USRE37599EExpiredUtilityPatentIndex 72

Poly(arylene ether) compositions and the method for their manufacture

Assignee: ALLIED SIGNAL INCPriority: Jun 26, 1995Filed: Sep 8, 2000Granted: Mar 19, 2002

Est. expiryJun 26, 2015(expired)· nominal 20-yr term from priority

Inventors:LAU KREISLER HENDRICKS NEIL WAN WILLIAM SMITH AARON

H10W 70/60H10W 74/40H10W 20/48C08G 2650/48C08G 2650/60C08G 65/4006Y10S428/901Y10T428/24917Y10T428/24802Y10T428/3154C08G 65/40

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Claims

Abstract

A method is disclosed for making hydroxy-substituted ethynylated biphenyl compounds and for reacting such compounds with a family of noncross-linking thermosetting poly(arylene ethers) to produce novel poly(arylene ether) compositions which, when cured at glass transition temperatures greater than about 350° C. to form thin films, possess properties such as low dielectric constant, low moisture absorption, and high thermal stability. These films are suitable for use as intermetal dielectrics for multilevel interconnection.

Claims

exact text as granted — not AI-modified

We claim:

1. A process for producing a poly(arylene ether) composition comprising:
reacting a compound of Formula A
where r is an integer of from about 0 to about 50,
or a compound of Formula D
wherein q is an integer of from about 0 to about 49 with a compound of formula B

HO—R—OH

wherein R is an aromatic nucleus which imparts a glass transition temperature of greater than 300° C. to the composition, under conditions sufficient to produce the composition.

2. The process of claim 1 wherein r is from about 1 to about 4.

3. The process of claim 2 wherein said compound of the formula A is comprised of hexafluorobenzene, decafluoro-biphenyl having ortho-, meta-, and para-catenation between its aromatic rings, perfluoro-para-terphenyl, perfluoro-meta-terphenyl, perfluoro-ortho-terphenyl, tetradecafluoro-para-terphenyl, tetradecafluoro-meta-terphenyl, tetradecafluoro-ortho-terphenyl, octadecafluoro-para,para-terphenyl or all positional isomers thereof due to ring catenation, perfluoro-para,para-tetraphenyl and all positional isomers thereof due to ring catenation, or mixtures thereof.

4. The process of claim 1 wherein q is from about 0 to about 3.

5. The process of claim 1 wherein the temperature of said reaction is from about 100° C. to about 175° C.

6. The process of claim 1 wherein the molar ratio of compounds having formula A or formula D to compounds having Formula B is about 1:1 to about 1:0.95.

7. A process of producing a composition of formula C
wherein m is an integer of from about 0 to about 50; and n is an integer of from about 1 to about 200; comprising:
reacting a compound of Formula A
wherein r is an integer of from about 0 to about 50 with a compound of formula B:

HO—R—OH

wherein R comprises:

or mixtures thereof, under conditions sufficient to produce the composition.

8. The process of claim 7 wherein said compound having formula B is comprised of:
or mixtures thereof.

9. The process of claim 7 wherein said R group is comprised of 2,2′-bis(phenylethynyl)-4,4′biphenylenediyl or 2,2′-bis(phenylethynyl)-5,5′-biphenylenediyl.

10. The process of claim 7 wherein m is from about 0 to about 4.

11. The process of claim 7 wherein n is from about 1 to about 200.

12. The process of claim 1 further comprising recovering the poly(arylene ether) composition.

13. The composition produced according to the process of claim 1 .

14. The composition produced according to the process of claim 12 .

15. The process of claim 1 wherein the compound having formula A and a first compound having formula B are further reacted with a compound containing formula Z under conditions sufficient to produce a product corresponding to formula C″
wherein
Z is comprised of 1,5-naphthalenediyl, an aromatic nucleus in a second compound having formula B which is independent from said first compound having formula B, or mixtures thereof;
Y is independently
or mixtures thereof:
T 1 , T 2 , and T 3 are independently comprised of an alkyl having from about 1 to about 10 carbons, an aryl, or mixtures thereof; a is independently an integer from about 1 to about 200; and b is an integer of from about 0 to about 20.

16. The process of claim 15 wherein said product is
wherein c is independently an integer from about 1 to about 200; and Z is comprised of 1,5-naphthalenediyl, an aromatic nucleus in a second compound having formula B which is independent from said first compound having formula B, or mixtures thereof.

17. The process of claim 15 wherein an inorganic base is optionally reacted with said compound having formula A, said first compound having formula B, and said compound containing formula Z.

