CN111471453B - 有机电致发光化合物及其制备方法和有机电致发光器件 - Google Patents

有机电致发光化合物及其制备方法和有机电致发光器件 Download PDF

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CN111471453B
CN111471453B CN201911131551.0A CN201911131551A CN111471453B CN 111471453 B CN111471453 B CN 111471453B CN 201911131551 A CN201911131551 A CN 201911131551A CN 111471453 B CN111471453 B CN 111471453B
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organic electroluminescent
tetrahydrofuran
reaction
organic
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CN111471453A (zh
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王士凯
汪康
贾宇
赵贺
邱镇
李贺
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及发光材料技术领域，具体是有机电致发光化合物，其结构式如化学式1所示：

Description

有机电致发光化合物及其制备方法和有机电致发光器件
技术领域
本发明涉及发光材料技术领域，具体是有机电致发光化合物及其制备方法和有机电致发光器件。
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EL装置中，当在阳极和阴极之间施加电压时，来自阳极的空穴和来自阴极的电子注入有机材料层。产生的激子在迁移至基态时产生具有特定波长的光。
决定有机EL装置中的发光效率的最重要因素是发光材料。到目前为止，荧光材料已经广泛用作发光材料。然而，鉴于电致发光机制，由于磷光材料在理论上与荧光材料相比使发光效率增强四倍，因此磷光发光材料的开发得到广泛研究。铱(III)络合物已广泛地被称为磷光掺杂材料。目前，4，4′-N，N′-二咔唑-联苯(CBP)、9，10-二(2-萘基)蒽(ADN)等作为已知的磷光主体材料得到广泛的应用。尽管这些材料提供良好发光特征，但其具有以下缺点：(1)由于其较低玻璃态转变温度和不良热稳定性，导致装置的寿命降低。(2)包含磷光主体材料的有机EL装置需要较高的驱动电压。同时，为了提高有机EL装置的效率和稳定性，需要其具有包含空穴注入层、空穴传输层、发光层、电子传输层和电子注入层的多层结构。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。因此，使用铜酞菁(CuPc)、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)等作为空穴传输材料。然而，使用这些材料的有机EL装置在量子效率和使用寿命方面存在问题，量子效率和寿命需要进一步提高。
发明内容
本发明的目的在于提供有机电致发光化合物及其制备方法和有机电致发光器件，以解决上述背景技术中提出的问题。
为实现上述目的，本发明提供如下技术方案：
有机电致发光化合物，其结构式如化学式1所示：
式中：
R1到R3各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、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C3-C7杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的C3-C30杂芳基、-NR4R5、-SiR6R7R8-、-SR9、-OR10、-COR11、-B(OR12)(OR13)；优选R1到R3为氢、甲基或异丙基；
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，具体为C3-C30脂环族环或芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；优选为萘、蒽或芘，或取代的萘、蒽或芘；其中所述取代基为甲基或苯基；
R4到R13各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的C3-C30杂芳基；
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，具体为C3-C30脂肪族环或芳香族环；
Ar1、Ar2和Ar3表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的C3-C30杂芳基、芳胺基或脂肪胺基；
或与相邻取代基连接形成单环或多环，具体为C3-C30脂环族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；
L为连接键或经取代或未经取代的C6-C30芳基、经取代或未经取代的C6-C30杂芳基；优选苯或氘代苯；
m、n、o为0到4的整数。
作为本发明进一步的方案：所述Ar1、Ar2和Ar3各自独立地选自经取代或未经取代C6-C20芳基、经取代或未经取代的C15-C26杂芳基或三芳基胺，Ar3表示经取代或未经取代的C6-C25芳基、经取代或未经取代的C5-C24杂芳基或三芳基胺。
作为本发明再进一步的方案：所述Ar1和Ar2各自独立地选自经取代或未经取代C10-C14芳基、经取代或未经取代的C18-C22杂芳基或三苯胺基；Ar3表示经取代或未经取代的C10-C20芳基、经取代或未经取代的C12-C18杂芳基或三苯胺基。
作为本发明再进一步的方案：所述有机电致发光化合物选自以下1-70所示结构中的任意一个：
所述有机电致发光化合物的制备方法，包括以下步骤：
步骤一、中间体1的制备；将化合物B溶于四氢呋喃(THF)，接着加入正丁基锂，搅拌均匀，再加入用四氢呋喃溶解的化合物A，室温下进行搅拌反应，制备得到中间体1；
步骤二、化学式1所示化合物的制备；将中间体1和化合物C溶解于四氢呋喃，接着加入MSA(甲磺酸)，室温下进行搅拌反应，制备得到化学式1所示的化合物；
合成路线如下：
其中R1、R2、R3、m、n、o、Ar1、Ar2、Ar3和L与上述化学式1中所定义相同；Hal表示卤素，优选为溴。
作为本发明再进一步的方案：步骤一中，所述中间体1的制备具体包括以下步骤：
在反应容器中加入化合物B和四氢呋喃之后，在氮气氛围下使用所述容器冷却到-78℃；
将正丁基锂缓慢逐滴添加到混合物中，在-78℃下搅拌2小时；
将溶解于四氢呋喃中的化合物A缓慢逐滴添加到混合物中；添加后，使反应温度缓慢升温到室温，并且搅拌混合物12小时；
