CN114621251A - 基于喹喔啉衍生物的稠环单元、含该单元的小分子、聚合物及制备方法与应用 - Google Patents
基于喹喔啉衍生物的稠环单元、含该单元的小分子、聚合物及制备方法与应用 Download PDFInfo
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- CN114621251A CN114621251A CN202210289755.2A CN202210289755A CN114621251A CN 114621251 A CN114621251 A CN 114621251A CN 202210289755 A CN202210289755 A CN 202210289755A CN 114621251 A CN114621251 A CN 114621251A
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- quinoxaline
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- 229920000642 polymer Polymers 0.000 title claims abstract description 71
- 238000002360 preparation method Methods 0.000 title claims abstract description 51
- 150000003384 small molecules Chemical class 0.000 title claims abstract description 20
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 150000003252 quinoxalines Chemical class 0.000 claims description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 24
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 14
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 6
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl tin Chemical group 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
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- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
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- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- VBZDMKSVSNFQSG-UHFFFAOYSA-N 2,3-dibromoquinoxaline Chemical class C1=CC=C2N=C(Br)C(Br)=NC2=C1 VBZDMKSVSNFQSG-UHFFFAOYSA-N 0.000 claims 1
- CTFNJPHOILFHEL-UHFFFAOYSA-N CC1=C(C=CC=C1)[P] Chemical compound CC1=C(C=CC=C1)[P] CTFNJPHOILFHEL-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 5
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- 125000003118 aryl group Chemical group 0.000 abstract 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
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Abstract
