CN112625278A - Low-dielectric polyimide film and preparation method thereof - Google Patents
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Abstract
A low dielectric polyimide film and a preparation method thereof belong to the technical field of microelectronics. The polyimide film is prepared by taking biphenyl tetracarboxylic dianhydride (BPDA) and 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB) as monomers and tri (4-aminophenyl) amine (TPA) as a cross-linking agent through an in-situ polymerization method to form a film of 5-15 micrometers, wherein the dielectric constant of the film is 1.76-2.80. The molar ratio of the total amount of amino groups to the total amount of anhydride groups involved in the polymerization process is 1: 1, wherein the molar percentage of the number of amino groups in the tris (4-aminophenyl) amine in the total number of amino groups is 0.1-20.0%. The film has the characteristics of low dielectric constant, stable thermodynamic property and good processing property, and has wide application prospect in the fields of flexible circuit boards, microelectronic packaging and the like.
Description
Technical Field
The invention relates to the technical field of microelectronics, in particular to a low dielectric polyimide film and a preparation method and application thereof.
Background
In recent years, the development of ultra-large scale circuits and microelectronics industry has led to the increasing integration and miniaturization of electronic and electrical devices. Meanwhile, the problems of signal transmission delay, crosstalk, loss increase, interconnection resistance-capacitance increase between metal layers and the like are brought, and the problems gradually become bottlenecks limiting the development of microelectronic technology. Therefore, new challenges are presented to the current conventional interlayer dielectric materials.
Polyimide is used as a high-performance polymer material taking an imide ring as a structure, has a temperature resistance of over 400 ℃, and is widely applied to the field of microelectronics due to the advantages of excellent mechanical properties, corrosion resistance, radiation resistance and the like. However, the conventional polyimide has a high dielectric constant (k ═ 3.0 to 3.4), and thus cannot satisfy the requirement of the currently required dielectric material (k < 2.8). Therefore, the research and development of the novel low-dielectric polyimide film have important significance for improving the performance of the integrated circuit, promoting the rapid development of the microelectronic industry and the like.
Disclosure of Invention
In order to solve the technical problems, the application provides a preparation method of a low dielectric polyimide film, in particular to a preparation method of a low dielectric cross-linked polyimide film, which can make up for the defects of the prior art. The product of the invention has the following characteristics: the preparation method is simple, easy to popularize and strong in practicability, and can greatly reduce the dielectric property of the polyimide film and keep good thermal stability and mechanical property.
The invention provides a low-dielectric polyimide film, wherein the polyimide is cross-linked polyimide, monomers used for polymerization are biphenyl tetracarboxylic dianhydride (BPDA) and 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB), and a cross-linking agent is tris (4-aminophenyl) amine (TPA).
In the polyimide film provided by the invention, the molar ratio of the total amount of amino groups to the total amount of anhydride groups involved in the polymerization process is 1: 1, wherein the molar percentage of the amino groups in the tris (4-aminophenyl) amine in the total amino groups is 0.1-20.0%
In the polyimide film provided by the invention, the thickness of the polyimide film is 5-15 μm.
In the polyimide film provided by the invention, the dielectric constant of the polyimide film is 1.76-2.80.
The polyimide film provided by the invention is characterized in that the preparation method comprises the following steps:
(1) adding tris (4-aminophenyl) amine into a polyamic acid solution with the mass concentration of 10-20%, stirring to obtain a polyamic acid solution with a cross-linked structure, uniformly casting the polyamic acid solution on a glass plate, placing the glass plate on a vacuum drying box to remove bubbles, and drying.
(2) And (2) placing the dried glass plate in the step (1) in a forced air drying oven for temperature programmed heat treatment to realize amidation.
(3) And (3) after the glass plate in the step (2) is cooled to room temperature, putting the glass plate into water for membrane stripping, and then carrying out vacuum drying on the membrane to obtain the cross-linked polyimide membrane.
Preferably, the polyamic acid solution of step (1) is obtained by in-situ polymerization of biphenyl tetracarboxylic dianhydride (BPDA), 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB) in a polar solvent.
Further preferably, the polar solvent is one of N, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMAC), and N-methylpyrrolidone (NMP).
Further preferably, the in situ polymerization conditions are N2Stirring for 3-8 h at room temperature in an atmosphere.
Preferably, the bubble removing time in the step (1) is 3-10 min.
Preferably, the temperature range of the thermal amidation in the step (2) is 80-300 ℃, further preferably, the temperature is respectively maintained for 1h at 80 ℃, 100 ℃, 200 ℃ and 300 ℃, and the temperature rise rate is controlled to be 2-6 ℃/min.
