CN109970576A - 一种有机电致发光化合物及其制备方法和应用 - Google Patents

一种有机电致发光化合物及其制备方法和应用 Download PDF

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CN109970576A
CN109970576A CN201910323298.2A CN201910323298A CN109970576A CN 109970576 A CN109970576 A CN 109970576A CN 201910323298 A CN201910323298 A CN 201910323298A CN 109970576 A CN109970576 A CN 109970576A
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organic electroluminescent
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CN109970576B (zh
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马晓宇
王永光
贺金新
姜晓晨
李文军
汪康
王进政
孙峰
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明属于发光材料技术领域，具体涉及一种有机电致发光化合物及其制备方法和应用。本发明的有机电致发光化合物结构式如化学式1所示：

Description

一种有机电致发光化合物及其制备方法和应用
技术领域
本发明属于发光材料技术领域，具体涉及一种有机电致发光化合物及其制备方法和应用。
背景技术
有机电致发光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材料层。为了提高有机电致发光元件的效率和稳定性，有机材料层通常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)。在这种有机发光元件中，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。其中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，目前使用铜酞菁(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。使用这些材料的有机电致发光元件虽然在空穴传输效率、发光效率、寿命等方面有所提高，但是在量子效率和使用寿命方面仍然不是很理想。因此需要开发新型结构的空穴传输材料以改善有机电致发光元件在量子效率和使用寿命上的不足。
发明内容
本发明的目的是提供一种具有极佳电流效率和功率效率以及长寿命的一种有机电致发光化合物及其制备方法和应用。
为了实现上述目的，本发明的技术方案具体如下：
一种有机电致发光化合物，其结构式如化学式1所示：
其中：
Ar1和Ar2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3到30元杂芳基；或与相邻取代基连接形成单环或多环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、氧或硫的杂原子；
R0为氢或者氘；t表示0到4的整数；
R1和R2各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；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、氧或硫的杂原子；
X为-O-、-S-、-C(R5)(R6)-、-N(R7)-或-Si(R8)(R9)-，Y为-[C(R3)c(R4)d]m-；
R3到R9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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；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、氧或硫的杂原子；
Q环表示经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；
G环表示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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；
a、b各自独立地表示0到4的整数，c、d各自独立地表示0到2的整数，m和n各自独立地表示0或1、且n为1时，m为0或1，当n为0时，R1可与通式中已示相连G环形成经取代或未经取代的多环C3-C30脂环族环或芳香族环，其碳原子可置换为氮、氧、硫和硅杂原子中的一个或以上。
在上述技术方案中，优选Ar1和Ar2各自独立地选自下述结构中的任意一个：
优选的部分选自下述结构中的任意一个：
上述结构中R为氢、卤素、氰基、C1-C30的烷基、C6-C50的芳基、C7-C50的芳烷基、C7-C50的芳基烷氧基、C7-C50的芳基烷巯基或C5-C50的杂芳基；
上述所述烷基为直链烷基、支链烷基、环烷基、至少1个取代基取代的直链烷基、至少1个取代基取代的支链烷基或至少1个取代基取代的环烷基；其中，所述取代基独立的选自卤素、氰基、羟基和巯基中的一种或几种。
