CN109553757B - 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用 - Google Patents

一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用 Download PDF

Info

Publication number
CN109553757B
CN109553757B CN201811573149.3A CN201811573149A CN109553757B CN 109553757 B CN109553757 B CN 109553757B CN 201811573149 A CN201811573149 A CN 201811573149A CN 109553757 B CN109553757 B CN 109553757B
Authority
CN
China
Prior art keywords
monomer
dimensional structure
polymer
naphthalene diimide
structural formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201811573149.3A
Other languages
English (en)
Other versions
CN109553757A (zh
Inventor
邓平
朱笔李
蔡洋
姬敬敬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fuzhou University
Original Assignee
Fuzhou University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fuzhou University filed Critical Fuzhou University
Priority to CN201811573149.3A priority Critical patent/CN109553757B/zh
Publication of CN109553757A publication Critical patent/CN109553757A/zh
Application granted granted Critical
Publication of CN109553757B publication Critical patent/CN109553757B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/124—Copolymers alternating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/143—Side-chains containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/145—Side-chains containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/149—Side-chains having heteroaromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3328—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms alkyne-based
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/91—Photovoltaic applications

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Photovoltaic Devices (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

本发明公开了一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用。其先通过炔键偶联反应合成一种带炔键的单体M1，然后将其与带溴基的单体M2加热聚合，通过炔键与溴的作用制得所述二维结构的萘二酰亚胺类受体聚合物。该聚合物中含有多个炔键，使分子间的共平面性和相互作用力得到了提高。该二维结构的萘二酰亚胺类受体聚合物具有迁移率高、化学稳定性好等优点，将其溶解于氯仿、氯苯等卤代溶剂中，可以通过溶液旋涂成膜，用于有机太阳能电池的制备中。

