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研究生：	陳姵瑜 Chen, Pei-Yu
論文名稱：	異山梨醇衍生生質聚醯亞胺於低介電負型光阻之設計與應用 Design and Application of Isosorbide-Derived Biobased Polyimides for Low-Dielectric Negative-Type Photoresists
指導教授：	林彥丞 Lin, Yan-Cheng
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2026
畢業學年度：	114
語文別：	英文
論文頁數：	144
中文關鍵詞：	生質聚醯亞胺、異山梨醇、感光聚醯亞胺、光鹼產生劑、低介電常數、負型光阻
外文關鍵詞：	Biobased polyimide, isosorbide, photosensitive polyimide, photobase generator, low dielectric constant, negative-type photoresist
相關次數：	點閱：14 下載：0
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低介電材料可有效降低訊號延遲與功率損耗，而生質高分子則有助於減少對石化資源的依賴並提升材料永續性，故本研究開發低介電性質、高熱穩定性之生質感光聚醯亞胺，以應用於先進封裝與高頻微電子領域。本研究以設計一種異山梨醇衍生二胺與三種商用芳香族二酸酐合成一系列生質聚醚醯亞胺，並透過醚鍵結構設計避免易受鹼性水解之酯鍵，以提升材料於鹼性顯影製程中的穩定性。所得聚醯亞胺展現良好熱穩定性，其 5% 熱重損失溫度為 437–443 °C，玻璃轉移溫度為 207–273 °C。所有薄膜於 10–38 GHz 頻率範圍內皆具有低於 3.0 之介電常數；三者之中綜合評估後，以 ISBA-ODPA 有良好機械、熱穩定與介電性能外，還有較佳的紫外線透光性、鹼性顯影能力與製程相容性，故選用其進行負型感光聚醯亞胺配方開發。添加肉桂酸型光鹼產生劑後，經曝光與曝光後烘烤，可透過光鹼催化之局部亞醯胺化反應產生足夠溶解度差異。於最佳化條件下，可成功形成清晰之 30 微米負型線寬圖案，並觀察到連續但解析度仍待改善之 10 微米圖案。結果顯示，醚鍵連接之異山梨醇衍生聚醯亞胺為具潛力之永續低介電負型感光聚醯亞胺材料。

Low-dielectric materials reduce signal delay and power loss, while biobased polymers improve sustainability by decreasing reliance on petrochemical resources. This study develops biobased photosensitive polyimides with low dielectric properties and high thermal stability for advanced packaging and high-frequency microelectronics. A series of biobased poly(ether imide)s were synthesized from an isosorbide derived diamine and three aromatic dianhydrides. Ether linkages were introduced to replace hydrolysis-prone ester bonds, enhancing stability during alkaline development. The resulting polymers exhibited good thermal stability, with 5% weight-loss temperatures of 437–443 °C and glass transition temperatures of 207–273 °C. All films showed dielectric constants below 3.0 at 10–38 GHz. Among the systems, ISBA-ODPA showed the best overall performance, including mechanical, thermal, and dielectric properties, as well as UV transparency, developability, and process compatibility, and was therefore selected for PSPI formulation. After incorporating a cinnamic acid-type photobase generator, sufficient dissolution contrast was achieved via photobase-catalyzed imidization. Under optimized conditions, well-defined negative-tone patterns with 30 μm line widths were successfully obtained, while continuous but less well-resolved 10 μm features were also observed. These results demonstrate that ether-linked isosorbide-based poly(ether imide)s are promising sustainable low-dielectric PSPI materials.

