CN1315808C - Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application - Google Patents
Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application Download PDFInfo
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- CN1315808C CN1315808C CNB2004100276997A CN200410027699A CN1315808C CN 1315808 C CN1315808 C CN 1315808C CN B2004100276997 A CNB2004100276997 A CN B2004100276997A CN 200410027699 A CN200410027699 A CN 200410027699A CN 1315808 C CN1315808 C CN 1315808C
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Abstract
The present invention relates to a vinyl monomer of an 8-hydroxyquinoline metal complex, which is in the structure disclosed as following and comprises a plurality of polymerizable functional groups, a preparation method thereof and purposes thereof. The preparation method comprises: vinyl monomers which comprise 8-hydroxyquinoline are synthesized and are then matched with metallic ions so as to generate the vinyl monomer of 8-hydroxyquinoline metal complexes, which comprises a plurality of polymerizable functional groups. Compared with luminescent materials prepared from other methods and raw materials, the synthesis method provided by the present invention and the prepared luminescent materials have the advantages of simple technology, less equipment investment and low cost. The materials have both superior processing performance and photoelectric performance, can be used as electroluminescent materials and electronic transporting materials in an organic/macromolecular electroluminescent flat-panel display device, and have important significance for developing the next generation of flat-panel display devices with superior performance.
Description
Technical field
The present invention relates to a class and contain oxine metal complexes vinyl monomer and method for making and purposes.Especially can form the oxine title complex vinyl monomer that contains a plurality of polymerizable functional groups and the method for making and the purposes of cross-linked polymer.
Technical background
The organic/polymer electroluminescent device is easy to realize large screen display because its driving voltage is low, the brightness height, and the visual angle is wide, and glow color is continuously adjustable etc., and advantage makes it become present information display technology field one big research focus.From the C.W.Tang of U.S. Kadak company in 1987 and co-worker thereof reported a kind of with oxine aluminium as luminescent layer, driving voltage is less than 10 volts, luminosity reaches 1000cd/m
2Since being the electroluminescent device of green light of 100h work-ing life, the researchist comes to realise wide application prospect and the value that oxine metal complexes (is representative with oxine aluminium and oxine zinc) is had in the organic electroluminescent field, thereby has dropped into a large amount of energy it is studied.Application to the oxine metal complexes is limited to dual mode usually in organic electroluminescence device at present: a kind of mode is the representative figure with Tang and Adachi, and it is directly used as the small molecules luminescent material; Another kind is that it is dispersed in certain polymeric matrix, formation mix up polymkeric substance as luminophore, mix up polymethylmethacrylate as oxine aluminium, polystyrene, PPV is in the materials such as PVK.Two kinds of methods all have obvious weak point in the practical application: it is to utilize the small molecules evaporation film-forming that common a kind of application mode in the past prepares electroluminescent device, because the high temperature during distillation easily makes small molecules produce oligopolymer or isomer, and device micromolecular crystallization of when work all can influence device lifetime greatly, and this mode be difficult for to realize the large-area device of preparation, with methods such as solution spin coating or spray printing relatively be a kind of expensive preparation technology; Though a kind of application mode in back solves these problems,, make material be separated within a short period of time and shortened the device working life because compatibility problem is difficult to solve between oxine metal complexes and polymeric matrix.The high molecular of oxine metal complexes is expected to address the above problem.At present the oxine metal complexes of synthetic high molecular research less, shortcoming such as there is preparation method's complexity mostly in the oxine metal complexes of the high molecular of bibliographical information, and productive rate is low, and the product solubility property is poor, and luminous efficiency is low.When the oxine metal complexes partly accounted for superpolymer weight and is generally 20% left and right sides, polymer just was difficult to be dissolved in usual vehicle.
Summary of the invention
The object of the invention is to provide a kind of solvability good, the luminous efficiency height, can form the oxine metal complexes vinyl monomer that contains a plurality of polymerizable functional groups of cross-linking copolymer.This material is convenient to prepare big area, multilayer organic/polymer display device cheaply.
Another object of the present invention provides the preparation method of this luminescent material, under the condition of common lab, and the vinyl monomer of the oxine metal complexes that contains a plurality of polymerizable functional groups that synthetic yield is very high.
A further object of the present invention provides the purposes of this luminescent material.