Description

一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与 应用
技术领域
本发明涉及一种含有多羰基、π-π堆积作用及多炔键构成的二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用，属于有机太阳能电池受体材料领域。
背景技术
太阳能电池是一种直接有效的将清洁的太阳能转化成电能的有效方式。因为可作为清洁廉价的新能源代替目前广泛开采的石油、煤、天然气等而受到人们极大关注。和其他太阳能电池一样，有机太阳能电池的原理也是利用光生伏特现象，不同之处则在于，其利用聚合物吸收光子后产生的激子扩散到共轭聚合物/PCBM异质结界面处而发生电荷分离（参见文献: M C Scharber and N S Sariciftci. Efficiency of bulk-heterojunctionorganic solar cells[J]. Progress in Polymer Science,2013,38(12):1929.）。
有机太阳能电池的研究核心是PCE（光电转化效率），因此，提高光电转化效率是这一领域科学家共同追求的目标。有机太阳能电池一般由给体材料与受体材料组成，其性能取决于聚合物骨架的化学结构。一种良好的有机太阳能受体材料应该具有与太阳光地面辐射光谱匹配的光谱响应范围，以及载流子迁移率高、电极对其收集效率高等等特点（参见文献：M Kaltenbrunner, M S White, E D Głowacki, et al.Ultrathin and lightweightorganic solar cells with high flexibility[J].Nature communications,2011,3(1):85-100.）。
发明内容
本发明的目的在于提供一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用，其具有光电转化效率高、化学稳定性好、平面性优异等优点，在有机太阳能电池受体材料领域具有巨大的应用前景。
为实现上述目的，本发明采用如下技术方案：
本发明第一个目的是保护一种二维结构的萘二酰亚胺类受体聚合物，其结构式为：
Figure 846646DEST_PATH_IMAGE001
，式中，R1为C6~C20的烷基链，R2为C20~C29，n≥1。
本发明第二个目的是保护所述二维结构的萘二酰亚胺类受体聚合物的制备方法，其是将单体M1、M2与催化剂Pd(PPh3)4、CuI溶于无水卤代有机溶剂中，在氮气下加热回流进行聚合后，经索氏提取进行提纯，高温真空干燥获得所述聚合物；
其中，单体M1的结构式为：
Figure 598701DEST_PATH_IMAGE002
（R1为C6~C20的烷基链）；
单体M2的结构为：
Figure 725225DEST_PATH_IMAGE003
（R2为C20~C29）；
所述卤代有机溶剂为氯苯、邻二氯苯等。
所述单体M1的制备方法如下：
（1）按摩尔比1:1.3将NDI化合物A（
Figure 116892DEST_PATH_IMAGE004
）与噻吩乙腈化合物B（
Figure 971585DEST_PATH_IMAGE005
）溶解于有机溶剂中，加入6%当量的PdCl2(PPh3)2与6%当量的CuI，80℃加热回流过夜后，经萃取、硅胶柱层析提纯、干燥，得到中间化合物C，其结构式为：
Figure 578147DEST_PATH_IMAGE006
；
（2）按摩尔比1:0.75将步骤（1）所得的中间化合物C与2,5-二溴对苯二甲醛加入有机溶剂中，再加入5mol%的四丁基氢氧化铵，50℃反应6小时，通过过滤重结晶的方法得到红色粉末，即为单体M1的前置体D，其结构式为：
Figure 430565DEST_PATH_IMAGE007
；
（3）将步骤（2）所得前置体D与过量三甲基硅基乙炔溶于有机溶剂，加入Pd(PPh3)4、CuI，加热回流后，经萃取、柱层析提纯、干燥得到带TMS保护的单体M1，再将其溶于二氯甲烷与甲醇的混合溶液中（1:1，v/v）中，加入5当量的碳酸钾进行去保护，脱掉TMS得到所述单体M1。
所述有机溶剂为三乙胺、甲醇、二氯甲烷、二异丙胺、叔丁醇等。
本发明第三个目的是保护所述二维结构的萘二酰亚胺类受体聚合物在制备有机太阳能电池上的应用。
本发明的显著优点:
（1）本发明所采用的原料相对廉价，合成路径不复杂；
（2）本发明所制得的聚合物具有高度平面性及化学稳定性好等优点；
（3）将本发明所得二维结构的萘二酰亚胺类受体聚合物易于旋涂成膜，具有较好吸光范围和良好的化学稳定性且其光伏器件性能较好。
附图说明
图1为实施例1中的异辛烷的NDI化合物A的核磁共振氢谱。
图2为实施例2所得间化合物C的核磁共振氢谱。
图3为实施例3所得单体M1前置体D的核磁共振氢谱。
图4为实施例4所得单体M1的核磁共振氢谱。
图5为实施例6所得聚合物在溶液状态及薄膜状态下的紫外光谱图。
图6为实施例6所得聚合物的CV曲线图。
图7为实施例6所得聚合物的器件性能。
具体实施方式
为了使本发明所述的内容更加便于理解，下面结合具体实施方式对本发明所述的技术方案做进一步的说明，但是本发明不仅限于此。
实施例1 含有异辛烷的NDI化合物A制备
按文献《Caitlin S. Sample, Eisuke Goto, Modular synthesis ofasymmetric rylene derivatives, Journal of Materials Chemistry C., 2017, 5,1052-1056》制备含有异辛烷的NDI化合物A，其结构式为：
Figure 508198DEST_PATH_IMAGE008
。
实施例2 中间化合物C的制备
将1.79 g（4.62 mmol）实施例1制得的含有异辛烷的NDI，与0.85g（5.76mmol）噻吩乙腈化合物B（
Figure 838685DEST_PATH_IMAGE009
）溶于20 mL三乙胺中，加入202.4mg（0.28mmol）PdCl2(PPh3)2与54.9mg（0.28mmol）CuI，在氮气氛围下80℃反应过夜，反应结束后旋干三乙胺，使用二氯甲烷萃取，经硅胶柱提纯（洗脱剂为石油醚:二氯甲烷=2:1，v/v），得到中间化合物C（
Figure 814600DEST_PATH_IMAGE010
），产率为52.31%。1H NMR (500 MHz, Chloroform-d) δ 8.67 (ddd, J =8.4, 4.7, 1.2 Hz, 2H), 8.58 (d, J = 7.6 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H),7.88 (dd, J = 8.3, 7.3 Hz, 1H), 7.37 (d, J = 3.7 Hz, 1H), 7.10 (dt,J = 3.6,1.1 Hz, 1H), 5.37 (s, 1H), 4.15 (qd, J = 12.9, 7.3 Hz, 2H), 3.99 (d, J = 1.0Hz, 2H), 2.28 – 2.21 (m, 1H), 2.11 – 2.01 (m, 1H), 2.01 – 1.94 (m, 1H), 1.70– 1.63 (m, 1H), 1.46 – 1.31 (m, 5H), 1.29 (d, J = 6.8 Hz, 3H), 0.93 (dt, J =27.6, 7.2 Hz, 7H)。
实施例3 前置体D的制备
将200mg（0.44 mmol）实施例2制得的中间化合物C，与60.54mg（0.33mmol）2,5-二溴对苯二甲醛溶于20 ml叔丁醇中，然后加入0.2mL、1mol/L的四丁基氢氧化铵，在氮气氛围下50℃搅拌反应6小时，反应结束后冷却至室温，甲醇过滤除去红色固体，使用氯仿与丙酮重结晶，得到单体M1的前置体D，产率为15.6%。1H NMR (400 MHz, Chloroform-d) δ 8.66(s, 4H), 8.58 (d, J = 8.0 Hz, 2H), 8.41 (s, 2H), 7.97 (d, J = 7.7 Hz, 2H),7.88 (s, 1H), 7.65 (s, 1H), 7.47 (d, J = 13.0 Hz, 4H), 4.13 (s, 4H), 1.95 (s,2H), 1.54 (s, 14H), 1.35 (d, J = 32.9 Hz, 20H), 0.91 (d, J = 22.7 Hz, 14H)。
实施例4 单体M1的制备
将400mg（0.34 mmol）实施例3制得的前置体D与过量三甲基硅基乙炔溶于有机溶剂，加入18.9 mg（0.016mmol）Pd(PPh3)4、3.13 mg（0.016 mmol）CuI，加热回流后，经萃取、快速粗糙二氯甲烷柱层析提纯、干燥，得到带TMS保护的单体M1，再将其溶于二氯甲烷与甲醇的混合溶液中（1:1，v/v）中，加入5当量的碳酸钾进行去保护，脱掉TMS经过二氯甲烷快速过柱得到所述单体M1（
Figure 103499DEST_PATH_IMAGE011
）。1H NMR (500 MHz, Chloroform-d) δ 8.72 – 8.64 (m, 4H), 8.63 – 8.54 (m, 4H),8.02 – 7.84 (m, 4H), 7.54 – 7.42 (m, 4H), 5.32 (s, 8H), 4.17 – 4.10 (m, 2H),2.02 (s, 2H), 1.28 (s, 2H), 1.25 (s, 26H), 1.24 (s, 4H), 0.93 – 0.84 (m, 6H)。
实施例5 单体M2的制备
按文献《Pahlavanlu, P.;Tilley, A. J.;McAllister, B. T.; Seferos, D.S., Microwave Synthesis of Thionated Naphthalene Diimide-Based SmallMolecules and Polymers. J Org Chem 2017, 82 (23), 12337-12345.》制备单体M2，其结构式为：
Figure 751649DEST_PATH_IMAGE012
。
实施例6 二维结构的萘二酰亚胺类受体聚合物的制备
将75 mg（0.069mmol）实施例4制得的单体M1与79.5 mg（0.069 mmol）与实施例5所得单体M2，7.9 mg（0.069mmol）Pd(PPh3)4、0.92 mg（0.6 mmol）CuI一同溶于5 mL氯苯与二异丙胺的混合溶液（1:1，v/v）中，在氮气气氛下80℃反应72小时，倒入甲醇中过滤，经过索氏提取得到聚合物，产率90%。
实施例7 二维结构的萘二酰亚胺类受体聚合物应用于有机太阳能电池器件中
将5-15mg的受体聚合物和给体材料PTB7-Th溶于氯苯中制成薄膜，夹在电池嵌在玻璃的阴极和阳极之间，制得有机太阳能器件的电极结构。其中聚合物与给体材料的质量比为1:1时，测得光电转换效率达到2.6%。填充因子达到66%。
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。

