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P-type conjugated polymer containing 3,4-dicyanothiophene, and preparation method and application thereof

A conjugated polymer and dicyano technology, applied in the field of p-type conjugated polymers and their preparation, can solve problems such as improvement, and achieve the effects of simple process, high dielectric constant and low manufacturing cost

Active Publication Date: 2019-08-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some wide-bandgap donor polymers have achieved high device performance in organic solar cells, most of the donor polymers have high HOMO, and it is difficult to make V oc Therefore, the design of donor polymers with deep HOMO energy levels is particularly important for breakthroughs in the photoelectric conversion efficiency of organic solar cells.

Method used

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  • P-type conjugated polymer containing 3,4-dicyanothiophene, and preparation method and application thereof
  • P-type conjugated polymer containing 3,4-dicyanothiophene, and preparation method and application thereof
  • P-type conjugated polymer containing 3,4-dicyanothiophene, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of Polymer PB3TCN-C66.

[0037] The chemical synthesis route of PB3TCN-C66 is shown below, and the specific reaction steps and reaction conditions are as follows:

[0038]

[0039] (1) Preparation of raw materials or intermediate reactants: raw material 1 according to the method reported in the literature (Wang, Y.; Hasegawa, T.; Matsumoto, H.; Mori, T.; Michinobu, T. Rational Design of High-Mobility Semicrystalline Conjugated Polymers with Tunable Charge Polarity:BeyondBenzobisthiadiazole-Based Polymers, Adv.Funct.Mater.2017,27,1604608.); raw material 2 according to the method reported in the literature (Balandier, J.; Quist, F.; Amato, C.; Bouzakraoui, S.; Cornol, J.; Sergeyev, S.; Geerts, Y. Synthesis of soluble oligothiophenes bearing cyanogroups, their optical and electrochemical properties, Tetrahedron 2010, 66, 9560-9572.) prepared. Raw material 5, tetrahexatriphenylphosphine palladium (Pd(PPh 3 ) 4 ), N-bromosuccinimide (NBS), tris(dibenzyliden...

Embodiment 2

[0047] Preparation of polymer PB3TCN-EH-EH.

[0048] The chemical synthesis route of PB3TCN-EH-EH is shown below, and the specific reaction steps and reaction conditions are as follows:

[0049]

[0050] (1) Preparation of raw materials or intermediate reactants: raw material 6 according to the method reported in the literature (Bundgaard, E.; Krebs, F.Low-Band-Gap Conjugated Polymers Based on Thiophene, Benzothiadiazole, and Benzobis (thiadiazole) Macromolecules 2006,39, 2823-2831.) According to the method reported in the literature (Balandier, J.; Quist, F.; Amato, C.; Bouzakraoui, S.; Cornol, J.; Sergeyev, S.; Geerts, Y.Synthesis of soluble oligothiophenes bearing cyano groups, theiroptical and electrochemical properties, Tetrahedron 2010, 66, 9560-9572.) prepared. Raw material 10, tetrahexa triphenylphosphine palladium (Pd(PPh 3 ) 4 ), N-bromosuccinimide (NBS), tris(dibenzylideneacetone) dipalladium (Pd 2 (dba) 3 ), three (o-methylphenyl) phosphorus (P (o-tol) 3 )...

Embodiment 3

[0058] Preparation of polymer PB3TCN-EH-C12.

[0059] The chemical synthesis route of PB3TCN-EH-C12 is shown below, and the specific reaction steps and reaction conditions are as follows:

[0060]

[0061] (1) Preparation of raw materials or intermediate reactants: raw material 11 according to the method reported in the literature (Wu, P.; Kim, F.; Champion, R.; Jenekhe, S. Conjugated Donor-Acceptor Copolymer Semiconductors. Synthesis, Optical Properties, Electrochemistry , and Field-EffectCarrier Mobility of Pyridopyrazine-Based Copolymers.Macromolecules 2008,41,7021-7028.) Raw material 12 according to the method reported in the literature (Balandier, J.; Quist, F.; Amato, C.; Bouzakraoui, S.; Cornol, J.; Sergeyev, S.; Geerts, Y. Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties, Tetrahedron 2010, 66, 9560-9572.)) prepared. Raw material 15, tetrahydryl triphenylphosphine palladium (Pd(PPh 3 ) 4 ), N-bromosuccinimide ...

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Abstract

The invention discloses a p-type conjugated polymer containing 3,4-dicyanothiophene, and a preparation method and an application thereof. The method comprises the following steps: mixing a thiophene unit monomer containing 3,4-dicyanothiophene, a monomer containing a conjugated unit Ar1 and a monomer containing a conjugated unit Ar2, then performing polymerization reaction under catalysis of a catalyst, and purifying the obtained reaction product to obtain the p-type conjugated polymer containing 3,4-dicyanothiophene. The polymer provided by the invention is simple to synthesize, the introduction of a cyano group can regulate the energy level of the molecule, and the cyano group has a low molecular orbital energy level and a wide optical band gap, and can achieve good optical absorption complementation with an n-type organic semiconductor material; and compared with conjugated polymers free from the cyano substituent, the conjugated polymer containing 3,4-dicyanothiophene has the advantages of large dipole moment, high dielectric constant, facilitation of the reduction of exciton binding energy, promotion of the separation of electrons and holes, and realization of the preparationof high-performance organic solar cells.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and specifically relates to a class of p-type conjugated polymers containing 3,4-dicyanothiophene, a preparation method and applications thereof. Background technique [0002] Organic solar cells have attracted much attention due to their low cost, light weight, flexibility, and large-area solution processing. The active layer of organic solar cells is usually composed of conjugated polymers as electron donors and fullerene derivatives as electron acceptors. Fullerene derivatives are limited by their narrow absorption spectrum, difficulty in structural modification, and high preparation costs. In the past three years, thanks to the development of A-D-A type non-fullerene small molecules (SMAs), the performance of fullerene as an electron acceptor material for organic solar cells has been improved and used on a large scale. The photoelectric conversion efficiency ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G2261/124C08G2261/143C08G2261/18C08G2261/3223C08G2261/3243C08G2261/91H10K85/113H10K30/30Y02E10/549
Inventor 段春晖张拨曹镛
Owner SOUTH CHINA UNIV OF TECH
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