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Heat-Curable Resin Composition

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Heat-Curable Resin Composition (19) TZZ¥_¥ _T (11) EP 3 135 722 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 01.03.2017 Bulletin 2017/09 C08K 5/3415 (2006.01) C08G 73/12 (2006.01) C08L 79/08 (2006.01) C08L 79/04 (2006.01) (2006.01) (21) Application number: 16185322.1 C08L 63/00 (22) Date of filing: 23.08.2016 (84) Designated Contracting States: (71) Applicant: Shin-Etsu Chemical Co., Ltd. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Chiyoda-ku, GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Tokyo 100-0004 (JP) PL PT RO RS SE SI SK SM TR Designated Extension States: (72) Inventors: BA ME • KUSHIHARA, Naoyuki Designated Validation States: Annaka-shi, Gunma 379-0224 (JP) MA MD • SUMITA, Kazuaki Annaka-shi,, Gunma 379-0224 (JP) (30) Priority: 24.08.2015 JP 2015164546 (74) Representative: Zacco GmbH Bayerstrasse 83 80335 München (DE) (54) HEAT-CURABLE RESIN COMPOSITION (57) Provided is a heat-curable resin composition for (A) a heat-curable resin; and use in electric and electronics industry which is suitable (B) a bismaleimide compound in liquid form at 25°C, and as an underfill and for performing potting, and is superior exhibits a viscosity of 1 mPa·s to 850 Pa·s when meas- in fluidity, moisture resistance reliability and adhesive- ured at 25°C in accordance with a method described in ness at a high temperature. The heat-curable resin com- JIS Z8803:2011. position of the invention contains EP 3 135 722 A1 Printed by Jouve, 75001 PARIS (FR) EP 3 135 722 A1 Description [Technical field] 5 [0001] The present invention relates to a heat-curable resin composition containing a heat-curable resin and a liquid bismaleimide compound. [Background art] 10 [0002] In recent years, electronic devices such as mobile phones, smartphones, ultrathin liquid crystal or plasma TVs and light laptop computers have been downsized in a growing manner. Electronic parts used in these electronic devices have, for example, been highly densely integrated or even packaged in a growing manner as well. Further, it is required that a resin material used in these electronic parts be low-expansion one for the sake of a thermal stress that occurs at the time of manufacture and use. Furthermore, since these electronic parts will generate larger amounts of heat as they 15 become highly integrated, it is required that the resin material also have a heat resistance. [0003] Conventionally, cyanic ester resins are superior in heat resistance and are known as heat-curable resins with low electric permittivities and low dielectric losses. However, while a cured product employing a novolac-type cyanic ester resin described in Patent document 1 is superior in terms of thermal expansion, the cured product has a high water absorption rate and may exhibit a reduced heat resistance after moisture absorption. 20 [0004] As a resin composition capable of forming a cured product superior in mechanical strength, adhesion strength to an adherend, film-forming property, heat resistance and pressure resistance, Patent document 2 discloses a resin composition containing a polyamideimide resin (VYLOMAX HR16NN by Toyobo Co., Ltd.), diphenylethane bismaleimide (BMI-70 by K-I Chemical Industry Co., LTD.) and an allylphenol resin (MEH-8000H by Showa Kasei Kogyo Co., Ltd.). Since this resin composition employs a thermoplastic high-molecular-weight polyamideimide resin, the resin composition 25 has a poor low-temperature meltability, and has a poor compatibility with a maleimide compound. Therefore, phase separation may occur at the time of curing a contacting film of such resin composition, which makes it difficult to obtain an uniform coating film. Further, since there is used a high-boiling solvent such as NMP or the like, there exists a problem that the solvent will remain at B-stage. [0005] In addition, as a resin composition exhibiting a favorable adhesion and capable of forming a cured product 30 superior in moisture resistance, Patent document 3 discloses an epoxy resin composition for semiconductor encapsu- lation which contains an epoxy resin, an imidazole compound and a maleimide compound. However, since this resin composition has a high elasticity, cracks may occur in the cured product thereof when subjected to a stress such as a large temperature change in, for example, a temperature cycling test. 35 [Prior art documents] [Patent documents] [0006] 40 [Patent document 1] JP-A-H11-124433 [Patent document 2] JP-A-2004-168894 [Patent document 3] Japanese Unexamined Patent Application Publication (Translation of PCT Application) No. 2014-521754 45 [Summary of the invention] [Problem to be solved by the invention] 50 [0007] Therefore, it is an object of the present invention to provide a heat-curable resin composition for use in electric and electronics industry which has a superior fluidity, a low viscosity, a superior moisture resistance reliability due to its low water absorption rate, a low elasticity; and is thus suitable as an underfill and for performing potting. [Means to solve the problem] 55 [0008] The inventors of the present invention diligently conducted a series of studies to solve the abovementioned problems, and completed the invention as follows. That is, the inventors found that the above objectives could be achieved by a heat-curable resin composition containing the following heat-curable resin and liquid bismaleimide compound. 