WO2013096841A1 - Transfert assisté de graphène - Google Patents

Transfert assisté de graphène Download PDF

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Publication number
WO2013096841A1
WO2013096841A1 PCT/US2012/071377 US2012071377W WO2013096841A1 WO 2013096841 A1 WO2013096841 A1 WO 2013096841A1 US 2012071377 W US2012071377 W US 2012071377W WO 2013096841 A1 WO2013096841 A1 WO 2013096841A1
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WO
WIPO (PCT)
Prior art keywords
graphene
receiving substrate
fluorinated polymer
transfer stamp
transfer
Prior art date
Application number
PCT/US2012/071377
Other languages
English (en)
Inventor
Ioannis Kymissis
Marshall Cox
Original Assignee
The Trustees Of Columbia University In The City Of New York
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by The Trustees Of Columbia University In The City Of New York filed Critical The Trustees Of Columbia University In The City Of New York
Publication of WO2013096841A1 publication Critical patent/WO2013096841A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/182—Graphene
    • C01B32/194—After-treatment

Definitions

  • graphene An allotrope of carbon in atomically thin planar form, graphene is emerging as a nanomaterial due to its unique combination of physical and electrical properties.
  • Graphene can be incorporated in organic semiconductor devices, e.g., as a transparent electrode for organic optoelectronics devices, and as a component into various electronic devices. In these device applications, there can be requirements that graphene be transferred onto device substrates.
  • the material that graphene is transferred onto can be sensitive to impurities.
  • the semiconducting layers are not exposed to any materials that can contaminate and/or degrade the performance of the semiconducting layers.
  • the transfer processes can also require the use of solvents or heat, which can damage the semiconducting properties of small molecule or polymer semiconducting materials in the organic electronics devices.
  • the disclosed subject matter provides techniques for transfer of graphene onto a receiving substrate.
  • Graphene can be adhered to a surface of a transfer stamp which includes a fluorinated polymer.
  • the transfer stamp can be positioned with the graphene contacting a surface of a receiving substrate, and pressure can be applied on the transfer stamp.
  • the fluorinated polymer can then be removed, leaving the graphene attached to the surface of the receiving substrate.
  • the transfer stamp can be removed from the receiving substrate, thus leaving the graphene attached to the surface of the receiving substrate with the fluorinated polymer adhering to the graphene. Thereafter, the fluorinated polymer can be removed.
  • the fluorinated polymer can be removed.
  • removing the fluorinated polymer can be performed without first removing the transfer stamp.
  • the fluorinated polymer is soluble in a fluorous solvent, such as segregated hydrofluoroether.
  • removing the fluorinated polymer can include using a fluorous solvent, such as a segregated hydrofluoroether, or using supercritical C0 2 .
  • the receiving substrate can include an inorganic material. In other embodiments, the receiving substrate can include a non-fluorinated organic material, such as an organic material used in organic electronics or semiconductor devices.
  • Figure 1 is a flowchart for an example method for graphene transfer according to some embodiments of the disclosed subject matter.
  • Figures 2a-2c are schematic diagrams for an example graphene transfer procedure according certain embodiments of the disclosed subject matter.
  • Figures 3a and 3b are Raman spectra of graphene on different substrates according to an example embodiment of the disclosed subject matter.
  • Figures 4a and 4b are SEM images of graphene transferred onto an example organic thin-film (in 4a) and onto silicon (in 4b), respectively, according certain embodiments of the disclosed subject matter.
  • Figure 5a is a plot of I-V curves of a control OLED versus an OLED including a graphene cathode transferred according to the disclosed subject matter;
  • Figure 5b depicts a photo of an OLED having a graphene cathode transferred according to the disclosed subject matter.
  • the disclosed subject matter relates to systems and methods for transfer of graphene onto a receiving substrate such as a semiconductor thin film.
  • Graphene transferred according to the disclosed subject matter can be used as a component in organic electronics devices, such as a transparent electrode for Organic Light Emitting Diodes (OLEDs),
  • OLEDs Organic Light Emitting Diodes
  • Graphene can be adhered to a surface of a transfer stamp which includes a fluorinated polymer (at 1 10).
  • the transfer stamp with the adhered graphene can be positioned on a receiving substrate such that the graphene is in contact with a surface of the receiving substrate (at 120).
  • Pressure can be applied on the transfer stamp against the receiving substrate (at 130), thus pushing the graphene against the surface of the receiving substrate.
  • the fluorinated polymer can be removed (at 140), e.g., by using a suitable solvent, leaving the graphene attached on the surface of the receiving substrate. This procedure is further described below in conjunction with Figures 2a-2c.
  • graphene can include single-layer graphene and graphene sheet that include multiple layers, e.g., 2-10 layers.
  • the physical characteristics and quality of graphene can depend on the conditions and parameters for manufacturing processes of the graphene, e.g., chemical vapor deposition, exfoliation, epitaxial growth, etc. Large areas (e.g., about 00 microns on edge or larger) of graphene can be produced, for example, by chemical vapor deposition on metal substrates, such as copper backing.
