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Bipolar organic dyes and preparation method thereof

A technology of organic dyes and general formulas, which is applied in the manufacture of coumarin dyes, photosensitive devices, semiconductors/solid-state devices, etc., can solve the problems of cumbersome preparation process, insufficient spectral response range, and high cost, and achieve product yield and purity High efficiency, easy preparation and operation, and high degree of commercialization of raw materials

Inactive Publication Date: 2013-04-24
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the preparation process of ruthenium series dyes is cumbersome, the spectral response range is not wide enough, and ruthenium is a noble metal, the cost is high, so people actively develop pure organic dyes
However, the sensitization of a single organic dye is limited by the absorption spectrum of the dye, and it is difficult to match the emission spectrum of the sun. Therefore, people have designed dyes with different structures to use together to make up for the shortcomings of their respective absorption spectra. Effect

Method used

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  • Bipolar organic dyes and preparation method thereof
  • Bipolar organic dyes and preparation method thereof
  • Bipolar organic dyes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of bipolar organic dye (I-1)

[0028]

[0029] Step 1 In a four-necked flask equipped with a stirrer, dissolve 0.2 mole of p-dimethylaminoaniline with 60 milliliters of 12% hydrogen chloride methanol solution, and then add 14.5 grams of Sodium nitrate reacts with diazonium. After 1 hour, the diazo solution was poured into a methanol solution of 0.22 mole salicylaldehyde to carry out the azo reaction. The azo reaction product system was poured into 100 ml of water, and the precipitate was collected. The filter cake was washed with methanol for 3 to 5 times and dried in vacuum to obtain 44.8 g of yellow-brown powder 4-p-dimethylaminophenylazosalicylaldehyde with a yield of 83.3% and a melting point of 133-135°C.

[0030] h 1 -NMR (CDCl 3, δ): 3.07 (s, 6H), 5.33 (s, 1H), 6.65-8.18 (m, 7H), 9.77 (s, 1H).

[0031] Elemental Analysis: C 15 h 15 N 3 o 2 Found (calculated): C66.88 (66.90), H5.60 (5.61), N15.57 (15.60).

[0032] The UV-visible ...

Embodiment 2

[0041] The preparation of embodiment 2 bipolar organic dyes (I-2)

[0042]

[0043] According to the preparation method and steps of Example 1, the salicylaldehyde in step 1 in the example was replaced with 4-dimethylaminosalicylaldehyde to prepare bright red bipolar organic dye (I-2), with a melting point of 214-215°C .

[0044] The UV-visible light absorption characteristic peak λmax=493nm and the fluorescence emission spectrum characteristic peak λmax=607nm of the bipolar organic dye (I-2) in N,N-dimethylformamide solution.

Embodiment 3

[0045] The preparation of embodiment 3 bipolar organic dyes (I-3)

[0046]

[0047] According to the preparation method and steps of Example 1, the salicylaldehyde in step 1 in the example was replaced with 4-diethylaminosalicylaldehyde to prepare bright purple organic dye (I-3), with a melting point of 202-203°C.

[0048] The UV-visible light absorption characteristic peak λmax=490nm and the fluorescence emission spectrum characteristic peak λmax=605nm of the bipolar organic dye (I-3) in N,N-dimethylformamide solution.

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Abstract

The invention relates to a bipolar organic dye, in particular to a D-N=N-pi-A organic dye, wherein D is an electron repulsive structural unit, N=N is an azo structural unit, pi is a coumarin conjugated structural unit, and A is a cyanoacetic acid electron acceptor structural unit. The invention aims to provide a functional organic dye which has the advantages of high tailorability of molecular design, wide spectral response range and lower synthesis cost, can be applied to the fields of organic electroluminescent materials, dye sensitized nano TiO2 solar cells and the like.

Description

technical field [0001] The invention relates to an organic dye, in particular to a bipolar organic dye composed of an electron-pushing group-azo-coumarin-cyanocarboxylic acid structural unit. It belongs to the field of fine chemicals. technical background [0002] In the past two decades, dye-sensitized nano-TiO 2 The research, application and commercial development of solar cells (dye-sensitized solar cells, DSSCs) as a new energy source have become the focus of the world's developed countries. Compared with monocrystalline silicon or polycrystalline silicon solar cells, this type of solar cell has the characteristics of a wide range of production raw materials and low manufacturing process costs. The role of organic dyes used on DSSCs is to absorb sunlight. The organic dye molecules absorb photons and are excited to change from the ground state to the excited state, and the generated electrons and holes are transferred to nano-TiO. 2 in the conduction band of the semico...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/02H01G9/20H01M14/00H01L51/42
CPCY02E10/542Y02E10/549
Inventor 贾海红丁志丹李赞周琴琴张田林
Owner HUAIHAI INST OF TECH