Photopolymers photoresist materials, processes, and applications

Photopolymers Photoresist Materials, Processes, and Applications Kenichiro Nakamura Photopolymers Optics and Photonics Series Editor Le Nguyen Binh Huawei Technologies, European Research Center, Munich, Germany Digital Optical Communications, Le Nguyen Binh Optical Fiber Communications Systems: Theory and Practice with MATLAB® and Simulink® Models, Le Nguyen Binh Ultra-Fast Fiber Lasers: Principles and Applications with MATLAB® Models, Le Nguyen Binh and Nam Quoc Ngo Thin-Film Organic Photonics: Molecular Layer Deposition and Applications, Tetsuzo Yoshimura Guided Wave Photonics: Fundamentals and Applications with MATLAB®, Le Nguyen Binh Nonlinear Optical Systems: Principles, Phenomena, and Advanced Signal Processing, Le Nguyen Binh and Dang Van Liet Wireless and Guided Wave Electromagnetics: Fundamentals and Applications, Le Nguyen Binh Guided Wave Optics and Photonic Devices, Shyamal Bhadra and Ajoy Ghatak Digital Processing: Optical Transmission and Coherent Receiving Techniques, Le Nguyen Binh 10 Photopolymers: Photoresist Materials, Processes, and Applications, Kenichiro Nakamura Photopolymers Photoresist Materials, Processes, and Applications Kenichiro Nakamura CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2015 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S Government works Version Date: 20140618 International Standard Book Number-13: 978-1-4665-1731-8 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint Except as permitted under U.S Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400 CCC is a not-for-profit organization that provides licenses and registration for a variety of users For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Introduction vii About the Author ix Basic Idea of Photopolymerization 1.1 Introduction 1.2 Radical Polymerization 1.3 Monomers for Photopolymerization 1.4 Initiators of Photopolymerization 28 1.5 Inhibition of Polymerization 41 1.6 Cationic Photopolymerization 46 1.7 Photocrosslinking 50 1.8 Scission of Polymers 54 References 58 Chemically Amplified Resists 61 2.1 Introduction 61 2.2 Chemical Amplification of Photopolymers 61 2.3 Polymers for Chemical Amplification .65 2.4 Photoacid Generator 79 References 93 Process of Chemically Amplified Resists 97 3.1 Introduction 97 3.2 Progress of Resolution Limit 97 3.3 Immersion Lithography 103 3.4 Double Patterning 106 3.5 EUV Lithography 109 3.6 Direct Self-Assembly (DSA) 115 References 118 4 Nanoimprint 121 4.1 Introduction 121 4.2 Thermal Nanoimprint 121 4.3 UV Nanoimprint 125 4.4 Cationic Polymerization of UV Nanoimprint 129 4.5 Ene-Thiol Polymerization of UV Nanoimprint 133 4.6 Soft Lithography 135 References 137 v vi Contents Industrial Application of Photopolymers 139 5.1 Introduction 139 5.2 Application to Electronics 139 5.3 Optical Adhesive Polymers 144 5.4 Holographic Photopolymers 152 5.5 Application to Medical Materials 159 5.6 Microelectromechanical Systems (MEMSs) 163 References 171 Introduction Recent development of photopolymers has highly contributed to the improvement of sophisticated industries, especially in the electronics, optical engineering, and medical fields Photopolymerization, photodegradation, and photo-crosslinking are basic ideas for photopolymers The progress of lithography technology, in which photofabrications are performed by images of photopolymers, has given high densities to microproducts Large-scale integrated (LSI) circuits are produced by lithography technology Giga-scale electronic circuits are applied to central parts of computers Microminiaturization made it possible to employ millions of transistors in a single circuit The reduction in size of transistors has dramatically lowered the cost of production and increased the speed of running electronic circuits The first integrated circuit (IC) was 64 kilo-bits random access memory (RAM) by lithography technology in 1960 Since 1960, the growth in the number of components per chips has increased by 107 Resolution of photofabrication is limited by wavelength of exposure The less time the wavelength is exposed, the higher the resolution is expected to be In those 30 years, wavelength shifted from i-line (365 nm) via ArF (193 nm) to EUV (13 nm) It is projected to soon reach T memory (tera 1012) Photopolymers are applied to many fields including semiconductor device manufacturing, printing boards, optical engineering, medical materials, curing, printing plates, and microelectromechanical systems (MEMSs) Application fields are still expanding because of developing photopolymers In this book, the progress