  • FIG 2a illustrates an example procedure to prepare a transfer stamp.
  • the transfer stamp (240 in Figures 2a-2c) can have a planar surface for contacting graphene during the transfer process.
  • the transfer stamp can include a base (210 in Figure 2a) made of various materials, such as plastic, metal, inorganic materials, etc. in certain embodiments, the transfer stamp can include a base made from a soft material, such as a pliant polymer, e.g., silicones including polydimethylsiloxane (PDMS).
  • the transfer stamp can include a passivation layer on the base, such as a Parylene C layer, serving as a chemically inert moisture and dielectric barrier (220 in Figure 2a shows a base coated with a passivation layer).
  • the transfer stamp can be sized suitably for handling by hand tools (such as tweezers), robotic hand, or other automated tools.
  • the contact surface of the transfer stamp can be made to be of similar size or larger size than the graphene to be transferred.
  • the stamp can have a contact surface of about 1 mm x 1 mm.
  • a plurality of transfer stamps e.g., one for each graphene sample
  • one transfer stamp can include an array or matrix of protrusions of areas each used for transferring an individual graphene sample.
  • the surface of the transfer stamp for contacting graphene can include a fluorinated polymer (230 in Figures 2a-2c),
  • the fluorinated polymer can be present as a coating or layer, e.g., by spin-coating, and can serve as a "sacrificial" layer in the transfer process (which will be later removed).
  • Fluorinated polymers can include polymers or copolymers that have appropriate molecular structure and fluorine content that render them soluble in supercritical C0 2 or the various fluorous solvents described below.
  • fluorinated polymer can include resorcinarene, a copolymer of perfiuorodecyl methacrylate and 2-nitrobenzyl methacrylate, derivatives thereof or other polymer photoresist or molecular glass photoresists having sufficient fluorine content.
  • fluorinated polymers include those disclosed in U.S. Patent Application Publication No. 2011/0159252, which is incorporated herein by reference in its entirety.
  • the graphene For adhering graphene onto the fluorinated polymer layer of the transfer stamp, the graphene can be first cut (e.g., by laser, plasma, Ni nanoparticle, etc.) into pieces with desired dimensions, for example, according to the electronics devices applications where the graphene is to be incorporated. If the graphene has been obtained from a CVD process, a metallic backing material used in the CVD process, e.g., copper foil, can be still attached to the graphene.
  • a metallic backing material used in the CVD process e.g., copper foil
  • adherence of the graphene with copper foil to the transfer stamp can be accomplished by placing the transfer stamp with the fluorinated polymer layer facing up, placing the graphene in contact with the fluorinated polymer layer of the transfer stamp, and pressing a second object, such as a glass-backed PDMS stamp, against the graphene and the transfer stamp.
  • a second object such as a glass-backed PDMS stamp
  • the graphene together with the copper foil can be transferred onto the fluorinated polymer layer of the transfer stamp 240.
  • the copper foil can then be removed by an etchant, e.g., ammonium persulfate, which results in the bare graphene (270) being left attached to the transfer stamp 240 (shown in Figure 2b).
  • Other metallic backing material for the graphene can be similarly removed by suitable etchants.
  • the transfer stamp with adhered graphene (metallic backing, if any, has been removed) can then be brought into contact with a surface of a receiving substrate (280), with the graphene (270) to contact the surface of the substrate (280).
  • Pressure can be applied for a duration of time, e.g., a few seconds or a few minutes, on the transfer stamp to press the graphene onto the substrate surface.
  • the amount of pressure and the time during which the pressure is applied can be selected based on factors such as ambient temperature and the adhesion of the graphene to the fluorinated polymer relative to its adhesion to the surface of the receiving surface.
  • Graphene can be transferred according to the above-outlined procedure to various substrates, including inorganic substrates, such as silicon, silica, metal, or substrates made of organic materials.
  • the surfaces of organic substrates can be low- energy, fragile, and chemically vulnerable surfaces.
  • the surfaces of the organic substrates comprise materials that are not fluorinated polymers discussed above, and thus are not soluble in the fiuorous solvents or supercritical C0 2 described below.
  • Example organic substrates can include small organic molecules as well as polymers commonly used in organic electronics or semiconductor devices, such as hole transport layer materials, hole injection layer materials, electron or hole transport layer materials, electron injection layer materials, phosphorescent host materials, fluorescent host materials, organic photovoltaic materials, organic thin film transistor materials, liquid crystal display materials, conducting polymers (such as PEDOT, polypyrrole, polyaniline), insulator polymers (such as PMMA, polycarbonate, PVA, etc.), etc.
  • the substrate can include organic electronics components of an OLED.
  • the graphene laminated on the surface of the substrate can constitute a component of the device, e.g., a transparent cathode.
  • the fluorinated polymer 230 when the transfer stamp is removed, the fluorinated polymer 230 can peel off from the stamp and stay adhered to the graphene 270, which is attached to the substrate surface (shown as configuration 290 in fA I JiJ I
