CN101263147A - 用于n掺杂有机电子元件中电子传输层的材料 - Google Patents

用于n掺杂有机电子元件中电子传输层的材料 Download PDF

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CN101263147A
CN101263147A CNA2006800323745A CN200680032374A CN101263147A CN 101263147 A CN101263147 A CN 101263147A CN A2006800323745 A CNA2006800323745 A CN A2006800323745A CN 200680032374 A CN200680032374 A CN 200680032374A CN 101263147 A CN101263147 A CN 101263147A
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安德烈亚斯·卡尼茨
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Ams Osram International GmbH
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/30—Doping active layers, e.g. electron transporting layers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
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    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
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Abstract

本发明涉及基于空间位阻施主芳基硼烷并且用于改善有机电子元件中电子注入和电子传输的新型材料，所述有机电子元件例如为有机发光二极管(OLED)、有机场效应晶体管(OFET)和基于有机光电的元件，尤其是有机太阳能电池。

Description

用于n掺杂有机电子元件中电子传输层的材料
技术领域
本发明涉及用于改善有机电子元件中电子注入和电子传输的新型材料，所述有机电子元件例如为有机发光二极管(OLED)、有机场效应晶体管(OFET)和有机太阳能电池。
背景技术
近年来，一些特别是用于有机发光二极管的材料日益为人所知，通过该材料OLED中电子注入和电子传输得到改善(文献：S.Yamaguchi，S.Akiyama，K.Tamao，J Am.Chem.Soc.2000，122 6335-6336)。
在同样的OLED效率下，这额外地引起工作电压的降低。所述材料是强电子施主并且以较少的量掺杂到OLED的电子传输层或发射层中。由此，这些添加物促进了电子传输材料或发射材料的还原(因此在电子传输材料或发射材料的LUMO[最低空轨道]中的电子摄入)，否则，仅仅是通过电场能进行还原。因此，在较弱的电场(这对应较低的工作电压)下达到同样的效率。
对于目前已知的材料，稳定性与促进注入和电子传输的效率还不能令人满意。
发明内容
因此，本发明的任务是提供用于改善有机元件中电子注入和/或电子传输的材料，从而克服现有技术中的缺点，尤其是提高促进注入和电子传输的效率所缺少的稳定性。
权利要求、实施例和说明书中公开了解决所述任务的方法和本发明的主题。
根据本发明，促进注入和电子传输的效率可以通过亚结构1和2的新型空间位阻施主芳基硼烷来进一步增强。此外，所述材料对空气稳定，对水解不敏感并且是可以升华的。
其中符合下列条件：
Do对应电子施主，尤其适合的是被芳香族(苯基或萘基)取代的氮。
R1和R2或者形成另一稠合的芳香环，或者R1形成到施主取代基的桥体，尤其适合的是硫，在这种情况下，R2是H或甲基。
R3和R4可以是氢或者共同形成稠合的芳香环。
典型的电子施主是芳香体系和所有富含电子的体系如噻吩、烷基取代的或含有硫的多环芳香体系，以及所有电负性较小的取代基，优选富含电子的电负性较小的取代基。
所述新型材料适用于通过与任意电子传输层和/或发射层的化学相互作用来改善电子传输和电子注入，因此，所述材料可以普遍地成功应用于聚合物电子元件中，对此理解为优选所有用于制造有机发光二极管(OLED)、有机场效应晶体管(OFET)和有机太阳能电池的技术。
实施例
1)
a)由二苯基胺和9-溴蒽通过Heck偶联来合成9-二苯基氨基-蒽。
b)由9-二苯基氨基-蒽、丁基锂和三溴化硼在-70℃合成10，10，10-三-9-二苯基氨基-蒽基-硼烷。
Figure A20068003237400051
a)根据Beilstein Handbuch 12，II，744合成3-甲基-1-萘胺。
b)由3-甲基-1-萘胺和溴苯通过Heck偶联来合成1-二苯基氨基-3-甲基-萘。
c)由1-二苯基氨基-3-甲基-萘和硫合成苯并-f-6-甲基-10-苯基-吩噻嗪。
d)由苯并-f-6-甲基-10-苯基-吩噻嗪、丁基锂和三溴化硼在-70℃合成7，7，7-三-苯并-f-6-甲基-10-苯基-吩噻嗪基-硼烷。
Figure A20068003237400052
a)由二苯基胺和9-溴蒽通过Heck偶联来合成9-二苯基氨基-蒽。
b)由9，10-二溴蒽、9-二苯基氨基-蒽、丁基锂和三溴化硼在-70℃合成四-(9-二苯基氨基-蒽-10-基)-9，10-亚蒽基二硼烷。
Figure A20068003237400061
本发明涉及基于空间位阻施主芳基硼烷并且用于改善有机电子元件的电子注入和电子传输的新型材料，所述有机电子元件例如为有机发光二极管(OLED)、有机场效应晶体管(OFET)和基于有机光电的元件，尤其是有机太阳能电池。

Claims (4)

1.一种用于n掺杂有机电子元件中电子传输层的材料，所述材料包含至少一种根据亚结构1和2的三空间位阻施主芳基硼烷之任一个的组分
Figure A20068003237400021
其中
Do对应电子施主，
R1和R2或者形成另一稠合的芳香环，或者R1形成到施主取代基的桥体，特别适合的是硫，在这种情况下，R2是H或甲基，
R3和R4可以是氢或者共同形成稠合的芳香环。
2.根据权利要求1的材料，其中结构1或2任一个中的Do选自包含氮和芳香族(苯基或萘基)取代基的官能团。
3.根据权利要求1或2任一项的材料用于n掺杂有机电子元件中电子传输层的用途。
4.一种有机电子元件，所述电子元件包含至少两个电极和有源层，其中在至少一个电极和有源层之间布置电子传输层，其用根据权利要求1或2任一项的材料掺杂。
CNA2006800323745A 2005-09-05 2006-08-23 用于n掺杂有机电子元件中电子传输层的材料 Pending CN101263147A (zh)

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CN103450238A (zh) * 2013-09-03 2013-12-18 太仓碧奇新材料研发有限公司 一种硼核星状空穴传输材料及其制备方法

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JP5750762B2 (ja) 2011-08-31 2015-07-22 住友化学株式会社 ボラン化合物と共役高分子化合物とを含む組成物及び素子
CN105359288B (zh) 2013-07-31 2017-09-12 富士胶片株式会社 有机半导体组合物、有机薄膜晶体管、电子纸及显示器件
CN103450237B (zh) * 2013-09-03 2015-11-18 太仓碧奇新材料研发有限公司 一种含硼杂环有机晶体管材料的制备方法
CN103450239B (zh) * 2013-09-03 2015-10-28 太仓碧奇新材料研发有限公司 一种单硼杂环有机电子传输材料及其制备方法

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CN103450238A (zh) * 2013-09-03 2013-12-18 太仓碧奇新材料研发有限公司 一种硼核星状空穴传输材料及其制备方法
CN103450238B (zh) * 2013-09-03 2016-06-22 太仓碧奇新材料研发有限公司 一种硼核星状空穴传输材料的制备方法

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KR101350728B1 (ko) 2014-01-13
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US20090114906A1 (en) 2009-05-07

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