本发明公开了基于喹喔啉衍生物的稠环单元、含该单元的小分子、聚合物及它们的制备方法与应用。本发明以喹喔啉衍生物为基础,构建了一类具有大稠环结构的新型芳香单元;并以基于喹喔啉衍生物的稠环单元构建了一系列小分子和共聚物,制备的小分子和聚合物具有宽光谱范围的吸收和高的载流子迁移率。基于此类基于喹喔啉衍生物的稠环单元的小分子和聚合物可作为活性层,应用在有机/聚合物光电探测器和有机/聚合物太阳电池等有机/聚合物电子器件中。
Description
技术领域
本发明属于高分子光电材料技术领域,具体涉及到基于喹喔啉衍生物的稠环单元、含该单元的小分子、聚合物及制备方法与应用。
背景技术
随着全球对于能源需求的逐年增加,石油、煤炭等传统能源的日益枯竭,以及对保护地球生态环境的需要,全世界越来越多的科学家将研究集中在氢气、太阳能等取之不尽用之不竭的可再生清洁能源。
已经成熟的无机硅、砷化镓、磷化铟等基于无机材料的光伏器件已经在市场上占有主导地位,然而由于其对材料纯度的要求高,加工过程中会产生高能耗及污染等问题,且其价格非常昂贵,因此在追求低成本和绿色环保的今天,其大规模应用受到了限制。
有机光电器件作为一种新型薄膜光伏电池技术,具有全固态、光伏材料性质可调范围宽、可实现半透明、柔性电池、具有大面积低成本制备潜力等突出优点。有机材料的光伏性能可调范围宽,可利用化学手段对材料的能级、载流子迀移率以及吸收等性能进行有效的调控。有机/聚合物光伏器件可采用打印、印刷等方法进行加工,可借鉴传统塑料的加工工艺,通过卷对卷滚动加工流程制造大面积、柔性的薄膜光伏器件,该生产工艺能够有效降低光伏电池的制造成本。有机光电器件几乎不受环境和场地限制,在许多场合可将光能转换为电能,同时与无机半导体光伏器件有非常强的互补性,无疑具有巨大的商业开发价值和市场竞争力。因此有机光电器件的研究引起了广泛关注,以有机光电器件为核心的科学研究已经成为一个世界范围内竞争激烈的材料科学前沿研究领域。
在众多光电材料中,含喹喔啉及其衍生物的光电材料在有机电致发光、有机太阳电池、化学和生物传感器以及有机场效应晶体管等材料中已经得到了广泛的应用。与喹喔啉及其衍生物相比,将喹喔啉及其衍生物稠环化之后其具有两个喹喔啉相连的结构,因此它具有喹喔啉及其衍生物基本优点的同时,还具有更大的刚性平面、更强的缺电子性。此外,喹喔啉及其衍生物稠环化后还具有一些特殊性能。本发明设计合成了一系列含喹喔啉衍生物的稠环单元,并将其用于有机光电器件中,展现出了良好的载流子迀移率与器件效率。
发明内容
为解决现有技术的缺点和不足之处,本发明的目的在于提供一类基于喹喔啉衍生物的稠环单元及含其的小分子、聚合物。基于喹喔啉衍生物的稠环单元具有较大共轭平面和强吸电性,
本发明另一目的在于提供含上述基于喹喔啉衍生物的稠环单元的小分子;基于该单体的小分子和聚合物具有较窄的带隙和较宽的吸收光谱,且光谱容易通过结构进行调节;同时该类小分子和聚合物还具有较高的载流子迁移率,有利于提高聚合物的外量子效率。
本发明的再一目的在于提供含上述基于喹喔啉衍生物的稠环单元的聚合物。
本发明的再一目的在于提供上述基于喹喔啉衍生物的稠环单元的制备方法。
本发明的再一目的在于提供上述含基于喹喔啉衍生物的稠环单元的小分子的制备方法。
本发明的另一目的在于提供上述含基于喹喔啉衍生物的稠环单元的聚合物的制备方法。
本发明的再一目的在于提供上述含基于喹喔啉衍生物的稠环单元的小分子、聚合物在有机/聚合物电子器件中的应用。
为实现上述目的,本发明采用如下技术方案:
基于喹喔啉衍生物的稠环单元,化学结构式为以下通式:
其中,X、Y各自为O、S、Se中的一种;
R为碳原子数1~30的烷基、碳原子数3~30的环烷基、碳原子数为6~60芳香族烃基或碳原子数为3~60的芳香族杂环基。优选的,R为碳原子数为5~20的烷基、碳原子数8~20的环烷基、碳原子数为10~40芳香族烃基或碳原子数为10~40的芳香族杂环基。
含所述基于喹喔啉衍生物的稠环单元的小分子,化学结构式为以下通式:
其中,Ar1、Ar2各自为H、D、F、CN、烯基、炔基、胺基、硝基、酰基、烷氧基、羰基、碳原子数6~100的芳香族烃基或碳原子数3~100的芳香族杂环基中的一种。X、Y和R的定义与上述相同。
含所述基于喹喔啉衍生物的稠环单元的聚合物,化学结构式满足以下通式:
式中,x、y为各单元的摩尔分数,其中0<x≤1,0≤y<1;n为重复单元数,n为2~1000范围内的整数;X、Y和R的定义与上述相同。
Ar3为碳原子数6~100的芳香族烃基或碳原子数3~100的芳香族杂环基。
进一步的,所述的基于喹喔啉衍生物的稠环单元,优选为以下结构或以下结构的卤代、氘代、烷基取代衍生物:
其中,R的定义与上述相同。
进一步的,所述的含基于喹喔啉衍生物的稠环单元的小分子,其中的Ar1、Ar2单元优选为以下结构或以下结构的卤代、氘代、烷基取代衍生物中的一种或多种:
其中,R1为碳原子数1~30的烷基、碳原子数3~30的环烷基、碳原子数为6~60芳香族烃基或碳原子数为3~60的芳香族杂环基。优选的,R1为碳原子数为5~20的烷基、碳原子数8~20的环烷基、碳原子数为10~40芳香族烃基或碳原子数为10~40的芳香族杂环基。
进一步的,所述的含基于喹喔啉衍生物的稠环单元的聚合物,其中的Ar3单元优选为以下结构或以下结构的卤代、氘代、烷基取代衍生物中的一种或多种:
其中,R1为碳原子数1~30的烷基、碳原子数3~30的环烷基、碳原子数为6~60芳香族烃基或碳原子数为3~60的芳香族杂环基。优选的,R1为碳原子数为5~20的烷基、碳原子数8~20的环烷基、碳原子数为10~40芳香族烃基或碳原子数为10~40的芳香族杂环基。
本发明还提供了制备上述的基于喹喔啉衍生物的稠环单元的方法,包括如下步骤:
通过草酰氯作为含活泼氢的试剂将含羧基的喹喔啉酰氯化,得到含酰氯基团的喹喔啉中间体;然后将含酰氯基团的喹喔啉中间体在三氯化铝的催化下与芳香族化合物发生亲电取代反应生成基于喹喔啉衍生物的稠环单元。
本发明还提供了含基于喹喔啉衍生物的稠环单元的小分子的制备方法,包括以下步骤:惰性气体保护下,将溴代的基于喹喔啉衍生物的稠环单元单体与烷基锡取代的Ar1、Ar2,在催化剂四(三苯基膦)钯和/或三(二亚苄基丙酮)二钯/三(邻甲基苯基膦)的条件下发生Stille偶联反应得到含基于喹喔啉衍生物的稠环单元的小分子。
本发明也提供了含基于喹喔啉衍生物的稠环单元的聚合物的制备方法,包括以下步骤:
在惰性气体保护下,将含双烷基锡官能团的Ar3单元单体与双溴代的基于喹喔啉衍生物的稠环单元单体溶解在溶剂中,然后加入催化剂,进行Stille聚合反应得到目标产物。
进一步的,所述的有机溶剂包括但不限于甲苯、四氢呋喃、二甲苯、氯苯、二氯苯中的至少一种;
进一步的,所述的Stille聚合催化剂为包括但不限于四(三苯基膦)钯、三(二亚苄基丙酮)二钯/三(邻甲基苯基膦)中的至少一种。
进一步的,所述的Stille聚合反应的温度为60~180℃,反应时间为0.5~36h。
进一步的,所述的含双烷基锡官能团的Ar3单元单体与双溴代的基于喹喔啉衍生物的稠环单元单体的用量满足含双烷基锡能团的单体总摩尔量与含双溴官能团的单体总摩尔量相等;所述的催化剂的用量为反应单体摩尔总量的2‰~3%;
进一步的,Stille聚合反应完成后可对所得产物进行纯化,具体为将所得反应液冷却至室温,滴加入搅拌中的甲醇中沉淀,过滤,干燥得粗产物,粗产物先后用甲醇、丙酮、二氯甲烷、氯仿、氯苯抽提,浓缩后再次沉析在甲醇溶液中,过滤,干燥,得目标产物。
进一步的,在Stille聚合反应完成后还可加入烷基锡噻吩,保温继续反应6~12小时;再加入溴代噻吩继续保温反应6~12小时;
更进一步的,所述的烷基锡噻吩的用量为反应单体摩尔总量的10~40%,所述的溴代噻吩的用量为烷基锡噻吩摩尔量的1~20倍。
本发明还提供了含基于喹喔啉衍生物的稠环单元的小分子、聚合物在制备有机/聚合物电子器件中的应用,包括有机/聚合物光电探测器、有机/聚合物太阳电池、有机/聚合物薄膜晶体管、有机/聚合物发光晶体管、有机/聚合物光电晶体管、有机/聚合物有机发光电化学电池中的应用。
进一步的,所述含基于喹喔啉衍生物的稠环单元的小分子、聚合物在制备有机/聚合物电子器件中的应用,包括如下步骤:将所述的含基于喹喔啉衍生物的稠环单元的小分子、聚合物溶于有机溶剂,或者与其他至少一种有机小分子或者聚合物混合溶于有机溶剂,然后通过旋涂、喷墨打印或印刷成膜,即得到所述有机/聚合物电子器件的活性层。
进一步的,所述的有机溶剂包括但不限于二甲苯、四氢呋喃、氯苯、二氯苯。
与现有技术相比,本发明具有如下优点和技术效果:
(1)这类聚合物在300~1000nm的宽光谱范围内的均有吸收,且吸收光谱容易通过聚合物单元种类和含量调节;
(2)这类聚合物具有较高的电子迁移率,有利于可以制备高效率的有机电子器件,特别是有机/聚合物光电探测器。
附图说明
图1为实施例中聚合物P1、IEICO-4F和P1:IEICO-4F混合薄膜的吸收光谱图。
图2为实施例中基于P1:IEICO-4F的聚合物光电探测器器件在0V偏压下的外量子效率曲线图。
具体实施方式
下面结合实施例和附图对本发明作进一步详细的描述,但本发明的实施方式不限于此。
