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基于氟代异靛蓝并[7, 6-
增强出版g ]异靛蓝的共轭聚合物的合成及其半导体性质Synthesis and Semiconducting Properties of Conjugated Polymers Based on Fluorinated Isoindigo[7, 6-
g ]isoindigo- 高分子学报 2017年第7期 页码：1141-1149
- 作者机构：
1.中国科学院长春应用化学研究所 高分子物理与化学国家重点实验室 长春 130022
2.天津大学材料科学与工程学院 天津化学化工协同创新中心 天津 300072
3.中国科学院大学 北京 100049
- 作者简介：
丁军桥, E-mail:junqiaod@ciac.ac.cn Jun-qiao Ding, E-mail:junqiaod@ciac.ac.cn
耿延候, E-mail:yanhou.geng@tju.edu.cn Yan-hou Geng, E-mail:yanhou.geng@tju.edu.cn
- 基金信息：国家重点研发计划(2016YFB0401100);国家自然科学基金(51333006)
DOI：10.11777/j.issn1000-3304.2017.17022
中图分类号：纸质出版日期：2017-7，
收稿日期：2017-1-24，
修回日期：2017-3-10，
扫 描 看 全 文
江宇, 高垚, 田洪坤, 丁军桥, 耿延候, 王佛松. 基于氟代异靛蓝并[7, 6-
g ]异靛蓝的共轭聚合物的合成及其半导体性质[J]. 高分子学报, 2017,(7):1141-1149.Yu Jiang, Yao Gao, Hong-kun Tian, Jun-qiao Ding, Yan-hou Geng, Fo-song Wang. Synthesis and Semiconducting Properties of Conjugated Polymers Based on Fluorinated Isoindigo[7, 6-
g ]isoindigo[J]. Acta Polymerica Sinica, 2017,(7):1141-1149.江宇, 高垚, 田洪坤, 丁军桥, 耿延候, 王佛松. 基于氟代异靛蓝并[7, 6-
g ]异靛蓝的共轭聚合物的合成及其半导体性质[J]. 高分子学报, 2017,(7):1141-1149. DOI： 10.11777/j.issn1000-3304.2017.17022.Yu Jiang, Yao Gao, Hong-kun Tian, Jun-qiao Ding, Yan-hou Geng, Fo-song Wang. Synthesis and Semiconducting Properties of Conjugated Polymers Based on Fluorinated Isoindigo[7, 6-
g ]isoindigo[J]. Acta Polymerica Sinica, 2017,(7):1141-1149. DOI： 10.11777/j.issn1000-3304.2017.17022.
摘要
采用Stille缩聚，合成了3个异靛蓝并[7，6-
g
]异靛蓝（DⅡD）和乙烯单元交替排列的共轭聚合物
P0F
、
P2F
和
P4F
，三者在DⅡD单元中分别含0、2和4个氟原子（F）.3个聚合物均具有良好的平面性，前线分子轨道几乎在整个共轭骨架上离域.它们均具有宽的吸收光谱，吸收范围在400~1000 nm，光学带隙约为1.25 eV；随着氟原子数目的增加，聚合物的最高占有分子轨道（HOMO）和最低空分子轨道（LUMO）能级依次下降0.1~0.2 eV.以这3个聚合物作为活性层，制备了顶栅-底接触型有机场效应晶体管器件，随着氟原子数目的增加，聚合物的传输性质由双极传输变为n型传输.
P0F
和
P2F
是双极传输型聚合物，空穴迁移率（
μ
h
）分别达到0.11和0.30 cm
2
V
-1
s
-1
，电子迁移率（
μ
e
）分别达到0.22和1.19 cm
2
V
-1
s
-1
.
P4F
是
n
型聚合物，
μ
e
达到0.18 cm
2
V
-1
s
-1
.
Abstract
Three alternating conjugated polymers of isoindigo[7
6-
g
]isoindigo (DⅡD) and vinylene
i.e
.
P0F
P2F
and
P4F
in which DⅡD units contain 0
2 and 4 fluorine (F) atoms
respectively
were synthesized
via
Stille polycondensation. The number-average molecular weights (
M
n
) were 3.94×104
4.45×104 and 1.93×104 for
P0F
P2F
and
P4F
respectively. All these three polymers are largely planar and their frontier molecular orbitals are well-delocalized along conjugated backbones as revealed by density functional theory (DFT) calculation. Their 5 wt% weight loss temperatures are above 360℃. They all have very broad absorption spectra in the range of 400~1000 nm and their optical band-gaps are
ca
. 1.25 eV. With an increase of F atoms
both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels decreased
from -5.26 and -3.57 eV for
P0F
to -5.48 and -3.68 eV for
P2F
and further to -5.62 and -3.82 eV for
P4F
. Thin films of the polymers were characterized by X-ray diffraction and atomic force microscopy (AFM). All these polymers formed ordered structure in their films with conjugated backbone adopting an edge-on arrangement. The portion of the ordered structure in the films increased from
P0F
to
P4F
along with the increase in F-atoms in DⅡD unit. Top-gate and bottom-contact (TGBC) organic field-effect transistors (OFETs) of the polymers were fabricated with poly(methylmethacrylate) as dielectric
via
solution spin casting with
o
-dichlorobenzene. The device performance was measured under ambient conditions. With increasing the number of F atoms
the transfer behaviour of the devices based on the polymers changed from ambipolar to unipolar n-type.
