Synthesis and Characterization of Naphtho[1,2-b:5,6-b']dithiophene(NDT) Derivatives for Organic Thin Film Transistors
- Alternative Title
- 유기 박막 트랜지스터를 위한 Naphtho[1,2-b:5,6-b']dithiophene(NDT) 유도체의 합성과 특성분석
- Abstract
- Chapter 1, 새로운 2,7-di(thiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (T-NDT-T) 유도체, 2,7-bis(5- octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (물질 1), 2,7-bis(5-(2-ethylhexyl)thiophen-2- yl)naphtho[1,2-b:5,6-b']dithiophene (물질 2)을 합성하였고, 유기 박막 트랜지스터 (OTFT)를 위한 용액 공정 가능한 유기 반도체로서 특성화하였다. 합성된 물질의 열적, 광학적, 전기화학적 특성을 분석하였다. NDT 유도체를 기반으로 제작된 모든 OTFT 는 공기 중에서 안정적인 p 채널 특성을 보였다. 특히, 물질 2 은 0.058 cm2/Vs 의 이동도를 보였고, 6.04 x 107 의 current on/off ratio 를 나타냈다. Chapter 2, Naphtho[1,2-b:5,6-b']dithiophene (NDT) 코어를 기반으로, 2,7-bis(phenylethynyl)naphtho[1,2-b:5,6- b']dithiophene (물질 3), 2,7-bis(thiophen-2-ylethynyl)naphtho[1,2-b:5,6-b']dithiophene (물질 4), 2,7-bis((5- octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (물질 5)을 합성하였다. NDT 유도체를 기반으로 제작된 모든 OTFT 는 공기 중에서 안정적인 p 채널 특성을 보였다. 특히, 물질 3 은 0.00016 cm2/Vs 의 이동도를 보였고, 4.42 × 105 의 current on/off ratio 를 나타냈다. Chapter 3, 선형 알킬기(octyl-)가 코어 한쪽 말단에 치환된 새로운 naphtho[1,2-b:5,6-b']dithiophene (NDT) 유도체, 2-octylnaphtho[1,2-b:5,6-b']dithiophene (물질 6), 2-octyl-7-(thiophen-2-yl)naphtho[1,2-b:5,6- b']dithiophene (물질 7). 2-octyl-7-(5-octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (물질 8), 2- (5-(octan-3-yl)thiophen-2-yl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (물질 9)을 합성하였다. NDT 유도체를 기반으로 제작된 모든 OTFT 는 공기 중에서 안정적인 p 채널 특성을 보였다. 특히, 물질 8 은 0.0043 cm2/Vs 의 이동도를 보였고, 물질 7 은 2.54 × 106의 current on/off ratio 를 나타냈다. Chapter 4, 선형 알킬기(octyl-)가 코어 한쪽 말단에 치환된 새로운 naphtho[1,2-b:5,6-b']dithiophene (NDT) 유도체, 2-octyl-7-(phenylethynyl)naphtho[1,2-b:5,6-b']dithiophene (물질 10), 2-octyl-7-((5- octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (물질 11), 2-((5-(2-ethylhexyl)thiophen- 2-yl)ethynyl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (물질 12)을 합성하였다. 합성된 물질들의 구조는 1H NMR 과 13C NMR 을 통해 확인되었다.|In chapter 1, Two new 2,7-di(thiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (T-NDT-T) derivatives, namely 2,7-bis(5-octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (compound 1) and 2,7-bis(5-(2-ethylhexyl)thiophen-2-yl)naphtho[1,2-b:5,6- b']dithiophene (compound 2), were synthesized and characterized as solution- processable organic semiconductors for organic thin-film transistor (OTFT) applications. The thermal, optical, and electrochemical properties of the synthesized compounds were systematically investigated. All OTFT devices fabricated using these NDT-based derivatives exhibited stable p-channel characteristics under ambient conditions. Notably, compound 2 demonstrated a hole mobility of 0.058 cm²/V·s and a current on/off ratio of 6.04 × 10⁷. In chapter 2, Based on the naphtho[1,2-b:5,6-b']dithiophene (NDT) core, three derivatives—2,7- bis(phenylethynyl)naphtho[1,2-b:5,6-b']dithiophene (compound 3), 2,7-bis(thiophen- 2-ylethynyl)naphtho[1,2-b:5,6-b']dithiophene (compound 4), and 2,7-bis((5- octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (compound 5)—were synthesized. All OTFT devices fabricated using these NDT-based derivatives exhibited stable p-channel characteristics under ambient conditions. Notably, compound 3 displayed a hole mobility of 0.00016 cm²/V·s and a current on/off ratio of 4.42 × 10⁵. In chapter 3, A series of new naphtho[1,2-b:5,6-b']dithiophene (NDT) derivatives, in which a linear alkyl chain (octyl) was substituted at one terminal position of the core, were synthesized: 2-octylnaphtho[1,2-b:5,6-b']dithiophene (compound 6), 2-octyl-7-(thiophen-2- yl)naphtho[1,2-b:5,6-b']dithiophene (compound 7), 2-octyl-7-(5-octylthiophen-2- yl)naphtho[1,2-b:5,6-b']dithiophene (compound 8), and 2-(5-(octan-3-yl)thiophen-2- yl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (compound 9). All OTFT devices fabricated using these NDT-based semiconductors exhibited stable p-channel characteristics under ambient conditions. Notably, compound 8 demonstrated a hole mobility of 0.0043 cm²/V·s, while compound 7 exhibited a current on/off ratio of 2.54 × 10⁶. In chapter 4, Three new naphtho[1,2-b:5,6-b']dithiophene (NDT) derivatives, in which a linear alkyl chain (octyl) was substituted at one terminal position of the core, were synthesized: 2-octyl-7-(phenylethynyl)naphtho[1,2-b:5,6-b']dithiophene (compound 10), 2-octyl-7- ((5-octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (compound 11), and 2-((5-(2-ethylhexyl)thiophen-2-yl)ethynyl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (compound 12). The structures of the synthesized compounds were confirmed by ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy.
