JP5328356B2 - 高効率リン光有機発光デバイスのための電子妨害層 - Google Patents
高効率リン光有機発光デバイスのための電子妨害層 Download PDFInfo
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/311—Phthalocyanine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Description
本発明は、有機発光デバイス(OLED)、及びより詳細には、電子妨害層を有するリン光OLEDに関する。
有機材料を用いるオプトエレクトロニクスデバイスは、多くの理由によりますます望ましいものとなってきている。そのようなデバイスを作るために用いられる多くの材料はかなり安価であり、そのため有機オプトエレクトロニクスデバイスは、無機デバイスに対して、コスト上の優位性についての潜在力をもっている。加えて、有機材料固有の特性、例えばそれらの柔軟性は、それらを柔軟な基材上への製作などの具体的用途に非常に適したものにしうる。有機オプトエレクトロニクスデバイスの例には、有機発光デバイス(OLED)、有機光トランジスタ、有機光電池、及び有機光検出器が含まれる。OLEDについては、有機材料は、従来の材料に対して性能的優位性をもちうる。例えば、有機発光層が発光する波長は、一般に、適切なドーパントで容易に調節されうる。
一つの態様では、本発明は、基材上に以下の順序で配置された、アノード;ホール輸送層;発光層ホストと発光性ドーパントを含む有機発光層;電子妨害層(electron impeding layer);電子輸送層;及び、カソード、を含む、有機発光デバイスを提供する。
CuPc(100Å)/NPD(300Å)/問題の材料(300Å)/BAlq2(400Å)/LiF(10Å)/Al(1000Å)、又は
CuPc(100Å)/NPD(300Å)/問題の材料(300Å)/Alq3(400Å)/LiF(10Å)/Al(1000Å)。
a)Alq3などの潜在的発光性電子輸送層と組み合わせてOLEDに用いた場合、充分な高電圧が厚いIMP層に印加されたときに、発光が電子輸送層で生じる。前記の電子輸送層は、ホールが電子輸送層中に押し込まれたときに通常は発光する材料ではなくてもよい。したがって、一つの態様では、本デバイスは、第一の有機層がAlq3である類似のデバイスにある材料が用いられた場合に、第二の有機層の厚さを増大させることが第一の有機層からの発光を引き起こすような材料から本質的になる有機層を含む。
b)電子妨害材料は、典型的且つ特定したホール阻止材料、例えばBphen、BAlq2、HPT、又はBAlqよりも小さな又は実質的に小さな相対電子移動度及び/又は相対電子伝導度を有することができる。IMP層はBphenの電子移動度の0.001以下、好ましくはBphenの電子移動度の0.0005以下、より好ましくはBphenの電子移動度の0.0001以下であることが好ましい。
c)電子妨害材料は、ホール輸送材料、すなわち、その電子移動度よりも大きなホール移動度を有する材料であることができる。したがって、一つの態様では、本デバイスはその電子移動度よりも大きなホール移動度を有する材料、例えばTCTA、Irppz、NPD、TPD、mCP、及びそれらの誘導体から本質的になる有機層を含む。
d)電子妨害材料は両極性材料であることができる。したがって、一つの態様では、本デバイスは両極性材料、例えばmCBPから本質的になる有機層を含む。
を含み、前記第二の有機層がホール輸送材料又は両極性材料から本質的になる。
本明細書で用いるように、略語は以下のように材料を表す。
CBP: 4,4'-N,N-ジカルバゾール-ビフェニル
m-MTDATA: 4,4’,4’’-トリス(3-メチルフェニルフェニルアミノ)トリフェニルアミン
Alq3: 8-トリス-ヒドロキシキノリンアルミニウム
Bphen: 4,7-ジフェニル-1,10-フェナントロリン
n-BPhen: n型ドープBPhen(リチウムでドープ)
F4-TCNQ: テトラフルオロ-テトラシアノ-キノジメタン
p-MTDATA: p型ドープm-MTDATA(F4-TCNQでドープ)
Ir(ppy)3: トリス(2-フェニルピリジン)-イリジウム
Ir(ppz)3: トリス(1-フェニルピラゾロト,N,C(2')イリジウム(III)
BCP: 2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン
TAZ: 3-フェニル-4-(1'-ナフチル)-5-フェニル-1,2,4-トリアゾール
CuPc: 銅フタロシアニン
ITO: インジウムスズ酸化物
NPD: N,N'-ジフェニル-N-N'-ジ(l-ナフチル)-ベンジジン
TPD: N,N'-ジフェニル-N-N'-ジ(3-トリル)-ベンジジン
BAlq: アルミニウム(III)ビス(2-メチル-8-ヒドロキシキノリナト)4-フェニルフェノラート
mCP: 1,3-N,N-ジカルバゾール-ベンゼン
DCM: 4-(ジシアノエチレン)-6-(4-ジメチルアミノスチリル-2-メチル)-4H-ピラン
DMQA: N,N'-ジメチルキナクリドン
PEDOT:PSS ポリスチレンスルホン酸(PSS)によるポリ(3,4-エチレンジオキシチオフェン)の水性分散体
本発明の具体的で代表的な実施形態を、このような実施形態がどのようになされうるかを含めてこれから記載する。特定の方法、材料、条件、プロセスパラメータ、装置などは本発明の範囲を必ずしも限定しないことがわかる。
本発明の具体例のデバイス(太字の数字)並びに比較デバイスを表1に列挙した。特定の方法、材料、条件、プロセスパラメータ、装置などは、本発明の範囲を必ずしも限定するものではないことが理解される。
実施例デバイスA〜Dは、厚さを変えた電子妨害層を含む。比較デバイスE及びFは、厚さを変えたホール阻止層を含む。
Claims (18)
- 基材上に以下の順序で配置された、
