WO2004087434A1 - Techniques et elements donneurs pour transferer des materiaux thermiquement sensibles vers des substrats par imagerie thermique - Google Patents

Techniques et elements donneurs pour transferer des materiaux thermiquement sensibles vers des substrats par imagerie thermique Download PDF

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Publication number
WO2004087434A1
WO2004087434A1 PCT/US2004/009187 US2004009187W WO2004087434A1 WO 2004087434 A1 WO2004087434 A1 WO 2004087434A1 US 2004009187 W US2004009187 W US 2004009187W WO 2004087434 A1 WO2004087434 A1 WO 2004087434A1
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Prior art keywords
layer
substrate
donor element
transfer
organic
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PCT/US2004/009187
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English (en)
Inventor
Graciela Blanchet Fincher
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E.I. Dupont De Nemours And Company
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Priority to JP2006509301A priority Critical patent/JP2006524916A/ja
Priority to EP04758354A priority patent/EP1606120A1/fr
Publication of WO2004087434A1 publication Critical patent/WO2004087434A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • B41M5/42—Intermediate, backcoat, or covering layers
    • B41M5/44—Intermediate, backcoat, or covering layers characterised by the macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/38207—Contact thermal transfer or sublimation processes characterised by aspects not provided for in groups B41M5/385 - B41M5/395
    • B41M5/38214—Structural details, e.g. multilayer systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • 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
    • H10K71/18—Deposition of organic active material using non-liquid printing techniques, e.g. thermal transfer printing from a donor sheet
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
    • B41M2205/30—Thermal donors, e.g. thermal ribbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • B41M5/42—Intermediate, backcoat, or covering layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate

Definitions

  • PROCESSES A N D DONOR ELEMENTS FOR TRANSFERRING THERMALLY SENSITIVE MATERIALS TO SUBSTRATES
  • This invention relates to processes for transferring fragile or thermally sensitive materials by a thermal imaging process.
  • This invention also relates to multi-layered structures useful in carrying out such processes. These processes include forming patterns of light-emitting
  • the invention relates to methods for forming thin film organic transistors (TFTs) and polymer light-emitting displays (PLEDs) by such thermal processes.
  • TFTs thin film organic transistors
  • PLEDs polymer light-emitting displays
  • Thin film transistors have been fabricated incorporating organic semiconducting materials, such as pentacene, polythieneylenevinylene, thiophene oligomers, benzothiophene dimers, and polyacetylenes.
  • Organic materials can also be used to form the other components of the transistor, such as the conducting layers that form the gate, source, and
  • Transistors made in whole or in part of organic materials may be less expensive and easier to manufacture than traditional transistors. While the same component densities as silicon transistors have not yet been achieved, the low cost of organic transistors means that they can be
  • organic transistors could be used in inexpensive or disposable items, such as electronic paper, posters and books, smart cards, toys, appliances and electronic bar codes for product identification.
  • Organic transistors can also be flexible, which is
  • flexible transistor arrays can be used in flexible electrophoretic displays, PLEDs and liquid crystal displays (LCDs) for computers, laptops and televisions. While the savings in fabrication costs are significant, further decreases in the fabrication costs of organic transistors would be advantageous.
  • Organic materials can be applied to a portion of a transistor by spin coating, casting, printing or other methods. Some organic materials can also be applied by physical vapor deposition processes. An electroactive polymer precursor can also be applied and converted to a polymer, typically by heat. Using a mask can provide direct patterning during deposition. If a photoresist is used during deposition, wet chemical etching after deposition is necessary, which may result in severe degradation of the organic semiconductor. While easier and less expensive than the fabrication techniques required by silicon based transistors, such methods are still complex, slow, lack sufficient resolution, expose the device to deleterious heat and chemical processes, and are more expensive than necessary. Fabricating organic transistors completely by printing techniques offers the potential for further cost reductions. F.
  • Ink-jet printing has also been used to apply organic semiconducting material. See U.S. 6,087,196; EP 0880303A1 ; WO 99/66483; and
  • thermal transfer processes are well known in applications such as color proofing. Such thermal transfer processes include, for example, dye sublimation, dye transfer, melt transfer, and ablative material transfer, and typically use a laser to induce the imagewise thermal transfer of material. These processes have been described in U.K. 2,083,726; U.S. 4,942,141 ; U.S. 5,019,549; U.S. 4,948,776; U.S. 5,156,938; U.S. 5,171 ,650; and U.S.
