Investigation of Acid-Catalyzed Insolubilization Reactions for Alicyclic Polymers with Carboxyl Groups.

Tsuchiya, Yuko; Hattori, Takashi; Yamanaka, Ryoko; Shiraishi, Hiroshi

doi:10.2494/photopolymer.10.579

Cited by 10 publications

(7 citation statements)

References 4 publications

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“…In the early stage of our research on negative-tone ArF single-layer resists 6-16 based on chemical amplification, we examined the use of acid-catalyzed insolubilization reactions between aliphatic carbinols and alicyclic polymers with carboxylic moiety. 6 Although the negative-tone resist exhibited high insolubilization reactivity, the obtained patterns showed swelling distortion in the sub-micrometer range. This distortion is due to the penetration of the aqueous-base developer into remaining carboxylic groups in the exposed area.…”

Section: Introductionmentioning

confidence: 97%

Development of high-performance negative-tone resists for 193-nm lithography

Hattori

Yokoyama

Kimura

et al. 2003

Advances in Resist Technology and Processing XX

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We have been developing negative-tone resist systems utilizing an acid-catalyzed intramolecular esterification of γ-and δ-hydroxy acid for ArF phase-shifting lithography. In this paper, α−acryloyloxy-β,β-dimethyl-γ-butyrolactone (DBLA), adamantane lactone acrylate (AdLA), and norbornane lactone acrylate (NLA) were examined as a precursor of hydroxy acid. It was found that AdLA and NLA are not hydrolyzed into hydroxy acid under an alkali hydrolysis condition. DBLA was found to produce γ-hydroxy acid, which is stable in the resist solution. The γ-hydroxy acid derived from DBLA becomes γ-lactone relatively easily by an acid-catalyzed reaction and can be used to make resists insoluble.Since the variation and the flexibility of the copolymer composition of the base polymer can be increased, the resist properties are controllable and the pattern quality can be improved by utilizing γ-hydroxy acid derived from DBLA.

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Section: Introductionmentioning

confidence: 97%

Development of high-performance negative-tone resists for 193-nm lithography

Hattori

Yokoyama

Kimura

et al. 2003

Advances in Resist Technology and Processing XX

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“…On the contrary, not so much research has been done on ArF negative resists. [13][14][15][16] In order to make good use of strong resolution enhancement, such as a phase-shifting mask, both positive and negative high-performance…”

Section: Introductionmentioning

confidence: 99%

Micro-Swelling-Free Negative Resists for ArF Phase-Shifting Lithography Utilizing Acid Catalyzed Intramolecular Esterificaton.

Hattori

Tsuchiya

Yokoyama

et al. 1999

J. Photopol. Sci. Technol.

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We have examined alicyclic polymers with a Y hydroxy acid structure in order to investigate the properties of y hydroxy acid and y lactone as function groups of ArF negative resist materials. From the viewpoint of transparency and dry-etching resistance, y hydroxy acid and 1-lactone structure were found to be suitable for ArF negative resist materials. The reactivity of the acid-catalyzed reaction of y hydroxy acid is affected by the polymer structure. Using ArF excimer laser stepper, 0.20µm line-and-space patterns without micro-swelling distortion were obtained from a negative resist consisting of an alicyclic polymer with the 1' hydroxy acid structure and a photoacid generator. Distortion was avoided because the number of carboxyl groups decreased drastically in the exposed area by the acid-catalyzed Intramolecular esterification of y hydroxy acid-to y lactone. As a result, y hydroxy acid and y lactone structure were found to be suitable function groups for ArF negative resist materials.

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“…[14] Although the negative resist exhibited high insolubilization reactivity, the obtained patterns showed swelling distortion in the sub-micrometer range.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, the resolution of ArF excimer-laser lithography must be strongly enhanced, for example by using a phase-shifting mask. [ 1,2] In order to make good use of strong resolution enhancement, positive [3][4][5][6][7][8][9][10][11][12][13] and negative [14][15][16][17][18][19][20][21][22][23] high-performance ArF resists are indispensable.…”

Section: Introductionmentioning

confidence: 99%