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Quinacridone derivative borate and preparation method and application thereof

A kind of compound and sulfonic acid group technology, applied in the field of quinacridone derivative boronate ester and preparation thereof, can solve the problems of difficult tin alkylation or boronate esterification, not much, etc.

Inactive Publication Date: 2012-12-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, quinacridones, especially polymers with quinacridones as units, are not widely used in optoelectronic devices at present, mainly because quinacridones are difficult to stannate or borate, which limits their inability to Reacts with most aromatic bromides via stille or Suzuki coupling reactions

Method used

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  • Quinacridone derivative borate and preparation method and application thereof
  • Quinacridone derivative borate and preparation method and application thereof
  • Quinacridone derivative borate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1: the synthesis (R 1 Synthesis of 2-octyl-dodecyl) quinacridone derivative boronate

[0087]Synthesize compound C-1 first, the structural formula is as follows:

[0088]

[0089] Compounds A-1 and B-1 of the following structures are involved in the synthesis process:

[0090]

[0091] First, in a system containing a strong base, a phase transfer catalyst, and toluene, quinacridone and R-Br react to obtain A-1. Compound A-1 reacts with liquid bromine under weakly acidic conditions to obtain B-1. For the specific preparation process of A-1 and B-1, please refer to the literature: Applied materials & interfaces, 2010, 2, 2679.

[0092] In a 250 ml two-necked flask, add 500 mg of B-1 to 80 ml of acetic anhydride, add three times the molar equivalent of malononitrile, heat to reflux overnight, evaporate the acetic anhydride, and the solid is subjected to silica gel column chromatography, petroleum ether: Elution with ethyl acetate=2:1 gave C-1 in 25% yi...

Embodiment 2

[0097] Embodiment 2: the synthesis (R 1 for decanyl)

[0098] Synthesize compounds A-2 and B-2 first, and the structural formula is as follows:

[0099]

[0100] First, add 1 gram of quinacridone, 2.1 grams of tetrabutylammonium bromide, and 0.8 grams of sodium hydride into a 500 ml two-necked bottle, use toluene as a solvent, protect the temperature with argon, raise the temperature to 120 ° C for 2 hours, and drop 1 -Decane bromide, cooled after reacting overnight, spin-dried toluene, and the solid was subjected to silica gel column chromatography, eluting with petroleum ether: dichloromethane = 2:1 to obtain light green powder A-2 with a yield of 30%. Molecular ion peak: 592.6.

[0101] In a 250 ml two-necked bottle, add 400 mg of A-2, 0.8 mg of potassium acetate, and 100 ml of acetic acid, heat to 80°C, and inject 0.05 ml of Br 2 After reacting for 4 hours, it was extracted with chloroform and chromatographed on a silica gel column, eluting with petroleum ether: ethy...

Embodiment 3

[0108] Embodiment 3: compound shown in preparation formula II (R 1 is 2-octyl-dodecyl, Ar is preferably Ar-1)

[0109]

[0110] The preparation of compounds D, E, and F is involved in the process of preparing Ar-1, and the structural formula is as follows:

[0111]

[0112] Preparation of compounds D, E, F:

[0113] Under strong basic conditions, cyanothiophene and dimethyl succinate react to obtain compound D;

[0114] Compound D reacts with 1-bromo-2-octyl-dodecane in DMF solution containing weak base and phase transfer catalyst to obtain E. In chloroform, add compound E and N-bromosuccinimide to obtain F; reference for specific preparation process: Macromolecules, 2010, 43, 821.

[0115] The reaction equation of the compound shown in the preparation formula II with quinacridone derivative borate is as follows:

[0116]

[0117] The specific preparation process is: under the protection of argon, add 54 mg of compound quinacridone derivative borate, 90 mg of comp...

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Abstract

The invention discloses a quinacridone derivative borate shown as a formula I and a preparation method and application thereof. The quinacridone derivative borate is synthesized for the first time, and small molecules and polymer which are obtained by reacting the quinacridone derivative borate with the common receptor unit are applied to an organic solar cell and a field effect transistor. The small molecules and polymer molecules containing the quinacridone derivative borate which serves as a monomer have high planarity, high solubility in the common organic solvent, and high film-forming property, can be processed into a solution, and can be used as a photoactive layer material in the organic solar cell and a charge transport layer material in the organic field effect transistor, the prepared solar cell has high open-circuit voltage and energy conversion efficiency, and the field effect transistor has high migration rate and air stability.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to quinacridone derivative borate and its preparation method and application. Background technique [0002] Compared with traditional inorganic optoelectronic devices, organic optoelectronic devices have the advantages of low cost, light weight, easy processing, and large-area flexible devices, and have become a research hotspot in recent years. The structure of organic molecules determines the performance of optoelectronic devices to a large extent, so it is very important to design and synthesize molecules with excellent structures and properties. Organic molecules used in solar cells must have a wide absorption band to absorb sunlight to the greatest extent; secondly, the molecules must have good planarity and crystallinity to form effective carrier transport channels (Ergang W., Zai F.M., Zhen Z., Koen V., Patrik H., Olle I., Feng L.Z., Mats ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C07D471/04C07D519/00C08G61/12H01L51/30H01L51/46
CPCY02E10/549
Inventor 付红兵李慧吴义室危浪
Owner INST OF CHEM CHINESE ACAD OF SCI
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