  • Laser-induced thermal transfer processes typically use a donor element, including a layer of material to be transferred (“transfer layer”), and a receiver element, including a surface for receiving the transferred material.
  • a donor element including a layer of material to be transferred (“transfer layer")
  • a receiver element including a surface for receiving the transferred material.
  • the substrate of the donor element or the receiver element is transparent, or both are transparent.
  • the donor element and receiver element are brought into close proximity or into contact with each other and selectively exposed to laser radiation, usually by an infrared laser. Heat is generated in the exposed portions of the transfer layer, causing the transfer of those portions of the transfer layer onto the surface of the receiver element. If the material of the transfer layer does not absorb the incoming laser radiation, the donor element must include a heating layer adjacent to the transfer layer.
  • An ejection layer of a vaporizable polymeric material which decomposes into gaseous molecules when heated, may be also provided between the heating layer and the donor support. Decomposition of the ejection layer provides additional force for propelling the exposed portions of the transfer layer onto the receiver element.
  • the exposure takes place only in a small, selected region of the assembly at a time, so that transfer of material from the donor element to the receiver element can be built up one pixel at a time.
  • Computer control facilitates the transfer at high speed and high resolution.
  • the entire assembly is irradiated and a mask is used to selectively expose desired portions of the thermally imageable layer (U.S. 5,937,272).
  • Laser-induced thermal transfer processes are generally faster and less expensive than the coating, deposition and patterning processes described above and allow the patterning of features at high resolution.
  • thermal transfer materials such as pentacene, fluorinated copper phthalocyanine, or organic light-emitting materials usually results in severe degradation and/or partial vaporization of the materials.
  • thermal transfer processes particularly laser- induced thermal transfer processes, that can be used in the application and patterning of organic semiconducting materials for the fabrication of organic transistors and other organic electronic devices, and of light- emitting materials for the fabrication of light-emitting devices such as displays.
  • the process of this invention provides a method for transferring fragile or thermally sensitive materials using a thermal imaging process.
  • the process of this invention comprises: a. forming a donor element comprising: i. a substrate; and ii. a transfer layer comprising a fragile or thermally-sensitive material and a protective layer located between the substrate and the fragile or thermally-sensitive layer; b. placing the transfer layer of the donor element in contact with a receiver element; and c. exposing selected areas of the donor element to laser radiation to transfer portions of the transfer layer onto a receiver element to form a patterned multilayer structure.
  • This invention also provides a thermally imageable donor element, comprising: a. a substrate; b. a heating layer; c. a protective layer; and d. a fragile or thermally sensitive layer.
  • FIGURES Figure 1 is a side view of a thermally imaged transistor.
  • Figure 2 is a side view of a top contact thin film transistor and a bottom contact thin film transistor.
  • Figure 3 is a side view of a polymer light-emitting diode (PLED).
  • Figure 4 is a graph of the IV characteristics of a printed transistor.
  • Figure 5 is a scanned image of a printed transistor.
  • organic electronic device refers to an electronic device in which any component, such as a semiconducting, conducting or light-sensitive component, is an organic material.
  • adjacent to does not necessarily mean that one layer is immediately next to another layer.
  • An intermediate layer or layers may be provided between layers said to be adjacent to each other.
  • the process of this invention provides a method for transferring thermally-sensitive or fragile materials from a donor element to a receiver element via thermal imaging. This process is especially useful for manufacturing organic electronic devices, e.g., TFTs and PLEDs.
  • the fragile or thermally-sensitive materials are incorporated into the transfer layer of the donor element, and are protected from the heat generated in the thermal transfer process by a protective layer. Examples of fragile or thermally-sensitive materials of particular interest are organic or inorganic semi-conductors, light-emitting polymers and small molecule light-emitters, but the process can also be used to transfer more robust materials.
  • the protective layer can comprise material that is also useful in constructing electronic devices. Dielectrics and charge injection materials are preferred protective layers in the manufacture for TFTs and PLEDs, respectively.
  • the process of this invention can also be used to transfer one or more electroactive layers simultaneously, resulting in both process simplification and improved registration fidelity in manufacturing multilayer electronic device structures.
  • a thermal imaging process for forming patterns of semiconductive material (e.g., p- or n-type organic or inorganic semiconductor) and a dielectric material, in which the materials are simultaneously transferred onto a patterned or unpatterned receiver to form a multilayer structure.
  • the multilayer structure can be used in an electronic device, including an organic electronic device.
