CN101000810B - Conduction composite - Google Patents
Conduction composite Download PDFInfo
- Publication number
- CN101000810B CN101000810B CN2007100262131A CN200710026213A CN101000810B CN 101000810 B CN101000810 B CN 101000810B CN 2007100262131 A CN2007100262131 A CN 2007100262131A CN 200710026213 A CN200710026213 A CN 200710026213A CN 101000810 B CN101000810 B CN 101000810B
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- CN
- China
- Prior art keywords
- polymer
- electrically conductive
- conductive composition
- conducting particles
- attritive powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
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- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZESXUEKAXSBANL-UHFFFAOYSA-N trifluoromethyl prop-2-enoate Chemical compound FC(F)(F)OC(=O)C=C ZESXUEKAXSBANL-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
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- 238000003466 welding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
Abstract
A conductive composite is prepared as forming said compound by conductive particles and polymer as well as solvent, using ethenyl as main chain and heterocycle as side chain of said polymer, The prepared conductive composite can be used to prepare OLED/PLED single color or full color luminous component and electrode of solar energy battery.
Description
Technical field
The present invention relates to electrically conductive composition.
The invention still further relates to the application of described electrically conductive composition in the electrode of monochromatic or panchromatic luminescent device and the solar battery of making OLED/PLED.
Background technology
Electrically conductive composition is widely used in electromagnetic shielding, antistatic, electrode etc., adopts methods such as coating, binder, printing ink to substitute traditional chemical plating, evaporation, welding, greatly reduces construction intensity, difficulty of processing, environmental pollution, reduces investment outlay, and reduces cost.
Electrically conductive composition generally adopts fluoropolymer resin, conducting particles hybrid systems, and after system drying or the curing, fluoropolymer resin is bonded together conducting particles, forms conductive path.In general, the polymer of employing comprises resinoids such as polyester, acrylic acid, vinyl, epoxy, polyurethane, phenolic aldehyde; Also can be their composition, their polymerization precursor, polymerization process be exactly a solidification process.
Fluoropolymer resin provides required surface property, anti-environmental change performance and mechanical performance for electrically conductive composition.Existing electrically conductive composition mainly uses epoxy resin or general acrylic resin or polyurethane resin to be binding material, and these materials are better aspect adhesive property, and raw material sources are extensive, and price is low, can satisfy the demand.
Make the material of apparatus heterocycle structure in the electrically conductive composition, generally as auxiliary material such as curing agent, dispersant, stabilizer etc.; As: the WO01/92416 patent of Japanese aginomoto is pulverized the latent curing agent of doing epoxy material after adopting the heterocycle glyoxaline compound with the epoxy addition; The same U.S. CN1087366 of W. R. Grace ﹠ Co patent also adopts similar techniques; Japan sun printing ink CN1384144 adopts as the imidazolium compounds with hydroxyl and aromatic rings of curing accelerator and makes printed substrate; Patent CN1537878 adopts the addition product that has substituent imdazole derivatives of long-chain and low-molecular-weight epoxy resin as latent curing agent, is applicable to the encapsulation of electronic devices and components; Patent CN1372269 has the tertiary amine structure and may be dissolved in the compound in the described organic carrier and have nitrogenous but sulfur heterocyclic ring structure and the compound that may be dissolved in the described organic carrier are not made a kind of have required time-independent viscosity and the conducting paste with stable viscosity characteristic.Patent CN1861685 adopts by azacyclo-components such as adding imidazoles in polymer, improve the anti-chemical oxidation performance of basis material, and then prolong chemical property and the useful life of proton exchange polymer membrane in electrochemical devices such as fuel cell and the conductivity that has also improved the polymer proton electric conducting material.
The material of heterocycle structure is used quite few therein, mainly is that water absorption is big, tends to reduce the performance of composition because heterocycle structure is particularly nitrogenous, oxygen element; Because the compound price of heterocycle structure is expensive, the source is few simultaneously.
