CN112538056A - 一种电子传输材料及包含该材料的有机电致发光器件 - Google Patents
一种电子传输材料及包含该材料的有机电致发光器件 Download PDFInfo
- Publication number
- CN112538056A CN112538056A CN201910892156.8A CN201910892156A CN112538056A CN 112538056 A CN112538056 A CN 112538056A CN 201910892156 A CN201910892156 A CN 201910892156A CN 112538056 A CN112538056 A CN 112538056A
- Authority
- CN
- China
- Prior art keywords
- mol
- electron transport
- compound
- transport material
- organic electroluminescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
技术领域
本发明涉及有机电致发光材料领域,具体涉及一种电子传输材料及包含该材料的有机电致发光器件。
背景技术
有机电致发光器件(Organic Light-emitting Devices,OLED)是利用如下原理的自发性发光器件:当施加电场时,荧光物质通过正极注入的空穴和负极注入的电子的重新结合而发光。这种自发光器件,具有电压低、亮度高、视角宽、响应快、温度适应性好等特性,并且超薄,能制作在柔性面板上等优点,广泛应用于手机、平板电脑、电视和照明等领域。
就当前有机电致发光产业的实际需求而言,目前有机电致发光材料的发展还远远不够,有机电致发光器件市场庞大,因而稳定、高效的有机电子传输材料对有机电致发光器件的应用和推广具有重要作用,同时也是有机电致发光大面积面板显示的应用推广的迫切需求。
有鉴于此,特提出本发明。
发明内容
本发明的首要目的是提供一种电子传输材料;
本发明的第二目的是提供一种有机电致发光器件;
本发明的第三目的是提供一种电子显示设备;
本发明的第四目的是提供一种OLED照明装置。
为了达到上述发明目的,本发明所采用的技术方案如下:
一种电子传输材料,其结构式如下所示:
其中,R1为氟原子、甲氧基、氰基、三氟甲基、三氟苯基、五氟苯基中的任意一种;
Ar为取代或未取代的亚苯基;
R2为取代或未取代的C6-C30的芳香族基团、取代或未取代的C5-C30的杂芳香族基团;
X1、X2、X3各自独立的为CH或N,且X1、X2、X3中至少一个为N。
进一步地,Ar为未取代的亚苯基或稠合取代的亚苯基。
进一步地,R2为萘基、蒽基、菲基、吡啶基、吖啶基、菲啶基、喹啉基、二苯并噻吩基、芴基、氧芴基中的任意一种。
进一步地,所述电子传输材料为以下结构式化合物中的任意一种:
本发明还提供了一种有机电致发光器件,包括阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、阴极,所述电子传输层中含有上述电子传输材料。
进一步地,所述有机电致发光器件中还含有空穴阻挡层,所述空穴阻挡层中含有所述电子传输材料。
本发明还进一步提供了一种含有上述有机电致发光器件的电子显示设备。
本发明还进一步提供了一种含有上述有机电致发光器件的OLED照明装置。
本发明中室温均为25±5℃。
本发明的有益效果:
本发明设计的电子传输材料由于高电子密度的菲基的引入,有效的增加了材料分子的电子云密度,大幅度提高了材料分子的电子迁移速率,进而提高使用该材料作为ETL材料的有机电致发光器件的效率。同时,由于该类材料具有较高的HOMO能级,能够有效的将空穴阻挡在发光层中,大幅度提高了复合激子的效率,进而显著提高有机电致发光器件的发光效率及寿命。
附图说明
图1为本发明提供的有机电致发光器件的结构示意图;
图中标号分别代表:
1-阴极、2-电子注入层、3-电子传输层、4-发光层、5-空穴传输层、6-空穴注入层、7-阳极。
具体实施方式
实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市售购买获得的常规产品。
实施例1:
电子传输材料(1)的制备方法如下:
S1:
将化合物1-a(2,4,6-trichloro-1,3,5-triazine)(10g,182.92g/mol,54.67mmol)、化合物1-b(phenanthren-9-ylboronic acid)(1eq,12.14g,222.09g/mol,54.67mmol)和碳酸钠(2eq,11.59g,105.99g/mol,109.34mmol)加入到乙二醇二胺醚(200g,化合物1-a的20倍质量)和水(200g,化合物1-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.5g,304.37g/mol,1.64mmol)和乙酸钯(II)(0.5%eq,0.061g,224.51g/mol,0.27mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物1-c(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(16.38g,收率92.2%),MS(EI):325(M+)。
S2:
将化合物1-c(16g,325g/mol,49.23mmol)、化合物1-d((4-cyanophenyl)boronicacid)(1eq,7.24g,147.05g/mol,49.23mmol)和碳酸钠(2eq,10.44g,105.99g/mol,98.46mmol)加入到乙二醇二胺醚(320g,化合物1-c的20倍质量)和水(320g,化合物1-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.45g,304.37g/mol,1.48mmol)和乙酸钯(II)(0.5%eq,0.055g,224.51g/mol,0.25mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物1-e(4-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(17.5g,收率90.7%),MS(EI):392(M+)。
