Synthesis and Characterization of Organic Compounds for Organic Thin-Film Transistors and Organic Light Emitting Diodes
- Abstract
- Chapter 1.
이 연구에서는 새로운 benzo[b]thieno[2,3-d]thiophene (BTT) 유도체, 2-(thiophene-2-yl)benzo[b]thieno[2,3-d] thiophene (화합물 1), 2-(5-(2-ethylhexyl)thiophene-2-yl)benzo[b]thieno[2,3-d]thiohpene (화합물 2), 및 2-(5-octylthiophene-2-yl)benzo[b]theino[2,3-d]thiohpene (화합물 3)은 유기 전계 효과 트랜지스터(OFET)용 용액 처리 가능한 유기 반도체(OSC)로 합성되고 특성화되었다. 개발된 유기화합물은 물리화학적 특성을 위해 열중량분석(TGA), 시차주사열량계(DSC), UV-vis 분광법, 순환전압전류법으로 분석하였다. 모든 BTT-유도체는 용액 전단법으로 코팅되었고 제작된 필름은 원자간력현미경(AFM) 및 θ-2θ X선 회절(XRD)로 특성화되었다. 새로 합성된 BTT 유도체의 전기적 성능을 조사하기 위해 하단 게이트/상단 접촉 OFET를 제작하고 주변 조건에서 특성화했다. 모든 화합물은 p-채널 활성을 나타내었고, 특히 화합물 3의 필름을 기반으로 하는 생성된 OFET는 0.11 cm2/Vs의 가장 높은 정공 이동도 및 8.7 × 106의 전류 온/오프 비율을 나타내었다.
Chapter 2.
새로 합성된 benzo[b]thieno[2,3-d]thiophene 유도체, 2-([2,2’-bithiophene]-5-yl)benzo[b]thieno[2,3-d]thiophene (4), 2-(5’-(2-ethylhexyl)-[2,2’-bithiophene]-5-yl)benzo[b]thieno[2,3-d]thiophene (5), 및 2-(5’-octyl-[2,2’-bithiophen]-5-yl)benzo[b]thieno[2,3-d]thiophene (6)는 유기 박막 트랜지스터(OTFT)용 용액 공정을 통해 유기 반도체(OSC)로 사용되었다. 세 가지 유기 화합물은 열중량 분석(TGA), 시차 주사 열량계(DSC), 순환 전압전류법(CV), UV-가시광선 분광법 및 밀도 기능 이론(DFT) 계산으로 특성화되었다. 용액 전단법(Solution-shearing, SS) 방법을 사용하여 화합물의 박막을 형성하고, 원자간력현미경(AFM) 및 θ-2θ X선 회절(XRD)을 사용하여 박막의 미세구조 및 형태를 조사하였다. 각 화합물의 박막을 기반으로 제작된 OTFT는 주변 조건에서 p-채널 활성을 나타냈고, 특히 화합물 5 기반 트랜지스터는 화합물 박막에 따라 최대 0.057 cm2/Vs의 정공 이동도와 107 이상의 전류 온/오프 비율을 나타냈다. 따라서 화합물 5의 박막은 우수한 표면 커버리지와 높은 필름 질감을 보여준다.
Chapter 3.
또 다른 아로마틱을 붙인 7개의 새로운 benzothieno[3,2-b]thiophene (BTT) 유도체, 2-(benzo[b]thiophen-5-yl)benzo[b]thieno[2,3-d]thiophene (7), 2-(benzo[b]thiophen-6-yl)benzo[b]thieno[2,3-d]thiophene (8), 2-(benzo[b]thieno[2,3-d]thiophen-2-yl)dibenzo[b,d]thiophene (9), functionalized with alkyne 2-(phenylethynyl)benzo[b]thieno[2,3-d]thiophene (10), 2-(thiophen-2-ylethynyl)benzo[b]thieno[2,3-d]thiophene (11), functionalized with alkene (E)-2-styrylbenzo[b]thieno[2,3-d]thiophene (12), and (E)-2-(2-(thiophen-2-yl)vinyl)benzo[b]thieno[2,3-d]thiophene (13)은 유기 박막 트랜지스터 (OTFT)에서 합성되고 특성화되었다. 모든 유기 화합물은 열중량 분석(TGA), 시차 주사 열량계(DSC), 순환 전압전류법(CV), UV-가시광선 분광법 및 밀도 기능 이론(DFT) 계산으로 특성화되었다. 이 연구에서 BTT 파생상품은 0.008 cm2/Vs만큼 높은 전하 캐리어 이동도와 6.57×106의 전류 온/오프 비율로 주변 OTFT에서 p-채널 특성을 나타냈습니다. 소자 특성은 해당 화합물의 막 형태 및 미세 구조와 상관관계가 있었다.
