GB2559337A - Method of producing PEDOT:PSS based electrodes - Google Patents
Method of producing PEDOT:PSS based electrodes Download PDFInfo
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- GB2559337A GB2559337A GB1701479.6A GB201701479A GB2559337A GB 2559337 A GB2559337 A GB 2559337A GB 201701479 A GB201701479 A GB 201701479A GB 2559337 A GB2559337 A GB 2559337A
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- pedot
- pss
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- 229920000144 PEDOT:PSS Polymers 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 27
- 125000000524 functional group Chemical group 0.000 claims abstract description 72
- 238000004873 anchoring Methods 0.000 claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 3
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 3
- 238000006664 bond formation reaction Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 80
- 239000000976 ink Substances 0.000 description 28
- 239000000758 substrate Substances 0.000 description 18
- 125000005372 silanol group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
- 238000000151 deposition Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- 229910002808 Si–O–Si Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005935 nucleophilic addition reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- -1 poly(styrenesulfonate) Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
-
- 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
- H10K71/60—Forming conductive regions or layers, e.g. electrodes
- H10K71/611—Forming conductive regions or layers, e.g. electrodes using printing deposition, e.g. ink jet printing
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/221—Carbon nanotubes
- H10K85/225—Carbon nanotubes comprising substituents
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a method of producing a PEDOT:PSS based electrode (300). A PEDOT:PSS (poly(3,4-ethylenedioxythiophene) polystyrene sulfonate) layer is provided on a surface (311) where the surface comprises at least one surface functional group (312). The PEDOT:PSS polymeric chains, present in said dried layer (320), comprise at least one hanging functional group (322). An adhesion promoter layer (329) is provided on the PEDOT:PSS dried layer (320) where the adhesion promoter layer comprises at least one organic solvent and at least one trialkoxysilane molecule (331). The at least one trialkoxysilane molecule comprises an anchoring functional group (333) and three alkoxysilane functional groups. The at least one organic solvent is evaporated (335). Covalent bonds are formed between some of the at least one surface functional group (312) and some of the three alkoxysilane functional groups (332) and between some of the anchoring functional groups (333) and some of the at least one hanging functional groups (322).
Description
(71) Applicant(s):
Saralon GmbH
Hall L, Lothringer StraBe 11, Chemnitz 09120, Germany (72) Inventor(s):
Moazzam Ali (56) Documents Cited:
GB 2525188 A US 20160056397 A1 (58) Field of Search:
INT CL C25B, H01L
Other: WPI, EPODOC, TXTE, XPESP (74) Agent and/or Address for Service:
Saralon GmbH
Hall L, Lothringer StraBe 11, Chemnitz 09120, Germany (54) Title of the Invention: Method of producing PEDOT:PSS based electrodes Abstract Title: Method of producing a PEDOT:PSS based electrode (57) The present invention relates to a method of producing a PEDOTPSS based electrode (300). A PEDOTPSS (poly (3,4-ethylenedioxythiophene) polystyrene sulfonate) layer is provided on a surface (311) where the surface comprises at least one surface functional group (312). The PEDOTPSS polymeric chains, present in said dried layer (320), comprise at least one hanging functional group (322). An adhesion promoter layer (329) is provided on the PEDOTPSS dried layer (320) where the adhesion promoter layer comprises at least one organic solvent and at least one trialkoxysilane molecule (331). The at least one trialkoxysilane molecule comprises an anchoring functional group (333) and three alkoxysilane functional groups. The at least one organic solvent is evaporated (335). Covalent bonds are formed between some of the at least one surface functional group (312) and some of the three alkoxysilane functional groups (332) and between some of the anchoring functional groups (333) and some of the at least one hanging functional groups (322).
/4
2/4
FIGURE 3Β '•s-j
FIGURE 3C
3/4
410; Providing a surface, wherein the surface comprises at least one surface functional group.
420: Providing a PPDOTtPSS dried layer on the surface, wherein PEDOT. PSS polymeric chams comprises at least one hanging lunefiou<tl group.
430: Providing an adhesion prornotor layer on the PI::DOT;PSS dried layer.