S3:
将化合物1-e(17g,392g/mol,43.37mmol)、化合物1-f((4-(naphthalen-1-yl)phenyl)boronic acid)(1eq,10.76g,248.1g/mol,43.37mmol)和碳酸钠(2eq,9.19g,105.99g/mol,86.74mmol)加入到乙二醇二胺醚(340g,化合物1-e的20倍质量)和水(340g,化合物1-e的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.4g,304.37g/mol,1.3mmol)和乙酸钯(II)(0.5%eq,0.049g,224.51g/mol,0.22mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(1)(4-(4-(4-(naphthalen-1-yl)phenyl)-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(21.88g,收率90.1%),MS(EI):560(M+)。
实施例2:
电子传输材料(2)的制备方法如下:
S1:
将化合物2-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物2-b((4-(trifluoromethyl)phenyl)boronic acid)(1eq,5.85g,190.04g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物2-a的20倍质量)和水(200g,化合物2-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物2-c(2-chloro-4-(phenanthren-9-yl)-6-(4-(trifluoromethyl)phenyl)-1,3,5-triazine)(11.86g,收率88.6%),MS(EI):435(M+)。
S2:
将化合物2-c(11g,435g/mol,25.29mmol)、化合物2-d((4-(naphthalen-1-yl)phenyl)boronic acid)(1eq,6.27g,248.1g/mol,25.29mmol)和碳酸钠(2eq,5.36g,105.99g/mol,50.58mmol)加入到乙二醇二胺醚(220g,化合物2-c的20倍质量)和水(220g,化合物2-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.23g,304.37g/mol,0.76mmol)和乙酸钯(II)(0.5%eq,0.028g,224.51g/mol,0.13mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(2)(2-(4-(naphthalen-1-yl)phenyl)-4-(phenanthren-9-yl)-6-(4-(trifluoromethyl)phenyl)-1,3,5-triazine)(13.77g,收率90.3%),MS(EI):603(M+)。
实施例3:
电子传输材料(6)的制备方法如下:
S1:
将化合物3-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物3-b((2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)boronic acid)(1eq,8.86g,288.04g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物3-a的20倍质量)和水(200g,化合物3-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物3-c(2-chloro-4-(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)-6-(phenanthren-9-yl)-1,3,5-triazine)(13.37g,收率81.5%),MS(EI):533(M+)。
S2:
将化合物3-c(13g,533g/mol,24.39mmol)、化合物3-d((4-(naphthalen-1-yl)phenyl)boronic acid)(1eq,6.05g,248.1g/mol,24.39mmol)和碳酸钠(2eq,5.17g,105.99g/mol,48.78mmol)加入到乙二醇二胺醚(260g,化合物3-c的20倍质量)和水(260g,化合物3-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.22g,304.37g/mol,0.73mmol)和乙酸钯(II)(0.5%eq,0.027g,224.51g/mol,0.12mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(6)(2-(4-(naphthalen-1-yl)phenyl)-4-(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)-6-(phenanthren-9-yl)-1,3,5-triazine)(14.94g,收率87.4%),MS(EI):701(M+)。
