JP2007231195A - High temperature curable polyorganosiloxane composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a composition excellent in gap-filling performance and giving a cured material without having void even by not loading high pressure. <P>SOLUTION: This curable component contains (A) a mixture obtained by subjecting the following (i) and (ii) to condensation reaction by (30/70) to (70/30) mass ratio for the (i) to (ii) and (B) at least 1 kind of organic peroxide selected from a diacylperoxide and dialkylperoxide, and curing at 130 to 250°C temperature. Provided that (i) an organopolysiloxane having a hydroxy group at the terminal of a molecular chain and having at least one alkenyl group in its molecule and (ii) an organopolysiloxane resin containing the (R<SP>2</SP><SB>3</SB>SiO<SB>1/2</SB>) unit and (SiO<SB>2</SB>) unit by 0.5 to 1.5 molar ratio of the (R<SP>2</SP><SB>3</SB>SiO<SB>1/2</SB>) unit to the (SiO<SB>2</SB>) unit [wherein, R<SP>2</SP>is a 1-10C substituted or non-substituted monovalent hydrocarbon group]. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a curable polyorganosiloxane composition, and more particularly to a curable composition that can be cured in an epoxy resin sealing process of a semiconductor device to form an adhesive layer without voids.

  A semiconductor device usually includes a step of adhering and fixing a large-diameter silicon wafer to a dicing mount for wafer dicing, a dicing step of cutting the fixed silicon wafer into a semiconductor chip, and a silicon chip A step of separating and separating from the dicing tape, and a step of adhering and fixing the semiconductor chip to the lead frame using a curable liquid adhesive (usually referred to as a die bond agent). It is manufactured through.

  Recently, in order to simplify the process and to avoid problems such as contamination of semiconductor parts due to liquid components when using liquid adhesive, the function of the dicing tape for silicon wafer adhesive fixing and the semiconductor chip A dicing / die bonding adhesive sheet having a function as a die bonding agent for adhering and fixing to a lead frame is used.

  As an adhesive sheet for dicing and die bonding, an adhesive composition containing a polyimide resin is proposed in Japanese Patent Laid-Open No. 9-67558 (Patent Document 1), but the polyimide resin has a high Tg and a high elastic modulus. In addition, it is insufficient to relieve the thermal stress between the semiconductor component and the adhesive base material, causing cracks and the like, leading to a decrease in the reliability of the semiconductor component.

Silicone adhesives having lower Tg and elastic modulus and exhibiting both adhesive properties and thermosetting properties are also known (Patent Documents 2 to 4). These are room temperature curable products that are crosslinked and cured by moisture and moisture in the air, and have a long period of several days to several weeks until a desired large adhesive force is obtained. As a pressure-sensitive adhesive for dicing and a pressure-sensitive adhesive for die bonding, there are problems in terms of productivity.
JP-A-9-67558 JP 7-53871 A JP 7-53942 A JP-A-7-70541

  The semiconductor substrate has a so-called gap due to a wiring pattern or the like on the surface and is not flat. When bonding the silicon chip to such a substrate, if the adhesive fills the gap and the air in the gap cannot be expelled, it will remain as a void in the cured adhesive, which is the solder reflow May explode in the process. In the case of using the above conventional composition, particularly a polyimide resin, it is necessary to apply a high load in order to fill the gap. However, for the purpose of reducing the size of the semiconductor package, the wafer may be as thin as about 100 μm, and the chip may be destroyed when the wafer is pressed under a high load. Then, an object of this invention is to provide the composition which is excellent in gap fill performance and gives the hardened | cured material which does not have a void even if high pressure is not loaded.

