A synergistic combination of rational polymer backbone design, sidechain dynamics. Low band gap polymers have been actively sought in order to better tune the absorption spectra of organic semiconductors to the solar spectrum. The relatively low dielectric constant of organic semiconductors and the relatively weak electronic interactions between organic molecules characteristically result in a tightly bound exciton being created upon absorption of a photon 4. Diketopyrrolopyrrolecontaining polymers for highperformance organic. Synthesis and properties of a novel narrow band gap. Diketopyrrolopyrrolebased donoracceptor conjugated. High performance solution processed organic field effect. Organic semiconductors have revolutionized many areas of organic electronics, for example, optoelectronics,15 sensors68 and printable.
Hydrogenbonded diketopyrrolopyrrole dpp pigments as organic semiconductors. Pdf hydrogenbonded diketopyrrolopyrrole dpp pigments as. Their characterization as organic semiconductors in vacuum. Progress in polymer science 38 20 19091928 contents lists available at sciencedirect progress in polymer science. The dppbased conjugated polymers usually show good electron and hole mobility and promising pce values in opvs due to large intermolecular interactions through. Significant improvement of semiconducting performance of. Charge carriers in organic semiconductors are transported viaahoppingprocess,asorganicmoleculesare. High thermoelectric power factor of a diketopyrrolopyrrolebased low bandgap polymer via finely tuned doping engineering. Since the report of the first diketopyrrolopyrrole dpp. Review insight into highperformance conjugated polymers for organic fieldeffect transistors jie yang, 1,2 3zhiyuan zhao, shuai wang,2 yunlong guo,1, and yunqi liu compared with traditional silicon electronics, electronic devices based on. Diketopyrrolopyrrole copolymers based chemical sensors for. Conspectusconjugated polymers have been extensively studied for application in organic solar cells. Diketopyrrolopyrroles dpps have recently gained attention as buildingblocks for organic semiconducting polymers and small molecules, however the semiconducting properties of their hydrogenbonded hbonded pigment forms have not been explored. Oh, supramolecular nanostructures of chiral perylene diimides.
The present invention relates to polymers comprising diketopyrrolopyrrole repeating units and their use as org. Energetic control of redoxactive polymers towards safe. Energetic control of redoxactive polymers towards safe organic bioelectronic materials alexander giovannitti, reem b. Insitu monitoring of molecular vibrations of two organic semiconductors in photovoltaic blends and their impact on thin film morphology wing c.
The polymers according to the invention have excellent solubility in organic solvents and excellent filmforming properties. The donoracceptor datype diketopyrrolopyrrole dppbased small molecules lgcd117 and lgcd118 were synthesized and used as the active layer of solutionprocessable organic fieldeffect. To improve the charge carrier mobility of diketopyrrolopyrrole donoracceptor copolymer semiconductors, the length of the donor building block is controlled using vinylene moieties, and its effects on crystalline structure and charge transport are systematically studied. A factfinding study on thiophenyl diketopyrrolopyrrole tdppcontaining polymers for electronically convertible transport characteristics in organic field effect transistors ofets is presented. Diketopyrrolopyrrole polymers as organic semiconductors. In this paper we report three thiazoleflanked diketopyrrolopyrrolebased donor acceptor alternating copolymers as new ambipolar semiconductors and their fieldeffect transistor devices with balanced hole and electron mobilities. Optical characterization of the hole polaron in a series. Hydrogenbonded diketopyrrolopyrrole dpp pigments as. Polymers free fulltext optical characterization of. Impact of alkyl substituents and tolerance of ethylhexyl stereoisomers. Semiconducting polymers are now used in a variety of applications, such as organic photovoltaics14, organic lightemitting diodes5,6, organic. The polymers according to the invention have excellent solubility in organic. Effect of methyl substitution on the diketopyrrolopyrrole.
