CN109180585A - 有机发光材料及其制备方法和含该材料的有机电致发光器件 - Google Patents

有机发光材料及其制备方法和含该材料的有机电致发光器件 Download PDF

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CN109180585A
CN109180585A CN201811180997.8A CN201811180997A CN109180585A CN 109180585 A CN109180585 A CN 109180585A CN 201811180997 A CN201811180997 A CN 201811180997A CN 109180585 A CN109180585 A CN 109180585A
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李文军
王辉
林文晶
李明
陈明
姚明明
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及发光材料领域，具体涉及一种有机发光材料及其制备方法和含该材料的有机电致发光器件。本发明的有机发光材料，其为下述结构式中的任意一种：上述结构式中：R为苯基或联苯基；Ar1和Ar2各自独立地选自取代或未取代的C6‑31的芳基、或者取代或未取代的C12‑30的杂芳基。本发明通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命。由本发明的机发光化合物制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。本发明的有机发光化合物的制备方法，重复性好，产率高。

Description

有机发光材料及其制备方法和含该材料的有机电致发光器件
技术领域
本发明涉及发光材料领域，具体涉及一种有机发光材料及其制备方法和含该材料的有机电致发光器件。
背景技术
有机电致发光器件由于其体积小、重量轻、驱动电压低、响应快、视角广以及可实现大面积全色平板显示等优点而成为研究的热点，并有着极好的商业和市场前景。多年来的研究不仅在有机电致发光理论上，而且在器件的实用性能，如亮度、驱动电压、寿命等诸多方面都有了长足的发展。目前有机电致发光器件的最大亮度超过140000cd/m2，驱动电压多低于10V，连续使用寿命长达50000h。
为了进一步提高有机电致发光器件的亮度、效率和寿命，通常在器件中使用多层结构。这些多层结构包括发光层及各种辅助有机层，如：空穴注入层、空穴传输层、电子传输层等。这些辅助有机层的作用是提高载流子(空穴和电子)在各层界面间的注入效率，平衡载流子在各层之间的传输，从而提高器件的亮度和效率。其中，空穴传输层的作用是提高空穴在器件中的传输速率，并有效地将电子阻挡在发光层内，实现载流子的最大复合；同时降低空穴在注入过程中的能量势垒，提高空穴的注入效率，从而提高器件的亮度、寿命和效率。
传统的空穴传输材料基本以三芳基衍生物为主。虽然其具有空穴传输能力和低驱动电压，但是为了获得合适的玻璃态转变温度而不得不在其结构上引入大量的取代基提升其分子量。但是这样确降低三重态能量或LUMO能量，从而导致有机电致发光器件的劣化。理想的空穴传输材料需要高玻璃态转变温度、空穴注入能力和空穴传输能力，以及适合三重态能量和LUMO能量。
发明内容
本发明要解决现有技术中的技术问题，提供一种有机发光材料及其制备方法和含该材料的有机电致发光器件，由本发明的材料制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。
为了解决上述技术问题，本发明的技术方案具体如下：
一种有机发光材料，其为下述结构式中的任意一种：
上述结构式中：
R为苯基或联苯基；
Ar1和Ar2各自独立地选自取代或未取代的C6-31的芳基、或者取代或未取代的C12-30的杂芳基。
在上述技术方案中，Ar1和Ar2各自独立地选自取代或未取代的C10-25的芳基、或者取代或未取代的C16-24的杂芳基。
在上述技术方案中，Ar1和Ar2各自独立地选自取代或未取代的C14-21的芳基、或者取代或未取代的C18-22的杂芳基。
