CN112047872B - 一种有机电致发光芴类化合物及其制备方法和应用 - Google Patents

一种有机电致发光芴类化合物及其制备方法和应用 Download PDF

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CN112047872B
CN112047872B CN202010987047.7A CN202010987047A CN112047872B CN 112047872 B CN112047872 B CN 112047872B CN 202010987047 A CN202010987047 A CN 202010987047A CN 112047872 B CN112047872 B CN 112047872B
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马晓宇
王永光
张雪
王进政
张鹤
黄悦
汪康
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明提供了一种有机电致发光芴类化合物，结构通式如说明书所示，本发明还提供了该有机电致发光芴类化合物在制备有机电致发光器件中的应用，本发明有机电致发光芴类化合物通过引入芳基胺和新颖芘类衍生物获得了空穴注入能力/传输能力，是一种高效率、长寿命的优质有机电致发光材料，提供的有机电致发光芴类材料的制备方法，制备步骤简单，产物纯度高。

Description

一种有机电致发光芴类化合物及其制备方法和应用
技术领域
本发明涉及有机光电材料领域，具体涉及一种有机电致发光芴类化合物及其制备方法和应用。
背景技术
电致发光装置(EL装置)为自动发光装置，其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。有机EL元件是利用了如下原理的自发光元件：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构:阳极、阴极以及介于两者之间的有机层。为了提高有机EL元件的效率和稳定性，有机材料层需要包括具有不同材料的多层，例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)，在这种有机发光二极管中，当在阳极和阴极之间施加电压时，来自阳极的空穴注入层和来自阴极的电子注入层产生的激子在迁移至基态时产生具有特定波长的光。
空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。根据现有的技术，在空穴传输层中或在空穴注入层中使用的空穴传输材料特别是如下所述的三芳胺衍生物，其能常含有至少两个三芳氨基基团或至少一个三芳基氨基基团和至少一个咔唑基团。这些化合物通常来源于二芳氨基基团取代的三苯胺(TPA型)、二芳基氨基取代的联苯衍生物(TAD类型)或这些基础化合物的组合，例如，作为用于OLED的具有空穴传输性质的材料的三芳基胺化合物的已知实例有4,4',4”-三-(3-甲基苯基-苯基氨基)-三苯基胺(MTDATA)、4，4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N，N′-二苯基-N，N′-双(3-甲基苯基)-(1，1′-联苯)-4，4′-二胺(TPD)等。然而，无论是对于荧光OLED，还是对于磷光OLED，使用这些材料的有机电致发光器件中时在发光效率、使用寿命和工作电压等方面仍需要进一步改进。
因此，研发一种适用于荧光或磷光OLED的发光效率高、使用寿命长和工作电压低的有机电致发光芴类化合物及其制备方法和应用是本领域人员亟需解决的技术问题。
发明内容
有鉴于此，本发明提供了一种有机电致发光芴类化合物及其制备方法和在制备有机电致发光器件中的应用。
为了实现上述目的，本发明采用如下技术方案：
一种有机电致发光芴类化合物，所述有机电致发光芴类化合物的结构通式如化学式1所示：
Figure BDA0002689603170000021
其中，Ar1、Ar2、Ar3、Ar4各自独立地选自：取代或非取代的C6-C60环烷基、取代或非取代的C6-C60芳基、取代或非取代的3元至60元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的3元至60元芳基氨基、取代或非取代的6元至60元芳氧基、取代或非取代的金刚烷基；
R1选自：氢、取代或非取代的C1-C10烷基、取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C6-C30芳基氨基、取代或非取代的C6-C30芳氧基；
L1、L2为连接键，或各自独立地选自：取代或非取代的C3-C30环烷基、取代或非取代的C3-C7杂环烷基、取代或非取代的C6-C30芳基、取代或非取代的C3-C30杂芳基；或L1、L2各自独立地与相邻取代基连接形成单环或多环。
优选地，上述Ar1、Ar2、Ar3、Ar4各自独立地选自：萘基、菲基、苯基、甲基苯基、芴基、二甲基苯基、二甲基芴基，三联苯基、联苯、二苯并呋喃、二苯并噻吩及其衍生物。
采用上述优选地有益效果是：从合成路线看：原料成本低,易获得,反应收率高、易处理、好提纯。从器件角度上看：能够有效的目的提高材料的效率和寿命，使材料拥有良好的热稳定性和成膜性，并使材料有较佳的空穴迁移率。
L1、L2表示在其所在环的任意位置。
进一步，所述单环或多环为取代或非取代的C6-C30脂肪族环或取代或非取代的C6-C30芳香族环；
所述脂肪族环或芳香族环中至少一个碳原子置换为氮、氧或硫。
优选的，上述有机电致发光芴类化合物的结构式为以下结构式中的任一种：
Figure BDA0002689603170000041
Figure BDA0002689603170000051
Figure BDA0002689603170000061
