501434-74-8

Usage

Uses

Used in Organic Electronics:
2,1,3-Benzothiadiazole, 4-bromo-7-(2-thienyl)is used as a component in organic semiconductor materials for its unique structural features and electronic properties. It contributes to the efficient performance of devices in this industry.
Used in Organic Photovoltaics:
In the field of organic photovoltaics, 2,1,3-Benzothiadiazole, 4-bromo-7-(2-thienyl)is used as a material to enhance the efficiency of solar cells, capitalizing on its high electron affinity and charge transport capabilities.
Used in Organic Light-Emitting Diodes (OLEDs):
2,1,3-Benzothiadiazole, 4-bromo-7-(2-thienyl)is utilized as a component in the development of organic light-emitting diodes, where its electronic properties aid in the creation of efficient and high-performing OLED devices.
Used in Other Optoelectronic Devices and Materials:
Beyond organic electronics, photovoltaics, and OLEDs, 2,1,3-Benzothiadiazole, 4-bromo-7-(2-thienyl)has been investigated for its potential use in a variety of other optoelectronic devices and materials, showing promise for future applications in this broad field.

Upstream product

• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 6165-68-0 thiophene boronic acid 

Downstream Products

• 1278585-90-2 4-[4-(1,2,2-triphenylvinyl)phenyl]-7-{5-[4-(1,2,2-triphenylvinyl)phenyl]-2-thienyl}-2,1,3-benzothiadiazole 
• 1542150-50-4 C₅₄H₄₅BF₂N₆O₆S₆ 

Relevant academic research and scientific papers

Molecular engineering of conjugated polymers for solar cells and field-effect transistors: Side-chain versus main-chain electron acceptors

Two model polymers, containing fluorene as an electron-donating moiety and benzothiadiazole (BT) as an electron-accepting moiety, have been synthesized by Suzuki coupling reaction. Both polymers are composed of the same chemical composition, but the BT acceptor can be either at a side-chain (i.e., S-polymer) or along the polymer main chain (i.e., M-polymer). Their optical, electrochemical, and photovoltaic properties, together with the field-effect transistor (FET) characteristics, have been investigated experimentally and theoretically. The FET carrier mobilities were estimated to be 5.20 × 10-5 and 3.12 × 10-4 cm2 V-1 s-1 for the S-polymer and M-polymer, respectively. Furthermore, polymeric solar cells (PSCs) with the ITO/PEDOT:PSS/S-polymer or M-polymer:PC71BM(1:4)/Al structure were constructed and demonstrated to show a power conversion efficiency of 0.82 and 1.24% for the S-polymer and M-polymer, respectively. The observed superior device performances for the M-polymer in both FET and PSCs are attributable to its relatively low band-gap and close molecular packing for efficient solar light harvesting and charge transport. This study provides important insights into the design of ideal structure-property relationships for conjugate polymers in FETs and PSCs.

A facile method to synthesize [A'(D'AD)2]-based push-pull small molecules for organic photovoltaics

An efficient route to synthesize, for the first time, a series of small molecules based on the [A'(D'AD)2] architecture was developed using selective direct heteroarylation of the C-H bond with a Pd(AcO)2/Bu4NBr simple catalytic system. The C-H arylation of the unsymmetrical compound 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(thiophen-2-yl)benzo[c][1,2,5] thiadiazole (5) showed that the (C5) in the ethyldioxythiophene moiety is more reactive towards C-H arylation than its counterpart in the thiophene unit. The new small molecules bear two different acceptors and/or donors, which led to decrease the electron band gap and improve the strength of the push-pull system as well as the amount of intramolecular charge transfer from donor to acceptor units. Lactams and imide containing acceptors are used as second electron withdrawing units due to their well conjugated structures, strong π-π interactions and high electron affinity as well as their potential as electron withdrawing units in photovoltaic conjugated materials. All small molecules showed broad absorption spectra with optical band gaps, which were estimated to be in the range of 1.72-1.29 eV. From cyclic voltammetry, the highest occupied molecular orbital (HOMO) energy level could be tuned by changing the second acceptor, suggesting high open circuit voltage (Voc). The EHID(EDBTT)2:PC71BM-based solar cells reached a maximum PCE of 3.24%.

