EP2084213A1 - Composition contenant une charge de silice traitée thermiquement pour une amélioration de l'efficacité - Google Patents

Composition contenant une charge de silice traitée thermiquement pour une amélioration de l'efficacité

Info

Publication number
EP2084213A1
EP2084213A1 EP07863777A EP07863777A EP2084213A1 EP 2084213 A1 EP2084213 A1 EP 2084213A1 EP 07863777 A EP07863777 A EP 07863777A EP 07863777 A EP07863777 A EP 07863777A EP 2084213 A1 EP2084213 A1 EP 2084213A1
Authority
EP
European Patent Office
Prior art keywords
filler
resin
resins
silica
thermally
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07863777A
Other languages
German (de)
English (en)
Inventor
Daniel Duffy
Yayun Liu
Allison Yue Xiao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2084213A1 publication Critical patent/EP2084213A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds

Definitions

  • This invention relates to compositions containing a curable resin and thermally treated silica
  • Silica fillers are used in numerous chemical compositions in the fabrication of semiconductor packages and microelectronic devices, and especially in underfill compositions
  • the semiconductor packages and microelectronic devices contain a large number of eiectrical circuit components that are electrically connected to each other and to a earner or substrate
  • One method for making these interconnections uses polymeric or metallic solder that is applied in bumps to the component or substrate terminals The terminals are aligned and contacted together and the resulting assembly is heated to reflow the metallic or polymeric solder and solidify the connection
  • the electronic assembly is subjected to cycles of elevated and lowered temperatures including solder joint and reflow processing and post thermal cycling testing Due to the differences in the coefficient of thermal expansion (CTE) for the electronic component, the interconnect material, and the substrate, this thermal cycling can stress or warp the components of the assembly and cause it to fail
  • CTE coefficient of thermal expansion
  • the gap between the component and the substrate is filled with a poiymeric encapsulant, an underfill, to reinforce the interconnect and balance the CTE mismatch, thus reducing warpage
  • the ability of the underfill to prevent warpage is dependent on the properties of the materials used to formulate the underfill composition
  • the underfill composition comprises a resin system filled with non-conductive filler, with silica being the filler commonly used
  • a measured amount of the underfill is dispensed along one or more peripheries of the electronic assembly and capillary action within the component-to-substrate gap draws the underfill inward.
  • the substrate may be preheated if needed to achieve the desired level of encapsulant viscosity for the optimum capillary action.
  • additional underfill encapsulant may be dispensed along the complete assembly periphery to help reduce stress concentrations and prolong the fatigue life of the assembled structure.
  • This underfilling or wicking process is time consuming and dependent on the flow properties of the underfill material. This makes a high viscosity material in general unsuitable because it slows down capillary flow action.
  • Figure 1 is a graph of viscosity versus temperature for a series of surface treated silica materials in a polyoctylmethyl silicone fluid.
  • Figure 2 is a chart showing the variations in activation energy for some different filler types and resins.
  • Figure 3 is a graph showing the dependence of activation energy on the combination of resin and filler.
  • Figure 4 is a graph illustrating that aluminum nitride particles can exhibit near zero activation energy above a critical surface coverage.
  • Figure 5 is a graph showing that the activation energy depends on filler loading.
  • Figures 6A and 6B present the meaning of the normalized activation energy parameter, Q, and of the normalized interfacial interaction parameter, F, in graphic format.
  • Figure 7 shows the range of F values where near zero Q values were observed for resin/filler pairs.
  • This invention is a curable composition
  • a curable composition comprising a curable resin and a thermally-treated silica filler.
  • the curable composition comprises (a) a thermally treated silica filler, (b) a curable resin (c) an initiator, and (d) optionally, adhesion promoters and/or wetting agents.
  • the curable resins can be cyanate ester resins, epoxy resins, maleimide resins, or acrylate or methacrylate resins.
  • the curable resin is a cyanate ester resin, or an epoxy resin, or a combination of cyanate ester resin and epoxy resin, and a thermally- treated silica filler, with initiator and optionally, adhesion promoters and wetting agents.