The adhesion promotor layer comprises at least one organic solvent and at least one trialkoxvdlane molecule. The at least one truihoxs silane molecule comprise-'
-440: Evaporating the at least one organic solvent,
450: Allowing covalent bonds formation between some of the at least one surface functional group and some of the three alkoxystlane functional groups and between some of the and toting functional group and some of the at least one hanging functional group.
4/4
-1 TITLE
Method of producing PEDOT:PSS based electrodes
CROSS-RELATION TO OTHER APPLICATIONS [0001] None
FIELD OF THE INVENTION [0002] The present disclosure relates to a production method of a strongly adhered PEDOT:PSS layer on a surface of a substrate.
BACKGROUND OF THE INVENTION [0003] Printed electronics is a field in which electronic devices are produced by printing methods and by using inks. One of the most commonly used ink in printed electronics is an aqueous dispersion of Poly(3,4-ethy!enedioxythiophene:poly(styrenesulfonate) (hereinafter referred to as PEDOT.’PSS). PEDOT:PSS is used as a transparent and conducting electrode. It is also used, but not limited to, in eSectrochromic devices. Water is most commonly used solvent for PEDQUPSS ink and the content of water in the ink is more than 95% by weight. Water based PEDOUPSS ink is deposited on a surface by using a printing method or by using a coating method. After that water is removed by a drying process. A dried layer of PEDQUPSS is left on the surface. Different additives are used in PEDOT:PSS ink to lower its surface tension in order to make PEDQUPSS adhesion stronger on the surface, as mentioned in US 20160056397 Al and EP 2015135 BI. In order to further increase the adhesion of PEDQUPSS on the surface, the surface is plasma or corona treated before depositing the PEDQUPSS ink. Corona and/or plasma treatment of a plastic substrate generate various reactive functional groups - hydroxyl, carboxyl, carbonyl, hydroperoxide etc. -- on the surface of the plastic. Plasma are/or corona treatment of plastic substrate are very common techniques to increase adhesion of ink on a surface. Despite all these efforts, the adhesion of PEDOUPSS on a plastic or on a glass surface is still not strong enough. A dried layer of PEDOUPSS deposited on a surface can easily be removed from the surface by a scotch-tape test. The reason behind this weak adhesion is that there is no or negligible covalent bonds between polymeric chains of PEDOUPSS and the surface. A covalent bond is a chemical bond that involves sharing of electron pairs between atoms e.g. the bond between hydrogen atom and the oxygen atom in a water molecule is a covalent bond. Covalent bonds make adhesion stronger.
-1[0004] Figure I shows a cross section view of a printed electronic device 100. A PEDOT:PSS dried layer 120 is provided on a surface I l l of a substrate 110. The PEDQEPSS dried layer 120 is produced by depositing a PEDOT;PSS wet layer on the surface 111 and then drying out water from the wet layer. On top of the PEDO'EPSS dried layer 120 are deposited other electronically functional layers e.g. semiconducting layer, conducting layer, electron blocking layer, hole blocking layer, light emitting particles, electrolyte layer, electronically insulating layer etc. The printed electronic device 100 can be, but not limited to, a solar cell, a lightemitting diode, a diode, an inorganic panicle based electroluminescent device, electrochemical light emitting cell, electrochromic device, transistor, sensor etc. In a non-limiting example, the printed electronic device 100 can be an OLED which comprises a semiconducting light emitting polymer layer 130 (e.g. Super Yellow from Merck), an electron transporting layer 140 (e.g. zinc oxide), a top conducting silver layer 150 and a barrier layer 160. In another non-limiting example, the printed electronic device 100 can be an alternating current driven electroluminescent device which comprises a zinc oxide particle based phosphor layer 130, a dielectric layer 140 (e.g. BaTiO3), a top conducting silver layer 150 and a barrier layer 160. The problem with all these printed electronic devices is that with time the performance of these devices decrease by mechanical bending of the device. This is due to the delamination of PEDOT:PSS dried layer 120 from the substrate 110.
