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Electron withdrawing group-containing phenylene vinylene compound, and preparation method and application thereof

A technology of p-phenylene vinylene and electron-withdrawing substituents, which is applied in the field of new p-phenylene vinylene compounds containing electron-withdrawing groups, and can solve the problems of low electron mobility and poor stability

Inactive Publication Date: 2015-07-08
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Aiming at the problem that the electron mobility is relatively low and the stability is relatively poor in the field effect transistor materials and solar cell materials based on p-phenylene vinylene compounds and polymers, the purpose of the present invention is to provide a new class of materials containing electron-withdrawing groups. P-phenylene vinylene compounds, and their application to the preparation of organic conjugated molecules, especially organic conjugated polymers

Method used

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  • Electron withdrawing group-containing phenylene vinylene compound, and preparation method and application thereof
  • Electron withdrawing group-containing phenylene vinylene compound, and preparation method and application thereof
  • Electron withdrawing group-containing phenylene vinylene compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0095]

[0096] The synthesis process of compound 1: Chloral hydrate (9.55g, 57.89mmol) and hydroxylamine hydrochloride (10.97g, 157.89mmol) were added in deionized water (150mL). Na2 SO 4 (100g, 684.19mmol) and H 2 SO 4 (40 mL, 1 M) was added as catalyst. After uniform stirring, 3-bromo-2-fluoroaniline (10 g, 52.63 mmol) was added. After mixing, it was heated to 130°C and refluxed for 30 minutes, then the system was lowered to 80°C and filtered to obtain the product, which was washed with water to obtain light yellow solid compound 1.

Embodiment 2

[0098]

[0099] Synthesis process of compound 2: Add concentrated sulfuric acid (100mL) into a 250ml round bottom flask, heat to 50°C, compound 1 is added in batches under stirring, then warm up to 70°C for 1 hour, and then pour the system into water to quench The reaction was quenched, and after filtration, the ethyl acetate liquid separation was carried out, and the compound 2 (7.80 g, yield 61%) was obtained after separation on a silica gel column. 1 H NMR (DMSO, 400MHz, ppm): δ11.74 (s, 1H), 7.40–7.37 (dd, J H-H =8.0,J H-F =5.6Hz,1H),7.32–7.30(d,J H-H =8.0Hz,1H). 13 CNMR(DMSO,100MHz,ppm):δ182.29–182.25(d,J F-C 4 =3.9Hz), 159.17, 145.23–142.78 (d,J F-C 1 =246Hz), 138.19–138.05(d, J F-C 2 =14.0Hz), 126.47–126.45(d, J F-C 4 =1.7Hz), 121.38–121.34(d, J F-C 3 =3.8Hz), 119.89–119.85(d, J F-C 3 =3.7Hz), 118.42–118.25(d, J F-C 2 =17.3Hz).EI-MS calcd.for[M+H] + :243;found:243.Elemental Anal.calcd.for C 8 h 3 BrFNO 2 :C,39.38;H,1.24;N,5.74;found:C,39.39;H,1.40...

Embodiment 3

[0101]

[0102] The synthesis process of compound 4: Dissolve compound 3 (2.2g, 3.22mmol) in a mixture of tetrahydrofuran (30mL) and N,N'-dimethylformamide (DMF) (30mL), and add compound 6- Bromo-5-fluoroisatin (2,750mg, 3.07mmol) and K 2 CO 3 (635 mg, 4.61 mmol). After reacting at 50°C for 8 hours, the solvent was removed under reduced pressure. After dissolving the residue with chloroform, wash with water, and use anhydrous Na 2 SO 4 dry. After the solvent was removed under reduced pressure, it was separated with a silica gel column (eluent: petroleum ether: dichloromethane = 1:1) to obtain an orange-yellow solid 4 (1.8 g, yield: 75%). 1 H NMR (CDCl 3 ,400MHz,ppm):δ7.34–7.29(m,2H),3.86–3.82(t,J=7.4Hz,2H),1.69–1.62(m,2H),1.30–1.22(m,71H),0.90 –0.86(t,J=6.8Hz,6H). 13 C NMR (CDCl 3 ,100MHz,ppm):δ181.7(s),157.6(s),146.09–143.62(d,J F–C 1 =248.5Hz), 137.88–137.78(d, J F–C 2 =9.7Hz), 128.19(s), 122.02–121.83(d, J F–C 2 =19.6Hz), 121.60–121.56(d, J F–C 3 =3.9Hz)...

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Abstract

The invention discloses an electron withdrawing group-containing phenylene vinylene compound, and a preparation method and an application thereof. The electron withdrawing group-containing phenylene vinylene compound monomer or polymers obtained by polymerizing the monomer and other aromatic compound monomers greatly improve the hole and electron mobility in a material as an organic semiconductor material due to the containing of a electron withdrawing substituent group, so the monomer or the polymers can be used in organic field effect transistors, organic solar batteries, organic light-emitting diodes and other photoelectric devices as an n-type material (for transferring electrons) or a bipolar transfer material (for transferring holes and electrons).

Description

technical field [0001] The invention relates to a new class of p-phenylene vinylene compounds containing electron-withdrawing groups, their preparation method, and their application as organic semiconductor materials, belonging to the fields of organic functional materials and organic electronics. Background technique [0002] Because organic molecules gather to form materials through weak intermolecular van der Waals forces, they mostly behave as electrically inert insulating materials. In the 1970s, scientists discovered that when polyacetylene was doped, its electrical conductivity would be greatly improved, reaching the level of a conductor, thus breaking the traditional concept that organic compounds cannot conduct electricity and opening up the field of organic electronics. The structure of organic conjugated molecules contains a conjugated system composed of delocalized π electrons, so it reflects special properties such as light, electricity, and magnetism, which has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C08G61/12H01L51/00H10K99/00
Inventor 裴坚雷霆王婕妤
Owner PEKING UNIV
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