CN112266353A - 一种芳香族蒽类有机发光化合物及其制备方法与应用 - Google Patents

一种芳香族蒽类有机发光化合物及其制备方法与应用 Download PDF

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CN112266353A
CN112266353A CN202011125408.3A CN202011125408A CN112266353A CN 112266353 A CN112266353 A CN 112266353A CN 202011125408 A CN202011125408 A CN 202011125408A CN 112266353 A CN112266353 A CN 112266353A
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汪康
张雪
王永光
孙向南
陈振生
金成寿
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明公开了一种芳香族蒽类有机发光化合物，其特征在于，所述芳香族蒽类有机发光化合物的结构通式如化学式I所示：

Description

一种芳香族蒽类有机发光化合物及其制备方法与应用
技术领域
本发明涉及有机光电材料技术领域，更具体的说是涉及一种芳香族蒽类有机发光化合物及其制备方法与应用。
背景技术
有机电致发光(EL)是指有机材料在电场作用下,将电能直接转化为光能的一种发光现象。关于有机发光二极管(OLED)的研究起始于上世纪50年代。有机EL材料自发明以来，因其相对于前两代显示(CRT以及LCD)器具有明显的优势，被产业广泛的应用。
为了制作效率高的有机发光器件，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EL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，平衡从阴阳两极注入的空穴和电子，从而利于空穴和电子在发光层的复合，提高器件的激子利用率，最终提高器件的发光效率和使用寿命。
三(8-羟基喹啉)铝(Alq3)作为电子传输材料自发明以来使用了将近30年，而且有较多的资料证明其比常规材料优异。但其作为电子传输材料，向其他层移动等因素制约了其应用。随着市场对OLED器件要求的进一步提高，更高发光效率、更长寿命、更低成本成为OLED器件发展的趋势。
因此，如何开发一种高电子传输性能电子传输材料，提高电子迁移率，促进载流子注入平衡，进而使器件发光效率更高、寿命更长的有机发光化合物是本领域技术人员亟需解决的问题。
发明内容
有鉴于此，本发明提供了一种高电子传输性能电子传输材料，提高电子迁移率，促进载流子注入平衡，进而使器件发光效率更高、寿命更长的芳香族蒽类有机发光化合物及其制备方法和应用。
为了实现上述目的，本发明采用如下技术方案：一种芳香族蒽类有机发光化合物，所述芳香族蒽类有机发光化合物的结构通式如化学式I所示：
Figure BDA0002733454190000021
其中，Ar1、Ar2、Ar3各自独立地表示取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷基、C2-C30烯基、C2-C30炔基、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基、C10-C60的稠环基、C10-C60的螺环基；
R1、R2各自独立地表示氢、氘、卤素、腈基、硝基、羟基、胺基、取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷基、C2-C30烯基、C2-C30炔基、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基；或，R1、R2各自与相邻取代基连接形成单环或多环；
L选自连接键、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基。
优选地，所述R1、R2各自与相邻取代基连接形成单环或多环时，所述单环或多环均为C3-C30脂肪族环或3-10元的芳香族环；
其中，所述脂肪族环或芳香族环中的碳原子至少一个替换为氮、氧及硫中的一种。
优选地，所述L选自苯、萘及联苯中的一种。
优选地，所述Ar3选自取代或非取代的3-30元杂芳基；
其中，所述杂芳基选自单环或稠环。
优选地，所述稠环的其中一个环为至少含有一个杂原子的3-10元的杂芳环；其余环为C3-C30环烷基、3-10元杂环烷基、C3-C30环烯基、C6-C30芳基、3-10元杂芳基中的任一种。
更加优选地，Ar3选自具有吸电子性基团，选自：三嗪、吡啶、咪唑及嘧啶中的任一种。
