CN108794382B - 一种多功能聚集诱导发光增强化合物及其制备方法与应用 - Google Patents
一种多功能聚集诱导发光增强化合物及其制备方法与应用 Download PDFInfo
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- CN108794382B CN108794382B CN201810699898.4A CN201810699898A CN108794382B CN 108794382 B CN108794382 B CN 108794382B CN 201810699898 A CN201810699898 A CN 201810699898A CN 108794382 B CN108794382 B CN 108794382B
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- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
- C08G61/124—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 nitrogen atom in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J5/18—Manufacture of films or sheets
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
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- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/60—Organic compounds having low molecular weight
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
本发明公开了一种多功能聚集诱导发光增强化合物及其制备方法与应用。该化合物中含有含有烷基链的蒽‑三苯乙烯咔唑结构,具有聚集诱导发光增强的性能,发光效率高、强度高,且具有良好的溶解性,易于制备成高质量的薄膜材料。该化合物的制备方法简单,易于纯化,且重现性良好。可用于有机电致发光器件的发光层,荧光传感,检测Fe3+离子以及检测硝基芳香爆炸物。
Description
技术领域
本发明涉及有机发光材料技术领域,尤其涉及一种多功能聚集诱导发光增强化合物及其制备方法与应用。
背景技术
在各类有机发光材料中,蒽因具有荧光量子效率高、易被取代修饰、取代基选择范围广等优点,使得蒽类发光材料成为有机电致发光材料行列中重要的一类。然而,蒽的刚性结构及其平面性导致其容易产生聚集荧光淬灭问题,同时,蒽类小分子发光材料成膜性差,在有机发光二极管(OLEDs)中容易再结晶。
目前,对于蒽类发光材料的研究集中在于蒽的不同衍生物,CN103664648A公开了一种含蒽类衍生物、其制备方法及有机电致发光显示器件,该蒽类衍生物的通式为其中,R1基团选自碳原子数为6-18的芳香基或稠环芳基,R2基团选自胺类化合物;CN103805164A公开了一种苯并蒽类有机发光材料及其制备方法和应用,该材料的结构通式为而CN101200634A公开了可溶性树枝取代的蒽分子蓝光材料及其制备方法与应用,其利用可溶性树枝基团和刚性基团对蒽的9、10位进行取代得到一种发光材料,其中可溶型树枝基团为含有增溶性烷基、烷氧基或者氟取代基的苯基,而刚性基团为芳烃、稠环芳烃或其衍生物。
