CN108218664A - 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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CN108218664A
CN108218664A CN201810091063.0A CN201810091063A CN108218664A CN 108218664 A CN108218664 A CN 108218664A CN 201810091063 A CN201810091063 A CN 201810091063A CN 108218664 A CN108218664 A CN 108218664A
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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。本发明提供的有机电致发光材料结构中含有的结构，

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。
目前来看，红光和绿光的发光材料由于其性能优秀，已经在商业上有所应用，而蓝光材料的宽能隙和高热稳定性，是一对矛盾，因此性能优异的蓝光材料较为缺乏。对于常用的蒽类荧光蓝光材料，发光效率较低；而对于Firpic等磷光蓝光材料来说，寿命又较低。因此，如何设计新的性能更好的蓝光材料，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独立的选自氢、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C3-C30杂芳基、取代或未取代的C18-C30三苯基硅基、取代或未取代的C12-C30二苯基膦、取代或未取代的C6-C30苯基砜基中的一种，并且R1、R2不同时为氢。
所述的芳基选自苯基、萘基、蒽基、菲基、苯并菲基、基、芘基、荧蒽基、苝基中的任一种。
优选的，所述的杂芳基选自咔唑基、咔唑并吲哚基、二苯并呋喃基、二苯并噻吩基、二苯并二氧噻吩基、吩噻嗪基、二氧化吩噻嗪基、吩噁嗪基、吖啶基、二甲基吖啶、二苯基吖啶、二苯并哌啶基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噁二唑基、噻二唑基、三氮唑基、吲哚基、喹啉基、异喹啉基、菲罗啉基中的任一种。
优选的，所述的有机电致发光材料，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第一电极与所述第二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有机电致发光材料。
优选的，所述有机化合物层包括发光层，所述发光层中含有所述有机电致发光材料。
优选的，所述有机化合物层包括电子传输层，所述电子传输层中含有本发明所述的有机电致发光材料。
本发明的有益效果：
本发明提供的有机电致发光材料结构中含有的结构，是和蒽、菲、芴等常见的主体结构，有着较高的三线态能级，但本身易于结晶，通过连接其他芳基或杂芳基基团，增加分子的体积，有效避免了结晶。此外，分子中通过连接砜、膦氧、硅等基团，有效地打断了共轭结构，三线态能级更高，HOMO与LOMO之间的能垒更大，更有利于作为蓝色发光材料使用；此外，连接砜、膦氧等基团还有利于电子的传输，使得载流子传输平衡。降低了驱动电压。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蓝色发光材料使用，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独立的选自氢、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C3-C30杂芳基、取代或未取代的C18-C30三苯基硅基、取代或未取代的C12-C30二苯基膦、取代或未取代的C6-C30苯基砜基中的一种，R1、R2不同时为氢。
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，例如可选自咔唑基、咔唑并吲哚基、二苯并呋喃基、二苯并噻吩基、二苯并二氧化噻吩基、吩噻嗪基、二氧化吩噻嗪基、吩噁嗪基、吖啶基、二甲基吖啶基、二苯基吖啶基、二苯并哌啶基、吡啶基、嘧啶基、哒嗪基、吡嗪基、喹啉基、三嗪基、噁二唑基、噻二唑基、三氮唑基、吲哚基、菲罗啉基、异喹啉基，但不限于此。
所述的苯基砜基是指磺酰基借助硫与一个苯基碳原子连结为特征的一类一价基团的有机化合物。
所述的二苯基膦氧基是指膦酰基借助磷原子与二个苯基碳原子连结为特征的一类一价基团的有机化合物。
所述的三苯基硅基是指三个苯基取代亚硅基中的氢原子所构成的基团。
所述取代基是指有机化合物基团除去一个或几个-H而形成的基团，如甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、苯并菲基、基、芘基、荧蒽基、苝基、甲苯基、甲氧基、甲硫基、苯氧基、苯硫基、芴基、9,9-二甲基芴基、9,9-二苯基芴基、二苯胺基、二甲胺基、咔唑基、咔唑并吲哚基、苯基取代咔唑基、二苯并呋喃基、二苯并噻吩基、二苯并二氧噻吩基、氰基、氟基、氘基、二苯基氧膦基、苯基砜基、苯基亚砜基、三苯基硅基、三甲基硅基、吩噻嗪基、吩噁嗪基、吖啶基、二甲基吖啶、二苯基吖啶、二苯并哌啶基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噁二唑基、噻二唑基、三氮唑基、联苯基、三联苯基、吲哚基、茚基、菲罗啉基、喹啉基、异喹啉基、硝基等，但不限于此。
优选的，所述的芳基的选自苯基、萘基、蒽基、菲基、苯并菲基、基、芘基、荧蒽基、苝基中的一个。
