CN115028998A - Preparation method of non-halogenated low-loss copper-clad plate for high-frequency and high-speed field - Google Patents

Preparation method of non-halogenated low-loss copper-clad plate for high-frequency and high-speed field Download PDF

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CN115028998A
CN115028998A CN202210824874.3A CN202210824874A CN115028998A CN 115028998 A CN115028998 A CN 115028998A CN 202210824874 A CN202210824874 A CN 202210824874A CN 115028998 A CN115028998 A CN 115028998A
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copper
clad plate
resin
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CN115028998B (en
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秦伟峰
李凌云
刘俊秀
付军亮
陈长浩
王丽亚
史晓杰
徐凤
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SHANDONG JINBAO ELECTRONICS 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
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • 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
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
    • 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
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • 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
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • 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
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
    • B32B2260/021—Fibrous or filamentary layer
    • 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
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/04—Impregnation, embedding, or binder material
    • B32B2260/046—Synthetic resin
    • 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
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2371/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2471/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2471/12—Polyphenylene oxides
    • 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
    • C08J2479/00—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 C08J2461/00 - C08J2477/00
    • C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2479/00—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 C08J2461/00 - C08J2477/00
    • C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34928—Salts
    • 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
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C08K5/5399—Phosphorus bound to nitrogen
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass

Abstract

The invention relates to a preparation method of a non-halogenated and low-loss copper-clad plate for the high-frequency and high-speed field, which has the key technology of a resin composition for manufacturing the copper-clad plate and a bonding sheet and the copper-clad plate manufactured by the resin composition, wherein the resin composition comprises the following components in percentage by weight: 20-100 parts of polyphenyl ether, 10-80 parts of modified cyanate ester resin, 10-30 parts of allyl compound, 50-200 parts of bismaleimide resin, 10-100 parts of curing cross-linking agent, 20-100 parts of halogen-free flame retardant, 10-60 parts of filler and a proper amount of solvent, wherein the total halogen content is less than 900ppm, and the halogen-free requirements of European Union and the like are met; the prepared copper-clad plate has the basic performance of the conventional halogen-free copper-clad plate, excellent dielectric property, dielectric constant DK of less than or equal to 3.4, dielectric loss factor Df of less than or equal to 0.0035 and higher glass transition temperature Tg value of more than or equal to 200 ℃.

Description

Preparation method of non-halogenated low-loss copper-clad plate for high-frequency and high-speed field
Technical Field
The invention belongs to the technical field of copper-clad plate production, and particularly relates to a preparation method of a non-halogenated low-loss copper-clad plate for the high-frequency and high-speed field.
Background
With the acceleration of 5G communication pace and the development of automobile industry towards intellectualization, electromotion and the like, the market demand for high-frequency/high-speed printed circuit boards (PCB for short) is increasing day by day, and the copper-clad plate is required to have lower dielectric constant and dielectric loss.
Many properties of the copper-clad plate are closely related to the base material, and the selection of the resin with excellent dielectric property is one of important ways for realizing the high-frequency/high-speed copper-clad plate. The prior resin suitable for the high-frequency/high-speed copper-clad plate mainly comprises polyimide, polytetrafluoroethylene, polyphenyl ether and other resins which have excellent dielectric properties but have certain defects. For example, polyphenyl ether is a high-performance thermoplastic engineering plastic, is difficult to dissolve in an organic solvent, has insufficient heat resistance, and cannot bear the soldering operation of more than 260 ℃ required by the PCB process; the maleimide resin has excellent heat resistance, good damp and heat resistance, low moisture absorption rate and low thermal expansion coefficient. However, the BMI melting temperature is relatively high, the difference between the BMI melting temperature and the solidification starting temperature is not large, the processing manufacturability is poor, the crosslinking density is high after solidification, the brittleness is large, the bismaleimide resin needs to be compounded with a toughening agent (such as diallyl bisphenol A, epoxy resin and other resins) in the copper-clad plate application, and the bismaleimide resin base copper-clad plate toughened by the method has high dielectric constant (3.9-4.6, 10GHz) and dielectric loss (0.008-0.013, 10GHz), so that the application of the bismaleimide resin base copper-clad plate in the field of 5G communication (high frequency/high speed) electronic products is limited; the unique triazine ring structure of the cyanate ester condensate endows the cyanate ester condensate with excellent dielectric property, lower moisture absorption rate, better dimensional stability, high temperature resistance and a molding process similar to that of epoxy resin. However, the triazine ring structure with a highly regular structure is formed by curing, the crosslinking density is high, so that the cured product of the triazine ring structure is high in brittleness, and the price of the cyanate ester is high, so that the application of the cyanate ester resin is further limited.
With the increasing market demand for high-frequency and high-speed copper-clad plates, the existing process can not meet the performance requirements of products.
Disclosure of Invention
According to the defects of the prior art, the invention aims to provide the preparation method of the non-halogenated low-loss copper-clad plate for the high-frequency high-speed field.
In order to realize the purposes, the adopted technical scheme is as follows:
a preparation method of a non-halogenated low-loss copper-clad plate for the high-frequency and high-speed field comprises the following steps:
(1) uniformly mixing 20-100 parts of polyphenyl ether, 10-80 parts of modified cyanate ester resin, 10-30 parts of allyl compound, 50-200 parts of bismaleimide resin, 10-100 parts of curing cross-linking agent, 20-100 parts of halogen-free flame retardant, 10-60 parts of filler and 5-100 parts of solvent to prepare glue solution;
(2) coating the glue solution obtained in the step (1) on electronic-grade glass cloth, and baking for 5-10min in an oven at the temperature of 130-;
(3) and (3) overlapping a plurality of prepregs prepared in the step (2), covering a copper foil on each of two surfaces of the prepregs, carrying out hot pressing for 240min at the pressure of 1.0-2.8MPa and the temperature of 180-.
Further, the molecular weight of the polyphenylene ether in the step (1) is 800-3000.
Further, the modified cyanate ester resin in the step (1) is a thermoplastic resin modified cyanate ester resin, and the thermoplastic resin is at least one of Polysulfone (PSU), Polyethersulfone (PES), Polyetherimide (PEI), Polycarbonate (PC), Polyetherketone (PEK), and polyphenylene oxide (PPO).
Further, the allyl compound in the step (1) is diallyl bisphenol A or diallyl bisphenol S.
Further, in the step (1), the bismaleimide resin is bismaleimide diphenyl methyl ether or bismaleimide diphenylmethane.
Still further, the curing crosslinking agent in the step (1) comprises the following components in percentage by weight:
10-50% of triallyl cyanurate
Triallyl isocyanurate 20-60%
10-50% of trimethylolpropane trimethacrylate.
Further, the halogen-free flame retardant in the step (1) comprises the following components in percentage by weight:
Figure BDA0003743623620000031
further, the filler in the step (1) is at least one of spherical silica micropowder and fused silica micropowder.
Further, in the step (1), the solvent is one or more selected from toluene, benzene, xylene, acetone, butanone, ethyl acetate and butyl acetate.
And further, the glue solution in the step (1) is a resin solution with solid content of 50-75%.
Compared with the prior art, the invention has the beneficial effects that:
(1) the polyphenyl ether adopted by the invention can react with the modified cyanate ester resin and the bismaleimide resin to form a cross-linked network structure, so that high addition amount can be realized, the dielectric properties and toughness of the cyanate ester resin and the bismaleimide resin can be effectively improved, and meanwhile, proper heat resistance can be kept;
(2) the non-halogenated low-loss copper-clad material prepared by the invention has good mechanical property and heat resistance, and simultaneously has good dielectric property: the dielectric constant Dk is less than or equal to 3.4 under 10GHz, the dielectric loss factor Df (10GHz) is less than or equal to 0.0035, the thermal expansion coefficient of the Z axis is less than or equal to 1.85%, the glass transition temperature Tg can reach more than 210 ℃, the peel strength is 1.51-1.85N/mm, the copper-clad plate can be used for meeting the technical requirement of the copper-clad plate under the 5G communication technical condition, the total halogen content is less than 900ppm, and the non-halogenation requirements of European Union and the like are met;
(3) the copper-clad plate prepared by the invention is halogen-free and environment-friendly, the method has simple process flow, is convenient to produce, has good product performance, and can better meet the market demand.
Detailed Description
The present invention is described below with reference to examples, which are provided for illustration only and are not intended to limit the scope of the present invention.
Example 1
A preparation method of a non-halogenated low-loss copper-clad plate for the high-frequency and high-speed field comprises the following steps:
(1) taking 50 parts of polyphenylene oxide with molecular weight of 2000, 60 parts of polyethersulfone cyanate, 20 parts of diallyl bisphenol A, 80 parts of bismaleimide diphenylmethane, 50 parts of curing crosslinking agent (30% of triallyl cyanurate, 30% of triallyl isocyanurate and 40% of trimethylolpropane trimethacrylate), 40 parts of halogen-free flame retardant (40% of DOPO (9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide), 40% of hexaphenoxycyclotriphosphazene and 20% of melamine-isocyanuric acid), 60 parts of filler spherical silicon micro powder, 60 parts of toluene and 30 parts of butanone, and uniformly mixing to prepare a glue solution;
(2) coating the glue solution obtained in the step (1) on electronic-grade glass cloth, and baking for 8min in a baking oven at 150 ℃ to obtain a prepreg;
(3) and (3) overlapping 6 prepregs prepared in the step (2), covering a copper foil on each of two surfaces of the prepregs, carrying out hot pressing for 240min under the conditions that the pressure is 2.8MPa and the temperature is 240 ℃, and cooling to obtain the copper-clad plate.
Example 2
A preparation method of a non-halogenated low-loss copper-clad plate for the high-frequency and high-speed field comprises the following steps:
(1) taking 80 parts of polyphenyl ether with the molecular weight of 3000, 50 parts of polyether ketone cyanate, 30 parts of diallyl bisphenol S, 60 parts of bismaleimide diphenyl methyl ether, 60 parts of a curing crosslinking agent (wherein 20% of triallyl cyanurate, 30% of triallyl isocyanurate and 50% of trimethylolpropane trimethacrylate) by weight, 45 parts of a halogen-free flame retardant (wherein 30% of DOPO (9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) by weight, 30% of hexaphenoxycyclotriphosphazene and 40% of melamine-isocyanuric acid by weight), 50 parts of filler fused silica micro powder, 50 parts of xylene and 30 parts of acetone by weight, and uniformly mixing to prepare a glue solution;
(2) coating the glue solution obtained in the step (1) on electronic-grade glass cloth, and baking for 10min in an oven at 140 ℃ to obtain a prepreg;
(3) and (3) overlapping 6 prepregs prepared in the step (2), covering a copper foil on each of two surfaces of the prepregs, hot-pressing for 200min under the conditions that the pressure is 2.5MPa and the temperature is 260 ℃, and cooling to obtain the copper-clad plate.
Comparative example 1
Comparative example 1 is different from example 1 in that polyphenylene ether having a molecular weight of 2000 was not added to the raw materials.
Comparative example 2
Comparative example 2 differs from example 1 in that no polyethersulfone cyanate was added to the feed.
Testing of
The copper-clad plates prepared in examples 1-2 and comparative examples 1-2 were subjected to heat resistance, glass transition temperature, dielectric constant and dielectric loss tests, and the test results are shown in table 1.
TABLE 1 comparison of Performance data for copper clad laminates of examples 1-2 and comparative examples 1-2
Figure BDA0003743623620000051
As can be seen from Table 1, compared with comparative examples 1-2, the copper-clad plate prepared in examples 1-2 has the advantages that the polyphenyl ether can react with the modified cyanate ester resin and the bismaleimide resin to form a cross-linked network structure, so that high addition amount is realized, dielectric properties and toughness of the cyanate ester resin and the bismaleimide resin are effectively improved, and meanwhile, proper heat resistance can be maintained, the dielectric constant Dk (10GHz) of the prepared copper-clad plate is 3.35-3.39, the dielectric loss factor Df (10GHz) is 0.0031-0.0032, the thermal expansion coefficient of the Z axis is 1.8-1.85, and the glass transition temperature Tg can reach more than 210 ℃.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (10)

1. A preparation method of a non-halogenated low-loss copper-clad plate for the high-frequency and high-speed field is characterized by comprising the following steps:
(1) uniformly mixing 20-100 parts of polyphenyl ether, 10-80 parts of modified cyanate ester resin, 10-30 parts of allyl compound, 50-200 parts of bismaleimide resin, 10-100 parts of curing cross-linking agent, 20-100 parts of halogen-free flame retardant, 10-60 parts of filler and 5-100 parts of solvent to prepare glue solution;
(2) coating the glue solution obtained in the step (1) on electronic-grade glass cloth, and baking for 5-10min in an oven at the temperature of 130-;
(3) and (3) overlapping a plurality of prepregs prepared in the step (2), covering a copper foil on each of two surfaces of the prepregs, carrying out hot pressing for 240min at the pressure of 1.0-2.8MPa and the temperature of 180-.
2. The production method as described in claim 1, wherein the polyphenylene ether in the step (1) has a molecular weight of 800-3000.
3. The preparation method according to claim 1, wherein the modified cyanate ester resin in step (1) is a thermoplastic resin modified cyanate ester resin, and the thermoplastic resin is at least one of Polysulfone (PSU), Polyethersulfone (PES), Polyetherimide (PEI), Polycarbonate (PC), Polyetherketone (PEK), and polyphenylene oxide (PPO).
4. The method according to claim 1, wherein the allyl compound in the step (1) is diallyl bisphenol a or diallyl bisphenol S.
5. The method according to claim 1, wherein the bismaleimide resin in the step (1) is bismaleimide diphenyl methyl ether or bismaleimide diphenylmethane.
6. The method according to claim 1, wherein the curing crosslinking agent in step (1) comprises the following components in percentage by weight:
10-50% of triallyl cyanurate
Triallyl isocyanurate 20-60%
10-50% of trimethylolpropane trimethacrylate.
7. The preparation method according to claim 1, wherein the halogen-free flame retardant in step (1) comprises the following components in percentage by weight:
9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) 10-40%
10 to 60 percent of hexaphenoxycyclotriphosphazene
5-50% of melamine-isocyanuric acid.
8. The method according to claim 1, wherein the filler in step (1) is at least one of spherical fine silica powder and molten fine silica powder.
9. The method according to claim 1, wherein the solvent in step (1) is one or more selected from toluene, benzene, xylene, acetone, methyl ethyl ketone, ethyl acetate and butyl acetate.
10. The preparation method according to claim 1, wherein the glue solution in the step (1) is a resin solution with a solid content of 50-75%.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117087264A (en) * 2023-06-15 2023-11-21 明光瑞智电子科技有限公司 High-frequency high-speed copper-clad plate and preparation method thereof

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US20130075138A1 (en) * 2011-09-22 2013-03-28 Li-Chih Yu Halogen-free resin composition and copper clad laminate and printed circuit board using same
CN103013110A (en) * 2011-09-27 2013-04-03 台光电子材料股份有限公司 Halogen-free resin composition as well as copper foil substrate and printed circuit board applying same
CN104177809A (en) * 2013-05-21 2014-12-03 台光电子材料股份有限公司 Low-dielectric halogen-free resin composition and application thereof
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