实施例中所用试剂如无特殊说明均可从市场常规购得。
实施例1
化合物6的制备
(1)化合物1的制备
氮气气氛下,将D-酒石酸二异丙酯(10mmol)和N-溴代丁二酰亚胺(40mmol)溶于20ml四氯甲烷中,75℃反应过夜。反应完毕冷却至室温后,抽滤,滤渣用正己烷冲洗3遍,将滤液旋干得到橘红色液体,产率72%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物2的制备
氮气保护下,将5,10-二溴萘并[1,2-c:5,6-c]双[1,2,5]噻二唑(10mmol)溶于100ml醋酸中,常温下将锌粉(200mmol)分五批加入反应液中,加热至100℃回流反应4小时。冷却至室温后,用乙酸乙酯萃取,饱和氯化钠水溶液洗涤3遍,旋干溶剂得到白色固体。氮气保护下,将固体溶于100ml 1,4-二氧六环中,再加入化合物1(40mmol),110℃加热搅拌12小时,冷却后用乙酸乙酯萃取,饱和氯化钠水溶液洗涤3遍,旋干溶剂得到白色固体,产率42%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(3)化合物3的制备
氮气保护下,将化合物2(10mmol)和氢氧化钠(60mmol)溶于20mL四氢呋喃中,60℃反应2小时。反应结束冷却到室温后,加入100ml稀盐酸溶液猝灭反应,将反应液缓慢倒入500mL冰水中,抽滤,滤渣用乙酸乙酯冲洗三遍,然后将滤液用乙酸乙酯萃取,饱和氯化钠水溶液洗涤3遍,旋干溶剂得到固体产物,产率70%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(4)化合物4的制备
氮气保护下,将化合物3(10mmol)和草酰氯(15ml)溶于60ml甲苯中,在室温下加入5ml N,N-二甲基甲酰胺,65℃反应3小时。反应结束冷却到室温,旋干溶剂得到固体产物,产率为72%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(5)化合物5的制备
氮气保护下,将噻吩(10mmol)溶于60ml无水四氢呋喃中,在冰水浴下用恒压滴液漏斗滴加溶于40ml无水四氢呋喃的正丁基锂(25mmol),滴加完毕后室温反应2小时。再用注射器滴加1-溴-2-丁基辛烷(30mmol),滴加完毕后50℃反应12小时。反应结束冷却到室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物通过蒸馏得到黄色液体产物,产率为77%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(6)化合物6的制备
氮气保护下,将化合物4(10mmol)和化合物5(22mmol)溶于100ml无水二氯甲烷中,冰水浴下将三氯化铝(50mmol)分三批加入反应液,室温反应2小时。反应结束后,将500ml冰水缓慢倒入反应中猝灭反应,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:3(v/v)作淋洗剂柱层析提纯,得固体产物,产率63%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物1~6的化学反应方程式如下所示:
实施例2
化合物8的制备
(1)化合物7的制备
氮气保护下,将硒吩(10mmol)溶于60ml无水四氢呋喃中,在冰水浴下用恒压滴液漏斗滴加溶于40ml无水四氢呋喃的正丁基锂(25mmol),滴加完毕后室温反应2小时。再用注射器滴加1-溴-2-丁基辛烷(30mmol),滴加完毕后50℃反应12小时。反应结束冷却到室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物通过蒸馏得到黄色液体产物,产率为72%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物8的制备
氮气保护下,将化合物4(10mmol)和化合物7(22mmol)溶于100ml无水二氯甲烷中,冰水浴下将三氯化铝(50mmol)分三批加入反应液,室温反应2小时。反应结束后,将500ml冰水缓慢倒入反应中猝灭反应,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:3(v/v)作淋洗剂柱层析提纯,得固体产物,产率63%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物7~8的化学反应方程式如下所示:
实施例3
化合物10的制备
(1)化合物9的制备
氮气保护下,将呋喃(10mmol)溶于60ml无水四氢呋喃中,在冰水浴下用恒压滴液漏斗滴加溶于40ml无水四氢呋喃的正丁基锂(25mmol),滴加完毕后室温反应2小时。再用注射器滴加1-溴-2-丁基辛烷(30mmol),滴加完毕后50℃反应12小时。反应结束冷却到室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物通过蒸馏得到黄色液体产物,产率为67%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物10的制备
氮气保护下,将化合物4(10mmol)和化合物7(22mmol)溶于100ml无水二氯甲烷中,冰水浴下将三氯化铝(50mmol)分三批加入反应液,室温反应2小时。反应结束后,将500ml冰水缓慢倒入反应中猝灭反应,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:3(v/v)作淋洗剂柱层析提纯,得固体产物,产率66%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物9~10的化学反应方程式如下所示:
实施例4
化合物12的制备
(1)化合物11的制备
氮气气氛中,冰浴下,将二噻吩并环戊二烯(1.78g,10mmol)、叔丁醇钠(2.88g,30mmol)、溴代十六烷(6.67g,22mmol)加入100mL四氢呋喃中,搅拌反应24小时。减压旋干四氢呋喃,用二氯甲烷萃取,饱和氯化钠水溶液洗涤3遍,旋干二氯甲烷。粗产物用石油醚作淋洗剂柱层析提纯,得到白色固体产物,产率90%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物12的制备
氮气保护下,将化合物11(3.14g,5mmol)溶于150mL无水四氢呋喃中,降温至-5℃,滴加正丁基锂(8mL,20mmol),-5℃下搅拌2小时。注入三甲基氯化锡的四氢呋喃溶液(45mL,45mmol),自然升至室温反应12小时。减压蒸馏除去四氢呋喃后,用二氯甲烷萃取产物,去离子水洗3遍后,旋干二氯甲烷。用异丙醇重结晶得到白色固体产物,产率87%。1H NMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物11~12的化学反应方程式如下所示:
实施例5
化合物14的制备
(1)化合物13的制备
氮气保护下,将3,3’-二溴2,2’-联噻吩(3.24g,10mmol)、2-辛基十二胺(3.57g,12mmol)叔丁醇钠(2.40g,25mmol)、三(二亚苄基丙酮)二钯(0.46g,0.5mmol)、2,2’-双-(二苯膦基)-1,1’-联萘(0.62g,1mmol)加入100mL无水甲苯中。加热至100℃反应12小时后,用饱和氯化钠水溶液洗涤3遍,旋干有机层的溶剂后,粗产物用石油醚作淋洗剂柱层析提纯,得到无色油状产物,产率70%。1H NMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物14的制备
化合物14的反应及提纯方法与化合物12类似,得到浅黄色油状产物,产率84%。1HNMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物13~14的化学反应方程式如下所示:
实施例6
化合物18的制备
(1)化合物15的制备
将4H-环戊并[2,1-B:3,4-B’]二噻吩-4-酮(1.92g,10mmol)溶于20mL氯仿和20mL三氟乙酸的混合溶剂中,随后加入过硼酸钠(2.9g,25mmol)常温反应4小时。用100mL二氯甲烷萃取产物,饱和氯化钠水溶液洗涤三遍,减压旋干溶剂后,粗产物用石油醚:二氯甲烷=1:1(v/v)作淋洗剂柱层析提纯,得到白色固体产物,产率25%。1H NMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
(2)化合物16的制备
氮气保护下,用溴代十六烷与镁屑在无水四氢呋喃中制备1-十六烷基溴化镁。将化合物15(2.08g,10mmol)溶于100mL无水四氢呋喃中,降温至-30℃后,缓慢将1-十六烷基溴化镁的四氢呋喃(25mL,25mmol)溶液滴加入反应瓶,自然升至室温继续12小时。加入20mL去离子水淬灭反应,减压旋干溶剂后用二氯甲烷萃取产物,饱和氯化钠水溶液洗涤三遍,减压旋干溶剂后,粗产物用石油醚:乙酸乙酯=6:1(v/v)作淋洗剂柱层析提纯,得到浅黄色油状产物,产率85%。1H NMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
