JP2011016837A - 複核錯体、有機金属錯体、及び有機金属錯体の作製方法 - Google Patents
複核錯体、有機金属錯体、及び有機金属錯体の作製方法 Download PDFInfo
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- JP2011016837A JP2011016837A JP2010208270A JP2010208270A JP2011016837A JP 2011016837 A JP2011016837 A JP 2011016837A JP 2010208270 A JP2010208270 A JP 2010208270A JP 2010208270 A JP2010208270 A JP 2010208270A JP 2011016837 A JP2011016837 A JP 2011016837A
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- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Abstract
【解決手段】一般式(1)であらわされる塩素架橋の複核錯体を中間生成物として、耐熱性に優れた有機金属錯体を合成する。また、合成された前記有機金属錯体を用いて電界発光素子に適用する。
(R1〜R7はそれぞれ、水素原子、ハロゲン原子、低級アルキル基、アルコキシル基、アシル基、ニトロ基、シアノ基、アミノ基、ジアルキルアミノ基、ジアリールアミノ基、ビニル基、アリール基、または複素環残基、のいずれかを表す。またXは、酸素原子または硫黄原子を表す。またYは、窒素原子をヘテロ原子として含む複素環残基を表す。)
【選択図】なし
Description
(非特許文献2)筒井哲夫、応用物理学会 有機分子・バイオエレクトロニクス分科会 第3回講習会テキスト、31−37(1993)
(R1〜R7はそれぞれ同一でも異なっていても良く、水素原子、またはハロゲン原子、または低級アルキル基、またはアルコキシ基、またはアシル基、またはニトロ基、またはシアノ基、またはアミノ基、またはジアルキルアミノ基、またはジアリールアミノ基、または置換基を有してもよいビニル基、または置換基を有してもよいアリール基、または置換基を有してもよい複素環残基、のいずれかを表す。また、R1とR2、R2とR3、R4とR5、R5とR6はそれぞれ互いに結合し、芳香族環を形成してもよい。またXは、酸素原子または硫黄原子を表す。またYは、窒素原子をヘテロ原子として含む複素環残基を表す。またMは、第9族原子または第10族原子を表す。)
(R1〜R7はそれぞれ同一でも異なっていても良く、水素原子、またはハロゲン原子、または低級アルキル基、またはアルコキシ基、またはアシル基、またはニトロ基、またはシアノ基、またはアミノ基、またはジアルキルアミノ基、またはジアリールアミノ基、または置換基を有してもよいビニル基、または置換基を有してもよいアリール基、または置換基を有してもよい複素環残基、のいずれかを表す。また、R1とR2、R2とR3、R4とR5、R5とR6はそれぞれ互いに結合し、芳香族環を形成してもよい。またXは、酸素原子または硫黄原子を表す。またYは、窒素原子をヘテロ原子として含む複素環残基を表す。またMは、第9族原子または第10族原子を表し、前記Mが第9族原子の場合はn=2、第10族原子の場合はn=1となる。またLは、ベータジケトン構造を有するモノアニオン性の二座キレート配位子、またはカルボキシル基を有するモノアニオン性の二座キレート配位子、またはフェノール性水酸基を有するモノアニオン性の二座キレート配位子、のいずれかを表す。)
(Xは、酸素原子または硫黄原子を表す。またMは、第9族原子または第10族原子を表す。)
(Xは、酸素原子または硫黄原子を表す。またMは、第9族原子または第10族原子を表し、前記Mが第9族原子の場合はn=2、第10族原子の場合はn=1となる。またLは、ベータジケトン構造を有するモノアニオン性の二座キレート配位子、またはカルボキシル基を有するモノアニオン性の二座キレート配位子、またはフェノール性水酸基を有するモノアニオン性の二座キレート配位子、のいずれかを表す。)
以下では、本発明の電界発光素子の実施形態について、詳細に説明する。
本実施の形態1では、本発明の有機金属錯体を含む発光層と、低分子系材料からなるホール注入層、ホール輸送層、ホールブロッキング層および電子輸送層を有する電界発光素子の素子構成について図1を用いて説明する。
なお、本実施の形態1においては、本発明の有機金属錯体から得られる発光を発光色とする電界発光素子である。
本実施の形態2では、本発明の有機金属錯体を含む発光層と、高分子系材料からなるホール注入層を有し、これらを湿式プロセスにて形成する電界発光素子の素子構成について図2を用いて説明する。
本実施の形態3では、本発明の有機金属錯体と蛍光性化合物の二種類のゲスト材料を含む発光層と、低分子系材料からなるホール注入層、ホール輸送層、ホールブロッキング層および電子輸送層を有する電界発光素子の素子構成について図3を用いて説明する。
なお、基板300、第1の電極301、第2の電極303、ホール注入層311、ホール輸送層312、ホールブロッキング層314、電子輸送層315については、実施の形態1と同様の材料を用いて、同様にして形成することができるため説明を省略する。
