Characterization of [1]Benzothieno[3,2-b]benzothiophene (BTBT) Derivatives with End-Capping Groups as Solution-Processable Organic Semiconductors for Organic Field-Effect Transistors
Source abstract
Abstract
Solution-processable [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives with various end-capping groups, 2-(phenylethynyl)benzo[b]benzo[4,5]thieno[2,3-d]thiophene (Compound 1), 2-octyl-7-(5-(phenylethynyl)thiophen-2-yl)benzo[b]benzo[4,5]thieno[2,3-d]thiophene (Compound 2), and triisopropyl((5-(7-octylbenzo[b]benzo[4,5]thieno[2,3-d]thiophen-2-yl)thiophen-2-yl)ethynyl)silane (Compound 3), have been synthesized and characterized as active layers for organic field-effect transistors (OFETs). Thermal, optical, and electrochemical properties of the newly synthesized compounds were characterized using thermogravimetric analysis (TGA), a differential scanning calorimeter (DSC), UV–vis spectroscopy, and cyclic voltammetry (CV). Thin films of each compound were formed using the solution-shearing method and the thin film surface morphology and texture of the corresponding films were characterized using atomic force microscopy (AFM) and θ–2θ X-ray diffraction (XRD). All semiconductors exhibited p-channel characteristics in ambient and Compound 1 showed the highest electrical performance with a carrier mobility of ~0.03 cm2/Vs and current on/off ratio of ~106.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Organic Light-Emitting Diodes Research
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 04107, Republic of Korea
Department of Smart Green Technology Engineering, Pukyong National University, Busan 48513, Republic of Korea
Department of Chemistry, Pukyong National University, Busan 48513, Republic of Korea
Funding
National Research Foundation of Korea
References (60)
Show source-provided references
1. Diperfluorophenyl fused thiophene semiconductors for n-type organic thin film transistors (OTFTs)10.1002/aelm.201500098 ↗
2. Green solvents for organic thin-film transistor processing10.1039/D0TC00512F ↗
3. Solution-processed nonvolatile organic transistor memory based on semiconductor blends10.1021/acsami.8b20571 ↗
4. Solution-Processable Dithienothiophenoquinoid (DTTQ) Structures for Ambient-Stable n-Channel Organic Field Effect Transistors10.1002/adfm.201606761 ↗
5. Deep blue phosphorescent organic light-emitting diodes with very high brightness and efficiency10.1038/nmat4446 ↗
6. Multifunctional Organic-Semiconductor Interfacial Layers for Solution-Processed Oxide-Semiconductor Thin-Film Transistor10.1002/adma.201607055 ↗
7. BODIPY-based semiconducting materials for organic bulk heterojunction photovoltaics and thin-film transistors10.1002/cplu.201800543 ↗
8. Dialkoxybithiazole: A new building block for head-to-head polymer semiconductors10.1021/ja3120532 ↗
9. Pentacene-based radio-frequency identification circuitry10.1063/1.1579554 ↗
10. Green solvent-processed organic electronic devices10.1039/D0TC03610B ↗
11. Solution-processable dithieno [3,2-b:2′,3′-d] thiophene derivatives for organic thin-film transistors and complementary-like inverters10.1016/j.orgel.2017.11.023 ↗
12. Synthesis and characterization of carbazole-and α-carboline-based thiophene derivatives as organic semiconductors for organic thin-film transistors10.1016/j.dyepig.2014.10.024 ↗
13. Recent progress in solution processable TADF materials for organic light-emitting diodes10.1039/C8TC01139G ↗
14. Diketopyrrolopyrrole-containing quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel organic field-effect transistors10.1021/ja3003183 ↗
