WO2016118071A1 - Procédé de production d'un matériau composite conducteur - Google Patents

Procédé de production d'un matériau composite conducteur Download PDF

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Publication number
WO2016118071A1
WO2016118071A1 PCT/SE2016/050045 SE2016050045W WO2016118071A1 WO 2016118071 A1 WO2016118071 A1 WO 2016118071A1 SE 2016050045 W SE2016050045 W SE 2016050045W WO 2016118071 A1 WO2016118071 A1 WO 2016118071A1
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Prior art keywords
polymer
solvent
nanotubes
dispersion
film
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PCT/SE2016/050045
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English (en)
Inventor
David BARBERO
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Barbero David
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Publication date
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Publication of WO2016118071A1 publication Critical patent/WO2016118071A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • 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
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
    • B29C59/02—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
    • B29C59/022—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing characterised by the disposition or the configuration, e.g. dimensions, of the embossments or the shaping tools therefor
    • B29C2059/023—Microembossing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • H10K30/35—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains comprising inorganic nanostructures, e.g. CdSe nanoparticles
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to a method for producing a conductive or semiconductive material comprising conducting or semiconducting nanotubes or nanowires, and at least an organic macromolecular material (e.g. short molecule, polymer, ... ) which can be processed in solution.
  • the invention also relates to the resulting material comprising a conductive or semiconductive nanoscale network made of nanotubes or nanowires.
  • Nanotubes and nanowires made of carbon, metal or other
  • semiconducting materials have several interesting properties for electronic devices (transistors, solar cells, electrodes, etc . ).
  • single walled carbon nanotubes possess high aspect ratio and high charge carrier mobilities, making them very attractive for next generation of carbon based electronic devices.
  • a semiconducting polymer such as poly-3-hexylthiophene (P3HT).
  • P3HT poly-3-hexylthiophene
  • Temperature annealing has also been shown to modify the crystallinity, and the optical and electrical properties of polythiophene polymers.
  • semiconductive materials formed by a method comprising low temperatures and being solvent based provide properties which are beneficial for opto-electronic applications using organic semiconductor materials.
  • the present invention relates to a method performed at low temperature (ideally room-temperature) and low pressure which provides well defined arrays of nano-engineered nanotube/nanowire networks with much improved charge transport in organic polymers comprising delocalized (conjugated) ⁇ - electrons, such as , for example but not limited to, a P3HT film matrix (Fig. 2).
  • the presented invention is controllable, scalable and enables the formation of nano- sized networks with exceptional properties not achieved by other methods. [0004].
  • Charge transport in P3HT was enhanced by approximately two orders of magnitude compared to a random network produced by traditional solution based methods and around 4-5 times more compared to our previous results with a thermal method.
  • nanotube loadings massively conductive networks due to the nanoscale interconnectivity of the nano-networks, and the improved dispersion of the nanotubes in the solvent.
  • the low amount of nanoitubes used reduces bundling, increases transparency and provides an economical solution for electronic applications.
  • the method is simple, fast and prevents any unwanted change in materials' properties which may be caused by the use of high temperatures
  • CN101328276 discloses a method for providing SWNT composite film the method comprising the use of gum arabicum and a step where the
  • the temperature is kept at 70 to 100 degrees C.
  • the polymer emulsions used are exemplified as styrene-acrylic emulsions, pure acrylic emulsions and epoxy emulsions.
  • the document does not disclose semiconductive polymers comprising monomers containing aromatic moieties.
  • P3HT does not to disclosed. The method involves a step with temperatures way above RT.
  • CN103739903A discloses high conductivity carbon nanotube rubber composite which is produced by using a latex. The document does not disclose the use of disclose semiconductive polymers comprising monomers containing aromatic moieties. P3HT apperas not to be disclosed.
  • CN103073891 discloses a method for the preparation of high- conductivity flexible conductive composite materials.
  • the method encompasses a stage where graphene and carbon nano-tube are uniformly dispersed (CNTs) in an aqueous solution and where further resorcinol, formaldehyde and catalyst (sodium carbonate) are added, whereby the reaction temperature is 85°C and the reaction time three days.
  • a graphene -CNT-resorcinol-formaldehyde organic gel is formed.
  • the CNTs are carbonized in a furnace at a temperature of 900-1000 degrees centigrade.
  • the material does not contain CNT.
  • the method encompasses high temperature stages. Additionally, P3 does not disclose semiconductive polymers comprising monomers containing aromatic moieties.
  • the present invention relates to a method for producing a conductive or semiconductive material comprising nanotubes and at least a first polymer, the method comprising the steps of:
  • the invention relates to a method for producing a semiconductive material.