  • the semiconducting and dielectric layers can be thermally transferred by the process of this invention onto a source and drain which have previously been deposited on a receiver substrate, and then a gate layer can be printed on top of the transferred semiconducting and dielectric layers to form a "bottom contact thin film transistor.”
  • the donor element comprises a flexible substrate, a heating layer coated with a dielectric layer, and a semiconducting layer on top of the dielectric layer.
  • An additional dielectric layer can be transferred by thermal imaging or other techniques to cover any irregularities of the first dielectric layer.
  • a gate layer (120) can be printed onto the dielectric layer(s) via thermal imaging or conventional methods to complete the fabrication of a transistor in a bottom-contact configuration. (See Figure 2.)
  • the gate would be printed on the receiver, and then the dielectric would be printed on the gate, either by thermal imaging or other printing method.
  • the semi- conductive layer is deposited next, and finally the source and drain are applied on top of the semi-conductive layer, either by thermal transfer or other printing methods.
  • the imaging process of this invention can pattern multiple layers of dielectric in addition to the semiconducting-dielectric layer, as long as the pattern for each of the multiple layers is the same. Sequential dielectric layers can be applied for electrical isolation.
  • a negative-imaging mode can also be used to simultaneously pattern one or more layers.
  • regions outside the desired pattern are removed by laser ablation or other means to form a patterned layer (e.g., a semiconducting layer, a dielectric layer or a dielectric + semiconducting layer).
  • the patterned layer(s) can then be laminated in registry onto printed source and drains or other components of the desired electronic device.
  • Such a negative-imaging process can also be used in conjunction with the process of this invention to form electronic devices.
  • a thin film transistor incorporating an organic semiconductor can be made by forming patterned dielectric and organic semiconducting layers on a donor via negative imaging. The patterned dielectric and organic semiconducting layers are then deposited over the source and drain via lamination, followed by deposition of the gate.
  • a pattern of dielectric material can be directly transferred via thermal transfer onto the gate layer.
  • the printing of the source and drain follows the transfer of the dielectric layer.
  • the organic semiconducting material with a protective layer is then transferred via the process of this invention onto the source and drain layer, followed by deposition of the gate.
  • a thermal transfer process is disclosed for forming patterns of light-emitting polymer (or small molecule emitters) and a charge-injection material, in which the polymer and charge-injection material are simultaneously transferred onto a receiver element.
  • the donor element comprises a substrate, a layer of charge-injection material adjacent to the substrate, and a layer of light-emitting polymer (or small molecule emitters) adjacent to the charge-injection layer.
  • the donor element can also contain a heating layer between the substrate and the charge-injection layer, as well as an optional ejection layer between the substrate and the heating layer.
  • the charge-injection layer serves as the protective layer, protecting the sensitive light-emitting polymer (or small molecule emitters) from direct exposure to the heat generated by the laser beam, and allowing the direct transfer of organic light-emitting polymers and small molecule light-emitters without degradation.
  • a thermally imageable donor element 10 is provided.
  • the donor element comprises a substrate (12), an optional ejection layer (14), a heating layer (18), and a transfer layer comprising a dielectric layer (16) and a semiconducting layer (15), as shown in Figure 1.
  • Figure 1 also shows a receiver element (20) comprising a base element (22) and an optional adhesive layer (24). The exposed portion of the transfer layer (17) is transferred onto the receiver element.
  • the substrate (12) is a material suitable for use in an electronic device.
  • the substrate (12) is preferably flexible and transparent, to facilitate the exposure of the donor element (10) by laser radiation, as described further, below.
  • Suitable transparent films include polyesters (most preferably polyethylene terephthalate), polyether sulfone, polyvinyl chloride, polyimides, poly(vinyl alcohol-co-acetal), polyethylenes, and cellulose esters, such as cellulose acetate.
  • Suitable dielectrics include polyhydroxystyrene, polyvinylpyridine, polyvinylphenol, glass resin, flurorinated co-polymers, and methacrylic copolymers.
  • Suitable organic semiconducting materials include pentacene, sexithiophene, tetracene, polythieneylenevinylene, thiophene oligomers, benzothiophene dimers, and polyacetylenes.
  • Suitable inorganic semiconducting materials include Zn ⁇ 2, CdS and amorphous silicon.
  • the ejection layer (14) comprises a material with a low decomposition temperature, preferably less than about 275 °C.
  • the ejection layer is preferably non-metallic. Suitable materials include nitrocellulose, polyvinyl chloride, chlorinated polyvinyl chloride, polymethylmethacrylate and polymethacrylate copolymers.
  • the ejection layer is typically about 1 micron thick.