优选的，所述的杂芳基选自取代或未取代的咔唑基、咔唑并吲哚基、二苯并呋喃基、二苯并噻吩基、二苯并二氧噻吩基、吩噻嗪基、二氧化吩噻嗪基、吩噁嗪基、吖啶基、二甲基吖啶、二苯基吖啶、二苯并哌啶基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噁二唑基、噻二唑基、三氮唑基、吲哚基、喹啉基、异喹啉基、菲罗啉基、芴基、二甲基芴基、二苯基芴基、茚基中的一个。
优选的，所述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：
1,6-二溴通过suzuki或者buchward反应生成目标产品。
其中，R1、R2独立的选自氢、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C3-C30杂芳基、取代或未取代的C18-C30三苯基硅基、取代或未取代的C12-C30二苯基膦、取代或未取代的C6-C30苯基砜基中的一种，R1、R2不同时为氢。
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至少一种本发明所述的有机电致发光材料。所述有机化合物层优选包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层，优选所述的发光层或电子传输层中含有本发明所述的有机电致发光材料。
实施例1：化合物1的制备
将6-溴100mmol加入到甲苯、乙醇、水的混合溶剂中，氮气保护下加入1当量的9-蒽硼酸，3当量的碳酸钠，0.01当量的四三苯基膦鈀，回流温度下反应5h，反应完成后过硅胶柱，得到产品1 85mmol。
实施例2：化合物4的制备
在反应容器中加入4-1 100mmol；6-溴100mmol，叔丁醇钾300mmol，Pd2(dba)31mmol，超声除氧的二甲苯，搅拌溶解，置换空气三次，加入配体三叔丁基磷4％(4mmol，50％m/V)，再次置换空气三次，回流反应6h。冷却至室温，加入足量二氯甲烷使得产品完全溶解，过少量硅胶漏斗，除掉催化剂和盐。滤液浓缩至粘稠状，过柱层析，得到产品4 80mmol。
实施例3：化合物14的制备
同实施例1，将Step1.中的9-蒽硼酸替换为9,9-二苯基-3-溴芴。
实施例4：化合物20的制备
同实施例1，将Step1.中的9-蒽硼酸替换为9-苯基-3-溴咔唑。
实施例5：化合物46的制备
取100mmol 6-溴加入无水THF溶解，降温到-78℃，加入1.5当量的正丁基锂，在该温度下反应2小时，加入1.5当量的三苯基氯硅烷，逐步升温到室温，反应1小时。反应完成后加入，去离子水，有机相用EtOAc萃取、有机相干燥、浓缩、过柱层析，得到产品46 60mmol。收率60％。
实施例6：化合物60的制备
Step1.在反应容器中加入二苯胺100mmol；6，12-二溴100mmol，叔丁醇钾300mmol，Pd2(dba)3 1mmol，超声除氧的二甲苯，搅拌溶解，置换空气三次，加入配体三叔丁基磷4％(4mmol，50％m/V)，再次置换空气三次，回流反应6h。冷却至室温，加入足量二氯甲烷使得产品完全溶解，过少量硅胶漏斗，除掉催化剂和盐。滤液浓缩至粘稠状，过柱层析，得到产品51-1 80mmol。
Step2.取51-1 80mmol，加入无水THF溶解，降温到-78℃，加入1.5当量的正丁基锂，在该温度下反应2小时，加入1.5当量的硼酸三甲脂，逐步升温到室温，反应1小时。反应完成后加入，去离子水，有机相用EtOAc萃取、有机相干燥、浓缩、过柱层析，得到产51-260mmol。收率60％。
Step3.取对51-2 60mmol，加入1当量的二苯基氧膦，碳酸钾1当量，NiBr0.2当量，超声除氧的二氯乙烷，搅拌溶解，置换空气三次，加入吡啶0.3当量，再次置换空气三次，回流反应24h。冷却至室温，过少量硅胶漏斗，除掉催化剂和盐。滤液浓缩至粘稠状，过柱层析，得到产品60 30mmol。
实施例7：化合物67的制备
将3，6-二溴-9-苯基咔唑100mmol加入到甲苯、乙醇、水的混合溶剂中，氮气保护下加入2当量的硼酸，3当量的碳酸钠，0.01当量的四三苯基膦鈀，回流温度下反应5h，反应完成后过硅胶柱，得到产品67 85mmol。
实施例8：化合物74的制备
取6，12-二硼酸100mmol，加入2当量的二苯基氧膦，碳酸钾1当量，NiBr 0.2当量，超声除氧的二氯乙烷，搅拌溶解，置换空气三次，加入吡啶0.3当量，再次置换空气三次，回流反应24h。冷却至室温，过少量硅胶漏斗，除掉催化剂和盐。滤液浓缩至粘稠状，过柱层析，得到产品74 70mmol。
实施例9：化合物75的制备
Step1.取6,12-二溴100mmol，加入2当量的苯硫醇，3当量叔丁醇钾，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75mmol化合物75-1。
Step2.75mmol化合物75-1，溶解于DCM中，冷却到0摄氏度，加入3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7540mmol。
实施例10：化合物76的制备
在反应容器中加入200mmol咔唑；6，12-二溴100mmol，叔丁醇钾300mmol，Pd2(dba)3 1mmol，超声除氧的二甲苯，搅拌溶解，置换空气三次，加入配体三叔丁基磷4％(4mmol，50％m/V)，再次置换空气三次，回流反应6h。冷却至室温，加入足量二氯甲烷使得产品完全溶解，过少量硅胶漏斗，除掉催化剂和盐。滤液浓缩至粘稠状，过柱层析，得到产品7675mmol。
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TPT-1蒸镀空穴传输层NPB蒸镀发光层材料ADN：5％DPAP-DPPA然后蒸镀电子传输层Alq3 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TPT-1蒸镀空穴传输层NPB蒸镀发光层材料CBP：5％化合物1然后蒸镀电子传输层Alq3 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：
将实施例1中的化合物1更改为化合物4。
应用实例3：