[0005] In some applications printed electronic device 200 is used as a sticker, as shown in Figure 2 A. A PEDOT PSS dried layer 220 is provided on a surface 211 of a substrate 210. The PEDOT:PSS dried layer 220 is produced by depositing a PEDOT:PSS wet layer on the surface 211 and then drying out water from the wet layer. On top of the PEDOT:PSS dried layer 220 are provided different electronically functional layers (e.g. 230, 240, 250). A barrier layer 260 can be provided too. A pressure sensitive adhesive layer 270 is provided on top of the barrier layer 260. A release paper 280 (e.g. silicone coated paper) is provided on top of the pressure sensitive adhesive layer 270. Before the application of the device 200, the release paper 280 is removed and the device 200 is fixed on another surface through the pressure sensitive adhesive layer 270. In a desired case, after removing the release paper 280 the device 200 should look like as shown in Figure 2B i.e. no damage in any layer. But in some cases, some part of the device 200 is also removed with the release paper 280, as shown in Figure 2C. This happened because of the weak adhesion of PEDOT:PSS dried layer 220 on the substrate 210,
-3[0006] Trialkoxysilane molecules are known for their adhesion promotion properties. Some example of trialkoxysilane molecules are, but not-limited to (3Glycidyloxypropyl)trimethoxysilane, (3-Glycidyloxypropyl)triethoxysilane, [2-(3,4Epoxycyclohexyl)ethyl]trimethoxysilane, 3 -[2-(2Aminoethylamino)ethylamino]propyltrimethoxysilane, (3-Aminopropyl)triethoxysilane, [3(2-Aminoethylamino)propyl]trimethoxysilane, (3-Mercaptopropyl)triethoxysilane and (3Aminopropyl)trimethoxysilane. Trialkoxysilane molecule comprises three alkoxysilane functional groups and a carbon chain with an anchoring functional group. For example, in (3Glycidyloxypropyl)trimethoxysilane, the anchoring functional group is epoxy and alkoxysilane functional group is methoxysilane. In (3-Aminopropyl)triethoxysilane the anchoring functional group is a primary amine and the alkoxysilane functional group is ethoxysilane. Trialkoxysilane molecules are mixed into an ink before printing the ink. After printing, the ink is dried by a drying or a curing step. Trialkoxysilane molecules are also present in the dried layer of the ink. Over time the three alkoxy silane functional groups of a trialkoxysilane molecule are hydrolyzed into three silanol functional groups in presence of water (water can come into the dried layer of the ink from moisture of the surrounding or some other source). Silanol functional groups are very reactive and they form covalent bonds with surface functional groups present on the surface of a substrate. They also react with each other and create a Si-O-Si covalent bond. They can also react with the material present in the ink e.g. surface hydroxyl functional group of an oxide particle or with hydroxyl function group present on polymeric chains. This way the adhesion between the dried ink layer and the surface of the substrate is enhanced. But the problem with PEDOT:PSS ink is that it comprises more than 95% water and the ink is acidic in nature. Therefore, after mixing trialkoxysilane molecules into the PEDOT:PSS ink, all the alkoxysilane functional groups immediately react with water and are converted into silanol functional groups. After that silanol functional groups react to each other in the PEDOT:PSS ink itself. Hence, trialkoxysilane molecule does not work as a good adhesion promotor for water based PEDOT:PSS ink.
[0007] Pre-treatment of a surface of a substrate with trialkoxysilane molecules is known in the literature to increase adhesion of PEDOT:PSS on the surface. But this too does not create strong adhesion. After treating a surface with trialkoxysilane molecules, alkoxysilane are hydrolyzed into silanol functional groups. The silanol functional groups covalently binds with the surface functional group or to each other. The unreacted anchoring functional group of the trialkoxysilane molecules are used to reacts with inks. When an aqueous ink of PEDOT:PSS is
-4printed on top of the treated surface, the H+ ions present in the PEDOT:PSS ink react with the anchoring functional group and make them useless for further covalent bond formation. For example, water and H+ ions react with an epoxy anchoring functional group and creates two hydroxyl group. There are very less chance that sulfonic acid or sulfonate of polymeric chain of PEDOT:PSS make nucleophilic addition to the epoxy anchoring functional group. This nucleophilic addition can make the adhesion of PEDOT:PSS on the surface stronger. But sulfonic acid and/or sulfonate functional groups are very less in number in a PEDOT:PSS ink and hence their chances to react with anchoring functional group is very low.
