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Home  >  Journal list  >  Polymer Journal  >  Vol.45  No.6 (2013)  >  pp.606-613

Polymer Journal
<<Previous article Vol.45  No.6 (2013)   pp.606 - 613 Next article>>

Synthesis of polymers with a norbornane backbone by radical copolymerization of alkyl 2-norbornene-2-carboxylates for photoresist applications

Eiji Ihara1, Satoru Ishii1, Kotaro Yokoyama1, Yuka Fujiwara1, Takafumi Ueda1, Kenzo Inoue1, Tomomichi Itoh1, Hikaru Momose2 and Mitsufumi Nodono2
1Department of Material Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, Ehime, Japan
2Corporate Research Laboratories, Mitsubishi Rayon Co., Ltd., Hiroshima, Japan

The radical copolymerization of alkyl 2-norbornene-2-carboxylates, 1a–c, with alkyl (meth)acrylates, to produce copolymers with norbornane in the main chain, is described here. γ-Butyrolactone- and hydroxy group-containing norbornene-based monomers (1b and 1c, respectively) were freshly synthesized, and their radical copolymerization behavior with n-butyl acrylate was examined. Methyl 2-norbornene-2-carboxylate, 1a, and the new monomers, 1b and 1c, were employed as comonomers for radical terpolymerization with lactone- and adamantane-containing (meth)acrylates to produce copolymers that could be applied as new, more chemically robust 193-nm photoresist materials. The dissolution rate of the spin-coated copolymer films after exposure to a photoacid generator, a significant characteristic in the photoresist application, was measured for various exposure doses of 193-nm ArF laser light under standard conditions in an aqueous alkaline solution.

radical copolymerization; 2-substituted norbornene; 193-nm photoresist material

Received: July 19, 2012 , Revised: August 24, 2012
Accepted: August 27, 2012 , Published online: November 14, 2012
© 2013 The Society of Polymer Science, Japan

NatureAbstract (Nature)


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