CN107445849A - 一种三并茚基有机半导体激光材料及其制备方法与应用 - Google Patents
一种三并茚基有机半导体激光材料及其制备方法与应用 Download PDFInfo
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Abstract
本发明涉及一种三并茚基有机半导体激光材料及其制备方法与应用,该材料以三并茚为核,二苯胺基团为封端单元,以不同链长芴基为桥连单元,该材料具有如下式I所示的结构通式:本发明材料制备简单,中间体成本低廉,反应过程容易控制,产品易于分离、收率高、纯度高,该类材料在有机激光器件中表现出良好的热稳定性、成膜稳定性、低阈值、高增益和高发光强度;在有机半导体激光和有机蓝光电致发光方面具有重要的潜在应用价值。
Description
技术领域
本发明属于光电材料与技术领域,具体涉及一种有机半导体激光材料及其制备方法与应用。
背景技术
有机半导体材料由于其良好的光学及电学性能、简单的制备过程以及结构和性能的可调制性,在有机发光二极管(OLED),有机场效应晶体管(OFET),有机太阳能电池(OPV)及有机激光(Organic Lasers)等领域得到了广泛的应用,已经成为有机光电子学研究的重要内容。近年来,有机半导体激光引起人们越来越多的关注。与激光染料相比,有机半导体激光材料除了具有有机激光染料的优点(高的发光效率,可调光谱范围宽,可视为四能级系统等) 外,还具有高的固态发光效率及成膜性好等特点,使其在激光应用方面引起人们的浓厚兴趣。然而,到目前为止,电泵浦有机半导体激光尚未能实现。设计开发具有低阈值、高增益、高载流子迁移率和优异稳定性的有机半导体激光材料是解决这一瓶颈问题的关键。为了获得优异的激光性能,人们设计开发了多种材料体系,包括小分子材料、聚合物材料及单分散大分子材料等。其中,具有多维空间拓扑结构单分散多臂结构共轭大分子材料是一类具有优异光电性能的发光材料体系,不但可以像小分子那样使用常规的硅胶柱层析进行提纯,还具有类似聚合物的良好的成膜性能。此外,由于它们所具有的空间多维结构减弱了分子间的相互作用,使得它们不但在极性溶剂中往往具有更好的溶解性形成表面形貌规整、均一的薄膜,同时该类材料还具有各向同性的光电性能。
对于多臂结构单分散共轭大分子而言,可以通过改变臂或核以及对分子端基修饰来优化分子结构及其光电性能。三并茚是具有C3结构空间对称性的稠环芳香类分子单元,利用其特殊的三维拓扑结构,可以构建出具有树枝状支化结构的多臂结构星状大分子。二苯胺是一类强给电子基团,通过引入二苯胺端基修饰,可以进一步改善分子的电学性能。目前未见任何文献或专利报道二苯胺端基修饰的三并茚基单分散有机半导体激光增益材料。聚合物材料体系虽可以较好地获得低阈值有机半导体材料,但其结构具有不确定性,而且其分散性较差等;小分子虽然结构明确,但是其溶液加工性能不理想。设计开发兼具聚合物材料体系和小分子材料体系两者的优点的材料体系对于开发高性能的有机半导体激光材料具有重要的意义。
发明内容
技术问题:本发明的目的是提供一种三并茚基有机半导体激光材料及其制备方法与应用,以解决目前有机半导体激光增益介质阈值高、稳定性差、材料制备复杂的问题,以及克服有机半导体激光材料优异光物理特性与电学性能难以兼具的难题。
技术方案:为实现上述目的,本发明采用以下的技术方案:
一种三并茚基有机半导体激光材料,该材料是以三并茚为核,二苯胺基团为封端单元,以不同链长芴基为桥连单元,该材料具有如下式I所示的结构通式:
其中,R为C1-C30的直链或支链烷基或烷氧基;n为重复单元,n为0~5的自然数。
所述的R为甲基、乙基、正己基、正辛基或异辛基中的一种。
上述的三并茚基有机半导体激光材料的制备方法,包括以下的合成路线及合成方法:
目标化合物TrnF制备:在N2保护下,将六溴三并茚核、二苯胺端基修饰的芴硼酸酯、碱性化合物与相转移催化剂置于微波反应器中,抽换N2后,进行避光处理,加入催化剂,放入微波反应器中,进行反应,反应结束柱色谱纯化得目标化合物TrnF。
本发明的有机半导体激光材料作为激光增益介质或发光材料应用于有机半导体激光和有机电致发光器件中。
有益效果:本发明的材料制备方法简单,中间体成本低廉,反应过程容易控制,产品易于分离、收率高、纯度高。另外,该类材料在有机激光器件应用中表现出优异的热稳定性能、成膜稳定性、低阈值特性和高发光强度;使其在有机半导体激光和有机电致发光方面具有重要的潜在应用价值。
附图说明
图1为Tr1F的1H NMR谱图。
图2为Tr1F的MALDI-TOF谱图。
图3为Tr2F的1H NMR谱图。
