CN105418357A - 一种苯并螺芴化合物及其在oled上的应用 - Google Patents

一种苯并螺芴化合物及其在oled上的应用 Download PDF

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CN105418357A
CN105418357A CN201510811465.XA CN201510811465A CN105418357A CN 105418357 A CN105418357 A CN 105418357A CN 201510811465 A CN201510811465 A CN 201510811465A CN 105418357 A CN105418357 A CN 105418357A
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benzo
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oled
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spiral shell
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CN105418357B (zh
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李崇
王立春
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

本发明公开了一种苯并螺芴化合物及其在OLED上的应用，本发明化合物以螺芴结构为中心骨架，可作为发光层或电子传输层材料应用于OLED器件。本发明化合物作为功能材料应用于OLED可以提升器件的发光效率，延长使用寿命。

Description

一种苯并螺芴化合物及其在OLED上的应用
技术领域
本发明涉及电致发光材料，尤其是涉及一种以螺芴为骨架的螺芴系化合物及其在OLED领域的应用。
背景技术
有机电致发光(OLED:OrganicLightEmissionDiodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。
OLED发光器件犹如三明治的结构，包括电极材料膜层，以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件，当对OLED发光器件的两端电极施加电压，并通过电场作用有机层功能材料膜层中正负电荷，正负电荷进一步在发光层中复合，即产生OLED电致发光。
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展，但是，和实际的产品应用要求相比，OLED器件的发光效率，使用寿命等性能还需要进一步提升。
对于OLED发光器件提高性能的研究包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能OLED的功能材料。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类，即电荷注入传输材料和发光材料，进一步，还可将电荷注入传输材料分为电子注入传输材料和空穴注入传输材料，还可以将发光材料分为主体发光材料和掺杂材料。为了制作高性能的OLED发光器件，要求各种有机功能材料具备良好的光电特性，譬如，作为电荷传输材料，要求具有良好的载流子迁移率，高玻璃化转化温度等，作为发光层的主体材料要求材料具有良好双极性，适当的HOMO/LUMO能阶等。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构，产业上应用的OLED器件结构，则包括空穴注入层、空穴传输层、发光层、电子注入层等多种膜层，也就是说应用于OLED器件的光电功能材料至少包含空穴注入材料，空穴传输材料，发光材料，电子注入材料等，材料类型和搭配形式具有丰富性和多样性的特点。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现，也可能完全迥异。
因此，针对当前OLED器件的产业应用要求，以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合，具有高性能的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。就当前OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料的开发显得尤为重要。
发明内容
针对现有技术存在的上述问题，本发明提供了一种苯并螺芴化合物及其在OLED上的应用。将本发明化合物作为功能材料应用于OLED可以提升器件的发光效率，延长使用寿命。
本发明的技术方案如下：
一种以通式(Ⅰ)和/或(Ⅱ)所示结构为骨架的苯并螺芴化合物，所述通式(Ⅰ)和通式(Ⅱ)为：
