CN111777609B - 一种含蒽类衍生物及其制备方法和应用 - Google Patents

一种含蒽类衍生物及其制备方法和应用 Download PDF

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CN111777609B
CN111777609B CN202010715719.9A CN202010715719A CN111777609B CN 111777609 B CN111777609 B CN 111777609B CN 202010715719 A CN202010715719 A CN 202010715719A CN 111777609 B CN111777609 B CN 111777609B
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anthracene
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CN111777609A (zh
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王永光
张雪
汪康
陈振生
王进政
张鹤
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明提供了一种含蒽类衍生物及其制备方法和应用，含蒽类衍生物具有式Ⅰ所示通式。该含蒽类衍生物制备的有机电致发光器件具有较高的发光效率。还具有较高的寿命及较低的驱动电压。有机电致发光器件的发光效率为32.7～38.1％；驱动电压为3.3～3.8V；T(95)为122～153h。

Description

一种含蒽类衍生物及其制备方法和应用
技术领域
本发明属于有机光电材料技术领域，尤其涉及一种含蒽类衍生物及其制备方法和应用。
背景技术
OLED，是指有机电致发光器件。由于其颜色明亮、视角宽、与全动视频相容、温度范围广、形状因子薄且适合、动力需求低且具有用于低成本制造工艺的潜能，所以OLEDs被看作是阴极射线管(CRTs)和液晶显示器(LCDs)的未来替代技术。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OLED器件中空穴传输材料的空穴迁移率一般远大于电子传输材料的电子迁移率，这种载流子传输速率不平衡会带来器件性能的显著下降。因此设计性质优异的电子传输材料非常重要。
通常来说，电子传输材料都是具有大的共轭结构的平面芳香族化合物，它们大多具有较好的电子接受能力，同时在一定的正向偏压下又可以有效的传递电子。目前传统的电子传输材料包括Alq3、TAZ、TPBi、Bphen、BCP等的电子迁移率都不是很高，与空穴传输材料较高的空穴迁移率相比所带来的不均衡会严重影响器件的稳定性。同时随着蓝光磷光器件以及白光器件的发展，这些材料低的三线态不能有效地把激子局限在发光层中，激子的扩散与复合淬灭会在很大程度上影响器件发光效率和发光纯度。另外这些材料的玻璃化转变温度比较低，这导致在器件工作过程中产生的热量带来材料本身的结晶，器件的稳定性会降低。
发明内容
有鉴于此，本发明的目的在于提供一种含蒽类衍生物及其制备方法和应用，该含蒽类衍生物制备的有机电致发光器件具有较高的发光效率。
本发明提供了一种含蒽类衍生物，具有式Ⅰ所示通式：
Figure BDA0002598068930000021
所述Y选自O、S、C(R3R4)、Si(R5R6)或N(R7)；
所述n1和n2的取值独立地选自1、2、3或4；
所述R1～R7独立地选自氢、经取代或未经取代的C1～C12的烷基、经取代或未经取代的C6～C30的芳基、或经取代或未经取代的3元～30元的杂芳基；
所述L选自经取代或未经取代的C6～C30的芳基；或经取代或未经取代的3元～30元的杂芳基；
所述X1～X8独立地选自C、O、S、N或Si，且至少含有O、S、N、Si中的一种；
所述Ar1选自经取代或未经取代的C6～C30芳基；或经取代或未经取代的3元～30元的杂芳基。
优选地，所述R1～R7独立地选自经取代或未经取代的C1～C6的烷基、经取代或未经取代的C6～C20的芳基、或经取代或未经取代的3元～10元的杂芳基；
所述L选自经取代或未经取代的C6～C20的芳基；或经取代或未经取代的3元～10元的杂芳基；
所述Ar1选自经取代或未经取代的C6～C20芳基；或经取代或未经取代的3元～10元的杂芳基。
优选地，所述Ar1选自
Figure BDA0002598068930000022
Figure BDA0002598068930000023
Figure BDA0002598068930000031
Figure BDA0002598068930000041
优选地，所述R1选自氢、CH3、
Figure BDA0002598068930000042
所述R2选自氢、-CH3、
Figure BDA0002598068930000043
所述L选自
Figure BDA0002598068930000044
所述Y选自
Figure BDA0002598068930000045
O、S或
Figure BDA0002598068930000046
优选地，所述含蒽类衍生物具体为化合物1～125中任一种。
本发明提供了一种上述技术方案所述含蒽类衍生物的制备方法，包括以下步骤：
将具有式Ⅱ结构的反应物和具有式Ⅲ结构的反应物在叔丁醇钠、Pd2(dba)3、三叔丁基膦存在下反应，终止反应后得到具有式Ⅰ结构的含蒽类衍生物；
