JP2019116625A - Resin composition, adhesive film and semiconductor device - Google Patents

Abstract

To provide a resin composition excellent in thermal conductivity, adhesiveness and film formability, particularly a resin composition excellent in thermal conductivity after curing.SOLUTION: The resin composition includes (A) an aminophenol type epoxy resin, (B) at least one kind selected from the group consisting of a phenoxy resin and a thermoplastic elastomer and (C) a highly thermally conductive inorganic filler. The dry matter of the resin composition can form a film having a film thickness of 30 to 200 μm and when a substrate with a dry matter of the resin composition having a film thickness of 30 to 200 μm and a width of 20 cm is wound on a reel of 50 mmφ, the substrate will not be fragmented even if it is bent.SELECTED DRAWING: None

Description

  The present invention relates to a resin composition, an adhesive film, and a semiconductor device, and in particular, a resin composition capable of forming a semiconductor device excellent in heat dissipation and having high reliability, an adhesive film, and the resin composition and the adhesive film. The present invention relates to a semiconductor device manufactured.

  2. Description of the Related Art In recent years, with the increase in the functionality and density of modules and electronic components, the amount of heat generated from heating elements such as modules and electronic components has increased. The heat from these heating elements is conducted to the substrate or the like and dissipated. In order to conduct the heat conduction efficiently, an adhesive having a high thermal conductivity is used as an adhesive between the heat generating element and the substrate. Also, for good handling, adhesive films with high thermal conductivity are used instead of adhesives.

  Here, if the heat conduction of the adhesive film is not good, there is a problem that heat is accumulated in the semiconductor device incorporating the module and the electronic component, and a failure of the semiconductor device is induced. Therefore, the development of films with high thermal conductivity is in progress at each company.

  The above-mentioned adhesive film is required to have not only thermal conductivity but also insulation property, heat resistance and connection reliability (adhesive strength). The thermal conductivity can be improved by using a large amount of high thermal conductivity filler in the adhesive film, but as the filler loading increases, the amount of resin component in the adhesive film decreases relatively To make it difficult to obtain desired adhesive strength. The problem of the decrease in adhesive strength due to the increase in the filler loading amount is not limited to the adhesive film of high thermal conductivity, but also occurs, for example, when the composition is filled with a filler from the viewpoint of reducing the thermal expansion coefficient.

  Film forming property and extensibility sufficient to be applied to processes such as film molding and coating as an epoxy resin directed to high thermal conductivity, and various physical properties such as thermal conductivity, heat resistance, and flexibility An epoxy resin having a biphenyl skeleton as an excellent epoxy resin (Patent Document 1), despite the introduction of a mesogenic group, the production is easy, the solubility in organic solvents is excellent, the toughness and the thermal conductivity An epoxy resin (Patent Document 2) which gives a cured product with excellent properties is disclosed.

JP 2012-107215 A JP, 2010-001427, A

  However, an epoxy resin having a thermal conductivity higher than that of the above-mentioned epoxy resin is required. The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a resin composition which is excellent in thermal conductivity, adhesiveness and film formability, particularly a resin composition which is excellent in thermal conductivity after curing. It is to be.

The present invention relates to a resin composition, an adhesive film, and a semiconductor device which solve the above problems by having the following constitution.
[1] (A) aminophenol type epoxy resin,
A resin composition comprising (B) at least one member selected from the group consisting of phenoxy resins and thermoplastic elastomers, and (C) high thermal conductivity inorganic fillers,
The dried product of the resin composition can form a film having a thickness of 30 to 200 μm, and
A resin composition which does not separate even when it is bent when a support having a dry product of a resin composition having a film thickness of 30 to 200 m and a width of 20 cm is wound on a 50 mm diameter reel .
[2] The resin composition according to [1], wherein the component (A) is represented by the following chemical formula (1).

