CN111233674A - 芴类化合物及其制备方法和有机电致发光器件 - Google Patents

芴类化合物及其制备方法和有机电致发光器件 Download PDF

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CN111233674A
CN111233674A CN202010152926.8A CN202010152926A CN111233674A CN 111233674 A CN111233674 A CN 111233674A CN 202010152926 A CN202010152926 A CN 202010152926A CN 111233674 A CN111233674 A CN 111233674A
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fluorene
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汪康
孙向南
王进政
刘昌�
金虎勇
李文军
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及一种芴类化合物及其制备方法和有机电致发光器件，属于发光材料领域。所述芴类化合物，其结构式如下：

Description

芴类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领域，具体涉及一种芴类化合物及其制备方法和有机电致发光器件。
背景技术
为了提高有机电致发光器件的亮度、效率和寿命，通常在器件中使用多层结构。这些多层结构包括发光层及各种辅助有机层，如空穴注入层、空穴传输层、电子传输层等。这些辅助有机层的作用是提高载流子(空穴和电子)在各层界面间的注入效率，平衡载流子在各层之间的传输，从而提高器件的亮度和效率。其中空穴传输层是用来增强器件的空穴传输能力，同时将电子阻挡在发光层内，从而提高电子与空穴的复合几率的。
基准的空穴传输层为了降低驱动电压而开发空穴移动度快的物质，为了提高空穴移动度开发了组装密度高HOMO价跟发光层HOMO价接近的物质，但空穴移动度快、物质一般呈现效率减少的倾向。空穴移动度比电子移动度快，会出现电子不均衡现象最终出现发光效率及寿命减少现象。
使用组装密度低的物质减少空穴移动度，因而调节发光层内的电子均衡情况会出现低的组装密度提高驱动电压，驱动电压提高增加电子加热而减少器件寿命情况发生，因此迫切要求组装密度高同时空穴俘获能力优秀的物质的开发。
发明内容
本发明的目的是为了提高显示器件的发光效率、稳定性及寿命，进而提供一种新型结构的芴类化合物及其制备方法和有机电致发光器件。
为了实现上述目的，本发明的技术方案具体如下：
本发明提供了一种芴类化合物，其结构式如下：
Figure BDA0002403064260000021
式中，Ar1和Ar2各自独立地为取代或未取代的C1-C30烷基、取代或未经取代的C1-C30烷基氨基、取代或非取代的C6-C30芳基氨基、取代或未取代的苯基、取代或未取代的C10-C30稠环芳基、或取代或未取代的3元到30元杂芳基；
Ar1和Ar2各自独立地优选为萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯基、9,9二甲基-9H-芴基、或9,9二苯基-9H-芴基等。
R1、R2、R3、R4各自独立地选自氢、或氢的同位素。
R5、R6、R7各自独立地选自氢、氢的同位素、卤素、氰基、羧基、硝基、羟基、磺酸基、磷酸基、硼烷基、取代或未取代的硅基、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、取代或未经取代的C6-C30芳基、取代或未经取代的3元到30元杂芳基、取代或未经取代的C1-C30烷氧基、取代或未经取代的C1-C30烷基氨基、取代或未经取代的C1-C30芳基氨基、取代或未经取代的C1-C30芳氧基、或取代或未经取代的C1-C30芳硫基。
R5、R6、R7各自独立地优选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基等。
R5、R6、R7取代基的位置为在所在苯环的任意位置，R5、R6的个数为0～4，R7的个数为0～5，且R5、R6、R7不能同时为氢或者氢的同位素。
在上述技术方案中，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。
在上述技术方案中，所述芴类化合物为下述结构中的任意一个：
Figure BDA0002403064260000041
Figure BDA0002403064260000051
Figure BDA0002403064260000061
Figure BDA0002403064260000071
Figure BDA0002403064260000081
本发明还提供了一种芴类化合物的制备方法，包括以下步骤：
化合物C的合成
向反应容器里按顺序加入化合物B和四氢呋喃溶剂，在氮气气氛下使所述容器冷却到-78℃；接着将正丁基锂逐滴添加到混合物中；在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃；此后，将溶解于四氢呋喃中的化合物A逐滴添加到混合物中；添加后，使反应温度升温到室温，并且搅拌混合物16小时；反应结束以后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，有机层用硫酸镁干燥以后的浓缩产品用柱色谱法纯化，得到化合物C；