Figure BDA0002598068930000047
式Ⅲ中，所述X选自卤素。
本发明提供了一种有机电致发光器件，包括第一电极、第二电极和置于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中包括上述技术方案所述的含蒽类衍生物。
本发明提供了一种含蒽类衍生物，具有式Ⅰ所示通式。该含蒽类衍生物制备的有机电致发光器件具有较高的发光效率。还具有较高的寿命及较低的驱动电压。实验结果表明：有机电致发光器件的发光效率为32.7～38.1％；驱动电压为3.3～3.8V；T(95)为122～153h。
附图说明
图1为本发明实施例1制备的化合物1的质谱图；
图2为本发明实施例1制备的化合物1的HNM图。
具体实施方式
本发明提供了一种含蒽类衍生物，具有式Ⅰ所示通式：
Figure BDA0002598068930000051
所述Y选自O、S、C(R3R4)、Si(R5R6)或N(R7)；
所述n1和n2的取值独立地选自1、2、3或4；
所述R1～R7独立地选自氢、经取代或未经取代的C1～C12的烷基、经取代或未经取代的C6～C30的芳基、或经取代或未经取代的3元～30元的杂芳基；
所述L选自经取代或未经取代的C6～C30的芳基；或经取代或未经取代的3元～30元的杂芳基；
所述X1～X8独立地选自C、O、S、N或Si，且至少含有O、S、N、Si中的一种；
所述Ar1选自经取代或未经取代的C6～C30芳基；或经取代或未经取代的3元～30元的杂芳基。
在本发明中，所述X1～X8独立地选自C、O、S、N或Si，且至少含有O、S、N、Si中的一种，且必须含有C；优选地，所述X1～X8选自C和N。
在本发明中，所述R1～R7独立地选自经取代或未经取代的C1～C6的烷基、经取代或未经取代的C6～C20的芳基、或经取代或未经取代的3元～10元的杂芳基；所述R1优选选自氢、-CH3、
Figure BDA0002598068930000052
所述R2优选选自氢、-CH3、
Figure BDA0002598068930000053
所述R3～R7选自甲基。
所述Y优选选自
Figure BDA0002598068930000061
O、S或
Figure BDA0002598068930000062
所述L优选选自经取代或未经取代的C6～C20的芳基；或经取代或未经取代的3元～10元的杂芳基；更优选选自
Figure BDA0002598068930000063
Figure BDA0002598068930000064
所述Ar1优选选自经取代或未经取代的C6～C20芳基；或经取代或未经取代的3元～10元的杂芳基，更优选选自
Figure BDA0002598068930000065
Figure BDA0002598068930000066
Figure BDA0002598068930000071
在本发明中，所述含蒽类衍生物优选具体为化合物1～125中任一种：
Figure BDA0002598068930000081
Figure BDA0002598068930000091
Figure BDA0002598068930000101
Figure BDA0002598068930000111
Figure BDA0002598068930000121
Figure BDA0002598068930000131
Figure BDA0002598068930000141
在本发明中，术语“经取代或未经取代的”意指被选自以下的一个、两个或更多个取代基取代：氘；卤素基团；腈基；羟基；经取代或未经取代的烷基；经取代或未经取代的环烷基；经取代或未经取代的烷氧基；经取代或未经取代的烯基；经取代或未经取代的烷基胺基；经取代或未经取代的杂环基胺基；经取代或未经取代的芳基胺基；经取代或未经取代的芳基；和经取代或未经取代的杂环基，或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代，或者不具有取代基。例如，“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之，联苯基可以为芳基，或可以解释为两个苯基相连接的取代基。
本发明提供了一种上述技术方案所述含蒽类衍生物的制备方法，包括以下步骤：
将具有式Ⅱ结构的反应物和具有式Ⅲ结构的反应物在叔丁醇钠、Pd2(dba)3、三叔丁基膦存在下反应，终止反应后得到具有式Ⅰ结构的含蒽类衍生物；
Figure BDA0002598068930000142
式Ⅲ中，所述X选自卤素，优选选自Br或Cl。
本发明优选将具有式Ⅱ结构的反应物和叔丁醇钠混合，氮气保护下，室温下搅拌8～12min；再加入具有式Ⅲ结构的反应物、Pd2(dba)3、三叔丁基膦。
在本发明中，所述反应的温度为105～120℃；反应的时间为10～14h。
本发明在反应期间采用TLC监测反应程度，直到原料全部反应完毕。反应结束后降温，加水终止反应，分液，收集有机相，旋干，得到固体；采用柱层析法提纯，得到具有式Ⅰ结构的含蒽类衍生物。
本发明提供了一种有机电致发光器件，包括第一电极、第二电极和置于两电极之间的一层或多层有机化合物层；
至少一层有机化合物层中包括上述技术方案所述的含蒽类衍生物。
所述有机电致发光器件包括第一电极和第二电极；所述第一电极为ITO透明电极；所述第二电极选自铝。