The polymer that contains heterocycle structure, heterocycle structure is many as the main chain research of polymer link, mainly is used as photoelectric material; As: patent CN1329100 discloses a class main chain by double bond containing copolymer type conjugated polymers such as fragrant heterocycle, fused ring compound or derivatives thereof and diaryl ethylene compounds and preparation method thereof, is used to make light-emitting diode, electroluminescent device, photo luminescent devices and other electrooptical device and product mainly as luminescent material; Japanese Matsushita Electric Industrial WO02/086913 makes conductivity organic film and manufacture method thereof with high conductivity and electrode, electric wire and the electronic device that uses it by polypyrrole, poly-inferior thienyl etc.; The solid electrolyte that Japanese Matsushita Electric Industrial WO01/20625 adopts is a kind of in the presence of oxidizing agent solution, the electric conductive polymer of being made through chemical oxidising polymerisation by heterocyclic monomer; Patent CN1450094 " containing conjugated polymer of pyridine and its production and use on a kind of main chain "; Patent CN1841573 " transparent conductive body " adopts the electroconductive polymer of at least a kind of compound of polyacetylene, polypyrrole, polythiophene, polyphenylacetylene, polyphenylene, polysilane, poly-fluorenes and polyaniline.
Heterocycle structure on the side chain of polymer link, the material that do not participate in linking uses many at aspects such as dyeing and finishing, hair dyeing, plating, medicine, electrochemical cell, nano material making; As: any of patent CN1554503 employing polyvinylpyrrolidone cooked protective agent making nm of gold and is used for biomedical sector, electronics industry, field of fine chemical; The U.S. receives act Er Dubang US646797 and adopts the photosensitive aqueous developable thick film composition of vinylpyrrolidone polymer; The Taiwan integrated circuit is made CN1676672 and is adopted low positive charge density polymer to comprise benzene or pyrrolidones functional group monomer and imidazoles or imdazole derivatives functional group monomer, can fill out the excessive covering that reduces metal on the plated metal under the ability at best ditch; The CN1145371 of BASF AG adopts at least a N-vinyl pyrrolidone that is selected from, the have hair made soluble copolymers of used for cosmetic of the monomer of N-caprolactam and N-vinyl imidazole and other monomer copolymerization; Patent CN1709964 adopts a kind of transparent polymer non-aqueous proton conducting material based on polyvinyl alcohol and nitrogen heterocyclic and preparation method thereof, can be widely used in various all solid state electrochemical devices; The golden patent CN1812170 in NEC east " polymer and use its electrochemical cell " adopts a kind of chain structure of the repetitive with proton conductive compound and the polymer of heterocyclic compound structure; Patent CN1749351 " transparent non-water proton conductive material of side group type azacyclic polymer and preparation method thereof " adopts side group type azacyclic polymer and lewis acidity component is compound, and add the micromolecule nitrogen heterocyclic, obtain a kind of novel full solid state polymer non-aqueous proton conducting material with higher proton conductivity, high transparent; The decentralized control agent that WO2005/012411 adopts promotes conductive filler generally evenly distributed in whole polymer composition.Described polymer composition does not have poly-ring aromatic compounds substantially.
Patent CN200510035789.5 adopts conducting resinl to make electrode, has simplified the processing technology of OLED/PLED greatly, has really realized all print mode.This patent has been explained processing technology and thinking, adopts commercially available conducting resinl processing, and device performance is unsatisfactory.
The conductive layer that the OLED/PLED device uses, its conductivity is a key factor, is macroscopical electrical property on the measurement plane direction but conductivity often reflects; And the electric charge of OLED/PLED device need be crossed over electrode interface, and the performance between the interface is very crucial to the transmission influence of electric charge.
Summary of the invention
The object of the invention is to provide a kind of electrically conductive composition at the defective of prior art existence.
The present invention also aims to provide the application of described electrically conductive composition in the electrode of monochromatic or panchromatic luminescent device and the solar battery of making OLED/PLED.