[3] The component according to the above [1] or [2], wherein the component (C) is at least one selected from the group consisting of MgO, Al ₂ O ₃ , AlN, BN, a diamond filler, ZnO and SiC Resin composition.
[4] An adhesive film formed from the resin composition according to any one of the above [1] to [3].
[5] A cured product of the resin composition of any one of [1] to [3] or a cured product of the adhesive film of [4].
[6] A semiconductor device using the cured product of the adhesive film according to the above [5].
[7] (A) Aminophenol type epoxy resin,
(B) at least one selected from the group consisting of phenoxy resins and thermoplastic elastomers, and
(C) High thermal conductivity inorganic filler
An adhesive film with a support having a dried product of the resin composition containing
When a support having a dry product of a resin composition with a film thickness of 30 to 200 μm and a width of 20 cm is wound on a 50 mmφ reel, it does not separate even when bent
Adhesive film with support. (A) at least one member selected from the group consisting of aminophenol type epoxy resin, (B) phenoxy resin and thermoplastic elastomer, and (C) high thermal conductivity inorganic filler, and relative to 1 part by weight of component (A) And the component (B) is 0.5 to 5 parts by mass.

  According to the invention [1], it is possible to provide a resin composition which is excellent in thermal conductivity, adhesiveness and film formability, in particular, a resin composition which is excellent in thermal conductivity after curing.

According to the invention [4], it is possible to provide an adhesive film which is excellent in thermal conductivity and adhesiveness, and particularly excellent in thermal conductivity after curing. According to the invention [ 6 ], a semiconductor device of high reliability can be provided by the cured product of the adhesive film which is excellent in thermal conductivity, adhesiveness and thermal conductivity. According to the invention [7], it is possible to provide a resin composition excellent in thermal conductivity, adhesiveness, and film formability, particularly an adhesive film with a support excellent in thermal conductivity after curing.

It is a schematic diagram for demonstrating the method of scraping application.

The resin composition of the present invention comprises (A) an aminophenol type epoxy resin,
A resin composition comprising (B) at least one member selected from the group consisting of phenoxy resins and thermoplastic elastomers, and (C) high thermal conductivity inorganic fillers,
The dried product of the resin composition can form a film having a thickness of 30 to 200 μm, and
When a support having a dry product of a resin composition having a film thickness of 30 to 200 μm and a width of 20 cm is wound on a 50 mmφ reel, it is characterized in that it is not divided even when bent. The resin composition of the present invention comprises (A) an aminophenol type epoxy resin, (B) at least one selected from the group consisting of a phenoxy resin and a thermoplastic elastomer, and (C) a high thermal conductivity inorganic filler, The component (B) is composed of 0.5 to 5 parts by mass with respect to 1 part by mass of the component (A). Here, (C) high thermal conductivity inorganic filler means an inorganic filler of 5 W / m · K or more.

  The component (A) imparts high thermal conductivity to the resin composition after curing. The aminophenol type epoxy resin of the component (A) in the present invention is one obtained by epoxidizing various aminophenols by a known method. Examples of aminophenols are 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-amino-m-cresol, 2-amino-p-cresol, 3-amino-o-cresol, 4-amino Examples thereof include, but are not limited to, aminophenols such as -m-cresol and 6-amino-m-cresol, aminocresols and the like.

  The component (A) has the following chemical formula (1):

Aminophenol-type epoxy resins are preferred because they make the resin composition after curing highly heat conductive. As a commercial item of (A) ingredient, Mitsubishi Chemical made amino phenol type epoxy resin (brand name: 630) is mentioned. The component (A) may be used alone or in combination of two or more.

  The component (B) imparts film formability to the resin composition. The phenoxy resin of the component (B) is not particularly limited, and is not limited to bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenol acetophenone skeleton, novolac skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, Those having one or more kinds of skeletons selected from naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton and trimethylcyclohexane skeleton are mentioned. As a commercial item of the phenoxy resin of (B) component, Mitsubishi Chemical made flexible phenoxy resin (brand name: YL7178, glass transition temperature: 15 degreeC) is mentioned.

