CN107337643A - 一种吖啶类化合物及其有机发光器件 - Google Patents

一种吖啶类化合物及其有机发光器件 Download PDF

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CN107337643A
CN107337643A CN201710568853.9A CN201710568853A CN107337643A CN 107337643 A CN107337643 A CN 107337643A CN 201710568853 A CN201710568853 A CN 201710568853A CN 107337643 A CN107337643 A CN 107337643A
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蔡辉
董秀芹
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明公开了一种吖啶类化合物及其有机发光器件。本发明的吖啶类化合物具有高的发光效率，高的发光效率表明该化合物可作为电子传输材料或发光主体材料，尤其是可以作为磷光绿色主体材料，应用在有机电子发光器件中，其制造成本较低，延长了有机电子发光器件的寿命，降低了有机电子发光器件的制造成本。

Description

一种吖啶类化合物及其有机发光器件
技术领域
本发明属于有机光电材料技术领域，尤其涉及一种吖啶类衍生物及其有机发光器件。
背景技术
对于有机电致发光材料的研究是1950年Bernose对含有有机色素的高分子薄膜施加高电流电压测到的。1965年，pope等人首次发现了蒽单晶的电致发光性质，这是有机化合物的首例电子发光现象。为了制作高效率的有机发光器件，研究者逐渐把器件内有机物层的结构从单层变为多层结构。把有机电致发光器件设计为多层结构是由于空穴和电子的移动速度不同，适当的设计出空穴注入层，空穴传输层，电子传输层及电子注入层，提高了空穴和电子的传输效率，使器件中空穴和电子达到均衡，从而提高发光效率。
目前有机电致器件中电子传输材料的代表物质如下：
激发子应具有将其能量转移给附近的带隙材料；否则，激发子的能量将转移至具有更低量子产量的主材料，并因此产生弱的发射或者不发射。但是至今没有理想的稳定高效率的有机发光材料用于有机物层。因此，现有技术还有待于更进一步的改进和发展。
目前要求的材料的特性是物质具备热稳定性和快速电子移动度及发光体的高效率及长寿命，本发明提供了比现阶段性能优越的材料。
发明内容
本发明提供了一种发光效率良好的电子传输材料，方法是通过将吖啶化合物改变结构提高电子迁移率。并且将这种吖啶化合物制备成器件，其具有很好的发光效率。
本发明是下列化学式1表示的吖啶类化合物:
[化学式1]
其中，L1～L3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基、取代或未取代的C6～C60芳胺基或取代或未取代的吖啶基。
优选的，所述含吖啶衍生物选自下面化学式[2～4]中的任意一种:
[化学式2]
[化学式3]
[化学式4]
其中，Ar1～Ar3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基或吖啶基。
优选的，吖啶类化合物选自下述化学式中任意一个化合物：
本发明还提供一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种本发明所述的吖啶类化合物。
本发明的有益效果：
本发明的吖啶类化合物是通过对吖啶的2和9位中引进芳香基、杂环基、稠环基、胺基等基团提高电子密度、电子传输技能能等优点。使用本发明的吖啶类化合物制造的器件具备高的亮度、优秀的耐热性、长寿命及高发光效率等优点。
具体实施方式：
下面将结合本发明实施例的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
按本发明，提供下列化学式1表示的吖啶类化合物：
[化学式1]
其中，L1～L3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基、取代或未取代的C6～C60芳胺基或取代或未取代的吖啶基。
优选的，所述吖啶类化合物选自下面化学式[2～4]中的任意一种:
[化学式2]
[化学式3]
[化学式4]
其中，Ar1～Ar3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基和吖啶基。
优选的，所述吖啶类化合物选自下述化学式中任意一个化合物：
本发明还提供了一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种本发明所述的吖啶类化合物。
上述有机化合物层其中至少包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。。
本发明的上述器件可以用在有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管领域。
有机发光器件利用薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属及具有导电性的氧化物及他们的合金形成阳极，其上述空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、阴极的制备方法同上所述。
下面提示本发明的另一方面是提供上述吖啶类化合物的制备方法，但下面实施例是理解本发明的内容提供而已，发明内容不限定在这个范围。
此外本发明没有具体介绍的制造方法是本行业常用的合成方法及参考其他实施例记载。
[实施例1]化合物A-1的合成
*中间体N,N-二苯基吖啶-3-胺的合成
氮气下反应容器里加入二苯胺(10.00g,59.1mmol)、3-溴吖啶(15.10g,58.51mmol)、三(二亚苄基丙酮)二钯(0.1g),三叔丁基膦(15％，0.15g),叔丁醇钠(0.9g),甲苯(400ml)，60℃下搅拌12小时。反应液冷却，硅胶滤斗过滤，溶液浓缩，用二氯甲烷和己烷进行柱层析得到N,N-二苯基吖啶-3-胺(12.80g，收率65％)。
*中间体N,9-溴-N,N-二苯基吖啶-3-胺的合成
反应容器里加入N-二苯基吖啶-2-胺(34.62g，100mmol)，用四氢呋喃(200ml)溶解。氮气和0℃下加入N-溴代丁二酰亚胺(18.0g,101mmol)，常温搅拌5小时。反应终结，用蒸馏水终止反应，用乙酸乙酯萃取有机物，过滤硅胶滤斗，浓缩有机溶剂用乙酸乙酯重结晶得到9,9-溴-N,N-二苯基吖啶-3-胺(37.42g,88％)。
*化合物A-1的合成
反应容器里加二苯基-4-硼酸(3.35g,16.9mmol)、9-溴-N,N-二苯基吖啶-3-胺(7.19g,16.9mmol)、四三苯基膦钯(0.7g,1.08mmol)、碳酸钾(5.3g,38.3mmol),甲苯60mL,乙醇20mL及蒸馏水20mL，120℃下搅拌3h。反应结束，蒸馏水停止反应用乙酸乙酯萃取。有机层用MgSO4干燥。减压蒸馏去掉溶剂，用硅胶柱子提纯得到化合物A-1(5.73g,68％)。
[实施例2]化合物A-6的合成
按照A-1合成方法得到A-6。
[实施例3]化合物A-14的合成按照A-1合成方法得到A-14。
[实施例4]化合物A-8的合成按照A-1合成方法得到A-8。
[实施例5]化合物A-7的合成按照A-1合成方法得到A-7。
[实施例6]化合物A-42的合成按照A-1合成方法得到A-42。
[实施例7]化合物A-43的合成按照A-1合成方法得到A-43。
[实施例8]化合物A-44的合成
按照A-1合成方法得到A-44。
[实施例9]化合物A-45的合成
*中间体9,10-双(氯甲基)蒽的合成
HCl(35.0～37.0％,20mL)和二氧六环(120mL)充分混合,反应体系里加入3-(二苯基-3-)吖啶(14.92g,45mmol)和多聚甲醛(4.0g,113mmol)，回流搅拌2h。然后常温搅拌16h。用水反应结束，用二氯甲烷分离有机层，再用硫酸镁干燥。减压蒸馏去掉有阶层用层析柱(Hx:EA＝4:1)分离得到化合物3-(二甲基-3)-9-(氯甲基)吖啶(15.39g,90％)。
*中间体3-(二苯基)吖啶-9-蒽的合成
氮气下反应容器里加入9,10-双(氯甲基)蒽(6.90g,18.2mmol)、DMSO(21mL)搅拌30分钟。钠(0.5g,21.7mmol)溶解在乙醇里再加入硝基丙烷搅拌3h。得到的物质加入DMSO反应体系里搅拌3h。反应结束，过滤得到固体物质，滤液里加入水，二氯甲烷萃取和减压蒸馏得到2-(二苯基)吖啶-9-蒽(3.27g,50％)。*化合物A-45的合成
氮气下反应容器里加入3-(二苯基)吖啶-9-蒽(3.60g，10mmol)、焦亚硫酸钠(2.10g，11mmol)、二氯甲烷(100mL)，回流5h，反应结束，加入水停止反应用二氯甲烷提取有机物，用柱层析和重结晶方法得到A-45(4.08g,78％)
所述方法制备的新的吖啶蒽化合物的FD-MS值是表1表示。
【表1】本发明实施例制备得到的吖啶类化合物的FD-MS值
器件制备实施例1：
将厚度为的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀空穴注入层蒸镀空穴传输层蒸镀AND(9，10-二(2-萘基)蒽)和掺杂材料TPPDA(N1,N1,N6,N6-tetraphenylpyrene-1,6-diamine)5％混合/蒸镀空穴阻挡层及电子传输层TPBi或实施例A物质/阴极上述过程有机物蒸镀速度是保持LiF是Al是
表2为本发明实施例制备的吖啶类化合物以及比较物质制备的发光器件的发光特性测试结果
[表2]发光器件的发光特性
从上述表2结果中，能看出本发明的吖啶类化合物的发光效率及寿命特性有显著的提高。
本发明利用吖啶配体制备的有机发光器件，可以得到发光效率和寿命良好的结果，所以本发明在OLED产业中有较高的实用性。本发明的有机发光器件在平面面板显示、平面发光体、照明用面发光OLED发光体、柔性发光体、复印机、打印机、LCD背光灯或计量机类的光源、显示板、标识等领域可广泛使用。

