CN109369420A - 一种含有七元环的有机芳香胺类发光材料 - Google Patents

一种含有七元环的有机芳香胺类发光材料 Download PDF

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CN109369420A
CN109369420A CN201811318996.5A CN201811318996A CN109369420A CN 109369420 A CN109369420 A CN 109369420A CN 201811318996 A CN201811318996 A CN 201811318996A CN 109369420 A CN109369420 A CN 109369420A
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layer
compound
aromatic amine
organic
heptatomic ring
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池胜华
房平磊
张世才
崔丽莎
程大兴
刘凯
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JIUMU CHEMICAL PRODUCT CO Ltd YANTAI
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JIUMU CHEMICAL PRODUCT CO Ltd YANTAI
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Abstract

本发明涉及一种含有七元环的有机芳香胺类发光材料，属于有机光电材料技术领域，以含有七元环的有机芳香胺为核心结构的有机化合物作为发光层或电子传输层材料用于OLED器件上。本发明具有较好的分子稳定性，制备出的OLED器件具备优越的光电性能，具有较高的热稳定性、较低的驱动电压和较高的效率，可延长器件的使用寿命，满足器件制造商的要求的优点。

Description

一种含有七元环的有机芳香胺类发光材料
技术领域
本发明涉及一种含有七元环的有机芳香胺类发光材料，属于有机光电材料技术领域，尤其涉及一种以三苯并环庚烯为中心结构的有机化合物材料及其在OLED发光显示器或照明器件的应用。
背景技术
有机电致发光(Organic Light Emitting Diode，简称OLED)，与液晶显示器相比，具有亮度高、体积薄、响应迅速、性能稳定、对比度高、宽视角、全彩色、工作温度范围宽等优点，很有希望替代现有的液晶显示和荧光灯照明，应用前景十分优越。
OLED器件的基本结构类似于“三明治”，包括一与电力正极相连的铟锡氧化物(ITO)，一金属阴极，以及被正极与阴极夹在中间的功能结构层。比较基础的，在结构层中会包括有空穴传输层(HTL)、发光层(EML)和电子传输层(ETL)，当电力供应至适当电压时，来自空穴传输层的正极空穴与来自电子传输层的阴极电荷就会在发光层中结合，产生光亮，即产生OLED电致发光。
形成结构层的有机功能材料可分为荧光材料和磷光材料两种，第一代的OLED是仅利用单重态激子发光的荧光发射材料，但其理论上的内量子效率只有25％；第二代的OLED是包含贵金属的磷光发射材料，通过贵金属与其配体间的自旋轨道耦合可综合利用25％的单重态和75％的三重态，内量子效率可达100％，但由于金属价格高昂、材料稳定性较差、使用寿命短、器件效率滚落严重、蓝光磷光薄弱等问题限制了应用；第三代的OLED是在2009年日本九州大学的Adachi教授发现的基于三线态-单线态跃迁的热激活延迟荧光(ThermallyActivated Delayed Fluorescence，简称TADF)新材料而发展的，该类材料具有小的单线态-三线态能级差(△EST)，可使75％的三重态激子通过逆系间穿越到单线态上发射出荧光，由此可同时利用生成概率25％的单重态激子和75％的三重态激子以获得高的发光效率，其内量子效率同样可达100％。
虽然目前的OLED器件中也有对第三代TADF材料的研究，但多数仍集中在器件的驱动电压、发光效率、使用寿命等性能优化方面，然而在面对面板制造企业提出的更高要求上，OLED材料现有的发展存在着很大的差距，尤其是对于第三代的TADF材料，因此，研制出发光效率高、发光层成膜性好、使用寿命长等更高性能的OLED发光材料成为了迫切需求。
发明内容
为解决以上技术上的不足，本发明提供了一种含有七元环的有机芳香胺类发光材料，具有较好的分子稳定性，制备出的OLED器件具备优越的光电性能，具有较高的热稳定性、较低的驱动电压和较高的效率，可延长器件的使用寿命，满足器件制造商的要求。
本发明的技术方案如下：一种含有七元环的有机芳香胺类发光材料，其特征在于：包括通式(1)所示的化合物，
通式(1)
