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KR-102960829-B1 - Curable resin, curable resin composition and cured product

KR102960829B1KR 102960829 B1KR102960829 B1KR 102960829B1KR-102960829-B1

Abstract

The purpose is to provide a curable resin, a resin composition, and a cured product thereof, which can be made to have excellent heat resistance (high glass transition temperature) and dielectric properties (low dielectric properties). Specifically, a curable resin (A) is provided that is characterized by containing both a structure represented by the following general formula (1) and a structure represented by the following general formula (2). (Details of the substituents and the number of substituents indicated in the above general formula (1) are as described in the text.) (Details of the substituents and the number of substituents indicated in the above general formula (2) are as described in the text.)

Inventors

  • 마츠오카, 류이치
  • 양, 리첸
  • 간나리, 히로요시

Assignees

  • 디아이씨 가부시끼가이샤

Dates

Publication Date
20260507
Application Date
20221006
Priority Date
20211118

Claims (10)

  1. Curable resin (A1) represented by the following general formula (A1), A curable resin (A2) having a repeating structure represented by the following general formula (A2a) and a terminal structure represented by the following general formula (A2b), and a curable resin (A3) having a repeating structure represented by the following general formula (A3a) and a terminal structure (A3b) represented by the following general formula (A3b) A curable resin, one type selected from the group consisting of (In the above general formula (A1), Ra is each independently an alkyl group, aryl group, aralkyl group, or cycloalkyl group having 1 to 12 carbon atoms, W is a hydrocarbon having 2 to 15 carbon atoms, n is an integer from 3 to 5, U is the following general formula (U1) or the following general formula (U2), and furthermore, a plurality of Us present in the resin each comprise one or more of the following general formulas (U1) and (U2).) (In the above general formulas (A2a)(A2b), Ra is each independently an alkyl group, an aryl group, an aralkyl group, or a cycloalkyl group having 1 to 12 carbon atoms, X represents a hydrocarbon group, Y represents any one of the following general formulas (Y1), (Y2), and (Y3), and U is the following general formula (U1) or the following general formula (U2), and furthermore, a plurality of Us in the resin each comprise one or more of the following general formulas (U1) and (U2).) (In the formula, Z represents a cycloaliphatic group, an aromatic group, or a complex cycloaliphatic group.) (In the above general formulas (A3a)(A3b), Ra is each independently an alkyl group, an aryl group, an aralkyl group, or a cycloalkyl group having 1 to 12 carbon atoms, and U is the following general formula (U1) or the following general formula (U2), and furthermore, a plurality of Us in the resin each comprise one or more of the following general formulas (U1) and (U2).)
  2. A curable resin composition containing the curable resin described in claim 1.
  3. A cured product obtained by curing the curable resin composition described in paragraph 2.
  4. A varnish obtained by diluting the curable resin composition described in paragraph 2 with an organic solvent.
  5. A prepreg having a reinforcing substrate and a semi-material of the varnish described in claim 4 impregnated in the reinforcing substrate.
  6. A circuit board obtained by laminating the prepreg described in paragraph 5 and a copper foil, and heat-press molding.
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Description

Curable resin, curable resin composition and cured product The present invention relates to a curable resin having a specific structure, a curable resin composition containing said curable resin, and a cured product obtained by said curable resin composition. With the recent increase in information and communication volume, information and communication in the high-frequency band has become active, and electrical insulating materials having low dielectric constant and low dielectric loss tangent are required to achieve superior electrical characteristics, particularly to reduce transmission loss in the high-frequency band. In addition, printed circuit boards or electronic components in which such electrical insulating materials are used are exposed to high-temperature solder reflow during mounting, so materials with excellent heat resistance and high glass transition temperatures are required. Especially these days, as lead-free solder with a high melting point is used from the perspective of environmental issues, there is a growing demand for electrical insulating materials with higher heat resistance. In response to these requirements, various vinyl group-containing curable resins having different chemical structures have been proposed. As such curable resins, for example, bisphenol divinylbenzyl ether or novolac polyvinylbenzyl ether has been proposed (see, for example, Patent Documents 1 and 2). However, these vinylbenzyl ethers cannot provide a cured product with sufficiently low dielectric properties, and the resulting cured product is problematic for stable use in the high-frequency range, and furthermore, bisphenol divinylbenzyl ether cannot be said to have sufficiently high heat resistance. Regarding vinylbenzyl ethers with improved properties as described above, several polyvinylbenzyl ethers of specific structures have been proposed to improve dielectric properties, etc. (e.g., see Patent Documents 3 to 5). However, although attempts have been made to suppress dielectric loss tangents and improve heat resistance, these improvements in properties are not yet sufficient, and further improvement in properties is desired. As such, conventional vinyl group-containing curable resins including polyvinylbenzyl ethers did not provide a curable product that combined the low dielectric loss tangent required for electrical insulation materials, particularly for high-frequency electrical insulation materials, and heat resistance capable of withstanding lead-free soldering. Hereinafter, embodiments of the present invention will be described in detail. <Curing Resin (A)> The curable resin (A) of the present embodiment is characterized by containing both a structure represented by the following general formula (1) and a structure represented by the general formula (2) described later. In the above general formula (1), Ra is independently an alkyl group, aryl group, aralkyl group, or cycloalkyl group having 1 to 12 carbon atoms, M is a methacryloyloxy group, h and i are independently integers from 1 to 4, and j is an integer from 0 to 2. In addition, in the above general formula (1), Ra and M may be bonded at any position on the aromatic ring, and the bonding site with the carbon atom is indicated as any position on the aromatic ring. In the above general formula (1), Ra each independently represents an alkyl group, an aryl group, an aralkyl group, or a cycloalkyl group having 1 to 12 carbon atoms, and preferably an alkyl group, an aryl group, or a cycloalkyl group having 1 to 4 carbon atoms. By having the above alkyl group having 1 to 12 carbon atoms, the planarity near any of the benzene ring, naphthalene ring, and anthracene ring described later is reduced, and the solvent solubility is improved due to the reduction in crystallinity, and the melting point is lowered, which is a preferred embodiment. In addition, by having the above Ra, steric hindrance is created and molecular mobility is reduced, so a cured product with a low dielectric loss tangent is obtained. In addition, it is preferable that the above Ra is located in an ortho position with respect to the crosslinking group M. It is preferable that at least one of the above Ra is located in an ortho position with respect to the crosslinking group M, so that the molecular mobility of the crosslinking group M is further reduced due to the steric hindrance of the above Ra, and a cured product with an even lower dielectric loss tangent is obtained. In the above general formula (1), M is a methacryloyloxy group that serves as a crosslinking group. By having a methacryloyloxy group in the above curable resin composition, a cured product having a low dielectric loss tangent is obtained compared to other crosslinking groups (e.g., vinylbenzyl ether group or dihydroxybenzene group, etc.). In addition, although the detailed reason why a cured product exhibiting low dielectric properties is obtained by having the above-mentioned methacryloyloxy group is not obvious