The invention provides the following oxine metal ion match vinyl monomer that contains a plurality of polymerizable functional groups of a kind of structure:
Wherein: M is selected from trivalent metallic element,
M is selected from divalent metal element,
R
1Be selected from C
2-C
18Hydrocarbon (containing aromatic hydrocarbons) base, ester group, ether, amido etc.The preferred C of carbon chain lengths wherein
2-C
8
R
2, R
3, R
4Be selected from hydrogen and C
1-C
18Hydrocarbon (containing aromatic hydrocarbons) base.Wherein preferred hydrogen and C
1-C
8Hydrocarbon (containing aromatic hydrocarbons) base.
Wherein trivalent metal, divalent metal element and monovalence metallic element can comprise main group metal element (as Al, Mg, Li etc.), thulium (as Eu, Sm etc.), transition metal (as Zn, Ru etc.), respectively preferred Al, Zn.
The oxine metal complexes vinyl monomer preparation method who contains a plurality of polymerizable functional groups is by the synthetic oxine vinyl monomer that contains, cooperate the vinyl monomer of the oxine metal complexes that contains a plurality of polymerizable functional groups that generates again with metal ion, its step comprises:
(a) but, get 100 parts of vinyl compounds that contain reactive functionality, the oxine that adds 0.1-100 part (preferred 0.5-50 part) modification, 0.01-20 part (preferred 0.01-2 part) catalyzer, 0.01-50 part (preferred 0.01-5 part) stopper, temperature are controlled at 40-150 ℃ and stir down, react 0.5 hour to two days, add 100-1000 part water then, the dropping weight concentration is that the weak ammonia of 1-10% obtains white precipitate, and the sherwood oil recrystallization obtains containing oxine part vinyl monomer.
(b), get the compound of 1 part of metal ion, the vinyl monomer that contains the oxine part that adding 0.5-50 part (preferred 1-10 part) makes through (a) step is dissolved in 5-100 part organic solvent, 20-150 ℃ is stirred down, fed nitrogen, anhydrous condition reaction down in 1-10 days, steam solvent or add precipitation agent, recrystallization, drying obtain containing the vinyl monomer of the oxine metal complexes of a plurality of polymerizable functional groups;
Wherein umber is all by the mole umber.
Step (a) but but described in the vinyl compound that contains reactive functionality in reactive functionality can be-CH
2OH ,-CH
2X (X is a halogen atom) ,-CH
2NH
3,-COOH ,-COCl ,-CONH
2,-COOOC-.Vinyl compound can be C
3-C
18The hydro carbons (containing aromatic hydrocarbons) that has ethylene linkage, ethers, ester compound.As vinylcarbinol, vinyl benzyl chloride, C
3-C
18Unsaturated acid, C
3-C
18Unsaturated hydroxy alkyl ester, acrylic acid hydroxy alkyl ethers etc.
The oxine of described modification is for having-CH
2X (X is a halogen atom) ,-CH
2OH ,-CH
2NH
2Oxine hydrochloride Deng functional group.
Described catalyzer is an alkaline matter, can be highly basic or strong base weak acid salt: NaOH, Na
2CO
3, NaHCO
3, KOH, K
2CO
3, KHCO
3, sodium-acetate, Potassium ethanoate etc.
Described stopper can be aromatic series phenols or aminated compounds, as Resorcinol, para benzoquinone, phenothiazine, beta-phenyl naphthylamines, p-ten.-butylcatechol, methylene blue, p methoxy phenol etc.
The compound of metal ion described in the step (b) is that the main group metal ion is (as Al
3+, Mg
2+, Li
+Deng), rare earth ion is (as Eu
3+, Sm
3+Deng), transition metal ion is (as Ru
3+Deng) salt, bases, organo-metallic etc., as AlCl
3, Mg (NO
3)
2, LiOH, zinc ethyl etc.The preferred Al of metal ion wherein
3+, Zn
2+
The preferred polar organic solvent of described organic solvent, as dehydrated alcohol, tetrahydrofuran (THF), toluene, dimethylbenzene, chloroform, benzene.
Described precipitation solvent can be selected from alkanes and water, as sherwood oil, and normal hexane, normal heptane, water etc.Preferred alkanes.