所述芳基优选为未取代的芳基或至少1个取代基取代的芳基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷基优选为未取代的芳基烷基或至少1个取代基取代的芳基烷基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷氧基优选为未取代的芳基烷氧基或至少1个取代基取代的芳基烷氧基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述芳基烷巯基优选为未取代的芳基烷巯基或至少1个取代基取代的芳基烷巯基；其中，所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
所述杂芳基优选为未取代的杂芳基或至少1个取代基取代的杂芳基；其中，杂芳基中的杂原子为氮、硫或氧；所述取代基独立的选择卤素、氨基、氰基、硝基、羟基或巯基；
且所述—R表示在其所在环的任意位置；
其中*为连接位置，表示在其所在环的任意位置。
在上述技术方案中，所述有机电致发光化合物选自以下结构中的任意一个：
本发明的有机电致发光化合物可通过所属领域的技术人员已知的合成方法制备。举例来说，优选其可以根据以下反应流程来制备。
一种有机电致发光化合物的制备方法，包括以下步骤：
步骤1、中间体C的合成：
将化合物B溶于THF中，降温至-78℃，在氮气气氛保护下，滴入正丁基锂溶液，反应，而后加入化合物A，升温至室温，继续反应；反应结束后，滴加饱和氯化铵水溶液，搅拌，加入乙酸乙酯分层、萃取，所得有机相用无水硫酸镁干燥，硅胶柱层析分离纯化，得到中间体C；
步骤2、化学式1所示化合物的合成：
将中间体C和化合物D溶于THF中，加入甲磺酸和多聚磷酸，常温搅拌反应18h；反应结束后，加水，搅拌洗涤，加入乙酸乙酯分层、萃取，所得有机相用饱和碳酸氢钠水溶液洗涤，并用无水硫酸镁干燥，硅胶柱层析分离纯化，得到化学式1所示化合物；
其合成路线如下：
其中、R0、R1、R2、Ar1、Ar2、X、Y、环G、环Q及a、b、n和t如上述式1中所定义，并且Z表示卤素。
在上述技术方案中，优选步骤1中滴入正丁基锂溶液后反应时间为3h，加入化合物A后反应时间为16h。
在上述技术方案中，优选步骤2中反应的时间为18h。
一种本发明所述的化学式1结构的化合物所制备有机电致发光器件的应用。
所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有化学式1所示结构的化合物；化学式1所示结构的化合物可以是单一形态或与其它物质(有机电致发光材料的常规材料)混合存在于有机物层中。所述第一和第二电极中的一个是阳极，且另一个是阴极。所述有机物层包含发光层，并且进一步包含至少一个选自空穴注入层、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组成的群组的层。
优选所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当化学式1结构的化合物存在于所述有机物层中的空穴传输层或者空穴注入层时，所述式化学式1结构的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所述的包含有化学式1结构的化合物制备的器件可以用于有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)。
本发明所述的器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明的有益效果是：
本发明提供用于有机电致发光装置中的可解决传统技术问题的空穴传输材料。传统的空穴传输材料基本以三芳基衍生物为主。虽然其具有空穴传输能力和低驱动电压，但是为了获得合适的玻璃态转变温度而不得不在其结构上引入大量的取代基提升其分子量。但是这样却降低三重态能量或LUMO能量，从而导致有机电致发光器件的劣化。理想的空穴传输材料需要高玻璃态转变温度、空穴注入能力和空穴传输能力，以及适合三重态能量和LUMO能量。因此，为了解决传统空穴传输材料中存在的问题而得到理想的材料，本发明提出向10,10-二苯基蒽的9-位引入芳基胺和杂环以及芳香环以及其他等取代基的解决方案。通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命；通过引入杂环以及芳香环以及其他取代基团等取代基获得适当玻璃态转变温度，从而获得了优质的有机电致发光材料。
本发明提供的有机电致发光化合物的制备方法简单、产率高。
由本发明提供的化合物制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。
具体实施方式
实施例1：制备化合物1
中间体C-1的合成：将溴苯(B-1)(15.7g，100mmol)至于250mL干燥的THF中搅拌，降温至-78℃，在氮气气氛保护下，滴入44mL正丁基锂溶液，继续反应3h。而后加入化合物A-1(34.6g，100mmol)，缓慢升温至室温，反应16h。反应结束后，缓慢滴加饱和氯化铵水溶液200mL，搅拌0.5h，加入300mL乙酸乙酯分层、萃取，所得有机相用无水硫酸镁干燥，硅胶柱层析分离纯化，得到33.9g中间体C-1，收率80％。
