1351986-34-9

Usage

Uses

Used in Organic Electronics Industry:
2,5-Dihydro-2,5-bis(2-octyldodecyl)-3,6-bis[5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-thiophen-2-yl]pyrrolo[3,4-c]pyrrol-1,4-dione is used as a key component in the development of highly efficient and durable organic electronic devices. Its tailored electronic properties, high stability, and potential for straightforward chemical modification contribute to the creation of advanced materials that can be used in various electronic applications, such as organic solar cells, organic light-emitting diodes (OLEDs), and organic field-effect transistors (OFETs). These devices benefit from the compound's ability to enhance performance, improve durability, and enable new functionalities.

Upstream product

• 5333-42-6 2-octyldodecan-1-ol 
• 69620-20-8 9-(bromomethyl)nonadecane 
• 1267540-02-2 2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Selenium in diketopyrrolopyrrole-based polymers: Influence on electronic properties and charge carrier mobilities

Diketopyrrolopyrrole (DPP)-based π-conjugated copolymers with thiophene have exceptionally high electron mobilities. This paper investigates electronic properties and charge carrier mobilities of selenophene containing analogues. Two new copolymers, with

Alcohol-Soluble n-Type Conjugated Polyelectrolyte as Electron Transport Layer for Polymer Solar Cells

(Chemical Presented). A novel alcohol-soluble n-type conjugated polyelectrolyte (n-CPE) poly-2,5-bis(2-octyldodecyl)-3,6-bis(thiophen-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-2,5-bis[6-(N,N,N-trimethylammonium)hexyl]-3,6-bis(thiophen-2-yl)-pyrrolo[3,4-c]pyrrole-1,4-dione (PDPPNBr) is synthesized for applications as an electron transport layer (ETL) in an inverted polymer solar cells (PSCs) device. Because of the electron-deficient nature of diketopyrrolopyrrole (DPP) backbone and its planar structure, PDPPNBr is endowed with high conductivity and electron mobility. The interfacial dipole moment created by n-CPE PDPPNBr can substantially reduce the work function of ITO and induce a better energy alignment in the device, facilitating electron extraction and decreasing exctions recombination at active layer/cathode interface. As a result, the power conversion efficiency (PCE) of the inverted devices based poly(3-hexylthiophene) (P3HT):(6,6)-phenyl-C61 butyric acid methyl ester (PC61BM) active layer with PDPPNBr as ETL achieves a value of 4.03%, with 25% improvement than that of the control device with ZnO ETL. Moreover, the universal PDPPNBr ETL also delivers a notable PCE of 8.02% in the devices based on polythieno[3,4-b]-thiophene-co-benzodithiophene (PTB7):(6,6)-phenyl-C71-butyric acid methyl ester (PC71BM). To our best knowledge, this is the first time that n-type conjugated polyelectrolyte-based cathode interlayer is reported. Quite different from the traditional p-type conjugated and nonconjugated polyelectrolytes ETLs, n-CPE PDPPNBr as ETL could function efficiently with a thickness approximate 30 nm because of the high conductivity and electron mobility. Furthermore, the PDPPNBr interlayer also can ensure the device with the improved long-term stability. The successful application of this alcohol solution processed n-type conjugated polyelectrolyte indicates that the electron-deficient planar structure with high electron mobility could be very promising in developing high performance and environmentally friendly polymer solar cells.

An ultra-low bandgap diketopyrrolopyrrole (DPP)-based polymer with balanced ambipolar charge transport for organic field-effect transistors

A new A1-A2 type polymer pDTDPP-TTF containing diketopyrrolopyrrole (DPP) and 2-ethylhexyl-3-fluorothieno[3,4-b]thiophene-2-carboxylate (TTF) as the main electron-accepting building blocks has been synthesized via Suzuki cross-coupling polycondensation. The introduction of TTF as an additional electron-deficient unit significantly lowers the LUMO energy level of this DPP containing polymer to -4.37 eV which is beneficial for efficient electron injection and transport. The pDTDPP-TTF polymer shows an ultra narrow optical bandgap of 1.06 eV with a broad absorption spectra covering the visible to near infrared region of up to 1300 nm. Solution-processed OFET devices with pDTDPP-TTF as the active semiconducting layer have been fabricated with the configurations of both bottom-gate bottom-contact (BG-BC) and top-gate bottom-contact (TG-BC). The BG-BC devices with SiO2 as a dielectric exhibit ambipolar behavior with a hole and electron mobility of 1.85 × 10-4 and 3.55 × 10-5 cm2 V-1 s-1, respectively. Improved OFET performance has been achieved in TG-BC devices by using PMMA as the dielectric; balanced ambipolar charge transport is obtained with a hole and electron mobility of 6.17 × 10-3 cm2 V-1 s-1 and 3.13 × 10-3 cm2 V-1 s-1, respectively. To the best of our knowledge, our work is among the very few examples of ultra-low bandgap semiconducting polymers with balanced ambipolar charge transport properties.

