CN108203407A - 芘类有机电致发光材料、发光器件及显示器 - Google Patents

芘类有机电致发光材料、发光器件及显示器 Download PDF

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CN108203407A
CN108203407A CN201711386906.1A CN201711386906A CN108203407A CN 108203407 A CN108203407 A CN 108203407A CN 201711386906 A CN201711386906 A CN 201711386906A CN 108203407 A CN108203407 A CN 108203407A
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phenyl
electroluminescence device
organic electroluminescence
carbazyl
carbon atom
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李现伟
赵二辰
牛天
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Abstract

本发明涉及显示技术领域，特别是涉及芘类有机电致发光材料、有机电致发光器件及显示器。根据本发明的化合物如式(1)和式(2)所示。

Description

芘类有机电致发光材料、发光器件及显示器
技术领域
本发明涉及显示技术领域，特别是涉及芘类有机电致发光材料、有机电致发光器件及显示器。
背景技术
有机电致发光器件(Organic Light Emitting Display，简称OLED)作为新型的平板显示器，与液晶显示器(Liquid Crystal Display，简称LCD)相比，具有薄、轻、宽视角、主动发光、发光颜色连续可调、成本低、响应速度快、能耗小、驱动电压低、工作温度范围宽、生产工艺简单、发光效率高及可柔性显示等优点，得到了产业界和科学界的极大关注。
有机电致发光器件的发展促进了人们对有机电致发光材料的研究。相对于无机发光材料，有机电致发光材料具有以下优点：有机材料加工性能好，可通过蒸镀或者旋涂的方法在任何基板上成膜；有机分子结构的多样性使得可以通过分子结构设计及修饰的方法来调节有机材料的热稳定性、机械性能、发光及导电性能，使得材料有很大的改进空间。
有机电致发光的产生靠的是在有机半导体材料中传输的载流子(电子和空穴)的重组。众所周知，有机材料的导电性很差，有机半导体中没有延续的能带，载流子的传输常用跳跃理论来描述。为了能使有机电致发光器件在应用方面达到突破，必须克服有机材料电荷注入及传输能力差的困难。科学家们通过器件结构的调整，例如增加器件有机材料层的数目，并且使不同的有机层扮演不同的器件层，例如有的功能材料可以促进电子从阴极注入，有的功能材料可以促进空穴从阳极注入，有的材料可以促进电荷的传输，有的材料则能起到阻挡电子或者空穴传输的作用，当然在有机电致发光器件里最重要的各种颜色的发光材料也要达到与相邻功能材料相匹配的目的，因此，效率好寿命长的有机电致发光器件通常是器件结构以及各种有机材料优化搭配的结果，这就为化学家们设计开发各种结构的功能化材料提供了极大的机遇和挑战。
发明内容
本发明提供了芘类有机电致发光材料、包含该化合物的有机电致发光器件及具有该有机电致发光器件的显示装置。
根据本发明的一方面，提供了芘类有机电致发光材料，该化合物如式(1)和式(2)所示：
其中X1，X2，X3，X4，X5，X6，分别独立的选自氢、碳原子数为1～20的脂肪族烷基；A选自碳原子数为6～30的芳基；n选自0或者1；Ar1、Ar2独立的选自碳原子数为6-30的芳基，所述Ar1，Ar2可以被一个或一个以上的碳原子数为1～20的脂肪族烷基、碳原子数为1～20的脂肪族烷氧基、碳原子数为6～
