Chemistry and Lithography

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Bellingham, WashingtonUSALibrary of Congress Cataloging-in-Publication Data Okoroanyanwu, Uzodinma. Chemistry and lithography / Uzodinma Okoroanyanwu. p. cm. --(Press monograph ; 192) ISBN 978-0-8194-7562-6 1.Lithography. 2.Chemistry, Technical.I. Society of Photo-optical Instrumentation Engineers. II. Title.NE2425.O38 2010 621.3815'31--dc22 2009036266 Published by SPIE P.O. Box 10 Bellingham, Washington98227-0010 USA Phone: +1 360.676.3290 Fax: +1 360.647.1445 Web: and John Wiley & Sons, Inc. 111 River Street Hoboken, New Jersey 07030 Phone: +1 201.748.6000 Fax: +1 201.748.6088 ISBN: 9781118030028 Copyright 2010 Society of Photo-Optical Instrumentation Engineers All rights reserved. No part of this publication may be reproduced or distributed in any form or by any means without written permission of the publisher. The content of this book reflects the work and thought of the author(s). Every effort has been made to publish reliable and accurate information herein, but the publisher is not responsible for the validity of the information or for any outcomes resulting from reliance thereon. Printed in the United States of America. Dedicated to the memory of the late Professor William C. Gardiner, Jr.,of The University of Texas at Austin, under whom I studied.ContentsPreface xxiAcronyms and Abbreviations xxvPart I: Origins, Inventions, and the Evolution of Lithography 11 Introduction to Lithography 32 Invention of Lithography and Photolithography 92.1 Introduction 92.2 Invention of Lithography 112.3 Invention of Photolithography 172.4 Pioneers of Photography 182.4.1 Joseph Nicephore NiepceThe inventor ofphotography and photolithography 192.4.2 Louis Jacques MandeDaguerre 252.4.3 William Henry Fox Talbot 263 Optical and Chemical Origins of Lithography 293.1 Introduction 293.2 Key Developments that Enabled the Invention andDevelopment of Lithography 333.2.1 Developments in optical physics 333.2.1.1 Tactile and emission theories of light 333.2.1.2 Early studies in optics and catoptrics 343.2.1.3 On the nature of light 383.2.1.4 Electromagnetic theory 503.2.1.5 Electromagnetic spectrum 553.2.1.6 Absorption of light 583.2.1.7 Chemical effects of light 583.2.1.8 The discovery of electrons 613.2.1.9 The discovery of x rays 623.2.1.10 Radioactivity 63vii3.2.1.11 The beginnings of quantum theory 643.2.1.12 Molecular theory of matter 653.2.1.13 Blackbody radiation 663.2.1.14 Plancks quantum hypothesis for blackbodyradiation 673.2.1.15 Einsteins quantum hypothesis for thephotoelectric effect 693.2.1.16 Bright and dark line spectra 713.2.1.17 Nuclear model of the atom 743.2.1.18 Bohrs model of the hydrogen atom 753.2.1.19 Implications of Bohrs theory 783.2.1.20 Quantum theory of light 793.2.1.21 Einsteins theory of relativity 833.2.2 Developments in optical instruments and glassmakingtechnologies 853.2.3 Developments in chemistry 953.2.3.1 The four-element theory 953.2.3.2 Chemistry as a distinct discipline 973.2.3.3 Alchemy 983.2.3.4 Early theories of combustion and calcination 993.2.3.5 Phlogiston theory 1003.2.3.6 Discovery of simple gases in common air 1023.2.3.7 Foundation of modern chemistry 1043.2.3.8 Post-Lavoisian evolution of chemistry 1093.2.3.9 Development of various elds in chemistry 1174 Evolution of Lithography 1374.1 Introduction 1374.2 Offset Lithography 1414.3 The Printed Circuit Board and the Developmentof the Electronics Industry 1424.4 The Transistor and Microelectronics Revolution 1454.4.1 The invention of the transistor 1454.4.2 Limits of discrete transistors 1474.5 The Integrated Circuit 1484.6 Other Notable Developments in TransistorTechnology 1484.7 Overall Device Technology Trends 1524.8 Semiconductor Lithography 1574.8.1 Optical lithography 1604.8.2 Challenges of decreasing exposure wavelength inoptical lithography 1654.9 X-ray Lithography 1654.10 Electron-Beam Lithography 1674.11 Ion-Beam Lithography 1694.12 Extreme Ultraviolet Lithography 170viii Contents4.13 Soft Lithography 1704.13.1 Microcontact printing 1714.13.2 Micromolding in capillaries 1724.13.3 Nanoskiving 1724.13.4 Step-and-ash imprint lithography 1724.13.5 Nanoimprint lithography 1724.14 Proximal Probe Lithography 1734.15 Atom Lithography 1754.16 Stereolithography 1764.17 Molecular Self-Assembly Lithography 176Part II: Lithographic Chemicals 1795 Lithographic Chemicals 1815.1 Introduction 1815.2 Resists 1815.2.1 Resist solvents 1845.2.2 Manufacture of resists 1845.3 Antireection Coatings 1865.4 Resist Developers and Rinses 1875.5 Resist Strippers and Cleaners 1895.6 Offset Lithographic Inks and Fountain Solutions 1935.6.1 Offset lithographic inks 1935.6.2 Fountain solutions 1946 Negative Resists 1956.1 Introduction 1956.2 Resins 1966.3 Types of Negative Resists 1996.3.1 Non-radiation-based negative resists 1996.3.1.1 Wax-lampblack-soap resists 1996.3.2 Radiation-induced negative resists 2006.3.2.1 Negative resists based on radiation-inducedcross-linking reactions 