图4为Tr2F的MALDI-TOF谱图。
图5为Tr3F的1H NMR谱图。
图6为Tr3F的MALDI-TOF谱图。
图7为目标分子Tr1F、Tr2F和Tr3F在溶液和薄膜下的吸收、荧光和放大自辐射(ASE) 发射光谱。
图8为目标分子Tr1F、Tr2F和Tr3F在不同电压下发光亮度和电流密度的变化曲线。
图9为目标分子Tr1F、Tr2F和Tr3F在不同退火温度下ASE阈值的变化曲线。
具体实施方式
本发明的三并茚基有机半导体激光材料,是以三并茚为核,二苯胺基团为封端单元,以不同链长芴基为桥连单元,该材料具有如下式I所示的结构通式。其合成方法是:将二苯胺与2,7-二溴芴化学反应进行单边端基修饰二溴芴,通过反应合成二苯胺基芴的单溴取代衍生物,然后进行硼酸酯化反应,最后将其与三并茚的六溴核通过Suzuki偶联反应,制备得到化合物TrnF。该类基于二苯胺端基修饰的以三并茚为核以芴链为臂的六取代星形的有机半导体激光材料具有低的ASE阈值,高的光增益系数及高的热稳定性和良好的电致发光性能。
其中,R为C1-C30的直链或支链烷基或烷氧基;n为重复单元,为0~5的自然数;N是氮原子;H是氢原子。
更具体地,所述的R可以为甲基、乙基、正己基、正辛基或异辛基中的一种。
代表性的例子说明如下:
其中,i是在CuI催化作用下发生偶联反应;ii是n-BuLi/异丙醇频哪醇硼酸酯作用下进行酯化反应;iii是在Pd(PPh3)4催化作用下发生Suzuki偶联反应;iv是在Pd(dppf)2Cl2/联硼酸频那醇酯作用下进行酯化反应;v是在Pd(PPh3)4催化作用下单体化合物3a,3b和3c分别与单体三并茚的六溴核进行Suzuki偶联反应。
以下通过具体若干具体实例对本发明做进一步说明,但实例不限制本发明的涵盖范围。
实施例1:
反应条件一:在N2保护条件下,将二苯胺(169.1mg,1mmol)、9,9-二己基-2,7-二溴芴 (980.2mg,2.0mmol)、叔丁醇钾(179.5mg,1.6mmol),碘化亚铜催化剂(9.5mg,0.05mmol)与相转移催化剂(0.5mL)溶于80mL的无水1,4-二氧六环溶液中,控温110℃条件下,锡箔纸避光,反应48h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2a(324.9mg),产率56.1%。
反应条件二:在N2保护条件下,将二苯胺(169.1mg,1mmol)、9,9-二己基-2,7-二溴芴 (1.2g,2.5mmol)、叔丁醇钾(202.1mg,1.8mmol),碘化亚铜催化剂(11.4mg,0.06mmol)与相转移催化剂(0.4mL)溶于80mL的无水1,4-二氧六环溶液中,控温110℃条件下,锡箔纸避光,反应48h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2a(418.8mg),产率72.3%。
反应条件三:在N2保护条件下,将二苯胺(169.1mg,1mmol)、9,9-二己基-2,7-二溴芴 (1.5g,3mmol)、叔丁醇钾(202.1mg,1.8mmol),碘化亚铜催化剂(15.2mg,0.08mmol)与相转移催化剂(0.6mL)溶于80mL的无水1,4-二氧六环溶液中,控温110℃条件下,锡箔纸避光,反应48h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2a(338.9mg),产率58.5%。
1H NMR(400MHz,CDCl3,δ):7.52(d,J=8.2Hz,1H),7.48–7.38(m,3H),7.27(s,1H),7.24(d,J=7.4Hz,3H),7.11(d,J=10.3,4.7Hz,5H),7.07–6.99(m,3H),1.94–1.77(m,4H),1.19–1.03(m,12H),0.81(t,J=7.2Hz,6H),0.71–0.58(m,4H);13C NMR(100MHz,CDCl3, δ):152.9,151.7,147.9,147.5,140.0,135.1,129.9,129.2,126.0,123.9,123.5,122.6,120.5,120.1, 119.1,55.3,31.5,29.5,24.8,23.8,22.6,14.0.MALDI-TOF-MS(m/z):calcdfor C37H42BrN,Exact Mass:579.25;Found:580.15(M+).Anal.Calcd for C37H42BrN:C,76.54;H,7.29;N,2.41.Found: C,76.24;H,7.59;N,2.18.