  • the ejection layer (14) may also contain a radiation-absorbing dye dissolved in the low decomposition temperature binder.
  • the absorbing dye absorbs radiation in the emission band of the exposure laser.
  • the exposure laser emits radiation in the infrared range and the absorbing dye is an infrared-absorbing dye.
  • a suitable infrared absorbing dye is TIC-5c (2-[2-[2-chloro-3[[1 ,3-dihydro-1 ,3,3-trimethyl-2H-indol-2- ylidene) ethylidene]-1-cyclopenten-1-y1]ethenyl]-1 ,3,3-trimethyl-3-H- indolium, salt with trifluoromethane sulfonic acid (1 :1 ), CAS # 128433-68- 1), available from E. I. DuPont de Nemours, Inc. (Wilmington, DE).
  • Alternative dyes which absorb at 830 nm include ADS 830 (2-[2-[2-chloro- 3-[2-[1 ,3-dihydro-1 ,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2- ylidene]ethylidene]-1-cyclohexen-1-yl]ethenyl]-1 ,1-dimethyl-3-(4- sulfobutyl)-1 H-benz[e]indolium, inner salt, free acid, CAS # 162411 -28-1 ); and SQS ((4-[[3-[[2,6-bis(1 ,1-dimethylethyl)-4H-thiopyran-4- ylidene]methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-2,6- bis(1 ,1-dimethylethyl)-thiopyrylium
  • the laser may emit in other wavelength bands, and then dyes are chosen that absorb radiation in that particular wavelength band.
  • the dielectric layer may also contain small amounts of dyes to absorb laser radiation such as the dyes listed above.
  • Gas formers may also be included in the ejection layer (14) to increase the propulsive force generated in the ejection layer.
  • Suitable gas formers include: diazo alkyls; diazonium salts; azido ( — N3) compounds; ammonium salts; oxides, which decompose to form oxygen; carbonates; and peroxides.
  • Diazo compounds such as 4-diazo-N, N' diethylaniline fluoroborate, may be used, for example.
  • Mixtures of gas formers can also be used.
  • the heating layer (18) is preferably a thin metal layer that absorbs the incoming radiation.
  • the metal is preferably Ni, Al, V or Cr, with a thickness such that the layer exhibits maximum absorption of the incoming laser beam (25-35%). Ni layers of 30-150 A are preferred.
  • the transfer layer of semiconducting (15) and dielectric (16) material may comprise organic semiconducting materials deposited via evaporation or solution onto a suitable dielectric.
  • Suitable dielectric layers for organic transistors include materials with high dielectric constant.
  • the capacitance of the dielectric layers is typically at least 10 -8 F/cm 2 .
  • the dielectric layers must provide suitable interfaces for the evaporated semiconductors such that their grain size, and therefore field- effect mobility, is large.
  • the receiver element (20) comprises a substrate (22) and an optional adhesive layer (24).
  • the substrate (22) is a dimensionally stable sheet material. Suitable sheet materials include transparent films of polyethylene terephthalate, polyether sulfone, polyimide, poly (vinyl alcohol-co-acetal), polyethylene or a cellulose ester, such as cellulose acetate.
  • the receiver substrate can also be an opaque material, such as polyethylene terephthalate filled with a white pigment such as titanium dioxide; ivory paper; or synthetic paper, such as Tyvek® spunbonded polyolefin.
  • the adhesive layer (24) of the receiver element (20) can be any low Tg polymer. Suitable adhesive materials include polycarbonates; polyurethanes; polyesters; polyvinyl chloride; styrene/acrylonitrile copolymers; poly(caprolactone); vinylacetate copolymers with ethylene and/or vinyl chloride; (meth)acrylate homopolymers (such as butyl- methacrylate) and copolymers; and mixtures thereof. Pressure-sensitive adhesives can also be used.
  • the donor element (10) of Figure 1 and the receiver element (20) are brought into contact to form an assembly (30).
  • the outer surface of the transfer layer (17) is in contact with the adhesive coating (24), if present. If the adhesive coating (24) is not present, then the outer surface of the transfer layer (17) contacts the receiver substrate (22).
  • Vacuum and/or pressure can be used to hold the donor element (10) and the receiver element (20) together to form the assembly (30).
  • the donor element (10) and the receiver element (20) can be held together by fusion of layers at the periphery of the assembly.
  • the donor element (10) and receiver element (20) can be taped together, and then taped to the imaging apparatus.
  • a pin/clamping system can also be used.