2006.3.3 Chemically amplied cross-linking negative resists 2246.3.3.1 Chemically amplied negative phenolic resistsbased on acid-catalyzed condensation/intermolecular dehydration cross-linkingreactions 2246.3.3.2 Chemically amplied negative resistsbased on radiation-induced polaritychanges 2266.3.4 Non-chemically amplied negative resists based onradiation-induced polarity changes 2276.3.4.1 Metal-chalcogenide resists 227Contents ix6.3.4.2 Ylide resists 2326.3.4.3 Diazo resists 2336.3.5 Chemically amplied negative resists based onradiation-induced polarity changes 2346.3.5.1 Chemically amplied negative resists basedon acid-catalyzed pinacol rearrangement 2346.3.5.2 Chemically amplied negative resists basedon acid-catalyzed intramolecular dehydration 2366.3.5.3 Chemically amplied condensation/intermolecular dehydration negative resistsbased on acid-catalyzed cross-linking withacid-sensitive electrophile (cross-linking agent) 2386.3.5.4 Chemically amplied methacrylate negativeresists based on acid-catalyzed esterication 2466.3.5.5 Chemically amplied methacrylate negativeresists based on acid-catalyzed deprotectionand development in supercritical CO22476.4 General Considerations on the Chemistry of Cross-Linking 2526.5 Negative Resists Arising from Polymerization of Monomersin the Presence of Polyfunctional Components 2566.6 General Considerations on the Chemistry of PhotoinitiatedRadical Polymerization Employed in Negative Resist Systems 2576.6.1 Photogeneration of radicals 2586.6.1.1 Initiators based on photofragmentation 2586.6.2 Radicals generated by hydrogen abstraction 2626.6.2.1 Other practical initiator systems based onhydrogen abstraction 2636.6.3 Dye-sensitized initiation 2666.6.4 The initiation step 2696.6.5 Propagation versus termination and the kineticchain length 2706.6.5.1 The steady state approximation 2706.7 General Considerations on Photoinitiated CondensationPolymerization 2726.7.1 The thiol-ene system 2726.8 General Considerations on the Photoinitiated CationicPolymerization Employed in Negative Resist Systems 2736.8.1 Initiation by onium salts 2736.8.1.1 Initiation 2736.8.1.2 Propagation 2746.9 Practical Negative Resist Compositions Arising fromPhotopolymerization of Monomers in the Presence ofPolyfunctional Components 2806.9.1 Negative resist composition 2806.9.2 Binders 280x Contents6.10 Lithographic Applications of Photopolymerization NegativeResists 2806.10.1 Lithographic offset plates 2816.10.2 Dry resists 2816.10.3 Printed circuit boards 2826.10.4 Solder mask 2836.10.5 IC device fabrication 2837 Positive Resists 2857.1 Introduction 2857.2 Types of Positive Resists 2867.2.1 Non-chemically amplied positive resists 2867.2.1.1 Non-chemically amplied positive resistsbased on functional group polarity switch 2867.2.1.2 Non-chemically amplied positive resistsbased on main chain scission 3237.2.2 Chemical amplication positive resists: the chemicalamplication concept 3357.2.2.1 Acid generators 3367.2.2.2 Chemical amplication positive resists andtheir imaging mechanisms 3437.2.2.3 Chemical amplication positive resists basedon deprotection 3437.2.2.4 Chemical amplication positive resists basedon Claisen rearrangement 3857.2.2.5 Chemical amplication positive resists basedon depolymerization 3877.3 Resist Materials for Multilayer Resist Systems 3917.3.1 Hard mask resist materials 3927.3.2 Top surface imaging resists 3937.3.3 Bilayer resists 3938 General Considerations on the Radiation and Photochemistryof Resists 3958.1 Interaction of Radiation with Resists 3958.2 Excited State Complexes 3978.2.1 Excimers 3978.2.2 Exciplexes 3988.3 Energy Transfer 3998.3.1 Dipole resonance transfer 4008.3.2 Exchange transfer 4018.3.3 The Perrin formula 4028.4 Energy Migration in Resist Polymers 4038.5 Spectral Sensitization 4068.6 Sensitization by Energy Transfer 407Contents xi8.6.1 Triplet sensitization 4078.6.2 Sensitization by electron transfer 4088.7 RadiationChemistryVersusPhotochemistryofResists 4098.8 Radiation Chemical Yield and Dosimetry 4118.9 Radiation Chemistry of Polymers 4118.9.1 Backbone scission and cross-linking 4118.9.2 Determination of the scission yield 4128.9.3 Determination of the cross-linking yield Gx4138.10 Sensitivity and Exposure Radiation 4148.11 Exposure Mechanisms of Resists and Exposure Radiation 4159 Antireection Coatings and Reectivity Control 4199.1 Introduction 4199.2 Antireection Coating Strategies 4219.2.1 Top antireection coatings 4219.2.2 Theory of top antireection coatings 4249.2.3 Reection and transmission amplitudes 4249.3 Bottom Antireection Coatings 4289.3.1 Organic bottom antireection coatings 4289.3.1.1 Design approaches to organic bottomantireection coatings 4289.3.2 Inorganic bottom antireection coatings 4319.4 Applications of Bottom Antireection Coatings 4329.4.1 Suppression of standing waves and reectivity effects 4329.4.2 Feature CD trimming 4359.4.3 Damascene applications involving silicon-containingresists and silicon-containing hard mask materials withantireection prope