CN104974469A - Resin combination, and prepreg and laminated board prepared from same - Google Patents
Resin combination, and prepreg and laminated board prepared from same Download PDFInfo
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- CN104974469A CN104974469A CN201510394927.2A CN201510394927A CN104974469A CN 104974469 A CN104974469 A CN 104974469A CN 201510394927 A CN201510394927 A CN 201510394927A CN 104974469 A CN104974469 A CN 104974469A
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Abstract
The invention discloses a resin combination comprising the following components according to the solid weight: (a) 2-50 parts of an acid anhydride; (b) 1-70 parts of benzoxazine resin; (c) 5-70 parts of epoxy resin; (d) not less than 1 part and less than 10 parts of cyanate resin; (e) 0-50 parts of a flame retardant; and f) 0-10 parts of a reaction auxiliary agent, wherein the reaction auxiliary agent is polycarbodiimide. An obtained laminated board has the advantages of high resistance to heat and humidity, high toughness, high glass transition temperature, lower dielectric constant and lower dielectric loss tangent value, and can satisfy requirements of printed circuit board on high performance such as high frequency, high speed and high density interconnection.
Description
Technical field
The invention belongs to technical field of electronic materials, relate to a kind of resin combination and the prepreg using it to make and veneer sheet.
Background technology
In today of information technology fast development, each electronic product of collection multifunction, diversification is just becoming a part indispensable in people's life, the relativity of information of electronic product progressively increases, information processing rate is also constantly accelerated, this just requires that electronic signal has higher transfer rate in the components and parts of printed circuit board and institute's load thereof, and this just requires that copper clad laminate material has lower specific inductivity; Simultaneously, in order to realize the high-fidelity of signal under high-speed transfer, concentrate to solve lightening and intensive lower the brought thermal losses of high speed of electronic product and be difficult to the problem of dissipation, require that baseplate material has lower dielectric loss tangent value, with the generation of the loss and heat that reduce signal.
At present, in resin combination for high-frequency high-speed substrate, the most frequently used resin is cyanate ester resin, but under cyanate ester resin has the existence of hydroxyl in system, the generation of its self-polymeric reaction of meeting catalysis, in collecting process, first hydroxyl can react with cyano group the binary intermediate producing a kind of imido-carbonic ester, thus accelerates the formation of triazine ring; As: a small amount of nonyl phenol is the catalyzer in cyanate curing reaction, is also by the atom N on reactive hydrogen attack-OCN, reduces the positive charge on C atom, thus promotes the generation of two-element active intermediate, accelerates curing reaction.Meanwhile, cross the existence of poly-hydroxy in resin system, also cause the too much residual of the binary intermediate of imido-carbonic ester, and imido-carbonic ester is after wet heat treatment, namely about 200 DEG C easily there is decomposition reaction, and this is also one of poor reason of cyanate ester resin humidity resistance.Therefore, there is certain restriction in the application of cyanate in high-frequency high-speed resin combination.In addition, in epoxy anhydride curing system, produce thermostability and the bad carboxyl of humidity resistance or hydroxyl when there is curing reaction, therefore also there is certain restriction in anhydride curing agent application in the epoxy.
As everyone knows, resin matrix is meeting moisture absorption in damp and hot environment, the moisture sucked makes the performance of baseplate material sharply decline, as thermal expansivity, thermotolerance, interlayer adhesion, specific inductivity, Dielectric loss tangent value etc. to the plasticizing of matrix and swelling action and because of the tiny crack that produced internal stress causes that do not mate of the damp and hot coefficient of expansion of resin and glasscloth; That is, each performance variation under dry and moisture absorption two states varies; Therefore, the humidity resistance of resin cured matter is the primary factor determining material over-all properties.Such as, Chinese invention patent application CN103937157A discloses the composition adding cyanate ester resin in a kind of epoxy anhydride benzo system, and wherein the content of cyanate ester resin is 10 ~ 80 parts.Although this technical scheme can improve second-order transition temperature and the dielectric properties of system, but humidity resistance can be caused more deteriorated, therefore cause the improvement of second-order transition temperature and dielectric properties can not meet the requirement of the contour performance printed circuit board of high density interconnect.
