CN113372553A - Low-melting-point circuit board substrate and preparation method thereof - Google Patents
Low-melting-point circuit board substrate and preparation method thereof Download PDFInfo
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- CN113372553A CN113372553A CN202110586374.6A CN202110586374A CN113372553A CN 113372553 A CN113372553 A CN 113372553A CN 202110586374 A CN202110586374 A CN 202110586374A CN 113372553 A CN113372553 A CN 113372553A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention discloses a circuit board substrate with low melting point and a preparation method thereof, belongs to the technical field of high molecular materials, and solves the technical problems of high melting point of thermoplastic polyimide and low bonding performance between the substrate and a copper substrate, 4 '-dimethyl diphenyl sulfide and methane chloride are grafted with methyl on a benzene ring of 4, 4' -dimethyl diphenyl sulfide under the catalysis of aluminum trichloride to prepare an intermediate 1, the methyl on the intermediate 1 is oxidized into carboxyl, then phosphorus pentoxide is catalyzed into an intermediate 3, a polymer containing thioether bonds in molecules is prepared by copolymerization of 1, 4-phenylenediamine, 1, 2-ethylenediamine and the intermediate 3, so that the melting temperature of the substrate is below 301 ℃, the glass transition temperature is kept above 185 ℃, the circuit board substrate has excellent processability and also keeps good heat resistance, meanwhile, the affinity of the base material and the metal base is improved, and the bonding strength is improved.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a circuit board substrate with a low melting point and a preparation method thereof.
Background
Polyimide resin is one of high polymer materials with the highest heat-resistant grade in industrial practical application at present, and has been widely applied to the fields of aerospace, mechanical and chemical engineering, electronics and electricity and the like due to the comprehensive properties of high thermal stability, solvent resistance, high mechanical strength, excellent insulating property, radiation resistance and the like.
Polyimide is classified into thermosetting and thermoplastic according to whether secondary processing is possible; the thermosetting polyimide is a reticular molecular chain formed by internal crosslinking of a prepolymer after processing and molding, and the material is not molten and insoluble and can not be subjected to secondary processing; the thermoplastic polyimide is polyimide with a linear molecular chain, and can be processed secondarily theoretically, but the general linear polyimide molecular chain contains a large number of benzene heterocycles, the rigidity of the molecular chain is high, and the acting force between the molecular chains is large, so that the general linear polyimide molecule cannot be processed secondarily. In addition, the existing polyimide base material has low bonding performance with a copper material substrate, an adhesive is needed, no matter what adhesive is adopted, the thermal stability is poor, the difference between the thermal expansion coefficient of the existing polyimide base material and the thermal expansion coefficient of the existing copper base material is large, and the heat dissipation performance of a circuit can be directly influenced by the adhesive, so that the flexibility performance and the flexibility service life of the flexible circuit board are greatly reduced.
Disclosure of Invention
The invention aims to provide a circuit board substrate with a low melting point and a preparation method thereof.
The technical problems to be solved by the invention are as follows: the thermoplastic polyimide has a high melting point, which causes the technical problem of inconvenient production and processing, and the technical problem of low bonding property between the existing polyimide base material and the copper base.
The purpose of the invention can be realized by the following technical scheme:
a circuit board substrate with a low melting point is prepared by copolymerizing 1, 4-phenylenediamine, 1, 2-ethylenediamine and an intermediate 3, and has the following general formula:
wherein, X is one of ether bond, thioether bond, ketone group and sulfone group.
Further, X is a thioether bond, and the specific preparation method comprises the following steps:
step S1: taking a reactor provided with a conduit, adding 4, 4' -dimethyl diphenyl sulfide and aluminum trichloride into the reactor, controlling the reaction temperature to be 65-70 ℃ under the protection of nitrogen, introducing methane chloride from the conduit, and filtering the reaction liquid to obtain an intermediate 1;
the specific reaction process is as follows:
step S2: taking a reactor provided with a stirrer, adding the intermediate 1 into the reactor, controlling the stirring speed at 120-;
the specific reaction process is as follows:
step S3: taking a reactor provided with a stirrer, adding the intermediate 2 and deionized water into the reactor, controlling the stirring speed to be 210-250r/min, adding phosphorus pentoxide into the reactor for three times, stirring and reacting for 3-4h after all the phosphorus pentoxide is added, filtering reaction liquid after the reaction is ended, washing the filtrate for 2-3 times by using ice water, taking lower layer clear liquid, and carrying out rotary evaporation until light yellow crystals are precipitated to obtain an intermediate 3;
the specific reaction process is as follows:
step S4: adding N, N-dimethylacetamide into a reactor with a stirrer, adding the intermediate 3, stirring until the intermediate 3 is completely dissolved, adding 1, 4-phenylenediamine and 1, 2-ethylenediamine into the reactor, heating to 52-55 ℃, controlling the stirring speed at 200-.
