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a kind of ab 2 Monomer and prepared donor-acceptor-donor-π bridge type hyperbranched conjugated polymer, preparation method and application thereof

A technology of hyperbranched conjugation and polymers, applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc.

Active Publication Date: 2021-02-12
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Hyperbranched conjugated polymers have excellent solubility because they are not easily entangled in solution like linear polymers, nor are they prone to aggregation due to intermolecular forces like some two-dimensional polymers. , good processability and other advantages, and because of its abundant and controllable modified end groups, it can be used to adjust the photoelectric properties of polymers, so it is used as donor materials, acceptor materials and electrodes in polymer solar cells Modified materials and other aspects have potential application value; but there are few reports on hyperbranched conjugated polymers for solar cells compared to linear conjugated polymers

Method used

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  • a kind of ab <sub>2</sub> Monomer and prepared donor-acceptor-donor-π bridge type hyperbranched conjugated polymer, preparation method and application thereof
  • a kind of ab <sub>2</sub> Monomer and prepared donor-acceptor-donor-π bridge type hyperbranched conjugated polymer, preparation method and application thereof
  • a kind of ab <sub>2</sub> Monomer and prepared donor-acceptor-donor-π bridge type hyperbranched conjugated polymer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A kind of AB 2 Monomer, its structure is shown in formula I:

[0056]

[0057] where R is -C 8 h 17 , and its preparation process is as follows:

[0058]

[0059] The first step, the synthesis of 1,3-dibromo-5-ethynyl-2-octyloxybenzene (M1), the specific method reference (Journal of Organic Chemistry, 69(10), 3336-3339; 2004) and (Journal of PolymerScience, Part A: Polymer Chemistry, 56(1), 96-104; 2018).

[0060] In the second step, the D-A-D unit (4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole) is replaced by iodine to obtain M2, the specific method reference (European Journal of Organic Chemistry, 2012(11), 2142-2151, S2142 / 1-S2142 / 93; 2012).

[0061] In the third step, M1 (9.00g), 228.8mg Pd (PPh 3 ) Cl 2 And 62.0mg CuI was added into a 500mL reaction flask, and vacuum pumping and nitrogen filling were repeated 3 times. Under the protection of nitrogen, 200 mL of THF that has been deoxidized and dehydrated and 1.80 mL of triethylamine were added success...

Embodiment 2

[0066] A kind of said donor-acceptor-donor-π bridge type (D-A-D-π type) hyperbranched conjugated polymer HBCP-Br, its structure is shown in formula II:

[0067]

[0068] where R is -C 8 h 17 .

[0069] Hyperbranched conjugated polymer HBCP-Br is based on the AB of embodiment 1 2 Monomer I is the raw material, prepared by Sonogashira coupling polymerization, the specific process is as follows:

[0070] Weigh AB 2 Monomer 1g, 30mg Pd(PPh 3 ) Cl 2 , 8mg CuI and 22mg PPh 3 Add it into the reaction bottle, repeat 3 times of vacuum pumping and nitrogen gas deoxygenation treatment, then add 20mL THF and 20mL triethylamine that have undergone strict dehydration and deoxygenation treatment, react under nitrogen protection at 60°C for 24 hours, filter, and remove the solvent under reduced pressure , the crude product was precipitated with petroleum ether and methanol successively, and the solid was collected and dried under vacuum to obtain 0.81 g of a hyperbranched polymer (H...

Embodiment 3

[0073] A kind of modification HBCP-CZ of described donor-acceptor-donor-π bridge type (D-A-D-π type) hyperbranched conjugated polymer, the hyperbranched polymer HBCP-Br prepared with embodiment 2 is The raw material is prepared by introducing a new donor or acceptor unit through the coupling reaction of its terminal -Br group. The specific process is as follows:

[0074] 100mg hyperbranched conjugated polymer HBCP-Br, 128mg 3-ethynyl-9-n-octylcarbazole, 8mg Pd(PPh 3 )Cl 2 , 2.14mg CuI and 4.43mg PPh 3 Add it into the reaction bottle, repeat the vacuum pumping and nitrogen gas removal treatment three times, then add 20mLTHF and 5mL triethylamine that have been strictly dewatered and deoxygenated, and react under nitrogen protection at 70°C for 24 hours. Filtrate with a short section of silica gel column, remove the solvent under reduced pressure, and then use petroleum ether and methanol to precipitate each time, collect the solid, and dry it under vacuum to obtain 91.2 mg of...

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Abstract

The invention discloses an AB 2 Monomer and prepared donor-acceptor-donor-π bridge hyperbranched conjugated polymer, preparation method and application thereof. The AB 2 The structure of the monomer is shown in formula I; by AB 2 The D-A-D-π type hyperbranched conjugated polymer can be obtained through the Sonogashira coupling polymerization reaction of the monomer. The D-A-D-π type hyperbranched conjugated polymer has a narrow molecular weight distribution, which is conducive to the preparation of a regular active layer in organic solar cells; the D-A-D-π type structure is conducive to Intramolecular charge transfer provides conditions for the further formation of hyperbranched conjugated polymers with lower HOMO energy levels and wider absorption in the visible region; at the same time, it contains a large number of terminal modifiable groups, which provide It provides a wide range of possibilities to adjust the photoelectric properties of polymers through terminal modification; through the method of terminal modification, the photoelectric properties of polymers can be adjusted; the hyperbranched conjugated polymers and their modifications are used in organic solar cells areas with potential applications.

Description

technical field [0001] The present invention relates to the technical field of organic solar cell materials, more specifically, to an AB 2 The monomer and the donor-acceptor-donor-π bridge (D-A-D-π) type hyperbranched conjugated polymer prepared therefrom and its preparation method and application. Background technique [0002] Solving energy and environmental problems by developing new materials and devices has always been the focus of scientific researchers, and solar cells are known as one of the most promising new energy devices. Organic polymer solar cells have become one of the most promising types of solar cells due to their highly tunable optical and electrical properties, flexibility and bendability, low cost, and wide range of synthesis sources. [0003] As an active donor material for organic solar cells, it needs to have a relatively broad absorption in the visible-near infrared region and a low HOMO energy level. Most of the polymers currently used in polymer ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/15C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G2261/415C08G2261/132C08G2261/18C08G2261/91C08G2261/72H10K85/113H10K30/00Y02E10/549
Inventor 梁晖罗栋潭清兰卢江
Owner SUN YAT SEN UNIV
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