Dinaphtho heterocyclic ring small molecular hole-transport material as well as synthesis method and application thereof

A technology of hole transport materials and heterocyclic small molecules, applied in luminescent materials, chemical instruments and methods, photovoltaic power generation, etc., can solve the problem of low energy conversion efficiency of perovskite solar cells, unstable battery device performance, and expensive materials. and other problems, to achieve the effects of low synthesis cost, improved environmental stability, and high glass transition temperature

Active Publication Date: 2019-03-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the chemical structure of spiro-OMeTAD is complicated, the synthesis route is long, the price is expensive, and the hole mobility of the material is low, which leads to the low energy conversion efficiency of perovskite solar cells.
Usually p-type doping with bis(trifluorometh

Method used

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  • Dinaphtho heterocyclic ring small molecular hole-transport material as well as synthesis method and application thereof
  • Dinaphtho heterocyclic ring small molecular hole-transport material as well as synthesis method and application thereof
  • Dinaphtho heterocyclic ring small molecular hole-transport material as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of compound I (the synthetic route is shown in the summary of the invention):

[0051] Synthesis of Intermediate I: Dioxaanthanthrene (2.86g, 10mmol) was dissolved in 2L of dichloromethane to obtain a saturated solution; liquid bromine (3.2g, 20mmol) was slowly added dropwise at -78°C . The resulting mixed solution was slowly raised to room temperature during 5 hours with stirring, and stirred and reacted at room temperature for 2 hours. As the reaction progressed, a yellow solid precipitated out of the reaction system. The resulting solid was filtered by suction and washed to obtain intermediate I (4.36 g, 99% yield).

[0052] Synthesis of Compound Ⅰ: Intermediate Ⅰ (880mg, 2mmol) was mixed with dimethoxydiphenylamine (1.08g, 4.4mmol), tris(dibenzylideneacetone)dipalladium (91mg, 0.1mmol), tetrafluoroborate tris tert-butylphosphine (58mg, 0.2mmol) and sodium tert-butoxide (577mg, 6mmol) were added to 50mL of toluene; under the protection of nitrogen, hea...

Embodiment 2

[0054] Preparation of compound II (the synthetic route is shown in the summary of the invention):

[0055] Synthesis of Intermediate II: Dithioxaanthanthrene (3.14g, 10mmol) was dissolved in 3L of dichloromethane to obtain a saturated solution; liquid bromine (3.2g, 20mmol) was slowly added dropwise at -78°C . The resulting mixed solution was slowly raised to room temperature during 5 hours with stirring, and stirred and reacted at room temperature for 2 hours. As the reaction progressed, a red solid precipitated out of the reaction system. The resulting solid was filtered by suction and washed to obtain intermediate II (4.63 g, 98% yield).

[0056] Synthesis of Compound Ⅱ: Intermediate Ⅱ (944mg, 2mmol) was mixed with dimethoxydiphenylamine (1.08g, 4.4mmol), tris(dibenzylideneacetone) dipalladium (91mg, 0.1mmol), tetrafluoroborate tris Tert-butylphosphine (58mg, 0.2mmol) and sodium tert-butoxide (577mg, 6mmol) were added together into 50mL of toluene, under the protection o...

Embodiment 3

[0058] Preparation of compound III (the synthetic route is shown in the summary of the invention):

[0059] Synthesis of Intermediate III: Dinaphthofuran (2.68g, 10mmol) was dissolved in 100mL of dichloromethane to obtain a saturated solution; liquid bromine (3.2g, 20mmol) was slowly added dropwise at -78°C. The resulting mixed solution was slowly raised to room temperature during 5 hours with stirring, and stirred and reacted at room temperature for 2 hours. As the reaction progressed, a white solid precipitated out of the reaction system. The resulting solid was filtered by suction and washed to obtain intermediate III (4.18 g, 99% yield).

[0060] Synthesis of compound Ⅲ: Intermediate Ⅲ (846mg, 2mmol) was mixed with dimethoxydiphenylamine (1.08g, 4.4mmol), tris(dibenzylideneacetone) dipalladium (91mg, 0.1mmol), tetrafluoroborate tris Tert-butylphosphine (58mg, 0.2mmol) and sodium tert-butoxide (577mg, 6mmol) were added together into 50mL of toluene, under the protection o...

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Abstract

The invention relates to the technical field of perovskite solar cells, and aims at providing a dinaphtho heterocyclic ring small molecular hole-transport material as well as a synthesis method and application thereof. An effective component of the material is any one of dioxaanthanthrene, dithioanthanthrene, dinaphthofuran, dinaphthothiophene or dinaphthopyrrole. According to the synthesis methoddisclosed by the invention, five kinds of small molecular hole-transport materials are designed and synthesized by taking the dioxaanthanthrene, the diethianthanthrene, the dinaphthofuran, the dinaphthothiophene and the dinaphthopyrrole as nuclei and introducing dialkoxy diphenylamine group to an active site. The material disclosed by the invention has the advantages of low synthesis cost, good film forming property and high hole mobility; the material as a non-doped hole-transport material can be applied to perovskite solar cell devices, so that higher device efficiency is achieved.

Description

technical field [0001] The invention belongs to the technical field of perovskite solar cells, and in particular relates to five types of dinaphthoheterocyclic small molecule hole transport materials and their synthesis methods and applications. Background technique [0002] In 2009, the Miyasaka group took the lead in applying organic-inorganic hybrid perovskites as light-absorbing materials to solar cells. The energy conversion efficiency of the cells was as high as 3.8%, which triggered extensive research in the world. The research on this new type of solar cells The report shows a blowout growth. By 2018, the energy conversion efficiency of 23.3% has been achieved, exceeding 1cm 2 The device achieved an energy conversion efficiency of 19.6% (Science, 2016, 353, 58-62). At the same time, solution-processed perovskite solar cells can achieve high efficiency and large-scale mass production through roll-to-roll. Compared with traditional silicon-based solar cells, the manuf...

Claims

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Application Information

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IPC IPC(8): C07D209/80C07D307/77C07D333/50C07D493/06C07D495/06C09K11/06H01L51/42H01L51/46H01L51/48
CPCC09K11/06C07D209/80C07D307/77C07D333/50C07D493/06C07D495/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/636H10K85/6576H10K85/6574H10K30/151H10K85/6572H10K30/50Y02E10/549H10K50/15H10K85/50
Inventor 王鹏许年胜郑艾彬王佳男魏月芳
Owner ZHEJIANG UNIV
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