实施例4:
电子传输材料(9)的制备方法如下:
S1:
将化合物4-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物4-b((4-cyanophenyl)boronic acid)(1eq,4.52g,147.05g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物4-a的20倍质量)和水(200g,化合物4-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物4-c(3-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(11.41g,收率94.6%),MS(EI):392(M+)。
S2:
将化合物4-c(11g,392g/mol,28.06mmol)、化合物4-d((4-(dibenzo[b,d]furan-3-yl)phenyl)boronic acid)(1eq,8.08g,288.1g/mol,28.06mmol)和碳酸钠(2eq,5.95g,105.99g/mol,56.12mmol)加入到乙二醇二胺醚(220g,化合物4-c的20倍质量)和水(220g,化合物4-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.26g,304.37g/mol,0.84mmol)和乙酸钯(II)(0.5%eq,0.031g,224.51g/mol,0.14mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(16)(4-(4-(4-(dibenzo[b,d]furan-3-yl)phenyl)-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(15.19g,收率90.2%),MS(EI):600(M+)。
实施例5:
电子传输材料(16)的制备方法如下:
S1:
将化合物5-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物5-b((3-cyanophenyl)boronic acid)(1eq,4.52g,147.05g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物5-a的20倍质量)和水(200g,化合物5-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物5-c(3-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(11.15g,收率92.4%),MS(EI):392(M+)。
S2:
将化合物5-c(11g,392g/mol,28.06mmol)、化合物5-d((4-(dibenzo[b,d]furan-3-yl)phenyl)boronic acid)(1eq,8.08g,288.1g/mol,28.06mmol)和碳酸钠(2eq,5.95g,105.99g/mol,56.12mmol)加入到乙二醇二胺醚(220g,化合物5-c的20倍质量)和水(220g,化合物5-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.26g,304.37g/mol,0.84mmol)和乙酸钯(II)(0.5%eq,0.031g,224.51g/mol,0.14mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(16)(3-(4-(4-(dibenzo[b,d]furan-3-yl)phenyl)-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(15.46g,收率91.8%),MS(EI):600(M+)。
实施例6:
电子传输材料(35)的制备方法如下:
S1:
将化合物6-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物6-b((4-fluorophenyl)boronic acid)(1eq,4.31g,140.04g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物6-a的20倍质量)和水(200g,化合物6-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物6-c(2-chloro-4-(4-fluorophenyl)-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,收率84.4%),MS(EI):385(M+)。
S2:
将化合物6-c(9g,385g/mol,23.38mmol)、化合物6-d((4-(quinolin-7-yl)phenyl)boronic acid)(1eq,5.82g,249.1g/mol,23.38mmol)和碳酸钠(2eq,4.96g,105.99g/mol,46.76mmol)加入到乙二醇二胺醚(180g,化合物6-c的20倍质量)和水(180g,化合物6-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.21g,304.37g/mol,0.7mmol)和乙酸钯(II)(0.5%eq,0.026g,224.51g/mol,0.12mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(35)(7-(4-(4-(4-fluorophenyl)-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)phenyl)quinoline)(11.04g,收率85.2%),MS(EI):554(M+)。