of photopolymers will be summarized and reviewed, from basic idea to industrial application I thank the many persons who supported the publication of this book by Tayor & Francis I express great pleasure to Prof Moriaki Wakaki of Tokai University for suggesting this book be published I thank Prof Minoru Tsuda of Chiba University and Prof C Grant Willson of Texas University for their help in expanding my knowledge of photopolymers I express many thanks to my son, Sohichiro Nakamura, and wife, Yukiko Nakamura, for supporting me during the preparation of this book Kenichiro Nakamura Tokyo November 2013 vii 162 Photopolymers: Photoresist Materials, Processes, and Applications O O O O Benzoylperoxide BPO + CH3 t-Bu N COOC2H5 N,N-methyl, ethylformate-p-tert-butyl aniline FIGURE 5.27 Thermal initiator of polymerization (benzoylperoxide/N,N-methyl, ethylformate-p-tert-butylaniline) Figures 5.27 and 5.28 Benzoylperoxide BPO/amine (N,N-methyl, ethylformatetert-butyl-qniline) initiates polymerization by heat Camphorquinone/amine (N,N-methyl, ethyl-p-methylaniline) initiates polymerization by visible light A stabilizer is added to the resin for stabilizing polymerization 4-Methoxyphenol and 2,4,6-tri-tert-butylphenol are effective stabilizers M Uo et al.36 reported on a dental composite resin cured under nearinfrared irradiation They showed the following composite resin (CR) The mixture of Bis-GMA and TEGDMA was used as the base resin matrix BisGMA and TEGDMA are mixed to be 2:1 in weight ratio H3C CH3 H3C C2H5 N O + O H3C camphorquinone CH3 N,N-methyl, ethyl-p-methylaniline FIGURE 5.28 Photoinitiator (camphorquinone/N,N-methyl, ethyl-p-methylaniline) 163 Industrial Application of Photopolymers 5.6 Microelectromechanical Systems (MEMSs) Microelectromechanical systems (MEMSs) are integrated micromechanical and electronic parts on silicon or glass plates They are produced by lithography technology Various sensors, micromotors, biochips, chemical reactors, biomolecular devices, microfluid lanes, and so on, are produced by MEMSs Kawai reported on fluid control MEMSs constructed with polymer materials (Figure 5.29).37 Figure 5.30 shows the basic structure of a fluid control channel A Si diaphragm is pushed down by Coulomb force The width of the microchannel is 50 μm Microdiaphragms are arranged along with the microchannel as shown in Figure 5.30 By compressing and expanding fluid in a microchannel by diaphragms in order, a certain fluid flow occurs, In Kawai’s study, 12 diaphragms are arranged and operated to control a reactive gas flow The fluid control MEMS is composed of a microdiaphragm and microchannel Figure 5.31 shows the fabrication process of a multilayer diaphragm structure A SiO2 layer (45 nm) is formed by thermal oxidation of Si substrate Circular resist masks are formed on the SiO2 surface by optical lithography A SiO2 mask is etched by 0.5 wt% aqueous solution F N Ti F F F N Bis(.eta.5,2,4-cyclopentadien-1-yl)-bis(2,6-difluoro3-(1H-pyrrol-1-yl)-phenyl titanium FIGURE 5.29 Diaphragm structure of Au/Si/resist multilayer film 164 Photopolymers: Photoresist Materials, Processes, and Applications ON ON OFF Gas flow FIGURE 5.30 Fluid flow operation by compression and expansion of diaphragms Thermal oxidation SiO2 layer Si wafer Optical lithography Resist mask SiO2 etching in HF aq_solution HF Resist film removal Acetone Anisotropic etching EPW Polymer coating Polymer film FIGURE 5.31 Fabrication of microdiaphragm structure 165 Industrial Application of Photopolymers Au spattering Spattered Au film Glass Polymer coating Polymer layer Resist patterning Resist pattern channel FIGURE 5.32 Fabrication of microchannel The resist layer is removed by acetone The Si substrate is etched by anisotropic etching Then the diaphragm structure is fabricated The resist film is coated by spin coating on the backside of the Si diaphragm The Au film is coated on the etched Si surface by the DC sputtering method Figure  5.32 shows fabrication of a microchannel A microchannel is formed on a glass substrate Au film is formed on the glass plate for the electrode A microchannel is produced by the photolithographic process An Au electrode is connected with an external electric circuit Figure 5.33 shows fabrication of fluid control MEMS Fluid control MEMS is completed by adhering to a diaphragm and microchannel The alignment of these two systems is carried out as shown in Figure  5.33 Figure  5.34 shows a fluid control MEMS assembled on a package Control signals are applied onto the pumping system Figure 5.35 shows details of the fluid control MEMS shown in Figure 5.34 Inlets and outlets