  As the thermoplastic elastomer of the component (B), urethane rubber, acrylic rubber, silicone rubber, vinyl alkyl ether rubber, polyvinyl alcohol rubber, polyvinyl pyrrolidone rubber, polyacrylamide rubber, cellulose rubber, natural rubber, butadiene rubber, chloroprene rubber, styrene・ Butadiene rubber (SBR), acrylonitrile butadiene rubber (NBR), styrene ethylene butadiene styrene rubber, styrene isoprene styrene rubber, styrene isobutylene rubber, isoprene rubber, polyisobutylene rubber, butyl rubber, (meth) acrylic acid Synthetic acrylic rubber obtained by polymerization of monomers containing alkyl ester, styrene-butadiene block copolymer (SBS), styrene-ethylene / butylene-styrene block Copolymer (SEBS), styrene-isoprene-styrene block copolymer (SIS), polybutadiene (PB), styrene- (ethylene-ethylene / propylene) -styrene block copolymer (SEEPS), ethylene-unsaturated carboxylic acid Acid copolymer (eg, ethylene-acrylic acid copolymer, ethylene-methacrylic acid copolymer, etc.), ethylene-unsaturated carboxylic acid ester copolymer (eg, ethylene-ethyl acrylate copolymer, ethylene-ethyl methacrylate) Copolymers and the like), and at least one selected from the group consisting of these carboxylic acid modified products (eg, maleic anhydride modified product). As a commercial item of the thermoplastic elastomer of (B) component, Nagase Chemtex-made acrylic acid ester copolymer (brand name: SG790, glass transition temperature: -32 degreeC) is mentioned. The component (B) may be used alone or in combination of two or more.

  The component (B) is also preferable to have a glass transition temperature (Tg) of less than 50 ° C. in order to give the film formability of the resin composition and the resin composition after curing to have appropriate flexibility. Furthermore, it is more preferable that (B) component is a phenoxy resin whose glass transition temperature (Tg) is less than 50 degreeC from the film moldability of a resin composition, and an adhesive viewpoint.

As the component (C), if the thermal conductivity is 5 W / m · K or more, a general inorganic filler can be used from the viewpoint of maintaining the insulating property. The component (C) is at least one or more selected from the group consisting of MgO, Al ₂ O ₃ , AlN, BN, a diamond filler, ZnO, and SiC in terms of thermal conductivity, insulation and thermal expansion coefficient. It is preferable that it is an inorganic filler. In addition, ZnO and SiC may be subjected to insulation treatment as needed. As an example of the measurement result of thermal conductivity of each material (unit: W / m · K), MgO is 37, Al ₂ O ₃ is 30, AlN is 200, BN is 30, diamond is 2000, ZnO is 54, SiC is 90. Commercial products of component (C) include magnesium oxide powder (product name: SMO-5, SMO-1, SMO-02, SMO-2) manufactured by Sakai Chemical Industry Co., Ltd., alumina (Al ₂ O ₃ ) powder manufactured by Showa Denko (product name) CBA09S), and alumina (Al ₂ O ₃ ) powder (trade name: DAW-03, ASFP-20) manufactured by Denki Kagaku Kogyo K.K.

  The average particle size of the component (C) (if it is not particulate, its average maximum diameter) is not particularly limited, but it is 0.05 to 50 μm to uniformly disperse the component (C) in the resin composition. Preferred. If the thickness is less than 0.05 μm, the viscosity of the resin composition may be increased to deteriorate the moldability. If it exceeds 50 μm, it may be difficult to uniformly disperse the component (C) in the resin composition. Here, the average particle size of the component (C) is measured by a dynamic light scattering nanotrack particle size analyzer. The component (C) may be used alone or in combination of two or more.

  The component (A) is preferably 1.5 to 15 parts by mass, more preferably 2 to 10 parts by mass, per 100 parts by mass of the resin composition (excluding the solvent).

  Component (B) is used in an amount of 0.5 to 5 parts by mass with respect to 1 part by mass of component (A) from the viewpoint of film formability of the resin composition, thermal conductivity of the resin composition after curing, and heat resistance. is there. If the amount of the component (B) is less than 0.5 parts by mass with respect to 1 part by mass of the component (A), the resin composition can not be formed into a film, and if it exceeds 5 parts by mass, the resin composition after curing Thermal conductivity will be low. Further, the total of (A) and (B) is 100 parts by mass of the resin composition (excluding the solvent) from the viewpoint of film formability of the resin composition, adhesiveness, and thermal conductivity of the resin composition after curing. On the other hand, it is preferable in it being 4-20 mass parts.