30的芳基、三甲基硅基取代；Y选自碳原子数为3～10的含氮杂环，取代的碳原子数为3～10的含氮杂环。
进一步的，X1，X2，X3，X4，X5，X6，分别独立的选自氢、甲基、乙基、丙基、丁基、戊基、己基；A选自苯基、联苯基、芴基、二甲基芴基、苯并二甲基戊基；Ar1、Ar2独立的选自苯基、萘基、联苯基、二甲基芴基、二苯基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯胺基苯基、二苯胺基咔唑基、二咔唑取代的咔唑基、菲基、咔唑基取代的苯基、咔唑基取代的联苯基、苯并吡咯并咔唑基取代的苯基、苯并吡咯并咔唑基取代的联苯基、茚并咔唑取代的苯基、茚并咔唑取代的联苯基；所述苯基、萘基、联苯基、二甲基芴基、二苯基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯胺基苯基、二苯胺基咔唑基、二咔唑取代的咔唑基、菲基、咔唑基取代的苯基、咔唑基取代的联苯基、苯并吡咯并咔唑基取代的苯基、苯并吡咯并咔唑基取代的联苯基、茚并咔唑取代的苯基、茚并咔唑取代的联苯基可以被至少一个甲基、乙基、丙基、丁基、戊基、己基、甲氧基、乙氧基、丙氧基、苯基、萘基、戊基、咔唑基所取代；Y选自吡啶、喹啉、异喹啉、嘧啶、三嗪、碳原子数为6-30的芳基取代的三嗪、苯并咪唑、碳原子数为6-30的芳基取代的苯并咪唑。
更进一步的，X1，X2，X3，X4，X5，X6选自氢；n选自0；Y选自吡啶、喹啉、异喹啉、嘧啶、三嗪、碳原子数为6-30的芳基取代的三嗪、苯并咪唑、碳原子数为6-30的芳基取代的苯并咪唑。
可选地，根据本发明的有机电致发光材料选自：
根据本发明的另一方面，提供了一种有机电致发光器件，所述有机电致发光器件含有本发明的芘类有机电致发光材料。
可选地，所述有机电致发光器件的有机发光层的客体材料和/或空穴传输材料和/或主体材料为根据本发明的有机电致发光材料。可选地，根据本发明的芘类有机电致发光材料在有机电致发光器件中为蓝色荧光客体材料。可选地，根据本发明的芘类有机电致发光材料在有机电致发光器件中为磷光主体材料。
根据本发明的另一方面，提供了一种显示器，该显示装置包括根据本发明的有机电致发光器件。
根据本发明的另一方面，提供了一种电子设备，所述电子设备显示器包括本发明所述的有机电致发光器件；所述电子设备包括电视、手机、手表、电子书、运动手环、平板电脑、带有电子显示功能的电子门票、车载仪表。
本发明的有益效果如下：
本发明提供的化合物可以用在有机电致发光器件的客体材料和/或空穴传输材料和/或主体材料。
具体实施方式
具体实施方式仅为对本发明的说明，而不构成对本发明内容的限制，下面将结合具体的实施方式对本发明进行进一步说明和描述。
为了更加详细地说明本发明的化合物，下面将列举上述具体化合物的合成方法对本发明进行进一步的描述。
实施例1化合物P-1的合成
合成方程式如下：
中间体M-1的合成
1000毫升三口瓶，氮气保护，加入24.8克(0.1mol)1-芘硼酸，15.8克(0.1mol)3-溴吡啶，500毫升甲苯，100毫升乙醇，100毫升水27.6克(0.2mol)碳酸钾，5.78克(0.005mol)四三苯基膦钯，加毕缓慢升温至70℃，反应4小时，降温。加水分液，有机层水洗，无水硫酸钠干燥，用硅胶柱分离，用石油醚：乙酸乙酯：二氯甲烷(体积比为6：2：2)作为洗脱剂进行洗脱，得到式M-1所示的2-(1-芘基)吡啶2.06克，收率为73.84％。
对得到的式M-1所示中间体进行MS测试，产品分子量m/e：279。
中间体M-2的合成