  • Said semiconductive material is preferable applied in photovoltaics and Organic Light-Emitting Diodes (OLEDS).
  • OLEDS Organic Light-Emitting Diodes
  • the invention is also directed to a conductive or semiconductive material obtainable by the method, and a photovoltaic component comprising the semiconductive material with SWNTs and a semiconductive polymer.
  • the dispersion comprises nanotubes and at least a first solvent.
  • the first solvent can be a mixture of several solvents.
  • the first solvent should facilitate the formation of a nanotube dispersion which preferably also exhibits properties facilitating the formation of a film on a substrate. It is preferable if the solvent has fast to moderate evaporating properties.
  • the first solvent has a vapour pressure above about 10 mmHg (at 20°C), above about 50 mmHg, above about 100 mmHg, above about 150 mmHg, above about 200 mmHg.
  • the properties of the first solvent is adjusted with regard to type of nanotube.
  • the first solvent is water, or a carbon based organic solvent, such as dichlorobenzene, chlorobenzene, trichlorobenzene, chloroform, toluene, xylene, dimethylformamide, or a fluorinated solvent or any mixtures of the exemplified solvents.
  • the first solvent may also be selected from non-chlorinated hydrocarbons or functionalised non-chlorinated hydrocarbons, such as non- chlorinated hydrocarbons comprising from 1 to 15 carbon atoms, possibly also comprising e.g. one or more hydroxyl groups.
  • the dispersion may also comprise a second polymer.
  • This second polymer may be the same as the first polymer comprised in the composition.
  • the second polymer may also be a different type of polymer with respect to the first polymer.
  • first and second polymers are of the same type.
  • the presence of a second polymer in the dispersion may facilitate the nanotubes to stay on the substrate during the film forming process.
  • the dispersion can have a concentration of nanotubes from about 0.00001 mg/ml up to about 10 mg/ml, suitably from about 0.0001 mg/ml up to about 10 mg/ml, suitably from about 0.0001 mg/ml up to about 5 mg/ml.
  • the first polymer of the present method can be selected from inorganic polymers, organic polymers or even mixtures thereof. According to an embodiment the first polymer is selected from organic polymers.
  • the first polymer is selected from conducting or semi-conducting polymers (with delocalized ⁇ electrons).
  • Semiconducting polymers can be used with this method to produce electronic devices such as photovoltaic components.
  • the first polymer is selected from semi-conducting polymers.
  • the semi-conducting polymers may be organic polymers comprising delocalized (conjugated) ⁇ - electrons. Delocalized ⁇ - electrons may also be referred to as conjugated ⁇ electrons.
  • Conjugated ⁇ - electrons or a conjugated system is a system of overlapping p-orbitals (bridging intervening sigma bonds) with delocalized electrons in compounds with alternating single and multiple, often double, bonds which normally decreases the overall energy of the compound and stability.
  • conjugated ⁇ - electrons may comprise heterocyclic aromatic monomers substituted with a moiety providing some steric properties to the overall polymeric network.
  • the moiety may be a straight or branched alkyl group, suitably straight alkyl group.
  • the polymer comprising delocalized (conjugated) ⁇ - electrons is suitably a polymer comprising heterocyclic aromatic monomers such as alkyl substituted thiophene monomers.
  • An example is a polythiophene polymer such as poly(3-hexylthiophene-2,5-diyl) also referred to as P3HT.
  • the polymer has suitably an average molecular weight form about 3-300 kg/mol.
  • a composition is deposited on the first film.
  • the composition comprises the first polymer and at least a second solvent.
  • This second solvent may be a mixtures of several solvents. It may also be similar or identical to the first solvent.
  • the second solvent will not evaporate too fast.
  • the second solvent may have a vapour pressure below about 200 mmHg (at 20°C), below about 150 mmHg, below about 100 mmHg, below about 50 mmHg.
  • the properties of the second solvent are chosen such to admitting dispersion of the first polymer and good film formation.
  • the second solvent may be selected form any of the exemplified first solvents, such as water, or a carbon based organic solvent, such as dichlorobenzene, chlorobenzene, trichlorobenzene, chloroform, toluene, xylene, dimethylformamide, or a fluorinated solvent or any mixtures of the exemplified solvents.
  • the second solvent is a mixture of chloroform and 1 ,2- dichlorobenzene.
  • the ratio of chloroform and 1 ,2-dichlorobenzene is in the range of from 95:5 to 60:40 based on weight.
  • the composition has a concentration of polymer below 8 wt %, preferably between 1 and 5 wt%.
  • the method comprises providing the dispersion and the composition, depositing the dispersion on a substrate thereby forming a first film, depositing the composition on the first film thereby forming a second film and thereafter imprinting the films, while the second film (composition) is still partially wet, with a mold providing patterns (three dimensional structure) in the nano-range, wherein the imprinting is conducted at a temperature below about 50°C.
  • the substrate and films are compressed during the imprint.
  • the method is conducted a low temperatures, such as below about 45°C, such as below about 40°C, below about 35°C, below about 30°C, such as up to about 10°C.
  • semiconducting polymers can been used which are temperature sensitive.
  • the films are imprinted.
  • the films obtain a specific three
  • the three dimensional geometric structure of the film is given by the three dimensional geometric structure of the mold.
  • the three dimensional geometric structure of the film has an implication on the properties of the conductive or semiconductive material.