  Component (C) is 40 to 95 parts by weight based on 100 parts by weight of the resin composition (excluding the solvent) from the viewpoint of the adhesiveness of the resin composition, the insulation of the resin composition after curing, and the thermal expansion coefficient. It is preferable that it is a mass part. When the amount of the component (C) exceeds 95 parts by mass, the adhesive strength of the resin composition tends to be reduced. On the other hand, when the component (C) is less than 40 parts by mass, even if the thermal conductivity of the high thermal conductivity inorganic filler is high, the thermal conductivity of the cured resin composition may be insufficient.

  The resin composition preferably further contains (D) a cured product. Examples of the component (D) include phenol-based curing agents, acid anhydride-based curing agents, amine-based curing agents, imidazole-based curing agents, carboxylic acid dihydrazide curing agents, and the like. Phenol-based curing agents, amine-based curing agents, acids It is preferable that it is at least one selected from the group consisting of an anhydride based curing agent and an imidazole based curing agent. Further, from the viewpoint of the adhesiveness of the resin composition, a phenol-based curing agent is more preferable, and from the viewpoint of the flowability and adhesiveness of the resin composition, an acid anhydride-based curing agent is more preferable. From the viewpoint of storage stability of the resin composition, an imidazole-based curing agent is more preferable.

  Examples of the phenolic curing agent include phenol novolac, cresol novolac and the like, and phenol novolac is preferable. In addition, since the curing speed of the phenol-based curing agent is slower than that of other curing agents such as acid anhydride-based curing agents, amine-based curing agents, and imidazole-based curing agents, a resin composition using other curing agents. If the curing speed of the resin composition is too fast, it can be used in combination with a phenolic curing agent in order to delay the curing speed of the resin composition.

  As the acid anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyl nadic anhydride, hydrogenated methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, Methylcyclohexenetetracarboxylic dianhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic dianhydride, ethylene glycol bisanhydro trimellitate, glycerin bis (anhydro trimellitate) mono Acetate, dodecenyl succinic anhydride, aliphatic dibasic acid polyanhydride, chlorendic anhydride, methyl butenyltetrahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, methylhymic anhydride, substituted with alkenyl group Succinic anhydride was, glutaric anhydride and the like, methyl butenyl tetrahydrophthalic acid anhydride are preferred.

  Examples of the amine curing agent include linear aliphatic amines, cyclic aliphatic amines, aliphatic aromatic amines, aromatic amines and the like, with preference given to aromatic amines. Examples of carboxylic acid dihydrazide curing agents include adipic acid dihydrazide, isophthalic acid dihydrazide, sebacic acid dihydrazide, dodecanoic acid dihydrazide and the like, with adipic acid dihydrazide being preferred.

  As the imidazole curing agent, a microencapsulated imidazole compound curing agent and an amine adduct type curing agent are preferable from the viewpoint of storage stability of the resin composition, and are dispersed in a liquid epoxy resin such as liquid bisphenol A type A microencapsulated imidazole compound curing agent is more preferable from the viewpoint of workability of the resin composition, curing speed, and storage stability. As the imidazole curing agent, 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2,4- Diamino-6- [2′-methylimidazolyl- (1 ′)] ethyl-s-triazine, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 3-Dihydro-1H-pyrrolo [1,2-a] benzimidazole and the like can be mentioned, and 2,4-diamino-6- [2'-methylimidazolyl- (1 ')] ethyl-s-triazine, 2 , 4-Diamino-6- [2'-undecylimidazolyl- (1)]-ethyl-s-triazine, 2 4-diamino-6- [2'-ethyl-4'-methylimidazolyl- - (1 ')] - ethyl -s- triazine, and curing rate of the resin composition, workability, preferable from the viewpoint of moisture resistance.