  • the heat treatment of the siiica significantly reduces the concentration of hydroxyl groups on the surface resulting in improved compatibility with the resins, and particularly with cyanate ester, improved flow behavior, reduction in CTE and enhancement of modulus.. Chip packages underfilled with resins and thermally treated silica have reduced warpage because of these property characteristics.
  • silica filler is supplied by the manufacturer with the surface treated with silanes or containing a high concentration of hydroxyl groups.
  • Some resins for example, cyanate esters, are reactive with hydroxyl groups and the reaction releases volatile materials. When underfills cure, volatiles escape from the underfill composition creating voids, which can lead to eventual failure of the ultimate electronic device. Removal of the hydroxyl groups would correct this problem.
  • the viscosity of a composition is determined by how filler and resin interact. By removing the hydroxyl groups, the surface energy of the silica is lowered, making the silica more compatible with the surface energy of particular resins, and especially cyanate esters, and consequently lowering the viscosity.
  • Cyanate esters suitable for use as underfill materials include those having the
  • X is a hydrocarbon group.
  • exemplary X entities include, but are not limited to, bisphenol A, bisphenol F, bisphenoi S, bisphenol E, bisphenol O, phenol or cresol novolac, dicyclopentadiene, polybutadiene, polycarbonate, polyurethane, polyether, or polyester.
  • cyanate ester materials include; AROCY L-10, AROCY XU366, AROCY XU371, AROCY XU378, XU71787.02L, and XU 71787.07L, available from Huntsman LLC; PRIMASET PT30, PRIMASET PT30 S75, PRIMASET PT60, PRIMASET PT60S, PRIMASET BADCY 1 PRIMASET DA230S, PRIMASET MethylCy, and PRIMASET LECY, available from Lonza Group Limited; 2-allyphe ⁇ ol cyanate ester, 4- methoxyphenol cyanate ester, 2,2-bis(4-cyanatophenol)-1 ,1 ,1 ,3,3,3-hexafluoropropane, bisphe ⁇ ol A cyanate ester, diallylbisphenol A cyanate ester, 4-phenylpheno] cyanate ester, 1,1,1-tris(4-cyanatophenyl)ethane, 4-
  • cyanate esters having the structure:
  • R 1 to R 4 independently are hydrogen
  • cyanate esters having the structure: in which R 1 to R 5 independently are hydrogen, C 1 - Cio alkyl, C 3 -C 8 cycloalkyi, C 1 -C 10 aikoxy, halogen, phenyl, phenoxy, and partially or fully fluorinated alkyl or aryl groups;
  • R 1 to R 4 independently are hydrogen, C 1 - C 10 alkyl, C 3 -C 8 cycloalkyi, C 1 -C 10 alkoxy, halogen, phenyi, phenoxy, and partially or fully fluorinated alkyl or aryl groups;
  • n is a number from 0 to 20
  • R 6 is hydrogen or d- C 10 alkyl
  • X is CH 2 or one of the following structures
  • Suitable epoxy resins include bisphenol, naphthalene, and aliphatic type epoxies
  • Commercially available materials include bisphenol type epoxy resins (EPICLON 830LVP 1 830CRP, 835LV, 850CRP) available from Dainippo ⁇ Ink & Chemicals, lnc , naphthalene type epoxy (EPICLON HP4032) available from Dainippon Ink & Chemicals, Inc., aliphatic epoxy resins (ARALDITE CY179, 184, 192, 175, 179) available from Ciba Specialty Chemicals, (Epoxy 1234, 249, 206) available from Dow Corporation, and (EHPE-3150) available from Daicel Chemical Industries, Ltd
  • Suitable epoxy resins include cycloaliphatic epoxy resins, btsphenol-A type epoxy resins, bisphenol-F type epoxy resins, epoxy novolac resins, biphenyl type epoxy resins, naphthalene type epoxy resins, dicyclopentadienephenol type epoxy resins [0032] Suitable maleimide resins include those having the generic structure
  • X 1 is an aliphatic or aromatic group.
  • exemplary X 1 entities include, poly(butadienes), poly(carbonates), poly(urethanes), poly(ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate, urea, ester, or ether. These types of resins are commercially available and can be obtained, for example, from Dainippon Ink and Chemical, Inc.
  • Additional suitable maleimide resins include, but are not limited to, solid aromatic bismaieimide (BMI) resins, particularly those having the structure
  • Q is an aromatic group.
  • aromatic groups include:
  • n 1 - 3
  • Bismaleimide resins having these Q bridging groups are commercially available, and can be obtained, for example, from Sartomer (USA) or HOS-Technic GmbH (Austria).
  • maleimide resins include the following:
  • C 36 represents a linear or branched hydrocarbon chain (with or without cyclic moieties) of 36 carbon atoms;
  • Suitable acrylate and methacrylate resins include those having the generic
  • Exemplary X 2 entities include poly(butadienes), poly-(carbonates), poly(urethanes), poly(ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate, urea, ester, or ether.
  • Commercially available materials include butyl (meth)acrylate, isobutyl (meth)acrylate, 2-ethyl hexy!