  • the donor element can be laminated to the receiver element. If the donor element (10) and the receiver element (20) are flexible, the assembly (30) can be conveniently mounted on a drum to facilitate laser imaging.
  • the assembly (30) is selectively exposed to laser radiation (R), in an exposure pattern of the desired pattern to be formed on the substrate. (See Figure 1 ).
  • the laser radiation or laser beam (R) is focused on portions of the interface between the dielectric layer (16) and the heating layer (18).
  • the exposed portions of the dielectric layer (16) heat the adjacent portions of the ejection layer (14), causing decomposition and vaporization of the ejection layer (14), propelling the exposed portions of the transfer layer (17) onto the receiver.
  • the desired portions of the transfer layer (17) of dielectric (16) and semiconducting material (15) are thereby transferred to the receiver element (20), leaving the unwanted pattern of material on the substrate (12).
  • the donor element (10) and receiver element (20) are separated, leaving the unwanted portions of a the dielectric (16) and semiconducting (15) layers on the substrate (12) and the imaged portions of the transfer layer (17) on the receiver element (20).
  • the resulting multilayer structure may then be further processed to form the desired organic electronic device.
  • an organic, thin film transistor of organic semiconducting material can be fabricated using the process of this invention.
  • Laser radiation is preferably applied through the substrate element (12), as shown in Figure 1.
  • Laser radiation may be provided at a laser fluence of up to about 600 mJ/cm 2 , preferably about 75-440 mJ/cm 2 .
  • Various types of lasers can be used to expose the transfer layer (17).
  • the laser preferably emits in the infrared, near-infrared or visible region. Particularly advantageous are diode lasers emitting in the region of 750 to 870 nm, due to their small size, low cost, stability, reliability, ruggedness and ease of modulation. Diode lasers emitting in the range of 780 to 850 nm are most preferred. Such lasers are available from Spectra Diode Laboratories (San Jose, CA).
  • the process of the present invention can also be used as a thermal imaging process to transfer layers of material as thin as about 100 A-150 A, by providing a protective layer that is directly exposed to the heat generated in the transfer process. Thicker layers can also be transferred (i.e., greater than 150 A).
  • Figure 2 shows a side view of a bottom contact configuration of a thin film polymeric transistor (104) fabricated on a substrate (100).
  • the transistor (104) comprises: a source (112) and a drain (114) on a substrate (100); organic semiconducting material (116) over each source (112) and drain (114); a layer of dielectric material (118) over the organic semiconducting material, forming an insulating layer; and a layer of conducting material over the insulating layer (118), forming a gate electrode (120).
  • FIG. 2 also shows a TFT (102) in a top-contact (bottom-gate) configuration.
  • This TFT comprises: a gate electrode (120) over a substrate (100); a layer of dielectric material (118) over the gate layer; a source (112) and drain (114) over the dielectric; a semiconducting layer (116) over the source (112) and drain (114); and an additional dielectric layer which serves as an encapsulating layer (119, not shown in this Figure).
  • the dielectric layer (118) is applied either by thermal imaging, or alternative methods, followed by deposition of the semi-conducting layer (116).
  • a set of sources (112) and drains (114) is applied on top of the pattern of organic semiconducting material (116).
  • the encapsulating layer (119) is applied over the sources (112) and drains (114).
  • the second dielectric layer acts as a barrier layer, as well as in assisting transferring the semiconducting layer without degradation. If the gate electrode (118), source (112) and drain (114) are connected to potential, current will flow from the source (112) through the organic semiconducting material (116) to the drain (114) when the gate electrode (118) is turned on.
  • the gap between the source (112) and the drain (114) may be as small as one pixel (5 microns) if produced via thermal imaging.
  • the thickness of the source (112) and drain (114) can be about 100 A to about 10,000 A.
  • the thickness of the dielectric layer (118) can be about 100 A to about 15,000 A.
  • the thickness of the semiconducting layer (116) can be about 50 A to about 2000 A if deposited via thermal evaporation and up to 10,000 A if cast from solution.
  • a pattern of organic semiconducting and dielectric materials is applied over the sources (112) and drains (114).
  • FIG. 3 shows a side view of a PLED.
  • a flexible substrate (200) is coated with ITO, which constitutes the anode (201) of the display.
  • the charge injection layer (202) and the light-emitting polymer (203) are coated on top.
  • the non-limiting examples demonstrate the processes for the transfer of thin dielectric and semiconducting layers, claimed and described herein. The amounts below are given as wt%.
  • the CREO unit comprised an 81.2 cm long drum with a 91 cm perimeter.
