JP5009341B2 - 金属錯体を含むキャリア輸送層を有する有機発光デバイス - Google Patents
金属錯体を含むキャリア輸送層を有する有機発光デバイス Download PDFInfo
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- JP5009341B2 JP5009341B2 JP2009170165A JP2009170165A JP5009341B2 JP 5009341 B2 JP5009341 B2 JP 5009341B2 JP 2009170165 A JP2009170165 A JP 2009170165A JP 2009170165 A JP2009170165 A JP 2009170165A JP 5009341 B2 JP5009341 B2 JP 5009341B2
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- layer
- emitting device
- light emitting
- metal
- blocking layer
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- 229910052726 zirconium Inorganic materials 0.000 description 1
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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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
R10、R13、R20及びR21はそれぞれ独立にN又はCであり、
R11及びR12はそれぞれ独立にN又はCであり、
環系A、B、G、K及びLはそれぞれ独立に、任意選択で最大5個のヘテロ原子を含む単環、二環もしくは三環の縮合脂肪族又は芳香族環系であり、
ZはC1〜C6アルキル、C2〜C8モノ−もしくはポリアルケニル、C2〜C8モノ−もしくはポリアルキニル、又は結合であり、
QはBH、N又はCHである]
Mは金属原子であり、
XはN又はCX’(式中、X’はH、C1〜C20アルキル、C2〜C40モノ−もしくはポリアルケニル、C2〜C40モノ−もしくはポリアルキニル、C3〜C8シクロアルキル、アリール、ヘテロアリール、アラルキル、ヘテロアラルキル、又はハロである)であり、
AはCH、CX’、N、P、P(=O)、アリール又はヘテロアリールであり、
R1及びR2はそれぞれ独立に、H、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、又はハロである、又は
R1及びR2は、これらを結合している炭素原子と共に、連結して縮合したC3〜C8シクロアルキル又はアリール基を形成し、
R3はH、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、又はハロであり、
nは1〜5である]
を有する化合物を含む。
前記正孔輸送層が第1のHOMOエネルギーを有し、前記正孔輸送層が、少なくとも1種の金属錯体を含み、
前記発光層が電子を輸送できる少なくとも1種の材料を含み、前記材料が第2のHOMOエネルギーを有し、且つ
前記阻止層が、前記第1と第2のHOMOエネルギーの間にあるHOMOエネルギーを有する材料を含むデバイスも提供する。
R10、R13、R20及びR21はそれぞれ独立にN又はCであり、
R11及びR12はそれぞれ独立にN又はCであり、
環系A、B、G、K及びLはそれぞれ独立に、任意選択で最大5個のヘテロ原子を含む単環、二環もしくは三環の縮合脂肪族又は芳香族環系であり、
ZはC1〜C6アルキル、C2〜C8モノ−もしくはポリアルケニル、C2〜C8モノ−もしくはポリアルキニル、又は結合であり、
QはBH、N又はCHである]
を含む正孔阻止層を含む。
Mは金属原子であり、
XはN又はCX’(式中、X’はH、C1〜C20アルキル、C2〜C40モノ−もしくはポリアルケニル、C2〜C40モノ−もしくはポリアルキニル、C3〜C8シクロアルキル、アリール、ヘテロアリール、アラルキル、ヘテロアラルキル、又はハロである)であり、
AはCH、CX’、N、P、P(=O)、アリール又はヘテロアリールであり、
R1及びR2はそれぞれ独立に、H、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、若しくはハロであり、又は
R1及びR2は、これらを結合している炭素原子と共に、連結して縮合したC3〜C8シクロアルキル又はアリール基を形成し、
R3はH、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、又はハロであり、
nは1〜5である]
の金属錯体が含まれる。
Mは金属原子であり、
XはN又はCX’(式中、X’はH、C1〜C20アルキル、C2〜C40モノ−もしくはポリアルケニル、C2〜C40モノ−もしくはポリアルキニル、C3〜C8シクロアルキル、アリール、ヘテロアリール、アラルキル、ヘテロアラルキル、又はハロである)であり、
R1及びR2はそれぞれ独立に、H、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、若しくはハロであり、又は
R1及びR2は、これらを結合している炭素原子と共に、連結して縮合したC3〜C8シクロアルキル又はアリール基を形成し、
R3はH、C1〜C20アルキル、C2〜C40アルケニル、C2〜C40アルキニル、C3〜C8シクロアルキル、アリール、アラルキル、又はハロである]
を有していてよい。
THF(3ml)中の1−フェニルピラゾール(1.0当量モル、6.93ミリモル)の溶液に臭化エチルマグネシウム(1.1当量モル、7.6ミリモル)を加えた。反応混合物をアルゴン雰囲気下で3時間還流させ、次いでドライアイス/アセトン浴中で冷却した。次いで、THF(8ml)中の臭化コバルト(II)(0.5当量モル、3.47ミリモル)の溶液を徐々にグリニャール試薬に加えた。反応混合物は直ちに黒変した。浴を取り外し、混合物を2日間撹拌した。
配位子合成(4−トリルフェニルピラゾール):250mlフラスコに、マグネチックスターラー、4−トリルホウ酸(16ミリモル、2.0当量)、ピラゾール(8ミリモル、1.0当量)、無水酢酸銅(12ミリモル、1.5ミリモル)、活性4Åモレキュラーシーブ6g、ピリジン(16ミリモル、2.0当量)及びジクロロメタン96mlを加えた。緩くキャップをしたフラスコ中で、反応物を空気下、周囲温度で2日間撹拌した。反応混合物をセライトでろ過し、水で洗浄してシリカゲルクロマトグラフィー(溶離液:酢酸エチル:ヘキサン=1:7)で精製した。
