JP5193218B2 - 新規の高導電性の有機電荷キャリア輸送材料 - Google Patents
新規の高導電性の有機電荷キャリア輸送材料 Download PDFInfo
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- JP5193218B2 JP5193218B2 JP2009536713A JP2009536713A JP5193218B2 JP 5193218 B2 JP5193218 B2 JP 5193218B2 JP 2009536713 A JP2009536713 A JP 2009536713A JP 2009536713 A JP2009536713 A JP 2009536713A JP 5193218 B2 JP5193218 B2 JP 5193218B2
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- C07D401/14—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 three or more hetero rings
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- 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
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- 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
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Led Devices (AREA)
- Light Receiving Elements (AREA)
- Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Photovoltaic Devices (AREA)
Description
図1は、正及び負の電界における材料の導電性を示す電流−電圧−特性曲線を示す。
最後に、図3は、化合物の光ルミネセンススペクトルを示す。
1) 4−ピリジンカルボキサミジン塩酸塩 1
500mlフラスコ中に、4−シアノピリジン(50.0g、470ミリモル、1当量)を、無水メタノール約230ml中のナトリウムメタノラート(3.0g、53ミリモル、0.11当量)と共に、室温で1.5時間撹拌する。白色がかった懸濁液に、塩化アンモニウム(27.7g、52ミリモル、1.1当量)を添加し、少なくとも24時間更に撹拌する。美しい微細粒の白色の沈殿物を吸引濾過し、母液が乾燥するまで回転蒸発器で濃縮する。フィルターケーキを母液からの残滓と1つにまとめ、水から再結晶させる。吸引濾過し、かつエーテルで洗浄した後に、生成物を真空中で室温で乾燥させる。
2) ビス(1,4−フェニレン)−2−(3−ジメチルアミノ−2−プロペン−ジメチル−イミニウム)−ジ−ペルクロラート 2
温度計、滴下漏斗、及び、取り付けられた乾燥管を有する還流冷却器を備えた、1000mlの三ッ口フラスコ中に、DMF(200ml、2.5モル、30当量)を装入し、氷/塩−冷却混合物を用いて約0℃に冷却する。冷却下に、ゆっくりと、オキシ塩化リン(46ml、0.5モル、6当量)を滴加し、その際、温度は0℃を超えてはならない。後撹拌を10分間行い、かつ、1,4−フェニレン二酢酸(16.3g、0.08モル、1当量)を反応混合物に添加する。引き続き、溶液を90℃で6時間加熱し、冷却し、かつ氷1kgに注ぐ。生成物を沈殿させるために、幾分かの水中に溶解された過塩素酸ナトリウム(30.8g、0.25モル、3当量)を、撹拌下に水溶液に添加する。沈殿物を吸引濾過し、メタノール/エーテル及び純粋なエーテルで洗浄し、次いで真空中で乾燥させる。収量:31.5g(理論値の71%)、白色結晶、M=527.4g・mol-1;融点:292〜296℃
3) ビス−2−(4−ピリジル)−ピリミド−5−イル−1,4−フェニレン
250mlのフラスコ中で、4−ピリジンカルボキサミジン塩酸塩1(5.5g、35ミリモル、2.2当量)を、ピリジン中のフェニレンビスビナミジニウム塩2(8.3g、18ミリモル、1当量)と一緒に、室温で8時間加熱する、生じた黄褐色の沈殿物を吸引濾過し、メタノール、メタノール/エーテル及び純粋なエーテルで洗浄し、次いで真空中で室温で乾燥させる。再結晶はDMSOから行うことができる。その後、生成物を320℃で昇華させる。
Claims (6)
- 材料が薄膜中で透明である、請求項1記載の電荷キャリア輸送材料。
- 混合物として存在する、請求項1又は2記載の電荷キャリア輸送材料。
- n型ドーピング又はp型ドーピングされている、請求項1から3までのいずれか1項記載の電荷キャリア輸送材料。
- 有機電子素子における、請求項1から4までのいずれか1項記載の電荷キャリア輸送材料の使用。
- 請求項1から4までのいずれか1項記載の電荷キャリア輸送材料をベースとする半導体層及び/又は導電性層を有する有機電子素子。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006053644A DE102006053644A1 (de) | 2006-11-14 | 2006-11-14 | Neuartiges hochleitfähiges organisches Ladungsträgertransportmaterial |
DE102006053644.4 | 2006-11-14 | ||
PCT/EP2007/062210 WO2008058929A1 (de) | 2006-11-14 | 2007-11-12 | Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010509781A JP2010509781A (ja) | 2010-03-25 |
JP2010509781A5 JP2010509781A5 (ja) | 2011-07-21 |
JP5193218B2 true JP5193218B2 (ja) | 2013-05-08 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009536713A Active JP5193218B2 (ja) | 2006-11-14 | 2007-11-12 | 新規の高導電性の有機電荷キャリア輸送材料 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8309284B2 (ja) |
EP (1) | EP2092041B9 (ja) |
JP (1) | JP5193218B2 (ja) |
KR (1) | KR101482512B1 (ja) |
