WO2015012385A1 - ディスプレイ基板用樹脂組成物、ディスプレイ基板用樹脂薄膜及びディスプレイ基板用樹脂薄膜の製造方法 - Google Patents
ディスプレイ基板用樹脂組成物、ディスプレイ基板用樹脂薄膜及びディスプレイ基板用樹脂薄膜の製造方法 Download PDFInfo
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- WO2015012385A1 WO2015012385A1 PCT/JP2014/069672 JP2014069672W WO2015012385A1 WO 2015012385 A1 WO2015012385 A1 WO 2015012385A1 JP 2014069672 W JP2014069672 W JP 2014069672W WO 2015012385 A1 WO2015012385 A1 WO 2015012385A1
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Classifications
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- 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
- C08G73/14—Polyamide-imides
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- 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
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- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- 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
- 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
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a 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
Definitions
- the present invention relates to a resin composition for display substrate, a resin thin film for display substrate, and a method for producing a resin thin film for display substrate.
- polyimide resin since polyimide resin has high insulation performance as well as heat resistance, it has been applied to electronic component materials such as FPC. In that application, it is often laminated with a metal such as silicon or copper, and attempts have been made to reduce the linear thermal expansion coefficient of the polyimide resin to the same level as silicon or metal.
- a metal such as silicon or copper
- polyimide resin for electronic component materials has high heat resistance and low linear expansion, it is generally low in transparency and cannot be used as an optical film as a substitute for glass. It was.
- Patent Document 1 discloses a polyimide film for a display substrate using a polyimide obtained from an alicyclic structure-containing tetracarboxylic dianhydride and various diamines.
- Patent Document 2 discloses a polyimide film for a display substrate using a polyimide obtained from an alicyclic tetracarboxylic dianhydride having a cyclohexane skeleton and an aromatic diamine containing a sulfone group.
- the tetracarboxylic dianhydride used in Patent Document 1 also contains an aromatic group.
- the transparency of the film obtained by intramolecular conjugation of the polyimide chain or charge transfer interaction is lowered as compared with tetracarboxylic dianhydride which does not contain an aromatic group and consists only of an alicyclic group.
- the acid dianhydride used in Patent Document 2 has a special structure called a cis-structure cyclohexane skeleton, the versatility is poor, and the production cost of polyimide becomes high, resulting in an expensive product. There's a problem.
- the alicyclic tetracarboxylic dianhydride has a problem in that a high molecular weight polymer that exhibits sufficient film toughness from the viewpoint of polymerization reactivity may not be obtained.
- 1,2,3,4-cyclobutanetetracarboxylic dianhydride (hereinafter referred to as CBDA), which is the most popular among tetracarboxylic dianhydrides, exhibits relatively high polymerization reactivity with diamine, Due to its three-dimensional structure, imidation reaction of the polyimide precursor hardly occurs, and a higher temperature is required to complete the imidization reaction, which causes coloring of the polyimide film, and the use of CBDA as a display substrate is not advantageous. Has been pointed out (Patent Document 1 and Patent Document 2).
- the present invention has been made in view of such circumstances, and the object thereof is not dependent on curing conditions as a flexible display substrate, and has a high heat resistance having sufficient transparency and an appropriate linear expansion coefficient. It is providing the resin composition for display substrates.
- the Ar 1 is represented by the following formula (2) (wherein k represents 1 or 2, p represents 1 or 2), and the Ar 2 is represented by the following formula (3) (wherein X represents Represents a fluoroalkylene group having 1 to 3 carbon atoms).
- the polyamic acid is represented by formulas (1-2) and (1-5) (wherein Ar 1 and Ar 2 have the same definitions as above, and Ar 4 is represented by formula (5) (wherein r represents a divalent group represented by the representative) 1, 2 or 3, n 2 and n 5 further comprising a repeating unit represented by the representative) the number of each repeating unit ⁇ 1> to ⁇ 5 Any composition of>.
- the organic solvent is represented by the following formula (A) or (B) (wherein R 1 and R 2 each independently represents an alkyl group having 1 to 4 carbon atoms, and h represents a natural number).
- ⁇ 8> A resin thin film for a display substrate produced using the resin composition for a display substrate according to any one of ⁇ 1> to ⁇ 7>.
- An image display device comprising the resin thin film for a display substrate according to ⁇ 8>.
- ⁇ 10> A method for producing a resin thin film for a display substrate using the display substrate resin composition according to any one of ⁇ 1> to ⁇ 7>.
- ⁇ 11> A method for producing an image display device using the resin thin film for a display substrate according to ⁇ 8>.
- the present invention it is possible to provide a highly heat-resistant resin composition for a display substrate that has sufficient transparency and an appropriate linear expansion coefficient without depending on curing conditions as a flexible display substrate.
- the resin composition for a display substrate of the present invention is not affected by the curing conditions for film production, and the required performance as a flexible display substrate, that is, sufficient heat resistance, high transparency, an appropriate linear expansion coefficient, and an appropriate A useful cured film having flexibility can be formed. Therefore, the cured film can be used for a base film for a flexible display.
- the resin composition for a display substrate of the present invention includes a polyamic acid containing repeating units represented by formulas (1-1) and (1-4); and an organic solvent.
- Ar 1 and Ar 2 are different from each other, and each independently represents a tetravalent group having an aromatic group having a substituent substituted with fluorine;
- Ar 3 represents a divalent group represented by the formula (4) (wherein q represents 1 or 2, and l represents 1 or 2);
- n 1 and n 4 represents the number of repeating units, n 1 and n 4 n is the ratio of the 1: n 4 is 50: 50 to 99: 1, preferably 70: 30 to 95: 5, more preferably Satisfies 70:30 to 90:10.
- Ar 1 in the above formula (1-1) may be represented by the following formula ( 2 ), and Ar 2 in the formula (1-4) may be represented by the following formula (3).
- k represents the number of trifluoromethyl groups substituted on the benzene ring and is 1 or 2, preferably 1, and p is 1 or 2, preferably 2.
- X represents a fluoroalkylene group having 1 to 3 carbon atoms.
- a preferred example of the group represented by the formula (2) is a group represented by the following formula (2-1), but is not limited thereto.
- Examples of the group represented by X in the formula (3) include a difluoromethylene group (—CF 2 —), a trifluoromethylfluoromethylene group (—CF (CF 3 ) —), 1,1,2,2-tetra Fluoroethylene group (—CF 2 CF 2 —), 1,1,1,3,3,3-hexafluoropropane-2,2-diyl group (—C (CF 3 ) 2 —), 1,1,2 , 2,3,3-hexafluorotrimethylene group (—CF 2 CF 2 CF 2 —) and the like, but 1,1,1,3,3,3-hexafluoropropane-2,2-diyl group Is preferred.
- Preferable examples of the group represented by formula (3) include, but are not limited to, the group represented by formula (3-1).
- Ar 3 represented by the above formula (4) include groups represented by formulas (4-1) to (4-6), but are not limited thereto.
- Ar 3 represented by the above formula (4) is preferably (4-1), (4-2), (4-3) or (4-5). From the viewpoint of availability, the formula (4) The group represented by -1) is more preferable.
- the polyamic acid described above preferably further includes repeating units represented by the formulas (1-2) and (1-5).
- Ar 1 and Ar 2 have the same definition as above, Ar 4 represents a divalent group represented by the formula (5) (wherein r represents 1, 2 or 3).
- n 2 and n 5 is a number of repeating units, n 2 and n 5 is the ratio of the n 2: n 5 is preferably 50: 50 to 99: 1, more preferably 70:30 to 95: 5 Even more preferably, 70:30 to 90:10 should be satisfied.
- n 2 is preferably 50: 50 to 99: 1, more preferably 70:30 to 95: 5, more Preferably, 75:25 to 90:10 is satisfied.
- r is 1, 2 or 3, preferably 1 or 2, and more preferably 1.
- Preferable examples of the group represented by the formula (5) include groups represented by the formulas (5-1) to (5-3), but are not limited thereto.
- the polyamic acid described above may further include repeating units represented by the formulas (1-3) and (1-6).
- Ar 1 and Ar 2 have the same definition as above, Ar 5 is represented by the formula (6) (wherein Y is —O— or —S—, preferably —O—, and s is 1 or 2, preferably 2).
- Y is —O— or —S—, preferably —O—, and s is 1 or 2, preferably 2).
- n 3 and n 6 represents represents the number of repeating units, n 3 and a ratio of n 6 n 3: n 6 is preferably 50: 50 to 99: 1, more preferably 70:30 to 95: 5 Even more preferably, 70:30 to 90:10 should be satisfied.
- n 3 is preferably 60: 40-99: 1, more preferably 70: 30-99: 1, more Preferably, 80:20 to 99: 1 is satisfied.
- Preferred examples of the group represented by the above formula (6) include groups represented by the formulas (6-1) to (6-5), but are not limited thereto.
- the polyamic acid containing the repeating units represented by the above formulas (1-1) and (1-4) may have the repeating units represented by the formulas (1-1) and (1-4) in any order (these Other units may be included between each unit). Further, polyamic acid further containing repeating units represented by the above formulas (1-2) and (1-5), that is, the above formulas (1-1), (1-2), (1-4) and (1
- the polyamic acid containing the repeating unit represented by -5) is obtained by repeating the repeating units represented by the formulas (1-1), (1-2), (1-4) and (1-5) in any order. It is preferable that these units be bonded together (other structural units may be included between these units).
- the repeating units represented by the formulas (1-1) to (1-6) are preferably bonded in any order (other structural units may be included between these units).
- the polyamic acid used in the present invention is a copolymer having the above structural unit, and the copolymer is any of a block copolymer, an alternating copolymer, a random copolymer, and the like. May be.
- the weight average molecular weight of the polyamic acid used in the present invention is 5000 or more, preferably 10,000 or more.
- the upper limit of the weight average molecular weight of the polyamic acid used in the present invention is usually 200,000 or less, but it is possible to prevent the viscosity of the resin composition (varnish) from becoming excessively high or to have a highly flexible resin thin film. In consideration of obtaining with good reproducibility, etc., it is preferably 150,000 or less, more preferably 100,000 or less.
- the weight average molecular weight in this invention is a polystyrene conversion measured value by gel permeation chromatography (GPC).
- the polyamic acid used in the present invention may contain other structural units (repeating units) in addition to the structural units (repeating units) represented by the above formulas (1-1) to (1-6).
- the content of such a structural unit should be less than 40 mol%, preferably less than 30 mol%, more preferably less than 20 mol%, and even more preferably less than 10 mol% in the entire repeating unit.
- the polyamic acid used in the present invention takes into consideration the structure derived from the acid dianhydrides represented by the formulas (7) to (8) and the diamines represented by the formulas (9) to (11). In addition, it can be obtained by reacting at a molar ratio satisfying the above-mentioned ratio of n 1 to n 6 .
- Ar 1 to Ar 5 have the same definition as above.
- Examples of the acid dianhydride represented by the above formula (8) include, but are not limited to, 4,4 '-(hexafluoroisopropylidene) diphthalic anhydride.
- 1,4-benzenediamine p-phenylenediamine
- 1,3-benzenediamine m-phenylenediamine
- 1,2-benzenediamine o-phenylenediamine
- diamine represented by the above formula (11) 4,4′-bis (4-aminophenoxy) biphenyl, 4,4′-bis (3-aminophenoxy) biphenyl, 1,4-bis (4-aminophenoxy) ), 1,3′-bis (4-aminophenoxy) benzene, 1,4-bis (3-aminophenoxy) benzene, and the like, but are not limited thereto.
- the charging ratio (molar ratio) of the acid dianhydrides represented by the formulas (7) to (8) and the diamines represented by the formulas (9) to (11) takes into consideration the molecular weight of the polyamic acid, etc.
- the amount of the acid anhydride component is usually about 0.9 to 1.1, preferably about 0.95 to 1.02, with respect to the amine component 1.
- the above reaction is preferably carried out in a solvent.
- various solvents can be used as long as they do not adversely affect the reaction.
- Specific examples include m-cresol, 2-pyrrolidone, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, 3-methoxy-N, N-dimethylpropylamide, 3-ethoxy-N, N-dimethylpropylamide, 3-propoxy-N, N-dimethylpropylamide, 3-isopropoxy-N, N-dimethylpropylamide, 3 -Protic solvents such as -butoxy-N, N-dimethylpropylamide, 3-sec-butoxy-N, N-dimethylpropylamide, 3-tert-butoxy-N, N-dimethylpropylamide, ⁇ -butyrolactone, etc.
- the reaction temperature may be appropriately set in the range from the melting point to the boiling point of the solvent used, and is usually about 0 to 100 ° C., preferably about 0 to 70 ° C., more preferably about 0 to 60 ° C., and still more preferably 0 to It should be about 50 ° C.
- the reaction time depends on the reaction temperature and the reactivity of the raw material, it cannot be defined unconditionally, but is usually about 1 to 100 hours.
- the filtrate is used as it is, or diluted or concentrated, and used as a resin composition (varnish) for a display substrate.
- the resin composition for display substrates of the present invention contains an organic solvent.
- This organic solvent is not specifically limited, For example, the thing similar to the specific example of the reaction solvent of the said reaction is mentioned. More specifically, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-ethyl-2-pyrrolidone, ⁇ - Examples include butyrolactone.
- an organic solvent may be used individually by 1 type, and may be used in combination of 2 or more type.
- a varnish obtained by dissolving or dispersing the isolated polyamic acid in a solvent is used as a resin composition for a display substrate. You may use as a thing. In this case, considering that a thin film having high flatness can be obtained with good reproducibility, it is preferable that the polyamic acid is dissolved in a solvent.
- the solvent used for dissolution and dispersion is not particularly limited, and examples thereof include the same specific examples of the reaction solvent for the above reaction, and these may be used alone or in combination of two or more. .
- the concentration of the polyamic acid with respect to the total mass of the varnish is appropriately set in consideration of the thickness of the thin film to be produced, the varnish viscosity, etc., but is usually about 0.5 to 30% by mass, preferably about 5 to 25% by mass. is there. Further, the viscosity of the varnish is appropriately set in consideration of the thickness of the thin film to be produced. However, in particular, when the purpose is to obtain a resin thin film having a thickness of about 5 to 50 ⁇ m with good reproducibility, it is usually at 25 ° C. It is about 500 to 50,000 mPa ⁇ s, preferably about 1,000 to 20,000 mPa ⁇ s.
- the resin composition for a display substrate of the present invention can also contain a crosslinking agent (hereinafter also referred to as a crosslinkable compound).
- a crosslinking agent hereinafter also referred to as a crosslinkable compound.
- the content of the crosslinking agent is usually about 20 parts by mass or less with respect to 100 parts by mass of the polyamic acid.
- crosslinkable compound As compounds containing two or more epoxy groups, cyclohexene such as Epolide GT-401, Epolide GT-403, Epolide GT-301, Epolide GT-302, Celoxide 2021, Celoxide 3000 (manufactured by Daicel Chemical Industries, Ltd.) Epoxy compounds having a structure; bisphenol A type epoxy compounds such as Epicoat 1001, Epicoat 1002, Epicoat 1003, Epicoat 1004, Epicoat 1007, Epicoat 1009, Epicoat 1010, Epicoat 828 (above, manufactured by Japan Epoxy Resins Co., Ltd.); Epicoat 807 Bisphenol F-type epoxy compounds (made by Japan Epoxy Resin Co., Ltd.); Epicoat 152, Epicoat 154 (above, Japan Epoxy Resin Co., Ltd.), EPPN 01, EPPN202 (above, Nippon Kayaku Co., Ltd.) and other phenol novolac epoxy compounds; ECON-102, ECON-103
- benzoguanamine derivative or glycoluril having a group in which the hydrogen atom of the amino group is substituted with a methylol group, an alkoxymethyl group or both, an average of 3.7 methoxymethyl groups are substituted per triazine ring MX-750, MW-30 substituted with an average of 5.8 methoxymethyl groups per triazine ring (above, manufactured by Sanwa Chemical Co., Ltd.); Cymel 300, Cymel 301, Cymel 303, Cymel 350, Methoxymethylated melamines such as Cymel 370, Cymel 771, Cymel 325, Cymel 327, Cymel 703, Cymel 712, etc .; Butoxymethylated melamines such as Cymel 506 and Cymel 508; carboxyl group-containing methoxymethylated isobutoxymethylated melamines such as Cymel 1141; methoxymethylated ethoxymethylated benzoguanamines such as Cymel 1123; Methoxy
- a resin thin film made of polyimide having high heat resistance, appropriate flexibility, and appropriate linear expansion coefficient can be obtained. It can.
- a substrate for example, plastic (polycarbonate, polymethacrylate, polystyrene, polyester, polyolefin, epoxy, melamine, triacetyl cellulose, ABS, AS, norbornene resin, etc.), metal, wood, paper, glass, slate, etc.
- plastic polycarbonate, polymethacrylate, polystyrene, polyester, polyolefin, epoxy, melamine, triacetyl cellulose, ABS, AS, norbornene resin, etc.
- metal wood, paper, glass, slate, etc.
- a glass substrate is optimal.
- the coating method is not particularly limited, but for example, cast coating method, spin coating method, blade coating method, dip coating method, roll coating method, bar coating method, die coating method, ink jet method, printing method (letter plate) , Intaglio, lithographic, screen printing, etc.).
- the heating temperature is preferably 450 ° C. or less from the viewpoint of the strength and / or toughness of the resulting resin thin film. Further, considering the heat resistance and linear expansion coefficient characteristics of the resin thin film obtained, the applied resin composition is heated at 50 ° C. to 100 ° C. for 5 minutes to 2 hours, and then the heating temperature is gradually increased as it is. In particular, it is desirable to heat at over 375 ° C. to 450 ° C. for 30 minutes to 4 hours. In particular, the applied resin composition is heated at 50 ° C. to 100 ° C. for 5 minutes to 2 hours, then over 100 ° C. to 200 ° C. for 5 minutes to 2 hours, and then over 200 ° C. to 375 ° C. for 5 minutes to 2 hours.
- Heating is preferably performed for a time, and finally at a temperature exceeding 375 ° C. to 450 ° C. for 30 minutes to 4 hours.
- the appliance used for heating include a hot plate and an oven.
- the heating atmosphere may be under air or under an inert gas, and may be under normal pressure or under reduced pressure.
- the thickness of the resin thin film is usually about 1 to 60 m, preferably about 5 to 50 ⁇ m, especially when used as a substrate for a flexible display.
- the thickness of the coating before heating is adjusted to obtain a resin having a desired thickness. A thin film is formed.
- the above-mentioned resin thin film satisfies each condition necessary for a base film of a flexible display substrate, and is optimal for use as a base film of a flexible display substrate.
- CF3-BP-TMA N, N ′-[2,2′-bis (trifluoromethyl) biphenyl-4,4′-diyl] bis (1,3-dioxo-1,3-dihydroisobenzofuran-5 Carbamide).
- 6FDA 4,4 ′-(hexafluoroisopropylidene) diphthalic anhydride (manufactured by AZ Electronic Material Co., Ltd.).
- CBDA 1,2,3,4-cyclobutanetetracarboxylic dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).
- PDA p-phenylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.).
- TFMB 2,2′-bis (trifluoromethyl) biphenyl-4,4′-diamine (manufactured by Tokyo Chemical Industry Co., Ltd.).
- BAPB Bis (4-aminophenoxy) biphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.).
- BAPPS Bis (4- (3-aminophenoxy) phenyl) sulfone (manufactured by Tokyo Chemical Industry Co., Ltd.).
- BAPS Bis (3-aminophenyl) sulfone (manufactured by Tokyo Chemical Industry Co., Ltd.).
- NMP N-methyl-2-pyrrolidone.
- IPMA 3-methoxy-N, N-dimethylpropanamide (manufactured by Idemitsu Kosan Co., Ltd.).
- TFMB 17.8 g (0.056 mol), BAPB 0.4 g (0.0012 mol), PDA 2.5 g (0.023 mol) were dissolved in IPMA 430 g, and 6FDA 6.3 g (0.014 mol)
- Mw of the obtained polymer was 40,700, and molecular weight distribution was 2.1.
- the obtained reaction solution was used as the resin composition for display substrate of Example 1 as it was.
- Mw polymer weight average molecular weight
- Mw molecular weight distribution
- a reaction solution containing a polymer having an Mw of 38,700 and a molecular weight distribution of 2.1 was obtained in the same manner as in Example 1, except that IPMA in Example 1 was replaced with NMP.
- the obtained reaction solution was used as the resin composition for display substrates of Example 2 as it was.
- ⁇ Measurement of film thickness The film thickness of the resin thin film was measured using a ULVAC contact type film thickness measuring instrument (Dektak 3ST).
- ⁇ Flexibility evaluation> The flexibility of the resin thin film peeled from the glass substrate was evaluated. Flexibility is evaluated by visually checking the fragility (crack, crack, tear, etc.) of the thin film when the peeled resin thin film is bent or pulled by hand. The case where it was not destroyed even when pulled was considered good, and the case other than that was regarded as bad. The resin thin film was peeled off by leaving the glass substrate on which the resin thin film was formed in pure water at 70 ° C.
- ⁇ Heat resistance evaluation> The 5% mass reduction temperature (Td 5% (° C.)) of the resin thin film was measured. The measurement was performed using TG / DTA2000SA manufactured by Bruker AXS Co., Ltd. (temperature increase rate: from 50 ° C. to 500 ° C. at 5 ° C. per minute).
- ⁇ Measurement of transmittance> The transmittance of the resin thin film was measured. The measurement was performed using a self-recording spectrophotometer (UV-3100PC) manufactured by Shimadzu Corporation. The obtained results are shown in Table 1. In addition, it describes about the transmittance
- thermomechanical analyzer (TMA-4000SA) manufactured by Bruker AXS Co., Ltd. (temperature increase rate: 50 ° C. to 300 ° C. at 5 ° C./min). Before the measurement, each thin film was heated once in advance (temperature increase rate: from 50 ° C. to 400 ° C. at 5 ° C. per minute).
- the resin thin films of Examples 3 and 4 were not only moderately flexible and high heat resistant, but also had excellent transparency and moderateness compared to the resin thin films of Comparative Examples 4-6. It has a good linear expansion coefficient. From the above, it can be seen that the resin composition of the present invention is suitable for producing a resin thin film (polyimide thin film) having various characteristics required for display substrate applications.
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Abstract
Description
しかしながら、ガラス代替となるフィルム材料には透明性に加えて、無機材料からなる微細な電子素子をフィルム上に形成する場合には高温プロセスが必要となることから高度な耐熱性を有する必要があること、更には、無機材料とフィルムの線熱膨張係数の違いにより、電子素子の形成後にフィルムの反りや電子素子が破壊されてしまう恐れがあることから、無機材料と同程度の低線熱膨性が求められる。
しかしながら、このような電子部品材料用のポリイミド樹脂は高度な耐熱性と低線膨張性を有しているものの、一般的には透明性が低く、ガラス代替となる光学フィルムとして用いることができなかった。
<1> 式(1-1)及び(1-4)(式中、Ar1及びAr2はそれぞれ異なり、それぞれ独立して、フッ素に置換された置換基を有する芳香族を有する4価の基を表し、Ar3は、式(4)(式中、qは、1または2を表し、lは1または2を表す)で表される2価の基を表し、n1及びn4は各繰り返し単位の数を表し、n1とn4との比であるn1:n4が50:50~99:1である)で表される繰り返し単位を含むポリアミック酸;及び有機溶媒;を含むディスプレイ基板用樹脂組成物。
<9> <8>のディスプレイ基板用樹脂薄膜を備える画像表示装置。
<10> <1>~<7>のいずれかのディスプレイ基板用樹脂組成物を用いるディスプレイ基板用樹脂薄膜の製造方法。
<11> <8>のディスプレイ基板用樹脂薄膜を用いる画像表示装置の製造方法。
本発明のディスプレイ基板用樹脂組成物は、フィルム作製のキュア条件に影響されることなく、フレキシブルディスプレイ基板としての要求性能、すなわち、充分な耐熱性、高い透明性、適度な線膨張係数及び適度な柔軟性を有する有用な硬化膜を形成することができる。したがって、該硬化膜は、フレキシブルディスプレイ用ベースフィルムなどに使用することができる。
本発明のディスプレイ基板用樹脂組成物は、式(1-1)及び(1-4)で表される繰り返し単位を含むポリアミック酸;及び有機溶媒;を含む。
式中、Ar1及びAr2はそれぞれ異なり、それぞれ独立して、フッ素に置換された置換基を有する芳香族を有する4価の基を表し;
Ar3は、式(4)(式中、qは、1または2を表し、lは1または2を表す)で表される2価の基を表し;
n1及びn4は各繰り返し単位の数を表し、n1とn4との比であるn1:n4が50:50~99:1、好ましくは70:30~95:5、より好ましくは70:30~90:10を満たす。
式(2)中、kはベンゼン環に置換するトリフルオロメチル基の数を示し、1又は2、好ましくは1であり、pは1又は2、好ましくは2であるのがよい。
式(3)中、Xは、炭素数1~3のフルオロアルキレン基を表す。
式(3)で表される基の好適な例として、式(3-1)で表される基が挙げられるが、これに限定されない。
式中、Ar1及びAr2は上記と同じ定義を有し、
Ar4は、式(5)(式中、rは1、2又は3を表す)で表される2価の基を表す。
n2及びn5は各繰り返し単位の数を表し、n2とn5との比であるn2:n5が好ましくは50:50~99:1、より好ましくは70:30~95:5、より一層好ましくは70:30~90:10を満たすのがよい。
式(5)で表される基の好適な例として、式(5-1)~(5-3)で表される基を挙げることができるが、これらに限定されない。
式中、Ar1及びAr2は上記と同じ定義を有し、
Ar5は、式(6)(式中、Yは-O-又は-S-、好ましくは-O-であるのがよく、sは1又は2、好ましくは2であるのがよい)で表される2価の基を表す。
n3及びn6は各繰り返し単位の数を表し、n3とn6との比であるn3:n6が好ましくは50:50~99:1、より好ましくは70:30~95:5、より一層好ましくは70:30~90:10を満たすのがよい。
また、上記式(1-2)及び(1-5)で表される繰り返し単位をさらに含むポリアミック酸、即ち上記式(1-1)、(1-2)、(1-4)及び(1-5)で表される繰り返し単位を含むポリアミック酸は、該式(1-1)、(1-2)、(1-4)及び(1-5)で表される繰り返し単位を任意の順序(これら各単位の間に他の構成単位を含んでも良い)で結合するのがよい。
さらに、上記式(1-3)及び(1-6)で表される繰り返し単位をさらに含むポリアミック酸、即ち上記式(1-1)~(1-6)で表される繰り返し単位を含むポリアミック酸は、該式(1-1)~(1-6)で表される繰り返し単位を任意の順序(これら各単位の間に他の構成単位を含んでも良い)で結合するのがよい。
なお、本発明における重量平均分子量とは、ゲルパーミエーションクロマトグラフィー(GPC)によるポリスチレン換算測定値である。
上記式(7)で表される酸二無水物として、N,N’-[2,2’-ビス(トリフルオロメチル)ビフェニル-4,4’-ジイル]ビス(1,3-ジオキソ-1,3-ジヒドロイソベンゾフラン-5-カルボアミド)等が挙げられるが、これらに限定されない。
上記式(11)で表されるジアミンとして、4,4’-ビス(4-アミノフェノキシ)ビフェニル、4,4’-ビス(3-アミノフェノキシ)ビフェニル、1,4-ビス(4-アミノフェノキシ)ベンゼン、1,3’-ビス(4-アミノフェノキシ)ベンゼン、1,4-ビス(3-アミノフェノキシ)ベンゼン等が挙げられるが、これらに限定されない。
具体例として、m-クレゾール、2-ピロリドン、N-メチル-2-ピロリドン、N-エチル-2-ピロリドン、N-ビニル-2-ピロリドン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、3-メトキシ-N,N-ジメチルプロピルアミド、3-エトキシ-N,N-ジメチルプロピルアミド、3-プロポキシ-N,N-ジメチルプロピルアミド、3-イソプロポキシ-N,N-ジメチルプロピルアミド、3-ブトキシ-N,N-ジメチルプロピルアミド、3-sec-ブトキシ-N,N-ジメチルプロピルアミド、3-tert-ブトキシ-N,N-ジメチルプロピルアミド、γ-ブチロラクトン等のプロトン性溶剤等を挙げることができるが、これらに限定されない。これらは単独で又は2種以上を組み合わせて使用してもよい。
反応時間は、反応温度や原料物質の反応性に依存するため一概に規定できないが、通常1~100時間程度である。
上記方法によって、目的とするポリアミック酸を含む反応溶液を得ることができる。
これらの中でも、平坦性の高い樹脂薄膜を再現性よく得ることを考慮すると、下記式(A)又は(B)(式中、R1及びR2は各々独立に、炭素原子数1~4のアルキル基を表し、hは自然数を表す)で表される溶媒であるのがよい。
また、ワニスの粘度も、作製する薄膜の厚み等勘案し適宜設定するものではあるが、特に5~50μm程度の厚さの樹脂薄膜を再現性よく得ること目的とする場合、通常、25℃で500~50,000mPa・s程度、好ましくは1,000~20,000mPa・s程度である。
エポキシ基を2個以上含有する化合物として、エポリードGT-401、エポリードGT-403、エポリードGT-301、エポリードGT-302、セロキサイド2021、セロキサイド3000(以上、ダイセル化学工業(株)製)等のシクロヘキセン構造を有するエポキシ化合物;エピコート1001、エピコート1002、エピコート1003、エピコート1004、エピコート1007、エピコート1009、エピコート1010、エピコート828(以上、ジャパンエポキシレジン(株)製)等のビスフェノールA型エポキシ化合物;エピコート807(ジャパンエポキシレジン(株)製)等のビスフェノールF型エポキシ化合物;エピコート152、エピコート154(以上、ジャパンエポキシレジン(株)製)、EPPN201、EPPN202(以上、日本化薬(株)製)等のフェノールノボラック型エポキシ化合物;ECON-102、ECON-103S、ECON-104S、ECON-1020、ECON-1025、ECON-1027(以上、日本化薬(株)製)、エピコート180S75(ジャパンエポキシレジン(株)製)等のクレゾールノボラック型エポキシ化合物;V8000-C7(DIC(株)製)等のナフタレン型エポキシ化合物;デナコールEX-252(ナガセケムテックス(株)製)、CY175、CY177、CY179、アラルダイトCY-182、アラルダイトCY-192、アラルダイトCY-184(以上、BASF社製)、エピクロン200、エピクロン400(以上、DIC(株)製)、エピコート871、エピコート872(以上、ジャパンエポキシレジン(株)製)、ED-5661、ED-5662(以上、セラニーズコーティング(株)製)等の脂環式エポキシ化合物;デナコールEX-611、デナコールEX-612、デナコールEX-614、デナコールEX-622、デナコールEX-411、デナコールEX-512、デナコールEX-522、デナコールEX-421、デナコールEX-313、デナコールEX-314、デナコールEX-312(以上、ナガセケムテックス(株)製)等の脂肪族ポリグリシジルエーテル化合物を挙げることができるが、これらに限定されない。
基体(基材)として、例えば、プラスチック(ポリカーボネート、ポリメタクリレート、ポリスチレン、ポリエステル、ポリオレフィン、エポキシ、メラミン、トリアセチルセルロース、ABS、AS、ノルボルネン系樹脂等)、金属、木材、紙、ガラス、スレート等が挙げられるが、得られる樹脂薄膜が良好な剥離性を示すことから、ガラス基体が最適である。
また、得られる樹脂薄膜の耐熱性と線膨張係数特性を考慮すると、塗布した樹脂組成物を50℃~100℃で5分間~2時間加熱した後に、そのまま段階的に加熱温度を上昇させて最終的に375℃超~450℃で30分~4時間加熱することが望ましい。
特に、塗布した樹脂組成物は、50℃~100℃で5分間~2時間加熱した後に、100℃超~200℃で5分間~2時間、次いで、200℃超~375℃で5分間~2時間、最後に375℃超~450℃で30分~4時間加熱することが好ましい。
加熱に用いる器具は、例えばホットプレート、オーブン等が挙げられる。加熱雰囲気は、空気下であっても不活性ガス下であってもよく、また、常圧下であっても減圧下であってもよい。
<無水物>
CF3-BP-TMA:N,N’-[2,2’-ビス(トリフルオロメチル)ビフェニル-4,4’-ジイル]ビス(1,3-ジオキソ-1,3-ジヒドロイソベンゾフラン-5-カルボアミド)。
6FDA:4,4’-(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(AZエレクトロニックマテリアル(株)製)。
CBDA:1,2,3,4-シクロブタンテトラカルボン酸二無水物(東京化成工業(株)製)。
PDA:p-フェニレンジアミン(東京化成工業(株)製)。
TFMB:2,2’ -ビス(トリフルオロメチル)ビフェニル‐4,4’-ジアミン(東京化成工業(株)製)。
BAPB:ビス(4-アミノフェノキシ)ビフェニル(東京化成工業(株)製)。
BAPPS:ビス(4-(3-アミノフェノキシ)フェニル)スルホン(東京化成工業(株)製)。
BAPS:ビス(3-アミノフェニル)スルホン(東京化成工業(株)製)。
NMP:N-メチル-2-ピロリドン。
IPMA:3-メトキシ-N,N-ジメチルプロパンアミド(出光興産(株)製)。
なお、ポリマーの重量平均分子量(以下、Mwと略す。)と分子量分布は、東ソー(株)製GPC装置(ShodexカラムSB803HQ及びSB804HQ)を用い、溶出溶媒としてジメチルホルムアミドを流量0.9mL/分、カラム温度40℃の条件で測定した。なお、Mwはポリスチレン換算値とした(以下、同じ)。
BAPPS 28.1g(0.063モル)をNMP 160gに溶解し、CBDA 12.5g(0.063モル)を添加した後、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは19,800、分子量分布は2.1であった。得られた反応溶液を、そのまま、比較例1の樹脂組成物とした。
BAPS 39.1g(0.16モル)をNMP 500gに溶解し、CBDA 30.95g(0.16モル)を添加した後、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは13,600、分子量分布は3.1であった。得られた反応溶液を、そのまま、比較例2の樹脂組成物とした。
TFMB 38.2g(0.12モル)、PDA 3.2g(0.029モル)をNMP 430gに溶解し、CBDA 28.6g(0.15モル)を添加した後、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは30,600、分子量分布は2.1であった。得られた反応溶液を、そのまま、比較例3の樹脂組成物とした。
[3]樹脂薄膜の作製(ポリイミドフィルムの作製)
実施例1~2および比較例1~3の樹脂組成物を、それぞれバーコーターでガラス基板上に塗布し、減圧下110℃で10分、230℃で30分、300℃で30分、350℃で120分間、順次加熱して樹脂薄膜(それぞれ、実施例3~4、比較例4~6の樹脂薄膜)を得た。
得られた樹脂薄膜の評価を以下の方法で行った。結果を表1に示す。なお、薄膜は、各評価のためにそれぞれ作製した。膜厚は、柔軟性評価に用いた樹脂薄膜の値を示した。
樹脂薄膜の膜厚を、(株)ULVAC製接触式膜厚測定器(Dektak 3ST)を用いて測定した。
<柔軟性評価>
ガラス基板から剥離した樹脂薄膜の柔軟性を評価した。柔軟性の評価は、剥離した樹脂薄膜を手で曲げたり引っ張ったりしたときの薄膜の壊れやすさ(クラック、ひび、破れ等)を目視で確認することで行い、手で90度に曲げても引っ張っても破壊されなかった場合を良好、それ以外の場合を不良とした。
なお、樹脂薄膜は、樹脂薄膜が形成されたガラス基板を70℃の純水中に静置することで剥離した。
樹脂薄膜の5%質量減少温度(Td5%(℃))を測定した。測定は、ブルカー・エイエックスエス(株)製TG/DTA2000SAを用いて行った(昇温レート:毎分5℃で50℃から500℃まで)。
<透過率の測定>
樹脂薄膜の透過率を測定した。測定は、(株)島津製作所製 自記分光光度計(UV-3100PC)を用いて行った。得られた結果を表1に示す。なお、450nmでの透過率について記載する。
樹脂薄膜から短冊状の小片(20mm×5mm)を切り出して、その線膨張係数を測定した。測定には、ブルカー・エイエックスエス(株)製熱機械分析装置(TMA-4000SA)を用いて行った(昇温レート:毎分5℃で50℃から300℃まで)。
なお、測定前に、各薄膜を予め一度加熱した(昇温レート:毎分5℃で50℃から400℃まで)。
以上のことから、本発明の樹脂組成物は、ディスプレイの基板用途に必要な各特性を有する樹脂薄膜(ポリイミド薄膜)を製造するのに適していることがわかる。
Claims (11)
- 請求項1~7のいずれか1項に記載のディスプレイ基板用樹脂組成物を用いて作製されるディスプレイ基板用樹脂薄膜。
- 請求項8に記載のディスプレイ基板用樹脂薄膜を備える画像表示装置。
- 請求項1~7のいずれか1項に記載のディスプレイ基板用樹脂組成物を用いるディスプレイ基板用樹脂薄膜の製造方法。
- 請求項8に記載のディスプレイ基板用樹脂薄膜を用いる画像表示装置の製造方法。
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CN105392821B (zh) | 2018-10-23 |
CN105392821A (zh) | 2016-03-09 |
KR20160037847A (ko) | 2016-04-06 |
TWI658098B (zh) | 2019-05-01 |
TW201522505A (zh) | 2015-06-16 |
KR102212979B1 (ko) | 2021-02-04 |
JPWO2015012385A1 (ja) | 2017-03-02 |
JP6485706B2 (ja) | 2019-03-20 |
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