目标化合物的合成
向反应容器里加入化合物C、化合物D、二氯甲烷，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中，室温下反应；反应结束以后用二氯甲烷和水提取有机物，有机层用硫酸镁干燥以后的浓缩产品用柱色谱法纯化，得到目标化合物；其合成路线如下：
Figure BDA0002403064260000091
式中，Ar1、Ar2、R5～R7与上述范围相同；Hal为卤素，优选为溴；R8与R1～R4范围相同。
本发明还提供一种由本发明提供的芴类化合物制备的有机电致发光器件。
在上述技术方案中，所述芴类化合物是作为空穴传输层材料。
本发明的有益效果是：
本发明提供的芴类化合物作为空穴传输层制备的有机电致发光器件表现出高的效率及长寿命。
本发明提供的芴类化合物的制备方法，其原料易得、制法简单、产率高，适用于工业化生产。
具体实施方式
实施例1
化合物2的合成
Figure BDA0002403064260000101
在反应容器中加入反应物溴苯B-2(60mmol)和200mL四氢呋喃之后，在氮气氛围下使所述容器冷却到-78℃。接着将正丁基锂(2.5M，60mmol)缓慢逐滴添加到混合物中。在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃。此后，将溶解于200mL四氢呋喃中的化合物A-2(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16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经萃取的有机层，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中间体C-2(19.2g，78％，MW:410.22)。
将中间体C-2(45mmol)、反应物D-2(46mmol)和500mL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(46mmol)缓慢逐滴添加到混合物中。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。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2(27.61g，86％，MW:713.42)。
实施例2
化合物28的合成
Figure BDA0002403064260000111
将反应物9-芴酮A-28(60mmol)，中间体B-28(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中间体C-2的合成方法，得到中间体C-28(13.33g，74％，MW:300.10)。
将中间体C-28(44mmol)、反应物D-28(45mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(45mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物28(26.46g，85％，MW:707.39)。
实施例3
化合物34的合成
Figure BDA0002403064260000112
将反应物7-苯基-9-芴酮A-34(60mmol)，反应物B-34(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到中间体C-34(16.25g，72％，MW:376.10)。
利用中间体C-34(40mmol)、反应物D-34(42mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(42mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物34(25.76g，81％，MW:795.21)。
实施例4
化合物62的合成
Figure BDA0002403064260000121
将反应物A-62(60mmol)，反应物B-62(60mmol)，正丁基锂(2.5M,60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到化合物C-62(24.5g，77％，MW:530.20)。
利用中间体C-62(45mmol)、反应物D-62(46mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(46mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物62(33.96g，83％，MW:909.25)。
实施例5
化合物69的合成
Figure BDA0002403064260000131
将反应物9-芴酮A-69(60mmol)，反应物体异丙苯B-69(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到中间体C-69(15.1g，80％，MW:314.25)
利用中间体C-69(45mmol)、反应物D-69(46mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(46mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物69(33.96g，83％，MW:909.25)。