The vinyl monomer that contains the oxine metal complexes of a plurality of polymerizable functional groups of the present invention can be used as electroluminescent material and the electron transport material in the organic electroluminescent flat panel display device.
The present invention is by the earlier synthetic good vinyl monomer that contains the oxine metal complexes of solvability, and after the spin-coating film, repolymerization has formed good film-forming property, and stability is high, oxine metal complexes content height, the luminescent material that luminous efficiency is high.
Synthetic of the present invention contain a plurality of polymerizable functional groups the oxine metal complexes vinyl monomer by infrared spectra,
1H-NMR, ultimate analysis proves its precise structure.The photoelectric properties of this luminescent material are tested: ultra-violet absorption spectrum and photoluminescence spectra have red shift with respect to corresponding oxine metal complexes small molecules.As: the oxine aluminium UV/vis λ that contains a plurality of polymerizable functional groups
Max=270nm, 393nm; The oxine zinc UV/vis λ that contains a plurality of polymerizable functional groups
Max=390nm), contain the oxine aluminium PL λ of a plurality of polymerizable functional groups
Max=544nm; The oxine zinc PL λ that contains a plurality of polymerizable functional groups
Max=560nm), prove described monomer and the identical glow peak of corresponding oxine metal complexes, PL luminous efficiency 30%-60%, (the oxine aluminium of many polymerizable functional groups of ITO/PEDT/ or zinc monomer/LiF/Al), there is red shift at the electroluminescent peak with respect to corresponding oxine metal complexes small molecules to electroluminescent device.As, contain the oxine aluminium fluores λ of a plurality of polymerizable functional groups
Max=580nm; The oxine zinc fluores λ that contains a plurality of polymerizable functional groups
Max=590nm.Internal quantum efficiency illustrates that greater than 0.1% this is the luminescent material that a class can be used to prepare electroluminescent device.
By synthetic method provided by the invention and prepared luminescent material, compare with the luminescent material of additive method and feedstock production that technology is simple, facility investment is few, with low cost, have good processing characteristics and photoelectric properties concurrently, can be used as electroluminescent material and electron transport material in the organic/polymer electroluminescent flat panel display device, significant for the flat panel display device of development superior performance of future generation.
Embodiment
Following umber is all by the mole umber.
Embodiment 1
100 parts of hydroxyethyl methylacrylates add and contain-CH
220 parts of the substituent oxine hydrochlorides of Cl, 1.5 under the catalysis of part sodium-acetate, 3 parts of para hydroxybenzene phenol are as stopper, temperature is controlled at 100 ℃ of stirrings, and 8h controls reaction, and reaction finishes to add 500 parts of water, dripping an amount of weight concentration is that 5% weak ammonia is to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing 3 CH
2=C (CH
3)-COO-CH
2CH
2-O-CH
2-the vinyl monomer of oxine part; Get 1 part of Tai-Ace S 150 and be dissolved in 50 parts of chloroforms, add 8 parts and contain 3 CH
2=C (CH
3)-COO-CH
2CH
2-O-CH
2-the vinyl monomer of oxine part, 120 ℃ of following stirring reactions 3 days left standstill 1 day, filtered to get filtrate, aqueous precipitation filters and obtains solid, sherwood oil recrystallization 3 times obtains containing 3 CH
2=C (CH
3)-COO-CH
2CH
2-O-CH
2-oxine aluminum complex vinyl monomer.
Get this monomer of 2.0g and be dissolved in the 20ml toluene, add the 0.02g bitter almond oil camphor, be spun on conductive glass (ito glass) sheet (1000nm), in nitrogen under the room temperature at ultraviolet lamp (300nm, 100mWcm
-2) descend 100s to obtain the cross-linked polymer luminescent material.
Embodiment 2
100 parts to vinyl chloride, adding-CH
210 parts of the substituent oxine hydrochlorides of OH, 0.5 under the catalysis of part sodium-acetate, 2 parts of benzoquinones are as stopper, temperature is controlled at 100 ℃ of stirrings, and 18h controls reaction, and reaction finishes to add 200 parts of water, drip an amount of weight concentration and be 3% weak ammonia to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing CH
2=CHOCH
2-the vinyl monomer of oxine part; Get 1 part of triethyl aluminum and be dissolved in 10 parts of toluene, add 10 parts and contain CH
2=CHOCH
2-the vinyl monomer of oxine part, 100 ℃ of following stirring reactions 3 days left standstill 1 day, filtered to get filtrate, and added methanol extraction, filtered and obtained solid, sherwood oil recrystallization 3 times obtains containing 3 CH
2=CHOCH
2-the monomer of oxine aluminum complex.
