偶氮系光敏感化合物合成及甲基丙烯酸酯系感光性高分子正、負型光阻製備與研究; The Study and Preparation of Synthetic Diazo-series Photosensitive Compounds and Positive/Negative Photo resist of Methacrylic Ester Series Photosensitive Polymers

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题名:	偶氮系光敏感化合物合成及甲基丙烯酸酯系感光性高分子正、負型光阻製備與研究;The Study and Preparation of Synthetic Diazo-series Photosensitive Compounds and Positive/Negative Photo resist of Methacrylic Ester Series Photosensitive Polymers
作者:	鄭宗興;Tzong-Shing Cheng
贡献者:	化學工程與材料工程研究所
关键词:	厚膜光阻;正型光阻;負型光阻;感光性高分子;導電光阻;photosensitive polymer;ultra thick photo resist;conductive photo resist;positive photo resist;negative photo resist
日期:	2004-10-20
上传时间:	2009-09-21 12:20:08 (UTC+8)
出版者:	國立中央大學圖書館
摘要:	本論文研究重點主要為研究Methacrylic Acid（MAA）及2-Hydroethyl Methacrylate（2-HEMA）與偶氮類光敏感化合物1,2-Naphthoquinone-2-diazido-5-sulfonyl Chloride（5-NDSC）之合成製備光阻材料添加之單體PAC(A)及PAC(B)，以及利用Tricyclo [5,2,1,02,6]decane-dimethanol（TDMol）與5-NDSC進行酯化反應以獲得雙偶氮類光敏感化合物PAC(C)，及利用1-Chloroadamantane（1-ClAd）分別與MAA、2-HEMA來製備Adamantyl methacrylate （AdMA）與Adamantyl hydroethyl methacrylate（AdHEMA），並利用合成共振光譜儀（NMR）及紅外線光譜儀（IR）研究其結構正確性，同時利用MAA及2-HEMA分別與Benzyl methacrylate （BzMA）、3,3,5-Trimethylcyclohexyl Methacrylate （THCHMA）、AdMA及AdHEMA來製備四種不同成分及比例下之光阻基材（THM, AHM, BHM and AHHM: Binder (1) to (4)），並進一步於對上述製備之前驅物與光阻基材中探討在不同成分及比例下所製備之正型光阻材料及熱性質。結果顯示此系列之光阻基材中熱裂解溫度皆達300℃以上且Tg點亦高達150℃（BHM, THM）（第二章及第三章），並利用田口工程技術延伸應用製備正型光阻材料最佳化配方調製以獲得及了解最佳化熱性質能力（第四章）。於第五章中則利用TDMol與Methyl Acrylate（MA）先行合成雙官能團架橋單體Dimethyl-acryl-tricyclo[5,2,1,02,6]decane-dimethyl ester （TA），並利用NMR判定其結構，再進行與dipentaerythrithol hexaacrylate（DHPA）及BHM共混下添加光啟始劑1-(4-methylthiophenyl-2- (N-morpholino) propan-1-one（PI-777）及光增感劑2-isopropylthioxanthone（ITX）以製備負型光阻材料（NPR），並探討其共混下之熱性質現象及厚膜光阻可行性，藉由near UV微影製程及電子顯微鏡（SEM）證明其縱深比達八倍以上。進一步於第六章中探討利用所製備負型光阻材料（NPR）添加導電粉體並利用濕式研磨及分散技術以獲得導電性負型光阻材料（CNPR），藉由四點探針電導儀以確立其導電性，其阻抗值介於5 ~ 10 ohm之間。此研究成果中成功製備出Acrylic series之正型與負型光阻材料，並且光阻基材可同時應用於正型與負型之間，並且此基材利用紫外線光譜儀（UV）測試結果顯示在300 nm波長以下逐一衰減，顯現光阻基材應用於KrF （248 nm）與ArF（193 nm）之可行性。 This thesis investigated in synthesized of photo active compound ((PAC (A), PAC (B) and PAC (C)) by using methacrylic acid (MAA), 2-Hydroethyl Methacrylate (2-HEMA) and Tricyclo [5,2,1,02,6]decane- dimethanol (TDMol) with an 1,2-Naphthoquinone-2-diazido-5-sulfonyl Chloride (5-NDSC) and prepared of photo resist binder (1) to binder (4) by free radical polymerization using MAA and 2-HEMA within Adamantyl methacrylate (AdMA), Adamantyl hydroethyl methacrylate (AdHEMA), 3,3,5-Trimethylcyclohexyl Methacrylate (THCHMA) and Benzyl methacrylate (BzMA).which analyzed thermal property and film performance discussion in chapter 2 to 4. It is found that the thermal reliability of positive photo resist within this acrylic series is excellent by I-line (365 nm wavelength) lithography process and scanning electronic microscopy (SEM). In the chapter 4, the major discussion about Taguchi method and formulation of positive photo resist, measured the thermo-decomposition temperature by TGA, It is found that the optimal formulation of positive photo resist on the lithography process is definitely verified after having SEM surface analysis on the result. The chapter 5 discussions about negative photo resist (NPR). It is applied to ultra thick photo resist (e.g. Micro electronic mechanical system,MEMS), and synthesized of difunctional monomer of Dimethyl-acryl-tricyclo [5,2,1,02,6]decane-dimethyl ester (TA) by esterification using Methyl Acrylate (MA) and Tricyclo [5,2,1,02,6]decane dimethanol (TDMol). The other hand, prepared of formula for ultra thick negative photo resist. A few designed formulas at difference ratios are conducted by co-mixing 1-(4-methylthiophenyl-2- (N-morpholino) propan-1-one (PI-777) of the photo initiator, 2-isopropylthioxanthone (ITX) of the photo sensitizer, TA and dipentaerythrithol hexaacrylate (DHPA) of multifunctional monomer. additionally, the prepared of conductive negative photo resist (CNPR), dispersion technology by wetting mill process. measured of Surface examination was obtained by 4-point probe, its electric conductivity is 5 to 10 ohm in 2 mil diameter of array conductive photo resist to discuss in chapter 6. It is Succeed in prepared of positive and negative photo resist in this study within acrylic series binder, measured the ultraviolet absorption by UV apparatus, It is found decrease below in UV absorption curve which start on 300 nm wavelength. This materials applied to KrF (248 nm) and ArF (193 nm) to thinkable.
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