WO2014073591A1 - Substrat pour dispositif flexible, dispositif flexible et procédé de production de celui-ci, stratifié et procédé de production de celui-ci, et composition de résine - Google Patents

Substrat pour dispositif flexible, dispositif flexible et procédé de production de celui-ci, stratifié et procédé de production de celui-ci, et composition de résine Download PDF

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Publication number
WO2014073591A1
WO2014073591A1 PCT/JP2013/080080 JP2013080080W WO2014073591A1 WO 2014073591 A1 WO2014073591 A1 WO 2014073591A1 JP 2013080080 W JP2013080080 W JP 2013080080W WO 2014073591 A1 WO2014073591 A1 WO 2014073591A1
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group
polyimide
substrate
amino
flexible device
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PCT/JP2013/080080
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English (en)
Japanese (ja)
Inventor
大和 齋藤
昭宏 和泉
省三 高田
土井　一郎
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旭化成イーマテリアルズ株式会社
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Priority to CN201380057552.XA priority Critical patent/CN104769021B/zh
Priority to KR1020157011891A priority patent/KR101709422B1/ko
Priority to JP2014545741A priority patent/JP6067740B2/ja
Publication of WO2014073591A1 publication Critical patent/WO2014073591A1/fr

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier
    • H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier the substrate being other than a semiconductor body, e.g. an insulating body
    • H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
    • H01L27/1259—Multistep manufacturing methods
    • H01L27/1262—Multistep manufacturing methods with a particular formation, treatment or coating of the substrate
    • H01L27/1266—Multistep manufacturing methods with a particular formation, treatment or coating of the substrate the substrate on which the devices are formed not being the final device substrate, e.g. using a temporary substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier
    • H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier the substrate being other than a semiconductor body, e.g. an insulating body
    • H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
    • H01L27/1218—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having at least one potential-jump barrier or surface barrier; including integrated passive circuit elements with at least one potential-jump barrier or surface barrier the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs with a particular composition or structure of the substrate
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L29/00—Semiconductor devices adapted for rectifying, amplifying, oscillating or switching, or capacitors or resistors with at least one potential-jump barrier or surface barrier, e.g. PN junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof  ; Multistep manufacturing processes therefor
    • H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
    • H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
    • H01L29/76—Unipolar devices, e.g. field effect transistors
    • H01L29/772—Field effect transistors
    • H01L29/78—Field effect transistors with field effect produced by an insulated gate
    • H01L29/786—Thin film transistors, i.e. transistors with a channel being at least partly a thin film
    • H01L29/78603—Thin film transistors, i.e. transistors with a channel being at least partly a thin film characterised by the insulating substrate or support
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2379/00—Other polymers having nitrogen, with or without oxygen or carbon only, in the main chain
    • B32B2379/08—Polyimides
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention particularly relates to a flexible device and a resin composition useful for the production thereof, a laminate and a method for producing the laminate, and a method for producing a flexible device using the laminate.
  • the present invention also relates to a flexible device substrate suitably used for a flexible device and a flexible device using the same.
  • the resin substrate under consideration is a heat treatment step of 400 ° C. or higher required in a device manufacturing process using a silicon-based semiconductor, and a temperature of 300 ° C. or higher required in a device manufacturing step using a metal oxide semiconductor. Resistant to the heat treatment process is required, and in order to suppress the dimensional difference during the heat treatment process caused by the difference in thermal expansion coefficient between the resin substrate and the silicon-based semiconductor or metal oxide semiconductor, the resin substrate and the inorganic substrate The process which peels a resin substrate from an inorganic substrate after device manufacture is required.
  • a polyimide having a thermal expansion coefficient close to that of a silicon-based semiconductor and having a heat resistance of 400 ° C. or higher is low in thermal expansion by molecular orientation, and thus has no adhesion to an inorganic substrate. For this reason, forming an inorganic layer for resin adhesion, such as a silicon nitride layer and an amorphous silicon layer, on the surface of an inorganic substrate has been performed.
  • an inorganic layer for resin adhesion such as a silicon nitride layer and an amorphous silicon layer
  • Patent Literature in the field of an interlayer insulating film (passivation film) and a surface protection film (overcoat film) of a semiconductor element, a resin composition containing polyimide, a silane coupling agent, and a solvent is known (Patent Literature). 3).
  • a photosensitive resin composition containing an alkali-soluble resin, a photoacid generator, a fatty acid alcohol compound, and an organosilicon compound is known as a surface protective film or an interlayer insulating film in a semiconductor device (see Patent Document 5). .
  • a positive photosensitive resin composition that is a polybenzoxazole-based heat-resistant polymer that can be applied as a surface protective film, an interlayer insulating film, or the like of an electronic component such as a semiconductor element is known (see Patent Document 6).
  • a flexible light-receiving element that includes a flexible transparent plastic substrate, an electrode layer, and a semiconductor layer, and the substrate is formed of a polyimide film containing polyimide as a main component (patent) Reference 7).
  • Patent Document 5 Patent Document 6, and Patent Document 7, there is no mention of peelability other than adhesion to an inorganic substrate.
  • Patent Document 5 forms a surface protective film or an interlayer insulating layer of a semiconductor device from a resin composition. In the examples, only sensitivity and adhesiveness experiments are conducted. In Patent Document 5, an inorganic substrate is used. On the other hand, a resin composition having a composition for achieving both adhesion and peelability is not envisaged.
  • Patent Document 6 a silane coupling agent is added to improve the adhesion of the positive photosensitive resin composition to the substrate, but peeling from the substrate is not assumed. Similarly, Patent Document 6 does not assume a resin composition having a composition for achieving both adhesiveness and peelability for an inorganic substrate.
  • Patent Document 7 describes a substrate made of a polyimide film. However, it does not assume that the substrate made of a polyimide film is peeled off from the inorganic substrate, and has both adhesion and peelability to the inorganic substrate.
  • the polyimide film which consists of a composition for making it do is not assumed.
  • any of the patent documents there is no disclosure of a composition that can reduce film thickness variation in a flexible device substrate mainly composed of polyimide. As shown in a comparative example to be described later, conventionally, a variation in the film thickness of a flexible device substrate mainly composed of polyimide has been likely to be large. Also, none of the patent documents discloses a flexible device substrate mainly composed of polyimide or a flexible device including a polyimide resin layer that exhibits good in-plane uniformity in property evaluation such as electrical properties. .
  • An object of the present invention is to provide a resin composition, a laminate, a method for producing the laminate, and a method for producing a flexible device. It is another object of the present invention to provide a flexible device substrate that is less likely to cause device malfunction when the device is configured, and a flexible device using the substrate.
  • the substrate for a flexible device of the present invention is represented by ( ⁇ ) a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, ( ⁇ ) a chemical structure represented by the following general formula (1) and / or the following general formula (2). ( ⁇ ) a compound having a chemical structure, ( ⁇ ) a chemical structure represented by the following general formula (3), a compound having one or more of the group consisting of a hydroxyl group, a carboxyl group and a sulfo group, ( ⁇ ) the following general formula ( 4) A compound having a chemical structure represented by 4) is contained.
  • the flexible device of the present invention is characterized in that a semiconductor device is formed on the flexible device substrate described above.
  • the flexible device of the present invention is characterized in that the semiconductor device is a thin film transistor.
  • the flexible device of the present invention is a polysilicon semiconductor or metal oxide semiconductor driven flexible display.
  • the flexible device of the present invention is represented by ( ⁇ ) polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, ( ⁇ ) a chemical structure represented by the following general formula (1) and / or the following general formula (2).
  • a compound having a chemical structure ( ⁇ ) a chemical structure represented by the following general formula (3), a compound having one or more members selected from the group consisting of a hydroxyl group, a carboxyl group and a sulfo group, ( ⁇ ) the following general formula (4) It contains the polyimide resin layer containing the compound which has a chemical structure represented by these.
  • the laminate of the present invention comprises an inorganic substrate, and a polyimide resin layer provided on the surface of the inorganic substrate, and (a) a polyimide resin layer containing polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, and the polyimide resin layer And the inorganic substrate have a 180 ° peel strength of 0.004 to 0.250 N / cm.
  • the polyimide resin layer has (b) a silicone surfactant or a fluorosurfactant, and (c) an amide group, an amino group, a carbamate group, a carboxyl group, an aryl group, and an acid anhydride. And an alkoxysilane compound having at least one functional group selected from the group consisting of a group and a polymerizable cyclic ether group.
  • the laminate of the present invention is characterized in that the inorganic substrate is a glass substrate.
  • the method for producing a flexible device of the present invention includes a step of forming a semiconductor device on the above-described laminate, and a step of peeling from the inorganic substrate thereafter.
  • the method for producing a flexible device of the present invention further includes a step of heating the laminate to 250 ° C. or higher.
  • the method for manufacturing a flexible device of the present invention is characterized in that the semiconductor device is a thin film transistor.
  • the method for producing a flexible device of the present invention is characterized in that the flexible device is a polysilicon semiconductor or metal oxide semiconductor drive flexible display.
  • the resin composition of the present invention includes (a) a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, or a polyimide precursor that becomes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher by imidization, and (b) At least one selected from the group consisting of a silicone-based surfactant or a fluorine-based surfactant and (c) an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, an amide group, and a polymerizable cyclic ether group And an alkoxysilane compound having a functional group of:
  • the component (b) has 2 to 1000 Si—O bonds in the molecule as a nonpolar site, and 1 to 100 polyether groups in the molecule as a polar site, It is a silicone-based surfactant having a hydroxyl group, a carboxyl group or a sulfo group.
  • the component (b) has 3 to 100 C—F group bonds in the molecule as nonpolar sites, and 1 to 100 polyether groups in the molecule as polar sites.
