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Oligomer (2,6-dimethylphenylene ether) Together with Fabrication Method and Cured Product Thereof

A technology of dimethylphenylene ether and oligomers, which is applied in the field of its preparation method and cured products and oligomers, which can solve the problems of reducing the force of intermolecular hydrogen bonds, difficult improvement of dielectric properties, and reduction of dielectric constant. , to achieve the effects of simplified steps, excellent organic solubility, and high glass transition temperature

Active Publication Date: 2021-11-05
CPC CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] With the advancement of semiconductor technology, the size of electronic components continues to shrink, making the line width of the metal wires in the circuit board thinner and thinner, and the line spacing between the wires is getting smaller and smaller, in order to meet the current needs, but in the metal distribution In the wire manufacturing process, there are two main problems that will affect its performance, one of which is the signal transmission delay (RC delay) caused by the metal wire and the dielectric layer, and the other is the signal interference between the metal wire wiring (cross talk), as can be seen from literature [1], the signal transmission speed will be related to the dielectric constant (dielectric constant; D k ) is inversely proportional to the square root, and the dielectric loss (dissipation factor; D f ) is lower, the easier it is to maintain the integrity of the signal, so reducing the dielectric constant and dielectric loss is a necessary trend, so how to prepare materials with excellent electrical properties has become the most important issue at present
[0003] Epoxy resin is a kind of thermosetting material. After reacting with hardener, it can form a three-dimensional network cross-linked structure, so that it has good mechanical properties, chemical resistance, adhesion, good thermal properties and insulation effects. For traditional phenol-type and amine-type hardeners, epoxy resin ring-opening polymerization produces highly polar secondary alcohols, making it difficult to improve the dielectric properties
In 2014, in the patent US 8,791,214 B2 published by DIC, multiple compounds containing phenolic groups such as phenol novolac (PN) and dicyclopentadiene phenol novolac (DCPDPN) were reacted with monofunctional or difunctional acid chlorides to obtain active ester groups. Hardener, and then cured with epoxy resin HP7200, the epoxy resin will undergo transesterification with active ester groups during the ring-opening process, and will not produce highly polar secondary alcohols, which is conducive to reducing the dielectric constant, although Modifying the hydroxyl group of the hardener to an ester group can reduce the dielectric properties, but also because the ester group will replace the hydroxyl group after the ring opening of the epoxy resin after the active ester group reacts with the epoxy resin, thereby reducing the intermolecular hydrogen bond force , so that the glass transition temperature (glass transition temperature; Tg) of the cured product decreases. Therefore, how to maintain the original thermal properties while reducing the dielectric properties is also very important.
[0011] In addition, the flame retardant properties of existing poly(2,6-dimethylphenylene ether) materials can only reach the V-1 level under the UL-94 specification test. To further reach the V-0 level, additional The flame retardant makes it reach the V-0 level. For example, GE Corporation of the United States published a patent US 6,352,782B2. Copolymerize to obtain flame-retardant poly(2,6-dimethylphenylene ether) resin. However, the dielectric constant at 1MHz will soar from 3.86 to 5.07, and the dielectric loss will also soar from 0.0024 to 0.0065. Loss of poly(2,6-dimethylphenylene ether) characteristic of excellent dielectric properties

Method used

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  • Oligomer (2,6-dimethylphenylene ether) Together with Fabrication Method and Cured Product Thereof
  • Oligomer (2,6-dimethylphenylene ether) Together with Fabrication Method and Cured Product Thereof
  • Oligomer (2,6-dimethylphenylene ether) Together with Fabrication Method and Cured Product Thereof

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preparation example Construction

[0053]

[0054] The preparation method of oligo(2,6-dimethylphenylene ether) in this embodiment includes the following steps.

[0055] First, step 1 is carried out, the (2,6-dimethylphenylene ether) oligomer at the end of the phenol shown in the formula (2) and the hexafluorobenzene ring or decafluorobiphenyl shown in the formula (3) are mixed in the base Under the catalysis of the active catalyst, the fluorine-containing (2,6-dimethylphenylene ether) oligomer represented by the formula (4) is obtained.