SUMMARY OF THE INVENTION [0008] The present invention relates to a method of producing a PEDOT :PSS based electrode. A surface is provided which comprises at least one surface functional group. A PEDOT:PSS dried layer is provided on the surface. PEDOT:PSS polymeric chains, present in the PEDOT:PSS dried layer, comprises at least one hanging functional group. An adhesion promotor layer is provided on top of the PEDOT:PSS dried layer. The adhesion promotor layer comprises at least one organic solvent and at least one trialkoxysilane molecule. The at least one trialkoxysilane molecule comprises an anchoring functional group and three alkoxysilane functional groups. The at least one trialkoxysilane molecule is less than 5% of the weight of the adhesion promotor layer. The at least one organic solvent is evaporated. After that covalent bonds formation between some of the at least one surface functional group and some of the three alkoxysilane functional groups and between some of the anchoring functional group and some of the at least one hanging functional group is allowed.
BRIEF DESCRIPTION OF THE DRAWINGS [0009] FIG. 1 is a cross sectional view of a printed electronic device, comprising PEDOT:PSS.
[00010] FIG. 2A is a cross sectional view of a printed electronic device, comprising a release liner.
-5[00011 ] FIG. 2B is a cross sectional view of a printed electronic device after perfectly removed release liner.
[00012] FIG. 2C is a cross sectional view of a damaged printed electronic device after removed release liner.
[00013] FIG. 3A is a cross [00014] FIG. 3B is a cross [00015] FIG. 3C is a cross adhesion promotor layer.
sectional view of a substrate and a PEDOT:PSS wet layer.
sectional view of a substrate and a PEDOT:PSS dried layer.
sectional view of a substrate, a PEDOT:PSS dried layer and a wet [00016] FIG. 3D is a cross sectional view of a substrate, a PEDOT:PSS dried layer and a dried adhesion promotor layer.
[00017] FIG. 3E is a cross sectional view of a substrate and a strongly adhered PEDOT:PSS dried layer.
[00018] FIG. 4 is a flow chart showing a manufacturing process to produce a strongly adhered PEDOT:PSS dried layer.
DETAIFED DESCRIPTION OF THE PREFERRED EMBODIMENTS [00019] The invention will now be described in detail. Drawings and examples are provided for better illustration of the invention. It will be understood that the embodiments and aspects of the invention described herein are only examples and do not limit the protector’s scope of the claims in any way. The invention is defined by the claims and their equivalents. It will be understood that features of one aspect or embodiment of the invention can be combined with the feature of a different aspect or aspects and/or embodiments of the invention.
[00020] The terms “print,” “printability,” “printing,” “printable” and “printed”, as used here, refer to production methods using functional inks. More specifically, these production methods include, but are not limited to, screen-printing, stenciling, flexography, gravure, off-set, thermal
-6transfer and ink-jet printing. These printing methods can be roll-to-roll or sheet-fed or manual. The term “ink” as used in this disclosure refers to a material that is in liquid or semi-solid or, paste form. It will be understood that, after printing of an ink on a surface, a drying or curing process may be required to convert the ink into a solid or a gel form. Typically, heat and/or radiation are used for the drying or curing processes. The drying or curing processes can also be self-activated. The term “functional group” as used here refers to a specific group of atoms or bonds within a molecule or a polymer that are responsible for a specific chemical reaction. For example, in a conjugated polymer double bonds between carbon atoms are called functional groups, which may participate in a radical reaction.