实施例2
反应条件一:在N2保护条件下,将反应产物2a(5.8g,10mmol)溶解于80mL已做鼓泡处理干燥的四氢呋喃溶剂中,将反应装置放入-78℃的冰水浴中(丙酮+干冰),抽取7.8mL的n-C4H9Li分多次少量加入反应装置;将n-C4H9Li全部注入(1.5h)后,加入4.5mL的异丙醇频哪醇硼酸酯;控温0℃条件下,反应12h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物3a(2.5g),产率40.1%。
反应条件二:在N2保护条件下,将反应产物2a(8.7g,15mmol)溶解于85mL已做鼓泡处理干燥的四氢呋喃溶剂中,将反应装置放入-78℃的冰水浴中(丙酮+干冰),抽取12mL 的n-C4H9Li分多次少量加入反应装置;将n-C4H9Li全部注入(1.5h)后,加入8mL的异丙醇频哪醇硼酸酯;控温0℃条件下,反应12h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物3a(4.8mg),产率50.6%。
反应条件三:在N2保护条件下,将反应产物2a(5.8g,10mmol)溶解于80mL已做鼓泡处理干燥的四氢呋喃溶剂中,将反应装置放入-78℃的冰水浴中(丙酮+干冰),抽取10mL 的n-C4H9Li分多次少量加入反应装置;将n-C4H9Li全部注入(1.5h)后,加入6mL的异丙醇频哪醇硼酸酯;控温0℃条件下,反应12h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物3a(2.8mg),产率45.3%。
1H NMR(400MHz,CDCl3,δ):7.78(d,J=8.1Hz,1H),7.71(d,J=10.7Hz,1H),7.64–7.49 (m,2H),7.26(s,1H),7.23(d,J=7.4Hz,3H),7.12(d,J=7.6Hz,5H),7.02(d,J=7.4Hz,3H), 1.98–1.77(m,4H),1.39(s,12H),1.06(t,J=18.9Hz,12H),0.79(t,J=7.2Hz,6H),0.62(d,J= 7.3Hz,4H);13C NMR(100MHz,CDCl3,δ):152.8,149.2,148.6,147.2,146.3,143.9,136.5,133.5, 129.8,128.7,123.8,123.4,122.5,120.8,119.4,118.4,83.7,55.2,40.3,31.3,29.6,24.8,23.7,14.0. MALDI-TOF-MS(m/z):calcd forC43H54BNO2,Exact Mass:627.42;Found:628.35(M+).Anal. Calcd for C43H54BNO2:C,82.28;H,8.67;B,1.72;N,2.23.Found:C,82.58;H,9.07;B,2.02;N, 2.53.
实施例3
反应条件一:在N2保护条件下,将反应产物3a(0.75g,1.2mmol)、9,9-二己基-2,7-二溴芴(1.2g,2.4mmol),Pd(PPh3)4(5.8mg,0.005mmol)催化剂溶于40mL的甲苯中,然后加入13 mL的K2CO3水溶液中,控温100℃反应24h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2b(0.72g),产率65.6%。
反应条件二:在N2保护条件下,将反应产物3a(0.94g,1.5mmol)、9,9-二己基-2,7-二溴芴(1.6g,3.2mmol),Pd(PPh3)4(11.6mg,0.01mmol)催化剂溶于45mL的甲苯中,然后加入15 mL的K2CO3水溶液中,控温100℃反应24h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2b(1.05g),产率76.5%。
反应条件三:在N2保护条件下,将反应产物3b(1.5g,1.5mmol)、9,9-二己基-2,7-二溴芴(1.6g,3.2mmol),Pd(PPh3)4(11.6mg,0.01mmol)催化剂溶于45mL的甲苯中,然后加入15 mL的K2CO3水溶液中,控温100℃反应24h;反应结束后冷却至室温经萃取和色谱柱纯化得到反应产物2c(1.37g),产率73.5%。
产物2b:1H NMR(400MHz,CDCl3,δ):7.74–7.56(m,8H),7.49(s,2H),7.28(s,2H),7.24 (s,2H),7.14(d,J=7.5Hz,5H),7.07–6.97(m,3H),1.97(t,J=28.5Hz,8H),1.21–1.00(m, 24H),0.89(t,J=6.8Hz,4H),0.79(d,J=8.7,7.1Hz,12H),0.72–0.66(m,4H);13CNMR(100 MHz,CDCl3,δ):153.3,152.43,151.5,151.1,148.0,147.2,141.1,140.3,139.9,139.5,139.1,136.0, 130.1,129.2,128.8,127.1,126.2,123.7,123.6-123.4,122.5,121.2,120.4,112.0,119.4,55.9,40.5, 31.5,29.6,24.1,23.9,14.0.MALDI-TOF-MS(m/z):calcd for C62H74BrN,Exact Mass:911.50; Found:913.12(M+).Anal.Calcd forC62H74BrN:C,81.55;H,8.17;N,1.53.Found:C,81.75;H, 8.37;N,1.43.
