CN110627659A - 有机发光化合物及其制备方法和器件 - Google Patents

有机发光化合物及其制备方法和器件 Download PDF

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CN110627659A
CN110627659A CN201910916424.5A CN201910916424A CN110627659A CN 110627659 A CN110627659 A CN 110627659A CN 201910916424 A CN201910916424 A CN 201910916424A CN 110627659 A CN110627659 A CN 110627659A
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substituted
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organic light
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汪康
孙向南
金成寿
张鹤
赵贺
孙峰
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及一种有机发光化合物及其制备方法和器件，所述有机发光化合物的结构如化学式1所示：

Description

有机发光化合物及其制备方法和器件
技术领域
本发明涉及发光材料技术领域，具体涉及一种有机发光化合物及其制备方法和器件。
背景技术
OLED有机半导体功能材料，作为新一代显示技术应运而生，从信息显示到固态照明器件，伴随着广阔的应用前景和技术上的突飞猛进，OLED已经逐渐迈入了产业化进程。
OLED是空穴和电子双注入型发光器件，将电能直接转化为有机半导体材料分子的光能。OLED通常为双加层结构，即有机功能层夹在透明导电阳极和金属阴极之间。在阳极接正极、金属阴极接负极的正向电压驱动下，空穴和电子分别从透明阳极和金属阴极注入有机功能层，经过其他功能层传输到发光层，在库伦作用力下相互靠近，最后成功俘获成为处于束缚能级的电子空穴对即激子，激子辐射退激发发出光子，即有机半导体材料发光。
目前有机电致发光材料的研究已经应用到很多领域，很多企业和人才已经纷纷投身到这一领域，大量性能优良的有机电致发光材料被陆续开发出来，但该技术的产业化进程仍然面临很多关键性问题，开发更多更高效性能的有机材料就显得尤为重要和迫切。
发明内容
本发明的目的是新型的具有蒽和胺结构的有机发光化合物及其制备方法和器件。含有该类材料的有机电致发光器件具有较高的发光效率以及较长的寿命。
为了实现上述目的，本发明的技术方案具体如下：
本发明提供一种有机发光化合物，其结构如化学式1所示：
其中，Ar1、Ar2各自独立地为经取代或未经取代的芳基、经取代或未经取代的芳基胺基、或者经取代或未经取代的杂环基，或者彼此结合成环；
Ar3为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂环基，或者与相邻基团彼此结合成环；
R为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、取代或未取代的芳基烷基、取代或未取代的芳基膦基、或者取代或未取代的杂环基，或者相邻基团彼此结合成环；
L为连接键，或者选自取代或未取代的烷基、取代或未取代的芳基、或取代或未取代的杂环基。
在上述技术方案中，Ar3优选自芳香取代基团，具体的优选为经取代或未经取代的苯基、联苯基、三联苯基、萘基、芴基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、芘基、和菲基中的一种。
在上述技术方案中，Ar3进一步优选为苯基、联苯基、三联苯基、萘基、芴基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、芘基、和菲基中的一种。
在上述技术方案中，L优选为苯基、联苯基、三联苯基、萘基、芘基、菲基、芴基、螺基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、和二苯并噻吩基中的一种。
在上述技术方案中，L进一步优选为苯基或联苯基。
本发明中的烷基优选指的是C1～C20的直链烷基、支链烷基、环烷基；芳基为含有6～60个碳原子的芳基；杂环基为含有3～20个碳原子的杂环烷基或者杂芳基。
在本发明中，相邻基团可任意指取代与相应取代基取代的原子直接连接的原子的取代基、在空间上最接近相应取代基设置的取代基，或者取代相应取代基取代的原子的另一取代基。与相邻基团结合形成环的含义是与相邻基团结合形成经取代或未经取代的脂肪族烃环、经取代或未经取代的芳族烃环、经取代或未经取代的脂肪族杂环、经取代或未经取代的芳族杂环、或经取代或未经取代的其稠环。
在本发明中，“经取代或未经取代的”意指经选自以下的一个或更多个取代基取代：氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基和杂环基，或者未经取代；或者意指经以上例示的取代基中两个或更多个取代基连接的取代基取代，或者未经取代。例如，两个或更多个取代基连接的取代基”可包括联苯基。换言之，联苯基可为芳基，或者可解释为两个苯基连接的取代基。
在上述技术方案中，本发明的有机发光化合物最优选自以下结构中的任意一种：
本发明还提供一种有机发光化合物的制备方法，包括以下步骤：
将原料A与B、四三苯基膦合钯、及碳酸钾，加入甲苯中进行偶合反应，生成中间体C；在NBS的作用下溴化，生成中间体D；中间体D在正丁基锂的作用下形成硼酸中间体E；中间体E与原料F在四三苯基膦钯与碳酸钾作用下形成化学式1所示化合物；
其合成路线如下：
其中，Hal代表卤素，其余取代基团与化学式1中的限定一致，这里不再赘述。
本发明还提供一种有机电致发光器件，包括阳极、阴极、及至于阳极和阴极之间的有机物层，所述有机物层含有本发明化学式1所示的化合物。
在上述技术方案中，本发明化学式1所示的化合物是作为空穴传输层材料。
本发明的有益效果是：
本发明提供的有机发光化合物是具有蒽和胺结构的新型结构的有机发光化合物，含有该类化合物的有机电致发光器件具有较高的发光效率以及较长的寿命。
本发明提供的有机发光化合物的制备方法，原料易得，合成步骤简单，产率较高。
具体实施方式
实施例1化合物4的制备：
在500mL的三口瓶，在通入氮气的保护下，加入27.06g化合物E-4(50mmol)、14.1g化合物F-4(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-4消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得27.97g化合物4，收率：80％，MW:700.02。
实施例2化合物7的制备：
在500mL的三口瓶，在通入氮气的保护下，加入24.46g化合物E-7(50mmol)、11.6g化合物F-7(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-7消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得23.59g化合物7，收率：79％，MW:597.10。
实施例3化合物14的制备：
在500mL的三口瓶，在通入氮气的保护下，加入31.51g化合物E-14(50mmol)、7.8g化合物F-14(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-14消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得27.15g化合物14，收率：82％，HPLC：99.8％，MW:662.42。
实施例4化合物31的制备：
在500mL的三口瓶，在通入氮气的保护下，加入29.46g化合物E-31(50mmol)、9.4g化合物F-31(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-31消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得25.54g化合物31，收率：77％，MW:663.15。
实施例5化合物33的制备：
在500mL的三口瓶，在通入氮气的保护下，加入32.3g化合物E-33(50mmol)、11.6g化合物F-33(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-33消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得28.29g化合物33，收率：75％，MW:754.81。
实施例6化合物34的制备：
在500mL的三口瓶，在通入氮气的保护下，加入39.82g化合物E-34(50mmol)、11.6g化合物F-34(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-34消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得32.56g化合物34，收率：72％，MW:903.79。
实施例7化合物45的制备
在500mL的三口瓶，在通入氮气的保护下，加入32.87g化合物E-45(50mmol)、11.6g化合物F-45(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-45消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得30.23g化合物45，收率：79％，MW:765.14。
实施例8化合物50的制备
在500mL的三口瓶，在通入氮气的保护下，加入39.86g化合物E-50(50mmol)、11.6g化合物F-50(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-50消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得33.0g化合物50，收率：73％，MW:905.21。
器件实施例1：
选取ITO玻璃为阳极，在蒸馏水中清洗2次，超声波洗涤30分钟，按异丙醇、丙酮、甲醇按顺序洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，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。在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA真空蒸镀厚度为60mm、空穴材料层为化合物4，真空蒸镀厚度为20nm、发光材料层按照90:10掺杂的CBP和Ir(ppy)3真空蒸镀厚度为30nm，电子传输层Alq3厚度为40nm、电子注入层LiF厚度为0.2nm，阴极Al厚度为150nm。
器件实施例2：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例2制备的化合物7。
器件实施例3：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例3制备的化合物14。
器件实施例4：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例4制备的化合物31。
器件实施例5：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例5制备的化合物33。
器件实施例6：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例6制备的化合物34。
器件实施例7：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例7制备的化合物45。
器件实施例8：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例8制备的化合物50。
器件对比例1：
本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为TCTA(4,4’,4”-三(咔唑-9-基)三苯胺)。
下表为本发明实施例制备的化合物以及TCTA制备的发光器件的发光特性测试结果。
由上表可知：与对比例化合物作为空穴传输层材料制备的有机电致发光器件相比，由本发明的化合物作为空穴传输层材料制备的有机电致发光器件具有更低的驱动电压，高的效率，及长寿命。
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 (9)