Therefore, develop a kind of resin combination with high wet-hot aging performance, high glass-transition temperature, high tenacity, lower specific inductivity and dielectric loss tangent value, to meet the requirement of high-frequency high-speed and the contour performance printed circuit board of high density interconnect, obviously there is positive realistic meaning.
Summary of the invention
Goal of the invention of the present invention is to provide a kind of resin combination and the prepreg using it to make and veneer sheet.
To achieve the above object of the invention, the technical solution used in the present invention is: a kind of resin combination, with solid weight meter, comprises following component:
(a) anhydride compound: 2 ~ 50 parts;
(b) benzoxazine resin: 1 ~ 70 part;
(c) epoxy resin: 5 ~ 70 parts;
(d) 1 part≤cyanate ester resin <10 part;
(e) fire retardant: 0 ~ 50 part;
(f) reaction promoter: 0 ~ 10 part;
Wherein, described reaction promoter is polycarbodiimide.
Above, the number-average molecular weight of described reaction promoter is 1000 ~ 28000g/mol.
Experiment finds: in resin combination, when epoxy resin and acid anhydrides react, produce the carboxyl that thermostability is bad, therefore thermotolerance and the second-order transition temperature of whole system can be affected, but after interpolation reaction promoter, not only the second-order transition temperature of cured article significantly improves, and humidity resistance also improves, and reduces specific inductivity and Dielectric loss tangent value further simultaneously; But when the content of reaction promoter is more than 10 parts, the consistency in resin combination and between other resins is bad, can separates out in resin system, the over-all properties of sheet material can be affected.
Preferably, the content of described cyanate ester resin is 3 ~ 6 parts.Experiment finds: in resin combination, when the content of cyanate ester resin is more than 10 parts, the humidity resistance of cured article obviously declines, and reduce the toughness of cured article, also affect second-order transition temperature and dielectric properties simultaneously, when the content of cyanate ester resin is less than 1 part, in resin curing system, the content of triazine ring reduces, and affects original excellent specific property of triazine ring; And when the content of cyanate ester resin is at 3 ~ 6 parts, humidity resistance, second-order transition temperature, dielectric properties and cured article toughness reach certain trim point the most significantly, excellent combination property, can meet the requirement of high-frequency high-speed and the contour performance printed circuit board of high density interconnect.
In technique scheme, in composition, curing catalyst can also be added.Described curing catalyst is metal salts of organic acids or imidazoles, and described organic metal salt is the lipid acid metal salts of organic acids of cobalt, nickel, manganese, zinc, copper etc., preferably octanoic acid zinc or cobalt octoate, and its content in resin combination is 0.001 ~ 3 part.
In technique scheme, mineral filler can also be added.Described mineral filler is selected from one or more in aluminium hydroxide, magnesium hydroxide, wollastonite, silicon dioxide powder, magnesium oxide, Calucium Silicate powder, silica microspheres, calcium carbonate, clay, kaolin, glass powder, mica powder, titanium dioxide, zinc borate, zinc molybdate.Mineral filler powder shaped can directly drop into or previously prepared fillers dispersed liquid or make lotion and drop in resin combination.The particle size range of mineral filler controls at 0.3 ~ 20 micron, and preferable particle size is 0.5 ~ 5 micron, and its content in resin combination is 5 ~ 60 parts.
In technique scheme, toughner can also be added.Described toughner is at least one in the epoxy resin of high molecular, phenoxy resin, rubber, cyclic olefin polymer, and its content in resin combination is 0.1 ~ 10 part.
Preferably, the content of described reaction promoter is 0.5 ~ 3 part.
Preferably, the mass ratio of described reaction promoter and anhydride compound is 1:6 ~ 10.
In technique scheme, described anhydride compound is selected from styrene-maleic anhydride, 3, and 3 ', 4,4 '-oxydiphthalic, 2,3,3', 4'-diphenyl ether tetraformic dianhydrides, 3,3', 4,4'-bibenzene tetracarboxylic dianhydride, 2,3,3', 4'-bibenzene tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, Bisphenol A Type Diether Dianhydride, 1, one or more in 2,4,5-pyromellitic acid dianhydride.
