Quinoid compounds and preparation method and applications thereof

A compound and quinone-based technology, which is applied in the preparation of carbon-based compounds, heterocyclic compounds, and organic compounds, can solve the problems of regulating the photophysical properties and carrier transport properties of materials, complex synthesis, and high price. Achieve the effect of improving electron transport performance, strong intermolecular force and low price

Active Publication Date: 2018-11-09
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of these structures is complex and requires the use of expensive palladium catalysts
In addition, most of these structures have dicyano groups as end groups, which are difficult to modify, so it is difficult to adjust the photophysical properties and carrier transport properties of materials through the adjustment of end groups.

Method used

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  • Quinoid compounds and preparation method and applications thereof
  • Quinoid compounds and preparation method and applications thereof
  • Quinoid compounds and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] The synthesis process of compound 1: the compound 9,9-dioctyl-2,7-dibromofluorene (1.5g, 2.73mmol) was dissolved in 40ml tetrahydrofuran, stirred evenly, cooled to -78°C, and then added BuLi dropwise (2.73ml, 6.84mmol, 2.5M), stirred at -78°C for 1h, added DMF (1.69ml, 21.88mmol) dropwise, kept stirring at -78°C for 2h, then raised to room temperature and continued to react for 1h. The reaction solution was poured into water and stirred for 20 min, CH 2 Cl 2 Extraction, washed with water, anhydrous MgSO 4 After drying, filtering, and removing the solvent under reduced pressure, it was separated with a silica gel column (petroleum ether: ethyl acetate = 20:1, volume ratio) to obtain a white solid (1.07 g, yield: 88%).

Embodiment 2

[0034]

[0035] Synthesis process of compound 2: Compound 1 (1g, 2.24mmol) and phenylpeptide (625mg, 4.70mmol) were dissolved in ethyl propionate 17.2ml, and a methanol solution of sodium methoxide (2.49ml, 5.4M) was added. After reacting at 70°C for 4 hours, the solvent was removed under reduced pressure. After dissolving the residue with water, add 2mol / L hydrochloric acid solution, extract the mixture with chloroform, wash with water, anhydrous MgSO 4 Dry and filter. After the solvent was removed under reduced pressure, it was separated with a silica gel column (eluent: petroleum ether: dichloromethane = 2:3, volume ratio) to obtain a dark red viscous product (1.44 g, yield: 95%). 1 H NMR (CDCl 3 , 400MHz, ppm): δ8.11-8.07(dd, J=4Hz, 4H), 7.94-7.90(dd, J=4Hz, 4H), 7.63-7.57(d, J=8Hz, 2H) 7.21(s, 2H) 7.11-7.05 (d, J = 8Hz, 2H) 4.35-4.31 (s, 2H) 1.93-1.85 (m, 4H) 1.32-0.98 (m, 36H) 0.93-0.82 (t, J = 6, 6H) ), 0.64-0.59 (m, 4H).

Embodiment 3

[0037]

[0038] The synthesis process of compound 3: Dissolve compound 2 (1 g, 1.47 mmol) in 31 ml of acetonitrile, slowly add 31 ml of bromine water dropwise, and react at room temperature for 12 h. Chloroform extraction reaction solution, washed with water, anhydrous MgSO 4 After drying, filtering, and removing the solvent under reduced pressure, it was separated by silica gel column (eluent: petroleum ether: dichloromethane = 1:1, volume ratio) to obtain yellow solid 3 (927 mg, yield: 93%). 1 HNMR (CDCl 3 , 400MHz, ppm): δ8.16-8.10(dd, J=4Hz, 4H), 8.00-7.94(dd, J=4Hz, 4H), 7.86-7.84(s, 2H), 7.65-7.59(s, 4H) 2.02-1.91 (m, 4H) 1.36-0.97 (m, 36H) 0.93-0.82 (t, J = 6, 6H) 0.68-0.57 (m, 4H). The H NMR spectrum of quinone compound 3 is as follows figure 1 shown.

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Abstract

Quinoid compounds and a preparation method and applications thereof are disclosed. The general structure of the compounds is shown in the description. The structures of the compounds can be easily modified, and the compounds have characteristics of good molecular skeleton planarity, high self-assembling capability, low energy level of the highest unoccupied orbit (LUMO), narrow band gaps, and insensitivity to water and oxygen, and therefore the compounds as organic semiconductor materials can greatly improve hole and electron transmission capability so that the compounds are applied as n type(electron transmitting) materials and bipolar materials (capable of transmitting holes and electrons) into organic field effect transistors, organic solar cells, perovskite solar cells, organic thermoelectric and organic light-emitting devices, and the like.

Description

technical field [0001] The invention relates to a class of novel quinone compounds and their preparation and application, belonging to the fields of organic functional materials and organic electronics. In particular, it relates to quinoid compounds with indandione and its derivatives as terminal groups. Background technique [0002] Organic field-effect transistors can be applied to electronic paper, electronic tags, active matrix drivers, and sensors due to their characteristics of simplicity, low cost, large-area flexible preparation, and easy integration. They are considered to have huge market potential. The core component of an organic field effect transistor is an organic semiconductor material. According to the transport type of carriers, semiconductor materials can be divided into p-type materials (hole transport), n-type materials (electron transport) and bipolar materials (both electron and hole transport). As far as the current research is concerned, the resear...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/683C07C49/697C07C49/755C07D495/04C07C47/546C07C45/00C07C45/59C07C45/67C09K11/06H01L51/50H01L51/54H01L51/42H01L51/46
CPCC09K11/06C07C49/683C07C49/697C07C49/755C07D495/04C09K2211/1011C09K2211/1092C07C2603/18C07C2602/08H10K85/626H10K85/615H10K85/6576H10K30/00H10K50/00Y02E10/549
Inventor 耿延候邓云峰杜天高瑞横白俊华
Owner TIANJIN UNIV
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