  • (meth)acrylate isodecyl (meth)acrylate, n-lauryl (meth)acrylate, alkyl (meth)-acrylate, tridecyl(meth)-acrylate, n-stearyl (meth)acrylate, cyclohexyl(meth)-acrylate, tetrahydrofurfuryl-(meth)acrylate, 2-phenoxy ethyl(meth)- acrylate, isobornyl(meth)acrylate, 1 ,4-butanediol di(meth)acry]ate, 1 ,6- hexanedio!
  • the acrylate resins are selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, lauryl acrylate, lauryl methacrylate, poly(butadiene) with acrylate functionality and poly(butadiene) with methacrylate functionality.
  • Suitable silica particles are spherical with average particle sizes of from 0.1 ⁇ , to 10 ⁇ and can be obtained, for example, from Admatechs as products SOE5 and SOE2. In one embodiment, mixtures of sizes can be used for increasing the total filler loading level and at the same time keeping the viscosity at a manageable level.
  • the thermal treatment procedure is conducted by placing aliquots, typically 10g to 50g, of silica powder as received from the supplier into ceramic crucibles and heating them in an oven preheated to a temperature or a range of temperatures between 400°C and 450°C for a period of 72 hours.
  • a suitable furnace is a Thermolyne F-A1740 muffle furnace.
  • the crucibles are removed from the furnace and allowed to cool to 80°C under dry air or nitrogen.
  • the treated silica is transferred hot (80 0 C) from crucibles to polymer based storage containers with an air tight seal (for example, 250ml amber Nalgene bottles) under a dry atmosphere.
  • Containers filled with treated silica can be stored in evacuated packaging (such as food-saver bags) for additional protection from ambient moisture and long term storage.
  • compositions were prepared and tested for flow capability using a resin composition and silica filler treated as described in the detailed description.
  • the resin composition consisted of 60% by weight of cyan ate ester (obtained as PRIMASET
  • the silica filler had a maximum particle size of 5 ⁇
  • Filled samples were prepared by combining the resin and filler in polypropylene cups with 3mm glass or zirconia milling media. The cups were placed into a Flaktek Speed Mixer and processed in three sequential 30 second mixing cycles at 1800 RPM, 2100 RPM and 2700 RPM respectively.
  • the flow velocity of the filled cyanate ester/epoxy resin compositions were measured with a custom designed instrumentation consisting of a rectangular capillary channel, a temperature controlled flow chamber, and an optical configuration and digital imaging system for flow front measurement.
  • the channel is constructed of an upper and lower substrate bonded together along their lengths on both sides and separated by some distance. Results reported here were obtained using two glass slides (75x25 mm) and a separation of 50 ⁇ .
  • the temperature controlled flow chamber is designed to hold the channel described above and provide a uniform temperature across the entire sampie and test vehicle. Flow behavior in the range of 20 0 C to 280°C can be investigated with this system. One end of the chamber allows access to the beginning of the channel so that the sample can be introduced.
  • Samples were introduced via syringe, and 0.05 to 0.1.2 ml of material was deposited.
  • the top of the chamber is designed so that the sample can be viewed as it flows down the channel.
  • the flow of the material in the channel is captured by a digital image acquisition system. Flow front position, velocity and estimated fill-time are obtained from digital image analysis.
  • the flow rate shows minimal dependence on the filler treatment at low filler loading levels. However, as the concentration increases past the percolation point, approximately 35% by weight, the filler surface properties begin to contribute significantly to the viscosity and therefore the flow rate. To meet thermal expansion and modulus performance requirements silica needs to be present at a level of least 40%.
  • the table above shows at least a five-fold improvement in the flow rate at 70% filler loading using the thermally treated filler. The thermally treated filler can enable high loading without compromising flow rate in the cyanate ester/epoxy system.
  • Warpage is measured as the height difference between the highest point and the lowest point of the underfilled package, relative to the substrate.
  • Compositions were prepared and tested for warpage using a resin system and thermally treated silica filler as described in the detailed description.
  • the resin formulations consisted of 55.8% by weight of cyanate ester (obtained as PRIMASET LECY from Lonza Ltd.), 37.2% by weight of Bis F-epoxy resin (prepared in-house by National Starch and Chemical Company), and 7% by weight of 3,3' diamino diphenyl sulfone (obtained from Aldrich). The resin components were mixed together before the filler was added.
