A-D-A-D-A type organic micromolecular solar cell donor materials, and preparation method and application thereof

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: 2019-09-13
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology provides two types of materials that are used for making electronic devices like solar batteries. These different substances help make them work better by enhancing their ability to absorb light energy more efficiently than other forms of chemicals commonly found on silicon or gallium arsenide semiconductors.

Problems solved by technology

Technological Problem addressed by this patented technical problem described in the patents relates to developing efficient light emitting diodes for use in electronic applications due to the limitations associated with current methods involving chemical synthesis processes. Specifically, there currently exist challenges related to controlling the size distribution of small molecules containing donor components during production process while maintaining optimal properties over various wavelength ranges.

Method used

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  • A-D-A-D-A type organic micromolecular solar cell donor materials, and preparation method and application thereof
  • A-D-A-D-A type organic micromolecular solar cell donor materials, and preparation method and application thereof
  • A-D-A-D-A type organic micromolecular solar cell donor materials, and preparation method and application thereof

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 organic micromolecular donor materials adopting 2,1,3-benzoselenadiazole and 3-(dicyanomethylidene)indan-1-one as electron acceptor units and triphenylamine as an electron donorunit, a preparation method thereof, and an application of the organic micromolecular donor materials in organic solar cell devices. The organic micromolecular donor materials are characterized in that the 2,1,3-benzoselenadiazole and 3-(dicyanomethylidene)indan-1-one which are used as the electron acceptor units and the triphenylamine which is used as the electron donor unit form an A-D-A-D-A structure. Compared with a 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 materials in order to easily improvethe device performances of solar cells. The organic micromolecular donor materials of the present invention are blended with an acceptor material fullerene PC71BM to form an active layer in order to obtain the organic solar cell devices.

Description

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Claims

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Application Information

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Owner JIANGXI NORMAL UNIV
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