In technique scheme, described benzoxazine resin is selected from bisphenol A-type benzoxazine resin, bisphenol-f type benzoxazine resin, 4, one or more in 4 ' diaminodiphenylmethane benzoxazine resin, diaminodiphenyl oxide benzoxazine resin, diaminodiphenylsulfone(DDS) benzoxazine resin, allyl group bisphenol A benzoxazine resin, its content range preferably 8 ~ 45 parts.
In technique scheme, described epoxy resin is selected from one or more in bisphenol A epoxide resin, bisphenol F epoxy resin, phosphorous epoxy resin, o-cresol formaldehyde epoxy resin, bisphenol-A phenolic epoxy resin, phenol novolac epoxy resins, trifunctional phenol-type epoxy resin, tetraphenyl ethane epoxy resin, biphenyl type epoxy resin, naphthalene nucleus type epoxy resin, dicyclopentadiene type epoxy resin, aralkyl novolac epoxy resin, glycidyl amine type epoxy resin, glycidyl ester type epoxy resin.
In technique scheme, described cyanate ester resin is selected from one or more in bisphenol A cyanate ester resin, Novolac Cyanate Ester Resins, bisphenol-f type cyanate ester resin, biphenyl type cyanate ester resin, naphthalene type cyanate ester resin, phosphorous cyanate ester resin, Epoxies Resins Modified Cyanater, bis-phenol M type cyanate ester resin and dicyclopentadiene type ethylene rhodanate.
Preferably, described fire retardant is phosphazene compound.Preferably, its content is 2 ~ 30 parts.Experiment finds: in resin combination, during with phosphonitrile as fire retardant, not only can meet flame retardant resistance (UL94V-0), and the humidity resistance of system can be improved further, simultaneously, phosphazene compound consistency in epoxy anhydride resin system is better, effectively can improve the surface smoothness of prepreg.
Certainly, fire retardant also can be other existing P contained compound or brominated flame-retardants.Described brominated flame-retardant is selected from least one in tribromo phenyl maleimide, tetrabromo-bisphenol allyl ethers, TDE, decabrominated dipheny ether, brominated Polystyrene, brominated polycarbonate, tetrabromo-bisphenol, brominated epoxy resin; Described phosphonium flame retardant is selected from containing at least one in DOPO and derivative thereof, phosphorus epoxy resin, phosphorus containing phenolic resin, phosphate compound, phosphorous cyanate, phosphorous bismaleimides.
The present invention asks to protect a kind of prepreg adopting above-mentioned resin combination to make simultaneously, and above-mentioned resin combination dissolution with solvents is made glue, is then immersed in by strongthener in above-mentioned glue; After flooding after strongthener baking, described prepreg can be obtained.
One or more in described solvent selected from acetone, butanone, mibk, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, ethylene glycol monomethyl ether, propylene glycol monomethyl ether.
Described strongthener can adopt glass-fiber-fabric, as D glass-fiber-fabric, E glass-fiber-fabric, NE glass-fiber-fabric, S glass-fiber-fabric and T glass-fiber-fabric.Here the thickness of glass-fiber-fabric is not particularly limited, but for producing the veneer sheet of thickness 0.03 ~ 0.20mm, general use fibrillation cloth, flat fabric.In addition, in order to improve the interface cohesion of resin and glass-fiber-fabric, glass-fiber-fabric generally all needs to carry out chemical treatment, and main method is coupling agent treatment, coupling agent used as epoxy silane, aminosilane, vinyl silanes etc.
Described prepreg be temperature at 150 ~ 180 DEG C, the time be under 1 ~ 15min dry preparation obtain.
The present invention asks to protect a kind of veneer sheet adopting above-mentioned resin combination to make simultaneously; tinsel is covered with by the single or double of above-mentioned prepreg at one; or after at least 2 are superposed by above-mentioned prepreg; tinsel is covered with at its single or double; in 0.2 ~ 2MPa pressure and 180 ~ 210 DEG C of temperatures systems 2 ~ 4 hours, described veneer sheet can be obtained.
The quantity of described prepreg determines according to the laminate thickness of customer requirement, available one or more.Described tinsel can be Copper Foil, and can be also aluminium foil, thickness be not particularly limited.
Because technique scheme is used, the present invention compared with prior art has following advantages:
1. experiment proves: compared with prior art (Chinese invention patent application CN103937157A), the veneer sheet that the present invention obtains has high wet-hot aging performance, high tenacity, high glass-transition temperature, lower specific inductivity and dielectric loss tangent value, can meet the requirement of high-frequency high-speed and the contour performance printed circuit board of high density interconnect;
2. experiment proves: after the present invention adds appropriate reaction promoter in epoxy anhydride resin combination, can improve the thermostability of cured article further, significantly improve second-order transition temperature and the humidity resistance of sheet material;
3. the present invention adopts phosphonitrile as fire retardant, not only can meet flame retardant resistance (UL94V-0), and the humidity resistance of system can be improved further, phosphazene compound consistency in epoxy anhydride resin system is better simultaneously, effectively can improve the surface smoothness of prepreg, the field such as high-frequency high-speed and high density interconnect can be applicable to better.
Embodiment
Below in conjunction with embodiment, the present invention is further described.
Embodiment
A kind of resin combination, with solid weight meter, comprises following component, shown in seeing table:
Table 1 composition Example formulations
Comparative example
A kind of resin combination, with solid weight meter, comprises following component, shown in seeing table:
Table 2 composition comparative examples formula
In table 1 and 2, component A represents cyanate resin alicyclic monomer or its prepolymer, B component represents anhydride compound, component C represents benzoxazine resin, D component representative ring epoxy resins, component E represent fire retardant, F component represents reaction promoter, G component represents curing catalyst, H component represents mineral filler.Specific as follows:
A1: bisphenol A cyanate ester resin;
A2: bisphenol-f type cyanate ester resin;
B1: styrene-maleic anhydride compound;
B2:3,3', 4,4'-bibenzene tetracarboxylic dianhydride compound;
C1: bisphenol A-type benzoxazine resin;
C2: bisphenol-f type benzoxazine resin;
D1: bisphenol A epoxide resin;
D2: naphthalene nucleus type epoxy resin;
E1: phosphazene compound, phosphorus content 12%wt;
E2: TDE;
F: reaction promoter: polycarbodiimide, its number-average molecular weight is 3000 ~ 4500g/mol; Lay mattress chemistry system;
G: curing catalyst: zinc octoate;
H: silicon-dioxide, particle diameter 0.5 ~ 5 micron.
Above-mentioned resin combination adopts conventional preparation method to obtain: cyanate ester resin, benzoxazine resin, anhydride compound, epoxy resin, fire retardant, reaction promoter, curing catalyst and appropriate mineral filler and solvent are joined in mixed glue still, solids content is 55 ~ 70%, stir, and slaking 4 ~ 8 hours, make compositions of thermosetting resin glue of the present invention;
Then strongthener is immersed in above-mentioned compositions of thermosetting resin glue; Then the strongthener after dipping is formed after toasting 3 ~ 7min drying under 155 ~ 175 DEG C of environment and namely form prepreg provided by the invention.
Adopt the veneer sheet that above-mentioned prepreg is obtained, its manufacture method comprises the steps:
1) by 8 described prepreg superpositions,
2) Copper Foil is covered with the two-sided of described prepreg,
3) hot compacting, the lamination of copper-clad laminate need meet following requirement: the temperature rise rate of (1) lamination: the temperature rise rate usually when material temperature 30 ~ 160 degrees Celsius should control at 0.8 ~ 5.0 DEG C/min; (2) pressure of lamination is arranged: outer material temperature need apply full pressure 70 ~ 110 degrees Celsius time, and full pressure pressure is about 300psi; (3), during solidification, control material temperature more than 190 DEG C, and be at least incubated 90min.
Table 3 and 4 is the performance test carried out embodiment and comparative example respectively, and result is as follows:
The performance data of table 3 embodiment
The performance data of table 4 comparative example
In upper table, the testing method of each performance is as follows:
(1) second-order transition temperature (Tg): according to dsc, measures according to the DSC method of IPC-TM-6502.4.25 defined.
(2) stripping strength (PS): according to " after the thermal stresses " experiment condition in IPC-TM-6502.4.8 method, the stripping strength of test metallic cover layer.
(3) wicking thermotolerance: the two sides band copper sample using 50 × 50mm, immerses in the scolding tin of 288 DEG C, the time of record sample layering bubble.
(4) wicking thermotolerance after moist process: by the substrate coupons of 20 pieces of 100 × 100mm 121 DEG C, keep 2hr in the pressure cooking treatment unit of 105Kpa after, immerses 2min in the solder bath of 288 DEG C, whether observation sample there is the phenomenons such as layering bubbling.
(5) heat decomposition temperature Td: measure according to IPC-TM-6502.4.26 method.
(6) specific inductivity: use flat band method according to IPC-TM-6502.5.5.9, measures the specific inductivity under 1GHz.
(7) dielectric loss angle tangent: use flat band method according to IPC-TM-6502.5.5.9, measures the dielectric loss factor under 1GHz.
(8) drop impact toughness (veneer sheet fragility): use Apparatus for Impacting at low-temp, Apparatus for Impacting at low-temp height of the fall 45cm, whereabouts weight weight 1kg.The judge that toughness is good and bad: cross bar is clear, illustrates that the toughness of product is better, represents with character ☆; Cross bar is fuzzy, illustrates that the poor toughness of product, fragility are large, represents with character ◎; Cross bar readability illustrates that toughness of products is general between clear and fuzzy, represents with character ◇.
(9) thermally stratified layer time T-300: measure according to IPC-TM-6502.4.24 method.
(10) thermal expansivity Z axis CTE (TMA): measure according to IPC-TM-6502.4.24 method.
(11) resistance to flame (flame retardancy): measure according to UL94 method.
(12) solvability: after mixed glue liquid, leaves standstill 24 hours, observing and whether has precipitation or demixing phenomenon, as not having, representing with character √, if having, with character × represent.
From table 3 and 4 contrasts, the veneer sheet that the present invention obtains not only humidity resistance is better, and when adding less cyanate, also excellent dielectric properties, high glass-transition temperature and higher toughness can be obtained, thus the field such as high-frequency high-speed and high density interconnect can be advantageously applied to.
And comparative example one and five (according to Chinese invention patent application CN103937157A) is although can improve second-order transition temperature and dielectric properties, after moist process, wicking thermotolerance is obviously poor, and the toughness of sheet material also obviously reduces simultaneously.
In comparative example two, when the content of cyanate is lower than 1 part, the ratio of the triazine ring in cured article reduces, thus affects dielectric properties and the thermotolerance of the excellence that triazine ring brings.
In comparative example three, when the content of reaction promoter is more than 10 parts, although can improve the second-order transition temperature of cured article, and consistency between other resins is poor, affect the stripping strength of Copper Foil, humidity resistance and thermally stratified layer performance etc., over-all properties is poor.
In comparative example four, when anhydride content exceedes certain limit, the humidity resistance after the humidity process of cured article and toughness obviously decline.
In sum, resin combination of the present invention has high wet-hot aging performance, high tenacity, high glass-transition temperature, lower specific inductivity and dielectric loss tangent value, can meet the requirement of high-frequency high-speed and the contour performance printed circuit board of high density interconnect.
Above embodiment, not the content of composition of the present invention is imposed any restrictions, every above embodiment is done according to technical spirit of the present invention or composition composition or content any trickle amendment, equivalent variations and modification, all still belong in the scope of technical solution of the present invention.
Claims (10)
1. a resin combination, is characterized in that, with solid weight meter, comprises following component:
(a) anhydride compound: 2 ~ 50 parts;
(b) benzoxazine resin: 1 ~ 70 part;
(c) epoxy resin: 5 ~ 70 parts;
(d) 1 part≤cyanate ester resin <10 part;
(e) fire retardant: 0 ~ 50 part;
(f) reaction promoter: 0 ~ 10 part;
Wherein, described reaction promoter is polycarbodiimide.
2. resin combination according to claim 1, is characterized in that: the content of described reaction promoter is 0.5 ~ 3 part.
3. resin combination according to claim 1, is characterized in that: the mass ratio of described reaction promoter and anhydride compound is 1:6 ~ 10.
4. resin combination according to claim 1, is characterized in that: described anhydride compound is selected from styrene-maleic anhydride, 3,3 ', 4,4 '-oxydiphthalic, 2,3,3', 4'-diphenyl ether tetraformic dianhydrides, 3,3', 4,4'-bibenzene tetracarboxylic dianhydride, 2,3,3', 4'-bibenzene tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, Bisphenol A Type Diether Dianhydride, 1, one or more in 2,4,5-pyromellitic acid dianhydride.
5. resin combination according to claim 1, it is characterized in that: described benzoxazine resin is selected from bisphenol A-type benzoxazine resin, bisphenol-f type benzoxazine resin, 4, one or more in 4 ' diaminodiphenylmethane benzoxazine resin, diaminodiphenyl oxide benzoxazine resin, diaminodiphenylsulfone(DDS) benzoxazine resin, allyl group bisphenol A benzoxazine resin.
6. resin combination according to claim 1, is characterized in that: described epoxy resin is selected from one or more in bisphenol A epoxide resin, bisphenol F epoxy resin, phosphorous epoxy resin, o-cresol formaldehyde epoxy resin, bisphenol-A phenolic epoxy resin, phenol novolac epoxy resins, trifunctional phenol-type epoxy resin, tetraphenyl ethane epoxy resin, biphenyl type epoxy resin, naphthalene nucleus type epoxy resin, dicyclopentadiene type epoxy resin, aralkyl novolac epoxy resin, glycidyl amine type epoxy resin, glycidyl ester type epoxy resin.
7. resin combination according to claim 1, is characterized in that: described cyanate ester resin is selected from one or more in bisphenol A cyanate ester resin, Novolac Cyanate Ester Resins, bisphenol-f type cyanate ester resin, biphenyl type cyanate ester resin, naphthalene type cyanate ester resin, phosphorous cyanate ester resin, Epoxies Resins Modified Cyanater, bis-phenol M type cyanate ester resin and dicyclopentadiene type ethylene rhodanate.
8. resin combination according to claim 1, is characterized in that: described fire retardant is phosphazene compound.
9. the prepreg adopting resin combination as claimed in claim 1 to make, is characterized in that: resin combination dissolution with solvents according to claim 1 is made glue, is then immersed in by strongthener in above-mentioned glue; After flooding after strongthener baking, described prepreg can be obtained.
10. the veneer sheet adopting resin combination as claimed in claim 1 to make, it is characterized in that: be covered with tinsel at one by the single or double of prepreg according to claim 9, or after at least 2 are superposed by prepreg according to claim 9, tinsel is covered with at its single or double, in 0.2 ~ 2MPa pressure and 180 ~ 210 DEG C of temperatures systems 2 ~ 4 hours, described veneer sheet can be obtained.
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| US20180362733A1 (en) * | 2017-06-14 | 2018-12-20 | Elite Electronic Material (Kunshan) Co., Ltd. | Resin composition and articles made therefrom |
| CN109233543A (en) * | 2017-05-03 | 2019-01-18 | 中山台光电子材料有限公司 | Resin combination and the article being made from it |
| CN113121957A (en) * | 2019-12-31 | 2021-07-16 | 广东生益科技股份有限公司 | Halogen-free thermosetting resin composition, and prepreg, laminated board and printed circuit board using same |
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| CN114702785A (en) * | 2022-03-22 | 2022-07-05 | 深圳市纽菲斯新材料科技有限公司 | Low dielectric resin composition, copper foil, and preparation method and application thereof |
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| CN107365476A (en) * | 2016-05-12 | 2017-11-21 | 中山台光电子材料有限公司 | Resin combination and by its obtained finished product |
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| CN113121957A (en) * | 2019-12-31 | 2021-07-16 | 广东生益科技股份有限公司 | Halogen-free thermosetting resin composition, and prepreg, laminated board and printed circuit board using same |
| WO2021212326A1 (en) * | 2020-04-21 | 2021-10-28 | 穗晔实业股份有限公司 | Thermosetting resin composition |
| CN114702785A (en) * | 2022-03-22 | 2022-07-05 | 深圳市纽菲斯新材料科技有限公司 | Low dielectric resin composition, copper foil, and preparation method and application thereof |
| CN114702785B (en) * | 2022-03-22 | 2023-12-19 | 深圳市纽菲斯新材料科技有限公司 | Low-dielectric resin composition, copper foil, and preparation method and application thereof |
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