  • the silica filler had a maximum particle size of 5 ⁇ (obtained as SOE2from Admatechs) and was loaded into the resin system at 40% and 60% by weight.
  • the resin and fillers were mixed by a high speed centrifuge mixer at 3000 rpm for five minutes and then degassed to remove trapped air in the formulations.
  • the warpage tests were conducted using flip chip test vehicles.
  • the die was 15X15mm with lead free solders and the substrate was a BT laminate 42X42mm.
  • the die and BT substrate were jointed together through a standard lead free reflow process.
  • test vehicles Prior to underfilling, test vehicles were heated in a165°C oven for two hours to remove absorbed moisture. The test vehicles were then kept at 110 0 C during underfilling.
  • the underfill formulations were dispensed from a syringe with 0.33mm needle by hand only along one side of the die. The filled packages were then cured at 165°C for 90 minutes.
  • the warpage of the test vehicles were measured using a laser profilometer (Cobra 3D, Optical Gaging Product) on the backside of the substrate along the two diagonal directions. The average height of the two curves was calculated as the warpage of the package. The warpage measurements were taken before underfilling and immediately after the cured packages being cooled to 25°C. The warpage increase after cure was used to compare the effect of filler on the warpage. The results are reported in Table 2.
  • Figure 1 shows a graph of viscosity versus temperature for a series of surface treated silica materials in a polyoctylm ethyl silicone (POMS) fluid.
  • the surface treatments were conducted with phenyl trialkoxy silane (phenyl in the Figure), phenyl amino trialkoxy silane (phenyl amino), and dimethyl silicone oligomer end terminated with a trialkoxy s ⁇ ane group (silicone).
  • the filler size and loading ievel are identical for this series.
  • the graph shows that with increasing temperature, the viscosity decreases, but at different rates for the different fillers.
  • the behavior of filled resin systems is an energy activated process.
  • the activation energy can be experimentally determined from the slope of the line resulting from a plot of the logarithm of viscosity versus reciprocal temperature.
  • POMS for example has an activation energy (Ea) of 2000K at a shear rate of 1 rad/s while a typical Bis-F epoxy is 9190K at the same rate.
  • Activation energies (Ea) were determined for silica and alumina fillers with a series of surface treatments in epoxy, poly(phenylmethyl)silicone (PPMS) and POMS.
  • the variations in activation energy for some different filler types and resins are shown in Figure 2 (activation energy values obtained from a plot of the natural log of the viscosity versus MT). A wide range of behaviors are exhibited; some systems mimic the activation energy of the unfilled resin; some remain invariant with temperature; and others thicken slightly with temperature.
  • a cyanate ester resin (PRIMASET L-10) was loaded with silica having the following surface modifications: treated with hexamethyldisilaza ⁇ e (HMDZ), treated with epoxy silane, thermally treated (calcinated), and untreated.
  • HMDZ hexamethyldisilaza ⁇ e
  • the untreated, epoxy silane treated and calcinated filler materials all thin with temperature, but the HMDZ treated material initially thins and then thickens with temperature. See Figure 3. This sort of behavior is not easily anticipated or even expected.
  • activation energy parameter is and the normalized interfacial
  • underfill formulations JKL and MNO
  • POMS as the resin
  • silica as the filler
  • Formulation JKL silica was surface treated with silicone
  • MNO silica was surface treated with phenyl silane.
  • the activation energy is positive for JKL and near zero for MNO.
  • These formulations were deposited between a silicon wafer and a glass substrate, and equilibrated at room temperature for several hours. Both formulations filled the volume under the wafer completely before heating and had a similar fillet shape and width.
  • the formulations were placed on a hot plate with a surface temperature of 12O 0 C for V-i hour, after which it was observed that the MNO formulation with the near- zero Ea (activation energy) remained under the wafer while JKL bled out.
  • the Ea determined from the Theological behavior clearly manifested itself in terms of the electronic materials relevant performance characteristic of bleed-out control.
  • the interfacial & Theological properties of the filled POMS resins had the following characteristics:
  • the Q versus loading level was mapped for a mafeimide resin and a cydoaSiphatic epoxy resin as a function of filler ioading and surface treatment, and the correlation predicts that these two materials should thin with temperature for all loading levels.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

