JP5073187B2 - 青色発光ポリマー及びこれを用いた有機電界発光素子 - Google Patents
青色発光ポリマー及びこれを用いた有機電界発光素子 Download PDFInfo
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Description
前記反応式(2)中、X5はハロゲン原子であり、nは0.01〜0.99の実数であり、zは5〜1000の実数である。
2−ブロモフルオレン24.5g(100mmol)をジメチルスルホキシド(DMSO)200mlに溶かした後、水酸化カリウム14.5g(259mmol)を添加し、20分間撹拌した。前記混合物に、ブロモオクタン42.5g(220mmol)を添加し、これを常温で16時間撹拌した。
2−ブロモ−9,9’−ジオクチルフルオレン(A’)40.8g(87mmol)を無水テトラヒドロフラン(THF)150mlに溶かした後、Mg2.11g(86.8mmol)、及び微量のヨウ素(I2)を添加した後、4時間還流させた。次に、反応混合物を室温に冷却した後、ホウ酸トリメチル27.14g(261.2mmol)をTHF150mlに溶解させた溶液を反応混合物に添加し、その結果物を−78℃に冷却した。その後室温で16時間撹拌した。
9,9’−ジオクチルフルオレニル−2−ホウ酸(B’)32.37g(74.58mmol)、1−アジド−2−ヨードベンゼン18.27g(74.56mmol)、及び5mol%のテトラキストリフェニルホスフィンパラジウム8.62g(7.46mmol)をトルエン200mlに溶かした後、2M炭酸ナトリウム(Na2CO3)100mlをさらに添加し、これを12時間還流させた。
2−(2−アジドフェニル)−9,9−ジオクチルフルオレン(C’)19.9gをo−ジクロロベンゼン100mlに溶かした後、180℃で12時間還流させた。
12,12−ジオクチル−6,12−ジヒドロ−6−アザ−インドロ[1,2−b]フルオレン(D’)4.4g(9.16mmol)、1−ブロモ−4−オクチルオキシベンゼン2.29g、トリス(ジベンジリデンアセトン)二パラジウム(0)0.18g、t−ブトキシナトリウム1.28g、及びt−ブチルホスフィン0.003gをキシレン50mlに溶かした後、120℃で24時間還流させた。
6−(4−ブチルフェニル)−12,12−ジオクチル−6,12−ジヒドロ−6−アザ−インドロ[1,2−b]フルオレン3.5g(5.72mmol)(E’)を150mlのクロロホルムに溶かした後、ここにトリフルオロ酢酸銀2.65g(11.4mmol)を添加した。その後ヨウ素3.03g(11.93mmol)をクロロホルム150mlに溶かした溶液を、前記混合物に徐々に滴加し、常温で6時間反応させた。
前記合成例1によって製造した化学式(17)のポリマーを用いて、有機EL素子を製造した。
11 ホール注入層
12 発光層
13 ホールブロッキング層
14 第2電極
15 電子輸送層
16 ホール輸送層
Claims (4)
- 下記化学式(5)で表される化合物であることを特徴とする、インドロカルバゾール系ポリマー:
zは5〜1,000の実数である。 - 前記ポリマーの重量平均分子量(Mw)が10,000〜200,000であり、分子量分布(MWD)が1.5〜5であることを特徴とする、請求項1に記載のインドロカルバゾール系ポリマー。
- 一対の電極間に有機膜を含む有機電界発光素子であって、
前記有機膜が請求項1または2に記載のインドロカルバゾール系ポリマーを含むことを特徴とする、有機電界発光素子。 - 前記有機膜が発光層またはホール輸送層であることを特徴とする、請求項3に記載の有機電界発光素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2004-0074826 | 2004-09-18 | ||
KR1020040074826A KR101030010B1 (ko) | 2004-09-18 | 2004-09-18 | 청색 발광 고분자 및 이를 채용한 유기 전계 발광 소자 |
Publications (2)
Publication Number | Publication Date |
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JP2006083386A JP2006083386A (ja) | 2006-03-30 |
JP5073187B2 true JP5073187B2 (ja) | 2012-11-14 |
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Application Number | Title | Priority Date | Filing Date |
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JP2005264209A Active JP5073187B2 (ja) | 2004-09-18 | 2005-09-12 | 青色発光ポリマー及びこれを用いた有機電界発光素子 |
Country Status (4)
Country | Link |
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US (1) | US7521525B2 (ja) |
JP (1) | JP5073187B2 (ja) |
KR (1) | KR101030010B1 (ja) |
CN (1) | CN1749295B (ja) |
Families Citing this family (32)
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US7402681B2 (en) * | 2004-12-14 | 2008-07-22 | Xerox Corporation | Compound with indolocarbazole moieties and devices containing such compound |
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CN101495535B (zh) * | 2006-07-21 | 2012-06-20 | 默克专利有限公司 | 茚并芴和噻吩的共聚物 |
JP5151122B2 (ja) * | 2006-11-22 | 2013-02-27 | ソニー株式会社 | 電極被覆材料、電極構造体、及び、半導体装置 |
GB2454890B (en) * | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
DE102008024182A1 (de) | 2008-05-19 | 2009-11-26 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtung |
WO2009148016A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
US8057919B2 (en) * | 2008-06-05 | 2011-11-15 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
JP5483962B2 (ja) * | 2008-09-04 | 2014-05-07 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
KR101609275B1 (ko) | 2008-12-16 | 2016-04-06 | 삼성디스플레이 주식회사 | 유기 화합물 및 이를 포함하는 유기 발광 소자 |
DE102009005288A1 (de) * | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP5390693B2 (ja) * | 2009-03-30 | 2014-01-15 | ドゥクサン ハイ メタル カンパニー リミテッド | 有機電子素子及びその化合物、端末 |