实施例6
化合物76的合成
Figure BDA0002403064260000132
将反应物芴酮A-76(60mmol)，反应物体异丙苯B-76(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到中间体C-76(16.48g，77％，MW:356.65)。
将中间体C-76(45mmol)、反应物D-76(46mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(46mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物76(31.2g，80％，MW:866.65)。
实施例7
化合物106的合成
Figure BDA0002403064260000141
将反应物A-106(60mmol)，反应物B-106(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到中间体C-106
(19.07g，76％，MW:418.23)。
将中间体C-106(44mmol)、反应物D-106(45mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(45mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物106(29.12g，83％，MW:797.40)。
实施例8
化合物114的合成
Figure BDA0002403064260000151
将反应物A-114(60mmol)，反应物B-114(60mmol)，正丁基锂(2.5M，60mmol)，四氢呋喃200mL按照实施例1中化合物C-2的合成方法得到化合物C-114(13.33g，74％，MW:300.10)。
将中间体C-114(44mmol)、反应物D-114(45mmol)、溶解于100mL二氯甲烷中的三氟化硼乙醚(45mmol)、二氯甲烷600mL按照和实施例中化合物2的合成方法得到化合物114(26.28g，81％，MW:737.40)。
其他化合物的合成方法均与上述所列举的实施例相同，所以在此不再一一例举，本发明又选取21个化合物做为实施例，其质谱和分子式列于下表1。
表1：
Figure BDA0002403064260000152
Figure BDA0002403064260000161
本发明提供了一种有机电致发光器件，包括以上有机发光化合物或上述制备方法制备的有机发光化合物。
本发明提供了一种有机电致发光器件，包括以上有机发光化合物或上述制备方法制备的有机发光化合物。
所述有机电致发光器件为本领域技术人员熟知的有机电致发光器件即可，本发明优选包括第一电极、第二电极和设置于所述第一电极与第二电极之间的一个或多个有机物层；至少一个所述有机物层包含上述有机发光化合物。
本发明中，所述有机物层是指有机电致发光器件第一电极和第二电极之间的全部层。所述有机物层中的至少一层为发光层。
当本发明有机物层包含空穴注入层、空穴传输层、发光辅助层和同时具备空穴注入和空穴传输技能层、发光层、电子传输层、电子注入层时，优选所述有机物层中至少一层包含空穴注入物质、空穴传输物质、发光辅助物质或既具备空穴注入又具备空穴传输技能的物质。当本发明有机物层为单层结构时，所述有机物层为发光层，当所述有机物层为多层结构时，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。
当所述有机物层包括空穴传输层或发光辅助层时，所述空穴传输层包括通式I所示的有机发光化合物。
本发明提供的有机发光化合物合成路线较短，工艺简单，原料易得，成本低，适合工业化生产。
为了更进一步的描述本发明，以下列举更具体的实施例。
有机电致发光器件的制备及性能评价实例
[实施例1]绿光有机电致发光器件(空穴传输层)
将本发明实施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2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LiF 0.2nm厚度、蒸镀阴极Al 150nm厚度，形成有机电致发光器件。
[实施例2]-[实施例29]绿光有机电致发光器件(空穴传输层)
用实施例2-8和表1记载的物质作为空穴传输材料替代实施例1中的化合物2以外，其他同实施例1同样的方法制备有机电致发光器件。
[比较例1]-[比较例3]
采用与实施例1的同样方法制备有机电致发光器件，其中[比较例1]中用比较化合物1替代化合物2、[比较例2]中用比较化合物2替代化合物2、[比较例3]中用比较化合物3替代化合物2。
Figure BDA0002403064260000181
本发明的实施例1-实施例29，比较例1-比较例3制备的有机电致发光器件加偏压以后用Photoresearch公司的PR-650测试电致发光特性(EL)，在5000cd/m2基准亮度下，用Mcscience制备的寿命装备测试T95。测定结果如表2表示。
表2
Figure BDA0002403064260000182
Figure BDA0002403064260000191
由上述表1的结果能确认使用本发明提供的芴类化合物作为空穴材料的有机电致发光器件表现出高的发光效率及长寿命，特别是：本发明的芴类化合物适用在空穴层时候，与比较化合物1(NPB)比能明显提高效率和寿命。
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 (7)