(3)化合物17的制备
氮气气氛下,将化合物16(6.61g,10mmol)溶于100mL乙酸中,加热至回流后,加入2mL浓盐酸,继续加热反应12小时。冷却至室温后,将反应液倒入500mL冰水中,用二氯甲烷萃取产物,减压旋干有机层溶剂后,粗产物用石油醚:二氯甲烷=4:1(v/v)作淋洗剂柱层析提纯,得到无色油状产物,产率90%。1H NMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
(4)化合物18的制备
化合物18的反应及提纯方法与化合物11类似,得到淡黄色油状产物,产率88%。1HNMR、13CNMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物15~18的化学反应方程式如下所示:
实施例7
聚合物P1的制备
氮气保护下,将化合物6(0.2mmol)和化合物12(0.2mmol)溶解在4mL无水甲苯中,再加入四(三苯基膦)钯(8mg)。140℃下反应24小时,用2-(三丁基锡)噻吩(20mg)进行第一次封端,反应6小时后,用2-溴噻吩(30mg)进行第二次封端,继续反应6小时。结束反应,待反应降到室温后,将反应液沉析在甲醇中,过滤得到的聚合物先后用甲醇、丙酮、二氯甲烷、氯仿、氯苯进行索氏抽提。将得到的氯苯溶液浓缩,再次沉析在甲醇中,过滤,干燥,得到黑色纤维状聚合物。1H NMR和元素分析结果表明所得到的化合物为目标产物。
合成聚合物P1的化学反应方程式如下所示:
实施例8
聚合物P2的制备
聚合物P2的反应及提纯方法与聚合物P1类似,得到黑色纤维状聚合物。1H NMR和元素分析结果表明所得到的化合物为目标产物。反应方程式如下:
实施例9
聚合物P3的制备
氮气气氛中,将化合物18(0.12mmol)、2,5-二(三甲基锡)噻吩(0.08mmol)、化合物6(0.2mmol)溶解在5mL无水氯苯中,再三(二亚苄基丙酮)二钯(3mg)和三(邻甲基苯基)磷(6mg)。140℃下反应24小时,用2-(三丁基锡)噻吩(20mg)进行第一次封端,反应6小时后,用2-溴噻吩(30mg)进行第二次封端,继续反应6小时。结束反应,待反应降到室温后,将反应液沉析在甲醇中,过滤得到的聚合物先后用甲醇、丙酮、二氯甲烷、氯仿、氯苯进行索氏抽提。将得到的氯苯溶液浓缩,再次沉析在甲醇中,过滤,干燥,得到黑色纤维状聚合物。。1H NMR和元素分析结果表明所得到的化合物为目标产物。图1为聚合物P3的吸收光谱图,由图可知P3在300~1000nm的宽波长范围内均有吸收。
合成聚合物P3的化学反应方程式如下所示:
实施例10
聚合物P4的制备
氮气气氛中,将化合物18(0.12mmol)、化合物14(0.08mmol)、化合物6(0.2mmol)溶解在5mL无水氯苯中,再三(二亚苄基丙酮)二钯(3mg)和三(邻甲基苯基)磷(6mg)。140℃下反应24小时,用2-(三丁基锡)噻吩(20mg)进行第一次封端,反应6小时后,用2-溴噻吩(30mg)进行第二次封端,继续反应6小时。结束反应,待反应降到室温后,将反应液沉析在甲醇中,过滤得到的聚合物先后用甲醇、丙酮、二氯甲烷、氯仿、氯苯进行索氏抽提。将得到的氯苯溶液浓缩,再次沉析在甲醇中,过滤,干燥,得到黑色纤维状聚合物。1H NMR和元素分析结果表明所得到的化合物为目标产物。反应方程式如下:
实施例11
化合物22的制备
(1)化合物19的制备
氮气保护下,将化合物11(5mmol)溶于150mL无水四氢呋喃中,降温至-5℃,滴加正丁基锂(5mmol),-5℃下搅拌2小时。注入三甲基氯化锡的四氢呋喃溶液(5mmol),自然升至室温反应12小时。减压蒸馏除去四氢呋喃后,用二氯甲烷萃取产物,去离子水洗3遍后,旋干二氯甲烷。用异丙醇重结晶得到白色固体产物,产率87%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物19的化学反应方程式如下所示:
(2)化合物20的制备