500毫升三口瓶中，加入2.79克(0.01mol)上步制备得到的式M-1所示2-(1-芘基)吡啶，150毫升DMF，控温25～30度滴加1.78克(0.01mol)N-溴代丁二酰亚胺的10毫升DMF溶液，加毕保持25～30度反应4小时，加水分液，二氯甲烷提取，有机层水洗，无水硫酸钠干燥，用硅胶柱分离，用石油醚：乙酸乙酯：二氯甲烷(体积比为6：2：2)作为洗脱剂进行洗脱，得到式M-2所示的2-(6-溴芘-1-基)吡啶1.76克，收率为49.30％。
对得到的式M-2所示的2-(6-溴芘-1-基)吡啶进行MS测试，产品分子量m/e：357，359。
对得到的式M-2所示2-(6-溴芘-1-基)吡啶进行了核磁检测，所得到的核磁图的解析数据如下：
1HNMR(500MHz，CDCl3)：δ8.54(d，1H)，δ8.38(m，1H)，δ8.26(m，1H)，δ8.01(m，2H)，δ7.92(m，2H)，δ7.70(d，2H)，δ7.38(m，1H)，δ7.14(m，1H)，δ6.90(m，1H)。
化合物P-1的合成
在1000毫升的三口瓶中，在氮气保护下，加入550毫升干燥的甲苯、3.64克(0.01mol)式M-2所示2-(6-溴芘-1-基)吡啶、2.17克(0.011mol)二(4-甲基苯基)胺、1.28克(0.013mol)叔丁醇钠、0.23克(0.0004mol)双(二亚苄基丙酮)钯、0.81克(0.0004mol)10％的三叔丁基膦的甲苯溶液，加热至回流反应8小时后降至室温，加入稀盐酸，分液，有机层用水洗涤到中性，用无水硫酸镁干燥后，用硅胶柱分离，石油醚：乙酸乙酯：二氯甲烷(体积比为1：3：1)作为洗脱剂进行洗脱，得到式P-1所示的产品3.16克，收率为66.67％。
对得到的化合物P-1，进行质谱检测，产品m/e：474。
对得到的式P-1所示产品进行了核磁检测，所得到的核磁图的解析数据如下：1HNMR(500MHz，CDCl3)：δ8.54(d，1H)，δ8.37(m，1H)，δ8.28(m，1H)，δ8.07(m，1H)，δ7.91(m，2H)，δ7.80(d，1H)，δ7.70(d，2H)，δ7.38(m，1H)，δ7.18～7.10(m，9H)，δ6.80(m，1H)，δ2.32(s，6H)。
实施例2
参照化合物P-1的合成，根据需要将其中的2-溴吡啶换成相应溴代物，将其中的二(4-甲基苯基)胺换成相应的二芳胺或者咔唑类化合物，合成了以下化合物，对所得到的化合物进行了质谱检测，质谱数据见下表：
实施例3化合物P-69的合成
中间体M-3的合成
500毫升三口瓶，氮气保护，加入3.88克(0.01mol)1，3-二溴-6，8-二甲基芘，1.23克(0.01mol)吡啶-2-硼酸，200毫升甲苯，50毫升乙醇，50毫升水27.6克(0.2mol)碳酸钾，5.78克(0.005mol)四三苯基膦钯，加毕缓慢升温至70℃，反应12小时，降温。加水分液，有机层水洗，无水硫酸钠干燥，用硅胶柱分离，用石油醚：乙酸乙酯：二氯甲烷(体积比为6：2：2)作为洗脱剂进行洗脱，得到式M-3所示的2-(3-溴-6,8-二甲基芘-1-基)吡啶1.09克，收率为28.24％。
对得到的式M-3所示2-(3-溴-6,8-二甲基芘-1-基)吡啶进行MS测试，产品分子量m/e：385，387。
对得到的式M-3所示2-(3-溴-6,8-二甲基芘-1-基)吡啶进行了核磁检测，所得到的核磁图的解析数据如下：
1HNMR(500MHz，CDCl3)：δ8.37(m，1H)，δ8.33(s，1H)，δ7.70(s，4H)，δ7.48(s，1H)，δ7.38(m，1H)，δ7.14(m，1H)，δ6.90(m，1H)，δ2.70(s，6H)。
化合物P-69的合成
在500毫升的三口瓶中，在氮气保护下，加入250毫升干燥的甲苯、3.86克(0.01mol)M-3所示2-(3-溴-6,8-二甲基芘-1-基)吡啶、2.36克(0.012mol)二(对甲基苯基)胺、1.44克(0.015mol)叔丁醇钠、0.23克(0.0004mol)双(二亚苄基丙酮)钯、0.81克(0.0004mol)10％的三叔丁基膦的甲苯溶液，加热至回流反应12小时后降至室温，加入稀盐酸，分液，有机层用水洗涤到中性，用无水硫酸镁干燥后，用硅胶柱分离，用石油醚：乙酸乙酯：二氯甲烷(体积比为1：1：1)作为洗脱剂进行洗脱，得到P-69所示化合物3.88克，收率为77.29％。