配位子合成(4−メトキシフェニルピラゾール):250mlフラスコに、マグネチックスターラー、4−メトキシホウ酸(16ミリモル、2.0当量)、ピラゾール(8ミリモル、1.0当量)、無水酢酸銅(12ミリモル、1.5ミリモル)、活性4Åモレキュラーシーブ6g、ピリジン(16ミリモル、2.0当量)、及びジクロロメタン96mlを加えた。緩くキャップをしたフラスコ中で、反応物を空気下、周囲温度で2日間撹拌した。反応混合物をセライトでろ過し、水で洗浄してシリカゲルクロマトグラフィー(溶離液:酢酸エチル:ヘキサン=1:7)で精製した。
配位子合成(4,5−ジフルオロフェニルピラゾール):250mlフラスコに、マグネチックスターラー、4,5−ジフルオロホウ酸(16ミリモル、2.0当量)、ピラゾール(8ミリモル、1.0当量)、無水酢酸銅(12ミリモル、1.5ミリモル)、活性4Åモレキュラーシーブ6g、ピリジン(16ミリモル、2.0当量)、及びジクロロメタン96mlを加えた。緩くキャップをしたフラスコ中で、反応物を空気下、周囲温度で2日間撹拌した。反応混合物をセライトでろ過し、水で洗浄してシリカゲルクロマトグラフィー(溶離液:酢酸エチル:ヘキサン=1:7)で精製した。
配位子合成(4−フルオロフェニルピラゾール):250mlフラスコに、マグネチックスターラー、4−フルオロホウ酸(16ミリモル、2.0当量)、ピラゾール(8ミリモル、1.0当量)、無水酢酸銅(12ミリモル、1.5ミリモル)、活性4Åモレキュラーシーブ6g、ピリジン(16ミリモル、2.0当量)、及びジクロロメタン96mlを加えた。緩くキャップをしたフラスコ中で、反応物を空気下、周囲温度で2日間撹拌した。反応混合物をセライトでろ過し、水で洗浄してシリカゲルクロマトグラフィー(溶離液:酢酸エチル:ヘキサン=1:7)で精製した。
配位子合成(4−tert−フェニルピラゾール):250mlフラスコに、マグネチックスターラー、4−tert−ホウ酸(16ミリモル、2.0当量)、ピラゾール(8ミリモル、1.0当量)、無水酢酸銅(12ミリモル、1.5ミリモル)、活性4Åモレキュラーシーブ6g、ピリジン(16ミリモル、2.0当量)、及びジクロロメタン96mlを加えた。緩くキャップをしたフラスコ中で、反応物を空気下、周囲温度で2日間撹拌した。反応混合物をセライトでろ過し、水で洗浄してシリカゲルクロマトグラフィー(溶離液:酢酸エチル:ヘキサン=1:7)で精製した。
トリス(2−アミノエチル)アミン(0.720g、5ミリモル、10mL)のメタノール溶液に、ピロール−2−カルボキシアルデヒド(1.430g、15ミリモル、100mL)のメタノール溶液を加えて配位子[(((ピロール−2−イル)メチリデン)アミノ)エチル]アミンを調製した。得られた黄色の溶液を室温で30分間攪拌した。硝酸ガリウム(III)水和物(1.280g、5ミリモル、150mL)のメタノール溶液を配位子溶液に加え室温で30分間攪拌した。溶液をろ過し、周囲温度で静置して結晶化させた。次いで粗生成物を235℃で昇華させた。
Co(ppz)3をHTLとして使用した構造ITO/HTL/Alq3/MgAgを用いて機能性OLEDを作製した。これらのデバイスは、HTLがトリアリールアミンから成る比較デバイスより低い効率を有した。NPDの薄層をCo(ppz)3層とAlq3層との間に挿入した場合、これらのデバイスで高い効率が達成された。NPDとCo(ppz)3のHOMOレベルはどちらも類似したエネルギー(NPDで5.5eV、Co(ppz)3で5.4eV)である。図13〜15を参照されたい。
Co(ppz)3正孔輸送層、Ga(pma)3電子阻止層及びAlq3発光層を用いて機能性OLEDを作製した。作動電圧は約3.5V(この電圧での外部輝度=Cd/m2)で、ピーク効率は1.2%より大きかった。図7〜10を参照されたい。
Co(ppz)3/Ga(pma)3正孔輸送層及びドープされたCBP発光層を用いて機能性OLEDを作製した。NPD正孔輸送層を用いて類似のデバイスも作製した。全体として、Co(ppz)3/Ga(pma)3デバイスは、NPD層を用いたデバイスより良好な性能であった。Co(ppz)3/Ga(pma)3では、低い電圧電流はより低く、スペクトルは青色発光(400nm未満)を示していない。Co(ppz)3/Ga(pma)3ベースのデバイスでは、NPDベースのデバイスの場合より、作動電圧は若干高く、量子効率はより低かった。これらのパラメータはどちらもデバイス最適化によって改善されると予想される。図11〜12を参照されたい。
Claims (18)
- 陽極、正孔輸送層、発光層、及び陰極をこの順に含む発光デバイスであって、前記正孔輸送層が、少なくとも1つの配位炭素原子を有する少なくとも1種の有機金属錯体を含み、且つ前記有機金属錯体が少なくとも1つの多座配位子を含む、発光デバイス。
- 前記正孔輸送層が本質的に前記有機金属錯体のみからなる請求項1に記載の発光デバイス。
- 前記正孔輸送層が前記有機金属錯体でドープされた有機マトリックスを含む請求項1に記載の発光デバイス。
- 前記有機金属錯体が、配位的に飽和されている請求項1〜3のいずれか一項に記載の発光デバイス。
- 前記有機金属錯体が配位数6を有する請求項1〜4のいずれか一項に記載の発光デバイス。
- 前記有機金属錯体が配位数4を有する請求項1〜4のいずれか一項に記載の発光デバイス。
- 前記有機金属錯体の前記金属が遷移金属である請求項1〜6のいずれか一項に記載の発光デバイス。
- 前記遷移金属が第1系列の遷移金属である請求項7に記載の発光デバイス。
- 前記遷移金属が第2又は第3系列の遷移金属である請求項7に記載の発光デバイス。
- 前記有機金属錯体の金属がFe、Co、Ru、Pd、Os又はIrである請求項1に記載の発光デバイス。
- 前記有機金属錯体の金属がFe又はCoである請求項1に記載の発光デバイス。
- 前記有機金属錯体の金属がFeである請求項1に記載の発光デバイス。
- 前記有機金属錯体の金属がCoである請求項1に記載の発光デバイス。
- 前記配位子が二座配位子である、請求項1に記載の発光デバイス。
- 前記配位子が三座配位子である、請求項1に記載の発光デバイス。
- 前記配位子が四座配位子である、請求項1に記載の発光デバイス。
- 前記配位子が六座配位子である、請求項1に記載の発光デバイス。
- 前記有機金属錯体の金属がCoである請求項14に記載の発光デバイス。
