3,6-Di(furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and bithiophene copolymer with rather disordered chain orientation showing high mobility in organic thin film transistors

Pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione or diketopyrrolopyrrole (DPP) is a useful electron-withdrawing fused aromatic moiety for the preparation of donor-acceptor polymers as active semiconductors for organic electronics. This study uses a DPP-furan-containing building block, 3,6-di(furan-2-yl)pyrrolo[3,4- c]pyrrole-1,4(2H,5H)-dione (DBF), to couple with a 2,2′-bithiophene unit, forming a new donor-acceptor copolymer, PDBFBT. Compared to its structural analogue, 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DBT), DBF is found to cause blue shifts of the absorption spectra both in solution and in thin films and a slight reduction of the highest occupied molecular orbital (HOMO) energy level of the resulting PDBFBT. Despite the fact that its thin films are less crystalline and have a rather disordered chain orientation in the crystalline domains, PDBFBT shows very high hole mobility up to 1.54 cm 2 V-1 s-1 in bottom-gate, top-contact organic thin film transistors.

Solution processable poly(2,5-dialkyl-2,5-dihydro-3,6-di-2-thienyl- pyrrolo[3,4-c]pyrrole-1,4-dione) for ambipolar organic thin film transistors

Solution processable diketopyrrolopyrrole (DPP)-bithiophene polymers (PDBT) with long branched alkyl side chains on the DPP unit are synthesized. These polymers have favourable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels for the injection and transport of both holes and electrons. Organic thin film transistors (OTFTs) using these polymers as semiconductors and gold as source/drain electrodes show typical ambipolar characteristics with very well balanced high hole and electron mobilities (μ h = 0.024 cm 2 V -1 s -1 and μ e = 0.056 cm 2 V -1 s -1). These simple and high-performing polymers are promising materials for ambipolar organic thin film transistors for low-cost CMOS-like logic circuits.

Excited-state dynamics in diketopyrrolopyrrole-based copolymer for organic photovoltaics investigated by transient optical spectroscopy

We investigate the photoexcited state dynamics in a donor-acceptor copolymer, poly{3,6-dithiophene-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]- pyrrole-1,4-dione-alt-naphthalene} (pDPP-TNT), by picosecond fluorescence and femtosecond transient absorption spectroscopies. Timeresolved fluorescence lifetime measurements of pDPP-TNT thin films reveal that the lifetime of the singlet excited state is 185 ± 5 ps and that singlet-singlet annihilation occurs at excitation photon densities above 6 × 1017 photons/cm3. From the results of singlet-singlet annihilation analysis, we estimate that the single-singlet annihilation rate constant is (6.0 ± 0.2) × 109cm3 s-1 and the singlet diffusion length is -7 nm. From the comparison of femtosecond transient absorption measurements and picosecond fluorescence measurements, it is found that the time profile of the photobleaching signal in the charge-transfer (CT) absorption band coincides with that of the fluorescence intensity and there is no indication of long-lived species, which clearly suggests that charged species, such as polaron pairs and triplet excitons, are not effectively photogenerated in the neat pDPP-TNT polymer.

Electron-accepting conjugated materials based on 2-Vinyl-4,5- dicyanoimidazoles for application in organic electronics

We report the Heck coupling of 2-vinyl-4,5-dicyanoimidazole (vinazene) with selected di- and trihalo aromatics in an effort to prepare linear and branched electron-accepting conjugated materials for application in organic electronics. By selecting the suitable halo-aromatic moiety, it is possible to tune the HOMO - LUMO energy levels, absorption, and emission properties for a specific application. In this regard, materials with strong photoluminescence from blue → green → red are reported that may have potential application in organic light-emitting diodes (OLEDs). Furthermore, derivatives with strong absorption in the visible spectrum, coupled with favorable HOMO-LUMO levels, have been used to prepare promising organic photovoltaic devices (OPVs) when combined with commercially available semiconducting donor polymers.

Electrical characteristics of lateral heterostructure organic field-effect bipolar transistors

We describe and discuss the unique electrical characteristics of an organic field-effect transistor in which the active layer consists of a type II lateral heterojunction located approximately midway between the source and drain. The two active semiconductors on either side of the junction transport only one carrier type each, with the other becoming trapped, which leads to devices that operate in only the steady state when there is balanced electron and hole injections from the drain and source. We describe the unique transfer characteristics of such devices in two material systems.