产物2c:1H NMR(400MHz,CDCl3,δ):7.83–7.57(m,14H),7.48(d,J=8.5Hz,2H),7.28 (s,2H),7.24(s,2H),7.14(d,J=7.6Hz,5H),7.03(d,J=14.7,7.6Hz,3H),2.14–1.86(m,12H), 1.21–1.02(m,36H),0.78(d,J=13.4,6.8Hz,30H);13C NMR(100MHz,CDCl3,δ):153.2, 152.7,152.2,151.4,151.1,148.3,147.5,141.0,140.0,139.6,139.5,138.8,136.3,129.9,129.1, 126.7,123.7,122.4,120.5,120.1,119.4,55.2,40.7,31.4,29.6,24.1,23.3,14.4.MALDI-TOF-MS (m/z):calcd for C87H106BrN,Exact Mass:1243.75;Found:1245.72(M+).Anal.Calcd for C87H106BrN:C,83.88;H,8.58;N,1.12.Found:C,83.68;H,8.78;N,1.33.
实施例4
反应条件一:在N2保护条件下,将反应物2b(1.8g,2mmol)与联硼酸频那醇酯(409.5 mg,2.4mmol)、Pd(dppf2)Cl2催化剂(14.2mg,0.02mmol)和KOAc(588.8mg,6mmol) 溶解在60mL无水二氧六环溶剂中,控温110℃条件下,避光反应24h;反应结束经色谱柱纯化得到反应产物3b(1.06g),产率55.4%。
反应条件二:在N2保护条件下,将反应物2b(1.8g,2mmol)与联硼酸频那醇酯(761.8 mg,3mmol)、Pd(dppf2)Cl2催化剂(14.2mg,0.02mmol)和KOAc(588.8mg,6mmol) 溶解在60mL无水二氧六环溶剂中,控温110℃条件下,避光反应24h;反应结束经色谱柱纯化得到反应产物3b(1.18g),产率61.7%。
反应条件三:在N2保护条件下,将反应物2c(1.2g,1mmol)与联硼酸频那醇酯(380.9 mg,1.5mmol)、Pd(dppf2)Cl2催化剂(7.2mg,0.01mmol)和KOAc(294.4mg,3mmol) 溶解在30mL无水二氧六环溶剂中,控温110℃条件下,避光反应24h;反应结束经色谱柱纯化得到反应产物3c(0.78g),产率60.7%。
产物3b:1H NMR(400MHz,CDCl3,δ):7.86–7.57(m,10H),7.29(d,J=6.0Hz,4H),7.20–7.11(m,5H),7.05(d,J=14.7,4.7Hz,3H),2.10–1.83(m,8H),1.43–1.37(m,12H),1.22– 1.02(m,24H),0.85–0.65(m,20H);13C NMR(100MHz,CDCl3,δ):152.4,152.1,151.4,150.2, 148.0,147.2,143.8,141.1,140.5,139.7,136.6,133.8,129.0,127.8,126.6,123.7,122.5,121.3, 120.4,119.5,119.1,55.2,40.2,31.7,29.6,24.9,23.5,14.1.MALDI-TOF-MS(m/z):calcd for C68H86BNO2,Exact Mass:959.68;Found:960.28(M+).Anal.Calcd for C68H86BNO2:C,85.06;H, 9.03;B,1.13;N,1.46.Found:C,85.16;H,9.33;B,1.36;N,1.26.