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Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4409942B2 (ja) * | 2001-08-29 | 2010-02-03 | ザ トラスティーズ オブ プリンストン ユニバーシテイ | 金属錯体を含むキャリア輸送層を有する有機発光デバイス |
KR100917347B1 (ko) * | 2001-08-29 | 2009-09-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 금속 착물들을 포함하는 캐리어 블로킹층들을 갖는 유기발광 디바이스들 |
US6951694B2 (en) * | 2002-03-29 | 2005-10-04 | The University Of Southern California | Organic light emitting devices with electron blocking layers |
WO2003088271A1 (en) * | 2002-04-08 | 2003-10-23 | The University Of Southern California | Doped organic carrier transport materials |
CN100387607C (zh) * | 2003-03-24 | 2008-05-14 | 南加利福尼亚大学 | Ir的苯基-吡唑配合物 |
EP1610594A4 (en) * | 2003-04-02 | 2009-11-25 | Fujifilm Corp | ORGANIC ELECTROLUMINESCENT ELEMENT AND ORGANIC ELECTROLUMINESCENT DISPLAY |
US6853133B2 (en) * | 2003-05-07 | 2005-02-08 | Eastman Kodak Company | Providing an emission-protecting layer in an OLED device |
EP1478026B1 (de) | 2003-05-15 | 2011-07-27 | Samsung Mobile Display Co., Ltd. | Photolumineszenzanzeigeelement und Display auf Basis von Photolumineszenzanzeigeelementen |
EP1478024A1 (de) * | 2003-05-15 | 2004-11-17 | Samsung SDI Co., Ltd. | Organische Leuchtdiode (OLED) und Display auf Basis von OLEDs |
JP4188846B2 (ja) * | 2003-05-15 | 2008-12-03 | 三星エスディアイ株式会社 | 発光抑制素子及びこれに基づいた画像表示装置 |
EP2924094B1 (en) | 2003-06-02 | 2017-04-05 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
JP4650265B2 (ja) * | 2003-07-23 | 2011-03-16 | 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、照明装置及び表示装置 |
DE10338550A1 (de) * | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
KR101246247B1 (ko) * | 2003-08-29 | 2013-03-21 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 전계발광소자 및 그것을 구비한 발광장치 |
US7332232B2 (en) * | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
DE102004010954A1 (de) * | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
JP4621201B2 (ja) | 2004-03-25 | 2011-01-26 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
WO2005099313A1 (ja) * | 2004-04-02 | 2005-10-20 | Idemitsu Kosan Co., Ltd. | 電子障壁層を介して2つの発光層を有する有機エレクトロルミネッセンス素子 |
KR100632632B1 (ko) | 2004-05-28 | 2006-10-12 | 삼성전자주식회사 | 나노 결정의 다층 박막 제조 방법 및 이를 이용한유·무기 하이브리드 전기 발광 소자 |
US20060073360A1 (en) * | 2004-09-28 | 2006-04-06 | Fuji Photo Film Co., Ltd. | Organic electroluminescent device |
US7597967B2 (en) * | 2004-12-17 | 2009-10-06 | Eastman Kodak Company | Phosphorescent OLEDs with exciton blocking layer |
US7683536B2 (en) * | 2005-03-31 | 2010-03-23 | The Trustees Of Princeton University | OLEDs utilizing direct injection to the triplet state |
JP2006310479A (ja) * | 2005-04-27 | 2006-11-09 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
US20070003786A1 (en) * | 2005-06-30 | 2007-01-04 | Eastman Kodak Company | Electroluminescent devices with nitrogen bidentate ligands |
JP4999291B2 (ja) | 2005-06-30 | 2012-08-15 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子およびそれを備える表示装置又は発光装置 |