Get this monomer monomer of 1.0g and be dissolved in the 30ml tetrahydrofuran (THF), add 0.01g benzoyl peroxide (BPO), be spun on (2000nm) on the conductive glass sheet, 120 ℃ of 6h of heating in nitrogen, 120 ℃ of 6h of after fixing obtain the cross-linked polymer luminescent material.
Embodiment 3
100 parts to vinyl benzyl chloride, adding-CH
210 parts of the substituent oxine hydrochlorides of OH, 0.5 under the catalysis of part sodium-acetate, 2 parts of benzoquinones are as stopper, temperature is controlled at 100 ℃ of stirrings, and 18h controls reaction, and reaction finishes to add 200 parts of water, drip an amount of weight concentration and be 3% weak ammonia to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing CH
2=CH-Ar-CH
2OCH
2-the vinyl monomer of oxine part; Get 1 part of triethyl aluminum and be dissolved in 10 parts of toluene, add 10 parts and contain CH
2=CH-Ar-CH
2OCH
2-the vinyl monomer of oxine part, 100 ℃ of following stirring reactions 3 days left standstill 1 day, filtered to get filtrate, and added methanol extraction, filtered and obtained solid, sherwood oil recrystallization 3 times obtains containing 3 CH
2=CH-Ar-CH
2OCH
2-the monomer of oxine aluminum complex.
Get this monomer of 0.5g and be dissolved in the 20ml chloroform, add the 0.1g benzil ketals, be spun on (1000nm) on the conductive glass sheet, room temperature is at ultraviolet lamp (300mm, 100mWcm in nitrogen
-2) descend 30s to obtain the cross-linked polymer luminescent material.
Embodiment 4
100 parts of amino hexenes of 6-add and contain-CH
250 parts of the substituent oxine hydrochlorides of Cl, under the catalysis of 1 part of sodium-acetate, 2.5 part benzoquinones is as stopper, temperature is controlled at 40 ℃ of stirrings, and 30h controls reaction, and reaction finishes to add 800 parts of water, dripping an amount of weight concentration is that 8% weak ammonia is to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing CH
2=CH-(CH
2)
3-CH
2NHOCH
2-the vinyl monomer of oxine part; Get 1 part of zinc chloride and be dissolved in 50 parts of chloroforms, add 3 parts and contain CH
2=CH-(CH
2)
5-CH
2NHOCH
2-the vinyl monomer of oxine part, stirring reaction is 8 days under the room temperature, leaves standstill 1 day, filters to get filtrate, aqueous precipitation filters and obtains solid, sherwood oil recrystallization 3 times obtains containing 2 CH
2=CH-(CH
2)
3-CH
2NHCH
2-the monomer of oxine Zn complex.
Get this monomer of 2.0g and be dissolved in the 20ml toluene, add 0.02g Diisopropyl azodicarboxylate (AIBN), be spun on that (2000nm) heats 100 ℃ of 10h on the conductive glass sheet in nitrogen, 150 ℃ of 0.5h of after fixing obtain the cross-linked polymer luminescent material.
Embodiment 5
100 parts of methacrylic chlorides add and contain-CH
210 parts of the substituent oxine hydrochlorides of OH, 2.5 under the catalysis of part sodium-acetate, 3 parts of para hydroxybenzene phenol are as stopper, temperature is controlled at 100 ℃ of stirrings, and 8h controls reaction, and reaction finishes to add 500 parts of water, dripping an amount of weight concentration is that 5% weak ammonia is to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing CH
2=C (CH
3)-COO-CH
2-the vinyl monomer of oxine part; Get 1 part of zinc acetate and be dissolved in 50 parts of chloroforms, add 8 parts and contain CH
2=C (CH
3)-COO-CH
2-the vinyl monomer of oxine part, 120 ℃ of following stirring reactions 3 days left standstill 1 day, filtered to get filtrate, aqueous precipitation filters and obtains solid, sherwood oil recrystallization 3 times obtains containing 2 CH
2=C (CH
3)-COO-CH
2-the monomer of oxine Zn complex.