产物3c:1H NMR(400MHz,CDCl3,δ):7.86–7.55(m,16H),7.28(d,J=1.9Hz,2H),7.24 (s,2H),7.14(d,J=7.5Hz,5H),7.06–6.99(m,3H),2.01(t,J=34.3Hz,12H),1.39(d,J=6.3Hz, 12H),1.23–0.96(m,36H),0.88–0.61(m,30H);13C NMR(100MHz,CDCl3,δ):153.2,152.4, 152.1,151.4,151.1,148.2,147.5,141.5,140.0,139.6,139.5,138.8,136.0,129.9,129.1,125.6, 123.7,122.4,120.4,120.1,119.4,55.2,40.2,31.4,29.6,24.2,23.3,14.4.MALDI-TOF-MS(m/z): calcd for C93H118BNO2,Exact Mass:1291.93;Found:1292.78(M+).Anal.Calcd for C93H118BNO2: C,86.40;H,9.20;B,0.84;N,1.08.Found:C,86.26;H,9.15;B,0.89;N,1.13.
实施例5
反应条件一:在N2保护下,称量化合物4(50mg,0.038mmol)、化合物3a(213.9mg,0.34mmol)、KOH(50.8mg,0.91mmol)、相转移催化剂四丁基嗅化铵(TBAB)(60.9mg) 置于微波高压反应管中,抽换N2后,进行避光处理,加入催化剂Pd(PPh3)4(8mg,0.007mmol),加入3mL无水无氧四氢呋喃,将反应管放入CEM单模微波反应腔中,控温150℃、反应时间30min。反应结束后,选用硅胶层析方法进行提纯处理,得到白色固体粉末Tr1F(77.46mg,产率为53%)。
反应条件二:在N2保护下,称量化合物4(50mg,0.038mmol)、化合物3b(328.4mg,0.34mmol)、KOH(50.8mg,0.91mmol)、相转移催化剂四丁基嗅化铵(TBAB)(85.8mg) 置于微波高压反应管中,抽换N2后,进行避光处理,加入催化剂Pd(PPh3)4(9mg,0.007mmol),加入3.5mL无水无氧四氢呋喃,将反应管放入CEM单模微波反应腔中,控温150℃、反应时间30min。反应结束后,选用硅胶层析方法进行提纯处理,得到白色固体粉末Tr2F(106.5 mg,产率为48%)。
反应条件三:在N2保护下,称量化合物4(50mg,0.038mmol)、化合物3c(442.1mg,0.34mmol)、KOH(50.8mg,0.91mmol)、相转移催化剂四丁基嗅化铵TBAB(108.6mg)置于微波高压反应管中,抽换N2后,进行避光处理,加入催化剂Pd(PPh3)4(10mg,0.007mmol),加入4mL无水无氧四氢呋喃,将反应管放入CEM单模微波反应腔中,控温150℃、反应时间30min。反应结束后,选用硅胶层析方法进行提纯处理,得到白色固体粉末Tr3F(119.1mg,产率为40%)。
产物Tr1F:1H NMR(400MHz,CDCl3,δ):8.50(s,3H),7.61(d,J=7.6Hz,3H),7.59–7.52 (m,9H),7.45(t,J=7.4Hz,6H),7.34(d,J=8.0Hz,3H),7.27(s,6H),7.25–7.21(m,18H),7.12 (t,J=7.5Hz,30H),7.01(d,J=13.8,10.2,4.0Hz,24H),3.07(s,6H),2.19(s,6H),1.81(d,J= 127.7Hz,24H),1.23–0.94(m,108H),0.77(d,J=14.5,7.1Hz,54H),0.65(t,J=6.3Hz,36H);13C NMR(100MHz,CDCl3,δ):152.7,152.2,150.7,150.1,148.0,146.8,145.1,141.2,140.2, 139.6,139.1,138.4,136.4,129.1,127.6,123.6,122.3,120.4,119.4,55.9,55.1,40.8,40.1,31.9, 31.4,30.1,29.5,24.1,22.9,22.6,22.3,14.01.MALDI-TOF-MS(m/z):calcd for C285H336N6, Molecular Weight:3845.86;Found:3846.56(M+).Anal.Calcd for C285H336N6:C,89.01;H,8.81;N, 2.19.Found:C,89.28;H,7.82;N,2.90.
