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Carbazole nine-element condensed ring central core-containing D(A-Ar)4 type organic photoelectric material, and preparation method and applications thereof

A fused ring and organic technology, applied in the field of organic optoelectronics, can solve the problems of low carrier mobility, low battery efficiency, narrow absorption spectrum, etc., and achieve the effects of wide ultraviolet absorption, good charge extraction performance, and improved fill factor

Inactive Publication Date: 2019-01-11
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, based on organic small molecule solar cell materials, there are still scientific problems such as narrow absorption spectrum, low carrier mobility, low cell efficiency and poor stability, and it is necessary to develop new high-performance organic small molecule photovoltaic donor materials

Method used

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  • Carbazole nine-element condensed ring central core-containing D(A-Ar)4 type organic photoelectric material, and preparation method and applications thereof
  • Carbazole nine-element condensed ring central core-containing D(A-Ar)4 type organic photoelectric material, and preparation method and applications thereof
  • Carbazole nine-element condensed ring central core-containing D(A-Ar)4 type organic photoelectric material, and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Nine-membered fused ring core D(A-Ar) containing carbazole 4 Butterfly-shaped organic small molecule TTDBC (DPP) 4 The synthetic route of is shown below.

[0053]

[0054] 1.1 Synthesis of 2,7-dibromo-3,6-diiodo-9-(2-octyldodecyl)carbazole (M1)

[0055] Under nitrogen protection, the compound 2,7-dibromo-9-H-carbazole (3g, 4.97mmol) and 50mL of acetic acid were successively added to a 100mL three-necked flask, and the reactant was dissolved at 80°C, and potassium iodide (2.22g, 13.41mmol) and potassium periodate (1.43 g, 6.71mmol), and continued to reflux for 12h. Cooled to room temperature and quenched with water, extracted with chloroform (100mL × 3) and washed with saturated sodium sulfite solution (100mL × 3), washed with anhydrous MgSO 4 Dry overnight, filter, and spin off the solvent under reduced pressure to give a gray crude product. The crude product was separated by silica gel column chromatography using petroleum ether (PE) as the eluent to obtain a wh...

Embodiment 2

[0065] D(A-Ar) 2 Performance characterization of small-molecule photovoltaic materials and fabrication and performance testing of photovoltaic devices.

[0066] D(A-Ar) 2 small molecule photovoltaic materials 1 The H NMR spectrum was measured by a Bruker Dex-400NMR instrument, the mass spectrum was measured by a Bruker Bifie MALDI TOF mass spectrometer, and the ultraviolet-visible absorption spectrum was measured by a HP-8453 ultraviolet-visible spectrometer.

[0067] Based on D(A-Ar) n The photovoltaic device structure of the type small molecule material is ITO / PEDOT:PSS / active layer / Ca / Al photovoltaic device. Including indium tin oxide conductive glass substrate layer (ITO), wherein the anode modification layer is a polydioxyethylene thiophene (PEDOT, 30nm) coating; the cathode is a deposition layer of Ca (10nm) / Al (100nm); the active layer material ( 30nm) is D(A-Ar) described in the present invention 4 Molecules and PCs 71 BM, its blending weight ratio is 1:3 (w / w, 1...

Embodiment 3

[0070] Small molecule TTDBC (DPP) 4 Photophysical Properties and Performance of Photovoltaic Devices

[0071] TTDBC (DPP) 4 The thermogravimetric curve of figure 1 shown. Its decomposition temperature is 390°C and it has good thermal stability.

[0072] TTDBC (DPP) 4 The UV absorption spectrum in DCM solution as figure 2 shown. Among them, the absorption peak at 345-600nm is the π-π* transition absorption peak of the complex, and the absorption band in the range of 600-830nm is attributed to the charge transfer (ICT) of the intramolecular donor-acceptor unit.

[0073] TTDBC (DPP) 4 The UV absorption spectrum in the film as image 3 shown. Compared with the solution state, the small molecule has a red shift of about 12nm in the thin film state. At the same time, at 644nm, a strong electronic oscillation shoulder peak appears, which is attributed to the TTDBC (DPP) 4 In the thin film state, due to the rigidity of the molecular skeleton, there is a strong stacking effe...

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Abstract

The invention belongs to the technical of organic photoelectric material, and more specifically relates to a carbazole nine-element condensed ring central core-containing D(A-Ar)4 type organic photoelectric material, and a preparation method and applications thereof. According to the preparation method, a three-element carbazole central ring unit and a thiophene derivative are subjected to coupling, ring closure reaction and coupling reaction are adopted so as to obtain an aromatic compound derivative containing a carbazole based nine-element condensed ring coplanar structure, and a D(A-Ar)4 butterfly type organic small molecular photovoltaic material containing a carbazole nine-element condensed ring center donor core. The aromatic compound derivative containing a carbazole based nine-element condensed ring coplanar structure, and the D(A-Ar)4 butterfly type organic small molecular photovoltaic material possesses high heat stability and excellent plane performance. The structure witha wide spectrum absorption range and an appropriate energy level is promising to be taken as organic solar energy cell donors or receptor materials.

Description

technical field [0001] The present invention specifically relates to D(A-Ar) whose molecular center donor nucleus comprises a carbazole nine-membered fused ring center nucleus 4 The butterfly-shaped small molecule material can be applied in the field of organic photoelectric technology. Background technique [0002] Organic solar cells have become a research hotspot in the field of photovoltaic materials because of their low cost, light weight, and large-area printing. [0003] As an important material in the photosensitive active layer that absorbs sunlight and converts it into electricity, organic small molecule donors have broad market applications due to their outstanding advantages such as simple purification, monodispersity, clear structure, easy modification and good reproducibility. prospect. Therefore, organic solar cell materials and batteries based on small molecules have received more and more attention. [0004] However, based on organic small molecule solar ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/655H10K85/6572H10K85/657H10K30/30Y02E10/549
Inventor 刘煜杨振朱卫国刘座吉李敏
Owner CHANGZHOU UNIV
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