CN115322364B - Ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound and preparation method thereof - Google Patents
Ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound and a preparation method thereof. The invention firstly reacts dihydroxyl column [5] aromatic compound with excessive decafluorobiphenyl to prepare an ABA monomer with high reactivity, and then the monomer is polymerized with decafluorobiphenyl and bisphenol fluorene in one step to obtain the ultra-low dielectric constant column [5] aromatic fluorine-containing polyarylether compound. The obtained column [5] arene fluorine-containing polyarylether compound not only has ultralow dielectric constant, but also has excellent solubility, thermal stability, oxidation stability, mechanical properties and the like.
Description
Technical Field
The invention relates to an ultralow dielectric constant column [5] arene fluorine-containing polyarylether compound and a preparation method thereof, belonging to the technical field of organic synthesis.
Background
The rapid development of ultra large scale integrated circuits (ULSI) has led to a miniaturization of the chip scale, more and more transistors being integrated in very narrow areas. Miniaturization of devices often creates problems with interconnect signal delay (RC delay), noise cross talk, and power consumption, which affect device performance. In order to reduce the resistance-capacitance (RC) delay, low dielectric constant materials are urgently needed. On the other hand, low dielectric constant materials are also required for the development of the power industry. To solve this problem, researchers have begun to explore a large number of materials with low dielectric constants. Such as polyimide, polyarylether, polyetherketone, heteroaromatic polymers, and fluoropolymers. The polyarylether is a high-performance special engineering plastic, is used as a semi-crystalline aromatic thermoplastic polymer material, has rigid phenylene and flexible ether bonds, has excellent properties such as good creep resistance, high strength, strong mechanical property and the like, and is widely applied to the fields of aerospace, chemical industry, precise instruments and the like. However, most polyarylethers have a high dielectric constant and water absorption. The introduction of fluorine element, while reducing both parameters and improving thermal stability, solubility, etc., still fails to meet the needs of technological development. .
Supermolecular chemistry is an emerging discipline, with macrocyclic host compounds being an important foundation, and column [5] arenes are considered to be a new generation of macrocyclic host compounds. The column [5] arene has wide modification, which makes it have potential application in the fields of supermolecular polymer, functional material, nanometer channel, molecular device, etc. The invention introduces the column [5] arene into the main chain of fluorine-containing polyarylether, realizes ultralow dielectric property, and has important significance in the fields of development of high-performance polyarylether, electronic packaging and the like.
Disclosure of Invention
The invention provides an ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound and a preparation method thereof, which are used for overcoming the defects of the prior art. The compound has excellent solubility, thermal stability, oxidation stability, mechanical property and ultralow dielectric constant and dielectric loss.
The aim is achieved by the following technical scheme:
an ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound has a chemical structure shown in a formula I.
I
Wherein x=10 to 80, y=10 to 50.
The preparation method of the ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound comprises the following steps:
(1) Dissolving dihydroxyl column [5] arene (synthesized according to chem. Commun., 2012,48, 9876-9878 literature) and decafluorobiphenyl in N-methyl pyrrolidone, then adding cesium fluoride, reacting for 3-5 days at normal temperature, slowly pouring the reactant into deionized water, then adding dichloromethane for extraction, and collecting dichloromethane phase; evaporating dichloromethane, sublimating excessive decafluorobiphenyl, and recycling; and finally, purifying the obtained object by using a silica gel column to obtain the high-reactivity ABA monomer. The following reaction scheme is as follows:
for ease of understanding, the planar structural formula of the ABA monomer is as follows:
(2) Bisphenol fluorene, decafluorobiphenyl, ABA type monomer and cesium fluoride are added into N-methyl pyrrolidone, and the mixture is reacted for 10 to 30 hours at normal temperature under the protection of argon; pouring the reactant into deionized water to separate out precipitate, filtering and collecting the precipitate, dissolving the precipitate with dichloromethane, pouring the solution into methanol to separate out the precipitate, and filtering and collecting the precipitate to obtain the ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound. The following reaction scheme is as follows:
wherein x=10 to 80, y=10 to 50.
Further, in the step (1), the dihydroxyl column [5] arene is calculated according to the mole ratio: decafluorobiphenyl: csf=1:8 to 10:3 to 6.
Further, in the step (1), the mobile phase is methylene dichloride and petroleum ether during column purification.
