WO2005080502A1 - アンダーフィル用液状エポキシ樹脂組成物および同組成物を用いて封止した半導体装置 - Google Patents
アンダーフィル用液状エポキシ樹脂組成物および同組成物を用いて封止した半導体装置 Download PDFInfo
- Publication number
- WO2005080502A1 WO2005080502A1 PCT/JP2004/002158 JP2004002158W WO2005080502A1 WO 2005080502 A1 WO2005080502 A1 WO 2005080502A1 JP 2004002158 W JP2004002158 W JP 2004002158W WO 2005080502 A1 WO2005080502 A1 WO 2005080502A1
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- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- resin composition
- coupling agent
- underfill
- agent
- Prior art date
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Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a liquid epoxy resin composition for underfill having excellent underfill penetration, moisture resistance, and thermal shock resistance, and a semiconductor device encapsulated with the composition.
- the underfill material for flip-chip type semiconductor devices described in Japanese Patent Application Publication No. 2001-55486 is 100 parts by weight of liquid epoxy resin, and has a maximum particle size of 5 ⁇ m or less.
- the curing accelerator contains 0.01 to 10 parts by weight.
- R 1 a R 2 b Si ( ⁇ R 3 ) c (OH) d ⁇ (c - d) / 2 (P)
- R 1 is a monovalent organic group which has 2 and R 3 are independently an unsubstituted or alkoxy-substituted monovalent hydrocarbon group having 1 to 8 carbon atoms
- a is 0.16 to 1.0
- b is 0 to 2.0
- c is 0.5 to 2.0
- d is 0 to 1.0
- the number of silicon atoms in one molecule of fe is 2 to 6.
- the above-mentioned 7 reactive functional groups Since the silicone compound is contained, it is possible to maintain good penetration characteristics into narrow gaps by blending a large amount of the inorganic filler as described above. Even when a silane coupling agent (ie, a reactive functional group-containing alkoxysilane compound) is added, the generation of voids can be reduced, and the flip sealed with the underfill material can be used. It is improving the reliability of chip-type semiconductor devices.
- a silane coupling agent ie, a reactive functional group-containing alkoxysilane compound
- the present invention has been made in view of the above problems, and has as its object to improve the disadvantages of the conventional epoxy resin composition for encapsulation, and to excel in underfill penetration, moisture resistance, and thermal shock resistance.
- An object of the present invention is to provide a liquid epoxy resin composition for underfill.
- the epoxy resin composition of the present invention contains an epoxy resin, a curing agent, a curing accelerator, an inorganic filler, and a coupling agent, and the coupling agent has a structure (A) represented by the following formula in one molecule.
- the content of the coupling agent in the resin composition is 0.05% to 1.0% by weight.
- the power coupling agent it is preferable to hydrolyze the power coupling agent with pure water or alcohol prior to blending with the other components of the resin composition.
- the alkoxy group of the coupling agent By hydrolyzing the alkoxy group of the coupling agent, the wettability of the coupling agent with the inorganic filler can be further improved.
- hydrolysis is performed in advance, variation during production can be reduced.
- those containing S, -OH, and nickel have high polarity, which contributes to improving the adhesion between the base material and the chip, thereby improving the reliability.
- the curing accelerator is preferably at least one selected from tertiary amines and microcapsule-type latent imidazole. Selection from these three types is desirable in terms of one-part properties and pot life.
- the inorganic filler preferably has a maximum particle size of 0.5 to 30 m. If the maximum particle size is less than Q.5jum, the viscosity increases and the underfill performance decreases. On the other hand, if the maximum particle size is 30 jm or more, the narrow gap of 30 iim or less cannot be counter-emitted.
- the curing agent is preferably an acid anhydride type, and preferably contains 5 to 40 wt% of trifunctional or more in the curing agent.
- a further object of the present invention is to provide a semiconductor device which is encapsulated using the above epoxy resin composition.
- the epoxy resin composition for underfill of the present invention contains an epoxy resin, a curing agent, a curing accelerator, an inorganic filler, and a coupling agent as essential components.
