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Electron-transport polymer semiconductor material based on pyridine substituted pyrrolopyrroledione and applied to organic field effect transistor

A technology for diketopyrrolopyrrole and electron transport, which is applied in silicon organic compounds, tin organic compounds, semiconductor devices, etc., and can solve the problems of difficult application of high-mobility conjugated polymers, poor reaction selectivity, and low reactivity.

Inactive Publication Date: 2018-10-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low reactivity of C-H bonds and poor reaction selectivity, it has been difficult to apply to the synthesis of high mobility conjugated polymers.

Method used

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  • Electron-transport polymer semiconductor material based on pyridine substituted pyrrolopyrroledione and applied to organic field effect transistor
  • Electron-transport polymer semiconductor material based on pyridine substituted pyrrolopyrroledione and applied to organic field effect transistor
  • Electron-transport polymer semiconductor material based on pyridine substituted pyrrolopyrroledione and applied to organic field effect transistor

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preparation example Construction

[0041] The preparation method of the polymer described in the present invention is described below. with R 1 and R 2 Taking 4-tetradecyl octadecyl as an example, the preparation process is as follows:

[0042] Step (1): 3,6-bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione:

[0043]

[0044] According to the above reaction equation, it is prepared according to the method provided in the literature (Adv. Mater., 2014, 26, 2636; Adv. Funct. Mater., 2015, 25, 2725). Mix 1 times molar amount of 5-bromo-2cyanopyridine with 1 times molar amount of sodium tert-amylate and tert-amyl alcohol. After replacing the gas with high-purity argon, the temperature was raised to 110°C, and after all the solids were dissolved, 0.5 times the molar amount of diethyl succinate was added at one time, and the reaction was carried out at 110°C for 12 hours. Cool, add methanol and acetic acid in turn, filter, wash the filter cake with water and ethanol respectively, and dry to obtai...

Embodiment 1

[0070] Example 1: Preparation of 3,6-bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione

[0071]

[0072] Under an inert atmosphere, 5-bromo-2cyanopyridine (9.02g, 49.2mmol) and sodium tert-amylate (5.42g, 49.2mmol) were dissolved in tert-amyl alcohol (100mL), heated to 110°C and stirred for 30min. Diethyl succinate (4.09 mL, 24.6 mmol) was added in one portion, and the reaction was stirred overnight at 110°C. After cooling down to room temperature, methanol (30 mL) was added in one portion, and after stirring for 5 min, acetic acid (30 mL) was added in one portion. The filter cake was obtained by filtration, washed with deionized water and methanol, and dried in a vacuum oven to obtain a dark red solid (6.04 g, yield 54.6%), which was directly used in the next step.

Embodiment 2

[0073] Example 2: 3,6-bis(5-bromopyridin-2-yl)-2,5-bis(2-decyltetradecyl)pyrrolo[3,4-c]pyrrole-1,4- Preparation of (2H,5 H)-diketones

[0074]

[0075] Under the protection of inert gas, 3,6-di(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione (0.40g, 0.89 mmol), anhydrous potassium carbonate (0.37 g, 2.68 mmol) and 18-crown-6-ether (5 mg) were dissolved in dry DMF (10 mL). After fully stirring and dissolving, add 1-iodo-2-decyltetradecyl (1.23g, 2.64mmol) at one time, react at 70°C for 24 hours, distill off DMF under reduced pressure, extract the solid residue with chloroform, anhydrous sulfuric acid Magnesium was dried, filtered and spin-dried. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane) to obtain a dark red solid (0.53 g, yield 51.3%). The structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3 ,δ):8.94(d,J=8.4Hz, 2H),8.74(d,J=2.0Hz,2H),8.02(dd,J 1 =8.4Hz,J 2 =2.0Hz,2H),4....

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Abstract

The invention provides an electron-transport polymer semiconductor material based on pyridine substituted pyrrolopyrroledione and applied to an organic field effect transistor. The material is represented as the structural formula (I). In the material, pyridine substituted pyrrolopyrroledione, having strong electron absorption capability and good planarity, serves as a first polymerization monomerand tetrafluorobithiophene and tetrafluorobithiophene ethylene serve as second polymerization monomers; a plurality of fluorine atoms are introduced onto the thiophene unit, so that highest occupiedmolecular orbital (HOMO) energy level and lowest unoccupied molecular orbital (LUMO) energy level of the polymer are both reduced, and the polymer shows an n-type transportation character. By means ofthe weak interactions of F-S and F-H, interchain interaction of the polymer is improved, so that the organic field effect transistor with the polymer semiconductor material has high electron mobilitycapable of reaching up to 2.45 cm<2> / V*s.

Description

technical field [0001] The invention relates to the technical field of semiconductor materials, in particular to the preparation of a polymer semiconductor material and its application to organic field effect transistors as a semiconductor material. Background technique [0002] Conjugated polymers have excellent solution processing properties, and can be used to prepare devices by wet processing methods such as printing and printing, and have attracted much attention in recent years. The organic field effect transistor (OFET), which is used as the semiconductor active layer, is expected to become the core technology of the new generation of flat panel display. According to the transport type of carriers, conjugated polymers can be classified into p-type (hole transport) and n-type (electron transport). In recent years, p-type polymers have been studied more and developed rapidly, and the mobility of some polymers has exceeded 10cm 2 / V s, and the device performance has go...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30C07D487/04C07D333/28C07F7/08C07F7/22
CPCC07D333/28C07D487/04C07F7/0812C07F7/0827C07F7/0829C07F7/083C08G61/12C08G61/122C08G61/126C08G2261/146C08G2261/1412C08G2261/124C08G2261/414C08G2261/3241C08G2261/3223C08G2261/3221C08G2261/92H10K85/113
Inventor 耿延候郭恺邓云峰
Owner TIANJIN UNIV
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