a)アノード;
b)ホール輸送層;
c)発光層ホストとリン光発光性ドーパントを含み、前記発光層ホストのHOMOが、前記リン光発光性ドーパントのHOMOよりも少なくとも0.5eV低く、且つ前記リン光発光ドーパントが500nm未満の発光スペクトルピークを示す、有機発光層;
d)本質的に両極性材料のみからなり、20Å〜75Åの厚さを有する、電子妨害層;
e)電子輸送層;及び
f)カソード
を含む、有機発光デバイス。 - 前記発光層ホストのHOMOが、前記リン光発光性ドーパントのHOMOよりも少なくとも0.5eV〜0.8eV低い、請求項1に記載のデバイス。
- 前記リン光発光性ドーパントが−5eV又はそれより高いHOMOを有する、請求項1に記載のデバイス。
- 前記両極性材料が、電子移動度よりも大きなホール移動度を有する、請求項1に記載のデバイス。
- 前記両極性材料が、TCTA、Ir(ppz) 3 、NPD、TPD、mCP、及びそれらの誘導体からなる群から選択される、請求項6に記載のデバイス。
- 前記両極性材料が3,3′−N,N−ジカルバゾールビフェニルである、請求項7に記載のデバイス。
- 前記電子妨害層が発光層ホストと同じ材料から本質的になる、請求項1に記載のデバイス。
- 前記電子妨害層が50Åの厚さを有する、請求項1に記載のデバイス。
- 前記電子妨害層材料のHOMOが、前記リン光発光性ドーパントのHOMOよりも少なくとも0.5eV低い、請求項1に記載のデバイス。
- 前記電子妨害層材料のバンドギャップが前記リン光発光性ドーパントのバンドギャップよりも大きい、請求項1に記載のデバイス。
- 前記有機発光層が(X≦0.2,Y≦0.3)のCIE座標をもつ光を発する、請求項1に記載のデバイス。
- アクティブマトリクス有機発光デバイスディスプレイに用いられる、請求項1記載のデバイス。
- 未修正外部量子効率が5%より大きな、請求項1記載のデバイス。
- 前記両極性材料が、Bphenの電子移動度の0.001以下の相対電子移動度を有する、請求項1に記載のデバイス。
- 前記両極性材料がBphenの電子移動度の0.0005以下の相対電子移動度を有する、請求項16に記載のデバイス。
- 前記両極性材料がBphenの電子移動度の0.0001以下の相対電子移動度を有する、請求項17に記載のデバイス。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2008035571A1 (ja) * | 2006-09-20 | 2010-01-28 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US7902374B2 (en) * | 2005-05-06 | 2011-03-08 | Universal Display Corporation | Stability OLED materials and devices |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
JP5520479B2 (ja) * | 2006-02-20 | 2014-06-11 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、白色発光素子、及び照明装置 |
CN101461073B (zh) | 2006-06-01 | 2013-01-02 | 株式会社半导体能源研究所 | 发光元件、发光器件和电子器件 |
US8241764B2 (en) * | 2006-09-21 | 2012-08-14 | Basf Aktiengesellschaft | OLED display with extended lifetime |
US9397308B2 (en) * | 2006-12-04 | 2016-07-19 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element, light emitting device, and electronic device |
US20080284318A1 (en) * | 2007-05-17 | 2008-11-20 | Deaton Joseph C | Hybrid fluorescent/phosphorescent oleds |
US20080286610A1 (en) * | 2007-05-17 | 2008-11-20 | Deaton Joseph C | Hybrid oled with fluorescent and phosphorescent layers |
US20080284317A1 (en) * | 2007-05-17 | 2008-11-20 | Liang-Sheng Liao | Hybrid oled having improved efficiency |
WO2008156879A1 (en) * | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
KR101375331B1 (ko) * | 2007-06-22 | 2014-03-18 | 삼성디스플레이 주식회사 | 백색 유기발광소자 및 그를 포함하는 표시장치와 조명장치 |
JP5119775B2 (ja) * | 2007-07-11 | 2013-01-16 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
TWI638583B (zh) | 2007-09-27 | 2018-10-11 | 半導體能源研究所股份有限公司 | 發光元件,發光裝置,與電子設備 |
CN102655223B (zh) * | 2007-10-19 | 2015-07-22 | 株式会社半导体能源研究所 | 发光元件、发光设备和电子设备 |
