WO2020218693A1 - Film de polyimide, stratifié plaqué de feuille métallique flexible comprenant celui-ci et procédé de fabrication de film de polyimide - Google Patents

Film de polyimide, stratifié plaqué de feuille métallique flexible comprenant celui-ci et procédé de fabrication de film de polyimide Download PDF

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Publication number
WO2020218693A1
WO2020218693A1 PCT/KR2019/013962 KR2019013962W WO2020218693A1 WO 2020218693 A1 WO2020218693 A1 WO 2020218693A1 KR 2019013962 W KR2019013962 W KR 2019013962W WO 2020218693 A1 WO2020218693 A1 WO 2020218693A1
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Prior art keywords
polyimide film
polyamic acid
tolidine
dianhydride
final
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PCT/KR2019/013962
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English (en)
Korean (ko)
Inventor
김기훈
이길남
최정열
백승열
조민상
Original Assignee
피아이첨단소재 주식회사
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Priority to CN201980095704.2A priority Critical patent/CN113728036B/zh
Publication of WO2020218693A1 publication Critical patent/WO2020218693A1/fr

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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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of 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 C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to a polyimide film, and more particularly, to a polyimide film having a low dielectric loss factor (Df), a flexible metal clad laminate including the same, and a method of manufacturing a polyimide film having a low dielectric loss factor (Df).
  • Df dielectric loss factor
  • Df low dielectric loss factor
  • polyimide In general, polyimide (PI) is based on an imide ring that has excellent chemical stability with a rigid aromatic backbone, and has the highest level of heat resistance, chemical resistance, electrical insulation, chemical resistance, and weather resistance among organic materials. Eggplant is a polymer material.
  • the polyimide film produced therefrom is in the spotlight as an insulating material for electronic components that require the above-described characteristics, and in fact, it is a thin circuit board with high circuit integration and flexibility, in a broader sense, the flexible metal foil clad laminate. It is widely used as an insulating film.
  • the dielectric dissipation factor (Df) refers to the degree of wasted electrical energy of the thin circuit board, and is closely related to the signal transmission delay that determines the communication speed.
  • the dielectric loss factor (Df) of the polyimide film ) As low as possible is an important factor in the performance of the thin circuit board.
  • the present invention provides a polyimide film having a low dielectric loss rate (Df), a flexible metal clad laminate including the same, and a method of manufacturing a polyimide film having a low dielectric loss rate (Df) by controlling the molecular weight. There is a purpose to do.
  • the polyimide film of the present invention to achieve the above object is a final comprising a first polyamic acid comprising a first block derived from pyromellitic dianhydride (PMDA) and m-tolidine (m-tolidine) It is prepared by imidizing polyamic acid, and the average molecular weight of the first block is 20,000 g/mol or less.
  • PMDA pyromellitic dianhydride
  • m-tolidine m-tolidine
  • the present invention provides a polyimide film having a low dielectric loss factor (Df) through molecular weight control, thereby providing a flexible metal clad laminate that can be applied to an electrical transmission circuit capable of communicating at a high frequency of at least 2 GHz or more, and further, a 5G band. .
  • Df dielectric loss factor
  • dianhydride is intended to include a precursor or derivative thereof, which may not be technically a dianhydride, but nevertheless will react with diamine to form a polyamic acid, which 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 present invention includes a polyimide film. It will be described in more detail below.
  • the polyimide film of the present invention already contains a final polyamic acid comprising a first polyamic acid comprising a first block derived from pyromellitic dianhydride (PMDA) and m-tolidine. It is manufactured by making it.
  • PMDA pyromellitic dianhydride
  • the average molecular weight of the first block is preferably 20,000 g/mol or less, more preferably 15,000 g/mol or less, and still more preferably 10,000 g/mol.
  • a polyimide film having a small average molecular weight is excellent in terms of dielectric loss factor (Df), and the polyimide film of the present invention having an average molecular weight of 20,000 g/mol or less in the first block satisfies a dielectric loss factor (Df) of 0.005 or less. .
  • the number of repeating units (or degree of polymerization) of the first block is preferably an integer of 5 to 55, more preferably 5 to 40, and even more preferably 5 to 30.
  • a polyimide film having a small number of repeating units and a small average molecular weight is excellent in terms of dielectric loss factor (Df)
  • the polyimide film of the present invention having a repeating unit number of 5 to 55 in the first block has a dielectric loss rate (Df) satisfies 0.005 or less.
  • the average molecular weight and the number of repeating units of the first block are too small, there may be limitations in exhibiting the excellent properties of the polyimide other than the dielectric loss rate (Df), so the average molecular weight is at least 2,000 g/mol or more, It is preferable that the number is 5 or more.
  • the first polyamic acid has a molar ratio of pyromellitic dianhydride (PMDA) and m-tolidine of 0.86:1 to 0.98:1, more preferably It is preferable to satisfy 0.86:1 to 0.975:1, more preferably 0.86:1 to 0.97:1.
