Molecular Design and Synthesis of 3-Oxocyclohexyl Methacrylate for ArF and KrF Excimer Laser Resist

Nozaki, Koji; Kaimoto, Yuko; Takahashi, Makoto; Takechi, Satoshi; Abe, Naomichi

doi:10.1021/cm00045a004

Cited by 36 publications

(26 citation statements)

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“…However, as the exposure wavelength becomes shorter, it appears to be difficult to balance the dry etch resistance with the transparency which is required for effective exposure. Strategies having been proposed to address such a problem include the incorporation of alicyclic moieties into acrylic-based polymer matrix [4][5][6][7][8][9][10][11] ; exploitation of cyclo-olefin based polymer materials [12][13][14][15]. Alternatively, we have proposed [ 16] that the dry etch resistance can be imparted to the matrix after the exposure is completed (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Cyclization Reaction in Acrylonitrile-Contained Acrylic Copolymers and Its Possible Application for the Improvement of Dry Etch Resistance for Photoresists.

Zhao

Sakurai

Ohfuji

et al. 1998

J. Photopol. Sci. Technol.

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Acrylonitrile (AN)/methacrylic acid (MAA) copolymer and AN/tert-butyl methacrylate (tBMA)/MAA terpolymer were prepared, and their dry etch resistance were measured The excellent dry etch resistance found in these materials were attributed to the contribution of some induced chemical reactions. To further understand their roles in the improvement of dry etch resistance, the reactions especially the thermally induced cyclization reaction were investigated in detail. It was found that thermally induced cyclization of the nitrile groups in carboxyl acid-contained copolymers closely depended on the content of the acidic component. Protection of the acid moiety through esterfication thus suppressed the occurrence of the reaction. Conversely, cleavage of the protection groups led to the resumption of the reaction. Attempt was made to correlate the increase of fry etch resistance upon thermal treatment with the formation of cyclized structures.

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Section: Introductionmentioning

confidence: 99%

Cyclization Reaction in Acrylonitrile-Contained Acrylic Copolymers and Its Possible Application for the Improvement of Dry Etch Resistance for Photoresists.

Zhao

Sakurai

Ohfuji

et al. 1998

J. Photopol. Sci. Technol.

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show abstract

“…In spite of the limitation in the matrix polymers for such short-wavelength light, transparent and etch-resistant materials have been reported in a few brief years by workers at Fujitsu [5][6][7][8][9], Matsushita [10], IBM/MIT team [1 1 ], NEC [12], and Toshiba [13]. Much efforts have been focused on methacrylate polymers with alicyclic pendant groups to demonstrate sub-0.2-µm resolution to date.…”

Section: Introductionmentioning

confidence: 99%

New Protective Groups in Alicyclic Methacrylate Polymers for 193-nm Resists.

Nozaki

Yano

1997

J. Photopol. Sci. Technol.

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“…Recently, design and synthesis of chemically amplified resists for 193-nm lithography has been studied actively. We have developed single-layer resist materials for 193-nm lithography to meet the abovementioned requirements [1][2][3][4][5]. The use of alicyclic methacrylate polymers, such as adamantyl methacrylate, is the principal concept for transparency with etch resistance.…”

Section: Introductionmentioning

confidence: 99%

“…The acid cleavage of the adamantyl group would promote the solubility in the exposed regions. The pyranyl (mevalonic lactone) substituent has a cyclic ~i-hydroxy ketone structure, which is suitable for chemical amplification [4]. Furthermore, it is so hydrophilic that it can cancel out the strong hydrophobicity of the adamantyl protective group.…”

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confidence: 99%