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Active ester resin, thermosetting resin composition, cured product of same, semiconductor encapsulation material, prepreg, circuit board, and build-up film
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Therefore, although the above-mentioned active ester compound obtained by esterifying the phenolic hydroxyl group in the phenol novolac resin has good dielectric properties, it contains a large amount of pendant aromatic hydrocarbon groups that are easy to burn in its molecular structure, so the cured product Poor flame retardancy, unable to construct the aforementioned halogen-free flame retardant system
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[0251] Next, the present invention will be specifically described by way of examples and comparative examples, and the following "parts" and "%" are based on mass unless otherwise specified. In addition, melt viscosity and softening point measurement at 180°C, GPC measurement, 13 C-NMR and FD-MS spectra were measured under the following conditions.
[0252] 1) Melt viscosity at 180°C: According to ASTM D4287.
[0253] 2) Softening point measurement method: according to JIS K7234.
[0254] 3) GPC:
[0255] Measuring device: "HLC-8220 GPC" manufactured by Tosoh Corporation,
[0256] Column: Guard column "HXL-L" manufactured by Tosoh Corporation
[0257] + "TSK-GEL G2000HXL" manufactured by Tosoh Corporation
[0258] + "TSK-GEL G2000HXL" manufactured by Tosoh Corporation
[0259] + "TSK-GEL G3000HXL" manufactured by Tosoh Corporation
[0260] + "TSK-GEL G4000HXL" manufactured by Tosoh Corporation
[0261] Detector: RI (differential refractometer)
[0262] Data processing...
manufacture example 1
[0284] 124g (0.59 mol), p-anisaldehyde 78.7g (0.59 mol), phenol novolac resin 161.2g (1.55 mol), and stirred while blowing nitrogen under the temperature condition of 90°C. After that, the temperature was raised to 140° C. and stirred for 4 hours, then the temperature was raised to 160° C. and stirred for 4 hours, and then heated to 180° C. and stirred for 2 hours. Thereafter, water was removed under heating and reduced pressure to obtain 350 g of a phenolic resin (A1-1) having the following structural unit A and structural unit B as repeating units.
[0285] Structural unit A
[0286] Structural unit B
[0287] The hydroxyl equivalent of the obtained phenolic resin (A1-1) was 228 g / equivalent, the softening point was 148°C, and the melt viscosity at 180°C was 400 dPa·s. The GPC spectrogram of gained phenolic resin (A1-1) is shown in figure 1 、C 13 The NMR spectrum is shown in figure 2 , MS spectrum is shown in image 3 . According to C 13 In the NMR spectrum, t...
manufacture example 2
[0289] Except having changed 161.2 g (1.55 mol) of phenol novolak resins into 248 g (1.55 mol) of 2,7- dihydroxynaphthalene, it obtained 490 g of phenolic resins (A1-2) by the method similar to manufacture example 1. The obtained phenol compound (A1-2) had a hydroxyl equivalent of 250 g / equivalent, a softening point of 140° C., and a melt viscosity at 180° C. of 300 dPa·s. The GPC spectrogram of gained phenolic resin (A1-2) is shown in Figure 4 .
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Abstract
This cured product is configured to exhibit both excellent heat resistance and excellent flame retardancy, while having low dielectric constant and low dielectric loss tangent. A phosphorus atom-containing compound (i), which is obtained by reacting (a1) an aromatic aldehyde that has an alkoxy group as a substituent on the aromatic nucleus with (a2) an organic phosphorus compound that has a P-H group or a P-OH group in a molecular structure, is reacted with (a3) a phenol substance, thereby obtaining (A1) a phosphorus atom-containing phenol substance; and then the thus-obtained phosphorus atom-containing phenol substance (A1) is reacted with (A2) an aromatic dicarboxylic acid, an acid anhydride thereof or a dihalide of an aromatic dicarboxylic acid, or a saturated dicarboxylic acid having 2-6 carbon atoms, an acid anhydride thereof or a dihalide of a saturated dicarboxylic acid having 2-6 carbon atoms so that some or all of the hydroxyl groups of the phenol substance (A1) form ester bonds.
Description
technical field [0001] The present invention relates to a thermosetting resin composition whose cured product exhibits excellent flame retardancy, heat resistance, and low dielectric loss tangent, and has excellent solvent solubility, its cured product, and an activity used for them Ester resin, and the thermosetting resin composition semiconductor sealing material, prepreg, circuit board, and laminated film. Background technique [0002] Cured products of epoxy resin compositions containing epoxy resins and their curing agents as essential components exhibit excellent heat resistance and insulation properties, and are therefore widely used in electronic parts such as semiconductors and multilayer printed circuit boards. [0003] In this electronic component application, particularly in the technical field of multilayer printed circuit board insulating materials, in recent years, signals in various electronic devices have been increased in speed and frequency. However, with...
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