That is, the present invention is as follows.
(A) A mixture obtained by subjecting (i) and (ii) below to a condensation reaction at a mass ratio of (i) to (ii) of 30/70 to 70/30,
(I) an organopolysiloxane having a hydroxyl group at the end of a molecular chain having at least one alkenyl group in the molecule represented by the following formula (1);

（Ｒ^１は、互いに独立に、炭素原子数１〜１０の置換もしくは非置換の一価炭化水素基であり、ｍは３０％トルエン溶液での粘度が、１，０００〜１００，０００ｍＰａ・ｓとなるような数である）、
（ｉｉ）（Ｒ^２ _３ＳｉＯ_１／２）単位と（ＳｉＯ_２）単位を、（Ｒ^２ _３ＳｉＯ_１／２）単位の（ＳｉＯ_２）単位に対するモル比０．５〜１．５で含み、但しＲ^２は炭素原子数１〜１０の置換もしくは非置換の一価炭化水素基である、オルガノポリシロキサンレジン、
及び
（Ｂ）ジアシルパーオキサイド及びジアルキルパーオキサイドから選ばれる少なくとも１種の有機過酸化物、
を含み、温度１３０〜２５０℃で硬化することを特徴とする組成物。

(R ¹ is, independently of each other, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and m is a viscosity in a 30% toluene solution of 1,000 to 100,000 mPa · s. ),
(Ii) comprising (R ² ₃ SiO _1/2 ) units and (SiO ₂ ) units in a molar ratio of (R ² ₃ SiO _1/2 ) units to (SiO ₂ ) units of 0.5 to 1.5, Where R ² is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, an organopolysiloxane resin,
And (B) at least one organic peroxide selected from diacyl peroxide and dialkyl peroxide,
And a composition that is cured at a temperature of 130 to 250 ° C.

  The composition of the present invention is in a flexible state when the silicon chip is pressure-bonded to the substrate, and is not completely cured even at a sealing molding temperature, for example, 170 ° C. The trapped air can be extracted by using the stationary pressure, and the generation of voids can be suppressed.

In the composition of the present invention, the component (A) is a reaction mixture obtained by subjecting the organopolysiloxane component (i) and the organosiloxane resin component (ii) to a condensation reaction.
The component (i) is an organopolysiloxane having a hydroxyl group at the end of a molecular chain having at least one alkenyl group in the molecule represented by the following formula (1).

Ｒ^１は、互いに独立に、炭素原子数１〜１０の置換もしくは非置換の一価炭化水素基であり、ｍは３０％トルエン溶液での粘度が、１，０００〜１００，０００ｍＰａ・ｓとなるような数である。上記Ｒ^１としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、tert-ブチル基、ヘキシル基等のアルキル基；ビニル基、アリル基、プロペニル基、イソプロペニル基、ブテニル基等のアルケニル基；シクロヘキシル基等のシクロアルキル基；フェニル基、トリル基、キシリル基、ナフチル基などのアリール基；ベンジル基、フェニルエチル基等のアラルキル基；３，３，３-トリフルオロプロピル基等のハロゲン置換炭化水素基、及びシアノ置換炭化水素等が挙げられる。これらの中で特に好ましくはメチル基、エチル基、ビニル基、プロピル基等である。

R ¹ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and m has a viscosity in a 30% toluene solution of 1,000 to 100,000 mPa · s. It is a number like this. Examples of R ¹ include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and hexyl; vinyl, allyl, propenyl, isopropenyl, butenyl, and the like. Alkenyl group; cycloalkyl group such as cyclohexyl group; aryl group such as phenyl group, tolyl group, xylyl group, naphthyl group; aralkyl group such as benzyl group, phenylethyl group; 3,3,3-trifluoropropyl group, etc. Examples include halogen-substituted hydrocarbon groups and cyano-substituted hydrocarbons. Among these, a methyl group, an ethyl group, a vinyl group, a propyl group and the like are particularly preferable.

  This component (i) is measured by a rotational viscometer, and the viscosity of a 30% by weight toluene solution at 25 ° C. is 1,000 to 100,000 mPa · s or less, preferably 5,000 to 75,000 mPa · s. is there. In the case of the diorganopolysiloxane having a too high solution viscosity, the composition becomes too high in viscosity, making it difficult to perform operations such as stirring and mixing during production, and it may be difficult to apply in a film form. .

