CN113512053B - 多稠环n型半导体材料的制备方法及其应用 - Google Patents
多稠环n型半导体材料的制备方法及其应用 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
本发明涉及一种超低LUMO能级的多SN杂稠环n型有机半导体材料，该材料可应用于有机场效应晶体管，有机薄膜太阳能电池及钙钛矿电池。以1,5‑二氨基萘为初始原料，经多步合成，得到5,11‑二氟喹喔啉[6,5‑f]喹喔啉，再与1,1‑二氰基乙烯‑2,2‑二硫醇钠反应，即得所述多稠环n型半导体材料。本发明所述材料由多个芳香环稠合而成，具有较大的平面结构，且四个强吸电子基团(氰基)能有效降低分子LUMO能级，是一种具有较好发展前景的n型半导体材料。
Description
技术领域
本发明涉及材料领域，具体涉及多稠环n型半导体材料的制备方法及其应用。
背景技术
有机场效应晶体管具有材料来源广，成膜技术多，加工温度低，电学性质易调控，可与柔性衬底兼容，适合批量生产和成本低等优点。其中，有机半导体作为有机场效应晶体管的活性层，受到了最为广泛的研究。
相对于已取得一定进展的p型半导体材料，n型半导体材料的发展仍相对滞后，这主要是因为n型半导体材料的载流子为电子，而电子极易与空气中的氧气和水反应，这意味着电子会在传输过程中被捕获而无电学响应。但是，n型半导体材料作为双极型逻辑互补电路中不可或缺的部分，其研究价值和应用价值非常高。具有超低LUMO能级的有机半导体材料能够在空气环境中稳定电子载流子，目前现有技术中少有提及相关材料的制备方法和相关应用。
因此，亟需一种具有超低LUMO能级且与金属电极功函匹配的新型n型半导体材料，并将其运用于制备有机场效应晶体管或电池中。
发明内容
本发明为了解决上述问题，提供了多稠环n型半导体材料的制备方法及其应用，所述多稠环n型半导体材料具有超低LUMO能级且能与金属电极功函匹配。
本发明目的之一在于提供一种多稠环n型半导体材料，技术方案如下：
多稠环n型半导体材料，所述材料的分子结构式如式Ⅰ所示：
所述R为助溶基团。
优选的，所述R为三异丙基硅炔基或2-辛基噻吩或正辛基苯基醚。
本发明目的之二在于提供上述多稠环n型半导体材料的制备方法，具体技术方案如下：
多稠环n型半导体材料的制备方法，其特征在于，所述制备步骤如下：
(1)式Ⅲ与二酮类化合物反应得到式Ⅱ化合物；
(2)式Ⅱ与1,1-二氰乙烯-2,2-二硫醇钠反应得到式Ⅰ化合物。
优选的，步骤(1)中反应溶剂为乙醇和乙酸溶液，反应温度为80℃，反应时间为23h。
优选的，所述乙醇和乙酸的体积比为1：1。
优选的，步骤(2)中反应溶剂为有机溶剂，所述的有机溶剂为甲苯、二甲苯、三甲苯、氯苯、二氯苯、三氯苯、DMF、DMSO中的至少一种。
优选的，步骤(2)反应温度为70℃，反应时间为2h。
优选的，步骤(2)中式Ⅱ和1,1-二氰乙烯-2,2-二硫醇钠的摩尔比为1：2.3。
优选的，化合物Ⅱ纯化处理时，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空抽滤获得纯化后的产物。
本发明目的之三在于提供上述方案中的多稠环n型半导体材料在制备有机场效应晶体管中的应用。
本发明目的之四在于提供上述方案中的多稠环n型半导体材料在制备电池中的应用，所述电池包括有机薄膜太阳能电池、钙钛矿电池中的一种或几种。
本发明的有益之处在于：本发明所述材料由多个芳香环稠合而成，具有较大的平面结构，且四个强吸电子基团(氰基)能有效降低分子LUMO能级，是一种具有较好发展前景的n型半导体材料。
具体实施方式
下面通过实施例对本发明进行进一步详细说明，应当理解，此处所描述的具体实施例仅用以解释本发明，并不用于限定本发明，本领域技术人员应该理解的是，在不偏离本发明的结构思路、使用范围下可以对本发明技术方案的细节和形式进行修改或替换，但这些修改和替换均落入本发明的保护范围内。
实施例1
本实施例公开一种电子受体，结构如下
上述电子受体化合物5的合成步骤如下
合成化合物4
氩气保护下，化合物1(174mg,0.47mmol)和1,6-双(三异丙基硅炔基)-1,5-二炔-3,4-二酮(452mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物5
氩气保护下，化合物4(988.6mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例2
本实施例公开一种电子受体，结构如下
上述电子受体化合物7的合成步骤如下
合成化合物6
氩气保护下，化合物1(174mg,0.47mmol)和1,6-双(三正丙基硅基炔基)-1,5-二炔-3,4-二酮(452mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物7
氩气保护下，化合物6(989mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例3
本实施例公开一种电子受体，结构如下
上述电子受体化合物9的合成步骤如下
合成化合物8
氩气保护下，化合物1(174mg,0.47mmol)和1,6-双(三乙基硅基炔基)-1,5-二炔-3,4-二酮(345.6mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物9
氩气保护下，化合物8(806mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例4
本实施例公开一种电子受体，结构如下
上述电子受体化合物11的合成步骤如下
合成化合物10