JP5018891B2 (ja) * | 2007-11-08 | 2012-09-05 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US8815411B2 (en) * | 2007-11-09 | 2014-08-26 | The Regents Of The University Of Michigan | Stable blue phosphorescent organic light emitting devices |
US8476822B2 (en) | 2007-11-09 | 2013-07-02 | Universal Display Corporation | Saturated color organic light emitting devices |
DE102008025755A1 (de) | 2008-05-29 | 2009-12-03 | Osram Opto Semiconductors Gmbh | Organisches Licht emittierendes Bauteil und Leuchtmittel mit einem solchen Bauteil |
US8062771B2 (en) * | 2009-02-03 | 2011-11-22 | Nitto Denko Corporation | Ambipolar host in organic light emitting diode |
US7893430B2 (en) * | 2009-02-26 | 2011-02-22 | Battelle Memorial Institute | OLED devices |
JP5939984B2 (ja) | 2009-10-28 | 2016-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ヘテロレプティックなカルベン錯体及び該錯体を有機エレクトロニクスで用いる使用 |
US8242489B2 (en) * | 2009-12-17 | 2012-08-14 | Global Oled Technology, Llc. | OLED with high efficiency blue light-emitting layer |
US8227801B2 (en) * | 2010-04-26 | 2012-07-24 | Universal Display Corporation | Bicarbzole containing compounds for OLEDs |
CN101851972A (zh) * | 2010-06-04 | 2010-10-06 | 大连皿能光电科技有限公司 | 后粘贴式太阳能发电幕墙组件 |
KR101182268B1 (ko) * | 2010-07-09 | 2012-09-12 | 삼성디스플레이 주식회사 | 유기 발광 장치 |
WO2012037269A1 (en) | 2010-09-16 | 2012-03-22 | Nitto Denko Corporation | Substituted bipyridines for use in organic light-emitting devices |
CN102587545A (zh) * | 2011-01-11 | 2012-07-18 | 上海泰莱钢结构工程有限公司 | 一种光伏建筑玻璃幕墙组件 |
KR102119353B1 (ko) * | 2011-06-08 | 2020-06-29 | 유니버셜 디스플레이 코포레이션 | 헤테로렙틱 이리듐 카르벤 착물 및 이를 사용한 발광 디바이스 |
KR20130022986A (ko) * | 2011-08-26 | 2013-03-07 | 엘지디스플레이 주식회사 | 유기전계 발광표시장치 |
US9328094B2 (en) | 2011-09-19 | 2016-05-03 | Nitto Denko Corporation | Substituted biaryl compounds for light-emitting devices |
CN102437290B (zh) * | 2011-09-28 | 2016-03-23 | 昆山维信诺显示技术有限公司 | 一种有机电致发光显示器用蓝光器件及其制备方法 |
KR101305869B1 (ko) * | 2011-10-12 | 2013-09-09 | 포항공과대학교 산학협력단 | 단순화된 유기 발광 소자 및 이의 제조 방법 |
JP5760941B2 (ja) * | 2011-10-18 | 2015-08-12 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP6024744B2 (ja) * | 2012-04-03 | 2016-11-16 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
JP5630511B2 (ja) * | 2013-02-06 | 2014-11-26 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US20160181545A1 (en) * | 2013-06-06 | 2016-06-23 | Merck Patent Gmbh | Organic electroluminescent device |
TWI581477B (zh) * | 2014-04-15 | 2017-05-01 | 豐彩科技有限公司 | 有機發光二極體結構及其製造方法 |
JP2017519238A (ja) * | 2014-04-22 | 2017-07-13 | 深▲ちぇん▼市国華光電科技有限公司 | 紙質効果を有する表示構造及びその製造方法 |
KR102408143B1 (ko) | 2015-02-05 | 2022-06-15 | 삼성전자주식회사 | 유기금속 화합물, 유기금속 화합물-함유 조성물 및 이를 포함한 유기 발광 소자 |