对得到的化合物P-69，进行质谱检测，产品m/e：502。
对得到的式P-69所示产品进行了核磁检测，所得到的核磁图的解析数据如下：1HNMR(500MHz，CDCl3)：δ8.37(m，1H)，δ8.12(s，1H)，δ7.70(s，4H)，δ7.49(s，1H)，δ7.38(m，1H)，δ7.17～7.10(m，9H)，δ6.90(m，1H)，δ2.79(s，6H)，δ2.32(s，6H)。
实施例4
参照化合物P-69的合成，只是根据需要将其中的吡啶-2-硼酸换成相应的硼酸，根据需要将其中的二(对甲基苯基)胺换成相应的芳香胺，对所得到的化合物进行了质谱检测，质谱数据见下表：
根据本发明的另一方面，提供了一种有机电致发光器件，该有机电致发光器件的客体材料和/或空穴传输材料和/或主体材料为根据本发明的有机电致发光材料。
有机电致发光器件的典型结构为：基片/阳极/空穴注入层/空穴传输层(HTL)/有机发光层主体材料：发光层客体材料/电子传输层(ETL)/电子注入层/阴极。有机电致发光器件结构可以为单发光层也可以是多发光层。
其中，基片可以使用传统有机电致发光器件中的基板，如：玻璃或塑料。阳极可以采用透明的高导电性材料，如：铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)。
空穴注入层的空穴注入材料(Hole Injection Material，简称HIM)，要求具有高的热稳定性(高的Tg)，与阳极有较小的势垒，能真空蒸镀形成无针孔薄膜。常用的HTM均为芳香多胺类化合物，主要是三芳胺类衍生物。
空穴传输层的空穴传输材料(Hole Transport Material，简称HTM)，要求具有高的热稳定性(高的Tg)，较高的空穴传输能力，能真空蒸镀形成无针孔薄膜。常用的HTM均为芳香多胺类化合物，主要是三芳胺类衍生物。
有机发光层包括主体材料(host)和客体材料，其中客体材料为发光材料，例如染料，主体材料需要具备以下特点：可逆的电化学氧化还原电位，与相邻的空穴传输层及电子传输层相匹配的HOMO能级及LUMO能级，良好且相匹配的空穴及电子传输能力，良好的高的热稳定性及成膜性，以及合适的单线态或者三线态能隙用来控制激子在发光层，还有与相应的荧光染料或者磷光染料间良好的能量转移。有机发光层的发光材料，以染料为例，需要具备以下特点：具有高的荧光或者磷光量子效率；染料的吸收光谱与主体的发射光谱有好的重叠，即主体与染料能量适配，从主体到染料能有效地能量传递；红、绿、蓝的发射峰尽可能窄，以获得好的色纯度；稳定性好，能够进行蒸镀等。
电子传输层的电子传输材料(Electron transport Material，简称ETM)要求ETM有可逆而且足够高的电化学还原电位，合适的HOMO能级和LUMO(Lowest UnoccupiedMolecular Orbital，最低未占分子轨道)能级值使得电子能够更好地注入，而且最好具有空穴阻挡能力；较高的电子传输能力，有好的成膜性和热稳定性。ETM一般为具有缺电子结构的共轭平面的芳香化合物。电子传输层采用Alq3(8-羟基喹啉铝)或者TAZ(3-苯基-4-(1’-萘基)-5-苯-1,2,4-三唑)或者TPBi(1,3,5-三(N-苯基-2-苯并咪唑)苯)或者取自这三种材料的任意两种的搭配。
根据本发明的另一方面，提供了一种显示器，该显示器包括根据本发明的有机电致发光器件。
根据本发明的另一方面，提供了一种电子设备，所述电子设备显示器包括本发明所述的有机电致发光器件；所述电子设备包括电视、手机、手表、电子书、运动手环、平板电脑、带有电子显示功能的电子门票。
