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Triazolyl silane coupling agent as well as preparation method and application thereof

A technology of triazolyl silane coupling agent and azolyl silane coupling agent, which is applied in the field of organosilicon compounds, can solve problems such as easy volatilization and poor copper discoloration effect, and achieve enhanced adhesion and improved discoloration problems Effect

Active Publication Date: 2022-05-10
波米科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when triazole or its derivatives are directly added to the resin, since the triazole or its derivatives are small molecular compounds, they are easily volatile during the high-temperature curing of the resin, resulting in a poor effect of inhibiting copper discoloration.

Method used

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  • Triazolyl silane coupling agent as well as preparation method and application thereof
  • Triazolyl silane coupling agent as well as preparation method and application thereof
  • Triazolyl silane coupling agent as well as preparation method and application thereof

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preparation example Construction

[0119] The present invention also provides a kind of preparation method of the triazolyl silane coupling agent shown in general formula (I)~(IV), the compound of structure shown in general formula (7) or (8) and general formula (9 ) or a compound of the structure shown in (10) undergoes an amidation reaction to obtain a triazolyl silane coupling agent of the structure shown in the general formula (I) or (III), and the imidization reaction is carried out after the amidation reaction , the step of obtaining a triazolylsilane coupling agent having a structure represented by general formula (II) or (IV).

[0120] Among them, the compound of the structure shown in the general formula (7) is a silane coupling agent, for example, it can be 3-(trimethoxysilyl) propyl succinic anhydride (trade name: X-12-967C, Japan Shin-Etsu Chemical).

[0121] The compound with the structure shown in general formula (8) is a silane coupling agent, for example, it can be 5-(trimethoxysilylpropyl)-bic...

Embodiment 1

[0157] Synthesis of silane coupling agent A-1:

[0158] To a 500mL three-necked flask equipped with a stirrer and a thermometer, 250mL of solvent N-methylpyrrolidone, 9.91g of 3,5-diamino-1,2,4-triazole (0.1mol, Aladdin chemical reagent) were added sequentially, Start stirring, and after 3,5-diamino-1,2,4-triazole is fully dissolved, slowly add 52.47 g of 3-(trimethoxysilyl)propyl succinic anhydride (0.2mol, X-12- 967C, Shin-Etsu Chemical Co., Ltd.), continue to react at 25°C for 20 hrs after the addition of the feed is completed, and carry out vacuum distillation and purification after the reaction to obtain the silane coupling agent A-1.

[0159]

[0160] The structural formula of the obtained silane coupling agent A-1 is shown in (A-1).

[0161] The NMR information of silane coupling agent A-1 is as follows:

[0162] 1 HNMR(DMSO):δ:0.87(t,4H),1.41(m,4H),1.64(m,4H),2.71(m,2H),2.90~3.10(m,4H),3.83(s,18H) ,10.36(s,1H),12.3(s,2H),13.75(s,2H).

Embodiment 2

[0164] Synthesis of silane coupling agent A-2:

[0165] To a 500mL three-necked flask equipped with a stirrer and a thermometer, 250mL of solvent N-methylpyrrolidone, 9.91g of 3,5-diamino-1,2,4-triazole (0.1mol, Aladdin chemical reagent) were added sequentially, Start stirring, and after 3,5-diamino-1,2,4-triazole is fully dissolved, slowly add 52.47 g of 3-(trimethoxysilyl)propyl succinic anhydride (0.2mol, X-12- 967C, Shin-Etsu Chemical), after the feeding is completed, continue the reaction at 25°C for 20hrs, then add 31.64g (0.4mol) of pyridine to the reaction system, stir evenly, slowly add 40.84g (0.4mol) of acetic anhydride, and react at 25°C for 20hrs, After the reaction is completed, distill under reduced pressure to remove the solvent, acetic anhydride, generated acetic acid and pyridine in the system to obtain purified silane coupling agent A-2.

[0166]

[0167] The structural formula of the obtained silane coupling agent A-2 is shown in (A-2).

[0168] The NM...

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Abstract

The invention discloses a triazolyl silane coupling agent as well as a preparation method and application thereof. The triazolyl silane coupling agent has a structural formula shown as follows: G1-R1-G2. R1 is an organic group as shown in a general formula (5) or (6), and in the general formula (6), X is a structure as shown in the general formula (5); wherein R4 is a hydrogen atom or a hydrocarbon group with 1-10 carbon atoms; r5 is an organic group having 4 to 40 carbon atoms; g1 and G2 are respectively and independently selected from one of structural formulas shown in general formulas (1)-(4), and R2 and R2'are independently selected from at least one of R3O, hydrogen atoms and alkyl with the carbon atom number of 1-10. The triazolyl silane coupling agent can significantly enhance the adhesiveness of heat-resistant resins such as polyimide and polybenzoxazole with a copper or copper alloy substrate after high-temperature thermocuring, and can significantly improve the discoloration problem of the copper or copper alloy substrate.

Description

technical field [0001] The application relates to a triazolyl silane coupling agent and its preparation method and application, belonging to the field of organosilicon compounds. Background technique [0002] In recent years, heat-resistant resins such as polyimide (PI) and polybenzoxazole (PBO) have been widely used in optical and electronic components such as liquid crystal display elements, organic EL display elements, and integrated circuit elements because of their excellent performance. Cured films such as insulating films, retardation films, and optical property films. The heat-cured film exists in the device as a permanent film, so the properties of the heat-cured film are very important. In order to ensure the reliability of semiconductor packaging, the adhesion of the cured film to the surface material of the semiconductor chip is very important. [0003] With the requirements of high integration, miniaturization and high speed of semiconductor devices, the wirin...

Claims

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Application Information

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IPC IPC(8): C07F7/18G03F7/004G03F7/038G03F7/039
CPCC07F7/1804C07F7/1892G03F7/0387G03F7/0382G03F7/0392G03F7/004
Inventor 李铭新张翠红王建伟门秀婷公聪聪王珂
Owner 波米科技有限公司
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