  • the CREO 3244 Spectrum Trendsetter Exposure Unit included a 20 watt infrared diode laser, which emitted a laser beam at 830 nm at 1 microsecond pulse width. The laser beam was split by a light valve to form an array of 240 overlapping 5 micron x 2 micron spots.
  • GMA is glycidyl methyl acrylate; MMA is methyl methacrylate; BA is butyl acrylate; and MAA is methacrylic acid.
  • the TFT in bottom contact configuration described in the following example was printed via thermal imaging using four donor elements.
  • Each of the donor elements included a 4 mil (0.0363 mm) thick substrate of Mylar®, 400D optical clarity, available from E. I. DuPont de Nemours, Inc. (Wilmington, DE) coated with 100 A of nickel by electron beam deposition, to about 40% optical transmission.
  • the polyaniline (PANI) used was prepared through emulsion polymerization following the procedure outlined in U.S. 5,863,465. Dinonylnaphthalene sulfonic acid (DNNSA) was used as the dopant.
  • the doped PANI is hereafter referred to as PANI-DNNSA.
  • PANI-DNNSA (5.9g, 32.9% solids in xylenes) was added to the nanotube/xylene mixture. The resulting mixture was dispersed for an additional 5 minutes, during which time the bottle was shaken two times in order to rinse the carbon nanotubes off the walls of the bottle.
  • the DNNSA-PANI/SWNT solution was coated to 1.2 micron in thickness onto the electron-beam deposited Ni layer using a # 10 Meyer rod. The film contained 3wt% NT and 97wt% polyaniline after drying.
  • the DNNSA-PANI/SWNT donor elements were used for the printing the gates and source and drains.
  • the donor element for the dielectric-semiconducting layer was prepared by coating poly-vinyl pyrelene to 1.1 micron in thickness on a Ni- coated Mylar® film. Pentacene (Sigma-Aldrich, Milwaukee, Wl) was then evaporated onto the dielectric-semiconducting layer using a Kurt Lesker evaporator. The pentacene film was evaporated at room temperature at a rate of 0.3 A over a 6" x 6" area. The thickness of the pentacene layer was 250 A, as measured using a quartz crystal. The 3" x 3" backplane was printed as follows.
  • the DNNSA-PANI/SWNT donor element and the receiver element were loaded onto a CREO 3244 Spectrum Trendsetter Exposure Unit.
  • the receiver element was a 4 mil Mylar® film coated with a 1.4 micron film obtained from a GMA 2%/MMA 51 %/BA 40%/MAA 3% latex (33 wt% solids), with a glass transition of 39 °C.
  • the source and drain layer was printed at a laser fluence of
  • the drum speed was maintained at 100 RPM.
  • the laser beam was focused at the interface between the layer of nickel and DNNSA-PANI/SWNT.
  • the nickel absorbed the incoming laser beam, partially decomposing the organics at its interface, and the gaseous decomposition products propelled the exposed portions of the DNNSA- PANI/SWNT conducting layer onto the receiver element.
  • the semiconductor - dielectric donor was loaded onto the 3244 Trendsetter in place of the DNNSA- PANI/SWNT donor element.
  • the semiconductor-dielectric donor element was exposed at 7 Watts. Registration to the pixel level was maintained after removal and repositioning the different donor elements. Since the glass transition of the coating on the receiver element was low, it was sufficiently tacky for the transferred semiconducting surface to adhere to the receiver element.
  • the gates were printed on top of the transferred dielectric layer using the DNSSA-PANI/ SWNT donor element previously described in the printing of the source and drains.
  • the gate layer was exposed at 3.6 Watts.
  • the IV characteristics of one of the printed transistors are shown in Figure 4 for gate voltages ranging from 0 to -100 V and Vsd in the same range.
  • a scanned image of the printed transistor is also shown in Figure 5.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)
  • Thin Film Transistor (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Formation Of Insulating Films (AREA)

Abstract

L'invention concerne des procédés permettant de former un matériau diélectrique semi-conducteur modelé sur un substrat par des techniques thermiques, qui consistent à chauffer un donneur pouvant thermiquement former une image comprenant un substrat et une couche de transfert de matériau semi-conducteur conjointement avec un diélectrique. Ledit donneur est exposé avec l'image positive du motif recherché à former sur le récepteur, de sorte que les parties exposées de la couche de matériau semi-conducteur et diélectrique sont simultanément transférées, formant ainsi le motif recherché du matériau semi-conducteur et diélectrique sur le récepteur. Le matériau semi-conducteur peut être modelé de manière à former un transistor en couches minces. On peut également utiliser ledit procédé pour modeler un polymère électroluminescent ou une petite molécule conjointement avec la couche d'injection de charge pour former l'afficheur électroluminescent destiné à des dispositifs électroniques organiques photosensibles. L'invention concerne en outre les éléments donneurs utiles dans cette technique, ainsi que des procédés de formation de transistors en couches minces et des éléments donneurs pouvant être utilisés dans ces techniques.