are arranged on both sides of the MEMS Fluid streams under control of the MEMS from inlets to outlets Various microsensors are produced by MEMS S Armbruster et al reported on a micropressure sensor.38 They produced a microcave on a Si surface The cave works as a sensor of pressure, because of the change in volume of the microcave Y Matsumoto and M Esashi reported on an electrostatic capacity 166 Photopolymers: Photoresist Materials, Processes, and Applications Resist film SU-8 pattern Polymer channel Fluid control MEMS FIGURE 5.33 Fabrication of fluid control MEMS type of pressure sensor.39 Displacement of a microcavity is converted to change the electrostatic capacity J H Kupers et al reported on a microsensor of pressure by using a surface acoustic wave (SAW).40 A SAW is generated from a wedge electrode on a LiNbO3 plate S Kobayashi et al reported on a microsensor applied to human touch.41 FIGURE 5.34 Picture of assembly of fluid control MEMS 167 Industrial Application of Photopolymers Top view 14 mm mm mm mm Inlet 500 µm mm 500 µm Outlet Curvature radius mm 50 µm mm 50 µm Curvature radius Inlet mm 100 µm 500 µm Outlet mm mm (a) Cross view 30 µm 200 nm µm 200 nm Micro channel Au Diaphragm Si substrate Polymer layer Resist Au Glass FIGURE 5.35 Details of fluid control MEMS shown in Figure 5.34 J A Geen et al reported on microsensors of acceleration.42 Movement of microweight on Si is detected as an acceleration change Acceleration displacement is converted to a change of electrostatic capacity A microsensor of acceleration may be applied to the sensors in an automobile collision, a user’s interface on a game machine, and a mobile information instrument.43 M Nagata et al reported on a microsensor of rotational accelerator for safety use in automobiles.44 J Seeger et al reported on sensors of hand deflection for cameras.45 The structure of the microgyroscope with two vibrational shafts to prevent hand deflection during photo taking is shown in Figure  5.36 A CMOS circuit is included in the base silicone wafer, and rotational deflection is detected as an electric signal A M Leung et al reported on the thermal detection microsensor of acceleration Gas in the inner cavity is moved by inertia, and the movement is detected by transfer of heat.46 The structure of the microthermal acceleration sensor is shown in Figure 5.37 T Murakoshi et al reported on a microrotational gyroscope for static floating for navigating precisely.47 The Si ring of 1.5 mm radius rotates at a high speed 168 Photopolymers: Photoresist Materials, Processes, and Applications Si 700 nm depth Ge 500 nm depth Al SiO2 30 µ depth Si Si (CMOS circuit) mm FIGURE 5.36 Microgyroscope with two vibration shafts to prevent hand deflection during photo taking of 75,000 rpm The angular velocities of two axes crossed perpendicularly and the acceleration speed of the third axis can be measured simultaneously N Asada et al reported on a microphotoscanner of two axes that works by magnetic induction.48 A micromirror is moved by coils in a cymbal structure crossed at two directions enclosed by permanent magnets A three-dimensional distance image sensor is produced by applying the photoscanner.49 Since light progresses 30 cm for ns, the traveling time of Thermal sensor Cavity Heater Thermal sensor Terminal Si FIGURE 5.37 Structure of microacceleration sensor, thermal type Si 169 Industrial Application of Photopolymers Thermal collector plate VO2 thin film Terminal One image element IC circuit FIGURE 5.38 Structure of a sensor element of an IR image laser light between emission and reflection from the object gives the distance from the object S Tohyama et al reported on an infrared (IR) image sensor.50 The structure of a unit image sensor is shown in Figure  5.38 Many elements are arranged on the IR image sensor IR light is converted to heat Then the heat warms the thermal collector plate on the image element Resistivity of the VO2 plate depends on the thermal temperature and is processed by the IC circuit MEMS was first developed by a group from Stanford University They developed gas chromatography on a 2-in silicon wafer.51 A microfluid tube for the separation column was produced by etching A valve for sample injection and thermal conductive detector were also produced on the silicone wafer Two-dimensional gas chromatography was developed by a group from Michigan University.52 Microfluid tubes were produced on a silicone wafer Two columns were used for two-dimensional separation A microsensor for density and amount of flow was developed from MEMS.53 The density of the microfluid and flowing amount of liquid