DE102009023155A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101333694B1 (ko) * | 2009-06-25 | 2013-11-27 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101174088B1 (ko) * | 2009-06-25 | 2012-08-14 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
DE102009030847A1 (de) * | 2009-06-26 | 2010-12-30 | Merck Patent Gmbh | Polymere enthaltend substituierte Anthracenyleinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
KR20110009920A (ko) * | 2009-07-23 | 2011-01-31 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101063940B1 (ko) * | 2009-08-26 | 2011-09-08 | 주식회사 두산 | 신규한 유기 화합물 및 이를 이용한 유기 발광 소자 |
KR20110120994A (ko) * | 2010-04-30 | 2011-11-07 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
WO2012014500A1 (ja) * | 2010-07-30 | 2012-02-02 | 保土谷化学工業株式会社 | インデノカルバ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 |
DE102010033080A1 (de) * | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
JP5590491B2 (ja) * | 2011-03-04 | 2014-09-17 | 国立大学法人広島大学 | 高分子化合物、高分子有機半導体材料及び有機半導体デバイス |
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JP6031030B2 (ja) * | 2011-06-27 | 2016-11-24 | 新日鉄住金化学株式会社 | 有機電界発光素子用重合体及びそれを用いた有機電界発光素子 |
KR20130015400A (ko) * | 2011-08-03 | 2013-02-14 | 삼성디스플레이 주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101930848B1 (ko) * | 2011-08-11 | 2018-12-20 | 삼성디스플레이 주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 |
EP2792699B1 (en) | 2011-12-12 | 2021-04-07 | NIPPON STEEL Chemical & Material Co., Ltd. | Cured product and organic electroluminescence element using same |
CN103936659B (zh) * | 2013-12-12 | 2016-06-22 | 石家庄诚志永华显示材料有限公司 | 含有碳桥联咔唑结构单元的化合物及其制备方法与应用 |
WO2016002646A1 (ja) * | 2014-07-03 | 2016-01-07 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
GB201418876D0 (en) * | 2014-10-23 | 2014-12-03 | Cambridge Display Tech Ltd | Organic light emitting device |
CN109824576B (zh) * | 2019-02-21 | 2021-01-19 | 青岛海洋生物医药研究院股份有限公司 | 一种有机光电材料中间体二甲基茚并咔唑的合成方法 |
KR102267797B1 (ko) * | 2020-02-24 | 2021-06-22 | 한국교통대학교 산학협력단 | 유기전계발광소자용 인데노피리딘계 공중합체 및 이를 포함하는 유기전계발광소자 |
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US5874179A (en) * | 1994-09-30 | 1999-02-23 | Hoechst Aktiengesellschaft | Nitrogen-containing polymers as electroluminescent materials |
DE69608446T3 (de) * | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2,7-aryl-9-substituierte fluorene und 9-substituierte fluorenoligomere und polymere |
US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
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KR100280125B1 (ko) * | 1998-11-17 | 2001-02-01 | 정선종 | 불소가 치환된 새로운 테트라페닐 유도체를 단량체로 사용하여제조되는 새로운 청색 발광 고분자 및 이를 이용한 전기 발광소자 |
KR100480769B1 (ko) * | 2001-06-13 | 2005-04-06 | 삼성에스디아이 주식회사 | 백색 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
DE10143353A1 (de) * | 2001-09-04 | 2003-03-20 | Covion Organic Semiconductors | Konjugierte Polymere enthaltend Spirobifluoren-Einheiten und deren Verwendung |
KR100528322B1 (ko) * | 2001-09-28 | 2005-11-15 | 삼성에스디아이 주식회사 | 청색 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
GB0226010D0 (en) * | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
KR100695106B1 (ko) * | 2002-12-24 | 2007-03-14 | 삼성에스디아이 주식회사 | 청색 발광 고분자 및 이를 채용한 유기 전계 발광 소자 |
US7138483B2 (en) * | 2003-02-12 | 2006-11-21 | E.I. Du Pont De Nemours And Company | Monomers, conjugated polymers and electronic devices using such polymers |
KR100718103B1 (ko) * | 2003-12-09 | 2007-05-14 | 삼성에스디아이 주식회사 | 발광 고분자 및 이를 이용한 유기 전계 발광 소자 |
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CN1749295B (zh) | 2011-09-14 |
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US7521525B2 (en) | 2009-04-21 |
JP2006083386A (ja) | 2006-03-30 |
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US20060063033A1 (en) | 2006-03-23 |
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