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第 36 卷第 4 期 精 细 化 工 Vol.36, No.4
201 9 年 4 月 FINE CHEMICALS Apr. 2019

功能材料
一种异靛蓝衍生半导体的合成、表征和 OTFT 应用

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陈少云，瞿 波，刘小英，李文杰，卓东贤
（泉州师范学院 化工与材料学院，福建 泉州 362000）

摘要：以 4-癸基十六烷基溴和 6-溴二氢吲哚-2,3-二酮为原料，将 4-癸基十六烷基侧链引入到（3E,7E）-3,7-双（2-
氧代二氢吲哚-3-亚基）苯并[1,2-b：4,5-b']二呋喃-2,6（3H,7H）-二酮（IBDF）中合成了 IBDF-26，再与（E）-1,2-
双（三丁基甲锡烷基）乙烯通过 Stille 偶合制备了基于异靛蓝衍生大稠环聚合物的半导体 PIBDFV-26。采用 TGA、
DSC、UV、CV、XRD、AFM 对 PIBDFV-26 的性能、结构、形貌进行了表征。结果表明，基于异靛蓝大稠环的
半导体 PIBDFV-26 在三氯乙烯（TCE）中的溶解性良好，具有良好的热稳定性，HOMO/LUMO 能级为
–5.96 eV/–4.62 eV，光学帯隙为 1.34 eV。XRD 结果表明，聚合物链沿边沿取向形成层状晶体结构，层间距为
–6
–7
2.55×10 mm，π–π 堆积距离为 3.46×10 mm。AFM 显示，退火处理的 PIBDFV-26 薄膜表面含有纳米级的晶状
颗粒。对 PIBDFV-26 组装的有机薄膜晶体管（OTFT）器件进行了测试，结果显示 OTFT 器件表现出电子传输
2
（negative，n）型沟道的电荷传输特性。150 ℃退火处理的聚合物薄膜的平均电子迁移率为 0.13 cm /(V∙s)。
关键词：异靛蓝；给体-受体；半导体；OTFT；电子迁移率；功能材料
中图分类号：O631 文献标识码：A 文章编号：1003-5214 (2019) 04-0602-07

Preparation and Characterization of an Isoindigo-Derived
Semiconductor and Its OTFT Application

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CHEN Shao-yun, QU bo, LIU Xiao-ying, LI Wen-jie, ZHUO Dong-xian
（College of Chemical Engineering and Materials Science, Quanzhou Normal University, Quanzhou 362000, Fujian, China）

Abstract: 6-Bromo-1-(4-decyl-hexadecyl)-1H-indole-2,3-dione was prepared from 4-decyl-1-hexadecyl
bromide with 6-bromoindoline-2,3-dione.Compound IBDF-26 was obtained by introducing 4-decyl-1-hexadecyl
side chain into (3E,7E)-3,7-bis(2-oxoindolin-3-ylidene)benzo [1,2-b: 4,5-b']difuran-2,6(3H,7H)-dione(IBDF).
Then a palladium-catalyzed Stille coupling reaction of intermediate IBDF-26 with (E)-1,2-bis
(tributylstannyl) etheneled to polymer semiconductor PIBDFV-26 based on isoindigo. The properties,
structure and morphology of PIBDFV-26 were characterized by TGA, DSC, UV, CV, XRD and AFM. The
results show that semiconductor PIBDFV-26 has good solubility in trichloroethylene (TCE), and processes
excellent thermal stability. The HOMO/LUMO energy level is –5.96 eV/–4.62 eV and the optical bandgap
is 1.34 eV. XRD results reveal that the polymer chains are likely packed in a lamellar crystalline structure
–6
with an edge-on orientation and the d-spacing and π–π stacking distance are 2.55×10 mm and 3.46 ×10 –7
mm, respectively. AFM shows that the surface of the annealed PIBDFV-26 film contains nano-crystalline
particles. PIBDFV-26 was assembled into an organic thin film transistor (OTFT) device and tested. The
results demonstrate that the OTFT device exhibits n-type charge transfer characteristic.The average electron
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mobility for a 150 ℃-annealed PIBDFV-26 film is 0.13 cm /(V∙s).
Key words: isoindigo; donor-acceptor; semiconductor; OTFT; electron mobility; functional materials
Foundation items: National Natural Science Foundation of China (51403212)； Natural Science
Foundation ofFujian Province (2015J05030)； Young and Middle-aged Teacher Education Research Project
(Technology) of Fujian Province (JA15398)

收稿日期：2018-07-03; 定用日期：2018-12-10; DOI: 10.13550/j.jxhg.20180489
基金项目：国家自然科学基金（51403212）；福建省自然科学基金资助项目（2015J05030）；福建省中青年教师教育科研项目（科技）
（JA15398）
作者简介：陈少云（1985—），女，讲师，E-mail：chshaoy@qztc.edu.cn。联系人：卓东贤（1983—），男，教授，E-mail：dxzhuo@qztc.edu.cn。