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(5-正辛基噻吩)乙烷-1,2-二酮(482mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物11
氩气保护下，化合物10(1045mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例5
本实施例公开一种电子受体，结构如下
上述电子受体化合物13的合成步骤如下
合成化合物12
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(5-正庚基噻吩)乙烷-1,2-二酮(451.4mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物13
氩气保护下，化合物12(988mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例6
本实施例公开一种电子受体，结构如下
上述电子受体化合物15的合成步骤如下
合成化合物14
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(5-正己基噻吩)乙烷-1,2-二酮(421.2mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物15
氩气保护下，化合物14(932mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例7
本实施例公开一种电子受体，结构如下
上述电子受体化合物17的合成步骤如下
合成化合物16
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(5-叔丁基噻吩)乙烷-1,2-二酮(360.7mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物17
氩气保护下，化合物16(820mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例8
本实施例公开一种电子受体，结构如下
上述电子受体化合物19的合成步骤如下
合成化合物18
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(4-正辛基噻吩)乙烷-1,2-二酮(482mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物19
氩气保护下，化合物18(1045mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例9
本实施例公开一种电子受体，结构如下
上述电子受体化合物21的合成步骤如下
合成化合物20
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(4-正庚基噻吩)乙烷-1,2-二酮(451.4mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物21
氩气保护下，化合物20(988mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
实施例10
本实施例公开一种电子受体，结构如下
上述电子受体化合物23的合成步骤如下
合成化合物22
氩气保护下，化合物1(174mg,0.47mmol)和1,2-双(3-(辛氧基)苯基)乙烷-1,2-二酮(503mg,1.08mmol)溶于15ml乙醇和15ml的乙酸溶液，80℃反应23h。反应结束后，将反应后制得的产物倒入冰水中，然后用二氯甲烷萃取，收集有机层后用无水硫酸镁干燥，并经过滤，旋蒸，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
合成化合物23
氩气保护下，化合物22(1085mg,1mmol)与1,1-二氰乙烯-2,2-二硫醇钠(560mg,3mmol)溶于30ml DMF中，在70℃下反应2h。反应结束后，旋蒸出DMF，柱层析分离，再旋蒸，真空干燥得到结构为
的产物。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等均应包含在本发明的保护范围之内。
Claims (9)
1.多稠环n型半导体材料，其特征在于，所述材料的分子结构式如式Ⅰ所示：
2.权利要求1所述多稠环n型半导体材料的制备方法，其特征在于，所述制备步骤如下：
(1)式Ⅲ与二酮类化合物反应得到式Ⅱ化合物；
(2)式Ⅱ与1,1-二氰乙烯-2,2-二硫醇钠反应得到式Ⅰ化合物。
3.根据权利要求2所述的制备方法，其特征在于，步骤(1)中反应溶剂为乙醇和乙酸溶液，反应温度为80℃，反应时间为23h。
4.根据权利要求3所述的制备方法，其特征在于，所述乙醇和乙酸的体积比为1：1。
5.根据权利要求2所述的制备方法，其特征在于，步骤(2)中反应溶剂为有机溶剂，所述的有机溶剂为甲苯、二甲苯、三甲苯、氯苯、二氯苯、三氯苯、DMF、DMSO中的至少一种。
6.根据权利要求5所述的制备方法，其特征在于，步骤(2)反应温度为70℃，反应时间为2h。
7.根据权利要求2所述的制备方法，其特征在于，步骤(2)中式Ⅱ和1,1-二氰乙烯-2,2-二硫醇钠的摩尔比为1：2.3。
8.权利要求1所述的多稠环n型半导体材料在制备有机场效应晶体管中的应用。
9.权利要求1所述的多稠环n型半导体材料在制备电池中的应用。
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