Claims (4)

1.一种二维结构的萘二酰亚胺类受体聚合物，其特征在于，其结构式为：
Figure DEST_PATH_IMAGE002
，式中，R1为C6~C20的烷基链，R2为C20~C29的烷基链，n≥1。
2.一种如权利要求1所述的二维结构的萘二酰亚胺类受体聚合物的制备方法，其特征在于，将单体M1、M2与催化剂Pd(PPh3)4、CuI溶于无水卤代有机溶剂中，在氮气下加热回流进行聚合后，经提纯、高温真空干燥获得所述聚合物；
其中，单体M1的结构式为：
Figure DEST_PATH_IMAGE004
；
单体M2的结构为：
Figure DEST_PATH_IMAGE006
。
3.根据权利要求2所述的二维结构的萘二酰亚胺类受体聚合物的制备方法，其特征在于，单体M1的制备方法如下：
（1）将NDI化合物A与噻吩乙腈化合物B溶解于有机溶剂中，加入PdCl2(PPh3)2、CuI，加热回流后，经萃取、提纯、干燥，得到中间化合物C，其结构式为：
Figure DEST_PATH_IMAGE008
；
其中，所述NDI化合物A的结构式为：
Figure DEST_PATH_IMAGE010
；
所述噻吩乙腈化合物B的结构式为：
Figure DEST_PATH_IMAGE012
；
（2）将步骤（1）所得的中间化合物C与2,5-二溴对苯二甲醛在有机溶剂中反应，得到前置体D，其结构式为：
Figure DEST_PATH_IMAGE014
；
（3）将步骤（2）所得前置体D与三甲基硅基乙炔溶于有机溶剂，加入Pd(PPh3)4、CuI，加热回流后，经萃取、柱层析提纯、干燥得到带TMS保护的单体M1，再将其溶于有机溶剂中，加入5当量的碳酸钾进行去保护，得到所述单体M1。
4.一种如权利要求1所述的二维结构的萘二酰亚胺类受体聚合物在制备有机太阳能电池上的应用。
CN201811573149.3A 2018-12-21 2018-12-21 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用 Active CN109553757B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811573149.3A CN109553757B (zh) 2018-12-21 2018-12-21 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811573149.3A CN109553757B (zh) 2018-12-21 2018-12-21 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用

