Conjugated polymer based on indolinone and naphthalimide units and preparation method thereof

A naphthalene diimide and conjugated polymer technology, which is applied in the field of organic semiconductor acceptor polymers and their preparation, can solve the problems of few application reports of synthetic polymers, and achieve good chemical stability, low price, and easy availability Effect

Active Publication Date: 2021-07-13
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, carbon-hydrogen activated coupling is generally applied to small molecular compounds, and there are few reports on the application of synthetic polymers.

Method used

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  • Conjugated polymer based on indolinone and naphthalimide units and preparation method thereof
  • Conjugated polymer based on indolinone and naphthalimide units and preparation method thereof
  • Conjugated polymer based on indolinone and naphthalimide units and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, preparation of conjugated polymer based on indolinone and naphthalimide unit conjugated polymer conjugated polymer

[0046] This example provides two kinds of soluble conjugated polymers based on indolinone and naphthalene diimide units, the structural formula of which is shown in Table 1 (wherein, n≥1), and its synthetic route can be found in figure 1 .

[0047]

[0048] 1.1. Preparation of monomer M1

[0049] The synthetic route of the first monomer M1 (M1-1, M1-2) of P1, P2 polymer is roughly the same, and it specifically comprises the following steps:

[0050] (a) Synthesis of intermediate compound C

[0051] The structural formula of intermediate compound C is

[0052]

[0053] Its detailed preparation method is: under the protection of nitrogen, put 6-bromo-2-indolinone (20mmol), 2-thiophene carboxaldehyde (22mmol) into a two-necked flask, and then add a certain amount of methanol, the reactant A suspension formed. Then measure 5ml of pipe...

Embodiment 2

[0075] Embodiment 2, the ultraviolet absorption spectrum and the electrochemical property of polymer P1

[0076] 2.1. UV absorption spectrum of polymer P1

[0077] Image 6 The ultraviolet absorption spectrum of polymer P1 in chloroform and film is given, and it can be seen that the polymer has two absorption peaks. In the film, NDI with side chains has a strong absorption at 350nm-550nm, and thiophene-2-indole Keto-thiophene has a strong absorption at 600nm-780nm, and generally speaking, it has a wide range of ultraviolet-visible light absorption. The onset absorption of the film (λonset film ) is 842nm, according to the formula Eg film =1240 / λonset film Eg can be obtained by eV calculation film =1.47eV, indicating that the polymer is a narrow bandgap polymer.

[0078] 2.2. Electrochemical properties of polymer P1

[0079] The electrochemical properties of the polymer were tested with platinum sheet as working electrode, platinum wire as counter electrode and saturated...

Embodiment 3

[0081] The ultraviolet absorption spectrum and electrochemical properties of embodiment 3, polymer P2

[0082] 3.1. UV absorption spectrum of polymer P2

[0083] Figure 7 The ultraviolet absorption spectrum of polymer P2 in chloroform and film is given, and it can be seen that the two absorption peaks of the polymer have similar absorption intensities. Therefore, polymer P2 has a wide range of UV-visible light absorption and high absorption intensity. The onset absorption of the film (λonset film ) is 845nm, according to the formula Eg film =1240 / λonset film Eg can be obtained by eV calculation film = 1.47eV.

[0084] 3.2. Electrochemical properties of polymer P2

[0085] The electrochemical properties of the polymer were tested with platinum sheet as working electrode, platinum wire as counter electrode and saturated calomel electrode as reference electrode. In anhydrous acetonitrile solvent, with the concentration of 0.1mol / L tetrabutylammonium hexafluorophosphate a...

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Abstract

The invention relates to a conjugated polymer based on indolinone and naphthalene diimide units and a preparation method thereof. The structural formula of the conjugated polymer is as follows: wherein, R 1 , R 2 , R 3 It is a branched alkyl chain, n≥1. The invention also relates to a method for the preparation of conjugated polymers based on indolinone and naphthalimide units. The conjugated polymer based on indolinone and naphthalimide units in the present invention has broad and strong absorption in the visible-near infrared region. The pendant alkyl groups on the naphthalimide and indolinones provide good solubility for the present invention so this material is solution processable. In the present invention, the conjugated polymer based on indolinone and naphthalene diimide units is formed by carbon-hydrogen activated polymerization. The method has simple synthesis steps and no metal by-products, and can obtain polymers with higher molecular weight and fewer structural defects. The polymerization method involved in the invention conforms to the principle of environmental protection and economical green chemistry.

Description

technical field [0001] The invention relates to an organic semiconductor acceptor polymer with strong absorption in the near-infrared region of visible light and a preparation method thereof, belonging to the field of acceptor materials for organic solar cells. Background technique [0002] Organic solar cells have attracted widespread attention in recent years because of their low cost, solution processing, and flexible devices. The main material of organic solar cells is organic conjugated polymer, and most of its polymerization methods use halogenated monomers and organometallic monomers for carbon-carbon bond coupling, such as Stille coupling and Suzuki coupling. This synthetic strategy can synthesize most conjugated polymers, but at the same time, there is a problem in these reactions that organometallic compounds (boric acid, borate, butyllithium or organotin reagents, etc.) must be used, and the use of these organometallic compounds Additional synthesis steps and pur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G61/124C08G61/122C08G2261/124C08G2261/1412C08G2261/18C08G2261/3223C08G2261/3241C08G2261/91H10K85/151Y02E10/549
Inventor 邓平林珍松郝祥宇
Owner FUZHOU UNIV
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