[00021] The present invention is about a method of production of a strongly adhered PEDOT:PSS layer on a surface of a substrate. Figure 3 A shows the first step of the production method in which a PEDOT:PSS wet layer 319 is deposited on the surface 311 of a substrate 310. The substrate can be, but not limited to, glass, plastic, PET, PEN, PP, PE, HDPE etc. The surface 311 can be corona treated or plasma treated to increase number of surface functional groups 312. In one non-limiting aspect, the surface functional group can be hydroxyl, hydroperoxide, carbonyl, carboxyl and a combination thereof. The PEDOT:PSS wet layer 319 comprises a plurality of PEDOT:PSS polymeric chains 321 dispersed in water. The PEDOT:PSS PEDOT:PSS polymeric chains 321 comprises some hanging functional group 322. These hanging functional group 322 are sulfonic acid and/or sulfonate hanging on the chain of PSS polymer. The deposition of PEDOT:PSS wet layer 319 can be done by using a printing method or by using a coating method. After the deposition of PEDOT:PSS wet layer 319, a drying process is used to evaporate water. The removal of water creates a solid film of a PEDOT:PSS dried layer 320, as shown in Figure 3B. In the next step as shown in Figure 3C, an adhesion promotor layer 329 is printed on top of the PEDOT:PSS dried layer 320. The adhesion promotor layer 329 comprises at least one organic solvent 335 and at least one trialkoxysilane molecule 331. The trialkoxysilane molecule 331 comprises an anchoring functional group 333 and three alkoxysilane functional groups 332. Non-limiting examples of trialkoxysilane molecule are (3-Glycidyloxypropyl)trimethoxysilane, (3Glycidyloxypropyl)triethoxysilane, [2-(3,4-Epoxycyclohexyl)ethyl]trimethoxysilane, 3-[2-(2Aminoethylamino)ethylamino]propyltrimethoxysilane, (3-Aminopropyl)triethoxysilane, [3(2-Aminoethylamino)propyl]trimethoxysilane, (3-Aminopropyl)trimethoxysilane. In a nonlimiting aspect, the alkoxysilane functional group 332 can be methoxysilane or ethoxysilane. In a non-limiting aspect, the anchoring functional group 333 can be epoxy or primary amine.
-Ί In a non-limiting aspect, the adhesion promotor layer 329 can further comprise a semiconducting polymer 334, as used in organic light emitting diode or in organic photovoltaic or in organic diode. In another non-limiting aspect, the adhesion promotor layer 329 can further comprise doped zinc oxide particle based phosphors 334. Doped zinc oxide particles are used as light emitting layer in an alternating current driven electroluminescent device. The at least one organic solvent 335 can be any organic liquid or a mixture of organic solvents that can dissolve the trialkoxysilane molecule.
[00022] In the next production step, as shown in Figure 3D, the organic solvent 335 is evaporated. And a dried adhesion promotor layer 330 is left on top of the PEDOT:PSS dried layer 320. The trialkoxysilane molecules 331 are very small in size compared to PEDOT:PSS polymeric chains 321, they can easily penertae into the PEDOT:PSS dried layer 320. Most of the bigger particle or polymer 334, if present in the adhesion promotor layer 330 remains on the top surface of the PEDOT :PSS dried layer 320. In the next production step, the PEDOT :PSS based electrode is allowed to stay in a humid environment, with a relative humidity level of more than 40%. In presence of water molecules, the three alkoxysilane functional groups 332 are hydrolyzed into three reactive silanol function groups. The reactive silanol group, if present close to the surface 311, can covalently bind with the surface functional groups 312 i.e. hydroxyl, hydroperoxide, carboxyl. Some of the silanol functional group will also react to each other and will create a network of Si-O-Si bonds. This network of Si-O-Si can also help to keep the PEDOT:PSS polymeric chains 321 locked to the surface 311. Some silanol functional group can also react with the hanging functional group 322 e.g. sulfonic acid and/or sulfonate of PEDOT:PSS polymeric chain. As the PEDOT:PSS dried layer 320 is closely packed and there is no liquid water present, it is very likely that the hanging functional group 322 will come close to the anchoring functional group 333 and can make covalent bonds. For example, epoxy functional group of (3-Glycidyloxypropyl)triethoxysilane can react with the sulfonate group by nucleophilic addition and can create covalent bond. In another example, amine functional group of (3-Aminopropyl)triethoxysilane can react with sulfonic acid and create N-0 bonds.
[00023] The at least one trialkoxysilane molecule 331 is less than 5% of the weight of the adhesion promotor layer 329. More specifically, weight percentage of trialkoxysilane molecule 331 is less than 2 %.
[00024] The method of producing a PEDOT:PSS based electrode is illustrated in Figure 4.