  • the resin composition of the present invention is characterized in that the component (b) is contained in an amount of 0.001 to 10 parts by mass with respect to 100 parts by mass of the component (a).
  • the component (c) is an alkoxysilane compound having at least one functional group selected from the group consisting of a carbamate group, a carboxyl group, an amide group, and an aryl group. .
  • the resin composition of the present invention is characterized in that the component (c) is contained in an amount of 0.001 to 9 parts by mass with respect to 100 parts by mass of the component (a).
  • the resin composition of the present invention is characterized by further containing (d) a solvent.
  • the component (d) is an aprotic polar solvent.
  • the manufacturing method of the laminated body of this invention forms the polyimide resin layer which consists of the process of expand
  • the method for manufacturing a laminate according to the present invention is characterized in that the inorganic substrate is a glass substrate.
  • the method for producing a flexible device of the present invention includes a step of forming a semiconductor device on the laminate obtained by the method for producing a laminate as described above, and then a step of peeling from the inorganic substrate. To do.
  • the method for producing a flexible device of the present invention further includes a step of heating the laminate to 250 ° C. or higher.
  • the method for manufacturing a flexible device of the present invention is characterized in that the semiconductor device is a thin film transistor.
  • the method for producing a flexible device of the present invention is characterized in that the flexible device is a polysilicon semiconductor or metal oxide semiconductor drive flexible display.
  • a resin composition, a laminate, and a laminate that have sufficient adhesion between a resin layer and an inorganic substrate in the process of manufacturing a flexible device, and that can easily peel only the inorganic substrate from the resin layer in the final stage.
  • the manufacturing method of a body and the manufacturing method of a flexible device can be provided.
  • the present inventors have controlled the 180 ° peel strength between the polyimide resin layer and the inorganic substrate, thereby allowing the adhesion and peeling between the polyimide resin layer and the inorganic substrate.
  • the polyimide resin layer formed using a resin composition containing a specific surfactant and a polyimide containing a specific alkoxysilane compound or a polyimide precursor is superior to an inorganic substrate. It has been found that it exhibits adhesion and easy peelability, and the present invention has been made based on this finding.
  • the polyimide resin layer in the present invention is a thin film having flexibility, for example, and is used for flexible devices such as flexible memories, sensors, and RF-IDs. Typically used for flexible displays.
  • the polyimide resin layer is first formed on a rigid substrate, It is necessary to form each functional layer that constitutes the device on the polyimide resin layer in order with the polyimide resin layer in close contact with the rigid substrate, and then peel off the completed flexible device from the rigid substrate.
  • the advantage of the polyimide resin layer is that it has good heat resistance against the curing process (including the drying process) applied to the device formation process. For this reason, even if a curing process is performed on the polyimide resin layer in the device formation process, no defects occur in the polyimide resin layer.
  • the polyimide resin layer has appropriate adhesion and peelability to an inorganic substrate which is a rigid substrate as described above.
  • FIG. 8 is a conceptual diagram showing a change in adhesion when an additive for increasing adhesion is added to polyimide.
  • FIG. 8 shows the adhesion to the inorganic substrate when the additive for improving the adhesion is added to the polyimide in the state where the additive for increasing the peelability is not added.
  • (2) shown in FIG. 8 shows the adhesion to the inorganic substrate when the additive for increasing the adhesiveness is added to the polyimide in the state where the additive for increasing the peelability is added.
  • the adhesion gradually increases as an additive for increasing the adhesion is added.
  • the 180 ° peel strength between the polyimide resin layer and the inorganic substrate can be appropriately controlled, and good adhesion and peelability can be obtained.
  • the present invention has been made based on the concept (2) shown in FIG.
  • the laminate according to the present embodiment includes an inorganic substrate, and (a) a polyimide resin layer containing polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher provided on the surface of the inorganic substrate,
  • the 180 ° peel strength between the polyimide resin layer and the inorganic substrate is 0.004 to 0.250 N / cm.
  • 180 ° peel strength is a test method for evaluating the peel strength of a laminated film or adhesive tape bonded by an adhesive layer, as defined in Japanese Industrial Standards (JIS Handbook Adhesion, K-6854). Yes, here, the adhesion to the polyimide resin layer formed on the surface of the inorganic substrate is shown.
  • the heat resistance adhesion between the polyimide resin layer (polyimide film) and the inorganic substrate is sufficient because the 180 ° peel strength between the polyimide resin layer and the inorganic substrate is 0.004 N / cm or more. It will be a thing.
  • the 180 ° peel strength is more preferably 0.010 N / cm or more, and further preferably 0.015 N / cm or more.
  • the peelability of the polyimide resin layer from the inorganic substrate can be controlled.
  • the 180 ° peel strength is more preferably 0.075 N / cm or less, and further preferably 0.050 N / cm or less.
  • the 180 ° peel strength is controlled by, for example, (b) a silicone-based surfactant or a fluorine-based surfactant, and (c) an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, as described later.
  • a silicone-based surfactant or a fluorine-based surfactant and (c) an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, as described later.
  • an alkoxysilane compound having at least one functional group selected from the group consisting of an amide group and a polymerizable cyclic ether group it can be carried out by adjusting these types and amounts.
  • the polyimide resin layer preferably has a thickness of 5 ⁇ m to 200 ⁇ m.
  • the thickness is preferably 10 ⁇ m to 30 ⁇ m. If it is 5 ⁇ m or more, the resin layer has excellent mechanical strength, and if it is 200 ⁇ m or less, the resin layer has excellent flexibility and lightness.
  • the thickness of the inorganic substrate is preferably 0.2 mm to 5 mm.
  • the resin composition of the present embodiment includes (a) a polyimide precursor having a 5% thermal decomposition temperature of 350 ° C. or higher or a polyimide precursor having a 5% thermal decomposition temperature of 350 ° C. or higher, and (b) a silicone-based surface activity. And (c) at least one functional group selected from the group consisting of an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, an amide group, and a polymerizable cyclic ether group. And having an alkoxysilane compound.
  • a polyimide resin layer made of polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, or formed by polyimidizing a polyimide precursor has a 5% thermal decomposition temperature of 350 ° C. or higher. Therefore, it is possible to form a polyimide resin layer that can withstand a heat treatment step, for example, exceeding 300 ° C., which is necessary for manufacturing a flexible display.
  • the thermal decomposition temperature refers to the thermal decomposition temperature obtained by TG / DTA measurement.
  • the 5% thermal decomposition temperature is a TG / DTA measurement.
  • the weight change due to thermal decomposition is 5%. It means the temperature when the temperature is reached.
  • the addition of a silicone surfactant or a fluorine surfactant improves the film thickness uniformity when a varnish-like composition is coated on an inorganic substrate.
  • the good uniformity of film thickness has the advantage that a polyimide resin layer can be stably formed on an inorganic substrate and appearance abnormality is unlikely to occur during heat treatment.
  • An alkoxysilane compound having at least one functional group selected from the group consisting of an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, an amide group and a polymerizable cyclic ether group is a functional group of the compound. Due to the direct bond between the group and the polymer and the intermolecular interaction, it is difficult to volatilize when the resin composition is heated. In addition, since the alkoxysilane compound is effectively taken into the polyimide resin layer by heat treatment during imidization / orientation, the polyimide resin layer is held at a desired thickness with respect to the inorganic substrate. And exhibit heat-resistant adhesion (initial adhesion and long-term adhesion) exceeding 300 ° C. in an inert atmosphere.
  • alkoxysilane compounds that do not have these functional groups volatilize except for compounds that adhere to and bind to the surface of the inorganic substrate during the heating process before imidization, and are not effectively retained in the composition.
  • the polyimide resin layer in close contact with the substrate becomes thin and has poor heat resistant adhesion.
  • the heat-resistant adhesion includes initial adhesion when handling the laminate and long-term adhesion during heat treatment during device formation.
  • the initial adhesion means that a polyimide precursor resin composition that becomes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher is coated on an inorganic substrate by imidization, and then polyimide is formed by heat treatment to form a polyimide resin layer.
  • a polyimide precursor resin composition that becomes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher is coated on an inorganic substrate by imidization, and then polyimide is formed by heat treatment to form a polyimide resin layer.
  • adhesion between the polyimide resin layer immediately after removing the solvent and the inorganic substrate under high-temperature conditions refers to adhesion at 300 ° C. or higher.
  • long-term adhesion means that a heat treatment is performed on a laminate composed of an inorganic substrate and a polyimide resin layer for a long time under a higher temperature condition, specifically, for example, at 300 ° C. to 500 ° C. for 6 minutes to 5 hours. Refers to adhesion after application. In the production of flexible devices, good initial adhesion and long-term adhesion have the advantage of suppressing appearance abnormalities such as peeling and swelling during heat treatment.
  • the polyimide resin layer easily peels from the inorganic substrate.
  • the polyimide resin layer does not peel off from the inorganic substrate by heat treatment during device formation, and the device can be formed well, and the polyimide resin layer can be easily peeled off from the inorganic substrate after forming the device, resulting in a good flexible device. It is done.
  • easy peelability means that a polyimide resin layer can be easily peeled from an inorganic substrate.
  • the excellent easy peelability has an advantage that the inorganic substrate can be easily peeled from the polyimide resin layer in the manufacture of the flexible device.
  • the polyimide resin layer can be peeled cleanly from the inorganic substrate, and a polyimide resin layer having a flat surface without any defects on the peeled surface can be obtained.
  • each component of the resin composition according to the present embodiment will be described in detail.
  • polyimide or polyimide precursor The polyimide or polyimide precursor according to the present embodiment is obtained by reacting tetracarboxylic dianhydride and diamine.