(I) As a suitable example of organopolysiloxane, what is represented by following formula (2) is mentioned.

式中、Ｍｅはメチル基、Ｖｉはビニル基を示し、ｐは１００以上の整数である。ｑは１以上の整数であり、好ましくはオルガノポリシロキサン１００ｇ中のＶｉの量が０．０００１〜０．２モル、より好ましくは０．００１〜０．００４となる数である。ｐ＋ｑの和はこのオルガノポリシロキサンの３０質量％トルエン溶液の２５℃における粘度が上述の粘度範囲となる数である。なお、この（ｉ）成分のオルガノポリシロキサンは、２種以上の組み合わせであってよい。

In the formula, Me represents a methyl group, Vi represents a vinyl group, and p is an integer of 100 or more. q is an integer of 1 or more, and is preferably a number such that the amount of Vi in 100 g of organopolysiloxane is 0.0001 to 0.2 mol, more preferably 0.001 to 0.004. The sum of p + q is the number at which the viscosity at 25 ° C. of a 30 mass% toluene solution of this organopolysiloxane falls within the above-mentioned viscosity range. The organopolysiloxane of component (i) may be a combination of two or more.

(Ii) organopolysiloxane resin ^is, _(R 2 _{3 SiO 1/2)} units and the (SiO ₂₎ ^units, the molar ratio of _(R 2 _{3 SiO 1/2)} units (SiO ₂₎ units 0.5 Resin containing at ˜1.5, preferably 0.6 to 1.0, ie, a resin that is solid at room temperature. When the resin has a molar ratio of less than 0.6, it is difficult to obtain a composition having sufficient adhesive strength and tackiness, and the same applies to resins having a molar ratio of more than 1.7.

R ² is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms. Examples of R ² include an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group, a cycloalkyl group such as a cyclohexyl group, an aryl group such as a phenyl group, an alkenyl group such as a vinyl group, an allyl group, and a hexenyl group. Among these, a methyl group is preferable.

This (ii) organopolysiloxane resin may have a hydroxyl group (silanol group) bonded to a silicon atom. In this case, the hydroxyl group content is 0.02 to 0.1 mol per 100 g of the organopolysiloxane resin. / 100 g, preferably about 0.02 to 0.05 mol / 100 g. When the hydroxyl group content exceeds the upper limit, the thermosetting property of the composition may be lowered. Further, the component (ii) is represented by a trifunctional unit represented by the formula: R ² SiO _3/2 and / or a formula: R ² ₂ SiO, as long as the object and effect of the present invention are not impaired. that bifunctional units (in each of the formulas above, R ² is same as that defined above), and may have a range that does not impair the object of the present invention.

  Preferable examples of this (ii) organopolysiloxane resin include organopolysiloxane resins represented by the following average composition formula (3).

Ｒ²は上述の１価炭化水素基であり、ａ、ｂ、ｃは、それらの合計が１である正の数であり、上述のとおり、ａ／ｂが０．５〜１．５である。ｃはＯＨ基量が上述した範囲となるような数である。好ましくは、ａ／（ｂ＋ｃ）＝０．５〜１．０であり、より好ましくは０．６〜０．９である。なお、（ｉｉ）成分のオルガノポリシロキサンレジンは、２種以上の組み合わせであってもよい。

R ² is the above-mentioned monovalent hydrocarbon group, a, b and c are positive numbers whose sum is 1, and as described above, a / b is 0.5 to 1.5. . c is a number such that the amount of OH groups falls within the range described above. Preferably, it is a / (b + c) = 0.5-1.0, More preferably, it is 0.6-0.9. The organopolysiloxane resin (ii) may be a combination of two or more.

  The proportion of the component (i) and component (ii) used is such that the mass ratio of component (i) / component (ii) is 30 to 70/70 to 30, preferably 40/60 to 60/40. It is a ratio.