其中，Ar1、Ar2通过C-C键或C-N键连接于结构的外侧；Ar1、Ar2分别为取代或未取代的苯基、萘基、菲基、荧蒽基、苯并蒽基、苯基萘基、联苯基、三联苯基、芘基、9，9-二甲基芴基、苯并9,9-二甲基芴基、二苯并呋喃基、苯并萘并呋喃基、二苯并噻吩基、苯并萘并噻吩基、邻二氮杂菲基、苯基吡啶基、苯基喹啉基、萘基吡啶基、二苯基苯并咪唑基、N-甲基咔唑基、N-苯基咔唑基、N-甲基苯并咔唑基、N-苯基苯并咔唑基、9，9-二苯基芴基、螺二芴基、二甲基茚并咔唑基、苯基苯并噻唑基、苯基苯并恶唑基、二吡啶喹喔啉基、二苯基喹喔啉基或苯基吲哚并咔唑基。
所述Ar1、Ar2分别选自：
中的任一种结构；Ar1与Ar2为两种不同的取代基。
该化合物结构式为：
一种包含所述苯并螺芴化合物的发光器件，所述化合物做作为OLED器件的发光层或者电子传输层，应用于OLED显示器以及OLED照明。
本发明有益的技术效果在于：
1.本发明化合物所应用的OLED器件在电场作用下，所产生的电致发光颜色可列举出不同色彩，即为红绿蓝等单独的特定色彩光，或者多种不同色彩光的组合光；
2.本发明化合物所应用的OLED器件可应用于PM驱动OLED显示，AM驱动OLED显示，或OLED照明领域。
附图说明
图1为本发明OLED器件结构示意图；
其中，1透明基板；2透明电极；3空穴注入层；4空穴传输层；5发光层；6电子传输层；7电子注入层；8反射电极。
具体实施方式
下面结合附图和实施例，对本发明进行具体描述。
实施例1：化合物D的合成：
氮气保护下向100mL三口瓶中加入2.65g(0.01mol)1-溴-2-萘甲酸甲酯，1.87g(0.012mol)对氯苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应8h，降至室温后加入20mL乙酸乙酯，20mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到灰白色固体2.42g，即为中间体A，收率82％；
将2.42g(0.008mol)中间体A加入三口瓶中，然后再加入80mL浓硫酸，室温搅拌1.5h，将反应液缓慢倒到冰水中，有白色固体析出，抽滤得白色固体2.64g，即为中间体B，收率45％；
氮气保护下向250mL三口瓶中加入0.29g(0.012mol)镁带，80mL四氢呋喃，一小勺碘，升温至45℃，将2.56g(0.011mol)2-溴联苯溶于20mL四氢呋喃后30min滴加到三口瓶中，保温反应2h，将中间体B2.64g(0.01mol)溶于30mL四氢呋喃中滴加到上述格氏试剂中，升温至60℃反应4h，降至室温后加入饱和氯化铵溶液淬灭反应，加入100mL乙酸乙酯，分液萃取，水洗有机相，有机相旋干后加入到三口瓶中，再加入100mL冰乙酸，2mL浓盐酸，回流反应2h，降至室温后有白色固体析出，抽滤得3.4g白色固体，即为中间体C，收率85％；
向100mL三口瓶中加入3.4g(0.0085mol)中间体C，1.58g(0.009)NBS，50mL二氯甲烷，回流反应6h，降至室温后加入30mL饱和亚硫酸钠溶液，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到浅黄色固体3.08g，即为产物D，收率76％。
元素分析结构：分子式C29H16BrCl，HPLC-MS：材料分子量为479.65，实际分子量479.79。
实施例2：化合物G的合成：
氮气保护下向100mL三口瓶中加入2.49g(0.01mol)2-溴-5-氯苯甲酸甲酯，3g(0.012mol)6-溴-2-萘硼酸，0.15g(2×10-4mol)Pd(PPh3)2Cl2，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应8h，降至室温后加入20mL乙酸乙酯，20mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到灰白色固体2.36g，即为中间体E收率63％；
将2.36g(0.0063mol)中间体E加入三口瓶中，然后再加入50mL浓硫酸，室温搅拌1.5h，将反应液缓慢都到冰水中，有白色固体析出，抽滤得白色固体3.43g，即为中间体F，收率42％；
氮气保护下向250mL三口瓶中加入0.29g(0.012mol)镁带，80mL四氢呋喃，一小勺碘，升温至45℃，将2.56g(0.011mol)2-溴联苯溶于20mL四氢呋喃后30min滴加到三口瓶中，保温反应2h。将中间体F3.43g(0.01mol)溶于30mL四氢呋喃中滴加到上述格氏试剂中，升温至60℃反应4h，降至室温后加入饱和氯化铵溶液淬灭反应，加入100mL乙酸乙酯，分液萃取，水洗有机相，有机相旋干后加入到三口瓶中，再加入100mL冰乙酸，2mL浓盐酸，回流反应2h，降至室温后有白色固体析出，抽滤得2.33g白色固体，即为产物G，收率65％。
元素分析结构：分子式C29H16BrCl，HPLC-MS：材料分子量为479.83，实际分子量479.79。
