WO2010118661A1 - 8-羟基喹啉或其衍生物的金属化合物的制备方法 - Google Patents
8-羟基喹啉或其衍生物的金属化合物的制备方法 Download PDFInfo
- Publication number
- WO2010118661A1 WO2010118661A1 PCT/CN2010/071409 CN2010071409W WO2010118661A1 WO 2010118661 A1 WO2010118661 A1 WO 2010118661A1 CN 2010071409 W CN2010071409 W CN 2010071409W WO 2010118661 A1 WO2010118661 A1 WO 2010118661A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- hydroxyquinoline
- aluminum
- water
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000005725 8-Hydroxyquinoline Substances 0.000 title claims abstract description 24
- 229960003540 oxyquinoline Drugs 0.000 title claims abstract description 24
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002736 metal compounds Chemical class 0.000 title abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002642 lithium compounds Chemical class 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- -1 Alkoxy aluminum Chemical compound 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical group [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical group [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 claims description 4
- 239000003021 water soluble solvent Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 150000004325 8-hydroxyquinolines Chemical class 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 10
- 230000002209 hydrophobic effect Effects 0.000 abstract 4
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000007086 side reaction 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
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
- 229940063655 aluminum stearate Drugs 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- SXXNJJQVBPWGTP-UHFFFAOYSA-K tris[(4-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-] SXXNJJQVBPWGTP-UHFFFAOYSA-K 0.000 description 2
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- LFHXPRTYXDXTDD-UHFFFAOYSA-H bis(2,2-dioxo-1,3,2,4-dioxathialumetan-4-yl) sulfate octahydrate Chemical compound O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LFHXPRTYXDXTDD-UHFFFAOYSA-H 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/30—Metal salts; Chelates
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
-
- 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
-
- 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
Definitions
- the present invention relates to a method for synthesizing an organic electroluminescent material, and more particularly to a method for preparing a high purity 8-hydroxyquinoline metal (Al, Li) compound.
- 8-hydroxyquinoline aluminum, 8-hydroxyquinoline lithium, bis(2-methyl-8-hydroxyquinoline) phenoxy aluminum is currently the most widely used three 8-hydroxyquinoline metal compounds. It has become a promising electron transport material in organic light-emitting materials and is widely used in various types of electroluminescent devices, and the performance of the device is improved (Liuown, et al. Synthetic Metals, 2002, 128, 221.). However, in the preparation process of the organic light-emitting device, a trace amount of impurities easily cause pinholes, short circuits, and black spots, thereby affecting the life of the device, and thus preparation of a high-purity material is critical.
- the problem to be solved by the present invention is that the yield of 8-hydroxyquinoline is low, the side reaction is large, and the production cycle is long.
- the present invention optimizes the reaction conditions and can control the progress of the reaction.
- a metal compound of a different ligand can be obtained.
- the reaction does not use a protic solvent, easily causes a coordination solvent, avoids the generation of side reactions, improves the yield and purity, and can be directly utilized after the reaction mother liquid is recovered, thereby reducing the cost.
- the reaction temperature is from 25 ° C to 120 ° C.
- the water-soluble solvent I, I I, I I I is one of toluene, xylene, petroleum ether, and halogenated hydrocarbon.
- the water solvents I, II, and III are toluene and xylene; and when the M is lithium, the water solvents I, II, and III are dichloromethane and chloroform.
- the Zengshui Solvent I, the Zengshui Solvent I I, and the Zengshui Solvent I I I are the same solvent.
- the aluminum alkoxide is aluminum isopropoxide.
- the inorganic lithium is hydrated lithium hydroxide or lithium hydroxide.
- the method further comprises a separation step of Mq n q m ', filtering the reaction solution, washing the filtrate, and drying.
- the drying is vacuum drying at a temperature of from 50 ° C to 250 ° C.
- the q' is a phenol and a derivative thereof, a biphenol, and an 8-hydroxyquinoline derivative different from q.
- the raw materials involved in the reaction are respectively dissolved in a water-soluble solvent (an organic solvent which is not miscible with water), and reacted under conditions of nitrogen gas filling and dropping of the raw materials.
- a water-soluble solvent an organic solvent which is not miscible with water
- the solvent and raw materials used are used directly, and no special treatment is required, but the environment for synthesis laboratory, drying and storage should be kept free of acid.
- the aluminum compound is made of organoaluminum and the lithium compound is inorganic aluminum, the aluminum compound is dissolved in the water solvent I, and the lithium compound is not dissolved. In order to facilitate the recycling of the solvent, it is preferred to use the same solvent as the raw material solvent.
- the amount of the solvent is not confirmed according to the solubility of the 8-hydroxyquinoline compound; if a large crystal is desired, the amount of the solvent can be increased; if it is a compound of a misaligned ligand, the compounds of different ligands are separately dissolved.