氮气保护下,将化合物6(5mmol)和化合物19(15mmol)溶解在20mL无水甲苯中,再加入四(三苯基膦)钯(20mg),140℃下反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:3(v/v)作淋洗剂柱层析提纯,得固体产物,产率66%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(3)化合物21的制备
氮气保护下,将化合物20(5mmol)溶解在20ml N,N-二甲基甲酰胺中,再加入2ml1,2-二氯乙烷,在冰水浴下搅拌30分钟,再加入三氯氧磷(30mmol),在冰水浴下搅拌1小时,升温到60℃反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:1(v/v)作淋洗剂柱层析提纯,得固体产物,产率87%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(4)化合物22的制备
氮气保护下,将化合物21(10mmol)和5,6-二氟-3-(二氰基亚甲基)靛酮(60mmol)溶解在60ml氯仿中,120℃反应12小时。反应结束后冷却到室温,将200ml无水甲醇加入反应液中,抽滤,滤渣用无水甲醇冲洗三次。滤渣用二氯甲烷和无水甲醇重结晶两次,得到固体产物,产率79%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物20~22的化学反应方程式如下所示:
实施例12
化合物26的制备
(1)化合物23的制备
氮气保护下,将化合物13(5mmol)溶于150mL无水四氢呋喃中,降温至-5℃,滴加正丁基锂(5mmol),-5℃下搅拌2小时。注入三甲基氯化锡的四氢呋喃溶液(5mmol),自然升至室温反应12小时。减压蒸馏除去四氢呋喃后,用二氯甲烷萃取产物,去离子水洗3遍后,旋干二氯甲烷。用异丙醇重结晶得到白色固体产物,产率87%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物23的化学反应方程式如下所示
(2)化合物24的制备
氮气保护下,将化合物6(5mmol)和化合物23(15mmol)溶解在20mL无水甲苯中,再加入四(三苯基膦)钯(20mg),140℃下反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:2(v/v)作淋洗剂柱层析提纯,得固体产物,产率69%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(3)化合物25的制备
氮气保护下,将化合物24(5mmol)溶解在20ml N,N-二甲基甲酰胺中,再加入2ml1,2-二氯乙烷,在冰水浴下搅拌30分钟,再加入三氯氧磷(30mmol),在冰水浴下搅拌1小时,升温到60℃反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:1(v/v)作淋洗剂柱层析提纯,得固体产物,产率84%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(4)化合物26的制备
氮气保护下,将化合物25(10mmol)和5,6-二氟-3-(二氰基亚甲基)靛酮(60mmol)溶解在60ml氯仿中,120℃反应12小时。反应结束后冷却到室温,将200ml无水甲醇加入反应液中,抽滤,滤渣用无水甲醇冲洗三次。滤渣用二氯甲烷和无水甲醇重结晶两次,得到固体产物,产率77%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物24~26的化学反应方程式如下所示
实施例13
化合物30的制备
(1)化合物23的制备
氮气保护下,将化合物17(5mmol)溶于150mL无水四氢呋喃中,降温至-5℃,滴加正丁基锂(5mmol),-5℃下搅拌2小时。注入三甲基氯化锡的四氢呋喃溶液(5mmol),自然升至室温反应12小时。减压蒸馏除去四氢呋喃后,用二氯甲烷萃取产物,去离子水洗3遍后,旋干二氯甲烷。用异丙醇重结晶得到白色固体产物,产率87%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物27的化学反应方程式如下所示:
(2)化合物28的制备
氮气保护下,将化合物6(5mmol)和化合物27(15mmol)溶解在20mL无水甲苯中,再加入四(三苯基膦)钯(20mg),140℃下反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:2(v/v)作淋洗剂柱层析提纯,得固体产物,产率69%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(3)化合物29的制备
