CN111153809A - 一种芳胺类化合物及其制备方法和应用 - Google Patents

一种芳胺类化合物及其制备方法和应用 Download PDF

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CN111153809A
CN111153809A CN202010041574.9A CN202010041574A CN111153809A CN 111153809 A CN111153809 A CN 111153809A CN 202010041574 A CN202010041574 A CN 202010041574A CN 111153809 A CN111153809 A CN 111153809A
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arylamine
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CN111153809B (zh
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金成寿
马晓宇
孙向南
邱镇
王进政
张鹤
张雪
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及有机电致发光材料技术领域，具体地涉及一种芳胺类化合物及其制备方法，该芳胺类化合物具有化学式I所示的结构：

Description

一种芳胺类化合物及其制备方法和应用
技术领域
本发明涉及有机电致发光材料技术领域，具体地涉及一种芳胺类化合物及其制备方法，以及包含该芳胺化合物的显示面板及显示装置，尤其是关于光的取出效率有大幅改善的有机EL器件。
背景技术
根据有机发光层发出光线的方向，OLED显示器可以分为底发射OLED显示器和顶发射OLED显示器。在底发射OLED显示器中，光线朝向基板发出，其中形成的薄膜晶体管部分不透射光线，导致发光面积减小。在顶发射OLED显示器中，透明电极形成在有机发光层上方，反射电极形成在有机发光层下方，所以光线向基板相反方向发出，从而增加了光线透射面积而改善了亮度。针对目前OLED器件光取出效率低的现状，在基底出光表面使用表面覆盖层工艺简单，发光效率提高较为显著，尤被人们关注。
在顶发射器件结构中的阴极表面覆盖一层盖帽层(CPL，亦称阴极覆盖层)，即光提取材料，以调节光学干涉距离，抑制外光发射，抑制表面等离子体的移动引起的消光。根据光学吸收和折射的原理，此表面覆盖层的材料的折射率应该越高越好。
现有的CPL材料存在的问题包括：(1)折射率不够高，光取出效果不够好；(2)在蓝光、绿光以及红光各自的波长区域所测定的折射率之差较大。因此发射蓝光、绿光以及红光的发光器件中的所有光无法同时获得高的光提取效率。
发明内容
鉴于此，本发明的目的在于提供一种芳胺类化合物及其制备方法，作为新的芳胺类CPL材料，此CPL材料在各个波长下的折射率尽可能高，以提高对各种不同颜色的光的提取效率。含有该材料的有机EL器件的发光效率、热稳定性、寿命、启动电压等性能得到极大的改善。
本发明的目的是这样实现的，一种芳胺类化合物，其具有化学式I所示的结构
Figure BDA0002367938940000021
其中：
L1-L3各自独立的表示连接键、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C3-C30)环烯基、经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(3元到10元)杂环基；经取代或未经取代的(C6-C30)稠环基；或与相邻取代基连接形成单环或多环(C3-C30)脂肪族环或(3元到10元)芳香族环，其碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上。
Ar1-Ar4各自独立地表示：氢、氢的同位素、取代或非取代的C1～C60的烷基、C3～C60的环烷基、取代或非取代的C2～C60的烯基、C3～C60的环烯基、取代或非取代的C3～C60的炔基、C3～C60的环炔基、取代或非取代的C6～C60的芳氧基、取代或非取代的C1～C20的烷氧基、取代或非取代的C6～C60的芳氨基、取代或非取代的C1～C20的烷氨基、取代或非取代的C6～C60的芳基或者(3元到10元)的杂环基；或与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30的脂肪族环或(3元到10元)芳香族环，其碳原子可置换成至少一个选自氮、氧或硫的杂原子。
在本说明书中，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；羰基；酯基；甲硅烷基；硼基；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，或者可以解释为两个苯基相连接的取代基。