  • FIG. 2c This can be attributed to the greater adhesion between the graphene with the surface of the receiving substrate than that between the fluorinated polymer coating with the underlying material of the stamp (e.g., Parylene C layer on the transfer stamp as shown).
  • the fluorinated polymer layer transferred along with the graphene can then be removed using a suitable solvent, such as supercritical C(3 ⁇ 4 or various fluorous solvents as further discussed below.
  • the solvent can be applied while the transfer stamp is still positioned on the substrate. This can also strip away the fluorinated polymer, and thereafter, the stamp can be removed, leaving the graphene attached to the substrate surface.
  • the solvent for removing the fluorinated polymer from the graphene can be a fluorous solvent (or mixtures of various fluorous solvents) that can dissolve the fluorinated polymer but does not dissolve or chemically react with the surface of the substrate.
  • fluorous solvents include perfluorinated or highly fluorinated liquids, which are immiscible with organic solvents and water.
  • HFEs hydrofluoroethers
  • methyl nonafluorobutyl ether methyl nonafluoroisobutyl ether
  • isomeric mixtures of methyl nonafluorobutyl ether and methyl nonafluoroisobutyl ether ethyl nonafluorobutyl ether
  • ethyl nonafluorobutyl ether ethyl
  • nonafluoroisobutyl ether isomeric mixtures of ethyl nonafluorobutyl ether and ethyl nonafluoroisobutyl ether, 3-ethoxy-l , 1 , 1 ,2,3,4,4,5,5,6,6,6-dodecafluoro-2- trifluoromethyl-hexane, 1,1, ,2,2,3 ,4,5, 5,5 -decafluoro-3 ⁇ methoxy-4-trifluoromethyl- pentane, 1,1,1 ,2,3,3-hexafluoro-4-(l , 1 ,2,3,3,3,-hexafluoropropoxy)-pentane, and combinations thereof.
  • the HFE can be generally described using the formula R h -0-R f , wherein R h is a straight-chained or branched alley! group, and Rf is a perfluorinated straight-chained or branched alkyl group.
  • fluorous solvents include chlorofluorocarbons (CFCs): C x Cl y F z , hydrochlorofluorocarbons (HCFCs): C x Cl y F z H w , hydrofluorocarbons (HFCs): C x F y H z , perfluorocarbons (FCs): C x F y , perfluoro ethers: C x F y OC z F w , perfluoroamines: (C x F y ) 3 N, trifluoromethyl (CF 3 )-substituted aromatic solvents: (CF 3 ) x Ph [benzotrifluoride, bis(trifluoromethyl)benzene].
  • the fluorous solvents can further include the fluorous or fluorinated solvents disclosed in U.S. Patent
  • This example describes the use of a fluorinated (Fl) polymer or resist material for the transfer of graphene onto organic thin films using an exemplary method of the disclosed subject matter.
  • TPBi, LumTec 2,2',2"-(l,3,5- benzinetriyl)-tris(l -phenyl- 1-H-benzimidazole (TPBi, LumTec) films were evaporated on indium Tin Oxide (ITO)-coated glass (LumTec) at 1 Angstrom per second to a thickness of 40 nm via an Angstrom Engineering thermal evaporator mated to an MBraun glovebox.
  • ITO indium Tin Oxide
  • LumTec indium Tin Oxide
  • organic LED (OLED) devices were evaporated on pre-patterned ITO substrates (LumTec) for graphene cathode lamination.
  • Poly(3,4- ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT:PSS, HC Stark) was spin- coated on cleaned substrates at 3000 rpm at 1000 rpm/s and baked at 120°C for 1 hour. Following the PEDOT deposition the substrates were taken into the nitrogen environment of the glovebox.
  • a transfer stamp was prepared as follows. PDMS was cured in a petri dish at 80°C for 1 hour. Small stamps of PDMS base were cut from this mold, and coated with 0.4g (approximately 400 nm) of Parylene-C via a Specialty Coating Systems Labcoter. These PDMS-Parylene stamps were then spin-coated with a fluorinated polymer (manufactured by Orthoganol, Inc.) at 3000 rpm and 1000 rpm/s acceleration.
  • a fluorinated polymer manufactured by Orthoganol, Inc.
  • the transfer stamp was placed, graphene-side down, onto the organic thin films in the desired location. Pressure was applied with a thumb for 5 seconds. The stamp was then removed from the substrate. The graphene was left on the substrate, along with a thin film of the fluorinated resist. This resist was removed by two subsequent spin-coats of a fluorous solvent described above.
  • Table 1 Peak characteristics of graphene transferred onto organic substrate as compared with graphene transferred onto Si substrate
  • Figure 4 shows SEM images taken at 10,000 times magnification at an 2 kV.
  • Figure 4b shows graphene transferred on silicon using the disclosed method, including its morphology and a high level of cleanliness.
  • Figure 4a shows graphene transferred on an organic thin-film of TPBi, illustrating the high fidelity transfer of graphene onto a low-energy surface with a transfer quality similar to that on silicon.
  • Aluminum cathode which gives a good match to the Lowest Unoccupied Molecular Orbital (LUMO) of the electron transporting material (in this case, TPBi).
  • An Aluminum cathode also reflects light with high efficiency, increasing the external quantum efficiency of the device when viewed through the anode, but resulting in an opaque device.
  • a graphene transferred onto organic substrate can serve as a transparent electrode and provide different architectures and devices.
  • Figure 5a shows the Current-Voltage characteristics of the graphene OLED device in comparison to a control device with an Aluminum cathode.
  • the graphene device requires higher voltage to turn on. As a result, the device requires significant current density before voltage can drop over the diode. This can be ameliorated by process iteration and refinement to transfer graphene with a lower roughness.
  • Figure 5b shows an image of the functional graphene OLED. The transparency of the device can be attributable to the presence of graphene in conjunction with an ⁇ anode.