然而,目前还未报道利用三苯乙烯咔唑取代蒽的9、10位碳原子,由此得到一种新型的聚集诱导发光增强材料,对蒽类有机发光材料的进一步研究及开发具有重要的现实意义。
发明内容
本发明的目的在于提供一种多功能聚集诱导发光增强化合物及其制备方法与应用。
本发明所采取的技术方案是:
本发明的目的之一在于提供一种具有聚集诱导发光增强的化合物,该化合物的通式如式(1)所示:
其中,烷基链长度n为1~12。
优选地,上述烷基链长度n为相同的取值。
更优选地,上述烷基链长度n为6。
本发明的另一目的在于提供上述具有聚集诱导发光增强性能的化合物的制备方法,包括如下步骤:
1)隔绝氧气,将对溴溴苄与亚磷酸三酯反应,得化合物1;
3)隔绝氧气,将化合物1和化合物2反应,得化合物3;
4)隔绝氧气,将化合物3与联硼酸频那醇酯反应,得化合物4;
5)隔绝氧气,将化合物4与9,10-二溴蒽反应,得目标化合物;
反应式如下:
其中,烷基链长度n为1~12。
优选地,上述烷基链长度n为相同的取值。
更优选地,上述烷基链长度n为6。
优选地,步骤1)中对溴溴苄与亚磷酸三酯的摩尔比为(5~10):1。
优选地,步骤1)中对溴溴苄与亚磷酸三酯的摩尔比为(6~8):1。
优选地,步骤1)中对溴溴苄与亚磷酸三酯的摩尔比为7:1。
优选地,步骤1)中的反应温度为100~200℃,反应时间为1~12h。
优选地,步骤1)中的反应温度为120~150℃,反应时间为5~10h。
优选地,步骤1)中的反应温度为140℃,反应时间为7h。
优选地,步骤1)中先升温至反应温度后加入亚磷酸三酯。
优选地,步骤2)中的反应温度为50~70℃,反应时间为1~60h,优选地,反应时间为12~60h,更优选地,反应时间为48h。
优选地,步骤2)中反应结束后还包括进行重结晶得到化合物2。
优选地,步骤2)在乙醇溶液中进行重结晶得到化合物2。
优选地,步骤3)中化合物1和化合物2的摩尔比为(7~12):1。
优选地,步骤3)中化合物1和化合物2的摩尔比为9:1。
优选地,步骤3)中的反应温度为室温,反应时间为1~24h,优选地,反应时间为8~16h,更优选地,反应时间为12h。
优选地,步骤4)中化合物3与联硼酸频那醇酯的摩尔比为1:(1~5)。
优选地,步骤4)中化合物3与联硼酸频那醇酯的摩尔比为1:(2~4)。
更优选地,步骤4)中化合物3与联硼酸频那醇酯的摩尔比为1:3。
优选地,步骤4)的反应温度为70~100℃,反应时间为1~24h。
优选地,步骤4)的反应温度为75~90℃,反应时间为12~18h。
优选地,步骤4)的反应温度为85℃,反应时间为15h。
优选地,步骤4)中先加化合物3,对反应体系进行搅拌、脱气、脱水处理后加入联硼酸频那醇酯。
优选地,步骤5)中化合物4与9,10-二溴蒽的摩尔比为(3~5):1。
更优选地,步骤5)中化合物4与9,10-二溴蒽的摩尔比为4:1。
优选地,步骤5)中的反应温度为70~100℃,反应时间为1~48h。
优选地,步骤5)中的反应温度为80~90℃,反应时间为12~36h。
更优选地,步骤5)中的反应温度为90℃,反应时间为24h。
优选地,步骤5)中先加入化合物4,对反应体系进行搅拌、脱气、脱水处理后加入9,10-二溴蒽。
优选地,步骤4)和步骤5)中反应结束后还包括进行过滤、减压蒸馏、并硅胶柱层析分离提纯得到化合物4和目标化合物。
优选地,步骤4)和步骤5)中硅胶柱层析分离提纯使用的洗脱剂为中极性溶剂和低极性溶剂的混合溶液。
优选地,中极性溶剂和低极性溶剂的体积比为(1~5):(5~1),更优选地为1:1。