The polymers of the present invention are typically used as organic semiconductors in form of thin organic layers or films, preferably less than 30 microns thick. By taking into account both the conjugated backbone and side chains of the polymer component, we have developed a dithienyldiketopyrrolopyrrole tdpp and selenophene containing polymer with hybrid siloxanesolubilizing groups ptdppsesi. Using unsorted singlewall carbon nanotubes to enhance mobility of diketopyrrolopyrrolequarterthiophene copolymer in thin. Synthesis of diketopyrrolopyrrolebased polymers with polydimethylsiloxane side chains and their application in organic fieldeffect transistors inori ohnishi riken center for emergent matter science cems, 21 hirosawa, wako 3510198, japan. Hydrogenbonded diketopyrrolopyrrole dpp pigments as organic semiconductors article pdf available in organic electronics 1512 december 2014 with 794 reads how we measure reads.
Hydrogenbonded diketopyrrolopyrrole dpp pigments as organic semiconductors author links open overlay panel eric daniel glowacki a halime coskun a martin a. Benzodithiophenedione and diketopyrrolopyrrole based. This cited by count includes citations to the following articles in scholar. In the present work, we have used these high mobility dpp copolymers as active semiconductors in ofet device based chemical sensors for sensing of volatile organic compounds vocs in air. Fine molecular tuning of diketopyrrolopyrrolebased.
Three diketopyrrolopyrrole dpp quaterthiophene conjugated polymers, pdpp4t1, pdpp4t2, and pdpp4t3, in which the molar ratios of the ureacontaining alkyl chains vs branching alkyl chains are 1. Solutionprocessable ambipolar diketopyrrolopyrrole. Investigation of thiophene flanked diketopyrrolopyrrole monomers with straight and branched alkyl chains and their electropolymerization study volume 32 issue 14 supreetha paleyanda ponnappa, sivanesan arumugam, sergei manzhos, jennifer macleod, henry j. Typically the semiconducting layer of the present invention is at most 1 micron 1. Apart from ofet and opv, there are very few reports about these materials for other organic electronic devices such as chemical sensors. Synthesis and performance characterization of polymer. We synthesize p29dpptbt with two vinylene linkages between thiophene units and compare it with p29. Synthesis and performance characterization of polymer semiconductors for organic thin film transistors by chang guo. Synthesis of bisthienyl diketopyrrolopyrrolebithiazole. Type organic semiconductors in organic electronics. Diketopyrrolopyrrole polymers for organic solar cells. Hydrogenbonded diketopyrrolopyrrole dpp pigments as organic semiconductors eric daniel glowackia.
A versatile building block for organic photovoltaic materials article pdf available in macromolecular research 2. Selfassembly polymorphism of regioisomeric diketopyrrolopyrrolebased. Solutionprocessable dad structured two organic small molecules bearing thienyl diketopyrrolopyrrole tdpp and furanyl diketopyrrolopyrrole fdpp as central acceptor units and cyano on the. Hydrogenbonded diketopyrrolopyrrole dpp pigments as organic. This polymer exhibits ambipolar charge transport when used as a single component active semiconductor in otfts with balanced hole and electron mobilities of 0. Material design and synthesis have played a significant role in the development of organic solar cells. Pdf hydrogenbonded diketopyrrolopyrrole dpp pigments. Additionally, the control of the ionization potential and electron affinity of donor and acceptor materials has been used to. Solution processable diketopyrrolopyrrole dpp cored. In addition, high efficiency of energy conversion, excellent fieldeffect mobility, good onoff current ratios andor excellent stability can be observed, when the polymers according to the invention are used in semiconductor devices or organic photovoltaic pv devices solar cells. Diketopyrrolopyrrole, organic field effect transistor. A comprehensive computational study is performed on model compounds based on 2,1,3benzochalcogenadiazoles and diketopyrrolopyrroles of a. Recent advances in the green, sustainable synthesis of.