由此可见，根据本发明的化合物、有机电致发光器件、显示器及带有显示装置的电子器件的可选因素较多，根据本发明的权利要求可以组合出不同的实施例。本发明的实施例仅作为对本发明的具体描述，并不作为对本发明的限制。下面将结合含有本发明的化合物的有机电致发光器件作为实施例对本发明进行进一步描述。
本发明中使用的几种材料具体结构见下：
实施例5
以本发明的化合物作为有机电致发光器件中的发光层客体材料，作为对比的有机电致发光器件，发光层客体材料选用D-46和D-47。
有机电致发光器件结构为：ITO/HIL02(100nm)/NPB(40nm)/EM1：发光层客体材料[5％](30nm)/ETL(20nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下：
将涂布了ITO透明导电层(作为阳极)的玻璃基板在清洗剂中进行超声处理，然后在去离子水中冲洗，再在丙酮与乙醇混合溶剂中超声除油，再在洁净环境下烘烤至完全除水，用紫外光和臭氧清洗，并用低能阳离子束轰击表面，以改善表面的性质，提高与空穴注入层的结合能力；
将上述玻璃基板置于真空腔内，抽真空至1×10-5～9×10-3Pa，在阳极上真空蒸镀HIL02作为空穴注入层，蒸镀速率0.1nm/s，蒸镀膜厚为100nm；
在空穴注入层上真空蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为40nm；
在空穴传输层之上真空蒸镀发光主体材料和客体材料，作为有机电致发光器件的发光层，蒸镀速率为0.1nm/s，蒸镀总膜厚为30nm；其中EM1：发光层客体材料[5％]”是指发光层客体材料的掺杂比例，即主体材料与发光层客体材料的重量份比为100:5；
在有机发光层之上真空蒸镀Alq3作为有机电致发光器件的电子传输层；其蒸镀速率为0.1nm/s，蒸镀总膜厚为20nm；
在电子传输层(ETL)上真空蒸镀0.5nm的LiF作为电子注入层；
在电子注入层之上真空蒸镀150nm的铝(Al)作为阴极。
有机电致发光器件性能见下表：
其中寿命数值为器件在750cd/m2的初始亮度下，保持电流密度不变，亮度降至初始亮度97％所需要的时间。
可以看出，本发明的化合物和对比例比较，提供了更短波长的蓝光，另外在相同的亮度条件下，采用本发明的化合物作为发光层客体材料制得的有机电致发光器件与采用D-46和D-47作为发光层客体材料制得的有机电致发光器件相比，具有较低的驱动电压、较高的电流效率和较长的寿命。
实施例6
以本发明的化合物作为红色磷光OLED有机电致发光器件中的主体材料，作为对比的有机电致发光器件，红光主体材料选用CBP和H-2。
有机电致发光器件结构为：ITO/NPB(20nm)/红光主体材料(30nm)：Ir(piq)3[5％]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮：乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上真空蒸镀空穴传输层NPB，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；
在空穴传输层之上真空蒸镀发光主体材料和染料，作为有机电致发光器件的发光层，蒸镀速率为0.1nm/s，蒸镀总膜厚为30nm；其中“Ir(piq)3[5％]”是指红光染料的掺杂比例，即红光主体材料与Ir(piq)3的重量份比为100:5；
在发光层之上依次真空蒸镀电子传输层TPBI和Alq3，其蒸镀速率均为0.1nm/s，蒸镀膜厚分别为10nm和15nm；
在电子传输层上真空蒸镀0.5nm的LiF，150nm的Al作为电子注入层和阴极。
有机电致发光器件性能见下表：
由上表可以看到，采用本发明化合作为红色磷光主体的有机电致发光器件相对于采用CBP和H-2作为主体的有机电致发光器件获得了较好的效果，获得了更高的电流效率和较低的驱动电压。