优选地,中极性溶剂选自乙酸乙酯、氯仿、二氯甲烷、乙醚、甲酸甲酯、硝基甲烷、乙酸丁酯、异丙醚中的至少一种;低极性选自环己烷、石油醚、己烷、异辛烷、三甲基戊烷、环戊烷、庚烷等烃类溶剂中的至少一种。
优选地,中极性溶剂选自二氯甲烷;低极性溶剂选自石油醚(PE)。
本发明还提供了由上述具有聚集诱导发光增强性能的化合物制备得到的光功能性薄膜。
优选地,该薄膜的分解温度为400~410℃。
上述薄膜热稳定性好、具有蓝绿色荧光且几乎不溶于普通溶剂中。
上述的普通溶剂指水、乙醇、甲醇、乙腈、盐酸、硫酸、磷酸、醋酸、乙二胺、氢氧化钠、氢氧化钾中的至少一种。
本发明针对上述化合物和薄膜的性能,还提供了其相应的应用。
上述化合物在制备有机电致发光器件发光层、检测硝基芳香爆炸物、检测Fe3+中的应用。
上述薄膜在制备有机电致发光器件的发光层、检测硝基芳香爆炸物、检测Fe3+离子等荧光薄膜传感中的应用。
本发明的有益效果是:
1、本发明提供了一种新型的有机发光化合物,该化合物含有烷基链的蒽-三苯乙烯咔唑结构。
2、通过在蒽的9、10位连接三苯乙烯基团,利用其具有多个刚性的苯环使之体积庞大,在聚集之后空间位阻效应使得基团之间扭曲,整个化合物呈扭曲的非平面空间结构,可以有效地降低其π-π聚集,因而具有较高的发光效率;而咔唑基团具有电化学活性,在化合物外围通过烷基链连接四个咔唑基,可使化合物通过电化学聚合方法一步得到交联结构,得到具有较高热稳定性的有机发光聚合物薄膜;另外,烷基链的引入增加了化合物的溶解度,从而使得利用电化学聚合方法得到的薄膜质量高。
3、该化合物发光效率高,且可以通过电化学方法简单方便地制备光功能性薄膜。
4、该化合物的制备方法简单,易于实现且重现性好。
5、该化合物可用于有机电致发光器件的发光层、检测硝基芳香爆炸物以及检测Fe3+离子。
6、该薄膜可用于有机电致发光器件的发光层、检测硝基芳香爆炸物以及检测Fe3+离子等荧光薄膜传感。
附图说明
图1:为TCzDPAn化合物的MS(MALDI-TOF)图;
图2:(A)TCzDPAn化合物粉末与其电聚合薄膜的热重曲线;(B)为TCzDPAn化合物粉末与其电聚合薄膜的示差量热扫描曲线(氮气气氛,扫速10℃/min,温度扫描范围-40~300℃,第二圈);
图3:为TCzDPAn化合物在水/THF混合溶液中的荧光光谱,其中,插图(上)为TCzDPAn化合物(10-5mol/L)在水/THF混合溶液中对应的荧光强度变化曲线;插图(下)为TCzDPAn化合物在纯THF、水/THF(水的体积分数为95%)混合溶液中的荧光照片,在常温下365nm紫外灯激发;
图4:为TCzDPAn化合物(器件Ⅰ)及其电聚合薄膜(器件Ⅱ)制备的多层电致发光器件,(A)为器件Ⅰ和器件Ⅱ各自对应的电流、电压和亮度之间的关系图;(B)为为器件Ⅰ和器件Ⅱ的电流效率曲线;(C)为器件Ⅰ和器件Ⅱ的电致光谱图;
图5:(A)为TCzDPAn化合物检测0.1mM浓度的不同金属离子时的荧光猝灭图;(B)为TCzDPAn电聚合薄膜检测0.1mM浓度的不同金属离子时的荧光猝灭图,其中I为荧光强度,I0为初始荧光强度;
图6:(A)在含有0.1mM的硝基芳香爆炸物溶液中,TCzDPAn电聚合薄膜的荧光率;(B)TCzDPAn电聚合薄膜的荧光强度随爆炸物TNP浓度的变化图;(C)TCzDPAn电聚合薄膜在TNP的饱和蒸汽下,不同时间的荧光光谱图;(D)TCzDPAn电聚合薄膜在TNP饱和蒸汽下荧光淬灭率随时间的变化图;(E)TCzDPAn电聚合薄膜循环性能测试图。
具体实施方式
下面进一步列举实施例以详细说明本发明。同样应理解,以下实施例只用于对本发明进行进一步说明,不能理解为对本发明保护范围的限制,本领域技术人员根据本发明阐述的原理做出的一些非本质的改进和调整均属于本发明的保护范围。下述示例具体的工艺参数等也仅是合适范围中的一个示例,即本领域技术人员可以通过本文的说明做合适范围内的选择,而并非要限定于下文示例的具体数据。