  • a polyimide precursor means what becomes a polyimide by imidation, and does not mean only a polyamic acid, The thing which a part of polyamic acid imidated and polyamic acid ester are also included.
  • polyamic acid is preferable from the viewpoints of solubility in a solvent to be used and heat resistance after polyimide formation.
  • polyimide or polyimide precursor is pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,3,3 ′, 4 ′.
  • -Biphenyltetracarboxylic dianhydride 2,2 ', 3,3'-biphenyltetracarboxylic dianhydride, p-phenylenebis (trimellitic acid monoester anhydride), 1,2,5,6-
  • the group consisting of naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3′-oxydiphthalic dianhydride, and 4,4′-oxydiphthalic dianhydride At least one selected from the group consisting of 80 mol% or more of all tetracarboxylic dianhydrides, and p-phenylenediamine, m-phenylenediamine, benzidine, 4,4 ′-(or , 4'-, 3,3'-, 2,4 '-) diamino-diphenyl ether, 5-amino-2- (p-amino-phenyl) benzox
  • the polyimide or polyimide precursor consists of a fluorine-containing aromatic acid dianhydride, an alicyclic acid dianhydride, and a sulfur-containing acid dianhydride as a tetracarboxylic dianhydride. It is a polyimide or polyamic acid obtained by reacting at least one selected from the group consisting of fluorine group-containing aromatic diamine, alicyclic diamine, and sulfur-containing diamine as at least one selected from the group, or diamine. It is preferable.
  • Fluorine group-containing aromatic acid dianhydrides include 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis (4- (3,4-dicarboxyphenoxy) Phenyl) hexafluoropropane dianhydride, 2,2-bis (4- (3,4-dicarboxybenzoyloxy) phenyl) hexafluoropropane dianhydride, and 2,2′-bis (trifluoromethyl)- 4,4′-bis (3,4-dicarboxyphenoxy) biphenyl dianhydride and the like.
  • alicyclic acid dianhydrides examples include bicyclo [2,2,2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 2,3,5,6-cyclohexanetetracarboxylic Acid dianhydride, 3,3 ′, 4,4′-bicyclohexyltetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, cyclobutanetetracarboxylic dianhydride, etc. Can be mentioned.
  • sulfur-containing dianhydride examples include bis (3,4-dicarboxyphenyl) sulfone dianhydride.
  • Fluorine group-containing aromatic diamines include 1,1,1,3,3,3-hexafluoro-2,2-bis (4-amino-phenyl) propane and 2,2′-bis (trifluoromethyl) benzidine 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, 2,2′-bis (3-amino-2,4-dihydroxyphenyl) hexafluoropropane, 2,2′-bis (4 -Amino-3,5-dihydroxyphenyl) hexafluoropropane, 2,2-bis [4- (3-amino-phenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, 2, Examples thereof include 2-bis [4- (4-amino-phenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane.
  • Examples of the alicyclic diamine include 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 4,4′-diaminodicyclohexylmethane, 4,4′-diaminodicyclohexylpropane, and 2,3-diaminobicyclo [2.2.
  • sulfur-containing diamine examples include 4,4 ′-(or 3,4′-, 3,3′-, 2,4 ′-) diamino-diphenylsulfone, 4,4 ′-(or 3,4′-, 3 , 3′-, 2,4 ′-) diamino-diphenyl sulfide, 4,4′-di (4-amino-phenoxy) phenyl sulfone, 4,4′-di (3-amino-phenoxy) phenyl sulfone, 3, 3'-diamino-diphenylsulfone, 3,3'-dimethyl-4,4'-diamino-biphenyl-6,6'-disulfone, bis (3-amino-phenyl) sulfide, bis (4-amino-phenyl) sulfide Bis (3-amino-phenyl) sulfoxide, bis (4-amino-phenyl) sulfoxide,
  • tetracarboxylic dianhydrides include 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride, 2,3,3 ′, 4′-benzophenone tetracarboxylic dianhydride, 2 , 2 ′, 3,3′-benzophenone tetracarboxylic dianhydride and the like. These tetracarboxylic dianhydrides may be used alone or in admixture of two or more.
  • tetracarboxylic dianhydride other conventionally known tetracarboxylic dianhydrides can be used as long as the effects of the present embodiment are exhibited.
  • Examples of other tetracarboxylic dianhydrides include 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride and 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride. 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane Dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, 2,2-bis (4- (4-amino-phenoxy) phenyl) propane, 1,3-dihydro-1,3-dioxo- 5-Isobenzofurancarboxylic acid-1,4-phenylene ester, 4- (2,5-dioxotetrahydrofuran-3-yl) -1,2,3,4-tetrahydronaphthalene-1,2-dicar
  • Examples of other diamines that can be used include the following. 3,3′-dimethyl-4,4′-diamino-biphenyl, 2,2′-dimethyl-4,4′-diamino-biphenyl, 3,3′-diethyl-4,4′-diamino-biphenyl, 2, 2'-diethyl-4,4'-diamino-biphenyl, 1,4-cyclohexyldiamine, p-xylylenediamine, m-xylylenediamine, 1,5-diamino-naphthalene, 3,3'-dimethoxybenzidine, 4 , 4 '-(or 3,4'-, 3,3'-, 2,4'-) diamino-diphenylmethane, 4,4 '-(or 3,4'-, 3,3'-, 2,4 '-) Diamino-diphenyl ether, 4,4'-benzophenonediamine,
  • a method for producing a polyimide precursor will be described.
  • all methods capable of producing a polyimide precursor including known methods, can be applied. Among these, it is preferable to perform the reaction in an organic solvent.
  • solvent used in such a reaction examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, ⁇ -butyrolactone, 1,2-dimethoxyethane, tetrahydrofuran, 1,3 -Dioxane, 1,4-dioxane, dimethyl sulfoxide, benzene, toluene, xylene, mesitylene, phenol, cresol, ethyl benzoate and butyl benzoate. These may be used alone or in combination of two or more.
  • N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone and ⁇ -butyrolactone are preferable, and N-methyl-2-pyrrolidone is particularly preferable.
  • the concentration of the reaction raw material in this reaction is usually 2% by mass to 80% by mass, preferably 5% by mass to 30% by mass.
  • the molar ratio of tetracarboxylic dianhydride to be reacted and diamine is in the range of 0.8 to 1.2. Within this range, the molecular weight can be increased, and the elongation and the like are excellent.
  • the molar ratio is preferably 0.9 to 1.1, more preferably 0.92 to 1.07.
  • the weight average molecular weight of the polyimide precursor is preferably 1,000 or more and 1,000,000 or less.
  • the weight average molecular weight refers to a molecular weight measured by gel permeation chromatography using polystyrene having a known number average molecular weight as a standard.
  • the weight average molecular weight is more preferably from 10,000 to 500,000, and most preferably from 20,000 to 300,000.
  • the weight average molecular weight is 1,000 or more and 1,000,000 or less, the strength and elongation of the resin layer obtained using the resin composition is improved, and the mechanical properties are excellent. Furthermore, it can be applied without bleeding at a desired film thickness during processing such as coating.
  • the polyimide precursor is obtained by the following method. First, polyamic acid is produced by subjecting the reaction raw material to a polycondensation reaction from room temperature to 80 ° C.
  • the end of the polymer main chain of the polyimide precursor can be end-capped with an end-capping agent made of a monoamine derivative or a carboxylic acid derivative.
  • an end-capping agent made of a monoamine derivative or a carboxylic acid derivative.
  • terminal blocking agent comprising a monoamine derivative
  • examples of the terminal blocking agent comprising a monoamine derivative include aniline, o-toluidine, m-toluidine, p-toluidine, 2,3-xylidine, 2,6-xylidine, 3,4-xylidine, and 3,5-xylidine.
  • Examples of the end-capping agent comprising a carboxylic acid derivative mainly include carboxylic anhydride derivatives.
  • carboxylic anhydride derivative examples include phthalic anhydride, 2,3-benzophenone dicarboxylic anhydride, 3,4-benzophenone dicarboxylic anhydride, 2,3-dicarboxyphenyl phenyl ether anhydride, 3,4-di Carboxyphenyl phenyl ether anhydride, 2,3-biphenyl dicarboxylic acid anhydride, 3,4-biphenyl dicarboxylic acid anhydride, 2,3-dicarboxyphenyl phenyl sulfone anhydride, 3,4-dicarboxyphenyl phenyl sulfone anhydride 2,3-dicarboxyphenyl phenyl sulfide anhydride, 3,4-dicarboxyphenyl phenyl sulfide anhydride, 1,2-naphthalenedicarboxylic anhydride, 2,3-naphthalenedicarboxylic anhydride, 1,8-naphthal
  • the obtained polyimide precursor solution may be used as it is without removing the solvent, and may further be used as a resin composition according to the present embodiment by blending necessary solvents, additives and the like.
  • Silicone-based surfactant or fluorine-based surfactant is not particularly limited as long as it has a siloxane structure as a nonpolar site.
  • the number of Si—O bonds in one molecule which is a nonpolar site is preferably 2 or more. From the viewpoint of uniform film formation with polyimide or a polyimide precursor, the number of Si—O bonds in one molecule which is a nonpolar site is preferably 1000 or less, more preferably 500 or less, and even more preferably 100 or less. is there.
  • the number of polyether groups, hydroxyl groups, carboxyl groups, or sulfo groups in one molecule, which is a polar site is preferably 1 or more.
  • the number of polyether groups, hydroxyl groups, carboxyl groups, or sulfo groups in one molecule that are polar sites is preferably 100 or less, more preferably 70 or less, and even more preferably 50 or less.
