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Method for preparing novel organic field effect transistor material

An organic field and transistor technology, which is applied in the field of preparation of new organic field effect transistor materials, can solve the problems of cumbersome synthesis methods and insufficient universality, and achieve the effect of simple and efficient synthesis methods

Inactive Publication Date: 2013-07-24
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The object of the present invention is to provide a kind of novel organic field effect transistor material pyrrolo[3,2- b ] The preparation method of pyrrole fused ring compound, in order to solve the problems such as the existing synthetic method is loaded down with trivial details and general applicability etc.

Method used

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  • Method for preparing novel organic field effect transistor material
  • Method for preparing novel organic field effect transistor material
  • Method for preparing novel organic field effect transistor material

Examples

Experimental program
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Effect test

Embodiment 1

[0027]

[0028] In the dry schlenk tube, under nitrogen protection, add 0.9g of diazocine compound, 15ml of dry chloroform, stir well, and cool to 0 o C, add 1.68g phosphorus pentachloride in three batches, naturally rise to room temperature, then heat to reflux, continue to stir for 4h, after the reaction is completed, cool to room temperature, solvent is concentrated under reduced pressure, flash column chromatography (silica gel, petroleum ether: Ethyl acetate = 10:1 rinse), to obtain 0.66 g of light yellow imidoyl chloride compound, yield 65%.

[0029] 1 H NMR (CDCl 3 ) δ: 7.38-7.34 (m, 4H); 7.15 (t, J=7.6Hz, 2H); 6.99 (d, J=8.1Hz, 2H). 13 C NMR (CDCl 3 ) δ: 156.3, 145.3, 131.6, 127.1, 126.1, 125.4, 122.0. IR (KBr, cm -1 ): 3160, 3034, 2900, 1649, 1598, 1481, 1439, 1397, 1216, 948, 755. Calculated HRMS(EI): C 14 h 8 Cl 2 N 2 274.0065, measured value: 297.0086[M+Na] + .

Embodiment 2

[0031]

[0032] Operation with reference to Example 1, yield 75%.

[0033] 1 H NMR (CDCl 3 ) δ: 7.51 (dd, J 1 =8.7Hz,J 2 =2.2Hz, 2H); 7.46 (d, J=2.2Hz,2H);

[0034] 6.88 (d, J=8.7Hz, 2H). 13 C NMR (CDCl 3 ) δ: 155.2, 144.0, 134.9, 129.7, 127.3, 123.8, 118.8. Calculated HRMS(EI): C 14 h 6 Br 2 Cl 2 N 2 429.8275, measured value: 452.8301[M+Na] + .

Embodiment 3

[0036]

[0037] Operation with reference to Example 1, yield 60%.

[0038] 1 H NMR (CDCl 3 ) δ: 7.88 (s, 2H); 7.77 (d, J=8.4Hz, 2H); 7.71 (d, J=8.4Hz, 2H), 7.49-7.47 (m, 2H), 7.43-7.41 (m, 4H ). 13 C NMR (CDCl 3 ) δ: 156.6, 141.5, 134.3, 130.2, 128.4, 128.3, 127.5, 126.7, 126.4, 118.9. IR (KBr, cm -1 ): 3054, 2928, 1654, 1594, 1495, 1389, 1174, 1114, 929, 772. Calculated HRMS(EI): C 22 h 12 Cl 2 N 2 374.0378, measured value: 397.0325[M+Na] + .

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Abstract

The present invention relates to a method for preparing a novel organic field effect transistor material of a pyrrolo[3,2-b]pyrrole fused ring compound. The method includes the main steps of: 1) producing 6,12-dichloro diazocine from a diazocine compound under the action of phosphorus pentachloride; and 2) producing the target pyrrolo[3,2-b]pyrrole fused ring compound through reductive coupling of 6,12-dichloro diazocine under the action of a zinc powder and acid. The invention is characterized in that: 1) compared with the conventional synthetic strategy by a C-N bond to build a key reaction, the synthetic route takes the C-C bond built reduction coupling reaction as a key step, and the mehtod is simple, efficient and wide in universality; 2) reaction raw materials and reagents are cheap and easily available, reaction operation is simple and easy for amplification and for industrial production; 3) the remaining pyrrolo[3,2-b]pyrrole fused ring compounds obtained by the invention are firstly synthesized except for DBPP which has been reported, and the method can provide a variety of novel organic semiconductor materials with potential application values.

Description

[0001] technical field [0002] The invention relates to a novel organic field effect transistor material pyrrolo[3,2- b ] The preparation method of pyrrole condensed ring compound. [0003] Background technique [0004] Among various organic semiconductor materials, linear acene molecules and oligothiophenes are the two most studied types. (See Anthony, J. E. Chem. Rev. 2006, 106 , 5028-5048. Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107 , 1066-1096.) For example, the linear acene molecule pentacene, the field effect mobility can reach 5.5 cm 2 ?V -1 ?s -1 , which has become a benchmark for evaluating the properties of other materials in the field of organic electronics. However, pentacene and other acene molecules with more benzene rings are less stable in air due to their higher HOMO (Highest Occupied Molecular Orbital) energy level, and are prone to photodegradation and Diels-Al De reaction, and difficult to dissolve in common organic solvents, these ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D495/22H01L51/30
Inventor 万晓波邱立赵娜
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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