在上述技术方案中，Ar1和Ar2各自独立地选自取代或未取代的C16-19的芳基、或者取代或未取代的C21的杂芳基。
在上述技术方案中，所述有机发光材料为下述结构中的任意一种：
一种有机发光材料的制备方法，包括以下步骤：
步骤1、中间体的合成
将化合物2和化合物1在甲苯中的脱气溶液用N2饱和；然后再加入(1,1'-双(二苯基膦)二茂铁和乙酸钯(II)，随后添加NaOtBu；将该反应混合物加热回流过夜；反应结束后，冷却至室温之后，添加水，将水相用甲苯洗涤，使用MgSO4干燥，并在真空下除去溶剂；使用庚烷/乙酸乙酯经由硅胶过滤粗产物，得到中间体1；
在避光条件下在0℃下将N-溴代丁二酰亚胺添加至中间体1的二氯甲烷溶液中，并且将该混合物在该温度下继续搅拌；该反应通过添加亚硫酸钠溶液而终止，并且再在室温下继续搅拌；在相分离之后，将有机相用水洗涤，并将水相用二氯甲烷提取；将合并的有机相用硫酸钠干燥，并在真空下蒸发；将残余物溶解于乙酸乙酯中，并经由硅胶过滤；然后将粗产物从庚烷中重结晶；得到中间体2；
合成路线如下：
步骤2、目标产物的合成
在氮气保护体系下，向反应瓶中加入中间体2，再加入化合物3或者化合物4，再加入叔丁醇钠和溶剂，对反应体系脱气，加入催化剂三(二亚苄基丙酮)二钯、三(叔丁基)膦，将反应体系的温度升至回流进行反应，反应结束后加入超纯水搅拌，抽滤，乙醇和超纯水淋洗，烘干后得目标产物；
化合物3和化合物4结构式如下：
其中：R为苯基或联苯基；Ar1和Ar2各自独立地选自取代或未取代的C6-31的芳基、或者取代或未取代的C12-30的杂芳基；
L为下述结构中的任意一种：
本发明还提供一种含有上述有机发光材料的有机电致发光器件。
在上述技术方案中，所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有上述有机发光材料；所述有机发光材料可以是单一形态或与其它物质混合存在于有机物层中。
所述有机物层至少包括空穴注入层，空穴传输层，既具备空穴注入又具备空穴传输技能层，电子阻挡层，发光层，空穴阻挡层，电子传输层，电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当上述有机发光材料存在于所述有机物层中的空穴传输层或者空穴注入层时，所述有机发光材料可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所述的包含有上述有机发光材料制备的器件可以用于有机发光器件(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(OTFT)。
本发明所述的有机电致发光器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明的有益效果是：
本发明提供用于有机EL装置中的可解决传统技术问题的空穴传输材料。传统的空穴传输材料基本以三芳基衍生物为主。虽然其具有空穴传输能力和低驱动电压，但是为了获得合适的玻璃态转变温度而不得不在其结构上引入大量的取代基提升其分子量。但是这样却降低三重态能量或LUMO能量，从而导致有机电致发光器件的劣化。理想的空穴传输材料需要高玻璃态转变温度、空穴注入能力和空穴传输能力，以及适合三重态能量和LUMO能量。因此，为了解决传统空穴传输材料中存在的问题而得到理想的材料，本发明提出向吖啶环上引入芳基胺的解决方案。通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命。
由本发明的有机发光材料制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。
本发明的有机发光材料的制备方法，重复性好，产率高。
具体实施方式
中间体2的合成
将57.9g(243.7mmol)溴苯和50.6g(203.1mmol)9-环己基吖啶在1000mL甲苯中的脱气溶液用N2饱和1小时。然后，首先将5.6g(10.1mmol)DPPF(1,1'-双(二苯基膦)二茂铁)，然后将2.28g(10.1mmol)乙酸钯(II)添加至该溶液，随后添加52.3g(528mmol)固体状态的NaOtBu。将该反应混合物加热回流过夜。在冷却至室温之后，小心地添加500mL水。将水相用3×50mL甲苯洗涤，使用MgSO4干燥，并在真空下除去溶剂。使用庚烷/乙酸乙酯(20:1)经由硅胶过滤粗产物，得到中间体1-1，产量：60g，理论值的75％，浅黄色晶体。
