WO2015010231A1 - Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium - Google Patents

Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium Download PDF

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Publication number
WO2015010231A1
WO2015010231A1 PCT/CN2013/079762 CN2013079762W WO2015010231A1 WO 2015010231 A1 WO2015010231 A1 WO 2015010231A1 CN 2013079762 W CN2013079762 W CN 2013079762W WO 2015010231 A1 WO2015010231 A1 WO 2015010231A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylate
range
composition
composition according
weight
Prior art date
Application number
PCT/CN2013/079762
Other languages
English (en)
Inventor
Yuanyuan Yu
Qizhuo Zhuo
Chuanguang Wang
Original Assignee
Ablestik (Shanghai) Limited
Henkel IP & Holding GmbH
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 Ablestik (Shanghai) Limited, Henkel IP & Holding GmbH filed Critical Ablestik (Shanghai) Limited
Priority to PCT/CN2013/079762 priority Critical patent/WO2015010231A1/fr
Priority to CN201380078137.2A priority patent/CN105492563B/zh
Priority to TW103124968A priority patent/TWI638021B/zh
Publication of WO2015010231A1 publication Critical patent/WO2015010231A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical

Definitions

  • Adhesives are used frequently in the fabrication of electronic devices, for example, to attach individual semiconductor dies to substrates.
  • a semiconductor die is adhered to its substrate with a paste or film adhesive.
  • the assembly is then subjected to heat to cure the adhesive so that it develops sufficient strength to survive subsequent processing steps and to eliminate voids formed by out-gassing during these later fabrication stages.
  • this cure schedule can be as long as an hour.
  • the active terminals on the surface of the semiconductor die are then connected to the active terminals on the substrate with metal wires in an automated operation known as wire bonding, which occurs at about 125° to 210°C. After wire bonding, the assembly is
  • the current trend in semiconductor packaging fabrication favors completing as many process steps as possible at the silicon wafer level, before the wafer is diced into individual semiconductor dies.
  • a further trend for stacked die packages is to combine or eliminate as many cure steps as possible. This allows multiple semiconductor dies to be processed at the same time, making the fabrication process more efficient.
  • One step that can occur at the wafer level is the application of the adhesive for attaching the semiconductor dies to substrates.
  • the adhesive is known as a wafer backside coating adhesive and is applied by screen or stencil printing, spin-coating, or nozzle spraying. Nozzle spraying can give more efficient and more uniform application, but the adhesive composition must be of the right rheology for a successful application.
  • the coating is thermally or photochemically treated to evaporate solvent and/or partially advance the adhesive resin (known as B-staging). This strengthens the adhesive for the further fabrication processes.
  • This invention is an adhesive composition that has sufficient mechanical and adhesive strength to withstand manufacturing operations at high temperatures without being fully cured.
  • the adhesive composition is exposed for a few seconds to several minitues at 100 ⁇ 150°C during the die attach process. Under these relatively mild conditions, the adhesive develops sufficient mechanical and adhesive strength to withstand the subsequent wire bonding operation, at temperatures typically 125° to 210°C, and molding operation, at temperatures typically 170° to 180°C, without out-gassing and creating voids.
  • the typical hour long heat cure after die attach can be skipped.
  • This skip-cure adhesive composition comprises (i) a low glass transition (Tg) acrylate monomer, (ii) a difunctional acrylate/epoxy compound, (iii) a phenoxy resin, and (iv) a solid epoxy resin. None of the materials in this composition is an elastomer or rubber.
  • Low glass transition (Tg) acrylate monomers are liquid at room temperature and have Tg values within the range of -90°C to 30°C.
  • Suitable acrylate monomers with Tg values within this range include tetrahydrofurfuryl acrylate, alkoxylated tetrahydrofurfuryl acrylate, lauryl acrylate, 2-phenoxyethyl acrylate, tridecyl acrylate, caprolactone acrylate, cyclic
  • the low Tg acrylate monomer will be present in any amount or range of amounts, within the range of 20% to 75% by weight or within the range of 40% to 65% by weight, of the adhesive composition.
  • the difunctional acrylate/epoxy resin will have both acrylate and epoxy functionality on one molecule, herein "acrylate/epoxy". Suitable compounds include 4-hydroxybutyl acrylate glycidylether, glycidyl acrylate, and glycidyl methacrylate.
  • the difunctional acrylate/epoxy resin will be present in any amount or range of amounts within the range of 0% to 20% by weight or within the range of 4% to 10% by weight of the adhesive composition.
  • the phenoxy resins are high molecular weight thermoplastic polyhydroxyethers with alpha-glycol terminal groups, which polyhydroxyethers are the reaction products of bisphenol-A and epichlorohydrin. Suitable phenoxy resins have molecular weights within the range of 10,000 to 50,000 Daltons. Phenoxy resins will be present in the adhesive composition in any amount or range of amounts within the range of 10% to 33% by weight of the composition.
  • the solid epoxy resin can be selected from commercially available resins. Suitable solid epoxy resins include the group of novolac epoxy resins, bis-phenol epoxy resins, aliphatic epoxy resins, and aromatic epoxy resins. In one embodiment, the epoxy resin has a weight average molecular weight of 5000 or less. The solid epoxy resin will be present in the adhesive composition in any amount or range of amounts, within the range of 0% to10% or within the range of 5% to 8% by weight .
  • Pigments or dyes can be added to visibly help distinguish between cured and un-cured adhesive.
  • the pigments and dyes can be any color; suitable colors include blue and red. When used, the pigment or dye will be present in any amount or range of amounts within the range of 0.01 % to 1.0% by weight of the composition.
  • the adhesive composition will further contain a photoinitiator and/or a latent catalyst.
  • the photoinitiator will be used to activate the acrylate functionality and the latent catalyst used to activate the epoxy functionality.
  • the photoinitiator will be in any amount or range of amounts within the range of 0.5% to 5% by weight of the composition, and the latent catalyst will be present in an amount or range of amounts within the range of 0.01 % to 1 % by weight of the composition.
  • a curing agent is any material or combination of materials that initiate, propagate, or accelerate cure of the coating and includes accelerators, catalysts, initiators, and hardeners.
  • compositions according to this invention and for comparison were prepared to contain the components shown in Tables 1 and 2.
  • Table 3 shows the chemical names and sources for the components used. These formulations were tested for performance in a test vehicle comprising a silicon die on a plastic ball grid array (PBGA) substrate, in which the adhesive is disposed between the silicon die and substrate and was applied at 1 10° to 130°C, with 1 to 1.5 Kg force, for 1 to 2 seconds.
  • the PBGA substrate has a roughness profile of about 6 to 8 ⁇ , compared to an Alloy 42 substrate, which has a roughness profile of about less than 1 ⁇ . The higher roughness level of the PBGA substrate makes it more difficult to achieve a satisfactory thermal budget.
  • Spray-ability was tested using a spray-coating machine from Asymtec, which can detect coating thickness at >10um and roughness at ⁇ 10% variation. Spray-ability was determined to be achieved for the purpose of the test if the composition formed a relatively uniform film having a coating thickness >10um and ⁇ 10% variation after UV irradiation.
  • Die shear green strength was tested at 175°C on Dage Bonding die tester. An acceptable die shear green strength was determined to be achieved at 0.100 Kg force. This level was deemed sufficient to withstand subsequent processing steps, such as wire-bonding and molding processes.
  • Hot die shear strength was tested using a Dage Bonding die tester at 260°C, after first heating the test vehicle at 175°C for four hours. An acceptable hot die shear strength was determined to be achieved at 1.OKg force. This level was deemed sufficient to pass reliability testing.
  • Moisture resistance was tested by conditioning the test vehicle in a humidity chamber at 85% relative humidity and 85°C for 168 hours, heating the test vehicle at 260°C for three minutes and cooling three times, and then using a C-SAM to check for delamination. Delamination is deemed a failure.
  • Thermal budget was tested by heating the test vehicle at 150°C or 175°C for a certain number of hours and then introducing it into a Lauffer Molding machine at 175°C to determine if deformable. Thermal budget is the length of time an adhesive will continue to re-flow and re- cure after initial cure, typically at the wire bonding temperature , without causing out-gassing and the formation of voids. (Thermal budget is necessary for die stacking operations.) A thermal budget of 175°C for one hour was deemed acceptable for wafer back side coating compositions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Cette invention porte sur une composition adhésive ayant une force mécanique et adhésive suffisante pour résister à des opérations de fabrication à des températures entre 125 et 210°C sans être durcie au préalable. En bref, le durcissement après l'opération de fixation de puce est omis, et l'adhésif peut fonctionner sans dégazage et création de vides pendant toute l'opération de liaison des fils, à des températures généralement de 125 à 210°C, et l'opération de moulage, à des températures généralement de 170 à 80°C. La composition adhésive comprend (i) un monomère acrylate à basse température de transition vitreuse (Tg), (ii) un composé d'acrylate/époxy difonctionnel, (iii) une résine phénoxy, et (iv) une résine époxy solide.
PCT/CN2013/079762 2013-07-22 2013-07-22 Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium WO2015010231A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/CN2013/079762 WO2015010231A1 (fr) 2013-07-22 2013-07-22 Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium
CN201380078137.2A CN105492563B (zh) 2013-07-22 2013-07-22 可b阶段化且无需固化的晶片背面涂覆粘合剂
TW103124968A TWI638021B (zh) 2013-07-22 2014-07-21 可ｂ階段化且可無需固化之晶圓背面塗覆黏著劑

