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A Class of Alkyl/Sulfanyl Aza-Heteroaromatic Terminations of d(a-ar) 2 Type conjugated compound and its preparation method and application

A technology of conjugated compound and sulfanyl nitrogen, which is applied in the field of D2-type conjugated compound and its preparation, can solve the problems of hindering the development of high-efficiency organic small molecule solar cells, low photoelectric conversion efficiency, etc., and achieves enhanced charge transport performance, The effect of good film formation and high carrier mobility

Active Publication Date: 2021-06-22
CHANGZHOU UNIV
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Problems solved by technology

[0005] At present, the photoelectric conversion efficiency of organic small molecule materials is still lower than that of polymer materials as a whole. The design principles of limited small molecule donor materials have seriously hindered the development of high-efficiency organic small molecule solar cells. How to obtain high efficiency through molecular structure design Photoelectric conversion efficiency of organic small molecule photovoltaic materials presents a huge challenge

Method used

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  • A Class of Alkyl/Sulfanyl Aza-Heteroaromatic Terminations of d(a-ar) <sub>2</sub> Type conjugated compound and its preparation method and application
  • A Class of Alkyl/Sulfanyl Aza-Heteroaromatic Terminations of d(a-ar) <sub>2</sub> Type conjugated compound and its preparation method and application
  • A Class of Alkyl/Sulfanyl Aza-Heteroaromatic Terminations of d(a-ar) <sub>2</sub> Type conjugated compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1, compound 2-octyl thiazole (TZR 1 ) synthetic route is as follows:

[0060]

[0061] Under nitrogen protection, in a 100mL there-necked flask, dissolve 2-bromothiazole (6.0g, 36.58 mmol) with dry ether, add dropwise 2.5M n-butyllithium (16.0ml, 40.24mmol), -78 After reacting at °C for two hours, n-octane bromide (7.0 g, 36.58 mmol) was added at one time, and after incubation for half an hour, the reaction was transferred to room temperature overnight. The solvent was directly spin-dried under reduced pressure to obtain a pale yellow liquid, which was separated by column chromatography with petroleum ether as an eluent to obtain the product (TZR 1 ) 6.0 g, 84% yield. 1 H NMR (500MHz, CDCl 3 )δ7.66(d, J=3.3Hz,1H),7.18(d,J=3.3Hz,1H),3.05–2.97(m,2H),1.79(dt,J=15.4,7.6 Hz,2H), 1.33–1.26(m, 11H), 0.87(s, 3H).

Embodiment 2

[0062] Example 2, 2-Octylthiazole-5-tributyltin (SnTZR 1 ) synthetic route is as follows:

[0063]

[0064] Under nitrogen protection, in a 100 mL three-necked flask, dissolve 2-octylthiazole (2.46 g, 10.8 mmol) with dry tetrahydrofuran, add 2.5M n-butyllithium (4.75 ml, 11.88 mmol) dropwise at -78°C, - After reacting at 78° C. for two hours, tributyltin chloride (3.22 ml, 11.88 mmol) was added at one time, and after the reaction was incubated for half an hour, the reaction was transferred to room temperature overnight. The solvent was directly spin-dried under reduced pressure to obtain a light yellow thick liquid (SnTZR 1 ), which was directly used in the next reaction. 1 H NMR (400MHz, CDCl 3 )δ7.58(s,1H),3.06–3.03(m,2H), 1.80(dt,J=15.0,7.4Hz,2H),1.58–1.51(m,6H),1.46(dt,J=16.1, 8.7Hz, 6H), 1.39-1.17(m, 22H), 0.89(t, J=7.2Hz, 12H).

Embodiment 3

[0065] Example 3,3-(5-Bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-6-(5-(2-octyl-5-thiazolyl)-2-thiophene base) diketopyrrolopyrrole (BrTDPP-TZR 1 ) synthetic route is as follows:

[0066]

[0067] Under nitrogen protection, 20 mL of toluene, 2-octylthiazole-5-tributyltin (286 mg, 0.59 mmol), 3,6-bis(5-bromo-2-thienyl)-2,5- Bis(2-ethylhexyl)-pyrrolopyrrole dione (400 mg, 0.59 mmol), tetrakistriphenylphosphine palladium (34 mg, 0.03 mmol). The mixture was heated to 80°C with stirring under nitrogen atmosphere, the reaction was stopped after 4 h, and the mixture was cooled to room temperature. The solvent was removed by rotary evaporation, and the mixed solution whose volume ratio of petroleum ether / dichloroalkane was 5:1 was the eluent to carry out column chromatographic separation to obtain the product (BrTDPP-TZR 1 ) 172 mg, 30.0% yield. 1 H NMR (400MHz, CDCl 3)δ8.90(d,J=4.1Hz,1H), 8.64(d,J=4.2Hz,1H),7.84(s,1H),7.27(s,1H),7.23(d,J=4.2Hz, 1H), 3.98(dt, J=13.7, 7.2Hz, 4H), 3...

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Abstract

The invention belongs to the technical field of organic optoelectronic materials, and in particular relates to a D(A-Ar) at the end of a class of alkyl / sulfanyl nitrogen heteroaromatic rings 2 Type conjugated compound and preparation method and application thereof. Taking 3,3'-difluoro-2,2'-bisthiophene donor unit as the central nucleus, through alkylation reaction, electrophilic substitution on bromine reaction and stille coupling reaction, D(A-Ar) was obtained 2 Conjugated Organic Small Molecule Photovoltaic Donor Materials with Type Structure. D(A-Ar) according to the present invention 2 The type conjugated compounds have good solubility and stability, wide spectral absorption range, strong light absorption ability and suitable electrochemical energy level, and are expected to be used as donor materials for organic solar cells. with fullerene PC 71 The maximum energy conversion efficiency and short-circuit current of single-layer device bulk heterojunction solar cells with BM as acceptor are as high as 8.91% and 16.75 mA cm, respectively ‑2 .

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of D(A-Ar) at the end of an alkyl / sulfanyl azaaryl ring 2 Type conjugated compound and its preparation method and application. Background technique [0002] With the rapid growth of the global population and the rapid development of the economy, the storage of fossil fuels, which used to be an important natural energy source, has decreased sharply and will be exhausted in the near future, and the excessive use of fossil fuels has also caused irreversible environmental problems. The frequency of smog weather is getting higher and higher. In addition to water energy, wind energy, geothermal energy, etc., solar energy is the most important renewable energy. Studies have shown that the energy from sunlight to the earth every year exceeds thousands of times the total energy consumed by human beings. It can be said to be inexhaustible. Inexhaustible. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C09K11/06H01L51/05H01L51/30H01L51/42H01L51/46H01L51/50H01L51/54
CPCC07D519/00C09K11/06C09K2211/1029C09K2211/1092C09K2211/1037H10K85/6576H10K85/6572H10K10/46H10K30/00H10K50/00Y02E10/549
Inventor 刘煜李敏朱卫国刘座吉杨振
Owner CHANGZHOU UNIV
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