また、電界発光層302は、本実施の形態3では、ホール注入層311、ホール輸送層312、発光層313、ホールブロッキング層314、電子輸送層315を積層することにより形成される。
本合成例では、上記構造式(13)で表される本発明の有機金属錯体(略称:Ir(ppt)2(acac))の合成法を例示する。
まず、o−ジクロロベンゼン・20mlを溶媒として、フェノチアジン(東京化成工業社製)を2.35g(11.8mmol)、2−ヨードピリジン(東京化成工業社製)を3.63g(17.7mmol)、炭酸カリウムを6.55g、銅粉末を1.5g、18−クラウン−6−エーテルを0.31g混合し、窒素雰囲気中で16時間還流した。その後、銅および無機塩を除去し、トルエン溶媒にてカラム精製を行うことにより、配位子ppt(10−(2−ピリジル)フェノチアジン)を得た(乳白色粉末、収率70%)。合成スキームの概要を下記(a−1)に示す。
次に、2−エトキシエタノール30mlと水10mlとの混合液を溶媒として、上記で得たpptを1.19g(4.3mmol)、塩化イリジウム(IrCl3・HCl・H2O)(キシダ化学社製)を0.50g(1.7mmol)混合し、窒素雰囲気下にて18時間還流することにより、複核錯体[Ir(ppt)2Cl]2を得た(黄色粉末、収率70%)。合成スキームの概要を下記(b−1)に示す。
さらに、2−エトキシエタノール30mlを溶媒として、上記で得られた[Ir(ppt)2Cl]2を0.78g(0.50mmol)、アセチルアセトンを0.15ml(1.5mmol)、炭酸ナトリウムを0.53g混合し、窒素雰囲気下にて18時間還流した。得られた黄色粉末を、ジクロロメタンを溶媒としてカラム精製することにより、本発明の有機金属錯体Ir(ppt)2(acac)を得た(黄色粉末、収率60%)。合成スキームの概要を下記(c−1)に示す。
下記構造式(29)で表される従来のイリジウム錯体(略称:Ir(tpy)2(acac))を合成し、分解温度TdをTG−DTAにより測定したところ、Td=298℃であった。
本合成例では、上記構造式(17)で表される本発明の有機金属錯体(略称:Ir(ppx)2(acac))の合成法を例示する。
まず、オルトジクロロベンゼン・20mlを溶媒として、フェノキサジンを1.73g、2−ヨードピリジンを2.90g、炭酸カリウムを5.24g、銅粉末を1.2g、18−クラウン−6−エーテルを0.25g混合し、窒素雰囲気下にて8時間還流した。その後、銅および無機塩を除去し、ジクロロメタン溶媒にてカラム精製を行うことにより、配位子ppx(1−(2−ピリジル)フェノキサジン)を得た(白色粉末、収率91%)。合成スキームの概要を下記(a−2)に示す。
次に、2−エトキシエタノール30mlと水10mlとの混合液を溶媒として、上記で得たppxを2.18g、塩化イリジウム(IrCl3・HCl・H2O)を1.00g混合し、窒素雰囲気下で14時間還流することにより、複核錯体[Ir(ppx)2Cl]2 を得た(黄色粉末、収率96%)。合成スキームの概要を下記(b−2)に示す。
さらに、2−エトキシエタノール30mlを溶媒として、上記で得られた[Ir(ppx)2Cl]2 を1.00g、アセチルアセトン(Hacac)を0.21ml、炭酸ナトリウムを0.71g混合し、窒素雰囲気下にて14時間還流した。得られた固体を、水、エタノール、エーテル溶媒にて洗浄することにより、本発明の有機金属錯体Ir(ppx)2(acac)を得た(黄色粉末、収率87%)。合成スキームの概要を下記(c−2)に示す。
本合成例では、上記構造式(18)で表される本発明の有機金属錯体(略称:Ir(ppx)2(pic))の合成法を例示する。原料としては、上述した合成例2のステップ2で得られる複核錯体[Ir(ppx)2Cl]2を用いた。
次に、Ir(ppx)2(pic)のジクロロメタン中における吸収スペクトルおよび発光スペクトル(フォトルミネッセンス)を図9に示す。本発明の有機金属錯体Ir(ppx)2(pic)は226nm、314nm、338nmおよび396nmに吸収ピークを有しており、合成例1と同様、オルトメタル錯体等によく見られる有機金属錯体特有の吸収スペクトルを呈していた。また、発光スペクトルは551nmにピークを有しており、黄緑色発光であった。
Claims (8)
- 下記一般式(1)で表される構造を有する塩素架橋の複核錯体。
- 下記一般式(2)で表される構造を有する有機金属錯体。
- 下記構造式(3)で表される構造を有する有機金属錯体。
- 下記構造式(4)で表される構造を有する有機金属錯体。
- 下記構造式(5)で表される構造を有する有機金属錯体。
- 下記構造式(6)で表される構造を有する有機金属錯体。
- 下記一般式(1)で表される塩素架橋の複核錯体と二座キレート配位子を混合し、
前記複核錯体の前記塩素架橋を前記二座キレート配位子で切断することにより有機金属錯体を生成する方法であって、
前記二座キレート配位子は、ベータジケトン構造を有するモノアニオン性の二座キレート配位子、カルボキシル基を有するモノアニオン性の二座キレート配位子、またはフェノール性水酸基を有するモノアニオン性の二座キレート配位子のいずれかであることを特徴とする有機金属錯体の作製方法。
- 請求項7において、
二座キレート配位子は、アセチルアセトン、マロン酸ジメチル、ピコリン酸、プロリン、サリチリデンアミン、サリチルアルデヒド、8−キノリノールのいずれかであることを特徴とする有機金属錯体の作製方法。
