CN104109347B - A kind of halogen-free thermosetting resin composite, prepreg and laminate - Google Patents
A kind of halogen-free thermosetting resin composite, prepreg and laminate Download PDFInfo
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- CN104109347B CN104109347B CN201410232136.5A CN201410232136A CN104109347B CN 104109347 B CN104109347 B CN 104109347B CN 201410232136 A CN201410232136 A CN 201410232136A CN 104109347 B CN104109347 B CN 104109347B
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Abstract
The invention discloses a kind of halogen-free thermosetting resin composite, prepreg and laminate, halogen-free thermosetting resin composite, with solid weight meter, including: (a) epoxy resin: 30 ~ 50 parts；(b) modified polyphenylene ether resin: 5 ~ 40 parts；(c) phosphorous active ester: 15 ~ 50 parts；(d) reinforcing agent: 0 ~ 20 part.The present invention devises the resin combination of a kind of halogen-free flameproof low-k with phosphorous active ester as fire retardant, the application of phosphorous active ester, avoid after introducing as fire retardant because of introducing phosphorous epoxy resin or phosphorus containing phenolic resin or phosphate ester, the rising of resin water absorption rate；It is simultaneously introduced appropriate modified polyphenylene ether resin, it is possible to obtain there is more excellent dielectric constant, is more beneficial for it and is applied to Halogen high speed contour performance printed wiring board field.
Description
Technical field
The invention belongs to technical field of electronic materials, relate to a kind of halogen-free resin composition and the prepreg using it to make and laminate, can be applicable to the fields such as high density interconnection integrated antenna package.
Background technology
For a long time, epoxy resin, owing to having the comprehensive advantages such as raw material sources is extensive, processability good, cost is relatively low, has obtained a large amount of in FR-4 laminate and has been widely applied.But, the high-speed high frequency transmitted along with information processing in recent years and information, laminate used for printed circuit is had higher requirement in terms of dielectric properties.In simple terms, i.e. laminate sheet material need to possess low dielectric constant and dielectric loss, interference between the delay of signal, distortion and loss, and signal during to reduce high-speed transfer.But, common epoxy resin dielectric constant and dielectric loss are higher, it is difficult to meet the application in terms of high frequency.Polyphenylene oxide is a kind of high performance resin, due to symmetry, less intermolecular force and higher aryl ratio that its strand is good, make it have the dielectric property of excellence, the lowest dielectric constant and dielectric loss, the frequency applications requirement to dielectric material performance can be met well.Meanwhile, polyphenylene oxide also has the impact flexibility etc. of higher glass transition temperature, low water absorption and excellence, has broad application prospects in high frequency laminate sheet material.
Simultaneously, progressively intensification along with environmental pollution, the living environment gone from bad to worse, the theme of " environmental protection " is gradually rooted in the hearts of the people, therefore, in copper-clad plate industry, green halogen-free board develops the Main way of development in recent years especially, and the main technological route being applied to halogen-free flameproof of phosphonium flame retardant.At present, widely used on copper-clad plate market phosphorus flame retardant: be broadly divided into response type and addition type two kinds.Response type is mainly DOPO compounds, based on phosphorous epoxy resin, phosphorus containing phenolic resin, phosphorus content is between 2-10%, but, actual application finds, using phosphorous epoxy resin is the resin combination of epoxy curing agent as matrix resin or employing phosphorus containing phenolic resin, and it has bigger water absorption rate and higher dielectric constant, and the humidity resistance of its sheet material made decreases；Addition type is mainly phosphine nitrile and phosphate compounds, the flame retarding efficiency relative response type of additive flame retardant is on the low side, needing to add more phosphorus content, to can be only achieved UL 94V-0 level fire-retardant, simultaneously, because of its relatively low fusing point (generally below 150 DEG C), in the course of processing of laminate, the surface of easy " migration " to sheet material.
Therefore, the application of above-mentioned phosphor-containing flame-proof technology, tend not to meet the requirement of the resin composition formula design of low-k, excellent humidity resistance, seek new halogen-free flame retardants, prepare and have halogen-free flameproof and high-fire resistance, the copper-clad plate of low-k concurrently, become one of direction of copper-clad plate future development.
Summary of the invention
The goal of the invention of the present invention is to provide a kind of halogen-free thermosetting resin composite and the prepreg using it to make and laminate, to improve the fire resistance of laminate, thermostability, dielectric properties, reduces water absorption rate.
