A non-doped hole transport material based on dicyanofluoranthene
A hole-transport material and non-doping technology, applied in the chemical industry, can solve the problems of increasing device cost, efficiency attenuation, battery performance attenuation, etc., and achieve high photoelectric conversion efficiency
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Embodiment 1
[0067] Synthesis of compound 2: The synthetic route is as attached image 3 .
[0068] Synthesis of Intermediate 2-1
[0069] In a 250mL schlenk bottle, add 2,7-dibromofluorenone (3.38g, 10mmol), 4,4-dimethyldiphenylamine (4.33g, 22mmol), Pd(dba) 2 (366mg, 0.4mmol), sodium tert-butoxide (2.4g, 25mmol), tri-tert-butyl phosphine (1.5mL, 0.6mmol,) and 40mL of dry toluene, heated to reflux under nitrogen for 12 hours, cooled, and dichloromethane After the methane was extracted and dried, the solvent was removed, and 4.95 g of dark red solid was obtained after separation on a silica gel column, with a yield of 86.8%. 1 H NMR (400MHz, Chloroform-d) δ 7.25 (d, J = 2.2 Hz, 2H, ArH), 7.17 (d, J = 8.1 Hz, 2H, ArH), 7.10-7.02 (m, 10H, ArH), 6.97(d,J=8.4Hz,8H,ArH),2.31(s,12H,-CH 3 ).
[0070] Synthesis of Intermediate 2-2
[0071] In a 100mL schlenk flask, add Intermediate 2-1 (1.14g, 2.0mmol) and 10mL dry tetrahydrofuran, slowly add methyl lithium (1.38mL, 2.2mmol) at -78℃, gradually warm to ro...
Embodiment 2
[0076] The synthesis of compound 3, the synthetic route is as attached Figure 7 .
[0077] Synthesis of Intermediate 3-1
[0078] In a 250mL schlenk bottle, add 2,7-dibromofluorenone (1.69g, 5mmol), 4,4-dimethoxydiphenylamine (2.29g, 10mmol), Pd(dba)2 (180mg, 0.2mmol) , Sodium tert-butoxide (1.2g, 12.5mmol), Tri-tert-butylphosphine (0.75mL, 0.3mmol,) and 40mL dry toluene, heated to reflux for 24 hours under nitrogen conditions, cooled, extracted with dichloromethane and dried The solvent was removed, and then separated by a silica gel column to obtain 2.60 g of dark red solid with a yield of 82.3%. 1 H NMR (400MHz, Chloroform-d) δ 7.17 (d, J = 2.2 Hz, 2H, ArH), 7.13 (d, J = 8.2 Hz, 2H, ArH), 7.03 (d, J = 8.8 Hz, 8H, ArH), 6.98–6.90(m,2H,ArH), 6.83(d,J=8.9Hz,8H,ArH), 3.80(s,12H,-OCH 3 ).
[0079] Synthesis of Intermediate 3-2
[0080] In a 100mL schlenk bottle, add Intermediate 3-1 (1.27g, 2.0mmol) and 10mL dry tetrahydrofuran, slowly add methyl lithium (1.38mL, 2.2mmol) at -78℃, gr...
Embodiment 3
[0085] Compounds 2 and 3 as the device performance of the hole transport layer of perovskite solar cells:
[0086] The hole mobility of compounds 2 and 3 under non-doped conditions measured by the method of space charge limiting current are 6.36×10 -5 And 1.17×10 -4 cm 2 V -1 s -1 (see Picture 11 ), and the hole mobility of the reference spiro-OMeTAD measured under the same conditions is 2.36×10 -5 cm 2 V -1 s -1 , Which shows that the compounds 2 and 3 designed in this patent have higher hole mobility and can meet the needs of the hole transport layer of the perovskite battery. Compounds 2 and 3 are used as hole transport materials for the preparation of formal planar structure perovskite solar cells without any doping. The specific device structure is FTO / SnO 2 / PCBM / mixed perovskite / HTL / MoO 3 / Au, the composition of the mixed perovskite is: (FAPbI 3 ) 0.85 (MAPbBr 3 ) 0.15 (FA:NH=CHNH 3 + ;MA:CH 3 NH 3 + ). When the light intensity is 100mW cm -2 Under the simulated sunlight A...
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