更加优选地Ar3选自下述结构中的任意一个：
Figure BDA0002733454190000031
其中*代表连接位置。
采用上述技术方案的有益效果：提升化合物在做成器件方面的性能；例如降低驱动电压，延长寿命，增加发光效率等。
在上述技术方案中，优选的芳香族蒽类有机发光化合物选自下述结构中的任意一个：
Figure BDA0002733454190000041
Figure BDA0002733454190000051
Figure BDA0002733454190000061
Figure BDA0002733454190000071
本发明还提供了一种芳香族蒽类有机发光化合物的制备方法，包括以下步骤：
化学式I的合成方法如下：
Figure BDA0002733454190000072
具体步骤如下：
(1)在氮气保护下，将原料A、原料B和NaOt-Bu溶解于干燥的甲苯中，加入Pd2(dba)3和P(t-Bu)3，升温至100-120℃，回流并搅拌反应10-14h；反应结束后萃取，合并有机相，干燥并过滤，减压浓缩过滤产物，使用硅胶柱色谱提纯浓缩产物，得到中间体C；
(2)将中间体C加入到二氯甲烷溶剂中，加NBS；反应结束后，将反应液浓缩，在搅拌条件下将浓缩后的反应液滴加到石油醚中，待固体析出完全，抽滤，烘干，得到中间体D；
(3)在氮气保护下，将中间体D和原料E、碳酸钾加入到混合溶剂中，加入Pd(PPh3)4，加热至90-120℃，得到化学式I所示的化合物。
本发明中的制备方法操作简便、低成本、环保，更加适用于大工业化生产。
优选地，步骤(1)中，所述原料A、原料B、NaOt-Bu、Pd2(dba)3和P(t-Bu)3的摩尔比为(48-52):(50-60):(140-160):(0.5-0.6):(2.5-3.0)；
所述甲苯与所述原料A的体积摩尔比为(1-5)mL：1mmol。
优选地，步骤(2)中，所述二氯甲烷与所述中间体C的体积摩尔比为(2-5)mL：1mmol；
所述烘干时间为4-12h，温度为60-80℃。
优选地，步骤(3)中，所述中间体D、原料E、碳酸钾和Pd(PPh3)4的摩尔比为(25-35):(33-38):(55-65):(0.2-0.4)；
所述混合溶剂为甲苯、乙醇和水按照体积比(2-6):(0.8-1.5):(0.8-1.5)混合得到的。
本发明还提供了一种芳香族蒽类有机发光化合物在有机电致发光器件中的应用。
本发明还提供了一种有机电致发光装置，包括第一电极、第二电极以及有机层；所述第一电极及第二电极之间至少设置一层有机层；
所述有机层包括发光层，发光层包括所述的芳香族蒽类有机发光化合物。
优选地，当本发明有机物层包含空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层时，优选至少一层包含空穴注入物质、空穴传输物质或既具备空穴注入又具备空穴传输技能的物质。
优选地，当本发明有机物层为单层结构时，所述有机物层为发光层，当所述有机物层为多层结构时，所述有机物层包括发光层；所述发光层中优选包括磷光主体、荧光主体、磷光掺杂材料与荧光掺杂材料中的一种或多种。
发光层可以发射红色、绿色或蓝色的光，并且可以由磷光材料或荧光材料形成；所述发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴与电子结合而发出在可见光区域内的光的材料，优选为对荧光或磷光具有有利的量子效率的材料。更加优选地为8-羟基喹啉铝配(Alq3)；基于咔唑的化合物；二聚苯乙烯基化合物；BAlq；10-羟基苯并喹啉-金属化合物；基于苯并唑、基于苯并噻唑和基于苯并咪唑的化合物；基于聚(对亚苯基亚乙烯基)(PPV)的聚合物；螺环化合物；聚芴；红荧烯等，但不限于此。
优选地，当所述有机物层包括电子传输层时，所述电子传输层包括式通式I所示的蒽类衍生物。更加优选地，所述电子传输层还包括金属化合物。所述金属化合物为本领域技术人员熟知的用于电子传输的物质即可，并无特殊的限制。
经由上述的技术方案可知，与现有技术相比，本发明公开提供了一种芳香族蒽类有机发光化合物及其制备方法与应用，该芳香族蒽类有机发光化合物的制备方法操作简便、低成本、环保等特点；将该芳香族蒽类有机发光化合物作为有机电致器件发光层应用于有机电致发光装置中，可以使有机电致发光器件的驱动电压降低、电流效率提高，增加器件的使用寿命。
具体实施方式
下面将结合本发明实施例，对本发明实施例中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。
实施例1
化合物1的制备，其合成路线如下：
Figure BDA0002733454190000101