  • the term nano range implies a value of any dimensional property such as one dimensional properties e.g. length, diameter, radius from around 1 nm up to around 100 pm.
  • the three dimensional geometric structure of the film should exhibit patterns with a height of from about 10 nm up to about 10 pm, suitably from about 30 nm up to about 10 pm.
  • the shortest length of the pattern is from 30 nm up to about 10 pm.
  • the three dimensional geometric structure of the film has the shape of pillars.
  • the pillars preferably have an average cross-section area of from about 10 "18 up to 10 "6 , suitably from about 10 "18 to about 10 "7 , preferably from about 10 "16 to about 10 " 8.
  • the pillars have a height of from about 5 nm up to about 10 pm, suitably from about 50 nm up to about 10 pm.
  • the pillars have a circular cross-section with a diameter of from 5 * 10 "9 to about 100 * 10 "6 .
  • Suitable methods of depositing the dispersion and composition for forming films include spin-coating, drop-casting, spray-coating or blade-coating. [00020].
  • the method also comprises imprinting the films with a mold.
  • the master molds can be formed by optical lithographical, electron-beam lithography, copolymer self-assembly, colloidal assembly, patterning, anodization techniques, etching, molding or nanoimprinting methods.
  • a flexible polymer mold is then replicated from the master mold by casting as described below.
  • a 10: 1 mixture of PDMS base and curing agent was degassed in a dessicator under rough vacuum and gently poured onto the silicon master mold, followed by curing in an oven for 5 hours at 150°C.
  • the PDMS replica mold was carefully detached and used for further imprinting steps.
  • a film of the macromolecular material was spin-coated or drop-casted on the substrate from solution, and was imprinted with the PDMS mold until solid nano- or micro- structures, replicating the mold, have formed and created a solid patterned film.
  • the mold is flexible and is fabricated from a material having an elastic Young's modulus below about 1 .8 GPa, suitably below about 1 .5 GPa, more preferably below about 1 .0 GPa.
  • Poly(dimethylsiloxane) PDMS is a preferred material of the mold.
  • the nanotubes or nanowires can be made of carbon, metal or a semiconducting material, and with a diameter as small as about 0.5 nm, and a length up to 100 microns.
  • the nanotubes are Single Wall Carbon Nanotubes (SWNTs).
  • SWNTs Single Wall Carbon Nanotubes
  • SWNTs can preferably have a diameter of from about 0.5 up to about 2 nm, and a length of from about 50 nm to about 1500nm.
  • the substrate can comprise several layers. Usually the substrate comprises at least one layer which can be silicon, conducting oxide, plastic substrate, another organic or inorganic film coating.
  • Fig. 1 shows different network configurations : nanoscale network vs. random
  • Fig 3 shows mobility data for a conductive polymer as function of nanotube concentration for 3 methods: (the current solvent low temperature method, thermal method, random network).
  • Fig 5 shows difference in bundle diameter between the room temprature solvent method and the thermal method.
  • the solvent method results in smaller bundles of nanotubes compared to thermal method (18nm vs 23nm) and much less larger bundles, resulting in reduced electrical network resistivity.
  • Fig. 6 shows the custom-made solvent imprint chamber
  • the samples were patterned using a exible polydimethylsiloxane (PDMS) mold.
  • the liquid PDMS solution (Sylgard 182) was mixed in a 10: 1 ratio with its precursor and degasified in a vacuum desiccator.
  • the still liquid mix was then poured on a patterned silicon master mold and placed in an oven at 150°C for several hours.
  • the cured PDMS was then peeled of the silicon master and used as a flexible mold.
  • the imprint chamber is shown in Fig. 2.
  • the flexible mold was attached to a moving 2 piston while the sample to be patterned was placed at the bottom of the chamber. A weight was placed on the piston before it is slowly lowered down on the sample at room temperature, adding a low pressure of 1 to 2 bar. Nitrogen then flowed through the chamber in order to dry the polymer film, allowing subsequent demolding of the sample.
  • the resulting features were characterized using optical microscopy, atomic force microscopy and scanning electron microscopy.
  • the conductivity, and/or charge carrier mobility were extracted from the l/V characteristics. The resulting conductivity data was deduced using voltage applied, current measured and the geometry of the sample measured by electron microscopy and atomic force microscopy characterization, with less than 5% error of measurement. The accuracy of measurement on the current measured and voltage applied were within 1 % each.
  • the conductivity of the samples depends strongly on the amount of nanotubes added to the dispersion.
  • a conductivity of approximately 0.01 S/m was obtained at low concentration of SWNTs (0.001 wt% of polymer) in the nano-network in polystyrene, whereas the random network gave no current at the same concentration.
  • a similar conductivity of 0.01 S/m was obtained in the random network by increasing the concentration of nanotubes by 5000 times. This shows the advantage of the method described in reducing the amount of nanotubes to still obtain good conductivity at very low concentration thanks to the formation of a percolated nanoscale network.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un procédé pour produire un matériau conducteur ou semi-conducteur qui comprend des nanotubes ou des nanofils, et au moins un polymère soit isolant soit conducteur qui peut comprendre un électron π délocalisé (conjugué).
PCT/SE2016/050045 2015-01-23 2016-01-25 Procédé de production d'un matériau composite conducteur WO2016118071A1 (fr)