15. Recent progress in the development of n-type organic semiconductors for organic field effect transistors10.1039/C7TC01680H ↗
16. Synthesis and characterization of solution-processable diketopyrrolopyrrole (DPP) and tetrathienothiophene (TTA)-based small molecules for organic thin film transistors and organic photovoltaic cells10.1016/j.dyepig.2016.05.041 ↗
17. High-performance bottom-contact organic thin-film transistors based on benzo[d,d′]thieno[3,2-b;4,5-b′]dithiophenes (BTDTs) derivatives10.1021/am3022448 ↗
18. Development of n-type organic semiconductors for thin film transistors: A viewpoint of molecular design10.1039/C3TC32046D ↗
19. Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors10.1021/ar990114j ↗
20. Thieno [3,4-c] pyrrole-4,6-dione-based polymer semiconductors: Toward high-performance, air-stable organic thin-film transistors10.1021/ja205398u ↗
21. Molecular phase engineering of organic semiconductors based on a [1]benzothieno[3,2-b][1] benzothiophene core10.1039/C6RA22999A ↗
22. High Performance OTFTs Fabricated Using a Calamitic Liquid Crystalline Material of 2-(4-Dodecyl phenyl)[1] benzothieno [3,2-b][1] benzothiophene10.1002/aelm.201600179 ↗
23. Low-temperature band transport and impact of contact resistance in organic field-effect transistors based on single-crystal films of Ph-BTBT-C1010.1103/PhysRevApplied.5.064017 ↗
24. 2, 7-Diphenyl[1]benzothieno [3,2-b]benzothiophene, a new organic semiconductor for air-stable organic field-effect transistors with mobilities up to 2.0 cm2V-1s-110.1021/ja064052l ↗
25. Bulky end-capped[1]benzothieno[3,2-b] benzothiophenes: Reaching high-mobility organic semiconductors by fine tuning of the crystalline solid-state order10.1002/adma.201500322 ↗
26. Low-voltage organic field effect transistors with a 2-tridecyl[1] benzothieno[3,2-b][1]benzothiophene semiconductor layer10.1021/ja307802q ↗
27. UV–deep blue–visible light-emitting organic field effect transistors with high charge carrier mobilities10.1002/adom.201600973 ↗
28. High Mobility in Solution-Processed 2,7-Dialkyl-[1]benzothieno[3,2-b][1] benzothiophene-Based Field-Effect Transistors Prepared with a Simplified Deposition Method10.1002/cplu.201300414 ↗
29. Ultra-high mobility transparent organic thin film transistors grown by an off-centre spin-coating method10.1038/ncomms4005 ↗
30. Liquid crystalline organic semiconductors for organic transistor applications10.1038/pj.2016.101 ↗
31. Liquid crystals for organic thin-film transistors10.1038/ncomms7828 ↗
32. Bernal, V., Giraldo, L., and Moreno-Piraján, J. (2018). Physicochemical Properties of Activated Carbon: Their Effect on the Adsorption of Pharmaceutical Compounds and Adsorbate–Adsorbent Interactions. C, 4.10.3390/c4040062 ↗
33. Influence of the alkyl chain length on the physicochemical properties and biological activity in a homologous series of dichlorprop-based herbicidal ionic liquids10.1016/j.molliq.2018.12.013 ↗
34. Othman Zailani, N.H.Z., Yunus, N.M., Ab Rahim, A.H., and Bustam, M.A. (2020). Thermophysical properties of newly synthesized ammonium-based protic ionic liquids: Effect of temperature, anion and alkyl chain length. Processes, 8.10.3390/pr8060742 ↗
35. Naphthyl and Thionaphthyl End-Capped Oligothiophenes as Organic Semiconductors: Effect of Chain Length and End-Capping Groups10.1002/adfm.200706198 ↗
36. A new rod-shaped BODIPY-acetylene molecule for solution-processed semiconducting microribbons in n-channel organic field-effect transistors10.1039/C7NJ00266A ↗
