IP Library › Granted Patent US 12703815
Granted Patent B2
US 12703815 · App. 18/073,351 · Granted Aug 11, 2026

Flux-compatible epoxy-anhydride adhesives compositions for low-gap underfill applications

Inventors: Sandeep Kapadia (Bellflower, CA); Laxmisha M. Sridhar (Monmouth Junction, NJ); Zhan Hang Yang (Rocky Hill, CT); Pukun Zhu (Irvine, CA); Sarah Liao (Claremont, CA)
Assignee: Henkel AG & Co. KGaA
C09J163/00C09J173/02C09J2301/408
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Quick Facts
Patent No.
US 12703815
App. No.
18/073,351
Granted
Aug 11, 2026
Kind
B2
Abstract

Provided are flux-compatible epoxy-anhydride compositions useful as low-gap underfill adhesives. The flux-compatible epoxy-anhydride compositions include an epoxy component and an anhydride composition comprising a monofunctional anhydride and at least one difunctional anhydride and optionally at least one polyfunctional anhydride. The flux-compatible compositions are useful as an underfilling sealant which (1) rapidly fills the underfill space in a semiconductor device, such as a flip chip assembly, (2) enables the device to be securely connected to a circuit board by short-time heat curing and with good productivity, and (3) demonstrates excellent solder reflow resistance.

Claims (15)

1 . A flux-compatible epoxy-anhydride adhesive for low-gap underfill applications comprising:

an anhydride component comprising one or more mono anhydride and a dianhydride, wherein the dianhydride comprises a mixture of 4,4′-(4,4′-isopropylidene diphenoxy)bis(phthalic anhydride) and 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; and

an epoxy resin component comprising an epoxy resin(s) selected from monofunctional and multifunctional glycidyl ethers, glycidyl esters, cycloaliphatic epoxy, and aromatic amine derived glycidyl resins.

2 . A flux-compatible epoxy-anhydride adhesive of claim 1 wherein the epoxy component is selected from one or more of bisphenol F diglycidyl ether, bisphenol A diglycidyl ether, diepoxide of a cycloaliphatic alcohol, hydrogenated bisphenol A diglycidyl ether, glycidyl esters of hexahydrophthallic anhydride, dicyclopentadiene-novolac glycidyl ether, cycloaliphatic epoxy, dicyclopentadiene dimethanol diglycidyl ether, phenol novaloc glycidyl ether, aromatic amine derived glycidyl systems, and epoxides of cyclic dienes and trienes.

3 . The flux-compatible epoxy-anhydride adhesive of claim 1 further comprising a maleimide-containing compound resin.

4 . The flux-compatible epoxy-anhydride adhesive of claim 3 , wherein the maleimide-containing compound is derived from 6-maleimidocaproic acid Fischer esterification with aliphatic diols.

5 . The flux-compatible epoxy-anhydride adhesive of claim 3 wherein the maleimide-containing compound is derived from maleinization of aromatic or aliphatic diamines or polyamines.

6 . The flux compatible epoxy-anhydride adhesive of claim 1 , wherein the anhydride composition further comprises a polyanhydride which is not a dianhydride.

7 . The flux compatible epoxy-anhydride adhesive of claim 6 wherein the polyanhydride component comprises one or more of polypropylene-graft-maleic anhydride, polyethylene-graft-maleic anhydride, butadiene-maleic anhydride copolymers, styrene-maleic anhydride copolymers and other copolymers and terpolymers of maleic anhydride.

8 . The flux-compatible epoxy-anhydride adhesive of claim 1 , wherein the mono anhydride comprises methyl nadic anhydride (MNA), and one or more of methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, hexahydro-4-methylphthalic anhydride (MHHPA), methyltetrahydrophthalic anhydride (MTHPA), methylcyclohexene-1,2-dicarboxylic anhydride, methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, (2-Dodecen-1-yl) succinic anhydride, glutaric anhydride, citraconic anhydride, methylsuccinic anhydride, 2,2,-dimethylsuccinic anhydride, 2,2, dimethylglutaric anhydride, 3-methylglutaric anhydride, 3,3-Tetramethyleneglutaric anhydride, and 3,3-Dimethylglutaric anhydride.

9 . The flux-compatible epoxy-anhydride adhesive of claim 1 , wherein the ratio of the mono anhydride and the dianhydride in the anhydride component is from about 1:1 to about 1:0.02.

10 . The flux-compatible epoxy-anhydride adhesive of claim 1 , wherein the ratio of the epoxy to the anhydride component is from about 1:1 to about 1:0.6.

11 . The flux-compatible epoxy-anhydride adhesive of claim 1 , further comprising imidazole or amine curing agents, accelerators, catalysts, flow modifiers, fillers, adhesion promoters and thixotropic agents.

12 . The flux-compatible epoxy-anhydride adhesive of claim 1 which is compatible with no-clean flux.

13 . The flux-compatible epoxy-anhydride adhesive of claim 1 , wherein the mono anhydride is methyl nadic anhydride (MNA).