- Examples of the epoxy resin used in the present invention include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, naphthalene ring-containing epoxy resin, and alicyclic type Epoxy resin, dicyclopentadiene-type epoxy resin having dicyclopentane skeleton, phenol novolak type Epoxy resin, cresol nopolak type epoxy resin, triphenyl methane type epoxy resin, aliphatic epoxy resin, triglycidyl isocyanurate, etc. are used, and one or two or more kinds selected from these are selected. Can be used.
- bisphenol A-type epoxy resin bisphenol F-type epoxy resin, biphenyl-type epoxy resin, naphthalene ring-containing epoxy resin, and alicyclic epoxy resin are particularly preferable from the viewpoint of improving the viscosity and physical properties of the cured product.
- the polyfunctional epoxy resin include the following compounds (1) to (3) (in the formula, “G ⁇ is a glycidyl group”).
- alicyclic epoxy resins and trifunctional epoxy resins may be used, such as trifunctional and tetrafunctional types.In view of reliability, Na ion, CI ion, Brion and the like may be used. It is preferable to use an epoxy resin containing as few impurities as possible.
- the curing agent used in the present invention may be any one that normally cures an epoxy resin.
- amine-based curing agents such as diaminodiphenylmethane and metaphenylenediamine
- acid anhydride curing agents such as anhydrous phthalic acid and pyromellitic anhydride
- phenol nopolak-based curing agents and aryl phenol curing agents And so on.
- polyfunctional acid anhydride curing agent include compounds having the structures shown in the following Examples (4) to (9), and the bifunctional type is preferred because of its low viscosity and low melting point.
- the chemical equivalent ratio of the curing agent to the epoxy resin to be blended is preferably in the range of 0.6 to 1.4. If the Tohoku ratio is less than 0.6, curing may become difficult, the heat resistance of the cured product may be reduced, and the strength of the cured product may be reduced. If the equivalent ratio is more than "1.4", the heat resistance of the cured product may be reduced, the adhesive strength after curing may be reduced, and the moisture absorption of the cured product may increase.
- a particularly preferred staring ratio of the curing agent to the epoxy resin is in the range of 0.75 to 1.00
- curing is preferably performed with as few impurities as possible, such as Na ion CI ion and Br ion.
- the curing accelerator used in the present invention preferably contains at least one of an imidazole skeleton, an amine compound, and a microcapsule-type curing accelerator.
- a known one such as a primary to tertiary amine or a salt thereof, a triazole or a salt thereof, an imidazole or a salt thereof, a diazabicycloalkene or a salt thereof, alone.
- a thermosetting resin film is formed around a core made of a compound having an S-dazole skeleton.
- fine spheres fine spheres (so-called microcapsules) provided with, or amine adduct particles are suitably used as a curing accelerator.
- the inorganic filler used in the present invention is not particularly limited.
- use of crystalline silica, fused silica, alumina, finely divided silica, magnesia, silicon nitride and the like can be mentioned.
- the addition amount is 40 wt% to 65 wt% of the whole resin composition. If it is less than 40 wt%, it is difficult to reduce the coefficient of linear expansion, which may eventually lead to cracking and destruction of the obtained semiconductor device.
- the content is 65 wt% or more, the viscosity may increase and the underfill penetration may decrease. In the case of flip chips, it is necessary to reduce the particle size of the filler. ic.1t. If the viscosity increases due to the fineness and the sedimentation during hardening is observed, the maximum particle size is 30 ⁇ . It is preferable that it is not more than rn.
- the coupling agent used in the present invention has two or more structures (A) represented by the following formula in one molecule, and is used in a resin composition.
- silane coupling agent having two or more structures (A) in one molecule is used, other coupling agents may be used in combination.
- silane coupling agent! a titanate coupling agent. That is, silane coupling agents such as ⁇ -glycidoxypropyltrimethoxysilane, r-glycidoxypropyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc.
- vinyl silanes such as toxic silane, and epoxy-, amino-, and vinyl-based polymer-type silanes.
- Epoxy silane, amino silane, and mercapto silane are particularly preferable.
- the titanate coupling agent include isopropyl triisostearoyl titanate, isopropyl tri (N-aminoethyl'aminoethyl) titanate, diisopropyl bis (dioctylphosphoret) titanate, and tetraisopropyl bis ( Dioctyl phosphite) Titanate, Tetra octyl bis (ditridecyl phosphite) titanate, Bis (Dioctyl benzoyl phosphate) is there.
