Synthesis and Properties of Novolac Resins using Phenols with Two Isopropylidene Groups:

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  • Hirohito Yamasaki
    * National Institute of Technology, Ube College, Department of Chemical & Biological Engineering
  • Ryota Yamasaki
    * National Institute of Technology, Ube College, Department of Chemical & Biological Engineering
  • Takafumi Yamamoto
    * National Institute of Technology, Ube College, Department of Chemical & Biological Engineering

Bibliographic Information

Other Title
  • イソプロピリデン基を二つもつフェノール類を用いた ノボラック樹脂の合成と性質:
  • イソプロピリデン基を二つもつフェノール類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
  • イソプロピリデンキ オ フタツ モツ フェノールルイ 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>As we proceeded with the development of a novolac resin with flexibility and high lithography performance, we focused on adopting a linear polymer structure with few branched structures similar to a dry film resist. s In our attempt to develop a flexible novolak resin for resists, we found that BisC/Glu novolak resins consisting of bisphenol C (BisC) and glutaraldehyde (Glu) containing contain a bulky isopropylidene group in the molecular chain skeleton as a phenolic (PhOH) component, exhibited the highest flexibility and high drawing ability that we have investigated. In this study, BisP/Glu and BisM/Glu novolak resins using bisphenol P (BisP, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl] benzene) with two isopropylidene groups and its structural isomer, bisphenol M (BisM, 1,3-bis[2-(4-hydroxyphenyl)-2-propyl] benzene), were newly synthesized and their properties were investigated. In addition, novolak resins with 3－10 mol% resorcinol (Res) or pyrogallol (PY) as comonomers added to the PhOH component were also investigated. In the case of the novolac resins without comonomer addition, most of it became insoluble in alkaline aqueous solution. On the other hand, the novolac resin containing the comonomer showed the general correlation that it became soluble in the alkaline aqueous solution in spite of the high molecular weight of 3600－15000, and that the dissolving rate in alkaline aqueous solution (DR) became slow as Mw increased. From the results of bending tests, it was found that the flexibility of BisP and/or BisM based novolak resins capable of DR measurement did not reach that of BisC/Glu novolak resins, and was comparable to BisC/Form novolak resins combined with formaldehyde (Form). The reason for the insufficient flexibility of the novolak resin was that the number of hydrogen bond formation were not enough. As an index of hydrogen bond forming ability, the O/C element ratio of novolak resin was calculated, and the obtained result supported the above.</p>

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