Abstract Dual functional photosensitive epoxy resins were synthesized by solution polycondensation of 1,3-bis(4-hydroxyphenyl)propenone (BHPP) and 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)propenone (HMPHPP) with epichlorohydrin. The characterization of synthesized epoxy resins comprised Fourier transform infrared (FTIR) spectroscopy, 1H-NMR, and 13C-NMR spectroscopic techniques. The thermal properties of the epoxy resins were studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) under a nitrogen atmosphere and found that the synthesized resins were stable up to 300 °C. The effect of curing agents diaminodiphenylsulfone (DDS) and diaminodiphenylmethane (DDM) on the thermal stability of epoxy resin was compared and found that DDS cured epoxy resin has higher thermal than DDM. The photocrosslinking properties of the epoxy resins were studied with UV-Visible spectroscopy, and we observed that the olefinic double bond undergoes 2π-2π cycloaddition and leads to cyclobutane ring. Also, the effect of solvents on the photocrosslinking of the epoxy resin was also studied. Solvents with higher polarity favored the 2π-2π cycloaddition. The dual functionality of the resins was confirmed by FTIR study. The storage stability of the synthesized epoxy resins remained over more than 60 days. The synthesized epoxy resins successfully applied as negative photoresists.

中文翻译：

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用于光刻胶应用的主链含光敏基团双官能环氧树脂的研究

摘要 采用 1,3-双(4-羟基苯基)丙烯酮 (BHPP) 和 3-(4-羟基-3-甲氧基苯基)-1-(4-羟基苯基)丙烯酮 (HMPHPP) 溶液缩聚反应合成双功能光敏环氧树脂与环氧氯丙烷。合成环氧树脂的表征包括傅里叶变换红外 (FTIR) 光谱、1H-NMR 和 13C-NMR 光谱技术。在氮气氛下通过热重分析 (TGA) 和差示扫描量热法 (DSC) 研究了环氧树脂的热性能，发现合成的树脂在高达 300 °C 时是稳定的。比较了固化剂二氨基二苯砜（DDS）和二氨基二苯甲烷（DDM）对环氧树脂热稳定性的影响，发现DDS固化的环氧树脂比DDM具有更高的热稳定性。用紫外-可见光谱研究环氧树脂的光交联性能，我们观察到烯烃双键发生 2π-2π 环加成并形成环丁烷环。此外，还研究了溶剂对环氧树脂光交联的影响。具有较高极性的溶剂有利于 2π-2π 环加成。FTIR 研究证实了树脂的双重功能。合成环氧树脂的储存稳定性保持超过 60 天。合成的环氧树脂成功地用作负性光刻胶。具有较高极性的溶剂有利于 2π-2π 环加成。FTIR 研究证实了树脂的双重功能。合成环氧树脂的储存稳定性保持超过 60 天。合成的环氧树脂成功地用作负性光刻胶。具有较高极性的溶剂有利于 2π-2π 环加成。FTIR 研究证实了树脂的双重功能。合成环氧树脂的储存稳定性保持超过 60 天。合成的环氧树脂成功地用作负性光刻胶。