To achieve the above object of the invention, the technical solution used in the present invention is:
A kind of halogen-free thermosetting resin composite, is in terms of 100 parts by solid weight sum, including:
(a) epoxy resin: 30 ~ 50 parts；
(b) modified polyphenylene ether resin: 5 ~ 40 parts；
(c) phosphorous active ester: 15 ~ 50 parts；
(d) reinforcing agent: 0 ~ 20 part.
In technique scheme, described epoxy resin is selected from: bisphenol A epoxide resin, bisphenol F 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, one or more mixture of glycidyl ester type epoxy resin.
In technique scheme, the structural formula of described phosphorous active ester compound is,
,
In formula, R1 is methyl, ethyl or the tert-butyl group；
Y is H or CH3；
Z isOr, wherein R is phenyl, naphthyl or C1～C5Alkyl；
N is the integer of 1～10；
X is:、、Or。
The preparation method of above-mentioned active ester compound, by phosphorus compound and hydroxy benzaldehyde, the addition 50～H of 70% mass concentration2SO4In, heat at 90～130 DEG C, condensing reflux 3～8hr, then product is washed by 3～10 alcohol, under the vacuum condition of 95～105 DEG C, be dried 3～6hr, obtain pre-product；Above-mentioned gained pre-product is dissolved in aromatic series organic solution, add benzoic acid or naphthyl, benzene alkylbenzoic acid compound, under the temperature conditions of 100～120 DEG C, add catalyst, condensing reflux 2～8hr, being dried 3～6hr after washing under the vacuum condition of 95～105 DEG C, i.e. obtain required phosphorous active ester compound, esterification yield is 65～85%；Wherein, described phosphorus compound is selected from 9,10-dihydro-9-oxy miscellaneous-10-phospho hetero phenanthrene-10-oxide, 10-(2,5-dihydroxy phenyl)-10-hydrogen-9-oxa--10-phospho hetero phenanthrene-10-oxide, 10-(2,5-dihydroxy naphthyl) one or more mixture in the phospho hetero phenanthrene compound such as-10-hydrogen-9-oxa--10-phospho hetero phenanthrene-10-oxide or 10-(2,5-dihydroxybiphenyl base)-10-hydrogen-9-oxa--10-phospho hetero phenanthrene-10-oxide.
Described aromatic organic solvent is selected from toluene, dimethylbenzene, ethylbenzene, isopropylbenzene.
Described catalyst is AlCl3。
Further technical scheme, in described phosphorous active ester compound, in mass, phosphorus content is 5.2～7.2%.
In technique scheme, described phosphorous active ester content is preferably 20-40 part.
In technique scheme, described modified polyphenylene ether resin is at least one in phenol modified polyphenylene ether resin or epoxide modified polyphenylene oxide resin, and its number-average molecular weight is 500 ~ 5000, and its content is preferably 10-30 part.
In technique scheme, described reinforcing agent is one or more in dicyandiamide, MDA, DADPS, diaminodiphenyl ether, and its content is preferably 0-10 part.
Further technical scheme, containing curing accelerator, one or more in 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole and triphenylphosphine of described curing accelerator, consumption is the 0.01 ~ 3% of weight epoxy.
Further technical scheme, containing inorganic filler, the consumption of described inorganic filler is the 0～35% of resin combination solid gross mass；Described inorganic filler is one or more the mixture in aluminium hydroxide, magnesium hydroxide, wollastonite, fine silica powder, magnesium oxide, calcium silicates, calcium carbonate, clay, Kaolin, glass dust, mica powder, titanium dioxide, Firebrake ZB, zinc molybdate.Particle diameter is 0.3～20 μm, preferential selection 0.5～5 μm.Above-mentioned inorganic filler can direct plunge into or previously prepared filler dispersion liquid or make mastic and put in resin combination.
Use the prepreg that above-mentioned halogen-free resin composition makes, halogen-free resin composition solvent is dissolved and makes glue, then reinforcing material is immersed in above-mentioned glue；By the reinforcing material heat drying after dipping, it is thus achieved that described prepreg.
The mixture of one or more in described solvent selected from acetone, butanone, methylisobutylketone, N, dinethylformamide, N, N-dimethyl acetylamide, ethylene glycol monomethyl ether, propylene glycol monomethyl ether.Described reinforcing material can use natural fiber, organic synthetic fibers, organic fabric or inorganic fabric.
Use above-mentioned prepreg, be covered with metal forming, hot forming at single or double, obtain described laminate.
The quantity of prepreg is that the laminate thickness according to customer requirement determines, available one or more.Described metal forming, can be Copper Foil, it is also possible to be aluminium foil, and their thickness is not particularly limited.
Owing to technique scheme is used, the present invention compared with prior art has the advantage that
1. the present invention devises the resin combination of a kind of halogen-free flameproof low-k with phosphorous active ester as fire retardant, the application of phosphorous active ester, avoid after introducing as fire retardant because of introducing phosphorous epoxy resin or phosphorus containing phenolic resin or phosphate ester, the rising of resin water absorption rate；
2. the present invention is simultaneously introduced appropriate modified polyphenylene ether resin, it is possible to obtain there is more excellent dielectric constant, is more beneficial for it and is applied to Halogen high speed contour performance printed wiring board field.
Accompanying drawing explanation
Fig. 1 be synthesis example one product nmr spectrum (13C)；
Fig. 2 be synthesis example one product nmr spectrum (1H)。
Detailed description of the invention
Below in conjunction with embodiment, the invention will be further described:
First carry out the synthesis of raw material.
Synthesis example one:
The preparation 1 of phosphorous active ester compound:
Weigh 10-(2,5-the dihydroxy phenyl)-10-hydrogen-9-oxa--10-phospho hetero phenanthrene-10-oxide of 0.6mol and the hydroxy benzaldehyde of 0.6mol, add the H of 65% mass concentration2SO4, condensing reflux 3～5hr under 100 DEG C of heating conditions, then this mixture is washed by 4～6 alcohol, obtain pre-product；Above-mentioned gained pre-product is dissolved in toluene solution, adds 0.2mol benzoic acid, under the temperature conditions of 120 DEG C, add the catalyst (AlCl of 0.05mol3), condensing reflux 4hr, after being then passed through washing for several times, under the vacuum condition of 105 DEG C, it is dried 4hr, i.e. obtains required phosphorous active ester compound, esterification yield is 70～80%, and phosphorus content is the phosphorous active ester compound of 6.4%, is designated as C1, and concrete structure is as follows:
X=, Y=H, Z=, R is phenyl, R1=CH3, n is 3 ~ 5.
The nmr spectrum of above-mentioned product (13C) as it is shown in figure 1, at 165ppm peak position relatively strong, show in resin containing active ester composition, nmr spectrum (1H) as in figure 2 it is shown, 7-8ppm is mainly on phenyl ring corresponding peak position, 3-4ppm is mainly DOPO and CH2The peak position of the correspondence that is connected, this synthesis compound described above meets the architectural feature of phosphorous active ester compound.
The preparation 2 of phosphorous active ester compound:
Weigh the 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide of 0.6mol and the hydroxy benzaldehyde of 0.6mol, add the H of 65% mass concentration2SO4, condensing reflux 3～5hr under 105 DEG C of heating conditions, then this mixture is washed by 4～8 alcohol, obtain pre-product；Above-mentioned gained pre-product is dissolved in toluene solution, adds 0.2mol benzoic acid, under the temperature conditions of 120 DEG C, add the catalyst (AlCl of 0.05mol3), condensing reflux 4hr, after being then passed through washing for several times, under the vacuum condition of 105 DEG C, it is dried 4hr, i.e. obtains required phosphorous active ester compound, esterification yield is 75～85%, and phosphorus content is the phosphorous active ester compound of 7.2%, is designated as C2, and concrete structure is as follows:
X=, Y=H, Z=, R is phenyl, R1=CH3, n is 3 ~ 5.
Embodiment:
According to weight ratio shown in table 1, epoxy resin, modified polyphenylene ether resin, phosphorous active ester compound, curing accelerator and inorganic filler and solvent are joined in mixed glue still, controlling glue solids content is 65%, stir, and ripening 8hr, make resin combination composition glue liquid；Then glass cloth is immersed in above-mentioned resin combination composition glue liquid；Then the glass cloth after dipping is formed prepreg after 155 ~ 175 DEG C of baking 4 ~ 7min；After prepreg is cut to certain size, 8 prepreg superpositions being formed folded structure, respectively place an electrolytic copper foil at folded structure, send into pressing in vacuum press, program is 150 DEG C/60min+200 DEG C/120min, prepares laminate.
Comparative example
Joining in mixed glue still according to weight ratio shown in table 1 by each component and solvent, controlling glue solids content is 65%, stirs, and ripening 8hr, makes resin combination composition glue liquid；Then glass cloth is immersed in above-mentioned resin combination composition glue liquid；Then the glass cloth after dipping is formed prepreg after 165 DEG C of baking 5min；After prepreg is cut to certain size, 8 prepreg superpositions being formed folded structure, respectively place an electrolytic copper foil at folded structure, send into pressing in vacuum press, program is 150 DEG C/60min+200 DEG C/120min, prepares laminate.
Table 1 composite formula
Component A: epoxy resin
A1: biphenyl type epoxy resin；
A2: dicyclopentadiene type epoxy resin；
B component: modified polyphenylene ether resin
B1: phenol modified polyphenylene ether resin, number-average molecular weight is 1000-2000；
B2: epoxide modified polyphenylene oxide resin, number-average molecular weight is 1500-4000；；
Component C: active ester
C1, C2: phosphorous active ester, is prepared by synthesis example one；
C3: without phosphorus active ester, DIC company of Japan, HPC8000-65T；
D component: other phosphorus-containing compounds
D1: phosphorous epoxy resin, CHIN YEE PE-315, phosphorus content 3.5%wt；
D2: phosphorus containing phenolic resin, Dow 92741 phosphorus content 9.2%wt；
Component E: reinforcing agent
E1: dicyandiamide；
E2: DADPS；
F component: curing accelerator, dimethyl-tetraethyl imidazoles；
G component: inorganic filler, silicon dioxide, particle diameter 0.5 ~ 5 micron.
Table 2 is the performance test carrying out embodiment one to five and comparative example one to four respectively, and result is as shown in the table:
The laminate properties data of table 2 embodiment and comparative example
In table, the method for testing of each performance is as follows:
(1) glass transition temperature (Tg):
According to differential scanning calorimetry, it is measured according to the DSC method of IPC-TM-650 2.4.25 defined.
(2) peel strength (PS):
According to " after the thermal stress " experiment condition in IPC-TM-650 2.4.8 method, the peel strength of test metallic cover layer.
(3) wicking thermostability:
Use the two sides band copper sample of 50 × 50mm, immerse in the scolding tin of 288 DEG C, the time that record sample layering is bubbled.
(4) wicking thermostability after moist process:
By the substrate coupons of 3 pieces of 100 × 100mm 121 DEG C, keep 3hr in the pressure cooking processing means of 105Kpa after, immerse 2min in the solder bath of 288 DEG C, observe whether sample occurs to be layered the phenomenons such as bubbling, 3 pieces all do not occur to be layered bubbling and are designated as 3/3,2 pieces do not occur to be layered bubbling and are designated as 2/3,1 piece does not occurs to be layered bubbling and is designated as 1/3, and 0 piece does not occurs to be layered bubbling and is designated as 0/3.
(5) heat decomposition temperature Td:
It is measured according to IPC-TM-650 2.4.26 method.
(6) dielectric constant:
Use flat band method according to IPC-TM-650 2.5.5.9, measure the dielectric constant under 1GHz.
(7) dielectric loss angle tangent:
Use flat band method according to IPC-TM-650 2.5.5.9, measure the dielectric loss factor under 1GHz.
(8) drop impact toughness (laminate 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 is clear, illustrates that the toughness of product is the best, represents with character ☆；Cross obscures, and illustrates that the poor toughness of product, fragility are big, represents with character ◎；Cross readability illustrates that between clear and fuzzy toughness of products is general, represents with character ◇.
(9) flame resistance (flame retardancy):
Measure according to UL94 method.
From upper table data, in the present invention being designed, the phosphorous active ester of synthesis is incorporated in resin combination, avoid resin system because introducing phosphorous epoxy resin or phosphorus containing phenolic resin and introducing as fire retardant (comparative example) after, the rising of resin water absorption rate, simultaneously, improve the humidity resistance of cyanate ester resin system, and there is relatively low dielectric properties constant and dielectric loss tangent value, high frequency requirement can be met.
Claims (7)
1. a halogen-free thermosetting resin composite, is in terms of 100 parts by solid weight sum, including:
(a) epoxy resin: 30 ~ 50 parts；
(b) modified polyphenylene ether resin: 5 ~ 40 parts；
(c) phosphorous active ester: 15 ~ 50 parts；
(d) reinforcing agent: 0 ~ 20 part；
The structural formula of described phosphorous active ester compound is,
,
In formula, R1 is methyl, ethyl or the tert-butyl group；
Y is H or CH3；
Z isOr, wherein R is phenyl, naphthyl or C1～C5Alkyl；
N is the integer of 1～10；
X is:、、Or。
Halogen-free thermosetting resin composite the most according to claim 1, it is characterised in that: described epoxy resin is selected from: bisphenol A epoxide resin, bisphenol F 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, one or more mixture of glycidyl ester type epoxy resin.
3. according to the halogen-free thermosetting resin composite described in claim 1, it is characterised in that: in described phosphorous active ester compound, in mass, phosphorus content is 5.2～7.2%.
4. according to the halogen-free thermosetting resin composite described in claim 1, it is characterised in that: described modified polyphenylene ether resin is at least one in phenol modified polyphenylene ether resin or epoxide modified polyphenylene oxide resin, and its number-average molecular weight is 500 ~ 5000.
5. according to the halogen-free thermosetting resin composite described in claim 1, it is characterised in that: described reinforcing agent is one or more in dicyandiamide, MDA, DADPS, diaminodiphenyl ether.
6. one kind uses the prepreg that halogen-free thermosetting resin composite as described in claim 1 makes, it is characterized in that: the halogen-free thermosetting resin composite solvent described in claim 1 is dissolved and makes glue, then reinforcing material is immersed in above-mentioned glue；By the reinforcing material heat drying after dipping, it is thus achieved that described prepreg.
7. one kind uses the laminate that halogen-free thermosetting resin composite as described in claim 1 makes, it is characterised in that: the single or double at least one prepreg obtained by claim 6 is covered with metal forming, hot forming, obtains described laminate.
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| CN105906785B (en) | 2015-02-19 | 2019-12-03 | Icl-Ip美国有限公司 | Fire Retardant of The Expoxy Resin containing phosphonate radical and phosphinic acids root functional group |
| CN105017723B (en) * | 2015-06-26 | 2017-12-26 | 四川东材科技集团股份有限公司 | A kind of extra-high voltage direct-current power transmission and transformation insulation stressed member and preparation method thereof |
| WO2018031103A1 (en) | 2016-08-11 | 2018-02-15 | Icl-Ip America Inc. | Curable epoxy composition |
| CN107759977A (en) * | 2017-09-20 | 2018-03-06 | 苏州巨峰新材料科技有限公司 | Copper-clad plate modified epoxy base prepreg and preparation method thereof |
| CN109988328A (en) * | 2017-12-29 | 2019-07-09 | 洛阳尖端技术研究院 | A kind of prepreg, composite material and preparation method and application |
| CN109735086B (en) * | 2019-01-08 | 2020-08-21 | 苏州生益科技有限公司 | High-frequency resin prepolymer and high-frequency resin composition, prepreg, laminated board and interlayer insulating film prepared from high-frequency resin prepolymer |
| CN115028967A (en) * | 2022-07-13 | 2022-09-09 | 山东金宝电子股份有限公司 | Resin composition and manufacturing method of high-frequency high-speed copper-clad plate |
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| JP5557033B2 (en) * | 2010-10-22 | 2014-07-23 | Ｄｉｃ株式会社 | Phosphorus atom-containing oligomer, production method thereof, curable resin composition, cured product thereof, and printed wiring board |
| CN102051022A (en) * | 2010-12-09 | 2011-05-11 | 广东生益科技股份有限公司 | Epoxy resin composition as well as prepreg and laminated board made of same |
| TWI554541B (en) * | 2011-05-10 | 2016-10-21 | Ajinomoto Kk | Resin composition |
| JP5500408B2 (en) * | 2012-03-21 | 2014-05-21 | Ｄｉｃ株式会社 | Active ester resin, thermosetting resin composition, cured product thereof, semiconductor sealing material, prepreg, circuit board, and build-up film |
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