杂环基是指包括含有至少一个杂原子的芳香族和非芳香族环状基团。任选地，所述至少一个杂原子选自O、S、N、P、B、Si和Se，优选地O、S或N。优选的非芳香族杂环基是含有包括至少一个杂原子的3到7个环原子的杂环基，并且包括吗啉基、哌啶基、吡咯烷、和环醚/硫醚，如四氢呋喃、四氢吡喃、四氢噻吩等。另外，杂环基可以是任选被取代的。
根据本发明的一些实施列，化学式I所示的芳胺类化合物可优选自以下具体结构中的一种，但不仅限于此：
Figure BDA0002367938940000041
Figure BDA0002367938940000051
Figure BDA0002367938940000061
Figure BDA0002367938940000071
本发明还提供了化学式I所示化合物的合成方法，此方法路线简短、原料易得、合成以及提纯难度较小，具体的合成方法如下所示：
合成路线1：
当
Figure BDA0002367938940000081
与
Figure BDA0002367938940000082
不相同时
Figure BDA0002367938940000083
1)、中间体I-3的合成：在氮气氛围下，将I-1(1.0eq)及I-2(1.0eq)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(2.0eq)三叔丁基膦(0.02eq)三(二亚苄基丙酮)二钯(0.01eq)，加热至80℃反应，待反应完毕后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到中间体I-3。
2)、化合物I的合成：在氮气氛围下，中间体I-3(1.0eq)及I-4(1.0eq)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(2.0eq)三叔丁基膦(0.02eq)三(二亚苄基丙酮)二钯(0.01eq)，加毕，加热至80℃反应，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到终产品化合物I。
合成路线2
当
Figure BDA0002367938940000091
与
Figure BDA0002367938940000092
相同时
Figure BDA0002367938940000093
化合物I的合成：在氮气氛围下，将I-1(1.0eq)及I-2(2.0eq)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(4.0eq)三叔丁基膦(0.04eq)三(二亚苄基丙酮)二钯(0.02eq)，加热至80℃反应，待反应完毕后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到目标化合物I。
本发明的有益效果为：对波长为450～635nm的可见光，本发明的芳胺化合物的折射率均大于2.0，符合发光器件对CPL的折射率要求，消光系数k值在蓝光波长450nm以后几乎为0，不会影响发光层材料在蓝光区域的发光。因此能够带来更高的发光效率。另外，本发明的芳胺化合物的玻璃化转变温度均高于155℃，因此显示这些芳胺化合物应用于发光器件时，在薄膜状态下有较高的稳定性。
具体实施方式
以下提供了用于制备化学式I所示化合物的具体实施例
实施例1：
Figure BDA0002367938940000101
1)、中间体1-3的合成：在氮气氛围下，将1-1(100mmol)及1-2(100mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(200mmol)三叔丁基膦(2mmol)三(二亚苄基丙酮)二钯(1mmol)，加热至80℃反应，待反应完毕后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到中间体1-3(42.53g，收率：81％，Mw：525.47)。
2)、目标产物化合物1的合成：在氮气氛围下，将中间体1-3(80mmol)及1-4(80mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(160mmol)三叔丁基膦(1.6mmol)三(二亚苄基丙酮)二钯(0.8mmol)，加热至80℃反应，待反应结束后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到化合物1(50.9g，收率：78％，Mw：816.74)。
实施例2：
Figure BDA0002367938940000111
1)、中间体40-3的合成：在氮气氛围下，将40-1(100mmol)及40-2(100mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(200mmol)三叔丁基膦(2mmol)三(二亚苄基丙酮)二钯(1mmol)，加热至80℃反应，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到产品(52.5g，收率：82％，Mw：640.05)。