化合物1的合成：将中间体C-1(33.9g，80mmol)和中间体D-1(31.8，80mmol)置于300mL干燥的THF中，加入甲磺酸(36g，375mmol)和多聚磷酸(36g)，常温搅拌反应18h。反应结束后，加水500mL，搅拌洗涤0.5h，加入500mL乙酸乙酯分层、萃取，所得有机相用饱和碳酸氢钠水溶液洗涤3次，并用无水硫酸镁干燥，硅胶柱层析分离纯化，得到48.2g化合物1。(收率75％，MW:803.06)。
实施例2：制备化合物12
按照实施例1的方法制备化合物12(收率为：77％，MW:959.58)。与实施例1的不同之处在于使用中间体B-12代替中间体B-1，使用中间体D-12代替中间体D-1。
实施例3：制备化合物19
按照实施例1的方法制备化合物19(收率为：82％，MW:942.43)。与实施例1的不同之处在于使用中间体B-19代替中间体B-1，使用中间体D-19代替中间体D-1。
实施例4：制备化合物26
按照实施例1的方法制备化合物26(收率为：81％，MW:919.41)。与实施例1的不同之处在于使用中间体B-26代替中间体B-1。
实施例5：制备化合物36
按照实施例1的方法制备化合物36(收率为：75％，MW:967.32)。与实施例1的不同之处在于使用中间体B-36代替中间体B-1，使用中间体D-36代替中间体D-1。
实施例6：制备化合物50
按照实施例1的方法制备化合物50(收率为：77％，MW:943.55)。与实施例1的不同之处在于使用中间体B-50代替中间体B-1。
实施例7：制备化合物55
按照实施例1的方法制备化合物55(收率为：80％，MW:979.43)。与实施例1的不同之处在于使用中间体B-55代替中间体B-1，使用中间体D-55代替中间体D-1。
实施例8：制备化合物61
按照实施例1的方法制备化合物61(收率为：75％，MW:975.16)。与实施例1的不同之处在于使用中间体B-61代替中间体B-1，使用中间体D-61代替中间体D-1。
实施例9：制备化合物71
按照实施例1的方法制备化合物71(收率为：76％，MW:818.31)。与实施例1的不同之处在于使用中间体B-71代替中间体B-1，使用中间体D-71代替中间体D-1。
实施例10：制备化合物83
按照实施例1的方法制备化合物83(收率为：79％，MW:844.30)。与实施例1的不同之处在于使用中间体B-83代替中间体B-1，使用中间体D-61代替中间体D-1。
实施例11：制备化合物86
按照实施例1的方法制备化合物86(收率为：81％，MW:923.42)。与实施例1的不同之处在于使用中间体B-12代替中间体B-1，使用中间体D-86代替中间体D-1。
实施例12：制造含有化合物1的有机电致发光器件
将涂层厚度为的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(ADN)和掺杂材料双(4,6-二氟苯基吡啶-N,C2)吡啶甲酰合铱(FIrpic)。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40nm的TPBi作为空穴阻挡层及电子传输层。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。对得到的器件的性能发光特性测试，测量采用KEITHLEY 2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率。
实施例13：制造含有化合物12的有机电致发光器件
将实施例12中的化合物1置换为化合物12，其他方法相同，制作含有化合物12的有机电致发光器件。
实施例14：制造含有化合物19的有机电致发光器件
将实施例12中的化合物1置换为化合物19，其他方法相同，制作含有化合物19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12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36的有机电致发光器件
将实施例12中的化合物1置换为化合物36，其他方法相同，制作含有化合物36的有机电致发光器件。
实施例17：制造含有化合物50的有机电致发光器件
将实施例12中的化合物1置换为化合物50，其他方法相同，制作含有化合物50的有机电致发光器件。
实施例18：制造含有化合物55的有机电致发光器件
将实施例12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19：制造含有化合物61的有机电致发光器件
将实施例12中的化合物1置换为化合物61，其他方法相同，制作含有化合物61的有机电致发光器件。
实施例20：制造含有化合物71的有机电致发光器件
将实施例12中的化合物1置换为化合物71，其他方法相同，制作含有化合物71的有机电致发光器件。
实施例21：制造含有化合物83的有机电致发光器件
将实施例12中的化合物1置换为化合物83，其他方法相同，制作含有化合物83的有机电致发光器件。
实施例22：制造含有化合物86的有机电致发光器件
将实施例12中的化合物1置换为化合物86，其他方法相同，制作含有化合物86的有机电致发光器件。
实施例23：按照实施例12的方法，将空穴传输层的材料由化合物1置换为N'-二(1-萘基)-N，N'-二苯基-(1,1'-联苯)-4，4'-二胺(NPD)。
用热重分析法测量实施例1～11合成的化合物的热分解温度。应用差示扫描量热法测量上述化合物的玻璃化转变温度Tg。结果如表1所示
表1
