A kind of hole transport material based on tetraaryl butadiene and its preparation method and application
A hole transport material and hole transport layer technology, applied in the preparation of aminohydroxy compounds, preparation of organic compounds, light-emitting materials, etc., can solve the problems of complicated and expensive synthesis, purification steps, limitations, etc., and achieve good optoelectronic properties and Thermal stability, improved hole mobility, low cost effects
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Embodiment 1
[0090] The synthesis of embodiment 1 compound CJ-03
[0091] The synthetic route of CJ-03 is as follows figure 1 As shown, the specific synthesis steps are as follows:
[0092] (1) Synthesis of compound 1
[0093]
[0094] Add 4,4'-dibromobenzophenone (1700.1 mg, 5.000 mmol, 1.00 equiv.), methyltriphenylphosphine bromide (3574.7 mg, 10.007 mmol, 2.00 equiv.) into a double-necked round bottom flask , Potassium tert-butoxide (1129.1 mg, 10.062 mmol, 2.01 equiv.) and tetrahydrofuran (20 mL), stirred, and reacted at room temperature under the protection of argon for 39.5 h. The solvent was distilled off under reduced pressure and separated by column chromatography (petroleum ether / ethyl acetate=50 / 1, v / v) to obtain a white solid (1257.0 mg, 74.37%), namely Compound 1.
[0095] Compound 1 1 H NMR spectrum as figure 2 Shown: 1 H NMR (300MHz, CDCl 3 ): δ(TMS, ppm)=7.47(d, J=9.0Hz, 4H), 7.18(d, J=9.0Hz, 4H), 5.46(s, 2H).
[0096] (2) Synthesis of compound 2
[0097]
...
Embodiment 2
[0119] The synthesis of embodiment 2 compound CJ-04
[0120] The synthetic route of CJ-04 is as follows figure 1 As shown, the specific synthesis steps are as follows: wherein steps (1) to (4) are the same as in Example 1;
[0121] (5) Synthesis of Compound 5
[0122]
[0123] Add 4-iodoanisole (2458.4 mg, 10.505 mmol, 2.06 equiv.), 1,10-phenanthroline monohydrate (199.4 mg, 1.006 mmol, 0.20 equiv.), iodide Cuprous (191.8mg, 1.007mmol, 0.20equiv.), potassium tert-butoxide (3370.6mg, 30.038mmol, 5.89equiv.), aniline (474.9mg, 5.099mmol, 1.00equiv.) and toluene (40mL), stirred, Heated to 130°C and refluxed for 39.0h under the protection of argon. The solvent was distilled off under reduced pressure and separated by column chromatography (petroleum ether / ethyl acetate=50 / 1, v / v) to obtain a yellow solid (946.4 mg, 60.78%), namely compound 5.
[0124] Compound 5 1 H NMR spectrum as Figure 14 Shown: 1 H NMR (400MHz, CDCl 3 ): δ(TMS,ppm)=7.16(t,J=8.0Hz,2H),7.04(d,J=8.0Hz,4...
Embodiment 3
[0155] The preparation of embodiment 3 perovskite solar cells
[0156] TiO 2 The preparation method of the dense layer is: adding titanium tetraisopropoxide (125 μL) into ethanol (845 μL) to obtain A solution. Add hydrochloric acid (2M, 11.6 μL) to ethanol (845 μL), solution B. Add solution B dropwise to solution A under stirring TiO 2 The preparation method of the mesoporous layer is as follows: dilute the titanium dioxide slurry (18 NR-T) in ethanol (w / w=1 / 7).
[0157] The preparation method of the perovskite precursor solution is: PbI 2 (1.2mmol / mL) and CH 3 NH 3 I (1.2 mmol / mL) was dissolved in DMF / DMSO (v / v=4 / 1).
[0158] The preparation method of HTM solution is: HTM [CJ-03 (60.0mg), CJ-04 (60.0mg) or spiro-OMeTAD (72.3mg)], Li-TFSI (9.1mg), FK209 (relative to the mole of HTM ratio of 15%) and t-BP (28.8 μL) were dissolved in chlorobenzene (1 mL).
[0159] A perovskite solar cell containing a hole transport material CJ-03 or CJ-04 is composed of a conductive subs...
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