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Hyperbranched conjugated polyelectrolyte based on tripolyindole and preparation method and use thereof

A technology of conjugated polyelectrolyte and tripolybenzazole, which is applied in the direction of circuits, photovoltaic power generation, electrical components, etc., can solve the problems of low device efficiency, poor film formation, difficult orthogonal solvent solution processing and preparation, etc., and achieve good transparency The effect of light efficiency and good thermal stability

Active Publication Date: 2020-01-17
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims to solve the technical problems in the prior art that the hole transport materials based on tripolybenzazole and its derivatives have poor film-forming properties, it is difficult to prepare devices by orthogonal solvent method solution processing, and the device efficiency is low, and provides a A kind of hyperbranched conjugated polyelectrolyte based on trimerindole and its preparation method and application

Method used

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  • Hyperbranched conjugated polyelectrolyte based on tripolyindole and preparation method and use thereof
  • Hyperbranched conjugated polyelectrolyte based on tripolyindole and preparation method and use thereof
  • Hyperbranched conjugated polyelectrolyte based on tripolyindole and preparation method and use thereof

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preparation example Construction

[0061] The present invention also provides a method for preparing a hyperbranched conjugated polyelectrolyte based on tripolybenzazole, comprising the following steps:

[0062] Step 1. In the presence of NaH, the compound of formula (V) is subjected to an electrophilic substitution reaction to form a small molecule compound of formula (VI);

[0063]

[0064] M is the following structure:

[0065]

[0066] The structure of R is shown in formulas (II), (III) and (IV):

[0067]

[0068] Step 2-1. In the presence of a catalyst, the compound of formula (VI) undergoes a Suzuki coupling reaction to form a hyperbranched conjugated polyelectrolyte of formula (I);

[0069]

[0070] Or step 2-2, in the presence of a catalyst, the compound of formula (VI) undergoes a Stille coupling reaction, thereby forming a hyperbranched conjugated polyelectrolyte of formula (I);

[0071]

[0072] Or step 2-3, in the presence of a catalyst, the compound of formula (VI) undergoes a dire...

Embodiment 1

[0082] A tripolybenzazole-based hyperbranched conjugated polyelectrolyte whose structure is TAT-H-P, the synthetic route is as follows:

[0083]

[0084] (1) Synthesis of the intermediate with the chemical structure a: under the protection of argon, add 2-indolinone (3 g, 22.5 mmol) and phosphorus oxychloride (10 mL) into a 100 mL two-neck flask, and heat to 100 ° C for 12 h. After the reaction, cool to room temperature, add ice water and stir, add sodium hydroxide aqueous solution to neutralize the acidity of the system until the pH is neutral. Filtrate, dissolve the filter residue in acetone, dry with anhydrous sodium sulfate, spin dry after filtration, and separate by column chromatography, the eluent is petroleum ether / ethyl acetate (5:1), and recrystallized in acetone to obtain 0.75g slightly yellow crystals. Rate 29.0%. 1H NMR (400MHz, DMSO) δ11.87(s, 3H), 8.68(d, J=7.5Hz, 3H), 7.73(d, J=7.8Hz, 3H), 7.36(dt, J=22.3, 7.2Hz ,6H).

[0085] (2) Synthesis of intermediat...

Embodiment 2

[0090] A tripolybenzazole-based hyperbranched conjugated polyelectrolyte whose structure is TAT-T-P, the synthetic route is as follows:

[0091]

[0092] Wherein, the synthesis of intermediates a, b, and c is the same as in Example 1.

[0093] Synthesis of TAT-T-P: Under argon protection, compound c (300mg, 0.28mmol), thiophene-2,5-diboronic acid dipinacol ester (72.1mg, 0.42mmol), tetrakis(triphenyl Phosphine) palladium (9.9mg, 0.0085mmol), sodium carbonate (226.5mg, 2.14mmol), 12mL DMF, 3mL water, react at 90°C for 12h. The capping reaction of thiophene-2-boronic acid pinacol ester took 12 hours, and the capping reaction of 2-bromothiophene took 12 hours. After the reaction, cool to room temperature, settle with acetone, filter, and dialyze in water (the molecular weight cut-off of the dialysis bag is 3500). Obtained 249.1mg black bright powder, yield 93.0%.

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Abstract

The invention belongs to the field of organic semiconductor photoelectric materials, in particular to a hyperbranched conjugated polyelectrolyte based on tripolyindole and a preparation method and anapplication thereof. The invention solves the technical problems in the prior art that the hole transport material based on tripolyindole and its derivatives has poor film forming property, it is difficult to prepare devices by using orthogonal solvent method solution, and the prepared devices have low efficiency. The hyperbranched conjugated polyelectrolyte material based on tripolyindole provided by the invention is neutral in pH and does not corrode corresponding electrodes and organic materials; the hole transport layer of the organic photoelectric device can be prepared by orthogonal solvent method solution processing. It has the advantages of good light transmittance in visible light region and good thermal stability. The hyperbranched conjugated polyelectrolyte based on tripolyindole prepared by the invention is used as a hole transport layer to prepare the organic photovoltaic device or the organic electroluminescent device, and the organic photovoltaic device or the organic electroluminescent device has higher efficiency.

Description

technical field [0001] The invention belongs to the field of organic semiconductor optoelectronic materials, and in particular relates to a trimerindole-based hyperbranched conjugated polyelectrolyte and its preparation method and application. Background technique [0002] Organic semiconductor materials have attracted extensive attention due to their advantages of light weight, low cost, flexibility, and large-area devices that can be prepared by solution processing, and have great application prospects. In the past ten years, as two important applications of organic semiconductor optoelectronic materials, organic light-emitting diodes (OLEDs) and organic solar cells (OPVs) have achieved important development. In these two types of devices, the interfacial layer plays an important role in improving the device performance. The interfacial layer includes a hole-transport layer and an electron-transport layer, which facilitate the ohmic contact between the corresponding elect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54
CPCC08G61/124C08G61/126C08G2261/411C08G2261/18C08G2261/512C08G2261/145C08G2261/592C08G2261/3241C08G2261/3223C08G2261/146H10K85/151Y02E10/549
Inventor 王利祥童辉陈永红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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