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a-d-a-d-a type organic small molecule solar cell donor material and its preparation method and application

An organic solvent, volume ratio technology, applied in organic chemistry, electrical solid devices, semiconductor/solid device manufacturing, etc., can solve problems such as device performance impact, analysis, unfavorable structure, etc., to improve device performance, enhance charge transfer, broaden The effect of absorption bands

Active Publication Date: 2020-07-31
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because the degree of polymerization of polymers is difficult to control, not only is it not conducive to the analysis of its structure, but also different degrees of polymerization will affect the performance of the device, resulting in differences in the performance of solar cells with the degree of polymerization of polymers.

Method used

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  • a-d-a-d-a type organic small molecule solar cell donor material and its preparation method and application
  • a-d-a-d-a type organic small molecule solar cell donor material and its preparation method and application
  • a-d-a-d-a type organic small molecule solar cell donor material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 3-(dicyanomethylene)indoketone

[0037]

[0038] Add 1,3-indandione (2.193g, 15mmol) into a 100ml round bottom flask, add sodium acetate (1.599g, 19.5mmol), 30ml of absolute ethanol in turn, add malononitrile (1.981g, 30mmol) Finally, quickly seal the bottle mouth with a drying tube. At this time, the solution in the bottle turns red. After reacting at room temperature for 40 minutes, pour the reaction solution into water, add hydrochloric acid to adjust the pH, add hydrochloric acid dropwise until the solution turns gray, and filter with suction. The filter residue was washed with a large amount of water, and then recrystallized with acetic acid to obtain light red needle-like crystals (2.132g, 10.98mmol, 73.2%). This light red acicular crystal is 3-(dicyano methylene) indoketone, and its nuclear magnetic resonance experiment data is as follows:

[0039] 1 H NMR (400MHz, CDCl 3 )δ8.70–8.63 (m, 1H), 8.00 (d, J=7.5Hz, 1H), 7.95–7.83 (m, 2H), 3.74 (d, J...

Embodiment 2

[0041] Synthesis of 4-{phenyl[4-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)phenyl]amino}benzaldehyde

[0042]

[0043] (1) Synthesis of 4-[-(4-bromophenyl)amino]benzaldehyde

[0044]

[0045] Add 4-bromo-triphenylamine (3.849g, 11.87mmol) into a 100ml three-neck round-bottomed flask, pass nitrogen gas, add anhydrous DMF (12ml, 152mmol) under nitrogen protection to dissolve, cool to 0°C, add trichloroxy Phosphorus (4.33ml, 29mmol) was reacted for 1 hour, heated to 50°C for 12 hours, stopped the reaction, cooled to room temperature, poured the reaction solution into ice water, adjusted the pH to neutral with saturated NaOH aqueous solution, and then raised the temperature to 70°C for reaction 1h, stop the reaction, cool to room temperature, filter with suction, dissolve the filter cake with dichloromethane, then extract with ethyl acetate and water, combine the organic phases, wash the organic phase with water, dry overnight with anhydrous magnesium sulfate, filter the s...

Embodiment 3

[0052] Synthesis of IND-TPA-Th-BSe

[0053]

[0054] (1) 4,4-((([2,1,3]-benzoselenadiazole-4,7-substituent bis(4-dodecylthiophene-5,2-substituent))bis( Synthesis of 4,1-phenylene))bis(aniline)benzaldehyde

[0055]

[0056] 4,7-(3-dodecylthiophen-2-yl)-2,1,3-dibenzoselenodiazol (1.023g, 1.22mmol) and 4-{phenyl[4-(4, 4,5,5-Tetramethyl-1,2,3-dioxaborolan-2-yl)phenyl]amino}benzaldehyde (1.456g, 3.65mmol) was added to a 100ml three-neck round bottom flask, and 10ml absolute ethanol, add 10ml 2M K 2 CO 3 Aqueous solution, add 50ml of toluene to dissolve, pass nitrogen, add tetrakis triphenylphosphine palladium (70mg, 0.061mmol) under the protection of nitrogen, continue to pass nitrogen for 30min, heat up to 80°C under nitrogen protection and reflux for 24h, stop the reaction, cool To room temperature, the solution was poured into water, extracted with dichloromethane, the organic phases were combined, washed with water, dried overnight with anhydrous magnesium sulfate, th...

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Abstract

The invention provides a class of organic small molecule donors with 2,1,3-benzoselenodiazole and 3-(dicyanomethylene) indoketone as electron acceptor units and triphenylamine as electron donor units. Bulk materials, their preparation methods, and their applications in organic solar cell devices. The organic small molecule donor material of the present invention uses 2,1,3-benzoselenadiazole and 3-(dicyanomethylene) indoketone as the electron acceptor unit, and triphenylamine as the electron donor unit, Form an A‑D‑A‑D‑A structure. Compared with the D‑A‑D structure, the A‑D‑A‑D‑A structure can effectively enhance the intramolecular charge transfer and broaden the absorption band of the material, which is conducive to improving the device performance of solar cells. With the organic small molecule donor material and acceptor material fullerene PC of the present invention 71 BM blended as the active layer, organic solar cell devices can be obtained.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to an A-D-A-D-A type organic small molecule solar cell donor material and its preparation method and application. Background technique [0002] In 1995, Heeger et al. made a breakthrough in the field of organic solar cell devices and proposed the concept of bulk heterojunction solar cells (Science, 1995, 270, 1789). The active layer of a bulk heterojunction organic solar cell includes a donor material and an acceptor material, wherein the donor material can be divided into a small molecule donor material and a polymer donor material. In recent years, organic polymer donor materials based on the D-A structure have developed rapidly, and people have systematically studied their band gap, energy level, carrier mobility and molecular planarity (Chemical Reviews, 2007, 38, 1324 ; Chemical Society Reviews, 2015, 44, 1113). Recently, a major breakthrough has been made in the e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D421/14H01L51/46
CPCC07D421/14H10K85/615H10K85/631H10K85/655H10K85/657Y02E10/549
Inventor 梁爱辉周文静张家雨胡斯帆谢琪刘志谦
Owner JIANGXI NORMAL UNIV
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