具体步骤如下：1)氮气保护下，将原料A-1(50mmol)、原料B-1(55mmol)和叔丁醇钠(150mmol)放入烧瓶并溶解于干燥的甲苯(200mL)中。然后，将Pd2(dba)3(0.56mmol)和P(t-Bu)3(2.8mmol)加入上述反应物中，使反应温度缓慢(1小时)升温到110℃，然后回流并搅拌12小时。反应后，使用硅藻土除去盐和催化剂，加水洗涤，保留有机相用二氯甲烷萃取。合并有机相，用无水硫酸镁干燥萃取产物并过滤。然后，在减压下浓缩过滤产物。并且使用旋转式蒸发器去除溶剂。获得中间体C-1(17.5g，产率为83％，Ms:422.18)。
2)氮气保护下，将中间体C-1(38mmol)加入到二氯甲烷(150mL)中，加入NBS。室温搅拌，用TLC监测反应进程。反应结束后，将反应液浓缩至粘稠状态，滴加到搅拌的石油醚中。待固体析出完全，抽滤，烘干，得到中间体D-1(16.7g，产率为88％，Ms:500.09)。
3)氮气保护下，将中间体D-1(30mmol)、反应物E-1(36mmol)、四(三苯基膦)钯(0.3mmol)和碳酸钾(60mmol)加入到甲苯(120mL)、乙醇(40mL)、水(40mL)的混合溶剂中，升温至110℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:7，得到化合物1(13.8g，产率为80％，Ms:574.24)。
实施例2
化合物18的合成，其合成路线如下：
Figure BDA0002733454190000111
具体步骤如下：
1)氮气保护下，将原料A-18(50mmol)、原料B-18(55mmol)和叔丁醇钠(150mmol)放入烧瓶并溶解于干燥的甲苯(200mL)中。然后，将Pd2(dba)3(0.56mmol)和P(t-Bu)3(2.8mmol)加入上述反应物中，使反应温度缓慢(1小时)升温到110℃，然后回流并搅拌12小时。反应后，使用硅藻土除去盐和催化剂，加水洗涤，保留有机相用二氯甲烷萃取。合并有机相，用无水硫酸镁干燥萃取产物并过滤。然后，在减压下浓缩过滤产物。并且使用旋转式蒸发器去除溶剂。获得中间体C-18(26.1g，产率为85％，Ms：613.25)。
2)将中间体C-18(38mmol)加入到二氯甲烷(150mL)中，加入NBS(41.8mmol)。室温搅拌，用TLC监测反应进程。反应结束后，将反应液浓缩至粘稠状态，滴加到搅拌的石油醚中。待固体析出完全，抽滤，烘干，得到中间体D-18(22.3g，产率为85％，Ms：691.66)。
3)氮气保护下，将中间体D-18(30mmol)、反应物E-18(36mmol)、四(三苯基膦)钯(0.3mmol)和碳酸钾(60mmol)加入到甲苯(120mL)、乙醇(40mL)、水(40mL)的混合溶剂中，升温至110℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:7，得到化合物18(16.7g，产率为81％，Ms:689.28)。
实施例3
化合物23的合成，其合成路线如下：
Figure BDA0002733454190000121
1)氮气保护下，将原料A-23(50mmol)、原料B-23(55mmol)和叔丁醇钠(150mmol)放入烧瓶并溶解于干燥的甲苯(200mL)中。然后，将Pd2(dba)3(0.56mmol)和P(t-Bu)3(2.8mmol)加入上述反应物中，使反应温度缓慢(1小时)升温到110℃，然后回流并搅拌12小时。反应后，使用硅藻土除去盐和催化剂，加水洗涤，保留有机相用二氯甲烷萃取。合并有机相，用无水硫酸镁干燥萃取产物并过滤。然后，在减压下浓缩过滤产物。并且使用旋转式蒸发器去除溶剂。获得中间体C-23(24.0g，产率为80％，Ms：599.24)。
2)将中间体C-23(38mmol)加入到二氯甲烷(150mL)中，加入NBS(41.8mmol)。室温搅拌，用TLC监测反应进程。反应结束后，将反应液浓缩至粘稠状态，滴加到搅拌的石油醚中。待固体析出完全，抽滤，烘干，得到中间体D-23(21.6g，产率为84％，Ms：677.15)。
3)氮气保护下，将中间体D-23(30mmol)、反应物E-23(36mmol)、四(三苯基膦)钯(0.3mmol)和碳酸钾(60mmol)加入到甲苯(120mL)、乙醇(40mL)、水(40mL)的混合溶剂中，升温至110℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:7，得到化合物23(17.4g，产率为86％，Ms：675.27)。
实施例4
化合物66的合成
Figure BDA0002733454190000141
