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CN-116891633-B - Curable composition, cured product, prepreg, circuit board, laminate film, semiconductor sealing material, and semiconductor device

CN116891633BCN 116891633 BCN116891633 BCN 116891633BCN-116891633-B

Abstract

Disclosed are a curable composition, a cured product, a prepreg, a circuit board, a laminate film, a semiconductor sealing material, and a semiconductor device, each of which exhibits a low dielectric loss tangent and a low moisture absorption rate when cured. The present disclosure relates to a curable composition comprising a polymaleimide compound (a) containing a mono-or condensed polycyclic aromatic group to which 2 or more linear or branched alkylene groups are bonded, and an unsaturated hydrocarbon compound (B) having a reactive double bond.

Inventors

  • HASHIMOTO SHINTARO
  • Green hills and sages
  • Intelligence of marching off into political wilderness is expanded

Assignees

  • DIC株式会社

Dates

Publication Date
20260505
Application Date
20230316
Priority Date
20220331

Claims (11)

  1. 1. A curable composition characterized by comprising: Polymaleimide compound (A) having a structural unit represented by the following general formula (1), and Unsaturated hydrocarbon compounds (B) having a reactive double bond, In the above general formula (1), R 1 each independently represents an alkyl group, R 2 independently represents an alkyl group, an alkoxy group or an alkylthio group having 1 to 10 carbon atoms, an aryl group, an aryloxy group or an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group or a mercapto group, R 3 、R 4 、R 5 and R 6 each independently represent a hydrogen atom or a methyl group, and one of R 3 and R 4 is a hydrogen atom and the other is a methyl group, one of R 5 and R 6 is a hydrogen atom and the other is a methyl group, X 1 represents a substituent represented by the following general formula (X), In the general formula (x), R 7 and R 8 each independently represent a hydrogen atom or a methyl group, and one of R 7 and R 8 is a hydrogen atom and the other is a methyl group, R 9 each independently represents an alkyl group, an alkoxy group or an alkylthio group having 1 to 10 carbon atoms, an aryl group, an aryloxy group or an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, t represents an integer of 0 to 4, R is an average value of substitution numbers of X 1 for each 1 benzene ring to which X 1 is attached, and represents a number of 0 to 4, p represents an integer of 1 to 3, q represents an integer of 0 to 4, and k represents an integer of 1 to 100.
  2. 2. The curable composition according to claim 1, wherein the blending ratio of the polymaleimide compound (A) to the unsaturated hydrocarbon compound (B) having a reactive double bond in parts by mass, namely, the polymaleimide compound (A), is 90:10 to 10:90.
  3. 3. The curable composition according to claim 1 or 2, wherein the blending ratio of the polymaleimide compound (A) and the unsaturated hydrocarbon compound (B) having a reactive double bond in parts by mass, namely, the polymaleimide compound (A), is 80:20 to 20:80.
  4. 4. The curable composition according to claim 1 or 2, wherein the blending ratio of the polymaleimide compound (A) and the unsaturated hydrocarbon compound (B) having a reactive double bond in parts by mass, namely, the polymaleimide compound (A), is 75:25 to 25:75.
  5. 5. The curable composition according to claim 1 or 2, further comprising an epoxy resin (C).
  6. 6. A cured product of the curable composition according to any one of claims 1 to 5.
  7. 7. A prepreg comprising a reinforcing substrate and a prepreg impregnated with the curable composition according to any one of claims 1 to 5.
  8. 8. A circuit board comprising a laminate of the prepreg according to claim 7 and a copper foil.
  9. 9. A laminated film comprising the curable composition according to any one of claims 1 to 5.
  10. 10. A semiconductor sealing material comprising the curable composition according to any one of claims 1 to 5.
  11. 11. A semiconductor device comprising the cured product of the semiconductor sealing material according to claim 10.