2)、目标产物化合物40的合成：在氮气氛围下，将40-3(80mmol)及40-4(80mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(160mmol)三叔丁基膦(1.6mmol)三(二亚苄基丙酮)二钯(0.8mmol)，加热至80℃反应，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到化合物40(55.0g，收率：78％，Mw：881.36)。
实施例3：
Figure BDA0002367938940000121
目标产物化合物13的合成：在氮气氛围下，将13-1(100mmol)及13-2(200mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(400mmol)三叔丁基膦(4mmol)三(二亚苄基丙酮)二钯(2mmol)，加热至100℃反应，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到化合物13(68.8g，收率：86％，Mw：800.34)。
实施例4：
Figure BDA0002367938940000122
目标产物化合物15的合成：在氮气氛围下，将15-1(100mmol)及15-2(200mmol)加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入叔丁醇钠(400mmol)三叔丁基膦(4mmol)三(二亚苄基丙酮)二钯(2mmol)，加热至100℃反应，待反应结束后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到化合物15(63.8g，收率：83％，Mw：768.68)。
因其他化合物的合成方法均与上述所列举的实施例相同，所以在此不再穷举，本发明又选取17个化合物作为实施例，其质谱和分子式列于下表1
化合物 分子式 质谱理论值 质谱测试值
2 C<sub>62</sub>H<sub>44</sub>N<sub>2</sub> 816.35 816.58
3 C<sub>64</sub>H<sub>46</sub>N<sub>2</sub> 842.37 842.82
6 C<sub>59</sub>H<sub>42</sub>N<sub>2</sub> 778.33 778.67
10 C<sub>56</sub>H<sub>36</sub>N<sub>2</sub>S<sub>2</sub> 800.23 800.54
18 C<sub>60</sub>H<sub>40</sub>N<sub>2</sub> 788.32 788.46
22 C<sub>54</sub>H<sub>36</sub>N<sub>2</sub> 712.29 712.65
26 C<sub>63</sub>H<sub>46</sub>N<sub>2</sub> 830.37 830.53
30 C<sub>60</sub>H<sub>32</sub>D<sub>8</sub>N<sub>2</sub>O<sub>2</sub> 828.36 828.62
35 C<sub>66</sub>H<sub>47</sub>N<sub>3</sub> 881.38 881.75
41 C<sub>60</sub>H<sub>42</sub>N<sub>4</sub> 818.34 818.71
45 C<sub>60</sub>H<sub>42</sub>N<sub>4</sub> 818.34 818.56
48 C<sub>58</sub>H<sub>40</sub>N<sub>6</sub> 820.33 820.86
50 C<sub>62</sub>H<sub>42</sub>N<sub>2</sub> 814.33 814.29
58 C<sub>58</sub>H<sub>40</sub>N<sub>2</sub>O<sub>2</sub> 796.31 796.96
63 C<sub>56</sub>H<sub>40</sub>N<sub>6</sub> 796.33 796.49
68 C<sub>60</sub>H<sub>44</sub>N<sub>2</sub> 792.35 792.52
75 C<sub>68</sub>H<sub>48</sub>N<sub>2</sub> 892.38 892.64
使用本发明化合物，在基板之上制作膜厚80nm的蒸镀膜，并使用分光测定装置测定于450nm、530nm、635nm的折射率。为了做比较，针对Alq3也进行测定。
表2中列举了本发明的芳胺化合物以及对比化合物Alq3的热性能和折射率测试结果。
Figure BDA0002367938940000141
