TWI287567B - Light-emitting element and iridium complex - Google Patents
Light-emitting element and iridium complex Download PDFInfo
- Publication number
- TWI287567B TWI287567B TW092120909A TW92120909A TWI287567B TW I287567 B TWI287567 B TW I287567B TW 092120909 A TW092120909 A TW 092120909A TW 92120909 A TW92120909 A TW 92120909A TW I287567 B TWI287567 B TW I287567B
- Authority
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- Taiwan
- Prior art keywords
- group
- light
- luminescent material
- emitting element
- ligand
- Prior art date
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- 229910052741 iridium Inorganic materials 0.000 title abstract description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 239000010410 layer Substances 0.000 claims description 45
- 239000000463 material Substances 0.000 claims description 39
- 239000003446 ligand Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000005215 alkyl ethers Chemical class 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
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- 235000019341 magnesium sulphate Nutrition 0.000 description 5
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- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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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
- 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
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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
- 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
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- C—CHEMISTRY; METALLURGY
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- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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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
- 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
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW092120909A TWI287567B (en) | 2003-07-30 | 2003-07-30 | Light-emitting element and iridium complex |
| KR1020040059657A KR20050014708A (ko) | 2003-07-30 | 2004-07-29 | 발광 요소 및 이리듐 착물 |
| US10/902,977 US7560176B2 (en) | 2003-07-30 | 2004-07-29 | Light-emitting element and iridium complex |
| JP2004221628A JP4410631B2 (ja) | 2003-07-30 | 2004-07-29 | 発光素子およびイリジウム錯体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW092120909A TWI287567B (en) | 2003-07-30 | 2003-07-30 | Light-emitting element and iridium complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200504180A TW200504180A (en) | 2005-02-01 |
| TWI287567B true TWI287567B (en) | 2007-10-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW092120909A TWI287567B (en) | 2003-07-30 | 2003-07-30 | Light-emitting element and iridium complex |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7560176B2 (enExample) |
| JP (1) | JP4410631B2 (enExample) |
| KR (1) | KR20050014708A (enExample) |
| TW (1) | TWI287567B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242369A (zh) * | 2013-05-02 | 2013-08-14 | 太原理工大学 | 一种芳香五元杂环取代喹啉铱(iii)配合物及其制备方法和应用 |
| TWI410426B (zh) * | 2010-05-21 | 2013-10-01 | Univ Nat Cheng Kung | 發光銥金屬錯化物和前驅物的低耗能製程 |
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| JP4578131B2 (ja) * | 2003-03-31 | 2010-11-10 | 三洋電機株式会社 | 発光素子用化合物およびそれを用いた有機発光素子 |
| US8097347B2 (en) * | 2004-07-21 | 2012-01-17 | Koninklijke Philips Electronics N.V. | Light-emitting electrochemical cell |
| TWI245587B (en) * | 2005-02-17 | 2005-12-11 | Au Optronics Corp | Organic electro luminescence devices, flat panel displays, and portable electronics using the same |
| US20060263630A1 (en) * | 2005-05-23 | 2006-11-23 | Chung Shan Institute Of Science And Technc | Iridium complex and electroluminescent device using the same |
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| US8133597B2 (en) | 2005-09-06 | 2012-03-13 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
| KR20070069314A (ko) * | 2005-12-28 | 2007-07-03 | 전자부품연구원 | Ｏｌｅｄ 소자 |
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| ATE522588T1 (de) | 2007-04-04 | 2011-09-15 | Basf Se | Iridium-triphenylen-komplexe und deren verwendung in oleds |
| TW200910661A (en) * | 2007-04-04 | 2009-03-01 | Koninkl Philips Electronics Nv | OLED with metal complexes having a high quantum efficiency |
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| JP3929690B2 (ja) * | 1999-12-27 | 2007-06-13 | 富士フイルム株式会社 | オルトメタル化イリジウム錯体からなる発光素子材料、発光素子および新規イリジウム錯体 |
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| KR100874290B1 (ko) * | 2001-02-14 | 2008-12-18 | 산요덴키가부시키가이샤 | 유기 전계 발광 소자, 발광 재료 및 유기 화합물 |
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| EP1426399A4 (en) * | 2001-09-04 | 2005-07-13 | Canon Kk | HIGHLY MOLECULAR COMPOUNDS AND ORGANIC LUMINESCENT DEVICES |
| JP5135660B2 (ja) | 2001-09-27 | 2013-02-06 | 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 |
| US6835469B2 (en) * | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| US7250512B2 (en) * | 2001-11-07 | 2007-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
-
2003
- 2003-07-30 TW TW092120909A patent/TWI287567B/zh not_active IP Right Cessation
-
2004
- 2004-07-29 JP JP2004221628A patent/JP4410631B2/ja not_active Expired - Fee Related
- 2004-07-29 KR KR1020040059657A patent/KR20050014708A/ko not_active Withdrawn
- 2004-07-29 US US10/902,977 patent/US7560176B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI410426B (zh) * | 2010-05-21 | 2013-10-01 | Univ Nat Cheng Kung | 發光銥金屬錯化物和前驅物的低耗能製程 |
| CN103242369A (zh) * | 2013-05-02 | 2013-08-14 | 太原理工大学 | 一种芳香五元杂环取代喹啉铱(iii)配合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050025995A1 (en) | 2005-02-03 |
| JP2005097549A (ja) | 2005-04-14 |
| JP4410631B2 (ja) | 2010-02-03 |
| TW200504180A (en) | 2005-02-01 |
| KR20050014708A (ko) | 2005-02-07 |
| US7560176B2 (en) | 2009-07-14 |
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