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JP-7856019-B2 - Resin compositions, resin coatings, dry films, and cured resin products

JP7856019B2JP 7856019 B2JP7856019 B2JP 7856019B2JP-7856019-B2

Inventors

  • 丸山 仁

Assignees

  • 信越化学工業株式会社

Dates

Publication Date
20260511
Application Date
20230206

Claims (9)

  1. A resin composition comprising (A) a polymer having a sylphenylene skeleton, an epoxy group-containing isocyanuric acid skeleton, and a norbornane skeleton in its main chain, wherein the polymer contains only repeating units represented by the following formula (A1) and repeating units represented by the following formula (A2) , and (B) an epoxy curing accelerator, which, by thermal curing, yields a cured resin product having a relative permittivity of 2.5 or less at 10 GHz and a dielectric loss tangent of 0.005 or less at 10 GHz. (In the formulas, a and b are positive numbers satisfying 0 < a < 1, 0 < b < 1, and a + b = 1. X1 is a divalent base represented by the following formula (X1). X2 is a divalent base represented by the following formula (X2).) (In the formula, R 11 and R 12 are each independently a hydrogen atom or a methyl group. R 13 is a hydroxylene group having 1 to 8 carbon atoms, and may have an ester bond or ether bond interposed between its carbon-carbon bonds. x and y are each independently integers from 0 to 7. Dashed lines represent bonds.) (In the formula, R 21 and R 22 are each independently saturated hydrocarbyl groups having 1 to 20 carbon atoms, which may contain a hydrogen atom or a heteroatom. z is an integer from 0 to 10. Dashed lines represent bonds.)
  2. The resin composition according to claim 1, wherein a is 0 < a ≤ 0.35.
  3. The resin composition according to claim 1, wherein (B) the epoxy curing accelerator is contained in an amount of 0.01 to 10 parts by mass per 100 parts by mass of (A) the polymer.
  4. Furthermore, the resin composition according to claim 1, further comprising (C) a solvent.
  5. The resin composition according to claim 1, wherein the curing temperature for thermosetting is 100 to 250°C.
  6. The resin composition according to claim 1, which is a material for a protective coating for electrical and electronic components.
  7. A resin film obtained from the resin composition according to any one of claims 1 to 6.
  8. A dry film comprising a support film and a resin coating according to claim 7 on the support film.
  9. A resin cured product obtained by heat-curing the resin film described in claim 7 at 100 to 250°C.

Description

This invention relates to resin compositions, resin coatings, dry films, and cured resin products. In recent years, the semiconductor industry has demanded lower dielectric properties for semiconductor encapsulation materials to meet the high-frequency requirements of mobile devices such as smartphones. While epoxy resins have traditionally been used as semiconductor encapsulants, a dry film-type semiconductor encapsulant using silicone resin, comprising a support film and a resin coating on the support film, has been proposed (Patent Document 1). This material allows for flat encapsulation without voids on substrates with uneven surfaces such as chips and wiring. However, in mobile communication devices such as mobile phones, their base station equipment, network infrastructure equipment such as servers and routers, and electronic devices such as large computers, the speed and capacity of signals used are increasing year by year. Consequently, further reduction in transmission loss is necessary, and therefore, semiconductor encapsulants require even lower dielectric strength. Japanese Patent Publication No. 2021-95524 [Resin composition] The resin composition of the present invention comprises a polymer having a silphenylene skeleton, an epoxy group-containing isocyanuric acid skeleton and a norbornane skeleton in its main chain, and (B) an epoxy curing accelerator. [(A) Polymer] The polymer of component (A) is a polymer whose main chain contains a sylphenylene skeleton, an epoxy group-containing isocyanuric acid skeleton, and a norbornane skeleton. Such polymers are preferably those containing a repeating unit represented by the following formula (A1) (hereinafter also referred to as repeating unit A1) and a repeating unit represented by the following formula (A2) (hereinafter also referred to as repeating unit A2). In equations (A1) and (A2), a and b are positive numbers satisfying 0 < a < 1, 0 < b < 1, and a + b = 1, but preferably a is 0 < a ≤ 0.35. If a is within this range, it exhibits excellent solubility in common organic solvents and is easy to handle. In formula (A1), X1 is a divalent group represented by the following formula (X1). (The dashed lines represent connecting moves.) In formula (X1), R11 and R12 are each independently a hydrogen atom or a methyl group, but are preferably hydrogen atoms. In formula (X1), R 13 is a hydrocarbylene group having 1 to 8 carbon atoms, and may have an ester bond or ether bond interposed between its carbon-carbon bonds, but it is preferable that there is no ester bond or ether bond interposed between the carbon-carbon bonds. The hydrocarbylene group may be linear, branched, or cyclic, and specific examples include alkanediyl groups such as methylene group, ethane-1,1-diyl group, ethane-1,2-diyl group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,2-diyl group, butane-1,3-diyl group, and butane-1,4-diyl group. Of these, R 13 is preferably a methylene group or an ethane-1,2-diyl group, and more preferably a methylene group. In equation (X1), x and y are each independent integers between 0 and 7, but preferably between 0 and 2. In formula (A2), X2 is a divalent group represented by the following formula (X2). (The dashed lines represent connecting moves.) In formula (X2), R21 and R22 are each independently a saturated hydrocarbyl group having 1 to 20 carbon atoms, which may contain a hydrogen atom or a heteroatom. The saturated hydrocarbyl group may be linear, branched, or cyclic. Specific examples include alkyl groups having 1 to 20 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups; and cyclic saturated hydrocarbyl groups having 3 to 20 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and adamantyl groups. Furthermore, the saturated hydrocarbyl group may contain heteroatoms. Specifically, some or all of the hydrogen atoms of the saturated hydrocarbyl group may be substituted with halogen atoms such as fluorine, chlorine, bromine, or iodine, and a carbonyl group, ether bond, thioether bond, etc., may be interposed between the carbon atoms. Hydrogen atoms or methyl groups are preferred for R21 and R22 . In equation (X2), z is an integer between 0 and 10, but preferably an integer between 0 and 2. The polymer of component (A) preferably has a weight-average molecular weight (Mw) of 3,000 to 100,000, and more preferably 5,000 to 50,000. When Mw is within this range, a solid polymer with no tackiness and excellent flexibility can be obtained, and it is also possible to form a dry film with a protective film. In this invention, Mw is a polystyrene-converted measurement obtained by gel permeation chromatography (GPC) using tetrahydrofuran as the elution solvent. The polymer of component (A) may consist of repeating units A1 and A2 bonded randomly or alternately, and may contain multiple blocks of each unit. The