Design of (X-DADAD)n type copolymers for efficient bulk heterojunction organic solar cells

We show that extended TBTBT structure (T = thiophene, B = benzothiadiazole) can be used as an electron-deficient building block for designing conjugated polymers with deeply lying HOMO energy levels and narrow band gaps. The first carbazole-TBTBT copolymer P2 demonstrated power conversion efficiencies exceeding 6% in bulk heterojunction solar cells in combination with advanced operational stability, unlike conventional donor polymers such as PTB7, PBDTTT-CF, etc.

Synthesis and properties of new benzothiadiazole-based push-pull dyes for p-type dye sensitized solar cells

We report the synthesis of three new push-pull dyes specially designed for the sensitization of mesoporous p type semi-conductor NiO for the construction of p type dye sensitized solar cells (pDSC). Their structure stems from the conjugation of the well-k

Low molecular weight organic compound having electron donor and acceptor and preparation method of the same, organic photoelectric device comprising the same

The present invention relates to a low molecular weight organic compound having an electron donor-acceptor introduced thereto, a method for preparing the same, and an organic photoelectric device comprising the same. The present invention provides a novel low molecular weight organic compound having an electron donor-acceptor represented by chemical formula 1. According to the present invention, it is possible to prepare a low molecular weight organic compound including a structure of [Aandprime;(Dandprime;AD)2] having a strong push-pull donor-acceptor system under the system of Pd(OAc)_2/Bu_4NBr catalyst with ease. When the low molecular weight organic compound having a structure of [Aandprime;(Dandprime;AD)2] is used for an active layer of an organic photoelectric device, it is possible to provide high intramolecular charge transportability (ICT) and high short current (Jsc).COPYRIGHT KIPO 2017

A strong influence of the positions of solubilizing alkyl side chains on optoelectronic and photovoltaic properties of TTBTBTT-based conjugated polymers

We report the synthesis and comparative study of five conjugated polymers P1-P5 with different arrangements of two solubilizing 2-ethylhexyl side chains in their repeating units. It has been shown that positioning of the alkyl substituents affects strongly frontier energy levels of the polymers and results in variation of their optical band gaps between 1.65 and 2.0 eV. The highest (2.8 × 10-4 cm2 V-1 s-1) and the lowest (2.4 × 10-5 cm2 V-1 s-1) charge carrier mobilities determined for the polymers P1 and P5, respectively, using a SCLC technique differ by more than one order of magnitude. GIWAXS measurements also revealed very different degrees of molecular ordering in the films of polymers P1-P5 which correlate well with the SCLC mobility data and solid state photoluminescence spectra of these materials. The bulk heterojunction solar cells based on the composites of polymers P1-P5 with [60]PCBM demonstrated power conversion efficiencies ranging from 0.6% (P5) to 5.1% (P1) thus evidencing a strong influence of the alkyl side chains on the photovoltaic performance of the designed polymer-based materials.

Phenothiazine derivatives-based D-π-A and D-A-π-A organic dyes for dye-sensitized solar cells

D-π-A and D-A-π-A-structured organic dyes represent different developmental directions of photosensitizers in dye-sensitized solar cells (DSSCs). In this work, two phenothiazine derivatives-based D-π-A and D-A-π-A-structured organic dyes have been synthesized and applied in DSSCs. The physical and electrochemical properties of both dyes have been investigated systematically. The results show that the D-A-π-A-structured dye exhibits a broader spectrum response but lower molar coefficient of extinction when compared to the D-π-A-structured dye. Regarding photovoltaic performance, the D-π-A-structured dye yields a higher efficiency (η) of 7.5% with a higher short-circuit current density (Jsc) of 16.36 mA cm -2 and open-circuit voltage (Voc) of 706 mV than that of the D-A-π-A-structured dye. Incident photon-to-electron conversion efficiency (IPCE) studies and impedance analysis also support these results. These results demonstrate that the phenothiazine derivatives-based D-π-A-structured organic dyes can compete with, and even exceed, D-A-π-A-structured organic dyes under the same test conditions. The Royal Society of Chemistry 2014.

Full emission color tuning in luminogens constructed from tetraphenylethene, benzo-2,1,3-thiadiazole and thiophene building blocks

Full color luminogens are constructed from tetraphenylethene, benzo-2,1,3-thiadiazole and thiophene building blocks. OLED fabricated using one of the luminogens exhibits orange-red electroluminescence with high luminance and efficiencies of 8330 cd m

CONJUGATED POLYMERS CONTAINING SPIROBIFLUORENE UNITS AND THE USE THEREOF

The present invention relates to novel conjugated polymers comprising spirobifluorene units and their use in optoelectronic devices, preferably in, for example, displays based on polymeric organic light-emitting diodes.