Chapter 4.
새로운 카바졸 기반 노란색 호스트 물질인 (5-(8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-yl)thiophen-2-yl)diphenylphosphine oxide (CTTPO)를 합성했습니다. 유기 발광 다이오드(OLED)와 소자의 성능을 확인했다. 이 물질은 정공 수송성을 갖는 카바졸과 전자 수송성을 갖는 디벤조티오펜 및 포스핀 옥사이드 단위를 갖는다. 이 구조는 단일항 에너지 3.60 eV, 삼중항 에너지 2.52 eV로 PO-01을 10% 도핑했을 때 최대 양자 효율 25.4%, 전력 효율 65.7 lm/W를 나타냈다.
In chapter 1.
In this study, novel benzo[b]thieno[2,3-d]thiophene (BTT) derivatives, 2-(thiophene-2-yl)benzo[b]thieno[2,3-d] thiophene (compound 1), 2-(5-(2-ethylhexyl)thiophene-2-yl)benzo[b]thieno[2,3-d]thiohpene (compound 2), and 2-(5-octylthiophene-2-yl)benzo[b]theino[2,3-d]thiohpene (compound 3), were synthesized and characterized as solution-processable organic semiconductors (OSCs) for organic field-effect transistors (OFETs). Developed organic compounds were analyzed by thermogravimetric analysis (TGA), differential scanning calorimeter (DSC), UV–vis spectroscopy, and cyclic voltammetry for physicochemical characteristics. All BTT-derivatives were coated by solution-shearing method and fabricated films were characterized by atomic force microscopy (AFM) and θ-2θ X-ray diffraction (XRD). To investigate the electrical performance of newly synthesized BTT derivatives, bottom-gate/top-contact OFETs were fabricated and characterized in ambient conditions. All compounds exhibited p-channel activity and especially, the resulting OFETs based on films of compound 3 showed the highest hole mobility of 0.11 cm2/Vs and current on/off ratio of 8.7 × 106.
In chapter 2.
Newly synthesized benzo[b]thieno[2,3-d]thiophene derivatives, 2-([2,2’-bithiophene]-5-yl)benzo[b]thieno[2,3-d]thiophene (4), 2-(5’-(2-ethylhexyl)-[2,2’-bithiophene]-5-yl)benzo[b]thieno[2,3-d]thiophene (5), and 2-(5’-octyl-[2,2’-bithiophen]-5-yl)benzo[b]thieno[2,3-d]thiophene (6), were employed as organic semiconductors (OSCs) via solution process for organic thin film transistors (OTFTs). Three organic compounds were characterized by thermogravimetric analysis (TGA), differential scanning calorimeter (DSC), cyclic voltammetry (CV), UV-visible spectroscopy, and density functional theory (DFT) calculation. Solution-shearing (SS) method was used to form thin films of the compounds, and microstructure as well as morphology of the thin films were investigated with atomic force microscopy (AFM) and θ-2θ X-ray diffraction (XRD). Fabricated OTFTs based on thin films of each compound exhibited p-channel activity in ambient condition, and especially transistors based on compound 5 featured hole mobility up to 0.057 cm2/Vs and current on/off ratio over 107, in accordance with thin films of compound 5 showing superb surface coverage and high film texture.
In chapter 3.