Electrically conductive composition of the present invention comprises polymer, conducting particles, solvent, wherein
Described polymer is to be main chain, side-chain structure unit polymer, copolymer or its blend based on heterocycle structure with vinyl or acrylic; Perhaps
With vinyl or acrylic is main body and other fluoropolymer resin are done in main chain, side-chain structure unit based on polymer, copolymer or its mixture of heterocycle structure copolymerization or blend;
Described conducting particles is that metal, alloy are the attritive powder of main body;
Described solvent is the solvent or the polymerisable liquid of dissolve polymer;
Described polymer and conducting particles volume ratio are at 1-3: between the 3-1.
Homopolymers or copolymer or mixture that described polymer is made of one or more construction units that contain in the following general formula (1) (2), or the polymerization precursor of these polymer; Or the polymerization precursor is with its mixture;
(1)
(2)
R in the formula (2)
1Expression hydrogen atom or methyl;
R in the formula (1) (2)
2For containing the substituting group of heterocycle structure;
The described substituting group that contains heterocycle structure is a kind of in carbazole, fluorenes, thiophene, thiadiazoles, pyrroles, pyridine, indoles, quinoline, thiazole, oxazole, imidazoles, triazole, tetrazolium, acridine, diazine, triazine, tetrazine, pyrimidine, purine, porphines, porphyrin, phthalein green grass or young crops, crown ether, acid imide, the lactams group; Or the incomplete hydrogenation of aforementioned group or complete a kind of in the group behind the hydrogenation; Or a kind of in the aldehyde of aforementioned group, ketone, alkyl, acid, amine or its Ionized deriveding group; Or a kind of in several groups that are combined into of aforementioned group.
Comparative optimization be deriveding group and carbazole, pyridines such as carbazole, pyridine, pyrrole group and aldehyde thereof, ketone, alkyl, acid, the pyrroles is incomplete or complete hydrogenation after group and deriveding group such as aldehyde, ketone, alkyl, acid thereof; Best is pyrrolidone-base;
Described polymer is with having copolymer or the mixture that one or more other construction units constitute in following general formula (3), (4) by one or more construction units in general formula (1), (2); Or the homopolymers that is made of one or more construction units that contain in general formula (1), (2) or copolymer or mixture are with the mixture of other class organic material; Or the polymerization precursor of these polymer; Or the polymerization precursor is with its mixture; Wherein, the construction unit content with general formula (1) (2) feature is the 50-100% quality;
R in the formula (4)
1Expression hydrogen atom or methyl.
The structure of general formula (3) (4) comparative optimization is general formula (4), the described construction unit of general formula (4) is various acrylic acid and monomers such as ester, various methacrylic acid and ester thereof thereof before polymerization not, as esters such as acrylic acid and methyl esters thereof, ethyl ester, propyl ester, butyl ester, monooctyl ester, lauryl, norborneol ester, esters such as methacrylic acid and methyl esters thereof, ethyl ester, propyl ester, butyl ester, monooctyl ester, lauryl, norborneol ester; And the acrylic or methacrylic acid esters of various fluorine-containing replacements, as fluorinated esters such as trifluoromethyl acrylate, acrylic acid 19 fluorine esters, dodecafluorhe-ptylacrylate, acrylic acid trifluoro ethyl ester, acrylic acid hexafluoro butyl ester, methacrylic acid ten difluoro heptyl esters, trifluoroethyl methacrylate, methacrylic acid hexafluoro butyl esters.
Described conducting particles is metal gold, silver, copper, aluminium, palladium, platinum, nickel, chromium, cobalt, zinc, gallium, iron or the wherein micro-alloy powder more than two kinds, perhaps its clad material attritive powder, the perhaps attritive powder of its mixture; Or based on aforesaid attritive powder, add the attritive powder of other type, the attritive powder total amount of other types is no more than 10% weight of conducting particles.
The attritive powder of described other type comprises: a) there is transport phenomena in silver powder, and other metals and oxide can add silver-colored electrically conductive composition on a small quantity, can improve the performance of electrically conductive composition, as add small amount of indium, V in system
2O
5, palladium, titanium, platinum, magnesium, silicon, strontium, europium, iridium, gallium, nickel, barium, lanthanum, boron, ruthenium, yttrium, cerium, gold and their mixture, all can suppress the silver migration, total amount surpasses 1.0% of conducting particles; B) in order to increase the demonstration contrast, can add carbon black; C) can add all kinds of carbon nano-structured materials; D) can add the organic conductive minuteness particle; Except that preceding described situation, can also add the attritive powder of other kind.The attritive powder of other type can add one or more.