The polyimide film prepared by the preparation method of the technical scheme or the polyimide film prepared by the preparation method of the technical scheme provided by the invention is applied to the fields of integrated circuits and microelectronics.
Compared with the prior art, the invention has the following beneficial effects:
compared with the common polyimide film, the low dielectric cross-linked polyimide film prepared by the invention effectively reduces the dielectric constant of polyimideAnd maintains good heat resistance. The dielectric constant of 100Hz frequency is reduced from 3.0 to 2.5 of polyimide, and the dielectric constant is gradually reduced with the increase of frequency, and the lowest value can be 1.76(f is 10)7Hz). Meanwhile, good thermal stability and mechanical property are kept, so that the polyimide film has great application potential in the fields of integrated circuits, microelectronic packaging and the like.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. Other advantages of the invention may be realized and attained by the instrumentalities and combinations particularly pointed out in the specification.
Drawings
The accompanying drawings are included to provide an understanding of the present invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the examples serve to explain the principles of the invention and not to limit the invention.
FIG. 1 is a Fourier infrared spectrum of a crosslinked polyimide (abbreviated as PI-1, PI-2) prepared in example 1 and a linear polyimide (abbreviated as PI-0) in comparative example 1
FIG. 2 is a DSC chart of the crosslinked polyimide (abbreviated as PI-1, PI-2) prepared in example 1 and the linear polyimide (abbreviated as PI-0) in comparative example 1.
FIG. 3 is a graph showing the dielectric constant with frequency of the crosslinked polyimide (abbreviated as PI-1, PI-2) prepared in example 1 and the linear polyimide (abbreviated as PI-0) in comparative example 1.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention are described in detail below. It should be noted that the embodiments and features of the embodiments of the present invention may be arbitrarily combined with each other without conflict.
The embodiment of the invention provides a low-dielectric polyimide film, wherein the polyimide is cross-linked polyimide, monomers used for polymerization are biphenyl tetracarboxylic dianhydride (BPDA) and 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB), and a cross-linking agent is tris (4-aminophenyl) amine (TPA).
In the embodiment of the invention, the molar ratio of the total amount of amino groups and the total amount of anhydride groups involved in the polymerization process is 1: 1, wherein the molar percentage of the number of amino groups in TPA in the total number of amino groups is 0.1-20.0%.
In the embodiment of the invention, the thickness of the low dielectric polyimide film is 5-15 μm.
In the embodiment of the invention, the dielectric constant of the low dielectric polyimide film is 1.76-2.80.
In the embodiment of the invention, the preparation method of the low dielectric polyimide film comprises the following steps,
(1) adding tris (4-aminophenyl) amine into a polyamic acid solution with the mass concentration of 10-20%, stirring to obtain a polyamic acid solution with a cross-linked structure, uniformly casting the polyamic acid solution on a glass plate, placing the glass plate on a vacuum drying box to remove bubbles, and drying. The polyamic acid solution is obtained by in-situ polymerization of biphenyl tetracarboxylic dianhydride (BPDA) and 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB) in a polar solvent under the condition of N2Stirring for 3-8 h at room temperature in an atmosphere; the polar solvent selected by the invention is one of N, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMAC) and N-methylpyrrolidone (NMP); according to the invention, the time for removing bubbles is 3-10 min.
(2) And (2) placing the dried glass plate in the step (1) in a forced air drying oven for temperature programmed heat treatment to realize amidation. In the invention, the temperature range of the programmed temperature rise is 80-300 ℃, preferably the temperature is respectively kept at 80 ℃, 100 ℃, 200 ℃ and 300 ℃ for 1h, and the temperature rise rate is controlled at 2-6 ℃/min.
(3) And (3) after the glass plate in the step (2) is cooled to room temperature, putting the glass plate into water for membrane stripping, and then carrying out vacuum drying on the membrane to obtain the cross-linked polyimide membrane.
The present invention will be described in detail below with reference to specific examples.
In the examples of the present invention, the biphenyl tetracarboxylic dianhydride, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, tris (4-aminophenyl) amine) was purchased from beijing rainbow lake integrated chemicals ltd.
