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WO2013125193A1 - Composition de résine, film de résine polyamide mettant en œuvre celle-ci, substrat d'affichage et procédé de fabrication - Google Patents

Composition de résine, film de résine polyamide mettant en œuvre celle-ci, substrat d'affichage et procédé de fabrication Download PDF

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Publication number
WO2013125193A1
WO2013125193A1 PCT/JP2013/000843 JP2013000843W WO2013125193A1 WO 2013125193 A1 WO2013125193 A1 WO 2013125193A1 JP 2013000843 W JP2013000843 W JP 2013000843W WO 2013125193 A1 WO2013125193 A1 WO 2013125193A1
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Prior art keywords
resin composition
polyimide
polyimide precursor
resin film
film
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PCT/JP2013/000843
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English (en)
Japanese (ja)
Inventor
由美子 荒川
上田　篤
匡之 大江
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HD MicroSystems Ltd
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Hitachi Chemical DuPont Microsystems Ltd
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Priority to JP2014500907A priority Critical patent/JP6172139B2/ja
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    • 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
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
    • 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

Definitions

  • the present invention relates to a resin composition having both moderate adhesion and good peelability. Moreover, it is related with the polyimide resin film using the resin composition of this invention, a display substrate, and its manufacturing method.
  • a display substrate used for these small and medium displays can be obtained by forming TFTs (thin film transistors) on a glass substrate.
  • TFTs thin film transistors
  • the glass substrate is excellent in heat resistance and dimensional stability, but has a problem that the strength decreases when the weight is reduced and the thickness is reduced. Therefore, a plastic substrate has been proposed as a substrate that replaces the glass substrate.
  • a plastic substrate is easy to mold, has high toughness, and is strong against bending. Therefore, the plastic substrate is suitable for reducing the weight and thickness of a semiconductor element, and is useful as a flexible base material.
  • a method of manufacturing a display substrate using a thin plastic substrate includes a step of forming a plastic substrate on a support, a step of forming a semiconductor element such as a TFT on the plastic substrate, and a support of the plastic substrate. A step of peeling from the substrate.
  • Patent Document 1 a plastic substrate is provided on a hard carrier substrate (support) via a release layer, a pixel circuit and a display layer are formed thereon, and then peeled off from the hard carrier substrate by a laser.
  • the manufacturing method of the display substrate is described. With a flexible display substrate manufactured by this method, a lightweight and thin substrate can be formed.
  • Patent Document 1 a plastic layer containing parylene is used as one having high heat resistance.
  • the formation of a plastic layer containing parylene has a problem that the process is complicated.
  • an excimer laser device or the like is necessary because the plastic substrate needs to be peeled off by a laser.
  • Patent Document 2 a method of providing a silane coupling layer between an inorganic layer (support) and a polyimide layer which is a plastic substrate has been proposed (for example, Patent Document 2).
  • the polyimide resin film is physically peeled from the support without requiring a laser in the peeling step.
  • the adhesion strength between the formed layer or film and the adherend is significantly increased. , Tend to increase adhesion. And in order to raise adhesive force, it is necessary to increase the compounding quantity of a silane coupling agent to some extent, and it has not been used for the purpose of peeling a layer or a film from an adherend.
  • appropriate adhesion strength is expressed by blending a small amount of a specific (b) alkoxysilane compound among the silane coupling agents into (a) the polyimide precursor. The present invention has been achieved.
  • the present invention relates to the following.
  • R 1 represents a divalent organic group having an aromatic ring
  • R 2 represents a tetravalent organic group having an aromatic ring.
  • (b) The resin composition, wherein the alkoxysilane compound is any compound represented by the general formula (2) or (3).
  • R 1 and R 2 each independently represents a monovalent organic group
  • a step of applying a resin composition to a support and heating to form a polyimide resin film, a step of forming a semiconductor element on the polyimide resin film, and a polyimide resin film on which the semiconductor element is formed The said resin composition used for the manufacturing method of a display substrate including the process of peeling from.
  • the substrate when a semiconductor element such as a TFT is formed, the substrate has sufficient adhesion with the support, and it is neatly cleaned by a physical method without using a laser when peeling from the support.
  • a resin composition capable of forming a polyimide resin film (plastic substrate) that can be peeled (good peelability) can be provided. Further, it is possible to provide a resin composition capable of forming a polyimide resin film with small thermal expansion even when exposed to high temperatures when forming a semiconductor element. When the thermal expansion of the polyimide resin film is small, dimensional deviation can be suppressed when forming a semiconductor element such as a TFT.
  • the polyimide resin film using the resin composition of this invention is excellent in a mechanical characteristic and heat resistance.
  • this invention can provide the manufacturing method of the display substrate using this resin composition. Furthermore, the present invention can provide a display substrate formed by the manufacturing method.
  • the resin composition of the present invention is a resin composition containing (a) a polyimide precursor, (b) an alkoxysilane compound, and (c) an organic solvent, and the content of (b) is (a).
  • the content is 0.01 to 2% by mass with respect to the polyimide precursor.
  • the resin composition of the present invention contains (a) a polyimide precursor.
  • a polyimide precursor By containing a polyimide precursor, it is possible to form a polyimide resin film excellent in heat resistance and mechanical properties.
  • a polyimide precursor is a polyamic acid which has a structural unit represented by General formula (1) from a viewpoint of heat resistance and mechanical characteristics.
  • R 1 represents a divalent organic group having an aromatic ring
  • R 2 represents a tetravalent organic group having an aromatic ring.
  • the polyimide precursor is generally obtained by polymerizing tetracarboxylic dianhydride and diamine. This polymerization can be performed by mixing both in an organic solvent.
  • tetracarboxylic dianhydrides used to synthesize polyimide precursors include pyromellitic dianhydride, cyclohexyltetracarboxylic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic acid.
  • Examples of the diamine used for synthesizing the polyimide precursor include p-phenylenediamine, m-phenylenediamine, benzidine, 3,3′-dimethyl-4,4′-diaminobiphenyl, and 2,2′-dimethyl- 4,4′-diaminobiphenyl, 3,3′-diethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, p-xylylenediamine, m-xylylenediamine, 1,5-diaminonaphthalene, 3,3'-dimethoxybenzidine, 4,4'- (or 3,4'-, 3,3'-, 2,4'-) diaminodiphenylmethane, 4,4'- (or 3,4'-, 3,3'-, 2,4 '-) diaminodiphenyl ether, 4,4'- (or 3,4'-, 3,3-,
  • the organic solvent used for synthesizing the polyimide precursor is N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, ⁇ -butyrolactone, ⁇ -caprolactone, ⁇ -caprolactone, Examples include ⁇ -valerolactone, dimethyl sulfoxide, 1,4-dioxane, cyclohexanone, and the like, and two or more of these may be used in combination.
  • the weight average molecular weight of the polyimide precursor is preferably 5,000 to 300,000, more preferably 10,000 to 300,000 in terms of the weight average molecular weight from the viewpoint of elongation of the cured film and solubility in a solvent. 15,000 to 200,000 is particularly preferable.
  • the weight average molecular weight can be calculated by measuring with a gel permeation chromatography method and converting with a standard polystyrene calibration curve.
  • the polyimide precursor represented by the general formula (1) is a divalent organic group having an aromatic ring, and R 1 is a residue of the diamine (a diamine obtained by removing two amino groups). Is preferably a divalent organic group represented by any one of the following structural formulas (4) to (6).
  • R ′ each independently represents a monovalent alkyl group.
  • R ′ represents a halogen atom (fluorine, chlorine or a part or all of hydrogen atoms in the alkyl group). , Bromine, iodine).
  • R 1 in the general formula (1) is a divalent organic group represented by any one of the structural formulas (3) to (6), it has excellent mechanical properties and heat resistance, and has a low thermal expansion coefficient. can do.
  • R ′ in the general formulas (4) and (5) representing a monovalent alkyl group is preferably an alkyl group having 1 to 3 carbon atoms.
  • R 1 in the general formula (1) is a divalent organic group represented by any one of the structural formulas (3) to (6), (a) as a diamine used in the synthesis of the polyimide precursor, p-phenylenediamine, m-phenylenediamine, benzidine, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-diethyl-4 4,2'-diaminobiphenyl, 2,2'-diethyl-4,4'-diaminobiphenyl.
  • diamines are preferably used in an amount of 40% by mass or more, more preferably 60% by mass or more, and more preferably 80 to 100% by mass, based on the total amount of (a) diamine used in the synthesis of the polyimide precursor. Further preferred.
  • R 2 representing a tetravalent organic group having an aromatic ring is a tetravalent organic group represented by the following structural formula (7) or (8). It is preferable that
  • R 2 is any one of the above groups, the mechanical properties and heat resistance are excellent, and the thermal expansion coefficient can be lowered.
  • R 2 in the general formula (1) is a tetravalent organic group represented by the structural formula (7) or (8), (a) a tetracarboxylic dianhydride used in the synthesis of the polyimide precursor Includes pyromellitic dianhydride and 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride.
  • tetracarboxylic dianhydrides are preferably used in an amount of 40% by mass or more, more preferably 60% by mass or more based on the total amount of tetracarboxylic dianhydrides used in the synthesis of (a) polyimide precursor. It is preferable to use 80 to 100% by mass.
  • the polyimide precursor is preferably contained in an amount of 5 to 100% by mass with respect to the entire resin composition.
  • the resin composition of the present invention contains 0.01 to 2% by mass of (b) an alkoxysilane compound with respect to (a) the polyimide precursor.
  • (B) When 0.01 to 2% by mass of the alkoxysilane compound is contained, when forming a semiconductor element such as a TFT, it has sufficient adhesion to the support and is peeled from the support. It is possible to provide a resin composition capable of forming a polyimide resin film (plastic substrate) that can be peeled cleanly (good peelability) by a physical method without using a laser.
  • the content of the (b) alkoxysilane compound is preferably 0.02 to 2% by mass, more preferably 0.05 to 1% by mass relative to the (a) polyimide precursor. It is more preferably from 05 to 0.5% by mass, particularly preferably from 0.1 to 0.5% by mass. 1 H NMR is mentioned as a method of confirming content of the (b) alkoxysilane compound in a resin composition.
  • (B) As the alkoxysilane compound, it is preferable to use any compound represented by the general formula (2) or (3).
  • R 1 and R 2 each independently represents a monovalent organic group
  • Examples of the compound represented by the general formula (2) or (3) include 3-ureidopropyltriethoxysilane, bis (2-hydroxyethyl) -3-aminopropyltriethoxysilane, and 3-glycidoxypropyltrimethoxysilane.
  • 3-ureidopropyltriethoxysilane, bis (2-hydroxy) are preferable from the viewpoint of providing a polyimide resin film having sufficient adhesion to the support and having good releasability when peeled from the support.
  • Ethyl) -3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, or phenyltrimethoxysilane is preferably used, and 3-ureidopropyltriethoxysilane is most preferably used.
  • the resin composition of the present invention contains (c) an organic solvent.
  • the organic solvent may be an organic solvent remaining when (a) the polyimide precursor is synthesized, or a further organic solvent may be used to adjust the viscosity of the resin composition. .
  • the organic solvent is (a) the organic solvent remaining when the polyimide precursor is synthesized, (c) the organic solvent includes N-methyl-2-pyrrolidone, N, N-dimethylformamide, N , N-dimethylacetamide, ⁇ -butyrolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -valerolactone, dimethyl sulfoxide, 1,4-dioxane, cyclohexanone and the like.
  • the above-mentioned solvents may be used, and propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl acetate, propylene Glycol monoethyl acetate, ethyl cellosolve, butyl cellosolve, toluene, xylene, ethanol, isopropyl alcohol, n-butanol, etc. may be used, and these may be used in combination of two or more.
  • the content of the organic solvent (c) is a mass ratio ((a) to the content of the polyimide precursor (a) from the viewpoint of applicability and the like capable of forming a good thin film.
  • the mass of the polyimide precursor / (c) the mass of the organic solvent) is preferably 5/95 to 95/5, more preferably 20/80 to 80/20, and 30/70 to 50/50. More preferably.
  • the mass ratio ((a) polyimide precursor mass / (c) organic solvent mass) is obtained by accurately measuring the total mass of the resin composition and the petri dish by placing the resin composition in a metal or glass petri dish.
  • the organic solvent is scattered at a temperature near the boiling point of the organic solvent, and the total mass of the petri dish and the resin composition after the treatment is accurately measured. From the total mass of the petri dish and the resin composition before and after the treatment, It is possible to calculate by dividing the mass and dividing the amount of the resin composition material after treatment by the amount of the resin composition material before treatment.
  • the temperature is made to scatter at or below the temperature at which the polyamic acid of the polyimide precursor is ring-closed to the polyimide. In general, the temperature should be lower than 150 ° C.
  • the resin composition of the present invention can impart photosensitivity as necessary.
  • an amine having an acryloyl group or a methacryloyl group is blended with polyamic acid (hydrogen atom of carboxylic acid bonded to R 2 in the general formula (1)) as a polyimide precursor.
  • Sex can be imparted.
  • examples of such amines include N, N-diethylaminopropyl methacrylate, N, N-dimethylaminopropyl methacrylate, N, N-diethylaminopropyl acrylate, N, N-diethylaminoethyl methacrylate, and the like. Not limited.
  • the resin composition of the present invention may contain other components (adhesion aid, acid generator, etc.) as long as the heat resistance and mechanical properties are not impaired.
  • the step of applying the resin composition to a support and heating to form a polyimide resin film, the step of forming a semiconductor element on the polyimide resin film, and the semiconductor element are formed. It is preferable to use for the manufacturing method of a display substrate including the process of peeling a polyimide resin film from a support body. Since the polyimide resin film of the present invention has good adhesion to the support (for example, 50 to 950 kg / cm 2 , stud pull evaluation method), a semiconductor element such as a TFT can be easily formed on the polyimide resin film. it can.
  • the polyimide resin film of the present invention has a low coefficient of thermal expansion (for example, a coefficient of thermal expansion at 100 to 200 ° C. of 15 ⁇ 10 ⁇ 6 / K or less) and a high glass transition temperature (for example, 250 ° C. or more). ), When forming a semiconductor element such as a TFT, even if it is exposed to a high temperature, dimensional deviation can be suppressed.
  • a low coefficient of thermal expansion for example, a coefficient of thermal expansion at 100 to 200 ° C. of 15 ⁇ 10 ⁇ 6 / K or less
  • a high glass transition temperature for example, 250 ° C. or more
  • the polyimide resin film of the present invention can be formed by heating the resin composition of the present invention. By heating, the polyimide precursor in the resin composition becomes polyimide, and good mechanical properties and heat resistance can be imparted to the polyimide resin film.
  • the polyimide resin film of the present invention is a so-called plastic substrate.
  • the method for producing a display substrate of the present invention comprises a step of applying a resin composition of the present invention to a support and heating to form a polyimide resin film, a step of forming a semiconductor element on the polyimide resin film, and the semiconductor element Each step of peeling the polyimide resin film on which is formed from the support.
  • the display substrate is not particularly limited, but refers to a substrate in which a semiconductor element such as a TFT is formed on a plastic substrate (in the present invention, a polyimide resin film).
  • the step of applying the resin composition of the present invention to the support is not particularly limited as long as it is a method capable of forming a uniform thickness on the support.
  • it can be applied by die coating, spin coating, or screen printing. is there.
  • the support to which the resin composition of the present invention is applied is not limited as long as it is a hard material having self-supporting properties, has heat resistance, and is smooth and free from the surface on which the resin composition is applied. That is, there is no particular limitation as long as it is difficult to deform even when exposed to high temperatures required in the manufacturing process of the display substrate.
  • a material having a glass transition temperature of 200 ° C. or higher, preferably 250 ° C. or higher examples of such a support include glass.
  • the thickness of the support is preferably from 0.3 to 5.0 mm, more preferably from 0.5 to 3.0 mm, and even more preferably from 0.7 to 1.5 mm.
  • the resin composition film formed in the step of applying the resin composition to the support is preferably subjected to a drying step. It is possible to remove the solvent in the resin composition stepwise by the drying step, thereby suppressing the surface roughness of the polyimide resin film after heat curing.
  • the drying step is preferably performed at 80 to 150 ° C. for 30 seconds to 5 minutes using a hot plate.
  • a polyimide resin film can be formed by heating the resin composition film. By this heating step, the imide ring of the polyimide precursor in the resin composition is closed, giving the polyimide resin film good mechanical properties and heat resistance.
  • the heating process can be any apparatus that can control the temperature increase rate and the atmosphere during curing, and can maintain a specific temperature for a certain period of time.
  • the temperature in the heating step is preferably 100 to 500 ° C., more preferably 200 to 475 ° C., and further preferably 250 to 450 ° C.
  • the heating time is preferably 1 minute to 6 hours, more preferably 3 minutes to 4 hours, and even more preferably 15 minutes to 2 hours.
  • the thickness of the polyimide resin film in the present invention is preferably 1 to 50 ⁇ m.
  • the thickness is 1 ⁇ m or more, the polyimide resin film has good mechanical properties, and it is possible to suppress the occurrence of defects in the polyimide resin film in the peeling process from the support. Further, when the thickness is 50 ⁇ m or less, it is possible to suppress the polyimide film surface roughness that is generated when the solvent is not uniformly vaporized during drying.
  • the thickness of the polyimide resin film is more preferably 3 to 40 ⁇ m, and further preferably 5 to 30 ⁇ m.
  • the method for producing a display substrate of the present invention includes a step of forming a semiconductor element such as a TFT on a polyimide resin film. Since the polyimide resin film obtained in the present invention is excellent in heat resistance and mechanical properties, the method for forming a semiconductor element or the like is not particularly limited, but the method for forming a semiconductor element differs depending on the type of device used for the display substrate. For example, when a TFT liquid crystal display device is manufactured, an amorphous silicon TFT, for example, can be formed thereon.
  • the TFT includes a gate metal layer, a silicon nitride gate dielectric layer, and an ITO pixel electrode. Further, a structure necessary for the liquid crystal display can be formed thereon by a known method.
  • the polyimide resin film is peeled off from the support after forming the semiconductor element.
  • the polyimide resin film using the resin composition of this invention has favorable peelability and a mechanical characteristic, it can peel cleanly with a physical method. Further, peeling may be performed by irradiating a laser or the like from the support side.
  • examples of the display substrate include flexible wiring plates, liquid crystal elements, and electronic paper.
  • it is optimal for application to a device that is desired to be thin and flexible.
  • a manufacturing example of a flexible liquid crystal display substrate using the method for manufacturing a display substrate of the present invention will be described with reference to the drawings.
  • a glass substrate 1 is prepared as a support, and the resin composition of the present invention is applied onto the glass substrate 1 by spin coating, and then baked on a hot plate at 130 ° C. for 2 minutes to obtain a thickness of about A film was formed to a thickness of 5 ⁇ m to obtain a resin composition film 2.
  • FIG. 2 using a curing furnace, heat curing at 200 ° C. for 30 minutes and further at 350 ° C. for 60 minutes to imidize the polyimide precursor in the resin composition, and the polyimide which is a solid resin film Resin film 3 was formed.
  • the film thickness of this polyimide resin film 3 is 3 ⁇ m.
  • a TFT electrode layer 4 is formed according to a known method.
  • a liquid crystal display element layer 5 and a cover film layer 6 are formed thereon according to a known method.
  • the polyimide resin film 3 on which the TFT electrode layer 4 and the like are formed is physically peeled from the glass substrate 1.
  • the thermal expansion coefficient of the polyimide resin film of the present invention is preferably 50 ⁇ 10 ⁇ 6 / K or less, more preferably 30 ⁇ 10 ⁇ 6 / K or less in the range of 100 to 200 ° C., and the support. More preferably, the coefficient of thermal expansion is comparable to that of a glass substrate (for example, glass substrate). The higher the coefficient of thermal expansion of the support and the polyimide resin film, the more reliable the substrate and polyimide film will not peel or warp during the process of semiconductor element formation.
  • a display substrate can be provided.
  • the coefficient of thermal expansion is obtained by cutting the polyimide film after dehydration ring closure into 5 mm x 15 mm, and increasing the temperature from 25 ° C to 450 ° C by 5 ° C per minute using a thermal mechanical analyzer (for example, manufactured by Rigaku Corporation). Can be measured.
  • the elongation at break of the polyimide resin film is preferably 5% or more (25 ° C.), more preferably 10% or more, and further preferably 15% or more.
  • the elongation at break can be measured by an autograph (for example, manufactured by Shimadzu Corporation) using a sample obtained by cutting a polyimide film after dehydration ring closure into 10 mm ⁇ 60 mm. If the elongation at break is 5% or more, there is a tendency that flexibility can be added because there is a likelihood even if it is bent.
  • the elastic modulus (tensile elastic modulus) of the polyimide resin is preferably 1 GPa or more (25 ° C.), more preferably 1.5 GPa or more, and further preferably 2 GPa or more.
  • the elastic modulus can be measured by an autograph (for example, manufactured by Shimadzu Corporation) using a sample obtained by cutting a polyimide film after dehydration ring closure into 10 mm ⁇ 60 mm. If the modulus of elasticity is 1 GPa or more, the coefficient of thermal expansion tends to be small, so deformation at high temperature exposure is small, that is, dimensional deviation is difficult to occur, and reliability of various devices using the polyimide resin of the present invention. Tend to improve. Furthermore, the adhesive force (stud pull evaluation method?) Between the formed polyimide resin and the substrate is 50 kg / cm 2 or more and 950 kg / cm 2 or less, more preferably 300 kg / cm 2 or less. When the adhesion is weaker than this range, the semiconductor element is formed and peeling from the support is likely to occur during lamination, and when the adhesion exceeds this range, the polyimide resin film or There is a possibility of damaging the semiconductor block.
  • an autograph for example, manufactured by Shimadzu Corporation
  • a polyimide precursor solution A having a viscosity of 1100 mPa ⁇ s (25 ° C.) was obtained.
  • the weight average molecular weight of this polyimide precursor was 70,000.
  • the content of the polyimide precursor was 13% by mass.
  • liquid polyimide precursor C having a viscosity of 13,000 mPa ⁇ s (25 ° C.).
  • the weight average molecular weight of this polyimide precursor was 72,000.
  • the content of the polyimide precursor was 13% by mass.
  • Example 1 0.013 g of UCT-801 (50% methanol solution of 3-ureidopropyltriethoxysilane: hereinafter the same) was added to 100 g of the polyimide precursor solution A, and then stirred for 3 hours to obtain a resin composition 1.
  • content of an alkoxysilane compound is 0.05 mass% with respect to (a) polyimide precursor.
  • the obtained resin composition 1 was applied onto a 6-inch silicon wafer by spin coating and then baked (dried) for 2 minutes on a hot plate at 130 ° C. to form a film having a thickness of 18 ⁇ m. Next, using a curing furnace, heat curing was performed at 200 ° C. for 30 minutes and further at 450 ° C.
  • the film thickness of the polyimide resin film after heat curing was 10 ⁇ m.
  • the polyimide resin film was measured for adhesion to the silicon substrate, thermal characteristics, and mechanical characteristics, and the results are shown in Table 1.
  • Adhesion was measured by a stud pull evaluation method (stud tensile peel strength measurement) using a Romulas (Thin Film Adhesion Strength Measuring Machine) manufactured by Quad Group. Specifically, a sample piece obtained by cutting a silicon substrate on which a polyimide resin film is formed by the above-mentioned method into 1 cm squares is prepared, and a stud pin with an epoxy resin is raised and fixed with a clip at the center, and the sample piece is heated in a 150 ° C. oven. An evaluation sample was prepared by heating and curing for a period of time and fixing the stud pin with epoxy resin to the polyimide resin film.
  • the sample for evaluation was set on a romulus, the load was increased at a rate of 5 kg / min, a tensile load was applied in the vertical direction, and the strength at which the polyimide resin film peeled from the silicon substrate was defined as the peel strength.
  • the thermal characteristics are as follows. When the temperature is raised from 25 ° C. to 450 ° C. at 5 ° C. per minute using a thermal mechanical analyzer manufactured by Rigaku Corporation, the temperature is in the range of 100 to 200 ° C. The expansion coefficient and 1% mass loss temperature were measured.
  • Example 2 0.052 g of UCT-801 was added to 100 g of polyimide precursor solution A, and then stirred for 3 hours to obtain a resin composition 2.
  • content of an alkoxysilane compound is 0.2 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution A).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 3 After adding 0.13 g of UCT-801 to 100 g of polyimide precursor solution A, the mixture was stirred for 3 hours to obtain Resin Composition 3. In addition, content of an alkoxysilane compound is 0.5 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution A). Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 4 After 0.26 g of UCT-801 was added to 100 g of the polyimide precursor solution A, the mixture was stirred for 3 hours to obtain a resin composition 4. In addition, content of an alkoxysilane compound is 1.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution A). Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 5 0.018 g of UCT-801 was added to 100 g of the polyimide precursor solution B, and then stirred for 3 hours to obtain a resin composition 5.
  • content of an alkoxysilane compound is 0.05 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 6 0.072 g of UCT-801 was added to 100 g of the polyimide precursor solution B, and then stirred for 3 hours to obtain a resin composition 6.
  • content of an alkoxysilane compound is 0.2 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 7 After adding 0.18 g of UCT-801 to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 7.
  • content of an alkoxysilane compound is 0.5 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 8 0.072 g of SIB1140.0 (50% methanol solution of bis (2-hydroxyethyl) -3-aminopropyltriethoxysilane) was added to 100 g of the polyimide precursor solution B, and then stirred for 3 hours to obtain a resin composition 8. It was. In addition, content of an alkoxysilane compound is 0.2 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B). Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 9 0.18 g of SIB-1140 was added to 100 g of polyimide precursor solution B, and then stirred for 3 hours to obtain a resin composition 9.
  • content of an alkoxysilane compound is 0.5 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 10 After adding 0.36 g of SIB-1140 to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 10.
  • content of an alkoxysilane compound is 1.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 11 0.072 g of KBM-103 (phenyltrimethoxysilane) was added to 100 g of the polyimide precursor solution B, followed by stirring for 3 hours to obtain a resin composition 11.
  • content of an alkoxysilane compound is 0.4 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 12 After adding 0.18 g of KBM-103 to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 12.
  • content of an alkoxysilane compound is 1.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 13 After adding 0.36 g of KBM-103 to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 13. In addition, content of an alkoxysilane compound is 2.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B). Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 14 0.072 g of KBM-403 (3-glycidoxypropyltriethoxysilane) was added to 100 g of the polyimide precursor solution B, followed by stirring for 3 hours to obtain a resin composition 14.
  • content of an alkoxysilane compound is 0.4 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B).
  • Film formation was performed in the same manner as in Example 1, and the polyimide resin film obtained was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 2.
  • Example 15 After 0.18 g of KBM-403 was added to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 15. In addition, content of an alkoxysilane compound is 1.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B). Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 3.
  • Example 16 After adding 0.36 g of KBM-403 to 100 g of the polyimide precursor solution B, the mixture was stirred for 3 hours to obtain a resin composition 16. In addition, content of an alkoxysilane compound is 2.0 mass% with respect to a polyimide precursor (The polyimide precursor component in the polyimide precursor solution B). Film formation was performed in the same manner as in Example 1, and the obtained polyimide resin film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 3.
  • Example 17 After adding 0.14 g of UCT-801 to 100 g of the liquid polyimide precursor C, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 17. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 18 After adding 0.27 g of UCT-801 to 100 g of the liquid polyimide precursor C, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 18. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 19 After adding 0.54 g of UCT-801 to 100 g of the liquid polyimide precursor C, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 19. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 20 After adding 0.18 g of UCT-801 to 100 g of the liquid polyimide precursor D, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 20. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 21 After adding 0.36 g of UCT-801 to 100 g of the liquid polyimide precursor D, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 21. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 22 After adding 0.54 g of UCT-801 to 100 g of the liquid polyimide precursor D, the mixture was stirred for 3 hours to obtain a liquid polyimide precursor resin composition 22. Film formation was performed in the same manner as in Example 1, and the obtained polyimide film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 1.
  • Example 1 The polyimide precursor solution A was formed into a film by the method described in Example 1, and the obtained polyimide resin film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 3.
  • Example 2 The polyimide precursor solution B was formed into a film by the method described in Example 1, and the resulting polyimide resin film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 3.
  • the polyimide precursor solution B was applied by spin coating onto a 6-inch silicon wafer pretreated with a silane coupling agent, and then baked on a hot plate at 130 ° C. for 2 minutes to form a film having a thickness of 18 ⁇ m. Subsequently, it was heated and cured at 200 ° C. for 30 minutes and further at 450 ° C. for 60 minutes using a curing furnace to obtain a resin film made of a polyimide resin film. The film thickness after imidization was 10 ⁇ m. The obtained polyimide resin film was evaluated for adhesion, thermal characteristics, and mechanical characteristics. The results are summarized in Table 3.
  • the content of the (b) alkoxysilane compound indicates the content (mass%) of the solid content of the component (b) relative to the polyimide precursor component (solid content) in the (a) polyimide precursor solution.
  • a resin film using a resin composition containing 0.01 to 2% by mass of an alkoxysilane compound has adhesion, peelability, and heat resistance (thermal expansion coefficient, 1% by mass). (Decrease temperature) and mechanical properties (breaking elongation and elastic modulus) were found to be excellent. Even if the polyimide resin films as in Examples 1 to 17 are thin films of 10 ⁇ m, semiconductor elements such as TFTs can be easily formed and can be easily peeled off from the support. On the other hand, in Comparative Examples 1 and 2 using a resin composition not containing a silane coupling agent, the adhesion decreased.

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WO2016024457A1 (fr) * 2014-08-12 2016-02-18 株式会社カネカ Solution d'acide polyamique modifié par de l'alkysilane, stratifié et dispositif flexible l'utilisant ainsi que procédé de fabrication de stratifié
WO2016158988A1 (fr) * 2015-03-31 2016-10-06 日産化学工業株式会社 Composition pour la formation d'une couche de libération, et couche de séparation
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WO2017119450A1 (fr) * 2016-01-08 2017-07-13 日産化学工業株式会社 Composition permettant de former un substrat pour dispositifs flexibles
WO2019111870A1 (fr) * 2017-12-04 2019-06-13 ユニチカ株式会社 Solution destinée à revêtir un substrat en verre
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JP2022515452A (ja) * 2018-12-24 2022-02-18 ピーアイ・アドバンスド・マテリアルズ・カンパニー・リミテッド ディスプレイ基板製造用ポリアミック酸組成物およびこれを利用してディスプレイ用基板を製造する方法
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