CN109912618A - Multifunctional organic acid anhydride and low-dielectric-constant hyperbranched polyimide film - Google Patents
Multifunctional organic acid anhydride and low-dielectric-constant hyperbranched polyimide film Download PDFInfo
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Abstract
The invention discloses a multifunctional organic acid anhydride and a low-dielectric-constant hyperbranched polyimide film, wherein the low-dielectric-constant hyperbranched polyimide film is formed by polymerizing aromatic dicarboxylic anhydride, aromatic diamine and the multifunctional organic acid anhydride, the ratio of the mole number of total acid anhydride to the mole number of total amino groups is 1:1 in the polymerization process, and the used catalyst accounts for 0.1-2 mol% of the total mole amount of total acid anhydride and diamine monomers. The multifunctional organic acid anhydride monomer forms a hyperbranched structure in the PI molecular structure, so that the stacking density of PI molecules is effectively reduced, and the molar polarization density of PI is reduced. Compared with the PI film synthesized without adding the polyfunctional organic acid anhydride provided by the invention, the dielectric constant of the polyimide film prepared by the invention is reduced by 13.1-31.6%, the lowest dielectric constant is 2.4, and the application requirements in the technical fields of future high frequency, high speed and 5G communication can be effectively met.
Description
Technical field
The present invention relates to polyimides tree film fields, and in particular to novel polyfunctionality organic acid anhydride and prepared therefrom low
Dielectric constant super-branched polyimide film.
Background technique
With the fast development of science and technology and information age, high-frequency high-speed communication is following one of the important trends.Mesh
Before, 4G communication has been obtained and is widely applied, and 5G will also be progressed into people's lives in the following 5-10.5G
It is 10 times of 4G or more that communication, which has more high-rate information transmission ability, signal transmission speed,.However 5G communication is to mobile communication
Equipment, RF base station, integrated circuit and relative electronic components made higher requirement.In the 5G epoch, electronic product
Middle integrated circuit develops towards high density direction, and various components and route feature sizes are gradually reduced, bring train of signal
It disturbs, the negative effect such as RC delay can cause signal propagation delay, and generate power dissipation, becomes the great resistance of 5G Communication Development
Hinder.In high-frequency high-speed communication process, transmission speed, delay size, signal interference and power consumption penalty of signal etc. mainly go to take
Certainly in the dielectric constant of integrated circuit dielectric (Dk).Dielectric constant is smaller, and signal transmission is faster, postpones smaller, power consumption also more
It is low.Therefore, developing the novel dielectric substance with low-k is that high frequency 5G field of communication technology needs urgently to solve
One of certainly the problem of.
Polyimides (PI) with excellent mechanics and heat resistance etc. is widely used in microelectronics and collection due to it
At in circuit field, especially apply in portable items of electronic.PI has flexibility well, can be used as the following flexibility
The substrate of display and flexible communication equipment uses.However the intrinsic dielectric constant of PI, generally between 3.0-3.6, dielectric properties are still
It is not able to satisfy the requirement (Dk < 2.8) of the following high-frequency high-speed 5G communication technology.In order to solve this problem, scientific circles are to low dielectric
Constant PI is conducted in-depth research, and achieves many phasic results.According to the basic theory of dielectric constant, material Jie is influenced
The principal element of electric constant has mole polarizability and polarizability density of dielectric molecule.The research work that science is ground is also main
In this two aspects expansion research.Such as fluorine atom is introduced in PI, and it is based on lower mole of polarizability (0.56) of C-F key, it can
To reduce dielectric constant.However this method is to the reduction limitation of dielectric constant, and the introducing of fluorine can greatly increase the system of PI
Standby cost.In addition, the introducing of fluorine also results in the negative shadows such as the increase of PI thermal expansion coefficient, adhesion property and creep-resistant property variation
It rings.By introducing porous structure in PI, the polar molecule density of unit volume in PI can be reduced, to efficiently reduce PI
Dielectric constant.The dielectric constant for preparing porous PI can be reduced to 2.0 even lower, and preparation method includes thermal decomposition method, changes
Learn etching method, microphase-separated method etc..However, many results of study show that the porous PI material of obtained low dielectric is often sacrificed
Its distinctive heat resistance and mechanical property.In addition, porous preparation is often uneven and uncontrollable, it is also difficult to amplification and industry
Change preparation production, is also unable to satisfy following growth requirement.Therefore, a kind of simple, easily industrialization, cheap preparation is found to have both
The method of low-k and the PI of superior heat resistance performance and mechanical property are a weights of the following high-frequency high-speed 5G Communication Development
It challenges.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of polyfunctionality organic acid anhydride and low dielectric is normal
Number super-branched polyimide film.The novel polyfunctionality organic acid anhydride can be used as branch centers site in PI, increase PI
Intrinsic free volume, reduce the stacking density of PI molecule, so that dielectric constant be effectively reduced, while keeping excellent heat-resisting of PI
And mechanical property.