实施例7
以本发明的化合物作为绿色磷光OLED有机电致发光器件中的主体材料，作为对比的有机电致发光器件，绿光主体材料选用CBP和H-2。
有机电致发光器件结构为：ITO/NPB(20nm)/绿光主体材料(30nm)：Ir(ppy)3[7％]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮：乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上真空蒸镀空穴传输层NPB，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；
在空穴传输层之上真空蒸镀发光主体材料和染料，作为有机电致发光器件的发光层，蒸镀速率为0.1nm/s，蒸镀总膜厚为30nm；其中“Ir(ppy)3[7％]”是指绿光染料的掺杂比例，即绿光主体材料与Ir(ppy)3的重量份比为100:7；
在发光层之上依次真空蒸镀电子传输层TPBI和Alq3，其蒸镀速率均为0.1nm/s，蒸镀膜厚分别为10nm和15nm；
在电子传输层上真空蒸镀0.5nm的LiF，150nm的Al作为电子注入层和阴极。
有机电致发光器件性能见下表：
由上表可以看到，采用本发明化合作为绿色磷光主体的有机电致发光器件相对于采用CBP和H-2作为主体的有机电致发光器件获得了较好的效果，获得了更高的电流效率和较低的驱动电压。
实施例8
以本发明的化合物作为红色磷光OLED有机电致发光器件中的空穴传输材料，作为对比的有机电致发光器件，空穴传输材料采用NPB和HT-48。
有机电致发光器件结构为：ITO/空穴传输材料(20nm)/CBP(30nm)：Ir(piq)3[5％]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮：乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上真空蒸镀空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；
在空穴传输层之上真空蒸镀发光主体材料和染料，作为有机电致发光器件的发光层，蒸镀速率为0.1nm/s，蒸镀总膜厚为30nm；其中“Ir(piq)3[5％]”是指红光染料的掺杂比例，即红光主体材料与Ir(piq)3的重量份比为100:5；
在发光层之上真空蒸镀电子传输层，电子传输层采用TPBI和Alq3，其蒸镀速率均为0.1nm/s，蒸镀膜厚分别为10nm和15nm；
在电子传输层上真空蒸镀0.5nm的LiF，150nm的Al作为电子注入层和阴极。
有机电致发光器件性能见下表：
由上表可以看到：采用本发明化合作为空穴传输材料的有机电致发光器件相对于采用NPB和HT-48作为空穴传输材料的有机电致发光器件，获得了更高的电流效率和较低的驱动电压。
实施例9HT-48的合成
在500毫升的三口瓶中，在氮气保护下，加入200毫升干燥的甲苯、2.81克(0.01mol)1-溴芘、8.16克(0.012mol)N4,N4-二([1,1'-联苯]-4-基)-N4'-(9,9-二甲基-9H-芴-3-基)-[1,1'-联苯]-4,4'-二胺、1.44克(0.015mol)叔丁醇钠、0.23克(0.0004mol)双(二亚苄基丙酮)钯、0.81克(0.0004mol)10％的三叔丁基膦的甲苯溶液，加热至回流反应8小时后降至室温，加入稀盐酸，分液，有机层用水洗涤到中性，用无水硫酸镁干燥后，用硅胶柱分离，用石油醚：乙酸乙酯：二氯甲烷(体积比为1：1：1)作为洗脱剂进行洗脱，得到HT-48所示化合物6.23克，收率为70.72％。
对得到的化合物HT-48，进行质谱检测，产品m/e：880。