通式(1)中，Ar1、Ar2为苯、联苯、菲中的一种；Ar3为苯、联苯、菲、芴、萘、咔唑、呋喃、噻吩、吡嗪、哒嗪、吡啶、咪唑、吲哚中的一种。
本发明的技术方案还包括：所述Ar3分别为：
本发明的技术方案还包括：所述化合物的分子结构式为：
此外，本发明还提供了含有七元环的有机芳香胺类化合物在有机电致发光器件中的用途。
另一方面，本发明还提供了一种有机电致发光器件，包括阳极层、阴极层和至少一层功能层，所述功能层中至少有一层包括所述含有七元环的有机芳香胺类化合物。
本发明还提供了一种有机电致发光器件，包括电子传输层，所述电子传输层为包括所述含有七元环的有机芳香胺类化合物。
本发明还提供了一种有机电致发光器件，包括发光层，所述发光层包括所述含有七元环的有机芳香胺类化合物。
本发明的有益效果是：设计了以三苯并环庚烯为核心的化合物，作为电子受体，可利于电子在发光层中的传输。此外，七元环骨架与芳香基团形成共轭结构使其空间位阻大，从而使得本发明化合物结构更加稳定，上述材料作为OLED发光器件的独立的空穴注入材料，单独的空穴传输材料或者空穴注入传输材料使用时，器件驱动电压能够明显降低，表明其有良好的空穴注入和空穴传输能力；同时，器件的发光效率，功率效率和外量子效率均得到很大改善；对于器件寿命提升非常明显。上述材料具有良好的应用效果，具有良好的产业化前景。
附图说明
图1是本发明的OLED器件结构示意图。
图中，1、透明基板层，2、ITO阳极层，3、空穴注入层(HIM)，4、空穴传输层(HTL)，5、发光层(EML)，6、电子传输层(ETL)，7、电子注入层，8、阴极反射电极层。
具体实施方式
以下通过实施例对本发明作进一步说明。
实施例1：化合物2的合成
500ml三口瓶，在通氮气的情况下，加入3.28g镁片(134mmol)，室温下，配制原料A40g(141mol)、THF 160g溶液，向三口瓶中加入少量配制液，使液面刚刚没过镁片，料加毕，搅拌升温，升温至64℃时，引发反应，降温至55℃-65℃，开始滴加原料A/THF溶液，控温55℃-65℃保温2h，TLC检测原料反应完毕；降温至室温，水解，用甲苯萃取，水洗，过硅胶柱，脱干溶剂，用甲苯重结晶，得35g白色中间体A，收率76.5％，纯度99.1％。三苯并环庚烯酮与原料A的摩尔比为1.1:1，原料A与镁片的摩尔比为1:0.95。
500ml三口瓶，在通氮气的情况下，加入35g化合物中间体A(104mmol)、25.7g原料B，加入350g二氯乙烷，控温0～10℃滴加三氟化硼乙醚溶液(BF3·Et2O 105g，3倍于中间体A)，滴毕，控温0～10℃保温，保温3h TLC检测原料反应完毕，水解，水洗，过硅胶柱，脱干溶剂，用甲苯重结晶得39g，收率66.3％，纯度99.9％。中间体A、原料B的摩尔比为1:1。
HPLC-MS：化合物2理论分子量为561.71，实际检测结果分子量为561.2。
实施例2：化合物14的合成
在氮气保护下，依次称取30g原料C(177mmol)、37.8g原料D(177mmol)、42.6g叔丁醇钠(443mmol)、0.40g Pd(OAc)2(1.77mmol)、1.55g C10104R3(3.54mmol)，用甲苯搅拌混合，加热至70～75℃，回流反应2～3小时，取样点板，显示无原料C剩余；自然冷却至室温，水洗，过硅胶柱，用甲苯精制，烘干得到43g中间体B，收率：80.4％，HPLC：99.6％。原料C、原料D、叔丁醇钠的摩尔比为1:1:2.5。
500ml三口瓶，在通氮气的情况下，加入30g化合物中间体A(90mmol)、27.1g中间体B，加入300g二氯乙烷，控温0～10℃滴加三氟化硼乙醚溶液(BF3·Et2O90g，3倍于中间体A)，滴毕，控温0～10℃保温，保温5h TLC检测原料反应完毕，水解，水洗，过硅胶柱，脱干溶剂，用甲苯重结晶得37g，收率66.7％，纯度99.9％。中间体A、中间体B的摩尔比为1:1。
HPLC-MS：化合物14理论分子量为617.8，实际检测结果分子量为617.2。
实施例3：化合物47的合成
在氮气保护下，依次称取30g原料C(177mmol)、70.5g原料E(177mmol)、42.6g叔丁醇钠(443mmol)、0.40g Pd(OAc)2(1.77mmol)、1.55g C10104R3(3.54mmol)，用甲苯搅拌混合，加热至70～75℃，回流反应3～5小时，取样TLC检测显示无原料C剩余；自然冷却至室温，水洗，过硅胶柱，用甲苯精制，烘干得到55g中间体C，收率：63.9％，HPLC：99.8％。原料C、原料E、叔丁醇钠的摩尔比为1:1:2.5。
500ml三口瓶，在通氮气的情况下，加入30g化合物中间体A(90mmol)、43.6g中间体C(90mmol)，加入300g二氯乙烷，控温0～10℃滴加三氟化硼乙醚溶液(BF3·Et2O 150g，5倍于中间体A)，滴毕，控温0～10℃保温，保温7h TLC检测原料反应完毕，水解，水洗，过硅胶柱，脱干溶剂，用DMF重结晶得34.2g，收率53.3％，纯度99.9％。中间体A、中间体C的摩尔比为1:1。