将上述溴苯替换为4-溴联苯，制备得到中间体1-2，其结构式如下：
在避光条件下在0℃下将N-溴代丁二酰亚胺(9.8g，55.3mmol)分份添加至中间体1-1(16.9g，55.3mmol)在二氯甲烷(140mL)中的溶液中，并且将该混合物在该温度下搅拌2小时。该反应通过添加亚硫酸钠溶液而终止，并且在室温下搅拌30分钟。在相分离之后，将有机相用水洗涤，并将水相用二氯甲烷提取。将合并的有机相用硫酸钠干燥，并在真空下蒸发。将残余物溶解于乙酸乙酯中，并经由硅胶过滤。然后将粗产物从庚烷中重结晶。制备得到中间体2-1，产率：14g，理论值的97％，无色固体。
将上述中间体1-1替换为中间体1-2，制备得到中间体2-2。中间体2-1和中间体2-2的结构式如下：
实施例1
化合物001的合成
在氮气保护体系下，加入10.0mmol中间体2-1与12.0mmol二苯胺，加入叔丁醇钠30mmol和溶剂30mL，溶剂为无水甲苯。对反应体系脱气，加入催化剂三(二亚苄基丙酮)二钯0.1mmol，三(叔丁基)膦1mmol将反应体系的温度升至回流，反应12小时。反应结束后加入超纯水搅拌，抽滤，乙醇和超纯水淋洗，烘干后得化合物001，产率85％，质谱：492.30。
实施例2-18
参照化合物001的合成，按照下表的原料合成下述物质。
表1
实施例19
化合物133的合成
在氮气保护体系下，加入10.0mmol中间体2-1与12.0mmol化合物19-1，加入碳酸钠25mmol和溶剂30mL，溶剂为甲苯和水，比例为2:1，对反应体系脱气，加入催化剂四三苯基膦钯0.2mmol，将反应体系的温度升至回流，反应24小时，使用石油醚：二氯甲烷＝2:1重结晶，得到化合物133，产率为75％，质谱数据为：720.38。
实施例20
化合物180的合成
在氮气保护体系下，加入10.0mmol中间体2-1与12.0mmol化合物20-1，加入碳酸钠25mmol和溶剂30mL，溶剂为甲苯和水，比例为2:1，对反应体系脱气，加入催化剂四三苯基膦钯0.2mmol，将反应体系的温度升至回流，反应24小时，使用石油醚：二氯甲烷＝2:1重结晶，得到化合物180，产率为75％，质谱数据为：810.40。
实施例21
化合物181的合成
在氮气保护体系下，加入10.0mmol中间体2-1与12.0mmol化合物21-1，加入碳酸钠25mmol和溶剂30mL，溶剂为甲苯和水，比例为2:1，对反应体系脱气，加入催化剂四三苯基膦钯0.2mmol，将反应体系的温度升至回流，反应24小时，使用石油醚：二氯甲烷＝2:1重结晶，得到化合物181，产率为75％，质谱数据为：836.43。
实施例22
化合物187的合成
在氮气保护体系下，加入10.0mmol中间体2-2与12.0mmol化合物22-1，加入碳酸钠25mmol和溶剂30mL，溶剂为甲苯和水，比例为2:1，对反应体系脱气，加入催化剂四三苯基膦钯0.2mmol，将反应体系的温度升至回流，反应24小时，使用石油醚：二氯甲烷＝2:1重结晶，得到化合物187，产率为75％，质谱数据为：760.40。
有机电致发光器件的制备
将涂层厚度为的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透明电极上蒸镀厚度为50nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将上述实施例1-22制备的化合物任意一种、或a-NPD在形成的空穴注入层上面真空蒸镀厚度为30nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为30nm的蓝色主体材料9,10-二(2-萘基)蒽(ADN)和掺杂材料N1，N1,N6,N6-四苯基芘-1,6-二胺(TPPDA)。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为40nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试，测量采用KEITHLEY吉时利2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率，发光颜色。结果见表2，表2为本发明实施例制备的化合物以及a-NPD制备的发光器件的发光特性测试结果。