The purpose of the present invention is achieved through the following technical solutions: a kind of polyfunctionality organic acid anhydride, its chemistry
Shown in the following structural formula of structural formula (1)~(3):
A kind of low-k super-branched polyimide film, it is prepared by the following method to obtain:
(1) it is organic that organic solvent, aromatic diamine, aromatic dibasic acid acid anhydride and polyfunctionality are sequentially added in the reaction vessel
Acid anhydrides reacts 2-12h at 0-35 DEG C under the protection of nitrogen, obtains polyamic acid precursor solution；In reaction system, fragrance two
The molar ratio of the total amount and aromatic diamine of first acid anhydrides and polyfunctionality organic acid anhydride is 1:1；Aromatic diamine, aromatic dibasic acid
In the total amount of acid anhydride and polyfunctionality organic acid anhydride, the molar content of polyfunctionality organic acid anhydride is 0.1-5%；And fragrant binary
The gross mass of amine, aromatic dibasic acid acid anhydride and polyfunctionality organic acid anhydride is the 8-30wt% of polyamic acid precursor solution；
(2) catalyst is added in the polyamic acid precursor solution that step (1) obtains, the dosage of catalyst is relative to poly-
The 0.1-2mol% of all acid anhydrides and diamines integral molar quantity used in amic acid precursor solution, agitating solution 1-6h, Zhi Houli
With casting machine, by above-mentioned polyamic acid precursor solution casting film at room temperature, and dried in 40-60 DEG C, then at 80-150 DEG C
1-6h is reacted, low-k super-branched polyimide film is obtained.
It further, further include that two-way drawing is carried out to the low-k super-branched polyimide film that step (2) obtain
The step of stretching.The biaxial tension specifically comprises the processes of: 100-250 DEG C of temperature, tensile strength 10-50Mpa, stretching time 5-
60min。
Further, shown in the following structural formula of chemical structural formula (4)~(13) of the aromatic dibasic acid acid anhydride:
Further, shown in the following structural formula of the chemical structural formula of the aromatic diamine (14)~(23):
Further, the organic solvent by N-Methyl pyrrolidone, n,N-Dimethylformamide, paracresol, o-cresol,
One of metacresol, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide, diethylene glycol monomethyl ether are a variety of mixed by any proportion
It is combined into.
Further, the catalyst is made of one or two in acetic anhydride or pyridine by the mixing of any proportion.
The invention has the advantages that present invention firstly provides three kinds of novel polyfunctionality organic acid anhydride monomers, and
Branch sites are utilized it as, by one-step synthesis method with low-k, the over-expense that heat resistance is good, tensile strength is high
Change Kapton.The introducing of novel polyfunctionality organic acid anhydride monomer, forms dissaving structure in PI molecular structure,
The stacking density of PI molecule is effectively reduced, reduces mole polarization density of PI.In addition, three kinds of novel polyfunctionality organic acid anhydrides
Monomer all has biggish intrinsic volume, and is non-aromatic system's alicyclic structure, and mole polarizability of itself is well below virtue
Fragrant series organic acid anhydride, therefore the dielectric constant of PI can be significantly reduced.Due to the content of the polyfunctionality organic acid anhydride of introducing
Control is in a certain range, little to the intrinsic excellent heat-resisting and Effect on Mechanical Properties of whole PI.In identical test condition
Under, it compares with the PI film that polyfunctionality organic acid anhydride provided by the invention synthesizes is not added with, the present invention is prepared poly-
The dielectric constant of imide membrane reduces 13.1-31.6%, and lowest dielectric constant 2.4 can effectively meet the following height
The application requirement of frequency high speed and 5G field of communication technology.