  Commercially available products of component (D) include phenol curing agents (product names: MEH 8000, MEH 8005) manufactured by Meiwa Kasei, acid anhydrides (grade: YH 306, YH 307) manufactured by Mitsubishi Chemical, 3 or 4-methyl-hexahydroanhydride manufactured by Hitachi Chemical Co., Ltd. Phthalic acid (product name: HN-5500), Nippon Kayaku amine curing agent (product name: Kayahard A-A), Nippon Finechem product adipic acid dihydrazide (product name: ADH), Asahi Kasei E-materials microencapsulated imidazole compound curing agent (Product name: HX3722, HX3742, HX3932HP, HX3941HP), Ajinomoto Finetechno amine adduct type curing agent (product name: PN-40J), Shikoku Kasei Kogyo's 2-ethyl-4-methylimidazole (product name: 2E4MZ), etc. may be mentioned. However, (B) ingredient is limited to these item names It is not fixed. The component (D) may be used alone or in combination of two or more.

  The component (D) is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the resin composition (excluding the solvent) from the viewpoint of storage stability of the resin composition and curability.

  In addition, the resin composition is an additive such as a coupling agent, a tackifier, an antifoaming agent, a flow control agent, a film forming aid, a dispersant, and an organic solvent as long as the effects of the present invention are not impaired. Can be included.

  Examples of the organic solvent include aromatic solvents such as toluene and xylene, and ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone. The organic solvents may be used alone or in combination of two or more. Moreover, the usage-amount of an organic solvent is although it does not specifically limit, It is preferable to use so that solid content may be 20-50 mass%. From the viewpoint of the workability of the resin composition, the resin composition preferably has a viscosity of 200 to 3000 mPa · s. The viscosity is a value measured at 25 ° C. and a rotation speed of 10 rpm using an E-type viscometer.

The resin composition can form a film having a film thickness of 30 to 200 μm, and winds a support having a dried product of the resin composition having a film thickness of 30 to 200 μm and a width of 20 cm on a 50 mmφ reel. When it is folded, it does not separate. A specific measuring method will be described later in the embodiment.

[Adhesive film]
The resin compositions described above are suitable for the formation of adhesive films. A resin composition can be obtained by dissolving or dispersing a raw material containing components (A) to (C) and the like in an organic solvent. An apparatus for dissolving or dispersing these raw materials is not particularly limited, but may be a lai-kai machine equipped with stirring and a heating apparatus, a three-roll mill, a ball mill, a planetary mixer, a bead mill and the like. . Moreover, you may use combining these apparatuses suitably.

  The adhesive film is obtained by applying the above-mentioned resin composition to a desired support and then drying it. The support is not particularly limited, and examples thereof include metal foils such as copper and aluminum, and organic films such as polyester resin, polyethylene resin, and polyethylene terephthalate resin. The support may be release-treated with a silicone compound or the like.

  The method for applying the resin composition to the support is not particularly limited, but the microgravure method, the slot die method and the doctor blade method are preferable in terms of film thickness reduction and film thickness control. By the slot die method, an adhesive film having a thickness of 10 to 300 μm after heat curing can be obtained.

  Drying conditions can be suitably set according to the kind and quantity of the organic solvent used for a resin composition, the thickness of application | coating, etc. For example, it shall be about 1 to 30 minutes at 50-120 degreeC. Can. The adhesive film obtained in this way has good storage stability. The adhesive film can be peeled from the support at a desired timing.

  The adhesive film can be thermally cured, for example, at 130 to 200 ° C. for 30 to 180 minutes to adhere the adherend. When bonding the adherend which is a heat generating body and the adherend which is a heat receiving body, the cured adhesive film releases heat from the adherend which is a heat generating body to the adherend which is a heat receiving body, It plays a role of heat transfer to dissipate heat on the side of the adherend that is the heat receiving body. Furthermore, the cured adhesive film plays a role of alleviating the stress caused by the difference in the thermal expansion coefficient between the adherend as the heat generating body and the adherend as the heat receiving body.

  The thickness of the adhesive film is preferably 10 μm to 300 μm, more preferably 10 μm to 100 μm, and further preferably 10 μm to 50 μm. If it is less than 10 μm, the desired insulation may not be obtained. If it exceeds 300 μm, there is a possibility that the heat dissipation of the adherend which generates heat can not be sufficiently achieved. As the thickness of the adhesive film becomes thinner, the distance between the adherend as the heat generating body and the adherend as the heat receiver becomes shorter, so from the viewpoint of efficient heat conduction, the thickness of the adhesive film is thinner. Is preferred.