实施例1
TCzDPAn化合物的合成:
1)化合物1的合成:
在装有回流装置和氩气保护的50mL三口瓶中加入对溴溴苄(5.15g,20.36mmol),升温至140℃搅拌熔解,通气15min后加入亚磷酸三乙酯(24.38g,143.79mmol),搅拌反应7h后减压蒸馏过量的亚磷酸三乙酯,冷却至室温,得化合物1;
2)化合物2的合成:
在装有回流装置,氩气保护的100mL的三口烧瓶中,依次加入化合物N-6-溴已基-9H-咔唑(1.03g,3.12mmol,结构式为),20mL DMF,K2CO3(0.26g,1.69mmol),NaI(0.18g,1.08mmol),4,4'-二羟基二苯甲酮(0.31g,1.42mmol)。在温度为60℃下搅拌反应48h后过滤,滤液进行减压蒸馏,得到的固体用乙醇重结晶得到白色固体产物,即:化合物2;
3)化合物3的合成:
在装有回流装置和氩气保护的50mL三口瓶中加入化合物1(1.38g,4.51mmol),加入45mL除水的THF溶剂中搅拌溶解,进行三次除水除氧操作,冰浴降温到0℃,迅速加入t-BuOK(0.05g,0.44mmol),充分溶解后加入化合物2(0.36g,0.51mmol),体系升至室温搅拌反应12h,反应结束后减压蒸馏除去THF,使用水与DCM分液萃取得到有机相,并加入MgSO4放置过夜,过滤并用PE洗涤,减压蒸馏除去DCM后得到淡黄色固体,即:化合物3;
4)化合物4的合成:
氩气保护下,往带有磁力搅拌的干燥的三口瓶中加入化合物3(2.00g,2.31mmol)和25mL 1,4-二氧己环,后对体系进行三次搅拌、脱气、脱水操作,按顺序加入联硼酸频那醇酯(1.76g,6.79mmol),KOAc(0.91g,9.18mmol)和Pd(dppf)Cl2(0.14g,0.19mmol),逐渐升温至85℃,反应15h。反应结束后,减压蒸馏除去1,4-dioxane,加入5%的NaOH溶液和DCM进行分液萃取,得到有机相加入MgSO4放置过夜,后过滤减压蒸馏出去DCM,得到淡黄色固体,所得固体用柱层析分离提纯(SiO2;洗脱剂:DCM:PE=1:1),得到淡黄色固体产物1.79g,产率85%(化合物4);
5)TCzDPAn化合物的合成:
氩气保护下,在干燥的三口瓶中加入化合物4(1.05g,1.15mmol)、60mL甲苯、2mLK2CO3(2mol/L)和适量AliquatR 336相转移剂,后对体系进行3次搅拌、脱气、脱水操作,按顺序加入0.10g(0.29mmol)9,10-二溴蒽、0.20g(0.17mmol)四(三苯基膦)钯(Pd(pph3)4),逐渐升温至90℃,反应24h,反应结束后,减压蒸馏除去甲苯,加入去离子水和DCM进行分液萃取,得有机相并加入MgSO4放置过夜,过滤,减压蒸馏除去DCM,得到淡黄色固体,所得固体用柱层析分离提纯(SiO2:洗脱剂:DCM:PE=1:1),得到淡黄色固体产物0.19g,产率74%(TCzDPAn);
具体反应路线如下:
实施例1中最终得到的淡黄色固体产物的1H NMR(500MHz,CDCl3)为:δ8.12(d,J=7.7Hz,4H),8.07(d,J=7.7Hz,4H),7.70(dd,J=6.8,3.2Hz,4H),7.48(t,J=7.5Hz,4H),7.45-7.40(m,8H),7.37(d,J=8.1Hz,4H),7.32(dd,J=9.4,3.5Hz,8H),7.25-7.15(m,16H),6.99(s,2H),6.89(d,J=8.6Hz,4H),6.85(d,J=8.7Hz,4H),4.34(t,J=7.1Hz,4H),4.29(t,J=7.1Hz,4H),3.94(q,J=6.3Hz,8H),1.98-1.86(m,8H),1.76(dd,J=14.5,9.4Hz,8H),1.59-1.41(m,20H);
