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Asymmetric fused heterocyclic small molecule electron acceptor material based on dithienopyrrole and application thereof

An electron acceptor material, phenopyrrole technology, which is applied in the field of organic solar cell materials, can solve the problems that there is no asymmetric acceptor material, the research direction of asymmetric small molecule acceptor is not deep enough, etc., and achieves good energy level matching. , the effect of wide light absorption range

Inactive Publication Date: 2019-12-17
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current research on asymmetric small molecule receptors is still not deep enough, there are few types of asymmetric small molecule receptors reported, and there is still a lot of room for improvement in their PCE
Most of the reported asymmetric acceptors are developed based on thiophene and polythiophene, and no asymmetric acceptor materials developed using DTP units have been reported yet.

Method used

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  • Asymmetric fused heterocyclic small molecule electron acceptor material based on dithienopyrrole and application thereof
  • Asymmetric fused heterocyclic small molecule electron acceptor material based on dithienopyrrole and application thereof
  • Asymmetric fused heterocyclic small molecule electron acceptor material based on dithienopyrrole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 takes the synthesis of IPT-2F as an example. Synthesis of compound 3:

[0054]

[0055] Under nitrogen protection, 2,5-dibromodiethyl terephthalate (compound 1) (3.93g, 10.34mmol), compound 2 (4.00g, 6.89mmol), and dry toluene (100mL) were added to In a 250mL double-necked flask, deoxygenate by bubbling nitrogen for half an hour, then quickly add Pd(PPh 3 ) 4 (159.25mg, 137.81μmol), the reaction solution was heated to 100°C and reacted for 48 hours. After the reaction stopped, the reaction solution was cooled to room temperature, and the toluene solvent was evaporated with a rotary evaporator. Then separated and purified by chromatographic column, using petroleum ether / ethyl acetate as eluent (15:1 by volume ratio), to obtain orange viscous liquid 3 (2.20 g, 54%). 1 H NMR (500MHz, CDCl 3 , δ): 7.95(d, J=1.9Hz, 2H), 7.17(d, J=5.3Hz, 1H), 7.04(s, 1H), 7.00(d, J=5.3Hz, 1H), 4.44(m , 2H), 4.24(m, 2H), 4.18(t, J=7.0Hz, 2H), 1.86(m, 2H), 1.42(t, J=7.1Hz, 3H...

Embodiment 2

[0069] Example 2 takes the synthesis of IPTT-2F as an example. Synthesis of Compound 8:

[0070]

[0071] Under the protection of nitrogen, sequentially add compound 3 (500 mg, 0.85 mmol), compound 5 (472.45 mg, 1.10 mmol), and dry toluene (12 mL) into a 20 mL reaction flask. Pd(PPh 3 ) 4 (48.92mg, 42.33μmol), the reaction solution was heated to 110°C and reacted for 12 hours. After the reaction stopped, the reaction liquid was cooled to room temperature, and the toluene solvent was evaporated with a rotary evaporator. Then separated and purified by chromatographic column, using petroleum ether / dichloromethane as eluent (volume ratio: 3:2), to obtain orange viscous liquid 8 (450 mg, 81%). 1 H NMR (500MHz, CDCl 3 , δ): 7.95(s, 1H), 7.85(s, 1H), 7.40(d, J=5.2Hz, 1H), 7.33-7.29(m, 2H), 7.18(d, J=5.3Hz, 1H) , 7.10(s, 1H), 7.02(d, J=5.3Hz, 1H), 4.28(m, 4H), 4.20(t, J=7.0Hz, 2H), 1.88(m, 2H), 1.36-1.22( m, 10H), 1.17(m, 6H), 0.87(t, J=6.8Hz, 3H). 13 C NMR (125MHz, CDCl 3...

Embodiment 3

[0082] Example 3 takes the synthesis of IPTTT-2F as an example. Synthesis of Compound 9:

[0083]

[0084] Under the protection of nitrogen, sequentially add compound 3 (500 mg, 0.85 mmol), compound 6 (534.17 mg, 1.10 mmol), and dry toluene (12 mL) into a 20 mL reaction flask. Pd(PPh 3 ) 4 (48.92mg, 42.33μmol), the reaction solution was heated to 110°C and reacted for 12 hours. After the reaction stopped, the reaction liquid was cooled to room temperature, and the toluene solvent was evaporated with a rotary evaporator. Subsequently, it was separated and purified by chromatographic column, using petroleum ether / dichloromethane as eluent (volume ratio 1:1), to obtain yellow solid 9 (500 mg, 84%). 1 H NMR (500MHz, CDCl 3 , δ): 7.95(s, 1H), 7.85(s, 1H), 7.40(d, J=5.2Hz, 1H), 7.33-7.29(m, 2H), 7.18(d, J=5.3Hz, 1H) , 7.10(s, 1H), 7.02(d, J=5.3Hz, 1H), 4.28(m, 4H), 4.20(t, J=7.0Hz, 2H), 1.88(m, 2H), 1.36-1.22( m, 10H), 1.17(m, 6H), 0.87(t, J=6.8Hz, 3H). 13 C NMR (125MHz, ...

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Abstract

The invention discloses an asymmetric fused heterocyclic small molecule receptor material based on dithienopyrrole and application thereof. The method comprises the following steps: firstly, the dithienopyrrole serving as a raw material is mixed with 2,5-dibromoterephthalic acid diethyl ester for unilateral coupling, and then the product is subject to secondary coupling with thiophene, bithiopheneand trithiophene respectively to obtain corresponding asymmetric coupling products, and the asymmetric fused heterocyclic small molecule electron acceptor material based on the dithiophene pyrrole issynthesized through a series of reaction steps such as cyclization, condensation and the like. The asymmetric fused heterocyclic micromolecules based on the dithienopyrrole synthesized by the invention have good thermal stability, solubility and film-forming property, have appropriate optical band gaps and strong light absorption capability, and obtain excellent photoelectric conversion efficiency when being used as electron acceptor materials of organic solar cells.

Description

technical field [0001] The invention relates to a class of asymmetric fused heterocyclic small molecule electron acceptor materials based on dithienopyrrole, which is used as an electron acceptor in organic solar cells and belongs to the field of organic solar cell materials. Background technique [0002] Today's society is supported by energy, and the shortage of energy is becoming more and more serious. Traditional petrochemical energy does not meet the requirements of future energy pattern and environmental protection due to its non-renewable energy materials and combustion pollution. As a clean and renewable green energy, solar energy is gradually becoming an important source of energy to drive social development. Under this background, countries all over the world are paying more and more attention to the research and development of solar-electric energy conversion materials and devices. [0003] At present, in the field of solar cell research and development, crystal...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/657H10K30/00Y02E10/549
Inventor 俞江升唐卫华杨琳强刘鑫张倬涵周杰耿仁勇
Owner NANJING UNIV OF SCI & TECH
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