P0F
and
P2F
were ambipolar polymers. Their hole mobility was 0.11 and 0.30 cm
2
V
-1
s
-1
respectively
and the electron mobility was 0.22 and 1.19 cm
2
V
-1
s
-1
respectively.
P4F
was a typical unipolar n-type semiconductor and its electron mobility was up to 0.18 cm
2
V
-1
s
-1
. The relatively lower mobility of
P4F
was attributed to its lower molecular weight. This study shows that DⅡD is a promising building block for conjugated polymers with high mobility and low band-gap.
关键词
氟代异靛蓝并[7 6-g]异靛蓝共轭聚合物有机场效应晶体管
Keywords
FluorinationIsoindigo[7 6-g]isoindigoConjugated polymersOrganic field-effect transistors
references
L T Dou , Y S Liu , Z R Hong , G Li , Y Yang . . Chem Rev , 2015 . 115 ( 23 ): 12633 - 12665 . DOI:10.1021/acs.chemrev.5b00165http://doi.org/10.1021/acs.chemrev.5b00165.
X G Guo , A Facchetti , T J Marks . . Chem Rev , 2014 . 114 ( 18 ): 8943 - 9021 . DOI:10.1021/cr500225dhttp://doi.org/10.1021/cr500225d.
A J Heeger . . Chem Soc Rev , 2010 . 39 ( 7 ): 2354 - 2371 . DOI:10.1039/b914956mhttp://doi.org/10.1039/b914956m.
H Sirringhaus . . Adv Mater , 2014 . 26 ( 9 ): 1319 - 1335 . DOI:10.1002/adma.201304346http://doi.org/10.1002/adma.201304346.
A Facchetti . . Mater Today , 2007 . 10 ( 3 ): 28 - 37 . DOI:10.1016/S1369-7021(07)70017-2http://doi.org/10.1016/S1369-7021(07)70017-2.
J Y Back , H Yu , I Song , I Kang , H Ahn , T J Shin , S K Kwon , J H Oh , Y H Kim . . Chem Mater , 2015 . 27 ( 5 ): 1732 - 1739 . DOI:10.1021/cm504545ehttp://doi.org/10.1021/cm504545e.
W M Zhang , Y Han , X X Zhu , Z P Fei , Y Feng , N D Treat , H Faber , N Stingelin , I McCulloch , T D Anthopoulos , M Heeney . . Adv Mater , 2016 . 28 ( 20 ): 3922 - 3927 . DOI:10.1002/adma.v28.20http://doi.org/10.1002/adma.v28.20.
J Li , Y Zhao , H S Tan , Y L Guo , C-A Di , G Yu , Y Q Liu , M Lin , S H Lim , Y H Zhou , H B Su , B S Ong . . Sci Rep , 2012 . 2 754 .
Y Olivier , D Niedzialek , V Lemaur , W Pisula , K Müllen , U Koldemir , J R Reynolds , R Lazzaroni , J Cornil , D Beljonne . . Adv Mater , 2014 . 26 ( 14 ): 2119 - 2136 . DOI:10.1002/adma.v26.14http://doi.org/10.1002/adma.v26.14.
H Usta , A Facchetti , T J Marks . . Acc Chem Res , 2011 . 44 ( 7 ): 501 - 520 . DOI:10.1021/ar200006rhttp://doi.org/10.1021/ar200006r.
J E Anthony , A Facchetti , M Heeney , S R Marder , X W Zhan . . Adv Mater , 2010 . 22 ( 34 ): 3876 - 3892 . DOI:10.1002/adma.200903628http://doi.org/10.1002/adma.200903628.
J Choi , H Song , N Kim , F S Kim . . Semicond Sci Technol , 2015 . 30 ( 6 ): 064002 DOI:10.1088/0268-1242/30/6/064002http://doi.org/10.1088/0268-1242/30/6/064002.
X Guo , M Baumgarten , K Müllen . . Prog Polym Sci , 2013 . 38 ( 12 ): 1832 - 1908 . DOI:10.1016/j.progpolymsci.2013.09.005http://doi.org/10.1016/j.progpolymsci.2013.09.005.
