JP2005190987A - 発光素子 - Google Patents
発光素子 Download PDFInfo
- Publication number
- JP2005190987A JP2005190987A JP2004298501A JP2004298501A JP2005190987A JP 2005190987 A JP2005190987 A JP 2005190987A JP 2004298501 A JP2004298501 A JP 2004298501A JP 2004298501 A JP2004298501 A JP 2004298501A JP 2005190987 A JP2005190987 A JP 2005190987A
- Authority
- JP
- Japan
- Prior art keywords
- ring
- light
- copper
- coordination compound
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- YNEYXHPHEAEPIE-UHFFFAOYSA-N CCCC1(C(C=CC2)=NC2F)S(=C)=S1 Chemical compound CCCC1(C(C=CC2)=NC2F)S(=C)=S1 YNEYXHPHEAEPIE-UHFFFAOYSA-N 0.000 description 1
- OGPIRWGZXGIDCT-UHFFFAOYSA-N C[Si](C)(C)C(c1nc(F)ccc1)[Si](C)(C)C Chemical compound C[Si](C)(C)C(c1nc(F)ccc1)[Si](C)(C)C OGPIRWGZXGIDCT-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- 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
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- 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
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
-
- 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
Abstract
Description
(1)MLCT(metal−to−ligand−charge−transfer)励起状態
(2)金属中心励起状態
(3)配位子中心(ππ*)励起状態
製造例1〜3で製造した化合物の粉末状態での発光特性の測定を行った。結果を表8に示す。また、代表例として例示化合物1001の発光スペクトルを図2に示す。
本実施例では、素子構成として、図1(d)に示す有機層が3層の素子を使用した。
ホール輸送層13(40nm):化合物FL1
発光層12(40nm,20nm):CBP/例示化合物1001(重量比10重量%)
電子輸送層16(50nm):BPhen
金属電極層1(1nm):KF
金属電極層2(100nm):Al
本実施例では、素子構成として、図1(d)に示す有機層が3層の素子を使用した。
脱水クロロベンゼン:10g
ポリビニルカルバゾール(平均分子量9600):92mg
例示化合物1001:8mg
金属電極層1(15nm):AlLi合金(Li含有量1.8重量%)
金属電極層2(100nm):Al
金属電極11をマイナス、透明電極14をプラスにしてDC電圧を印加して素子特性を評価した。
発光層の例示化合物1001の濃度を50重量%(実施例4)、100重量%、つまり例示化合物1001のみ(実施例5)とした以外は、実施例2と同様にして素子を作成した。600cd/m2の輝度のときの効率を表10に示す。
例示化合物1001に替えて例示化合物1007を用いた以外は実施例1、2、5と同様にして素子を作成した。600cd/m2の輝度のときの効率を表11に示す。
例示化合物1001を例示化合物1176に変更した以外は実施例3と同様にして素子を作成した。600cd/m2の輝度のときの効率を表12に示す。
12 発光層
13 ホール輸送層
14 透明電極
15 透明基板
16 電子輸送層
17 励起子拡散防止層
Claims (9)
- 前記銅配位化合物の銅原子間隔が3.2オングストローム以下であることを特徴とする請求項1〜6のいずれかに記載の発光素子。
- 前記銅配位化合物の銅が一価のイオンであることを特徴とする請求項1〜7のいずれかに記載の発光素子。
- 発光層が前記銅配位化合物100%の部分を含むことを特徴とする請求項1〜8のいずれかに記載の発光素子。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004298501A JP4328702B2 (ja) | 2003-12-01 | 2004-10-13 | 有機el素子 |
PCT/JP2004/017331 WO2005054404A1 (en) | 2003-12-01 | 2004-11-16 | Luminescent device |
US10/577,160 US7875366B2 (en) | 2003-12-01 | 2004-11-16 | Luminescent device |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003401821 | 2003-12-01 | ||
JP2004298501A JP4328702B2 (ja) | 2003-12-01 | 2004-10-13 | 有機el素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005190987A true JP2005190987A (ja) | 2005-07-14 |
JP4328702B2 JP4328702B2 (ja) | 2009-09-09 |
Family
ID=34656189
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004298501A Expired - Fee Related JP4328702B2 (ja) | 2003-12-01 | 2004-10-13 | 有機el素子 |
Country Status (3)
Country | Link |
---|---|
US (1) | US7875366B2 (ja) |
JP (1) | JP4328702B2 (ja) |
WO (1) | WO2005054404A1 (ja) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010114428A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 有機el表示装置 |
JP2010114429A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 表示装置 |
JP2010114425A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 有機el表示装置 |
WO2012056931A1 (ja) * | 2010-10-28 | 2012-05-03 | 住友化学株式会社 | 燐光発光素子 |
JP2014140048A (ja) * | 2008-10-10 | 2014-07-31 | Canon Inc | 有機el表示装置 |
JP2014532034A (ja) * | 2011-08-02 | 2014-12-04 | サイノーラ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 光電子デバイスのためのデュアルコア銅(i)錯体による一重項収穫 |
JP2018125563A (ja) * | 2012-02-09 | 2018-08-09 | 株式会社半導体エネルギー研究所 | 発光方法、発光素子、発光装置、電子機器および照明装置 |
JP2019062240A (ja) * | 2012-04-13 | 2019-04-18 | 株式会社半導体エネルギー研究所 | 発光装置、電子機器、照明装置 |