Get this monomer of 0.5g and be dissolved in the 20ml chloroform, add the 0.1g benzil ketals, be spun on (1000nm) on the conductive glass sheet, room temperature is at ultraviolet lamp (300nm, 100mWcm in nitrogen
-2) descend 90s to obtain the cross-linked polymer luminescent material.
Embodiment 6
100 parts of chlorallylenes add and contain-CH
230 parts of the substituent oxine hydrochlorides of OH, 0.2 under the catalysis of part sodium-acetate, 4 parts of benzoquinones are as stopper, temperature is controlled at 120 ℃ of stirrings, and 8h controls reaction, and reaction finishes to add 500 parts of water, dripping an amount of weight concentration is that 8% weak ammonia is to neutral, obtain white precipitate, sherwood oil recrystallization 3 times obtains containing CH
2=CH-CH
2-O-CH
2-the vinyl monomer of oxine part; Get 1 part of zinc ethyl and be dissolved in 30 parts of dehydrated alcohols, add 10 parts and contain CH
2=CH-CH
2-O-CH
2-the vinyl monomer of oxine part, 150 ℃ of following stirring reactions 1 day left standstill 1 day, filtered to get filtrate, aqueous precipitation filters and obtains solid, sherwood oil recrystallization 3 times obtains containing 2 CH
2=CH-CH
2-O-CH
2-the monomer of oxine Zn complex.
Get this monomer of 2.0g and be dissolved in the 20ml toluene, add 0.02g Diisopropyl azodicarboxylate (AIBN), be spun on that (2000nm) heats 120 ℃ of 1h on the conductive glass sheet in nitrogen, 120 ℃ of 0.5h of after fixing obtain the cross-linked polymer luminescent material.
Claims (10)
1, the oxine metal ion match vinyl monomer that contains a plurality of polymerizable functional groups that structure is following:
Wherein: M is selected from trivalent metallic element,
M is selected from divalent metal element,
R
1Be selected from C
2-C
18Aryl, ester group, ether or amido,
R
2, R
3, R
4Be selected from hydrogen and C
1-C
18Alkyl.
2, the vinyl monomer of claim 1, wherein trivalent metal, divalent metal element are selected from main group metal element, thulium or transition metal respectively.
3, claim 1 or 2 vinyl monomer, wherein M is Al, m is Zn.
4, claim 1 or 2 vinyl monomer, wherein R
1Be selected from C
2-C
8Aryl, ester group, ether or amido, R
2Be selected from hydrogen and C
1-C
8Alkyl.
5, the method for making of the arbitrary vinyl monomer of claim 1～4 is to contain the oxine vinyl monomer by synthetic, cooperates the vinyl monomer of the oxine metal complexes that contains a plurality of polymerizable functional groups that generates again with metal ion, and its step comprises:
(a) but, get 100 parts of vinyl compounds that contain reactive functionality, the oxine that adds the modification of 0.1-100 part, 0.01-20 part highly basic or strong base weak acid salt catalyzer, 0.01-50 part aromatic series phenols or aminated compounds stopper, temperature are controlled at 40-150 ℃ and stir down, react 0.5 hour to two days, add 100-1000 part water then, the dropping weight concentration is that the weak ammonia of 1-10% obtains white precipitate, and the sherwood oil recrystallization obtains containing oxine part vinyl monomer;
(b), get the compound of 1 part of metal ion, add 0.5-50 part and be dissolved in 5-100 part organic solvent through the vinyl monomer that contains the oxine part that (a) step makes, 20-150 ℃ is stirred down, fed nitrogen, anhydrous condition reaction down in 1-10 days, steam solvent or add precipitation agent, recrystallization, drying obtain containing the vinyl monomer of the oxine metal complexes of a plurality of polymerizable functional groups;
Wherein umber is all by the mole umber.