Seven new benzothieno[3,2-b]thiophene (BTT) derivatives, which were another aromatic attached 2-(benzo[b]thiophen-5-yl)benzo[b]thieno[2,3-d]thiophene (7), 2-(benzo[b]thiophen-6-yl)benzo[b]thieno[2,3-d]thiophene (8), 2-(benzo[b]thieno[2,3-d]thiophen-2-yl)dibenzo[b,d]thiophene (9), functionalized with alkyne 2-(phenylethynyl)benzo[b]thieno[2,3-d]thiophene (10), 2-(thiophen-2-ylethynyl)benzo[b]thieno[2,3-d]thiophene (11), functionalized with alkene (E)-2-styrylbenzo[b]thieno[2,3-d]thiophene (12), and (E)-2-(2-(thiophen-2-yl)vinyl)benzo[b]thieno[2,3-d]thiophene (13) were synthesized and characterized in organic thin-film transistors (OTFTs). All organic compounds were characterized by thermogravimetric analysis (TGA), differential scanning calorimeter (DSC), cyclic voltammetry (CV), UV-visible spectroscopy, and density functional theory (DFT) calculation. The BTT derivatives in this study, exhibited p-channel characteristic in ambient OTFTs, with a charge carrier mobility as high as 0.008 cm2/Vs and a current on/off ratio of 6.57×106. The device characteristics were correlated with the film morphologies and microstructures of the corresponding compounds.
In chapter 4.
We synthesized a new carbazole-based yellow host material, (5-(8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-yl)thiophen-2-yl)diphenylphosphine oxide (CTTPO) for an organic light emitting diode (OLED) and confirmed the device's performance. This material has carbazole having hole transport properties and dibenzothiophene and phosphine oxide units having electron transport properties. This structure showed a maximum quantum efficiency of 25.4%, and power efficiency of 65.7 lm/W when PO-01 was doped with 10% with singlet energy of 3.60 eV and triplet energy of 2.52 eV.
- Issued Date
- 2022
- Awarded Date
- 2022. 8
- Type
- Dissertation
- Publisher
- 부경대학교
- Alternative Author(s)
- Soomin Ryu
- Affiliation
- 부경대학교 대학원
- Department
- 대학원 스마트그린기술융합공학과
- Advisor
- 서성용
- Table Of Contents
- Chapter 1. Synthesis and Characterization of Benzo[b]thieno[2,3-d]thiophene (BTT) Derivatives as Solution-Processable Organic Semiconductors for Organic Field-Effect Transistors 1
1.1 Introduction 1
1.2 Experimental 5
1.2.1 General Methods 5
1.2.2 Synthesis 5
1.2.2.1 Synthesis of 2-bromobenzo[b]thieno[2,3-d]thiophene (1a) 5
1.2.2.2 Synthesis of 2-(thiophen-2-yl)benzo[b]thieno[2,3-d]thiophene (1) 5
1.2.2.3 Synthesis of 2-(5-(2-ethylhexyl)thiophen-2-yl)benzo[b]thieno[2,3-d]thiophene (2) 6
1.2.2.4 Synthesis of 2-(5-octylthiophen-2-yl)benzo[b]thieno[2,3-d] thiophene (3) 7
1.2.3 Theoretical calculation 7
1.2.4 Device fabrication 8
1.2.5 Film and device characterization 8
1.3 Results and Discussion 10
1.3.1 Synthesis 10
1.3.2 Thermal, optical, and electrochemical properties 10
1.3.3 Theoretical calculation 17
1.3.4 Thin-film morphology and microstructure 19
1.3.5 Electrical performance of OFETs 23
1.4 Conclusion 27
Chapter 2. Solution Processable Benzo[b]thieno[2,3-d]thiophene Derivatives as Small Molecular Organic Semiconductors for Organic Thin-Film Transistors 28
