Syntheses And Device Performances Of Novel Three-dimensional Rigid Conjugated Molecules

Three-dimensional（3D）organic conjugated materials have unique stereoscopic molecular configurations,which are beneficial to the realization of multidirectional charge transport and the regulation of molecular solid-state self-assembly structures,so they show significant research value in the field of organic electronics.Due to the lack of efficient chemical synthesis methods,currently there are relatively few types of 3D materials compared to one-dimensional and two-dimensional materials.Trinaphtho[3.3.3]propellane is an ideal molecular unit for constructing 3D organic conjugated compounds due to its large rigid conjugated plane and multiple reactive sites.Based on the above discussion,the syntheses of 3D rigid conjugated molecules are researched through direct functionalization and lateral conjugate expansion by selecting trinaphtho[3.3.3]propellane as the core molecular framework in this thesis,and the device performances of the target compounds are initially explored.The main contents of the thesis are as follows:（1）The bay-substituted hexacyano-triperyleno[3.3.3]propellane triimides（compound 11）is designed and synthesized by using trinaphtho[3.3.3]pro-pellane as the starting material.Borylated dibutyl naphthalate is used as the reactant for Suzuki coupling in the synthetic route,which effectively solves the problems of poor solubility and low yield of intermediate products in the initial route.The introduction of the cyano groups significantly reduces the LUMO energy level of the molecule,making it has stable electron transport ability.As indicated by the test results of the devices,compound 11 emits red light in OLED,and it shows electron mobility of 6.5×10^-4 cm² V^-1 s^-1 in OFET and power conversion efficiency of 3.97%in OSC,reflecting its wide application value as an n-type organic semiconductor material.（2）The benzofuran-fused triperyleno[3.3.3]propellane triimides（compound 16）is prepared by the nucleophilic substitution and coupling cyclization of bay-substituted hexabromopropellane derivative,and it has adequate solubility without the introduction of lateral alkyl chains.The structures of benzofuran are fused on the side of the perylene cores close to the imide groups in the subunits.The increase in the degree of conjugation leads to a clear red-shift of the maximum absorption wavelength in the UV-vis spectrum,and the energy levels and band gaps of the molecule are also changed.When using it as the emissive layer of OLED,the maximum emission wavelength in the EL spectrum is 652 nm,and the device shows the luminance of 294.43 cd/m²,illustrating the good performance of this 3D compound as a red-light material.