The attritive powder granularity of described conducting particles is less than 100 μ m.
Described solvent is alkane, aromatic hydrocarbons, alcohol, ether, ketone, phenol, ester, acid, their halogen substituent or their mixture; Or vinyl or acrylic are main chain, side-chain structure unit liquid oligomer or the monomer with heterocycle structure.That not exclusively enumerates has: hexane, octane, benzinum, benzene and substituent thereof, methyl alcohol, ethanol, isopropyl alcohol, ether, glycol ether, propylene glycol, acetone, butanone, cyclohexanone, isophorone, phenol and cresols, ethyl acetate, butyl acetate, various glycol ether ester and various propylene glycol ether-ether, acetate and their various halogen substituents also comprise the mixture of these solvents.
Comparative optimization be the acrylic or methacrylic acid ester monomer of various fluorine-containing replacements, the use of fluorine material can reduce the surface tension of electrically conductive composition, improve interface performance, can reduce the moisture absorption of electrically conductive composition simultaneously, best is methacrylic acid hexafluoro butyl ester monomer.
Described electrically conductive composition also comprises other compositions, and its consumption is less than 10% weight of total amount.
The present invention can also add other material except that aforesaid basis (polymer, conducting particles, solvent); As: a) in order to be fit to construction method, can add different chemical assistants, the chemical assistant of not exclusively enumerating has: levelling agent, adhesion promoter, wetting agent, defoamer, anti-settling agent, viscosity modifier, coupling agent etc.; B) can also add some functional materials, increase whiteness, add dyestuff etc. as adding ultramarine; Other material that adds can be one or more, and total amount is no more than 10% of electrically conductive composition total amount.
Other composition also comprises organic material, promptly various other base polymers, such as extensive stock fluidized polymer resin such as polyacrylate, polyester, polyamide, polyketone etc.; Also comprise various oligomers and various micromolecule organic material, for example all kinds of surperficial auxiliary agents.
Therefore, best polymer is polyvinylpyrrolidone and poly-(vinylpyrrolidone-methacrylic acid hexafluoro butyl ester) copolymer, and methacrylic acid hexafluoro butyl ester content is between 3-5% weight in the copolymer.
There are very strong charge interaction in N five-membered ring in the polyvinylpyrrolidone and ketone groups with silver and gold.
Foregoing polymer mainly is to be used for not reaction type electrically conductive composition of volatile-type, and the present invention can also adopt the electrically conductive composition of response type.
Utilize foregoing polymer form and type, adopt its polymerization precursor (oligomer and monomer), or the same mixture of polymers of polymerization precursor, by adding dissimilar auxiliary agents, form the polymeric material of electrically conductive composition, can be the one pack system form, it also can be the bi-component form, by the reaction formation of different modes, form the method for polymer, the process of polymerization is exactly to solidify dry process; Different reaction formations can be: but a) by adding the material of anaerobic digestion free radical, under anaerobic initiated polymerization precursor polymeric; B) by adding the oxysensible material that forms free radical, initiated polymerization precursor polymeric in the presence of oxygen; As borine amine complex and acid combination; C) by adding different OR agent, initiated polymerization precursor polymeric in use; D) by adding the compound that can form free radical, initiated polymerization precursor polymeric under the condition of heat; And other can the initiated polymerization precursor polymeric method.
If the present invention adopts the electrically conductive composition of response type, its solvent can be: vinyl or acrylic are main chain, side-chain structure unit liquid oligomer or the monomer with heterocycle structure; Can also be that vinyl or acrylic are that main chain, side-chain structure unit are that main component contains a small amount of other vinyl or the liquid oligomer of acrylic or the mixture of monomer with the liquid oligomer or the monomer of heterocycle structure.