18. The process of claim 17 wherein said inorganic base is potassium carbonate.

19. The process of claim 17 wherein the molar ratio of said compound having formula Z to said first compound having formula B is about 20 to about 1.

20. The process of claim 17 wherein Z is 1,5-naphthalenediyl.

21. The process of claim 1 wherein the compound having formula D and a first compound having formula B are further reacted with a compound containing formula Z under conditions sufficient to produce a product corresponding to formula D″
wherein
Z is comprised of 1,5-naphthalenediyl, an aromatic nucleus in a second compound having formula B which is independent from said first compound having formula B, or mixtures thereof;
Y is independently
T 1 , T 2 , and T 3 are independently comprised of an alkyl having from about 1 to about 10 carbons, an aryl, or mixtures thereof; d is independently an integer from about 1 to about 200; b is an integer of from about 0 to about 20; and q is independently an integer of from about 0 to about 20.

22. A film comprised of the composition of claim 13 .

23. A substrate coated with the composition of claim 13 .

24. A film comprised of the composition of claim 14 .

25. A microelectronic device containing the film of claim 22 .

26. A microelectronic device containing the film of claim 24 .

27. A composition having formula C
R is an aromatic nucleus which imparts a glass transition temperature of greater than 300° C. to the composition;
m is an integer of from about 0 to about 50; and
n is an integer of from about 1 to about 200.

28. A composition having formula D″:
wherein
Z is comprised of 1,5-naphthalenediyl, an R group wherein R is an aromatic nucleus which imparts a glass transition temperature of greater than 260° C. to the composition, or mixtures thereof;
Y is
T 1 , T 2 , and T 3 are independently comprised of an alkyl having from about 1 to about 10 carbons, an aryl, or mixtures thereof;
d is independently an integer from about 1 to about 200;
b is an integer of from about 0 to about 20; and
q is an integer of from about 0 to about 20.

29. A composition having formula C″:
wherein
Z is comprised of 1,5-naphthalenediyl, an R group wherein R is an aromatic nucleus which imparts a glass transition temperature of greater than 260° C. to the composition, or mixtures thereof;
Y is independently
and mixtures thereof;
T 1 , T 2 , and T 3 are independently comprised of an alkyl having from about 1 to about 10 carbons, an aryl, or mixtures thereof;
a is independently an integer from about 1 to about 200; and
b is an integer of from about 0 to about 20.

30. A process for producing a fluorinated poly(arylene ether) mixture for spin-coating onto a substrate comprising:
a) forming a solution from a composition of the formula C
wherein
R is an aromatic nucleus which imparts a glass transition temperature of greater than 300° C. to the composition;
m is an integer of from about 0 to about 50; and
n is an integer of from about 1 to about 200 and an aprotic solvent; and
b) filtering the solution through at least one filter having a pore size of about 0.1 micrometers.

31. The process of claim 30 wherein said aprotic solvent is comprised of cyclic ketones, cyclic amides, and mixtures thereof.

32. The process of claim 30 wherein said aprotic solvent is comprised of cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, N-methylpyrrolidinone, N-cyclohexyl-pyrrolidinone, or mixtures thereof.

33. The process of claim 32 wherein said solvent is cyclopentanone.

34. The process of claim 30 wherein said solution is comprised of, based upon the total weight of said solution, from about 50% to about 99% of said solvent and from about 1 to about 50% of said fluorinated poly(arylene ether) composition.

35. The process of claim 34 wherein said solution is comprised of, based upon the total weight of said solution, from about 80% to about 97% of said solvent and from about 3 to about 20% of said fluorinated poly(arylene ether) composition.

36. The process of claim 30 wherein said solution is filtered sequentially through at least two filters, each of said filters having a different pore size.

37. A process for producing a cured, coated substrate comprising:
a) forming a solution from a composition of the formula C
wherein
R is an aromatic nucleus which imparts a glass transition temperature of greater than 300° C. to the composition;
m is an integer of from about 0 to about 50; and
n is an integer of from about 1 to about 200 and an aprotic solvent;
b) filtering the solution;
c) applying the solution of step b via spin-coating onto a substrate to form a film thereon; and
d) heating the film of step c under conditions sufficient to cure the film.

38. A composition having the formula:
wherein
c is an integer from about 1 to about 200; and
Z is comprised of 1,5-naphthalenediyl, an R group wherein R is an aromatic nucleus which imparts a glass transition temperature of greater than 260° C. to the composition, or mixtures thereof.

39. A film comprised of the composition of claim 27 .

40. A substrate coated with the film of claim 39 .

41. A microelectronic device containing the film of claim 39 .

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