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Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101054663B1 (ko) * | 2003-02-14 | 2011-08-08 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 금속 착체, 이들 착체를 사용하는 전계 발광 재료 및이들 착체를 사용하는 전계 발광 소자 |
US7764012B2 (en) * | 2004-04-16 | 2010-07-27 | Semiconductor Energy Laboratory Co., Ltd | Light emitting device comprising reduced frame portion, manufacturing method with improve productivity thereof, and electronic apparatus |
US7667389B2 (en) * | 2004-12-06 | 2010-02-23 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element, light emitting device, and electronic device |
TWI307250B (en) * | 2005-03-23 | 2009-03-01 | Au Optronics Corp | Organic electroluminescent device |
WO2006109878A1 (en) | 2005-04-11 | 2006-10-19 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and vapor deposition apparatus |
US7745019B2 (en) * | 2005-04-28 | 2010-06-29 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element and light emitting device and method of manufacturing light emitting element |
US20060244373A1 (en) * | 2005-04-28 | 2006-11-02 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and method for manufacturing thereof |
US8415878B2 (en) | 2005-07-06 | 2013-04-09 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and electronic device |
US7935957B2 (en) * | 2005-08-12 | 2011-05-03 | Semiconductor Energy Laboratory Co., Ltd. | Memory device and a semiconductor device |
DE102007033746A1 (de) | 2006-10-12 | 2008-04-17 | Giesecke & Devrient Gmbh | Verwaltung von Datenobjekten in einem Haldenspeicher |
US8425801B2 (en) * | 2009-04-10 | 2013-04-23 | Idemitsu Kosan Co., Ltd. | Composite organic electroluminescent material and production method thereof |
EP2471889A4 (en) | 2009-08-27 | 2013-06-26 | Sumitomo Chemical Co | METAL COMPLEX COMPOSITION AND COMPLEX POLYMER |
WO2011024737A1 (ja) | 2009-08-27 | 2011-03-03 | 独立行政法人産業技術総合研究所 | イリジウム錯体ならびに該化合物からなる発光材料 |
US9312505B2 (en) * | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9957260B2 (en) | 2013-08-09 | 2018-05-01 | Kyushu University, National University Corporation | Organic metal complex, light emitting material, delayed fluorescent material, and organic light emitting device |
US10115912B2 (en) | 2015-04-28 | 2018-10-30 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
