US2001020071A1PendingUtilityA1

High performance cyanate-bismaleimide-epoxy resin compositions for printed circuits and encapsulants

Priority: Oct 10, 1997Filed: May 7, 2001Published: Sep 6, 2001

Est. expiryOct 10, 2017(expired)· nominal 20-yr term from priority

Inventors:Miguel A. Capote Edward S. Harrison Yong-Joon Lee Howard Arthur Lenos

H10W 74/47H10W 70/69C08G 59/226C08G 59/36C08G 59/38C08G 59/4014C08G 59/4042C08G 73/0655H05K 3/287Y10S428/901

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References

Claims

Abstract

A thermosetting resin system including an epoxy resin, a bismaleimide, a cyanate ester and a co-curing agent that is an aromatic moiety having unsaturated aliphatic groups and glycidyl ether groups is provided. Preferred co-curing agents are 2-allylphenyl glycidyl ether and 2,2′-diallylbisphenol A diglycidyl ether. The resin system can be employed as an encapsulant for electronic components and as dielectric layers with microvias on printed circuits.

Claims

exact text as granted — not AI-modified

What is claimed is:

1 . A curable composition that comprises:
(a) a cyanate ester; (b) a bismaleimide; (c) a co-curing agent having the structure R 1 —Ar—R 2 wherein Ar is at least one unsaturated aromatic carboxylic moiety, R 1 is at least one unsaturated aliphatic moiety, R 2 is at least one glycidyl moiety with the proviso that when two or more unsaturated aromatic carboxylic moieties are present, at least one of the unsaturated aromatic carboxylic moieties has an unsaturated aliphatic moiety and an epoxide moiety attached thereto; (d) an epoxy resin; and (e) optionally, a free-radical initiator.

2 . The composition of claim 1 wherein the co-curing agent is selected from the group consisting of compounds having the structures I, II:

wherein each of R 1 and R 2 are each selected from H, —CH 3 or CF 3 , and mixtures thereof.

3 . The composition of claim 1 wherein the co-curing agent is selected from 2-allyphenyl glycidyl ether, 2,2′-diallybisphenol A diglycidyl ether, and mixtures thereof.

4 . The composition of claim 1 the cyanate ester is selected from the group consisting of compounds having the structures I, II, III:

wherein x is a divalent moiety, and mixtures thereof.

5 . The composition of claim 1 wherein the cyanate ester is

wherein n is an integer from 0 to 200.

6 . The composition of claim 1 wherein the resin composition does not include a solvent.

7 . The composition of claim 1 wherein the epoxy resin is selected from the group consisting of bisphenol A based epoxy resin, bisphenol F based epoxy resin, epoxy novolac, epoxy cresol novolac, triphenylomethane triglycidyl ether, N,N-diglycydyl-4-glycidylpxyaniline, and 4,4′-methylenebis(N,N-diglycidylaniline).

8 . The composition of claim 1 comprising a heat triggered initiator.

9 . The composition of claim 1 comprising an energetically triggered initiator.

10 . The composition of claim 1 further comprising a cyanate ester trimerization catalyst.

11 . The composition of claim 1 wherein the cyanate ester comprises about 1.5 to 5 molar equivalent parts of the composition, the bismaleimide comprises about 0.5 to 1.5 molar equivalent parts of the composition, the co-curing agent comprises about 0.5 to 1.5 molar equivalents of the composition, and the epoxy resin comprising about 1.5 to 5 molar equivalent parts of the composition.

12 . The composition of claim 1 wherein the epoxide molar equivalent concentration in the resin composition is equal to or less than the cyanate ester molar concentration.

13 . The composition of claim 1 wherein the co-curing agent molar equivalent concentration is less than the lesser of either (i) the cyanate ester molar concentration or (ii) the bismaleimide molar concentration.

14 . A process of forming vias in a polymer composition comprising the steps of:
(a) applying a layer of a resin composition that comprises
(i) a cyanate ester;
(ii) a bismaleimide;
(iii) a co-curing agent having the structure R 1 —Ar—R 2 wherein Ar is at least one unsaturated aromatic carboxylic moiety, R 1 is at least one unsaturated aliphatic moiety, R 2 is at least one glycidyl moiety with the proviso that when two or more unsaturated aromatic carboxylic moieties present, at least one of the unsaturated aromatic carboxylic moieties has an unsaturated aliphatic moiety and an epoxide moiety attached thereto;
(iv) an epoxy resin; and (v) a radiation triggered free-radical initiator;
(b) covering the layer of resin composition with a mask having windows through which radiation can be transmitted;
(c) exposing part of the resin composition to radiation to at least partially cure the resin composition in exposed areas;
(d) removing non-cured portions of the resin composition; and
(e) completing the cure of the resin composition.