  The composition of this invention contains the said (i) component and (ii) component as a condensation reaction mixture. The condensation reaction is performed by dissolving both components in a solvent such as toluene in which both components are soluble and mixing them, and using a basic catalyst such as ammonia or an alkaline catalyst at room temperature to reflux temperature. After the reaction, water produced by the condensation reaction is removed by azeotropic distillation with toluene or the like.

  (B) As at least one organic peroxide selected from diacyl peroxide and dialkyl peroxide, for example, benzoyl peroxide, bis (3-methylbenzoyl) peroxide, bis (4-methylbenzoyl) peroxide, Diacyl peroxide and dicumyl peroxide, bis (t-butyl) peroxide, 2,5-dimethyl-2,5-bis (t-), such as 2,4-dichlorobenzoyl peroxide and p-chlorobenzoyl peroxide Butylperoxy) hexane, dialkyl peroxides such as t-butylcumyl peroxide, and mixtures thereof. Dicumyl peroxide, bis (t-butyl) peroxide, 2,5-dimethyl-2,5-bis (t-butyl) having a decomposition temperature of 160 ° C. or higher, preferably 170 ° C. or higher, with a half-life of 1 minute. Peroxy) hexane, t-butylcumyl peroxide, and the like are preferable because they can be easily adjusted so that the composition is cured when the epoxy resin for sealing the semiconductor chip is thermally cured. The blending amount of the organic peroxide is adjusted depending on the amount of alkenyl group in the components (i) and (ii), but typically, the total amount of (i) and (ii) is 100 mass. 0.1 to 10 parts by mass, more typically 0.5 to 5 parts by mass with respect to parts.

  The composition of the present invention cures at 130-250 ° C. The curing temperature can be measured by DSC, for example, as shown in FIG. 1, where the horizontal axis is temperature (° C.). As shown in the figure, since the exothermic peak width is usually wide, it is sufficient that the start to the end of the exotherm is substantially observed in the above temperature range. If it is within this temperature range, it is in a semi-cured state at a normal epoxy resin sealing temperature of 120 to 250 ° C., and even if air is trapped between the substrate and the composition layer, the air Is easy to come off. In order to adjust to the desired curing temperature within the above temperature range, (C) a curing retarder for delaying the decomposition of the organic peroxide can be added. Examples of the curing retarder include mercaptans such as α-methylstyrene dimer and derivatives thereof, n-butyl mercaptan, t-butyl mercaptan, n-dodecyl mercaptan and the like. From the viewpoint of odor, it is preferable to use α-methylstyrene dimer. Although the compounding quantity of this hardening retarder is suitably adjusted depending on an organic peroxide and desired hardening temperature, it is typically 0.01-5 mass parts, More preferably, it is 0.1-1 Part by mass.

  When the composition of the present invention is applied on a film, it is diluted with an organic solvent so that the viscosity is easy to apply. Examples of the organic solvent include toluene, xylene, hexane, heptane, ethanol, isopropyl alcohol, acetone, methyl ethyl ketone, and the like. The amount of the organic solvent used may be adjusted according to the desired viscosity, but typically 20 parts per 100 parts by weight of the total amount of the components (A) and (B) and optionally used (C). About 400 parts by mass, more typically about 30-300 parts by mass.

  Moreover, in order to improve the adhesive strength of the hardened | cured material of this invention composition, you may add an adhesion aid. Examples of the adhesion assistant include vinyltrimethoxysilane, vinylmethyldimethoxysilane, vinyltriethoxysilane, acryloxypropyltrimethoxysilane, acryloxypropylmethyldimethoxysilane, acryloxypropyltriethoxysilane, and methacryloxypropyltrimethoxy. Mention may be made of silane compounds such as silane, methacryloxypropylmethyldimethoxysilane, methacryloxypropyltriethoxysilane, glycidoxypropyltrimethoxysilane, glycidoxypropyltriethoxysilane, and mixtures thereof. The compounding amount of the adhesion assistant varies depending on the types of the above components (i) and (ii), but is typically 0.2 to 20 with respect to 100 parts by mass of the total amount of the components (A) to (C). It is about 1 to 10 parts by mass, more typically about 1 to 10 parts by mass.

