CN107652969A - 一种有机电致发光材料及其有机发光器件 - Google Patents

一种有机电致发光材料及其有机发光器件 Download PDF

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CN107652969A
CN107652969A CN201711089075.1A CN201711089075A CN107652969A CN 107652969 A CN107652969 A CN 107652969A CN 201711089075 A CN201711089075 A CN 201711089075A CN 107652969 A CN107652969 A CN 107652969A
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明提供一种有机电致发光材料及其有机发光器件，属于有机光电材料技术领域。本发明的一种有机电致发光材料结构中含有芴的结构，不同于常见的9,9‑二苯基芴或9,9‑二甲基芴，本发明的化合物结构共轭范围较小，三线态能级更高，相对来说载流子传输能力更强。同时通过在结构中引入刚性结构，有效的提高了化合物的玻璃化转化温度，与现有技术相比，可以解决现有技术中有机光电材料发光效率低、驱动电压较高等发光性能差的技术问题。与现有技术相比，本发明一种有机电致发光器件驱动电压最低达到3.6V，发光效率达到48.7cd/A。

Description

一种有机电致发光材料及其有机发光器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种有机电致发光材料及其有机发光器件。
背景技术
有机电致发光是指有机材料在电场作用下，受到电流和电场的激发而发光的现象。有机电致发光二极管(OLED)是利用这种现象实现显示的新一代显示技术。自1987年美国Kodak公司Tang C.W.和Vanslyke S.A.制作了第一个性能优良的有机电致发光器件以来，有机电致发光显示由于其具有的优点引起了人们的极大兴趣。
有机电致发光材料按照技术更新可以分为两代，第一代是荧光材料，其内量子效率最高只能达到25％；第二代是重金属配合物为主要发光材料的磷光显示材料。为了避免效率滚降的问题，通常采用客体材料掺杂在主体材料中的办法。
芴类化合物是一种常用的主体材料，但目前常见的芴类材料其发光性能不理想，表现为发光效率较低，驱动电压较高。如何设计新的性能更好的芴类结构的主体材料，一直是本领域技术人员亟待解决的问题。
发明内容
有鉴于此，本发明的目的在于提供一种有机电致发光材料及其有机发光器件，采用本发明所述有机电致发光材料制备的有机发光器件，具有更高的发光效率，及更低的驱动电压。
本发明首先提供了一种有机电致发光材料，其结构通式如I所示：
其中，R1、R2独立的选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳醚、取代或未取代的C3-C50杂芳基中的一种；
L选自选自取代或未取代的砜基、取代或未取代的膦氧基、取代或未取代的羰基、取代或未取代的C3-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一种。
优选的，所述的一种有机电致发光材料，R1、R2独立的选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种；
L选自如下基团：
R11、R12、R13选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种。
优选的，所述的一种有机电致发光材料，选自如下结构中的任意一种：
本发明还提供一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，至少一个有机化合物层含有所述的任一种有机电致发光材料。
优选的，有机化合物层包括发光层，发光层中含有任一种有机电致发光材料。
本发明的有益效果：
本发明的一种有机电致发光材料结构中含有芴的结构，不同于常见的9,9-二苯基芴或9,9-二甲基芴，本发明的化合物结构共轭范围较小，三线态能级更高，相对来说载流子传输能力更强。同时通过在结构中引入刚性结构，有效的提高了化合物的玻璃化转化温度，与现有技术相比，将其应用于有机发光器件，特别是作为发光层中的主体材料使用，具有相对较高的发光效率和较低的驱动电压。
具体实施方式
下面将结合本发明实施例的技术方案进行清楚、完整地描述，显然，所描述的实施例仅是本发明一部分实施例，而不是全部的实施例。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。
本发明首先提供一种有机电致发光材料，结构通式如I所示：
其中，R1、R2独立的选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳醚、取代或未取代的C5-C50杂芳基中的一种；
L选自选自取代或未取代的砜基、取代或未取代的膦氧基、取代或未取代的羰基、取代或未取代的C3-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一种。
按照本发明，所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后，剩下一价基团的总称，其可以为单环芳基或稠环芳基，例如可选自苯基、联苯基、萘基、蒽基、菲基或芘基等，但不限于此。
所述芳胺是指具有芳香性取代基的胺，即-NH2、-NH-或含氮基团连接到芳香烃上。
所述芳醚是指具有芳香性取代基的醚，即Ar1—O—Ar2或Ar1—O—R，式中Ar1和Ar2为芳香基，R为烷基。
所述杂芳基是指芳香族烃基中的一个或多个芳核碳被杂原子替代得到的基团的总称，所述杂原子包括但不限于氧、硫和氮原子，所述芳族杂环可以为单环或稠环，例如可选自吡啶基、嘧啶基、苯并嘧啶基、咔唑基、三嗪基、苯并噻唑基或苯并咪唑基等，但不限于此。
所述取代基是指取代有机化合物中氢原子的基团除去一个或几个-H而形成称作取代基的基团，如甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、苯并菲基、基、苝基、芘基、苯甲基、甲氧基、甲硫基、苯氧基、苯硫基、芴基、9,9-二甲基芴基、二苯胺基、二甲胺基、咔唑基，9-苯基咔唑基、呋喃基、噻吩基、氰基、氟基、氘基、三苯基硅基、三甲基硅基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、嘧啶基、联苯基、三联苯基、硝基等，但不限于此。
优选的，所述的一种有机电致发光材料，R1、R2独立的选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种；
L选自如下基团：
R11、R12、R13选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种。
所述的一种有机电致发光材料，其特征在于，选自如下结构中的任意一种：
本发明所述一种有机电致发光材料的制备方法，包括所示的原料通过如下路线反应生成式I所示的一种有机电致发光材料：
其中，R1、R2独立的选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳醚、取代或未取代的C3-C50杂芳基中的一种；