US20090039771A1 (en) | 2005-07-01 | 2009-02-12 | Konica Minolta Holdings, Inc. | Organic electroluminescent element material, organic electroluminescent element, display device and lighting device |
GB0518968D0 (en) | 2005-09-16 | 2005-10-26 | Cdt Oxford Ltd | Organic light-emitting device |
US20090066227A1 (en) * | 2005-12-20 | 2009-03-12 | Canon Kabushiki Kaisha | Organic light-emitting device |
KR101275809B1 (ko) * | 2006-02-08 | 2013-06-18 | 삼성디스플레이 주식회사 | 전이금속 화합물 및 이를 이용한 유기 전계 발광 소자 |
US20070207345A1 (en) * | 2006-03-01 | 2007-09-06 | Eastman Kodak Company | Electroluminescent device including gallium complexes |
FR2898910B1 (fr) * | 2006-03-23 | 2008-06-20 | Centre Nat Rech Scient | Nouveau procede d'application en couche mince de materiaux moleculaires a transition de spin |
JP4994688B2 (ja) * | 2006-03-27 | 2012-08-08 | 昭和電工株式会社 | キャリア輸送性および燐光発光性を有する化合物を用いた有機発光素子 |
CN101079471B (zh) * | 2006-05-25 | 2010-06-09 | 清华大学 | 一种有机电致发光器件 |
US7598381B2 (en) * | 2006-09-11 | 2009-10-06 | The Trustees Of Princeton University | Near-infrared emitting organic compounds and organic devices using the same |
WO2008075615A1 (en) | 2006-12-21 | 2008-06-26 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and light-emitting device |
KR101118808B1 (ko) * | 2006-12-28 | 2012-03-22 | 유니버셜 디스플레이 코포레이션 | 긴 수명의 인광 유기 발광 소자(oled) 구조체 |
DE102007002420A1 (de) * | 2007-01-17 | 2008-07-24 | Universität Regensburg | Polymere Anionen/Kationen |
KR100846597B1 (ko) * | 2007-01-24 | 2008-07-16 | 삼성에스디아이 주식회사 | 함불소 화합물 및 탄소계 화합물을 포함하는 유기 발광소자 |
WO2008108254A1 (en) * | 2007-03-07 | 2008-09-12 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and light-emitting device |
JP5530608B2 (ja) | 2007-09-13 | 2014-06-25 | 株式会社半導体エネルギー研究所 | 発光素子および発光装置 |
US8003008B1 (en) | 2007-10-08 | 2011-08-23 | Clemson University | Color-tailored polymer light emitting diodes including emissive colloidal particles and method of forming same |
US8040053B2 (en) * | 2008-02-09 | 2011-10-18 | Universal Display Corporation | Organic light emitting device architecture for reducing the number of organic materials |
KR100922757B1 (ko) * | 2008-02-19 | 2009-10-21 | 삼성모바일디스플레이주식회사 | 수명을 향상시킨 유기 발광 소자 |
US8896201B2 (en) | 2008-02-19 | 2014-11-25 | Samsung Display Co., Ltd. | Organic light emitting device |
US8324800B2 (en) * | 2008-06-12 | 2012-12-04 | Global Oled Technology Llc | Phosphorescent OLED device with mixed hosts |
EP2329544B1 (en) * | 2008-09-04 | 2017-05-17 | Universal Display Corporation | White phosphorescent organic light emitting devices |
TW201035058A (en) * | 2009-03-31 | 2010-10-01 | Chien-Hong Cheng | Organometallic compound and organic light-emitting diode including the same |
DE102009057167A1 (de) | 2009-12-05 | 2011-06-09 | Merck Patent Gmbh | Elektronische Vorrichtung enthaltend Metallkomplexe |
US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