1)氮气保护下，将原料A-66(50mmol)、原料B-66(55mmol)和叔丁醇钠(150mmol)放入烧瓶并溶解于干燥的甲苯(200mL)中。然后，将Pd2(dba)3(0.56mmol)和P(t-Bu)3(2.8mmol)加入上述反应物中，使反应温度缓慢(1小时)升温到110℃，然后回流并搅拌12小时。反应后，使用硅藻土除去盐和催化剂，加水洗涤，保留有机相用二氯甲烷萃取。合并有机相，用无水硫酸镁干燥萃取产物并过滤。然后，在减压下浓缩过滤产物。并且使用旋转式蒸发器去除溶剂。获得中间体C-66(25.4g，产率为81％，Ms：627.24)。
2)将中间体C-66(38mmol)加入到二氯甲烷(150mL)中，加入NBS(41.8mmol)。室温搅拌，用TLC监测反应进程。反应结束后，将反应液浓缩至粘稠状态，滴加到搅拌的石油醚中。待固体析出完全，抽滤，烘干，得到中间体D-66(23.0g，产率为86％，Ms：705.15)。
3)氮气保护下，将中间体D-66(30mmol)、反应物E-66(36mmol)、四(三苯基膦)钯(0.3mmol)和碳酸钾(60mmol)加入到甲苯(120mL)、乙醇(40mL)、水(40mL)的混合溶剂中，升温至110℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:7，得到化合物66(17.5g，产率为83％，Ms：703.85)。
实施例5
化合物80的合成，其合成路线如下：
Figure BDA0002733454190000151
具体步骤如下：
1)氮气保护下，将原料A-80(50mmol)、原料B-80(55mmol)和叔丁醇钠(150mmol)放入烧瓶并溶解于干燥的甲苯(200mL)中。然后，将Pd2(dba)3(0.56mmol)和P(t-Bu)3(2.8mmol)加入上述反应物中，使反应温度缓慢(1小时)升温到110℃，然后回流并搅拌12小时。反应后，使用硅藻土除去盐和催化剂，加水洗涤，保留有机相用二氯甲烷萃取。合并有机相，用无水硫酸镁干燥萃取产物并过滤。然后，在减压下浓缩过滤产物。并且使用旋转式蒸发器去除溶剂。获得中间体C-80(22.6g，产率为84％，Ms：537.20)。
2)将中间体C-80(38mmol)加入到二氯甲烷(150mL)中，加入NBS(41.8mmol)。室温搅拌，用TLC监测反应进程。反应结束后，将反应液浓缩至粘稠状态，滴加到搅拌的石油醚中。待固体析出完全，抽滤，烘干，得到中间体D-80(19.4g，产率为83％，Ms：615.11)。
3)氮气保护下，将中间体D-80(30mmol)、反应物E-80(36mmol)、四(三苯基膦)钯(0.3mmol)和碳酸钾(60mmol)加入到甲苯(120mL)、乙醇(40mL)、水(40mL)的混合溶剂中，升温至110℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:7，得到化合物80(15.1g，产率为82％，Ms：613.23)。
其他化合物的合成方法均与上述所列举的实施例相同，所以在此不再一一例举，部分质谱和分子式列于下表1。
实施例 化合物 分子式 质谱理论值 质谱测试值
实施例6 5 C<sub>51</sub>H<sub>35</sub>N<sub>3</sub> 689.28 689.24
实施例7 10 C<sub>47</sub>H<sub>31</sub>D<sub>4</sub>N<sub>3</sub> 645.31 645.32
实施例8 15 C<sub>51</sub>H<sub>32</sub>N<sub>6</sub> 728.27 728.54
实施例9 24 C<sub>50</sub>H<sub>33</sub>N<sub>3</sub> 675.27 675.84
实施例10 30 C<sub>49</sub>H<sub>30</sub>D<sub>5</sub>N<sub>5</sub>S 730.29 730.65
实施例11 34 C<sub>58</sub>H<sub>38</sub>N<sub>6</sub> 818.32 818.69
实施例12 40 C<sub>50</sub>H<sub>32</sub>FN<sub>3</sub> 693.26 693.41
实施例13 44 C<sub>58</sub>H<sub>39</sub>N<sub>5</sub> 805.32 805.17
实施例14 52 C<sub>50</sub>H<sub>37</sub>D<sub>4</sub>N<sub>3</sub> 687.36 687.45
实施例15 58 C<sub>49</sub>H<sub>31</sub>N<sub>7</sub> 717.26 717.46
实施例16 64 C<sub>50</sub>H<sub>32</sub>FN<sub>3</sub> 693.26 693.52
