The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate

doi:10.7517/j.issn.1674-0475.2007.05.357

Imaging Science and Photochemistry ›› 2007, Vol. 25 ›› Issue (5): 357-363.DOI: 10.7517/j.issn.1674-0475.2007.05.357

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The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate

HUI Chuang, MENG Qing-wei, GONG Bin, QU Jing-ping

The State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, Liaoning, P. R. China

Received:2007-01-09 Revised:2007-03-08 Online:2007-09-23 Published:2007-09-23

Abstract

Abstract: 2-methyl adamantine-2-yl methacrylate and 2-ethyl adamantine-2-yl methacrylate are two important monomers of matrix polymer for 193 nm photoresist. The two compounds are synthesized based on utilizing methylmagnesium iodide(ethylmagnesium iodide) as Grinard reagent reacted with 2-adamantone to provide 2-methyl(ethyl) adamantine-2-yl which then esterified with methacryloyl chloride in the presence of NaH to provide the target compounds with the yields of 50—60%. The structures of the compounds are confirmed by ¹HNMR, IR, MS and Elementary Analysis. The hydrolysis test was carried out using TsOH·H₂O as catalyst and the hydrolysis mechanism was discussed. The calculated hydrolysis rate constants k are -1.52 and -3.90, respectively.

Key words: 193 nm photoresist, 2-alkyl adamantine-2-yl methacrylate, 2-adamantone, hydrolysis

CLC Number:

HUI Chuang, MENG Qing-wei, GONG Bin, QU Jing-ping. The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate[J]. Imaging Science and Photochemistry, 2007, 25(5): 357-363.

References

[1] 郑金红,黄志齐,陈欣,等.193 nm光刻胶的研制[J].感光科学与光化学,2005,23(4):300-311.Zheng J H,Huang Z Q,Chen X,et al.The study of 193 nm photoresist[J].Photographic Science and Photochemistry,2005,23(4):300-311.
[2] 郑金红,黄志齐,文武.ULSI用193 nm光刻胶的研究进展[J].精细化工,2005,22(5):348-353.Zheng J H,Huang Z Q,Wen W.Progress of 193 nm photoresist for ULSI supporting materials[J].Fine Chemicals,2005,22(5):348-353.
[3] Hasegawa E,Maeda K,Iwasc S.Molecular design and development of photoresists for ArF excimer laser lithography[J].Polym.Adv.Technol.,2000,11:560-569.
[4] Okoroanyanwu U,Byers J,Shimokawa T,et al.Alicyclic polymers for 193 nm resist application:lithographic evaluation[J].Chem.Master.,1998,10:3328-3333.
[5] Seo H L,Jin S H,Choi S J,et al.Design and synthesis of new photoresist materials for ArF lithography[J].J.Appl.Polym.Sci.,2004,92:165-170.
[6] Uekono A,Ohdaira T,Suzuki R,et al.Characterization of photoresists for ArF-excimer laser lithography using monoenergetic positron beams[J].J.Polym.Sci.B,:Polym.Phys.,2004,42:341-346.
[7] Okoroanyanwu U,Shimokawa T,Byers J,et al.Alicyclic polymers for 193 nm resist applicat synthesis and characterization[J].Chem.Master.,1998,10:3319-3327.
[8] Klopp J M,Pasini D,Byers J D,et al.Microlithographic assessment of a novel family of transparent and etch-resistant chemically amplified 193 nm resists based on cyclopolymers[J].Chem.Mater.,2001,13(11):4147-4153.
[9] Taylor J C,LeSuer R J,Chambers C R,et al.Experimental techniques for detection of components extracted from model 193 nm immersion lithography photoresists[J].Chem.Mater.,2005,17(16):4194-4203.
[10] Dreibelbis R L,Khatri H N,Walborsky H M.Cyclopropanes.XXXVI.stereochemistry of the decomposition of an optically active 1-pyrazoline[J].J.Org.Chem.,1975,40(14):2074-2079.

The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate

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