CN (1) | CN101679850B (ja) |
AT (1) | ATE481463T1 (ja) |
DE (2) | DE102006053644A1 (ja) |
WO (1) | WO2008058929A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009047880A1 (de) | 2009-09-30 | 2011-03-31 | Osram Opto Semiconductors Gmbh | Organische elektronische Vorrichtung und Verfahren zu dessen Herstellung |
EP2395571B1 (en) | 2010-06-10 | 2013-12-04 | Novaled AG | Organic electronic device comprising an organic semiconducting material |
DE102012205945A1 (de) | 2012-04-12 | 2013-10-17 | Siemens Aktiengesellschaft | Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe |
DE102012217574A1 (de) | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Phosphoroxo-Salze als n-Dotierstoffe für die organische Elektronik |
DE102012217587A1 (de) | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik |
DE102015210388A1 (de) | 2015-06-05 | 2016-12-08 | Siemens Aktiengesellschaft | Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik |
DE102016208298A1 (de) | 2016-05-13 | 2017-11-16 | Siemens Aktiengesellschaft | Organische elektronenleitende Schicht mit n-Dotierstoff |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS6025973A (ja) * | 1983-07-20 | 1985-02-08 | Chisso Corp | ピリミジン類 |
DE4423098A1 (de) * | 1994-07-01 | 1996-01-04 | Hoechst Ag | Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien |
EP1063554B1 (en) | 1994-12-28 | 2004-03-03 | Seiko Epson Corporation | Polarization luminaire and projector using it |
CN1064046C (zh) * | 1997-11-12 | 2001-04-04 | 南开大学戈德防伪技术公司 | 螺环类光致变色化合物及其制备方法 |
GB0225244D0 (en) * | 2002-10-30 | 2002-12-11 | Ciba Sc Holding Ag | Electroluminescent device |
KR100573137B1 (ko) * | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
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2006
- 2006-11-14 DE DE102006053644A patent/DE102006053644A1/de not_active Withdrawn
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2007
- 2007-11-12 CN CN2007800422590A patent/CN101679850B/zh active Active
- 2007-11-12 DE DE502007005097T patent/DE502007005097D1/de active Active
- 2007-11-12 JP JP2009536713A patent/JP5193218B2/ja active Active
- 2007-11-12 US US12/514,986 patent/US8309284B2/en active Active
- 2007-11-12 KR KR20097012297A patent/KR101482512B1/ko active IP Right Grant
- 2007-11-12 WO PCT/EP2007/062210 patent/WO2008058929A1/de active Application Filing
- 2007-11-12 EP EP07822496A patent/EP2092041B9/de active Active
- 2007-11-12 AT AT07822496T patent/ATE481463T1/de active
Also Published As
Publication number | Publication date |
---|---|
ATE481463T1 (de) | 2010-10-15 |
DE102006053644A1 (de) | 2008-06-12 |
EP2092041A1 (de) | 2009-08-26 |
EP2092041B9 (de) | 2011-11-09 |
KR101482512B1 (ko) | 2015-01-13 |
WO2008058929A1 (de) | 2008-05-22 |
US8309284B2 (en) | 2012-11-13 |
US20100112471A1 (en) | 2010-05-06 |
DE502007005097D1 (de) | 2010-10-28 |
CN101679850A (zh) | 2010-03-24 |
CN101679850B (zh) | 2013-05-29 |
KR20090106472A (ko) | 2009-10-09 |
EP2092041B1 (de) | 2010-09-15 |
JP2010509781A (ja) | 2010-03-25 |
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