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Soluble benzenetetracarboxylic diimide group-containing full-conjugated polymer and preparation method thereof

A tetracarbonyldiimide group, conjugated polymer technology, applied in the field of soluble fully conjugated polymers, to achieve the effect of reducing steric hindrance, easy to arrange regularly, and mild polymerization conditions

Inactive Publication Date: 2012-06-20
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of polymers based on this structure has not been reported

Method used

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  • Soluble benzenetetracarboxylic diimide group-containing full-conjugated polymer and preparation method thereof
  • Soluble benzenetetracarboxylic diimide group-containing full-conjugated polymer and preparation method thereof
  • Soluble benzenetetracarboxylic diimide group-containing full-conjugated polymer and preparation method thereof

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preparation example Construction

[0026] The preparation method of each monomer is described as follows:

[0027] Preparation of monomer S1 before polymerization

[0028] The schematic diagram of the synthesis route of monomer S1 (dibromobenzenetetracarbonyldiimide and its derivatives) is as follows figure 2 shown. Monomer S1 is prepared by the literature method, and the detailed preparation method can be found in the literature report (J.Org.Chem.2008, 73, 4065-4075.).

[0029] Preparation of monomer S2 before polymerization

[0030] The schematic diagram of the synthesis route of monomer S2 (1,4 diynylbenzene) is as follows image 3 shown. Monomer S2 is prepared by using p-dibromobenzene as a raw material by a literature method, and the detailed preparation method can be found in literature reports (Synthetic Communications, 1996, 26, 2309-2316).

[0031] Preparation of monomer S3 before polymerization

[0032] The schematic diagram of the synthetic route of monomer S3 (p-2-alkynyl (2,5-trifluor...

Embodiment 1

[0033] Embodiment 1, synthetic polymer P1

[0034] The schematic diagram of the synthetic route of polymer P1 is as follows: Figure 5 As shown, the specific steps are: add 1mmol monomer S1 into a 100mL glass reaction bottle (at this time, R1 corresponding to monomer S1 is as shown in Table 1, which is -CH 2 CH(C 8 h 17 )C 10 h 21 ) and 1mmol monomer S2, then add 15mL dry toluene and 10mL dry triethylamine, stir and add 0.05mmol ditriphenylphosphine palladium dichloride and 0.1mmol cuprous iodide, react at 60°C for 24 hours Stop the reaction, pour into 200mL methanol for precipitation, and filter with suction to obtain a solid. The polymer was sequentially extracted with methanol, acetone and n-hexane Soxhlet, finally dissolved with chloroform, and finally precipitated with methanol to obtain the orange polymer P1, whose structural formula is shown in Table 1. Electrochemical test graph of polymer P1 as Figure 6 As shown, it can be seen from the figure that the start...

Embodiment 2～3

[0035] Embodiment 2~3, synthetic polymer P2~P3

[0036] The specific steps are the same as in Example 1: add 1 mmol of monomer S1 into a 100mL glass reaction bottle (at this time, R1 corresponding to monomer S1 is shown in Table 1, which are: -CH 2 CH(C 2 h 5 )C 4 h 9 ,-C 12 h 25 ) and 1mmol monomer S2, then add 15mL dry toluene and 10mL dry triethylamine, stir and add 0.05mmol ditriphenylphosphine palladium dichloride and 0.1mmol cuprous iodide, and react at 30°C for 2 hours Stop the reaction, pour into 200mL methanol for precipitation, and filter with suction to obtain a solid. The polymers were sequentially extracted with methanol, acetone and n-hexane Soxhlet, and finally dissolved in chloroform, and finally precipitated with methanol to obtain orange polymers P2-P3, whose structural formulas are shown in Table 1.

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Abstract

The invention discloses a soluble benzenetetracarboxylic diimide group-containing full-conjugated polymer and a preparation method thereof. The structural formula of the full-conjugated polymer is as the follow, wherein R1 is alkyl, R2 is hydrogen or trifluoromethyl, and n is more than or equal to 1. The preparation method comprises: adopting dibromobenzene tetracarboxylic diimide and 1,4-diethynylbenzene or a derivative of the 1,4-diethynylbenzene are adopted as monomers, and a copolymerization reaction is performed under a Heck reaction condition to obtain the full-conjugated polymer. Compared to the prior art, the polymer of the present invention has the following advantages that: the strong electron-deficient benzenetetracarboxylic diimide group is introduced in the molecule of the polymer, such that the polymer has low HUMO energy level, and the electrophilic capacity of the polymer is strong; the triple bond is introduced in the polymer, such that the steric hindrance between the donor unit and the receptor unit is reduced, the polymer is regularly aligned, and the electron mobility rate of the field effect transistor device containing the polymer of the present invention can be improved, therefore, wide application prospects are provided for the fields of polymer field effect transistors, thin film transistors and the like.

Description

technical field [0001] The invention relates to a soluble fully conjugated polymer containing a strongly electron-deficient benzenetetracarbonyldiimine group and a preparation method thereof. Background technique [0002] Polymer field effect transistors (FETs) and thin film transistors (TFTs), because of their light weight, simple preparation process, large-area film formation, and flexibility, have become the focus of attention in recent years; compared to p-type Organic semiconductor materials, designing organic semiconductor materials with n-type properties is more challenging, ((a) Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem. , Int. Ed. 47, 4070 (2008). (b) Mas-Torrent, M.; Rovira, C. Chem. Soc. Rev. 37, 827 (2008).). Therefore, it is of great scientific and practical significance to explore and design new n-type organic semiconductor materials. In 1996, tetracarbonyl dianhydride and tetracarbonyl diimide were first reported to have n-type...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D487/04H01L51/30
Inventor 胡超张清张国兵邓平曹康丽
Owner SHANGHAI JIAO TONG UNIV
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