Citation: CHEN Jin-Ping, HAO Qing-Shan, WANG Shuang-Qing, YANG Shu-Min, ZHAO Jun, WU Yan-Qing, ZENG Yi, YU Tian-Jun, YANG Guo-Qiang, LI Yi. Qualitative and Quantitative Measurement of Outgassing of Molecular Glass Photoresists under Extreme Ultraviolet Lithography[J]. Chinese Journal of Analytical Chemistry, ;2020, 48(12): 1658-1665. doi: 10.19756/j.issn.0253-3820.201366 shu

Qualitative and Quantitative Measurement of Outgassing of Molecular Glass Photoresists under Extreme Ultraviolet Lithography

1.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
2.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
3.
Shanghai Synchrotron Radiation Facility, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201204, China;
4.
University of Chinese Academy of Sciences, Beijing 100039, China

Received Date: 24 June 2020
Revised Date: 27 October 2020

Fund Project: This work was supported by the National Science and Technology Major Project of the Ministry of Science and Technology of the People's Republic of China (Nos. 2018ZX02102005, 2011ZX02701).

A system was set up for quantitative and qualitative analysis of outgassing of photoresists using pressure rise method. The outgassing of molecular glass photoresist films (Film A, B, C and D) based on 9, 9'-spirobifluorene (SP) derivatives was evaluated by the system. Film A was formed by SP with substituent group of tert-butyloxycarbonyl (Boc), and Film B and C were prepared by covering Film A with top-coating material in different thicknesses. Film D was formed by SP with substituent group of adamantyl acetate (Ad). The components of residual gas during the EUV irradiation were detected by the quadruple mass spectrometer (QMS). In the case of Film A, it showed that the source of the outgassing was mainly from the acid catalytic reaction of substituent of Boc group, releasing isobutylene (C₄H₈) and CO₂ gas, along with a small amount of benzene component produced by the decomposition of photo acid generator (PAG). Film B and C, covered with protective layer, were similar to that of film A, but the ion abundance decreased obviously. Ion peak of CO₂ molecule and the fragment peaks of adamantane substituent were observed in mass spectra of Film D. The amount of outgassing for different films was analyzed in-situ by an ion gauge, and it was found that the rate of outgassing was fast in the initial stage of exposure, and then slow down, suggesting that the molecules on the surface of the films were more likely to release gas. Besides, the top-coating could significantly reduce the rate of outgassing comparing the results of Film A and Film B/C, for instance, the outgassing could be reduced from 1.19×10¹⁵ molecule/cm² to 2.35×10¹⁴ molecule/cm² under the exposure dose of 10 mJ/cm² by covering with 30-nm thickness of top-coating material, suggesting that the top-coating was an effective method to reduce outgassing. By comparing the outgassing of Film D and Film A that was formed by the resist materials with different peripheral substituent groups, it was found that the outgassing of Film D was decreased by 10 times than that of Film A, indicating that the substituent group of the photoresist materials had a significant effect on the outgassing, and the substituent group with higher molecular weight and thermal activation energy (E_a) was useful to reduce outgassing.
- Photoresist,
- Outgassing,
- Molecular glass,
- Extreme ultraviolet,
- Lithography
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