实施例3：化合物A1的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例1中制备的化合物D，1.72g(0.01mol)2-萘硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应8h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体4.26g中间体，收率81％；
将4.26g(0.008mol)中间体加入三口瓶中，再加入1.98g(0.008mol)4-(1-萘基)苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体A14.66g，收率84％。
元素分析结构:分子式C55H34，HPLC-MS：材料分子量为695.12，实际分子量694.86。
实施例4：化合物A2的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例1中制备的化合物D，2.48g(0.01mol)4-(1-萘基)苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体5.12g中间体，收率85％；
将5.12g(0.0085mol)中间体加入三口瓶中，再加入1.46g(0.0085mol)2-萘硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体A24.84g，收率82％。
元素分析结构:分子式C55H34，HPLC-MS：材料分子量为695.12，实际分子量694.86。
实施例5：化合物B1的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例1中制备的化合物D，2.88g(0.01mol)5-硼酸-7,7-二甲基苯并芴，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体5.14g中间体，收率80％；
将5.14g(0.008mol)中间体加入三口瓶中，再加入1.37g(0.008mol)1-萘硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体B14.76g，收率81％。
元素分析结构:分子式C58H38，HPLC-MS：材料分子量为735.15，实际分子量734.92。
实施例6：化合物C1的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例1中制备的化合物D，1.22g(0.01mol)苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体4.10g中间体，收率86％；
将4.10g(0.0086mol)中间体加入三口瓶中，再加入2.13g(0.0086mol)4-(2-萘基)苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体C14.71g，收率85％。
元素分析结构:分子式C51H32，HPLC-MS：材料分子量为644.97，实际分子量644.80。
实施例7：化合物D1的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例1中制备的化合物D，2.87g(0.01mol)3-硼酸-9-苯基咔唑，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体5.64g中间体，收率88％；
将5.64g(0.0088mol)中间体加入三口瓶中，再加入1.51g(0.0088mol)1-萘硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体D15.16g，收率80％。
元素分析结构:分子式C57H35N，HPLC-MS：材料分子量为734.05，实际分子量733.89。
实施例8：化合物E1的合成
氮气保护下向100mL三口瓶中加入4.78g(0.01mol)实施例2中制备的化合物G，1.99g(0.01mol)4-(3-吡啶基)-苯硼酸，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后加入50mL乙酸乙酯，50mL水，分液萃取，水洗有机相，有机相旋干后，通过柱层析分离得到固体4.70g中间体，收率85％；
将4.70g(0.0085mol)中间体加入三口瓶中，再加入2.67g(0.0085mol)1-苯基-2-(4-硼酸苯基)苯并咪唑，0.23g(2×10-4mol)Pd(PPh3)4，4.14g(0.03mol)无水碳酸钾，30mL甲苯，30mL甲醇，10mL水，回流反应12h，降至室温后直接过滤，滤干后滤饼分别用50ml乙醇和50ml水淋洗，抽干后滤饼倒入单口烧瓶中用500ml二氯甲烷溶解，过硅胶柱子，洗脱液旋干，得到白色固体E15.59g，收率85％。
元素分析结构:分子式C59H37N3，HPLC-MS：材料分子量为788.11，实际分子量787.95。
下面通过应用例1～6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