Figure BDA0002689603170000071
Figure BDA0002689603170000081
本发明还提供一种有机电致发光芴类化合物的制备方法，包括以下步骤：
(1)将化合物A和化合物B溶于DMF中，在氮气保护下，加入CuI、邻菲罗啉、CS2CO3，升温搅拌，降温，加水搅拌，待固体析出完毕后，抽滤，得目标产物，将目标产物用二氯甲烷溶解，用管柱色谱法纯化剩余物质，得中间体C；
(2)在氮气保护下，将中间体C、化合物D、四(三苯基膦)钯和碳酸钾加入到甲苯、乙醇、水的混合溶剂中，升温回流反应，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，再用乙醇淋洗，干燥滤饼，置于1,4-二氧六环中重结晶，得中间体E；
(3)在氮气保护下，将中间体E、化合物F、四(三苯基膦)钯和碳酸钾加入到甲苯、乙醇、水的混合溶剂中，升温回流反应，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，再用乙醇淋洗，干燥滤饼，用管柱色谱法纯化剩余物质，得如化学式1所示的有机电致发光芴类化合物；
上述如化学式1所示的有机电致发光芴类化合物的合成路线为：
Figure BDA0002689603170000091
进一步，步骤(1)中，上述化合物A、化合物B、CuI、邻菲罗啉、CS2CO3的摩尔比为1:1-1.2:0.05-0.3:0.05-0.3:2-3；上述目标产物和二氯甲烷的质量体积比为1g:10-30mL；上述用管柱色谱法纯化剩余物质所用洗脱剂为：体积比为8:1的石油醚和二氯甲烷。
优选地，步骤(1)中，上述化合物A、化合物B、CuI、邻菲罗啉、CS2CO3的摩尔比为1:1:0.25:0.25:3。
采用上述进一步的有益效果是：原料A得到充分反应，最大限度提高中间体C的产率。
进一步，步骤(1)中，上述升温至155℃搅拌24h，降温至30℃，加水搅拌10min。
采用上述进一步的有益效果是：能够使中间体C在水中直接析出，充分搅拌后抽滤得到目标产物，乙醇和石油醚冲洗后晾干即可投下一步反应。
进一步，步骤(2)中，上述中间体C、化合物D、四(三苯基膦)钯、碳酸钾的摩尔比为1:1-1.1:0.005-0.02:2-3；所述苯、乙醇、水的体积比为1-3:1-3:1；所述干燥滤饼和1,4-二氧六环的质量体积比为1g:10-50mL；所述升温至100℃回流反应8h。
优选地，上述中间体C、化合物D、四(三苯基膦)钯、碳酸钾的摩尔比为1:1.1:0.01:3；苯、乙醇、水的体积比为2:2:1；
采用上述进一步的有益效果是：降到温室后，析出固体，得到中间体杂质很少，只需要1,4-二氧六环重结晶一次即可。
进一步，步骤(3)中，中间体E、化合物F、四(三苯基膦)钯和碳酸钾的摩尔比为1:1-1.3:0.005-0.02:2-3；所述苯、乙醇、水的体积比为1-3:1-3:1；上述用色谱法纯化产物所用洗脱剂为：体积比为1:9的乙酸乙酯和石油醚；升温至110℃回流反应8h。
优选地，中间体E、化合物F、四(三苯基膦)钯和碳酸钾的摩尔比为1:1.1:0.005:3；苯、乙醇、水的体积比为2:2:1；
采用上述进一步的有益效果是：降温后析出固体，产品杂质点少，易于提纯，损失率小，工艺路线优选。
本发明还提供一种根据上述有机电致发光芴类化合物在制备有机电致发光器件中的应用。
本发明还提供一种有机电致发光器件,包括依次蒸镀的第一电极、有机电致发光材料层、第二电极；其中，上述有机电致发光材料层包括上述有机电致发光芴类化合物。
进一步，上述有机电致发光材料层包括依次蒸镀的发光层、空穴注入层、空穴传输层、电子传输层、电子注入层、空穴阻挡层以及电子阻挡层中的一层或几层，且至少其中一层包括上述有机电致发光芴类化合物。
采用上述进一步的有益效果是：使用本发明芴类化合物做为空穴注入层/空穴转输层使之具有更高传输效率、可靠的稳定性，更长的使用寿命。
上述“取代或非取代的”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；取代或非取代的烷基；取代或非取代的环烷基；取代或非取代的烷氧基；取代或非取代的烯基；取代或非取代的烷基胺基；取代或非取代的杂环基胺基；取代或非取代的芳基胺基；取代或非取代的芳基；取代或非取代的杂环基，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。
本发明的有益效果是：本发明有机电致发光芴类化合物通过引入芳基胺和新颖芘类衍生物获得了空穴注入能力/传输能力，是一种高效率、长寿命的优质有机电致发光材料。
本发明提供的有机电致发光芴类材料的制备方法，制备步骤简单，产物纯度高。
具体实施方式
以下的实施例在于详细说明本发明，只是本发明的较佳实施例，并非限制本发明。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的合成
Figure BDA0002689603170000121
(1)在反应容器中加入化学式化合物A-1(80mmol)和化合物B-1(88mmol)溶于DMF(300mL)之后，在氮气保护下加入CuI(20mmol)、邻菲罗啉(20mmol)、CS2CO3(240mmol)，添加后，升温到155℃，并且搅拌混合物24h，将反应液降到30℃，加水80mL，搅拌10分钟，有固体析出，抽滤，得目标产物。将目标产物用二氯甲烷100mL溶解，用管柱色谱法纯化剩余物质，(石油醚：二氯甲烷＝8：1)得到中间体C-1(27.9g，产率为82％，Ms:424.94)。
(2)氮气保护下，将中间体C-1(60mmol)、化合物D-1(66mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(132mmol)加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃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，再用少量乙醇淋洗，干燥滤饼，置于1,4-二氧六环中重结晶(240mL)，得到中间体E-1(22.5g，产率为80％，Ms:468.14)。