PCT/US2004/009187 2003-03-27 2004-03-25 Techniques et elements donneurs pour transferer des materiaux thermiquement sensibles vers des substrats par imagerie thermique WO2004087434A1 (fr)

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JP2006509301A JP2006524916A (ja) 2003-03-27 2004-03-25 感熱性材料を基材に転写するための方法およびドナー要素
EP04758354A EP1606120A1 (fr) 2003-03-27 2004-03-25 Techniques et elements donneurs pour transferer des materiaux thermiquement sensibles vers des substrats par imagerie thermique

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WO2006048015A1 (fr) 2004-11-01 2006-05-11 Nanofiber A/S Decollement en douceur de nanofibres organiques
WO2006055701A2 (fr) * 2004-11-19 2006-05-26 Massachusetts Institute Of Technology Transistors organiques basse tension sur substrats flexibles avec isolants a dielectrique de grille eleve selon procede en temperature ambiante
JP2006190756A (ja) * 2005-01-05 2006-07-20 Konica Minolta Holdings Inc 有機薄膜トランジスタおよびその製造方法
JP2006351613A (ja) * 2005-06-13 2006-12-28 Matsushita Electric Ind Co Ltd 電界効果トランジスタ、その製造方法および電子機器
JP2006351543A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd ナノ導電性膜のパターニング方法
JP2006352143A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd 有機半導体のパターニング方法
WO2007094757A2 (fr) * 2005-02-22 2007-08-23 Eastman Kodak Company Procédé de transfert adhésif d'une couche de nanotubes de carbone
WO2008010978A2 (fr) 2006-07-17 2008-01-24 E. I. Du Pont De Nemours And Company Compositions métalliques, donneurs d'imagerie thermique et compositions multicouches à motifs en dérivant
JP2008085312A (ja) * 2006-08-30 2008-04-10 Semiconductor Energy Lab Co Ltd 半導体装置の作製方法
JP2008537631A (ja) * 2005-03-31 2008-09-18 スリーエム イノベイティブ プロパティズ カンパニー ディスプレイの製造方法
GB2453766A (en) * 2007-10-18 2009-04-22 Novalia Ltd Method of fabricating an electronic device
WO2010015822A1 (fr) * 2008-08-05 2010-02-11 Cambridge Display Technology Limited Procédé de fabrication de transistors à couches minces organiques utilisant un processus d'impression par transfert thermique induit par laser
JP2010262980A (ja) * 2009-04-30 2010-11-18 Jsr Corp ナノインプリントリソグラフィー用硬化性組成物及びナノインプリント方法
EP2482355A1 (fr) * 2006-07-17 2012-08-01 E. I. du Pont de Nemours and Company Transistor à couche mince comportant de nouvelles compositions conductrices et diélectriques
US8343779B2 (en) 2007-04-19 2013-01-01 Basf Se Method for forming a pattern on a substrate and electronic device formed thereby
US8659014B2 (en) 2006-08-30 2014-02-25 Semiconductor Energy Laboratory Co., Ltd. Method for manufacturing semiconductor device
US20150372234A1 (en) * 2013-03-19 2015-12-24 Fujifilm Corporation Method for producing organic semiconductor element

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FR2894514B1 (fr) * 2005-12-08 2008-02-15 Essilor Int Procede de transfert d'un motif micronique sur un article optique et article optique ainsi obtenu
US7744717B2 (en) * 2006-07-17 2010-06-29 E. I. Du Pont De Nemours And Company Process for enhancing the resolution of a thermally transferred pattern
KR20090111091A (ko) * 2008-04-21 2009-10-26 (주)모디스텍 도전 필름 구조와 패터닝법
KR102480950B1 (ko) * 2014-12-24 2022-12-23 올싸거널 인코포레이티드 전자 장치의 포토리소그래피 패터닝

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US4942141A (en) 1989-06-16 1990-07-17 Eastman Kodak Company Infrared absorbing squarylium dyes for dye-donor element used in laser-induced thermal dye transfer
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US8034400B2 (en) 2004-11-01 2011-10-11 Nanofiber A/S Soft-lift off of organic nanofibers
