JP4766527B2 - アントラセン誘導体及びこれを用いた有機電界発光素子 - Google Patents
アントラセン誘導体及びこれを用いた有機電界発光素子 Download PDFInfo
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- JP4766527B2 JP4766527B2 JP2007292144A JP2007292144A JP4766527B2 JP 4766527 B2 JP4766527 B2 JP 4766527B2 JP 2007292144 A JP2007292144 A JP 2007292144A JP 2007292144 A JP2007292144 A JP 2007292144A JP 4766527 B2 JP4766527 B2 JP 4766527B2
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Description
(1)
(39)
1−1. 2,7−ジブロモ−9,10−ジヒドロキシ−9,10−ジフェニルアントラセンの合成
下記反応式1によって、2,7−ジブロモ−9,10−ジヒドロキシ−9,10−ジフェニルアントラセンを合成した。
(反応式1)
下記反応式2によって、2,7−ジブロモ−9,10−ジフェニルアントラセンを合成した。
(反応式2)
下記反応式3によって、前記化学式2のアントラセン誘導体、すなわち、2,7,9,10−テトラフェニルアントラセンを合成した。
(反応式3)
前記1−1及び1−2と同一の方法によって、2,7−ジブロモ−9,10−ジフェニルアントラセンを合成した。次に、下記反応式4によって、前記化学式4のアントラセン誘導体、すなわち、2,7−ジ(4’−ビフェニル)−9,10−ジフェニルアントラセンを合成した。
(反応式4)
ITOガラスの発光面積が2mm×2mmになるように基板上にパターニングした後、洗浄した。前記基板を真空チャンバに装着した後、ベース圧力を1×10−6torrにした後、公知の方法を使って、前記ITOガラス上に、CuPC(200Å)、NPD(400Å)、前記合成例1で製造された化学式2の化合物+C545T(5%)(200Å)、Alq3(350Å)、LiF(5Å)、Al(1000Å)の順序で成膜した。製造した有機電界発光素子の発光特性は、0.4mAで1839cd/m2(6.61V)であった。
化学式2の化合物の代りに前記合成例2で製造された化学式4の化合物を使った点を除いて、実施例1と全く同一の方法によって有機電界発光素子を製造した。製造した有機電界発光素子の発光特性は、0.4mAで1485cd/m2(6.18 V)であった。
化学式2の化合物の代りに9,10−ジ(2−ナフチル)アントラセンを使った点を除いて、実施例1と全く同一の方法によって有機電界発光素子を製造した。製造した有機電界発光素子の発光特性は、0.4mAで1048cd/m2(5.65V)であった。
Claims (5)
- 下記化学式1で表されることを特徴とするアントラセン誘導体。
(前記化学式1において、
R1はフェニル基であり、
R2はそれぞれ独立して、置換されたまたは非置換の炭素数6〜20のアリール基であり、
前記置換されたアリール基は、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、シアノ基、炭素数1〜10のアルキルアミノ基、炭素数1〜10のアルキルシリル基、ハロゲン原子、炭素数6〜10のアリール基、炭素数6〜10のアリールオキシ基、炭素数6〜10のアリールアミノ基、炭素数6〜10のアリールシリル基、及び炭素数3〜19のヘテロアリール基からなる群から選択される一つ以上の置換基によって置換されたものである。) - 下記化学式2〜化学式16で表される群から選択される何れか一つの化合物であることを特徴とする請求項1記載のアントラセン誘導体。
- アノードと、
カソードと、
前記アノードとカソードとの間に介在する請求項1又は請求項2記載のアントラセン誘導体を含む層とを備えることを特徴とする有機電界発光素子。 - 前記アノードとカソードとの間に正孔注入層、正孔輸送層、正孔阻止層、電子輸送層、電子注入層及び電子阻止層からなる群から選択される一つ以上の層をさらに含むことを特徴とする請求項3記載の有機電界発光素子。
- 前記アントラセン誘導体は、前記アノードとカソードとの間の発光層中に含まれることを特徴とする請求項3記載の有機電界発光素子。
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EP2075308A3 (en) * | 2007-12-25 | 2010-04-14 | Yamagata Promotional Organization for Industrial Technology | organic electroluminescence material and element using the same |
JP4662384B2 (ja) * | 2007-12-25 | 2011-03-30 | 財団法人山形県産業技術振興機構 | 有機エレクトロルミネッセンス材料およびそれを用いた素子 |
JP5532705B2 (ja) * | 2008-07-01 | 2014-06-25 | 東レ株式会社 | 発光素子 |
KR101233377B1 (ko) * | 2008-12-30 | 2013-02-18 | 제일모직주식회사 | 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
JP5770977B2 (ja) * | 2009-03-31 | 2015-08-26 | 株式会社半導体エネルギー研究所 | オキサジアゾール誘導体、オキサジアゾール誘導体を用いた発光素子、発光装置、電子機器、および照明装置 |
US9153790B2 (en) * | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
KR101368164B1 (ko) | 2009-05-29 | 2014-02-27 | 이데미쓰 고산 가부시키가이샤 | 안트라센 유도체 및 그것을 이용한 유기 전계 발광 소자 |
JP5716015B2 (ja) | 2009-06-05 | 2015-05-13 | 北京維信諾科技有限公司 | 有機elおよびそのテスト方法 |
US8771840B2 (en) * | 2009-11-13 | 2014-07-08 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device |
KR101411122B1 (ko) * | 2009-11-13 | 2014-06-25 | 베이징 비젼녹스 테크놀로지 컴퍼니 리미티드 | 유기 재료 및 그 재료를 이용한 유기 el 디바이스 |
JP5756761B2 (ja) * | 2010-02-10 | 2015-07-29 | Lumiotec株式会社 | 有機el照明装置 |
KR101191644B1 (ko) | 2010-05-18 | 2012-10-17 | 삼성디스플레이 주식회사 | 유기 재료와 이를 이용한 유기 발광 장치 |
KR101950363B1 (ko) | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
DE112011104615B4 (de) | 2010-12-28 | 2022-04-28 | Semiconductor Energy Laboratory Co., Ltd. | Organoborverbindung und Verfahren zum Herstellen derselben |
TWI518078B (zh) | 2010-12-28 | 2016-01-21 | 半導體能源研究所股份有限公司 | 充當發光元件材料之苯並[b]萘並[1,2-d]呋喃化合物 |
KR101998430B1 (ko) | 2011-04-25 | 2019-10-17 | 호도가야 가가쿠 고교 가부시키가이샤 | 유기 전계발광 소자 |
US9312500B2 (en) | 2012-08-31 | 2016-04-12 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
CN103664746B (zh) * | 2012-09-03 | 2016-11-16 | 乐金显示有限公司 | 蒽化合物以及包含该蒽化合物的有机发光二极管 |
CN105143186A (zh) | 2013-02-22 | 2015-12-09 | 出光兴产株式会社 | 蒽衍生物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
CN107602467A (zh) * | 2017-09-18 | 2018-01-19 | 长春海谱润斯科技有限公司 | 一种含蒽类化合物及其合成方法和有机电致发光器件 |
JP7325731B2 (ja) | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
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US7169482B2 (en) * | 2002-07-26 | 2007-01-30 | Lg.Philips Lcd Co., Ltd. | Display device with anthracene and triazine derivatives |
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