2 EP 3 135 722 A1 [0009] Specifically, the present invention is to provide the following heat-curable resin composition. [1] A heat-curable resin composition containing: 5 (A) a heat-curable resin; and (B) a bismaleimide compound in liquid form at 25°C, wherein the heat-curable resin composition exhibits a viscosity of 1 mPa·s to 850 Pa·s when measured at 25°C in accordance with a method described in JIS Z8803:2011. 10 [2] The heat-curable resin composition according to [1], wherein the heat-curable resin (A) includes a heat-curable resin component (A1) and a curing agent (A2). [3] The heat-curable resin composition according to [2], wherein the heat-curable resin component (A1) is at least one selected from an epoxy resin, a phenolic resin, an unsaturated imide resin, a cyanate resin, an isocyanate resin, a benzoxazine resin, an oxetane resin, an amino resin, an unsaturated polyester resin, an allyl resin, a dicyclopen- 15 tadiene resin, a silicone resin, a triazine resin and a melamine resin. [4] The heat-curable resin composition according to [3], wherein the heat-curable resin component (A1) is an epoxy resin or a cyanate resin, and the curing agent (A2) is a curing agent for either an epoxy resin or a cyanate resin. [5] The heat-curable resin composition according to any one of [1] to [4], wherein the bismaleimide compound (B) in liquid form at 25°C is a compound represented by the following formula (1): 20 25 30 wherein R1 represents at least one kind of divalent organic group selected from the group consisting of a linear or branched alkylene group having 1 to 40 carbon atoms; a divalent cyclic hydrocarbon group that has 3 to 20 carbon atoms and may also have a hetero atom(s); -O-; -NH-; -S- ; and -SO 2-. [6] The heat-curable resin composition according to [5], wherein the bismaleimide compound represented by the 35 formula (1) is at least one kind of bismaleimide compound selected from the group consisting of bismaleimide compounds represented by the following formulae (1-1), (1-2) and (1-3): 40 45 50 55 3 EP 3 135 722 A1 wherein n represents 1 to 10, and m represents 8 to 40 5 10 15 wherein n represents 1 to 10, and m represents 8 to 40 20 25 wherein n represents 1 to 10, and m represents 8 to 40 30 [Effects of the invention] [0010] The heat-curable resin composition of the present invention does not employ a solvent, but has a superior workability and exhibits an unimpaired resin reliability even under a high-humidity/temperature condition and a high- 35 temperature condition. [Mode for carrying out the invention] [0011] The present invention is described in detail hereunder. 40 (A) Heat-curable resin [0012] A heat-curable resin (A) of the present invention includes a heat-curable resin component (A1) and a curing agent (A2). 45 (A1) Heat-curable resin component [0013] Examples of such heat-curable resin component (A1) include an epoxy resin, a phenolic resin, an unsaturated imide resin, a cyanate resin, an isocyanate resin, a benzoxazine resin, an oxetane resin, an amino resin, an unsaturated 50 polyester resin, an allyl resin, a dicyclopentadiene resin, a silicone resin, a triazine resin and a melamine resin. Each of these resins may be used singularly, or two or more of them may be used in combination. Among the above resins, preferred are an epoxy resin and a cyanate resin in terms of moldability of the composition and electrical insulation property of the cured product thereof. [0014] Examples of the above epoxy resin include a bisphenol A-type epoxy resin; a bisphenol F-type epoxy resin; a 55 bisphenol S-type epoxy resin; a phenol novolac type epoxy resin; a cresol novolac type epoxy resin; a bisphenol A novolac-type epoxy resin; a bisphenol F novolac-type epoxy resin; a stilbene type epoxy resin; a triazine skeleton- containing epoxy resin; an fluorene skeleton-containing epoxy resin; a triphenol alkane type epoxy resin; a biphenyl type epoxy resin; a xylylene type epoxy resin; a biphenyl aralkyl type epoxy resin; a naphthalene type epoxy resin; a dicy- 4 EP 3 135 722 A1 clopentadiene type epoxy resin; an alicyclic epoxy resin; an aminophenol type epoxy resin; a hydrogenated bisphenol type epoxy resin; an alcohol ether type epoxy resin; multifunctional phenols; diglycidyl ether compounds of polycyclic aromatics such as anthracene; and a phosphorus-containing epoxy resin obtained by introducing an phosphorus com- pound into any of these epoxy materials.
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