所述有机化合物层包括依次接触的空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层和电子注入层。所述有机电致发光器件包括一层或多层有机化合物层；所述有机化合物层包括空穴注入层和/或空穴传输层；优选所述空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层中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。具体实施例中，所述空穴注入层包括4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)；厚度为80nm。所述空穴传输层包括N'-二(1-萘基)-N，N'-二苯基-(1,1'-联苯)-4，4'-二胺(NPB)；所述空穴传输层的厚度为30nm。
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。
所述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。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，并且优选为对荧光或磷光具有有利的量子效率的材料。其具体实例包括：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。具体实施例中，所述发光层包括4,4'-N,N'-联苯二咔唑("CBP")和FIr6；所述发光层的厚度为20nm。
所述空穴阻挡层可存在，也可以不存在；所述空穴阻挡层包括双(2-甲基-8-羟基喹啉-N1,O8)-(1,1’-联苯-4-羟基)铝(BAlq)；厚度为10nm。
所述电子传输层包括式通式I所示的含蒽类衍生物。在本发明的一些具体实施例中，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金属化合物即可，并无特殊的限制。具体实施例中，所述电子传输层的厚度为40nm。具体实施例中，所述电子传输层中的含蒽类衍生物具体为上述化合物1、化合物2，化合物9，化合物21，化合物30，化合物38，化合物45，化合物53，化合物62，化合物71，化合物75，化合物78，化合物82，化合物90，化合物95，化合物105和化合物118中的一种或多种。
所述电子注入层优选为氟化锂；电子注入层的厚度为1nm。
根据所使用的材料，根据本说明书的有机发光器件可以为顶部发射型、底部发射型或双侧发射型。
在制造有机发光器件时，可以通过溶液涂覆法和真空沉积法使通式I所示的蒽类衍生物形成为有机材料层。在此，溶液涂覆法意指旋涂、浸涂、喷墨印刷、丝网印刷、喷洒法等，但不限于此。
本发明所述的器件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。
为了进一步说明本发明，下面结合实施例对本发明提供的一种含蒽类衍生物及其制备方法和应用进行详细地描述，但不能将它们理解为对本发明保护范围的限定。
实施例1
Figure BDA0002598068930000161
将反应物B-1(50mmol)加到四口烧瓶中，再加入叔丁醇钠(100mmol)，氮气保护，室温下搅拌10分钟。再分别加入反应物A-1(42mmol)、Pd2(dba)3(0.5mmol)、三叔丁基膦(1mmol)，升温到110℃搅拌过夜。期间用TLC监测反应程度，直到原料全部反应完毕。降温，加水中止反应，分液，收集有机相旋干得到深色固体。柱层析法提纯，二氯甲烷：石油醚＝1:4作为洗脱剂冲洗出全部产品点，得到化合物1(19.7g，产率85％)。
图1为本发明实施例1制备的化合物1的质谱图；图2为本发明实施例1制备的化合物1的HNM图。
实施例2
Figure BDA0002598068930000171
将反应物B-38(50mmol)加到四口烧瓶中，再加入叔丁醇钠(100mmol)，氮气保护，室温下搅拌10分钟。再分别加入反应物A-38(42mmol)、Pd2(dba)3(0.5mmol)、三叔丁基膦(1mmol)，升温到110℃搅拌过夜。期间用TLC监测反应程度，直到原料全部反应完毕。降温，加水中止反应，分液，收集有机相旋干得到深色固体。柱层析法提纯，二氯甲烷：石油醚＝1：4作为洗脱剂冲洗出全部产品，得到化合物38(22.7g，产率81％)。
实施例3
Figure BDA0002598068930000172
将反应物B-75(50mmol)加到四口烧瓶中，再加入叔丁醇钠(100mmol)，氮气保护，室温下搅拌10分钟。再分别加入反应物A-75(42mmol)、Pd2(dba)3(0.5mmol)、三叔丁基膦(1mmol)，升温到110℃搅拌过夜。期间用TLC监测反应程度，直到原料全部反应完毕。降温，加水中止反应，分液，收集有机相旋干得到深色固体。柱层析法提纯，二氯甲烷：石油醚＝1：4作为洗脱剂冲洗出全部产品点，得到化合物75(23.6g，产率78％)。
实施例4
Figure BDA0002598068930000181
将反应物B-105(50mmol)加到四口烧瓶中，再加入叔丁醇钠(100mmol)，氮气保护，室温下搅拌10分钟。再分别加入反应物A-105(42mmol)、Pd2(dba)3(0.5mmol)、三叔丁基膦(1mmol)，升温到110℃搅拌过夜。期间用TLC监测反应程度，直到原料全部反应完毕。降温，加水中止反应，分液，收集有机相旋干得到深色固体。柱层析法提纯，二氯甲烷：石油醚＝1：4作为洗脱剂冲洗出全部产品点，得到化合物105(28.7g，产率86％)。
其他化合物的合成方法与上述相同，在此不一一赘述，其他合成实施例质谱或分子式如下表1所示：
表1其它化合物的质谱或分子式
化合物 分子式 质谱理论值 质谱测试值
