Organic semiconductor materials containing 2,9-dialkyl-6-alkoxy phenanthridine unit and preparation method and application thereof

An organic semiconductor, alkoxyphenanthridine technology, applied in the field of organic optoelectronic materials, can solve the problems of insufficient blue spectrum, narrow polymer energy band, etc., and achieve the effects of easy purification, improved open circuit voltage, and improved color purity.

Active Publication Date: 2016-08-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the S, S-dioxy-dibenzothiophene unit has a strong electron-withdrawing ability, which directly causes the doped polymer to have a narrow energy band and the spectrum is not blue enough.

Method used

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  • Organic semiconductor materials containing 2,9-dialkyl-6-alkoxy phenanthridine unit and preparation method and application thereof
  • Organic semiconductor materials containing 2,9-dialkyl-6-alkoxy phenanthridine unit and preparation method and application thereof
  • Organic semiconductor materials containing 2,9-dialkyl-6-alkoxy phenanthridine unit and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1, 3,8-dibromo-6-((2-octyldodecyl)oxy)phenanthridine (abbreviated as Br 2 -PO) synthesis

[0049] The chemical reaction process is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:

[0050]

[0051] Among them, (I) chromium trioxide, glacial acetic acid, 60°C (II) sodium azide, concentrated sulfuric acid, ice bath for 4 hours; (III) 2-octyl dodecyl bromide, potassium carbonate, DMF, reflux for 12 hours.

[0052] (1) Dissolve 2,7-dibromofluorene (19.5g, 60mmol) in 400ml of glacial acetic acid and stir, add chromium trioxide (18.1g, 180mmol) and heat to 60°C, react overnight, pour the reaction the next day into crushed ice, filtered and washed the filter cake with water three times, and dried the filter cake to obtain a yellow solid (compound 1, 19.1 g, yield 95%). The raw material 2,7‐dibromofluorene was ordered from Aldrich Company.

[0053] (2) Dissolve 2,7-dibromofluorenone (compound 1, 2.36g, 7mmol) ...

Embodiment 2

[0055] Example 2, 3,8-dibromo-2,9-dioctyl-6-((2-octyldodecyl)oxy)phenanthridine (abbreviated as Br 2 -PO88) synthesis

[0056]

[0057] Among them, (I) ethylene glycol, trimethyl orthoformate, toluene, p-toluenesulfonic acid, reflux; (II) n-octane bromide, magnesium chips, tetrahydrofuran, Ni(dppf)Cl 2 , heated to reflux for two days, 2M HCl; (Ⅲ) liquid bromine, iron powder, chloroform; (Ⅳ) sodium azide, concentrated sulfuric acid; (Ⅴ) 2-octyl dodecyl bromide, potassium carbonate, DMF, reflux 12 hours.

[0058] (1) Order 3,6-dibromofluorene raw material fluorene from Aldrich Company.

[0059] (2) Synthesis of compound 4[3,6-dibromospiro[fluorene-9,2'-[1,3]dioxolane]

[0060] Compound 3 (10 g, 30 mmol), 8 ml of ethylene glycol, and 0.05 g of p-toluenesulfonic acid were dissolved in 200 ml of toluene, and 9 g of trimethyl orthoformate was added after argon gas flowed for 10 min, and heated to reflux for one day. The next day, the reaction solution was washed three times w...

Embodiment 3

[0069] The synthesis of embodiment 3, polymer PDBTPO

[0070] The polymerization reaction process is shown in the following formula, and the specific steps and reaction conditions are as follows:

[0071]

[0072] Among them, (I) chlorobenzene, Pd 2 (dba) 3 , P(o-tol) 3 , microwave reaction, 140°C, 45 minutes.

[0073] Weigh monomer Br 2 -PO (61.3mg, 0.1mmol), monomer DBT (88.2mg, 0.1mmol) were placed in a microwave reaction tube, chlorobenzene (3mL) was added, and argon was passed for 20 minutes. Then add the catalyst Pd 2 (dba) 3 (3mg) and ligand P(o-tol) 3 (7 mg), argon gas was passed through the reaction tube to fill the reaction tube with argon gas, the lid was closed, microwave reaction was carried out, and the reaction was carried out at 140° C. for 45 minutes. After the reaction is over, drop the reaction solution into methanol to precipitate the polymer, then wash the polymer with methanol, acetone, and n-hexane in a Soxhlet extractor, filter the head, and ...

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Abstract

The invention discloses organic semiconductor materials containing 2,9-dialkyl-6-alkoxy phenanthridine and a preparation method and an application thereof. The organic semiconductor materials are prepared by carrying out a reaction of 2,9-dialkyl-6-alkoxy phenanthridine halogenated derivatives and a monomer containing an aromatic group structure under a metal catalyst, wherein the aromatic group and a 2,9-dialkyl-6-alkoxy phenanthridine unit are connected in a conjugate manner. The invention discloses a method for synthesis of 2,9-dialkyl-6-alkoxy phenanthridine by a phenanthridone isomerization reaction; a series of organic semiconductor materials containing the 2,9-dialkyl-6-alkoxy phenanthridine unit are synthesized and are applied in the field of organic optoelectronic devices, and solar cell devices with high open circuit voltage and deep blue polymer blue light devices are obtained.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of organic semiconductor materials containing 2,9-dialkyl-6-alkoxyphenanthridine units, a preparation method thereof and its application in the technical field of organic photoelectric materials. Background technique [0002] Due to their unique photophysical properties, organic optoelectronic materials have many advantages such as light weight, simple processing, low cost, and the ability to make large-area flexible devices, and have received extensive attention in the past decade. [0003] In terms of organic solar cells, a research group reported in Nature Communication this year that the energy conversion efficiency of single-layer polymer batteries has exceeded 10% (DOI: 10.1038 / ncomms6293), which indicates that organic solar cells will have broad commercial prospects. However, compared with inorganic solar cells, the energy conver...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/42H01L51/46H01L51/50H01L51/54
CPCC09K11/06C08G61/122C08G61/126C08G2261/95C08G2261/354C08G2261/91C08G2261/12C08G2261/1424C08G2261/314C08G2261/3241C08G2261/3223C09K2211/1458C09K2211/1466C09K2211/1483H10K85/113H10K30/00H10K50/00Y02E10/549
Inventor 黄飞黄允平应磊曹镛
Owner SOUTH CHINA UNIV OF TECH
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