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Axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material and its preparation method and application

A small molecule acceptor, axisymmetric technology, applied in semiconductor/solid-state device manufacturing, electrical components, electric solid-state devices, etc., can solve the problems of limiting photocurrent and energy conversion efficiency, so as to improve energy conversion efficiency and broaden the absorption range , the effect of improving the utilization rate

Active Publication Date: 2020-07-28
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] A variety of small molecule acceptor materials with naphthalene cores have been reported, but the bridging rings are basically five-membered bridging rings, the absorption spectrum starts at about 730nm, and the optical bandgap is about 1.70eV, which limits the photocurrent and energy conversion efficiency. Further improve

Method used

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  • Axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material and its preparation method and application
  • Axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material and its preparation method and application
  • Axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material and its preparation method and application

Examples

Experimental program
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Embodiment 1

[0071] The preparation method of the axisymmetric six-member bridged ring naphthalene nuclear small molecule acceptor material PTT-IC, the specific steps are as follows:

[0072]

[0073] (1) Synthesis of Compound 1: Naphthalene-1,4-bisboronic acid pinacol ester (1.32g, 3.47mmol), 2-bromothieno[3,2-b]thiophene-3-carboxylic acid ethyl ester ( 2.53g, 8.68mmol), 45mL toluene, 20mL ethanol, 20mL K 2 CO 3 The solution (2mol / L) was added to a 250mL reaction flask, and 180mg of tetrakis(triphenylphosphine)palladium was added under the protection of argon, and refluxed for 24h. Pour into water after cooling, extract with dichloromethane, dry over anhydrous magnesium sulfate, spin off the solvent, and purify the crude product by column chromatography, using petroleum ether / dichloromethane (2:1) as eluent, to obtain 1.66g gray solid , and the yield was 88.1%. 1 H NMR (400MHz, CDCl 3 )δ: 7.80(s,2H),7.61(s,2H),7.54(d,J=5.1Hz,2H),7.45-7.39(m,2H),7.34(d,J=5.0Hz,2H), 4.06(br,4H), 0.8...

Embodiment 2

[0082] A preparation method of axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material PTT-2FIC, the main technical scheme of this embodiment 2 is basically the same as the steps (1) to (4) of embodiment 1, in this implementation Features not explained in Example 2 are explained in Example 1, and will not be repeated here. The difference between this embodiment and embodiment 1 is:

[0083]

[0084] Add compound 4 (120mg, 0.11mmmol), 5,6-difluoro-3-(dicyanomethylene) indoketone (147mg, 0.64mmol) and 30mL chloroform in turn to a 100mL reaction flask, and add under nitrogen protection 0.5mL pyridine, heated to reflux reaction overnight, after cooling, precipitated with methanol, the crude product was purified by column chromatography, petroleum ether / dichloromethane (1:1) was the eluent, and 86mg blue-black solid was obtained. The yield was 52.1%. 1 H NMR (500MHz, CDCl 3 )δ: 8.69 (s, 2H), 8.50 (dd, J = 9.8, 6.5Hz, 2H), 8.13 (s, 2H), 7.63...

Embodiment 3

[0088] A preparation method of axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material PT-IC, the specific steps are as follows:

[0089]

[0090] (1) Synthesis of Compound 5: Naphthalene-1,4-bisboronic acid pinacol ester (1.20g, 3.15mmol), ethyl 2-bromothiophene-3-carboxylate (1.73g, 7.35mmol), 20mL toluene , 10mL ethanol, 10mL K 2 CO 3 The solution (2mol / L) was added to a 100mL reaction flask, and 100mg tetrakis(triphenylphosphine)palladium was added under the protection of argon, and refluxed for 24h. Cool to room temperature, extract with dichloromethane, wash with saturated sodium chloride solution, dry over anhydrous magnesium sulfate, spin off the solvent, and purify the crude product by column chromatography, using petroleum ether / dichloromethane (2:1) as eluent, 1.28 g of gray solid were obtained, yield 98.1%. 1 H NMR (500MHz, CDCl 3 )δ: 7.68-7.65 (m, 4H), 7.51 (s, 2H), 7.42-7.40 (m, 4H), 3.94 (q, J = 7.1Hz, 4H), 0.76 (t, J = 6...

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Abstract

The invention discloses an axisymmetric hexahydric bridged ring naphthalene nucleus small-molecule receptor material and a preparation method and application thereof, and relates to the field of organic solar cell materials. The structure general formula of the receptor material is shown in the description, wherein Ar1 and Ar2 refers to independent aromatic groups, and R1 refers to a C2-C12 alkylor alkyl aromatic group. Compared with the prior art, the receptor material has the advantages that an obvious red-shift absorption spectrum is achieved, the sunlight utilization rate of an organic solar cell is increased, short-circuit current of the organic solar cell can be obviously increased, and the energy conversion efficiency is high when the material is applied to the solar cell.

Description

technical field [0001] The invention relates to the field of organic solar cells, in particular to an axisymmetric six-membered bridged ring naphthalene nuclear small molecule acceptor material and a preparation method and application thereof. Background technique [0002] In recent years, non-fullerene acceptor materials have become one of the research hotspots. Compared with traditional fullerene derivative acceptor materials, non-fullerene acceptor materials have the following outstanding advantages: 1) Strong light-absorbing properties in the visible and even near-infrared regions; 2) The electrochemical energy level can be easily adjusted , so as to obtain higher open circuit voltage; 3) higher shape stability; 4) low synthesis cost, etc. The reported energy conversion efficiency of organic solar cells based on non-fullerene acceptors has reached 17.3%. [0003] Excellent organic solar cells have 20mA / cm 2 above the high short-circuit current. The absorption of sola...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22H01L51/46
CPCY02E10/549
Inventor 曹佳民胡威徐永卓杜思颖
Owner HUNAN UNIV OF SCI & TECH
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