对得到的式HT-48所示产品进行了核磁检测，所得到的核磁图的解析数据如下：1HNMR(500MHz，CDCl3)：δ8.31(m，1H)，δ8.06(m，5H)，δ7.91(m，2H)，δ7.81(d，1H)，δ7.76(m，4H)，δ7.70(d，1H)，δ7.60～7.28(m，27H)，δ6.77(d，1H)，δ1.69(s，6H)。
显然，本领域的技术人员可以对本发明进行各种改动和变型而不脱离本发明的精神和范围。这样，倘若本发明的这些修改和变型属于本发明权利要求及其等同技术的范围之内，则本发明也意图包含这些改动和变型在内。

Claims (10)

1.芘类有机电致发光材料，如式(1)和式(2)所示：
其中X1，X2，X3，X4，X5，X6分别独立的选自氢、碳原子数为1～20的脂肪族烷基；
A选自碳原子数为6～30的芳基；
n选自0或者1；
Ar1、Ar2独立的选自碳原子数为6-30的芳基，所述Ar1，Ar2可以被一个或一个以上的碳原子数为1～20的脂肪族烷基、碳原子数为1～20的脂肪族烷氧基、碳原子数为6～30的芳基、三甲基硅基取代；
Y选自碳原子数为3～10的含氮杂环，取代的碳原子数为3～10的含氮杂环。
2.根据权利要求1所述的芘类有机电致发光材料，其中：
X1，X2，X3，X4，X5，X6分别独立的选自氢、甲基、乙基、丙基、丁基、戊基、己基；
A选自苯基、联苯基、芴基、二甲基芴基、苯并二甲基芴基；
Ar1、Ar2独立的选自苯基、萘基、联苯基、二甲基芴基、二苯基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯胺基苯基、二苯胺基咔唑基、二咔唑取代的咔唑基、菲基、咔唑基取代的苯基、咔唑基取代的联苯基、苯并吡咯并咔唑基取代的苯基、苯并吡咯并咔唑基取代的联苯基、茚并咔唑取代的苯基、茚并咔唑取代的联苯基；所述苯基、萘基、联苯基、二甲基芴基、二苯基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯胺基苯基、二苯胺基咔唑基、二咔唑取代的咔唑基、菲基、咔唑基取代的苯基、咔唑基取代的联苯基、苯并吡咯并咔唑基取代的苯基、苯并吡咯并咔唑基取代的联苯基、茚并咔唑取代的苯基、茚并咔唑取代的联苯基可以被至少一个甲基、乙基、丙基、丁基、戊基、己基、甲氧基、乙氧基、丙氧基、苯基、萘基、戊基、咔唑基所取代；
Y选自吡啶、喹啉、异喹啉、嘧啶、三嗪、碳原子数为6-30的芳基取代的三嗪、苯并咪唑、碳原子数为6-30的芳基取代的苯并咪唑。
3.根据权利要求2所述的芘类有机电致发光材料，其中：
X1，X2，X3，X4，X5，X6选自氢；
n选自0；
Y选自吡啶、喹啉、异喹啉、嘧啶、三嗪、碳原子数为6-30的芳基取代的三嗪、苯并咪唑、碳原子数为6-30的芳基取代的苯并咪唑。
4.根据权利要求1所述的芘类有机电致发光材料，选自以下结构：
5.一种有机电致发光器件，其特征在于，所述有机电致发光器件含有权利要求1-4任一所述的芘类有机电致发光材料。
6.根据权利要求5所述的有机电致发光器件，其特征在于，所述有机电致发光器件的客体材料为权利要求1-4任一所述的芘类电致发光材料。
7.根据权利要求5所述的有机电致发光器件，其特征在于，所述有机电致发光器件的空穴传输材料为权利要求1-4任一所述的芘类电致发光材料。
8.根据权利要求5所述的有机电致发光器件，其特征在于，所述有机电致发光器件的主体材料为权利要求1-4任一所述的芘类电致发光材料。
9.一种显示器，其特征在于，包括如权利要求5-8任一所述的有机电致发光器件。
10.一种电子设备，所述电子设备显示器包括如权利要求5-7任一所述的有机电致发光器件；
所述电子设备包括电视、手机、手表、电子书、运动手环、平板电脑、带有电子显示功能的电子门票、车载仪表。
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Application publication date: 20180626