可溶性有機半導體多環芳香族衍生物之合成及其應用於有機薄膜電晶體

Synthesis of Soluble Organic Semiconducting Materials Based on Polycyclic Aromatic Hydrocarbon derivatives and Application on Organic Thin Film Transistor

李維峯(Wei-Feng Lee)

指導教授 ： 郭欽湊

大同大學/工程學院/化學工程學系所/碩士(2012年)

摘要

本研究利用格里納反應合成出一系列包含三種可溶性有機半導體材料的多環芳香族碳氫化合物，第一系列為雙噻吩蒽衍生物，共三種化合物：6,13-bis(triisopropylsilylethynyl) anthradithiophene (TIPS-ADT) (6), 6,13-bis(triethylsilylethynyl) anthradithiophene (TES-ADT) (7), and 6,13-bis (trimethylsilylethynyl) anthradithiophene (TMS-ADT) (8)。第二系列為五環素衍生物，共五種化合物： 6,13-bis(triisopropylsilylethynyl) pentacene (TIPS-PEN) (9), 6,13-bis (triethylsilylethynyl) pentacene (TES-PEN) (10), 6,13-bis(trimethylsilylethynyl) pentacene (TMS-PEN) (11), 6,13-bis(5-(tri -isopropylsilyl)thiophen-2-yl) pentacene (TIPST-PEN) (12), and 6,13-bis ((5-(triisopropylsilyl)thiophen-2-yl)ethynyl) pentacene (TIPSTE-PEN) (13)。第三系列為蒽衍生物，共三種化合物：6,13-bis(triisopropyl -silylethynyl) anthracene (TIPS-AN) (14), 6,13-bis(triethylsilylethynyl) anthracene (TES-AN) (15), and 6,13-bis(trimethylsilylethynyl) anthracene (TMS-AN) (16)。上述之化合物經FT-IR、1H-NMR、EA及熔點鑑定無誤。由UV-Vis光譜可得到五環素衍生物的吸收波峰在640 nm，雙噻吩蒽衍生物的吸收波峰在550 nm，蒽衍生物的吸收波峰在440 nm。由螢光光譜測定出五環素衍生物的放光波峰在650 nm，雙噻吩蒽衍生物的放光波峰在560 nm，蒽衍生物的放光波峰在470 nm；其分別激發出粉紅色、橘色及藍色光。由UV-Vis及CV可計算出各化合物之能隙，其中五環素衍生物的能隙約為1.89 ± 0.03 eV，雙噻吩蒽衍生物的能隙約為2.18 ± 0.01 eV，蒽衍生物的能隙約為2.75 ± 0.01 eV。
將合成出的多環芳香族碳氫化合物應用作為有機薄膜電晶體脂半導體材質，其中TIPS-PEN與TES-ADT有較好的特性，其載子位移率與開關電流比分別為9.34 x 10^-2 cm^2/Vs和2.47 x 10^5及6.33 x 10^-2 cm^2/Vs 和8.41 x 10^5。

關鍵字

雙噻吩蒽 ； 蒽 ； 薄膜電晶體 ； 有機半導體 ； 五環素衍生物

並列摘要

A series of polycyclic aromatic hydrocarbons (PAHs), which contains three soluble organic semiconductor material systems have been synthesized successfully by Grignard reaction. The first system is based on anthradithiophene (ADT), three anthradithiophene derivatives: 6,13-bis(tri -isopropylsilylethynyl) anthradithiophene (TIPS-ADT) (6), 6,13-bis (triethylsilylethynyl) anthradithiophene (TES-ADT) (7), and 6,13-bis(tri -methylsilylethynyl) anthradithiophene (TMS-ADT) (8). The second system is based on pentacene (PEN), five pentacene derivatives: 6,13-bis(triiso -propylsilylethynyl) pentacene (TIPS-PEN) (9), 6,13-bis (triethylsilylethynyl) pentacene (TES-PEN) (10), 6,13-bis(trimethylsilylethynyl) pentacene (TMS-PEN) (11), 6,13-bis(5-(triisopropylsilyl)thiophen-2-yl) pentacene (TIPST-PEN) (12), and 6,13-bis((5-(triisopropyl silyl)thiophen-2-yl)ethynyl) pentacene (TIPSTE-PEN) (13). The final system is based on anthracene (AN), three anthracene derivatives: 6,13-bis(triisopropylsilylethynyl) anthracene (TIPS-AN) (14), 6,13-bis (triethylsilylethynyl) anthracene (TES-AN) (15), and 6,13-bis(trimethylsilylethynyl) anthracene (TMS-AN) (16) The structure of above PAHs derivatives has been confirmed by FT-IR, 1H-NMR, EA, and melting point. The UV-Vis absorption peak of PAHs is 640 nm for pentacene derivatives, 550 nm for anthradithiophene derivatives, and 440 nm for anthracene derivatives. The photoluminescent peak of pentacene, anthrdithiophene, and anthracene derivatives occurs at 650 nm, 560 nm, and 470 nm, respectively, which correspond to the emission of pink, orange, and blue light. Accroding to the measurements of UV-Vis and cyclic voltammetry, it is found that the band gap of pentacene, anthradithiophene, and anthracene derivatives is 1.89 ± 0.03, 2.18 ± 0.01, and 2.75 ± 0.01 eV, respectively.
The characteristics of organic thin-film transistor (OTFT) fabricated with PAHs derivatives acted as a semiconducting material have been investigated. The charge transport mobility and on/off current ratio of PAH derivative OTFTs are 9.34 x 10^-2 cm^2/Vs and 2.47 x 10^5 of TIPS-PEN, and 6.33 x 10^-2 cm^2/Vs and 8.41 x 10^5 of TES-ADT, respectively.

並列關鍵字

anthradithiophene ； anthracene ； OTFT ； organic semiconductor ； pentacene derivatives

參考文獻

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