将实施例1中的化合物1更改为化合物14。
应用实例4：
将实施例1中的化合物1更改为化合物20。
应用实例5：
将实施例1中的化合物1更改为化合物46。
应用实例6：
将实施例1中的化合物1更改为化合物60。
应用实例7：
将实施例1中的化合物1更改为化合物67。
应用实例8：
将实施例1中的化合物1更改为化合物76。
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
对比应用实施例2：
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TPT-1蒸镀空穴传输层NPB蒸镀发光层材料CBP：5％DPAVBi然后蒸镀电子传输层Alq3 阴极LiFAl上述过程有机物蒸镀速度是保持LiF是Al是
应用实例9：
在已经准备好的ITO透明电极上依次蒸镀空穴注入层TPT-1蒸镀空穴传输层NPB蒸镀发光层材料CBP：5％DPAVBi然后蒸镀电子传输层化合物74阴极LiFAl上述过程有机物蒸镀速度是保持LiF是Al是
应用实例10：
将实施例9中的化合物74更改为化合物75。
测量实施例2：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3中：
表3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 (7)

1.一种有机电致发光材料，其结构通式如I所示：
其中，R1、R2独立的选自氢、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C3-C30杂芳基、取代或未取代的C18-C30三苯基硅基、取代或未取代的C12-C30二苯基膦、取代或未取代的C6-C30苯基砜基中的一种，并且R1、R2不同时为氢。
2.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，所述的芳基选自苯基、萘基、蒽基、菲基、苯并菲基、基、芘基、荧蒽基、苝基中的任一种。
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，所述的杂芳基选自咔唑基、咔唑并吲哚基、二苯并呋喃基、二苯并噻吩基、二苯并二氧噻吩基、吩噻嗪基、二氧化吩噻嗪基、吩噁嗪基、吖啶基、二甲基吖啶、二苯基吖啶、二苯并哌啶基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噁二唑基、噻二唑基、三氮唑基、吲哚基、喹啉基、异喹啉基、菲罗啉基中的任一种。
4.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：
5.一种有机发光器件，包括第一电极、第二电极和置于所述第一电极与所述第二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4任一项中所述的有机电致发光材料。
6.根据权利要求5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，所述发光层中含有如权利要求1至4任一项中所述的有机电致发光材料。
7.根据权利要求5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电子传输层，所述电子传输层中含有如权利要求1至4任一项中所述的有机电致发光材料。
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CN110467914A (zh) * 2018-05-10 2019-11-19 北京大学深圳研究生院 一种热激活延迟荧光材料及其制备方法、oled器件
CN110746425A (zh) * 2019-10-21 2020-02-04 清华大学 一种新型有机化合物及其应用
CN111253393A (zh) * 2020-02-05 2020-06-09 北京大学 长寿命三线态激子限域材料及其在oled器件中的应用
CN113166088A (zh) * 2018-12-20 2021-07-23 默克专利有限公司 用于电子器件的材料
WO2022177288A1 (ko) * 2021-02-16 2022-08-25 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
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CN110467914A (zh) * 2018-05-10 2019-11-19 北京大学深圳研究生院 一种热激活延迟荧光材料及其制备方法、oled器件
CN110467914B (zh) * 2018-05-10 2023-09-05 北京大学深圳研究生院 一种热激活延迟荧光材料及其制备方法、oled器件
CN113166088A (zh) * 2018-12-20 2021-07-23 默克专利有限公司 用于电子器件的材料
JP7553009B2 (ja) 2019-04-05 2024-09-18 三星ディスプレイ株式會社 有機電界発光素子及び有機電界発光素子用化合物
CN110746425A (zh) * 2019-10-21 2020-02-04 清华大学 一种新型有机化合物及其应用
CN111253393A (zh) * 2020-02-05 2020-06-09 北京大学 长寿命三线态激子限域材料及其在oled器件中的应用
CN111253393B (zh) * 2020-02-05 2022-01-25 北京大学 长寿命三线态激子限域材料及其在oled器件中的应用
WO2022177288A1 (ko) * 2021-02-16 2022-08-25 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자

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