PL222231B1 - Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanie - Google Patents
Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanieInfo
- Publication number
- PL222231B1 PL222231B1 PL391776A PL39177610A PL222231B1 PL 222231 B1 PL222231 B1 PL 222231B1 PL 391776 A PL391776 A PL 391776A PL 39177610 A PL39177610 A PL 39177610A PL 222231 B1 PL222231 B1 PL 222231B1
- Authority
- PL
- Poland
- Prior art keywords
- compounds
- reaction
- precursor
- temperature
- acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 230000008569 process Effects 0.000 title claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Chemical group 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910001412 inorganic anion Inorganic materials 0.000 claims abstract description 3
- -1 straight or branched Chemical group 0.000 claims abstract description 3
- 239000011593 sulfur Chemical group 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910001868 water Inorganic materials 0.000 claims description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002243 precursor Substances 0.000 claims description 10
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229960003540 oxyquinoline Drugs 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 claims description 2
- KESRRRLHHXXBRW-UHFFFAOYSA-N C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 Chemical compound C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 KESRRRLHHXXBRW-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- SPVXKVOXSXTJOY-UHFFFAOYSA-N selane Chemical compound [SeH2] SPVXKVOXSXTJOY-UHFFFAOYSA-N 0.000 claims description 2
- 229910000058 selane Inorganic materials 0.000 claims description 2
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 abstract 1
- 239000011701 zinc Substances 0.000 description 14
- 239000007850 fluorescent dye Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 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 4
- XOWIZHGUWJSHBR-UHFFFAOYSA-N CC(C)(C)[Zn] Chemical class CC(C)(C)[Zn] XOWIZHGUWJSHBR-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- JQOATXDBTYKMEX-UHFFFAOYSA-N CC[Zn] Chemical class CC[Zn] JQOATXDBTYKMEX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- 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
- 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
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- 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
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
-
- 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
- C09K2211/186—Metal complexes of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Electroluminescent Light Sources (AREA)
- Quinoline Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL391776A PL222231B1 (pl) | 2010-07-07 | 2010-07-07 | Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanie |
| CN201180042983.XA CN103221509B (zh) | 2010-07-07 | 2011-07-06 | 发光化合物、发光化合物的制备方法和其应用 |
| KR1020137002799A KR20130094297A (ko) | 2010-07-07 | 2011-07-06 | 발광 화합물, 발광 화합물의 제조 방법 및 그것의 용도 |
| JP2013518306A JP2013537517A (ja) | 2010-07-07 | 2011-07-06 | 発光化合物、発光化合物の調製方法およびその用途 |
| PCT/PL2011/000070 WO2012005615A1 (en) | 2010-07-07 | 2011-07-06 | Luminescent compounds, method of preparation of luminescent compounds and applications thereof |
| BR112013000426A BR112013000426A2 (pt) | 2010-07-07 | 2011-07-06 | compostos luminescentes, métodos de preparação de compostos luminescentes e aplicações dos mesmos |
| EP11748764.5A EP2591065A1 (en) | 2010-07-07 | 2011-07-06 | Luminescent compounds, method of preparation of luminescent compounds and applications thereof |
| AU2011274586A AU2011274586B2 (en) | 2010-07-07 | 2011-07-06 | Luminescent compounds, method of preparation of luminescent compounds and applications thereof |
| CA2804366A CA2804366A1 (en) | 2010-07-07 | 2011-07-06 | Luminescent compounds, method of preparation of luminescent compounds and applications thereof |
| US13/808,907 US9217104B2 (en) | 2010-07-07 | 2011-07-06 | Luminescent compounds, method of preparation of luminescent compounds and applications thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL391776A PL222231B1 (pl) | 2010-07-07 | 2010-07-07 | Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL391776A1 PL391776A1 (pl) | 2012-01-16 |