对具有透明基板层1的透明电极层2(透明电极层2的膜厚为220nm)进行光刻和蚀刻，形成所需的规则的透明电极层2的图形，随即对上述玻璃透明基板层1进行洗涤，即依次进行碱洗涤、纯水洗涤、干燥后再进行紫外线-臭氧洗涤以清除透明电极层2表面的有机残留物；
在进行了上述洗涤之后的透明基板层1的阳极上，利用真空蒸镀装置(钼坩埚、蒸镀速度0.1nm/s、真空度约5.0x10-5Pa)，蒸镀下列结构式(1)所示的化合物作为空穴类材料的NPB、制作膜厚为60nm的层，此层为空穴注入层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5.0x10-5Pa)，蒸镀下列结构式(2)所示的化合物TCTA作为空穴传输层4使用，其膜厚为10nm；
接着上述空穴传输层4之上，结构式(3)所示的化合物作为主体材料的MAND，与作为蓝光掺杂材料的DSA-Ph[即结构式(4)所示的化合物]掺杂共蒸，DSA-Ph掺杂MAND的掺杂浓度为5％的重量比，其膜厚为25nm，这层有机材料作为器件的发光层5使用；
在上述发光层上，通过真空蒸镀装置(Mo坩埚、蒸镀速度0.1nm/s、真空度5.0×10-5Pa)，蒸镀下式所示的作为电子传输性材料的Bphen即式(5)所示的化合物，制作膜厚为30nm的电子传输层6；
在电子传输层6上，通过真空蒸镀装置(Mo坩埚，蒸镀速度0.1nm/s、真空度约5.0×10-5Pa)，制作膜厚为1nm的氟化锂(LiF)层，此层为电子注入层7；
在电子注入层7上，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)，制作膜厚为150nm的铝(Al)层，此层为反射电极层8使用。
按照上述方式完成OLED发光器件后，用公知的驱动电路将阳极和阴极连接起来，测量器件的发光效率，发光光谱以及器件的电流-电压特性。上述器件发光特性的测量是利用辉度测定器(株式会社TOPCON制，商品名BM7)进行的。
应用例1～6
本发明所述应用例1～6为采用本发明合成化合物作为OLED器件中发光层或传输层材料的应用，与对比例1相比，应用例1～6所述器件的制作工艺完全相同，并且所采用了相同的基板材料和电极材料，电极材料的膜厚也保持一致，所不同的是对器件中所使用的部分材料进行了一些调整，应用例中发光层或电子传输层材料分别换成了本发明材料，对比例1和应用例1～6所制作的器件各主要结构层所用化合物如表1所示。对比例1和应用例1～6所制作的OLED发光器件的结果如表2所示。
表1
表2
由表2的结果可以看出，采用本发明化合物作为OLED材料制备的OLED发光器件，对比既存材料应用的OLED发光器件，器件的发光效率，器件的色纯度等性能均有良好的表现；从以上数据应用来看，本发明所述化合物在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。

Claims (4)

1.一种以通式(Ⅰ)和/或(Ⅱ)所示结构为骨架的苯并螺芴化合物，其特征在于所述通式(Ⅰ)和通式(Ⅱ)为：
其中，Ar1、Ar2通过C-C键或C-N键连接于结构的外侧；Ar1、Ar2分别为取代或未取代的苯基、萘基、菲基、荧蒽基、苯并蒽基、苯基萘基、联苯基、三联苯基、芘基、9，9-二甲基芴基、苯并9,9-二甲基芴基、二苯并呋喃基、苯并萘并呋喃基、二苯并噻吩基、苯并萘并噻吩基、邻二氮杂菲基、苯基吡啶基、苯基喹啉基、萘基吡啶基、二苯基苯并咪唑基、N-甲基咔唑基、N-苯基咔唑基、N-甲基苯并咔唑基、N-苯基苯并咔唑基、9，9-二苯基芴基、螺二芴基、二甲基茚并咔唑基、苯基苯并噻唑基、苯基苯并恶唑基、二吡啶喹喔啉基、二苯基喹喔啉基或苯基吲哚并咔唑基。
2.根据权利要求1所述的苯并螺芴化合物，其特征在于所述Ar1、Ar2分别选自：
中的任一种结构；Ar1与Ar2为两种不同的取代基。
3.根据权利要求1所述的苯并螺芴化合物，其特征在于该化合物结构式为：
4.一种包含权利要求1～3任一项所述苯并螺芴化合物的发光器件，其特征在于所述化合物做作为OLED器件的发光层或者电子传输层，应用于OLED显示器以及OLED照明。
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WO2018008718A1 (ja) * 2016-07-07 2018-01-11 保土谷化学工業株式会社 ベンゾアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子
CN108264456A (zh) * 2016-12-30 2018-07-10 湖北尚赛光电材料有限公司 2,8-二溴屈的合成方法及其合成中间体
WO2018146894A1 (ja) * 2017-02-09 2018-08-16 学校法人関西学院 有機電界発光素子
WO2019076709A1 (en) * 2017-10-19 2019-04-25 Basf Se NOVEL SUBSTITUTED BENZONAPHTHATHIOPHENES COMPOUNDS FOR ORGANIC ELECTRONIC ELEMENTS
