Preparation method and application of organic conjugated micro-molecules rich in nitrogen and sulfur

An organic field and reaction technology, applied in the fields of organic chemistry, semiconductor/solid-state device manufacturing, electrical components, etc., can solve the problems of lagging development of n-type materials, and achieve the effect of good application prospects, good electron mobility, and simple synthesis route.

Inactive Publication Date: 2016-08-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, p-type materials are represented by pentacene, and their development is earlier and more mature, while the development of n-type materials is relatively lagging behind.

Method used

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  • Preparation method and application of organic conjugated micro-molecules rich in nitrogen and sulfur
  • Preparation method and application of organic conjugated micro-molecules rich in nitrogen and sulfur
  • Preparation method and application of organic conjugated micro-molecules rich in nitrogen and sulfur

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of 5,9-dihydro-2,3,7,8-tetrachloropyrazino[2,3-g]quinoxaline compound shown in embodiment 1, formula III

[0038] 1) Synthesis of 5,9-dihydro-1,4,6,9-tetrahydro-pyrazino[2,3-g]quinoxaline-2,3,7,8-tetraketone

[0039] Add 5.1 g of 1,2,4,5-benzenetetraaminotetrahydrochloride into 10% dilute hydrochloric acid solution with 3.8 g of oxalic acid dissolved in it at room temperature, and stir the nitrogen mixture for 0.5 hour; then heat to 100°C and stir After reacting for 12 hours, cool to room temperature, a brown solid precipitated out, suction filtered, washed with distilled water several times until the pH value of the extracted water was about 7.0, then vacuum-dried the obtained solid, and weighed to obtain 4.40 g of a brown solid.

[0040] The structural characterization data are as follows:

[0041] Mass Spectrum: [MS(EI)] m / z: 246 (M + ).

[0042] H NMR spectrum: 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 8.0 (s, 4H), 8.09 (s, 2H).

[0043] 2) Synthesis of 5,9-d...

Embodiment 2、5

[0048] Example 2, 5,11-dihydro-2,2'-([1,3]dithiolo[4,5-e]pyrazino[2,3-g][1,3]dithio Alcoho[4,5-b]quinoxaline-2,8-diylidene) dimalononitrile compound (compound DTYM)

[0049] 1) Synthesis of 1,1-dicyanoethylene-2,2-disulfide sodium salt

[0050] Under stirring, slowly add 6.6g of malononitrile into the suspension of 8.0g of sodium hydroxide in 100mL of ethanol, keep the temperature at 10-15°C, after the addition, weigh 7.6g of carbon disulfide dropwise with a syringe Add it to the reaction solution. After the dropwise addition, continue to react under ice bath conditions for 30 minutes, and then gradually rise to room temperature for 2 hours to obtain a yellow viscous solid, which is filtered by suction, washed with absolute ethanol, and then dried to obtain a light yellow solid powder. 17g.

[0051] The structural characterization data are as follows:

[0052] Elemental analysis: Molecular formula: C 4 N 2 S 2 Na; theoretical value: S, 34.4; found value: S, 33.2.

[005...

Embodiment 3

[0058] Embodiment 3, the ultraviolet-visible absorption performance, electrochemical performance, thermal performance and field effect transistor performance of the obtained compound DTYM prepared in embodiment 2

[0059] 1) UV-Vis absorption properties of compound DTYM

[0060] figure 1 is the UV-Vis absorption spectrum of compound DTYM in the film. Depend on figure 1 It can be seen that the maximum absorption peak position of the compound DTYM in the film is 472 nanometers, and the calculated optical band gap is 2.2 electron volts (the optical band gap is calculated according to the formula E g =1240 / λ calculation, where E g is the optical band gap, and λ is the boundary value of the UV absorption curve).

[0061] 2) Electrochemical properties of the compound DTYM

[0062] figure 2 is the cyclic voltammetry curve of compound DTYM. The electrolytic cell adopts a three-electrode system, with platinum as the working electrode, platinum wire as the counter electrode, sil...

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Abstract

The invention discloses organic conjugated micro-molecules rich in nitrogen and sulfur, and a preparation method and application thereof. The organic conjugated micro-molecules rich in nitrogen and sulfur have a structure shown by formula (I), wherein R is hydrogen, alkyl or aryl. The invention also provides a preparation method of the compound of formula (I). The synthetic route of the organic conjugated micro-molecules is simple and effective; raw materials are commercial cheap products, and the synthesis cost is low; and a synthetic method has universality, and can be popularized and applied to synthesis of other various substituent substituted tetrathiophene derivatives. OFETs (organic field-effect transistors) prepared by taking 5,11-dihydro-2,2'-([1,3]) dithiol [4,5-e] pyrazine [2,3-g][1,3] dithiol [4,5-b] quinoxaline-2,8-diidene) di-malononitrile compound (DTYM), synthesized by the method disclosed by the invention, as an organic semiconductor layer are relatively high in mobility and on / off ratio, the highest electron mobility is 0.005cm<2>V<-1>s<-1>, the on / off ratio is greater than 10<3>, and the organic conjugated micro-molecules have a good application prospect in n-type OFET devices.

Description

technical field [0001] The invention relates to a preparation method and application of a nitrogen-sulfur-rich organic conjugated small molecule. Background technique [0002] Organic field-effect transistors (OFETs for short) are active devices that use π-conjugated organic compounds as semiconductor materials and control the conductivity of materials through electric fields. Since it was reported in 1986 (Tsumura, A.; Koezuka, H.; Ando, ​​T. Appl. Phys. Lett, 1986, 49, 1210), OFET has made great progress. OFETs have many excellent properties, such as easy preparation and functionalization of organic semiconductor materials, low device preparation temperature, good flexibility, good compatibility with plastic substrates, and large-area preparation. attention. OFET devices are key components of organic optoelectronic devices and circuits, and have shown great development and application prospects in smart cards, electronic labels, electronic paper, memory, sensors, and act...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/30
Inventor 刘云圻程诚王翰林刘洪涛黄剑耀陈华杰于贵
Owner INST OF CHEM CHINESE ACAD OF SCI
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