实施例7:
电子传输材料(57)的制备方法如下:
S1:
将化合物7-a(2,4-dichloro-6-(phenanthren-9-yl)pyrimidine)(10g,324g/mol,30.86mmol)、化合物7-b((2',4',6'-trifluoro-[1,1'-biphenyl]-4-yl)boronicacid)(1eq,7.78g,252.06g/mol,30.86mmol)和碳酸钠(2eq,6.54g,105.99g/mol,61.72mmol)加入到乙二醇二胺醚(200g,化合物7-a的20倍质量)和水(200g,化合物7-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物7-c(4-chloro-2-(phenanthren-9-yl)-6-(2',4',6'-trifluoro-[1,1'-biphenyl]-4-yl)pyridine)(12.79g,收率83.6%),MS(EI):496(M+)。
S2:
将化合物7-c(12g,496g/mol,24.19mmol)、化合物7-d((4-(dibenzo[b,d]furan-3-yl)phenyl)boronic acid)(1eq,6.97g,288.1g/mol,24.19mmol)和碳酸钠(2eq,5.13g,105.99g/mol,48.38mmol)加入到乙二醇二胺醚(240g,化合物7-c的20倍质量)和水(240g,化合物7-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.22g,304.37g/mol,0.73mmol)和乙酸钯(II)(0.5%eq,0.026g,224.51g/mol,0.12mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(57)(2-(4-(dibenzo[b,d]furan-3-yl)phenyl)-4-(phenanthren-9-yl)-6-(2',4',6'-trifluoro-[1,1'-biphenyl]-4-yl)pyrimidine)(15.41g,收率90.5%),MS(EI):704(M+)。
实施例8:
电子传输材料(72)的制备方法如下:
S1:
将化合物8-a(4,6-dichloro-2-(phenanthren-9-yl)pyrimidine)(10g,324g/mol,30.77mmol)、化合物8-b((4-methoxyphenyl)boronic acid)(1eq,4.68g,152.06g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物8-a的20倍质量)和水(200g,化合物8-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物8-c(4-chloro-6-(4-methoxyphenyl)-2-(phenanthren-9-yl)pyrimidine)(11.25g,收率92.3%),MS(EI):396(M+)。
S2:
将化合物8-c(11g,396g/mol,27.28mmol)、化合物8-d((4-(phenanthridin-9-yl)phenyl)boronic acid)(1eq,8.31g,299.11g/mol,27.28mmol)和碳酸钠(2eq,5.78g,105.99g/mol,54.56mmol)加入到乙二醇二胺醚(220g,化合物8-c的20倍质量)和水(220g,化合物8-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.25g,304.37g/mol,0.82mmol)和乙酸钯(II)(0.5%eq,0.031g,224.51g/mol,0.14mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(72)(9-(4-(6-(4-methoxyphenyl)-2-(phenanthren-9-yl)pyrimidin-4-yl)phenyl)phenanthridine)(13.91g,收率82.9%),MS(EI):615(M+)。
实施例9:
电子传输材料(84)的制备方法如下:
S1:
将化合物9-a(4,6-dichloro-2-(phenanthren-9-yl)pyrimidine)(10g,324g/mol,30.77mmol)、化合物9-b((3-cyanophenyl)boronic acid)(1eq,4.52g,147.05g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物9-a的20倍质量)和水(200g,化合物9-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物9-c(3-(6-chloro-2-(phenanthren-9-yl)pyrimidin-4-yl)benzonitrile)(10.76g,收率89.4%),MS(EI):391(M+)。
S2:
将化合物9-c(10g,391g/mol,25.58mmol)、化合物9-d(4-(4-chlorophenyl)dibenzo[b,d]thiophene)(1eq,7.78g,304.07g/mol,25.58mmol)和碳酸钠(2eq,5.42g,105.99g/mol,51.16mmol)加入到乙二醇二胺醚(200g,化合物9-c的20倍质量)和水(200g,化合物9-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.23g,304.37g/mol,0.77mmol)和乙酸钯(II)(0.5%eq,0.029g,224.51g/mol,0.13mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(84)(3-(6-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-2-(phenanthren-9-yl)pyrimidin-4-yl)benzonitrile)(13.8g,收率87.7%),MS(EI):615(M+)。