Example 1
0.5090g of 6FAPB is dissolved in 3.927ml of DMAC, and the mixture is stirred until the mixture is completely dissolved; 0.3530g of BPDA were then added in three portions and the mixture was stirred at N2Stirring for 5h at room temperature under an atmosphere to obtain a homogeneous viscous solution with the mass concentration of 18%. Then 0.0023g TPA is added, stirred for 5min in ice-water bath, and after the TPA is completely dissolved, the mixed system is placed in a vacuum drying oven at 60 ℃ to remove bubbles for 3 min. Finally, the polyimide film is cast on a dry glass plate by a tape casting method, is placed in a blast drying oven, and is subjected to thermal amidation in a temperature gradient of 80-300 ℃ (the temperature gradient is 1 hour at 80 ℃, 100 ℃, 200 ℃ and 300 ℃, and the heating rate is 6 ℃/min), so that the crosslinked polyimide film PI-1 can be obtained, and the dielectric constant of the crosslinked polyimide film PI-1 is 2.15(f is 10 DEG)7Hz)。
Example 2
0.5040g of 6FAPB is dissolved in 3.927ml of DMAC, and the mixture is stirred until the mixture is completely dissolved; 0.3530g of BPDA were then added in portions and under N2Stirring for 5h at room temperature under an atmosphere to obtain a homogeneous viscous solution with the mass concentration of 18%. Then 0.0050g of TPA was added, and stirred in an ice-water bath for 5min, and after it was completely dissolved, the above mixed system was placed in a vacuum drying oven to remove bubbles for 3 min. Finally, the polyimide film is cast on a dry glass plate by a tape casting method, is placed in a blast drying oven, and is subjected to thermal amidation in a temperature gradient of 80-300 ℃ (the temperature gradient is 1 hour at 80 ℃, 100 ℃, 200 ℃ and 300 ℃, and the heating rate is 6 ℃/min), so that the crosslinked polyimide film PI-2 can be obtained, and the dielectric constant of the crosslinked polyimide film PI-2 is 1.76(f is 10 DEG)7Hz)。
Comparative example 1
0.5140g of 6FAPB is dissolved in 3.950ml of DMAC, and the mixture is stirred until the mixture is completely dissolved; 0.3530g of BPDA were then added in portions and under N2Stirring for 5h at room temperature under an atmosphere to obtain a homogeneous viscous solution with the mass concentration of 18%. And putting the mixed system in a vacuum drying oven, vacuumizing and removing bubbles for 3 min. Finally, the non-crosslinking agent is cast on a dry glass plate by a tape casting method, the glass plate is placed in a blast drying oven, and thermal amidation is carried out in a temperature gradient of 80-300 ℃ (the temperature is 80 ℃, 100 ℃, 200 ℃ and 300 ℃ for 1 hour respectively, and the heating rate is 6 ℃/min), so that the non-crosslinking agent can be obtainedThe dielectric constant of the linear polyimide film PI-0 of (2.20) (f is 10)7Hz)。
Test example 1
Fourier infrared spectrum test: the prepared cross-linked polyimide film is cut into small blocks of 30mm multiplied by 30mm and is obtained by testing a single reflection Attenuated Total Reflectance (ATR) accessory in a Fourier transform infrared spectrometer, and the scanning range is 3500-500 cm-1。
Differential scanning calorimetry: weighing 4-6mg of the composite film, pressing a sample into an aluminum crucible by using a sample preparation device, putting the aluminum crucible into a differential scanning calorimeter (Shimadzu, DSC-60), and testing a DSC curve with the temperature range of 50-400 ℃ at the temperature rise speed of 10 ℃/min in the nitrogen atmosphere.
And (3) dielectric property test: the method comprises the steps of respectively evaporating copper electrodes on two surfaces of a film by using a high-vacuum resistance evaporation coating machine, then placing the film coated with the copper electrodes into a precision impedance analyzer (Agilent 4294A), clamping the copper electrodes by using a clamp, and testing 100Hz-10 at room temperature7Dielectric properties in the Hz range.
FIG. 1 is a Fourier infrared spectrum of a crosslinked polyimide (abbreviated as PI-1, PI-2) prepared in example 1 and a linear polyimide (abbreviated as PI-0) in comparative example 1
FIG. 2 is a DSC chart of the crosslinked polyimide (abbreviated as PI-1, PI-2) prepared in example 1 and the linear polyimide (abbreviated as PI-0) in comparative example 1.