(3)氮气保护下，将中间体E-1(45mmol)、化合物F-1(54mmol)、四(三苯基膦)钯(0.45mmol)和碳酸钾(60mmol)加入到甲苯(180mL)、乙醇(60mL)、水(60mL)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，洗脱剂体积比为乙酸乙酯：石油醚＝1:9，得到化合物1(19.7g，产率为73％，Ms:601.25)。
实施例2化合物29的合成
Figure BDA0002689603170000131
(1)在反应容器中加入化学式化合物A-29(80mmol)和化合物B-29(88mmol)溶于DMF(300mL)之后，在氮气保护下加入CuI(20mmol)、邻菲罗啉(20mmol)、CS2CO3(240mmol)。添加后，升温到155℃，并且搅拌混合物24h。将反应液降到30℃，加水80mL，搅拌10分钟，有固体析出，抽滤，得目标产物。将目标产物用二氯甲烷100mL溶解，用管柱色谱法纯化(石油醚：二氯甲烷＝8：1)得到中间体C-29(27.9g，产率为82％，Ms:424.94)。
(2)氮气保护下，将中间体C-29(60mmol)、化合物D-29(66mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(132mmol)加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃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，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(240mL)，得到中间体E-29(30.9g，产率为85％，Ms:606.19)。
(3)氮气保护下，将中间体E-29(45mmol)、化合物F-29(54mmol)、四(三苯基膦)钯(0.45mmol)和碳酸钾(60mmol)加入到甲苯(180mL)、乙醇(60mL)、水(60mL)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，洗脱剂体积比为乙酸乙酯：石油醚＝1:9，得到化合物29(25.6g，产率为77％，Ms:739.30)。
实施例3化合物45的合成
Figure BDA0002689603170000141
(1)在反应容器中加入化学式化合物A-45(80mmol)和化合物B-45(88mmol)溶于DMF(300mL)之后，在氮气保护下加入CuI(20mmol)、邻菲罗啉(20mmol)、CS2CO3(240mmol)。添加后，升温到155℃，并且搅拌混合物24h。将反应液降到30℃，加水80mL，搅拌10分钟，有固体析出，抽滤，得目标产物。将目标产物用二氯甲烷100mL溶解，用管柱色谱法纯化(石油醚：二氯甲烷＝8：1)得到中间体C-45(25.5g，产率为75％，Ms:424.94)。。
(2)氮气保护下，将中间体C-45(60mmol)、化合物D-45(66mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(132mmol)加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃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，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(240mL)，得到中间体E-45(29.2g，产率为82％，Ms:594.19)。
(3)氮气保护下，将中间体E-45(45mmol)、化合物F-45(54mmol)、四(三苯基膦)钯(0.45mmol)和碳酸钾(60mmol)加入到甲苯(180mL)、乙醇(60mL)、水(60mL)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，洗脱剂体积比为乙酸乙酯：石油醚＝1:9，得到化合物45(28.6g，产率为79％，Ms:804.33)。
实施例4化合物63的合成
Figure BDA0002689603170000151
(1)在反应容器中加入化学式化合物A-63(80mmol)和化合物B-63(88mmol)溶于DMF(300mL)之后，在氮气保护下加入CuI(20mmol)、邻菲罗啉(20mmol)、CS2CO3(240mmol)。添加后，升温到155℃，并且搅拌混合物24h。将反应液降到30℃，加水80mL，搅拌10分钟，有固体析出，抽滤，得目标产物。将目标产物用二氯甲烷100mL溶解，用管柱色谱法纯化(石油醚：二氯甲烷＝8：1)得到中间体C-63(25.5g，产率为75％，Ms:424.94)。
(2)氮气保护下，将中间体C-63(60mmol)、化合物D-63(66mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(132mmol)加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃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，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(240mL)，得到中间体E-63(32.5g，产率为81％，Ms:669.20)。