Claims (5)

1.一种吖啶类化合物，其特征在于，所述吖啶类化合物，分子通式为：
[化学式1]
其中，L1～L3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基、取代或未取代的C6～C60芳胺基或取代或未取代的吖啶基。
2.根据权利要求1所述的吖啶类化合物，选自下面化学式[2～4]中的任意一种:
[化学式2]
[化学式3]
[化学式4]
其中，Ar1～Ar3是互相一样或不一样的取代或未取代C6～C60芳基、取代或未取代的C5～C60稠环基或吖啶基。
3.根据权利要求1或2所述的吖啶化合物，其特征在于，所述吖啶类化合物选自下述化学式A-1～化学式A～52中任意一个特定的吖啶类化合物：
4.一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机物层，至少一个有机物层包含所述权利要求1～3任意一项所述的吖啶类化合物。
5.根据权利要求4所述的有机发光器件，其特征在于，所述有机物层至少包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
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CN110423220A (zh) * 2019-06-05 2019-11-08 维思普新材料（苏州）有限公司 一种9-苯基吖啶类化合物的制备方法

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CN106749215A (zh) * 2016-12-09 2017-05-31 中节能万润股份有限公司 一种基于单取代基吖啶的化合物、制备方法及其应用

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CN105938874A (zh) * 2015-03-06 2016-09-14 三星显示有限公司 有机发光装置
CN106749215A (zh) * 2016-12-09 2017-05-31 中节能万润股份有限公司 一种基于单取代基吖啶的化合物、制备方法及其应用

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