实施例17 70 C<sub>54</sub>H<sub>33</sub>D<sub>5</sub>N<sub>2</sub>S 751.31 751.26
实施例18 72 C<sub>54</sub>H<sub>35</sub>N<sub>3</sub> 725.28 725.36
实施例19 75 C<sub>52</sub>H<sub>34</sub>N<sub>4</sub> 714.28 714.54
实施例20
采用实施例1中的化合物1的芳香族蒽类有机发光化合物制备有机电致发光装置，具体工艺如下:
将费希尔公司涂层厚度为
Figure BDA0002733454190000171
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30min，用蒸馏水反复清洗2次，超声波洗涤10min，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5min，送到蒸镀机里。
将已经准备好的ITO透明电极上蒸镀厚度为80nm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。在形成的空穴注入层上面真空蒸镀厚度为30nm的N'-二(1-萘基)-N，N'-二苯基-(1，1'-联苯)-4，4'-二胺(NPB)作为空穴传输层。然后在上述空穴传输层上蒸镀厚度为20nm的4，4'-N，N'-联苯二咔唑("CBP")作为主体材料以及掺杂有5％FIrpic的发光材料。接着在上述发光层上真空蒸镀厚度为10nm的双(2-甲基-8-羟基喹啉-N1，08)-(1，1’-联苯-4-羟基)铝(BAlq)作为空穴阻挡层。在上述空穴阻挡层上真空蒸镀厚度为40nm化合物1，作为电子传输层。在上述电子传输层上真空蒸镀厚度为1nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为100nm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。以此完成了有机电致发光器件的制备。
参照上述方法，将器件实施例1中使用的化合物1分别替换为5，10，15，18，23，24，30，34，40，44，52，58，64，66，70，72，75，80作为电子传输层，制备得到相应的有机电致发光器件作为实施例21-38。
对比例1
按照器件实施例1相同的方法制备有机电致发光器件，电子传输层化合物结构如下：
Figure BDA0002733454190000181
对比例2
按照器件实施例1相同的方法制备有机电致发光器件，电子传输层化合物结构如下：
Figure BDA0002733454190000182
对上述制备的有机电致发光器件加以正向直流偏置电压，利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性，并在1000cd/m2的基准灰度下利用McScience公司的寿命测定装置测定了T95的寿命。结果见表2。
Figure BDA0002733454190000183
Figure BDA0002733454190000191
与对比例相比，驱动电压下降1.8-2.7V，发光效率提升7.8-15.9％之间，器件寿命提高45-72h。由上述表2的结果能确认使用本发明提供的化合物作为电子传输材料制备的有机电致发光器件表现出高的发光效率及长寿命并降低驱动电压。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其它实施例中实现。因此，本发明将不会被限制于本文所示的这些实施例，而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。

Claims (10)

1.一种芳香族蒽类有机发光化合物，其特征在于，所述芳香族蒽类有机发光化合物的结构通式如化学式I所示：
Figure FDA0002733454180000011
其中，Ar1、Ar2、Ar3各自独立地表示取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷基、C2-C30烯基、C2-C30炔基、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基、C10-C60的稠环基、C10-C60的螺环基；
R1、R2各自独立地表示氢、氘、卤素、腈基、硝基、羟基、胺基、取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷基、C2-C30烯基、C2-C30炔基、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基；或，R1、R2各自与相邻取代基连接形成单环或多环；