| PL222231B1 true PL222231B1 (pl) | 2016-07-29 |
Family
ID=44511446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL391776A PL222231B1 (pl) | 2010-07-07 | 2010-07-07 | Związki luminescencyjne, sposób wytwarzania związków luminescencyjnych oraz ich zastosowanie |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9217104B2 (enExample) |
| EP (1) | EP2591065A1 (enExample) |
| JP (1) | JP2013537517A (enExample) |
| KR (1) | KR20130094297A (enExample) |
| CN (1) | CN103221509B (enExample) |
| BR (1) | BR112013000426A2 (enExample) |
| CA (1) | CA2804366A1 (enExample) |
| PL (1) | PL222231B1 (enExample) |
| WO (1) | WO2012005615A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9778510B2 (en) * | 2013-10-08 | 2017-10-03 | Samsung Electronics Co., Ltd. | Nanocrystal polymer composites and production methods thereof |
| EP3503234B1 (en) | 2017-12-20 | 2020-11-04 | Novaled GmbH | Organic electronic device comprising an inverse coordination complex and a method for preparing the same |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4720432A (en) | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
| JPH0528678A (ja) | 1991-07-16 | 1993-02-05 | Canon Electron Inc | 記録再生装置のアクセス機構 |
| JP3585060B2 (ja) | 1995-05-10 | 2004-11-04 | ソニー株式会社 | 亜鉛複核錯体、その製造方法及び光学的素子 |
| JP3564859B2 (ja) * | 1996-04-01 | 2004-09-15 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| JP3760508B2 (ja) * | 1996-06-10 | 2006-03-29 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを用いた有機エレクトロルミネッセンス素子 |
| KR100373203B1 (ko) * | 1999-03-31 | 2003-02-25 | 주식회사 엘지화학 | 새로운 큐마린계 착물 및 이를 이용한 유기 발광 소자 |
| WO2001092437A1 (en) * | 2000-06-01 | 2001-12-06 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element material and organic electroluminescent element |
| WO2004073030A2 (en) | 2003-02-06 | 2004-08-26 | Georgia Tech Research Corporation | Metal 8-hydroxyquinoline -functionalized polymers and related materials and methods of making and using the same |
| JP4328702B2 (ja) | 2003-12-01 | 2009-09-09 | キヤノン株式会社 | 有機ｅｌ素子 |
| JP4741920B2 (ja) * | 2005-09-29 | 2011-08-10 | 富士フイルム株式会社 | 有機電界発光素子 |
| JP4478166B2 (ja) * | 2006-11-09 | 2010-06-09 | 三星モバイルディスプレイ株式會社 | 有機金属錯体を含む有機膜を備えた有機発光素子 |
| KR100836020B1 (ko) * | 2007-01-04 | 2008-06-09 | (주)그라쎌 | 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고있는 표시소자 |
| KR100850886B1 (ko) | 2007-09-07 | 2008-08-07 | (주)그라쎌 | 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고있는 표시소자 |
| KR100923566B1 (ko) * | 2007-10-25 | 2009-10-27 | (주)그라쎌 | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
| KR100910151B1 (ko) * | 2007-11-22 | 2009-07-30 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로 채용하고있는 전기발광소자 |
| PL213271B1 (pl) * | 2008-08-22 | 2013-02-28 | Politechnika Warszawska | Prekursory nanocząstek tlenku cynku i sposób wytwarzania prekursorów nanocząstek tlenku cynku |
-
2010
- 2010-07-07 PL PL391776A patent/PL222231B1/pl unknown
-
2011
- 2011-07-06 BR BR112013000426A patent/BR112013000426A2/pt not_active IP Right Cessation
- 2011-07-06 WO PCT/PL2011/000070 patent/WO2012005615A1/en not_active Ceased
- 2011-07-06 US US13/808,907 patent/US9217104B2/en not_active Expired - Fee Related
- 2011-07-06 CN CN201180042983.XA patent/CN103221509B/zh not_active Expired - Fee Related
- 2011-07-06 JP JP2013518306A patent/JP2013537517A/ja active Pending
- 2011-07-06 CA CA2804366A patent/CA2804366A1/en not_active Abandoned
- 2011-07-06 KR KR1020137002799A patent/KR20130094297A/ko not_active Withdrawn
- 2011-07-06 EP EP11748764.5A patent/EP2591065A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN103221509B (zh) | 2016-08-03 |
| WO2012005615A1 (en) | 2012-01-12 |
| US20130131345A1 (en) | 2013-05-23 |
| US9217104B2 (en) | 2015-12-22 |
| CN103221509A (zh) | 2013-07-24 |
| PL391776A1 (pl) | 2012-01-16 |
| CA2804366A1 (en) | 2012-01-12 |
| EP2591065A1 (en) | 2013-05-15 |
| JP2013537517A (ja) | 2013-10-03 |
| AU2011274586A1 (en) | 2013-01-24 |
| KR20130094297A (ko) | 2013-08-23 |
| BR112013000426A2 (pt) | 2016-05-17 |
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