & Xiaoya Liu

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  1. Hu Li
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  2. Zhen Zhou
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  3. Jingcheng Liu
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  4. Wenjia Xu
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  5. Ren Liu
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  6. Xiaoya Liu
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Correspondence to Jingcheng Liu or Xiaoya Liu.

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Li, H., Zhou, Z., Liu, J. et al. One-pot synthesis of molecular glass photoresists based on β-cyclodextrin containing a t-butyloxy carbonyl group for i-line lithography. Polym. Bull. 74, 1091–1101 (2017). https://doi.org/10.1007/s00289-016-1765-5

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  • DOI: https://doi.org/10.1007/s00289-016-1765-5

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