Claims (10)
1. A method of producing a PEDOT:PSS based electrode (300), comprising the steps of:
a. providing a surface (311), wherein the surface (311) comprises at least one surface functional group (312);
b. providing a PEDOT:PSS dried layer (320) on the surface (311), wherein PEDOT:PSS polymeric chains (321) comprises at least one hanging functional group (322);
c. providing an adhesion promotor layer (329) on the PEDOT:PSS dried layer (320), the adhesion promotor layer (329) comprises at least one organic solvent (335) and at least one trialkoxysilane molecule (331), the at least one trialkoxysilane molecule (331) comprises an anchoring functional group (333) and three alkoxysilane functional groups (332), the at least one trialkoxysilane molecule (331) is less than 5% of the weight of the adhesion promotor layer (329);
d. evaporating the at least one organic solvent (335); and
e. allowing covalent bonds formation between some of the at least one surface functional group (312) and some of the three alkoxysilane functional groups (332) and between some of the anchoring functional group (333) and some of the at least one hanging functional group (322).
2. The method of claim 1, wherein the step of allowing covalent bond formation is done in a humid environment with a relative humidity of more than 40%.
3. The method of claim 1, wherein the PEDOT:PSS dried layer (320) is provided by printing a PEDOT:PSS wet layer (319) on the surface (311) and then drying out water from the PEDOT:PSS wet layer (319).
4. The method of claim 1, wherein the anchoring functional group (333) is an epoxy.
5. The method of claim 1, wherein the anchoring functional group (333) is a primary amine.
6. The method of claim 1, wherein the at least one hanging functional group (322) is selected from a group of sulfonic acid, sulfonate and combinations thereof.
-97. The method of claim 1, wherein the at least one trialkoxysilane molecule (331) is selected from a group of (3-Glycidyloxypropyl)trimethoxysilane, (3Glycidyloxypropyl)triethoxysilane, [2-(3,4-Epoxycyclohexyl)ethyl]trimethoxysilane, 3-[2-(2-Aminoethylamino)ethylamino]propyltrimethoxysilane, (3Aminopropyl)triethoxysilane, [3-(2-Aminoethylamino)propyl]trimethoxysilane, (3Aminopropyl)trimethoxysilane and combinations thereof.
8. The method of claim 1, wherein the adhesion promotor layer (329) further comprises at least one semiconducting polymer (334).
9. The method of claim 1, wherein the adhesion promotor layer (329) further comprises at least one zinc oxide particle based phosphors (334).
10. The method of claim 1, wherein the at least one surface functional group (312) is selected from a group of hydroxyl, hydroperoxide, carboxyl and a combination thereof.
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| GB1701479.6A GB2559337A (en) | 2017-01-30 | 2017-01-30 | Method of producing PEDOT:PSS based electrodes |
| PCT/EP2018/025018 WO2018137892A1 (en) | 2017-01-30 | 2018-01-23 | Method of producing pedot:pss based electrodes |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1701479.6A GB2559337A (en) | 2017-01-30 | 2017-01-30 | Method of producing PEDOT:PSS based electrodes |
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| GB201701479D0 GB201701479D0 (en) | 2017-03-15 |
| GB2559337A true GB2559337A (en) | 2018-08-08 |
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| CN115521702B (en) * | 2022-09-23 | 2023-10-17 | 湖南纳昇电子科技有限公司 | PEDOT (polyether urethane) PSS (polyphenylene sulfide) electronic coating capable of enhancing reflection and high in hardness as well as preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2525188A (en) * | 2014-04-14 | 2015-10-21 | Univ Sheffield Hallam | Electrically conducting PEDOT sol-gel derived coating |
| US20160056397A1 (en) * | 2013-03-29 | 2016-02-25 | Heraeus Deutschland GmbH & Co. KG | Non-Polar Solvents As An Adhesion Promoter Additive In PEDOT/PSS Dispersions |
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| EP2015135B1 (en) | 2002-03-07 | 2012-02-01 | Acreo AB | Electrochemical device |
| WO2014006700A1 (en) * | 2012-07-04 | 2014-01-09 | シャープ株式会社 | Process for producing organic thin film |
| KR102245645B1 (en) * | 2014-09-02 | 2021-04-29 | 광주과학기술원 | Pedot:pss based electrode and method for manufacturing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20160056397A1 (en) * | 2013-03-29 | 2016-02-25 | Heraeus Deutschland GmbH & Co. KG | Non-Polar Solvents As An Adhesion Promoter Additive In PEDOT/PSS Dispersions |
| GB2525188A (en) * | 2014-04-14 | 2015-10-21 | Univ Sheffield Hallam | Electrically conducting PEDOT sol-gel derived coating |
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| GB201701479D0 (en) | 2017-03-15 |
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