13C NMR(500MHz,CDCl3)为:δ140.45,131.60,131.07,129.85,129.31,128.90,125.62,125.58,124.89,122.87,120.38,120.33,118.77,118.73,114.65,114.18,108.64,67.99,67.79,67.69,42.97,42.91,29.19,28.95,27.09,25.96;
质谱(MS(MALDI-TOF))m/z:1747.961([M]+,calcd for C126H114N4O4,1748.900);Anal.Calc.for C126H114N4O4:C 86.56,H 6.57,N 3.20,O 3.60;Found:C 86.82,H 6.71,N3.12%,(见图1);
由此可知,实施例1得到的黄色固体物质的化学式为C126H114N4O4,其结构式如下:
实施例2
实施例3
实施例4
TCzDPAn电聚合薄膜材料的制备
采用循环伏安法在CHI 660D电化学工作站(上海辰华仪器有限公司)进行TCzDPAn的电化学聚合,具体为:
(1)电极预处理:采用三电极体系,工作电极为ITO玻璃(1.5cm×1.5cm,工作面积为1cm2),依次使用异丙醇、蒸馏水、ITO清洗液、异丙醇进行超声清洁,每种溶剂超声洗涤30min,烘干待用;对电极为钛片(1.5cm×3cm),经砂纸打磨后,再依次用丙酮、无水乙醇、蒸馏水进行清洗,烘干待用;参比电极为Ag/Ag+电极(上海辰华科学仪器有限公司);
(2)电解质溶液的配制:称取0.1937g的正四丁基六氟磷酸铵(TBAPF6)和3mg实施例1中的TCzDPAn化合物,放入进样瓶中,加入2.5mL色谱纯的二氯甲烷溶解,后再加入2.5mL的乙腈,超声充分混合均匀后待用;
(3)镀膜:构建三电极体系,ITO玻璃为工作电极,采用循环伏安法制备电聚合发光薄膜,高电位为0.85V,扫描速率为100mv/s。
性能检测:
1、TCzDPAn化合物及其电聚合薄膜的热性能及发光性能
由图2(A)可知:TCzDPAn化合物(实施例1)和TCzDPAn电聚合薄膜分别在390℃和408℃开始分解,这说明两者均具有良好的热性能,TCzDPAn电聚合薄膜的Td相对TCzDPAn化合物稍有提高,表明TCzDPAn化合物聚合后提高了材料的耐热性。
由图2(B)的DSC曲线图可知:TCzDPAn化合物具有玻璃化转变温度,出现在75.3℃,而TCzDPAn电聚合薄膜在这段测试温度区间并没有出现玻璃化转变温度,这是由于TCzDPAn化合物电聚合后形成了交联网状结构。
由图3可知:在THF溶液中TCzDPAn化合物的最大荧光发射波长为457nm,是一种深蓝色发光材料(见插图(下)),且TCzDPAn化合物在纯THF溶液中发光微弱,其荧光发射强度仅有274a.u.,但当THF溶液被稀释时,出现荧光强度增强的现象,且随着THF溶液稀释程度的增加而增强,当水的体积分数达到95%时,其溶液荧光强度为5092a.u.,是纯THF溶液的19倍,因而TCzDPA化合物具有明显的聚集诱导发光增强效应(AIEE)。
2、TCzDPAn化合物及其电聚合薄膜在OLED中的应用