Q Meng , W P Hu . . Phys Chem Chem Phys , 2012 . 14 ( 41 ): 14152 - 14164 . DOI:10.1039/c2cp41664fhttp://doi.org/10.1039/c2cp41664f.
X K Gao , Y B Hu . . J Mater Chem C , 2014 . 2 ( 17 ): 3099 - 3117 . DOI:10.1039/C3TC32046Dhttp://doi.org/10.1039/C3TC32046D.
J D Yuen , F Wudl . . Energy Environ Sci , 2013 . 6 ( 2 ): 392 - 406 . DOI:10.1039/c2ee23505fhttp://doi.org/10.1039/c2ee23505f.
S Holliday , J E Donaghey , I McCulloch . . Chem Mater , 2014 . 26 ( 1 ): 647 - 663 . DOI:10.1021/cm402421phttp://doi.org/10.1021/cm402421p.
D Venkateshvaran , M Nikolka , A Sadhanala , V Lemaur , M Zelazny , M Kepa , M Hurhangee , A J Kronemeijer , V Pecunia , I Nasrallah , I Romanov , K Broch , I McCulloch , D Emin , Y Olivier , J Cornil , D Beljonne , H Sirringhaus . . Nature , 2014 . 515 ( 7527 ): 384 - 388 . DOI:10.1038/nature13854http://doi.org/10.1038/nature13854.
T Lei , J H Dou , Z J Ma , C J Liu , J Y Wang , J Pei . . Chem Sci , 2013 . 4 ( 6 ): 2447 - 2452 . DOI:10.1039/c3sc50245ghttp://doi.org/10.1039/c3sc50245g.
H J Yun , S J Kang , Y Xu , S O Kim , Y H Kim , Y Y Noh , S K Kwon . . Adv Mater , 2014 . 26 ( 43 ): 7300 - 7307 . DOI:10.1002/adma.v26.43http://doi.org/10.1002/adma.v26.43.
D Khim , Y R Cheon , Y Xu , W T Park , S K Kwon , Y Y Noh , Y H Kim . . Chem Mater , 2016 . 28 ( 7 ): 2287 - 2294 . DOI:10.1021/acs.chemmater.6b00298http://doi.org/10.1021/acs.chemmater.6b00298.
Y Q Zheng , T Lei , J H Dou , X Xia , J Y Wang , C J Liu , J Pei . . Adv Mater , 2016 . 28 ( 33 ): 7213 - 7219 . DOI:10.1002/adma.201600541http://doi.org/10.1002/adma.201600541.
Y Gao , X J Zhang , H K Tian , J D Zhang , D H Yan , Y H Geng , F S Wang . . Adv Mater , 2015 . 27 ( 42 ): 6753 - 6759 . DOI:10.1002/adma.201502896http://doi.org/10.1002/adma.201502896.
T Lei , X Xia , J Y Wang , C J Liu , J Pei . . J Am Chem Soc , 2014 . 136 ( 5 ): 2135 - 2141 . DOI:10.1021/ja412533dhttp://doi.org/10.1021/ja412533d.
H J Son , W Wang , T Xu , Y Y Liang , Y Wu , G Li , L P Yu . . J Am Chem Soc , 2011 . 133 ( 6 ): 1885 - 1894 . DOI:10.1021/ja108601ghttp://doi.org/10.1021/ja108601g.
T Lei , J H Dou , Z J Ma , C H Yao , C J Liu , J Y Wang , J Pei . . J Am Chem Soc , 2012 . 134 ( 49 ): 20025 - 20028 . DOI:10.1021/ja310283fhttp://doi.org/10.1021/ja310283f.
Y Jiang , Y Gao , H K Tian , J Q Ding , D H Yan , Y H Geng , F S Wang . . Macromolecules , 2016 . 49 ( 6 ): 2135 - 2144 . DOI:10.1021/acs.macromol.6b00004http://doi.org/10.1021/acs.macromol.6b00004.
Y Zhu , R D Champion , S A Jenekhe . . Macromolecules , 2006 . 39 ( 25 ): 8712 - 8719 . DOI:10.1021/ma061861ghttp://doi.org/10.1021/ma061861g.
S Z Bisri , C Piliego , J Gao , M A Loi . . Adv Mater , 2014 . 26 ( 8 ): 1176 - 1199 . DOI:10.1002/adma.v26.8http://doi.org/10.1002/adma.v26.8.
R Noriega , J Rivnay , K Vandewal , F P V Koch , N Stingelin , Smith , P , M F Toney , A Salleo . . Nat Mater , 2013 . 12 ( 11 ): 1038 - 1044 . DOI:10.1038/nmat3722http://doi.org/10.1038/nmat3722.
H N Tsao , K Müllen . . Chem Soc Rev , 2010 . 39 ( 7 ): 2372 - 2386 . DOI:10.1039/b918151mhttp://doi.org/10.1039/b918151m.
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