could be measured by the sensor A microsensor for blood pressure was developed from MEMS.54 The diameter of the sensor was 125 μm Then the microsensor could be introduced into blood vessels by a catheter A wireless micropressure sensor buried inside a human body was developed from MEMS.55 A microcoil and capacitor were produced on a silica glass chip Logic circuit (LC) oscillation frequency depends on pressure A pressure signal was sent by wireless wave to a detector outside the body A soft-MEMS glucose sensor was developed by S Iguchi et al.56 The structure of the flexible glucose sensor is shown in Figure 5.39 The glucose sensor consists of an enzyme-immobilized membrane and film-like oxygen electrode (Pt working electrode and Ag/AgCl reference/counter electrode) The sensor is constructed by immobilizing the enzyme membrane onto the sensitive area of the oxygen electrode The electrode reaction is given by Equation (5.6): 170 Photopolymers: Photoresist Materials, Processes, and Applications Gas-permeable membrane Enzyme membrane Pt electrode Ag/AgCl electrode Non-permeable membrane mm Membrane with electrolyte FIGURE 5.39 Structure of a flexible MEMS glucose sensor Cathode (Pt) O2 + 2H2O + 4e– → 4OH– Anode (Ag/AgCl) 4Ag + 4Cl– → 4AgCl+ 4e– (5.6) The electric current between both electrodes is measured, and the concentration of glucose is calculated by the following equation: Output (μA) = –0.06 + 1.822 [glucose (mmol/L)] (5.7) A microchamber array of bio-MEMS was developed on a silicone wafer.57–60 The microchamber (multifunctional flow system) contains: Introduction unit of reagent Separation and reaction unit Amplification unit of gene or protein Gene detection unit Plastid extraction unit A total of 1248 microchambers of 50 nl volume were integrated in the microchamber array Amplification and analysis of the gene were performed by the microchamber array The microcylinder array (diameter μm) was arranged by MEMS technology on a silicone wafer (6 cm 2).61 Figure 5.40 shows the microcylinder array The cylinders can be applied to microvessels of picoliters (10 –12) 171 Industrial Application of Photopolymers z y x Micro cylinder 5µmφ z y FIGURE 5.40 Structure of a microcylinder array to nanoliters (10 –9) Therefore, the microcylinder array can be applied to mixing, reaction, separation, extraction, and phase separation The microcylinder array is reported to be an effective tool for analysis of DNA and protein.62,63 References W M Moreau, Semiconductor 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23 (2005) 361 63 W Chen, Y Yang, C Rinadi, D Zhou, and Q Shen, Lab Chip, (2009) 2947 MATERIALS SCIENCE Photopolymers Photoresist Materials, Processes, and Applications Advancements in photopolymers have led to groundbreaking achievements in the electronics, print, optical engineering, and medical fields At present, photopolymers have myriad applications in semiconductor device manufacturing, printed circuit boards (PCBs), ultraviolet (UV) curing, printing plates, 3-D printing, microelectromechanical systems (MEMS), and medical materials Processes such as photopolymerization, photodegradation, and photocrosslinking, as well as lithography technology in which photofabrications are performed by images of photopolymers, have given rise to very large scale integrated (VLSI) circuits, microproducts, and more Addressing topics such as chemically amplified resists, immersion lithography, extreme ultraviolet (EUV) lithography, and nanoimprinting, Photopolymers: Photoresist Materials, Processes, and Applications covers photopolymers from core concepts to industrial applications, providing the chemical formulae and structures of the materials discussed as well as practical case studies from some of the world’s largest corporations Offering a state-of-the-art review of progress in the development of photopolymers, this book provides valuable insight into current and future opportunities for photopolymer use K15098 ISBN-13: 978-1-4665-1728-8 90000 781466 517288 ... Transmission and Coherent Receiving Techniques, Le Nguyen Binh 10 Photopolymers: Photoresist Materials, Processes, and Applications, Kenichiro Nakamura Photopolymers Photoresist Materials, Processes, and. .. dilution and adhesion: CH3 CH3 CH2=CCOOC2H4-N O (-CH2-C-)n COOC2H4-N O (1.45) 16 Photopolymers: Photoresist Materials, Processes, and Applications TABLE 1.6 Monofunctional Methacrylates and Acrylamides... Viscosity 14 Photopolymers: Photoresist Materials, Processes, and Applications 15 Basic Idea of Photopolymerization Ethylphosphoric acid-methacrylate gives a polymer for the adhesiveness and modification