A furan-containing conjugated polymer for high mobility ambipolar organic thin film transistors

Furan substituted diketopyrrolopyrrole (DBF) combined with benzothiadiazole based polymer semiconductor PDPP-FBF has been synthesized and evaluated as an ambipolar semiconductor in organic thin-film transistors. Hole and electron mobilities as high as 0.20 cm 2 V -1 s -1 and 0.56 cm 2 V -1 s -1, respectively, are achieved for PDPP-FBF.

Synthesis, characterization and organic field effect transistor performance of a diketopyrrolopyrrole-fluorenone copolymer

A diketopyrrolopyrrole (DPP) with fluorenone (FN) based low band gap alternating copolymer (PDPPT-alt-FN) has been synthesized via Suzuki coupling. PDPPT-alt-FN exhibits a deep HOMO level with a lower band gap. Fabricated organic thin film transistors using PDPPT-alt-FN as a channel semiconductor show p-channel behaviour with the highest hole mobility of 0.083 cm2 V-1 s-1 measured in air.

A fluorenone based low band gap solution processable copolymer for air stable and high mobility organic field effect transistors

A fluorenone based alternating copolymer (PFN-DPPF) with a furan based fused aromatic moiety has been designed and synthesized. PFN-DPPF exhibits a small band gap with a lower HOMO value. Testing this polymer semiconductor as the active layer in organic thin-film transistors results in hole mobilities as high as 0.15 cm2 V-1 s-1 in air.

Organic non-fullerene acceptors for organic photovoltaics

Heterojunction organic photovoltaics have been the subject of intensive academic interest over the past two decades, and significant commercial efforts have been directed towards this area with the vision of developing the next generation of low-cost solar cells. Materials development has played a vital role in the dramatic improvement of organic solar cell performance in recent years, and this is driven primarily by the advancement of p-type semiconductors as donor materials. With the highest performing solar cells today dominated by acceptors based on members of the fullerene family, much less attention has been devoted to other classes of n-type acceptors. In this review, we will provide an overview of the progress in the synthesis, characterization and implementation of the various classes of non-fullerenebased n-type organic acceptors for photovoltaic applications.

Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives : novel acceptors for organic solar cells

Novel low bandgap solution processable diketopyrrolopyrrole (DPP) based derivatives functionalized with electron withdrawing end capping groups (trifluoromethylphenyl and trifluorophenyl) were synthesized, and their photophysical, electrochemical and photovoltaic properties were investigated. These compounds showed optical bandgaps ranging from 1.81 to 1.94 eV and intense absorption bands that cover a wide range from 300 to 700 nm, attributed to charge transfer transition between electron rich phenylene-thienylene moieties and the electron withdrawing diketopyrrolopyrrole core. All of the compounds were found to be fluorescent in solution with an emission wavelength ranging from 600 to 800 nm. Cyclic voltammetry indicated reversible oxidation and reduction processes with tuning of HOMO-LUMO energy levels. Bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor with these new acceptors were used for fabrication. The best power conversion efficiencies (PCE) using 1:2 donor-acceptor by weight mixture were 1% under simulated AM 1.5 solar irradiation of 100 mW cm-2. These findings suggested that a DPP core functionalized with electron accepting end-capping groups were a promising new class of solution processable low bandgap n-type organic semiconductors for organic solar cell applications.

Pyridine-incorporated dihexylquaterthiophene : a novel blue emitter for organic light emitting diodes (OLEDs)

The synthesis and characterisation of 2,5-bis(5′-hexyl-[2,2′- bithiophen]-5-yl)pyridine (Th4PY) and its use as a blue emitter in organic light emitting diodes (OLEDs) is reported. Th4PY was synthesised in high yield using a straightforward Suzuki coupling route with commercially available starting materials. As Th4PY is both soluble and has low molecular weight, blue OLEDs were fabricated using both spin-coating and vacuum deposition thin film processing techniques to study the effect of processing on device performance. OLED devices using a spin-coated layer consisting of 4′,4′′- tris(N-carbazolyl)triphenylamine (TCTA) and 2-(4-biphenylyl)-5-(4-tert- butylphenyl)-1,3,4-oxadiazole (PBD) as a host matrix together with Th4PY as emitter exhibited highly efficient sky-blue emission with a low turn-on voltage of 3V, a maximum brightness close to 15000cdm-2 at 8V, and a maximum luminous efficiency of 7.4cdA -1 (6.3lmW -1) with CIE coordinates of x≤0.212, y≤0.320. The device performance characteristics are compared using various matrices and processing techniques. The promising sky-blue OLED performance, solution processability, and ambient stability make Th4PY a promising blue emitter for application in OLEDs.

