CN101273480A - 用于改善有机电子元件中空穴注入的新型材料及该材料的应用 - Google Patents
用于改善有机电子元件中空穴注入的新型材料及该材料的应用 Download PDFInfo
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- RNKGDBXXIBUOTR-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1-carbonitrile Chemical class O=C1C=CC(=O)C(C#N)=C1 RNKGDBXXIBUOTR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
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- H10K50/15—Hole transporting layers
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
本发明涉及用于空穴传输层的p型掺杂的新型材料，如式(1)给出的噻唑啉化合物，其中通过所述材料的较高蒸发温度和/或玻璃形成特性来克服现有技术的缺点，尤其是已知p型掺杂材料的较差可蒸发性。
Description
技术领域
本发明涉及用于改善有机电子元件中空穴注入和空穴传输的新型材料，所述电子元件是例如有机发光二极管(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中空穴注入和空穴传输得到显著改善(文献：Gufeng He，Martin Pfeiffer，Karl Leo，Appl.Phys.Lett.85(2004)3911-3913)。
在同样的OLED效率下，这额外地引起工作电压的降低。所述材料是强电子受主并且以较少的量掺杂到OLED的空穴传输层中。由此，这些添加物促进了空穴传输材料的氧化(由此形成空穴)，否则，这仅仅是通过电场能引起氧化。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。
对于改善空穴传输(也称为p掺杂)的方法，所用材料的物理性质在蒸发过程中存在问题。其中涉及蒸发性极难控制的氟化的四氰基苯醌二甲烷，以致于这类掺杂剂不能用于批量生产的装置中，因为所述材料通过不可控制的分布会污染装置。
发明内容
因此，本发明的任务是提供用于改善有机半导体元件中空穴注入的材料，从而克服现有技术中的缺点，尤其是已知材料在蒸发过程中差的可控制性。
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。
提出了具有较高蒸发温度和/或玻璃形成特性的受主材料，由此受控制地蒸发。具有玻璃形成特性的材料是无定形材料，并且由于无结晶性而保证了材料中晶界的消失，从而在空穴传输材料和p掺杂材料之间形成能量上有利的电子传输或空穴传输。较高的蒸发温度使得所述材料可以被可控制地蒸发。
所要求的上述特性可以通过下面结构1的杂环苯醌二甲烷衍生物来实现。
取代基R1至R5互相独立地代表氢、氯、氟、硝基和/或氰基。
另外，R1至R5可以互相独立地被苯基取代基和/或可以形成稠合的芳香族取代基的结构单元替代，其在周围又可以除了氢以外还带有氯和/或氟取代基。
一般合成途径：
所述化合物通过对应的2-二氰基亚甲基-4-芳基-取代的噻唑啉的氧化偶联来合成。
所述新型材料适用于通过与任意空穴传输层的化学相互作用来改善空穴传输和空穴注入，因此，所述材料可以普遍地成功应用于聚合物电子(或者称为有机电子)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)的技术和/或有机光电元件(如有机太阳能电池)的技术。
由此提供了具有空穴传输层的有机电子元件，所述空穴传输层用改善空穴传输特性的材料掺杂或掺入。
加入的所述材料的量根据基体材料而变化。总的来说以常用的掺杂量来掺杂。另外还可以参考开头提到的出版物中的现有技术。
实施例：
1.芳基甲基酮的溴化
在冰醋酸中用溴来溴化相应的芳基甲基酮。
2.芳基酰基硫氰酸酯的合成
在沸腾的乙醇中用硫氰酸钾来转化1.)中的溴甲基芳基酮。
3.2-二氰基亚甲基-4-芳基-噻唑啉的合成
在沸腾的乙醇中用丙二腈和三乙胺将2.)中的芳基酰基硫氰酸酯转化成相应的噻唑啉衍生物。
4.4，4’-二芳基-醌基-5，5’-二噻唑基-2，2’-二氰基二甲烷的合成
在-70℃用丁基锂将3.)中对应的噻唑啉衍生物去质子化，随后用氧化剂(例如CuCl2)将其氧化成期望的4，4’-二芳基-醌基-5，5’-二噻唑基-2，2’-二氰基二甲烷。
Claims (4)
1.一种用于掺杂有机半导体元件的空穴传输层的材料，其特征在于，在所述材料中，受主特性与高于150℃的蒸发温度和/或玻璃形成特性结合存在。
2.根据权利要求1的用于掺杂的材料，其特征在于，所述材料包含下面结构1的杂环苯醌二甲烷衍生物
其中，可以互相独立地选择取代基R1至R5，并且代表氢、氯、氟、硝基和/或氰基，
或者取代基R1至R5互相独立地被苯基取代基和/或可形成稠合的芳香族取代基的结构单元替代，其在周围又可以除了氢以外还带有氯和/或氟取代基。
3.根据权利要求1或2任一项的材料在有机电子元件例如有机发光二极管(OLED)、有机场效应晶体管(OFET)和/或有机光电元件如有机太阳能电池中的用途。
4.一种具有至少两个电极和位于它们之间的有源层的有机电子元件，其中在至少一个电极和有源层之间布置空穴传输层，其特征在于，所述空穴传输层用根据权利要求1～3任一项的材料来掺杂。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005042105 | 2005-09-05 | ||
| DE102005042105.9 | 2005-09-05 | ||
| PCT/EP2006/065726 WO2007028733A1 (de) | 2005-09-05 | 2006-08-28 | Neue materialien zur verbesserung der lochinjektion in organischen elektronischen bauelementen und verwendung des materials |
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| CN101273480A true CN101273480A (zh) | 2008-09-24 |
| CN101273480B CN101273480B (zh) | 2010-09-15 |
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| Country | Link |
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| US (1) | US7947975B2 (zh) |