High more its combination property of the polymer molecular weight that the present invention relates to is good more, molecular weight ranges from several ten thousand to up to a million can, consider dissolving and operating position, be 100,000 to 600,000 than preferable scope, best is 300,000 to 500,000.
Invent employed conducting particles, its yardstick can be from several nanometers to tens micron; Do transparency electrode and adopt nano material relatively good, its scope is below 380 nanometers, and than preferably being lower than 100 nanometers, best is about 15 nanometers; Its scope of non-transparent electrode is at the 1-20 micron, and than preferably 2-10 micron, best is the 5-9 micron; This is located said size and is meant average-size;
The conducting particles that the present invention uses, its shape is based on sheet, dendritic, colored bone shape etc.
Solvent used in the present invention, consider the dissolving situation of luminescent layer and its decorative layer, avoiding stinging end situation takes place, consider luminescent material and decorative layer thereof relatively multipotency molten with hydrocarbon and halogenated hydrocarbons thereof in, the ratio of solvent that the present invention selects is preferably alcohol or ethyl cellosolve acetate or propylene-glycol ethyl ether acetic acid esters or based on its mixed solvent.
The use amount situation of each material of electrically conductive composition that the present invention relates to: polymer and conducting particles volume ratio are between 1: 3 to 3: 1, and more excellent is between 1.5: 1 to 1: 1.5, and best is between 1.2: 1 to 1: 1.2.Can regulate the viscosity of composition to adapt to different fields of employment and occupation mode by the amount of adjusting solvent.
The present invention compared with prior art has following advantage and characteristics:
(1) adopt the surveyor's chain structure based on the vinyl of heterocycle structure or acrylic acid series polymeric compounds binding material first as electrically conductive composition;
(2) the heterocycle structure polymer dissolution performance of side chain type is better than the polymer of the heterocycle structure of backbone chain type greatly, and filming performance is good; Synthetic simultaneously simple, with low cost;
(3) heterocycle structure is with existing charge interaction between conducting particles, and heterocycle structure all has conjugation with luminescent material, thereby more helps the transmission of electric charge between different interfaces.
Embodiment
Prepare example:
Polymer:
Prepare example 1 (PFV):
N-vinylpyrrolidone 48 grams, methacrylic acid hexafluoro butyl ester 2 grams, ethanol 50 grams, azodiisobutyronitrile (being called for short AIBN) 0.25 gram.
0.25 gram AIBN is dissolved in 20 gram ethanol, takes out 10 grams and mixes (abbreviation mix monomer) with N-vinylpyrrolidone 48 grams, methacrylic acid hexafluoro butyl ester 2 grams.
The four-hole boiling flask of the belt stirrer of 250ML stirs, nitrogen filled protection, 70 ℃ of heating temperature controls; add 30 gram ethanol earlier, add the AIBNA ethanol liquid of 8 grams and the mix monomer of 5 grams again, drip remaining mix monomer again; added in 30 minutes, and added remaining AIBN ethanol liquid again, continue reaction 5 hours.
Vacuumize earlier, drier 48 hours (45 ℃) in vacuum drying chamber.
Obtain transparent solid material, be called for short PFV.(the PFV molecular weight is 110,000.)
Prepare example 2 (PPK3):
N-vinylpyrrolidone 35 grams, N-vinylcarbazole 15 grams, ethanol 150 grams, azodiisobutyronitrile (being called for short AIBN) 0.25 gram.
0.25 gram AIBN is dissolved in 20 gram ethanol, takes out 10 grams and N-vinylpyrrolidone 35 grams, N-vinylcarbazole 15 grams mix (abbreviation mix monomer).
The four-hole boiling flask of the belt stirrer of 250ML stirs nitrogen filled protection; 70 ℃ of heating temperature controls; add 30 gram ethanol earlier, add the AIBNA ethanol liquid of 8 grams and the mix monomer of 5 grams again, drip remaining mix monomer again; added in 30 minutes; add remaining AIBN ethanol liquid again, react after 90 minutes, drip remaining ethanol; added in 60 minutes, and continued reaction 150 minutes again.
