JP5805209B2 - 発光装置に使用するためのベンゾイミダゾール誘導体 - Google Patents
発光装置に使用するためのベンゾイミダゾール誘導体 Download PDFInfo
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- SCMBZUMKWXVQOD-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)nc2c1cccc2 SCMBZUMKWXVQOD-UHFFFAOYSA-N 0.000 description 1
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Description
本願は、2010年12月22日出願の米国特許仮出願第61/426,259号および2011年2月23日出願の米国特許出願第13/033,473号の優先権を主張するものであり、該米国特許仮出願および該米国特許出願の両方は、それら全体が参照により本明細書に組み込まれる。
〔実施例1.1〕
〔実施例2.1〕(装置−A)
装置(装置A)を次に述べるのと同様の手法で作製した。約14オーム/平方のシート抵抗を有するITO基板を超音波洗浄し、洗剤、水、アセトンそしてイソプロピルアルコール(IPA)で順次洗浄し、その後、80℃のオーブンの中で約30分間、周囲環境で乾燥させた。次に、基板を約200℃で約1時間、周囲環境で焼成し、その後、約30分間のUV−オゾン処理に付した。次に、そのアニールした基板上にPEDOT:PSS(正孔注入材料)を約4000rpmで約30秒間スピンコートした。その後、そのコート層を約100℃で30分間、周囲環境で焼成し、続いて200℃で30分間、グローブボックス(N2環境)内で焼成した。その後、その基板を真空チャンバに移し、そこで約2×10−7トールのベース圧力下、速度約0.1nm/秒で4,4’−ビス[N−(ナフチル)−N−フェニル−アミノ]ビフェニル(NPB)を真空蒸着した。ビス(1−フェニルイソキノリン)(アセチルアセトナート)イリジウム(III)(「Ir(piq)2acac」)(10重量%)を発光層としてホスト−2ホスト材料と共にそれぞれ約0.01nm/秒および約0.10nm/秒で共蒸着して、適切な厚さ比を生じさせた。
他の装置は、Ir(piq)2acacの代わりに、発光性錯体として600nmでピーク波長を発光するビス(フェニルキノリン)インジウムアセチルアセトナート(Ir(PQ)2acac)(6重量%)をそれぞれのホスト材料と共に使用したこと、およびITO厚が150ではなく55nmであったことを除き、実施例2.1に従って組み立てた。発光素子およびホストの蒸着速度は、それぞれ0.006nm/秒および0.1nm/秒であった。
他の装置(装置D[ホスト−3]、装置E[ホスト−4]、比較装置X[ホスト−X]および比較装置Y[NPB])は、化合物ホスト−1(94%)とビス(2−フェニルキノリル−N,C2’)アセチルアセトナートイリジウム(III)(Ir(PQ)2acac)(6%)との混合物の代わりに、化合物ホスト−3(94%)とビス(2−フェニルキノリル−N,C2’)アセチルアセトナートイリジウム(III)(Ir(PQ)2acac)との混合物、化合物ホスト−4(94%)とビス(2−フェニルキノリル−N,C2’)アセチルアセトナートイリジウム(III)(Ir(PQ)2acac)との混合物、比較化合物X、4’’−(1−フェニル−1H−ベンゾ[d]イミダゾール−2−イル)−N,N−ジ−p−トリル−[1,1’:4’,1’’−テルフェニル]−4−アミン(94%)とビス(2−フェニルキノリル−N,C2’)アセチルアセトナートイリジウム(III)(Ir(PQ)2acac)(6%)との混合物、および比較化合物Y、4,4’−ビス[N−(ナフチル)−N−フェニル−アミノ]ビフェニル(NPB)(94%)とビス(2−フェニルキノリル−N,C2’)アセチルアセトナートイリジウム(III)(Ir(PQ)2acac)(6%)との混合物をNPBの頂部にそれぞれ共蒸着させて、30nm厚の発光層20を形成したことを除き、実施例2.2に従って組み立てた。
〔実施例3.1〕
すべてのスペクトルをPR670で測定し、I−V−L特性をKeithley 2400 SourceMeter(Keithley Instruments,Inc.、米国オハイオ州クリーヴランド)で得た。すべての装置操作を、窒素を満たしたグローブボックス内で行った。
ホスト−2:Ir(PQ)2acacおよびホスト−1:Ir(PQ)2acacをそれぞれ含み、実施例2.2に従って作製した発光装置、装置BおよびCを試験して、装置の寿命(5000nitでT50(時))を判定した。すべてのスペクトルをPR670で測定し、I−V−L特性をKeithley 2400 SourceMeter(Keithley Instruments,Inc.、米国オハイオ州クリーヴランド)で得た。すべての装置操作を、窒素を満たしたグローブボックス内で、封入せずに行った。
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201061426259P | 2010-12-22 | 2010-12-22 | |
US61/426,259 | 2010-12-22 | ||
US13/033,473 | 2011-02-23 | ||
US13/033,473 US8426040B2 (en) | 2010-12-22 | 2011-02-23 | Compounds for use in light-emitting devices |
PCT/US2011/066536 WO2012088294A1 (en) | 2010-12-22 | 2011-12-21 | Benzoimidazole derivatives for use in light - emitting devices |
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JP2014502966A JP2014502966A (ja) | 2014-02-06 |
JP5805209B2 true JP5805209B2 (ja) | 2015-11-04 |
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JP2013546377A Expired - Fee Related JP5805209B2 (ja) | 2010-12-22 | 2011-12-21 | 発光装置に使用するためのベンゾイミダゾール誘導体 |
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US (2) | US8426040B2 (ja) |
EP (1) | EP2655338B1 (ja) |
JP (1) | JP5805209B2 (ja) |
KR (1) | KR20140035316A (ja) |
CN (1) | CN103502223B (ja) |
TW (1) | TWI557114B (ja) |
WO (1) | WO2012088294A1 (ja) |
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KR101257695B1 (ko) | 2008-12-24 | 2013-04-24 | 제일모직주식회사 | 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
JP2010278390A (ja) * | 2009-06-01 | 2010-12-09 | Fujifilm Corp | 有機電界発光素子 |
US8420235B2 (en) | 2009-06-04 | 2013-04-16 | Nitto Denko Corporation | Emissive diaryl acetylenes |
US20100326526A1 (en) | 2009-06-29 | 2010-12-30 | Nitto Denko Corporation | Emissive aryl-heteroaryl compounds |
JP5773585B2 (ja) | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
US8426040B2 (en) | 2010-12-22 | 2013-04-23 | Nitto Denko Corporation | Compounds for use in light-emitting devices |
US8933243B2 (en) | 2011-06-22 | 2015-01-13 | Nitto Denko Corporation | Polyphenylene host compounds |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2014510393A (ja) * | 2011-01-27 | 2014-04-24 | 日東電工株式会社 | 場合によっては置換されているテルフェニルおよびクアテルフェニル化合物を含有する光線療法装置および方法 |
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US9373797B2 (en) | 2016-06-21 |
JP2014502966A (ja) | 2014-02-06 |
TWI557114B (zh) | 2016-11-11 |
CN103502223A (zh) | 2014-01-08 |
KR20140035316A (ko) | 2014-03-21 |
US8426040B2 (en) | 2013-04-23 |
US20110140093A1 (en) | 2011-06-16 |
EP2655338A1 (en) | 2013-10-30 |
WO2012088294A1 (en) | 2012-06-28 |
CN103502223B (zh) | 2015-09-30 |
TW201231458A (en) | 2012-08-01 |
EP2655338B1 (en) | 2016-02-24 |
US20130146856A1 (en) | 2013-06-13 |
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