氮气保护下,将化合物28(5mmol)溶解在20ml N,N-二甲基甲酰胺中,再加入2ml1,2-二氯乙烷,在冰水浴下搅拌30分钟,再加入三氯氧磷(30mmol),在冰水浴下搅拌1小时,升温到60℃反应12小时。反应结束后冷却至室温,用乙酸乙酯萃取产物,饱和氯化钠水溶液洗涤三遍,除去有机相溶剂后,粗产物物石油醚:二氯甲烷=1:1(v/v)作淋洗剂柱层析提纯,得固体产物,产率84%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
(4)化合物30的制备
氮气保护下,将化合物29(10mmol)和5,6-二氟-3-(二氰基亚甲基)靛酮(60mmol)溶解在60ml氯仿中,120℃反应12小时。反应结束后冷却到室温,将200ml无水甲醇加入反应液中,抽滤,滤渣用无水甲醇冲洗三次。滤渣用二氯甲烷和无水甲醇重结晶两次,得到固体产物,产率77%。1H NMR、13C NMR、MS和元素分析结果表明所得到的化合物为目标产物。
合成化合物28~30的化学反应方程式如下所示:
实施例14
聚合物光电探测器的制备
取预先做好的方块电阻为15Ω的氧化铟锡(ITO)玻璃,依次用丙酮,洗涤剂,去离子水和异丙醇超声清洗,等离子处理10分钟。在ITO上旋涂参杂有聚苯乙烯磺酸的聚乙氧基噻吩(PEDOT:PSS)膜,厚度为40nm。PEDOT:PSS膜在真空烘箱里80℃下干燥8小时。随后将质量比为1:1的聚合物P1和IEICO-4F的邻二氯苯溶液(1wt.%)旋涂在PEDOT:PSS膜的表面,厚度为100nm。然后在活性层上旋涂一层约5nm厚的PFN-Br薄膜。最后蒸镀100nm厚的金属Al层,器件结构为ITO/PEDOT:PSS/P1:IEICO-4F/PFN-Br/Al。
图2为基于P1:IEICO-4F的聚合物光电探测器器件在0V偏压下的外量子效率曲线图,由图可知,该器件在300-1000nm宽波段范围内均有相应,具有较高的外量子效率。
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 (10)
5.制备权利要求1或2所述的一类基于喹喔啉的稠环单元的方法,其特征在于包括如下步骤:
通过草酰氯作为含活泼氢的试剂将含羧基的喹喔啉酰氯化,得到含酰氯基团的喹喔啉中间体;然后将含酰氯基团的喹喔啉中间体在三氯化铝的催化下与芳香族化合物发生亲电取代反应生成基于喹喔啉衍生物的稠环单元。
6.制备权利要求3所述的含基于喹喔啉衍生物的稠环单元的小分子的方法,其特征在于包括以下步骤:
惰性气体保护下,将溴代的基于喹喔啉衍生物的稠环单元单体与烷基锡取代的Ar1、Ar2,在催化剂四(三苯基膦)钯和/或三(二亚苄基丙酮)二钯/三(邻甲基苯基)磷(质量比为1:1~1:3)的作用下发生Stille偶联反应得到含基于喹喔啉衍生物的稠环单元的小分子。
7.制备权利要求4所述的含基于喹喔啉衍生物的稠环单元的聚合物的方法,其特征在于,包括以下步骤:
在惰性气体保护下,将含双烷基锡官能团的Ar3单元单体与双溴代的基于喹喔啉衍生物的稠环单元单体溶解在溶剂中,然后加入催化剂,进行Stille聚合反应得到目标产物。
8.根据权利要求7所述的制备含基于喹喔啉衍生物的稠环单元的聚合物的方法,其特征在于:在Stille聚合反应完成后还可加入烷基锡噻吩,保温继续反应6~12小时;再加入溴代噻吩继续保温反应6~12小时。
9.根据权利要求7所述的制备含基于喹喔啉衍生物的稠环单元的聚合物的方法,其特征在于:所述的溶剂包括甲苯、四氢呋喃、二甲苯、氯苯、二氯苯中的一种以上;所述的含双烷基锡官能团的Ar3单元单体与双溴代的基于喹喔啉衍生物的稠环单元单体的用量满足含双烷基锡能团的单体总摩尔量与含双溴官能团的单体总摩尔量相等;所述的Stille聚合催化剂为四(三苯基膦)钯、三(二亚苄基丙酮)二钯/三(邻甲基苯基膦)中的一种以上;所述的催化剂的用量为所有反应单体摩尔总量的2‰~3%。
10.权利要求3所述的小分子、权利要求4所述的聚合物在制备有机/聚合物电子器件中的应用,其特征在于,有机/聚合物电子器件包括有机/聚合物光电探测器、有机/聚合物太阳电池、有机/聚合物薄膜晶体管、有机/聚合物发光晶体管、有机/聚合物光电晶体管、有机/聚合物有机发光电化学电池中的应用。
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