Synthesis and Properties of Bisphenol A - Bis(methoxymethyl)biphenyl Novolac Resin:

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  • Hirohito Yamasaki
    National Institute of Technology, Ube College, Department of Chemical & Biological Engineering
  • Sayuri Nakano
    National Institute of Technology, Ube College, Department of Chemical & Biological Engineering
  • Takahisa Furumoto
    Meiwa Plastic Industries, Ltd., Technical Engineering Department
  • Sadaaki kuroiwa
    Meiwa Plastic Industries, Ltd., Technical Engineering Department
  • Seiichirou takabayashi
    Meiwa Plastic Industries, Ltd., Technical Engineering Department

Bibliographic Information

Other Title
  • ビス（メトキシメチル）ビフェニルを用いた ノボラック樹脂の合成と性質:
  • ビス(メトキシメチル)ビフェニルを用いたノボラック樹脂の合成と性質 : ビスフェノール類に着眼した柔軟性をもつフォトレジスト材の開発
  • ビス(メトキシメチル)ビフェニル オ モチイタ ノボラック ジュシ ノ ゴウセイ ト セイシツ : ビスフェノールルイ ニ チャクガン シタ ジュウナンセイ オ モツ フォトレジストザイ ノ カイハツ
  • Development of Photo-resist Material Having Flexibility Noticed with Bisphenol unit
  • ビスフェノール類に着眼した柔軟性をもつフォトレジスト材の開発

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Abstract

<p>Cresol formaldehyde novolac resins (Cre/Form) are used as photo-resist materials because they can be applied minutely onto hard silicon wafers, which are used in the process of making integrated semiconductor circuits. Resins with high hardness cannot be applied minutely onto flexible bases, such as polyimide films. To develop flexible novolac resins for photo-resists, bisphenol A (BisA), which has a bulky isopropylidene group, was incorporated into the molecular backbone chain of novolac resins as a phenolic (PhOH) component. The resulting resins were much more flexible than cresol (Cre) novolac resin. In this study, BisA/BMMB and (BisA/PY)/BMMB novolac resins, where 4,4'-bis(methoxymethyl)biphenyl (BMMB) is as a comonomer and pyrogallol (PY) is added to the PhOH component, were synthesized and investigated. The chain length of BMMB was elongated through a polycondensation reaction confirmed by TOF-MASS measurements. By increasing the BMMB component in the feed, it was observed that the dissolving ratio for alkaline aq. solution (DR) decreased with increasing Mw. The maximum Mw of the BisA/BMMB and (BisA/PY)/BMMB novolac resins were 2000 and 7200, respectively. To prepare cast films, resins meeting the condition of DR below 500Å/s were chosen. Cast films of thickness 5 μm onto the polyimides, were prepared by spin-coating, heat-setting and then exposing to developer solution. The flexibility of the obtained resins were evaluated by observation of the bent parts with microscope. The order of flexibility of the obtained novolac resins was PY/BMMB > (BisA/PY)/BMMB >> BisA/BMMB. The lithographic performance of the novolac resins, coated with a thickness of 1.5 μm onto the silicon wafers was examined. The residual membrane thickness of PY/BMMB novolac resin, which showed the highest flexibility, was 81%. Therefore, (BisA/PY)/BMMB novolac resin showed excellent performance compared to Cre novolac resin, in terms of flexibility and fine drawing ability, in this study. The residual membrane thickness of (BisA/PY)/BMMB novolac resin was high (≒100%) and the resist pattern could draw up to 4 μm clearly.</p>

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