Detailed description of the invention
Fig. 1 is a kind of low-k super-branched polyimide film chemical structural schematic diagram.
Specific embodiment
In order to better understand the present invention, below with reference to specific embodiment, the present invention will be further described in detail,
But the scope of protection of the invention is not limited to range represented by embodiment, the process conditions such as temperature, time in preparation method
Selection can adaptation to local conditions and to result have no substantial effect reality.
Parameter measurement
Dielectric constant
Functionalized carbon quantum dot/polyimide composite film is dried in 105 DEG C of baking ovens in advance and is handled for 24 hours, polyimides
Film dimensions be 2 × 2cm, 25 μm of thickness.Using Agilent vector network analyzer N5230A, polyamides is tested using resonator method
The dielectric constant of imines film, test frequency are respectively 1MHz.
Tensile strength
Mechanical property is tested by universal testing machine KSM-20KN, the tensile strength of test parameter material.
Thermal stability
The decomposition temperature (Tw) when 5wt% is reduced using TGA/DSC test glass transition temperature (Tg) and weight.Heating
Rate is 10 DEG C/min, and 800 DEG C of maximum temperature, nitrogen protection is used in test process.
Embodiment 1
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.7mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride A (0.1mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree, the low-k super-branched polyimide film chemical of preparation
Structure is as shown in Figure 1.
Embodiment 2
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.4mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride A (0.2mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 3
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (8.5mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride A (0.5mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 4
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.7mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride B (0.1mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 5
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.4mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride B (0.2mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 6
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (8.5mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride B (0.5mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 7
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.6mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride C (0.1mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 8
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (9.2mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride C (0.2mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Embodiment 9
30mL DMAC N,N' dimethyl acetamide, ODA (10mmol), a-BPDA (8.8mmol) are sequentially added in the reaction vessel
And above-mentioned polyfunctionality organic acid anhydride C (0.3mmol), 10h is reacted at 25 DEG C under the protection of nitrogen, before obtaining polyamic acid
Liquid solution；Pyridine (0.15mmol) is added in above-mentioned polyamic acid precursor solution, agitating solution 6h utilizes casting machine later,
It is dried by the molten precursor of above-mentioned polyamic acid casting film at room temperature, and in 50 DEG C, then at 100 DEG C of reaction 4h, obtains low dielectric
Constant super-branched polyimide film is later removed Kapton using peel-off device from casting belt.Above-mentioned polyamides
After the removing of imines film, further progress stretch processes are orientated in the face to increase polyimides.Drawing process are as follows: temperature
150 DEG C, tensile strength 40Mpa, stretching time 30min of degree.
Comparative example
30mL n,N-dimethylacetamide, ODA (10mmol), a-BPDA (10mmol) are sequentially added in the reaction vessel,
10h is reacted at 25 DEG C under the protection of nitrogen, obtains polyamic acid precursor solution；Add in above-mentioned polyamic acid precursor solution
Enter pyridine (0.15mmol), agitating solution 6h, utilizes casting machine later, the molten precursor of above-mentioned polyamic acid is cast system at room temperature
Film, and dried in 50 DEG C, then at 100 DEG C of reaction 4h, low-k super-branched polyimide film is obtained, utilizes removing later
Equipment removes Kapton from casting belt.After above-mentioned Kapton removing, further progress biaxial tension work
Skill is orientated in the face to increase polyimides.Drawing process are as follows: 150 DEG C of temperature, tensile strength 40Mpa, stretching time
30min。
Performance parameter test, test parameter packet are carried out according to film sample obtained by above-described embodiment 1-9 and comparative example
Dielectric constant Dk, tensile strength, thermal stability are included, test result is as shown in table 1.