A diketopyrrolopyrrole-thiazolothiazole copolymer for high performance organic field-effect transistors

A diketopyrrolopyrrole-thiazolothiazole copolymer with a short π-π stacking distance (3.52 ), due to the introduction of heteroaromatic rings, exhibits a high charge mobility above 3.40 cm2 V-1 s -1 at a relatively gentle annealing temperature. The Royal Society of Chemistry 2013.

Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications

A series of copolymers containing the benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) unit has been designed and synthesised with bisthienyl-diketopyrrolopyrrole (DPP), dithienopyrrole (DTP), benzothiadiazole (BT), benzodithiophene (BDT) or 4,4′-dialkoxybithiazole (BTz) comonomers. The resulting polymers possess a conjugation pathway that is orthogonal to the more usual substitution pathway through the 2,6-positions of the BBT unit, facilitating intramolecular non-covalent interactions between strategically placed heteroatoms of neighbouring monomer units. Such interactions enable a control over the degree of planarity through altering their number and strength, in turn allowing for tuning of the band gap. The resulting 4,8-BBT materials gave enhanced mobility in p-type organic field-effect transistors of up to 2.16 × 10-2 cm2 V-1 s-1 for pDPP2ThBBT and good solar cell performance of up to 4.45% power conversion efficiency for pBT2ThBBT.

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: What did we find out?

The primary role of substituted side chains in organic semiconductors is to increase their solubility in common organic solvents. In the recent past, many literature reports have suggested that the side chains play a critical role in molecular packing and strongly impact the charge transport properties of conjugated polymers. In this work, we have investigated the influence of side-chains on the charge transport behavior of a novel class of diketopyrrolopyrrole (DPP) based alternating copolymers. To investigate the role of side-chains, we prepared four diketopyrrolopyrrole-diketopyrrolopyrrole (DPP-DPP) conjugated polymers with varied side-chains and carried out a systematic study of thin film microstructure and charge transport properties in polymer thin-film transistors (PTFTs). Combining results obtained from grazing incidence X-ray diffraction (GIXD) and charge transport properties in PTFTs, we conclude side-chains have a strong influence on molecular packing, thin film microstructure, and the charge carrier mobility of DPP-DPP copolymers. However, the influence of side-chains on optical properties was moderate. The preferential "edge-on" packing and dominant n-channel behavior with exceptionally high field-effect electron mobility values of >1 cm2 V-1 s-1 were observed by incorporating hydrophilic (triethylene glycol) and hydrophobic side-chains of alternate DPP units. In contrast, moderate electron and hole mobilities were observed by incorporation of branched hydrophobic side-chains. This work clearly demonstrates that the subtle balance between hydrophobicity and hydrophilicity induced by side-chains is a powerful strategy to alter the molecular packing and improve the ambipolar charge transport properties in DPP-DPP based conjugated polymers. Theoretical analysis supports the conclusion that the side-chains influence polymer properties through morphology changes, as there is no effect on the electronic properties in the gas phase. The exceptional electron mobility is at least partially a result of the strong intramolecular conjugation of the donor and acceptor as evidenced by the unusually wide conduction band of the polymer. the Partner Organisations 2014.

A highly crystalline low band-gap polymer consisting of perylene and diketopyrrolopyrrole for organic photovoltaic cells

A new, low band-gap donor-acceptor-type conjugated polymer, PDPP-PER, comprising 3,9-perylene (PER) and diketopyrrolo[3,4-c]pyrrole (DPP) was synthesized. The crystallinity of the synthesized polymer film significantly improved with thermal annealing to 150°C. The PCE of the PDPP-PER device reached 6.35% with a high open-circuit voltage of 0.79 V.

Incorporation of fused tetrathiafulvalene units in a DPP-terthiophene copolymer for air stable solution processable organic field effect transistors

A new terthiophene-diketopyrrolopyrrole (DPP) copolymer has been synthesised in which the central thiophene ring within the terthiophene repeat unit is attached to a fused tetrathiafulvalene (TTF). The electrochemical and absorption data of the polymer, p(DPP-TTF), are presented, and the multi-redox states are investigated by UV-vis spectroelectrochemistry. Bottom gate/bottom contact field effect transistors were fabricated from films of p(DPP-TTF) annealed at 200 °C. The material, which under these conditions forms a fibrous structure, exhibited hole mobilities of 4 ± 2 × 10 -2 cm2 V-1 s-1 with an on/off ratio of 1 × 104. The transistors showed little sign of degradation over 15 days of exposure under ambient conditions, demonstrating excellent air-stability. This characteristic is attributed to the incorporation of the TTF unit into the polymer.