The specific reaction process is as follows:
further, in step S1, the ratio of 4, 4' -dimethyl diphenyl sulfide to methyl chloride is 100 mL: 0.21-0.24m3And the introduction speed of the monochloromethane is 0.15-0.18m3/h。
Further, in step S4, the amount ratio of the intermediate 3, 1, 4-phenylenediamine to 1, 2-ethylenediamine is 2 mol: 2.25-2.4 mol: 1.15-1.3 mol.
The invention has the beneficial effects that:
the invention relates to a low-melting-point circuit board substrate, which is prepared by preparing an intermediate 3, wherein the intermediate 3 is prepared by grafting methyl on a benzene ring of 4, 4' -dimethyl diphenyl sulfide under the catalysis of aluminum trichloride to prepare an intermediate 1, oxidizing the methyl on the intermediate 1 into carboxyl, catalyzing the carboxyl by phosphorus pentoxide to prepare an intermediate 3, copolymerizing 1, 4-phenylenediamine, 1, 2-ethylenediamine and the intermediate 3 to prepare a polymer containing an imide ring (-CO-N-CO-) on a main chain, taking the polymer as a circuit board substrate, reducing the melting temperature of the polymer due to introduction of thioether bonds into polyimide molecules, and testing the low-melting-point circuit board substrate prepared by the invention has the melting temperature of below 301 ℃, the glass transition temperature is kept above 185 ℃, and the high-temperature-resistant glass has excellent processability and keeps good heat resistance.
According to the circuit board base material with the low melting point, thioether bonds are introduced into molecules, and due to the fact that lone-pair electrons exist on sulfur atoms, the base material has good affinity with metal, so that the base material and a metal substrate in a circuit board have stronger bonding strength, and the influence of an adhesive on heat dissipation of the circuit is avoided.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A circuit board substrate with a low melting point is prepared by copolymerizing 1, 4-phenylenediamine, 1, 2-ethylenediamine and an intermediate 3, and has the following general formula:
wherein the structural formula of the intermediate 3 is as follows:
example 2
The preparation method of the intermediate 3 comprises the following steps:
step A1: taking a reactor provided with a conduit, adding 4, 4 '-dimethyl diphenyl sulfide and aluminum trichloride into the reactor, controlling the reaction temperature to be 65 ℃ under the protection of nitrogen, and introducing methane chloride, 4, 4' -dimethyl diphenyl sulfide and methane chloride from the conduit with the dosage ratio of 100 mL: 0.21m3The introduction speed of the monochloromethane is controlled to be 0.15m3After all the chloromethane is introduced, filtering the reaction liquid to prepare an intermediate 1;
step A2: taking a reactor provided with a stirrer, adding the intermediate 1 into the reactor, controlling the stirring speed to be 120r/min and the reaction temperature to be 78 ℃, adding potassium permanganate into the reactor, and controlling the dosage ratio of the intermediate 1 to the potassium permanganate to be 100 mL: 5.5g, reacting for 1h, and filtering and removing excessive potassium permanganate in the reaction liquid to obtain an intermediate 2;
step A3: taking a reactor with a stirrer, adding the intermediate 2 and deionized water into the reactor, controlling the stirring speed to be 210r/min, taking phosphorus pentoxide, evenly dividing into three parts, adding into the reactor three times, adding the time interval T of 10min (the total volume/L of the intermediate 2 and the deionized water), stirring and reacting for 3h after all the phosphorus pentoxide is added, filtering the reaction solution after the reaction is ended, washing the filtrate for 2 times by using ice water, taking the lower layer clear solution for rotary evaporation until light yellow crystals are precipitated, and preparing an intermediate 3, wherein the dosage ratio of the intermediate 2, the deionized water and the phosphorus pentoxide is 100 mL: 4.7 mL: 11.5 g.