Further, the mass of the N-methyl pyrrolidone solvent in the step (1) is 5-20 times of the mass of the dihydroxy column [5] arene.
Further, the mass of the deionized water in the step (1) is 8-10 times of that of the N-methyl pyrrolidone solvent; the mass of the dichloromethane is 0.2-2 times of that of the deionized water.
Further, in the step (2), the molar amount of bisphenol fluorene is equal to the sum of the molar amounts of decafluorobiphenyl and ABA type monomer, the decafluorobiphenyl and ABA type monomer are mixed according to any proportion, and the molar amount of CsF is 2-6 times of the molar amount of bisphenol fluorene.
A column [5] arene fluorine-containing polyarylether film is prepared by the following method: and dissolving the obtained column [5] arene fluorine-containing polyarylether compound in N-methyl pyrrolidone to prepare the fluorine-containing polyarylether film with the concentration of 5-10 wt%, casting the fluorine-containing polyarylether film on a glass plate which is horizontally placed, drying the fluorine-containing polyarylether film in a blast oven at 80 ℃ for 12-36 h, and then drying the fluorine-containing polyarylether film in a vacuum oven at 80 ℃ for 12-36 h to obtain the column [5] arene fluorine-containing polyarylether film.
The preparation method of the present invention is a preferable scheme, and reasonable temperature, time and other reaction conditions which can be foreseen by the person skilled in the art are all within the scope of the present invention, and are not limited to the above reaction conditions.
The invention synthesizes ABA monomer first and then performs polycondensation reaction according to a certain proportion, and compared with the prior art, the invention has the following beneficial effects:
(1) The adopted raw materials are common chemical raw materials, so that the price is low and the raw materials are easy to obtain; few reaction byproducts, high yield and easy column purification;
(2) The obtained ABA type monomer belongs to a macrocyclic main compound, has large self molecular weight and small reaction steric hindrance, and can obviously improve the molecular weight of a product when used for polymerization;
(3) The obtained column [5] arene fluorine-containing polyarylether compound material has ultrahigh fluorine content, and also has a porous column [5] arene structure, unique structure, easy dissolution in common solvents such as dichloromethane, chloroform, N-methylpyrrolidone and the like, and convenient processing and forming.
(4) The obtained column [5] arene fluorine-containing polyarylether compound material has ultralow dielectric constant and wide application prospect in the field of semiconductor packaging.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of an ABA type monomer in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance fluorine spectrum of an ABA type monomer in example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of a column [5] arene type fluorine-containing polyarylether compound in example 2 of the present invention;
FIG. 4 is a nuclear magnetic resonance fluorine spectrum of a column [5] arene type fluorine-containing polyarylether compound in example 2 of the present invention;
FIG. 5 is a differential scanning calorimetric graph of a column [5] arene-type fluorine-containing polyarylether compound in example 2 of the present invention;
FIG. 6 is a thermogravimetric analysis of column [5] arene-type fluorine-containing polyarylether compound of example 2 of the present invention;
FIG. 7 is an infrared spectrum of a column [5] arene type fluorine-containing polyarylether compound in example 2 of the present invention;
FIG. 8 shows the dielectric properties of the column [5] arene-type fluorine-containing polyarylether film of example 2 of the present invention, curve a being the dielectric loss curve and curve b being the dielectric constant curve;
FIG. 9 is a scanning electron micrograph of a column [5] arene type fluorine-containing polyarylether film of example 2 of the present invention, the left view being the film surface and the right view being the film cross section;
FIG. 10 is a graph showing the water contact angle of column [5] arene-type fluorine-containing polyarylether films in example 2 of the present invention.
Detailed Description
The invention is further illustrated below in connection with specific examples, but the invention is not limited to these examples only.
