CN107721806A - 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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CN107721806A
CN107721806A CN201711089116.7A CN201711089116A CN107721806A CN 107721806 A CN107721806 A CN 107721806A CN 201711089116 A CN201711089116 A CN 201711089116A CN 107721806 A CN107721806 A CN 107721806A
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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

本发明提供了一种有机电致发光材料及其有机发光器件，涉及有机光电材料技术领域。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。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，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。

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C3-C50杂芳基中的一种；
R2、R3独立的选自氢、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，R1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C3-C30杂芳基中的一种；
R2、R3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杂芳基中的一种；
优选的，所述的一种有机电致发光材料，所述的杂芳基选自如下结构中的任意一种：
X，Y或者Z有且只有一个选自N原子；
M选自O，S，NR43或者CR44R45；
R21到R45选自氢、取代或未取代的C1-C10的烷基、取代或未取代的C6-C30芳基；
*表示键结位点。
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包含任一种本发明所述有机电致发光材料。
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选自取代或未取代的C6-C50芳基、取代或未取代的C10-C50稠环芳基、取代或未取代的C6-C50芳胺、取代或未取代的C3-C50杂芳基中的一种；
R2、R3独立的选自氢、取代或未取代的C6-C50芳基、取代或未取代的C10-C50稠环芳基、取代或未取代的C6-C50芳胺、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，R1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C3-C30杂芳基中的一种；
R2、R3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杂芳基中的一种。
优选的，所述的一种有机电致发光材料，所述的杂芳基选自如下结构中的任意一种：
X，Y或者Z有且只有一个选自N原子；
M选自O，S，NR43或者CR44R45；
R21到R45选自氢、取代或未取代的C1-C10的烷基、取代或未取代的C6-C30芳基；*表示键结位点。
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
其中，R1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C3-C50杂芳基中的一种；
R2、R3独立的选自氢、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，优选所述的发光层中含有本发明所述的有机电致发光材料。
实施例1：化合物A-3的制备
取100mmol芴酮，加入甲苯溶解，加入1.5当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1当量的2-硼酸-三亚苯，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，萃取合并有机相，有机相干燥、浓缩、过柱层析，得到产品60mmol。收率60％。
实施例2：化合物A-11的制备
合成方法同实施例1，将2-硼酸-三亚苯替换为(4-(二苯基氨基)苯基)硼酸。
实施例3：化合物B-1的制备
合成方法同实施例1，将2-硼酸-三亚苯替换为(4-(9H-咔唑基)苯基)苯硼酸。
实施例4化合物B6的制备
Step1.取100mmol的2-溴吡啶，加入100mmol的(氧-9H-芴基)硼酸，300mmo碳酸钠，0.1mmol四三苯基磷钯，甲苯，乙醇、水的混合溶剂，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品84mmol化合物B-6-2。
Step1.取84mmol化合物B-6-2，加入甲苯溶解，加入1.5当量的4-甲基苯磺酰肼，在80℃反应4小时，加入1当量的(4-(9H-咔唑基)苯基)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50mmol。收率60％。
实施例5：化合物B-9的制备
同实施例4，将Step1.中2-溴吡啶替换为2-氯-4,6-二苯基-1,3,5-三氮唑。
实施例6：化合物B-15的制备
同实施例4，将Step1.中2-溴吡啶替换为3-溴二苯并[b,d]呋喃。
实施例7：化合物B-17的制备
同实施例4，将Step1.中2-溴吡啶替换为2-溴-9-苯基-咔唑。
实施例8：化合物E-9的制备
Step1.将3-溴-9H-芴酮100mmol，加入100mmol的咔唑，300mmol叔丁醇钾，1mmolPd2(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，过柱，得到产品E-9-1，89mmol。
Step2.将产品E-9-1，89mmol，加入溶剂乙醇和甲苯的混合溶剂，加入3当量的雷尼镍和3当量的水合肼。室温搅拌5小时，过滤，滤液浓缩，过柱层析，得到产品E-9-2 60mmol。
Step3.将产品E-9-2 60mmol，加入60mmol的2-溴吡啶，300mmol碳酸铯，5mmol醋酸钯，DMF，氩气置换三次，加入5mmol三环己基膦，再次氩气置换三次，回流温度下反应10h，过柱，得到产品E-9，39mmol。
实施例9化合物E18的制备
Step1.取100mmol的2-溴吡啶，加入100mmol的(氧-9H-芴基)硼酸，300mmo碳酸钠，0.1mmol四三苯基磷钯，甲苯，乙醇、水的混合溶剂，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品84mmol化合物E-18-1。
Step2.将产品E-18-1，84mmol，加入溶剂乙醇和甲苯的混合溶剂，加入3当量的雷尼镍和3当量的水合肼。室温搅拌5小时，过滤，滤液浓缩，过柱层析，得到产品E-18-260mmol。
Step3.将产品E-18-2 60mmol，加入60mmol的2-溴吡啶，300mmol碳酸铯，5mmol醋酸钯，DMF，氩气置换三次，加入5mmol三环己基膦，再次氩气置换三次，回流温度下反应10h，过柱，得到产品E-18，39mmol。
实施例10：化合物O-20的制备
同实施例9，将step1中的2-溴吡啶更换为2-溴-9,9-二甲基芴-9H-芴；将step3中的2-溴吡啶更换为2-溴嘧啶。
实施例11：化合物J-22的制备
同实施例8，将Step3中的2-溴吡啶更换为2-溴嘧啶。
实施例12：化合物J-24的制备
同实施例4，将Step1.中2-溴吡啶替换为3-溴二苯并[b,d]呋喃。将Step2中的(4-(9H-咔唑基)苯基)苯硼酸替换为(9,9-二甲基-9H-芴酮)硼酸。
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
化合物 FD-MS
A-3 M/z:392.27，C31H20(392.16)
A-11 M/z:409.54，C31H23N(409.18)
B-1 M/z:407.25，C31H21N(407.17)
B-6 M/z:484.03，C36H24N2(484.19)
B-9 M/z:638.63，C46H30N4(638.25)
B-15 M/z:573.29，C43H27NO(573.21)
B-17 M/z:648.36，C49H32N2(648.26)
E-9 M/z:408.36，C30H20N2(408.16)
E-18 M/z:320.36，C23H16N2(320.13)
J-22 M/z:436.36，C32H24N2(436.19)
J-24 M/z:409.36，C29H19N3(409.16)
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蒸镀空穴传输层蒸镀发光层A-3: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A-3换成化合物A-11。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A-3换成化合物B-1。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A-3换成化合物B-6。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A-3换成化合物B-9。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A-3换成化合物B-15。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A-3换成化合物B-17。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A-3换成化合物E-9。测量该器件的发光性能，结果见表2。
应用实例9：
将应用实施例1中的化合物A-3换成化合物E-18。测量该器件的发光性能，结果见表2。
应用实例10：
将应用实施例1中的化合物A-3换成化合物J-22。测量该器件的发光性能，结果见表2。
应用实例11：
将应用实施例1中的化合物A-3换成化合物J-24。测量该器件的发光性能，结果见表2。
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蒸镀空穴传输层蒸镀发光层主体mCP:Firpic 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12：
在已经准备好的ITO透明电极上依次蒸镀空穴注入层蒸镀空穴传输层蒸镀发光层A-3:客体掺杂Firpic 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13：
将应用实施例1中的化合物A-3换成化合物A-11。测量该器件的发光性能，结果见表2。
应用实例14：
将应用实施例1中的化合物A-3换成化合物B-1。测量该器件的发光性能，结果见表2。
应用实例15：
将应用实施例1中的化合物A-3换成化合物B-6。测量该器件的发光性能，结果见表2。
应用实例16：
将应用实施例1中的化合物A-3换成化合物B-9。测量该器件的发光性能，结果见表2。
应用实例17：
将应用实施例1中的化合物A-3换成化合物B-15。测量该器件的发光性能，结果见表2。
应用实例18：
将应用实施例1中的化合物A-3换成化合物B-17。测量该器件的发光性能，结果见表2。
应用实例19：
将应用实施例1中的化合物A-3换成化合物E-9。测量该器件的发光性能，结果见表2。
应用实例20：
将应用实施例1中的化合物A-3换成化合物E-18。测量该器件的发光性能，结果见表2。
应用实例21：
将应用实施例1中的化合物A-3换成化合物J-22。测量该器件的发光性能，结果见表2。
应用实例22：
将应用实施例1中的化合物A-3换成化合物J-24。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 (6)