| EP (1) | EP1938398B1 (zh) |
| JP (1) | JP4922301B2 (zh) |
| KR (1) | KR101339712B1 (zh) |
| CN (1) | CN101273480B (zh) |
| DE (1) | DE502006007053D1 (zh) |
| WO (1) | WO2007028733A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483529A (zh) * | 2019-08-09 | 2019-11-22 | 宁波卢米蓝新材料有限公司 | 一种稠杂环化合物及其应用 |
| CN113809246A (zh) * | 2020-06-15 | 2021-12-17 | Tcl科技集团股份有限公司 | 复合材料及其制备方法和量子点发光二极管 |
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| JP5306341B2 (ja) * | 2007-07-04 | 2013-10-02 | コーニンクレッカ フィリップス エヌ ヴェ | パターン化された層を基板上に形成する方法 |
| JP5488473B2 (ja) * | 2008-11-19 | 2014-05-14 | 日産化学工業株式会社 | 電荷輸送性ワニス |
| KR102442614B1 (ko) | 2015-08-07 | 2022-09-14 | 삼성디스플레이 주식회사 | 디벤조보롤계 화합물 및 이를 포함한 유기 발광 소자 |
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| DE3515373A1 (de) * | 1985-04-27 | 1986-11-06 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| JPH09512572A (ja) | 1994-04-28 | 1997-12-16 | ビーエーエスエフ アクチェンゲゼルシャフト | チアゾールメチン染料 |
| EP0941990A3 (de) | 1998-03-09 | 2002-07-24 | Siemens Aktiengesellschaft | Verfahren zur Herstellung von Azamethinen sowie Azamethine selbst |
| JP2000196140A (ja) * | 1998-12-28 | 2000-07-14 | Sharp Corp | 有機エレクトロルミネッセンス素子とその製造法 |
| WO2002012212A1 (de) | 2000-08-07 | 2002-02-14 | Siemens Aktiengesellschaft | Di(het)arylaminothiazol-derivate und ihre verwendung in organischen lichtemittierenden dioden (oleds) und organischen photovoltaischen bauelemente |
| DE10357044A1 (de) * | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
| WO2006102620A2 (en) * | 2005-03-24 | 2006-09-28 | Northwestern University | TWISTED π-ELECTRON SYSTEM CHROMOPHORE COMPOUNDS WITH VERY LARGE MOLECULAR HYPERPOLARIZABILITIES AND RELATED COMPOSITIONS AND DEVICES |
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- 2006-08-28 KR KR1020087007903A patent/KR101339712B1/ko active IP Right Grant
- 2006-08-28 CN CN2006800323603A patent/CN101273480B/zh active Active
- 2006-08-28 DE DE502006007053T patent/DE502006007053D1/de active Active
- 2006-08-28 EP EP06778379A patent/EP1938398B1/de active Active
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483529A (zh) * | 2019-08-09 | 2019-11-22 | 宁波卢米蓝新材料有限公司 | 一种稠杂环化合物及其应用 |
| CN110483529B (zh) * | 2019-08-09 | 2021-04-13 | 宁波卢米蓝新材料有限公司 | 一种稠杂环化合物及其应用 |
| CN113809246A (zh) * | 2020-06-15 | 2021-12-17 | Tcl科技集团股份有限公司 | 复合材料及其制备方法和量子点发光二极管 |
| CN113809246B (zh) * | 2020-06-15 | 2024-06-11 | Tcl科技集团股份有限公司 | 复合材料及其制备方法和量子点发光二极管 |
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| Publication number | Publication date |
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| JP2009507386A (ja) | 2009-02-19 |
| CN101273480B (zh) | 2010-09-15 |
| JP4922301B2 (ja) | 2012-04-25 |
| EP1938398A1 (de) | 2008-07-02 |
| WO2007028733A1 (de) | 2007-03-15 |
| US7947975B2 (en) | 2011-05-24 |
| EP1938398B1 (de) | 2010-05-26 |
| US20090152535A1 (en) | 2009-06-18 |
| KR20080052634A (ko) | 2008-06-11 |
| DE502006007053D1 (de) | 2010-07-08 |
| KR101339712B1 (ko) | 2013-12-11 |
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