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March 29, 2026ACS Applied Polymer Materials1 citations

Synthesis and Properties of a Biophenolic End-Capped Polyimide Photoresist with High Film Retention and Sensitivity

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CJChangwei JiWWWei WeiXLXiaojie Li

Key Points

  • The aim is to synthesize and characterize a new biophenolic polyimide photoresist with enhanced properties.
  • Synthesis of methyl gallate derivative and subsequent end-capping with GEA.
  • Preparation of poly(amic acid) copolymer from ODPA and 6FAP.
  • Esterification of carboxylic groups using DMFDMA to create the final polymer.
  • Characterization using FT-IR, 1H NMR, UV-vis, and GPC techniques.
  • Evaluation of lithographic performance of the formulated photoresist.
  • Formulated photoresist exhibits high sensitivity with an exposure threshold less than 100 mJ/cm2.
  • Achieved development retention rate over 95% and curing retention rate over 85% at 2 μm film thickness.
  • Maximum resolution capability of 5 μm line/space patterns.
  • Good performance maintained even at 11.5 μm film thickness, with over 90% development retention and over 75% curing retention.

Abstract

A gallic acid derivative, methyl gallate, derived from renewable resources, was used as a starting material to synthesize 3,4,5-trihydroxy-N-(2-hydroxyethyl)benzamide (GEA). GEA was employed as an end-capping agent and incorporated into a poly(amic acid) copolymer based on 4,4′-oxydiphthalic anhydride (ODPA) and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP). Subsequent esterification of the carboxylic acid groups with dimethylformamide dimethyl acetal (DMFDMA) yielded the final polymer, designated as OFPAE-G. The structure and properties of the polymers were characterized using Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR), ultraviolet–visible spectroscopy (UV–vis), and gel permeation chromatography (GPC). UV–vis analysis indicated excellent optical transmittance of the polymer at 365, 405, and 436 nm. The lithographic performance of a positive-tone photoresist formulated from the gallic acid-end-capped, photosensitive polyimide (PSPI) was evaluated. Results demonstrate that the formulated photoresist exhibits high sensitivity (Eth 95% and a curing retention rate >85%. Well-defined patterns were achieved, with a maximum resolution of 5 μm line/space (L/S). Even at an 11.5 μm film thickness, the photoresist maintained good photosensitivity, achieving a development retention rate >90% and a curing retention rate >75%. The photoresist showed good application prospects in OLED displays, MEMS, and chip packaging.

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Cite This Study

Ji et al. (2026) studied this question.

synapsesocial.com/papers/69c8c1f4de0f0f753b39c2c2https://doi.org/10.1021/acsapm.6c00187
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