2 C<sub>41</sub>H<sub>33</sub>N<sub>3</sub> 567.27 567.79
9 C<sub>51</sub>H<sub>39</sub>N<sub>3</sub> 693.31 693.74
21 C<sub>45</sub>H<sub>32</sub>N<sub>4</sub>S 660.23 660.75
30 C<sub>36</sub>H<sub>23</sub>N<sub>3</sub>O 513.18 513.57
45 C<sub>44</sub>H<sub>30</sub>N<sub>4</sub>O 630.24 630.56
53 C<sub>36</sub>H<sub>23</sub>N<sub>3</sub>S 529.16 529.71
62 C<sub>49</sub>H<sub>33</sub>N<sub>3</sub>S 695.24 695.48
71 C<sub>49</sub>H<sub>31</sub>N<sub>3</sub>SSe 773.14 773.57
78 C<sub>46</sub>H<sub>29</sub>N<sub>3</sub>S 655.21 655.86
82 C<sub>47</sub>H<sub>33</sub>N<sub>3</sub> 639.27 639.80
90 C<sub>51</sub>H<sub>35</sub>N<sub>3</sub>S 721.26 751.42
95 C<sub>54</sub>H<sub>38</sub>N<sub>6</sub> 770.32 770.80
118 C<sub>47</sub>H<sub>33</sub>N<sub>3</sub> 639.27 639.16
器件实施例1
将费希尔公司涂层厚度为
Figure BDA0002598068930000191
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％FIr6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。
器件实施例2～17
参照器件实施例1的方法，将器件实施例1中使用的化合物1分别替换为化合物2，化合物9，化合物21，化合物30，化合物38，化合物45，化合物53，化合物62，化合物71，化合物75，化合物78，化合物82，化合物90，化合物95，化合物105，化合物118作为电子传输层，制备得到相应的有机电致发光器件。
器件比较例1
参照器件实施例1的方法制备有机光电致发光器件，电子传输层化合物结构如下：
Figure BDA0002598068930000192
器件比较例2
参照器件实施例1的方法制备有机光电致发光器件，电子传输层化合物结构如下：
Figure BDA0002598068930000193
本发明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PhotoResearch公司的PR-650光度测量设备测定有机电致发光特性，并在5000cd/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：
表2器件比较例1～2和器件实施例1～17制备的器件的性能测试结果
Figure BDA0002598068930000201
与比较例相比，驱动电压下降约2.0V，发光效率提升7.4～15.4％之间，器件寿命提高42～78h。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。
由以上实施例可知，本发明提供了一种含蒽类衍生物，具有式Ⅰ所示通式。该含蒽类衍生物制备的有机电致发光器件具有较高的发光效率。还具有较高的寿命及较低的驱动电压。实验结果表明：有机电致发光器件的发光效率为32.7～38.1％；驱动电压为3.3～3.8V；T(95)为122～153h。
以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。

Claims (3)

1.一种含蒽类衍生物，其特征在于，所述含蒽类衍生物具体为以下化合物中任一种：
Figure 568965DEST_PATH_IMAGE001
Figure 767865DEST_PATH_IMAGE002
。
2.一种权利要求1所述含蒽类衍生物的制备方法，包括以下步骤：
将具有式Ⅱ结构的反应物和具有式Ⅲ结构的反应物在叔丁醇钠、Pd2(dba)3、三叔丁基膦存在下反应，终止反应后得到权利要求1所述的含蒽类衍生物；
Figure 246754DEST_PATH_IMAGE004
式Ⅱ；
Figure 983765DEST_PATH_IMAGE005
式Ⅲ；
式Ⅲ中，所述X选自卤素；
所述R1和R2选自的取代基同权利要求1；所述n1和n2的取值为1；
所述X1~X8选自的取代基同权利要求1；
所述L选自的取代基同权利要求1；
所述Y选自的取代基同权利要求1。
3.一种有机电致发光器件，包括第一电极、第二电极和置于两电极之间的有机化合物层；
所述有机化合物层包括依次接触的空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层和电子注入层; 所述空穴阻挡层可存在，也可以不存在；
所述电子传输层包括权利要求1所述的含蒽类衍生物或权利要求2所述制备方法制备的含蒽类衍生物。
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