EXAMPLE 1 preparation of highly reactive ABA monomer
9.00 g (11.68 mmol) dihydroxy column [5]]Aromatic hydrocarbon and decafluorobiphenyl 19.50g (93.45 mmol) are dissolved in 120ml of N-methylpyrrolidone, the mixture is placed on a magnetic stirring table and stirred by a magnet, 5.32g (35.04 mmol) CsF is weighed after the mixture is dissolved, and the mixture is placed in a reaction kettle to react for 5 days under the protection of argon at normal temperature. Slowly pouring the reactant into deionized water, then adding dichloromethane for extraction, and collecting a dichloromethane phase; evaporating dichloromethane, sublimating excessive decafluorobiphenyl by using a sublimating device, and recycling the excess decafluorobiphenyl; and finally, purifying the obtained viscous liquid by using a silica gel column to obtain the high-reactivity ABA type monomer. Yield: 90%. The nuclear magnetic resonance hydrogen spectrum of the compound is shown in figure 1: 1 H NMR (400 MHz, CDCl 3 ppm) delta 3.56 (s, 2H), 3.68 (s, 2H), 3.69 (s, 2H), 3.72 (s, 2H), 3.78 (s, 2H), 3.79 (s, 4H), 3.81 (s, 4H), 3.82 (s, 4H), 3.83 (s, 4H), 3.86 (s, 4H), 3.90 (s, 4H), 3,92 (s, 4H), 6.64 (s, 2H), 6.75 (s, 2H), 6.79 (s, 2H), 6.83 (s, 2H), 6.84 (s, 2H). The nuclear magnetic resonance fluorine spectrum of the compound is shown in figure 2: 19 F NMR -155(s, 4F),-150(s, 2F),-145(s, 4F),-135(s, 4F)。
EXAMPLE 2 preparation of column [5] arene-type fluorine-containing polyarylether Compound
0.6755g (0.5 mmol) of ABA type monomer, 0.5011g (0.15 mmol) of decafluorobiphenyl, 0.7008g (2 mmol) of bisphenol fluorene and NMP (45 mL) are placed in a 50mL three-neck flask equipped with a magnetic stirrer, the mixture is placed on a magnetic stirring table and stirred by a magnet, after the mixture is dissolved, 0.9g (6 mmol) of cesium fluoride is weighed and poured into the three-neck flask, the mixture is reacted for 24 hours at normal temperature under the protection of argon, the reactant is poured into deionized water to precipitate, the precipitate is filtered and collected, the precipitate is redissolved in dichloromethane, then the precipitate is poured into methanol to precipitate, the precipitate is filtered and collected, and the precipitate is dried for 24 hours at 80 ℃ in a vacuum oven to obtain the ultra-low dielectric constant column [5]]Aromatic fluorine-containing polyarylether compounds. Yield: 98%. The nuclear magnetic resonance hydrogen spectrum is shown in figure 3: 7.75 (s, 4H), 7.49 (s, 4H), 7.38 (s, 4H), 7.15 (s, 8H), 6.90 (s, 8H), 6.84 (s, 2H), 6.83 (s, 2H), 6.79 (s, 2H), 6.75 (s, 2H), 6.64 (s, 2H), 3.92 (s, 4H), 3.90 (s, 4H), 3.86 (s, 4H), 3.83 (s, 4H), 3.82 (s, 4H), 3.81 (s, 4H), 3.79 (s, 4H), 3.78 (s, 2H), 3.72 (s, 2H), 3.69 (s, 2H), 3.68 (s, 2H), 3.56 (s, 2H). The nuclear magnetic resonance fluorine spectrum is shown in FIG. 4, and the characteristic peak of F on the polymer can be seen. The differential scanning calorimetry curve is shown in FIG. 5, from which it is seen that the glass transition temperature of the polymer is 255 ℃. The thermogravimetric curve is shown in FIG. 6, from which the 5wt% thermogravimetric temperature of the polymer is 425 ℃. The infrared spectrum is shown in fig. 7: 1650 cm -1 Left and right are-c=o stretching vibration peaks; 2970-3000 cm -1 Left and right are-CH 3 and-CH 2 Is a stretching vibration peak of (2); 1230 cm -1 The left and right are the stretching vibration peaks of aryl ether bond Ar-O-Ar; 1460 cm -1 The left and right are C-H bending vibration peaks of methylene; 1250 cm -1 The left and right are C-H bending vibration peaks of methyl; 1507 cm -1 The left and right are the stretching vibration peaks of benzene ring c=c; 730cm -1 The left and right are the absorption peaks of C-F construction.
