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Dicyanovinyl substituted quinacridone derivatives with alcohol/water solubility and applications thereof

A water-soluble, dicyandiamide technology, applied in organic chemistry, semiconductor/solid-state device manufacturing, electrical solid-state devices, etc., can solve problems such as unsuitability and unfavorable device stability

Active Publication Date: 2017-03-08
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These materials are sensitive to water and oxygen in the air, so it is not good for the stability of the device
In addition, the method of vacuum thermal evaporation is required to prepare thin films, so it is not suitable for solution inkjet printing process

Method used

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  • Dicyanovinyl substituted quinacridone derivatives with alcohol/water solubility and applications thereof
  • Dicyanovinyl substituted quinacridone derivatives with alcohol/water solubility and applications thereof
  • Dicyanovinyl substituted quinacridone derivatives with alcohol/water solubility and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Compound DCNQA-C 4 -Synthesis of Br:

[0021]

[0022] Put quinacridone (3.12g, 10mmol), 1,4-dibromobutane (10.8g, 50mmol), sodium hydride (1.43g, 50mmol), and 50mL dry tetrahydrofuran into a 100 three-necked flask, and heat to reflux for 24 hours , cooled to room temperature, added 50mL of methanol to neutralize the remaining sodium hydride, added 200mL of water and 500mL of dichloromethane to separate the liquid, and spin-dried the organic solvent to obtain a solid that was recrystallized with chloroform / petroleum ether to obtain the red product QA-C 4 -Br2.91g, yield 62.5%, put into next step directly.

[0023]The QA-C synthesized in the previous step 4 -Br (2.91g, 5.0mmol), malononitrile (0.66g, 10.0mmol), 500mL of anhydrous and dry dichloromethane were placed in a 1L two-necked bottle, and TiCl was slowly added dropwise in sequence 4 (28.50g, 150.0mmol) , Dried pyridine (63.20g, 800.0mmol), after the dropwise addition, the system was stirred at ro...

Embodiment 2

[0024] Example 2: Compound DCNQA-C 5 -Synthesis of Br:

[0025]

[0026] QA-C 5 -Synthetic method of Br and QA-C 4 -Br is exactly the same, except that 1,5-dibromopentane is used as starting material instead of 1,4-dibromobutane (yield 60.2%).

[0027] DCNQA-C 5 -The second step synthesis of Br and DCNQA-C 4 -Br method is exactly the same, just use QA-C 5 -Br as starting material (dark green solid, 72.2% yield). The molecular ion mass determined by mass spectrometry is: 704.5 (calculated value: 704.1); theoretical element content (%) C 36 h 30 Br 2 N 6 : C, 61.31; H, 4.30; N, 11.72; Measured element content (%): C, 61.20; H, 4.28; N, 11.90. The above analysis results indicated that the obtained product was the expected product.

Embodiment 3

[0028] Example 3: Compound DCNQA-C 6 -Synthesis of Br:

[0029]

[0030] QA-C 6 -Synthetic method of Br and QA-C 4 -Br is exactly the same, except that 1,6-dibromohexane is used as starting material instead of 1,4-dibromobutane (65.9% yield).

[0031] DCNQA-C 6 -The second step synthesis of Br and DCNQA-C 4 -Br method is exactly the same, just use QA-C 6 -Br as starting material (dark green solid, 75.1% yield). The molecular ion mass determined by mass spectrometry is: 732.5 (calculated value: 732.1); theoretical element content (%) C 38 h 34 Br 2 N 6 : C, 62.14; H, 4.76; N, 11.44; Measured element content (%): C, 62.29; H, 4.70; N, 11.37. The above analysis results indicated that the obtained product was the expected product.

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Abstract

A dicyanovinyl-substituted quinacridone derivative with alcohol / water solubility and its application as a cathode interface modification material for organic / polymer photovoltaic cells belongs to the technical field of polymer photovoltaic cells. Its general structural formula is as follows, wherein, n is an integer from 4 to 14, R1 can be an ionic group such as N-pyridyl salt, trimethyl quaternary ammonium salt, R2 can be H, F, Cl, and the number of carbon atoms is 1 to 4 alkyl, pyridyl, phenyl and other groups. The cathode interface modification material with dicyanovinyl substituted quinacridone as the core of the present invention has the characteristics of high electron mobility. When the thickness of the cathode interface modification layer changes within the range of 5 to 40 nanometers, the organic / polymer Photovoltaic cells and maintain their high photoelectric conversion efficiency.

Description

technical field [0001] The invention belongs to the technical field of polymer photovoltaic cells, in particular to a dicyanovinyl-substituted quinacridone derivative with alcohol / water solubility and its application as a cathode interface modification material for organic / polymer photovoltaic cells. Background technique [0002] Polymer solar cells have received great attention due to their light weight, low cost, and large-area solution processing on flexible substrates. At present, polymer photovoltaic cells have made significant progress in the design of photoactive layer materials, device structure and device interface optimization, and the highest power conversion efficiency (PCE) has exceeded 10%. [0003] Traditional inorganic cathode interfacial layers include metal oxides (ZnO, TiO 2 etc.) and inorganic salts (such as LiF, CsCO 3 Wait). These materials are sensitive to water and oxygen in the air, which is detrimental to the stability of the device. In addition...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C08G61/12H01L51/44
CPCC07D471/04C08G61/12H10K85/6572H10K30/81Y02E10/549
Inventor 王悦
Owner JILIN UNIV