由表2可知，对波长为450～635nm的可见光，本发明的芳胺化合物的折射率均大于2.0，符合发光器件对CPL的折射率要求，消光系数k值在蓝光波长450nm以后几乎为0，不会影响发光层材料在蓝光区域的发光。因此能够带来更高的发光效率。另外，本发明的芳胺化合物的玻璃化转变温度均高于155℃，因此显示这些芳胺化合物应用于发光器件时，在薄膜状态下有较高的稳定性。
由以上数据可知，本发明提供的新型芳胺类化合物具有较高的折射率，当其用作有机发光显示装置的盖帽层时，可以提高顶发射有机光电装置的光取出效率。本发明提供的新型芳胺类化合物在蓝光区域具有较小的消光系数，对蓝光几乎没有吸收，利于提升发光效率。同时有效阻挡外部环境中的水和氧，可保护OLED显示面板不受水和氧的侵蚀，可以达成高效率、长寿命的有机EL器件。
因此，本发明提供了一种含有化学式I所示化合物的有机发光器件。此类有机发光器件包括阳极、阴极、位于所述阳极与所述阴极之间的有机层以及位于阴极外侧的盖帽层。所述有机层包括空穴注入层、空穴传输层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层和电子注入层中的一种或几种的组合。所述盖帽层、有机层中的至少一者的材料为本发明所述的芳胺类化合物，尤其是盖帽层包含本发明所述的芳胺类化合物。
本发明中的有机EL器件中，前述盖帽层的厚度为10nm～200nm之范围较佳，50nm～150nm之范围更佳。
本发明之有机EL器件中，在透射前述盖帽层的光的波长为450nm～750nm之范围，该覆盖层之折射率为2.0以上较佳。消光系数k值接近于0为最佳。
本发明之有机EL器件中，前述盖帽层可以使用1种材料也可利用将2种以上不同的构成材料予以叠层而制作。
在本发明的实施例中，有机发光器件可以这样制作：在透明或不透明的光滑的基板上形成阳极，在阳极上形成有机层，在有机层上形成阴极。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。最后在阴极上制备一层盖帽层。盖帽层的材料为本发明所述的芳胺类化合物。盖帽层可以通过蒸镀或溶液法加工制备。溶液加工法包括喷墨打印法、旋转涂布、刮刀涂布、丝网印刷等方法。在本发明中优选蒸镀的方法制作有机电致发光器件。
下面通过实施例和对比例进一步说明化学式I所示芳胺化合物在实际应用中取得的技术效果。这些实施例只是用于说明本发明，本发明不限于以下实施例。凡是对本发明技术方案进行修改或者等同替换，而不脱离本发明技术方案的范围，均应涵盖在本发明的保护范围中。
器件实施例1
实施例提供了一种有机发光器件。有机发光器件包括：基板、ITO阳极、空穴注入层、空穴传输层、发光层、第一电子传输层、第二电子传输层、阴极(镁银电极，镁银质量比为9:1)和盖帽层(CPL)，其中ITO阳极的厚度是15nm，空穴注入层的厚度是5nm、空穴传输层的厚度是70nm、发光层的厚度是25nm、第一电子传输层的厚度是30nm、第二电子传输层的厚度是5nm、镁银电极的厚度是14nm和盖帽层(CPL)的厚度是100nm。
本发明的有机发光器件的制备步骤如下：
将玻璃基分别在异丙醇和去离子水中超声处理30分钟，然后暴露在臭氧下约10分钟来进行清洁；将所得的具有ITO阳极的玻璃基板安装到真空沉积设备上；在ITO阳极层上，通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN，厚度为5nm，该层作为空穴注入层；在空穴注入层上真空蒸镀空穴传输层材料为TAPC，厚度为70nm，作为空穴传输层；空穴传输层上共沉积发光层，其中，CBP作为主体材料，Ir(ppy)3作为掺杂材料，Ir(ppy)3和CBP的质量比为0.5:9.5，厚度为25nm；在发光层上真空蒸镀第一电子传输层，第一电子传输层的材料为TPBI，厚度为30nm；在第一电子传输层上真空蒸镀第二电子传输层，第二电子传输层的材料为Alq3，厚度为5nm；在第二电子传输层上真空蒸镀镁银电极，其中，质量比Mg:Ag为9:1，厚度为14nm，作为阴极；在阴极上真空蒸镀本案设计的化合物1，厚度为100nm，作为阴极盖帽层使用。
有机发光器件实施例2～21
按照有机发光器件实施例1的方法制备有机发光器件2至器件21。不同之处是将CPL层材料化合物1分别换为化合物2，3，6，10，13，15，18，22，26，30，35，40，41，45，48，50，58，63，68，75，其他如发光层和辅助层材料均相同
器件对比例1
按照器件实施例1的方法制备有机发光器件对比例1。不同之处是将CPL层材料化合物1换为CBP，其他如发光层和辅助层材料均相同。
对器件1至器件21、对比器件1的发光性能进行测试，测试结果见表3。电流密度：10mA/cm2。
表3器件发光性能测试结果
Figure BDA0002367938940000181
Figure BDA0002367938940000191
