Crystalline Organic Pigment-Based Field-Effect Transistors
Crystalline Organic Pigment-Based Field-Effect Transistors
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DOI：
10.1021/acsami.7b03170
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发表时间：
2017-07-05
影响因子：
9.5
通讯作者：
Zhu, Yu
中科院分区：
文献类型：
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作者：
Zhang, Haichang;Deng, Ruonan;Zhu, Yu
本文研究了三种具有稠合氢键的共轭色素分子3，7-二苯基吡咯并[2，3-f]吲哚-2，6（1H，5 H）-二酮（BDP）、（E）-6，6 '-二溴-[3，3'-联吲哚亚基]-2，2 '-二酮（IIDG）和3，6-二（噻吩-2-基）-2，5-二氢吡咯并[3，4-c]吡咯-1，4-二酮（TDPP）。将不溶性颜料分子用叔丁氧羰基（t-Boc）基团官能化以形成具有潜在氢键的可溶性颜料前体（BDP-Boc、TTDG-Boc和TDPP-Boc）。得到了可溶性颜料前体的单晶。在简单的热退火后，t-Boc基团被去除，并且具有潜在氢键的可溶性颜料前体分子被转化为具有稠合氢键的原始颜料分子。结构分析表明，高度结晶的可溶性前体直接转化为高度结晶的不溶性颜料，这通常只能通过气相途径如物理气相传输实现。热退火处理后的独特晶体结构表明，稠合氢键是分子重排形成固态新晶体的关键，这导致有机场效应晶体管（OFET）器件中电荷迁移率提高2个数量级以上。这项工作表明，晶体OFET器件与不溶性颜料分子可以制造由其可溶性前体。结果表明，多种市售共轭颜料可作为高性能OFFEs的潜在活性材料。
Three conjugated pigment molecules with fused hydrogen bonds, 3,7-diphenylpyrrolo [2,3-f]indole-2,6 (1H,5H)-dione (BDP), (E)-6,6'-dibromo-[3,3'-biindolinyli-dene]-2,2'-dione (IIDG), and 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo-[3,4-c]pyrrole-1,4-dione (TDPP), were studied in this work. The insoluble pigment molecules were functionalized with tert-butoxylcarbonyl (t-Boc) groups to form soluble pigment precursors (BDP-Boc, TTDG-Boc, and TDPP-Boc) with latent hydrogen bonding. The single crystals of soluble pigment precursors were obtained. Upon simple thermal annealing, the t-Boc groups were removed and the soluble pigment precursor molecules with latent hydrogen bonding were converted into the original pigment molecules with fused hydrogen bonding. Structural analysis indicated that the highly crystalline soluble precursors were directly converted into highly crystalline insoluble pigments, which are usually only achievable by gas-phase routes like physical vapor transport. The distinct crystal structure after the thermal annealing treatment suggests that fused hydrogen bonding is pivotal for the rearrangement of molecules to form a new crystal in solid state, which leads to over 2 orders of magnitude enhancement in charge mobility in organic field-effect transistor (OFET) devices. This work demonstrated that crystalline OFET devices with insoluble pigment molecules can be fabricated by their soluble precursors. The results indicated that a variety of commercially available conjugated pigments could be potential active materials for high-performance OFETs.