(3)氮气保护下，将中间体E-63(45mmol)、化合物F-63(54mmol)、四(三苯基膦)钯(0.45mmol)和碳酸钾(60mmol)加入到甲苯(180mL)、乙醇(60mL)、水(60mL)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，洗脱剂体积比为乙酸乙酯：石油醚＝1:9，得到化合物63(31.4g，产率为76％，Ms:918.37)。
实施例5化合物88的合成
Figure BDA0002689603170000161
(1)在反应容器中加入化学式化合物A-88(80mmol)和化合物B-88(88mmol)溶于DMF(300mL)之后，在氮气保护下加入CuI(20mmol)、邻菲罗啉(20mmol)、CS2CO3(240mmol)。添加后，升温到155℃，并且搅拌混合物24h。将反应液降到30℃，加水80mL，搅拌10分钟，有固体析出，抽滤，得目标产物。将目标产物用二氯甲烷100mL溶解，用管柱色谱法纯化(石油醚：二氯甲烷＝8：1)得到中间体C-88(26.5g，产率为78％，Ms:424.94)。
(2)氮气保护下，将中间体C-88(60mmol)、化合物D-88(66mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(132mmol)加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃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，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(240mL)，得到中间体E-88(26.1g，产率为82％，Ms:530.21)。
(3)氮气保护下，将中间体E-88(45mmol)、化合物F-88(54mmol)、四(三苯基膦)钯(0.45mmol)和碳酸钾(60mmol)加入到甲苯(180mL)、乙醇(60mL)、水(60mL)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，洗脱剂体积比为乙酸乙酯：石油醚＝1:9，得到化合物88(26.5g，产率为72％，Ms:819.38)。
实施例6至实施例20
其他部分化合物质谱和分子式列于下表1。
表1：
Figure BDA0002689603170000171
Figure BDA0002689603170000181
器件实施例1：制造含有化合物1的有机电致发光器件
将涂层厚度为
Figure BDA0002689603170000182
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。然后将实施例1制备的的化合物1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(AND)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的Alq3作为电子传输层。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。
将器件实施例1中的化合物1分别置换为化合物5，16，24，29，31，38，45，46，51，56，61，63，70，80，84，88，90，100，108其他方法相同，分别制作含有化合物5，16，24，29，31，38，45，46，51，56，61，63，70，80，84，88，90，100，108的有机电致发光器件实施例2-器件实施例20。
器件对比例1：制造含有对比化合物1的有机电致发光器件。
按照器件实施例1的方法，将空穴传输层的化合物1置换为对比化合物1，其他方法相同，制作含有对比化合物1的有机电致发光器件。
Figure BDA0002689603170000191
表2：器件实施例1-20以及器件对比例1的发光特性测试结果(亮度值为5000cd/m2)
Figure BDA0002689603170000192
Figure BDA0002689603170000201
上述表2的结果能确认使用本发明提供的化合物作为空穴材料制备的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。与器件对比例1相比，驱动电压下降1.4V，发光效率提升10.3-17.8％，同时器件寿命提高19-37h。
以上的说明是本发明的简单的说明而已，本发明的应用不限于上述举例，对本领域普通技术人员来说，可以根据上述说明范围内加以改进或变换，所有这些改进和变换应属于本发明权利要求的保护范围。假如本发明实施例是为了说明本发明而已，发明内容范围不是限定在这个范围。本发明的保护范围是必须下面权利要求范围内解析，跟本发明同等范围的一切技术是包含在本发明的权利范围内。

Claims (4)

1.一种有机电致发光芴类化合物，其特征在于，所述有机电致发光芴类化合物的结构式为以下结构式中的任一种：
Figure FDA0003420874260000011
Figure FDA0003420874260000021
2.一种根据权利要求1所述有机电致发光芴类化合物在制备有机电致发光器件中的应用。
3.一种有机电致发光器件,其特征在于，包括依次蒸镀的第一电极、有机电致发光材料层、第二电极；其中，所述有机电致发光材料层包括权利要求1所述有机电致发光芴类化合物。
4.根据权利要求3所述一种有机电致发光器件,其特征在于，所述有机电致发光材料层包括依次蒸镀的发光层、空穴注入层、空穴传输层、电子传输层、电子注入层、空穴阻挡层以及电子阻挡层中的一层或几层，且至少其中一层包括权利要求1所述有机电致发光芴类化合物。
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