37. Acetylenic spacers in phenylene end-substituted oligothiophene core for highly air-stable organic field-effect transistors10.1039/b923352k ↗
38. High performance asymmetrical push–pull small molecules end-capped with cyanophenyl for solution-processed solar cells10.1039/C4CC04020A ↗
39. Development and Characterization of Solution-Processable Dithieno [3,2-b:2’,3’-d] thiophenes Derivatives with Various End-capped Groups for Organic Field-Effect Transistors10.1002/cplu.202200267 ↗
40. Synthesis and characterization of 2,7-diethynyl-benzo[b]benzo[4,5]thieno[2,3-d] thiophene derivative as organic semiconductors for organic thin-film transistors10.1016/j.synthmet.2016.08.002 ↗
41. Efficient Diketopyrrolopyrrole-Based Small-Molecule Bulk-Heterojunction Solar Cells with Different Electron-Donating End-Groups10.1002/asia.201402223 ↗
42. Functionalized Arylacetylene Oligomers for Organic Thin-Film Transistors (OTFTs)10.1002/adma.200401998 ↗
43. Solution-processable low-molecular weight extended arylacetylenes: Versatile p-type semiconductors for field-effect transistors and bulk heterojunction solar cells10.1021/ja910420t ↗
44. Phenanthrene-functionalized 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4–c]pyrrole-1,4-diones as donor molecules for solution-processed organic photovoltaic cells10.1016/j.solmat.2011.05.006 ↗
45. New Conjugated Molecules with Two and Three Dithienyldiketopyrrolopyrrole (DPP) Moieties Substituted at meta Positions of Benzene toward p-and n-Type Organic Photovoltaic Materials10.1002/asia.201400089 ↗
46. Marrocchi, A., Silvestri, F., Seri, M., Facchetti, A., Taticchi, A., and Marks, T.J. (2009). Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells: Olefinic versus acetylenic spacers. Chem. Commun., 1380–1382.10.1039/b820829h ↗
47. Ethynylene-linked donor–acceptor alternating copolymers10.1021/ma400238t ↗
48. Small Molecular Aryl Acetylenes: Chemically Tailoring High-Efficiency Organic Semiconductors for Solar Cells and Field-Effect Transistors10.1002/cplu.201400001 ↗
49. Benzothienobenzothiophene-based conjugated oligomers as semiconductors for stable organic thin-film transistors10.1021/am500598f ↗
50. [1]Benzothieno[3,2-b][1] benzothiophene-based liquid crystalline organic semiconductor for solution-processed organic thin film transistors10.1016/j.jiec.2022.07.005 ↗
51. Modification of alkyl side chain on thiophene-containing benzothieno [3,2-b]benzothiophene-based organic semiconductors for organic field-effect transistors10.1016/j.synthmet.2022.117173 ↗
52. Critical assessment of charge mobility extraction in FETs10.1038/nmat5035 ↗
53. Avoid the kinks when measuring mobility10.1126/science.aaf9062 ↗
54. Design, synthesis, and self-assembly of oligothiophene derivatives with a diketopyrrolopyrrole core10.1021/jp804816c ↗
55. Effect of the number of thiophene rings in polymers with 2,1,3-benzooxadiazole core on the photovoltaic properties10.1016/j.orgel.2013.07.009 ↗
56. Bodipy-backboned polymers as electron donor in bulk heterojunction solar cells10.1039/b927350f ↗
57. Density Functional Theory Study of Silolodithiophene Thiophenepyrrolopyrroledione-based Small Molecules: The Effect of Alkyl Side Chain Length in Electron Donor Materials10.1002/bkcs.10096 ↗
58. Influence of alkyl side-chain length on the carrier mobility in organic semiconductors: Herringbone vs. pi–pi stacking10.1039/C6TC00755D ↗
59. Effect of the degree of the gate-dielectric surface roughness on the performance of bottom-gate organic thin-film transistors10.1002/admi.201902145 ↗
60. Reduced roughness for improved mobility in benzodipyrrolidone-based, n-type OFETs10.1039/C4TC01790K ↗