HPLC-MS：化合物47理论分子量为802.01，实际检测结果分子量为801.34。
实施例4：化合物83的合成
在氮气保护下，依次称取30g原料C(177mmol)、42.6g叔丁醇钠(443mmol)、0.40gPd(OAc)2(1.77mmol)、1.55g C10104R3(3.54mmol)，用甲苯搅拌混合，加热至70～75℃，滴加52.68g原料F(173mmol)的THF溶液，回流反应2～3小时，取样TLC检测显示无原料C剩余；自然冷却至室温，水洗，过硅胶柱，用甲苯精制，烘干得到30g中间体D，收率：43.2％，HPLC：99.6％。原料C、原料F、叔丁醇钠的摩尔比为1:0.98:2.5。
500ml三口瓶，在通氮气的情况下，加入25g化合物中间体A(75mmol)、29.3g中间体D，加入250g二氯乙烷，控温0～10℃滴加三氟化硼乙醚溶液(BF3·Et2O125g，5倍于中间体A)，滴毕，控温0～10℃保温，保温8h TLC检测原料反应完毕，水解，水洗，过硅胶柱，脱干溶剂，用DMF重结晶得27g，收率51.0％，纯度99.9％。中间体A、中间体D的摩尔比为1:1。
HPLC-MS：化合物83理论分子量为707.90，实际检测结果分子量为707.32。
实施例5：化合物86的合成
在氮气保护下，依次称取30g原料C(177mmol)、34.9g原料G(177mmol)、42.6g叔丁醇钠(443mmol)、0.40g Pd(OAc)2(1.77mmol)、1.55g C10104R3(3.54mmol)，用二甲苯搅拌混合，加热至120～130℃，回流反应5～7小时，取样TLC检测显示无原料C剩余；自然冷却至室温，水洗，过硅胶柱，用THF精制，烘干得到31.6g中间体E，收率：62.5％，HPLC：99.9％。原料C、原料G、叔丁醇钠的摩尔比为1:1:2.5。
500ml三口瓶，在通氮气的情况下，加入30g化合物中间体A(90mmol)、25.6g中间体E(90mmol)，加入300g二氯乙烷，控温0～10℃滴加三氟化硼乙醚溶液(BF3·Et2O 150g，5倍于中间体A)，滴毕，控温0～10℃保温，保温10h TLC检测原料反应完毕，水解，水洗，过硅胶柱，脱干溶剂，用DMF重结晶得26.0g，收率48.3％，纯度99.9％。中间体A、中间体E的摩尔比为1:1。
HPLC-MS：化合物86理论分子量为601.73，实际检测结果分子量为601.34。
下面通过应用实施例1～5详细说明本发明合成的化合物在OLED器件上的应用效果。
对比例1
对比例1中，对具有透明基板层1的透明电极层2(透明电极层2的膜厚215nm)进行光刻和蚀刻，形成规则的透明电极层2的图形，玻璃透明基板层1依次进行碱洗、高纯水洗涤，干燥后再对透明电极层2表面进行UV-臭氧洗涤去除有机残留物。洗涤后，对透明基板层1的阳极进行蒸镀(钼坩锅、蒸镀速度0.1nm/s、真空度约5.0*10-5Pa)，蒸镀下述结构式(1)所示有机化合物作为空穴类材料，制作膜厚为60nm，该层作为空穴注入层3：
在空穴注入层3上，通过真空蒸镀装置(钼坩埚、蒸镀速度0.1nm/s，真空度约5.0*10-5Pa)，蒸镀结构式(2)有机化合物作为空穴传输层4使用，其膜厚为10nm。
器件的发光层5是将结构式(3)化合物蒸镀在空穴传输层4之上(钼坩埚、蒸镀速度0.1nm/s，真空度约5.0*10-5Pa)。
电子传输层6是在发光层5上，通过蒸镀装置(钼坩埚、蒸镀速度0.1nm/s，真空度约5.0*10-5Pa)，将结构式(4)化合物作为电子传输材料蒸镀到发光层上面，制作出膜厚度为25nm的电子传输层。
电子注入层7为膜厚1nm的氟化锂(LiF)层，此层通过真空蒸镀装置(钼坩埚、蒸镀速度0.1nm/s，真空度约5.0*10-5Pa)蒸镀制备。
反射电极层8为膜厚140nm的铝(Al)层，此层通过真空蒸镀装置(BN坩埚、蒸镀速度0.1nm/s，真空度约5.0*10-5Pa)蒸镀制备。
器件制作完成后，用公知的驱动电路将阳极和阴极连接起来，利用辉度测定仪(株式会社TOPCON制，商品名BM7)测量器件的发光效率，发光光谱以及器件的电流-电压特性。
本发明的应用例1～5器件的制作工艺与对比例1相同，使用相同的基板和电极材料，同时保证电极材料的膜厚度相同，不同之处仅将发光层或电子传输材料分别换成本发明材料，对比例1和应用例1～5所制作的器件各主要结构层所用化合物如表1所示：
表1
对比例1和应用例1～5所制作的OLED发光器件的结果如表2所示。
表2
由表2分析得出，采用本发明有机化合物作为OLED发光材料制备的发光器件，与现应用的OLED发光器件相比，器件驱动电压能够明显降低，表明其有良好的空穴注入能力；此外，器件的发光效率及外量子效率均得到很大改善；对于器件寿命提升非常明显。具有良好的工业化前景。
以上所述，仅是本发明的较佳实施例，并非对本发明做任何形式上的限制，凡在本发明的精神和原则之内所做任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。