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2013/079762 WO2015010231A1 (fr) 2013-07-22 2013-07-22 Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium

Publications (1)

Publication Number Publication Date
WO2015010231A1 true WO2015010231A1 (fr) 2015-01-29

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2013/079762 WO2015010231A1 (fr) 2013-07-22 2013-07-22 Adhésifs de stade b et à durcissement pouvant être omis destinés à revêtir la face arrière de tranches de silicium

Country Status (3)

Country Link
CN (1) CN105492563B (fr)
TW (1) TWI638021B (fr)
WO (1) WO2015010231A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6843815B1 (en) * 2003-09-04 2005-01-18 3M Innovative Properties Company Coated abrasive articles and method of abrading
CN1632024A (zh) * 2004-12-22 2005-06-29 华南理工大学 结构压敏粘合剂
CN101368078A (zh) * 2008-09-19 2009-02-18 航天材料及工艺研究所 一种用于软木粘接和修补的粘胶剂及配制方法
CN101720344A (zh) * 2008-05-16 2010-06-02 Posco公司 用于预涂钢板的树脂组合物以及具有良好的加工性、耐热性以及耐蚀性的钢板

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1089356C (zh) * 1995-04-04 2002-08-21 日立化成工业株式会社 粘合剂、胶膜及带粘合剂底面的金属箔
US20070179232A1 (en) * 2006-01-30 2007-08-02 National Starch And Chemical Investment Holding Corporation Thermal Interface Material
TWI357922B (en) * 2007-12-24 2012-02-11 Eternal Chemical Co Ltd Coating compositions and curing method thereof
TW200948888A (en) * 2008-04-16 2009-12-01 Henkel Corp Flow controllable B-stageable composition
JP2013057017A (ja) * 2011-09-08 2013-03-28 Sekisui Chem Co Ltd 絶縁材料、積層体、接続構造体、積層体の製造方法及び接続構造体の製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6843815B1 (en) * 2003-09-04 2005-01-18 3M Innovative Properties Company Coated abrasive articles and method of abrading
CN1632024A (zh) * 2004-12-22 2005-06-29 华南理工大学 结构压敏粘合剂
CN101720344A (zh) * 2008-05-16 2010-06-02 Posco公司 用于预涂钢板的树脂组合物以及具有良好的加工性、耐热性以及耐蚀性的钢板
CN101368078A (zh) * 2008-09-19 2009-02-18 航天材料及工艺研究所 一种用于软木粘接和修补的粘胶剂及配制方法

Also Published As

Publication number Publication date
TWI638021B (zh) 2018-10-11
CN105492563B (zh) 2019-04-23
CN105492563A (zh) 2016-04-13
TW201520297A (zh) 2015-06-01

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