- These coupling agents can be used alone, or two or more of them can be mixed and used.
- the coupling agent may be used by treating the filler in advance by a wet method or a dry method, or may be used by an integral blend method in which the filler is mixed with a resin.
- the epoxy resin composition of the present invention When the epoxy resin composition of the present invention is produced, the above-mentioned epoxy resin, curing agent, curing accelerator, coupling agent and other components are mixed together or separately, if necessary. B. Stir, dissolve, mix and disperse while performing heat treatment. Next, an inorganic filler is added to the obtained mixture, and the mixture is stirred, dissolved, mixed and dispersed while performing a cooling and heating treatment as needed, to obtain a liquid epoxy resin composition.
- a dispersing planetary mixer, a ball mill, a bead mill, a three-plate mill, or the like may be effectively used in the steps of stirring, dissolving, mixing, and dispersing.
- epoxy resin examples include bis-A epoxy resin (Japan Epoxy Resin Co., Ltd.
- methyl tetrahydrophthalic anhydride As the acid anhydride of the hardener, methyl tetrahydrophthalic anhydride (Shin Nippon Rika Co., Ltd.)
- imidazole-based microcapsule-type latent catalysts As curing accelerators, imidazole-based microcapsule-type latent catalysts (Asahi Kasei Epoxy, HX3941 HR, Amine-modified catalysts (Asahi Denka Kogyo Co., Ltd. EH3849S), imidazole (Shikoku Kasei Kogyo Co., Ltd., 1 B2PZ), phosphorus-based Catalyst (Hokuko Chemical Industry Co., Ltd.) Use either TPP (triphenylphosphine)).
- QS-4 Mitsubishi Rayon Co., Ltd., maximum particle size 14 m
- SO-E2 Admatex Co., Ltd., max. 3 im>
- QS-9 Mitsubishi Rayon Co., Ltd., max. 35 m
- QS-8 Koryo Rayon Co., Ltd., max. 30 wm
- AA04 Suditomo Chemical Co., Ltd., max. 0.5 m
- This coupling agent 1 has the following structure (18), and the molecule S is 178.
- This coupling agent is prepared by adding 0.2 mol of pure water and 0.05 mol of ethanol to “I mol” of the coupling agent No. 1 and stirring the mixture, and leaving the mixture at 35 ° C. for 3 hrs to leave the coupling agent No. 1 Was obtained by hydrolysis.
- This force coupling agent the molecular weight 120 of (CH 3) 2 Si (OCH 3) 2 pure water 0.2mol against 1 mol, adding ethanol O.05mol was ⁇ , obtained by leaving 3hrs at 35C It has the following structure (19), and the average degree of polymerization is 1.1.
- This coupling agent has the following structure (20), the average degree of polymerization is 1.1, and the molecular weight is 161.
- This coupling agent has the following structure (2 ⁇ ), a homopolymerization degree of 2.2, and a molecular weight of 114.
- an epoxy silane coupling agent (Shinichi Nihonichi (Shima A187) was used in a predetermined amount.
- Example 1 As an example, a method for producing the epoxy resin composition of Example 1 will be specifically described. First, bisphenol A type epoxy resin, MH-700, a curing agent acid anhydride and PMDA, a multifunctional acid anhydride B, imidazole "tB2PZ", a curing accelerator The mixing agent No. 2 and the synthetic silica QS-4, an inorganic filler, were blended in the blending amounts shown in Table 1, mixed with a mixer for 30 minutes, and then kneaded with three rolls. The obtained kneaded material was mixed again with a mixer for 30 minutes to obtain the epoxy resin composition of Example 1.
- the epoxy resin compositions of Examples 2 to 21 were prepared by substantially the same method as described above so as to have the composition shown in Tables 1 to 3, respectively.
- the case where the coupling agent containing two structures (A) was not used was used as the comparative example 1, and the case where the compounding amount of the coupling agent No. 1 was less than 0.05 ⁇ %.
- the epoxy resin composition thus obtained and the semiconductor device sealed using the epoxy resin composition were evaluated for the following physical properties.
- the semiconductor device used in the test was composed of electrodes on the FR5 grade circuit board and electrodes on the periphery of the chip of a 0.4 mm thick, 1 Omm square CMOS gate array element, with a height of 70 jtm. They are connected by solder bumps.
- the epoxy resin composition is applied to the end of one side of the chip with a dispenser. Immediately after the substrate is placed on a hot plate at 80 ° C, the resin composition is applied to the opposite side of the side. The time to reach the side of was measured. When the measurement time was 60 seconds or less, it was evaluated as " ⁇ " when it was 2 minutes or less, and as "X" when it was 2 minutes or more, and evaluated.
- the semiconductor component in which the epoxy resin composition was infiltrated was cured at a temperature of 150 ° C. for 2 hours 1 ⁇ .
- the results of confirming the electrical operation of the semiconductor parts after curing are good.
- One cycle 30 minutes at 55 ° C, 5 minutes at room temperature, 30 minutes at 150 ° C, 5 minutes at room temperature
- the device was subjected to a temperature cycle test of the gas phase to confirm the operation of the device after 1 000 cycles, and passed or failed. If the number of defective samples in 10 test samples is 0-3, it is evaluated as " ⁇ ", if 4-6, it is evaluated as "mu”, and if it is 7-1 ⁇ , it is evaluated as "X" ⁇ .
- the results of confirming the electrical operation of the semiconductor component after curing are good. Then, it was subjected to a pressure and cooker test at 2 atm of 121 ° C, and the operation of the device was confirmed after 168 hours, and the pass / fail was judged. 1 ⁇ If the number of defective samples in the test sample is 0-3, it is evaluated as 4-6 if it is 4-6, and if it is 10-10, it is evaluated as ⁇ .
- Tables 1 to 3 show the evaluation results of _t notes 1 to 3, respectively.
- the liquid epoxy for underfill of the present invention containing a coupling agent having two or more of the above structure (A) in one molecule in the range of 0.05 wt% to 1.5 t%.
- a favorable underfill can be ensured and the infiltration property can be ensured in response to a demand for high filling of the inorganic filling material. Since excellent moisture resistance and thermal shock resistance are still achieved, the semiconductor device encapsulated with the epoxy resin composition of the present invention has high reliability.
- Multifunctional acid anhydride B PMDA 19.2 19.2 19.2 19.2 19.2 19.2 7.7 9.7 Cured microphone 0 cuff ° Cellular imida 1 / -HX-3941 HP 8.7
- No. 1 0.4 16.0 contains 2 of the structure A in one molecule Allinge No. 2 3.0 3.0 2.5
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- Polymers & Plastics (AREA)
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- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
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- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
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Priority Applications (2)
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PCT/JP2004/002158 WO2005080502A1 (ja) | 2004-02-24 | 2004-02-24 | アンダーフィル用液状エポキシ樹脂組成物および同組成物を用いて封止した半導体装置 |
JP2006510142A JPWO2005080502A1 (ja) | 2004-02-24 | 2004-02-24 | アンダーフィル用液状エポキシ樹脂組成物および同組成物を用いて封止した半導体装置 |
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PCT/JP2004/002158 WO2005080502A1 (ja) | 2004-02-24 | 2004-02-24 | アンダーフィル用液状エポキシ樹脂組成物および同組成物を用いて封止した半導体装置 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007169445A (ja) * | 2005-12-21 | 2007-07-05 | Matsushita Electric Works Ltd | アンダーフィル用液状エポキシ樹脂組成物及び半導体装置 |
JP2008050544A (ja) * | 2006-08-28 | 2008-03-06 | Matsushita Electric Works Ltd | エポキシ樹脂組成物、半導体装置及び半導体装置の製造方法。 |
WO2008072491A1 (ja) * | 2006-12-11 | 2008-06-19 | Sharp Kabushiki Kaisha | Icチップ実装パッケージ及びその製造方法 |
WO2012018684A1 (en) | 2010-08-04 | 2012-02-09 | 3M Innovative Properties Company | Encapsulating resin composition |
CN102850721A (zh) * | 2005-11-25 | 2013-01-02 | 日立化成工业株式会社 | 电子零件用液状树脂组合物及电子零件装置 |
JP2014111704A (ja) * | 2012-11-07 | 2014-06-19 | Panasonic Corp | 半導体封止用エポキシ樹脂組成物および半導体装置 |
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JPH04216819A (ja) * | 1990-12-17 | 1992-08-06 | Toshiba Chem Corp | 一液性エポキシ樹脂組成物 |
JPH0867805A (ja) * | 1994-08-29 | 1996-03-12 | Matsushita Electric Works Ltd | 液状エポキシ樹脂組成物 |
JPH10231351A (ja) * | 1997-02-18 | 1998-09-02 | Sumitomo Bakelite Co Ltd | 液状注入封止アンダーフィル材料 |
JP2000198831A (ja) * | 1998-12-28 | 2000-07-18 | Nagase Chiba Kk | エポキシ樹脂組成物およびそれを用いてlsiを封止する方法 |
JP2001031841A (ja) * | 1999-07-21 | 2001-02-06 | Hitachi Chem Co Ltd | 電子部品封止用エポキシ樹脂組成物 |
JP2001055486A (ja) * | 1999-06-09 | 2001-02-27 | Shin Etsu Chem Co Ltd | フリップチップ型半導体装置用アンダーフィル材及びフリップチップ型半導体装置 |
JP2002012742A (ja) * | 2000-06-28 | 2002-01-15 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物及び半導体装置 |
JP2002097341A (ja) * | 2000-09-20 | 2002-04-02 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物及び半導体装置 |
JP2002105172A (ja) * | 2000-10-04 | 2002-04-10 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物及び半導体装置 |
JP2003201386A (ja) * | 2001-10-30 | 2003-07-18 | Hitachi Chem Co Ltd | 封止用エポキシ樹脂成形材料及び電子部品装置 |
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2004
- 2004-02-24 JP JP2006510142A patent/JPWO2005080502A1/ja active Pending
- 2004-02-24 WO PCT/JP2004/002158 patent/WO2005080502A1/ja active Application Filing
Patent Citations (11)
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JPH02210853A (ja) * | 1989-02-10 | 1990-08-22 | Nitto Denko Corp | 半導体装置 |
JPH04216819A (ja) * | 1990-12-17 | 1992-08-06 | Toshiba Chem Corp | 一液性エポキシ樹脂組成物 |
JPH0867805A (ja) * | 1994-08-29 | 1996-03-12 | Matsushita Electric Works Ltd | 液状エポキシ樹脂組成物 |
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JP2001055486A (ja) * | 1999-06-09 | 2001-02-27 | Shin Etsu Chem Co Ltd | フリップチップ型半導体装置用アンダーフィル材及びフリップチップ型半導体装置 |
JP2001031841A (ja) * | 1999-07-21 | 2001-02-06 | Hitachi Chem Co Ltd | 電子部品封止用エポキシ樹脂組成物 |
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JP2002097341A (ja) * | 2000-09-20 | 2002-04-02 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物及び半導体装置 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102850721A (zh) * | 2005-11-25 | 2013-01-02 | 日立化成工业株式会社 | 电子零件用液状树脂组合物及电子零件装置 |
JP2007169445A (ja) * | 2005-12-21 | 2007-07-05 | Matsushita Electric Works Ltd | アンダーフィル用液状エポキシ樹脂組成物及び半導体装置 |
JP4534980B2 (ja) * | 2005-12-21 | 2010-09-01 | パナソニック電工株式会社 | アンダーフィル用液状エポキシ樹脂組成物及び半導体装置 |
JP2008050544A (ja) * | 2006-08-28 | 2008-03-06 | Matsushita Electric Works Ltd | エポキシ樹脂組成物、半導体装置及び半導体装置の製造方法。 |
WO2008072491A1 (ja) * | 2006-12-11 | 2008-06-19 | Sharp Kabushiki Kaisha | Icチップ実装パッケージ及びその製造方法 |
US8193627B2 (en) | 2006-12-11 | 2012-06-05 | Sharp Kabushiki Kaisha | IC chip mounting package provided with IC chip located in device hole formed within a package base member |
WO2012018684A1 (en) | 2010-08-04 | 2012-02-09 | 3M Innovative Properties Company | Encapsulating resin composition |
JP2014111704A (ja) * | 2012-11-07 | 2014-06-19 | Panasonic Corp | 半導体封止用エポキシ樹脂組成物および半導体装置 |
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