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Fluorinated Thiophene-Phenylene Co-Oligomers for Optoelectronic Devices.
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2020-02-03 , DOI: 10.1021/acsami.9b20295 Andrey Yu Sosorev 1, 2, 3 , Vasiliy A Trukhanov 1, 3 , Dmitry R Maslennikov 1, 2, 3 , Oleg V Borshchev 3 , Roman A Polyakov 3 , Maxim S Skorotetcky 3 , Nikolay M Surin 3 , Maxim S Kazantsev 4 , Dmitry I Dominskiy 1, 3 , Viktor A Tafeenko 5 , Sergey A Ponomarenko 3, 5 , Dmitry Yu Paraschuk 1, 3
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2020-02-03 , DOI: 10.1021/acsami.9b20295 Andrey Yu Sosorev 1, 2, 3 , Vasiliy A Trukhanov 1, 3 , Dmitry R Maslennikov 1, 2, 3 , Oleg V Borshchev 3 , Roman A Polyakov 3 , Maxim S Skorotetcky 3 , Nikolay M Surin 3 , Maxim S Kazantsev 4 , Dmitry I Dominskiy 1, 3 , Viktor A Tafeenko 5 , Sergey A Ponomarenko 3, 5 , Dmitry Yu Paraschuk 1, 3
Affiliation
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Organic optoelectronics requires materials combining bright luminescence and efficient ambipolar charge transport. Thiophene-phenylene co-oligomers (TPCOs) are promising highly emissive materials with decent charge-carrier mobility; however, they typically show poor electron injection in devices, which is usually assigned to high energies of their lowest unoccupied molecular orbitals (LUMOs). A widely used approach to lower the frontier orbitals energy levels of a conjugated molecule is its fluorination. In this study, we synthesized three new fluorinated derivatives of one of the most popular TPCOs, 2,2'-(1,4-phenylene)bis[5-phenylthiophene] (PTPTP) and studied them by cyclic voltammetry, absorption, photoluminescence, and Raman spectroscopies. The obtained data reveal a positive effect of fluorination on the optoelectronic properties of PTPTP: LUMO levels are finely tuned, and photoluminescence quantum yield and absorbance are increased. We then grew crystals from fluorinated PTPTPs, resolved their structures, and showed that fluorination dramatically affects the packing motif and facilitates π-stacking. Finally, we fabricated thin-film organic field-effect transistors (OFETs) and demonstrated a strong impact of fluorination on charge injection/transport for both types of charge carriers, namely, electrons and holes. Specifically, balanced ambipolar charge transport and electroluminescence were observed only in the OFET active channel based on the partially fluorinated PTPTP. The obtained results can be extended to other families of conjugated oligomers and highlight the efficiency of fluorination for rational design of organic semiconductors for optoelectronic devices.
中文翻译：
光电器件用氟化噻吩-苯撑共聚体。
有机光电子需要结合了明亮的发光和有效的双极性电荷传输的材料。噻吩-苯撑低聚物（TPCO）是具有良好电荷载流子迁移率的高发射材料。然而，它们通常在设备中显示出较差的电子注入，这通常被分配给它们最低的未占据分子轨道（LUMO）的高能量。降低共轭分子前沿轨道能级的一种广泛使用的方法是氟化。在这项研究中，我们合成了三种最受欢迎的TPCO之一的新的氟化衍生物2,2'-（1,4-亚苯基）双[5-苯基噻吩]（PTPTP），并通过循环伏安法，吸收法，光致发光法，和拉曼光谱学。获得的数据表明氟化对PTPTP的光电性能有积极影响：微调LUMO的水平，并增加光致发光的量子产率和吸收率。然后，我们从氟化的PTPTPs中生长出晶体，解析了它们的结构，结果表明氟化作用显着影响堆积图案并促进π堆积。最后，我们制造了薄膜有机场效应晶体管（OFET），并证明了氟化对两种类型的电荷载流子（即电子和空穴）对电荷注入/传输的强烈影响。具体而言，仅在基于部分氟化的PTPTP的OFET有源通道中观察到平衡的双极性电荷传输和电致发光。
更新日期：2020-02-14
中文翻译：
光电器件用氟化噻吩-苯撑共聚体。
有机光电子需要结合了明亮的发光和有效的双极性电荷传输的材料。噻吩-苯撑低聚物（TPCO）是具有良好电荷载流子迁移率的高发射材料。然而，它们通常在设备中显示出较差的电子注入，这通常被分配给它们最低的未占据分子轨道（LUMO）的高能量。降低共轭分子前沿轨道能级的一种广泛使用的方法是氟化。在这项研究中，我们合成了三种最受欢迎的TPCO之一的新的氟化衍生物2,2'-（1,4-亚苯基）双[5-苯基噻吩]（PTPTP），并通过循环伏安法，吸收法，光致发光法，和拉曼光谱学。获得的数据表明氟化对PTPTP的光电性能有积极影响：微调LUMO的水平，并增加光致发光的量子产率和吸收率。然后，我们从氟化的PTPTPs中生长出晶体，解析了它们的结构，结果表明氟化作用显着影响堆积图案并促进π堆积。最后，我们制造了薄膜有机场效应晶体管（OFET），并证明了氟化对两种类型的电荷载流子（即电子和空穴）对电荷注入/传输的强烈影响。具体而言，仅在基于部分氟化的PTPTP的OFET有源通道中观察到平衡的双极性电荷传输和电致发光。
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