A kind of heteropolytriyne cross-conjugated polymer, its preparation and application
A cross-conjugation and polymer technology, applied in the field of organic optoelectronic polymer materials, can solve the problems of affecting the photostability of spiro-OMeTAD devices, accelerating the degradation of perovskite, and deteriorating the long-term stability of devices, etc., and the preparation method is simple and easy line, high energy conversion efficiency, low cost effect
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Embodiment 1
[0064] Synthesis of Compound P1: The synthetic route is shown in the instructions attached figure 1 .
[0065] Synthesis of Intermediate 2
[0066] 2,7-bis(4,4'-dimethyldiphenylamine) fluorenone (1,1.00g, 1.75mmol), carbon tetrabromide (1.16g, 3.50mmol), triphenylphosphine (1.78g, 6.79mmol) and 100-120mL of dry DCM were added into a 250mL round bottom flask, heated to 40-50°C for 24-32h. After the reaction solution was cooled to room temperature, it was extracted with water, dried by adding anhydrous sodium sulfate, filtered, and separated through a silica gel column after removing the solvent (eluent: petroleum ether: dichloromethane = 10:1) to obtain 0.90 g of a dark red solid , and the yield was 70.9%. 1 H NMR (400MHz, Chloroform-d) δ8.30 (d, J = 2.1Hz, 2H, ArH), 7.36 (d, J = 8.2Hz, 2H, ArH), 7.11–6.93 (m, 18H, ArH), 2.30(s,12H, -CH 3 ). 13 C NMR (101MHz, Chloroform-d) δ138.98, 132.28, 132.12, 132.02, 131.94, 129.81, 128.55, 128.43, 124.24, 121.27, 119.23, 90.83, 20.8...
Embodiment 2
[0072] The synthesis of compound P2, the synthetic route is as attached to the description Figure 4 .
[0073] Compound 2 (0.40g, 0.55mmol), 1,4-diethynylbenzene (0.07g, 0.55mmol), Pd(PPh 3 ) 4 (0.03g, 0.02mmol), CuI (0.03g, 0.17mmol), iPr 2 NH (20mL) and dry THF (40mL) were added to a 250mL dry Schlenk bottle under N 2 Carry out three freeze-vacuum-thaw cycle deoxygenation operations under the same conditions, and then heat to 70-80°C to react for 72-80h. After cooling, add water and dichloromethane for extraction, dry and spin dry to obtain a brown solid, which is dissolved in a small amount of chloroform, reprecipitated in methanol, and filtered. Put the obtained precipitate into a Soxhlet extractor for extraction, successively extract with 50-60 mL of methanol, acetone and n-hexane for 24-30 h, remove small molecules and catalysts, and obtain 0.12 g of the product with a yield of 31.6%. 1 H NMR(400MHz,Chloroform-d)δ8.61(br,2H,ArH),7.38(br,2H,ArH),7.10-6.79(br,18H,ArH...
Embodiment 3
[0077] Device performance of compounds P1 and P2 as hole transport layers in perovskite solar cells:
[0078] The highest occupied molecular orbital (HOMO) energy levels of polymers P1 and P2 were tested by cyclic voltammetry, and the test results were as follows Figure 7 As shown, their calculated HOMO energy levels are -5.06 and -5.08eV, respectively. The lowest unoccupied molecular orbital (LUMO) energy levels of the two polymers were calculated from the optical band gaps obtained by UV absorption spectra to be -2.36 and -2.63eV.
[0079] Subsequently, using the space charge limited current (SCLC) method, the hole mobilities of compounds P1 and P2 were measured to be 1.85×10 -6 and 2.17×10 -6 cm 2 V -1 the s -1 (See Figure 8), indicating that the compounds P1 and P2 designed in this patent have higher hole mobility.
[0080] The above experimental results show that the two polymers P1 and P2 designed in this patent can meet the requirements of the hole transport layer ...
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