  • the maximum value of the molecular weight of the silicone-based surfactant to be added is that the silicone-based surfactant gathers at the interface between the polyimide resin layer and the inorganic substrate due to the solvent drying of the varnish and the heating in the curing process.
  • the size is adjusted so as to obtain good peelability from the inorganic substrate. Therefore, the molecular weight of the silicone surfactant is preferably 20000 or less, and more preferably 5000 or less.
  • the minimum molecular weight of the silicone surfactant to be added is that the silicone surfactant does not volatilize and remains in the polyimide resin layer by heating in the solvent drying and curing process of the varnish, and the polyimide resin layer is inorganic.
  • the size is adjusted so as to obtain good peelability from the substrate. Therefore, the molecular weight of the silicone surfactant is preferably 50 or more, and more preferably 100 or more.
  • the fluorosurfactant according to the present embodiment is not particularly limited as long as it has a C—F group bonding structure as a nonpolar site, but it is 3 or more and 100 or less in the molecule as a nonpolar site.
  • the number of C—F bonds in one molecule which is a nonpolar site is preferably 3 or more. From the viewpoint of uniform film formation with polyimide or polyimide precursor, the number of C—F bonds in one molecule which is a nonpolar site is preferably 100 or less, more preferably 70 or less, and even more preferably 50 or less. is there.
  • the number of polyether groups, hydroxyl groups, carboxyl groups, or sulfo groups in one molecule, which is a polar site is preferably 1 or more.
  • the number of polyether groups, hydroxyl groups, carboxyl groups, or sulfo groups in one molecule that are polar sites is preferably 100 or less, more preferably 70 or less, and even more preferably 50 or less.
  • the maximum value of the molecular weight of the fluorosurfactant to be added is that the fluorosurfactant gathers at the interface between the polyimide resin layer and the inorganic substrate due to the solvent drying of the varnish and the heating in the curing process.
  • the size is adjusted so as to obtain good peelability from the substrate. Therefore, the molecular weight of the fluorosurfactant is preferably 10,000 or less, and more preferably 5000 or less.
  • the minimum molecular weight of the fluorosurfactant to be added is that the fluorosurfactant does not volatilize and remains in the polyimide resin layer by heating in the solvent drying and curing process of the varnish, and the polyimide resin layer inorganic substrate Is adjusted to such a size that good peelability can be obtained. Therefore, the molecular weight of the fluorosurfactant is preferably 50 or more, and more preferably 100 or more.
  • silicone surfactants include polyoxyethylene (POE) -modified organopolysiloxane, polyoxyethylene / polyoxypropylene (POE / POP) -modified organopolysiloxane, POE sorbitan-modified organopolysiloxane, and POE glyceryl-modified organopolysiloxane. And organopolysiloxane modified with a hydrophilic group.
  • POE polyoxyethylene
  • POP polyoxypropylene
  • DBE-712 DBE-821 (manufactured by Amax Co.), KF-6015, KF-6016, KF-6017, KF-6028 (manufactured by Shin-Etsu Chemical Co., Ltd.), ABIL-EM97 (manufactured by Goldschmidt), Polyflow KL-100, Polyflow KL-401, Polyflow KL-402, Polyflow KL-700 (manufactured by Kyoeisha Chemical Co., Ltd.) and the like can be mentioned.
  • Fluorosurfactants include anionic fluorosurfactants such as perfluoroalkyl carboxylates, perfluoroalkyl phosphates, perfluoroalkyl sulfonates, perfluoroalkylethylene oxide adducts, and perfluoroalkyls.
  • anionic fluorine-based surfactants such as amine oxide, perfluoroalkyl polyoxyethylene ethanol, perfluoroalkyl alkoxylate, and fluorinated alkyl ester can be exemplified.
  • the addition amount of the component (b) added to the resin composition of the present embodiment is 0.001 mass relative to 100 mass parts of the polyimide or polyimide precursor from the viewpoint of peelability of the polyimide resin layer from the glass substrate. Part or more is preferable, and more preferably 0.01 part by weight or more. On the other hand, from the viewpoint of the adhesion of the polyimide resin layer to the glass substrate and the heat resistance of the polyimide, the addition amount is preferably 10 parts by mass or less, more preferably 5 parts by mass or less. When the addition amount is 10 parts by mass or less, contamination of the device due to generation of outgas can be prevented in the device manufacturing process.
  • the addition amount of the component (b) can be measured by liquid chromatography mass spectrometry (LC-MS).
  • the alkoxysilane compound according to the present embodiment is at least one selected from the group consisting of an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, an amide group, and a polymerizable cyclic ether group. It is not particularly limited as long as it is an alkoxysilane compound having a kind of functional group. By having these functional groups, compatibility with polyamic acid or polyimide is improved, polyimide by reaction with aromatic stacking, intermolecular interaction of imide, amino group or acid anhydride group in polyamic acid or polyimide Adhesion of the resin layer to the glass substrate is improved.
  • the alkoxysilane compound according to the present embodiment has at least one functional group selected from the group of carbamate group, carboxyl group, amide group and aryl group, so that the release property of the polyimide resin layer from the glass substrate is good. From the viewpoint of becoming.
  • the alkoxysilane compound according to the present embodiment is specifically a silane compound represented by the following general formula (I).
  • R 1 represents an amino group, carbamate group, carboxyl group, aryl group, acid anhydride group, amide group in a linear, branched, or cyclic organic group having 1 to 20 carbon atoms.
  • R 2 has a carbon atom number containing a photopolymerizable unsaturated double bond group or a polymerizable cyclic ether bond group 2-20 groups, aryl groups having 6-20 carbon atoms, alkylaryl groups having 2-20 carbon atoms, mercapto groups or alkyls having 1-20 carbon atoms which may be substituted with amino groups Group, a cycloalkyl group having 5 to 20 carbon atoms, or a group having 4 to 20 carbon atoms including a carboxyl group or a dicarboxylic anhydride group, and R 3 represents a methoxy group, an ethoxy group, a propoxy group, Iso At least one monovalent organic group selected from the group consisting of propoxy group, a hydroxyl group, or a chlorine (Cl), and a is an integer of 0 or 1.
  • ⁇ ⁇
  • the alkoxysilane compound having an amino group is an alkoxysilane compound having an amino group in a linear, branched, or cyclic organic group in which R 1 has 1 to 20 carbon atoms.
  • R 1 has 1 to 20 carbon atoms.
  • the alkoxysilane compound having a carbamate group is an alkoxysilane compound having a carbamate group in a linear, branched, or cyclic organic group in which R 1 has 1 to 20 carbon atoms.
  • Examples include (3-trimethoxysilylpropyl) -t-butyl carbamate and (3-triethoxysilylpropyl) -t-butyl carbamate.
  • the alkoxysilane compound having an acid anhydride group is an alkoxysilane compound having a dicarboxylic anhydride group in a linear, branched, or cyclic organic group having 1 to 20 carbon atoms in R 1. is there.
  • Preferred organic groups as R 1 include, for example, a succinic anhydride group (R 1 -1), a cyclohexanedicarboxylic anhydride group (R 1 -2), a 4-methyl-cyclohexanedicarboxylic anhydride group (R 1- 3), 5-methyl-cyclohexanedicarboxylic anhydride group (R 1 -4), bicycloheptane dicarboxylic anhydride group (R 1 -5), 7-oxa-bicycloheptane dicarboxylic anhydride group (R 1 -6) ) And phthalic anhydride groups (R 1 -7).
  • R 1 -1 succinic anhydride group
  • R 1 -2 a cyclohexanedicarboxylic anhydride group
  • R 1- 3 4-methyl-cyclohexanedicarboxylic anhydride group
  • R 1 -4 4-methyl-cyclohexanedicarboxylic anhydride group
  • the alkoxysilane compound having a carboxyl group is an alkoxysilane compound containing a carboxyl group in a linear, branched or cyclic organic group having 1 to 20 carbon atoms in R 1 .
  • the alkoxysilane compound having an aryl group, number of carbon atoms of R 1 is 1 to 20 linear, branched, or in the cyclic organic group, 1 aromatic ring of 6 to 20 carbon atoms It is an alkoxysilane compound having two or more.
  • An example is the hydrochloride of trimethoxysilane.
  • the alkoxysilane compound having an amide group is an alkoxysilane having an amide group in a linear, branched, or cyclic organic group having 1 to 20 carbon atoms as R 1 in the general formula (I).
  • the alkoxysilane compound having an amide group is a reaction of an alkoxysilane compound having an amino group with a carboxylic acid, an acid chloride, a dicarboxylic acid anhydride, or a tetracarboxylic acid anhydride, or a carboxyl group, an acid chloride group, or an acid anhydride. It is obtained by a reaction between an alkoxysilane compound having a physical group and an amine.
  • an amino group-containing alkoxysilane compound and a dicarboxylic acid anhydride or a tetracarboxylic acid anhydride are obtained, or an acid anhydride group is obtained. It is preferable that it is an alkoxysilane compound which has an amide group obtained by reaction with the alkoxysilane compound which has and an amine.
  • examples of the alkoxysilane compound having an amino group include the compounds described above.
  • examples of the dicarboxylic acid anhydride include succinic anhydride, cyclohexane dicarboxylic acid anhydride, 4-methyl-cyclohexane dicarboxylic acid anhydride, 5-methyl-cyclohexane dicarboxylic acid anhydride, bicycloheptane dicarboxylic acid anhydride, 7-oxabicyclo Heptanedicarboxylic anhydride, tetrahydrophthalic anhydride, trimellitic anhydride, pyromellitic anhydride, adipic anhydride, phthalic anhydride, (3-trimethoxysilylpropyl) succinic anhydride, (3-tri And polybasic acid anhydrides such as ethoxysilylpropyl) succinic anhydride.
  • tetracarboxylic acid anhydride examples include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, and 2,3,3 ′, 4′-biphenyltetracarboxylic acid.
  • Acid dianhydride 2,2 ', 3,3'-biphenyltetracarboxylic dianhydride, p-phenylenebis (trimellitic acid monoester anhydride), 1,2,5,6-naphthalenetetracarboxylic acid Examples include dianhydrides, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3′-oxydiphthalic dianhydride, and 4,4′-oxydiphthalic dianhydride. These may be used alone or in combination of two or more.
  • examples of the alkoxysilane compound having an acid anhydride group include the compounds described above.
  • examples of amines include ammonia, methylamine, ethylamine, propylamine, isopropylamine, butylamine, t-butylamine, pentylamine, hexylamine, 2-ethylhexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine.
  • the alkoxysilane compound having a polymerizable cyclic ether group refers to a linear, branched or cyclic organic group having 1 to 20 carbon atoms in R 1 , such as a glycidyl group or an epoxycyclohexyl group, It is an alkoxysilane compound having a reactive cyclic ether group.
  • alkoxysilane compounds that can be added in combination with the above include methyltrimethoxysilane, methyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, diethyldimethoxysilane, diethyl Diethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, cyclohexyltrimethoxysilane, cyclohexyltriethoxysilane, cyclohexylmethyldimethoxysilane, cyclohexylmethyldiethoxysilane, dicyclopentyldimethoxysilane, dicyclopentyldiethoxysilane, octadecyltrimethoxysilane , Octadecyltriethoxysilane, 3-mercaptopropyltrime
  • the amount of component (c) added to the resin composition of the present embodiment is 0.001 mass relative to 100 mass parts of the polyimide or polyimide precursor. Part or more is preferable, and more preferably 0.01 part by weight or more.
  • the addition amount is preferably 9 parts by mass or less, more preferably 5 parts by mass or less.
  • the amount of component (c) added can be measured by liquid chromatography mass spectrometry (LC-MS).
  • the resin composition of the present embodiment may be dissolved in a solvent to take the form of a varnish-like resin composition.
  • a solvent used here, N-methyl-2-pyrrolidone (NMP), ⁇ -butyrolactone, N, N-dimethylacetamide, N, N-dimethylformamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether , Propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, pyrubin
  • NMP N-methyl-2-pyrrolidone
  • ⁇ -butyrolactone N, N-dimethylacetamide, N, N-dimethylformamide, di
  • aprotic polar solvents are more preferred, and specific examples include N-methyl-2-pyrrolidone (NMP) and ⁇ -butyrolactone. Particularly preferred is N-methyl-2-pyrrolidone (NMP).
  • the amount of such a solvent used varies depending on the film thickness obtained, and is used in the range of 10 to 10,000 parts by mass with respect to 100 parts by mass of the polyimide or polyimide precursor.
  • the resin composition and polyimide resin layer of the present embodiment may contain other components than those described above, but the other additive components do not affect the 180 ° peel strength between the polyimide resin and the inorganic substrate. The amount is adjusted so that both good adhesion and releasability can be achieved.
  • the laminated body of the present embodiment is a varnish-like polyimide precursor composition which is converted to a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher by imidization treatment on an inorganic substrate and subjected to heat treatment.
  • a method of forming a polyimide resin layer by polyimidizing a polyimide precursor, or by applying a polyimide composition having a 5% thermal decomposition temperature of 350 ° C. or more on an inorganic substrate and performing a heat treatment to remove the solvent can get.
  • the inorganic substrate is preferably transparent from the viewpoint of positioning in the device forming step, and a glass substrate is particularly preferable.
  • glass substrates alkali-free glass substrates, soda-lime glass substrates, quartz glass substrates, etc. are used, but alkali-free glass substrates are used in many semiconductor manufacturing processes, and alkali-free glass substrates as inorganic substrates. Is preferred.
  • the inorganic substrate includes those obtained by treating the surface of the inorganic substrate with a coupling agent in advance in order to control adhesion and peelability with the polyimide composition film.
  • the method for producing the laminate of the present embodiment can be performed by developing the resin composition of the present embodiment on an inorganic substrate and performing a heat treatment by a known method.
  • Examples of the developing method include known coating methods such as spin coating, slit coating, and blade coating. Further, the heat treatment is performed on the inorganic substrate after the resin composition is developed, and is heat-treated at a temperature of 300 ° C. or lower for 1 to 300 minutes mainly for the purpose of solvent removal, and further at a temperature of 300 to 550 ° C. in an inert atmosphere such as nitrogen. The polyimide precursor is converted into a polyimide by heat treatment at 1 to 300 minutes.
  • the laminate of the present embodiment exhibits excellent heat resistance, dimensional stability, and heat adhesion to an inorganic substrate by heat-treating the resin composition of the present embodiment. It can be applied as a substrate.
  • a laminated body at a temperature exceeding 300 ° C. in an inert atmosphere such as a heat aging process or an excimer laser process when forming a low-temperature polysilicon thin semiconductor or oxide semiconductor, more specifically, at 300 ° C. to 500 ° C.
  • the polyimide resin layer does not peel off and a device can be formed satisfactorily.
  • the prepared polyimide resin layer can be peeled off.
  • the “resin adhesive layer” is an inorganic layer or an organic layer provided on the surface of an inorganic substrate for resin adhesion. In the present embodiment, the resin adhesive layer may or may not be provided.
  • the polyimide resin layer can be peeled cleanly from the inorganic substrate, and the polyimide resin layer can be formed without any defects on the peeled surface.
  • 1 to 7 are schematic cross-sectional views showing the manufacturing process of a flexible display using the resin composition according to the present embodiment.
  • a first substrate 11 made of an alkali-free glass substrate is prepared.
  • a polyimide precursor resin composition that becomes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher is applied to the surface of the first substrate 11 by the imidization treatment of the present embodiment described above.
  • the first polyimide resin layer 12 is formed by a method of forming a polyimide by heat treatment or a method of applying a polyimide resin composition having a 5% thermal decomposition temperature of 350 ° C. or higher and then removing the solvent by heat treatment. To do.
  • a first barrier layer 101 is formed on the first polyimide resin layer 12 of the first substrate 11.
  • a semiconductor layer 102, a gate insulating film 103, a gate electrode 104, an interlayer insulating film 105, a contact hole 106, and source / drain electrodes 107a and 107b are sequentially formed on the first barrier layer 101.
  • a thin film transistor (TFT) 108 is formed.
  • the semiconductor layer 102 is formed of polysilicon.
  • the semiconductor layer 102 is formed by first forming amorphous silicon, crystallizing it, and changing it to polysilicon.
  • crystallization methods for example, RTA (Rapid Thermal Annealing), SPC (Solid Phase Crystallization), ELA (Excimer Laser Crystallization), MIC (Metal Induced Crystallization), and MI (Metal Induced Crystallization). Lateral Solidification).
  • a display element is formed on the TFT 108.
  • a planarization layer 109 is formed on the source / drain electrodes 107a and 107b.
  • a contact hole 110 is formed in one electrode 107b of the source / drain electrodes 107a and 107b and is electrically connected to the first electrode 111.
  • the 1st electrode 111 functions as one electrode among the electrodes with which an organic light emitting element is equipped later.
  • a pixel definition film 112 patterned with an insulating material is formed on the first electrode 111 so that at least a part of the first electrode 111 is exposed.
  • an intermediate layer 113 including a light emitting layer is formed on the exposed portion of the first electrode 111.
  • a second electrode 114 facing the first electrode 111 is formed around the intermediate layer 113.
  • the sealing member 201 shown in FIG. 5 is manufactured separately, and the sealing member 201 is coupled to the upper portion of the organic light emitting device, and then the second substrate 202 of the sealing member 201 is separated.
  • the sealing member 201 has a second polyimide resin layer 203 formed on one main surface of a second substrate 202 made of an alkali-free glass substrate, for example, and further on the surface of the second polyimide resin layer 203.
  • the second barrier layer 204 is formed.
  • the second polyimide resin layer 203 can be formed using the resin composition of the present embodiment.
  • FIG. 6 after the sealing member 201 is disposed on the organic light emitting element 210, these are bonded.
  • heat treatment is performed in the state shown in FIG. 6 in the presence of oxygen, for example, at 300 ° C. to 350 ° C. in an air atmosphere. Accordingly, the first substrate 11 in contact with the first polyimide resin layer 12 can be peeled off, and the second substrate 202 in contact with the second polyimide resin layer 203 can be peeled off. As a result, a flexible display 100 as shown in FIG. 7 is obtained.
  • the first polyimide resin layer 12 formed by polyimidizing the polyimide precursor has a 5% thermal decomposition temperature of 350 ° C. or higher. Has heat resistance to withstand.
  • the semiconductor layer 102 can withstand a process such as polysilicon formation.
  • An alkoxysilane compound having at least one functional group selected from the group consisting of an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, an amide group and a polymerizable cyclic ether group does not have these groups.
  • it interacts with polyimide and is less likely to volatilize when the resin composition is heated, and is effectively incorporated into the polyimide resin layer during imidization / orientation at 400 ° C. or higher.
  • the polyimide resin layer is maintained at a desired thickness, and exhibits good heat-resistant adhesion (long-term adhesion) during long-time heat treatment.
  • the first substrate 11 and The laminated body composed of the first polyimide resin layer 12 is allowed to stand for 6 minutes to 5 hours until the temperature reaches 350 ° C. to 500 ° C. and the formation of polysilicon is completed.
  • the first polyimide resin layer 12 is excellent in long-term adhesion by using the resin composition of the present embodiment, the first polyimide resin layer 12 becomes the first substrate 11 during the polysiliconization. It is possible to suppress the occurrence of problems such as peeling from the surface.
  • the alkoxysilane compound is introduced into the polyimide by heat treatment when forming the polyimide, for example, it exhibits heat-resistant adhesion (initial adhesion) exceeding 400 ° C. in an inert atmosphere. Thereby, in the manufacture of the flexible display 100, there is an effect of suppressing the appearance abnormality.
  • the resin composition and the polyimide resin layer of the present embodiment have a silicone surfactant or a fluorosurfactant. Thereby, the peelability with respect to an inorganic substrate can be improved.
  • a polyimide resin layer while adding a silicone surfactant or a fluorine-type surfactant to a polyimide or a polyimide precursor, and adding the alkoxysilane compound which has a predetermined functional group, a polyimide resin layer It is possible to form a resin composition having good adhesion and peelability to an inorganic substrate and a laminate using the resin composition.
  • the polysilicon semiconductor driven flexible display has been described as an example.
  • the flexible device manufacturing method according to the present embodiment is also applied to a metal oxide semiconductor driven flexible device such as IGZO. can do.
  • the glass substrate from which the polyimide resin layer has been peeled off by the method of the present embodiment can peel off the polyimide resin layer entirely from the glass substrate due to easy release of polyimide. Therefore, it is possible to recycle the used glass substrate by passing the glass substrate surface through an easy glass substrate cleaning process using oxygen plasma, acid, or alkali solution.
  • the flexible device substrate in the present invention has a flexible film shape, for example, and is used for flexible devices such as flexible memories, sensors, and RF-IDs. Typically used for flexible displays.
  • the surface of the flexible device substrate that forms the functional layers of the device has high flatness.
  • the film thickness variation of the flexible device substrate must be reduced.
  • the flexible device substrate is required to have good flexibility, and in order to obtain good flexibility, the thickness together with the composition of the flexible device substrate is also an important factor.
  • the flexible device substrate having flexibility is carried, for example, to a roll-to-roll process and used for a device formation process. Therefore, in general, the flexible device substrate is marketed in the state of a flexible device including each functional layer of the device, but the flexible device substrate may be marketed alone.
  • the substrate for a flexible device of the present embodiment includes ( ⁇ ) a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, ( ⁇ ) a chemical structure represented by the following general formula (1) and / or the following general formula (2). ( ⁇ ) a compound having a chemical structure represented by the following general formula (3), a compound having one or more of the group consisting of a hydroxyl group, a carboxyl group and a sulfo group, ( ⁇ ) The compound which has a chemical structure represented by Formula (4) is contained.
  • the polyimide used in the present embodiment has a 5% thermal decomposition temperature of 350 ° C. or higher.
  • Such a polyimide is typically obtained by imidizing a polyimide precursor obtained by reacting tetracarboxylic dianhydride and diamine by heat treatment or the like.
  • the polyimide precursor used here is pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,3,3 ′, in terms of heat resistance and mechanical strength.
  • the polyimide or polyimide precursor consists of a fluorine-containing aromatic acid dianhydride, an alicyclic acid dianhydride, and a sulfur-containing acid dianhydride as a tetracarboxylic dianhydride. It is a polyimide or polyamic acid obtained by reacting at least one selected from the group consisting of fluorine group-containing aromatic diamine, alicyclic diamine, and sulfur-containing diamine as at least one selected from the group, or diamine. It is preferable.
  • Fluorine group-containing aromatic acid dianhydrides include 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis (4- (3,4-dicarboxyphenoxy) Phenyl) hexafluoropropane dianhydride, 2,2-bis (4- (3,4-dicarboxybenzoyloxy) phenyl) hexafluoropropane dianhydride, and 2,2′-bis (trifluoromethyl)- 4,4′-bis (3,4-dicarboxyphenoxy) biphenyl dianhydride and the like.
  • alicyclic acid dianhydrides examples include bicyclo [2,2,2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 2,3,5,6-cyclohexanetetracarboxylic Acid dianhydride, 3,3 ′, 4,4′-bicyclohexyltetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, cyclobutanetetracarboxylic dianhydride, etc. Can be mentioned.
  • sulfur-containing dianhydride examples include bis (3,4-dicarboxyphenyl) sulfone dianhydride.
  • Fluorine group-containing aromatic diamines include 1,1,1,3,3,3-hexafluoro-2,2-bis (4-amino-phenyl) propane and 2,2′-bis (trifluoromethyl) benzidine 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, 2,2′-bis (3-amino-2,4-dihydroxyphenyl) hexafluoropropane, 2,2′-bis (4 -Amino-3,5-dihydroxyphenyl) hexafluoropropane, 2,2-bis [4- (3-amino-phenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, 2, Examples thereof include 2-bis [4- (4-amino-phenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane.
  • Examples of the alicyclic diamine include 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 4,4′-diaminodicyclohexylmethane, 4,4′-diaminodicyclohexylpropane, and 2,3-diaminobicyclo [2.2.
  • sulfur-containing diamine examples include 4,4 ′-(or 3,4′-, 3,3′-, 2,4 ′-) diamino-diphenylsulfone, 4,4 ′-(or 3,4′-, 3 , 3′-, 2,4 ′-) diamino-diphenyl sulfide, 4,4′-di (4-amino-phenoxy) phenyl sulfone, 4,4′-di (3-amino-phenoxy) phenyl sulfone, 3, 3'-diamino-diphenylsulfone, 3,3'-dimethyl-4,4'-diamino-biphenyl-6,6'-disulfone, bis (3-amino-phenyl) sulfide, bis (4-amino-phenyl) sulfide Bis (3-amino-phenyl) sulfoxide, bis (4-amino-phenyl) sulfoxide,
  • tetracarboxylic dianhydrides include 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride, 2,3,3 ′, 4′-benzophenone tetracarboxylic dianhydride, 2 , 2 ′, 3,3′-benzophenone tetracarboxylic dianhydride and the like. These tetracarboxylic dianhydrides may be used alone or in admixture of two or more.
  • tetracarboxylic dianhydride other conventionally known tetracarboxylic dianhydrides can be used as long as the effects of the present embodiment are exhibited.
  • Examples of other tetracarboxylic dianhydrides include 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride and 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride. 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane Dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, 2,2-bis (4- (4-amino-phenoxy) phenyl) propane, 1,3-dihydro-1,3-dioxo- 5-Isobenzofurancarboxylic acid-1,4-phenylene ester, 4- (2,5-dioxotetrahydrofuran-3-yl) -1,2,3,4-tetrahydronaphthalene-1,2-dicar
  • Examples of other diamines that can be used include the following. 3,3′-dimethyl-4,4′-diamino-biphenyl, 2,2′-dimethyl-4,4′-diamino-biphenyl, 3,3′-diethyl-4,4′-diamino-biphenyl, 2, 2'-diethyl-4,4'-diamino-biphenyl, 1,4-cyclohexyldiamine, p-xylylenediamine, m-xylylenediamine, 1,5-diamino-naphthalene, 3,3'-dimethoxybenzidine, 4 , 4 '-(or 3,4'-, 3,3'-, 2,4'-) diamino-diphenylmethane, 4,4 '-(or 3,4'-, 3,3'-, 2,4 '-) Diamino-diphenyl ether, 4,4'-benzophenonediamine,
  • diamines may be used alone or in combination of two or more.
  • a method for producing the polyimide precursor all methods that can produce a polyimide precursor, including known methods, can be applied. Among these, it is preferable to perform the reaction in an organic solvent.
  • solvent used in such a reaction examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, ⁇ -butyrolactone, 1,2-dimethoxyethane, tetrahydrofuran, 1,3 -Dioxane, 1,4-dioxane, dimethyl sulfoxide, benzene, toluene, xylene, mesitylene, phenol, cresol, ethyl benzoate and butyl benzoate. These may be used alone or in combination of two or more.
  • N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone and ⁇ -butyrolactone are preferable, and N-methyl-2-pyrrolidone is particularly preferable.
  • the concentration of the reaction raw material in this reaction is usually 2% by mass to 80% by mass, preferably 5% by mass to 30% by mass.
  • the molar ratio of tetracarboxylic dianhydride to be reacted and diamine is in the range of 0.8 to 1.2. Within this range, the molecular weight can be increased, and the elongation and the like are excellent.
  • the molar ratio is preferably 0.9 to 1.1, more preferably 0.92 to 1.07.
  • the weight average molecular weight of the polyimide precursor is preferably 1,000 or more and 1,000,000 or less.
  • the weight average molecular weight refers to a molecular weight measured by gel permeation chromatography using polystyrene having a known number average molecular weight as a standard.
  • the weight average molecular weight is more preferably from 10,000 to 500,000, and most preferably from 20,000 to 300,000.
  • the weight average molecular weight is 1,000 or more and 1,000,000 or less, the strength and elongation of the resin layer obtained using the resin composition is improved, and the mechanical properties are excellent. Furthermore, it can be applied without bleeding at a desired film thickness during processing such as coating.
  • the polyimide precursor is obtained by the following method. First, polyamic acid is produced by subjecting the reaction raw material to a polycondensation reaction from room temperature to 80 ° C.
  • the end of the polymer main chain of the polyimide precursor can be end-capped with an end-capping agent made of a monoamine derivative or a carboxylic acid derivative.
  • an end-capping agent made of a monoamine derivative or a carboxylic acid derivative.
  • terminal blocking agent comprising a monoamine derivative
  • examples of the terminal blocking agent comprising a monoamine derivative include aniline, o-toluidine, m-toluidine, p-toluidine, 2,3-xylidine, 2,6-xylidine, 3,4-xylidine, and 3,5-xylidine.
  • Examples of the end-capping agent comprising a carboxylic acid derivative mainly include carboxylic anhydride derivatives.
  • carboxylic anhydride derivative examples include phthalic anhydride, 2,3-benzophenone dicarboxylic anhydride, 3,4-benzophenone dicarboxylic anhydride, 2,3-dicarboxyphenyl phenyl ether anhydride, 3,4-di Carboxyphenyl phenyl ether anhydride, 2,3-biphenyl dicarboxylic acid anhydride, 3,4-biphenyl dicarboxylic acid anhydride, 2,3-dicarboxyphenyl phenyl sulfone anhydride, 3,4-dicarboxyphenyl phenyl sulfone anhydride 2,3-dicarboxyphenyl phenyl sulfide anhydride, 3,4-dicarboxyphenyl phenyl sulfide anhydride, 1,2-naphthalenedicarboxylic anhydride, 2,3-naphthalenedicarboxylic anhydride, 1,8-naphthal
  • the obtained polyimide precursor solution may be used as it is without removing the solvent, and may further be used as a resin composition according to the present embodiment by blending necessary solvents, additives and the like. Then, as will be described later, this resin composition is applied to the surface of the inorganic substrate, subjected to a predetermined heat treatment or the like to form a polyimide resin layer, and peeled off from the inorganic substrate, thereby forming a flexible resin composed of the polyimide resin layer.
  • a device substrate can be obtained.
  • This flexible device substrate includes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher in a state where a predetermined heat treatment is performed on the polyimide or the polyimide precursor.
  • the compound having the chemical structure represented by the general formula (1) is a compound derived from a bifunctional silicone compound.
  • examples of this compound include silicone oils typified by dimethylsiloxane and modified products thereof, or silicone surfactants having a hydrophilic group bonded to dimethylsiloxane.
  • This compound should just have the structure of General formula (1) in the molecule
  • this compound may be reacted and decomposed by heat in the flexible device substrate.
  • surface tension can be controlled and the surface roughness of the substrate for flexible devices can be reduced.
  • the compound having the chemical structure represented by the general formula (2) is a compound derived from a fluorinated hydrocarbon.
  • a typical example of this compound is a fluorosurfactant, specifically, an anionic fluorosurfactant such as perfluoroalkyl carboxylate, perfluoroalkyl phosphate, perfluoroalkyl sulfonate, Nonionic fluorinated surfactants such as perfluoroalkylethylene oxide adducts, perfluoroalkylamine oxides, perfluoroalkyl polyoxyethylene ethanol, perfluoroalkyl alkoxylates, fluorinated alkyl esters and the like can be mentioned.
  • the compound represented by the general formula (2) it is only necessary to have a structure derived from a fluorinated hydrocarbon. Therefore, the above fluorosurfactant itself may be used, or the fluorosurfactant. Those obtained by removing the hydrophilic group may be used.
  • this compound may be reacted and decomposed by heat in the flexible device substrate.
  • surface tension can be controlled and the surface roughness of the substrate for flexible devices can be reduced.
  • the compound having one or more chemical groups represented by the general formula (3), a hydroxyl group, a carboxyl group, and a sulfo group is a compound derived from a surfactant.
  • Typical examples of this compound are silicone-based and fluorine-based surfactants.
  • examples of this compound include silicone-based surfactants having a hydrophilic group bonded to dimethylsiloxane, perfluoroalkyl carboxylates, perfluoroalkyls.
  • Anionic fluorosurfactants such as phosphate esters and perfluoroalkyl sulfonates, perfluoroalkyl ethylene oxide adducts, perfluoroalkyl amine oxides, perfluoroalkyl polyoxyethylene ethanol, perfluoroalkyl alkoxylates, fluorine Nonionic fluorine-based surfactants such as alkylated alkyl esters.
  • phosphate esters and perfluoroalkyl sulfonates perfluoroalkyl ethylene oxide adducts, perfluoroalkyl amine oxides, perfluoroalkyl polyoxyethylene ethanol, perfluoroalkyl alkoxylates
  • fluorine Nonionic fluorine-based surfactants such as alkylated alkyl esters.
  • the compound represented by the general formula (3) it is only necessary to have a hydrophilic group of a surfactant. Therefore, the above-mentioned silicone-based
  • this compound may react and decompose by heat in the substrate for flexible devices.
  • surface tension can be controlled and the surface roughness of the substrate for flexible devices can be reduced.
  • the compound having the chemical structure represented by the general formula (4) is a compound derived from a trifunctional silicone compound.
  • this compound include hydrolysis condensates of trifunctional alkoxysilanes.
  • Trifunctional alkoxysilanes used to obtain this compound include aminopropyltrimethoxysilane, aminopropyltriethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl).
  • this compound may react and decompose by heat in the flexible device substrate.
  • this compound is included, the film thickness dispersion
  • the addition amount of the ( ⁇ ) component contained in the flexible device substrate of the present embodiment is 0.0001 to 9 parts by mass with respect to 100 parts by mass of the ( ⁇ ) polyimide from the viewpoint of film thickness uniformity and flexibility.
  • the amount is preferably part by mass, more preferably 0.001 part by mass to 5 parts by mass.
  • the addition amount of the ( ⁇ ) component contained in the flexible device substrate of the present embodiment is 0.0001 parts by mass with respect to 100 parts by mass of the polyimide ( ⁇ ) from the viewpoint of film thickness uniformity and flexibility. It is preferably from 10 parts by mass, more preferably from 0.0001 parts by mass to 5 parts by mass.
  • 1 to 7 are schematic cross-sectional views showing the manufacturing process of a flexible display using the resin composition according to the present embodiment.
  • a first substrate 11 made of an alkali-free glass substrate is prepared.
  • a polyimide precursor resin composition that becomes a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher by the imidization treatment of the present embodiment described above.
  • the first polyimide resin layer 12 is then applied by a method of applying a polyimide by heat treatment or a polyimide resin composition having a 5% thermal decomposition temperature of 350 ° C. or higher and then removing the solvent by heat treatment.
  • a first barrier layer 101 is formed on the first polyimide resin layer 12 of the first substrate 11.
  • a semiconductor layer 102, a gate insulating film 103, a gate electrode 104, an interlayer insulating film 105, a contact hole 106, and source / drain electrodes 107a and 107b are sequentially formed on the first barrier layer 101.
  • a thin film transistor (TFT) 108 is formed.
  • the semiconductor layer 102 is formed of polysilicon.
  • the semiconductor layer 102 is formed by first forming amorphous silicon, crystallizing it, and changing it to polysilicon.
  • crystallization methods for example, RTA (Rapid Thermal Annealing), SPC (Solid Phase Crystallization), ELA (Excimer Laser Crystallization), MIC (Metal Induced Crystallization), and MI (Metal Induced Crystallization). Lateral Solidification).
  • a display element is formed on the TFT 108.
  • a planarization layer 109 is formed on the source / drain electrodes 107a and 107b.
  • a contact hole 110 is formed in one electrode 107b of the source / drain electrodes 107a and 107b and is electrically connected to the first electrode 111.
  • the 1st electrode 111 functions as one electrode among the electrodes with which an organic light emitting element is equipped later.
  • a pixel defining film 112 patterned with an insulating material is formed on the first electrode 111 so as to expose at least a part thereof.
  • an intermediate layer 113 including a light emitting layer is formed on the exposed portion of the first electrode 111.
  • a second electrode 114 facing the first electrode 111 is formed around the intermediate layer 113.
  • the sealing member 201 shown in FIG. 5 is manufactured separately, and the sealing member 201 is coupled to the upper portion of the organic light emitting device, and then the second substrate 202 of the sealing member 201 is separated.
  • the sealing member 201 has a second polyimide resin layer 203 formed on one main surface of a second substrate 202 made of an alkali-free glass substrate, for example, and further on the surface of the second polyimide resin layer 203.
  • the second barrier layer 204 is formed.
  • the second polyimide resin layer 203 can be formed using the resin composition of the present embodiment.
  • FIG. 6 after the sealing member 201 is disposed on the organic light emitting element 210, these are bonded.
  • Each of the first polyimide resin layer 12 and the second polyimide resin layer 203 corresponds to a flexible device substrate.
  • the flexible device substrate is a thin film-like insulating substrate having flexibility.
  • a substrate generally refers to a base material or a support member that can form a functional layer on the surface thereof, but a flexible plate-like material that is bonded to the surface of a device and has a covering function or a protective function. Including.
  • the flexible device includes ( ⁇ ) a polyimide having a 5% thermal decomposition temperature of 350 ° C. or higher, ( ⁇ ) a chemical structure represented by the above general formula (1) and / or the above general formula (2). ) A compound having a chemical structure represented by ( ⁇ ), ( ⁇ ) a compound having one or more of the group consisting of a chemical structure represented by the above general formula (3), a hydroxyl group, a carboxyl group, and a sulfo group, ( ⁇ ) It can be set as the structure containing the polyimide resin layer containing the compound which has a chemical structure represented by said General formula (4), and the polyimide resin layer does not need to comprise the board
  • the polyimide resin layer may be a layer present in the flexible device as well as a layer appearing on the surface of the flexible device.
  • the flexible device substrate of the present embodiment described above has the following effects. That is, in this embodiment, the film thickness variation of the flexible device substrate can be reduced.
  • the film thickness can be measured, for example, with an optical film thickness meter.
  • the thickness of the flexible device substrate of the present embodiment is preferably 5 ⁇ m to 200 ⁇ m.
  • the thickness is preferably 10 ⁇ m to 30 ⁇ m. If it is 5 ⁇ m or more, it is excellent in mechanical strength, and if it is 200 ⁇ m or less, it is excellent in flexibility and lightness.
  • the film thickness variation of the substrate can be suppressed to 50 nm or less (film thickness variation with respect to a width of 10 cm) with respect to the above-described thin thickness dimension.
  • a flexible device manufactured using the flexible device substrate of the present embodiment or a flexible device having a flexible polyimide resin layer exhibits good in-plane uniformity in property evaluation such as electrical properties. Can do. This is because the film thickness variation of the substrate for flexible devices is small and the flatness of the substrate surface is high, so that each layer constituting the device, which is formed on the substrate surface, can be uniformly formed in the plane.
  • NMP N-methyl-2-pyrrolidone
  • Example 1 to 26 and Comparative Examples 1 to 4 Preparation of polyamic acid and polyimide composition
  • Various components were prepared and mixed as shown in Table 1 and Table 2. This was pressure filtered through a PTFE filter having a pore size of 2.5 microns to obtain varnish compositions of Examples 1 to 26 and Comparative Examples 1 to 4.
  • the used (B) silicone compound or fluorine compound and (C) alkoxysilane compound are as follows.
  • the alkoxysilane compound included in Comparative Example 4 is methyltrimethoxysilane, and is selected from the group consisting of an amide group, an amino group, a carbamate group, a carboxyl group, an aryl group, an acid anhydride group, and a polymerizable cyclic ether group. This does not correspond to an alkoxysilane compound having at least one functional group.
  • Adhesion of the cured polyimide resin layer (in Tables 3 and 4, referred to as post-cure adhesion)
  • the adhesion between the non-alkali glass substrate and the polyimide resin layer was About the property, the state of the coating film was confirmed visually by the following criteria.
  • 180 ° peel strength evaluation (referred to as 180 ° peel strength in Tables 3 and 4)
  • a varnish-like composition obtained in Examples 1 to 26 and Comparative Examples 1 to 4 was coated on a glass substrate, and after curing, a polyimide resin layer having a thickness of 20 ⁇ m was cut into a length of 10 mm and a width of 10 mm, and a width of 10 mm.
  • the width of 1.0 mm at the center of was masked with tape.
  • the humidity is adjusted for 24 hours or more in an environment of temperature 23 ⁇ 2 ° C. and humidity 50 ⁇ 5% RH, and in that environment, a 1.0 mm wide polyimide resin layer masked with tape is peeled from the glass substrate at an angle of 180 °.
  • the stress was measured at a peeling rate of 50 mm / min.
  • A The polyimide resin layer adhered to the glass substrate can be easily peeled off.
  • ⁇ The polyimide resin layer in close contact with the glass substrate is in close contact, and there is a catch at the time of peeling, but the polyimide resin layer can be peeled off without tearing.
  • X The polyimide resin layer is not adhered to the glass substrate, or the polyimide resin layer is adhered and does not peel off, and the film is torn.
  • the polyimide resin layer is peeled from the inorganic substrate.
  • the component (c) has at least one functional group selected from the group consisting of a carbamate group, a carboxyl group, an amide group and an aryl group.
  • the resin compositions according to Examples 1 to 26 can be suitably used as a substrate for a flexible device, and the laminate can be suitably used as a substrate for producing a flexible device.
  • Example 27 (A) P-1 shown in Synthesis Example 1 as a polyamic acid, (B) DBE-712 (manufactured by AMAX Co.) as a silicone compound, (C) 3-aminopropyltriethoxysilane and phthalic anhydride as an alkoxysilane compound (D) N-methyl-2-pyrrolidone (NMP) as a solvent was prepared and mixed at a mass ratio of 10.0: 0.05: 0.05: 89.90. This was pressure filtered with a PTFE filter having a pore size of 2.5 microns to obtain a varnish-like composition.
  • NMP N-methyl-2-pyrrolidone
  • the varnish-like composition was coated on a non-alkali glass substrate whose surface was cleaned by an alkali cleaning method and a plasma cleaning method using a bar coater so that the film thickness after curing was 20 ⁇ m.
  • the obtained coating film was cured under conditions of 140 ° C. ⁇ 1 hr + 250 ° C. ⁇ 1 hr + 350 ° C. ⁇ 1 hr.
  • Example 28 (A) P-1 shown in Synthesis Example 1 as polyamic acid, (B) LE-605 (manufactured by Kyoeisha Chemical Co., Ltd.) as fluorine compound, (C) 3-aminopropyltriethoxysilane and phthalic anhydride as alkoxysilane compound (D) N-methyl-2-pyrrolidone (NMP) as a solvent was prepared and mixed at a mass ratio of 10.0: 0.09: 0.01: 89.90. This was pressure filtered with a PTFE filter having a pore size of 2.5 microns to obtain a varnish-like composition.
  • NMP N-methyl-2-pyrrolidone
  • the varnish-like composition was coated on a non-alkali glass substrate whose surface was cleaned by an alkali cleaning method and a plasma cleaning method using a bar coater so that the film thickness after curing was 20 ⁇ m.
  • the obtained coating film was cured under conditions of 140 ° C. ⁇ 1 hr + 250 ° C. ⁇ 1 hr + 350 ° C. ⁇ 1 hr.
  • the varnish-like composition was coated on a non-alkali glass substrate whose surface was cleaned by an alkali cleaning method and a plasma cleaning method using a bar coater so that the film thickness after curing was 20 ⁇ m.
  • the obtained coating film was cured under conditions of 140 ° C. ⁇ 1 hr + 250 ° C. ⁇ 1 hr + 350 ° C. ⁇ 1 hr.
  • the varnish-like composition was coated on a non-alkali glass substrate whose surface was cleaned by an alkali cleaning method and a plasma cleaning method using a bar coater so that the film thickness after curing was 20 ⁇ m.
  • the obtained coating film was cured under conditions of 140 ° C. ⁇ 1 hr + 250 ° C. ⁇ 1 hr + 350 ° C. ⁇ 1 hr.
  • the varnish-like composition was coated on a non-alkali glass substrate whose surface was cleaned by an alkali cleaning method and a plasma cleaning method using a bar coater so that the film thickness after curing was 20 ⁇ m.
  • the obtained coating film was cured under conditions of 140 ° C. ⁇ 1 hr + 250 ° C. ⁇ 1 hr + 350 ° C. ⁇ 1 hr.
  • ⁇ Sputter cleaning conditions> Measurement condition
  • the vertical axis represents Total Counts (0.0005 amu).
  • the vertical axis represents Total Counts (0.0009 amu). Although not described, the right end of the horizontal axis in FIG. 10 indicates 59.5.
  • the vertical axis represents Total Counts (0.0008 amu). Although not shown, the left end of the horizontal axis in FIG. 11 indicates 44.5, and the right end indicates 45.5.
  • Example 29 The laminated body obtained in Example 27 was used as a substrate for manufacturing a flexible device, and a first barrier layer was formed on the laminated body. Further, on the first barrier layer, a semiconductor layer, a gate insulating film, a gate electrode, an interlayer insulating film, a contact hole, and a source / drain electrode were sequentially formed to form a thin film transistor (TFT). Thereafter, the TFT device was peeled from the alkali-free glass substrate to obtain a flexible TFT device. The current-voltage characteristics of the obtained flexible TFT device were evaluated and confirmed to show good in-plane uniformity.
  • TFT thin film transistor
  • Example 30 Using the laminate obtained in Example 28 as a substrate for manufacturing a flexible device, a first barrier layer was formed on the laminate. Further, on the first barrier layer, a semiconductor layer, a gate insulating film, a gate electrode, an interlayer insulating film, a contact hole, and a source / drain electrode were sequentially formed to form a thin film transistor (TFT). Thereafter, the TFT device was peeled from the alkali-free glass substrate to obtain a flexible TFT device. The current-voltage characteristics of the obtained flexible TFT device were evaluated and confirmed to show good in-plane uniformity.
  • TFT thin film transistor
  • the present invention is not limited to this.
  • the present invention can also be applied to other flexible devices such as solar cell substrates, flexible wiring boards, and flexible memories.
  • the present invention can be used, for example, as a substrate, particularly in the production of flexible devices, and can be suitably used, for example, in the production of flexible displays and solar cells.

Abstract

La présente invention peut concerner une composition de résine, un stratifié, un procédé de production d'un stratifié, et un procédé de production d'un dispositif flexible, de telle manière qu'une adhérence suffisante soit obtenue entre une couche de résine et un substrat inorganique au cours de la production d'un dispositif flexible, et seul le substrat inorganique peut être facilement décollé de la couche de résine dans l'étape finale. La présente invention permet en outre de produire un substrat pour des dispositifs flexibles et un dispositif flexible au moyen dudit substrat, les variations d'épaisseur de film étant faibles et le dispositif étant moins sujet à un mauvais fonctionnement lorsque le dispositif est construit.
PCT/JP2013/080080 2012-11-08 2013-11-07 Substrat pour dispositif flexible, dispositif flexible et procédé de production de celui-ci, stratifié et procédé de production de celui-ci, et composition de résine WO2014073591A1 (fr)

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CN201380057552.XA CN104769021B (zh) 2012-11-08 2013-11-07 柔性器件用基板、柔性器件及其制造方法、层积体及其制造方法、以及树脂组合物
KR1020157011891A KR101709422B1 (ko) 2012-11-08 2013-11-07 플렉서블 디바이스용 기판, 플렉서블 디바이스 및 그 제조 방법, 적층체 및 그 제조 방법, 그리고 수지 조성물
JP2014545741A JP6067740B2 (ja) 2012-11-08 2013-11-07 フレキシブルデバイスの製造方法、積層体及びその製造方法、並びに、樹脂組成物

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