L选自连接键、取代或非取代的C6-C30芳基、取代或非取代的3-30元杂芳基。
2.根据权利要求1所述的一种芳香族蒽类有机发光化合物，其特征在于，所述R1、R2各自与相邻取代基连接形成单环或多环时，所述单环或多环均为C3-C30脂肪族环或3-10元的芳香族环；
其中，所述脂肪族环或芳香族环中的碳原子至少一个替换为氮、氧及硫中的一种。
3.根据权利要求1所述的一种芳香族蒽类有机发光化合物，其特征在于，所述L选自苯、萘及联苯中的一种。
4.根据权利要求2或3所述的一种芳香族蒽类有机发光化合物，其特征在于，所述Ar3选自取代或非取代的3-30元杂芳基；
其中，所述杂芳基选自单环或稠环。
5.根据权利要求4所述的一种芳香族蒽类有机发光化合物，其特征在于，所述稠环的其中一个环为至少含有一个杂原子的3-10元的杂芳环；其余环为C3-C30环烷基、3-10元杂环烷基、C3-C30环烯基、C6-C30芳基、3-10元杂芳基中的任一种。
6.一种芳香族蒽类有机发光化合物的制备方法，其特征在于，包括以下步骤：化学式I的合成方法如下：
Figure FDA0002733454180000021
Figure FDA0002733454180000031
具体步骤如下：
(1)在氮气保护下，将原料A、原料B和NaOt-Bu溶解于干燥的甲苯中，加入Pd2(dba)3和P(t-Bu)3，升温至100-120℃，回流并搅拌反应10-14h；反应结束后萃取，合并有机相，干燥并过滤，减压浓缩过滤产物，使用硅胶柱色谱提纯浓缩产物，得到中间体C；
(2)将中间体C加入到二氯甲烷溶剂中，加NBS；反应结束后，将反应液浓缩，在搅拌条件下将浓缩后的反应液滴加到石油醚中，待固体析出完全，抽滤，烘干，得到中间体D；
(3)在氮气保护下，将中间体D和原料E、碳酸钾加入到混合溶剂中，加入Pd(PPh3)4，加热至90-120℃，得到化学式I所示的化合物。
7.根据权利要求6所述的一种芳香族蒽类有机发光化合物的制备方法，其特征在于，步骤(1)中，所述原料A、原料B、NaOt-Bu、Pd2(dba)3和P(t-Bu)3的摩尔比为(48-52):(50-60):(140-160):(0.5-0.6):(2.5-3.0)；
所述甲苯与所述原料A的体积摩尔比为(1-5)mL：1mmol。
8.根据权利要求6所述的一种芳香族蒽类有机发光化合物的制备方法，其特征在于，步骤(2)中，所述二氯甲烷与所述中间体C的体积摩尔比为(2-5)mL：1mmol；
所述烘干时间为4-12h，温度为60-80℃。
9.根据权利要求6所述的一种芳香族蒽类有机发光化合物的制备方法，其特征在于，步骤(3)中，所述中间体D、原料E、碳酸钾和Pd(PPh3)4的摩尔比为(25-35):(33-38):(55-65):(0.2-0.4)；
所述混合溶剂为甲苯、乙醇和水按照体积比(2-6):(0.8-1.5):(0.8-1.5)混合得到的。
10.一种根据权利要求1-5任一项所述的芳香族蒽类有机发光化合物或权利要求7-9任一项所述方法制备的芳香族蒽类有机发光化合物在有机电致发光器件中的应用。
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617456A (zh) * 2008-12-16 2012-08-01 乐金显示有限公司 电子输送-注入化合物及使用它的有机电致发光器件
CN108440396A (zh) * 2018-03-23 2018-08-24 吉林奥来德光电材料股份有限公司 一种有机发光材料及其制备方法和应用
CN110128329A (zh) * 2018-02-02 2019-08-16 北京鼎材科技有限公司 含氮杂环的芳胺类衍生物及其应用和有机电致发光器件
CN110627659A (zh) * 2019-09-26 2019-12-31 吉林奥来德光电材料股份有限公司 有机发光化合物及其制备方法和器件

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617456A (zh) * 2008-12-16 2012-08-01 乐金显示有限公司 电子输送-注入化合物及使用它的有机电致发光器件
CN110128329A (zh) * 2018-02-02 2019-08-16 北京鼎材科技有限公司 含氮杂环的芳胺类衍生物及其应用和有机电致发光器件
CN108440396A (zh) * 2018-03-23 2018-08-24 吉林奥来德光电材料股份有限公司 一种有机发光材料及其制备方法和应用
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