Vacuumize earlier, drier 48 hours (45 ℃) in vacuum drying chamber.
Obtain transparent solid material, be called for short PPK3.(the PPK3 molecular weight is 100,000)
Embodiment:
Embodiment 1:
Poly N-ethylene pyrrolidones (K90, commercially available) 0.25 gram, methyl alcohol 1.30 gram stirring and dissolving, flake silver powder (commercially available average dimension 6-9 micron) 2.25 grams, high speed dispersion 4-6 hour.
Embodiment 2:
K90 in the PFV0.25 gram alternate embodiment 1 that preparation example 1 is made, other is with embodiment 1.
Embodiment 3:
The PPK3 0.25 for preparing example 2 making restrains poly N-ethylene pyrrolidones (K90, commercially available) in the alternate embodiment 1, and other is with embodiment 1.
Comparative Examples
Comparative Examples 1:
Commercially available prod 1, component is ominous.
Comparative Examples 2:
B66 (ROHM AND HAAS, polymethacrylate resin) 0.25 gram, ethyl cellosolve acetate 1.30 grams, other is with embodiment 1.
Comparative Examples 3:
TPU5715P (promise reputation noveon) substitutes the B66 in the Comparative Examples 3, and other is with Comparative Examples 3.
Result of use:
Following result of use is given an example, but the present invention is not limited to this.
Resistance:
Electrically conductive composition is coated on the sheet glass, places 24 hours dryings on request, adopts the method measuring resistance of four point probe then; Measurement result sees Table 1.
Table 1
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Prepare example 1 | Prepare example 2 | Prepare example 3 | |
| Resistance * 10 6Ω*m | 3 | 2.8 | 3.1 | 3 | 1.5 | 1.6 |
Device performance
Device architecture:
The ITO/PEDOT/P-PPV/PFN/ electrically conductive composition.Performance sees Table 2
Table 2
| Electrically conductive composition | Efficient (QE) % | Brightness Cd/M 2 | Open bright voltage *1V |
| Embodiment 1 | 3.7 | 14500 | 4.6 |
| Embodiment 2 | 3.8 | 6800 | 5.0 |
| Embodiment 3 | 2.4 | 5800 | 4.35 |
| Comparative Examples 1 | 2.9 | 2500 | 7.4 |
| Comparative Examples 2 | 3.2 | 2400 | 7.3 |
| Comparative Examples 3 | 2.7 | 2300 | 8.0 |
| The evaporation example *2 | 5.0 | 30000 | 5.5 |
In the table, open bright voltage
* 1: brightness is 1Cd/M
2The time driving voltage.
The evaporation example
* 2Structure: ITO/PEDOT/P-PPV/PFN/Ag.
From table 1,2, electrically conductive composition electric conductivity of the present invention is good, uses on the organic luminescent device of PLED, opens bright voltage and compares remarkable reduction with the evaporation structure.
Claims (5)
1. an electrically conductive composition is characterized in that comprising polymer, conducting particles, solvent, wherein
Described polymer is to be main chain, the side-chain structure unit polymer based on heterocycle structure with vinyl or acrylic; Perhaps
With vinyl or acrylic is main body and other fluoropolymer resin are done in main chain, side-chain structure unit based on the polymer of heterocycle structure copolymerization or blend;
Described conducting particles is that metal, alloy are the attritive powder of main body;
Described solvent is the solvent or the polymerisable liquid of dissolve polymer;
Described polymer and conducting particles volume ratio are at 1-3: between the 3-1;
The attritive powder granularity of described conducting particles is less than 100 μ m;
Described polymer is the copolymer that is made of two kinds of construction units in the following general formula (1);
R in the formula (1)
2For containing the substituting group of heterocycle structure;
The described substituting group that contains heterocycle structure is a kind of in carbazole, the pyrrolidones;
Perhaps described polymer is with having the copolymer that more than one other construction units constitute in the following general formula (4) by more than one construction units in the general formula (1)
R in the formula (4)
1Expression hydrogen atom or methyl, R
3Expression hydrogen atom or methyl, ethyl, propyl group, butyl, octyl group, lauryl, norborny or ten difluoro heptyl, trifluoroethyl, hexafluoro butyl.
