CN106366334B - Preparation method of polyimide film with low dielectric constant and low dielectric loss factor - Google Patents

Preparation method of polyimide film with low dielectric constant and low dielectric loss factor Download PDF

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CN106366334B
CN106366334B CN201610753368.4A CN201610753368A CN106366334B CN 106366334 B CN106366334 B CN 106366334B CN 201610753368 A CN201610753368 A CN 201610753368A CN 106366334 B CN106366334 B CN 106366334B
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low dielectric
dielectric constant
polyimide film
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dianhydride
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CN106366334A (en
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岑建军
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NINGBO JINSHAN NEW MATERIAL Co.,Ltd.
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    • 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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • 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
    • C08J2427/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2427/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2427/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2427/18—Homopolymers or copolymers of tetrafluoroethylene
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/011—Nanostructured additives

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  • Health & Medical Sciences (AREA)
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  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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Abstract

The invention discloses a preparation method of a polyimide film with low dielectric constant and low dielectric loss factor, which comprises the steps of preparing a polyamide acid solution from dianhydride and diamine, and preparing the polyimide film together with additives such as nano fluorine-containing polymer powder, nano aluminum oxide powder, nano silicon dioxide powder and the like, and is characterized in that the additives account for 10-50% of the polyamide acid by weight; the polyimide film with low dielectric constant and low dielectric loss factor, which is obtained by the invention, realizes the dielectric constant less than or equal to 2.6 and the dielectric loss factor less than or equal to 0.003 on the basis of keeping good mechanical properties, and has the advantages of simple process, easily purchased raw materials and low price.

Description

Preparation method of polyimide film with low dielectric constant and low dielectric loss factor
Technical Field
The invention relates to a preparation method of a polyimide film, in particular to a preparation method of a polyimide film with low dielectric constant and low dielectric loss factor.
Background
With the development of technology and product requirements, the size of the printed circuit board tends to be light, thin, short and small, and the high frequency substrate with high transmission rate gradually becomes the key point of development in response to the high frequency of the wireless network and communication products. As a material used for a high-frequency communication substrate, it is essential that data can be transmitted quickly and data loss or interference during transmission cannot be caused. It is known that the delay caused by the transmission of electronic signals between metal wires is a main reason for the limited speed of semiconductor devices. In order to reduce the time delay of signal transmission, a material with a low dielectric constant can be used as an inter-wire insulating layer to reduce the capacitance between wires, increase the operation speed of the device and reduce noise interference. The insulating layer blocks the passage of current and has a low Dielectric Constant (D)k) The insulating material can avoid forming unnecessary stray capacitance (stray capacitance) on the circuit. In addition, the material wastes electricity if it is lost, so the dielectric loss Factor (D) of the material is requiredf) The smaller the better.
Polyimide (PI) has good heat resistance, chemical resistance, mechanical strength, high electrical resistance, and the like, and has been widely used in the electronics industry, for example, as a material for printed circuit boards. However, polyimide films are known to have high dielectric constants and high dissipation factors, and thus have drawbacks and limitations as high-frequency materials. At present, the dielectric constant of PI material is mainly reducedThe following aspects are to be focused on: (1) fluorine-containing dianhydride and diamine monomers are adopted, but the fluorine-containing monomers have complex preparation process and high cost, so that the prepared polyimide is expensive; (2) the additive is removed by heating or solvent extraction to obtain the polyimide with a porous structure, and gaps are introduced into the polyimide, for example, melamine is adopted as a pore-forming agent in the patent CN201410481836.8, a honeycomb-shaped polyimide film prepared by CN200610053038.0 and CN201410454474.3 are introduced into a nano-scale aperture, but the porous polyimide has the advantages of reduced structural strength and large effective volume, and is not beneficial to the application of the polyimide in large-scale integrated circuit devices. Recently, patent publications such as CN201510136576.5, CN201510160254.4, CN201410733633.3, and CN201520175411.4 of damei corporation adopt a multi-layer polyimide structure to prepare a polyimide film with a low dielectric constant, but the related multi-layer film preparation process is complicated. On the other hand, the related patents are mainly focused on the reduction of the dielectric constant, and the dielectric loss factor is less concerned, and the dielectric loss factor of the polyimide film is generally more than 0.004. Therefore, it is necessary to find a method for preparing a polyimide film with a simple synthesis process and a greatly reduced dielectric constant and dissipation factor, and particularly, it is required to prepare Dk≤2.6，DfThe polyimide film material less than or equal to 0.003 is a new requirement for polyimide film.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provide a preparation method of a polyimide film with low dielectric constant and low dielectric dissipation factor, which has low cost and simple process and can reduce the dielectric constant and the dissipation factor.
In order to achieve the above object, the present invention provides a method for preparing a polyimide film with a low dielectric constant and a low dielectric dissipation factor, comprising the following steps:
(1) putting diamine into a reaction kettle, dissolving the diamine by using a polar aprotic solvent, then adding dianhydride into the reaction kettle in batches, and stirring to prepare the needed polyamic acid solution;
(2) uniformly mixing three additives, namely nanoscale fluorine-containing polymer powder, nanoscale aluminum oxide powder and nanoscale silicon dioxide powder, then adding the mixture into a polar aprotic solvent, and uniformly dispersing to prepare slurry;
(3) adding the prepared slurry into a reaction kettle of the prepared polyamic acid solution, adding a polar aprotic solvent to adjust and control the viscosity of a final reaction product to be 80000 +/-1000 CP, and defoaming, casting and forming a film.
Wherein the diamine is one or two of 4, 4-diaminodiphenyl ether, p-phenylenediamine, 4-diaminodiphenylmethane and 2, 2-bis [4- (4-aminophenoxy) phenyl ] propane; wherein the dianhydride is one or two of pyromellitic dianhydride (PMDA), 3',4,4' -biphenyl tetracarboxylic dianhydride (BPDA), 3',4,4' -Benzophenone Tetracarboxylic Dianhydride (BTDA), 4,4 '-diphenyl ether dianhydride (ODPA) and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride (6FPA), and the dianhydride and the diamine are not simultaneously one; the polar aprotic solvent is one or more of dimethylacetamide, N-methylpyrrolidone and dimethylformamide.
The total weight of the three additives of the nanometer fluorine-containing polymer powder, the nanometer aluminum oxide powder and the nanometer silicon dioxide powder accounts for 10 to 50 percent of the weight of the polyimide resin. The weight ratio of the three additives of the nanometer fluorine-containing polymer powder, the nanometer aluminum oxide powder and the nanometer silicon dioxide powder is as follows: nano fluorine-containing polymer powder: nano-level aluminum oxide powder: nano-scale silicon dioxide powder =40% -60%: 20% -40%: 10% -30%, the percentage refers to the total weight of the three additives; the prepared polyimide film has dielectric constant not more than 2.6 and dielectric loss factor not more than 0.003.
The nanometer fluorine-containing polymer powder can greatly reduce the dielectric constant and the dielectric loss factor, avoids the problem of high price caused by introducing fluorine-containing dianhydride or diamine monomer, can play a role in reducing the dielectric constant to a certain extent, can effectively reduce the dielectric loss factor through filling, and plays a certain role in enhancing the whole substrate.
The polyimide film with low dielectric constant and low dielectric loss factor, which is obtained by the invention, realizes the dielectric constant less than or equal to 2.6 and the dielectric loss factor less than or equal to 0.003 on the basis of keeping good mechanical properties. The method has the following specific advantages:
(1) by adopting a copolymerization method, the dianhydride and the diamine are not simultaneously one, so that the final film performance can be conveniently regulated and controlled, and the product is ensured to have excellent mechanical properties;
(2) the dianhydride and the diamine are commercial raw materials, so the cost is low;
(3) the single-layer structure is adopted, and the preparation process is simple;
(4) the comprehensive performance optimization of the film low dielectric constant and low dielectric loss factor is realized by adjusting the balance of three additives, namely the nanoscale fluorine-containing polymer powder, the nanoscale aluminum oxide powder and the nanoscale silicon dioxide powder.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1:
the preparation method of the polyimide film with the low dielectric constant and the low dielectric loss factor provided by the embodiment comprises the following specific steps:
(1) 4, 4-diaminodiphenyl ether (1 mol, 200.2 g) is put into a reaction kettle and dissolved by dimethyl acetamide, then a mixture of pyromellitic dianhydride (PMDA, 0.8 mol, 174.5 g) and 3,3',4,4' -benzophenonetetracarboxylic dianhydride (BTDA, 0.2 mol, 64.4 g) is added into the reaction kettle in batches and stirred to prepare the required polyamic acid solution;
(2) uniformly mixing three additives, namely nano-scale Polytetrafluoroethylene (PTFE) (50.0 g), nano-scale aluminum oxide powder (30.0 g) and nano-scale silicon dioxide powder (20.0 g), adding the mixture into dimethyl acetyl, and fully stirring to prepare slurry;
(3) and adding the prepared slurry into a reaction kettle of the prepared polyamic acid solution, adding a solvent to adjust and control the viscosity of a final reaction product, and defoaming, casting and forming a film.
The polyimide film with a low dielectric constant and a low dielectric dissipation factor obtained in this example had a dielectric constant of 2.5 and a dielectric dissipation factor of 0.002.
Example 2:
the preparation method of the polyimide film with low dielectric constant and low dielectric dissipation factor provided in this embodiment is substantially the same as that of embodiment 1, except that the three additives are different in mixture ratio, wherein the three additives include 60.0 g of nano-Polytetrafluoroethylene (PTFE), 20.0 g of nano-alumina powder, and 20.0 g of nano-silica powder.
The polyimide film with a low dielectric constant and a low dielectric dissipation factor obtained in this example had a dielectric constant of 2.4 and a dielectric dissipation factor of 0.002.
Example 3:
the preparation method of the polyimide film with low dielectric constant and low dielectric dissipation factor provided in this embodiment is substantially the same as that of embodiment 1, except that the three additives are different in mixture ratio, wherein the three additives include 50.0 g of nano-Polytetrafluoroethylene (PTFE), 30.0 g of nano-alumina powder, and 20.0 g of nano-silica powder.
The polyimide film with a low dielectric constant and a low dielectric dissipation factor obtained in this example had a dielectric constant of 2.6 and a dielectric dissipation factor of 0.003.

Claims (3)

1. A preparation method of a polyimide film with low dielectric constant and low dielectric loss factor is characterized by comprising the following steps:
(1) putting diamine into a reaction kettle, dissolving the diamine by using a polar aprotic solvent, then adding dianhydride into the reaction kettle in batches, and stirring to prepare the needed polyamic acid solution;
(2) uniformly mixing three additives of nanoscale fluorine-containing polymer powder, nanoscale aluminum oxide powder and nanoscale silicon dioxide powder, then adding the mixture into a polar aprotic solvent, and uniformly dispersing to prepare slurry, wherein the weight ratio of the three additives of the nanoscale fluorine-containing polymer powder, the nanoscale aluminum oxide powder and the nanoscale silicon dioxide powder is as follows: nano fluorine-containing polymer powder: nano-level aluminum oxide powder: nano-scale silicon dioxide powder =40% -60%: 20% -40%: 10 to 30 percent of the polyimide resin, wherein the total weight of the three additives of the nano fluorine-containing polymer powder, the nano aluminum oxide powder and the nano silicon dioxide powder accounts for 10 to 50 percent of the weight of the polyimide resin;
(3) adding the prepared slurry into a reaction kettle of the prepared polyamic acid solution, adding a polar aprotic solvent to adjust and control the viscosity of a final reaction product to be 80000 +/-1000 CP, and defoaming, casting and forming a film.
2. The method according to claim 1, wherein the polyimide film has a low dielectric constant and a low dielectric dissipation factor, and the method comprises the steps of: wherein the diamine is one or two of 4, 4-diaminodiphenyl ether, p-phenylenediamine, 4-diaminodiphenylmethane and 2, 2-bis [4- (4-aminophenoxy) phenyl ] propane; wherein the dianhydride is one or two of pyromellitic dianhydride (PMDA), 3',4,4' -biphenyl tetracarboxylic dianhydride (BPDA), 3',4,4' -Benzophenone Tetracarboxylic Dianhydride (BTDA), 4,4 '-diphenyl ether dianhydride (ODPA) and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride (6FPA), and the dianhydride and the diamine are not simultaneously one; the polar aprotic solvent is one or more of dimethylacetamide, N-methylpyrrolidone and dimethylformamide.
3. The method for preparing a polyimide film with a low dielectric constant and a low dielectric dissipation factor according to claim 1 or 2, wherein: the prepared polyimide film has dielectric constant not more than 2.6 and dielectric loss factor not more than 0.003.
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CN108454192B (en) * 2017-02-17 2020-01-14 昆山雅森电子材料科技有限公司 Double-sided copper foil substrate for PI type high-frequency high-speed transmission and preparation method thereof
CN107190566A (en) * 2017-04-27 2017-09-22 广东粤特变压器有限公司 A kind of new heat modification insulating paper preparation method based on nano modification Kapton
CN108859316B (en) * 2017-05-10 2020-02-21 昆山雅森电子材料科技有限公司 Composite LCP high-frequency high-speed double-sided copper foil substrate and preparation method thereof
CN108882501A (en) * 2017-05-10 2018-11-23 昆山雅森电子材料科技有限公司 Combined type LCP high-frequency high-speed FRCC substrate and preparation method thereof
CN109206906B (en) * 2018-09-12 2021-02-09 无锡创彩光学材料有限公司 Low-dielectric-constant polyimide film with excellent water resistance
CN110655789A (en) * 2019-09-23 2020-01-07 宁波今山新材料有限公司 Low-dielectric low-loss 5G application material and preparation method thereof
CN118749011A (en) * 2022-02-25 2024-10-08 株式会社钟化 Polyimide film for graphite sheet, and method for producing these
CN114479324A (en) * 2022-03-08 2022-05-13 山东森荣新材料股份有限公司 PTFE (polytetrafluoroethylene) protective film for high-frequency copper-clad plate and preparation process thereof

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CN104691066A (en) * 2013-12-05 2015-06-10 达迈科技股份有限公司 Low dielectric constant multilayer polyimide film, laminate thereof, and method for producing same
CN104530703A (en) * 2015-01-20 2015-04-22 无锡顺铉新材料有限公司 Low-dielectric constant polyimide and preparation method thereof

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