1.一种芴类化合物，其特征在于，其结构式如下：
Figure FDA0002403064250000011
式中，Ar1和Ar2各自独立地为取代或未取代的C1-C30烷基、取代或未经取代的C1-C30烷基氨基、取代或非取代的C6-C30芳基氨基、取代或未取代的苯基、取代或未取代的C10-C30稠环芳基、或取代或未取代的3元到30元杂芳基；
R1、R2、R3、R4各自独立地选自氢、或氢的同位素；
R5、R6、R7各自独立地选自氢、氢的同位素、卤素、氰基、羧基、硝基、羟基、磺酸基、磷酸基、硼烷基、取代或未取代的硅基、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、取代或未经取代的C6-C30芳基、取代或未经取代的3元到30元杂芳基、取代或未经取代的C1-C30烷氧基、取代或未经取代的C1-C30烷基氨基、取代或未经取代的C1-C30芳基氨基、取代或未经取代的C1-C30芳氧基、或取代或未经取代的C1-C30芳硫基；
R5、R6、R7取代基的位置为在所在苯环的任意位置，R5、R6的个数为0～4，R7的个数为0～5，且R5、R6、R7不能同时为氢或者氢的同位素。
2.根据权利要求1所述的芴类化合物，其特征在于，Ar1和Ar2各自独立地选自萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯基、9,9二甲基-9H-芴基、或9,9二苯基-9H-芴基中的一种。
3.根据权利要求1所述的芴类化合物，其特征在于，R5、R6、R7各自独立地选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基中的一种。
4.根据权利要求1所述的芴类化合物，其特征在于，其为下述结构中的任意一个：
Figure FDA0002403064250000021
Figure FDA0002403064250000031
Figure FDA0002403064250000041
Figure FDA0002403064250000051
Figure FDA0002403064250000061
5.一种权利要求1-4任意一项所述的芴类化合物的制备方法，其特征在于，包括以下步骤：
化合物C的合成
向反应容器里按顺序加入化合物B和四氢呋喃溶剂，在氮气气氛下使所述容器冷却到-78℃；接着将正丁基锂逐滴添加到混合物中；在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃；此后，将溶解于四氢呋喃中的化合物A逐滴添加到混合物中；添加后，使反应温度升温到室温，并且搅拌混合物16小时；反应结束以后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，有机层用硫酸镁干燥以后的浓缩产品用柱色谱法纯化，得到化合物C；
目标化合物的合成
向反应容器里加入化合物C、化合物D、二氯甲烷，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中，室温下反应；反应结束以后用二氯甲烷和水提取有机物，有机层用硫酸镁干燥以后的浓缩产品用柱色谱法纯化，得到目标化合物；其合成路线如下：
Figure FDA0002403064250000071
式中，Ar1、Ar2、R5～R7与上述范围相同；Hal为卤素；R8与R1～R4范围相同。
6.一种由权利要求1-4任意一项所述的芴类化合物制备的有机电致发光器件。
7.根据权利要求6所述的有机电致发光器件，其特征在于，所述芴类化合物是作为空穴传输层材料。
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CN111793002A (zh) * 2020-07-23 2020-10-20 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机电致发光器件
CN111960953A (zh) * 2020-08-26 2020-11-20 长春海谱润斯科技有限公司 一种含有芴的芳胺化合物及其有机电致发光器件
CN113387871A (zh) * 2021-06-11 2021-09-14 长春海谱润斯科技股份有限公司 三芳胺衍生物及其有机电致发光器件
WO2022004994A1 (ko) * 2020-06-30 2022-01-06 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20220048180A (ko) * 2020-10-12 2022-04-19 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자
CN114751832A (zh) * 2022-06-14 2022-07-15 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物、其制备方法及应用

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WO2022004994A1 (ko) * 2020-06-30 2022-01-06 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN111793002A (zh) * 2020-07-23 2020-10-20 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机电致发光器件
CN111960953A (zh) * 2020-08-26 2020-11-20 长春海谱润斯科技有限公司 一种含有芴的芳胺化合物及其有机电致发光器件
CN111960953B (zh) * 2020-08-26 2021-10-15 长春海谱润斯科技股份有限公司 一种含有芴的芳胺化合物及其有机电致发光器件
KR20220048180A (ko) * 2020-10-12 2022-04-19 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자
WO2022080715A1 (ko) * 2020-10-12 2022-04-21 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자
CN116057040A (zh) * 2020-10-12 2023-05-02 株式会社Lg化学 新型化合物及包含其的有机发光器件
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CN113387871A (zh) * 2021-06-11 2021-09-14 长春海谱润斯科技股份有限公司 三芳胺衍生物及其有机电致发光器件
CN114751832A (zh) * 2022-06-14 2022-07-15 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物、其制备方法及应用

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