Table 1: the properties of film sample obtained by different embodiments
| Sample | Dk | Tensile strength/Mpa | Tg/℃ | Tw/℃ |
| Embodiment 1 | 3.05 | 110.6 | 392 | 571 |
| Embodiment 2 | 2.76 | 105.2 | 387 | 568 |
| Embodiment 3 | 2.62 | 98.3 | 381 | 565 |
| Embodiment 4 | 3.01 | 104.7 | 389 | 572 |
| Embodiment 5 | 2.82 | 101.2 | 384 | 569 |
| Embodiment 6 | 2.65 | 97.8 | 381 | 567 |
| Embodiment 7 | 2.87 | 100.9 | 388 | 565 |
| Embodiment 8 | 2.54 | 96.2 | 384 | 562 |
| Embodiment 9 | 2.40 | 94.5 | 379 | 554 |
| Comparative example | 3.51 | 115.2 | 394 | 573 |
As shown in table 1, by the result of above-described embodiment it is found that the thin hydridization of super-branched polyimide made from through the invention
Film has low dielectric constant, while having high thermal stability and mechanical property, can satisfy the following high-frequency high-speed 5G communication and
The application requirement of related microelectronic industry.
Claims (7)
1. a kind of polyfunctionality organic acid anhydride, which is characterized in that shown in the following structural formula of its chemical structural formula (1)~(3):
2. a kind of low-k super-branched polyimide film, which is characterized in that it is prepared by the following method to obtain:
(1) organic solvent, aromatic diamine, aromatic dibasic acid acid anhydride and polyfunctionality organic acid are sequentially added in the reaction vessel
Acid anhydride reacts 2-12h at 0-35 DEG C under the protection of nitrogen, obtains polyamic acid precursor solution；In reaction system, fragrant binary
The molar ratio of the total amount and aromatic diamine of acid anhydrides and polyfunctionality organic acid anhydride is 1:1；Aromatic diamine, aromatic dibasic acid acid anhydride
In the total amount of polyfunctionality organic acid anhydride, the molar content of polyfunctionality organic acid anhydride is 0.1-5%；And aromatic diamine,
The gross mass of aromatic dibasic acid acid anhydride and polyfunctionality organic acid anhydride is the 8-30wt% of polyamic acid precursor solution.
(2) catalyst is added in the polyamic acid precursor solution that step 1 obtains, the dosage of catalyst is relative to polyamic acid
The 0.1-2mol% of all acid anhydrides and diamines integral molar quantity used in precursor solution, agitating solution 1-6h utilize curtain coating later
Machine is dried by above-mentioned polyamic acid precursor solution casting film at room temperature, and in 40-60 DEG C, then at 80-150 DEG C of reaction 1-
6h obtains low-k super-branched polyimide film.
3. low-k super-branched polyimide film according to claim 2, which is characterized in that further include to step 2
The low-k super-branched polyimide film of acquisition carries out the step of biaxial tension.The concrete technology of the biaxial tension
Are as follows: 100-250 DEG C of temperature, tensile strength 10-50Mpa, stretching time 5-60min.
4. low-k super-branched polyimide film according to claim 2, which is characterized in that the fragrance binary
Shown in the following structural formula of the chemical structural formula of acid anhydrides (4)~(13):
5. low-k super-branched polyimide film according to claim 2, which is characterized in that the fragrance binary
Shown in the following structural formula of the chemical structural formula of amine (14)~(23):
6. low-k super-branched polyimide film according to claim 2, which is characterized in that the organic solvent
By N-Methyl pyrrolidone, N,N-dimethylformamide, paracresol, o-cresol, metacresol, DMAC N,N' dimethyl acetamide, diformazan
One of base sulfoxide, diethylene glycol monomethyl ether are a variety of by any proportion mixing composition.
7. low-k super-branched polyimide film according to claim 2, which is characterized in that the catalyst
It is made of one or two in acetic anhydride or pyridine by the mixing of any proportion.
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| CN114749038A (en) * | 2021-01-11 | 2022-07-15 | 中化(宁波)润沃膜科技有限公司 | High-flux reverse osmosis composite membrane and preparation method thereof |
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