DE102010013495A1 (de) | 2010-03-31 | 2011-10-06 | Siemens Aktiengesellschaft | Dotierstoff für eine Lochleiterschicht für organische Halbleiterbauelemente und Verwendung dazu |
JP5639181B2 (ja) * | 2010-09-24 | 2014-12-10 | 株式会社日立製作所 | 有機発光装置及びこれを用いた光源装置 |
US8933436B2 (en) | 2010-10-13 | 2015-01-13 | The Regents Of The University Of Michigan | Ordered organic-organic multilayer growth |
JP6015451B2 (ja) * | 2011-01-12 | 2016-10-26 | 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、照明装置及び表示装置 |
KR20130007307A (ko) | 2011-06-30 | 2013-01-18 | 삼성디스플레이 주식회사 | 유기 발광 표시 장치 |
DE102011084639A1 (de) | 2011-10-17 | 2013-04-18 | Osram Opto Semiconductors Gmbh | Organisches elektronisches bauelement mit dotierstoff, verwendung eines dotierstoffs und verfahren zur herstellung des dotierstoffs |
US10818853B2 (en) | 2015-06-04 | 2020-10-27 | University Of Southern California | Organic electroluminescent materials and devices |
KR102684614B1 (ko) * | 2015-12-21 | 2024-07-15 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도 |
KR101928934B1 (ko) * | 2016-02-23 | 2018-12-13 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN105576146B (zh) | 2016-03-23 | 2017-09-26 | 京东方科技集团股份有限公司 | 发光器件及其制造方法和显示装置 |
KR102562899B1 (ko) * | 2016-06-02 | 2023-08-04 | 삼성디스플레이 주식회사 | 발광 소자 |
CN108206241B (zh) * | 2016-12-19 | 2020-02-04 | 上海和辉光电有限公司 | 发光器件及制备方法,及有机电致发光显示器 |
KR102478039B1 (ko) | 2017-02-20 | 2022-12-14 | 노발레드 게엠베하 | 전자 반도전성 소자, 전자 반도전성 소자를 제조하기 위한 방법, 및 화합물 |
US11094903B2 (en) | 2017-04-07 | 2021-08-17 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element having an organic compound and a transition metal forming SOMO |
CN109216565B (zh) * | 2017-06-30 | 2021-05-18 | 昆山国显光电有限公司 | 有机电致发光器件及其制备方法 |
CN109427985B (zh) | 2017-08-31 | 2019-12-24 | 昆山国显光电有限公司 | 有机电致发光器件及显示装置 |
CN209104191U (zh) * | 2018-09-18 | 2019-07-12 | 云谷(固安)科技有限公司 | 一种有机发光二极管和显示面板 |
Family Cites Families (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4359507A (en) * | 1981-11-19 | 1982-11-16 | Atlantic Richfield Company | Mixed ethylene and propylene carbonate-containing organic polyisocyanate adhesive binder composition |
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
US5141671A (en) | 1991-08-01 | 1992-08-25 | Eastman Kodak Company | Mixed ligand 8-quinolinolato aluminum chelate luminophors |
US5294870A (en) | 1991-12-30 | 1994-03-15 | Eastman Kodak Company | Organic electroluminescent multicolor image display device |
JP3332491B2 (ja) | 1993-08-27 | 2002-10-07 | 三洋電機株式会社 | 有機el素子 |
US5504183A (en) * | 1994-09-12 | 1996-04-02 | Motorola | Organometallic fluorescent complex polymers for light emitting applications |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US6358631B1 (en) | 1994-12-13 | 2002-03-19 | The Trustees Of Princeton University | Mixed vapor deposited films for electroluminescent devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5693962A (en) * | 1995-03-22 | 1997-12-02 | Motorola | Full color organic light emitting diode array |