La présente invention concerne une composition durcissable contenant une résine durcissable et une charge de silice traitée thermiquement, qui, lorsqu'elle sert de matière de remplissage diélectrique dans des boîtiers de semi-conducteurs, permet d'améliorer le comportement de l'écoulement, de réduire le coefficient de dilatation thermique et d'améliorer le module, ce qui entraîne une diminution du gauchissement. Dans un mode de réalisation, la composition durcissable selon l'invention contient : (a) une charge de silice traitée thermiquement; (b) une résine durcissable; (c) un initiateur; et (d) éventuellement des promoteurs d'adhésion et/ou des agents mouillants. Les résines durcissables selon l'invention peuvent être des résines d'ester de cyanate, des résines époxydes, des résines maléimides ou des résines acrylate ou méthacrylate.
EP07863777A 2006-11-02 2007-11-01 Composition contenant une charge de silice traitée thermiquement pour une amélioration de l'efficacité Withdrawn EP2084213A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85624506P 2006-11-02 2006-11-02
PCT/US2007/083319 WO2008057931A1 (fr) 2006-11-02 2007-11-01 Composition contenant une charge de silice traitée thermiquement pour une amélioration de l'efficacité

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EP2084213A1 true EP2084213A1 (fr) 2009-08-05

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EP (1) EP2084213A1 (fr)
JP (1) JP2010509410A (fr)
KR (1) KR20090090324A (fr)
CN (1) CN101535379A (fr)
TW (1) TW200920779A (fr)
WO (1) WO2008057931A1 (fr)

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US8970034B2 (en) 2012-05-09 2015-03-03 Micron Technology, Inc. Semiconductor assemblies and structures
MX2016010401A (es) * 2014-02-14 2016-11-30 Rhodia Operations Procedimiento para la preparacion de silices precipitadas, silices precipitadas y sus usos, en particular para el refuerzo de polimeros.
CN106133045B (zh) 2014-04-03 2018-11-20 株式会社Lg化学 在基于氰酸酯的树脂中具有优良分散性的二氧化硅溶胶组合物及其制备方法
KR101745676B1 (ko) 2014-05-30 2017-06-09 주식회사 엘지화학 시아네이트계 수지에 대한 분산성이 우수한 실리카졸 조성물 및 이의 제조 방법
CN111065603B (zh) * 2018-08-17 2021-04-23 浙江三时纪新材科技有限公司 一种半导体封装材料的制备方法以及由此得到的半导体封装材料
US11746183B2 (en) * 2018-09-11 2023-09-05 United States Of America As Represented By The Administrator Of Nasa Durable contamination resistant coatings

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KR20090090324A (ko) 2009-08-25
WO2008057931A1 (fr) 2008-05-15
TW200920779A (en) 2009-05-16
CN101535379A (zh) 2009-09-16
JP2010509410A (ja) 2010-03-25

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