- Issued Date
- 2025
- Awarded Date
- 2025-08
- Type
- Dissertation
- Publisher
- 국립부경대학교 대학원
- Alternative Author(s)
- JANG HYEON JU
- Affiliation
- 국립부경대학교 대학원
- Department
- 대학원 스마트그린기술융합공학과
- Advisor
- 서성용 (SungYong Seo)
- Table Of Contents
- Chapter 1. Solution-Processable 2,7-di(thiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene Derivative Derivatives as Small Molecular Organic Semiconductors for Organic Field-Effect Transistors 1
1.1. Introduction 1
1.2. Experimental details 5
1.2.1. General Methods 5
1.2.2. Synthesis 5
1.2.2.1. Synthesis of 2,7-dibromonaphtho[1,2-b:5,6-b']dithiophene (1a) 5
1.2.2.2. Synthesis of 2,7-bis(5-octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (1) 5
1.2.2.3. Synthesis of 2,7-bis(5-(2-ethylhexyl)thiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (2) 6
1.2.3. Theoretical Calculation 7
1.2.4. Device Fabrication 7
1.2.5. Device and Film Characterization 8
1.3. Results and Discussion 9
1.3.1. Synthesis 9
1.3.2. Optical properties 11
1.3.3. Electrochemical properties 11
1.3.4. Theoretical calculation 15
1.3.5. Thermal and crystalline properties 17
1.3.6. Organic field-effect transistor characterization 19
1.4. Conclusion 23
Chapter 2. Synthesis and Characterization of Naphtho[1,2-b:5,6-b']dithiophene(NDT) Derivatives as Solution-Processable Organic Semiconductors for Organic Thin-Film Transistors 24
2.1. Introduction 24
2.2. Experiment details 28
2.2.1. General Methods 28
2.2.2. Synthesis 28
2.2.2.1. Synthesis of 2,7-bis(phenylethynyl)naphtho[1,2-b:5,6-b']dithiophene (3) 28
2.2.2.2. Synthesis of 2,7-bis((trimethylsilyl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (1b) 29
2.2.2.3. Synthesis of 2,7-bis(thiophen-2-ylethynyl)naphtho[1,2-b:5,6-b']dithiophene (4) 29
2.2.2.4. Synthesis of 2,7-bis((5-octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (5) 30
2.2.3. Theoretical Calculation 31
2.2.4. Device Fabrication 32
2.2.5. Device and Film Characterization 33
2.3. Results and Discussion 33
2.3.1. Synthesis 33
2.3.2. Optical properties 35
2.3.3. Electrochemical properties 35
2.3.4. Theoretical calculation 39
2.3.5. Thermal and crystalline properties 41
2.3.6. Organic field-effect transistor characterization 43
2.4. Conclusion 46
Chapter 3. Octyl-Substituted NDT Derivatives as Small Molecular Organic Semiconductors for Organic Field-Effect Transistors 47
3.1. Introduction 47
3.2. Experiment details 51
3.2.1. General Methods 51
3.2.2. Synthesis. 51
3.2.2.1. Synthesis of 2-octylnaphtho[1,2-b:5,6-b']dithiophene (6) 51
3.2.2.2. Synthesis of 2-iodo-7-octylnaphtho[1,2-b:5,6-b']dithiophene (6a). 52
3.2.2.3. Synthesis of 2-octyl-7-(thiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (7) 53
3.2.2.4. Synthesis of 2-octyl-7-(5-octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene (8) 54
3.2.2.5. Synthesis of 2-(5-(octan-3-yl)thiophen-2-yl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (9) 55
3.2.3. Theoretical Calculation 56
3.2.4. Device Fabrication 56
3.2.5. Device and Film Chracterization 57
3.3. Results and Discussion 58
3.3.1. Synthesis 58
3.3.2. Optical properties 60
3.3.3. Electrochemical properties 60
3.3.4. Theoretical calculation 64
3.3.5. Thermal and crystalline properties 66
3.3.6. Organic field-effect transistor characterization 68
3.4. Conclusion 71
Chapter 4. Synthesis and Characterization of Octyl-Substituted NDT Derivatives as Solution-Processable Organic Semiconductors for Organic Thin-Film Transistors 72
4.1. Introduction 72
4.2. Experiment details 75
4.2.1. General Methods 75
4.2.2. Synthesis. 75
4.2.2.1. Synthesis of 2-octyl-7-(phenylethynyl)naphtho[1,2-b:5,6-b']dithiophene (10) 75
4.2.2.2. Synthesis of trimethyl((7-octylnaphtho[1,2-b:5,6-b']dithiophen-2-yl)ethynyl)silane (6b) 76
4.2.2.3. Synthesis of 2-octyl-7-((5-octylthiophen-2-yl)ethynyl)naphtho[1,2-b:5,6-b']dithiophene (11) 77
4.2.2.4. Synthesis of 2-((5-(2-ethylhexyl)thiophen-2-yl)ethynyl)-7-octylnaphtho[1,2-b:5,6-b']dithiophene (12) 78
4.2.3. Device Fabrication 79
4.3. Results and Discussion 80
4.3.1. Synthesis 80
4.3.2. Organic field-effect transistor characterization 82
4.4. Conclusion 85
References 86
APPENDIX 98
- Degree
- Master
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