Example 3
The preparation method of the intermediate 3 comprises the following steps:
step A1: taking a reactor provided with a conduit, adding 4, 4 '-dimethyl diphenyl sulfide and aluminum trichloride into the reactor, controlling the reaction temperature to be 68 ℃ under the protection of nitrogen, and introducing methane chloride, 4, 4' -dimethyl diphenyl sulfide and methane chloride from the conduit at a dosage ratio of 100 mL: 0.22m3The introduction speed of the monochloromethane is controlled to be 0.16m3After all the chloromethane is introduced, filtering the reaction liquid to prepare an intermediate 1;
step A2: taking a reactor provided with a stirrer, adding the intermediate 1 into the reactor, controlling the stirring speed to be 140r/min and the reaction temperature to be 80 ℃, adding potassium permanganate into the reactor, and controlling the dosage ratio of the intermediate 1 to the potassium permanganate to be 100 mL: 5.5g, reacting for 1h, and filtering and removing excessive potassium permanganate in the reaction liquid to obtain an intermediate 2;
step A3: taking a reactor with a stirrer, adding the intermediate 2 and deionized water into the reactor, controlling the stirring speed to be 230r/min, taking phosphorus pentoxide, evenly dividing into three parts, adding into the reactor three times, adding the time interval T of 10min (the total volume/L of the intermediate 2 and the deionized water), stirring and reacting for 3h after all the phosphorus pentoxide is added, filtering the reaction solution after the reaction is ended, washing the filtrate for 2 times by using ice water, taking the lower layer clear solution for rotary evaporation until light yellow crystals are precipitated, and preparing an intermediate 3, wherein the dosage ratio of the intermediate 2, the deionized water and the phosphorus pentoxide is 100 mL: 4.7 mL: 11.5 g.
Example 4
The preparation method of the intermediate 3 comprises the following steps:
step A1: taking a reactor provided with a conduit, adding 4, 4 '-dimethyl diphenyl sulfide and aluminum trichloride into the reactor, controlling the reaction temperature to be 70 ℃ under the protection of nitrogen, and introducing methane chloride, 4, 4' -dimethyl diphenyl sulfide and methane chloride from the conduit at a dosage ratio of 100 mL: 0.24m3The introduction speed of the monochloromethane is controlled to be 0.18m3After all the chloromethane is introduced, filtering the reaction liquid to prepare an intermediate 1;
step A2: taking a reactor provided with a stirrer, adding the intermediate 1 into the reactor, controlling the stirring speed to be 150r/min and the reaction temperature to be 85 ℃, adding potassium permanganate into the reactor, and controlling the dosage ratio of the intermediate 1 to the potassium permanganate to be 100 mL: 5.5g, reacting for 1.15h, and filtering and removing excessive potassium permanganate in the reaction liquid to obtain an intermediate 2;
step A3: taking a reactor with a stirrer, adding the intermediate 2 and deionized water into the reactor, controlling the stirring speed to be 250r/min, taking phosphorus pentoxide, evenly dividing into three parts, adding into the reactor three times, adding the time interval T of 10min (the total volume/L of the intermediate 2 and the deionized water), stirring and reacting for 4h after all the phosphorus pentoxide is added, filtering the reaction solution after the reaction is ended, washing the filtrate for 3 times by using ice water, taking the lower layer clear solution for rotary evaporation until light yellow crystals are precipitated, and preparing an intermediate 3, wherein the dosage ratio of the intermediate 2, the deionized water and the phosphorus pentoxide is 100 mL: 4.7 mL: 11.5 g.
Example 5
A preparation method of a low-melting-point circuit board substrate comprises the following steps:
step S: adding N, N-dimethylacetamide into a reactor with a stirrer, adding the intermediate 3 prepared in the embodiment 3, stirring until the intermediate 3 is completely dissolved, adding 1, 4-phenylenediamine and 1, 2-ethylenediamine into the reactor, heating to 52 ℃, controlling the stirring speed at 200r/min, and carrying out heat preservation reaction for 3 hours to obtain the low-melting-point circuit board substrate.
Example 6
A preparation method of a low-melting-point circuit board substrate comprises the following steps:
step S: adding N, N-dimethylacetamide into a reactor with a stirrer, adding the intermediate 3 prepared in the embodiment 4, stirring until the intermediate 3 is completely dissolved, adding 1, 4-phenylenediamine and 1, 2-ethylenediamine into the reactor, heating to 54 ℃, controlling the stirring speed to be 250r/min, and carrying out heat preservation reaction for 4 hours to obtain the low-melting-point circuit board substrate.