摘要 i
ABSTRACT ii
誌謝 iii
CONTENTS iv
LIST OF FIGURES ix
LIST OF TABLES xiv
LIST OF SCHEMES xv
LIST OF ABBREVIATIONS xvi
Chapter 1 Introduction 1
1-1 Background and Preface 1
1-1-1 Development of High-Frequency Communication and Advanced Packaging 1
1-1-2 Environmental Concerns and Sustainable Polymer Materials 2
1-2 Polyimides (PIs) 5
1-2-1 Molecular Structure and Classification of PIs 5
1-2-2 Synthetic Approaches of PIs 6
1-2-3 Structure–Property Relationships of PIs 8
1-2-4 Applications of PIs 10
1-3 Biobased PIs 12
1-3-1 Development of Biobased Polymeric Materials 12
1-3-2 Biobased Monomers for PIs 15
1-3-3 Isosorbide-Derived PIs 17
1-4 Low Dielectric PIs 18
1-4-1 Fundamentals of Dielectric Properties 18
1-4-2 Factors Affecting Dk 20
1-4-3 Factors Affecting Df 23
1-4-4 Recent Progress in Low-k PIs 25
1-5 Photosensitive Polyimides (PSPIs) 27
1-5-1 Positive-Type and Negative-Type PSPIs 29
1-5-2 Photobase Generators (PBGs) 31
1-5-3 Biobased poly(ether imides)-Based PSPIs 33
1-6 Motivation 35
1-7 Research Objectives and Scope 36
Chapter 2 Experimental Methods 37
2-1 Research Methods 37
2-2 Materials and Reagents 39
2-3 Design and Synthesis of Biobased Monomers 42
2-3-1 Synthesis of Isosorbide-Derived Diamine (ISBA) 42
2-3-2 Synthesis of Isosorbide-Derived Dianhydride (ISBESA) 43
2-4 Preparation of Biobased Poly(amic acid) Precursors 44
2-4-1 Polyaddition of ISBA with Aromatic Dianhydrides 44
2-4-2 Control of Molecular Weight and Inherent Viscosity 46
2-5 Fabrication of Biobased PI Films 47
2-5-1 Thermal Imidization Procedures 47
2-5-2 Film Casting and Post-Treatment 48
2-6 Synthesis and Formulation of Photosensitive Components 49
2-6-1 Synthesis of Photobase Generator (PBG) 50
2-6-2 Preparation of Biobased PSPI Coating Solutions 52
2-7 Photolithographic Processing of Negative-Type PSPIs 53
2-7-1 Film Coating and Prebake Conditions 53
2-7-2 UV Exposure and Post-Exposure Bake 54
2-7-3 Alkaline Development and Hard Bake 55
2-8 Characterization Techniques 56
2-8-1 Structural and Chemical Analysis 57
2-8-2 Thermal and Thermomechanical Properties 62
2-8-3 Mechanical Properties 66
2-8-4 Optical Properties 67
2-8-5 Surface and Thickness Analysis 68
2-8-6 Dielectric Property Measurement 69
2-8-7 Photopatterning and Morphological Analysis 70
Chapter 3 Results and Discussion 72
3-1 Synthesis and Structural Characterization of Biobased PIs 72
3-1-1 Chemical Structure and Imidization Behavior 72
3-1-2 Molecular Weight and Distribution of Biobased PAA Precursors 79
3-2 Thermal and Thermomechanical Properties of Biobased PIs 81
3-2-1 Thermal Stability 81
3-2-2 Glass Transition Temperature 83
3-2-3 Coefficient of Thermal Expansion 85
3-3 Mechanical Properties of Biobased PIs 87
3-4 Dielectric Properties of Biobased PIs 89
3-4-1 Dielectric Constant (Dk) 89
3-4-2 Dissipation Factor (Df) 92
3-5 Optical Properties of Biobased PIs 94
3-5-1 Optical Transparency and UV Absorption Behavior 94
3-5-2 Yellow Index and Visual Appearance 97
3-6 Photolithographic Performance of Biobased PSPIs 98
3-6-1 Dissolution Behavior and Process Window 98
3-6-2 Optical Microscopy Analysis of Pattern Resolution 100
3-6-3 SEM Analysis of Line–Space Fidelity and Thickness Retention 101
3-7 Comparison with Other Biobased PIs 103
Chapter 4 Conclusion and Future Work 105
4-1 Conclusion 105
4-2 Future Work 107
Appendix 109
References 117
                                    

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