Description

Curable composition, cured product, prepreg, circuit board, laminate film, semiconductor sealing material, and semiconductor device Technical Field The present disclosure relates to a curable composition, a cured product, a prepreg, a circuit board, a laminate film, a semiconductor sealing material, and a semiconductor device. Background A prepreg obtained by impregnating glass cloth with a thermosetting resin such as an epoxy resin or a BT (bismaleimide-triazine) resin, and heat-drying the same, a laminate obtained by heat-curing the prepreg, and a multilayer board obtained by combining the laminate and the prepreg and heat-curing the same are widely used as a circuit board material for electronic devices. Among these, the packaging substrate, which is one of the printed wiring boards that functions as an interposer for mounting semiconductors, is increasingly thinned, and warpage of the packaging substrate at the time of mounting is a problem, so that a material exhibiting high heat resistance is required in order to suppress warpage of the packaging substrate at the time of mounting. In addition, in recent years, the signal has been accelerated and the frequency has been increased, and it has been desired to provide a thermosetting composition capable of forming a cured product which maintains a sufficiently low dielectric constant in these environments and exhibits a sufficiently low dielectric loss tangent. In particular, in various electric material applications, particularly advanced material applications, further improvements in properties such as heat resistance and dielectric characteristics and materials and compositions having these properties have been demanded recently. For these demands, maleimide resins are attracting attention as materials having both heat resistance and low dielectric constant and low dielectric loss tangent. However, conventional maleimide resins, although exhibiting high heat resistance, are high in hygroscopicity and have not achieved dielectric properties (dielectric constant, dielectric loss tangent) as required for advanced material applications. For example, patent document 1 discloses a thermosetting composition containing a polymaleimide resin having an indane ring and triallyl cyanurate or an aromatic diamine as a material for a printed board having a dielectric constant of 4.0 or less as a laminate without impairing heat resistance. Prior art literature Patent literature Patent document 1 Japanese patent laid-open No. 5-247202 Disclosure of Invention Problems to be solved by the invention However, the thermosetting composition of patent document 1 does not discuss dielectric loss tangent, and therefore dielectric constant and dielectric loss tangent do not reach the level required for advanced material use, and low hygroscopicity at high temperature and low dielectric constant and low dielectric loss tangent are not simultaneously achieved. Accordingly, an object of the present disclosure is to provide a curable composition, a cured product, a prepreg, a circuit board, a laminate film, a semiconductor sealing material, and a semiconductor device, which exhibit low dielectric loss tangent and low dielectric constant while having low hygroscopicity at the time of curing. Means for solving the problems The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that by using a curable composition containing a polymaleimide compound (a) containing a mono-or condensed polycyclic aromatic ring having 2 or more linear or branched alkylene groups bonded thereto and an unsaturated hydrocarbon compound (B) having a reactive double bond, both hygroscopicity at the time of curing and low dielectric loss tangent and low dielectric constant can be achieved at a high level, and have completed the present invention. ADVANTAGEOUS EFFECTS OF INVENTION According to the present disclosure, a curable composition capable of achieving a high level of both low hygroscopicity, low dielectric constant and low dielectric loss tangent at the time of curing, and a cured product, prepreg, circuit board, laminate film, semiconductor sealing material and semiconductor device thereof can be provided. Such a curable composition is particularly useful for electronic component sealing material applications and the like. Drawings FIG. 1A is a GPC chart of the polymaleimide compound (A-1) and shows the GPC measurement result of the polymaleimide compound (A-1) of the present example. FIG. 1B is an FD-MS diagram of the polymaleimide compound (A-1) and shows the FD-MS measurement result of the polymaleimide compound (A-1) of the present example. FIG. 1C is a 13 C-NMR chart of the polymaleimide compound (A-1) and shows the 13 C-NMR measurement result of the polymaleimide compound (A-1) of this example. Detailed Description Hereinafter, embodiments of the present invention (referred to as "the present embodiment") will be described in detail, but the p