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Conjugated polymer containing Indacene tetrone and application of conjugated polymer in organic electronic device

A technology of organic electronic devices and conjugated polymers, applied in the field of polymer materials, to achieve the effect of medium and wide bandgap absorption, cheap raw materials, and low-cost preparation

Active Publication Date: 2021-08-17
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current literature, the use of indacenetetraketone units in organic porous polymers (CN 112574407A, CN 112574395 A, CN 109265657 A, etc.), the preparation of photovoltaic donor / acceptor small molecules (Adv.Funct.Mater.2014,24,4645- 4653; Thin Solid Films 2015,583,34-39; WO 2011 / 105624 Al.), nonlinear optical materials (Proceedings of SPIE 2013,8827.), but used to prepare conjugated polymers and apply them to organic electronics The field of devices has not been reported yet

Method used

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  • Conjugated polymer containing Indacene tetrone and application of conjugated polymer in organic electronic device
  • Conjugated polymer containing Indacene tetrone and application of conjugated polymer in organic electronic device
  • Conjugated polymer containing Indacene tetrone and application of conjugated polymer in organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis route of the conjugated polymer P1 containing the provincial tetraenone is as follows:

[0036]

[0037] (1) Synthesis of Compound 4

[0038]Amphalophenylene tetramethlorhydride (23 mmol, 5g), acetoacetyl (69 mmol, 8.94 g), triethylamine (275 mmol, 12 27.8 g) was dissolved in acetic anhydride (80 mL), heated at 100 ° C for 2 hours, then The reaction liquid was cooled in a refrigerator at 3 ° C for 24 hours to obtain a mixture of solid precipitated. The solid was filtered and washed with a small amount of acetic anhydride and diethyl ether to give the intermediate 2. The resulting intermediate 2 is dissolved in water and used in an ice bath. 2 SO 4 Acidification of solids. The reaction liquid was then filtered, ethanol was washed, and the temperature was dried in the fume housing for 24 hours, and the residual moisture was removed from the oil pump to obtain Compound 3. A large amount of acetic acetonitrile was added to compound 3, and after stirring for 3 ho...

Embodiment 2

[0044] The synthesis method of Compound 6 has been given in Example 1, and the polymer P2 in Example 2 obtained by the same similar method, the synthetic route is as follows:

[0045]

[0046] The resulting compound 6 (0.1 mmol, 112.1 mg), double tin monomer 8 (0.1 mmol, 94.1 mg), and catalyst Pd 2 (DBA) 3 (0.003mmol, 2.7mg) and ligand p (o-tol) 3 (0.024 mmol, 7.3 mg) was dissolved in 4 ml of anhydrous oxygen-oxygenlobenzene under an argon atmosphere, and the reaction solution was stirred at 80 ° C for 1.8 hours. Subsequently, the reaction liquid dropped into 150 ml of methanol and filtered the obtained blue precipitate, and further use methanol, n-hexane, dichloromethane, chloroform and chlorobenzene, and low molecular weight groups by the rope extractor. share. The solution of the chloroprene phase was concentrated and precipitated in 100 ml of methanol, i.e., the target polymer P2, the weight was 86 mg, and the yield was 54%. GPC: Mn = 25.4kda, PDI = 1.71 (eg figure 2 ). Anal...

Embodiment 3

[0048] The synthesis method of Compound 6 has been given in Example 1, and the polymer P3 in Example 3 obtained by the same similar method, the synthetic route is as follows:

[0049]

[0050] The obtained compound 6 (0.1 mmol, 112.1 mg), double tin monomer 9 (0.1 mmol, 97.3 mg), and catalyst Pd 2 (DBA) 3 (0.003mmol, 2.7mg) and ligand p (o-tol) 3 (0.024 mmol, 7.3 mg) was dissolved in an argon atmosphere of 4 ml anhydrous oxygenlobenzene, and the reaction liquid was stirred at 80 ° C for 1.6 hours. Subsequently, the reaction liquid dropped into 150 ml of methanol and filtered the obtained blue precipitate, and further use methanol, n-hexane, dichloromethane, chloroform and chlorobenzene, and low molecular weight groups by the rope extractor. share. The solution of the chloroprene phase was concentrated and precipitated in 100 ml of methanol, and the target polymer P3 was obtained. Weight of 82 mg, 50% yield. GPC: Mn = 27.0kda, PDI = 2.88 (eg image 3 ). Anal.calcd for (c 96 Hide 1...

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Abstract

The invention discloses a conjugated polymer containing Indacene tetrone and application of the conjugated polymer in an organic electronic device. The conjugated polymer ontaining Indacene tetrone has a structure shown in the specification, wherein n is an integer between 1 and 100, A1 and A2 are identical or different conjugated units, and C is a conjugated unit. Indacene tetrone has four electron-withdrawing carbonyl groups, so that the electronegativity of a polymer main chain can be enhanced, and an electron transmission effect is achieved. In addition, carbonyl reduces delocalization of electrons in the whole conjugated main chain, and the purpose of medium-wide band gap optical absorption can be achieved. The conjugated polymer with Indacene tetrone as the electron-deficient unit can be applied to the field of organic electronic devices (including polymer solar cells, n-type field effect transistors, perovskite solar cells, organic thermoelectric devices and organic photodetectors).

Description

Technical field [0001] The present invention relates to the field of polymeric materials, and more particularly to a conjugated polymer that is a provincial tetraenone and its application in organic electronic devices. Background technique [0002] In recent years, the use of clean energy by low-cost technological means, which has caused more and more attention, and organic solar cells (OSCs) have emerged as it is easy to prepare, flexible, and large-scale processed advantages. Compared to inorganic silicon solar cells, organic solar cell materials have a wide range of sources, rich species, easy to regulate, and solution processability can help achieve low cost, large-scale preparation of flexible large-area devices, and inorganic semiconductor solar energy Battery formation is complementary, thus showing huge business development value and market competitiveness. [0003] Since 2015, organic solar cells have developed rapidly, and the highest photovoltaic efficiency of devices ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/30H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/145C08G2261/18C08G2261/3223C08G2261/3243C08G2261/91C08G2261/92C08G2261/95H10K85/113H10K10/46H10K30/00Y02E10/549
Inventor 杨楚罗贾建超
Owner SHENZHEN UNIV