  Moreover, it is more preferable that the hardened | cured adhesive film is 2 W / m * K or more in heat conductivity. Moreover, when the heat conductivity of the hardened | cured adhesive film is less than 2 W / m * K, there exists a possibility that the heat transfer from the heat generating body to the heat receiver may become inadequate. The volume resistivity and thermal conductivity of the cured adhesive film can be controlled by the type and content of the component (C).

  The peel strength of the cured adhesive film is preferably more than 5 N / cm. When the peel strength of the cured adhesive film exceeds 5 N / cm, the reliability of a semiconductor device using the cured adhesive film can be enhanced.

It is preferable that the cured adhesive film has a volume resistivity of 1 × 10 ¹⁰ Ω · cm or more. If the volume resistivity of the cured adhesive film is less than 1 × 10 ¹⁰ Ω · cm, the insulation required for the semiconductor device may not be satisfied.

[Adhesive film with support]
  The adhesive film with a support of the present invention is (A) an aminophenol type epoxy resin,
(B) at least one selected from the group consisting of phenoxy resins and thermoplastic elastomers, and
(C) High thermal conductivity inorganic filler
An adhesive film with a support having a dried product of the resin composition containing
When a support having a thickness of 30 to 200 μm and a dried product of a resin composition having a width of 20 cm is wound on a 50 mmφ reel, it is not divided even if it is bent. A specific measuring method will be described later in the embodiment.

[Semiconductor device]
The semiconductor device of the present invention uses the cured product of the adhesive film described above. A highly reliable semiconductor device can be provided by the cured product of the adhesive film having excellent thermal conductivity and adhesive strength. As a semiconductor device, one obtained by bonding a heat generating body such as a module or an electronic component and a heat receiving body such as a substrate with a cured product of an adhesive film or a heat of a substrate which receives heat from the heat generating body and Furthermore, the thing which adhere | attached the heat sink etc. which receive heat with the hardened | cured material of an adhesive film is mentioned.

  The present invention will be described by way of examples, but the present invention is not limited thereto. In the following examples, parts and% indicate parts by mass and% by mass unless otherwise specified.

[Examples 3-5 , 7-12 , comparative examples 1-4 , reference examples 1-3 ]
After blending (A) component, (B) component, and an appropriate amount of toluene in the formulation shown in Table 1 and Table 2, they are put into a reaction kettle heated to 80 ° C. and rotated at a rotation speed of 150 rpm While performing atmospheric pressure mixing for 3 hours, a clear was produced. The component (C), the component (D) and other components were added to the produced clear and dispersed by a planetary mixer to produce a resin composition for an adhesive film.

〔Evaluation method〕
1. Measurement of Thermal Conductivity The obtained resin composition for an adhesive film was scraped and applied onto a 50 μm-thick PET film to which a release agent had been applied so that the film thickness after drying was 200 to 400 μm. The schematic diagram for demonstrating the method of scraping application to FIG. 1 is shown. First, spacers are stacked in two rows so as to have an appropriate thickness on a PET film with a release agent, and then adhesive tape is attached (FIG. 1 (A)). An appropriate amount of the adhesive film composition is poured onto the release agent-added PET film (FIG. 1 (B)). A slide glass is placed on the spacer, and the adhesive film composition is scraped off and applied (Fig. 1 (C) to (E)). Next, after the composition for an adhesive film applied was sufficiently dried, the obtained adhesive film was cured under conditions of 180 ° C. × 60 minutes and 0.1 MPa using a vacuum press. The cured adhesive film was cut into 10 × 10 mm to prepare a test piece for thermal conductivity measurement. The thermal conductivity of the prepared test piece for thermal conductivity measurement was measured with a thermal conductivity meter (Xe flash analyzer, model number: LFA 447 Nanoflash) manufactured by NETZSCH. Tables 1 and 2 show the measurement results of the thermal conductivity.