Abstract

La présente invention concerne des techniques pour transférer du graphène sur un substrat receveur tel qu'une couche mince de semi-conducteur organique. Le graphène peut être collé à une surface d'un transfert qui comprend un polymère fluoré. Le transfert peut être positionné avec le graphène en contact avec une surface d'un substrat receveur, et une pression peut être appliquée sur le transfert. Le polymère fluoré peut ensuite être enlevé, en laissant le graphène fixé à la surface du substrat receveur.
PCT/US2012/071377 2011-12-22 2012-12-21 Transfert assisté de graphène WO2013096841A1 (fr)

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US61/579,347 2011-12-22

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Cited By (8)

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WO2015021479A1 (fr) * 2013-08-09 2015-02-12 The Trustees Of Columbia University In The City Of New York Systèmes et procédés pour assembler des matériaux bidimensionnels
JP2015156367A (ja) * 2013-12-27 2015-08-27 ザ・ボード・オブ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・イリノイ ナノ構造材料積層体転移方法及びデバイス
WO2016204602A1 (fr) * 2015-06-18 2016-12-22 Universiti Putra Malaysia Procédé de transfert de matériaux à base de graphène utilisant un hydrogel
US9704956B2 (en) 2010-12-21 2017-07-11 The Trustees Of Columbia University In The City Of New York Electrical devices with graphene on boron nitride
WO2017197257A1 (fr) * 2016-05-13 2017-11-16 Massachusetts Institute Of Technology Transfert de nanofilm, et cellules solaires et diodes électroluminescentes organiques et pérovskites visiblement transparentes pourvues d'une couche de nanofilm
EP3321734A1 (fr) * 2016-11-11 2018-05-16 Shin-Etsu Chemical Co., Ltd. Procédé de fabrication d'un film de graphène et procédé de fabrication de pellicule l'utilisant
GB2571066A (en) * 2015-06-18 2019-08-21 Univ Putra Malaysia Method for transferring graphene-based materials using hydrogel
CN112048279A (zh) * 2020-09-11 2020-12-08 为远材料科技(辽宁)有限责任公司 光释放胶及其制备方法和石墨烯的转移方法