  Other fillers such as silica fine powder, alumina fine powder, titanium oxide, carbon black, and conductive particles in amounts that do not impair the object of the present invention; colorants such as inorganic or organic pigments and dyes; You may mix | blend additives, such as an agent, suitably.

  The composition of the present invention can be prepared by mixing the condensate (A), (B) and other additives with a mixer or the like.

  The composition of the present invention can be applied onto a film substrate to form a tacky and adhesive film. Examples of the film substrate include polyethylene, polypropylene, polyester, polyamide, polyimide, polyamideimide, polyetherimide, polytetrafluoroethylene, paper, and metal foil. You may process these film base-material surfaces with a mold release agent. The composition of the present invention is applied directly on the film substrate or applied in a solvent and dried to form a layer. The thickness of the layer is not limited and can be selected according to the purpose. Usually 0.01 to 0.2 mm.

  If the composition is applied diluted with a solvent, the solvent is dried. Drying conditions are performed at a temperature at which the composition does not cure. Although it depends on the target film thickness, it is usually 2 hours or more at room temperature and 1 to 20 minutes at 40 to 120 ° C. If the temperature is higher and the heating time is longer, the silicone composition starts to cure, and the object of the present invention may not be achieved.

  Furthermore, it is preferable to laminate a film base material on the upper surface of the composition layer as a protective film. When using a protective film, the protective film is peeled off, and the exposed composition layer is pressure-bonded to the substrate. After the target step is achieved in this state, the other film substrate is then peeled off and another substrate is removed. Crimp and heat bond to the material. When the film of the present invention is used as a film for dicing-die bonding, the protective film substrate of the film is peeled off, pressure bonded and fixed to the wafer, and dicing (cutting separation) is performed in this state. Next, in the pick-up process, the semiconductor chip to which the silicone adhesive is attached is peeled off from the base film and taken out, and is pressure-bonded to a base such as a lead frame and thermally bonded. At this time, the pressure bonding temperature is preferably 180 ° C. or lower, particularly 160 ° C. or lower. When the pressure bonding temperature exceeds the above temperature, the silicon chip is warped, which is not preferable because it causes chip cracking, poor electrical connection, and the like. In addition, since the curing of the composition proceeds when the crimping temperature exceeds the above temperature, gap fill, that is, the gap between wirings on the substrate cannot be completely filled with the composition, resulting in voids and reduced reliability. In addition, since the adhesive force decreases with sufficient curing of the resin, the chip is liable to be displaced due to molding pressure when sealing with an epoxy resin. The pressure at the time of pressure bonding is preferably 0.01 to 0.5 MPa, and particularly preferably 0.01 to 0.3 MPa for about 1 to 10 seconds. If the applied pressure is less than 0.01 MPa, the silicon chip cannot be sufficiently fixed. Further, if it exceeds 0.5 MPa, the silicon chip may be destroyed.

  When the composition of the present invention is not coated on a film, it is directly applied to a substrate such as a lead frame so as to have a desired thickness, or is coated and dried in a state dissolved in a solvent, The adherend is fixed on the applied composition by pressure bonding, and the composition is heated to cure and used.

  As described above, the curing of the composition is 130 to 250 ° C., preferably 150 to 220 ° C., more preferably 160 to 200 ° C., and the curing time in the above temperature range is 15 to 120 minutes, preferably 30 to 60 minutes. Within this temperature range, even if bubbles remain between the substrate and the element, the bubbles can be extracted with a sealing molding pressure.

  The base material to which the composition of the present invention is applied is not limited to the above lead frame, but may be a metal such as Fe, Al, Cr, Ni, Si, Cu, Ag, Au, glass, silicon nitride, silicon carbide, etc. It may be an inorganic substance, ceramics, or an organic substance such as epoxy, bakelite, polyimide, polyamide, polyester, or silicone resin.