- the above reaction temperature is controlled at 25 ° C - 120 ° C, and the product is quickly precipitated. After all the stirring is completed until the product is no longer precipitated, the target product can be separated by suction filtration, the solvent is washed, and the purity of the product is 99. Above %, the yield is greatly improved compared with the method of the comparative literature.
- the metal compound obtained by the above process solves the problems of low yield and many side reactions existing at present, and has the following advantages:
- the synthesis process uses a water solvent, which does not require a protic solvent, and easily causes a coordination solvent, thereby avoiding the problem of complexing of solvent molecules.
- the obtained product has no coordinating solvent molecules, and no pinholes are generated during the preparation of the device, and the brightness, efficiency and life of the device are not affected.
- the solvent and raw materials are made of industrial raw materials, and no special treatment is required, which simplifies the reaction step, and the obtained product can be directly used in the light-emitting device.
- the by-product obtained is neutral, avoiding the generation of acidic substances in the prior process, causing side reactions caused by the generation of acidic substances, and not obtaining by-products during product sublimation and use.
- the synthesized 8-hydroxyquinoline metal complex also contains no ionic impurities. Further, in the preparation process of the present invention, the sewage from the washing is not generated, and environmental pollution can be prevented.
- the 8-hydroxyquinoline lithium product has high yield, and the compound is stable, and there is no decomposition in the heating and sublimation processes.
- Comparative Example 1 Synthesis of 8-hydroxyquinoline aluminum by using aluminum stearate as a raw material (refer to World Patent WO0125211)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/264,070 US20120130074A1 (en) | 2009-04-13 | 2010-03-30 | Method for Preparation Metal Compounds of 8-Hydroxyquinoline or Derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100818461A CN101514188B (zh) | 2009-04-13 | 2009-04-13 | 8-羟基喹啉类金属化合物的制备方法 |
CN200910081846.1 | 2009-04-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010118661A1 true WO2010118661A1 (zh) | 2010-10-21 |
Family
ID=41038822
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2010/071409 WO2010118661A1 (zh) | 2009-04-13 | 2010-03-30 | 8-羟基喹啉或其衍生物的金属化合物的制备方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20120130074A1 (zh) |
KR (1) | KR20110123802A (zh) |
CN (1) | CN101514188B (zh) |
WO (1) | WO2010118661A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114621753A (zh) * | 2022-03-03 | 2022-06-14 | 青岛大学 | 一种利用铝络合物制备的青色荧光材料及方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101514188B (zh) * | 2009-04-13 | 2013-05-01 | 广东阿格蕾雅光电材料有限公司 | 8-羟基喹啉类金属化合物的制备方法 |
CN101768435B (zh) * | 2009-12-31 | 2012-08-22 | 北京化工大学 | 三(8-羟基喹啉-5-磺酸根)合铝配阴离子插层水滑石复合发光材料及其制备方法 |
CN104151238B (zh) * | 2014-07-30 | 2016-01-20 | 南昌航空大学 | 一种直接制备纯8-羟基喹啉铝的方法 |
CN105439950B (zh) * | 2015-12-26 | 2020-05-22 | 南昌航空大学 | 一种制备发光材料8-羟基喹啉钙的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07196620A (ja) * | 1994-01-10 | 1995-08-01 | Nippon Steel Chem Co Ltd | 8−オキシキノリン−アルミニウム塩の製造方法 |
CN101514188A (zh) * | 2009-04-13 | 2009-08-26 | 北京阿格蕾雅科技发展有限公司 | 8-羟基喹啉类金属化合物的制备方法 |
-
2009
- 2009-04-13 CN CN2009100818461A patent/CN101514188B/zh not_active Expired - Fee Related
-
2010
- 2010-03-30 WO PCT/CN2010/071409 patent/WO2010118661A1/zh active Application Filing
- 2010-03-30 US US13/264,070 patent/US20120130074A1/en not_active Abandoned
- 2010-03-30 KR KR1020117023420A patent/KR20110123802A/ko not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07196620A (ja) * | 1994-01-10 | 1995-08-01 | Nippon Steel Chem Co Ltd | 8−オキシキノリン−アルミニウム塩の製造方法 |
CN101514188A (zh) * | 2009-04-13 | 2009-08-26 | 北京阿格蕾雅科技发展有限公司 | 8-羟基喹啉类金属化合物的制备方法 |
Non-Patent Citations (3)
Title |
---|