使用TCzDPAn化合物的旋涂薄膜及其电聚合薄膜制备的有机电致发光器件的电致光谱如图4(C)所示,由图4(C)可知:使用TCzDPAn化合物的旋涂薄膜制备的OLED器件(器件Ⅰ)发蓝光,峰值为468nm,启动电压为4.8V,最高亮度达到1282cd/m2(图4(A)),最大流明效率为0.38cd/A(图4(B)中的器件Ⅰ曲线);
使用TCzDPAn电聚合薄膜的器件II的最大发射强度峰位为512nm,比用TCzDPAn化合物旋涂得到的薄膜红移了44nm,CIEx,y值为(0.30,0.51),颜色偏绿;由图4(A)可以看出:电聚合薄膜的器件启动电压为4.2V,最高亮度达到923cd/m2;由图4(B)可知,其最大流明效率为0.28cd/A,具体数值列于下表1:
由上可知:两个器件的亮度均能满足平面显示器(200~400cd/m2)的要求,表明这种新型的AIEE材料在OLED中具有潜在应用,并且,采用电聚合薄膜制备的器件II,显示了更低的滚降性能,表明电聚合薄膜比旋涂薄膜更加稳定。
表1
注:器件I的结构为:ITO/PEDOT:PSS(40nm)/TCzDPAn化合物的旋涂薄膜(~70nm)/CsF(1nm)/Al(100nm);
器件II的结构为:ITO/PEDOT:PSS(40nm)/TCzDPAn电聚合薄膜(~70nm)/CsF(1nm)/Al(100nm)。
3、TCzDPAn化合物及其电聚合薄膜在检测Fe3+中的应用
由图5可知:在0.1mM的金属离子中,TCzDPAn化合物及TCzDPAn电聚合薄膜对Fe3+离子均有检测效果,特别是TCzDPAn电聚合薄膜,对Fe3+离子的淬灭率远远超过其他金属离子,有87.3%的荧光淬灭,这说明TCzDPAn电聚合薄膜对Fe3+离子具有良好的识别功能。
4、TCzDPAn电聚合薄膜的在检测硝基芳香爆炸物中的应用
由图6(A)可知:TCzDPAn电聚合薄膜对硝基芳香爆炸物中的TNP具有识别作用,在0.1mM的硝基芳香爆炸物中,硝基芳香爆炸物中的TNP对TCzDPAn电聚合薄膜的荧光淬灭率达90.37%,这说明可在溶液中实现对TNP的高灵敏性传感;由图6(B)可知:TCzDPAn电聚合薄膜的荧光光谱随着爆炸物TNP浓度的增加而不断淬灭。
将TCzDPAn电聚合薄膜置于TNP的饱和蒸汽下,测试其荧光猝灭光谱(图6(C)、(D)),可以看到,随着暴露时间的增加,荧光强度也随之降低,在200s附近,荧光猝灭达到响应平衡,荧光猝灭率可达69.55%,这说明具有交联结构、性能更稳定的电聚合薄膜可用于爆炸物气氛的检测;由图6(E)可知:TCzDPAn电聚合薄膜具有很好的循环性能,循环四次后,仍有79.29%的荧光保持率,具有重复利用的特点。
注:以上TCzDPAn化合物均为实施例1中合成的化合物。
Claims (9)
3.根据权利要求2所述的制备方法,其特征在于:步骤1)中亚磷酸三酯与对溴溴苄的摩尔比为(5~10):1。
4.根据权利要求2所述的制备方法,其特征在于:步骤3)中化合物1和化合物2的摩尔比为(7~12):1。
5.根据权利要求2所述的制备方法,其特征在于:步骤4)中化合物3与联硼酸频那醇酯的摩尔比为1:(1~5)。
6.根据权利要求2所述的制备方法,其特征在于:步骤5)中化合物4与9,10-二溴蒽的摩尔比为(3~5):1。
7.一种光功能性薄膜,其特征在于:该薄膜由权利要求1所述的化合物制备得到。
8.权利要求1所述的聚集诱导发光增强化合物在制备有机电致发光器件发光层、检测硝基芳香爆炸物、检测Fe3+中的应用。
9.权利要求7所述的薄膜在制备有机电致发光器件的发光层、检测硝基芳香爆炸物、检测Fe3+等荧光薄膜传感中的应用。
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