Claims (7)

1.一种含有七元环的有机芳香胺类发光材料，其特征在于：包括通式(1)所示的化合物，
通式(1)中，Ar1、Ar2为苯、联苯、菲中的一种；Ar3为苯、联苯、菲、芴、萘、咔唑、呋喃、噻吩、吡嗪、哒嗪、吡啶、咪唑、吲哚中的一种。
2.如权利要求1所述的一种含有七元环的有机芳香胺类发光材料，其特征在于：所述Ar3分别为：
3.如权利要求1所述的一种含有七元环的有机芳香胺类发光材料，其特征在于所述化合物的分子结构式为：
4.如权利要求1至3中任一化合物在有机电致发光器件中的用途。
5.一种有机电致发光器件，其特征在于：包括阳极层、阴极层和至少一层功能层，所述功能层中至少有一层包括权利要求1至3中任一项的化合物。
6.一种有机电致发光器件，其特征在于：包括电子传输层，所述电子传输层为权利要求1至3中任一项的化合物。
7.一种有机电致发光器件，其特征在于：包括发光层，所述发光层包括权利要求1至3中任一项的化合物。
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CN111471453A (zh) * 2019-11-19 2020-07-31 吉林奥来德光电材料股份有限公司 有机电致发光化合物及其制备方法和有机电致发光器件
CN111471453B (zh) * 2019-11-19 2024-05-28 吉林奥来德光电材料股份有限公司 有机电致发光化合物及其制备方法和有机电致发光器件
CN113912471A (zh) * 2021-10-21 2022-01-11 上海八亿时空先进材料有限公司 蒽衍生物、有机电致发光材料、发光装置及消费型产品
CN113912471B (zh) * 2021-10-21 2022-04-01 上海八亿时空先进材料有限公司 蒽衍生物、有机电致发光材料、发光装置及消费型产品
WO2023065996A1 (zh) * 2021-10-21 2023-04-27 上海八亿时空先进材料有限公司 蒽衍生物、有机电致发光材料、发光装置及消费型产品

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