Example 3 preparation of column [5] arene type fluorine-containing polyarylether film
The resulting column [5]]Dissolving aromatic fluorine-containing polyarylether compound in N-methyl pyrrolidone to prepare the mixture with the concentration of 8 percent wt percent, casting the mixture on a glass plate which is horizontally placed, drying the mixture in a blast oven at 80 ℃ for 24 hours, and then drying the mixture in a vacuum oven at 80 ℃ for 24 hours to obtain a column [5]]Aromatic hydrocarbon type fluorine-containing polyarylether film. The dielectric loss and dielectric constant were measured as shown in fig. 8, respectively: the dielectric constant and dielectric loss gradually decrease with increasing frequency at 10 6 At the frequency of Hz, the dielectric loss and dielectric constant were 0.0096 and ultra-low 1.65, respectively. Scanning electron micrographs of the surface and cross section of the films were tested, as shown in fig. 9, with the left plot showing the surface of the film and the right plot showing the cross section of the film, and it can be seen that the film was relatively dense. The water contact angle of the film surface was 98.8 °, as shown in fig. 10, indicating good hydrophobicity.
The foregoing description is only of the preferred embodiments of the invention, and all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (8)
1. An ultralow dielectric constant column [5] arene fluorine-containing polyarylether compound is characterized by having a chemical structural formula as follows:
wherein x=10 to 80, y=10 to 50.
2. The method for preparing the ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound according to claim 1, which is characterized by comprising the following specific steps:
(1) Dissolving a dihydroxyl column [5] aromatic compound and decafluorobiphenyl into N-methylpyrrolidone, then adding cesium fluoride, reacting for 3-5 days at normal temperature, slowly pouring reactants into deionized water, then adding dichloromethane for extraction, and collecting a dichloromethane phase; evaporating dichloromethane, sublimating excessive decafluorobiphenyl, and recycling; finally, purifying the obtained substance by using a silica gel column to obtain an ABA type monomer with high reactivity;
the chemical structural formula of the obtained ABA type monomer is shown as follows:
(2) Bisphenol fluorene, decafluorobiphenyl, ABA type monomer and cesium fluoride are added into N-methyl pyrrolidone, and the mixture is reacted for 10 to 30 hours at normal temperature under the protection of argon; pouring the reactant into deionized water to separate out precipitate, filtering and collecting the precipitate, dissolving the precipitate with dichloromethane, pouring the solution into methanol to separate out the precipitate, and filtering and collecting the precipitate to obtain the ultra-low dielectric constant column [5] arene fluorine-containing polyarylether compound.
3. The method for producing an ultra-low dielectric constant column [5] aromatic hydrocarbon type fluorine-containing polyarylether compound according to claim 2, wherein in the step (1), the dihydroxy column [5] aromatic hydrocarbon compound: decafluorobiphenyl: the molar ratio of CsF is 1:8-10:3-6.
4. The method for producing an ultra-low dielectric constant column [5] aromatic fluorine-containing polyarylether compound according to claim 2, wherein the mobile phase is methylene chloride and petroleum ether in the purification by passing through the column in the step (1).
5. The method for preparing an ultra-low dielectric constant column [5] arene type fluorine-containing polyarylether compound according to claim 2, wherein the mass of the N-methylpyrrolidone in the step (1) is 5 to 20 times the mass of the dihydroxy column [5] arene.
6. The method for preparing an ultra-low dielectric constant column [5] aromatic hydrocarbon type fluorine-containing polyarylether compound according to claim 2, wherein the mass of deionized water in the step (1) is 8-10 times that of N-methylpyrrolidone; the mass of the dichloromethane is 0.2-2 times of that of the deionized water.
7. The method for preparing an ultra-low dielectric constant column [5] aromatic hydrocarbon type fluorine-containing polyarylether compound according to claim 2, wherein the molar amount of bisphenol fluorene in the step (2) is equal to the sum of the molar amounts of decafluorobiphenyl and ABA type monomer, and the molar amount of CsF is 2-6 times the molar amount of bisphenol fluorene.
8. A column [5] arene type fluorine-containing polyarylether film prepared from the ultra-low dielectric constant column [5] arene type fluorine-containing polyarylether compound of claim 1, which is characterized by the following preparation method: dissolving an ultralow dielectric constant column [5] arene type fluorine-containing polyarylether compound in N-methyl pyrrolidone to prepare the fluorine-containing polyarylether film with the concentration of 5-10 wt%, casting the fluorine-containing polyarylether film on a glass plate which is horizontally placed, drying the fluorine-containing polyarylether film in a blast oven at 80 ℃ for 12-36 hours, and then drying the fluorine-containing polyarylether film in vacuum at 80 ℃ for 12-36 hours to obtain the column [5] arene type fluorine-containing polyarylether film.
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