WO2006048015A1 (fr) 2004-11-01 2006-05-11 Nanofiber A/S Decollement en douceur de nanofibres organiques
US7408187B2 (en) 2004-11-19 2008-08-05 Massachusetts Institute Of Technology Low-voltage organic transistors on flexible substrates using high-gate dielectric insulators by room temperature process
WO2006055701A2 (fr) * 2004-11-19 2006-05-26 Massachusetts Institute Of Technology Transistors organiques basse tension sur substrats flexibles avec isolants a dielectrique de grille eleve selon procede en temperature ambiante
WO2006055701A3 (fr) * 2004-11-19 2006-08-10 Massachusetts Inst Technology Transistors organiques basse tension sur substrats flexibles avec isolants a dielectrique de grille eleve selon procede en temperature ambiante
JP2006190756A (ja) * 2005-01-05 2006-07-20 Konica Minolta Holdings Inc 有機薄膜トランジスタおよびその製造方法
WO2007094757A2 (fr) * 2005-02-22 2007-08-23 Eastman Kodak Company Procédé de transfert adhésif d'une couche de nanotubes de carbone
WO2007094757A3 (fr) * 2005-02-22 2007-11-01 Eastman Kodak Co Procédé de transfert adhésif d'une couche de nanotubes de carbone
JP2008537631A (ja) * 2005-03-31 2008-09-18 スリーエム イノベイティブ プロパティズ カンパニー ディスプレイの製造方法
JP2006351613A (ja) * 2005-06-13 2006-12-28 Matsushita Electric Ind Co Ltd 電界効果トランジスタ、その製造方法および電子機器
JP2006352143A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd 有機半導体のパターニング方法
KR101174871B1 (ko) * 2005-06-18 2012-08-17 삼성디스플레이 주식회사 유기 반도체의 패터닝 방법
KR101223718B1 (ko) * 2005-06-18 2013-01-18 삼성디스플레이 주식회사 나노 도전성 막의 패터닝 방법
JP2006351543A (ja) * 2005-06-18 2006-12-28 Samsung Sdi Co Ltd ナノ導電性膜のパターニング方法
WO2008010978A2 (fr) 2006-07-17 2008-01-24 E. I. Du Pont De Nemours And Company Compositions métalliques, donneurs d'imagerie thermique et compositions multicouches à motifs en dérivant
EP2482355A1 (fr) * 2006-07-17 2012-08-01 E. I. du Pont de Nemours and Company Transistor à couche mince comportant de nouvelles compositions conductrices et diélectriques
US8659014B2 (en) 2006-08-30 2014-02-25 Semiconductor Energy Laboratory Co., Ltd. Method for manufacturing semiconductor device
JP2008085312A (ja) * 2006-08-30 2008-04-10 Semiconductor Energy Lab Co Ltd 半導体装置の作製方法
US8343779B2 (en) 2007-04-19 2013-01-01 Basf Se Method for forming a pattern on a substrate and electronic device formed thereby
GB2453766A (en) * 2007-10-18 2009-04-22 Novalia Ltd Method of fabricating an electronic device
US8969127B2 (en) 2007-10-18 2015-03-03 Novalia Ltd Apparatus for and method of fabricating an electronic device by transfer of material onto a substrate
WO2010015822A1 (fr) * 2008-08-05 2010-02-11 Cambridge Display Technology Limited Procédé de fabrication de transistors à couches minces organiques utilisant un processus d'impression par transfert thermique induit par laser
GB2462591B (en) * 2008-08-05 2013-04-03 Cambridge Display Tech Ltd Organic thin film transistors and methods of making the same
US8476121B2 (en) 2008-08-05 2013-07-02 Cambridge Display Technology Limited Organic thin film transistors and methods of making them
JP2010262980A (ja) * 2009-04-30 2010-11-18 Jsr Corp ナノインプリントリソグラフィー用硬化性組成物及びナノインプリント方法
US20150372234A1 (en) * 2013-03-19 2015-12-24 Fujifilm Corporation Method for producing organic semiconductor element
US9711725B2 (en) 2013-03-19 2017-07-18 Fujifilm Corporation Method for producing organic semiconductor element

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EP1606120A1 (fr) 2005-12-21
CN1764551A (zh) 2006-04-26
TW200508049A (en) 2005-03-01
KR20050109604A (ko) 2005-11-21
JP2006524916A (ja) 2006-11-02

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