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Synthesis and applications of trapezoid condensed polycyclic conjugation semiconductor molecules and polymers

A polymer, fused polycyclic technology, applied in the direction of semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems that have not been used to synthesize polymers

Inactive Publication Date: 2013-12-04
HUNAN AOXINKE MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Also, such small molecules have not been used to date to synthesize polymers

Method used

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  • Synthesis and applications of trapezoid condensed polycyclic conjugation semiconductor molecules and polymers
  • Synthesis and applications of trapezoid condensed polycyclic conjugation semiconductor molecules and polymers
  • Synthesis and applications of trapezoid condensed polycyclic conjugation semiconductor molecules and polymers

Examples

Experimental program
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Effect test

Embodiment 1

[0058] Synthesis of dihexyl 2-bromo-5-thieno[3,2-b]thienyl terephthalate (Intermediate 4):

[0059] The specific steps are:

[0060] In a solution of thieno[3,2-b]thiophene (3.51g, 25mmol) in anhydrous tetrahydrofuran (50ml) at -70°C, add 2.5M n-butyllithium hexane solution (10.5ml, 26.5mmol) dropwise with stirring , the dropping time is 15 minutes. Stirring of the resulting mixture was continued for 1 hour with cooling. Tributyltin chloride (7.42ml, 26.5mmol) was added in one go with a syringe, and the resulting yellow solution was stirred at low temperature for 10 minutes. The cooling bath was removed, and the reaction was continued at room temperature for 1 hour. The solvent was removed from the obtained mixture with a rotary evaporator, and the remaining liquid was dissolved in petroleum ether. The solution was filtered with a microporous membrane filter, and the filtrate was spin-dried in vacuum. The remaining oily liquid was dissolved in toluene (30ml), and 2,5-dibr...

Embodiment 2

[0062] Synthesis of intermediate 5

[0063] The specific steps are:

[0064] According to the synthesis method similar to intermediate 4, n-butyllithium was added dropwise to a solution of thieno[3,2-b]thiophene (0.673g, 4.8mmol) in anhydrous tetrahydrofuran (20ml) at -70°C with stirring Hexane solution (2.5M, 3.90ml, 9.75mmol), the dropwise addition time was 5 minutes. Stirring of the resulting mixture was continued for 1 hour with cooling. Tributyltin chloride (2.65ml, 9.77mmol) was added in one portion with a syringe, and the resulting yellow solution was stirred at low temperature for 10 minutes. The cooling bath was removed, and the reaction was continued at room temperature for 1 hour. The solvent was removed from the obtained mixture with a rotary evaporator, and the remaining liquid was dissolved in petroleum ether. The solution was filtered with a microporous membrane filter, and the filtrate was spin-dried in vacuum. The remaining oily liquid (this is Intermedia...

Embodiment 3

[0066] Synthesis of compound 7 (R=4-n-hexadecylphenyl)

[0067] The specific steps are:

[0068] First, a solution of 4-n-hexadecyl-1-bromobenzene (9.76g, 25mmol) in anhydrous tetrahydrofuran (150ml) was cooled to -25°C, and then 2.5M n-butylene was added dropwise thereto within 30 minutes under stirring Lithium hexane solution (10ml, 25mmol). The obtained slightly yellow emulsion mixture was stirred at the same temperature for 1 hour, and then compound 5 (2.14 g, 2.5 mmol) was added as a solid. The mixture was first cooled and stirred for 4 hours, and then stirred at room temperature for 4 hours until all the solids were dissolved. Distilled water (50 ml) was added to the reaction flask, followed by vigorous stirring at room temperature for 20 minutes. The mixture was transferred into a separatory funnel, the upper orange organic phase was separated, the lower aqueous phase was extracted with ether (50ml), the organic phases were combined, dried over anhydrous magnesium su...

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Abstract

The invention relates to small molecules and polymers which have a linear polycyclic conjugation structure and are condensed together, a synthesis method thereof, and applications thereof as a semiconductor active material on organic filed effect triodes, organic solar energy batteries, and other organic electronic devices. The synthesis method of the compounds with such structure comprises following steps: taking 2,5-dibromo-1,4-diethyl phthalate and condensed heterocyclic conjugation molecules as the primary raw material, then subjecting the primary materials to carry out cross-coupling to form a conjugation molecule intermediate containing four ester groups, then subjecting the ester groups to react with an organic lithium reagent so as to generate an intermediate with four alcohol groups, and finally subjecting the intermediate with four alcohol groups to carry out four ring-closure reactions under the acidic condition so as to obtain a highly-conjugated trapezoid polycyclic structure. The molecules with this structure can directly be used as a molecule type organic semiconductor material and can be used as a monomer synthesis polymer semiconductor material. These materials have an excellent organic solvent solubility, a solution processing property, and a high light, heat, and voltage stability. The organic field effect triode prepared by the materials has a charge transfer rate more than 0.8 cm2 / Vs, and has a potential application prospect on the field of organic electronics.

Description

technical field [0001] The present invention relates to a class of semiconductor small molecules and polymers containing ladder-shaped fused polycyclic conjugated structures, in particular to four small molecule derivatives containing 10 to 17 linearly fused polycyclic conjugated structures And polymer materials, their synthesis methods, and their application as semiconducting active materials in organic field effect triodes, organic solar cells and other organic electronic devices. Background technique [0002] Compared with traditional silicon semiconductors, organic semiconductor materials have many advantages such as light weight, low cost, good flexibility, simple manufacturing process, and soft processing temperature. Therefore, the application and research and development of organic semiconductor materials in microelectronic fields such as e-books, organic solar cells, organic sensors, organic radio frequency electronic tags (RFID) and even flexible displays have attr...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08G61/02C07D495/22H01L51/30H01L51/46
CPCY02E10/549
Inventor 周玉桐周剑波
Owner HUNAN AOXINKE MATERIAL
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