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Conjugated polymer based on trifluoromethyl substituted quinoxaline as well as preparation method and application of conjugated polymer
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A technology of conjugated polymers and trifluoromethyl, applied in the field of conjugated polymers based on trifluoromethyl substituted quinoxalines and its preparation, can solve the problems of lengthy synthetic routes, low yields, complex molecular structures, etc. , to achieve the effect of simple synthesis method, high yield and improved photovoltaic performance
Pending Publication Date: 2022-08-09
POLYROCKS TECH&RES CO LTD
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However, the current high-efficiency polymer donor materials such as PM6 and D18 have complex molecular structures, tedious synthetic routes, and low yields; and the fluorination of polymer donor materials is generally to directly introduce fluorine atoms on the aromatic ring, which has been difficult. Meet the needs of actual use
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Embodiment 1
[0061] A conjugated polymer P1 based on trifluoromethyl substituted quinoxaline, its structural formula is as follows:
[0066] Compound 1 (797.7 mg, 3 mmol) was dissolved in toluene (40 mL), stirred at room temperature and slowly added dropwise ethyl trifluoropyruvate (680.4 mg, 4 mmol). After 1 h of reaction, a white solid precipitated out of the solution. The reaction mixture was stirred at room temperature for 30 min, then refluxed in a flask equipped with a water separator for 2 h, and the reaction solution was concentrated under vacuum to give compound 2 (929.8 mg, yield: 83.3%) as a white solid without further purification.
[0067] Compound 2 (929.8 mg, 2.5 mmol), potassiumcarbonate (414.6 mg, 3.0 mmol) and 1-bromo-2-hexyldecane (916.2 mg, 3.0 mmol) were dissolved in N,N-dimethylformamide solution ( 30mL). The mixture was refluxed for 12 h, then cooled to ro...
Embodiment 2
[0072] A conjugated polymer P2 based on trifluoromethyl substituted quinoxaline, its structural formula is as follows:
[0076] The same as the preparation of compound 2 in Example 1, only the amount of compound 1 such as o-phenylenediamine is replaced with compound 3, and finally a light yellow oily substance M2 is obtained. 1 H NMR (600MHz, Chloroform-d) δ4.61 (d, J=5.4Hz, 2H), 1.94 (hept, J=6.1Hz, 1H), 1.53–1.37 (m, 8H), 1.35–1.24 (m, 16H),0.90(td,J=6.9,3.1Hz,6H).
[0077] (2) Synthesis of P2:
[0078] The same as the preparation of P1 in Example 1, only the amount of monomer M1 was replaced with the trifluoromethyl-containing quinoxaline precursor M2 in Example 2 (GPC: Mn=36.5KDa, PDI=2.3) .
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Abstract
The invention relates to a conjugated polymer based on trifluoromethyl substituted quinoxaline, a preparation method of the conjugated polymer and application of the conjugated polymer in an organic photovoltaic device. The conjugated polymer based on trifluoromethyl substituted quinoxaline is formed by copolymerization of trifluoromethyl substituted quinoxaline, a conjugated aromatic ring and a derivative unit thereof. The method has the advantages of simple synthesis method, high yield and lower cost; meanwhile, trifluoromethyl has a strong electron-withdrawing induction effect, lipophilicity and a stable C-F bond, and compared with a traditional donor material, trifluoromethyl is introduced into the conjugated polymer, the photovoltaic performance of trifluoromethyl is improved more remarkably, and the conjugated polymer has a good commercialization prospect.
Description
technical field [0001] The invention relates to the field of optoelectronic technology, in particular to a conjugated polymer based on trifluoromethyl substituted quinoxaline, a preparation method and application thereof. Background technique [0002] With the development of human beings, traditional fossil energy has been continuously consumed, and environmental pollution has become increasingly serious. The world energy system is facing the dual challenges of "more energy" demand and "lower carbon emission". And solar energy is an inexhaustible clean energy, so the research and utilization of organic solar cells is also considered to be one of the most effective ways to solve the energy crisis. [0003] The upper limit of the energy conversion efficiency of organic solar cells is mainly determined by the active layer material, which is composed of two parts, the donor and the acceptor. At present, the construction of efficient polymer-donor photovoltaic materials is gener...
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