JP6114805B2 - 空間電荷移動化合物、これを含む有機発光ダイオード素子及び表示装置 - Google Patents
空間電荷移動化合物、これを含む有機発光ダイオード素子及び表示装置 Download PDFInfo
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- JP6114805B2 JP6114805B2 JP2015235442A JP2015235442A JP6114805B2 JP 6114805 B2 JP6114805 B2 JP 6114805B2 JP 2015235442 A JP2015235442 A JP 2015235442A JP 2015235442 A JP2015235442 A JP 2015235442A JP 6114805 B2 JP6114805 B2 JP 6114805B2
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- 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
- H10K85/611—Charge transfer complexes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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Description
1.化合物1の合成
(1)化合物aの合成
(1)化合物cの合成
(1)化合物dの合成
ITO基板の発光面積が3mm×3mmのサイズとなるようパターニングした後、洗浄した。次に、前記基板を真空蒸着チャンバー内に移送した。ベース圧力が約10−6〜10−7Torrとなるようにした後、陽極であるITOの上に、i)正孔注入層、500Å(NPB、N,N′−ジ(ナフタレン−1−イル)−N,N′−ジフェニル−ベンジジン)、ii)正孔輸送層、100Å(mCP、N,N′−ジカルバゾリル−3,5−ベンゼン)、iii)発光物質層、350Å(ホスト、ビス{2−[ジ(フェニル)ホスフィノ]フェニル}エーテルオキシド)/ドーパント(6%))、iv)電子輸送層、300Å(1,3,5−トリ(フェニル−2−ベンズイミダゾール)−ベンゼン)、v)電子注入層(LiF)、vi)陰極(Al)を順次に積層した。
前述した素子において、発光物質層のドーパントに下記化学式(6)の化合物を利用した。
前述した素子において、発光物質層のドーパントに化合物1を利用した。
前述した素子において、発光物質層のドーパントに化合物3を利用した。
前述した素子において、発光物質層のドーパントに化合物5を利用した。
Claims (10)
- 前記空間電荷移動化合物の一重項エネルギーと三重項エネルギーとの差は、0.3eV以下である、請求項1に記載の空間電荷移動化合物。
- 前記空間電荷移動化合物の一重項エネルギーと三重項エネルギーとの差は、0.3eV以下である、請求項3に記載の有機発光ダイオード素子。
- 前記空間電荷移動化合物はドーパントとして利用され、前記有機発光層はホストをさらに含む、請求項3に記載の有機発光ダイオード素子。
- 前記ホストの最高被占軌道のレベル(HOMOHost)と前記ドーパントの最高被占軌道のレベル(HOMODopant)との差(|HOMOHost−HOMODopant|)、または前記ホストの最低空軌道のレベル(LUMOHost)と前記ドーパントの最低空軌道のレベル(LUMODopant)との差(|LUMOHost−LUMODopant|)は、0.5eV以下である、請求項5に記載の有機発光ダイオード素子。
- 前記空間電荷移動化合物はホストとして利用され、前記有機発光層はドーパントをさらに含む、請求項3に記載の有機発光ダイオード素子。
- 前記空間電荷移動化合物は第1ドーパントとして利用され、前記有機発光層はホスト及び第2ドーパントをさらに含み、
前記第1ドーパントの第1三重項エネルギーは、前記ホストの第2三重項エネルギーより小さく、かつ前記第2ドーパントの第3三重項エネルギーより大きい、請求項3に記載の有機発光ダイオード素子。 - 前記有機発光層は、正孔注入層と、正孔輸送層と、発光物質層と、電子輸送層と、電子注入層とを含み、
前記正孔注入層と、前記正孔輸送層と、前記発光物質層と、前記電子輸送層と、前記電子注入層のうち、少なくとも一つが前記空間電荷移動化合物を含む、請求項3に記載の有機発光ダイオード素子。 - 基板と、
前記基板上に位置する請求項3に記載の有機発光ダイオード素子と、
前記有機発光ダイオード素子を覆う封止フィルムと、
前記封止フィルム上のカバーガラスとを含む表示装置。
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KR10-2014-0173911 | 2014-12-05 | ||
KR20140173911 | 2014-12-05 | ||
KR10-2015-0144199 | 2015-10-15 | ||
KR1020150144199A KR102469690B1 (ko) | 2014-12-05 | 2015-10-15 | 공간 전하 이동 화합물, 이를 포함하는 유기발광다이오드소자 및 표시장치 |
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JP6770900B2 (ja) * | 2017-01-12 | 2020-10-21 | 日本放送協会 | 有機エレクトロルミネッセンス素子 |
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