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Alkyl/sulfanyl N-heterocyclic terminal D (A-Ar) type 2 conjugate compound as well as preparation method and application thereof

A technology of conjugated compound and sulfanyl nitrogen is applied in the field of D2-type conjugated compound and its preparation, which can solve the problems of low photoelectric conversion efficiency, hinder the development of high-efficiency organic small molecule solar cells, etc., and achieve high energy conversion efficiency, The effect of high hole mobility

Active Publication Date: 2019-07-12
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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  • Alkyl/sulfanyl N-heterocyclic terminal D (A-Ar) type 2 conjugate compound as well as preparation method and application thereof
  • Alkyl/sulfanyl N-heterocyclic terminal D (A-Ar) type 2 conjugate compound as well as preparation method and application thereof
  • Alkyl/sulfanyl N-heterocyclic terminal D (A-Ar) type 2 conjugate compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1, compound 2-octylthiazole (TZR 1 ) synthetic route is as follows:

[0061]

[0062] Under nitrogen protection, in a 100mL three-necked flask, dissolve 2-bromothiazole (6.0g, 36.58mmol) with dry ether, add dropwise 2.5M n-butyllithium (16.0ml, 40.24mmol) at -78°C, -78 After reacting at ℃ for two hours, n-octane bromide (7.0 g, 36.58 mmol) was added all at once, and after keeping the reaction for half an hour, it was turned to room temperature for overnight reaction. The solvent was directly spin-dried under reduced pressure to obtain a light yellow liquid, which was separated by column chromatography using petroleum ether as an eluent to obtain the product (TZR 1 ) 6.0 g, yield 84%. 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=15.4,7.6Hz,2H), 1.33–1.26(m,11H),0.87(s,3H).

Embodiment 2

[0063] Example 2,2-octylthiazole-5-tributyltin (SnTZR 1 ) The synthetic route is as follows:

[0064]

[0065] Under nitrogen protection, in a 100mL three-necked flask, dissolve 2-octylthiazole (2.46g, 10.8mmol) in dry tetrahydrofuran, add dropwise 2.5M n-butyllithium (4.75ml, 11.88mmol) at -78°C, - After two hours of reaction at 78°C, tributyltin chloride (3.22ml, 11.88mmol) was added in one go, and after half an hour of incubation, the reaction was carried out at room temperature overnight. The solvent was directly spin-dried under reduced pressure to obtain light yellow thick liquid (SnTZR 1 ), used directly 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

[0066] 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:

[0067]

[0068] Under nitrogen protection, add 20mL of toluene, 2-octylthiazole-5-tributyltin (286mg, 0.59mmol), 3,6-bis(5-bromo-2-thienyl)-2,5- Bis(2-ethylhexyl)-diketopyrrolopyrrole (400 mg, 0.59 mmol), tetrakistriphenylphosphine palladium (34 mg, 0.03 mmol). Stir and heat to 80°C under nitrogen atmosphere, stop the reaction after 4h, and cool to room temperature. The solvent was removed by rotary evaporation, and the mixed solution of sherwood oil / dichloromethane volume ratio of 5:1 was used as the eluent to carry out column chromatography separation to obtain the product (BrTDPP-TZR 1 ) 172 mg, yield 30.0%. 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), 3.02(t, J=7.7Hz, 2H), 1.82(dt, J=15.3, 7...

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Abstract

The invention belongs to the technical field of organic photoelectric materials and particularly relates to an alkyl / sulfanyl N-heterocyclic terminal D (A-Ar) type 2 conjugate compound as well as a preparation method and application thereof. A conjugate organic small molecule photovoltaic donor material with a D (A-Ar) type 2 structure is obtained by taking 3,3'-difluoro-2,2'-bisthiophene donor unit as a center core and carrying out alkylation reaction, electrophilic substitution bromination reaction and stille coupling reaction. The D (A-Ar) type 2 conjugate compound disclosed by the invention has the advantages of good solubility and stability, wide spectral absorption range, high light absorption capacity and proper electrochemical energy level and capability of being expected to be used in donor materials of organic solar cells. The maximum energy conversion efficiency and short-circuit current of a single-layer device body heterojunction solar cell with Fullerene PC71BM as a receptor respectively reach 8.91 percent and 16.75mA cm<-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 Applications(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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