US10818861B2 (en) | 2012-04-13 | 2020-10-27 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4478555B2 (ja) * | 2004-11-30 | 2010-06-09 | キヤノン株式会社 | 金属錯体、発光素子及び画像表示装置 |
JP5084204B2 (ja) * | 2006-09-06 | 2012-11-28 | キヤノン株式会社 | 発光素子及び高分子混合金属錯体 |
JP5110851B2 (ja) * | 2006-11-01 | 2012-12-26 | キヤノン株式会社 | 有機発光素子 |
JP5305637B2 (ja) | 2007-11-08 | 2013-10-02 | キヤノン株式会社 | 有機金属錯体及びこれを用いた有機発光素子並びに表示装置 |
DE102008048336A1 (de) | 2008-09-22 | 2010-03-25 | Merck Patent Gmbh | Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen |
JP5562657B2 (ja) * | 2009-01-23 | 2014-07-30 | 住友化学株式会社 | 有機電界発光素子 |
WO2011070963A1 (ja) * | 2009-12-07 | 2011-06-16 | 新日鐵化学株式会社 | 有機発光材料及び有機発光素子 |
PL222231B1 (pl) | 2010-07-07 | 2016-07-29 | Inst Chemii Fizycznej Polskiej Akademii Nauk | Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanie |
JP2015185829A (ja) | 2014-03-26 | 2015-10-22 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用発光材料、および有機エレクトロルミネッセンス素子 |
CN104910897B (zh) * | 2015-06-17 | 2017-01-04 | 中国计量学院 | 一种Cu3I2阳离子型亚铜簇合物绿色磷光材料 |
CN111909183B (zh) * | 2020-08-28 | 2022-07-29 | 江西理工大学 | 一种叔丁基吡啶吡唑铜[i]双核配合物刺激响应发光变色材料的制备方法 |
CN113717397B (zh) * | 2021-09-02 | 2022-04-05 | 暨南大学 | 一种金属团簇基晶态多孔材料的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2814435B2 (ja) * | 1987-03-02 | 1998-10-22 | イーストマン・コダック・カンパニー | 改良薄膜発光帯をもつ電場発光デバイス |
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
JP2940514B2 (ja) | 1997-05-07 | 1999-08-25 | 日本電気株式会社 | 有機エレクトロルミネッセント素子 |
US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
JP4255635B2 (ja) * | 2000-11-30 | 2009-04-15 | 株式会社半導体エネルギー研究所 | 発光装置 |
US6764776B2 (en) | 2000-11-30 | 2004-07-20 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device |
JP2003332074A (ja) | 2002-05-09 | 2003-11-21 | Canon Inc | 金属配位化合物を用いた発光素子 |
JP4208657B2 (ja) | 2003-07-15 | 2009-01-14 | キヤノン株式会社 | 発光素子 |
JP4557651B2 (ja) | 2003-10-01 | 2010-10-06 | キヤノン株式会社 | 発光性銅配位化合物及び有機発光素子 |
-
2004
- 2004-10-13 JP JP2004298501A patent/JP4328702B2/ja not_active Expired - Fee Related
- 2004-11-16 US US10/577,160 patent/US7875366B2/en not_active Expired - Fee Related
- 2004-11-16 WO PCT/JP2004/017331 patent/WO2005054404A1/en active Application Filing
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010114428A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 有機el表示装置 |
JP2010114429A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 表示装置 |
JP2010114425A (ja) * | 2008-10-10 | 2010-05-20 | Canon Inc | 有機el表示装置 |
JP2014140048A (ja) * | 2008-10-10 | 2014-07-31 | Canon Inc | 有機el表示装置 |
WO2012056931A1 (ja) * | 2010-10-28 | 2012-05-03 | 住友化学株式会社 | 燐光発光素子 |
US9537117B2 (en) | 2011-08-02 | 2017-01-03 | Cynora Gmbh | Singlet harvesting with dual-core copper (I) complexes for optoelectronic devices |
JP2014532034A (ja) * | 2011-08-02 | 2014-12-04 | サイノーラ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 光電子デバイスのためのデュアルコア銅(i)錯体による一重項収穫 |
JP2018125563A (ja) * | 2012-02-09 | 2018-08-09 | 株式会社半導体エネルギー研究所 | 発光方法、発光素子、発光装置、電子機器および照明装置 |
US10326093B2 (en) | 2012-02-09 | 2019-06-18 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
US10693093B2 (en) | 2012-02-09 | 2020-06-23 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
US11495763B2 (en) | 2012-02-09 | 2022-11-08 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
JP2019062240A (ja) * | 2012-04-13 | 2019-04-18 | 株式会社半導体エネルギー研究所 | 発光装置、電子機器、照明装置 |
US10818861B2 (en) | 2012-04-13 | 2020-10-27 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
US11393997B2 (en) | 2012-04-13 | 2022-07-19 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
Also Published As
Publication number | Publication date |
---|---|
US20070072001A1 (en) | 2007-03-29 |
WO2005054404A1 (en) | 2005-06-16 |
US7875366B2 (en) | 2011-01-25 |
JP4328702B2 (ja) | 2009-09-09 |
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