2. Measurement of Peel Strength A copper foil having one surface roughened was prepared. Copper foil was pasted on both sides of the adhesive film obtained by carrying out similarly to the time of evaluation of heat conductivity with a roughening side inside. Using a vacuum press, thermocompression bonding was performed under the conditions of 180 ° C. × 60 minutes and 0.1 MPa for curing. The cured product was cut to a width of 10 mm to prepare a sample for peel strength measurement. The prepared sample for measurement of peel strength was peeled off with an autograph manufactured by Shimadzu Corporation (model number: ASG-J-5 kNJ), and the peel strength was measured. For the measurement results, the average value of each N = 5 was calculated. Tables 1 and 2 show the results of peel strength.

3. Film moldability The obtained composition for an adhesive film was applied on a 50 μm-thick PET film to which a release agent was applied, using a coating machine so that the film thickness was 20 cm and the film thickness after drying was 30 to 200 μm. Applied. The applied composition for an adhesive film was dried at 80 ° C. for 20 minutes. This film was wound on a reel of 50 mm in diameter and 40 cm in width, and film formability was evaluated. If it does not break even if it is bent is "5", if it is bent if it is partially broken it is "4", if it is broken if it is broken it is "3" The case where it can not be used was "1". Tables 1 and 2 show the results of film formability.

As can be seen from Tables 1 and 2, in all of Examples 3 to 5 and 7 to 12, all the results of the thermal conductivity, the peel strength, and the film formability were good. On the other hand, Comparative Example 1 using a naphthalene type epoxy resin instead of the aminophenol type epoxy resin had a low thermal conductivity. The thermal conductivity was also low in Comparative Example 2 in which a naphthalene type polyfunctional epoxy resin was used instead of the aminophenol type epoxy resin. The thermal conductivity was also low in Comparative Example 3 in which a bisphenol A epoxy resin was used instead of the aminophenol epoxy resin. In Comparative Example 4 where the component (B) was too small relative to the component (A), the composition for an adhesive film could not be formed into a film, and the thermal conductivity and the peel strength could not be measured.

  As described above, the composition of the present invention can provide a resin composition which is excellent in thermal conductivity, adhesiveness, film formability, and in particular, in thermal conductivity after curing.

The resin composition preferably further contains (D) a curing agent . Examples of the component (D) include phenol-based curing agents, acid anhydride-based curing agents, amine-based curing agents, imidazole-based curing agents, carboxylic acid dihydrazide curing agents, and the like. Phenol-based curing agents, amine-based curing agents, acids It is preferable that it is at least one selected from the group consisting of an anhydride based curing agent and an imidazole based curing agent. Further, from the viewpoint of the adhesiveness of the resin composition, a phenol-based curing agent is more preferable, and from the viewpoint of the flowability and adhesiveness of the resin composition, an acid anhydride-based curing agent is more preferable. From the viewpoint of storage stability of the resin composition, an imidazole-based curing agent is more preferable.

Claims (7)

(A) aminophenol type epoxy resin,
A resin composition comprising (B) at least one member selected from the group consisting of phenoxy resins and thermoplastic elastomers, and (C) high thermal conductivity inorganic fillers,
The dried product of the resin composition can form a film having a thickness of 30 to 200 μm, and
A resin composition which does not separate even when it is bent when a support having a dry product of a resin composition having a film thickness of 30 to 200 m and a width of 20 cm is wound on a 50 mm diameter reel . The resin composition according to claim 1, wherein the component (A) is represented by the following chemical formula (1).
The resin composition according to claim 1, wherein the component (C) is at least one selected from the group consisting of MgO, Al ₂ O ₃ , AlN, BN, a diamond filler, ZnO, and SiC.   The adhesive film formed from the resin composition of any one of Claims 1-3. A cured product of the resin composition according to any one of claims 1 to 3 or a cured product of the adhesive film according to claim 4.   A semiconductor device using the cured product according to claim 5. (A) aminophenol type epoxy resin,
(B) at least one selected from the group consisting of phenoxy resins and thermoplastic elastomers, and
(C) High thermal conductivity inorganic filler
An adhesive film with a support having a dried product of the resin composition containing
When a support having a dry product of a resin composition with a film thickness of 30 to 200 μm and a width of 20 cm is wound on a 50 mmφ reel, it does not separate even when bent
Adhesive film with support.