由上表3可以看出，采用本发明的芳胺化合物作为CPL材料的器件的驱动电压均低于对比器件1。与对比器件1相比，采用本发明的芳胺化合物作为CPL材料的器件的亮度和寿命均有显著提升。因此，本发明的芳胺类化合物能够提升发光器件发光效率并延长器件的寿命，是理想的CPL材料。
本发明的又一方面还提供一种显示装置，其包括如上所述的有机发光显示面板。
本申请虽然以较佳实施例公开如上，但并不是用来限定权利要求，任何本领域技术人员在不脱离本申请构思的前提下，都可以做出若干可能的变动和修改，因此本申请的保护范围应当以本申请权利要求所界定的范围为准。

Claims (7)

1.一种芳胺类化合物，其特征在于：该化合物具有化学式I所示的结构
Figure FDA0002367938930000011
其中：L1-L3各自独立的表示连接键、经取代或未经取代的C1-C30烷基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C6-C30芳基、经取代或未经取代的(3元到10元)杂环基；经取代或未经取代的C6-C30稠环基；或与相邻取代基连接形成单环或多环C3-C30脂肪族环或3元到10元芳香族环，其碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上；
其中L1-L3带有取代基，取代基可以为氢的同位素；
Ar1-Ar4各自独立地表示：氢、氢的同位素、取代或非取代的C1～C60的烷基、C3～C60的环烷基、取代或非取代的C2～C60的烯基、C3～C60的环烯基、取代或非取代的C3～C60的炔基、C3～C60的环炔基、取代或非取代的C6～C60的芳氧基、取代或非取代的C1～C20的烷氧基、取代或非取代的C6～C60的芳氨基、取代或非取代的C1～C20的烷氨基、取代或非取代的C6～C60的芳基或者3元到10元的杂环基；或与相邻取代基连接形成经取代或未经取代的单环或多环C3-C30的脂肪族环或3元到10元芳香族环，其碳原子可置换成至少一个选自氮、氧或硫的杂原子。
2.根据权利要求1所述的一种芳胺类化合物，其特征在于：所述杂环基是指包括含有至少一个杂原子的芳香族和非芳香族环状基团。
3.根据权利要求1所述的一种芳胺类化合物，其特征在于：所述至少一个杂原子选自O、S、N、P、B、Si和Se，优选地O、S或N；优选的非芳香族杂环基是含有包括至少一个杂原子的3到7个环原子的杂环基，并且包括吗啉基、哌啶基、吡咯烷、和环醚/硫醚，如四氢呋喃、四氢吡喃、四氢噻吩；另外，杂环基可以是任选被取代的。
4.根据权利要求1所述的一种芳胺类化合物，其特征在于：其特征在于：所述芳胺类化合物选自以下结构中的任意一种：
Figure FDA0002367938930000021
Figure FDA0002367938930000031
Figure FDA0002367938930000041
Figure FDA0002367938930000051
5.一种如权利要求1所述的芳胺类化合物的制备方法，其特征在于：该方法具体的合成路线如下：
当
Figure FDA0002367938930000061
与
Figure FDA0002367938930000062
不相同时
Figure FDA0002367938930000063
1)、中间体I-3的合成：在氮气氛围下，将1.0eq I-1及1.0eq I-2加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入2.0eq叔丁醇钠、0.02eq三叔丁基膦、0.01eq三(二亚苄基丙酮)二钯，加热至80℃反应，待反应完毕后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到中间体I-3；
2)、化合物I的合成：在氮气氛围下，1.0eq中间体I-3及1.0eq I-4加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入2.0eq叔丁醇钠、0.02eq三叔丁基膦、0.01eq三(二亚苄基丙酮)二钯，加毕，加热至80℃反应，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到终产品芳胺类化合物I。
6.一种如权利要求1所述的芳胺类化合物的制备方法，其特征在于：该方法具体的合成路线如下：
当
Figure FDA0002367938930000071
与
Figure FDA0002367938930000072
相同时
Figure FDA0002367938930000073
化合物I的合成：在氮气氛围下，将1.0eq I-1及2.0eq I-2加至甲苯中搅拌，加热至50℃搅拌15min后，依次加入4.0eq叔丁醇钠、0.04eq三叔丁基膦、0.02eq三(二亚苄基丙酮)二钯，加热至80℃反应，待反应完毕后，抽滤后浓缩的产品经硅胶漏斗及重结晶得到目标芳胺类化合物I。
7.一种有机EL器件，包括权利要求1所述芳胺类化合物。
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