Naphthalene flanked diketopyrrolopyrrole based organic. Developing efficient and wide spectrally acting photocatalysts for lightdriven hydrogen production from water is highly desirable for solar energy conversion. Seon jeng lee, seok heon jung, jinkyun lee, cheawon kim, and mi jung lee investigation of charge injection characteristics in diketopyrrolopyrrole ambipolar. Investigation of charge injection characteristics in. Insitu monitoring of molecular vibrations of two organic. The present invention relates to polymers comprising a repeating unit of the formula i and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor andor a solar cell, or a device containing a diode andor an organic field effect transistor, andor a solar cell. Estimated mobility of ambipolar organic semiconductors. Organic electronics, which include organic thin film transistors otfts and. Investigation of structureproperty relationships in. As a result, the power conversion efficiencies pces of solar cells based on conjugated polymers as. Dppbased polymer semiconductors have achieved record high mobility values for. Synthetic routes to the dpp monomer with pdms side chains and to the random copolymers with various pdms contents. High thermoelectric power factor of a diketopyrrolopyrrole.
Here, we design and synthesize three new diketopyrrolopyrrole dpp derivatives with naphthalene, possessing largescaled. Diketopyrrolopyrrolle polymers for efficient organic solar. Synthesis of diketopyrrolopyrrolebased polymers with. A new, solutionprocessable, lowbandgap, diketopyrrolopyrrolebenzothiadiazolebased, donoracceptor polymer semiconductor pdpptbt is reported. Diketopyrrolopyrroles dpps have recently gained attention as buildingblocks for organic semiconducting polymers and small molecules, however the. Diketopyrrolopyrrole copolymers based chemical sensors for the detection and discrimination of volatile organic compounds. We demonstrated a new design concept for stretchable semiconducting polymers, which involves introducing chemical moieties to promote dynamic noncovalent crosslinking of. Here, we report the synthesis of a new diketopyrrolopyrrole dpp derivative, pyrazine. Pdf an ultralow bandgap diketopyrrolopyrrole dppbased. Influencing the photovoltaic properties and aggregation of.
Systematic sidechain engineering has been performed for diketopyrrolopyrroleselenophene vinylene selenophene dppsvs polymers to determine the optimal sidechain geometries for the most efficient charge transport, and the structureproperty relationship has been thoroughly investigated using a range of analyses. In designing new polymers, particular attention has been given to tuning the absorption spectrum, molecular energy levels, crystallinity, and charge carrier mobility to enhance performance. The polymers according to the invention have excellent solubility. Investigation of thiophene flanked diketopyrrolopyrrole. Insight into highperformance conjugated polymers for. Conjugated terpolymers synthesized by incorporating anthracene units into the backbones of the diketopyrrolopyrrolebased polymers as electron donors for photovoltaic cells. Pdf diketopyrrolopyrroles dpps have recently gained attention as building blocks for organic semiconducting polymers and small molecules, however. The title organic molecules, recently used as building blocks of ambipolar. Swapping fieldeffect transistor characteristics in. Polymers a b s t r a c t polymer solar cells have many intrinsic advantages, such as their light weight. Their excellent printability, light weight, mechanical robustness and flexibility are.
Mccullochalkyl chain extension as a route to novel thieno3,2bthiophene flanked diketopyrrolopyrrole polymers for use in organic solar cells and field effect transistors. The polymers of the invention can be used alone or in combination as the organic semiconductor layer of the semiconductor device. In addition, ambipolar polymer semiconductors, in which both. A lowbandgap diketopyrrolopyrrolebenzothiadiazolebased. Cn101479272b diketopyrrolopyrrole polymers as organic. Wo2008000664a1 diketopyrrolopyrrole polymers as organic. The present invention relates to polymers comprising a repeating unit of the formula and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor andor a solar cell, or a device containing a diode andor an organic field effect transistor, andor a solar cell. High mobility diketopyrrolopyrrole dppbased organic. David kilcoyne, prashant sonar, xiaojing zhou, paul c. The present invention relates to polymers comprising a repeating unit of the formula l and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor andor a solar cell, or a device containing a diode andor an organic field effect transistor, andor a solar cell.
1276 858 157 309 1477 92 1238 73 1617 1190 514 133 1644 1618 219 553 476 445 157 1467 883 337 1679 1440 81 727 741 1365 427 242 606 400 941