实施例10:
电子传输材料(94)的制备方法如下:
S1:
将化合物10-a(2,4-dichloro-6-(phenanthren-9-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物10-b((2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)boronic acid)(1eq,8.86g,288.04g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物10-a的20倍质量)和水(200g,化合物10-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物10-c(2-chloro-4-(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)-6-(phenanthren-9-yl)-1,3,5-triazine)(13.46g,收率82.1%),MS(EI):533(M+)。
S2:
将化合物10-c(13g,533g/mol,24.39mmol)、化合物10-d((4-(naphthalen-1-yl)-9H-fluoren-1-yl)boronic acid)(1eq,8.2g,336.13g/mol,24.39mmol)和碳酸钠(2eq,5.42g,105.99g/mol,48.78mmol)加入到乙二醇二胺醚(260g,化合物10-c的20倍质量)和水(260g,化合物10-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.22g,304.37g/mol,0.73mmol)和乙酸钯(II)(0.5%eq,0.027g,224.51g/mol,0.12mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(94)(2-(4-(naphthalen-1-yl)-9H-fluoren-1-yl)-4-(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)-6-(phenanthren-9-yl)-1,3,5-triazine)(14.78g,收率76.8%),MS(EI):789(M+)。
实施例11:
电子传输材料(103)的制备方法如下:
S1:
将化合物11-a(2,4,6-trichloro-1,3,5-triazine)(10g,182.92g/mol,54.67mmol)、化合物11-b(phenanthren-1-ylboronic acid)(1eq,12.14g,222.09g/mol,54.67mmol)和碳酸钠(2eq,11.59g,105.99g/mol,109.34mmol)加入到乙二醇二胺醚(200g,化合物11-a的20倍质量)和水(200g,化合物11-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.5g,304.37g/mol,1.64mmol)和乙酸钯(II)(0.5%eq,0.061g,224.51g/mol,0.27mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物11-c(2,4-dichloro-6-(phenanthren-1-yl)-1,3,5-triazine)(15.92g,收率89.6%),MS(EI):325(M+)。
S2:
将化合物11-c(15g,325g/mol,46.15mmol)、化合物11-d((2-cyanophenyl)boronic acid)(1eq,6.79g,147.05g/mol,46.15mmol)和碳酸钠(2eq,9.78g,105.99g/mol,92.3mmol)加入到乙二醇二胺醚(300g,化合物11-c的20倍质量)和水(300g,化合物11-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.42g,304.37g/mol,1.38mmol)和乙酸钯(II)(0.5%eq,0.052g,224.51g/mol,0.23mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物11-e(2-(4-chloro-6-(phenanthren-1-yl)-1,3,5-triazin-2-yl)benzonitrile)(13.77g,收率76.1%),MS(EI):392(M+)。
S3:
将化合物11-e(13g,392g/mol,33.16mmol)、化合物11-f((4-(dibenzo[b,d]furan-3-yl)naphthalen-1-yl)boronic acid)(1eq,11.21g,338.11g/mol,33.16mmol)和碳酸钠(2eq,7.03g,105.99g/mol,66.32mmol)加入到乙二醇二胺醚(260g,化合物11-e的20倍质量)和水(260g,化合物11-e的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.3g,304.37g/mol,1mmol)和乙酸钯(II)(0.5%eq,0.037g,224.51g/mol,0.17mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(103)(2-(4-(4-(dibenzo[b,d]furan-3-yl)naphthalen-1-yl)-6-(phenanthren-1-yl)-1,3,5-triazin-2-yl)benzonitrile)(15.63g,收率72.5%),MS(EI):650(M+)。