2. electrically conductive composition as claimed in claim 1, it is characterized in that described conducting particles is metal gold, silver, copper, aluminium, palladium, platinum, nickel, chromium, cobalt, zinc, gallium, iron or the micro-alloy powder more than two kinds wherein, perhaps its clad material attritive powder, the perhaps attritive powder of its mixture; Or based on aforesaid attritive powder, add the attritive powder of other type, the attritive powder of described other type comprises: indium, V
2O
5, palladium, titanium, platinum, magnesium, silicon, strontium, europium, iridium, gallium, nickel, barium, lanthanum, boron, ruthenium, yttrium, cerium, gold or their mixture, carbon black; The attritive powder total amount of other types is no more than 10% weight of conducting particles.
3. electrically conductive composition as claimed in claim 1 is characterized in that described solvent is alkane, aromatic hydrocarbons, alcohol, ether, ketone, phenol, ester, acid, their halogen substituent or their mixture; Or vinyl or acrylic are main chain, side-chain structure unit liquid oligomer or the monomer with heterocycle structure.
4. electrically conductive composition as claimed in claim 1 is characterized in that also comprising other compositions, and described other compositions comprise polyacrylate, polyester, polyamide, polyketone, and its consumption is less than 10% weight of total amount.
5. the application of the described electrically conductive composition of one of claim 1-4 in the electrode of monochromatic or panchromatic luminescent device and the solar battery of making OLED/PLED.
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| CN103646686A (en) * | 2007-09-13 | 2014-03-19 | 汉高股份两合公司 | Conductive composition |
| JP5560014B2 (en) * | 2009-09-30 | 2014-07-23 | 太陽ホールディングス株式会社 | Conductive paste |
| EP2547735B1 (en) * | 2010-03-19 | 2016-03-16 | Carestream Health, Inc. | Anti-corrosion agents for transparent conductive film |
| JP2015026567A (en) * | 2013-07-29 | 2015-02-05 | 富士フイルム株式会社 | Composition for conductive film formation and method for producing conductive film |
| EP3043354B1 (en) * | 2015-01-12 | 2018-01-03 | Heraeus Deutschland GmbH & Co. KG | Use of an electrically conductive composition as an electrically conductive adhesive for mechanically and electrically connecting electrical conductors to electrical contacts of solar cells |
| EP3618081A4 (en) | 2017-04-28 | 2020-12-23 | Nanchang Unitetec Technology Co., Ltd. | ELECTROMAGNETIC SHIELDING FILM FOR CABLES |
| CN111244307B (en) * | 2018-11-29 | 2021-10-22 | Tcl科技集团股份有限公司 | Quantum dot light-emitting diode and preparation method thereof |
| CN111640876B (en) * | 2019-03-01 | 2021-10-22 | Tcl科技集团股份有限公司 | Composite material, preparation method thereof and quantum dot light-emitting diode |
| CN114752090B (en) * | 2022-03-21 | 2024-03-22 | 复旦大学 | A Co/PEDOT composite flexible self-supporting film and its preparation and application |
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| US20030054093A1 (en) * | 2001-04-17 | 2003-03-20 | Yasuko Tomida | Metal composition for making conductive film, metal composition for making electron emission element, and method for making electron emission element and image forming apparatus using the same |
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| US6117366A (en) * | 1997-07-23 | 2000-09-12 | Samsung Display Devices Co., Ltd. | Electrically conductive composition including metal particles |
| CN1211592A (en) * | 1997-08-29 | 1999-03-24 | 纳幕尔杜邦公司 | Thick film compositions for making medical electrodes |
| US20030054093A1 (en) * | 2001-04-17 | 2003-03-20 | Yasuko Tomida | Metal composition for making conductive film, metal composition for making electron emission element, and method for making electron emission element and image forming apparatus using the same |
| US20030216532A1 (en) * | 2001-04-17 | 2003-11-20 | Canon Kabushiki Kaisha | Metal composition for making a conductive film and metal composition for making an electron emission element |
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