产物Tr2F:1H NMR(400MHz,CDCl3,δ):8.59(s,3H),7.75–7.52(m,60H),7.36(s,3H), 7.28(s,6H),7.22(d,J=15.3Hz,18H),7.16–7.12(m,30H),7.02(t,J=7.9Hz,18H),3.16(s, 6H),2.29(s,6H),2.17–1.86(m,48H),1.20–1.01(m,180H),0.82–0.74(m,104H),0.73–0.67 (m,36H);13C NMR(100MHz,CDCl3,δ):152.8,152.4,151.4,150.5,148.1,147.1,145.2,141.8, 140.3,140.1,139.1,138.4,136.0,133.1,129.1,128.6,126.1,125.1,124.3,123.7,122.4,121.1, 120.4,119.4,114.1,56.0,55.1,41.0,40.2,31.8,31.4,30.2,29.6,23.8,22.9,22.4,14.0. MALDI-TOF-MS(m/z):calcd for C435H528N6,MolecularWeight:5841.05;Found:5838.68(M+). Anal.Calcd for C435H528N6:C,89.45;H,9.11;N,1.44.Found:C,89.28;H,8.82;N,1.90.
产物Tr3F:1H NMR(400MHz,CDCl3,δ):8.58(s,3H),7.96–7.72(m,36H),7.71–7.55(m, 60H),7.49(s,3H),7.28(s,12H),7.25(s,12H),7.14(s,30H),7.03(d,J=15.2,7.5Hz,18H),3.13 (s,6H),2.32(s,6H),2.19–1.87(m,72H),1.19–0.96(m,252H),0.89–0.75(m,174H),0.69(d,J =8.6Hz,36H);13C NMR(100MHz,CDCl3,δ):152.4,151.7,151.4,150.6,148.1,147.1,145.2, 140.9,140.5,140.5,139.2,138.5,136.1,133.1,129.1,126.1,123.7,122.4,122.0,121.2,121.1, 120.2,119.4,56.1,55.2,41.0,40.3,31.9,31.5,30.2,29.6,23.8,23.1,22.4,14.1.MALDI-TOF-MS (m/z):calcd for C585H720N6,MolecularWeight:7836.24;Found:7839.61(M+).Anal.Calcd for C585H720N6:C,89.67;H,9.26;N,1.07.Found:C,89.28;H,9.82;N,0.90。
Claims (6)
1.一种三并茚基有机半导体激光材料,其特征在于:该材料是以三并茚为核,二苯胺基团为封端单元,以不同链长芴基为桥连单元,该材料具有如下式I所示的结构通式:
其中,R为C1-C30的直链或支链烷基或烷氧基;n为重复单元,n为0~5的自然数。
2.如权利要求1所述的三并茚基有机半导体激光材料,其特征在于:所述的R为甲基、乙基、正己基、正辛基或异辛基中的一种。
3.一种如权利要求1或2所述的三并茚基有机半导体激光材料的制备方法,其特征在于:包括以下的合成方法:
目标化合物TrnF制备:在N2保护下,将六溴三并茚核(1)、二苯胺端基修饰的芴硼酸酯(2)、碱性化合物与相转移催化剂置于微波反应器中,抽换N2后,进行避光处理,加入催化剂,放入微波反应器中,进行反应,反应结束柱色谱纯化得目标化合物TrnF。
4.如权利要求3所述的三并茚基有机半导体激光材料的制备方法,其特征在于:所述相转移催化剂为四丁基嗅化铵;所述催化剂为Pd(PPh3)4催化剂;所述碱性化合物为KOH。
5.一种如权利要求1或2所述的三并茚基有机半导体激光材料在有机半导体激光和有机电致发光器件中的应用。
6.如权利要求5所述的应用,其特征在于:该材料作为激光增益介质或发光材料应用于有机半导体激光和有机电致发光器件中。
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CN108832482A (zh) * | 2018-06-12 | 2018-11-16 | 南京邮电大学 | 一种非掺杂自发辐射光放大薄膜器件及其制备方法 |
CN110922334A (zh) * | 2019-11-28 | 2020-03-27 | 西安戴森电子技术有限公司 | 一种茚三酮有机激光材料及其制备方法 |
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CN108832482A (zh) * | 2018-06-12 | 2018-11-16 | 南京邮电大学 | 一种非掺杂自发辐射光放大薄膜器件及其制备方法 |
CN110922334A (zh) * | 2019-11-28 | 2020-03-27 | 西安戴森电子技术有限公司 | 一种茚三酮有机激光材料及其制备方法 |
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