CN109704913A (zh) * 2018-12-27 2019-05-03 瑞声科技（南京）有限公司 一种螺芴化合物及其应用
WO2019085684A1 (zh) * 2017-11-03 2019-05-09 江苏三月光电科技有限公司 一种含有氰基苯或者硫氰基苯的化合物及其在有机电致发光器件上的应用
CN109824684A (zh) * 2017-11-23 2019-05-31 江苏三月光电科技有限公司 一种螺芴衍生物类有机化合物及其在有机电致发光器件上的应用
CN112479904A (zh) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 一种以茚并蒽衍生物为核心的有机化合物及其应用
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JPWO2018008718A1 (ja) * 2016-07-07 2019-04-18 保土谷化学工業株式会社 ベンゾアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子
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CN106432158A (zh) * 2016-09-19 2017-02-22 江苏三月光电科技有限公司 一种有机发光化合物材料及其应用
CN106432260A (zh) * 2016-09-19 2017-02-22 江苏三月光电科技有限公司 一种有机发光材料及其在oled上的应用
CN108264456A (zh) * 2016-12-30 2018-07-10 湖北尚赛光电材料有限公司 2,8-二溴屈的合成方法及其合成中间体
CN110249442A (zh) * 2017-02-09 2019-09-17 学校法人关西学院 有机电场发光元件
JPWO2018146894A1 (ja) * 2017-02-09 2019-11-21 学校法人関西学院 有機電界発光素子
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WO2018146894A1 (ja) * 2017-02-09 2018-08-16 学校法人関西学院 有機電界発光素子
JP7113455B2 (ja) 2017-02-09 2022-08-05 学校法人関西学院 有機電界発光素子
WO2019076709A1 (en) * 2017-10-19 2019-04-25 Basf Se NOVEL SUBSTITUTED BENZONAPHTHATHIOPHENES COMPOUNDS FOR ORGANIC ELECTRONIC ELEMENTS
US11355715B2 (en) 2017-10-19 2022-06-07 Clap Co., Ltd. Substituted benzonaphthathiophene compounds for organic electronics
CN109748821A (zh) * 2017-11-03 2019-05-14 江苏三月光电科技有限公司 一种含有氰基苯或者硫氰基苯的化合物及其在有机电致发光器件上的应用
WO2019085684A1 (zh) * 2017-11-03 2019-05-09 江苏三月光电科技有限公司 一种含有氰基苯或者硫氰基苯的化合物及其在有机电致发光器件上的应用
CN109748821B (zh) * 2017-11-03 2021-03-30 中节能万润股份有限公司 一种含有氰基苯或者硫氰基苯的化合物及其在有机电致发光器件上的应用
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CN109824684B (zh) * 2017-11-23 2021-03-23 中节能万润股份有限公司 一种螺芴衍生物类有机化合物及其在有机电致发光器件上的应用
US11296290B2 (en) 2018-03-07 2022-04-05 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
US11690236B2 (en) 2018-03-07 2023-06-27 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
CN109704913A (zh) * 2018-12-27 2019-05-03 瑞声科技（南京）有限公司 一种螺芴化合物及其应用
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CN112479904B (zh) * 2019-09-11 2023-04-07 江苏三月科技股份有限公司 一种以茚并蒽衍生物为核心的有机化合物及其应用

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