Example 7
A preparation method of a low-melting-point circuit board substrate comprises the following steps:
step S: adding N, N-dimethylacetamide into a reactor with a stirrer, adding the intermediate 3 prepared in the embodiment 4, stirring until the intermediate 3 is completely dissolved, adding 1, 4-phenylenediamine and 1, 2-ethylenediamine into the reactor, heating to 55 ℃, controlling the stirring speed to be 300r/min, and carrying out heat preservation reaction for 5 hours to obtain the low-melting-point circuit board substrate.
Comparative example 1
This comparative example is a commercially available polyimide solution (Changzhou Anxin materials Co., Ltd.: PAA-1)
The low melting point wiring board substrates obtained in examples 5 to 7 and comparative example 1 were coated on the surface of a copper plate by a coater to set the coating amount to 14.5g/m3And drying under the protection of nitrogen to prepare a sample, and carrying out performance test on the sample:
adopting a differential scanning calorimeter to test the melting point of a sample, setting the heating rate at 10 ℃/min under the nitrogen atmosphere, and testing the melting point and the glass transition temperature of the sample;
testing the dielectric constant and the surface resistivity of the sample according to GB/T1408.1-2006;
tensile strength testing was performed on the specimens according to ASTM D638;
specific test data are shown in table 1:
TABLE 1
As is clear from Table 1, in examples 5 to 7, the melting temperature is not higher than 301 ℃ and is reduced by 75 ℃ compared with comparative example 1, the glass transition temperature is reduced to 185 ℃ or higher, and good processability and heat resistance are achieved because thioether bonds are introduced into the polyimide molecules to lower the melting temperature of the polymer; the dielectric constant and the surface resistivity are both higher than those of the comparative example 1, which shows that the low-melting-point circuit board substrate prepared by the invention has good insulating property; the tensile strength is up to 118MPa, because of the lone pair electrons on the sulfur atom, the base material has good affinity with metal, so that the base material and a metal substrate in the circuit board have stronger bonding strength, and the adhesion reliability of the base material is improved.
The foregoing is merely exemplary and illustrative of the principles of the present invention and various modifications, additions and substitutions of the specific embodiments described herein may be made by those skilled in the art without departing from the principles of the present invention or exceeding the scope of the claims set forth herein.
Claims (4)
1. The circuit board substrate with the low melting point is characterized by being prepared by copolymerizing 1, 4-phenylenediamine, 1, 2-ethylenediamine and an intermediate 3, and having the following general formula:
wherein, the structural formula of the intermediate 3 is shown as follows.
2. The preparation method of the low-melting-point circuit board substrate as claimed in claim 1, wherein X is a thioether bond, and the preparation method specifically comprises the following steps:
step S1: adding 4, 4' -dimethyl diphenyl sulfide and aluminum trichloride into a reactor, controlling the reaction temperature to be 65-70 ℃ under the protection of nitrogen, introducing methane chloride, and filtering the reaction liquid to obtain an intermediate 1;
step S2: adding the intermediate 1 into a reactor, reacting at 78-85 ℃, adding potassium permanganate into the reactor under the stirring condition, reacting for 1-1.15h, and filtering the reaction solution to obtain an intermediate 2;
step S3: adding the intermediate 2 and deionized water into a reactor, adding phosphorus pentoxide into the reactor for three times under the stirring condition, stirring and reacting for 3-4h after all the phosphorus pentoxide is added, filtering reaction liquid after the reaction is ended, washing filtrate by using ice water, taking lower layer clear liquid, and performing rotary evaporation to separate out light yellow crystals to obtain an intermediate 3;
step S4: adding N, N-dimethylacetamide into a reactor, adding the intermediate 3, stirring until the intermediate 3 is completely dissolved, adding 1, 4-phenylenediamine and 1, 2-ethylenediamine into the reactor, heating to 52-55 ℃, stirring, keeping the temperature and reacting for 3-5h to obtain the low-melting-point circuit board substrate.
3. The method for preparing a low-melting-point wiring board substrate according to claim 2, wherein in step S1, the ratio of 4, 4' -dimethyl diphenyl sulfide to methyl chloride is 100 mL: 0.21-0.24m3And the introduction speed of the monochloromethane is 0.15-0.18m3/h。
4. The method for preparing a low-melting-point wiring board substrate according to claim 2, wherein in the step S4, the ratio of the intermediate 3, 1, 4-phenylenediamine to 1, 2-ethylenediamine is 2 mo: 2.25-2.4 mol: 1.15-1.3 mol.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115413118A (en) * | 2022-09-30 | 2022-11-29 | 深圳市米韵科技有限公司 | HDI circuit board substrate material and preparation method thereof |
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