Publications (2)

Publication Number Publication Date
CN109553757A CN109553757A (zh) 2019-04-02
CN109553757B true CN109553757B (zh) 2021-03-02

Family

ID=65870679

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811573149.3A Active CN109553757B (zh) 2018-12-21 2018-12-21 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用

Country Status (1)

Country Link
CN (1) CN109553757B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110204545B (zh) * 2019-06-05 2021-02-02 南京邮电大学 一种基于苝酰亚胺的有机光伏材料及其制备方法与应用
CN114133391A (zh) * 2021-12-06 2022-03-04 福州大学 母核取代萘二酰亚胺电化学聚合单体及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102295754B (zh) * 2010-06-28 2012-12-26 海洋王照明科技股份有限公司 含萘四羧酸二酰亚胺-萘并二噻吩的共聚物、制备方法及其应用
DE102011006885A1 (de) * 2011-04-06 2012-10-11 Leibniz-Institut Für Polymerforschung Dresden E.V. Verfahren zur Herstellung von konjugierten Polymeren
CN105885017A (zh) * 2015-01-07 2016-08-24 宁波智锐新材料有限公司 一种含三键的萘四羧酸二酰亚胺类新型高分子聚合物

Also Published As

Publication number Publication date
CN109553757A (zh) 2019-04-02

Similar Documents

Publication Publication Date Title
CN102906152B (zh) 含芴、蒽和苯并噻二唑单元的聚合物及其制备方法和应用
CN110734539B (zh) 基于五元或七元芳香稠环的聚合物及其在有机光电器件中的应用
CN112225882B (zh) 一类含非稠环受体单元的n-型聚合物及其制备方法与应用
CN110028654B (zh) 基于萘酰亚胺-硒吩衍生物的有机n型半导体聚合物材料及其制备方法与应用
CN101787020A (zh) 一种可溶液加工的有机共轭分子及在太阳能电池中的应用
CN109553757B (zh) 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用
CN110156616A (zh) 基于芴乙烯桥联芳香环核的免掺杂空穴传输材料的合成方法及其在钙钛矿电池中的应用
CN102453228B (zh) 含芴、蒽和苯并二噻吩单元有机半导体材料及其制备方法和应用
CN102146153A (zh) 苝四羧酸二酰亚胺-咔唑-二噻吩基苯并噻二唑共轭聚合物及其制备方法和应用
CN103080183B (zh) 含芴有机半导体材料,其制备方法和应用
CN102295748B (zh) 含蒽和吡咯并吡咯二酮单元的芴类聚合物、制备方法及其应用
CN108069982B (zh) 一种不对称氰亚甲基靛酮受体材料及其制备方法和应用
CN103965449A (zh) 一种含铱光功能聚合物及其制备方法
CN114479019B (zh) 一种三嗪类聚合物材料及其制备方法和在光电器件中的应用
CN102286141A (zh) 含芴、蒽和噻吩并噻吩单元的有机半导体材料、制备方法及其应用
CN109776769A (zh) 一种基于噻吩、苝二酰亚胺和异靛蓝单元的三元共聚物及其制备方法
CN102146151A (zh) 苝四羧酸二酰亚胺共轭聚合物及其制备方法和应用
CN102477143B (zh) 一种含芴的有机半导体材料及其制备方法和应用
CN114621276A (zh) 一种苯并噻二唑硼氮衍生物及其应用
CN105367756B (zh) 一种吲哚衍生物与苯并二噻吩双锡共聚物的制备和用途
CN110964041B (zh) 一种基于苯并酰亚胺的受体材料及其制备方法和应用
CN102161750B (zh) 含蒽和苯并噻二唑类共聚物及其制备方法和应用
CN113956447A (zh) 基于稠环酰亚胺结构的电子型聚合物及其制备方法和器件应用
CN102295750B (zh) 含咔唑卟啉-蒽共聚物、制备方法及其应用
CN102372838B (zh) 基于芴、蒽和喹喔啉的有机半导体材料及其制备方法和应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant