CN109734910A - A kind of polyimides and its preparation method and application - Google Patents
A kind of polyimides and its preparation method and application Download PDFInfo
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- CN109734910A CN109734910A CN201910067437.XA CN201910067437A CN109734910A CN 109734910 A CN109734910 A CN 109734910A CN 201910067437 A CN201910067437 A CN 201910067437A CN 109734910 A CN109734910 A CN 109734910A
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Abstract
The present invention provides a kind of polyimides and its preparation method and application, and in the prior art, the modifying agent that polyphenylene oxide is typically used as epoxy resin uses, the epoxy reaction with epoxy resin.And the advantages of polyphenyl ether structure is introduced into polyimide resin by the present invention, and polyimides provided by the invention is made to have water absorption rate low, and dielectric constant is low, and dielectric loss is small, good stability of the dimension, meanwhile, the cohesive force of polyimides and copper foil that the present invention obtains is strong.
Description
Technical field
The invention belongs to the technical field of high molecular material, it is related to a kind of polyimides and its preparation method and application.
Background technique
Flexible circuit board is due to high flexural property, having been widely used for densification, lightness and portable
Communication field and each electronic product in.In recent years, information technology revolution entering signal high speed transmits the high frequency stage.
In order to handle ever-increasing data, the frequency of electronic equipment is higher and higher.This just proposes the electrical property of substrate higher
It is required that be reduced as far as the loss of high-frequency signal and delay.
With the arrival of 5G communication times, dielectric constant and loss of traditional polyimides since water absorption rate is high, under high frequency
Height, the unsuitable high-frequency high-speed field that is applied to are applied；It would therefore be desirable to be modified to it, by polyimides
It is modified, water absorption rate can be reduced, reduce its dielectric loss and constant, promote high frequency performance.CN107286650A is provided
A kind of manufacturing method of the polyimides of low-k and the application of polyimide film, including fluoro containing polymers dispersion liquid is provided
(A) and the aromatic diamine (B) that is dissolved in the first solvent (C)；Above-mentioned fluoro containing polymers dispersion liquid (A) includes fluoro containing polymers
(a-1), the second solvent (a-2) and dispersing agent (a-3)；Fluoro containing polymers dispersion liquid (A) and aromatic diamine (B) is mixed, with shape
At in the first mixture；Aromatic tetracarboxylic dianhydride (D) is added in the first mixture, to form polyamic acid solution；To poly-
Amide acid solution carries out solvent step and heating stepses, polyimides is made.The patent, can be with by introducing fluorochemical monomer
Water absorption rate, dielectric constant and loss are reduced simultaneously, but the introducing of fluorine element, the removing that can reduce polyimides and copper foil are strong
Degree.CN108948354A discloses a kind of modified polyimide resin and preparation method thereof and application, includes the following steps:
Dianhydride and diamines are subjected to pre-polymerization, obtain prepolymer polyamic acid；By prepolymer polyamic acid and synthesis bismaleimide three
The material copolymerization of piperazine resin, obtains modified prepolymers；And solidify modified prepolymers, obtain modified polyimide resin；Its
The warpage performance of polyimides is improved in the form of copolymerization, but does not pay close attention to its dielectric properties excessively.
Therefore, the polyimides with low water absorption, low-k and low loss factors is still a technical problem.
Summary of the invention
The purpose of the present invention is to provide a kind of polyimides and its preparation method and application.Polyamides provided by the invention is sub-
Amine has water absorption rate low, and dielectric constant and dielectric loss are smaller under high frequency, while the feature strong with copper foil cohesive force, are suitable for
High-frequency high-speed circuit substrate.
To achieve this purpose, the present invention adopts the following technical scheme:
In a first aspect, the polyimides has structure shown in formula I the present invention provides a kind of polyimides:
Wherein, Ar is the residue of dianhydride compound, and R is the residue of aromatic diamine or the residue of Amino End Group polyphenylene oxide, m are
2-10000, such as 3,4,5,10,50,100,500,800,1000,2000,3000,5000,8000,9000,9500 etc..
In the prior art, the modifying agent that polyphenylene oxide is typically used as epoxy resin uses, anti-with the epoxy group of epoxy resin
It answers.And polyphenyl ether structure is introduced into polyimide resin by the present invention, make polyimides provided by the invention have water absorption rate it is low,
The advantages of dielectric constant is low, dielectric loss is small and good stability of the dimension, meanwhile, polyimides that the present invention obtains and copper foil it is viscous
It is strong to tie power.
Preferably, the raw material for preparing of the polyimides includes Amino End Group polyphenylene oxide, aromatic diamine and dianhydride compound.
Preferably, mole of the sum of the mole of the Amino End Group polyphenylene oxide and aromatic diamine with the dianhydride compound
The ratio of amount is 0.98-1.02, such as 0.99,1.00,1.01 etc..
It preferably, is in terms of 100% by the integral molar quantity of the Amino End Group polyphenylene oxide and aromatic diamine, the Amino End Group is poly-
The mole of phenylate is 5-60%, such as 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55% etc.,
It is preferred that 20-60%, more preferable 25-40%.
Preferably, the Amino End Group polyphenylene oxide has the structure as shown in Formula II:
Wherein, n 1-100, such as 2,4,6,10,15,20,30,40,50,60,70,80,90 etc..
Preferably, average functionality >=1.8 of the Amino End Group polyphenylene oxide, such as 1.9,2,2.2 etc..
Preferably, glass transition temperature >=150 DEG C of the Amino End Group polyphenylene oxide, for example, 160 DEG C, 170 DEG C, 180 DEG C,
200 DEG C etc..
Preferably, 1% thermal decomposition temperature >=300 DEG C of the Amino End Group polyphenylene oxide, such as 310 DEG C, 320 DEG C, 340 DEG C
Deng.
Preferably, the preparation method of the Amino End Group polyphenylene oxide includes the following steps: terminal hydroxy group polyphenylene oxide and bromine source is anti-
It answers, obtains the polyphenylene oxide of end bromo, then reacted with amine source, obtain the Amino End Group polyphenylene oxide.
Wherein, the structural formula of the terminal hydroxy group polyphenylene oxide is as follows:
Preferably, bromide source is the bromo- acetyl bromide of 2-.
Preferably, the amine source is triethylamine.
Preferably, the aromatic diamine is selected from diaminodiphenyl ether (ODA), bis- [4- (4- amino-benzene oxygen) benzene of 2,2-
Base] propane, bis- (4- amino-benzene oxygen) benzene (BAPP) of 1,3-, bis- (4- amino-benzene oxygen) benzene (TPE-R) of 1,4-, 4,4'- diamino
Base -2,2'- dimethyl diphenyl (m-TB), p-phenylenediamine (PDA), 4,4'- diamino -2,2'- bis trifluoromethyl biphenyl (TFDB)
In bis- (the 4- phenalgin oxygroup) biphenyl (BAPB) of 4,4'- any one or at least two combination.
Preferably, the aromatic diamine be 4,4'- diamino -2,2'- bis trifluoromethyl biphenyl and diaminodiphenyl ether,
Bis- [4- (4- amino-benzene oxygen) phenyl] propane of 2,2-, bis- (4- amino-benzene oxygen) benzene of 1,3-, 1,4- bis- (4- amino-benzene oxygens)
Any one in benzene, 4,4'- diamino -2,2'- dimethyl diphenyl, p-phenylenediamine or bis- (the 4- phenalgin oxygroup) biphenyl of 4,4'-
Or at least two obtained compositions, such as 4, the group of 4'- diamino -2,2'- bis trifluoromethyl biphenyl and diaminodiphenyl ether
It closes, combination, the 4,4'- diamino-of 4,4'- diamino -2,2'- bis trifluoromethyl biphenyl and bis- (4- amino-benzene oxygen) benzene of 1,3-
The combination etc. of 2,2'- bis trifluoromethyl biphenyl and p-phenylenediamine and bis- (the 4- phenalgin oxygroup) biphenyl of 4,4'-.
Include 4,4'- diamino -2,2'- bis trifluoromethyl biphenyl in optimization aromatic diamines of the present invention, is contained by introducing
Fluorine monomer can obtain the excellent low water absorption polyamide imines of high frequency performance.
Preferably, the dianhydride compound is selected from pyromellitic acid anhydride (PMDA), 3,3', 4,4'- biphenyltetracarboxyacid acids two
Acid anhydride (BPDA), 4,4'- (hexafluoro isopropyl alkene) two anhydride phthalic acids (6-FDA), bis- (trimellitic anhydride) phenyl esters (TAHQ), 4,4'- biphenyl
Ether dianhydride (ODPA), 3,3', 4,4'- benzophenone tetracarboxylic dianhydride (BTDA) or 4,4'- (4,4'- isopropyl diphenoxy) are double
In (phthalic anhydride) (BPADA) any one or at least two combination.
Preferably, the dianhydride compound is 4,4'- (hexafluoro isopropyl alkene) two anhydride phthalic acids and/or bis- (trimellitic anhydride) benzene
Ester and pyromellitic dianhydride, 3,3', 4,4'- biphenyltetracarboxylic dianhydride, 4,4'- biphenyl ether dianhydride, 3,3', 4,4'- benzophenone
Any one in tetracarboxylic acid dianhydride or 4,4'- (4,4'- isopropyl diphenoxy) bis- (phthalic anhydrides) or at least two
Obtained composition, such as 4, combination, 4,4'- (the hexafluoro isopropyl of 4'- (hexafluoro isopropyl alkene) two anhydride phthalic acids and pyromellitic dianhydride
Alkene) two anhydride phthalic acids and 4,4'- biphenyl ether dianhydride and 3,3', the combination of 4,4'- benzophenone tetracarboxylic dianhydride, (hexafluoro is different by 4,4'-
Propylene) two anhydride phthalic acids and bis- (trimellitic anhydride) phenyl esters and 4,4'- (4,4'- isopropyl diphenoxy) it is bis- (phthalic anhydride)
Combination etc..
4,4'- (hexafluoro isopropyl alkene) two anhydride phthalic acids and/or bis- (inclined benzene are preferably included in dianhydride compound provided by the invention
Three acid anhydrides) fluorine and/or ester acid anhydride be introduced into polyimides by phenyl ester by selection fluorochemical monomer and/or ester-containing anhydride monomer, and it can be with
Obtain the excellent low water absorption polyamide imines of high frequency performance.
Second aspect, the present invention provides the preparation method of the polyimides according to first aspect, the preparation side
Method includes the following steps:
Amino End Group polyphenylene oxide, aromatic diamine and dianhydride compound are mixed, polyamic acid is obtained, then carries out hot imines
Change reaction, obtains the polyimides.
Preferably, the mixing carries out in a solvent, obtains polyamic acid solution.
Preferably, the solvent includes appointing in dimethylformamide, dimethyl acetamide or n-vinyl pyrrolidone
It anticipates a kind of or at least two combinations.
Preferably, the solid content of the polyamic acid solution be 10-20wt%, such as 12wt%, 14wt%, 16wt%,
18wt% etc..
Preferably, the viscosity of the polyamic acid solution be 10000-50000cps, such as 20000cps, 30000cps,
40000cps etc..
Preferably, solvent is removed before carrying out hot imidization reaction.
Preferably, it is described remove solvent temperature be 80-120 DEG C, such as 85 DEG C, 90 DEG C, 95 DEG C, 100 DEG C, 105 DEG C,
110 DEG C, 115 DEG C etc., time 5-15min, such as 8min, 10min, 12min etc. is 100-120 DEG C further preferred, 5-
10min。
Preferably, the condition of hot imidization reaction are as follows: in 150-220 DEG C of (such as 160 DEG C, 170 DEG C, 180 DEG C, 190
DEG C, 200 DEG C, 210 DEG C etc.) under keep after 45-75min (such as 50min, 60min, 70min etc.) at 220-260 DEG C (such as 230
DEG C, 240 DEG C, 250 DEG C etc.) under keep 15-45min (such as 20min, 25min, 30min, 35min, 40min etc.), finally exist
45-75min (such as 50min, 60min, 70min etc.) is kept under 280-320 DEG C (such as 290 DEG C, 300 DEG C, 310 DEG C etc.).
The third aspect, the present invention provides a kind of Kapton, the raw material for preparing of the Kapton includes
Polyimides described in first aspect.
Fourth aspect, the present invention provides a kind of copper-clad plate, the copper-clad plate includes polyimides described in the third aspect
Film.
5th aspect, the present invention provides a kind of answering in flexible circuit board of the copper-clad plate according to fourth aspect
With.
Compared with the existing technology, the invention has the following advantages:
(1) in the prior art, the modifying agent that polyphenylene oxide is typically used as epoxy resin uses, the epoxy group with epoxy resin
Reaction.And polyphenyl ether structure is introduced into polyimide resin by the present invention, and polyimides provided by the invention is made to have water absorption rate
Low, the advantages of dielectric constant is low, dielectric loss is small and good stability of the dimension, meanwhile, the polyimides and copper foil that the present invention obtains
Cohesive force it is strong.
(2) present invention has the polyimides finally obtained by the way that polyphenylene oxide to be introduced into the main chain of polyimides
Lower water absorption rate and lower dielectric constant and dielectric loss, at the same with copper foil peel strength with higher, wherein inhale
Water rate is lower than 0.8%, and dielectric constant is lower than 3.45 (10GHz), and dielectric loss is lower than 0.0047 (10GHz), the stripping with copper foil layer
From intensity in 1N/mm or more.
Specific embodiment
The technical scheme of the invention is further explained by means of specific implementation.Those skilled in the art should be bright
, the described embodiments are merely helpful in understanding the present invention, should not be regarded as a specific limitation of the invention.
Preparation example 1
This preparation example provides a kind of Amino End Group polyphenylene oxide, has the following structure:
The preparation method is as follows:
100g terminal hydroxy group polyphenylene oxide (SA 90, molecular weight 1800) is dissolved in the methylene chloride of 250mL, is added appropriate
The triethylamine of 3mL；Under stiring, it is slowly added to the bromo- acetyl bromide of 2- of 25mL, after reacting 2h at room temperature, reaction solution is concentrated
It to 100mL, is deposited in the ethyl alcohol of 600mL, obtains brown solid, be filtered, washed, 80 DEG C of drying obtain end bromo polyphenylene oxide.
1H NMR(500MHz,CD2Cl2, 298K) and δ [ppm]=7.14-7.65 (phenyl ring hydrogen), 2.13 (methyl hydrogens), 2.30
(end bromine hydrogen)
The end 70g bromo polyphenylene oxide is dissolved in the methylene chloride of 250mL, under stiring, the triethylamine of 3mL, room is added
Temperature is lower to react 5h, and reaction solution is concentrated into 100mL, is deposited in the ethyl alcohol of 600mL, brown solid is obtained, is filtered, washed, and 80
DEG C drying obtains Amino End Group polyphenylene oxide；Wherein, (gel chromatography is mark with polystyrene using THF as solvent to molecular weight 2200
Sample), degree of functionality 1.9, glass transition temperature be 158 DEG C (differential scanning calorimeter determine, warming and cooling rate be 10 DEG C/
Min), 1% thermal decomposition temperature is 375 DEG C of (thermogravimetric analyzer, N2Atmosphere, 10 DEG C/min).
1H NMR(500MHz,CD2Cl2, 298K) and δ [ppm]=7.14-7.65 (phenyl ring hydrogen), 2.13 (methyl hydrogens), 2.30
(Amino End Group hydrogen)
Embodiment 1-6
It is prepared Kapton (raw material dosage unit is mmol) by component shown in table 1, and according to following production side
Legal system makees single-side coated copper plate:
The Amino End Group polyphenylene oxide that the aromatic diamine of formula ratio and preparation example are prepared is dissolved in the dimethyl of 15mL
In formamide, at room temperature after stirring and dissolving, it is put into ice water.Under stiring, dianhydride compound is added, after stirring 3h in ice water,
It adds micro dianhydride compound and adjusts viscosity, obtain the thick yellow polyamic acid solution that viscosity is 20000cps or so.
Polyamic acid solution is uniformly coated on low profile copper foil with 250 μm of wet film of thickness, 120 DEG C of dry 10min
After removing solvent, it is put into nitrogen protection baking oven；In 150 DEG C of holding 20min, 200 DEG C of holding 20min, 250 DEG C are kept
20min, 300 DEG C of holdings 20min, 35 DEG C of holding 20min.Single-side coated copper plate is obtained after cooling.
Comparative example 1-3
Kapton (raw material dosage unit is mmol) is prepared by component shown in table 2, and is provided according to embodiment
Production method make single-side coated copper plate.
Table 1
Performance test
The embodiment 1-6 and comparative example 1-3 single-side coated copper plate provided is tested for the property, the method is as follows:
(1) water absorption rate: by Kapton after 105 DEG C of dry 2h, cooling weighing is put into water, is taken afterwards for 24 hours
Out, after drying surface moisture with blotting paper, quality is weighed again.It is secondary of poor quality divided by initial weight i.e. acquisition water absorption rate；
(2) dielectric constant and dielectric loss: by Kapton after 105 DEG C of dry 2h, at 23 DEG C, the item of 50RH%
48h is balanced under part, resonant cavity test, test frequency 10GHz are separated by the medium that agilent company produces；
(3) peel strength: the method to single-side coated copper plate referring to IPC-TM-650 2.4.9 is tested.
Test result is shown in Table 2.
Table 2
By embodiment and performance test it is found that the present invention is made most by the way that polyphenylene oxide to be introduced into the main chain of polyimides
The polyimides obtained afterwards has lower water absorption rate and lower dielectric constant and a dielectric loss, at the same with copper foil have compared with
High peel strength, wherein water absorption rate is lower than 0.8%, and dielectric constant is lower than 3.45 (10GHz), and dielectric loss is lower than 0.0047
(10GHz), the peel strength with copper foil layer is in 1N/mm or more.By embodiment 2-4 it is found that by introducing fluorochemical monomer or containing
Ester anhydride monomer can obtain the excellent low water absorption polyamide imines of high frequency performance.By the comparison of embodiment 1-6 it is found that in this hair
In bright, preferably the mole of Amino End Group polyphenylene oxide is 20-60%, and the polyimides obtained at this time has more excellent comprehensive
Energy.It can be seen that by the comparison of embodiment 1,3-4 and comparative example 1-3 and do not add Amino End Group polyphenylene oxide, can not obtain while having
There is the polyimides of low water absorption, low-k and low-dielectric loss and high-peeling strength.
The Applicant declares that the present invention is explained by the above embodiments polyimides of the invention and preparation method thereof and answering
With, but the invention is not limited to above-mentioned method detaileds, that is, it is real not mean that the present invention must rely on above-mentioned method detailed ability
It applies.It should be clear to those skilled in the art, any improvement in the present invention, to the equivalent of each raw material of product of the present invention
Replacement and addition, the selection of concrete mode of auxiliary element etc., all of which fall within the scope of protection and disclosure of the present invention.
Claims (10)
1. a kind of polyimides, which is characterized in that the polyimides has structure shown in formula I:
Wherein, Ar is the residue of dianhydride compound, and R is the residue of aromatic diamine or the residue of Amino End Group polyphenylene oxide, m 2-
10000。
2. polyimides according to claim 1, which is characterized in that the raw material for preparing of the polyimides includes Amino End Group
Polyphenylene oxide, aromatic diamine and dianhydride compound；
Preferably, the sum of mole of the Amino End Group polyphenylene oxide and aromatic diamine and the mole of the dianhydride compound
Than for 0.98-1.02；
It preferably, is the Amino End Group polyphenylene oxide in terms of 100% by the integral molar quantity of the Amino End Group polyphenylene oxide and aromatic diamine
Mole be 5-60%, preferably 20-60%.
3. polyimides according to claim 2, which is characterized in that the Amino End Group polyphenylene oxide has to be tied as shown in Formula II
Structure:
Wherein, n 1-100.
4. polyimides according to claim 3, which is characterized in that the preparation method of the Amino End Group polyphenylene oxide includes such as
Lower step: terminal hydroxy group polyphenylene oxide is reacted with bromine source, is obtained the polyphenylene oxide of end bromo, is then reacted with amine source, obtain the end
Amino polyphenylene oxide；
Wherein, the structural formula of the terminal hydroxy group polyphenylene oxide is as follows:
Preferably, bromide source is the bromo- acetyl bromide of 2-；
Preferably, the amine source is triethylamine.
5. the polyimides according to any one of claim 2-4, which is characterized in that the aromatic diamine is selected from two
Bis- [4- (4- amino-benzene oxygen) phenyl] propane of amino-diphenylethers, 2,2-, bis- (4- amino-benzene oxygen) benzene of 1,3-, the bis- (4- of 1,4-
Amino-benzene oxygen) benzene, 4,4'- diamino -2,2'- dimethyl diphenyl, p-phenylenediamine, the double fluoroforms of 4,4'- diamino -2,2'-
In base biphenyl or bis- (the 4- phenalgin oxygroup) biphenyl of 4,4'- any one or at least two combination；
Preferably, the aromatic diamine is 4,4'- diamino -2,2'- bis trifluoromethyl biphenyl and diaminodiphenyl ether, 2,2-
Bis- [4- (4- amino-benzene oxygen) phenyl] propane, bis- (4- amino-benzene oxygen) benzene of 1,3-, 1,4- bis- (4- amino-benzene oxygen) benzene, 4,
In 4'- diamino -2,2'- dimethyl diphenyl, p-phenylenediamine or bis- (the 4- phenalgin oxygroup) biphenyl of 4,4'- any one or at least
Two kinds of obtained compositions；
Preferably, the dianhydride compound is selected from pyromellitic acid anhydride, 3,3', 4,4'- biphenyltetracarboxylic dianhydrides, 4,4'- (six
Fluorine isopropyl alkene) two anhydride phthalic acids, bis- (trimellitic anhydride) phenyl esters, 4,4'- biphenyl ether dianhydride, 3,3', 4,4'- benzophenone tetracarboxylic
In dianhydride or 4,4'- (4,4'- isopropyl diphenoxy) bis- (phthalic anhydrides) any one or at least two combination；
Preferably, the dianhydride compound be 4,4'- (hexafluoro isopropyl alkene) two anhydride phthalic acids and/or bis- (trimellitic anhydride) phenyl esters with
Pyromellitic dianhydride, 3,3', 4,4'- biphenyltetracarboxylic dianhydride, 4,4'- biphenyl ether dianhydride, 3,3', 4,4'- benzophenone tetramethyl
In acid dianhydride or 4,4'- (4,4'- isopropyl diphenoxy) bis- (phthalic anhydrides) any one or at least two obtain
Composition.
6. the preparation method of polyimides described in any one of -5 according to claim 1, which is characterized in that the preparation side
Method includes the following steps:
Amino End Group polyphenylene oxide, aromatic diamine and dianhydride compound are mixed, polyamic acid is obtained, it is anti-then to carry out hot imidization
It answers, obtains the polyimides.
7. preparation method according to claim 6, which is characterized in that the mixing carries out in a solvent, obtains polyamide
Acid solution；
Preferably, the solvent includes any one in dimethylformamide, dimethyl acetamide or n-vinyl pyrrolidone
Kind or at least two combination；
Preferably, the solid content of the polyamic acid solution is 10-20wt%；
Preferably, the viscosity of the polyamic acid solution is 10000-50000cps；
Preferably, solvent is removed before carrying out hot imidization reaction；
Preferably, the temperature for removing solvent is 80-120 DEG C, time 5-15min, further preferred 100-120 DEG C, 5-
10min；
Preferably, the condition of the hot imidization reaction are as follows: at 150-220 DEG C after holding 45-75min at 220-260 DEG C
15-45min is kept, finally keeps 45-75min at 280-320 DEG C.
8. a kind of Kapton, which is characterized in that the raw material for preparing of the Kapton includes in claim 1-5
Described in any item polyimides.
9. a kind of copper-clad plate, which is characterized in that the copper-clad plate includes Kapton according to any one of claims 8.
10. application of the copper-clad plate according to claim 9 in flexible circuit board.
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| CN113913149A (en) * | 2021-11-18 | 2022-01-11 | 广州联茂电子科技有限公司 | Improved polyimide adhesive, flexible metal foil substrate and preparation method |
| CN114854012A (en) * | 2022-06-20 | 2022-08-05 | 杭州福斯特电子材料有限公司 | Polyimide resin, polyimide film, preparation method of polyimide film and copper clad plate |
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