Dimer radical ions of aromatic molecules in which excess charge is localized in a pair of rings have been extensively investigated. While dimer radical cations of aromatics have been previously produced in the condensed phase, the number of molecules that form dimer anions is very limited. In this study, we report the formation of intramolecular dimer radical ions (cations and anions) of diphenyl sulfone derivatives (DPs) by electron beam pulse radiolysis in the liquid phase at room temperature. The density functional theory (DFT) calculations also showed the formation of the dimer radical ions. The torsion barrier of the phenyl ring of DPs was also calculated. It was found that the dimer radical ions show the larger barrier than the neutral state. Finally, stability of the dimer radical anion is dependent on not only the inductive effect of the sulfonyl group but the conjugation involving the d-orbital of the S atom and the phenyl rings.
Efforts are being focused on increasing the power of extreme ultraviolet (EUV) light sources used in semiconductor manufacturing to increase the throughput. As a result, the investigation of the effect of high power sources on resist materials is a critical issue. A chemically amplified resist (CAR) and a non-CAR were irradiated with 13.5 nm EUV high-flux pulses from a soft X-ray free-electron laser (FEL). In the non-CAR, the positive-tone resist (ZEP520A) exhibited lower sensitivity at high irradiation densities, while the negative-tone resist exhibited a higher sensitivity. In addition, the dose rate did not considerably affect the sensitivity of the CAR.
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