US5554220A (en) | 1995-05-19 | 1996-09-10 | The Trustees Of Princeton University | Method and apparatus using organic vapor phase deposition for the growth of organic thin films with large optical non-linearities |
JPH09279134A (ja) * | 1996-04-11 | 1997-10-28 | Shinko Electric Ind Co Ltd | 有機el素子 |
JP4030608B2 (ja) * | 1996-05-01 | 2008-01-09 | 三菱化学株式会社 | 有機電界発光素子及びその製造方法 |
US6048630A (en) | 1996-07-02 | 2000-04-11 | The Trustees Of Princeton University | Red-emitting organic light emitting devices (OLED's) |
JPH1079297A (ja) * | 1996-07-09 | 1998-03-24 | Sony Corp | 電界発光素子 |
US5998803A (en) | 1997-05-29 | 1999-12-07 | The Trustees Of Princeton University | Organic light emitting device containing a hole injection enhancement layer |
US6045930A (en) | 1996-12-23 | 2000-04-04 | The Trustees Of Princeton University | Materials for multicolor light emitting diodes |
US5861219A (en) | 1997-04-15 | 1999-01-19 | The Trustees Of Princeton University | Organic light emitting devices containing a metal complex of 5-hydroxy-quinoxaline as a host material |
US5986401A (en) | 1997-03-20 | 1999-11-16 | The Trustee Of Princeton University | High contrast transparent organic light emitting device display |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5811833A (en) | 1996-12-23 | 1998-09-22 | University Of So. Ca | Electron transporting and light emitting layers based on organic free radicals |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6150043A (en) | 1998-04-10 | 2000-11-21 | The Trustees Of Princeton University | OLEDs containing thermally stable glassy organic hole transporting materials |
US6030715A (en) | 1997-10-09 | 2000-02-29 | The University Of Southern California | Azlactone-related dopants in the emissive layer of an OLED |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6387544B1 (en) | 1998-04-10 | 2002-05-14 | The Trustees Of Princeton University | OLEDS containing thermally stable glassy organic hole transporting materials |
US6210814B1 (en) | 1998-04-10 | 2001-04-03 | The University Of Southern California | Color-tunable organic light emitting devices |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6166489A (en) | 1998-09-15 | 2000-12-26 | The Trustees Of Princeton University | Light emitting device using dual light emitting stacks to achieve full-color emission |
US6214631B1 (en) | 1998-10-30 | 2001-04-10 | The Trustees Of Princeton University | Method for patterning light emitting devices incorporating a movable mask |
US6274980B1 (en) | 1998-11-16 | 2001-08-14 | The Trustees Of Princeton University | Single-color stacked organic light emitting device |
JP2000196140A (ja) * | 1998-12-28 | 2000-07-14 | Sharp Corp | 有機エレクトロルミネッセンス素子とその製造法 |
US6160267A (en) * | 1999-01-05 | 2000-12-12 | Regents Of The University Of Minnesota | Vapochromic led |
JP2000315577A (ja) * | 1999-04-28 | 2000-11-14 | Canon Inc | 有機発光素子 |