1.一种有机电致发光材料，其结构通式如I所示：
其中，R1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C3-C50杂芳基中的一种；
R2、R3独立的选自氢、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，R1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C3-C30杂芳基中的一种；
R2、R3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杂芳基中的一种。
3.根据权利要求1所述的一种有机电致发光材料，所述的杂芳基选自如下结构中的任意一种：
X，Y或者Z有且只有一个选自N原子；
M选自O，S，NR43或者CR44R45；
R21到R45选自氢、取代或未取代的C1-C10的烷基、取代或未取代的C6-C30芳基；
*表示键结位点。
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包含如权利要求1至4中所述的任一种有机电致发光材料。
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，发光层中包含如权利要求1至4中所述的任一种有机电致发光材料。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109574917A (zh) * 2018-12-03 2019-04-05 武汉尚赛光电科技有限公司 一种芴酮衍生物及其制备和应用
WO2022055321A1 (ko) * 2020-09-14 2022-03-17 주식회사 동진쎄미켐 신규한 캡핑층용 화합물 및 이를 포함하는 유기 발광 소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109574917A (zh) * 2018-12-03 2019-04-05 武汉尚赛光电科技有限公司 一种芴酮衍生物及其制备和应用
WO2022055321A1 (ko) * 2020-09-14 2022-03-17 주식회사 동진쎄미켐 신규한 캡핑층용 화합물 및 이를 포함하는 유기 발광 소자

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