High mobility organic thin film transistor and efficient photovoltaic devices using versatile donor-acceptor polymer semiconductor by molecular design

In this work, we report a novel donor-acceptor based solution processable low band gap polymer semiconductor, PDPP-TNT, synthesized via Suzuki coupling using condensed diketopyrrolopyrrole (DPP) as an acceptor moiety with a fused naphthalene donor building block in the polymer backbone. This polymer exhibits p-channel charge transport characteristics when used as the active semiconductor in organic thin-film transistor (OTFT) devices. The hole mobilities of 0.65 cm2 V-1 s-1 and 0.98 cm2 V -1 s-1 are achieved respectively in bottom gate and dual gate OTFT devices with on/off ratios in the range of 105 to 10 7. Additionally, due to its appropriate HOMO (5.29 eV) energy level and optimum optical band gap (1.50 eV), PDPP-TNT is a promising candidate for organic photovoltaic (OPV) applications. When this polymer semiconductor is used as a donor and PC71BM as an acceptor in OPV devices, high power conversion efficiencies (PCE) of 4.7% are obtained. Such high mobility values in OTFTs and high PCE in OPV make PDPP-TNT a very promising polymer semiconductor for a wide range of applications in organic electronics.

A low-bandgap diketopyrrolopyrrole-benzothiadiazole-based copolymer for high-mobility ambipolar organic thin-film transistors

A new, solution-processable, low-bandgap, diketopyrrolopyrrole- benzothiadiazole-based, donor-acceptor polymer semiconductor (PDPP-TBT) is reported. This polymer exhibits ambipolar charge transport when used as a single component active semiconductor in OTFTs with balanced hole and electron mobilities of 0.35 cm2 V-1s-1 and 0.40 cm 2 V-1s-1, respectively. This polymer has the potential for ambipolar transistor-based complementary circuits in printed electronics.

High-mobility organic thin film transistors based on benzothiadiazole- sandwiched dihexylquaterthiophenes

We report here the synthesis, characterization, and organic thin-film transistor (OTFT) mobilities of 4,7-bis(5-(5-hexylthiophen-2-yl)thiophen-2-yl) benzo[1,2,5]thiadiazole (DH-BTZ-4T). DH-BTZ-4T was prepared in one high-yield step from commercially available materials using Suzuki chemistry and purified by column chromatography. OTFTs with hole mobilities of 0.17 cm2/(Vs) and on/off current ratios of 1 × 105 were prepared from DH-BTZ-4T active layers deposited by vacuum deposition. As DH-BTZ-4T is soluble in common solvents, solution processed devices were also prepared by spin coating yielding preliminary mobilities of 6.0 × 10-3 cm 2/(Vs). The promising mobilities and low band gap (1.90 eV) coupled with solution processability and ambient stability makes this material an excellent candidate for application in organic electronics.

Furan containing diketopyrrolopyrrole copolymers : synthesis, characterization, organic field effect transistor performance and photovoltaic properties

In this work, we report design, synthesis and characterization of solution processable low band gap polymer semiconductors, poly{3,6-difuran-2-yl-2,5-di(2- octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-phenylene} (PDPP-FPF), poly{3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1, 4-dione-alt-naphthalene} (PDPP-FNF) and poly{3,6-difuran-2-yl-2,5-di(2- octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-anthracene} (PDPP-FAF) using the furan-containing 3,6-di(furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DBF) building block. As DBF acts as an acceptor moiety, a series of donor-acceptor (D-A) copolymers can be generated when it is attached alternatively with phenylene, naphthalene or anthracene donor comonomer blocks. Optical and electrochemical characterization of thin films of these polymers reveals band gaps in the range of 1.55-1.64 eV. These polymers exhibit excellent hole mobility when used as the active layer in organic thin-film transistor (OTFT) devices. Among the series, the highest hole mobility of 0.11 cm 2 V -1 s -1 is achieved in bottom gate and top-contact OTFT devices using PDPP-FNF. When these polymers are used as a donor and [70]PCBM as the acceptor in organic photovoltaic (OPV) devices, power conversion efficiencies (PCE) of 2.5 and 2.6% are obtained for PDPP-FAF and PDPP-FNF polymers, respectively. Such mobility values in OTFTs and performance in OPV make furan-containing DBF a very promising block for designing new polymer semiconductors for a wide range of organic electronic applications.