6, the method for claim 5, wherein step (a) but but described in the reactive functionality of the vinyl compound that contains reactive functionality be-CH
2OH ,-CH
2X ,-CH
2NH
3,-COOH ,-COCl ,-CONH
2Or-COOOC-, vinyl compound is C
3-C
18The hydro carbons, ethers or the ester compound that have ethylene linkage; The oxine of described modification is for having-CH
2X ,-CH
2OH or-CH
2NH
2The oxine hydrochloride of functional group; Described highly basic or strong base weak acid salt catalyzer are selected from NaOH, Na
2CO
3, NaHCO
3, KOH, K
2CO
3, KHCO
3, sodium-acetate or Potassium ethanoate; Described aromatic series phenols or aminated compounds stopper are selected from Resorcinol, para benzoquinone, phenothiazine, beta-phenyl naphthylamines, p-ten.-butylcatechol, methylene blue or p methoxy phenol; Wherein X is a halogen atom.
7, the method for claim 6, wherein step (a) but described in the vinyl compound that contains reactive functionality be selected from vinylcarbinol, vinyl benzyl chloride, C
3-C
18Unsaturated acid, C
3-C
18Unsaturated hydroxy alkyl ester or acrylic acid hydroxy alkyl ethers.
8, claim 5 or 6 method, wherein the compound of metal ion described in the step (b) is selected from salt, bases or the organo-metallic of main group metal ion, rare earth ion, transition metal ion; Described organic solvent is selected from polar organic solvent; Described precipitation solvent is selected from alkanes and water.
9, claim 5 or 6 method, wherein described in the step (b) in the compound of metal ion metal ion be selected from Al
3+Or Zn
2+Described organic solvent is selected from dehydrated alcohol, tetrahydrofuran (THF), toluene, dimethylbenzene, chloroform or benzene; Described precipitation solvent is selected from sherwood oil, normal hexane or the normal heptane in the alkanes.
10, the arbitrary vinyl monomer of claim 1～4 is as electroluminescent material and electron transport material in the organic electroluminescent flat panel display device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100276997A CN1315808C (en) | 2004-06-18 | 2004-06-18 | Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application |
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|---|---|---|---|
| CNB2004100276997A CN1315808C (en) | 2004-06-18 | 2004-06-18 | Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application |
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|---|---|
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| CN1315808C true CN1315808C (en) | 2007-05-16 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1315807C (en) * | 2004-04-30 | 2007-05-16 | 中国科学院广州化学研究所 | Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use |
| CN105176520B (en) * | 2015-09-01 | 2017-06-20 | 华南理工大学 | One kind is based on 4,4′The preparation and application of the luminous and material of main part of substitution benzil core |
| CN106892868B (en) * | 2017-02-28 | 2018-10-09 | 广东工业大学 | A kind of 8-hydroxyquinoline Zn complex and preparation method thereof with one-dimensional catenary structure |
| CN108530356A (en) * | 2018-06-08 | 2018-09-14 | 广州工程技术职业学院 | It is a kind of based on the 8-hydroxyquinoline aluminium green light material that can gather and preparation method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000252072A (en) * | 1999-03-03 | 2000-09-14 | Honda Motor Co Ltd | Organic electroluminescent element and manufacture thereof |
| CN1282735A (en) * | 2000-08-26 | 2001-02-07 | 暨南大学 | Amphiphili 8-hydroxyquinoline complex, its preparing process and its application in electroluminescence |
| JP2002352959A (en) * | 2001-05-28 | 2002-12-06 | Canon Inc | Organic light-emitting element and manufacturing method therefor, display using the element, photosensitizer exposure equipment using the element, and illumination equipment using the element |
| CN1569836A (en) * | 2004-04-30 | 2005-01-26 | 中国科学院广州化学研究所 | Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use |
-
2004
- 2004-06-18 CN CNB2004100276997A patent/CN1315808C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000252072A (en) * | 1999-03-03 | 2000-09-14 | Honda Motor Co Ltd | Organic electroluminescent element and manufacture thereof |
| CN1282735A (en) * | 2000-08-26 | 2001-02-07 | 暨南大学 | Amphiphili 8-hydroxyquinoline complex, its preparing process and its application in electroluminescence |
| JP2002352959A (en) * | 2001-05-28 | 2002-12-06 | Canon Inc | Organic light-emitting element and manufacturing method therefor, display using the element, photosensitizer exposure equipment using the element, and illumination equipment using the element |
| CN1569836A (en) * | 2004-04-30 | 2005-01-26 | 中国科学院广州化学研究所 | Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use |
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