实施例12:
电子传输材料(107)的制备方法如下:
S1:
将化合物12-a(2,4-dichloro-6-(phenanthren-1-yl)-1,3,5-triazine)(10g,325g/mol,30.77mmol)、化合物12-b((4-fluorophenyl)boronic acid)(1eq,4.31g,140.04g/mol,30.77mmol)和碳酸钠(2eq,6.52g,105.99g/mol,61.54mmol)加入到乙二醇二胺醚(200g,化合物12-a的20倍质量)和水(200g,化合物12-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.28g,304.37g/mol,0.92mmol)和乙酸钯(II)(0.5%eq,0.035g,224.51g/mol,0.15mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到化合物12-c(2-chloro-4-(4-fluorophenyl)-6-(phenanthren-1-yl)-1,3,5-triazine)(10.07g,收率85%),MS(EI):385(M+)。
S2:
将化合物12-c(9g,385g/mol,23.38mmol)、化合物12-d((9,9-dimethyl-4-(phenanthren-3-yl)-9H-fluoren-1-yl)boronic acid)(1eq,9.68g,414.18g/mol,23.38mmol)和碳酸钠(2eq,4.96g,105.99g/mol,46.76mmol)加入到乙二醇二胺醚(180g,化合物12-c的20倍质量)和水(180g,化合物12-c的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.21g,304.37g/mol,0.7mmol)和乙酸钯(II)(0.5%eq,0.027g,224.51g/mol,0.12mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(107)(2-(9,9-dimethyl-4-(phenanthren-3-yl)-9H-fluoren-1-yl)-4-(4-fluorophenyl)-6-(phenanthren-1-yl)-1,3,5-triazine)(10.22g,收率60.8%),MS(EI):719(M+)。
实施例13:
电子传输材料(121)的制备方法如下:
将化合物13-a(4-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(10g,392g/mol,25.51mmol)、化合物13-b((4-(quinolin-6-yl)naphthalen-1-yl)boronic acid)(1eq,7.63g,299.11g/mol,25.51mmol)和碳酸钠(2eq,5.41g,105.99g/mol,51.02mmol)加入到乙二醇二胺醚(200g,化合物13-a的20倍质量)和水(200g,化合物13-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.23g,304.37g/mol,0.77mmol)和乙酸钯(II)(0.5%eq,0.029g,224.51g/mol,0.13mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(121)(4-(4-(phenanthren-9-yl)-6-(4-(quinolin-6-yl)naphthalen-1-yl)-1,3,5-triazin-2-yl)benzonitrile)(12.95g,收率83.1%),MS(EI):611(M+)。
实施例14:
电子传输材料(128)的制备方法如下:
将化合物14-a(3-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(10g,392g/mol,25.51mmol)、化合物14-b((4-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)boronic acid)(1eq,9.03g,354.09g/mol,25.51mmol)和碳酸钠(2eq,5.41g,105.99g/mol,51.02mmol)加入到乙二醇二胺醚(200g,化合物14-a的20倍质量)和水(200g,化合物14-a的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.23g,304.37g/mol,0.77mmol)和乙酸钯(II)(0.5%eq,0.029g,224.51g/mol,0.13mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,再经过柱层析提纯后得到电子传输材料(128)(3-(4-(4-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)benzonitrile)(13.32g,收率78.4%),MS(EI):666(M+)。
性能测试:
应用例1:
采用ITO作为反射层阳极基板材料,并依次用水、丙酮、N2等离子对其进行表面处理;
在ITO阳极基板上方,沉积厚度为10nm的HAT-CN形成空穴注入层(HIL);