MATSUMURA, MICHIO ET AL.: "Organic electroluminescent devices having derivatives of aluminum-hydroxyquinoline complex as light emitting materials.", JAPANESE JOURNAL OF APPLIED PHYSICS, PART 1: REGULAR PAPERS, SHORT NOTES & REVIEW PAPERS., vol. 35, no. 10, 1996, pages 5357 - 5360 * |
RAJESWARAN, M ET AL.: "Bis(2,6-diphenylphenolato) (2-methylquinolin-8- olato) aluminium (III).", ACTA CRYSTALLOGR., vol. 62, 2006, pages M2216 - 2217 * |
SCHMITZ, CHRISTOPH ET AL.: "Lithium-Quinolate Complexes as Emitter and Interface Materials in Organic Light-Emitting Diodes.", CHEMISTRY OF MATERIALS., vol. 12, no. 10, 2000, pages 3012 - 3019 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114621753A (zh) * | 2022-03-03 | 2022-06-14 | 青岛大学 | 一种利用铝络合物制备的青色荧光材料及方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20110123802A (ko) | 2011-11-15 |
CN101514188B (zh) | 2013-05-01 |
US20120130074A1 (en) | 2012-05-24 |
CN101514188A (zh) | 2009-08-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2019153980A1 (zh) | 一种喹啉三唑类稀土配合物及其制备方法和应用 | |
WO2010118661A1 (zh) | 8-羟基喹啉或其衍生物的金属化合物的制备方法 | |
CN108147960B (zh) | 一种功能修饰铝金属有机框架材料及其制备方法 | |
CN109438488A (zh) | 一种液体草酸硼酸锂盐的制备方法 | |
Shi et al. | Synthesis and characterization of polymorphs of photoluminescent Eu (III)-(2, 5-furandicarboxylic acid, oxalic acid) MOFs | |
Liu et al. | Auxiliary ligand-controlled supramolecular assembly of three Cd (II) coordination polymers based on a (E)-3-(quinolin-4-yl) acrylic acid: syntheses, structures and photoluminescent properties | |
CN110684042A (zh) | 一种双草酸硼酸锂的制备方法 | |
KR101871215B1 (ko) | 2,6-비스[3'(n-카르바졸릴)페닐]피리딘 화합물의 합성방법 | |
Li et al. | Construction of three pH-dependent luminescent metal–organic frameworks with 3-(4-carboxyphen-yl)-1, 3-benzoimidazole | |
Wang et al. | Hydrothermal synthesis, crystal structure, and photoluminescence of novel lanthanide metal organic frameworks constructed from 1, 4-benzene-dicarboxylic acid and 1, 2, 4, 5-benzenetetracarboxylic acid as ligands | |
Shi et al. | Synthesis and crystal structure of metal-organic frameworks [Ln2 (pydc-3, 5) 3 (H2O) 9] n3nH2O (Ln= Sm, Eu, Gd, Dy; pydc-3, 5= pyridine-3, 5-dicarboxylate) along with the photoluminescent property of its europium one | |
Lin et al. | Enhanced fluorescence by increasing dimensionality: a novel three-dimensional luminescent metal–organic framework with rigidified ligands | |
Sanwaria et al. | Non-aqueous synthesis of nano-sized aluminium (III) isopropoxide derivatives with 8-hydroxyquinoline and their sol–gel transformation to nano-sized δ-alumina | |
Song et al. | Luminescent properties of Ag (I)/Cu (I) coordination polymers: crystal structures and high intensity luminescence of a PMMA-doped hybrid material based on a quinoline-2, 3-dicarboxylic acid ligand | |
Yu et al. | Syntheses and luminescence of three lanthanide complexes constructed by flexible carboxylate ligand | |
CN113234099B (zh) | 一种烷基硼酸酯类化合物的光化学合成方法 | |
CN115010763A (zh) | 一种圆偏振磷光铂(ii)配合物及其制备方法与应用 | |
CN109320528B (zh) | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 | |
Zhou et al. | Two 2-D 4-connected lanthanide coordination framework based on benzimidazole-5, 6-dicarboxylate and acetate mixed ligands | |
CN105439950B (zh) | 一种制备发光材料8-羟基喹啉钙的方法 | |
CN113149871A (zh) | 一种一步原位催化反应生成对称磺酸基1,1ˊ-联萘酚绿色合成方法 | |
Liu et al. | Copper (ii) and cobalt (ii) complexes based on bis-benzimidazolyl ligand with 1, 2-bis (2′-ethoxy) phenyl linker: synthesis, crystal structure and conformations | |
CN109251213B (zh) | 一种多齿8-羟基喹啉类锌配合物二聚晶体及其制备方法和应用 | |
Iijima et al. | Synthesis of reactive [Al (Et)(q′) 2](q′= 2-methyl-8-quinolinolato) serving as a precursor of light emitting aluminum complexes: Reactivity, optical properties, and fluxional behavior of the aluminum complexes | |
CN105777666A (zh) | 一种碘原子取代含甲基的氟代苯并杂环化合物的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10764074 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 20117023420 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13264070 Country of ref document: US |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 10764074 Country of ref document: EP Kind code of ref document: A1 |