Claims
- 1. A compound having the following structure:
- 2. A compound according to claim 1 wherein M is a saturated non-crosslinkable moiety.
- 3. A compound according to claim 2, wherein M is an alkylcarboxylate, an alkyl ether, aryl ether, or a succinimide.
- 4. A compound according to claim 3, wherein M is an alkylcarboxylate.
- 5. A compound according to claim 1 wherein each Q is phenylene, X is O, m is 0, L is not present, n is 1, and k is 1.
- 6. A compound according to claim 5 having the structure
- 7. A compound having the structure
- 8. A low shrinkage adhesive composition comprising a compound according to claim 1 and a curing catalyst.
- 9. A composition according to claim 8, further comprising a maleimide having the structure:
- 10. A composition according to claim 9 wherein X′ is selected from
(I) straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, (II) siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— or (CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, (III) polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— or [(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, (IV) aromatic moieties having the structure: 20 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, or 21 wherein
Z is O or NR, wherein R is hydrogen or lower alkyl, (V) urethanes having the structure 22 wherein:
each R1 is independently hydrogen or lower alkyl, each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to about 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50, (VI) aromatic moieties having the structure: 23 wherein
each Ar is a monosubstituted, disubstituted or trisubstituted aromatic or heteroaromatic ring having in the range of 3 up to about 10 carbon atoms, n is 1 up to about 50, and Z is selected from:
straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, aromatic moieties having the structure: 24 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, as well as mixtures of any two or more thereof.
- 11. A composition according to claim 10, wherein the maleimide is liquid at ambient temperature.
- 12. A low shrinkage thermosetting resin composition comprising:
A) a compound according to claim 1, B) a maleimide, C) a coupling agent, and D) a cure initiator.
- 13. A resin composition according to claim 12, wherein said maleimide has the structure:
- 14. A composition according to claim 13 wherein X′ is selected from
(I) straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, (II) siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— or (CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, (III) polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— or [(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, (IV) aromatic moieties having the structure: 2627 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, or 28 wherein
Z is O or NR, wherein R is hydrogen or lower alkyl, (V) urethanes having the structure 29 wherein:
each R1 is independently hydrogen or lower alkyl, each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to about 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50, (VI) aromatic moieties having the structure: 30 wherein
each Ar is a monosubstituted, disubstituted or trisubstituted aromatic or heteroaromatic ring having in the range of 3 up to about 10 carbon atoms, n is 1 up to about 50, and Z is selected from:
straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, aromatic moieties having the structure: 31 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, as well as mixtures of any two or more thereof.
- 15. A composition according to claim 14, wherein the maleimide is liquid at ambient temperature.
- 16. A low shrinkage formulation comprising:
in the range of about 10 up to 80 weight percent of a thermosetting resin composition according to claim 14, and in the range of about 20 up to 90 weight percent of a filler.
- 17. A formulation according to claim 16, wherein the filler is conductive.
- 18. A formulation according to claim 17, wherein said conductive filler is electrically conductive.
- 19. A formulation according to claim 17, wherein said conductive filler is thermally conductive.
- 20. A formulation according to claim 16, further comprising an acrylate derivative of oligomers of optionally substituted cyclopentadiene.
- 21. A method for reducing the shrinkage upon cure of a thermosetting resin composition, said method comprising combining the resin with a compound according to claim 1.
- 22. The method according to claim 21, wherein the thermosetting resin composition comprises a maleimide having the structure:
- 23. A method according to claim 22 wherein X′ is selected from
(I) straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, (II) siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— or (CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, (III) polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— or [(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, (IV) aromatic moieties having the structure: 33 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, or 34 wherein
Z is O or NR, wherein R is hydrogen or lower alkyl, (V) urethanes having the structure 35 wherein:
each R1 is independently hydrogen or lower alkyl, each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to about 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50, (VI) aromatic moieties having the structure: 36 wherein
each Ar is a monosubstituted, disubstituted or trisubstituted aromatic or heteroaromatic ring having in the range of 3 up to about 10 carbon atoms, n is 1 up to about 50, and Z is selected from:
straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl, siloxanes having the structure: —(CR2)m′—[Si(R′)2—O]q′—Si(R′)2—(CR2)n′— wherein
each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50, polyalkylene oxides having the structure: —[(CR2)r—O—]q′—(CR2)s— wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, aromatic moieties having the structure: 37 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, as well as mixtures of any two or more thereof.
- 24. The method according to claim 23, wherein the maleimide is liquid at ambient temperature.
- 25. A method for improving adhesive strength of a thermosetting resin composition, said method comprising combining the resin with a compound according to claim 1.
- 26. A method for the preparation of a low shrinkage thermosetting resin composition, said method comprising combining the resin with a compound according to claim 1.
- 27. A method for attaching a semiconductor device to a substrate, said method comprising:
(a) applying an adhesive composition according to claim 14 to the surface of said device and/or the surface of said substrate, (b) contacting said surface of said device with said surface of said substrate, and thereafter (c) subjecting said adhesive composition to a temperature sufficient to cure said adhesive composition.
- 28. A method for improving the bond between a semiconductor device and a substrate said method comprising
(a) applying an adhesive composition according to claim 14 to the surface of said device and/or the surface of said substrate; (b) conducting said surface of said device with said surface of said substrate, and thereafter (c) subjecting said adhesive composition to a temperature sufficient to cure said adhesive composition.
RELATED APPLICATIONS
[0001] This application is a continuation-in-part of PCT Application No. US01/30423 filed Sep. 27, 2001, which claims priority from U.S. Application No. 60/237,775 filed Sep. 30, 2000.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60237775 |
Sep 2000 |
US |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
PCT/US01/30423 |
Sep 2001 |
US |
Child |
10137064 |
Apr 2002 |
US |