  • PMDA pyromellitic dianhydride
  • m-tolidine 0.86:1 to 0.98:1, more preferably It is preferable to satisfy 0.86:1 to 0.975:1, more preferably 0.86:1 to 0.97:1.
  • the final polyamic acid further includes a second polyamic acid including a second block derived from dianhydride and m-tolidine.
  • the second block is biphenyl-tetracarboxylic acid dianhydride (BPDA), oxydiphthalic anhydride (4,4'-oxidiphthalic anhydride, ODPA), and benzophenone tetracarboxylic acid. It is preferable to be derived from at least one dianhydride selected from dianhydride (3,3',4,4'-benzophenone tetracarboxylic dianhydride, BTDA) and m-tolidine, but the type of dianhydride is not particularly limited thereto.
  • the final polyamic acid comprising the first polyamic acid and the second polyamic acid is the sum of the dianhydride (PMDA) of the first polyamic acid and the dianhydride (BPDA) of the second polyamic acid and the molar ratio of m-tolidine is 0.96: It is preferable to satisfy 1 to 0.98:1, and more preferably to satisfy 0.97:1. Thereafter, a final molar ratio of 0.995 to 0.997:1 is formed using a PMDA solution.
  • m-tolidine includes m-tolidine contained in the first polyamic acid and the second polyamic acid.
  • the viscosity of the final polyamic acid is preferably 190,000 cP to 210,000 cP, more preferably 200,000 cP.
  • the viscosity of the first polyamic acid and the second polyamic acid is also preferably 190,000 cP to 210,000 cP, and more preferably 200,000 cP.
  • the polyimide film of the present invention described so far satisfies the dielectric loss factor (Df) of 0.005 or less, more preferably 0.0045 or less, and still more preferably 0.004 or less.
  • Df dielectric loss factor
  • the dielectric loss factor (Df) is generally used as an index indicating the ease of dissipation (dielectric loss), and the higher the dielectric loss rate (Df), the more easily the charge is lost, and on the contrary, the lower the dielectric loss rate (Df), the higher the charge is. It can be difficult to lose. That is, dielectric loss rate (Df) is a measure of power loss. As the dielectric loss rate (Df) is lower, the communication speed can be maintained faster while the signal transmission delay due to power loss is reduced. This is a strong requirement.
  • the polyimide film of the present invention which satisfies at least 2GHz or more, and furthermore, a dielectric loss factor (Df) of 0.005 or less, more specifically 0.0045 or less, and more specifically 0.004 or less under high frequency in 5G band, is It is possible to provide a flexible metal foil laminate that can be applied to an electrical transmission circuit capable of communication.
  • Df dielectric loss factor
  • Second aspect manufacturing method of polyimide film
  • the present invention includes a method for producing a polyimide film. It will be described in more detail below.
  • the manufacturing method of the polyimide film of the present invention includes (a) a first block derived by polymerizing pyromellitic dianhydride (PMDA) and m-tolidine in an organic solvent. Preparing polyamic acid, (b) biphenyl-tetracarboxylic acid dianhydride (BPDA), oxydiphthalic anhydride (4,4'-oxidiphthalic anhydride, ODPA), and benzophenone tetracar.
  • PMDA pyromellitic dianhydride
  • ODPA oxydiphthalic anhydride
  • benzophenone tetracar benzophenone tetracar.
  • BTDA hexalic dianhydrides
  • step (a) the molar ratio of pyromellitic dianhydride (PMDA) and m-tolidine is 0.86:1 to 0.98:1, more preferably 0.86:1 to 0.975:1, and even more preferably 0.86:1 to It is desirable to satisfy 0.97:1.
  • PMDA pyromellitic dianhydride
  • the final polyamic acid comprising the first polyamic acid and the second polyamic acid is the sum of the dianhydride of the first polyamic acid (PMDA) and the dianhydride of the second polyamic acid and the molar ratio of m-tolidine It is preferable to satisfy 0.96:1 to 0.98:1, and more preferably to satisfy 0.97:1.
  • m-tolidine includes m-tolidine contained in the first polyamic acid and the second polyamic acid.
  • the first polyamic acid or the second polyamic acid may be prepared by a random polymerization method or a block polymerization method, but the polymerization method is not particularly limited thereto. .
  • the organic solvent is preferably an organic polar solvent, more preferably an aprotic polar solvent, specifically N,N-dimethylformamide (DMF), N, It is preferable to be at least one solvent selected from N-dimethylacetamide, N-methyl-pyrrolidone (NMP), gamma butyrolactone (GBL), and Diglyme, but the type of solvent is particularly limited thereto. no.
  • a separate filler may be further added for the purpose of improving various properties of the polyimide film, such as sliding properties, thermal conductivity, corona resistance, and loop hardness.
  • a filler selected from silica, titanium oxide, alumina, silicon nitride, boron nitride, calcium hydrogen phosphate, calcium phosphate, and mica may be added.
  • the average particle diameter of such a filler can be determined according to the characteristics of the polyimide film to be improved and the type of filler, but considering the reduction in mechanical properties due to the modification effect and surface property damage, 0.05 to 100 ⁇ m, more preferably 0.1 It is preferably in the range of 75 ⁇ m, more preferably 0.1 to 50 ⁇ m.
  • the amount of the filler added can also be determined according to the properties of the polyimide film to be improved and the type of filler, but considering the modification effect and the decrease in mechanical properties, 0.01 to 100 parts by weight per 100 parts by weight of the polyimide film, more It is preferably contained in an amount of 0.015 to 90 parts by weight, more preferably 0.02 to 80 parts by weight.
  • the final polyamic acid is preferably prepared by copolymerizing the first polyamic acid and the second polyamic acid in an organic solvent, and after forming a film of the final polyamic acid prepared in this way on a support, imidization is performed. It is desirable to proceed.
  • 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 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 thermal imidization method it is preferable to induce the imidation reaction at a temperature of 100 to 600°C, more preferably 200 to 500°C, and even more preferably 300 to 500°C.
  • the present invention includes a flexible metal foil laminate comprising the polyimide film of the present invention described above and an electrically conductive metal foil. It will be described in more detail below.
  • the electrically conductive metal foil is preferably made of at least one metal selected from copper, stainless steel, nickel, and aluminum, or an alloy containing the same, and most preferably copper foil, but is not particularly limited thereto.
  • a rust prevention layer, a heat-resistant layer, or an adhesive layer may be applied to the surface of the metal foil, and the thickness of the metal foil may be any thickness capable of exhibiting a sufficient function depending on the application.
  • the flexible metal foil laminate of the present invention has a structure in which a metal foil is laminated on one side of a polyimide film, or an adhesive layer containing a thermoplastic polyimide is included on one side of the polyimide film, and the metal foil is laminated thereto.
  • NMP was added while injecting nitrogen into a 500ml reactor equipped with a stirrer and a nitrogen injection/discharging tube, and after setting the temperature of the reactor to 30°C, PMDA and m-tolidine were added to completely dissolve. Thereafter, stirring was continued for 120 minutes while raising the temperature of the reactor to 40° C. in a nitrogen atmosphere to prepare a first polyamic acid having a viscosity at 23° C. of 500 to 2,500 cP.
  • the first polyamic acid thus prepared includes a first block derived by polymerizing PMDA and m-tolidine.
  • the second polyamic acid When preparing the second polyamic acid, the amount of BPDA and m-tolidine was added so that the sum of the dianhydrides (PMDA and BPDA) of the final polyamic acid and the molar ratio of m-tolidine was 0.97:1. Thereafter, a final molar ratio of 0.995 to 0.997:1 is formed using a PMDA solution.
  • the second polyamic acid thus prepared includes a second block derived by polymerizing BPDA and m-tolidine.
  • the first polyamic acid prepared above and the second polyamic acid were mixed, the temperature of the reactor was raised to 40° C. in a nitrogen atmosphere, and stirring was continued for 120 minutes while heating to a final polyamic acid having a final viscosity of 200,000 cP at 23° C. Was prepared.
  • the viscosity and the molar ratio of the dianhydride and diamine were adjusted using a PMDA solution, and the final molar ratio was formed from 0.995 to 0.997:1.
  • the final polyamic acid thus prepared was removed from air bubbles through high-speed rotation of 1,500 rpm or more, and then coated on a glass substrate using a spin coater. Thereafter, a gel film was prepared by drying at a temperature of 120° C. for 30 minutes under a nitrogen atmosphere, which was heated up to 450° C. at a rate of 2° C./min, heat-treated at 450° C. for 60 minutes, and then 2 to 30° C. By cooling again at a rate of °C/min, a final polyimide film was obtained, dipping in distilled water, and peeling from the glass substrate.
  • the molar ratio of PMDA and m-tolidine takes into account the molecular weight of PMDA (about 218 g/mol) and the molecular weight of m-tolidine (about 212 g/mol), and the molecular weight at which two water molecules escape by dehydration during their polymerization reaction (about 218 g/mol) 36g/mol), calculate the unit body molecular weight (about 394.42g/mol) of the first block, and divide the average molecular weight of the target first block by the unit body molecular weight of the first block calculated previously, and the number of repeating units (degree of polymerization) After obtaining, it was calculated by applying it to the Carothers equation. And after the production of the polyimide films of Examples 1 to 4 and Comparative Examples 1 to 4, it was confirmed to have an average molecular weight of the target first block.
  • Table 2 below shows the dielectric loss factor (Df) of the polyimide films of Examples 1 to 4 and Comparative Examples 1 to 4 prepared above, and the dielectric loss factor (Df) is measured by rolling copper foil on both sides of the polyimide film- After performing the two-roll lamination to prepare a flexible metal foil laminate, this was measured by standing for 72 hours using an ohmmeter Agilent 4294A.
  • the polyimide film of Examples 1 to 4 satisfies the dielectric loss factor (Df) of 0.005 or less, and is applicable to an electrical transmission circuit in which signal transmission is performed at high frequency, whereas the polyimide films of Comparative Examples 1 to 4 Since the polyimide film has a relatively high dielectric loss factor (Df), it can be expected to be difficult to apply to the same.
  • Df dielectric loss factor
  • An embodiment of the polyimide film of the present invention, a flexible metal foil laminate including the same, and a method of manufacturing a polyimide film are described in the present invention.
  • the present invention provides a polyimide film having a low dielectric loss factor (Df) through molecular weight control, thereby providing a flexible metal clad laminate that can be applied to an electrical transmission circuit capable of communicating at a high frequency of at least 2 GHz or more, and further, a 5G band. .
  • Df dielectric loss factor

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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)
  • Laminated Bodies (AREA)
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Abstract

La présente invention concerne un film de polyimide ayant un faible facteur de dissipation diélectrique (Df), un stratifié plaqué de feuille métallique flexible comprenant celui-ci et un procédé de fabrication du film de polyimide ayant un faible Df. Le film de polyimide selon la présente invention est fabriqué par imidisation d'un acide polyamique final comprenant un premier acide polyamique comprenant un premier bloc dérivé du dianhydride pyromellitique (PMDA) et de m-tolidine, la masse moléculaire moyenne du premier bloc étant inférieure ou égale à 20 000 g/mol.
PCT/KR2019/013962 2019-04-23 2019-10-23 Film de polyimide, stratifié plaqué de feuille métallique flexible comprenant celui-ci et procédé de fabrication de film de polyimide WO2020218693A1 (fr)

Priority Applications (1)

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CN201980095704.2A CN113728036B (zh) 2019-04-23 2019-10-23 聚酰亚胺薄膜、包含其的柔性金属箔层压板及聚酰亚胺薄膜制备方法

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KR1020190047042A KR102202484B1 (ko) 2019-04-23 2019-04-23 폴리이미드 필름, 이를 포함하는 연성금속박적층판 및 폴리이미드 필름의 제조방법
KR10-2019-0047042 2019-04-23

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KR102437830B1 (ko) * 2020-11-17 2022-08-31 피아이첨단소재 주식회사 치수안정성이 개선된 저유전 폴리이미드 필름 및 그 제조방법

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KR20130080433A (ko) * 2010-03-31 2013-07-12 제이에스알 가부시끼가이샤 기판의 제조 방법 및 그것에 이용되는 조성물
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KR20170061348A (ko) * 2015-11-26 2017-06-05 주식회사 엘지화학 본딩 시트 및 연성 인쇄 회로 기판
KR101906393B1 (ko) * 2017-11-03 2018-10-11 에스케이씨코오롱피아이 주식회사 초박막 블랙 폴리이미드 필름 및 이의 제조방법

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