L选自选自取代或未取代的砜基、取代或未取代的膦氧基、取代或未取代的羰基、取代或未取代的C3-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一种。
本发明还提供一种有机发光器件，所述有机发光器件为本领域技术人员所熟知的有机发光器件即可。本发明所述有机发光器件包括第一电极、第二电极和置于两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含所述的任一种有机电致发光材料。所述有机化合物层包括发光层，发光层中含有所述的任一种有机电致发光材料。
实施例1：化合物1的制备
Step1.取100mmol 3-溴-9H-芴酮，加入1当量的3-硫醇-9H-芴酮，300mmol叔丁醇钾，1mmol Pd2(dba)3，甲苯，氩气置换三次，加入1mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，粗产品过硅胶柱，得到产品72mmol化合物1-1。
Step2.取72mmol化合物1-1，溶解于DCM中，冷却到0摄氏度，加入2当量的m-CPBA，逐渐升温到室温，搅拌反应6小时，反应完成后，用饱和无水亚硫酸氢钠洗涤，有机相干燥，旋干，得到的产品过硅胶柱，得到目标产品1-250mmol。
Step3.取50mmol 1-2，加入甲苯溶解，加入2.5当量的4-甲基苯磺酰肼，在80℃反应4小时，加入2当量的苯硼酸，和4当量碳酸钾，在回流温度下反应5小时。冷却到室温，用去离子水洗涤溶液，有机相干燥、浓缩、过柱层析，得到产品1 30mmol。总收率30％。
实施例2：化合物6的制备
合成方法同实施例1，将苯硼酸替为：
实施例3：化合物26的制备
Step1.取100mmol l 3-溴-9H-芴酮，加入甲苯溶解，加入1.2当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1.2当量的苯硼酸，和2当量碳酸钾，在回流温度下反应5小时。冷却到室温，用去离子水洗涤溶液，有机相干燥、浓缩、过柱层析，得到产品26-1 80mmol。
Step2.取到产品26-1 80mmol，加入无水THF溶解，降温到-78℃，滴加正丁基锂1.2当量，在此温度下反应1h。再次滴加Ph-PCl2＝O的THF溶液1.2当量，继续搅拌1h。缓慢升温到室温继续反应3h。反应完成后，用去离子水淬灭反应，DCM萃取，干燥，浓缩，得到的粗品过硅胶柱，得到产品26 50mmol。总收率50％
实施例4：化合物33的制备
合成方法同实施例3，将苯硼酸替为:4-吡啶硼酸。
实施例5：化合物45的制备
Step1.取100mmol 3-溴-9H-芴酮，加入甲苯溶解，加入1.2当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1.2当量的苯硼酸，和2当量碳酸钾，在回流温度下反应5小时。冷却到室温，用去离子水洗涤溶液，有机相干燥、浓缩、过柱层析，得到产品26-1 80mmol。
Step2.将产品26-1 80mmol，加入40mmol，四三苯基磷钯0.4mmol，碳酸钾120mmol，甲苯、乙醇、水的混合溶剂，氮气置换三次，回流温度下反应6h。反应完成后，旋干溶剂，过硅胶柱，得到产品45 30mmol。
实施例6：化合物61的制备
Step1.取100mmol芴酮，加入甲苯溶解，加入1.2当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1.2当量的苯硼酸，和2当量碳酸钾，在回流温度下反应5小时。冷却到室温，用去离子水洗涤溶液，有机相干燥、浓缩、过柱层析，得到产品61-1 80mmol。
Step2.将120mmol无水三氯化铝加入反应器中，加入干燥的THF。在15℃下加入160mmol草酰氯，继续滴加61-1 80mmol的二氯甲烷溶液，反应液在室温下搅拌1小时，加入冰水淬灭反应，反应液用DCM萃取，干燥浓缩，粗品过硅胶柱得到产品61 40mmol。
实施例7：化合物66的制备
合成方法同实施例6，将将苯硼酸替为:
实施例8：化合物72的制备
Step1.取100mmol 3-溴-9H-芴酮，加入甲苯溶解，加入1.2当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1.2当量的3-吡啶硼酸，和2当量碳酸钾，在回流温度下反应5小时。冷却到室温，用去离子水洗涤溶液，有机相干燥、浓缩、过柱层析，得到产品72-180mmol。
Step2.在氮气的保护下，取原料产品72-1 80mmol，加入适量的无水THF溶解后，降温到-78℃，滴加正丁基锂100mmol，保温反应0.5小时，快速滴加硼酸三异丙脂100mmol，缓慢升温到室温，反应30min。反应完毕后，反应-液到入稀盐酸水溶液中中，有固体物质析出过滤，粗品过硅胶柱得到产品硼酸72-2 60mmol。
Step3.取硼酸72-2 60mmol，加入0.5当量碳酸钠180mmol，四三苯基磷钯0.6mmol，甲苯，乙醇，水的混合溶剂，氩气置换三次，回流温度下反应5h，反应结束后，加入去离子水，分出有机相，水洗三次，浓缩，得到的粗产品过硅胶柱，得到产品72 22mmol。
本发明实施例制备得到的一种有机电致发光材料的FD-MS值见表1所示。
表1本发明实施例制备的化合物FD-MS值
对比应用实施例1：
将ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30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。
在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀空穴传输层蒸镀发光层主体mCP:客体掺杂Ir(ppy)3 5％然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例1：
在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀空穴传输层蒸镀发光层主体1：客体掺杂Ir(ppy)3 5％然后蒸镀电子传输层阴极上述过程有机物蒸镀速度是保持LiF是Al是
应用实例2：
将应用实施例1中的化合物1换成化合物6。测量该器件的发光性能，结果见表2。
应用实例3：
将应用实施例1中的化合物1换成化合物26。测量该器件的发光性能，结果见表2。
应用实例4：
将应用实施例1中的化合物1换成化合物33。测量该器件的发光性能，结果见表2。
应用实例5：
将应用实施例1中的化合物1换成化合物45。测量该器件的发光性能，结果见表2。
应用实例6：
将应用实施例1中的化合物1换成化合物61。测量该器件的发光性能，结果见表2。
应用实例7：
将应用实施例1中的化合物1换成化合物66。测量该器件的发光性能，结果见表2。
应用实例8：
将应用实施例1中的化合物1换成化合物72。测量该器件的发光性能，结果见表2。
测量实施例1：对比样品以及样品的发光性能
对比样品以及样品是采用Keithley SMU235，PR650评价发光效率和驱动电压，结果列于表2中：
表2本发明实施例制备的发光器件的发光特性
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (5)