将氯化铵水溶液添加到反应溶液中，以完成反应，并且用乙酸乙酯萃取反应溶液；
使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用管柱色谱法纯化剩余物质获得中间体1。
作为本发明再进一步的方案：步骤二中，所述化学式1所示化合物的制备具体包括以下步骤：
将中间体1、化合物C和二氯甲烷加入反应容器中之后，用氮气充分置换空气三次；
将溶解于100mL二氯甲烷中的三氟化硼乙醚缓慢逐滴添加到前述混合物中；
在室温下搅拌混合物2小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物；
使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学式1所示的化合物。
有机电致发光器件，含有所述有机电致发光化合物。
与现有技术相比，本发明的有益效果是：
本发明有机电致发光化合物作为空穴材料的有机电致发光器件具有效率高、寿命长的优点，并有效降低了启动电压，解决了现有有机EL装置的量子效率和寿命不理想的问题。
具体实施方式
下面结合具体实施方式对本专利的技术方案作进一步详细地说明。
实施例1：制备化合物1
在反应容器中加入化合物1-2[溴苯(60mmol)]和200mL四氢呋喃之后，在氮气氛围下使用所述容器冷却到-78℃；接着将正丁基锂(2.5M，60mmol)缓慢逐滴添加到混合物中搅拌2h；此后，将溶解于200mL四氢呋喃中的化合物1-1[二苯并环庚酮(60mmol)]缓慢逐滴添加到混合物中；添加后，使反应温度缓慢升温到室温，并且搅拌混合物12小时；接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液；接着使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用管柱色谱法纯化剩余物质获得化合物1-3(12.7g，产率为74％，MW：286.43)。
将化合物1-3(44mmol)、化合物1-4[三苯基胺(46mmol)]和200mLTHF加入反应容器中之后，将MSA(220mmol)缓慢逐滴添加到混合物中；在室温下搅拌混合物5小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化合物1(18.97g，产率为84％，MW：513.74)。
实施例2：制备化合物5
按照实施例1的方法制备化合物5(产率为82％，MW：589.12)；与实施例1的不同之处在于使用中间体5-2代替中间体1-2。
实施例3：制备化合物7
按照实施例1的方法制备化合物7(产率为80％，MW：613.22)；与实施例1的不同之处在于使用中间体7-2代替中间体1-2，使用中间体7-4代替中间体1-4。
实施例4：制备化合物13
按照实施例1的方法制备化合物13(产率为77％，MW：829.45)；与实施例1的不同之处在于使用中间体13-4代替中间体1-4。
实施例5：制备化合物24
按照实施例1的方法制备化合物24(产率为83％，MW：830.51)；与实施例1的不同之处在于使用中间体24-2代替中间体1-2，使用中间体24-4代替中间体1-4。
实施例6：制备化合物26
按照实施例1的方法制备化合物26(产率为80％，MW：720.53)；与实施例1的不同之处在于使用中间体26-2代替中间体1-2。
实施例7：制备化合物39
按照实施例1的方法制备化合物39(产率为84％，MW：657.33)；与实施例1的不同之处在于使用中间体39-2代替中间体1-2，使用中间体39-4代替中间体1-4。
实施例8：制备化合物55
按照实施例1的方法制备化合物55(产率为80％，MW：719.13)；与实施例1的不同之处在于使用中间体55-2代替中间体1-2，使用中间体55-4代替中间体1-4。
实施例9：制备化合物64
按照实施例1的方法制备化合物64(产率为79％，MW：761.43)；与实施例1的不同之处在于使用中间体64-2代替中间体1-2，使用中间体64-4代替中间体1-4。
实施例10：制造含有化合物1的有机电致发光器件
将本发明合成例合成的化合物作为空穴材料，采用通常方法制备有机电致发光器件；首先ITO(阳极)上面蒸镀N1-(萘-2-yl)-N4，N4-二(4-(萘-2-yl(苯基)氨基)苯基)-N1-苯基苯-1，4-二胺(“2-TNATA”)60nm厚度，紧接着蒸镀本发明合成的化合物1厚度60nm、主体物质4，4'-N，N'-二咔唑-联苯(“CBP”)和掺杂物质三(2-苯基吡啶)合铱(“Ir(ppy)3”)按照90：10重量比混合蒸镀30nm厚度、蒸镀空穴阻挡层(“BAlq”)10nm厚度、蒸镀“Alq3”40nm厚度、蒸镀电子注入层LiF0.2nm厚度、蒸镀阴极Al 150nm厚度，形成有机电致发光器件。
实施例11：制造含有化合物5的有机电致发光器件
将实施例10中的化合物1置换为化合物5，其他方法相同，制作含有化合物5的有机电致发光器件。
实施例12：制造含有化合物7的有机电致发光器件
将实施例10中的化合物1置换为化合物7，其他方法相同，制作含有化合物7的有机电致发光器件。
实施例13：制造含有化合物13的有机电致发光器件
将实施例10中的化合物1置换为化合物13，其他方法相同，制作含有化合物13的有机电致发光器件。
实施例14：制造含有化合物24的有机电致发光器件
将实施例10中的化合物1置换为化合物24，其他方法相同，制作含有化合物24的有机电致发光器件。
实施例15：制造含有化合物26的有机电致发光器件
将实施例10中的化合物1置换为化合物26，其他方法相同，制作含有化合物26的有机电致发光器件。
实施例16：制造含有化合物39的有机电致发光器件
将实施例10中的化合物1置换为化合物39，其他方法相同，制作含有化合物39的有机电致发光器件。
实施例17：制造含有化合物55的有机电致发光器件
将实施例10中的化合物1置换为化合物55，其他方法相同，制作含有化合物55的有机电致发光器件。
实施例18：制造含有化合物64的有机电致发光器件
将实施例10中的化合物1置换为化合物64，其他方法相同，制作含有化合物64的有机电致发光器件。
实施例19：制造含有比较化合物1的有机电致发光器件
按照实施例10的方法，将空穴传输层的材料由化合物1置换为比较化合物1，其他方法相同，制作含有比较化合物1的有机电致发光器件。
实施例20：制造含有比较化合物2的有机电致发光器件
按照实施例10的方法，将空穴传输层的材料由化合物1置换为比较化合物2，其他方法相同，制作含有比较化合物2的有机电致发光器件。
表1为本发明实施例制备的化合物以及比较化合物制备的有机电致发光器件的发光特性测试结果。
表1
表1中比较化合物1的各项表征数据设为1，作为比较基准。
由上述表1的结果能确认使用本发明提供的化合物作为空穴材料的有机电致发光器件具有效率高、寿命长的优点，并有效降低了启动电压。
上面对本发明的较佳实施方式作了详细说明，但是本发明并不限于上述实施方式，在本领域的普通技术人员所具备的知识范围内，还可以在不脱离本发明宗旨的前提下作出各种变化。