2.1 Introduction 28
2.2 Experimental 33
2.2.1 General methods and material characterization 33
2.2.2 Synthesis 34
2.2.2.1 Synthesis of 2-(5-iodothiophen-2-yl)benzo[b]thieno[2,3-d]thiophene (4b) 34
2.2.2.2 Synthesis of 2-([2,2'-bithiophen]-5-yl)benzo[b]thieno[2,3-d]thiophene (1) 34
2.2.2.3 Synthesis of 2-(5'-(2-ethylhexyl)-[2,2'-bithiophen]-5-yl)benzo[b]thieno[2,3-d]thiophene (5) 35
2.2.2.4 Synthesis of 2-(5'-octyl-[2,2'-bithiophen]-5-yl)benzo[b]thieno[2,3-d]thiophene (6) 36
2.2.3 Theoretical calculation 36
2.2.4 Device fabrication 37
2.2.5 Device characterization 38
2.3 Results and discussion 38
2.3.1 Synthesis 38
2.3.2 Thermal, optical, and electrochemical properties 40
2.3.3 Thermal calculation 48
2.3.4 Thin film morphology and microstructure 50
2.3.5 Fabrication and Characterization of OTFTs 55
2.4 Conclusion 60
Chapter 3. Benzo[b]thieno[2,3-d]thiophene (BTT) Derivatives as Solution-Processable Organic Semiconductors for Organic Thin Film Transistors 61
3.1 Introduction 61
3.2 Experimental 64
3.2.1 Materials and Methods 64
3.2.2 Synthesis 64
3.2.2.1 Synthesis of benzo[b]thieno[2,3-d]thiophene (14) 64
3.2.2.2 Synthesis of benzo[b]thieno[2,3-d]thiophen-2-yltributylstannane (15) 65
3.2.2.3 Synthesis of 2-(benzo[b]thiophen-5-yl)benzo[b]thieno[2,3-d]thiophene (7) 65
3.2.2.4 Synthesis of 2-(benzo[b]thiophen-6-yl)benzo[b]thieno[2,3-d]thiophene (8) 66
3.2.2.5 Synthesis of 2-(benzo[b]thieno[2,3-d]thiophen-2-yl)dibenzo[b,d]thiophene (9) 66
3.2.2.6 Synthesis of 2-bromobenzo[b]thieno[2,3-d]thiophene (16) 67
3.2.2.7 Synthesis of 2-(phenylethynyl)benzo[b]thieno[2,3-d]thiophene (10) 67
3.2.2.8 Synthesis of (benzo[b]thieno[2,3-d]thiophen-2-ylethynyl)trimethylsilane (17) 68
3.2.2.9 Synthesis of 2-ethynylbenzo[b]thieno[2,3-d]thiophene (18) 68
3.2.2.10 Synthesis of 2-(thiophen-2-ylethynyl)benzo[b]thieno[2,3-d]thiophene (11) 68
3.2.2.11 Synthesis of (E)-2-(2-(thiophen-2-yl)vinyl)benzo[b]thieno[2,3-d]thiophene (13) 69
3.2.2.12 Synthesis of (E)-2-styrylbenzo[b]thieno[2,3-d]thiophene (12) 69
3.2.3 Theoretical calculation 70
3.2.4 Device fabrication 70
3.3 Results and discussion 71
3.3.1 Synthesis 71
3.3.2 Thermal, optical, and electrochemical properties 75
3.3.3 Theoretical calculation 82
3.3.4 Thin-film transistor characterization 87
3.4 Conclusion 90
Chapter 4. Synthesis of Novel Dibenzothiophene Derivatives as a Yellow Host Material for Phosphorescent Organic Light-Emitting Diodes 91
4.1 Introduction 91
4.2 Experimental 93
4.2.1 General Methods 93
4.2.2 Synthesis 93
4.2.2.1 Synthesis of 2,8-dibromodibenzo[b,d]thiophene (20) 93
4.2.2.2 Synthesis of 9-(8-bromodibenzo[b,d]thiophen-2-yl)-9H-carbazole (21) 93
4.2.2.3 Synthesis of 9-(8-(thiophen-2-yl)dibenzo[b,d]thiophene-2-yl)-9H-carbazole (22) 94
4.2.2.4 Synthesis of (5-(8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-yl)thiophen-2-yl)diphenylphosphine oxide (19, CTTPO) 94
4.2.3 Device fabrication 95
4.3 Results and discussion 98
4.4 Conclusion 118
References 119
APPENDIX 141
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