853234-57-8Relevant articles and documents
Ultralow bandgap molecular semiconductors for ambient-stable and solution-processable ambipolar organic field-effect transistors and inverters
Ozdemir, Resul,Choi, Donghee,Ozdemir, Mehmet,Kwon, Guhyun,Kim, Hyekyoung,Sen, Unal,Kim, Choongik,Usta, Hakan
, p. 2368 - 2379 (2017/03/14)
The design and development of novel ambipolar semiconductors is very crucial to advance various optoelectronic technologies including organic complementary (CMOS) integrated circuits. Although numerous high-performance ambipolar polymers have been realized to date, small molecules have been unable to provide high ambipolar performance in combination with ambient-stability and solution-processibility. In this study, by implementing highly π-electron deficient, ladder-type IFDK/IFDM acceptor cores with bithiophene donor units in D-A-D π-architectures, two novel small molecules, 2OD-TTIFDK and 2OD-TTIFDM, were designed, synthesized and characterized in order to achieve ultralow band-gap (1.21-1.65 eV) semiconductors with sufficiently balanced molecular energetics for ambipolarity. The HOMO/LUMO energies of the new semiconductors are found to be ?5.47/?3.61 and ?5.49/?4.23 eV, respectively. Bottom-gate/top-contact OFETs fabricated via solution-shearing of 2OD-TTIFDM yield perfectly ambient stable ambipolar devices with reasonably balanced electron and hole mobilities of 0.13 cm2 V?1 s?1 and 0.01 cm2 V?1 s?1, respectively with Ion/Ioff ratios of ～103-104, and 2OD-TTIFDK-based OFETs exhibit ambipolarity under vacuum with highly balanced (μe/μh ～ 2) electron and hole mobilities of 0.02 cm2 V?1 s?1 and 0.01 cm2 V?1 s?1, respectively with Ion/Ioff ratios of ～105-106. Furthermore, complementary-like inverter circuits were demonstrated with the current ambipolar semiconductors resulting in high voltage gains of up to 80. Our findings clearly indicate that ambient-stability of ambipolar semiconductors is a function of molecular orbital energetics without being directly related to a bulk π-backbone structure. To the best of our knowledge, considering the processing, charge-transport and inverter characteristics, the current semiconductors stand out among the best performing ambipolar small molecules in the OFET and CMOS-like circuit literature. Our results provide an efficient approach in designing ultralow band-gap ambipolar small molecules with good solution-processibility and ambient-stability for various optoelectronic technologies, including CMOS-like integrated circuits.
Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents
Ozdemir, Mehmet,Choi, Donghee,Kwon, Guhyun,Zorlu, Yunus,Kim, Hyekyoung,Kim, Myung-Gil,Seo, SungYong,Sen, Unal,Citir, Murat,Kim, Choongik,Usta, Hakan
, p. 212 - 226 (2016/01/09)
A series of indeno[1,2-b]fluorene-6,12-dione-thiophene derivatives with hydrocarbon substituents at α,ω-positions as side groups have been designed and synthesized. The new compounds were fully characterized by 1H/13C NMR, mass spectrometry, cyclic voltammetry, UV-vis absorption spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and melting point measurements. The solid state structure of the indeno[1,2-b]fluorene-6,12-dione acceptor core has been identified based on single-crystal X-ray diffraction (XRD). The structural and electronic properties were also studied using density functional theory calculations, which were found to be in excellent agreement with the experimental findings and provided further insight. The detailed effects of alkyl chain size and orientation on the optoelectronic properties, intermolecular cohesive forces, thin-film microstructures, and charge transport performance of the new semiconductors were investigated. Two of the new solution-processable semiconductors, 2EH-TIFDKT and 2OD-TIFDKT, were deposited as thin-films via solution-shearing, drop-casting, and droplet-pinned crystallization methods, and their morphologies and microstructures were investigated by X-ray diffraction (XRD) and atomic force microscopy (AFM). The solution-processed thin-film transistors based on 2EH-TIFDKT and 2OD-TIFDKT showed ambipolar device operations with electron and hole mobilities as high as 0.12 cm2 V-1 s-1 and 0.02 cm2 V-1 s-1, respectively, with Ion/Ioff ratios of 105 to 106. Here, we demonstrate that rational repositioning of the β-substituents to molecular termini greatly benefits the π-core planarity while maintaining a good solubility, and results in favorable structural and optoelectronic characteristics for more efficient charge-transport in the solid-state. The ambipolar charge carrier mobilities were increased by two-three orders of magnitude in the new indeno[1,2-b]fluorene-6,12-dione-thiophene core on account of the rational side-chain engineering.
Conjugated monomers and polymers and preparation and use thereof
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, (2009/07/02)
Disclosed are new conjugated compounds (e.g., monomers and polymers) that include ladder-type moieties which can be used for preparing semiconducting materials. Such conjugated compounds can exhibit high n-type carrier mobility and/or good current modulat
CONJUGATED MONOMERS AND POLYMERS AND PREPARATION AND USE THEREOF
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Page/Page column 66, (2009/03/07)
Disclosed are new conjugated compounds (e.g., monomers and polymers) that include ladder-type moieties which can be used for preparing semiconducting materials. Such conjugated compounds can exhibit high n-type carrier mobility and/or good current modulat
Design, synthesis, and characterization of ladder-type molecules and polymers. air-stable, solution-processable n-channel and ambipolar semiconductors for thin-film transistors via experiment and theory
Usta, Hakan,Risko, Chad,Wang, Zhiming,Huang, Hui,Deliomeroglu, Murat K.,et al.
supporting information; experimental part, p. 5586 - 5608 (2009/09/25)
The design, synthesis, and characterization of new high-performance n-channel molecular/ polymeric semiconductors that are solution-processable and air-stable is of great interest for the development of p - n junctions, bipolar transistors, and organic co
Air-stable, solution-processable n-channel and ambipolar semiconductors for thin-film transistors based on the indenofluorenebis(dicyanovinylene) core
Usta, Hakan,Facchetti, Antonio,Marks, Tobin J.
supporting information; experimental part, p. 8580 - 8581 (2009/02/03)
We present here the synthesis, characterization, and field-effect performance of a novel n-channel semiconducting molecule TIFDMT and of the corresponding thiophene-based copolymer P-IFDMT4 based on the indenofluorenebis(dicyanovinylene) core. TIFDMT-based field-effect transistors fabricated by spin-coating exhibit high electron mobilities of 0.10-0.16 cm2/V s in air, low turn-on voltages (～0 to +5 V), and high on/off ratios of 107-108. These devices also exhibit excellent air stability over a prolonged time of storage in ambient conditions. P-IFDMT4-based devices exhibit the first example of an air-stable ambipolar polymer processable from solution. Copyright
Synthesis of a double spiro-polyindenofluorene with a stable blue emission
Vak, Doojin,Lim, Bogyu,Lee, Soo-Hyoung,Kim, Dong-Yu
, p. 4229 - 4232 (2007/10/03)
(Chemical Equation Presented) A novel polyindenofluorene containing a double spiro-anthracene structure with solublizing alkyl groups was synthesized. Enhanced spectral stability of the polymer was investigated by heat treatment and photoirradiation in ai