Hereinafter, although a preparation example, an Example, and a comparative example are shown and demonstrated about this invention, this invention is not limited to these. In the following, “parts” and “%” mean mass parts and mass%, respectively.
[Example 1]
(A) Raw rubber-like dimethylpolysiloxane having both ends of the molecular chain blocked with hydroxyl groups as component (i), the viscosity of which is 30% toluene solution at 25 ° C. is 42,000 mPa · s, and per 100 g 50 parts of dimethylpolysiloxane having 0.002 mol of vinyl group, and (ii) a ratio of 0.75 mol of (CH ₃ ) SiO _1/2 units and 1 mol of SiO ₂ units as component, and 0.02 mol / 50 parts of methylpolysiloxane resin containing 100 g of hydroxyl group was dissolved in 100 parts of toluene. To the obtained solution, 0.5 part of 28% aqueous ammonia was added and stirred at room temperature for 16 hours to cause a condensation reaction. Subsequently, it heated at 120-130 degreeC, condensed water was removed with toluene by azeotropic dehydration, and the reaction mixture was obtained.
To 100 parts of the reaction mixture obtained above, 100 parts of toluene was again added and dissolved. 100 parts of this toluene solution, 8 parts of a compound represented by the following structural formula (4) as an adhesion assistant, and 4 parts of dicumyl peroxide as a component (B) were added and mixed. The composition was applied to a PET film surface-treated with a fluorine-based release agent having a thickness of 50 microns and dried at 100 ° C. for 5 minutes to form a 0.025 mm thick layer. Moreover, when the curing temperature of the composition after drying was measured by DSC (in air, 10 ° C./min, control aluminum pan), it was cured at 150 to 200 ° C.

[Example 2]
A layer having a thickness of 0.025 mm was formed in the same manner as in Example 1 except that 1 part of α-methylstyrene dimer was further added and mixed as component (C).

[Reference Example 1]
A layer having a thickness of 0.025 mm was formed in the same manner as in Example 1 except that the composition was dried at 150 ° C. for 5 minutes.

[Reference Example 2]
A layer having a thickness of 0.025 mm was formed in the same manner as in Example 1 except that 4 parts of p-menthane hydroperoxide was used as the component (B).

[Reference Example 3]
A layer having a thickness of 0.025 mm was formed in the same manner as in Example 1 except that 90 parts of component (i) and 10 parts of component (ii) were reacted.

[Evaluation methods]
Using each of the obtained sheets, a semiconductor device was prepared by the following method, and the gap fill property and the solder reflow resistance were examined. The results are shown in Table 1.

Preparation of Semiconductor Device The composition layer side of each sheet was pasted on the back surface of a silicon wafer having a thickness of 150 μm and diced to a size of 10 mm × 10 mm. This was picked up together with this layer, and the silicon chip with the composition layer thus picked up was die-attached at a temperature, pressure and time shown in Table 1 on a substrate having 15 μm convex portions coated with solder resist ink. The presence or absence of voids between the silicon chip and the substrate was confirmed using an ultrasonic laceration device (QUANTAM350 manufactured by SONIX). Next, wire bonding is performed, molding is performed with a sealant (trade name KMC2520VA, manufactured by Shin-Etsu Chemical Co., Ltd.) (molding conditions: temperature 175 ° C., about 75 MPa, 90 seconds), and heat curing is performed at 180 ° C. for 3 hours. The adhesive film and the sealing resin were cured.

About the apparatus by which the gap fill property was obtained, the presence or absence of an internal void was confirmed with the ultrasonic wound apparatus similarly to the above.

Solder reflow resistance The obtained device was absorbed in a constant temperature and humidity layer under the conditions of 85 ° C., 60% Rh, 168 hr, and then passed through an IR reflow furnace (temperature 260 ° C., 10 seconds) three times. Later, it was observed whether cracks, voids, or the like were generated inside the semiconductor device with an ultrasonic flaw detector.

In Reference Example 1, the composition used was the same as in Example 1, but the drying temperature was too high and curing progressed. As a result, voids remained after molding. The p-menthane hydroperoxide used in Reference Example 2 is neither a diacyl peroxide nor a dialkyl peroxide. Since the composition of Reference Example 2 did not progress and did not adhere sufficiently, voids remained after the sealing step. In the composition used in Reference Example 3, the ratio of component (i) to component (ii) was outside the scope of the present invention, and voids remained. On the other hand, none of the semiconductor devices produced in Examples 1 and 2 had voids, and no cracks were generated in the reflow process.

  The composition of the present invention is suitably used for the production of a semiconductor device using a thin silicon wafer, and can provide a highly reliable semiconductor device free from voids.

2 is a DSC chart of the composition prepared in Example 1.

Claims (10)

(A) A mixture obtained by subjecting (i) and (ii) below to a condensation reaction at a mass ratio of (i) to (ii) of 30/70 to 70/30,
(I) an organopolysiloxane having a hydroxyl group at the end of a molecular chain having at least one alkenyl group in the molecule represented by the following formula (1);

(R ¹ is, independently of each other, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and m is a viscosity in a 30% toluene solution of 1,000 to 100,000 mPa · s. ),
(Ii) having (R ² ₃ SiO _1/2 ) units and (SiO ₂ ) units at a molar ratio of (R ² ₃ SiO _1/2 ) units to (SiO ₂ ) units of 0.5 to 1.5. Wherein R ² is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, an organopolysiloxane resin,
And (B) at least one organic peroxide selected from diacyl peroxide and dialkyl peroxide,
And a composition that is cured at a temperature of 130 to 250 ° C.   (B) At least one organic peroxide selected from diacyl peroxide and dialkyl peroxide is added in an amount of 0.1 to 100 parts by mass in total of (i) organopolysiloxane and (ii) organopolysiloxane resin. The composition of claim 1 comprising 10 parts by weight. The composition according to claim 1 or 2, which is cured at a temperature of 150 to 220 ° C. (I) The composition according to any one of claims 1 to 3, wherein the organopolysiloxane is represented by the following formula (2).

(In the formula, Me represents a methyl group, Vi represents a vinyl group, p is an integer of 100 or more, q is an integer of 1 or more, and the sum of p + q is 25 of a 30% by mass toluene solution of this organopolysiloxane. (The number is such that the viscosity at 1000 ° C. is 1,000 to 100,000 mPa · s) (Ii) The composition according to any one of claims 1 to 4, wherein the organopolysiloxane resin is represented by the following average composition formula (3).

(R ² is the above-mentioned monovalent hydrocarbon group, a / b = 0.5 to 1.5, and c is the amount of hydroxyl group per 100 g of organopolysiloxane resin is 0.02 to 0.1. Mol / 100g) (B) At least one organic peroxide selected from diacyl peroxide and dialkyl peroxide is dicumyl peroxide, bis (t-butyl) peroxide, 2,5-dimethyl-2,5-bis (t The composition according to any one of claims 1 to 5, which is at least one selected from (-butylperoxy) hexane and t-butylcumyl peroxide. 7. The composition according to claim 1, further comprising at least one (C) curing retardant selected from α-methylstyrene dimer and derivatives thereof, n-butyl mercaptan, t-butyl mercaptan and n-dodecyl mercaptan. A composition according to claim 1. In the adhesive sheet which consists of a film base material and the adhesive layer given to at least one side of this film base material, this adhesive layer is from the composition of any one of Claims 1-7. An adhesive sheet characterized by comprising: The sheet according to claim 8, which is an adhesive sheet for dicing and die bonding. The semiconductor device provided with the semiconductor chip joined on the board | substrate through the hardened | cured material obtained from the composition of any one of Claims 1-7.

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