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A-D-A type organic small molecular receptor containing thienocarbazole seven-membered condensed ring and preparation method thereof

A technology of small molecule receptors and carbazoles, which is applied in the field of organic small molecule receptor materials and their preparation, can solve the problems that n-type organic small molecule receptor materials have not been reported, and achieve the availability and popularization of raw materials High, synthetically simple effects

Inactive Publication Date: 2017-06-13
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although p-type DTCC derivative units are widely used to synthesize high-performance p-type polymer semiconductor materials, DTCC-based n-type organic small molecule acceptor materials are still not reported.

Method used

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  • A-D-A type organic small molecular receptor containing thienocarbazole seven-membered condensed ring and preparation method thereof
  • A-D-A type organic small molecular receptor containing thienocarbazole seven-membered condensed ring and preparation method thereof
  • A-D-A type organic small molecular receptor containing thienocarbazole seven-membered condensed ring and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A kind of organic small molecule acceptor whose chemical structural formula is DTCC-IC, its synthetic route is as follows:

[0054]

[0055] (1) The chemical structural formula is the synthesis of the intermediate of a: with (2.7g, 5.1mmol) carbazole borate ester, (3.7g, 15.3mmol) thiophene ester halogenated compound, (13.8g, 100.0mmol) anhydrous K 2 CO 3 , an appropriate amount of water, 2 drops of tetrabutylammonium bromide, 0.5g of palladium catalyst, and 100mL of toluene were added to the reaction flask. Protected under nitrogen, protected from light, reacted at 100°C for 24 hours. Cool to room temperature, extract with dichloromethane and water, anhydrous MgSO 4 Dried, spin-dried and passed through the column to obtain a yellow solid, namely intermediate a, with a yield of 75%. 1 H NMR (400MHz, CDCl 3 ),δ(ppm):8.08–8.10(d,2H),7.54–7.56(m,4H),7.36–7.38(dd,2H),7.27–7.28(d,2H),4.30(t,2H), 4.17–4.22(m,4H),1.85–1.91(m,2H),1.23–1.42(m,10H),1.12–1.16(t,3H),0.82–0....

Embodiment 2

[0060] The synthetic route of the small organic molecule receptor whose chemical structural formula is DTCC8-IC is as follows:

[0061]

[0062] (1) chemical structural formula is the synthesis of the intermediate of a with embodiment 1

[0063] (2) Synthesis of an intermediate whose chemical structural formula is e: with (0.6g, 25mmol) magnesium chips, an appropriate amount of elemental iodine as a catalyst, (5.0g, 18.6mmol) p-bromooctylbenzene, 120mL THF, join the reaction flask middle. Under nitrogen protection, it was initiated at 100°C. After reacting at this temperature for 12 hours, (1.5 g, 2.6 mmol) THF solution of intermediate a was added into the reaction system at room temperature, and then the temperature was raised to 110° C. and stirred for 12 hours. Cool to room temperature, extract with dichloromethane and water, wash over anhydrous MgSO 4 After being dried and spin-dried through the column, 100 mL of acetic acid was added, and stirred at 100° C. for 6 ho...

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Abstract

The invention discloses an A-D-A type organic small molecular receptor containing thienocarbazole seven-membered condensed ring (DTCC) as well as a preparation method and application thereof. The structural formula of the small molecular receptor is as shown in I. An intermediate and a synthetic route of a target organic small molecular receptor provided by the invention have the advantages of being simple and efficient, low in price of raw materials, easily available in raw material, high in universality, good in repeatability and the like, and can be popularized and applied to synthesizing various DTCC-based A-D-A type organic small molecular receptors. The organic small molecular receptor has the advantages of being stable in structure, universe and easily available in raw material and relatively low in production cost. The organic small molecular receptor for preparing a non-fullerene polymer solar battery can obtain the energy conversion efficiency of about 4.8-6%, so that an excellent potential of the small molecular receptor applied to the organic solar battery is fully exhibited, and the receptor has certain actual application value.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials, and relates to an organic small molecule acceptor material for organic solar cells and a preparation method thereof. Background technique [0002] Solar energy has the characteristics of inexhaustibility, inexhaustibility, and no space limitation. It is a kind of renewable energy with the most development potential. In recent years, organic solar cells (Organic Solar Cells, OSCs) have attracted much attention due to their advantages of light weight, flexibility, low cost, and large-area processing by solution method. Among them, bulk heterojunction organic solar cells have achieved rapid development. Currently, the power conversion efficiency (PCE) of single-junction OSCs devices based on fullerene-derived acceptors exceeds 10%. However, fullerene-derived receptors have some essential defects, such as weak light-harvesting ability in the visible region, difficulties in synthesis a...

Claims

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Application Information

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IPC IPC(8): C07D495/14H01L51/42H01L51/46
CPCC07D495/14H10K85/657H10K30/00Y02E10/549
Inventor 陈华杰曹群芳蔡国胜郑丽萍
Owner XIANGTAN UNIV
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