[0056]

[0057] In formula (2) - formula (4), R 0 with R 1 Each is independently hydrogen, C1-C6 alkyl or phenyl, X is -NR-, -CO-, -SO-, -CS-, -SO 2 -, -CH 2 -, -O-, null, -C(CH 3 ) 2 -or n and m are each independently an integer of 0 to 300. q is an integer of 0 to 1.

[0058] In one embodiment, the alkaline catalyst is potassium carbonate (K 2 CO 3 ), sodium carbonate (Na 2 CO 3 ), potassium hydroxide (KOH), sodium hydroxide (NaOH), sodium bicarbonate (NaH...

Embodiment 1

[0098] The synthesis of embodiment 1 fluorine-containing (2,6-dimethylphenylene ether) oligomer

[0099] In a 100 ml three-neck reactor, add 5 g (3.125 mmole) of SA90, 2.91 g (3.125*5 mmol) of Hexafluorobenzene (Hexafluorobenzene), 0.95 g (3.125*2.2 mmol) of potassium carbonate (K 2 CO 3 ) and 20 grams of dimethylacetamide (N,N-Dimethyl acetamide). Next, under a nitrogen atmosphere, the temperature was raised to 80° C., and the reaction was carried out for 36 hours. After the reaction, cool to room temperature. The mixture was poured into methanol water to precipitate, and washed several times with methanol water. Finally, suction and filtration, the filter cake was vacuum-dried at 60°C to obtain a white powdery product, as shown in the figure below, with a yield of 92%. Wherein, n and m are independently integers from 0 to 300.

[0100]

[0101] Next, the product's 1 H NMR spectrum. With high-resolution nuclear magnetic resonance spectrometer (400MHz Nuclear Magneti...

Embodiment 2

[0108] Example 2 Synthesis of fluorine-containing (2,6-dimethylphenylene ether) bisphenol oligomer

[0109]In a 100 ml three-neck reactor, add 2.34 g (1.553*4 mmole) of dicyclopentadiene-2,6-bisphenol, 0.47 g (3.125*5 mmol) of potassium carbonate and 4 g (1.553*2.2 mmol) of dimethyl Dimethylformamide was heated to 120° C. under nitrogen atmosphere and stirred for 30 minutes. Another 3 grams (1.553 mmole) of the fluorine-containing (2,6-dimethylphenylene ether) oligomer of Example 1 was dissolved in 18 grams of dimethylformamide, and then added dropwise to the three-neck reactor And maintained at 120°C for 12 hours. After the reaction, cool to room temperature. The mixture was poured into methanol water to precipitate, and washed several times with methanol water. Finally, air filtration was performed, and the filter cake was vacuum-dried at 60° C. to obtain a brown powder product, as shown in the figure below, with a yield of 85%. Wherein, n and m are independently integer...

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Abstract

The invention discloses an oligomer (2,6-dimethylphenylene ether) together with a fabrication method and cured product thereof. The oligomer (2,6-dimethylphenylene ether) includes a structure shown shown in the formula (1), wherein R0, R1, R2 and R3 are separately independent hydrogen, C1-C6 alkyl or phenyl; N and m are each independently an integer from 0 to 300; q is an integer from 0 to 1; X and Y are each independently-NR-,-CO-,-SO-,-CS-,-SO2-,-CH2-,-O-, null,-C (CH3) 2-or and Z is hydrogen.

Description

technical field [0001] The present invention relates to an oligomer, its preparation method and cured product, and in particular to an oligomer (2,6-dimethylphenylene ether), its preparation method and its cured product. Background technique [0002] With the advancement of semiconductor technology, the size of electronic components continues to shrink, making the line width of the metal wires in the circuit board thinner and thinner, and the line spacing between the wires is getting smaller and smaller, in order to meet the current needs, but in the metal distribution In the wire manufacturing process, there are two main problems that will affect its performance, one of which is the signal transmission delay (RC delay) caused by the metal wire and the dielectric layer, and the other is the signal interference between the metal wire wiring (cross talk), as can be seen from literature [1], the signal transmission speed will be related to the dielectric constant (dielectric co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48
CPCC08G65/485C08G65/44
Inventor 李圣德林庆炫谢怡轩陈维彦徐伟智高瑞富黄铭郁林建琛王逸萍
Owner CPC CORPORATION
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