Preparation and application of A2-pi-A1-pi-A2 type small molecule receptor materials taking thiazolothiazole as core

A technology of small molecule acceptors and thiazolo, which is applied in the field of organic photovoltaics, can solve the problems of high synthesis cost and difficult adjustment of film formation stability, and achieve fewer synthesis steps, optimized absorption and carrier mobility, and strong application potential Effect

Active Publication Date: 2018-11-13
CHANGZHOU UNIV
View PDF3 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis cost of acceptor materials based on the large fused ring center structure is high, and the stability of film formation is difficult to adjust

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation and application of A2-pi-A1-pi-A2 type small molecule receptor materials taking thiazolothiazole as core
  • Preparation and application of A2-pi-A1-pi-A2 type small molecule receptor materials taking thiazolothiazole as core
  • Preparation and application of A2-pi-A1-pi-A2 type small molecule receptor materials taking thiazolothiazole as core

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] A with thiazolothiazole as the nucleus 2 -π-A 1 -π-A 2 Synthesis of small molecule receptor material TTz1.

[0051] The synthetic route of TTz1 is as follows:

[0052]

[0053] 1.1 Synthesis of 2-bromo-3-(2-butyloctyl)thiophene (2)

[0054] In a 250 mL three-necked flask, sequentially add compound 1 (10 g, 39.6 mmol), N-bromosuccinimide (8.46 g, 47.6 mmol), and 150 mL of glacial acetic acid. Under the protection of light, react at room temperature for 12 hours, stop the reaction, transfer the reaction solution to a separatory funnel, add 50mL distilled water, extract with dichloromethane, dry with anhydrous magnesium sulfate, remove the organic solvent by distillation under reduced pressure, and remove the residue with petroleum ether Column chromatography was used as the eluent to obtain compound 2 as a colorless oil (12.2 g, yield 93%). 1 H NMR (400MHz, CDCl 3 )δ7.18(d, J=5.6Hz, 1H), 6.76(d, J=5.6Hz, 1H), 2.49(d, J=7.2Hz, 2H), 1.65(dd, J=11.1, 5.9Hz, 1H), 1....

Embodiment 2

[0066] A with thiazolothiazole as the nucleus 2 -π-A 1 -π-A 2 Synthesis of small molecule receptor material TTz2.

[0067] The synthetic route of TTz2 is as follows:

[0068]

[0069] In a 100mL two-neck flask, sequentially add compound 7 (200mg, 0.21mmol), compound 8 (382mg, 2.07mmol), triethylamine (0.5mL) and chloroform (60mL), under the protection of nitrogen, reflux reaction at 65°C 24h. Cool to room temperature, pour into 200mL of anhydrous methanol for precipitation, filter with suction, and use chloroform as eluent to separate the crude product by column chromatography, and recrystallize from chloroform and acetone to obtain a maroon solid compound with metallic luster TTz2 (230 mg, 83% yield). 1 H NMR (400MHz, CDCl 3 )δ8.32(s,1H),7.95(s,1H),7.76(d,J=7.7Hz,1H),7.56(d,J=7.7Hz,1H),4.35-4.29(m,2H), 2.94-2.82 (m, 2H), 1.89 (t, J=16.9Hz, 1H), 1.51-1.26 (m, 19H), 0.97-0.87 (m, 6H).

Embodiment 3

[0071] Performance characterization of small molecule acceptor materials TTz1 and TTz2 and preparation and testing of photovoltaic devices:

[0072] of the synthesized compound 1 The H NMR spectrum was measured by Bruker Dex-300 NMR or 400NMR instrument, the UV-visible absorption spectrum was measured by Shimadzu UV-800 UV-visible spectrophotometer, and the cyclic voltammetry curve was tested by CHI630E electrochemical analyzer.

[0073] An organic solar cell device based on this type of small molecule acceptor material includes an indium tin oxide (ITO) conductive glass anode, a cathode modification layer, a photoactive layer, an anode modification layer, and a cathode. The active layer material is the small molecule acceptor material described in the present invention and a commercially purchased polymer donor material, and the blending weight ratio is 1:2.

[0074] 3.1 Determination of photophysical properties of small organic molecule receptors TTz1 and TTz2

[0075] fi...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
optical band gapaaaaaaaaaa
open-circuit voltageaaaaaaaaaa
energy conversion efficiencyaaaaaaaaaa
Login to view more

Abstract

The invention relates to preparation of A2-pi-A1-pi-A2 type small molecule receptor materials taking thiazolothiazole weak electronic receptor groups as cores, and application of the materials servingas electron acceptor materials in photo-active layers in the field of organic photovoltaic cells. The small molecule receptor materials only contain single / double aromatic rings, and have the characteristics of being simple in structure, less in synthesis step, excellent in performance and the like. By utilizing the small molecule receptor materials and polymeric donor materials, bulk heterojunction organic solar cells are made by virtue of a solution processing method, and the maximum energy conversion efficiency of battery components reaches 8.77%. The A2-pi-A1-pi-A2 type small molecule receptor materials disclosed by the invention realize high-efficiency energy conversion in the organic polymer solar cells, and have excellent application prospects.

Description

technical field [0001] The invention relates to the field of organic photovoltaics, in particular to a class of A with a simple structure and a weak electron acceptor unit of thiazolothiazole as the core. 2 -π-A 1 -π-A 2 The preparation of small molecule acceptor materials, and the application of such materials as electron acceptors in the photoactive layer in the field of organic photovoltaic cells. Background technique [0002] With the rapid development of today's world economy, energy and environmental crises are becoming more and more serious, and people's demand for clean energy is becoming more and more urgent. As an inexhaustible and inexhaustible green energy, how to efficiently utilize solar energy has become a research hotspot for scientists. Organic solar cells (OSCs) can efficiently convert solar energy into electrical energy, and have the characteristics of low cost, light weight, translucency, flexibility and bendability, which make it show great applicatio...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04H01L51/46H01L51/42
CPCC07D513/04H10K85/649H10K85/655H10K85/656H10K85/6565H10K85/657H10K85/6576H10K30/00Y02E10/549
Inventor 朱卫国彭文红张斌朱梦冰顾子倩马超
Owner CHANGZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap