JP5413127B2 - Semiconductor sealing resin composition, semiconductor device using the same, and method for producing semiconductor sealing resin composition - Google Patents

Description

  The present invention relates to a resin composition for semiconductor encapsulation, a semiconductor device, and a method for producing a resin composition for semiconductor encapsulation.

  The demand for miniaturization, weight reduction, and high performance of electronic devices is not limited, and the integration and density of semiconductor elements (hereinafter, also referred to as “elements” and “chips”) have progressed year by year. Furthermore, surface mounting technology has appeared and is becoming popular in the mounting method of semiconductor devices (hereinafter also referred to as “packages”). Due to such advances in peripheral technology of semiconductor devices, demands for resin compositions for sealing semiconductor elements have become severe. For example, in the surface mounting process, a semiconductor device that has absorbed moisture is exposed to a high temperature during the soldering process, and cracks and internal delamination occur due to explosive stress of water vapor that is rapidly vaporized, thereby significantly reducing the operational reliability of the semiconductor device. Furthermore, the lead-free use of the lead is switched to lead-free solder having a higher melting point than before, and the mounting temperature is about 20 ° C. higher than that of the conventional one, so that the stress during the soldering process becomes more serious. Thus, due to the spread of surface mounting technology and switching to lead-free soldering, solder resistance has become one of the important technical issues for semiconductor sealing resin compositions.

  Also, against the background of environmental problems in recent years, there has been an increasing social demand to eliminate the use of flame retardants such as brominated epoxy resins and antimony oxide, which have been used in the past, without using these flame retardants. Therefore, a technology for imparting the same flame retardance as that of the prior art has become necessary. As such an alternative flame-retarding technique, for example, a technique of applying a low-viscosity crystalline epoxy resin and blending more inorganic fillers has been proposed (see, for example, Patent Document 1 and Patent Document 2). However, it cannot be said that these methods also sufficiently satisfy solder resistance and flame retardancy.

In recent years, a structure in which chips are stacked in one package has appeared. In such a semiconductor device, since the thickness of the resin-encapsulated portion is thinner than before, there is a problem that wire flow is likely to occur and unfilling is likely to occur.
As a technique for further improving the fluidity of the resin composition in order to prevent such wire flow or unfilling, there is a technique using a low molecular weight epoxy resin or a phenol resin curing agent. However, when a low molecular weight epoxy resin is used, in the process of manufacturing the resin composition, the resin compositions may be fixed to each other or the productivity may be lowered due to the resin composition adhering to the inside of the apparatus. This is called poor handling.

  Similarly, when a low molecular weight epoxy resin is used, there is a problem that continuous moldability is lowered. That is, continuous moldability is a problem that may occur when a resin composition for sealing is continuously filled and molded in a mold in a manufacturing process of a semiconductor device, and is formed into a tablet shape in advance for sealing. When the resin compositions adhere to each other or the resin composition adheres to the inside of the continuous molding equipment, poor conveyance and equipment stoppage occur, and further, the adhered resin composition (tablet) must be discarded. . In addition, when the resin composition is filled in the mold for sealing, cured, and released, a part of the resin is lost and remains in the air vent part of the mold, resulting in a defective filling in subsequent molding. In some cases, the moldability is lowered. In particular, a semiconductor package in which a plurality of semiconductor chips are stacked has a higher loss cost due to a decrease in continuous formability than a conventional single-layer chip semiconductor package, and the semiconductor package has good continuous formability. It was important. Thus, since continuous moldability will fall if it is going to improve the fluidity | liquidity of a resin composition, it was important to make both compatible.

  Further, as the number of stacked chips increases, the number of wire bonding processes increases, and the time spent on the process increases, resulting in a problem that the surface of the metal lead frame is easily oxidized. Generally, when the oxidation of the metal lead frame surface proceeds, the adhesion between the cured resin composition and the metal lead frame surface may be reduced. In order to prevent oxidation of the lead frame, a technique has been adopted in which the metal lead frame is plated with gold to increase the anti-oxidation property, but the sealing resin tends to be less compatible with gold than copper or the like. As a result, the adhesion between the lead frame metal surface and the resin composition decreased, and the solder resistance tended to decrease.

  Conventionally, a resin composition for semiconductor encapsulation uses a phenol resin and an epoxy resin obtained by epoxidation of a precursor phenol resin as a material, and a mixture thereof is widely used (for example, Patent Documents 3 to 3). 4).

  Patent Document 3 describes a resin composition in which a phenolic resin and an epoxy resin obtained by epoxidizing a phenolic resin are mixed. Patent Document 4 discloses a resin composition in which a plurality of epoxy resins and a phenol resin are mixed as a reference example. Each of the mixtures of these resin compositions is characterized in that a plurality of epoxy resins individually epoxidized and a phenol resin are mixed after previously epoxidizing a phenol resin as a precursor.

  However, generally, when a phenol resin is epoxidized, the viscosity of the resin composition decreases and good fluidity can be obtained. On the other hand, epoxidation tends to lower the softening point of the resin composition. Due to the lowering of the softening point, the resin compositions may adhere to each other in the production process of the resin composition, or the resin composition may adhere to the inside of the apparatus, resulting in blocking, and handling properties may be reduced.

JP-A-7-130919 JP-A-8-20673 Japanese Patent Laid-Open No. 7-196892 JP 2009-73862 A

  In view of the above situation, the present invention provides a resin composition for encapsulating a semiconductor excellent in the balance of fluidity, continuous moldability, handling properties and adhesion, and reliability obtained by encapsulating a semiconductor element with a cured product thereof. An object of the present invention is to economically provide a semiconductor device excellent in performance.

  As a result of intensive studies, the present inventor can mix resin components even when a precursor phenol resin having a low softening point is used by epoxidizing after mixing the resin components in the state of the precursor phenol resin. I found out. As a result, a low-viscosity resin composition can be obtained, and the room for selection of the precursor phenolic resin is widened. Therefore, for semiconductor encapsulation with excellent balance of fluidity, continuous moldability, handling properties and adhesion. The inventors have found that a resin composition can be obtained and have reached the present invention.

  The object of the present invention is achieved by the present invention described in the following [1] to [13].

（ただし、上記一般式（１）において、Ｒ１は炭素数１〜６の炭化水素基、Ｒ２は炭素数１〜１０の炭化水素基であり、互いに同じでも異なっていてもよい。Ｒｘ及びＲｙは水素原子または炭素数１〜６の炭化水素基であり、互いに同じでも異なっていてもよい。ｉは１〜４の整数であり、ｊは０〜３の整数である。ｎは０〜１０の整数であり、ｍは０〜１０の整数であり、ｍ＋ｎ≧２である。繰り返し数ｎで表される構造単位と繰り返し数ｍで表される構造単位は、連続で並んでいても、お互いが交互に並んでいても、ランダムに並んでいてもよいが、それぞれの間には必ず−Ｃ（ＲｘＲｙ）−を有する構造をとる。）

（ただし、上記一般式（２）において、Ｒ３は、炭素数１〜１０の炭化水素基であり、互いに同じでも異なっていてもよい。Ｒｐ、Ｒｑ、Ｒｒ及びＲｓは、水素原子または炭素数１〜６の炭化水素基であり、互いに同じでも異なっていてもよい。ｋは０〜３の整数である。ｌは０〜１０の整数である。）
［２］［１］に記載の半導体封止用樹脂組成物において、エポキシ樹脂（Ａ）の軟化点が、５０℃以上８０℃以下であることを特徴とする半導体封止用樹脂組成物。
［３］［１］又は［２］に記載の半導体封止用樹脂組成物において、一般式（１）中のＲ１がメチル基であり、かつ、ｉ＝２であることを特徴とする半導体封止用樹脂組成物。
［４］［１］又は［２］に記載の半導体封止用樹脂組成物において、エポキシ樹脂（Ａ）のエポキシ当量が２２０ｇ／ｅｑ以上、３００ｇ／ｅｑ以下であることを特徴とする半導体封止用樹脂組成物。
［５］［１］又は［２］に記載の半導体封止用樹脂組成物において、一般式（１）で表される構造を有する化合物が、置換又は無置換のフェノール、キシレン、及びホルマリンから合成されることを特徴とする半導体封止用樹脂組成物。
［６］［１］乃至［５］いずれかに記載の半導体封止用樹脂組成物の硬化物で半導体素子を封止して得られることを特徴とする半導体装置。
［７］［６］に記載の半導体装置において、前記半導体素子がリードフレーム上にマウントされたものであることを特徴とする半導体装置。
［８］一般式（１）で表される構造を有する化合物と一般式（２）で表される化合物とを混合する工程と、
混合された一般式（１）で表される構造を有する化合物と一般式（２）で表される化合物とを、エポキシ化してエポキシ樹脂（Ａ）を得る工程と、
を含み、エポキシ樹脂（Ａ）と、フェノール樹脂系硬化剤（Ｂ）と、無機充填剤（Ｃ）と、を含むことを特徴とする半導体封止用樹脂組成物の製造方法。

（ただし、上記一般式（１）において、Ｒ１は炭素数１〜６の炭化水素基、Ｒ２は炭素数１〜１０の炭化水素基であり、互いに同じでも異なっていてもよい。Ｒｘ及びＲｙは水素原子または炭素数１〜６の炭化水素基であり、互いに同じでも異なっていてもよい。ｉは１〜４の整数であり、ｊは０〜３の整数である。ｎは０〜１０の整数であり、ｍは０〜１０の整数であり、ｍ＋ｎ≧２である。繰り返し数ｎで表される構造単位と繰り返し数ｍで表される構造単位は、連続で並んでいても、お互いが交互に並んでいても、ランダムに並んでいてもよいが、それぞれの間には必ず−Ｃ（ＲｘＲｙ）−を有する構造をとる。）

（ただし、上記一般式（２）において、Ｒ３は、炭素数１〜１０の炭化水素基であり、互いに同じでも異なっていてもよい。Ｒｐ、Ｒｑ、Ｒｒ及びＲｓは、水素原子または炭素数１〜６の炭化水素基であり、互いに同じでも異なっていてもよい。ｋは０〜３の整数である。ｌは０〜１０の整数である。）
［９］［８］に記載の半導体封止用樹脂組成物の製造方法において、エポキシ樹脂（Ａ）の軟化点が、５０℃以上８０℃以下であることを特徴とする半導体封止用樹脂組成物の製造方法。
［１０］［８］又は［９］に記載の半導体封止用樹脂組成物の製造方法において、一般式（１）中のＲ１がメチル基であり、かつ、ｉ＝２であることを特徴とする半導体封止用樹脂組成物の製造方法。
［１１］［８］又は［９］に記載の半導体封止用樹脂組成物の製造方法において、エポキシ樹脂（Ａ）のエポキシ当量が２２０ｇ／ｅｑ以上、３００ｇ／ｅｑ以下であることを特徴とする半導体封止用樹脂組成物の製造方法。
［１２］［８］又は［９］に記載の半導体封止用樹脂組成物の製造方法において、一般式（１）で表される構造を有する化合物が、置換又は無置換のフェノール、キシレン、及びホルマリンから合成されることを特徴とする半導体封止用樹脂組成物の製造方法。 [1] An epoxy resin (A), a phenol resin-based curing agent (B), and an inorganic filler (C) are included, and the epoxy resin (A) has a structure represented by the general formula (1). compound with epihalohydrin and epoxy resin are reacted, the general formula (2) and the compound represented by the epihalohydrin saw contains a reaction with epoxy resin, and a compound having a structure represented by the general formula (1) and general A resin composition for encapsulating a semiconductor, which is an epoxy resin that is epoxidized after being mixed with a compound represented by the formula (2) .

(However, in the above general formula (1), R1 is a hydrocarbon group having 1 to 6 carbon atoms, R2 is a hydrocarbon group having 1 to 10 carbon atoms, and may be the same or different. A hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, which may be the same or different from each other, i is an integer of 1 to 4, j is an integer of 0 to 3, and n is 0 to 10 M is an integer of 0 to 10, and m + n ≧ 2.The structural unit represented by the number of repetitions n and the structural unit represented by the number of repetitions m may be mutually aligned. (Although they may be arranged alternately or randomly, a structure having -C (RxRy)-is necessarily provided between them.)

(However, in the said General formula (2), R3 is a C1-C10 hydrocarbon group, and may mutually be same or different. Rp, Rq, Rr, and Rs are a hydrogen atom or carbon number 1. And may be the same or different from each other, k is an integer of 0 to 3, and l is an integer of 0 to 10.)
[2] The resin composition for encapsulating a semiconductor according to [1], wherein the softening point of the epoxy resin (A) is 50 ° C. or more and 80 ° C. or less.
[ 3 ] The semiconductor sealing resin composition according to [1] or [2], wherein R1 in the general formula (1) is a methyl group and i = 2. Resin composition for stopping.
[ 4 ] The semiconductor sealing resin composition according to [1] or [2], wherein the epoxy equivalent of the epoxy resin (A) is 220 g / eq or more and 300 g / eq or less. Resin composition.
[ 5 ] In the semiconductor sealing resin composition according to [1] or [2], the compound having the structure represented by the general formula (1) is synthesized from substituted or unsubstituted phenol, xylene, and formalin. A resin composition for encapsulating a semiconductor, characterized in that:
[ 6 ] A semiconductor device obtained by sealing a semiconductor element with a cured product of the semiconductor sealing resin composition according to any one of [1] to [ 5 ].
[ 7 ] The semiconductor device according to [ 6 ], wherein the semiconductor element is mounted on a lead frame.
[ 8 ] mixing the compound having the structure represented by the general formula (1) and the compound represented by the general formula (2);
Epoxidizing the mixed compound having the structure represented by the general formula (1) and the compound represented by the general formula (2) to obtain an epoxy resin (A);
A process for producing a resin composition for semiconductor encapsulation, comprising: an epoxy resin (A), a phenol resin curing agent (B), and an inorganic filler (C).

(However, in the above general formula (1), R1 is a hydrocarbon group having 1 to 6 carbon atoms, R2 is a hydrocarbon group having 1 to 10 carbon atoms, and may be the same or different. A hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, which may be the same or different from each other, i is an integer of 1 to 4, j is an integer of 0 to 3, and n is 0 to 10 M is an integer of 0 to 10, and m + n ≧ 2.The structural unit represented by the number of repetitions n and the structural unit represented by the number of repetitions m may be mutually aligned. (Although they may be arranged alternately or randomly, a structure having -C (RxRy)-is necessarily provided between them.)

(However, in the said General formula (2), R3 is a C1-C10 hydrocarbon group, and may mutually be same or different. Rp, Rq, Rr, and Rs are a hydrogen atom or carbon number 1. And may be the same or different from each other, k is an integer of 0 to 3, and l is an integer of 0 to 10.)
[ 9 ] In the method for producing a resin composition for encapsulating a semiconductor according to [ 8 ], the softening point of the epoxy resin (A) is from 50 ° C. to 80 ° C. Manufacturing method.
[ 10 ] In the method for producing a resin composition for encapsulating a semiconductor according to [ 8 ] or [ 9 ], R1 in the general formula (1) is a methyl group, and i = 2. A method for producing a semiconductor sealing resin composition.
[ 11 ] In the method for producing a resin composition for encapsulating a semiconductor according to [ 8 ] or [ 9 ], the epoxy equivalent of the epoxy resin (A) is 220 g / eq or more and 300 g / eq or less. The manufacturing method of the resin composition for semiconductor sealing.
[ 12 ] In the method for producing a resin composition for encapsulating a semiconductor according to [ 8 ] or [ 9 ], the compound having a structure represented by the general formula (1) is substituted or unsubstituted phenol, xylene, and A method for producing a resin composition for semiconductor encapsulation, which is synthesized from formalin.

  According to the present invention, a semiconductor sealing resin composition having an excellent balance of fluidity, continuous moldability, handling properties and adhesion, and a semiconductor having excellent reliability obtained by sealing a semiconductor element with a cured product thereof The device can be obtained economically.

It is the figure which showed the cross-sectional structure about an example of the semiconductor device using the resin composition for semiconductor sealing which concerns on this invention. It is the figure which showed the cross-sectional structure about an example of the single-side sealing type semiconductor device using the resin composition for semiconductor sealing which concerns on this invention. It is a GPC chart of the epoxy resin 1 used in the Example. It is a GPC chart of the epoxy resin 2 used in the Example. It is a GPC chart of the epoxy resin 3 used in the Example. It is a GPC chart of the epoxy resin 4 used in the Example. It is a GPC chart of the epoxy resin 5 used in the Example. It is a GPC chart of the epoxy resin 6 used in the Example. It is a GPC chart of the epoxy resin 7 used in the Example. It is a GPC chart of the epoxy resin 8 used in the Example. It is a GPC chart of the epoxy resin 9 used in the Example.

  The resin composition for semiconductor encapsulation of the present invention comprises an epoxy resin (A), a phenol resin-based curing agent (B), and an inorganic filler (C), and the epoxy resin (A) is represented by the general formula ( The epoxy resin which the compound and epihalohydrin which the compound which has the structure represented by 1) reacted, and the epoxy resin which the compound represented by General formula (2) and epihalohydrin reacted are characterized by the above-mentioned. Thereby, the resin composition for semiconductor sealing which is excellent in the balance of fluidity | liquidity, continuous moldability, handling property, and adhesiveness can be obtained. Moreover, the semiconductor device of the present invention is obtained by sealing a semiconductor element with a cured product of the above-described resin composition for encapsulating a semiconductor. Thereby, a highly reliable semiconductor device can be obtained economically. Hereinafter, the present invention will be described in detail. In addition, the numerical range represented by “to” in the present specification includes both the upper limit value and the lower limit value.

[Epoxy resin (A)]
The epoxy resin (A) will be described. In the resin composition for semiconductor encapsulation of the present invention, a compound having a structure represented by the following general formula (1) (phenol resin; referred to as precursor phenol resin 1) is reacted with epihalohydrin as the epoxy resin (A). An epoxy resin (A1) obtained by reacting a compound represented by the following general formula (2) (phenol resin; precursor phenol resin 2) with epihalohydrin: Use.

  The epoxy resin (A1) has a similar skeleton structure as compared with the epoxy resin (A2), and generally exhibits the same characteristics, but further exhibits the following characteristics by having the substituent R1. Since the substituent R1 in the general formula (1) is hydrophobic and has a bulky structure, the resin composition has a characteristic that the water absorption can be reduced and the elastic modulus at the reflow temperature (240 ° C. to 260 ° C.). Can be reduced. Therefore, the solder resistance of the semiconductor sealed package is further improved, and in particular, it has an effect of suppressing the occurrence of internal cracks. Furthermore, since the elastic modulus in the high temperature range is reduced, a quick foam layer can be formed in the combustion test, and better flame resistance can be obtained. Further, as the characteristics of the epoxy resin alone, the bulkiness of the substituent R1 restricts the mobility of the resin skeleton, increases the softening point, and the hydrophobicity of the substituent R1 makes the moisture absorption of the epoxy resin. The phenomenon that the apparent softening point due to is lowered is less likely to occur. As a result, the epoxy resin (A1) has good handling properties in the production process of the resin composition. Furthermore, the epoxy resin (A1) has an effect of reducing and preventing the interfacial peeling between these metals and the resin composition even when the surface is generally a copper oxide surface or a gold plating surface on which adhesion is difficult to maintain. Good solder resistance can also be obtained when this metal lead frame is used. The reason for this is not clear, but one reason is due to the electron donating property of the substituent R1.

  On the other hand, if the epoxy resin (A1) is used excessively, the curing rate decreases, and a cured product having sufficient hardness and strength cannot be obtained. Therefore, when the cured product is released from the sealing mold, a minute defect of the cured resin product occurs in the mold air vent (air venting of 2 to 3 mm in width and about 10 to 100 μm in height). It remains in the part, resulting in poor filling due to insufficient air venting in the subsequent molding, and the continuous moldability is lowered. In addition, sufficient adhesion to the copper surface cannot be obtained. Moreover, depending on the synthesis method, the epoxy resin (A1) tends to have a high molecular weight and a high viscosity, and the fluidity tends to be lowered.

  The epoxy resin (A2) is a known epoxy resin and has good curability, flame resistance, and solder resistance. However, when the molecular weight is lowered to improve the fluidity, the softening point is remarkably lowered, and the resin compositions adhere to each other in the production process of the resin composition or the resin composition adheres to the inside of the apparatus to induce blocking. Therefore, the handling property tends to be lowered.

  The epoxy resin (A) in the present invention combines the epoxy resin (A1) and the epoxy resin (A2) to provide excellent adhesion to copper, copper oxide and gold surfaces, and a good balance between fluidity and continuous moldability. To do.

  The compounding of the epoxy resin (A) includes the method of separately epoxidizing the precursor phenol resins 1 and 2 to obtain the epoxy resin (A1) and the epoxy resin (A2) separately, and the precursor phenol resins 1 and 2 There is a method of mixing and epoxidizing at the same time to obtain a mixture of the epoxy resin (A1) and the epoxy resin (A2). Either method may be taken, but the latter method is preferred. The latter method will be described in detail below.

  The blending of the epoxy resin (A) is preferably performed by previously mixing the precursor phenol resin 1 of the epoxy resin (A1) and the precursor phenol resin 2 of the epoxy resin (A2) and then epoxidizing. This makes it possible to obtain an epoxy resin mixture in which the epoxy resins (A1) and (A2) are uniformly dispersed, rather than epoxidizing the epoxy resins (A1) and (A2) separately and mixing them. A tendency to improve fluidity and flame resistance of the resin composition can be obtained. Moreover, an epoxy resin (A) can suppress blocking at the time of manufacture by including an epoxy resin (A1) and (A2), and can make handling property favorable.

In general, when a phenol resin is epoxidized, the softening point of the resin is lowered. For this reason, when the softening point of the precursor phenol resin is excessively low, the epoxy resin or the resin composition adheres to each other in the epoxidation process or the resin composition manufacturing process, or the epoxy resin or the resin composition in the manufacturing facility. As a result, the handleability deteriorates. Moreover, when using several types of epoxy resins, after compounding each precursor phenol resin individually, it mix | blends into a resin composition normally. Here, when even one kind of epoxy resin having low handling properties is used, there arises a problem that the epoxy resins cannot be mixed well. Conventionally, a technique has been taken in which the softening point of each precursor phenol resin is designed to be high in consideration of a decrease in softening point due to epoxidation and a certain margin. Thus, when the handling property of each epoxy resin is ensured, the margin of the softening point of each epoxy (or precursor phenol) resin is added, and as a result, the fluidity of the resin composition tends to decrease.
On the other hand, in this invention, even if it is a case where the resin of the softening point lower than before is used for the precursor phenol resin 2, since it mixes with the precursor phenol resin 1 previously and epoxidizes, an epoxy resin Mixing of (A1) and epoxy resin (A2) becomes good. Furthermore, it becomes possible to use a plurality of types of epoxy resins with improved fluidity while maintaining handling properties. Moreover, the room for selection of the precursor phenol resin is widened, and the manufacturing margin is improved.

  As a softening point of an epoxy resin (A), 50 degreeC or more is preferable. Thereby, a favorable handling property is obtained. Moreover, as a softening point of an epoxy resin (A), 80 degrees C or less is preferable and 65 degrees C or less is more preferable. By setting it to 80 ° C. or lower, the viscosity is lowered, and the balance between high fluidity and anti-blocking property can be improved. Further, by setting the temperature to 65 ° C. or lower, the viscosity can be further reduced as compared with the conventional case, and the moldability can be improved even in a thin semiconductor package or a semiconductor package in which a plurality of chips are stacked.

  The epoxy equivalent of the epoxy resin (A) is preferably 220 g / eq or more and 300 g / eq or less. By setting the upper limit value of the epoxy equivalent of the epoxy resin (A) to the above value, the resin composition can have good curability and continuous moldability. By setting the lower limit value of the epoxy equivalent of the epoxy resin (A) to the above value, the resin composition can have good solder resistance and flame resistance.

(However, in the above general formula (1), R1 is a hydrocarbon group having 1 to 6 carbon atoms, R2 is a hydrocarbon group having 1 to 10 carbon atoms, and may be the same or different. A hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, which may be the same or different from each other, i is an integer of 1 to 4, j is an integer of 0 to 3, and n is 0 to 10 M is an integer of 0 to 10, and m + n ≧ 2.The structural unit represented by the number of repetitions n and the structural unit represented by the number of repetitions m may be mutually aligned. (Although they may be arranged alternately or randomly, a structure having -C (RxRy)-is necessarily provided between them.)

(However, in the said General formula (2), R3 is a C1-C10 hydrocarbon group, and may mutually be same or different. Rp, Rq, Rr, and Rs are a hydrogen atom or carbon number 1. And may be the same or different from each other, k is an integer of 0 to 3, and l is an integer of 0 to 10.)

  The above -C (RxRy)-indicates that both Rx and Ry are bonded to C. Examples of Rx, Ry, Rp, Rq, Rr and Rs are hydrogen atom, methyl group, ethyl group, propyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, 2-methylbutyl group 3-methylbutyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,2-dimethylbutyl group, 2, 3-dimethylbutyl group, 2,4-dimethylbutyl group, 3,3-dimethylbutyl group, 3,4-dimethylbutyl group, 4,4-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, cyclohexyl group And a phenyl group. These may be the same as or different from each other.

Next, a method for synthesizing the epoxy resins (A1) and (A2) will be described.
There is no limitation in particular about the synthesis | combining method of the epoxy resin (A1) and (A2) used with the resin composition for semiconductor sealing of this invention, You may use a commercial item. For example, as a commercial item of an epoxy resin (A2), Mitsui Chemicals, Inc. E-XLC-3, Nippon Kayaku Co., Ltd. NC-2000, etc. can be mentioned.

  Examples of methods for synthesizing the epoxy resins (A1) and (A2) include the precursor phenol resin 1 and / or the precursor phenol resin 2 dissolved in excess epihalohydrins, and then alkali metals such as sodium hydroxide and potassium hydroxide. Examples thereof include a method of reacting at 50 to 150 ° C., preferably 60 to 120 ° C. for 1 to 10 hours in the presence of a hydroxide. After completion of the reaction, excess epihalohydrin is distilled off, the residue is dissolved in a solvent such as toluene, methyl isobutyl ketone, filtered, washed with water to remove inorganic salts, and then the epoxy resin is removed by distilling off the solvent. (A1) and / or an epoxy resin (A2) can be obtained.

  Epihalohydrin used for the synthesis of epoxy resins (A1) and (A2) includes epichlorohydrin, epibromohydrin, epiiodohydrin, β-methylepichlorohydrin, β-methylepibromohydrin, β-methylepiiodohydrin. Can be mentioned.

[Precursor phenolic resin 1]
Next, a synthesis example of the compound (precursor phenol resin 1) having a structure represented by the general formula (1) will be described.

  The polymerization method of the precursor phenol resin 1 is not particularly limited. For example, a method obtained by polycondensation of a phenol compound and a compound represented by the following general formula (4) (hereinafter referred to as “No. 1), an alkyl-substituted aromatic compound represented by the following general formula (5) and an aldehyde are subjected to a polymerization reaction, and then further condensed with an aldehyde and a phenol compound. And the like (hereinafter, also referred to as “second production method”). These polymerization methods may be appropriately combined for polymerization.

  Among these, the 2nd manufacturing method is preferable at the point that a raw material can be obtained cheaply. Further, commercially available phenol resins having the same structure may be used, and examples thereof include Nicanol GLP manufactured by Mitsubishi Gas Chemical Co., Ltd. and SYSTER GP-90 manufactured by FUDO Co., Ltd.

  Here, in General formula (4), R6 is a C1-C6 hydrocarbon group mutually independently, and b is an integer of 1-4. R7, R8, R9 and R10 are each independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. X is a halogen atom, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. R13 and R14 are each independently a hydrocarbon group having 1 to 6 carbon atoms or a hydrogen atom.

  Here, in General formula (5), R6 is mutually independently a C1-C6 hydrocarbon group, b is an integer of 1-4.

  Examples of the phenol compound include phenol, o-cresol, p-cresol, m-cresol, phenylphenol, ethylphenol, n-propylphenol, iso-propylphenol, t-butylphenol, xylenol, methylpropylphenol, methylbutylphenol, Examples include, but are not limited to, dipropylphenol, dibutylphenol, nonylphenol, mesitol, 2,3,5-trimethylphenol, 2,3,6-trimethylphenol, and the like. Among these, phenol and o-cresol are preferable, and phenol is preferable because it exhibits good reactivity. In the production of the precursor phenol resin 1, these phenol compounds may be used alone or in combination of two or more.

  Examples of the hydrocarbon group having 1 to 6 carbon atoms in R7, R8, R9, R10 and R6 in the compound represented by the general formula (4) used for the production of the precursor phenol resin 1 include a methyl group, Ethyl group, propyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, 2-methylbutyl group, 3-methylbutyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2,4-dimethylbutyl group, 3,3-dimethylbutyl group, Examples include 3,4-dimethylbutyl group, 4,4-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, cyclohexyl group, and phenyl group.

  = CR13R14 (alkylidene group) in the compound represented by the general formula (4) used for the production of the precursor phenol resin 1 includes a methylidene group, an ethylidene group, a propylidene group, an n-butylidene group, an isobutylidene group, t- Butylidene group, n-pentylidene group, 2-methylbutylidene group, 3-methylbutylidene group, t-pentylidene group, n-hexylidene group, 1-methylpentylidene group, 2-methylpentylidene group, 3-methylpentylene Ridene group, 4-methylpentylidene group, 2,2-dimethylbutylidene group, 2,3-dimethylbutylidene group, 2,4-dimethylbutylidene group, 3,3-dimethylbutylidene group, 3,4- Dimethylbutylidene group, 4,4-dimethylbutylidene group, 2-ethylbutylidene group, 1-ethylbutylidene group, and cyclohexane Shiriden group, and the like.

  In X in the compound represented by the general formula (4) used for the production of the precursor phenol resin 1, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy group, ethoxy group, propoxy group, n-butoxy group, isobutoxy group, t-butoxy group, n-pentoxy group, 2-methylbutoxy group, 3-methylbutoxy group, t-pentoxy group, n-hexoxy group, 1-methylpentoxy group, 2-methylpentoxy group, 3-methylpentoxy group, 4-methylpentoxy group, 2,2-dimethylbutoxy group, 2,3- Dimethylbutoxy group, 2,4-dimethylbutoxy group, 3,3-dimethylbutoxy group, 3,4-dimethylbutoxy group, 4,4-dimethylbutoxy group, 2-ethylbutoxy group, 1-ethylbutoxy group, etc. Can be mentioned.

  In the production of the precursor phenol resin 1, the compound represented by the general formula (4) may be used singly or in combination of two or more. Among these, from the viewpoint of a balance between flame resistance and moisture resistance of the resin composition prepared by epoxidation of the precursor phenol resin 1, it is preferable that R6 is a methyl group and b is 1 to 3. When X is a methoxy group, it is preferable because the reaction by-product can be easily distilled off and handled. When X is a halogen atom, the hydrogen halide generated due to the presence of a small amount of moisture is converted to an acid catalyst. Can be used as

  In R6 in the compound represented by the general formula (5) used for the production of the precursor phenol resin 1, the hydrocarbon group having 1 to 6 carbon atoms includes a methyl group, an ethyl group, a propyl group, and an n-butyl group. , Isobutyl group, t-butyl group, n-pentyl group, 2-methylbutyl group, 3-methylbutyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl Group, 4-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2,4-dimethylbutyl group, 3,3-dimethylbutyl group, 3,4-dimethylbutyl group, 4, Examples include 4-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, cyclohexyl group, and phenyl group. Examples of the alkyl-substituted aromatic compound represented by the general formula (5) include toluene, o-xylene, m-xylene, p-xylene, 1,3,5-trimethylbenzene, 1,2,3. -Trimethylbenzene, 1,2,4-trimethylbenzene, ethylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,3,5-triethylbenzene, 1,2,3-triethylbenzene, n-1,2, , 4-triethylbenzene, cumene, o-cymene, m-cymene, p-cymene, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, pentylbenzene, dipentylbenzene, tetramethylbenzene and the like. Among these, toluene, dimethylbenzene, trimethylbenzene, and tetramethylbenzene are preferable from the viewpoint of the raw material price and the balance between flame resistance and moisture resistance of the resin composition prepared by epoxidizing the precursor phenol resin 1. From the viewpoint of fluidity, dimethylbenzene is more preferable. In the production of the precursor phenol resin 1, the compound represented by the general formula (5) may be used alone or in combination of two or more.

  Examples of aldehydes used in the production of the precursor phenol resin 1 include formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, pentylaldehyde, hexylaldehyde, heptane aldehyde, and benzaldehyde. Among these, formaldehyde and paraformaldehyde are preferable from the viewpoint of curability of the resin composition obtained after epoxidation of the precursor phenol resin 1 and raw material costs.

[First production method of precursor phenol resin 1]
The method for synthesizing the precursor phenol resin 1 is not particularly limited. For example, in the case of the first production method, the compound represented by the general formula (4) is 0 with respect to 1 mol of the phenol compound. 0.1 to 0.6 mol, formic acid, oxalic acid, p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, Lewis acid, etc. It is obtained by reacting for 2 to 20 hours while discharging generated gas and moisture out of the system at a temperature of 0 ° C., and distilling off the remaining monomer by a method such as vacuum distillation or steam distillation. Can do.

  The precursor phenol resin 1 obtained by the first production method is a mixture of polymers represented by the following general formula (6), where n is an integer of 0 to 20.

  Here, R61 is mutually independently a C1-C10 hydrocarbon group, and a is an integer of 0-3. R6 is independently a hydrocarbon group having 1 to 6 carbon atoms, and b is an integer of 1 to 4. R7, R8, R9 and R10 are each independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. The terminal of the molecule is a hydrogen atom or a substituted or unsubstituted hydroxyphenyl group.

  The average value of n is 1 to 20, more preferably 3 to 10. When an average value is smaller than the said lower limit, there exists a possibility that the handleability and sclerosis | hardenability of the resin composition obtained by preparing after the epoxidation of the precursor phenol resin 1 may fall. In addition, when the average value is larger than the above upper limit, the viscosity of the precursor phenol resin 1 itself and the epoxy resin (A1) obtained by epoxidizing the precursor phenol resin 1 itself is high. The fluidity of the composition may be reduced. Note that the value of n can be obtained by GPC.

  As a method of adjusting the average value of n of the precursor phenol resin 1 obtained by the first production method, for example, by taking methods such as increasing phenols, decreasing the catalyst, and lowering the reaction temperature, the average value of n Can be reduced.

[Second production method of precursor phenol resin 1]
Moreover, among the synthesis methods of precursor phenol resin 1, in the case of the 2nd manufacturing method, aldehydes are 1-2.5 with respect to 1 mol of alkyl-substituted aromatic compounds represented by General formula (5). Mole, 0.1 to 2.5 mol of a strong acid such as paratoluenesulfonic acid, xylenesulfonic acid or sulfuric acid is added as a catalyst, and the reaction is carried out at a temperature of 100 to 150 ° C. for 0.5 to 5 hours. -Obtain formaldehyde resin. Subsequently, 1 to 20 mol of phenol compound, 0 to 2.5 mol of aldehydes, acidic catalyst 0.005 to oxalic acid, p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, Lewis acid, etc. While adding 0.05 mol and discharging the generated gas out of the system by nitrogen flow at a temperature of 50 to 200 ° C., a co-condensation reaction is carried out for 2 to 20 hours. It can be obtained by distilling off by a method such as distillation.

  The precursor phenol resin 1 obtained by the second production method is a mixture of polymers represented by the following general formula (7).

(However, in the said General formula (7), R1 is mutually independently a C1-C6 hydrocarbon group, i is an integer of 1-4. R2 is mutually independent, C1 Is a hydrocarbon group having from 1 to 10, and j is an integer from 0 to 3. Rt, Ru, Rv and Rw are each independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and n is 0. Is an integer of -20, and m is an integer of 0-20.

  Examples of Rt, Ru, Rv and Rw in the compound represented by the general formula (7) include hydrogen atom, methyl group, ethyl group, propyl group, n-butyl group, isobutyl group, t-butyl group, n -Pentyl group, 2-methylbutyl group, 3-methylbutyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2, 2-dimethylbutyl group, 2,3-dimethylbutyl group, 2,4-dimethylbutyl group, 3,3-dimethylbutyl group, 3,4-dimethylbutyl group, 4,4-dimethylbutyl group, 2-ethylbutyl group , 1-ethylbutyl group, cyclohexyl group, phenyl group and the like. These may be the same as or different from each other.

  The precursor phenol resin 1 obtained by the second production method is a polymer represented by the general formula (7), wherein n is an integer of 0 to 20, and m is an integer of 0 to 20, and the repetition number n. The structural unit represented by the above and the structural unit represented by the number of repetitions m are alternately combined, block-shaped, irregularly-bonded, regularly-bonded, etc. It's okay.

  When the values of n and m are described as average values, the average value of n is 1 to 10, more preferably 2 to 4, and the average value of m is 0.2 to 10, more preferably 0.8 to 4. is there. The average value of m + n is preferably 2-15, and more preferably 2-10. When the average value of n is smaller than the said lower limit, there exists a possibility that the flame resistance, moisture resistance, and adhesiveness of the resin composition prepared after epoxidation of the precursor phenol resin 1 may fall. When the average value of n is larger than the upper limit, the fluidity of the resin composition prepared after epoxidation of the precursor phenol resin 1 may be lowered. Moreover, when the average value of m is smaller than the said lower limit, there exists a possibility that the sclerosis | hardenability and solder crack resistance of the resin composition obtained by preparing after the epoxidation of the precursor phenol resin 1 may fall. When the average value of m is larger than the above upper limit value, the fluidity of the resin composition obtained after the epoxidation of the precursor phenol resin 1 may be lowered. Moreover, when the average value of m + n is smaller than the said lower limit, there exists a possibility that sclerosis | hardenability and intensity | strength may fall. When the average value of m + n is larger than the above upper limit value, the fluidity of the resin composition obtained after the epoxidation of the precursor phenol resin 1 may be lowered. In addition, the value of n and m can be calculated by the intensity ratio of the signal derived from the hydroxyl group and the signal derived from the alkyl substituent contained in the skeleton by H-NMR or C-NMR measurement. Similarly, the value corresponding to n and m in the epoxy resin obtained by epoxidizing the compound of the general formula (7) is also a signal derived from a hydroxyl group contained in the skeleton by H-NMR or C-NMR measurement. And the intensity ratio of signals derived from alkyl substituents.

Here, as a method of adjusting the average value of n in the second manufacturing method,
(I) In the reaction between the alkyl-substituted aromatic compound and the aldehyde, the amount of the aldehyde is increased to such an extent that gelation does not occur, the reaction temperature is increased, and the amount of the catalyst is increased
(Ii) increasing the amount of formaldehyde in the reaction between the aromatic hydrocarbon-formaldehyde resin and the phenol compound;
Thus, the average value of n can be increased.

In addition, as a method of adjusting the average value of m in the second manufacturing method,
(Iii) In the reaction of an aromatic hydrocarbon-formaldehyde resin with a phenol compound, increase the average value of m by a method such as decreasing the compounding ratio of phenol compound / aldehydes, increasing the reaction temperature, or increasing the amount of catalyst. Can do.

  As a method of adjusting the average value of m + n, it can be adjusted by appropriately combining the methods (i) to (iii) described above.

  In the precursor phenol resin 1 obtained by the second production method, there are 1 to 2 nuclear components (components where n = m = 0, components where n = 0 and m = 1, components where n = 1 and m = 0) May be included. About these content rates, the content calculated | required by the area method of a gel permeation chromatograph (GPC) has preferable 20% or less, More preferably, it is 15% or less. When the amount of 1 to 2 nuclei is larger than the above upper limit, the solder resistance and curability of the resin composition obtained after epoxidation are lowered. As a method for adjusting the above-mentioned 1-2 nuclei, the 1-2 nuclei component can be reduced in the precursor phenol resin 1 by a known method such as steam distillation or vacuum distillation.

[Precursor phenolic resin 2]
Next, a synthesis example of the phenol resin (precursor phenol resin 2) represented by the general formula (2) will be described.

  Although it does not specifically limit as a polymerization method of the precursor phenol resin 2, For example, it can obtain by polycondensing the above-mentioned phenol compound and the compound represented by following General formula (3). Further, commercially available phenol resins having the same structure may be used, and examples thereof include MEH-7800SS manufactured by Meiwa Kasei Co., Ltd., XLC-3L manufactured by Mitsui Chemicals, Inc., and XLC-4L manufactured by Mitsui Chemicals.

  Here, in General formula (3), R4, R5, R15, and R16 are a hydrogen atom or a C1-C6 hydrocarbon group mutually independently. X is a halogen atom, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. R11 and R12 are each independently a hydrocarbon group having 1 to 5 carbon atoms or a hydrogen atom.

  Examples of the hydrocarbon group having 1 to 6 carbon atoms in R4, R5, R15 and R16 in the compound represented by the general formula (3) used for the production of the precursor phenol resin 2 include a methyl group, an ethyl group, Propyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, 2-methylbutyl group, 3-methylbutyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methyl Pentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2,4-dimethylbutyl group, 3,3-dimethylbutyl group, 3,4 -A dimethylbutyl group, 4, 4- dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, a cyclohexyl group, a phenyl group, etc. are mentioned.

  = CR11R12 (alkylidene group) in the compound represented by the general formula (3) used for the production of the precursor phenol resin 2 includes methylidene group, ethylidene group, propylidene group, n-butylidene group, isobutylidene group, t- Butylidene group, n-pentylidene group, 2-methylbutylidene group, 3-methylbutylidene group, t-pentylidene group, n-hexylidene group, 1-methylpentylidene group, 2-methylpentylidene group, 3-methylpentylene Ridene group, 4-methylpentylidene group, 2,2-dimethylbutylidene group, 2,3-dimethylbutylidene group, 2,4-dimethylbutylidene group, 3,3-dimethylbutylidene group, 3,4- Dimethylbutylidene group, 4,4-dimethylbutylidene group, 2-ethylbutylidene group, 1-ethylbutylidene group, and cyclohexane Shiriden group, and the like.

  The method for synthesizing the precursor phenol resin 2 is not particularly limited. For example, in the first production method of the precursor phenol resin 1, the compound represented by the general formula (3) is used instead of the compound represented by the general formula (4). The precursor phenol resin 2 can be obtained by using this compound.

  In the resin composition for semiconductor encapsulation of the present invention, other epoxy resins can be used as long as the effect of using the epoxy resin (A) is not impaired.

For example, crystalline epoxy resins such as biphenyl type epoxy resins, bisphenol type epoxy resins, stilbene type epoxy resins, dihydroanthracenediol type epoxy resins; novolac type epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins; Polyfunctional epoxy resins such as methane type epoxy resins and alkyl-modified triphenol methane type epoxy resins; Aralkyl type epoxy resins such as phenol aralkyl type epoxy resins having a biphenylene skeleton; Dihydroxynaphthalene type epoxy resins, hydroxynaphthalene and / or dihydroxynaphthalene Epoxy resin obtained by glycidyl etherification of dimer, naphthol aralkyl type epoxy resin having phenylene skeleton, hydroxyna Naphthol-type epoxies such as resins obtained by epoxidizing novolak-type naphthol resins obtained by reacting naphthols such as tarene or dihydroxynaphthalene with aldehyde compounds such as formaldehyde, acetaldehyde, benzaldehyde, salicylaldehyde in the presence of an acid catalyst. Resin; Novolac type epoxy resin having methoxynaphthalene skeleton; Triazine core-containing epoxy resin such as triglycidyl isocyanurate and monoallyl diglycidyl isocyanurate; Bridged cyclic hydrocarbon compound modified phenol type such as dicyclopentadiene modified phenol type epoxy resin Although an epoxy resin is mentioned, it is not limited to these. These epoxy resins preferably do not contain Na ⁺ ions or Cl ⁻ ions, which are ionic impurities, as much as possible from the viewpoint of moisture resistance reliability of the obtained resin composition for semiconductor encapsulation. Moreover, it is preferable that the epoxy equivalent of an epoxy resin is 100 g / eq or more and 500 g / eq or less from a sclerosing | hardenable viewpoint of the resin composition for semiconductor sealing.

  Among them, biphenyl type epoxy resins and bisphenol type epoxy resins are preferable from the viewpoint of fluidity, and phenol aralkyl type epoxy resins having a biphenylene skeleton and novolac type epoxy resins having a methoxynaphthalene skeleton are preferable from the viewpoint of solder resistance. . From the viewpoint of low warpage in a single-side sealed semiconductor device, a triphenolmethane type epoxy resin, a naphthol aralkyl type epoxy resin having a phenylene skeleton, a dihydroanthracenediol type epoxy resin, and the like are preferable. If such an epoxy resin is used in combination with the epoxy resin (A), the balance of handling property, solder resistance, flame resistance and continuous formability is stably improved while improving fluidity. The effect is obtained.

  In the case where such other epoxy is used in combination, the lower limit of the blending ratio of the epoxy resin (A) is preferably 30% by mass or more, and 50% by mass or more with respect to the total epoxy resin. Is more preferable, and 70% by mass or more is particularly preferable. When the blending ratio is within the above range, the fluidity and handling properties of the resin composition are compatible, and the effect of improving the balance of continuous moldability and adhesion can be obtained.

  In addition, the phenol resin as a hardening | curing agent mentioned later and an epoxy resin are equivalent ratio (EP) / (OH) of the number of epoxy groups (EP) of all the epoxy resins, and the number of phenolic hydroxyl groups (OH) of all the phenol resins. However, it is preferable to mix | blend so that it may become 0.8 or more and 1.3 or less. When the equivalent ratio is within the above range, sufficient curing characteristics can be obtained when the resulting resin composition is molded.

[Phenolic resin curing agent (B)]
Next, the phenol resin curing agent (B) will be described. The phenol resin-based curing agent (B) is a monomer, oligomer or polymer in general having two or more phenolic hydroxyl groups in one molecule, and its molecular weight and molecular structure are not particularly limited. For example, a phenol novolak resin , Novolak resins such as cresol novolac resin and naphthol novolak resin; polyfunctional phenol resins such as triphenolmethane phenol resin; modified phenol resins such as terpene modified phenol resin and dicyclopentadiene modified phenol resin; phenylene skeleton and / or Aralkyl type resins such as phenol aralkyl resins having a biphenylene skeleton, phenylene and / or naphthol aralkyl resins having a biphenylene skeleton; and bisphenol compounds such as bisphenol A and bisphenol F The compound having the structure represented by the general formula (1) used as the precursor phenol resin 1 of the epoxy resin (A1) may be used, and these may be used alone or in combination of two or more. May be. Such a phenol resin curing agent (B) provides a good balance of flame resistance, moisture resistance, electrical properties, curability, storage stability, and the like. Particularly, from the viewpoint of curability, the hydroxyl equivalent is preferably 90 g / eq or more and 250 g / eq or less.

  In the present invention, other curing agents can be used in combination. Examples of the curing agent that can be used in combination include a polyaddition type curing agent, a catalyst type curing agent, and a condensation type curing agent.

  Examples of the polyaddition type curing agent include aliphatic polyamines such as diethylenetriamine (DETA), triethylenetetramine (TETA), and metaxylenediamine (MXDA), diaminodiphenylmethane (DDM), m-phenylenediamine (MPDA), and diamino. In addition to aromatic polyamines such as diphenylsulfone (DDS), polyamine compounds including dicyandiamide (DICY), organic acid dihydralazide, and the like; alicyclic acid anhydrides such as hexahydrophthalic anhydride (HHPA) and methyltetrahydrophthalic anhydride (MTHPA) , Acid anhydrides including aromatic acid anhydrides such as trimellitic anhydride (TMA), pyromellitic anhydride (PMDA), benzophenone tetracarboxylic acid (BTDA); novolac-type phenolic resin, phenol poly Polyphenol compounds such as chromatography; polysulfide, thioester, polymercaptan compounds such as thioethers; isocyanate prepolymer, isocyanate compounds such as blocked isocyanate; and organic acids such as carboxylic acid-containing polyester resins.

  Examples of the catalyst-type curing agent include tertiary amine compounds such as benzyldimethylamine (BDMA) and 2,4,6-trisdimethylaminomethylphenol (DMP-30); 2-methylimidazole, 2-ethyl-4 -Imidazole compounds such as methylimidazole (EMI24); Lewis acids such as BF3 complexes.

  Examples of the condensation type curing agent include urea resins such as methylol group-containing urea resins; melamine resins such as methylol group-containing melamine resins.

  In the case where such other curing agents are used in combination, the lower limit of the blending ratio of the phenol resin curing agent (B) is preferably 20% by mass or more, and 30% by mass with respect to the total curing agent. More preferably, it is more preferably 50% by mass or more. When the blending ratio is within the above range, good fluidity can be exhibited while maintaining flame resistance and solder resistance.

  The lower limit of the blending ratio of the entire curing agent is not particularly limited, but is preferably 0.8% by mass or more and more preferably 1.5% by mass or more in the total resin composition. preferable. When the lower limit value of the blending ratio is within the above range, good curability can be obtained. Further, the upper limit of the blending ratio of the entire curing agent is not particularly limited, but is preferably 10% by mass or less and more preferably 8% by mass or less in the entire resin composition. . When the upper limit of the blending ratio is within the above range, good solder resistance can be obtained.

[Inorganic filler (C)]
As an inorganic filler (C) used for the resin composition for semiconductor encapsulation of the present invention, an inorganic filler generally used in this field can be used. Examples thereof include fused silica, spherical silica, crystalline silica, alumina, silicon nitride, and aluminum nitride. The particle size of the inorganic filler is desirably 0.01 μm or more and 150 μm or less from the viewpoint of filling properties in the mold cavity.

  The amount of the inorganic filler (C) in the resin composition for semiconductor encapsulation is preferably 80% by mass or more, more preferably 83% by mass or more, based on the total mass of the resin composition for semiconductor encapsulation. Yes, more preferably 86% by mass or more. When the lower limit value is within the above range, an increase in moisture absorption and a decrease in strength due to curing of the resulting resin composition can be reduced, and therefore a cured product having good solder crack resistance can be obtained. Moreover, the amount of the inorganic filler in the resin composition for semiconductor encapsulation is preferably 93% by mass or less, more preferably 91% by mass or less, with respect to the total mass of the resin composition for semiconductor encapsulation. More preferably, it is 90 mass% or less. When the upper limit is within the above range, the resulting resin composition has good fluidity and good moldability.

  In addition, when using inorganic flame retardants such as metal hydroxides such as aluminum hydroxide and magnesium hydroxide, zinc borate, zinc molybdate and antimony trioxide described later, these inorganic flame retardants and the above It is desirable that the total amount of the inorganic filler is within the above range.

[Other ingredients]
The semiconductor sealing resin composition of the present invention may contain a curing accelerator (D). The curing accelerator (D) only needs to accelerate the reaction between the epoxy group of the epoxy resin and the hydroxyl group of the phenol resin curing agent (B), and a generally used curing accelerator (D) is used. it can.

  Specific examples of the curing accelerator (D) include phosphorus atom-containing compounds such as organic phosphines, tetra-substituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, adducts of phosphonium compounds and silane compounds; Examples thereof include nitrogen atom-containing compounds such as 1,8-diazabicyclo (5,4,0) undecene-7, benzyldimethylamine, and 2-methylimidazole. Among these, a phosphorus atom-containing compound is preferable from the viewpoint of curability, and from the viewpoint of balance between fluidity and curability, a tetra-substituted phosphonium compound, a phosphobetaine compound, an adduct of a phosphine compound and a quinone compound, a phosphonium compound A catalyst having latency such as an adduct of silane compound and silane compound is more preferable. In view of fluidity, tetra-substituted phosphonium compounds are particularly preferable. From the viewpoint of solder resistance, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds are particularly preferable, and in view of latent curability. An adduct of a phosphonium compound and a silane compound is particularly preferable. Further, from the viewpoint of continuous moldability, a tetra-substituted phosphonium compound is preferable.

  Examples of the organic phosphine that can be used in the resin composition for encapsulating a semiconductor of the present invention include a first phosphine such as ethylphosphine and phenylphosphine; a second phosphine such as dimethylphosphine and diphenylphosphine; trimethylphosphine, triethylphosphine, and tributyl. Third phosphine such as phosphine and triphenylphosphine can be used.

  Examples of the tetra-substituted phosphonium compound that can be used in the semiconductor sealing resin composition of the present invention include compounds represented by the following general formula (8).

  In the general formula (8), P represents a phosphorus atom, R17, R18, R19 and R20 each independently represents an aromatic group or an alkyl group, and A represents a functional group selected from a hydroxyl group, a carboxyl group and a thiol group. Represents an anion of an aromatic organic acid having at least one of the groups in the aromatic ring, and AH is an aromatic organic having at least one functional group selected from a hydroxyl group, a carboxyl group, and a thiol group in the aromatic ring Represents an acid, x and y are integers of 1 to 3, z is an integer of 0 to 3, and x = y.

  Although the compound represented by General formula (8) is obtained as follows, for example, it is not limited to this. First, a tetra-substituted phosphonium halide, an aromatic organic acid and a base are mixed in an organic solvent and mixed uniformly to generate an aromatic organic acid anion in the solution system. Subsequently, when water is added, the compound represented by the general formula (8) can be precipitated. In the compound represented by the general formula (8), R17, R18, R19, and R20 bonded to the phosphorus atom are phenyl groups and AH is bonded to the phosphorus atom from the viewpoint of excellent balance between the yield at the time of synthesis and the curing acceleration effect. A compound having a hydroxyl group in an aromatic ring, that is, a phenol compound, and A is preferably an anion of the phenol compound.

  Examples of the phosphobetaine compound that can be used in the semiconductor sealing resin composition of the present invention include compounds represented by the following general formula (9).

  In General formula (9), X1 represents a C1-C3 alkyl group, Y1 represents a hydroxyl group, f is an integer of 0-5, g is an integer of 0-4.

  The compound represented by the general formula (9) is obtained, for example, as follows. First, it is obtained through a step of bringing a triaromatic substituted phosphine, which is a third phosphine, into contact with a diazonium salt and replacing the triaromatic substituted phosphine with a diazonium group of the diazonium salt. However, the present invention is not limited to this.

  Examples of the adduct of a phosphine compound and a quinone compound that can be used in the resin composition for semiconductor encapsulation of the present invention include compounds represented by the following general formula (10).

  In General Formula (10), P represents a phosphorus atom, R21, R22, and R23 each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, and R24, R25, and R26 independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R24 and R25 may be bonded to each other to form a ring.

  Examples of the phosphine compound used as an adduct of a phosphine compound and a quinone compound include an aromatic ring such as triphenylphosphine, tris (alkylphenyl) phosphine, tris (alkoxyphenyl) phosphine, trinaphthylphosphine, and tris (benzyl) phosphine. Those having a substituent such as a substituent or an alkyl group or an alkoxyl group are preferred, and examples of the substituent such as an alkyl group and an alkoxyl group include those having 1 to 6 carbon atoms. From the viewpoint of availability, triphenylphosphine is preferable.

  In addition, examples of the quinone compound used for the adduct of the phosphine compound and the quinone compound include o-benzoquinone, p-benzoquinone, and anthraquinones. Among them, p-benzoquinone is preferable from the viewpoint of storage stability.

  As a method for producing an adduct of a phosphine compound and a quinone compound, the adduct can be obtained by contacting and mixing in a solvent capable of dissolving both organic tertiary phosphine and benzoquinone. The solvent is preferably a ketone such as acetone or methyl ethyl ketone, which has low solubility in the adduct. However, the present invention is not limited to this.

  In the compound represented by the general formula (10), R21, R22 and R23 bonded to the phosphorus atom are phenyl groups, and R24, R25 and R26 are hydrogen atoms, that is, 1,4-benzoquinone and triphenyl A compound to which phosphine has been added is preferred in that it reduces the thermal elastic modulus of the cured product of the resin composition.

  Examples of the adduct of a phosphonium compound and a silane compound that can be used in the semiconductor sealing resin composition of the present invention include compounds represented by the following formula (11).

  In the general formula (11), P represents a phosphorus atom, and Si represents a silicon atom. R27, R28, R29 and R30 each independently represent an organic group having an aromatic ring or a heterocyclic ring, or an aliphatic group, and X2 is an organic group bonded to the groups Y2 and Y3. X3 is an organic group bonded to the groups Y4 and Y5. Y2 and Y3 represent a group formed by releasing a proton from a proton donating group, and groups Y2 and Y3 in the same molecule are bonded to a silicon atom to form a chelate structure. Y4 and Y5 represent a group formed by releasing a proton from a proton donating group, and groups Y4 and Y5 in the same molecule are bonded to a silicon atom to form a chelate structure. X2 and X3 may be the same or different from each other, and Y2, Y3, Y4, and Y5 may be the same or different from each other. Z1 is an organic group having an aromatic ring or a heterocyclic ring, or an aliphatic group.

  In the general formula (11), as R27, R28, R29 and R30, for example, phenyl group, methylphenyl group, methoxyphenyl group, hydroxyphenyl group, naphthyl group, hydroxynaphthyl group, benzyl group, methyl group, ethyl group, n-butyl group, n-octyl group, cyclohexyl group, and the like. Among these, an aromatic group having a substituent such as phenyl group, methylphenyl group, methoxyphenyl group, hydroxyphenyl group, hydroxynaphthyl group, or the like. A substituted aromatic group is more preferred.

  Moreover, in General formula (11), X2 is an organic group couple | bonded with Y2 and Y3. Similarly, X3 is an organic group bonded to the groups Y4 and Y5. Y2 and Y3 are groups formed by proton-donating groups releasing protons, and groups Y2 and Y3 in the same molecule are combined with a silicon atom to form a chelate structure. Similarly, Y4 and Y5 are groups formed by proton-donating groups releasing protons, and groups Y4 and Y5 in the same molecule are combined with a silicon atom to form a chelate structure. The groups X2 and X3 may be the same or different from each other, and the groups Y2, Y3, Y4, and Y5 may be the same or different from each other. The groups represented by -Y2-X2-Y3- and Y4-X3-Y5- in the general formula (11) are composed of groups in which a proton donor releases two protons. Examples of proton donors include catechol, pyrogallol, 1,2-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,2′-biphenol, 1,1′-bi-2-naphthol, salicylic acid, Examples include 1-hydroxy-2-naphthoic acid, 3-hydroxy-2-naphthoic acid, chloranilic acid, tannic acid, 2-hydroxybenzyl alcohol, 1,2-cyclohexanediol, 1,2-propanediol, and glycerin. Among these, catechol, 1,2-dihydroxynaphthalene, and 2,3-dihydroxynaphthalene are more preferable from the viewpoint of easy availability of raw materials and a curing acceleration effect.

  Z1 in the general formula (11) represents an organic group or an aliphatic group having an aromatic ring or a heterocyclic ring, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, and a hexyl group. Reactions such as aliphatic hydrocarbon groups such as octyl group and aromatic hydrocarbon groups such as phenyl group, benzyl group, naphthyl group and biphenyl group, glycidyloxypropyl group, mercaptopropyl group, aminopropyl group and vinyl group Among them, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and a biphenyl group are more preferable from the viewpoint of thermal stability.

  As a method for producing an adduct of a phosphonium compound and a silane compound, a silane compound such as phenyltrimethoxysilane and a proton donor such as 2,3-dihydroxynaphthalene are added to a flask containing methanol and dissolved, and then room temperature. Sodium methoxide-methanol solution is added dropwise with stirring. Furthermore, when a solution prepared by dissolving a tetra-substituted phosphonium halide such as tetraphenylphosphonium bromide in methanol in methanol is added dropwise with stirring at room temperature, crystals are precipitated. The precipitated crystals are filtered, washed with water, and vacuum dried to obtain an adduct of a phosphonium compound and a silane compound. However, it is not limited to this.

  The lower limit of the blending ratio of the curing accelerator (D) that can be used in the semiconductor sealing resin composition of the present invention is preferably 0.1% by mass or more in the total resin composition. Sufficient curability can be obtained when the lower limit of the blending ratio of the curing accelerator (D) is within the above range. Moreover, it is preferable that the upper limit of the mixture ratio of a hardening accelerator (D) is 1 mass% or less in all the resin compositions. Sufficient fluidity | liquidity can be obtained as the upper limit of the mixture ratio of a hardening accelerator (D) is in the said range.

  In the present invention, a compound (E) in which a hydroxyl group is bonded to each of two or more adjacent carbon atoms constituting an aromatic ring (hereinafter, also simply referred to as “compound (E)”) can be used. The compound (E) in which a hydroxyl group is bonded to each of two or more adjacent carbon atoms constituting an aromatic ring can be used to cause a crosslinking reaction between the epoxy resin (A) and the phenol resin-based curing agent (B). Even when a phosphorus atom-containing curing accelerator having no latent property is used as the curing accelerator (D) to be promoted, the reaction during the melt-kneading of the resin composition can be suppressed, and the resin can be stabilized. A composition can be obtained. The compound (E) also has an effect of lowering the melt viscosity of the resin composition and improving fluidity. As the compound (E), a monocyclic compound represented by the following general formula (12) or a polycyclic compound represented by the following general formula (13) can be used. You may have the substituent of.

  In General Formula (12), when one of R31 and R35 is a hydroxyl group and one is a hydroxyl group, the other is a hydrogen atom, a hydroxyl group or a substituent other than a hydroxyl group, and R32, R33, and R34 are a hydrogen atom, It is a hydroxyl group or a substituent other than a hydroxyl group.

  In General Formula (13), when one of R36 and R42 is a hydroxyl group and one is a hydroxyl group, the other is a hydrogen atom, a hydroxyl group or a substituent other than a hydroxyl group, and R37, R38, R39, R40, and R41 are , A hydrogen atom, a hydroxyl group or a substituent other than a hydroxyl group.

  Specific examples of the monocyclic compound represented by the general formula (12) include catechol, pyrogallol, gallic acid, gallic acid ester, and derivatives thereof. Specific examples of the polycyclic compound represented by the general formula (13) include 1,2-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, and derivatives thereof. Among these, a compound in which a hydroxyl group is bonded to each of two adjacent carbon atoms constituting an aromatic ring is preferable because of easy control of fluidity and curability. In consideration of volatilization in the kneading step, it is more preferable that the mother nucleus is a compound having a low volatility and a highly stable weighing naphthalene ring. In this case, specifically, the compound (E) can be a compound having a naphthalene ring such as 1,2-dihydroxynaphthalene, 2,3-dihydroxynaphthalene and derivatives thereof. These compounds (E) may be used individually by 1 type, or may use 2 or more types together.

  The lower limit of the compounding ratio of the compound (E) is preferably 0.01% by mass or more, more preferably 0.03% by mass or more, and particularly preferably 0.05% by mass or more in the total resin composition. It is. When the lower limit value of the compounding ratio of the compound (E) is within the above range, a sufficient viscosity reduction and fluidity improvement effect of the resin composition can be obtained. Further, the upper limit of the compounding ratio of the compound (E) is preferably 1% by mass or less, more preferably 0.8% by mass or less, and particularly preferably 0.5% by mass or less in the total resin composition. is there. When the upper limit value of the compounding ratio of the compound (E) is within the above range, there is little possibility of causing a decrease in the curability of the resin composition and a decrease in the physical properties of the cured product.

  In the resin composition for semiconductor encapsulation of the present invention, a coupling agent (F) such as a silane coupling agent is added to improve the adhesion between the epoxy resin (A) and the inorganic filler (C). Can do. Examples thereof include, but are not limited to, epoxy silane, amino silane, ureido silane, mercapto silane, and the like, and react between the epoxy resin (A) and the inorganic filler (C) to form an epoxy resin ( Any material that improves the interfacial strength between A) and the inorganic filler (C) may be used. Moreover, a silane coupling agent can also raise the effect of the compound (E) of reducing the melt viscosity of a resin composition and improving fluidity | liquidity by using together with the above-mentioned compound (E).

  Examples of the epoxy silane include γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, β- (3,4 epoxycyclohexyl) ethyltrimethoxysilane. Etc. Examples of the aminosilane include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, and N-β (aminoethyl) γ-aminopropyl. Methyldimethoxysilane, N-phenylγ-aminopropyltriethoxysilane, N-phenylγ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, N-6- (aminohexyl) 3 -Aminopropyltrimethoxysilane, N- (3- (trimethoxysilylpropyl) -1,3-benzenedimethanane, etc. In addition, examples of ureidosilane include γ-ureidopropyltriethoxysilane, hexa Methyl disilazane, etc. of aminosilane It may be used as a latent aminosilane coupling agent in which a primary amino moiety is protected by reacting with a ketone or aldehyde, and examples of mercaptosilane include γ-mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane. In addition to silane coupling agents that exhibit the same functions as mercaptosilane coupling agents by thermal decomposition such as bis (3-triethoxysilylpropyl) tetrasulfide and bis (3-triethoxysilylpropyl) disulfide These silane coupling agents may be pre-hydrolyzed, and these silane coupling agents may be used alone or in combination of two or more. Good.

  In the case of the present invention, mercaptosilane is preferable from the viewpoint of the balance between solder resistance and continuous formability, and aminosilane is preferable from the viewpoint of fluidity, and is suitable for organic members such as polyimide on the silicon chip surface and solder resist on the substrate surface. Epoxysilane is preferable from the viewpoint of adhesion.

  The lower limit of the blending ratio of the coupling agent (F) such as a silane coupling agent that can be used in the resin composition for semiconductor encapsulation of the present invention is preferably 0.01% by mass or more in the total resin composition, More preferably, it is 0.05 mass% or more, Most preferably, it is 0.1 mass% or more. If the lower limit of the blending ratio of the coupling agent (F) such as a silane coupling agent is within the above range, the interface strength between the epoxy resin (A) and the inorganic filler (C) does not decrease, and the semiconductor Good solder crack resistance in the apparatus can be obtained. Moreover, as an upper limit of the mixture ratio of coupling agents (F), such as a silane coupling agent, 1 mass% or less is preferable in all the resin compositions, More preferably, it is 0.8 mass% or less, Most preferably, it is 0.8. 6% by mass or less. If the upper limit of the blending ratio of the coupling agent (F) such as a silane coupling agent is within the above range, the interface strength between the epoxy resin (A) and the inorganic filler (C) does not decrease, and the semiconductor Good solder crack resistance in the apparatus can be obtained. Moreover, if the blending ratio of the coupling agent (F) such as a silane coupling agent is within the above range, the water absorption of the cured product of the resin composition does not increase, and good solder crack resistance in a semiconductor device. Can be obtained.

  In the resin composition for semiconductor encapsulation of the present invention, an inorganic flame retardant (G) can be added in order to improve flame retardancy. Among these, a metal hydroxide or a composite metal hydroxide that inhibits the combustion reaction by dehydrating and absorbing heat during combustion is preferable in that the combustion time can be shortened. Examples of the metal hydroxide include aluminum hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, and zirconia hydroxide. The composite metal hydroxide is a hydrotalcite compound containing two or more metal elements, wherein at least one metal element is magnesium, and the other metal elements are calcium, aluminum, tin, titanium, iron Any metal element selected from cobalt, nickel, copper, or zinc may be used, and as such a composite metal hydroxide, a magnesium hydroxide / zinc solid solution is easily available on the market. Of these, aluminum hydroxide and magnesium hydroxide / zinc solid solution are preferable from the viewpoint of the balance between solder resistance and continuous moldability. An inorganic flame retardant (G) may be used independently or may be used 2 or more types. Further, for the purpose of reducing the influence on the continuous moldability, a surface treatment may be performed with a silicon compound such as a silane coupling agent or an aliphatic compound such as wax.

  In the semiconductor sealing resin composition of the present invention, in addition to the components described above, colorants such as carbon black, bengara and titanium oxide; natural waxes such as carnauba wax; synthetic waxes such as polyethylene wax; stearic acid and zinc stearate Release agents such as higher fatty acids and their metal salts or paraffin; low-stress additives such as silicone oil and silicone rubber may be appropriately blended.

  The resin composition for semiconductor encapsulation of the present invention uses an epoxy resin (A), a phenol resin curing agent (B), an inorganic filler (C), and other additives as described above, for example, using a mixer or the like. The mixture is uniformly mixed at room temperature, and then melt-kneaded using a kneader such as a heating roll, a kneader or an extruder, if necessary, and then cooled and pulverized as necessary to obtain a desired degree of dispersion. And fluidity can be adjusted.

[Semiconductor device]
Next, the semiconductor device of the present invention will be described. As a method for producing a semiconductor device using the resin composition for semiconductor encapsulation of the present invention, for example, after a lead frame or a circuit board on which a semiconductor element is mounted is placed in a mold cavity, the resin for semiconductor encapsulation is used. The method of sealing this semiconductor element by shape | molding and hardening a composition with shaping | molding methods, such as a transfer mold, a compression mold, and an injection mold, is mentioned.

  Examples of the semiconductor element to be sealed include, but are not limited to, an integrated circuit, a large-scale integrated circuit, a transistor, a thyristor, a diode, and a solid-state imaging element.

  The material of the lead frame is not particularly limited, and copper, copper alloy, 42 alloy (Fe-42% Ni alloy) or the like can be used. The surface of the lead frame is plated with, for example, pure copper strike plating, silver plating (mainly the wire joint at the tip of the inner lead), or nickel / palladium / gold multi-layer plating (PPF (Palladium Pre-Plated Frame)). May be. As a result, copper, copper alloy, gold or 42 alloy exists on the surface of the lead frame where adhesion is a problem. Conventionally, from the viewpoint of adhesion to the lead frame, the semiconductor sealing resin composition was selected and used in accordance with the type of metal of the lead frame. Since the component (A1) is contained, there is room for selection of the type of the metal layer on the surface of the lead frame, and the process margin is improved.

  As a form of the obtained semiconductor device, for example, dual in-line package (DIP), chip carrier with plastic lead (PLCC), quad flat package (QFP), low profile quad flat package ( LQFP), Small Outline Package (SOP), Small Outline J Lead Package (SOJ), Thin Small Outline Package (TSOP), Thin Quad Flat Package (TQFP), Tape Carrier Package ( TCP), ball grid array (BGA), chip size package (CSP), matrix array package ball grid array (MAPBGA), chip stacked chip support 'S package and the like, but not limited thereto.

  Moreover, since the component (A1) contained in the epoxy resin (A) of the resin composition for semiconductor encapsulation has R1 (a hydrocarbon group having 1 to 6 carbon atoms), the hygroscopicity can be lowered. Therefore, the solder resistance when an organic substrate such as BGA is used can be improved.

  A semiconductor device in which a semiconductor element is encapsulated by a molding method such as transfer molding of a resin composition for encapsulating a semiconductor is used as it is or at a temperature of about 80 ° C. to 200 ° C. for about 10 minutes to 10 hours. After this resin composition is completely cured, it is mounted on an electronic device or the like.

  FIG. 1 is a view showing a cross-sectional structure of an example of a semiconductor device using the resin composition for encapsulating a semiconductor according to the present invention. The semiconductor element 1 is fixed on the die pad 3 via the die bond material cured body 2. The electrode pad of the semiconductor element 1 and the lead frame 5 are connected by a wire 4. The semiconductor element 1 is sealed with a cured body 6 of a semiconductor sealing resin composition.

  FIG. 2 is a view showing a cross-sectional structure of an example of a single-side sealed semiconductor device using the resin composition according to the present invention. The semiconductor element 1 is fixed on the substrate 8 via the solder resist 7 and the die bond material cured body 2. The electrode pads of the semiconductor element 1 and the electrode pads on the substrate 8 are connected by wires 4. Only the single side | surface side in which the semiconductor element 1 of the board | substrate 8 was mounted is sealed by the hardening body 6 of the resin composition for sealing. The electrode pads on the substrate 8 are bonded to the solder balls 9 on the non-sealing surface side on the substrate 8 inside. Such a semiconductor device is economically obtained because the semiconductor element 1 is encapsulated with the resin composition for encapsulating a semiconductor according to the present invention, so that the semiconductor device is excellent in reliability and productivity.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail with reference to an Example, this invention is not limited to description of these Examples at all.

  Each component used for the resin composition for semiconductor sealing obtained by the Example and comparative example which are mentioned later is demonstrated. Unless otherwise specified, the amount of each component is part by mass.

(Epoxy resin raw material phenol resin)
In synthesizing the following epoxy resins 1 to 9, the following phenol resin was used as a raw material (precursor).

Phenolic resin 1: FUSTER Co., Ltd., SYSTER GP-90 represented by the following general formula (14). Hydroxyl equivalent weight 197 g / eq, softening point 86 ° C. In formula (14), z is an integer of 1-40.

Phenol resin 2: manufactured by Mitsubishi Gas Chemical Co., Inc., represented by the following general formula (15), Nikanol GLP. Hydroxyl equivalent weight 163 g / eq, softening point 84 ° C. In the following general formula (15), the right end of the molecule is a hydrogen atom. In addition, the phenol resin 2 is one in which the structural unit represented by the repeating number t and the structural unit represented by the repeating number s are alternately bonded, those bonded in a block shape, those bonded irregularly, regular It is a mixture such as those bound to

(However, in the said General formula (15), s and t are integers of 1-2.)

Phenol resin 3: Phenol aralkyl resin having a phenylene skeleton (Mitsui Chemicals, XLC-4L. Hydroxyl equivalent 170 g / eq, softening point 62 ° C.)

Phenol resin 4: Phenol aralkyl resin having a phenylene skeleton (Maywa Kasei Co., Ltd., MEH-7800SS. Hydroxyl equivalent 170 g / eq, softening point 65 ° C.)

Phenol resin 5: Phenol aralkyl resin having a phenylene skeleton (Mitsui Chemicals, XLC-3L. Hydroxyl equivalent 170 g / eq, softening point 71 ° C.)

(Epoxy resin)
The following epoxy resins 1-14 were used as the epoxy resin.

Epoxy resin 1: 30 parts by mass of phenol resin 1, 70 parts by mass of phenol resin 3, 333 parts by mass of epichlorohydrin, and 66 parts by mass of dimethyl sulfoxide were added. After being heated to 45 ° C and dissolved, 25 parts by mass of sodium hydroxide (solid fine particles, 99% purity reagent) is added over 2 hours, the temperature is raised to 50 ° C, and the temperature is further increased to 70 ° C for 2 hours. The reaction was allowed to warm for 2 hours. After the reaction, after adding 150 parts by mass of distilled water and shaking, the operation (water washing) of discarding the aqueous layer was repeated until the washing water became neutral, and then the epichlorohydrin and Dimethyl sulfoxide was distilled off. 282 parts by mass of methyl isobutyl ketone was added to the obtained solid and dissolved, heated to 70 ° C., 8 parts by mass of a 30% by mass aqueous sodium hydroxide solution was added over 1 hour, and the reaction was further continued for 1 hour. The water layer was discarded. After 150 parts by mass of distilled water was added to the oil layer and washed with water, the same washing operation was repeated until the washed water became neutral, and then methyl isobutyl ketone was distilled off by heating under reduced pressure to obtain epoxy resin 1 (epoxy equivalent). 245 g / eq, an ICI viscosity of 1.0 dPa · s at a softening point of 52 ° C. and 150 ° C.). A GPC chart is shown in FIG.

Epoxy resins 2 to 9: The phenol resins were blended as shown in Table 1, and other operations were performed in the same manner as epoxy resin 1 to obtain epoxy resins 2 to 9. The epoxy equivalent, softening point, and ICI viscosity at 150 ° C. of these epoxy resins are shown in Table 1, and GPC charts are shown in FIGS.

Epoxy resin 10: Phenolic aralkyl type epoxy resin having a phenylene skeleton (Nippon Kayaku Co., Ltd., NC2000, epoxy equivalent 238 g / eq, softening point 52 ° C., ICI viscosity 0.9 dPa · s at 150 ° C.)

Epoxy resin 11: biphenyl type epoxy resin (Japan Epoxy Resin Co., Ltd., YX4000K. Epoxy equivalent 185 g / eq, softening point 107 ° C.)

Epoxy resin 12: bisphenol A type epoxy resin (Japan Epoxy Resin Co., Ltd., YL6810. Epoxy equivalent 172 g / eq, softening point 45 ° C.)

Epoxy resin 13: Bisphenol F type epoxy resin (manufactured by Toto Kasei Co., Ltd., YSLV-80XY. Epoxy equivalent 190 g / eq, softening point 80 ° C.)

Epoxy resin 14: Orthocresol novolak type epoxy resin (Dainippon Ink & Chemicals, N-660, epoxy equivalent 210 g / eq, softening point 62 ° C.)

(Curing agent)
The following curing agents 1 to 4 were used as curing agents.

Curing agent 1: Phenol aralkyl resin having a phenylene skeleton (Maywa Kasei Co., Ltd., MEH-7800SS. Hydroxyl equivalent 170 g / eq, softening point 65 ° C.)

Curing agent 2: Phenol aralkyl resin having a biphenylene skeleton (Maywa Kasei Co., Ltd., MEH-7851SS. Hydroxyl equivalent 203 g / eq, softening point 67 ° C.)

Curing agent 3: A separable flask equipped with a stirrer, thermometer, reflux condenser, and nitrogen inlet, 116.3 parts by weight of formaldehyde 37% aqueous solution (formalin 37% by Wako Pure Chemical Industries), 98 parts by weight, sulfuric acid After weighing 37.7 parts by mass and 100 parts by mass of m-xylene (special grade reagent manufactured by Kanto Chemical Co., Ltd., m-xylene, boiling point 139 ° C., molecular weight 106, purity 99.4%), heating was started while replacing with nitrogen. The system was stirred for 6 hours while maintaining the temperature range of 90 to 100 ° C. and cooled to room temperature, and then the system was neutralized by gradually adding 150 parts by mass of 20% by mass sodium hydroxide. To this reaction system, 839 parts by mass of phenol and 338 parts by mass of α, α′-dichloro-p-xylene were added and heated while performing nitrogen substitution and stirring, while maintaining the system temperature in the range of 110 to 120 ° C. The reaction was allowed for 5 hours. The hydrochloric acid gas generated in the system by the above reaction was discharged out of the system by a nitrogen stream. After completion of the reaction, unreacted components and water were distilled off under reduced pressure conditions at 150 ° C. and 2 mmHg. Next, after adding 200 parts by mass of toluene and dissolving it uniformly, it was transferred to a separatory funnel, and after adding 150 parts by mass of distilled water and shaking, the operation of rinsing the aqueous layer (washing) was carried out to neutralize the washing water. Then, the oil layer is subjected to a vacuum treatment at 125 ° C. to distill off volatile components such as toluene and residual unreacted components, and the phenol resin curing agent 3 (hydroxyl equivalent: 180 g) represented by the following general formula (19) / Eq, ICI viscosity at a softening point of 67 ° C. and 150 ° C. 0.60 dPa · s, p in the general formula (19) is an integer of 0-20, q is an integer of 0-20, and r is an integer of 0-20. The average value of p, q, and r is 1.8, 0.3, and 0.6, respectively, in the general formula (19), where the left end of the molecule is a hydrogen atom and the right end Is a phenol or xylene structure .) Was obtained. However, the curing agent 3 is one in which the structural unit represented by the repeating number p, the structural unit represented by the repeating number q, and the structural unit represented by the repeating number r are combined in a block shape. , A mixture of irregularly coupled, regularly coupled, etc.

Curing agent 4: Phenol novolak resin (manufactured by Sumitomo Bakelite Co., Ltd., PR-HF-3. Hydroxyl equivalent weight 104 g / eq, softening point 80 ° C.)

(Inorganic filler)
As the inorganic filler, 100 parts by mass of fused spherical silica FB560 (average particle size 30 μm) manufactured by Denki Kagaku Kogyo Co., Ltd., 6.5 parts by mass of synthetic spherical silica SO-C2 (average particle size 0.5 μm) manufactured by Admatex, A blend of 7.5 parts by mass of synthetic spherical silica SO-C5 (average particle size 1.5 μm) manufactured by Mattex was used.

(Curing accelerator)
The following curing accelerators 1-5 were used.

Curing accelerator 1: Curing accelerator represented by the following formula (20)

Curing accelerator 2: Curing accelerator represented by the following formula (21)

Curing accelerator 3: Curing accelerator represented by the following formula (22)

  Curing accelerator 4: Curing accelerator represented by the following formula (23)

Curing accelerator 5: Triphenylphosphine (Hokuko Chemical Industries, Ltd., TPP)

(Compound (E) in which a hydroxyl group is bonded to each of two or more adjacent carbon atoms constituting an aromatic ring)
As the compound E, the compound represented by the following general formula (24) (Tokyo Chemical Industry Co., Ltd., 2,3-naphthalenediol, purity 98%) was used.

(Silane coupling agent)
The following silane coupling agents 1 to 3 were used.

Silane coupling agent 1: γ-mercaptopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-803).
Silane coupling agent 2: γ-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-403).
Silane coupling agent 3: N-phenyl-3-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-573)

(Flame retardants)
The following flame retardants 1-2 were used.
Flame retardant 1: Aluminum hydroxide (Sumitomo Chemical Co., Ltd., CL310)
Flame retardant 2: Magnesium hydroxide / zinc hydroxide solid solution composite metal hydroxide (Echo Mug Z-10, manufactured by Tateho Chemical Co., Ltd.)

(Coloring agent)
Carbon black (MA600) manufactured by Mitsubishi Chemical Industries, Ltd. was used as a colorant.

(Release agent)
As a release agent, carnauba wax (Nikko carnauba, melting point 83 ° C.) manufactured by Nikko Fine Co., Ltd. was used.

  The following measurements and evaluations were performed on the resin compositions for semiconductor encapsulation obtained in Examples and Comparative Examples described later.

(Evaluation item)
Manufacturability during manufacture: obtained by melting and kneading the resin composition with a heating roll, cooling with a spot cooler, then roughly pulverizing manually, then pulverizing with a hammer crusher, and a temperature atmosphere of 22 to 25 ° C. Below, the pulverized product was tableted into a tablet over 3 hours including the waiting time. The case where any one of the troubles shown in 1) and 2) below is indicated as x, and the case where the tablet is obtained satisfactorily without causing any troubles in the following 1) and 2) is indicated as ◯. did.
1) When the resin composition adheres in the hammer crusher or adheres to the wall surface of the hammer crusher 2) When the resin adheres to the inner surface of the mold during the tablet molding process, and the appearance of the tablet is damaged

  Spiral flow: Using a low-pressure transfer molding machine (KTS-15, manufactured by Kotaki Seiki Co., Ltd.), a spiral flow measurement mold according to EMMI-1-66 was applied at 175 ° C., injection pressure 6.9 MPa, pressure holding time The resin composition was injected under the condition of 120 seconds, and the flow length was measured. The spiral flow is a fluidity parameter, and the larger the value, the better the fluidity. The unit is cm.

  Flame resistance: Resin composition using a low-pressure transfer molding machine (KTS-30, manufactured by Kotaki Seiki Co., Ltd.) under conditions of a mold temperature of 175 ° C., an injection time of 15 seconds, a curing time of 120 seconds, and an injection pressure of 9.8 MPa. Was molded by injection to produce a 3.2 mm thick flame resistant test piece. About the obtained test piece, the flame resistance test was done according to the specification of UL94 vertical method. The table shows Fmax, ΣF, and the fire resistance rank (class) after determination.

  Wire flow rate: 208 pin QFP package (dimension; 28 × 28 × 2) for wire flow rate evaluation test using tableted resin composition on low pressure transfer molding machine at 175 ° C., 6.9 MPa, 120 seconds .4 mm, Cu lead frame, test element: 9 × 9 mm, wire: Au, diameter 1.2 mils, length of about 5 mm) each was molded into 10 packages, and the molded 208-pin QFP package was observed with a soft X-ray transmission device . As a method of calculating the wire flow rate, the flow rate of the most flowed (deformed) wire in one package is (F), the length of the wire is (L), and the flow rate = F / L × 100 (%) was calculated and the average value of 10 packages was shown. The wire flow rate (%) was determined to be less than 5%, and 5% or more to be rejected.

  Continuous moldability: The obtained resin composition was adjusted with a powder molding press (S-20-A, manufactured by Tamagawa Machinery Co., Ltd.) to have a weight of 15 g, size φ18 mm × height of about 30 mm, and tableting pressure Tablets were obtained by tableting at 600 Pa. A tablet supply magazine loaded with the obtained tablet was set in the molding apparatus. For molding, using a low-pressure transfer automatic molding machine (manufactured by Daiichi Seiko Co., Ltd., GP-ELF) as a molding device, the resin composition under conditions of a mold temperature of 175 ° C., a molding pressure of 9.8 MPa, and a curing time of 120 seconds 80 pin QFP (Cu lead frame, package outer dimensions: 14 mm x 20 mm x 2.0 mm thickness, pad size: 8.0 mm x 8.0 mm, chip size 7.0 mm x 7 0.0 mm × 0.35 mm thickness) was continuously performed up to 400 shots. At this time, the molding state of the package (whether or not unfilled) is confirmed every 50 shots, and the number of shots where unfilled can be confirmed first, or if there is no unfilled, a ○ mark in the table Described in the section “Bad”. Incidentally, the tablets in the magazine set in the molding apparatus are in a standby state in the magazine of the molding apparatus until they are actually used for molding, and a maximum of 13 tablets are stacked vertically at a surface temperature of about 30 ° C. Was in a state. The tablet is fed and transported in the molding device by raising the push-up pin from the bottom of the magazine, so that the tablet on the top is pushed out from the top of the magazine and lifted by the mechanical arm to the transfer molding pot. Be transported. At this time, if the tablet sticks up and down during standby in the magazine, a conveyance failure occurs. In the section of conveyance failure in the table, the number of shots in which conveyance failure could be confirmed first, or a circle mark when no conveyance failure occurred.

  Solder resistance test 1: Using a low-pressure transfer molding machine (Daiichi Seiko Co., Ltd., GP-ELF), the resin composition was molded under conditions of a mold temperature of 180 ° C., an injection pressure of 7.4 MPa, and a curing time of 120 seconds. The lead frame or the like on which the semiconductor element (silicon chip) is injected is sealed and molded, and 80 pQFP (Cu lead frame with Cu strike plating on the surface, size is 14 × 20 mm × thickness 2.00 mm, semiconductor The element was 7 × 7 mm × thickness 0.35 mm, and the semiconductor element and the inner lead portion of the lead frame were bonded with a 25 μm diameter gold wire. Six semiconductor devices heat-treated at 175 ° C. for 4 hours as post-cure were humidified for 168 hours at 85 ° C. and 60% relative humidity, and then subjected to IR reflow treatment (260 ° C. condition). The presence or absence of peeling and cracks inside these semiconductor devices was observed with an ultrasonic flaw detector (manufactured by Hitachi Construction Machinery Finetech Co., Ltd., mi-scope 10), and the occurrence of either peeling or cracking was regarded as defective. When the number of defective semiconductor devices is n, n / 6 is displayed.

  Solder resistance test 2: In the above-described solder resistance test 1, before injecting the resin composition, a lead frame on which a semiconductor element (silicon chip) is mounted is treated on a hot plate at 250 ° C. for 120 seconds. The test was conducted in the same manner as in the solder resistance test 1 except that the lead frame surface was oxidized and sealed.

  Solder resistance test 3: In the solder resistance test 1 described above, a Cu lead frame subjected to nickel / palladium / gold plating treatment was used instead of the Cu lead frame, and the humidification conditions were 60 ° C., relative humidity 60%, 96 The test was conducted in the same manner as the solder resistance test 1 except that the time was set.

  About an Example, a reference example, and a comparative example, according to the compounding quantity shown to Table 2 and 3, each component was mixed at normal temperature using the mixer, and the powdery intermediate body was obtained. The obtained powdery intermediate was loaded into an automatic supply device (hopper), quantitatively supplied to a heating roll at 80 ° C. to 100 ° C., and melt kneaded. Then, it was cooled and then pulverized to obtain a resin composition for semiconductor encapsulation. Said measurement and evaluation were performed using the obtained resin composition for semiconductor sealing. The results are shown in Tables 4 and 5.

  Examples 1 to 6 and 9 to 20 are all represented by general formula (2) and any one of phenol resins 1 and 2 corresponding to the compound having a structure represented by general formula (1). Epoxy resins 1 to 6 obtained by epoxidizing after previously mixing any one of phenol resins 3 to 5 corresponding to the compound are blended. In Examples 7 and 8, both the epoxy resin 7 obtained by epoxidizing any one of the phenol resins 1 and 2 corresponding to the compound having the structure represented by the general formula (1) or 8 and an epoxy resin 10 corresponding to an epoxy resin obtained by reacting a compound represented by the general formula (2) with epihalohydrin. In any of the resin compositions of Examples 1 to 20, excellent results were obtained in the balance of handling property, fluidity (spiral flow), flame resistance, wire flow rate, continuous formability (fillability), and solder resistance. It was. Examples 1, 2, and 3 were prepared by mixing the epoxy resin 7 obtained by epoxidizing the phenol resin 1 alone and the epoxy resin obtained by epoxidizing the phenol resin 3 alone. Attempting to prepare the same resin composition as in Example 1, but at the stage of melt-kneading and cooling, it became partially soft clay and could not be coarsely pulverized, and it was judged that good mixing was not possible Therefore, the preparation and evaluation of the resin composition were stopped. Moreover, the epoxy resin 8 obtained by epoxidizing the phenol resin 2 alone and the epoxy resin 9 obtained by epoxidizing the phenol resin 4 alone are mixed and the same as in Example 6. In the reference example in which the resin composition was prepared, the handling failure (2) occurred, and the yield decreased. The evaluation results of the recovered resin composition showed the same characteristics as in Examples except that the continuous moldability was slightly inferior.

  According to the present invention, a resin composition for encapsulating a semiconductor having a good balance between continuous moldability and adhesion, and a cured product thereof encapsulating a semiconductor element while achieving both excellent fluidity and practical handling properties Thus, a highly reliable semiconductor device can be obtained economically. In particular, it is suitable for sealing a semiconductor device having a structure in which chips are stacked in one package or a wire diameter smaller than that of a conventional device.

DESCRIPTION OF SYMBOLS 1 Semiconductor element 2 Die-bonding material hardening body 3 Die pad 4 Wire 5 Lead frame 6 Hardening body of sealing resin composition 7 Solder resist 8 Substrate 9 Solder ball

Claims (12)

Epoxy resin (A),
A phenolic resin-based curing agent (B);
An inorganic filler (C);
Including
Epoxy resin (A)
An epoxy resin in which a compound having a structure represented by the general formula (1) and an epihalohydrin are reacted;
Look including the general formulas epoxy resin compound and the epihalohydrin are reacted represented by (2), and
A resin composition for semiconductor encapsulation, which is an epoxy resin that is epoxidized after mixing the compound having the structure represented by the general formula (1) and the compound represented by the general formula (2) .

(However, in the above general formula (1), R1 is a hydrocarbon group having 1 to 6 carbon atoms, R2 is a hydrocarbon group having 1 to 10 carbon atoms, and may be the same or different. A hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, which may be the same or different from each other, i is an integer of 1 to 4, j is an integer of 0 to 3, and n is 0 to 10 M is an integer of 0 to 10, and m + n ≧ 2.The structural unit represented by the number of repetitions n and the structural unit represented by the number of repetitions m may be mutually aligned. (Although they may be arranged alternately or randomly, a structure having -C (RxRy)-is necessarily provided between them.)

(However, in the said General formula (2), R3 is a C1-C10 hydrocarbon group, and may mutually be same or different. Rp, Rq, Rr, and Rs are a hydrogen atom or carbon number 1. And may be the same or different from each other, k is an integer of 0 to 3, and l is an integer of 0 to 10.) In the resin composition for semiconductor encapsulation according to claim 1,
A resin composition for semiconductor encapsulation, wherein the epoxy resin (A) has a softening point of 50 ° C. or higher and 80 ° C. or lower. In the resin composition for semiconductor encapsulation according to claim 1 or 2,
A resin composition for encapsulating a semiconductor, wherein R1 in the general formula (1) is a methyl group and i = 2. In the resin composition for semiconductor encapsulation according to claim 1 or 2,
An epoxy equivalent of the epoxy resin (A) is 220 g / eq or more and 300 g / eq or less, a resin composition for semiconductor encapsulation. In the resin composition for semiconductor encapsulation according to claim 1 or 2,
A resin composition for encapsulating a semiconductor, wherein the compound having a structure represented by the general formula (1) is synthesized from substituted or unsubstituted phenol, xylene, and formalin. Wherein a obtained by encapsulating a semiconductor element with a cured product of the resin composition for semiconductor encapsulation according to any one of claims 1 to 5. The semiconductor device according to claim 6 .
A semiconductor device, wherein the semiconductor element is mounted on a lead frame. Mixing the compound having the structure represented by the general formula (1) and the compound represented by the general formula (2);
Epoxidizing the mixed compound having the structure represented by the general formula (1) and the compound represented by the general formula (2) to obtain an epoxy resin (A);
A process for producing a resin composition for semiconductor encapsulation, comprising: an epoxy resin (A), a phenol resin curing agent (B), and an inorganic filler (C).

(However, in the above general formula (1), R1 is a hydrocarbon group having 1 to 6 carbon atoms, R2 is a hydrocarbon group having 1 to 10 carbon atoms, and may be the same or different. A hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, which may be the same or different from each other, i is an integer of 1 to 4, j is an integer of 0 to 3, and n is 0 to 10 M is an integer of 0 to 10, and m + n ≧ 2.The structural unit represented by the number of repetitions n and the structural unit represented by the number of repetitions m may be mutually aligned. (Although they may be arranged alternately or randomly, a structure having -C (RxRy)-is necessarily provided between them.)

(However, in the said General formula (2), R3 is a C1-C10 hydrocarbon group, and may mutually be same or different. Rp, Rq, Rr, and Rs are a hydrogen atom or carbon number 1. And may be the same or different from each other, k is an integer of 0 to 3, and l is an integer of 0 to 10.) In the manufacturing method of the resin composition for semiconductor sealing of Claim 8 ,
The softening point of an epoxy resin (A) is 50 degreeC or more and 80 degrees C or less, The manufacturing method of the resin composition for semiconductor sealing characterized by the above-mentioned. In the manufacturing method of the resin composition for semiconductor sealing of Claim 8 or 9 ,
The manufacturing method of the resin composition for semiconductor sealing characterized by R1 in General formula (1) being a methyl group, and i = 2. In the manufacturing method of the resin composition for semiconductor sealing of Claim 8 or 9 ,
The epoxy equivalent of an epoxy resin (A) is 220 g / eq or more and 300 g / eq or less, The manufacturing method of the resin composition for semiconductor sealing characterized by the above-mentioned. In the manufacturing method of the resin composition for semiconductor sealing of Claim 8 or 9 ,
A method for producing a resin composition for encapsulating a semiconductor, wherein the compound having a structure represented by the general formula (1) is synthesized from substituted or unsubstituted phenol, xylene, and formalin.

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