Applications Claiming Priority (2)

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SE1550067 2015-01-23
SE1550067-1 2015-01-23

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WO2016118071A1 true WO2016118071A1 (fr) 2016-07-28

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040110856A1 (en) * 2002-12-04 2004-06-10 Young Jung Gun Polymer solution for nanoimprint lithography to reduce imprint temperature and pressure
US20040241900A1 (en) * 2001-09-27 2004-12-02 Jun Tsukamoto Organic semiconductor material and organic semiconductor element employing the same
US20060081882A1 (en) * 2004-10-15 2006-04-20 General Electric Company High performance field effect transistors comprising carbon nanotubes fabricated using solution based processing
JP2012135071A (ja) * 2010-12-20 2012-07-12 National Institute Of Advanced Industrial & Technology アクチュエータ用複合導電性薄膜、アクチュエータ素子

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040241900A1 (en) * 2001-09-27 2004-12-02 Jun Tsukamoto Organic semiconductor material and organic semiconductor element employing the same
US20040110856A1 (en) * 2002-12-04 2004-06-10 Young Jung Gun Polymer solution for nanoimprint lithography to reduce imprint temperature and pressure
US20060081882A1 (en) * 2004-10-15 2006-04-20 General Electric Company High performance field effect transistors comprising carbon nanotubes fabricated using solution based processing
JP2012135071A (ja) * 2010-12-20 2012-07-12 National Institute Of Advanced Industrial & Technology アクチュエータ用複合導電性薄膜、アクチュエータ素子

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOULANGER, N. ET AL.: "Nano-engineering of SWNT networks for enhanced charge transport at ultralow nanotube loading", ADVANCED MATERIALS, vol. 26, no. 19, 2014, pages 3111 - 3117 *
BOULANGER, N. ET AL.: "Nanostructured networks of single wall carbon nanotubes for highly transparent, conductive, and anti-reflective flexible electrodes", APPLIED PHYSICS LETTERS, vol. 103, no. 2, 2013, pages 021116.1 - 021116.5 *
BOULANGER, N. ET AL.: "SWNT nano-engineered networks strongly increase charge transport in P3HT", NANOSCALE, vol. 6, no. 20, 2014, pages 11633 - 11636 *
MEIER, R. ET AL.: "Film thickness controllable wet-imprinting of nanoscale channels made of conducting or thermoresponsive polymers", JOURNAL OF MATERIALS CHEMISTRY, vol. 22, no. 1, 2012, pages 192 - 198 *

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