Identification of diazonaphthoquinone esters of polyhydroxybenzophenone compounds

DiCarlo, John; Evans, Otis; Fedyk, John; Ficner, Stanley A.; Khadim, Mohammad A.; Dammel, Ralph R.

doi:10.1117/12.175383

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“…Therefore, the distribution of I-1_E in PF2_E should be the intermediate state of the simulated films PF1 and PF2 (see Figure ). It should be pointed out that the pure fully esterified compounds for tri- or tetra-hydroxybenzophenone were reported as undesirable DNQ PACs due to their low solubility in common casting solvents; therefore, the current commercial or lab prepared DNQ PACs tend to be a mixture of esters of such backbones. In other words, the skin layer formation should be always observed by the use of mixed esters as DNQ PAC in the experimental site.…”

Section: Resultsmentioning

confidence: 99%

A Computational Probe into the Dissolution Inhibitation Effect of Diazonaphthoquinone Photoactive Compounds on Positive Tone Photosensitive Polyimides

Zheng

Sittert

2017

J. Phys. Chem. C

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Positive tone photosensitive polyimides (p-PSPIs) composed of poly(amic acid) (PAA) and a diazonaphthoquinone photoactive compound (DNQ PAC) have been greatly contributed to the progress of microelectronics. However, the relationships among PAC molecular structures, hydrogen-bonding interactions, and dissolution inhibitation for p-PSPIs have not been well understood. In this study, multiscale molecular modeling was utilized to evaluate such relationships. Density functional theory (DFT) calculations were used to predict the polarity of various DNQ PAC models and their corresponding indenylidene ketene (IK) compounds. Molecular dynamics (MD) simulations were performed to mimic the interactions between DNQ PAC and PAA polymer chains by calculating parameters such as the energy of mixing (ΔE mix) and Flory–Huggins parameter (χAB). The computational results showed that χAB values of PACs containing mono functional phenols significantly differed before and after UV exposure. Their corresponding suppositional p-PSPI films were found to form a “skin layer” by covering a high concentration of PAC on the surface of the film. Experimental dissolution behavior measurements of selected p-PSPI films strongly supported the computational observations. Succinctly, this work demonstrated the applicability of atomistic molecular simulations for the evaluation of dissolution inhibitation effect of DNQ PACs and to understand the possible dissolution inhibition mechanisms of p-PSPIs.

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Section: Resultsmentioning

confidence: 99%