1.一种有机电致发光材料，其结构通式如I所示：
其中，R1、R2独立的选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳醚、取代或未取代的C3-C50杂芳基中的一种；
L选自取代或未取代的砜基、取代或未取代的膦氧基、取代或未取代的羰基、取代或未取代的C3-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一种。
2.根据权利要求1所述的一种有机电致发光材料，其中，R1、R2独立的选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种；
L选自如下基团：
R11、R12、R13选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳醚、取代或未取代的C3-C30杂芳基中的一种。
所述杂芳基中的杂原子为B、N、O、S、Si或P中的至少一种。
3.根据权利要求1所述的一种有机电致发光材料，其特征在于，选自如下结构中的任意一种：
4.一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，其特征在于，至少一个有机化合物层含有如权利要求1至3中所述的任一种有机电致发光材料。
5.根据权利要求4中所述的一种有机发光器件，其特征在于，所述有机化合物层包括发光层，发光层中含有如权利要求1至3中所述的任一种有机电致发光材料。
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107759593A (zh) * 2017-11-08 2018-03-06 长春海谱润斯科技有限公司 一种有机电致发光材料及其有机发光器件
CN112010843A (zh) * 2019-05-30 2020-12-01 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物及其应用
WO2021235546A1 (ja) * 2020-05-22 2021-11-25 国立大学法人東海国立大学機構 フルオレニリデン－アクリダン誘導体、フルオレニリデン－アクリダン誘導体の製造方法、メカノクロミズム材料、電荷輸送材料、及び電子デバイス

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107759593A (zh) * 2017-11-08 2018-03-06 长春海谱润斯科技有限公司 一种有机电致发光材料及其有机发光器件
CN112010843A (zh) * 2019-05-30 2020-12-01 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物及其应用
CN112010843B (zh) * 2019-05-30 2022-03-08 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物及其应用
WO2021235546A1 (ja) * 2020-05-22 2021-11-25 国立大学法人東海国立大学機構 フルオレニリデン－アクリダン誘導体、フルオレニリデン－アクリダン誘導体の製造方法、メカノクロミズム材料、電荷輸送材料、及び電子デバイス

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