在空穴注入层(HIL)上方蒸镀NPD形成厚度为120nm的空穴传输层(HTL);
将9,10-Bis(2-naphthyl)anthraces(ADN)作为蓝光主体材料、BD-1作为蓝光掺杂材料(BD-1用量为ADN重量的5%)以不同速率蒸发在空穴传输层(HTL)上形成厚度为20nm的发光层;
将电子传输材料1蒸镀到发光层上得到厚度为35nm的电子传输层(ETL),在电子传输层(ETL)上方蒸镀厚度为2nm的LiQ形成电子注入层(EIL);
此后将镁(Mg)和银(Ag)以9:1的比例混合蒸镀得到厚度为15nm的阴极,在上述阴极封口层上沉积65纳米厚度的DNTPD,此外,在阴极表面以UV硬化胶合剂和含有除湿剂的封装薄膜(seal cap)进行密封,以保护有机电致发光器件不被大气中的氧气或水分所影响至此制备获得有机电致发光器件。
应用例2-14
分别以本发明实施例2-14中的电子传输材料2、6、9、16、35、57、72、84、94、103、107、121、128作为电子传输层(ETL),其他部分与应用例1一致,据此制作出应用例2-14的有机电致发光器件。
对照例1、2
与应用例1的区别在于,使用PBD、p-EtAZ作为电子传输层(ETL),其余与应用例1相同。
上述应用例制造的有机电致发光器件及对照例制造的有机电致发光器件的特性是在电流密度为10mA/cm2的条件下测定的,结果如表1所示。
表1:
由如上表1的实验对比数据可知,采用本发明电子传输材料制备的有机电致发光器件与对照例相比,电压大幅度降低,发光效率显著提高。由此可见,本发明的化合物能使器件的驱动电压大大降低,大幅度减少了电能的消耗、显著提高了发光效率。另外通过降低驱动电压,有机电致发光器件的寿命有显著提高。
分别用光电子发射谱仪(AC-2型PESA)、以及紫外分光光度计(UV759CRT型)测试并计算PBD、p-EtAZ及本发明电子传输材料1、2、6、9、16、35、57、72、84、94、103、107、121、128的最高占据分子轨道HOMO能级及最低占据分子轨道LUMO能级,结果如下表2所示,测试环境为大气环境。
表2:
由上表2可知本发明电子传输材料均具有较大的电子亲和势(LUMO能级)使电子较易由负极注入,而较大的电离能(HOMO能级)可将空穴限制在发光层与电子传输层界面上。
Claims (9)
2.如权利要求1所述的电子传输材料,其特征在于,Ar为未取代的亚苯基或稠合取代的亚苯基。
4.如权利要求1所述的电子传输材料,其特征在于,R2为萘基、蒽基、菲基、吡啶基、吖啶基、菲啶基、喹啉基、二苯并噻吩基、芴基、氧芴基中的任意一种。
6.一种有机电致发光器件,其特征在于,包括阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、阴极,所述电子传输层中含有如权利要求1-5中任一项所述的电子传输材料。
7.如权利要求6所述的有机电致发光器件,其特征在于,所述有机电致发光器件中还含有空穴阻挡层,所述空穴阻挡层中含有所述电子传输材料。
8.一种电子显示设备,其特征在于,含有如权利要求6所述的有机电致发光器件。
9.一种OLED照明装置,其特征在于,含有如权利要求6所述的有机电致发光器件。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910892156.8A CN112538056B (zh) | 2019-09-20 | 2019-09-20 | 一种电子传输材料及包含该材料的有机电致发光器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910892156.8A CN112538056B (zh) | 2019-09-20 | 2019-09-20 | 一种电子传输材料及包含该材料的有机电致发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN112538056A true CN112538056A (zh) | 2021-03-23 |
CN112538056B CN112538056B (zh) | 2022-06-28 |
Family
ID=75012304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910892156.8A Active CN112538056B (zh) | 2019-09-20 | 2019-09-20 | 一种电子传输材料及包含该材料的有机电致发光器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN112538056B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113024515A (zh) * | 2019-12-25 | 2021-06-25 | 南京高光半导体材料有限公司 | 一种有机电致发光化合物及有机电致发光器件 |
CN113321641A (zh) * | 2021-05-08 | 2021-08-31 | 烟台显华化工科技有限公司 | 一种化合物、电子传输材料、有机电致发光器件和显示装置 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102227485A (zh) * | 2008-12-24 | 2011-10-26 | 第一毛织株式会社 | 有机光电装置用的新化合物和含该化合物的有机光电装置 |
CN109564974A (zh) * | 2017-03-08 | 2019-04-02 | 株式会社Lg化学 | 有机发光器件 |
CN109836419A (zh) * | 2017-11-24 | 2019-06-04 | 株式会社Lg化学 | 新型杂环化合物及利用其的有机发光元件 |
