Controllable radiation curable photoiniferter prepared adhesives for attachment of microelectronic devices and a method of attaching microelectronic devices therewith

• US 5,356,947 A
• Filed: 10/29/1992
• Issued: 10/18/1994
• Est. Priority Date: 03/29/1990
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Ali, Mahfuza B., Pujol, Jean M.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US07/968,251
• Time in Patent Office: 719 Days
• Field of Search: 522/57, 522/149, 522/173, 522/174, 522/904, 522/182, 522/18, 522/90, 522/96, 522/100, 522/103, 522/166, 522/81, 522/83, 528/69, 528/356, 528/363, 528/364, 528/366, 528/390, 526/258, 526/260, 525/260, 428/40, 428/355
• US Class Current: 522/57
• CPC Class Codes: C08F 287/00 Macromolecular compounds obtained by polymerising monomers on to block polymers
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• CPC Class Codes: H01L 2224/2919 with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
• CPC Class Codes: H01L 2224/8319 Arrangement of the layer connectors prior to mounting
• CPC Class Codes: H01L 2224/8385 using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester
• CPC Class Codes: H01L 24/28 Structure, shape, material or disposition of the layer connectors prior to the connecting process
• CPC Class Codes: H01L 24/83 using a layer connector
• CPC Class Codes: H01L 2924/00 Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
• CPC Class Codes: H01L 2924/01005 Boron [B]
• CPC Class Codes: H01L 2924/01006 Carbon [C]
• CPC Class Codes: H01L 2924/01013 Aluminum [Al]
• CPC Class Codes: H01L 2924/01015 Phosphorus [P]
• CPC Class Codes: H01L 2924/0102 Calcium [Ca]
• CPC Class Codes: H01L 2924/01023 Vanadium [V]
• CPC Class Codes: H01L 2924/01024 Chromium [Cr]
• CPC Class Codes: H01L 2924/01025 Manganese [Mn]
• CPC Class Codes: H01L 2924/01029 Copper [Cu]
• CPC Class Codes: H01L 2924/01032 Germanium [Ge]
• CPC Class Codes: H01L 2924/01042 Molybdenum [Mo]
• CPC Class Codes: H01L 2924/01045 Rhodium [Rh]
• CPC Class Codes: H01L 2924/01047 : Silver [Ag]
• CPC Class Codes: H01L 2924/01049 : Indium [In]
• CPC Class Codes: H01L 2924/0105 : Tin [Sn]
• CPC Class Codes: H01L 2924/01052 : Tellurium [Te]
• CPC Class Codes: H01L 2924/01055 : Cesium [Cs]
• CPC Class Codes: H01L 2924/01057 : Lanthanum [La]
• CPC Class Codes: H01L 2924/01067 : Holmium [Ho]
• CPC Class Codes: H01L 2924/01073 : Tantalum [Ta]
• CPC Class Codes: H01L 2924/01074 : Tungsten [W]
• CPC Class Codes: H01L 2924/01075 : Rhenium [Re]
• CPC Class Codes: H01L 2924/01077 : Iridium [Ir]
• CPC Class Codes: H01L 2924/01079 : Gold [Au]
• CPC Class Codes: H01L 2924/01088 : Radium [Ra]
• CPC Class Codes: H01L 2924/014 : Solder alloys
• CPC Class Codes: H01L 2924/0665 : Epoxy resin
• CPC Class Codes: H01L 2924/07802 : not being an ohmic electrical conductor
• CPC Class Codes: H01L 2924/10253 : Silicon [Si]
• CPC Class Codes: Y10S 522/904 : Monomer or polymer contains initiating group
• CPC Class Codes: Y10T 428/2839 : with release or antistick coating

Abstract

The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.

Claims

1. An adhesive comprising the condensation reaction product of

(a) a polymer prepared by the ultraviolet light induced polymerization of

(i) monofunctional acrylate monomers chosen from the group consisting of methyl (meth)acrylate, isooctyl acrylate, ethyl acrylate, isobornyl acrylate, norbornyl acrylate, butyl acrylate, phenethyl methacrylate, dimethylaminoethyl methacrylate and trimethoxysilylpropyl methacrylate and mixtures thereof, and

(ii) difunctional ethylenically-unsaturated monomers chosen from the group consisting of 2-vinyl-4,4-dimethyl-2-oxazoline-5-one, hydroxyethyl (meth)acrylate, glycidyl (meth)acrylate, isocyanatoethyl methacrylate, (meth)acrylic acid, pentaerythritol tri(meth)acrylate and dimethylamino methacrylate and mixtures thereof;

and

(iii) a photoiniferter chosen from the group consisting of xylylene bis (N,N-diethyldithiocarbamate), benzyl carbazolyl thiocarbamate, xylylene carbazolyldithiocarbamate, durene α

,α

'"'"',α

",α

'"'"'"-tetrakis (N,N-diethyldithiocarbamate), benzyl N,N-diethyldithiocarbamate, and mixtures thereof;

with

(b) a condensation-reactive ethylenically-unsaturated monomer chosen from the group consisting of 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, hydroxyethyl methacrylate, hydroxyethyl acrylate, glycidyl acrylate, glycidyl methacrylate, isocyanatoethyl methacrylate, acrylic acid, methacrylic acid, dimethylaminoethyl methacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, and mixtures thereof;

wherein no additional photoinitiator other than said photoiniferter is present, and

wherein said condensation reaction product is controllably crosslinked in a stepwise fashion by intermittent controlled exposure to an ultraviolet radiation source.

2. The adhesive of claim 1 wherein said difunctional ethylenically-unsaturated monomer is 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, said monofunctional acrylate monomer is dimethylaminoethyl methacrylate and said condensation reactive ethylenically-unsaturated monomer is selected from the group consisting of hydroxyethyl methacrylate, hydroxyethyl acrylate, and mixtures thereof.

3. The adhesive of claim 2 wherein the weight ratio of 2-vinyl-4,4-dimethyl-2-oxazolin-5-one to dimethylaminoethyl methacrylate ranges from about 90:

10 to about 10;

90.

4. The adhesive of claim 1 wherein said iniferter comprises xylylene bis (N,N-diethyl dithiocarbamate).

5. The adhesive of claim 1 which further comprises about 0.1 to about 5.0 weight percent of a sensitizer.

6. The adhesive of claim 1 which further comprises up to about 60 weight percent of a filler.

7. The adhesive of claim 1 which further comprises about 0.1 to about 20 percent of a coupling agent.

8. The adhesive of claim 7 wherein said coupling agent comprises trimethoxysilylpropyl methacrylate.

9. The adhesive of claim 1 which further comprises about 1 to about 10 weight percent of multifunctional monomer.

10. The adhesive of claim 1 which further comprises about 1 to about 10 weight percent of a multifunctional monomer wherein said multifunctional monomer is selected from the group consisting of pentaerythritol trimethacrylate, pentaerythritol triacrylate, ethoxylated bisphenol A dimethacrylate, and mixtures thereof.

11. A film of the adhesive composition of claim 1 coated on a release backing.