Claims (4)

1.有机电致发光化合物，其特征在于：所述有机电致发光化合物选自以下1、5、7、13、24、26、39、55或64结构式中的任意一个：
2.基于权利要求1所述的有机电致发光化合物的制备方法，其特征在于：包括以下步骤：
步骤一、中间体1的制备；将化合物B溶于四氢呋喃，接着加入正丁基锂，搅拌均匀，再加入用四氢呋喃溶解的化合物A，室温下进行搅拌反应，制备得到中间体1；
步骤二、有机电致发光化合物的制备；将中间体1和化合物C溶解于四氢呋喃，接着加入MSA，室温下进行搅拌反应，制备得到有机电致发光化合物；
所述化合物A为1-1结构式:
所述化合物B选自以下1-2、5-2、7-2、24-2、26-2、39-2、55-2或64-2结构式中的任意一个：
所述化合物C选自以下1-4、7-4、13-4、24-4、39-4、55-4或64-4结构式中的任意一个:
3.根据权利要求2所述的有机电致发光化合物的制备方法，其特征在于：
步骤一中，所述中间体1的制备具体包括以下步骤：
在反应容器中加入化合物B和四氢呋喃之后，在氮气氛围下使用所述容器冷却到-78℃；
将正丁基锂缓慢逐滴添加到混合物中，在-78℃下搅拌2小时；
将溶解于四氢呋喃中的化合物A缓慢逐滴添加到混合物中；添加后，使反应温度缓慢升温到室温，并且搅拌混合物12小时；
将氯化铵水溶液添加到反应溶液中，并且用乙酸乙酯萃取反应溶液；
使用硫酸镁干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用管柱色谱法纯化剩余物质获得中间体1。
4.有机电致发光器件，其特征在于：含有如权利要求1所述的有机电致发光化合物。
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