EP1449238B1 (en) * | 1999-05-13 | 2006-11-02 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
JP2001043977A (ja) * | 1999-05-27 | 2001-02-16 | Tdk Corp | 発光ダイオード |
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 |
WO2001015244A1 (en) | 1999-08-20 | 2001-03-01 | Emagin Corporation | Organic light emitting diode device with high work function metal-oxide anode layer and method of fabrication of same |
JP3924648B2 (ja) * | 1999-11-02 | 2007-06-06 | ソニー株式会社 | 有機電界発光素子 |
EP2911211B1 (en) * | 1999-12-01 | 2018-05-02 | The Trustees of Princeton University | Complexes of form l2mx |
JP3929689B2 (ja) * | 2000-03-28 | 2007-06-13 | 富士フイルム株式会社 | 高効率赤色発光素子、イリジウム錯体から成る発光素子材料及び新規イリジウム錯体 |
JP2001181617A (ja) * | 1999-12-27 | 2001-07-03 | Fuji Photo Film Co Ltd | オルトメタル化白金錯体からなる発光素子材料および発光素子 |
JP2001181616A (ja) * | 1999-12-27 | 2001-07-03 | Fuji Photo Film Co Ltd | オルトメタル化パラジウム錯体からなる発光素子材料および発光素子 |
US6689493B2 (en) * | 2000-02-18 | 2004-02-10 | Nec Corporation | Organic electroluminescent element and organic electroluminescent display |
JP4890669B2 (ja) * | 2000-03-13 | 2012-03-07 | Tdk株式会社 | 有機el素子 |
JP4048521B2 (ja) | 2000-05-02 | 2008-02-20 | 富士フイルム株式会社 | 発光素子 |
US6765348B2 (en) * | 2001-01-26 | 2004-07-20 | Xerox Corporation | Electroluminescent devices containing thermal protective layers |
JP3812730B2 (ja) * | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP2002334786A (ja) * | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002343568A (ja) * | 2001-05-10 | 2002-11-29 | Sony Corp | 有機電界発光素子 |
JP4158426B2 (ja) * | 2001-06-08 | 2008-10-01 | 東レ株式会社 | 発光素子 |
AU2002320158A1 (en) * | 2001-06-21 | 2003-01-08 | The Trustees Of Princeton University | Organic light-emitting devices with blocking and transport layers |
US6699597B2 (en) * | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
JP4409942B2 (ja) * | 2001-08-29 | 2010-02-03 | ザ トラスティーズ オブ プリンストン ユニバーシテイ | 金属錯体を含むキャリア輸送層を有する有機発光デバイス |
KR100917347B1 (ko) * | 2001-08-29 | 2009-09-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 금속 착물들을 포함하는 캐리어 블로킹층들을 갖는 유기발광 디바이스들 |
US6835469B2 (en) * | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
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KR20040039321A (ko) | 2004-05-10 |
JP2010010691A (ja) | 2010-01-14 |
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CN1628491A (zh) | 2005-06-15 |
EP2259360A2 (en) | 2010-12-08 |
JP4409942B2 (ja) | 2010-02-03 |
CN100511760C (zh) | 2009-07-08 |
JP2005502166A (ja) | 2005-01-20 |
CN101694867A (zh) | 2010-04-14 |
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EP2259360A3 (en) | 2011-08-10 |
WO2003022008A1 (en) | 2003-03-13 |
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US7078113B2 (en) | 2006-07-18 |
KR100937900B1 (ko) | 2010-01-21 |
US7288331B2 (en) | 2007-10-30 |
US20060257685A1 (en) | 2006-11-16 |
CN101694867B (zh) | 2014-10-22 |
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