US10326086B2 (en) | 2015-02-06 | 2019-06-18 | Samsung Electronics Co., Ltd. | Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound or composition |
KR102637099B1 (ko) | 2016-04-08 | 2024-02-19 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
CN105895819B (zh) * | 2016-04-28 | 2018-07-06 | 京东方科技集团股份有限公司 | 一种oled器件及其制备方法、oled显示面板 |
CN105870349B (zh) * | 2016-06-06 | 2017-09-26 | 京东方科技集团股份有限公司 | 发光二极管及其制备方法、发光器件 |
JP6768534B2 (ja) * | 2016-07-20 | 2020-10-14 | 株式会社Joled | 有機電界発光素子、有機電界発光装置および電子機器 |
JP2018022862A (ja) * | 2016-07-20 | 2018-02-08 | 株式会社Joled | 有機電界発光素子、有機電界発光装置および電子機器 |
US10935492B2 (en) | 2018-04-13 | 2021-03-02 | Applied Materials, Inc. | Metrology for OLED manufacturing using photoluminescence spectroscopy |
CN108767129B (zh) | 2018-05-31 | 2021-01-26 | 京东方科技集团股份有限公司 | 量子点发光二极管及其制备方法、显示面板 |
KR20210101631A (ko) | 2020-02-10 | 2021-08-19 | 삼성전자주식회사 | 유기 발광 소자 |
WO2024069881A1 (ja) * | 2022-09-29 | 2024-04-04 | シャープディスプレイテクノロジー株式会社 | 発光素子、表示装置、発光素子の製造方法 |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4720432A (en) * | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US6548956B2 (en) | 1994-12-13 | 2003-04-15 | The Trustees Of Princeton University | Transparent contacts for organic devices |
ATE320085T1 (de) | 1996-08-12 | 2006-03-15 | Univ Princeton | Nichtpolymeres biegsames organisches lichtemittierendes bauelement und herstellungsverfahren |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6830828B2 (en) * | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
GB9822963D0 (en) | 1998-10-20 | 1998-12-16 | Agner Erik | Improvements in or relating to chromatography |
US6310360B1 (en) | 1999-07-21 | 2001-10-30 | The Trustees Of Princeton University | Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
JP3669333B2 (ja) * | 2001-02-06 | 2005-07-06 | ソニー株式会社 | 有機電界発光素子及び表示装置 |
EP2276084A1 (en) | 2001-03-14 | 2011-01-19 | The Trustees of Princeton University | Materials and devices for blue phosphorescence based organic light emitting diodes |
JP2002359076A (ja) * | 2001-03-27 | 2002-12-13 | Konica Corp | 有機エレクトロルミネッセンス素子、表示装置、発光方法、表示方法および透明基板 |
JP4493915B2 (ja) | 2001-05-16 | 2010-06-30 | ザ、トラスティーズ オブ プリンストン ユニバーシティ | 高効率多色電界リン光oled |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
EP2555274B1 (en) | 2001-08-29 | 2020-06-24 | The Trustees of Princeton University | Organic light emitting devices having carrier blocking layers comprising metal complexes |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
KR100596028B1 (ko) * | 2001-11-12 | 2006-07-03 | 네오뷰코오롱 주식회사 | 고효율 유기 전계발광 소자 |