15 . The process of claim 14 wherein the co-curing agent is selected from the group consisting of compounds having the structures I, II:

wherein each of R 1 and R 2 are each selected from H, —CH 3 or CF 3 and mixtures thereof.

16 . The process of claim 14 wherein the co-curing agent is selected from 2-allyphenyl glycidyl ether, 2,2′-diallybisphenol A diglycidyl ether, and mixtures thereof.

17 . The process of claim 14 the cyanate ester is selected from the group consisting of compounds having the structures I, II, III:

wherein x is a divalent moiety, and mixtures thereof.

18 . The process of claim 14 wherein the cyanate ester is

wherein n is an integer from 0 to 200.

19 . The process of claim 14 wherein the resin composition does not include a solvent.

20 . The process of claim 14 wherein the epoxy resin is selected from the group consisting of bisphenol A based epoxy resin, bisphenol F based epoxy resin, epoxy novolac, epoxy cresol novolac, triphenylomethane triglycidyl ether, N,N-diglycydyl-4-glycidylpxyaniline, and 4,4′-methylenebis(N,N-diglycidylaniline).

21 . The process of claim 14 wherein the resin composition comprises a heat triggered initiator.

22 . The process of claim 14 wherein the resin composition comprises an energetically triggered initiator.

23 . The process of claim 14 further comprising a cyanate ester trimerization catalyst.

24 . The process of claim 14 wherein the cyanate ester comprises about 1.5 to 5 molar equivalent parts of the composition, the bismaleimide comprises about 0.5 to 1.5 molar equivalent parts of the composition, the co-curing agent comprises about 0.5 to 1.5 molar equivalents of the composition, and the epoxy resin comprising about 1.5 to 5 molar equivalent parts of the composition.

25 . The process of claim 14 wherein the epoxide molar equivalent concentration in the resin composition is equal to or less than the cyanate ester molar concentration.

26 . The process of claim 14 wherein the co-curing agent molar equivalent concentration is less than the lesser of either (i) the cyanate ester molar concentration or (ii) the bismaleimide molar concentration.

27 . An electrical component assembly, comprising:
(a) an electrical component having a plurality of electrical terminations; (b) a component carrying substrate having a plurality of electrical terminations corresponding to the terminations of the electrical component; and (c) a thermally curable adhesive composition that comprises:
(i) a cyanate ester;
(ii) a bismaleimide;
(iii) a co-curing agent having the structure R 1 —Ar—R 2 wherein Ar is at least one unsaturated aromatic carboxylic moiety, R 1 is at least one unsaturated aliphatic moiety, R 2 is at least one glycidyl moiety with the proviso that when two or more unsaturated aromatic carboxylic moieties are present, at least one of the unsaturated aromatic carboxylic moieties has an unsaturated aliphatic moiety and an epoxide moiety attached thereto;
(iv) an epoxy resin; and
(v) optionally, a free-radical initiator.

28 . The electrical component assembly of claim 27 wherein the co-curing agent is selected from the group consisting of compounds having the structures I, II

wherein each of R 1 and R 2 are each selected from H, —CH 3 or CF 3 , and mixtures thereof.

29 . The electrical component assembly of claim 27 wherein the co-curing agent is selected from 2-allyphenyl glycidyl ether, 2,2′-diallybisphenol A diglycidyl ether, and mixtures thereof.

30 . The electrical component assembly of claim 27 the cyanate ester is selected from the group consisting of compounds having the structures I, II, III:

wherein x is a divalent moiety, and mixtures thereof.

31 . The electrical component assembly of claim 27 wherein the cyanate ester is

wherein n is an integer from 0 to 200.

32 . The electrical component assembly of claim 27 wherein the composition does not include a solvent.

