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Receptor material based on di(bithiophene)six-membered heterocycle as well as preparation method and application of receptor material

A six-membered heterocycle and dithiophene technology, which is applied in the field of organic photovoltaic materials, can solve the problems of poor electron donating ability and light absorption ability, and achieve the effects of good thermal stability, broadened absorption spectrum, and strong light absorption ability

Active Publication Date: 2020-04-17
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved in the present invention is: in order to solve the technical problem of poor electron-donating ability and light-absorbing ability existing in the existing non-fullerene acceptor materials, the application provides a kind of based on bis(dithiophene) and hexa-membered Heterocyclic acceptor material and its preparation method and application

Method used

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  • Receptor material based on di(bithiophene)six-membered heterocycle as well as preparation method and application of receptor material
  • Receptor material based on di(bithiophene)six-membered heterocycle as well as preparation method and application of receptor material
  • Receptor material based on di(bithiophene)six-membered heterocycle as well as preparation method and application of receptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) Preparation of compound 2

[0057] Weigh compound 1 (740mg, 2.97mmol) in 100mL Schlenk, vacuum dry for 0.5h, change argon 3 times during this period, add 10mL of anhydrous Et 2 O dissolved. The freshly prepared LDA (3.56mmol) was placed in a -78°C cryostat, TMSCl (0.6mL, 6.53mmol) was dropped into the LDA, stirred for 10min, the solution of compound 1 was added dropwise, and the reaction was allowed to rise to room temperature overnight. Add CH dropwise at low temperature (-90℃~-60℃) 3 The reaction was quenched with OH, the solvent was spin-dried, extracted with DCM, dried, filtered and spin-dried to obtain a crude product. 300-400 mesh silica gel column chromatography, using HEX as eluent, obtained 791 mg of compound 3 with a yield of 83%.

[0058]

[0059] Characterization data of compound formula 2: 1 H NMR (300MHz, CDCl 3 )δ7.20(s,1H),4.13(s,3H),0.37(s,9H). 13 C NMR (75MHz, CDCl 3 )δ148.09, 142.68, 137.98, 133.22, 126.02, 95.25, 77.67, 77.25, 76.82, 59...

Embodiment 2

[0085] (1) Preparation of compound 8-1: the method is the same as in Example 1;

[0086] (2) Preparation of compound 9-2:

[0087] Weigh compound formula 8-1 (77mg, 0.0617mmol) and bisfluorocyanindanone (57mg, 0.25mmol) into 50mL Schlenk, vacuum dry for 0.5h, change argon 3 times during this period, add 6mL of anhydrous CHCl 3 And 0.2mL pyridine, react overnight at room temperature. Add CH to the reaction solution 3 OH, until a large amount of blue solids are precipitated, and the solids are washed with CH 3 OH washed several times, 300-400 mesh silica gel column chromatography, HEX:CHCl 3 =1:2 was the eluent, and 76 mg of compound 9-2 was obtained with a yield of 74%.

[0088]

[0089] Characterization data of compound formula 9-2: 1 H NMR (400MHz, CDCl 3 )δ8.96(d, J=10.1Hz, 2H), 8.45-8.32(m, 2H), 7.62(dt, J=10.9, 7.6Hz, 2H), 7.53(d, J=7.9Hz, 4H), 7.33(d, J=8.0Hz, 4H), 6.98(s, 1H), 6.68(s, 1H), 4.34(t, J=7.2Hz, 2H), 4.23(t, J=7.0Hz, 2H), 4.11(t, J=7.0Hz, 2H), 3.87...

Embodiment 3

[0091] (1) Preparation of compound 7-1: the method is the same as in Example 1;

[0092] (2) Preparation of compound 8-2:

[0093] Weigh compound 7-1 (115mg, 0.13mmol), 5-bromo-3-hexyloxythiophene-2-carbaldehyde (84mg, 0.2879mmol), K 2 CO 3 (90mg, 0.654mmol) and Pd(PPh 3 ) 4 (8mg, 0.0065mmol) in 100mL Schlenk, vacuum-dry for 0.5h, change argon 3 times during this period, add 10mL of anhydrous THF and 5mL of oxygen-free water, transfer to 90°C oil bath and reflux overnight. The solvent was spin-dried, extracted with DCM, dried, filtered and spin-dried to obtain a crude product. 300-400 mesh silica gel column chromatography with DCM as the eluent gave 104.8 mg of compound 8-2 with a yield of 77%.

[0094]

[0095] Characterization data of compound formula 8-2: HRMS (DART) calcd for [C 71 h 91 o 7 S 6 ] 1046.3234, found 1047.33073.

[0096] (3) Preparation of compound formula 9-3:

[0097] Weigh compound formula 8-2 (65mg, 0.064mmol) and cyanoindanone (50mg, 0.26mmo...

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Abstract

The invention relates to an acceptor material based on a di(bithiophene)six-membered heterocycle as well as a preparation method and an application of the acceptor material. According to the small molecule acceptor material, an asymmetric five-membered fused ring structure composed of two fused dithiophenes and a six-membered ring containing an oxygen group heteroatom is used as a parent nucleus;conjugated groups are introduced into the two sides of the parent nucleus to serve as pi bridges, electron withdrawing terminal groups which are connected with the pi bridge and have specific structures are designed on the two sides of the parent nucleus; finally, a series of brand-new A-D-A type small molecule receptor materials with good solubility and good thermal stability are formed; the parent nucleus of the acceptor material has strong electron donating capability, the pi bridge effectively prolongs the conjugate length of the molecule; the terminal electron withdrawing group A can effectively adjust the lowest unoccupied molecular orbital (LUMO) energy level of molecules, widens the absorption spectrum of the material, reduces the optical band gap of the material, and enhances theintermolecular charge transfer ability, thereby enhancing the photocurrent, and is especially suitable for preparing solar cells with high short-circuit current and high energy conversion efficiency.

Description

technical field [0001] The invention relates to an acceptor material based on a bis(dithiophene)hexa-membered heterocycle, a preparation method and application thereof, and belongs to the technical field of organic photovoltaic materials. Background technique [0002] In order to alleviate the pressure brought by the current energy crisis, countries around the world have widely attached importance to the utilization of clean energy, among which solar energy is feasible to meet global energy demand. As a widely used technology, solar cells are expected to solve the energy crisis and environmental pollution problems caused by large-scale production and consumption of fossil fuels in the long term. Organic solar cells have unique advantages such as low cost, light weight, good flexibility, translucency, adjustable color, and large-area printing preparation, which have attracted widespread attention from academia and industry. [0003] For high-performance organic solar cells, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/46
CPCC07D495/22H10K85/655H10K85/657Y02E10/549
Inventor 宋金生杨丽思王华
Owner HENAN UNIVERSITY
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