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N-type conjugated polymer containing oligomeric ethylene glycol side chain modified naphthalene diimide unit and application of conjugated polymer in organic photoelectric devices

A technology of oligoethylene glycol and naphthalene diimide, which is applied in the field of n-type conjugated polymers, can solve the problems of poor stability and difficulty in controlling the morphology of the blended film of the photoactive layer, and achieve excellent stability Effect

Inactive Publication Date: 2018-12-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the disadvantages of difficult control and poor stability of the blended film morphology of the photoactive layer in the device structure of the bulk heterojunction organic / polymer solar cell in the above-mentioned prior art, the object of the present invention is to provide a n-type conjugated polymer acceptor material with mixed active layer morphology, mixed with polymer donor to prepare polymer / polymer solar cell devices with ideal morphology and long-term stability

Method used

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  • N-type conjugated polymer containing oligomeric ethylene glycol side chain modified naphthalene diimide unit and application of conjugated polymer in organic photoelectric devices
  • N-type conjugated polymer containing oligomeric ethylene glycol side chain modified naphthalene diimide unit and application of conjugated polymer in organic photoelectric devices
  • N-type conjugated polymer containing oligomeric ethylene glycol side chain modified naphthalene diimide unit and application of conjugated polymer in organic photoelectric devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of Naphthalimide Monomer (Structure 3) Modified with Oligoethylene Glycol Side Chain.

[0028] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0029]

[0030] (1) Raw materials or intermediate reactants, tetraethylene glycol monomethyl ether, diisopropyl azodicarboxylate, phthalimide, triphenylphosphine, hydrazine hydrate, 2,6-dibromonaphthalene-1 ,4,5,8-Tetracarboxylic dianhydride is used directly as a commercial product.

[0031] (2) Preparation of intermediate 1

[0032] Under nitrogen protection, tetraethylene glycol monomethyl ether (6g), phthalimide (4.5g) and triphenylphosphine (8.5g) were dissolved in 150 ml of dichloromethane, at 0 ° C 6.5 g of diisopropyl azodicarboxylate was slowly added dropwise to the reaction liquid, and stirred at room temperature for 12 hours. After the reaction was completed, the solvent was removed, and purified by silica gel column to obtain 7 g o...

Embodiment 2

[0038] Preparation of n-Type Conjugated Polymer (NOE10) Containing Naphthalimide Units Modified by Oligoethylene Glycol Side Chains

[0039] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0040]

[0041] (1) Raw materials or intermediate reactants, monomer 4, monomer 5, and tetrakistriphenylphosphine palladium are used directly as commercial products.

[0042] (2) Under nitrogen protection, dissolve monomer 3 (0.02 mmol), monomer 4 (0.18 mmol), monomer 5 (0.2 mmol) and 3 mg of tetraphenylphosphine palladium in 2 ml of chlorine In benzene, stir at 120°C for 12 hours. After the reaction, the polymer was precipitated in methanol, extracted with methanol, acetone, and n-hexane, and finally extracted with chloroform to obtain the final polymer. The final polymer NOE10 was obtained after precipitation with methanol again, 180 mg, and the yield was 90%.

Embodiment 3

[0044] The polymer material obtained in Example 2 is taken as an example to illustrate the application of this polymer material as a polymer acceptor in polymer / polymer solar cell devices.

[0045] The following examples will illustrate the n-type conjugated polymer containing oligoethylene glycol side chain modified naphthalene diimide units proposed by the present invention and its application process in organic photoelectric devices, but the present invention does not limited to the examples given.

[0046] The specific preparation process of the device is as follows:

[0047]Spin-coat a layer of 40nm PEDOT:PSS hole transport layer on ITO, then spin-coat the photoactive layer of polymer donor PBDT-TAZ and NOE10 blended with about 100nm, and then spin-coat about 5nm of amine-based polymer The quaternary ammonium bromide salt of fluorene (PFN-Br) was used as the cathode interface layer, and then a 100 nanometer Ag layer was evaporated to complete the preparation of the devic...

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Abstract

The invention relates to an N-type conjugated polymer containing an oligomeric ethylene glycol side chain modified naphthalene diimide unit and an application of the conjugated polymer in organic photoelectric devices. A structural formula of the N-type conjugated polymer containing the oligomeric ethylene glycol side chain modified naphthalene diimide unit is shown in the specification; wherein Ar1 and Ar2 are aromatic groups; R1 and R2 are H, C1-50 alkyl straight or branched chains; m is an integer with a range of 1-10; x is greater than 0 and less than 1, y is greater than 0 and less than 1, and the sum of x and y is 1; and n is a natural number with a range of 1-10000. The polymer has suitable electron transport properties and is suitable for use in the organic photoelectric devices with suitable blend film morphology, and the produced device has high performance and / or good long-term stability.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to n-type conjugated polymers containing oligoethylene glycol side chain modified naphthalene diimide units and their application in organic photoelectric devices. Background technique [0002] Due to the increasing global demand for energy, the depletion of traditional energy sources such as oil and coal, and the need to protect the earth's ecological environment, more and more scientists around the world are focusing their research on the development and utilization of wind energy, geothermal energy, solar energy, etc. Inexhaustible renewable clean energy. [0003] Organic / polymer solar cells based on organic / polymer materials, as a new type of thin-film photovoltaic cell technology, have the advantages of all-solid-state, translucent, and flexible devices. In addition, organic / polymer solar cells can be fabricated into large-area devices using low-cost roll-to-roll...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46H01L51/48
CPCC08G61/122C08G61/126C08G2261/3223C08G2261/18C08G2261/3241C08G2261/124C08G2261/1424C08G2261/91H10K85/00H10K30/15Y02E10/549
Inventor 段春晖刘熙黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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