表2为本发明实施例制备的化合物以及NPD制备的发光器件的发光特性测试结果。
表2
从上表可看成本发明提供的化合物有适合的玻璃态转变温度，由本发明提供的化合物作为空穴传输层制备的发光器件的发光效率及寿命相对于NPD作为空穴传输层制备的发光器件有显著的提高。
以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。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，还可以对本发明进行若干改进和修饰，这些改进和修饰也落入本发明权利要求的保护范围内。

Claims (10)

1.一种有机电致发光化合物，其特征在于，其结构式如化学式1所示：
其中：
Ar1和Ar2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3到30元杂芳基；或与相邻取代基连接形成单环或多环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、氧或硫的杂原子；
R0为氢或者氘；t表示0到4的整数；
R1和R2各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、胺基、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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；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、氧或硫的杂原子；
X为-O-、-S-、-C(R5)(R6)-、-N(R7)-或-Si(R8)(R9)-，Y为-[C(R3)c(R4)d]m-；
R3到R9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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；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、氧或硫的杂原子；
Q环表示经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；
G环表示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3到7元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3到30元杂芳基；
a、b各自独立地表示0到4的整数，c、d各自独立地表示0到2的整数，m和n各自独立地表示0或1、且n为1时，m为0或1，当n为0时，R1可与通式中已示相连G环形成经取代或未经取代的多环C3-C30脂环族环或芳香族环，其碳原子可置换为氮、氧、硫和硅杂原子中的一个或以上。
2.根据权利要求1所述的有机电致发光化合物，其特征在于，Ar1和Ar2各自独立地选自下述结构中的任意一个：
其中，R为氢、卤素、氰基、C1-C30的烷基、C6-C50的芳基、C7-C50的芳烷基、C7-C50的芳基烷氧基、C7-C50的芳基烷巯基或C5-C50的杂芳基。
3.根据权利要求1所述的有机电致发光化合物，其特征在于，的部分选自下述结构中的任意一个：
其中，R为氢、卤素、氰基、C1-C30的烷基、C6-C50的芳基、C7-C50的芳烷基、C7-C50的芳基烷氧基、C7-C50的芳基烷巯基或C5-C50的杂芳基。
4.根据权利要求1所述的有机电致发光化合物，其特征在于，其选自以下结构中的任意一个：
5.一种权利要求1-4任意一项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1、中间体C的合成：
将化合物B溶于THF中，在氮气气氛保护下，滴入正丁基锂溶液，反应，而后加入化合物A，升温至室温，继续反应；反应结束后，滴加饱和氯化铵水溶液，搅拌，加入乙酸乙酯分层、萃取，所得有机相用无水硫酸镁干燥，硅胶柱层析分离纯化，得到中间体C；
步骤2、化学式1所示化合物的合成：
将中间体C和化合物D溶于THF中，加入甲磺酸和多聚磷酸，常温搅拌反应18h；反应结束后，加水，搅拌洗涤，加入乙酸乙酯分层、萃取，所得有机相用饱和碳酸氢钠水溶液洗涤，并用无水硫酸镁干燥，硅胶柱层析分离纯化，得到化学式1所示化合物；
其合成路线如下：
其中，Z表示卤素。
6.根据权利要求5所述的有机电致发光化合物的制备方法，其特征在于，步骤1中滴入正丁基锂溶液后反应时间为3h，加入化合物A后反应时间为16h。
7.根据权利要求5所述的有机电致发光化合物的制备方法，其特征在于，步骤2中反应的时间为18h。
8.一种权利要求1-4任意一项所述的有机电致发光化合物用于制备有机电致发光器件的应用。
9.根据权利要求8所述的应用，其特征在于，所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含权利要求1-4任意一项所述的有机电致发光化合物；权利要求1-4任意一项所述的有机电致发光化合物可以是单一形态或与其它物质混合存在于有机物层中。
10.根据权利要求8所述的应用，其特征在于，所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
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