表2为本发明实施例制备的化合物以及a-NPD和对比样品制备的发光器件的发光特性测试结果。
表2
从表2可知，由本发明提供的有机发光材料作为空穴传输层制备的有机电致发光器件的发光效率及寿命相对于由a-NPD作为空穴传输层制备的有机电致发光器件有显著的提高。
显然，上述实施例仅仅是为清楚地说明所作的举例，而并非对实施方式的限定。对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。

Claims (10)

1.一种有机发光材料，其特征在于，其为下述结构式中的任意一种：
上述结构式中：
R为苯基或联苯基；
Ar1和Ar2各自独立地选自取代或未取代的C6-31的芳基、或者取代或未取代的C12-30的杂芳基。
2.根据权利要求1所述的有机发光材料，其特征在于，Ar1和Ar2各自独立地选自取代或未取代的C10-25的芳基、或者取代或未取代的C16-24的杂芳基。
3.根据权利要求1所述的有机发光材料，其特征在于，Ar1和Ar2各自独立地选自取代或未取代的C14-21的芳基、或者取代或未取代的C18-22的杂芳基。
4.根据权利要求1所述的有机发光材料，其特征在于，Ar1和Ar2各自独立地选自取代或未取代的C16-19的芳基、或者取代或未取代的C21的杂芳基。
5.根据权利要求1所述的有机发光材料，其特征在于，其为下述结构中的任意一种：
6.一种权利要求1所述的有机发光材料的制备方法，其特征在于，包括以下步骤：
步骤1、中间体的合成
将化合物2和化合物1在甲苯中的脱气溶液用N2饱和；然后再加入(1,1'-双(二苯基膦)二茂铁和乙酸钯(II)，随后添加NaOtBu；将该反应混合物加热回流过夜；反应结束后，冷却至室温之后，添加水，将水相用甲苯洗涤，使用MgSO4干燥，并在真空下除去溶剂；使用庚烷/乙酸乙酯经由硅胶过滤粗产物，得到中间体1；
在避光条件下在0℃下将N-溴代丁二酰亚胺添加至中间体1的二氯甲烷溶液中，并且将该混合物在该温度下继续搅拌；该反应通过添加亚硫酸钠溶液而终止，并且再在室温下继续搅拌；在相分离之后，将有机相用水洗涤，并将水相用二氯甲烷提取；将合并的有机相用硫酸钠干燥，并在真空下蒸发；将残余物溶解于乙酸乙酯中，并经由硅胶过滤；然后将粗产物从庚烷中重结晶；得到中间体2；
合成路线如下：
步骤2、目标产物的合成
在氮气保护体系下，向反应瓶中加入中间体2，再加入化合物3或者化合物4，再加入叔丁醇钠和溶剂，对反应体系脱气，加入催化剂三(二亚苄基丙酮)二钯、三(叔丁基)膦，将反应体系的温度升至回流进行反应，反应结束后加入超纯水搅拌，抽滤，乙醇和超纯水淋洗，烘干后得目标产物；
化合物3和化合物4结构式如下：
其中：R为苯基或联苯基；Ar1和Ar2各自独立地选自取代或未取代的C6-31的芳基、或者取代或未取代的C12-30的杂芳基；
L为下述结构中的任意一种：
7.一种含有权利要求1-5任意一项所述有机发光材料的有机电致发光器件。
8.根据权利要求7所述的有机电致发光器件，其特征在于，包括：第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有权利要求1-5任意一项所述有机发光材料；所述有机发光材料可以是单一形态或与其它物质混合存在于有机物层中。
9.根据权利要求8所述的有机电致发光器件，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，既具备空穴注入又具备空穴传输技能层，电子阻挡层，发光层，空穴阻挡层，电子传输层，电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
10.根据权利要求7-9任意一项所述的有机电致发光器件，其特征在于，其可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
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