US20030230980A1 (en) * | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
JP3970253B2 (ja) * | 2003-03-27 | 2007-09-05 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
KR20040094078A (ko) * | 2003-05-01 | 2004-11-09 | 학교법인 영남학원 | 백색 유기발광소자 |
JP2004362914A (ja) * | 2003-06-04 | 2004-12-24 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
US7018723B2 (en) * | 2003-07-25 | 2006-03-28 | The University Of Southern California | Materials and structures for enhancing the performance of organic light emitting devices |
US6881502B2 (en) | 2003-09-24 | 2005-04-19 | Eastman Kodak Company | Blue organic electroluminescent devices having a non-hole-blocking layer |
TW200531587A (en) * | 2003-12-09 | 2005-09-16 | Showa Denko Kk | Polymer for anode buffer layer, coating solution for anode buffer layer, and organic light emitting device |
US7151339B2 (en) | 2004-01-30 | 2006-12-19 | Universal Display Corporation | OLED efficiency by utilization of different doping concentrations within the device emissive layer |
JP4546203B2 (ja) * | 2004-06-15 | 2010-09-15 | キヤノン株式会社 | 発光素子 |
US20060008670A1 (en) * | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
US7709100B2 (en) * | 2004-07-07 | 2010-05-04 | Universal Display Corporation | Electroluminescent efficiency |
US20060006792A1 (en) | 2004-07-09 | 2006-01-12 | Eastman Kodak Company | Flat panel light emitting devices with two sided |
TWI240593B (en) | 2004-10-15 | 2005-09-21 | Ind Tech Res Inst | Top-emitting organic light emitting diode (OLED) |
KR100670803B1 (ko) * | 2004-12-21 | 2007-01-19 | 한국전자통신연구원 | 쇼키 장벽 금속 산화물 반도체 전계 효과 트랜지스터의양극 전도성을 이용한 소자 |
US7683536B2 (en) * | 2005-03-31 | 2010-03-23 | The Trustees Of Princeton University | OLEDs utilizing direct injection to the triplet state |
US7807275B2 (en) * | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPWO2008035571A1 (ja) * | 2006-09-20 | 2010-01-28 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
JP5556014B2 (ja) * | 2006-09-20 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
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KR20140007019A (ko) | 2014-01-16 |
US20070075631A1 (en) | 2007-04-05 |
JP2009510796A (ja) | 2009-03-12 |
KR101384449B1 (ko) | 2014-04-10 |
EP1932193B1 (en) | 2014-07-30 |
WO2007044236A3 (en) | 2007-12-21 |
KR20080063765A (ko) | 2008-07-07 |
TWI413287B (zh) | 2013-10-21 |
EP1932193A2 (en) | 2008-06-18 |
CN101278419A (zh) | 2008-10-01 |
CN101278419B (zh) | 2012-05-23 |
US8148891B2 (en) | 2012-04-03 |
KR101567661B1 (ko) | 2015-11-10 |
TW200721564A (en) | 2007-06-01 |
WO2007044236A2 (en) | 2007-04-19 |
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