JP6847589B2 (ja) | 2015-05-20 | 2021-03-24 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
KR102486382B1 (ko) * | 2015-08-03 | 2023-01-09 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
JP6935176B2 (ja) | 2015-08-31 | 2021-09-15 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
US10774032B2 (en) * | 2015-09-22 | 2020-09-15 | Florida State University Research Foundation, Inc. | Organometal halide perovskit nanoplatelets, devices, and methods |
US9938309B2 (en) | 2015-12-28 | 2018-04-10 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
US10975113B2 (en) * | 2017-04-21 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003146996A (ja) * | 2000-09-26 | 2003-05-21 | Canon Inc | 発光素子、表示装置及び発光素子用金属配位化合物 |
JP2003342284A (ja) * | 2002-05-30 | 2003-12-03 | Canon Inc | 金属配位化合物、発光素子及び表示装置 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP2004155728A (ja) * | 2002-11-07 | 2004-06-03 | Mitsubishi Chemicals Corp | 金属錯体の製造方法 |
KR101054663B1 (ko) * | 2003-02-14 | 2011-08-08 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 금속 착체, 이들 착체를 사용하는 전계 발광 재료 및이들 착체를 사용하는 전계 발광 소자 |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003146996A (ja) * | 2000-09-26 | 2003-05-21 | Canon Inc | 発光素子、表示装置及び発光素子用金属配位化合物 |
JP2003342284A (ja) * | 2002-05-30 | 2003-12-03 | Canon Inc | 金属配位化合物、発光素子及び表示装置 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016184773A (ja) * | 2011-02-16 | 2016-10-20 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、及び照明装置 |
US10403839B2 (en) | 2011-02-16 | 2019-09-03 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
US11038135B2 (en) | 2011-02-16 | 2021-06-15 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
US11812626B2 (en) | 2011-02-16 | 2023-11-07 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
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KR101054663B1 (ko) | 2011-08-08 |
US20060106211A1 (en) | 2006-05-18 |
EP1598361A1 (en) | 2005-11-23 |
EP1598361B1 (en) | 2013-05-29 |
JPWO2004081019A1 (ja) | 2006-06-08 |
JP5171910B2 (ja) | 2013-03-27 |
JP4628108B2 (ja) | 2011-02-09 |
TWI347349B (en) | 2011-08-21 |
US7176307B2 (en) | 2007-02-13 |
TW200420178A (en) | 2004-10-01 |
WO2004081019A1 (ja) | 2004-09-23 |
US20050006625A1 (en) | 2005-01-13 |
US7041390B2 (en) | 2006-05-09 |
KR20050106412A (ko) | 2005-11-09 |
EP1598361A4 (en) | 2009-08-26 |
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