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WO2010132552A1 (fr) * 2009-05-12 2010-11-18 The Board Of Trustees Of The University Of Illinois Ensembles imprimés de diodes électroluminescentes inorganiques microscopiques ultraminces pour dispositifs d'affichage déformables et semi-transparents
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US20100143726A1 (en) * 2007-04-11 2010-06-10 Goelzhaeuser Armin Method for Transferring a Nanolayer
US20110159252A1 (en) * 2008-05-23 2011-06-30 Ober Christopher K Orthogonal Procesing of Organic Materials Used in Electronic and Electrical Devices
US20100101710A1 (en) * 2008-10-27 2010-04-29 Samsung Electronics Co., Ltd. Method for removing a carbonization catalyst from a graphene sheet and method for transferring the graphene sheet
WO2010132552A1 (fr) * 2009-05-12 2010-11-18 The Board Of Trustees Of The University Of Illinois Ensembles imprimés de diodes électroluminescentes inorganiques microscopiques ultraminces pour dispositifs d'affichage déformables et semi-transparents

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9704956B2 (en) 2010-12-21 2017-07-11 The Trustees Of Columbia University In The City Of New York Electrical devices with graphene on boron nitride
WO2015021479A1 (fr) * 2013-08-09 2015-02-12 The Trustees Of Columbia University In The City Of New York Systèmes et procédés pour assembler des matériaux bidimensionnels
JP2015156367A (ja) * 2013-12-27 2015-08-27 ザ・ボード・オブ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・イリノイ ナノ構造材料積層体転移方法及びデバイス
US20160365478A1 (en) * 2013-12-27 2016-12-15 The Board Of Trustee Of The University Of Illinois Nanostructure material stack-transfer methods and devices
TWI688115B (zh) * 2013-12-27 2020-03-11 伊利諾大學受託人董事會 轉移奈米結構材料堆疊體之方法及裝置
GB2571066A (en) * 2015-06-18 2019-08-21 Univ Putra Malaysia Method for transferring graphene-based materials using hydrogel
WO2016204602A1 (fr) * 2015-06-18 2016-12-22 Universiti Putra Malaysia Procédé de transfert de matériaux à base de graphène utilisant un hydrogel
US20170331069A1 (en) * 2016-05-13 2017-11-16 Massachusetts Institute Of Technology Nano-Film Transfer and Visibly Transparent Organic and Perovskite Solar Cells and LEDs with a Nano-Film Layer
CN109478600A (zh) * 2016-05-13 2019-03-15 麻省理工学院 纳米薄膜转移以及具有纳米薄膜层的可见透明有机和钙钛矿太阳能电池和led
WO2017197257A1 (fr) * 2016-05-13 2017-11-16 Massachusetts Institute Of Technology Transfert de nanofilm, et cellules solaires et diodes électroluminescentes organiques et pérovskites visiblement transparentes pourvues d'une couche de nanofilm
JP2018077412A (ja) * 2016-11-11 2018-05-17 信越化学工業株式会社 グラフェン膜の製造方法及びこれを用いたペリクルの製造方法
US10053367B2 (en) 2016-11-11 2018-08-21 Shin-Etsu Chemical Co., Ltd. Method of manufacturing graphene film and method of manufacturing pellicle using the same
EP3321734A1 (fr) * 2016-11-11 2018-05-16 Shin-Etsu Chemical Co., Ltd. Procédé de fabrication d'un film de graphène et procédé de fabrication de pellicule l'utilisant
CN112048279A (zh) * 2020-09-11 2020-12-08 为远材料科技(辽宁)有限责任公司 光释放胶及其制备方法和石墨烯的转移方法

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