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Synthesis method of molecular glass and application of molecular glass as high-frequency low-dielectric-constant material

A molecular glass and hydrogen atom technology, applied in organic chemistry and other fields, can solve problems such as uncontrollable polymer synthesis, thermal instability of thin films, aggregation and crystallization, etc.

Active Publication Date: 2021-09-24
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In terms of low-dielectric thin-film substrate materials, film-forming property is a key performance parameter. At present, polymer materials with an amorphous state are generally used, and uniform and dense thin films can be formed by solution processing methods, but polymers have Disadvantages of uncontrollable synthesis and difficult purification
Small molecular compounds can well solve the problems of uncontrollable synthesis and difficult purification, but because the molecular weight of general small molecular compounds is not large enough, the formed film is thermally unstable and prone to aggregation and crystallization.

Method used

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  • Synthesis method of molecular glass and application of molecular glass as high-frequency low-dielectric-constant material
  • Synthesis method of molecular glass and application of molecular glass as high-frequency low-dielectric-constant material
  • Synthesis method of molecular glass and application of molecular glass as high-frequency low-dielectric-constant material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0216] Embodiment 1. Synthesis of double substituted 1,3,5-triazine S1

[0217]

[0218] Under the protection of nitrogen gas, add 180mmol magnesium chips, 100mL tetrahydrofuran and a grain of iodine (about 40mg) to a 250mL dry three-necked flask, then slowly add 120mmol 4-bromotoluene dropwise to keep the solution slightly boiling, and stir at reflux for 1h to obtain 4 - Methylphenyl Grignard reagent.

[0219] Take another 500mL dry three-necked flask, add 80mmol 2,4,6-trichloro-1,3,5-triazine under nitrogen protection, add 120mmol 4-methylbenzene Grignard reagent dropwise, and stir at -5°C Reacted for 19 hours. Quenched with ammonium chloride, extracted with ethyl acetate, concentrated to remove the solvent and followed by column chromatography to obtain 16.97 g of white solid compound 1 with a yield of 88%. 1 H NMR (CDCl 3 ,400MHz),δ(ppm)8.37(d,J=8.1Hz,2H),7.31(d,J=8.1Hz,2H),2.44(s,3H). 13 C NMR (CDCl 3 ,126MHz), δ(ppm)174.74,171.85,146.07,129.99,129.86,21.93.

[0...

Embodiment 2

[0223] Embodiment 2. Synthesis of Molecular Glass Monomer M1

[0224]

[0225] Take a 500mL single-necked bottle, add 13.2mmol intermediate S2, 48.0mmol NaOH and 80mL H 2 O, stirred at room temperature for 0.5h. Continue to add 120mL CHCl 3 , 24 mmol intermediate S1 and 0.13 mmol phase transfer catalyst cetyltrimethylammonium bromide. Raise the temperature to 60°C and react for 14h under vigorous stirring. After stopping the reaction, it was extracted with dichloromethane, dried, and the solvent was removed under reduced pressure. Column chromatography gave 7.70 g of white amorphous "molecular glass" monomer M1, yield: 75%.

[0226] 1 H NMR (500MHz, CDCl 3 )δ8.33(dd, J=11.6,8.3Hz,6H),8.10(s,2H),7.19(dd,J=15.0,5.0Hz,6H),7.13(dd,J=8.4,2.0Hz,2H ),7.06(dd,J=16.1,8.1Hz,4H),5.80(ddt,J=13.0,10.0,6.5Hz,2H),4.99–4.76(m,4H),3.31(d,J=6.3Hz, 4H), 3.11(s,8H), 2.31(s,6H), 1.72(s,6H).

[0227] 13 C NMR (CDCl 3 ,126MHz),δ(ppm)174.55,173.79,171.83,151.70,148.46,148.29,146.05,143.4...

Embodiment 3

[0228] Embodiment 3. the synthesis of intermediate S2'

[0229]

[0230] Take 250mL sealed tube, add 50mL acetone, 25mmol K 2 CO 3 , 10mmol of bisphenol AF, first stirred at room temperature for 30min, continued to add S2, and heated to 70°C for overnight reaction. After the reaction was stopped, the insoluble impurities were removed by suction filtration, and the solvent was spin-dried to obtain 4.11 g of the diallyl-substituted target intermediate as a colorless transparent liquid with a yield of 98.9%. The obtained intermediate was directly placed into a 50 mL single-necked flask, nitrogen was replaced 3 times, and reacted at 210° C. for 9 h. After the reaction was stopped, column chromatography was separated to obtain 3.771 g of light yellow liquid, yield: 91.7%.

[0231] 1 H NMR (CDCl 3 , 400MHz) δ(ppm) δ7.16(d, J=8.8Hz, 2H), 7.11(s, 2H), 6.80(d, J=8.5Hz, 2H), 5.97(m, 2H), 5.55(s ,2H,OH),5.12(dd,J=12.0,10.3Hz,4H),3.38(d,J=6.2Hz,4H). 19 F NMR (CDCl 3 , 376MHz) δ(...

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Abstract

The invention provides a synthesis method of molecular glass and application of the molecular glass as a high-frequency low-dielectric-constant material. Specifically, the invention provides a molecular glass monomer, the molecular glass monomer has a molecular structure as shown in a formula (I) in the specification; the molecular glass monomer has excellent processability and can form infusible and insoluble resin after high-temperature treatment; and the molecular glass only shows glass transition but has no melting point during heating and is similar to an amorphous state. The resin obtained by curing the molecular glass has high heat resistance and low water absorption, especially shows excellent dielectric constant and dielectric loss at high frequency, and can be widely applied to the fields of high-frequency communication, microelectronic industry, aerospace and the like as low-dielectric-constant matrix resin or a packaging material.

Description

technical field [0001] The invention relates to the field of high-performance low-permittivity thermosetting resin materials, in particular to a directly thermally curable "molecular glass" monomer, its preparation method and its application as a high-frequency low-permittivity material. Background technique [0002] With the rapid development of high-frequency communication technology, 5G communication technology will rely more on new materials than any previous generation, mainly because of the high signal transmission speed (about 10Gbps) and low signal delay (<1ms) of 5G communication. And features such as multi-user access. In the existing 5G technology, sub-6GHz and millimeter waves will be used for signal transmission. In the millimeter wave frequency, when the electric field passes through the medium, the heat loss due to the alternating polarization of the medium molecules and the back and forth collision of the lattice will be intensified. Studies have shown th...

Claims

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Application Information

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IPC IPC(8): C07D251/22C08F112/34
CPCC07D251/22C08F112/34
Inventor 房强黄港孙晶
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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