33 . The electrical component assembly of claim 27 wherein the epoxy resin is selected from the group consisting of bisphenol A based epoxy resin, bisphenol F based epoxy resin, epoxy novolac, epoxy cresol novolac, triphenylomethane triglycidyl ether, N,N-diglycydyl-4-glycidylpxyaniline, and 4,4′-methylenebis(N,N-diglycidylaniline).

34 . The electrical component assembly of claim 27 wherein the resin composition comprises a heat triggered initiator.

35 . The electrical component assembly of claim 27 wherein the resin composition comprises an energetically triggered initiator.

36 . The electrical component assembly of claim 27 wherein the resin composition further comprises a cyanate ester trimerization catalyst.

37 . The electrical component assembly of claim 27 wherein the cyanate ester comprises about 1.5 to 5 molar equivalent parts of the composition, the bismaleimide comprises about 0.5 to 1.5 molar equivalent parts of the composition, the co-curing agent comprises about 0.5 to 1.5 molar equivalents of the composition, and the epoxy resin comprising about 1.5 to 5 molar equivalent parts of the composition.

38 . The electrical component assembly of claim 27 wherein the epoxide molar equivalent concentration in the resin composition is equal to or less than the cyanate ester molar concentration.

39 . The electrical component assembly of claim 27 wherein the co-curing agent molar equivalent concentration is less than the lesser of either (i) the cyanate ester molar concentration or (ii) the bismaleimide molar concentration.

40 . A process of forming vias in a polymer composition comprising the steps of:
(a) applying a layer of a resin composition that comprises:
(i) a cyanate ester;
(ii) a bismaleimide;
(iii) a co-curing agent having the structure R 1 —Ar—R 2 wherein Ar is at least one unsaturated aromatic carboxylic moiety, R 1 is at least one unsaturated aliphatic moiety, R 2 is at least one glycidyl moiety with the proviso that when two or more unsaturated aromatic carboxylic moieties are present, at least one of the unsaturated aromatic carboxylic moieties has an unsaturated aliphatic moiety and an epoxide moiety attached thereto;
(iv) an epoxy resin; and
(v) optionally, a free-radical initiator;
(b) covering the layer of resin composition with a mask having openings through which radiation can be transmitted; (c) exposing part of the resin composition to radiation to at least partially cure the resin composition in exposed areas; (d) removing non-cured portions of the resin composition; and (e) completing the cure of the resin composition.

41 . The process of claim 40 wherein the co-curing agent is selected from the group consisting of compounds having the structures I, II:

wherein each of R 1 and R 2 are each selected from H, —CH 3 or CF 3 and mixtures thereof.

42 . The process of claim 40 wherein the co-curing agent is selected from 2-allyphenyl glycidyl ether, 2,2′-diallybisphenol A diglycidyl ether, and mixtures thereof.

43 . The process of claim 40 the cyanate ester is selected from the group consisting of compounds having the structures I, II, III:

wherein x is a divalent moiety, and mixtures thereof.

44 . The process of claim 40 wherein the cyanate ester is

wherein n is an integer from 0 to 200.

45 . The process of claim 40 wherein the resin composition does not include a solvent.

46 . The process of claim 40 wherein the epoxy resin is selected from the group consisting of bisphenol A based epoxy resin, bisphenol F based epoxy resin, epoxy novolac, epoxy cresol novolac, triphenylomethane triglycidyl ether, N,N-diglycydyl-4-glycidylpxyaniline, and 4,4 ′-methylenebis(N,N-diglycidylaniline).

47 . The process of claim 40 wherein the resin composition comprises a heat triggered initiator.

48 . The process of claim 40 wherein the resin composition comprises an energetically triggered initiator.

49 . The process of claim 40 further comprising a cyanate ester trimerization catalyst.

50 . The process of claim 40 wherein the cyanate ester comprises about 1.5 to 5 molar equivalent parts of the composition, the bismaleimide comprises about 0.5 to 1.5 molar equivalent parts of the composition, the co-curing agent comprises about 0.5 to 1.5 molar equivalents of the composition, and the epoxy resin comprising about 1.5 to 5 molar equivalent parts of the composition.

51 . The process of claim 40 wherein the epoxide molar equivalent concentration in the resin composition is equal to or less than the cyanate ester molar concentration.

52 . The process of claim 40 wherein the co-curing agent molar equivalent concentration is less than the lesser of either (i) the cyanate ester molar concentration or (ii) the bismaleimide molar concentration.

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