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Preparation method and application of conjugated molecule based on fluoro-benzo-thiadiazole

A technology of benzothiadiazole and conjugated molecules is applied in the field of preparation of conjugated molecules, and can solve the problems of unstable structure, low light absorption rate and high cost

Inactive Publication Date: 2018-07-10
SHENZHEN SENIOR TECH MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the light absorption rate of the above-mentioned acceptor materials is low, the structure is unstable in thin film devices, and the cost is high, so we have to find and design new non-fullerene acceptor materials

Method used

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  • Preparation method and application of conjugated molecule based on fluoro-benzo-thiadiazole
  • Preparation method and application of conjugated molecule based on fluoro-benzo-thiadiazole
  • Preparation method and application of conjugated molecule based on fluoro-benzo-thiadiazole

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preparation example Construction

[0022] The embodiment of the present invention discloses a preparation method of a conjugated molecule based on fluorobenzothiadiazole, comprising the following steps: using toluene as a solvent, tetrakis(triphenylphosphine)palladium as a catalyst, and IDTT-2Sn and 2-((6-fluoro-7-ylbenzo[c][1,2,5]thiadiazole-4-yl)methylene)malononitrile is reacted at 90~110℃ to obtain Conjugated molecules of benzothiadiazoles. The reaction process is as follows:

[0023]

[0024] In the present invention, a fluorine atom is connected to the small molecule of benzothiadiazole to improve the overall electronegativity and electron mobility of the conjugated molecule, and enhance its absorption spectrum, which can be used as an acceptor material to prepare solar cell devices , for higher performance.

[0025] As a preferred version, the 2-((6-fluoro-7-ylbenzo[c][1,2,5]thiadiazole-4-yl)methylene)malononitrile is prepared according to the following method: Using basic alumina as a catalyst, re...

Embodiment 1

[0038] 5-fluoro-3-methyl-1,2-phenylenediamine

[0039] In a 250mL three-necked flask, add the initial raw material 4-fluoro-2methyl-1,6-nitroaniline (5g, 29.4mmol), add reduced iron powder (8.2g, 147mmol), and ethanol (50mL) as a solvent , after the addition is complete, perform pumping and ventilation, make the reaction under a nitrogen atmosphere, and then heat to reflux at 80°C. After the temperature reaches the set value, dilute 30.6mL hydrochloric acid (12molL-1) and 20mL ethanol solvent, and then slowly Drop into the reaction bottle, after the drop is completed, continue to heat the reaction under reflux for more than 5 hours, HCl will volatilize during the reaction, and treat the tail gas with aqueous sodium carbonate solution. After the reaction was completed, the reaction solution was poured into aqueous sodium hydroxide solution, stirred for 5 minutes, added ethyl acetate for extraction, allowed to stand for layers, poured out the upper liquid, then added anhydrous m...

Embodiment 2

[0055] Manufacturing process of polymer solar cell devices:

[0056]The device was fabricated by combining with the donor material DTBDT-TFBTz (structure as follows),

[0057]

[0058] The structure of the polymer solar cell device is ITO / PEDOT:PSS / active layer / PFN / Al. First, a 40nm-thick anode modification layer PEDOT:PSS was spin-coated on the ITO substrate after plasma treatment for 3 minutes, and annealed at 150°C for 20 minutes. Then, the acceptor material IDTT-fBT-2CN and the donor material DTBDT-TFBTz were blended (mixing ratio 1:1, wt / wt), using chloroform as a solvent, and then spin-coated on PEDOT:PSS as a photoactive layer, The thickness is about 80nm, and it is divided into 5 groups of samples, namely no annealing treatment, 80°C, 100°C, 120°C, 150°C annealing treatment, and the annealing time is 10min. PEDOT:PSS and active layer thickness were tested using Tencor Alpha-step 500 surface profiler. The cathode modification layer PFN was dissolved in methanol (0...

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Abstract

The invention provides a preparation method and an application of a conjugated molecule based on fluoro-benzo-thiadiazole. The preparation method includes the steps: taking methylbenzene as a solvent;taking tetra (triphenylphosphine) palladium as a catalyst; reacting IDTT-fBT (thiophene-fluorobenzothiadiazole) and 2-((6-fluoro-7-benzo[c] [1, 2 and 5] thiadiazole-4-radical) methylene) propane dinitrile at the temperature of 90-110 DEG C to the conjugated molecule based on the fluoro-benzo-thiadiazole. Compared with the prior art, the benzo-thiadiazole has suitable LUMO (lowest unoccupied molecular orbital) and HOMO (highest occupied molecular orbital) energy levels and excellent planarity, so that a conjugated structure of a molecule can be effectively expanded, a fluorine atom is introduced onto a benzene ring, the charge transfer rate in the molecule can be increased as the fluorine atom has high electronegativity, spectrums are absorbed by the fluorine atom, the conjugated moleculecan serve as a receptor material to prepare solar cell devices, and high performance is acquired.

Description

technical field [0001] The invention relates to the technical field of organic polymer solar cells, in particular to a preparation method and application of a fluorobenzothiadiazole-based conjugated molecule. Background technique [0002] Due to the increasingly serious energy problem, the contemporary demand for new sustainable energy is becoming more and more urgent. Current research mainly focuses on polymer solar cells (PSCs). Through decades of development, the energy conversion efficiency of polymer solar cells has reached more than 10% from less than 1% initially. However, due to limitations in efficiency, lifespan, and cost, it is still far from being widely used on a large scale. [0003] In polymer solar cells, traditional acceptor materials generally use C60 and its derivatives. In the prior art, C60 and its derivatives have been widely reported. For example, the Chinese patent literature with application number 200910089025.2 reports a class of acceptor materi...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/46
CPCC07D495/22H10K85/657H10K85/6576Y02E10/549
Inventor 严含陈勇陈秀峰
Owner SHENZHEN SENIOR TECH MATERIAL
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