FIG. 3 is a graph showing the change of dielectric constant with frequency of the crosslinked polyimides (abbreviated as PI-1 and PI-2) prepared in example 1 and the linear polyimide (abbreviated as PI-0) in comparative example 1
As can be seen from the figure, the polyimide with a cross-linked structure is successfully prepared by using the biphenyl tetracarboxylic dianhydride and the 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene as the polymerization monomers and the tri (4-aminophenyl) amine as the cross-linking agent. Compared with linear polyimide obtained by the same proportioning and experimental conditions, the addition of the cross-linking agent can obviously reduce the dielectric constant of the polyimide, and the dielectric constant is gradually reduced along with the increase of frequency, and can be as low as 1.76(f is 10)7Hz), the glass transition temperature (Tg) does not decrease significantly. It is composed ofThe reason is that the dielectric constant of the material is mainly related to the molar volume and molar polarizability of dipoles, the cross-linked network structure enables polyimide molecules to have larger free volume, the number of dipoles in unit volume can be reduced, and the cross-linked network structure enables the dipoles on the rigid polyimide molecular chains to be more difficult to rotate, so that the purpose of reducing the dielectric constant is achieved.
Although the embodiments of the present invention have been described above, the above description is only for the convenience of understanding the present invention, and is not intended to limit the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. The low-dielectric polyimide film is characterized in that the polyimide is cross-linked polyimide, monomers used for polymerization are biphenyl tetracarboxylic dianhydride (BPDA) and 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB), and a cross-linking agent is tris (4-aminophenyl) amine (TPA).
2. The low dielectric polyimide film of claim 1, wherein a molar ratio of a total amount of amino groups to a total amount of acid anhydride groups involved in the polymerization process is 1: 1, wherein the mole percentage of the amino group number in the tri (4-aminophenyl) amine in the total amino group number is 0.1-20.0%.
3. The low dielectric polyimide film according to claim 1, wherein the polyimide film has a thickness of 5 to 15 μm.
4. The low dielectric polyimide film according to claim 1, wherein the polyimide film has a dielectric constant of 1.76 to 2.80.
5. The method for preparing a low dielectric polyimide film according to any one of claims 1 to 4, comprising the steps of:
(1) adding tris (4-aminophenyl) amine into a polyamic acid solution with the mass concentration of 10-20%, stirring to obtain a polyamic acid solution with a cross-linking structure, uniformly casting the polyamic acid solution on a glass plate, and placing the glass plate in a vacuum drying oven to remove bubbles and dry;
(2) placing the dried glass plate obtained in the step (1) in a forced air drying oven for temperature programmed heating treatment to realize amidation;
(3) and (3) after the glass plate in the step (2) is cooled to room temperature, putting the glass plate into water for membrane stripping, and then carrying out vacuum drying on the membrane to obtain the cross-linked polyimide membrane.
6. The method according to claim 5, wherein the polyamic acid solution of step (1) is obtained by in-situ polymerization of biphenyl tetracarboxylic dianhydride (BPDA), 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene (6FAPB) in a polar solvent.
7. The method according to claim 6, wherein the polar solvent is one of N, N-Dimethylformamide (DMF), N-Dimethylacetamide (DMAC) and N-methylpyrrolidone (NMP).
8. The method of claim 6, wherein the in situ polymerization condition is N2Stirring for 3-8 h at room temperature in an atmosphere.
9. The preparation method according to claim 5, wherein the stirring conditions in the step (1) are stirring in an ice-water bath for 3-10 min; the bubble removing time is 3-10 min.
10. The method according to claim 5, wherein the temperature range of the heat treatment in the step (2) is 80 to 300 ℃, and the temperature rise rate is controlled to be 2 to 6 ℃/min.
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CN117820640A (en) * | 2024-01-05 | 2024-04-05 | 中南大学 | Cross-linked polyimide dielectric film material and preparation method thereof |
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CN110734559A (en) * | 2018-07-18 | 2020-01-31 | 北京化工大学 | Cross-linked polyimide film and preparation method and application thereof |
US20200369832A1 (en) * | 2019-05-21 | 2020-11-26 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Crosslinked polymide, polymide film and method for preparing thereof, organic light emitting diode device |
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US20110136061A1 (en) * | 2003-03-28 | 2011-06-09 | Hiroshi Itatani | Crosslinked polyimide, composition comprising the same and process for producing the same |
CN110734559A (en) * | 2018-07-18 | 2020-01-31 | 北京化工大学 | Cross-linked polyimide film and preparation method and application thereof |
CN109734954A (en) * | 2019-01-15 | 2019-05-10 | 东华大学 | A kind of flexible polyimide aeroge and its preparation method and application with good moisture resistance |
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CN114231029A (en) * | 2021-12-29 | 2022-03-25 | 山东华夏神舟新材料有限公司 | Cross-linked high-transparency polyimide film and preparation method thereof |
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CN117820640A (en) * | 2024-01-05 | 2024-04-05 | 中南大学 | Cross-linked polyimide dielectric film material and preparation method thereof |
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