WO2019143223A1 (ko) * | 2018-01-22 | 2019-07-25 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
-
2019
- 2019-09-20 CN CN201910892156.8A patent/CN112538056B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102227485A (zh) * | 2008-12-24 | 2011-10-26 | 第一毛织株式会社 | 有机光电装置用的新化合物和含该化合物的有机光电装置 |
CN109564974A (zh) * | 2017-03-08 | 2019-04-02 | 株式会社Lg化学 | 有机发光器件 |
CN109836419A (zh) * | 2017-11-24 | 2019-06-04 | 株式会社Lg化学 | 新型杂环化合物及利用其的有机发光元件 |
WO2019143223A1 (ko) * | 2018-01-22 | 2019-07-25 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113024515A (zh) * | 2019-12-25 | 2021-06-25 | 南京高光半导体材料有限公司 | 一种有机电致发光化合物及有机电致发光器件 |
CN113024515B (zh) * | 2019-12-25 | 2022-05-31 | 南京高光半导体材料有限公司 | 一种有机电致发光化合物及有机电致发光器件 |
CN113321641A (zh) * | 2021-05-08 | 2021-08-31 | 烟台显华化工科技有限公司 | 一种化合物、电子传输材料、有机电致发光器件和显示装置 |
CN113321641B (zh) * | 2021-05-08 | 2023-07-25 | 烟台显华化工科技有限公司 | 一种化合物、电子传输材料、有机电致发光器件和显示装置 |
Also Published As
Publication number | Publication date |
---|---|
CN112538056B (zh) | 2022-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101380335B1 (ko) | 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치 | |
KR101111120B1 (ko) | 방향족 화합물 및 이를 이용한 유기전계발광소자 | |
EP2952511A1 (en) | Organic compound, organic optoelectronic device and display device | |
CN103570629B (zh) | 一种含有嘧啶或吡嗪或三嗪基团的苯并蒽衍生物及应用 | |
CN112375053B (zh) | 一种化合物及有机电致发光器件 | |
KR20110041726A (ko) | 방향족 화합물 및 이를 이용한 유기전계발광소자 | |
CN105294663B (zh) | 一种含吡啶化合物及其有机电致发光器件 | |
KR20110041728A (ko) | 방향족 화합물 및 이를 이용한 유기전계발광소자 | |
JP2007291064A (ja) | 有機発光素子用アミノ化合物およびそれを有する有機発光素子 | |
KR20160047296A (ko) | 유기 전계 발광 소자 | |
EP4001284A1 (en) | Novel boron compound and organic light-emitting device comprising same | |
CN111675701B (zh) | 一种基于三苯胺结构的有机电致发光化合物及有机电致发光器件 | |
KR20130121597A (ko) | 트리페닐아민을 사용한 정공 수송 물질 및 이를 포함한 유기 전계 발광 소자 | |
CN112538056B (zh) | 一种电子传输材料及包含该材料的有机电致发光器件 | |
CN112552270A (zh) | 一种有机电致发光化合物及有机电致发光器件 | |
CN112442043A (zh) | 一种性能优良的绿色磷光主体材料及有机电致发光器件 | |
CN102786376A (zh) | 新型化合物、有机发光装置和平板显示装置 | |
CN106831798B (zh) | 含有五元环结构的化合物及其有机电致发光器件 | |
CN107428641B (zh) | 有机化合物及包含该有机化合物的有机电致发光元件 | |
WO2008035517A1 (fr) | Dérivés d'amine aromatique et dispositif organique électroluminescent fabriqué en les utilisant | |
EP4122936A1 (en) | Novel boron compound and organic light-emitting element comprising same | |
CN112961144B (zh) | 一种化合物、混合物及有机电致发光器件 | |
Sun et al. | Three times lifetime improvement of red-emitting organic light-emitting diodes based on bipolar host material | |
CN109378397B (zh) | 一种有机电致发光器件 | |
CN112028879A (zh) | 一种电子传输材料、有机电致发光器件和显示装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |