WO2021091012A1 - Film de polyimide présentant de faibles propriétés diélectriques et son procédé de fabrication - Google Patents

Film de polyimide présentant de faibles propriétés diélectriques et son procédé de fabrication Download PDF

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Publication number
WO2021091012A1
WO2021091012A1 PCT/KR2019/016855 KR2019016855W WO2021091012A1 WO 2021091012 A1 WO2021091012 A1 WO 2021091012A1 KR 2019016855 W KR2019016855 W KR 2019016855W WO 2021091012 A1 WO2021091012 A1 WO 2021091012A1
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Prior art keywords
mol
polyimide film
content
less
dianhydride
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PCT/KR2019/016855
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English (en)
Korean (ko)
Inventor
조민상
백승열
전진석
이길남
Original Assignee
피아이첨단소재 주식회사
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Priority to CN201980101939.8A priority Critical patent/CN114616269B/zh
Publication of WO2021091012A1 publication Critical patent/WO2021091012A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • 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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4

Definitions

  • the present invention relates to a polyimide film, and more particularly, to a high-thickness polyimide film having low dielectric properties and reducing the number of bubbles in the produced film, and a method of manufacturing the same.
  • Polyimide (PI) is a polymer material that has the highest level of heat resistance, chemical resistance, electrical insulation, chemical resistance, and weather resistance among organic materials based on an imide ring that has excellent chemical stability with a rigid aromatic backbone. to be.
  • Polyimide films are in the spotlight as materials for various electronic devices requiring the above-described properties.
  • polyimides are soluble in organic solvents in the form of poly(amic acid) and do not dissolve when they become polyimide, so the processing of polyimide uses a solution of polyamic acid, and by drying the solution It is generally carried out by heating and imidating after obtaining a desired film, molded article, or coating film.
  • the residual thermal stress in the multilayer substrate significantly lowers the reliability of the device.
  • polyimide exhibiting a low coefficient of thermal expansion generally has a rigid and linear main chain structure, so most of them have poor water vapor permeability and film formation. It has a problem that it is easy to cause foaming depending on the conditions.
  • the generation of such bubbles may adversely affect the surface roughness of the prepared polyimide film, and may reduce the electrical, optical, and mechanical properties of the polyimide film as a whole.
  • an object of the present invention is to provide a low-dielectric, high-thickness polyimide film.
  • a dianhydride component including biphenyltetracarboxylic dianhydride (BPDA) and pyromellitic dianhydride (PMDA), and oxydianiline (ODA) , Obtained by imidization reaction of a polyamic acid solution containing a diamine component including paraphenylene diamine (PPD) and m-tolidine,
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • ODA oxydianiline
  • the content of the oxydianiline is 10 mol% or more and 30 mol% or less
  • the content of paraphenylene diamine is 10 mol% or more and 30 mol% or less
  • the m -The content of tolidine is 60 mol% or more and 80 mol% or less
  • the content of the biphenyltetracarboxylic dianhydride is 30 mol% or more and 50 mol% or less
  • the content of the pyromellitic dianhydride may be 50 mol% or more and 70 mol% or less.
  • the phosphorus compound may contain more than 0.1% by weight and less than 3.5% by weight based on the solid content of the dianhydride component and the diamine component.
  • the phosphorus-based compound is triphenyl phosphate (TPP), tricxylenyl phosphate (TXP), tricresyl phosphate (TCP), resorcinol diphenyl phosphate, and ammonium It may be any one or more selected from the group consisting of polyphosphate (ammonium polyphosphate).
  • the polyimide film may have an elastic modulus of 4.5 GPa or more and a thickness of 70 ⁇ m or more.
  • the number of bubbles per 1 m 2 of the polyimide film may be less than 50.
  • Another aspect of the present invention is (a) a dianhydride component including biphenyltetracarboxylic dianhydride (BPDA) and pyromellitic dianhydride (PMDA), and oxydianiline (ODA), paraphenylene.
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • ODA oxydianiline
  • the content of the oxydianiline is 10 mol% or more and 30 mol% or less
  • the content of paraphenylene diamine is 10 mol% or more and 30 mol% or less
  • the m -Prov ides a method for producing a polyimide film in which the content of tolidine is 60 mol% or more and 80 mol% or less.
  • Another aspect of the present invention provides a protective film and a carrier film including the polyimide film.
  • the present invention provides a polyimide film containing a phosphorus compound in which the composition ratio and solid content of the dianhydride and diamine components are controlled, thereby providing a high-thickness polyimide film having a low dielectric property having a thickness of 70 ⁇ m or more having an elastic modulus of 4.5 GPa or more. Provides.
  • the produced polyimide film was observed to have a film thickness of 70 ⁇ m or more and a relatively thick film, but the number of bubbles in the film was less than 50/m 2. It was possible to obtain a high-thickness film of excellent quality that did not.
  • Such a polyimide film has excellent mechanical properties of high elasticity, as well as low surface roughness and suppressed bubble formation, and particularly improves surface quality, so that it can be applied to fields requiring a polyimide film having such various properties.
  • dianhydric acid is intended to include a precursor or derivative thereof, which may not technically be a dianhydride acid, but nevertheless will react with a diamine to form a polyamic acid, and the polyamic acid is again polyamic acid. Can be converted to mid.
  • Ranges of numerical values are intended to include the endpoints and all integers and fractions within that range, unless stated otherwise, when a range is referred to herein. It is intended that the scope of the invention is not limited to the specific values recited when defining the range.
  • the polyimide film according to an embodiment of the present invention includes a dianhydride component including biphenyltetracarboxylic dianhydride (BPDA) and pyromellitic dianhydride (PMDA), and oxydianiline (ODA), para. Obtained by imidization reaction of a polyamic acid solution containing a diamine component including phenylene diamine (PPD) and m-tolidine,
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • ODA oxydianiline
  • the content of the oxydianiline is 10 mol% or more and 30 mol% or less
  • the content of paraphenylene diamine is 10 mol% or more and 30 mol% or less
  • the m -The content of tolidine is 60 mol% or more and 80 mol% or less
  • Paraphenylene diamine is a rigid monomer, and as the content of paraphenylene diamine (PPD) increases, the synthesized polyimide has a more linear structure and contributes to the improvement of mechanical properties such as the elastic modulus of the polyimide.
  • PPD paraphenylene diamine
  • the elastic modulus of the polyimide film having a high thickness may decrease.
  • the bubbles generated in the polyimide film correspond to poor quality that greatly affects the appearance and mechanical properties of the polyimide film, so even if the other properties of the manufactured polyimide film are excellent, the polyimide film with a large number of bubbles is actually It is difficult to apply to products.
  • a phosphorus-based compound having plasticizer properties that can increase flexibility between polyimide chains by giving free volume to strong bonds between polyimide chains induced by paraphenylene diamine was added.
  • the polyimide film may contain an inorganic filler.
  • the inorganic filler include silica (especially spherical silica), titanium oxide, alumina, silicon nitride, boron nitride, calcium hydrogen phosphate, calcium phosphate, mica, and the like.
  • the particle diameter of the filler is not particularly limited, and may be determined according to the film properties to be modified and the type of filler to be added. In general, the average particle diameter is 0.05 to 100 ⁇ m, preferably 0.1 to 75 ⁇ m, more preferably 0.1 to 50 ⁇ m, and particularly preferably 0.1 to 25 ⁇ m.
  • the particle diameter is less than this range, the modification effect is difficult to appear, and if it exceeds this range, the surface properties may be greatly impaired, or the mechanical properties may be greatly reduced.
  • the amount of the filler added is not particularly limited, and may be determined according to the film properties to be modified, the filler particle size, or the like. In general, the amount of the filler added is 0.01 to 100 parts by weight, preferably 0.01 to 90 parts by weight, more preferably 0.02 to 80 parts by weight, based on 100 parts by weight of the polyimide.
  • the amount of the filler added is less than this range, the effect of modifying by the filler is difficult to appear, and if it exceeds this range, there is a possibility that the mechanical properties of the film will be greatly impaired.
  • the method of adding the filler is not particularly limited, and any known method may be used.
  • the inorganic filler is included in the polyimide film to provide an anti-blocking property that prevents the polyimide films from adhering to each other during production or use by causing roughness to appear on the surface of the polyimide film.
  • the inorganic filler is usually used as an additive for a polyimide film, but in particular, spherical silica particles and the like are excellent in anti-blocking properties.
  • spherical silica particles as an inorganic filler, if the average diameter of the spherical silica particles exceeds 1 ⁇ m, the surface roughness increases, causing scratches on the surface of the object in contact with the polyimide film, resulting in product defects.
  • the average diameter of the spherical silica particles is less than 0.1 ⁇ m, anti-blocking properties for preventing the blocking phenomenon of the film are not exhibited.
  • the spherical silica particles are used in excess of an appropriate amount, the particles are aggregated and bonded to the film, and when used in an amount less than an appropriate amount, difficulties arise in the progress of the winding step due to the phenomenon that the films adhere to each other after surface treatment of the film.
  • the phosphorus compound having plasticizer properties used to inhibit bubble formation may contain more than 0.1% by weight and less than 3.5% by weight based on the solid content of the dianhydride component and diamine component used in the synthesis of polyimide, and in particular It is preferable to include 0.5 to 3.0% by weight.
  • the phosphorus compound When the phosphorus compound is included in an amount of 0.1% by weight or less, the effect of suppressing bubble formation is not sufficiently exhibited, and when it is included in an amount of 3.5% by weight or more, the elastic modulus of the polyimide film is decreased.
  • the phosphorus-based compounds used include triphenyl phosphate (TPP) and ammonium polyphosphate, trixylenyl phosphate (TXP), tricresyl phosphate (TCP), reso Resorcinol diphenyl phosphate and ammonium polyphosphate.
  • TPP triphenyl phosphate
  • TXP trixylenyl phosphate
  • TCP tricresyl phosphate
  • reso Resorcinol diphenyl phosphate and ammonium polyphosphate.
  • TPP triphenyl phosphate
  • ammonium polyphosphate but is not limited thereto, and flexibility between polyimide chains is provided by providing a free volume.
  • phosphorus compounds having plasticizer properties capable of increasing the phosphorus compound any phosphorus compound capable of contributing to the inhibition of bubble formation may be used.
  • the polyimide film according to the embodiment of the present application is a high-thickness polyimide film having high elasticity properties having an elastic modulus of 4.5 GPa or more and a thickness of 70 ⁇ m or more.
  • the elastic modulus of the polyimide film exhibited an excellent elastic modulus of 4.5 GPa or more depending on the content of paraphenylene diamine (PPD), and the polyimide film of such an excellent elastic modulus can be applied in various fields, but in particular, a carrier film or a protective film Suitable.
  • PPD paraphenylene diamine
  • the polyimide film exhibits a low surface roughness, which is directly related to the average diameter of the inorganic filler, and generally, as the average diameter of the inorganic filler increases, the surface roughness also increases. This increase in surface roughness causes scratches on the surface of the object in contact with the polyimide film, resulting in product defects.
  • the polyimide film is a high-thickness polyimide film having a thickness of 70 ⁇ m or more, and the thickness of the polyimide film is preferably 75 ⁇ m or more.
  • the number of bubbles per 1 m 2 is less than 50, and the number of bubbles decreases as the content of the phosphorus compound to be added increases.
  • the number of bubbles can be minimized (the presence of bubbles is not confirmed by observation), while maintaining the elastic modulus and surface roughness appropriate for the application of the product.
  • a dianhydride component including (a) biphenyltetracarboxylic dianhydride (BPDA) and pyromellitic dianhydride (PMDA), and oxydianiline (ODA), paraphenylene diamine.
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • ODA oxydianiline
  • the content of the oxydianiline is 10 mol% or more and 30 mol% or less
  • the content of paraphenylene diamine is 10 mol% or more and 30 mol% or less
  • the m -It relates to a method for producing a polyimide film, wherein the content of tolidine is 60 mol% or more and 80 mol% or less.
  • a thermal imidization method or a chemical imidization method may be applied, and a method in which a thermal imidization method and a chemical imidization method are combined may also be applied.
  • the thermal imidization method is a method of inducing an imidation reaction with a heat source such as hot air or an infrared dryer, excluding a chemical catalyst
  • the chemical imidization method is a method using a dehydrating agent and an imidizing agent.
  • the prepared polyimide film is suitable for a protective film or a carrier film, but is not limited thereto, and may be used in various fields to which the properties of the prepared polyimide film can be applied.
  • the polyimide film of the present invention can be prepared by a conventional method known in the art as follows. First, a polyamic acid solution is obtained by reacting the aforementioned dianhydride acid and a diamine component in an organic solvent.
  • the solvent is generally an amide-based solvent, such as an aprotic solvent, such as N,N'-dimethylformamide, N,N'-dimethylacetamide, N-methyl-pyrrolidone, or Combinations of these can be used.
  • an aprotic solvent such as N,N'-dimethylformamide, N,N'-dimethylacetamide, N-methyl-pyrrolidone, or Combinations of these can be used.
  • the input form of the dianhydride and diamine components can be added in the form of powder, lump or solution, and it is preferable to add in powder form at the beginning of the reaction to proceed with the reaction, and then in the form of a solution to control the polymerization viscosity. .
  • the obtained polyamic acid solution may be mixed with an imidization catalyst and a dehydrating agent and applied to a support.
  • the catalyst used examples include tertiary amines (eg, isoquinoline, ⁇ -picoline, pyridine, etc.), and examples of the dehydrating agent include anhydrous acid, but are not limited thereto.
  • the support used in the above may include a glass plate, an aluminum foil, a circulating stainless steel belt, or a stainless drum, but is not limited thereto.
  • the film applied on the support is gelled on the support by dry air and heat treatment.
  • the gelled film is separated from the support and heat-treated to complete drying and imidization.
  • the heat-treated film may be heat-treated under a certain tension to remove residual stress in the film generated during the film forming process.
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA fatigue Meliticdianhydride
  • ODA oxydianiline
  • PPD paraphenylene diamine
  • m-tolidine a controlled composition ratio to completely dissolve.
  • stirring was continued for 120 minutes while heating the reactor by raising the temperature of the reactor to 40° C. in a nitrogen atmosphere to prepare a polyamic acid having a primary reaction viscosity of 1,500 cP.
  • a high-thickness polyimide film was prepared using an applicator.
  • dianhydride component 40 mol% and 60 mol% of biphenyltetracarboxylic dianhydride (BPDA) and pyromellitic dianhydride (PMDA) were used, respectively, and dianhydride 100 mol% of the diamine component was reacted based on 100 mol% of the component.
  • BPDA biphenyltetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • composition ratio of the diamine components oxydianiline (ODA), paraphenylene diamine (PPD) and m-tolidine is oxydianiline, paraphenylene diamine and m-tolidine when the total content of diamine is 100 mol%. 15 mol%, 15 mol% and 70 mol% were used, respectively.
  • TPP triphenyl phosphate
  • Example 1 0.5 20-30 pcs 5.87
  • Example 2 1.0 10-15 pcs 5.61
  • Example 3 1.5 5-7 pieces 5.42
  • Example 4 2.0 2-3 pieces 5.35
  • Example 5 2.5 0 units 5.02
  • Example 6 3.0 0 units 4.76 Comparative Example 1 0.0 63 ⁇ 68 pcs 6.25 Comparative Example 2 0.1 60 ⁇ 68pcs 6.05 Comparative Example 3 3.5 0 units 4.43 Comparative Example 4 4.0 0 units 4.13
  • the modulus of elasticity of the polyimide films prepared in all Examples and Comparative Examples was tested 3 times according to ASTM D 882 regulations using a Standard Instron testing apparatus, and an average value was taken.
  • the average number of bubbles was first photographed using a film defect analysis device equipped with an imaging device, and the average number of bubbles was obtained through a procedure of directly checking the image of the captured polyimide film with the naked eye.
  • a film having a certain width and length was collected as a sample and the number of bubbles was measured, and the number of bubbles measured thereafter was converted into the number of bubbles per 1 m 2.
  • TPP triphenyl phosphate
  • TPP triphenyl phosphate
  • TPP triphenyl phosphate
  • Examples of the polyimide film and the method of manufacturing the polyimide film according to the present invention are only preferred embodiments that enable those skilled in the art to easily implement the present invention. Since it is not limited, this does not limit the scope of the present invention.
  • the present invention provides a polyimide film containing a phosphorus compound in which the composition ratio and solid content of the dianhydride and diamine components are controlled, thereby providing a high-thickness polyimide film having a low dielectric property having a thickness of 70 ⁇ m or more having an elastic modulus of 4.5 GPa or more. Provides.
  • Such a polyimide film has excellent mechanical properties of high elasticity, as well as low surface roughness and suppressed bubble formation, and particularly improves surface quality, so that it can be applied to fields requiring a polyimide film having such various properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

La présente invention concerne un film de polyimide présentant de faibles propriétés diélectriques et dans lequel le nombre de bulles a été réduit, et un procédé de fabrication d'un film de polyimide le comprenant, et fournit un film de polyimide qui contient un composé de phosphore et est obtenu au moyen d'une réaction d'imidisation d'une solution de poly(acide amique) comprenant : un composant dianhydride d'acide comprenant un dianhydride biphényl-tétracarboxylique (BPDA) et un dianhydride pyromellitique (PMDA) ; et un composant diamine comprenant de l'oxydianiline (ODA), de la para-phénylènediamine (PPD) et de la m-tolidine.
PCT/KR2019/016855 2019-11-07 2019-12-02 Film de polyimide présentant de faibles propriétés diélectriques et son procédé de fabrication WO2021091012A1 (fr)

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CN201980101939.8A CN114616269B (zh) 2019-11-07 2019-12-02 低介电质的聚酰亚胺薄膜及其制备方法

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KR1020190141453A KR102347589B1 (ko) 2019-11-07 2019-11-07 저유전 폴리이미드 필름 및 그 제조방법
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WO2023211225A1 (fr) * 2022-04-29 2023-11-02 피아이첨단소재 주식회사 Film de polyimide ayant de faibles propriétés diélectriques et de résistance à la chaleur et son procédé de préparation

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