JP2014502966A - 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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- ULSBUTCFWCFFGN-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1)c1cccc2ccccc12 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1)c1cccc2ccccc12 ULSBUTCFWCFFGN-UHFFFAOYSA-N 0.000 description 2
- 0 *c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1 Chemical compound *c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1 0.000 description 1
- HQJQYILBCQPYBI-UHFFFAOYSA-N Brc(cc1)ccc1-c(cc1)ccc1Br Chemical compound Brc(cc1)ccc1-c(cc1)ccc1Br HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 1
- CTNARACDINQFFL-UHFFFAOYSA-N CC(C(C=C1)c2nc(cccc3)c3[n]2-c2ccccc2)C=C1c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound CC(C(C=C1)c2nc(cccc3)c3[n]2-c2ccccc2)C=C1c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 CTNARACDINQFFL-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N Cc(cc1)ccc1Br Chemical compound Cc(cc1)ccc1Br ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- NFCPRRWCTNLGSN-UHFFFAOYSA-N Nc(cccc1)c1Nc1ccccc1 Chemical compound Nc(cccc1)c1Nc1ccccc1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- 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
- XQVWYOYUZDUNRW-UHFFFAOYSA-N c(cc1)ccc1Nc1c(cccc2)c2ccc1 Chemical compound c(cc1)ccc1Nc1c(cccc2)c2ccc1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
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Abstract
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。
Claims (10)
- 請求項1〜5のいずれか一項に記載の化合物を含む発光装置。
- 前記化合物が、発光層中のホストである、請求項6に記載の発光装置。
- 前記発光層と陽極との間に配置された正孔輸送層をさらに含む、請求項7に記載の発光装置。
- 前記発光層と陰極との間に配置された電子輸送層をさらに含む、請求項7に記載の発光装置。
Applications Claiming Priority (5)
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 true JP2014502966A (ja) | 2014-02-06 |
JP5805209B2 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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WO2014039721A1 (en) * | 2012-09-07 | 2014-03-13 | Nitto Denko Corporation | Top-emitting white organic light-emitting diodes having improved efficiency and stability |
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TWI622497B (zh) * | 2012-12-17 | 2018-05-01 | 日東電工股份有限公司 | 包含發光層之發光裝置 |
CN103012479A (zh) * | 2012-12-25 | 2013-04-03 | 东莞有机发光显示产业技术研究院 | 一种磷氧基类电子传输材料及其制备方法和应用 |
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WO2015066354A1 (en) | 2013-10-30 | 2015-05-07 | Nitto Denko Corporation | Light-emitting compounds for light-emitting devices |
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- 2011-12-21 EP EP11811611.0A patent/EP2655338B1/en not_active Not-in-force
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CN103502223A (zh) | 2014-01-08 |
US9373797B2 (en) | 2016-06-21 |
US20110140093A1 (en) | 2011-06-16 |
TWI557114B (zh) | 2016-11-11 |
EP2655338A1 (en) | 2013-10-30 |
JP5805209B2 (ja) | 2015-11-04 |
CN103502223B (zh) | 2015-09-30 |
EP2655338B1 (en) | 2016-02-24 |
WO2012088294A1 (en) | 2012-06-28 |
TW201231458A (en) | 2012-08-01 |
KR20140035316A (ko) | 2014-03-21 |
US20130146856A1 (en) | 2013-06-13 |
US8426040B2 (en) | 2013-04-23 |
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