CN107721805A - 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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CN107721805A
CN107721805A CN201711089106.3A CN201711089106A CN107721805A CN 107721805 A CN107721805 A CN 107721805A CN 201711089106 A CN201711089106 A CN 201711089106A CN 107721805 A CN107721805 A CN 107721805A
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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，驱动电压最低达到3.6V，发光效率达到40.6cd/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C6-C50芳硫醚、取代或未取代的C5-C50杂芳基中的一种；L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C5-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si和P中的至少一种；
n为1或2。
优选的，n为2。
优选的，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C6-C30芳硫醚、取代或未取代的C5-C30杂芳基中的一种。
优选的，L选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芴基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芘基、取代或未取代的基、取代或未取代的芴基、取代或未取代的二苯基并噻吩、取代或未取代的二苯基并呋喃、取代或未取代的二甲基芴、取代或未取代的二苯基芴、取代或未取代的吩噻嗪、取代或未取代的吩噁嗪、取代或未取代的呋喃基、取代或未取代的噻吩基、取代或未取代的吖啶、取代或未取代的三苯胺、取代或未取代的咔唑、取代或未取代的苯基咔唑、取代或未取代的二萘嵌苯。
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。
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。
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C6-C50芳硫醚、取代或未取代的C5-C50杂芳基中的一种；L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C5-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si和P中的至少一种；
n为1或2。
优选的，n为2。
优选的，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C6-C30芳硫醚、取代或未取代的C5-C30杂芳基中的一种。
优选的，L选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芴基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芘基、取代或未取代的基、取代或未取代的芴基、取代或未取代的二苯基并噻吩、取代或未取代的二苯基并呋喃、取代或未取代的二甲基芴、取代或未取代的二苯基芴、取代或未取代的吩噻嗪、取代或未取代的吩噁嗪、取代或未取代的呋喃基、取代或未取代的噻吩基、取代或未取代的吖啶、取代或未取代的三苯胺、取代或未取代的咔唑、取代或未取代的苯基咔唑、取代或未取代的二萘嵌苯。
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C6-C50芳硫醚、取代或未取代的C5-C50杂芳基中的一种；L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C5-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si和P中的至少一种；
n为1或2。
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任一种有机电致发光材料。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。
Step1.取100mmol 1,4-苯二硼酸，200mmol 3-溴-9-芴酮，300mmol碳酸钾，1mmol四三苯基膦鈀，甲苯、乙醇、水混合溶剂溶解，氮气置换三次，升温到回流反应3小时。反应完成后，旋干溶剂，过柱层析得到产品1-1 80mmol。
Step2.取80mmol 1-1，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 60mmol。总收率60％。
实施例2：化合物2的制备
合成方法同实施例1，将1,4-苯二硼酸替换为1,3-苯二硼酸。
实施例3：化合物7的制备
合成方法同实施例2，将苯硼酸替换为(4-(9H-咔唑基)苯基)苯硼酸。
实施例4：化合物10的制备
合成方法同实施例1，将苯硼酸替换为9,9-二甲基-9H-芴硼酸。
实施例5：化合物18的制备
合成方法同实施例1，将1,4-苯二硼酸替换为蒽-9,10-二硼酸。
实施例6：化合物25的制备
同实施例5，将苯硼酸替换为9,9-二甲基-9H-芴硼酸。
实施例7：化合物27的制备
同实施例5，将苯硼酸替换为4-吡啶硼酸。
实施例8：化合物51的制备
Step1.取100mmol N,N-二苯基苯-1,4-二胺，200mmol 3-溴-9-芴酮，300mmol碳酸钾，1mmolPd2(dba)3，甲苯溶剂溶解，氮气置换三次，加入4mmol三叔丁基膦，升温到回流反应3小时。反应完成后，旋干溶剂，过柱层析得到产品51-1 80mmol。
Step2.取80mmol 51-1，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51 60mmol。总收率60％。
将Step2.中苯硼酸替换为(4-(9H-咔唑基)苯基)苯硼酸。
实施例10：化合物105的制备
Step1.取100mmol蒽硼酸，100mmol 3-溴-9-芴酮，300mmol碳酸钾，1mmol四三苯基膦鈀，甲苯、乙醇、水混合溶剂溶解，氮气置换三次，升温到回流反应3小时。反应完成后，旋干溶剂，过柱层析得到产品105-1 80mmol。
Step2.取80mmol 105-1，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(9-苯基-9H-咔唑基-3-yl)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10560mmol。总收率60％。
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
1 M/z:558.41，C44H30(558.23)
2 M/z:558.54，C44H30(558.23)
7 M/z:888.25，C68H44N2(888.35)
10 M/z:790.13，C62H46(790.36)
18 M/z:658.42，C52H34(658.27)
25 M/z:890.27，C70H50(890.39)
27 M/z:660.36，C50H32N2(660.26)
51 M/z:740.05，C56H40N2(740.32)
57 M/z:1053.2，C80H51N3(1053.41)
105 M/z:583.38，C45H29N(583.23)
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，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。
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:客体掺杂然后蒸镀电子传输层阴极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化合物1:客体掺杂5％的然后蒸镀电子传输层阴极LiFAl上述过程有机物蒸镀速度是保持LiF是Al是
应用实例2：
将应用实施例1中的化合物1换成化合物2。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7。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10。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18。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25。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27。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51。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1换成化合物57。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1换成化合物105。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 (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C6-C50芳硫醚、取代或未取代的C5-C50杂芳基中的一种；L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C5-C50杂芳基中的一种；
所述杂芳基中的杂原子为B、N、O、S、Si和P中的至少一种；
n为1或2。
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，n为2。
3.根据权利要求1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C6-C30芳硫醚、取代或未取代的C5-C30杂芳基中的一种。
4.根据权利要求1所述的一种有机电致发光材料，L选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芴基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芘基、取代或未取代的基、取代或未取代的芴基、取代或未取代的二苯基并噻吩、取代或未取代的二苯基并呋喃、取代或未取代的二甲基芴、取代或未取代的二苯基芴、取代或未取代的吩噻嗪、取代或未取代的吩噁嗪、取代或未取代的呋喃基、取代或未取代的噻吩基、取代或未取代的吖啶、取代或未取代的三苯胺、取代或未取代的咔唑、取代或未取代的苯基咔唑、取代或未取代的二萘嵌苯。
5.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：
6.一种有机发光器件，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5中所述的任一种有机电致发光材料。
7.根据权利要求6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5中所述的任一种有机电致发光材料。
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WO2024167188A1 (ko) * 2023-02-06 2024-08-15 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

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KR20190139404A (ko) * 2018-06-08 2019-12-18 주식회사 트리엘 신규한 유기발광소자용 화합물 및 이를 포함하는 유기막 재료용 코팅액 조성물
KR102140677B1 (ko) 2018-06-08 2020-08-03 주식회사 트리엘 신규한 유기발광소자용 화합물 및 이를 포함하는 유기막 재료용 코팅액 조성물
WO2020045904A1 (ko) * 2018-08-31 2020-03-05 주식회사 엘지화학 유기 발광 소자용 잉크 조성물
US11377570B2 (en) 2018-08-31 2022-07-05 Lg Chem, Ltd. Ink composition for organic light emitting device
US11760764B2 (en) 2020-05-22 2023-09-19 Aligos Therapeutics, Inc. Methods and compositions for targeting PD-L1
WO2024167188A1 (ko) * 2023-02-06 2024-08-15 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

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