1.一种有机发光化合物，其特征在于，其结构如化学式1所示：
其中，Ar1、Ar2各自独立地为经取代或未经取代的芳基、经取代或未经取代的芳基胺基、或者经取代或未经取代的杂环基，或者彼此结合成环；
Ar3为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂环基，或者与相邻基团彼此结合成环；
R为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、取代或未取代的芳基烷基、取代或未取代的芳基膦基、或者取代或未取代的杂环基，或者相邻基团彼此结合成环；
L为连接键，或者选自取代或未取代的烷基、取代或未取代的芳基、或取代或未取代的杂环基。
2.根据权利要求1所述的有机发光化合物，其特征在于，Ar3选自经取代或未经取代的苯基、联苯基、三联苯基、萘基、芴基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、芘基、和菲基中的一种。
3.根据权利要求1所述的有机发光化合物，其特征在于，Ar3选自苯基、联苯基、三联苯基、萘基、芴基、芘基、和菲基中的一种。
4.根据权利要求1所述的有机发光化合物，其特征在于，L为苯基、联苯基、三联苯基、萘基、芘基、菲基、芴基、螺基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、和二苯并噻吩基中的一种。
5.根据权利要求1所述的有机发光化合物，其特征在于，L为苯基或联苯基。
6.根据权利要求1所述的有机发光化合物，其特征在于，其选自以下结构中的任意一种：
7.一种权利要求1-6任意一项所述的有机发光化合物的制备方法，其特征在于，包括以下步骤：
将原料A与B、四三苯基膦合钯、及碳酸钾，加入甲苯中进行偶合反应，生成中间体C；在NBS的作用下溴化，生成中间体D；中间体D在正丁基锂的作用下形成硼酸中间体E；中间体E与原料F在四三苯基膦钯与碳酸钾作用下形成化学式1所示化合物；
其合成路线如下：
其中，Hal代表卤素。
8.一种有机电致发光器件，包括阳极、阴极、及至于阳极和阴极之间的有机物层，其特征在于，所述有机物层含有权利要求1-6任意一项所述的有机发光化合物。
9.根据权利要求8所述的有机电致发光器件，其特征在于，所述的有机发光化合物是作为空穴传输层材料。
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