Patent US5965679A successfully refreshed from Google Patents.
US5965679A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyphenylene oligomers and polymers
Assignee: Dow Chemical Co
•
Filing: 1997-04-01
•
Granted: 1999-10-12
•
Expires: 2017-04-01
Abstract
Abstract An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least some of the polyfunctional compounds contain three or more reactive groups. Such oligomers and uncured polymers may be cured to form cured polymers which are useful as dielectrics in the microelectronics industry, especially for dielectrics in integrated circuits.
Inventors
- 👤 James P. Godschalx
- 👤 Duane R. Romer
- 👤 Ying Hung So
- 👤 Zenon Lysenko
- 👤 Michael E. Mills
- 👤 Gary R. Buske
- 👤 Paul H. Townsend, III
- 👤 Dennis W. Smith, Jr.
- 👤 Steven J. Martin
- 👤 Robert A. DeVries
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 07:57
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/10; C08G2261/00; C08G2261/30; C08G2261/31; C08G2261/312
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
60 words
An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least one of the polyfunctional compounds contain three or more groups selected from the group consisting of acetylene groups and cyclopentadienone groups.
Claim 2
Dependent Claim
60 words
An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least one of the polyfunctional compounds contain three or more groups selected from the group consisting of acetylene groups and cyclopentadienone groups.
Claim 3
Dependent Claim
40 words
The oligomer, uncured polymer or cured polymer of claim 1 wherein the polyfunctional compounds containing the cyclopentadienone groups contain two cyclopentadienone groups and at least some of the polyfunctional compounds containing aromatic acetylene groups contain three or more acetylene groups.
Claim 4
Dependent Claim
83 words
The oligomer, uncured polymer or cured polymer of claim 2 comprising the reaction product of: (a) a biscyclopentadienone of the formula: ##STR38## (b) a polyfunctional acetylene of the formula: ##STR39## (c) and, optionally, a diacetylene of the formula: ##STR40## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and Ar 1 , Ar 2 and Ar 3 are independently an unsubstituted aromatic moiety, or inertly-substituted aromatic moiety, and y is an integer of three or more.
Claim 5
Dependent Claim
38 words
An uncured or cured polymer formed by heating the oligomer or uncured polymer of claim 3 at a temperature and for a time to react a sufficient number of the pendant and terminal acetylene groups to achieve gelation.
Claim 6
Dependent Claim
126 words
The oligomer, uncured polymer or cured polymer of claim 3 formed by the reaction of: (a) Compounds K and G; (b) Compounds K, H and G; (c) Compounds K, H and L; (d) Compounds K, H and Q; (e) Compounds K and N; (f) Compounds K, O and G; (g) Compounds K, P and G; (h) Compounds K, O and L; (i) Compounds K, P and L; (j) Compounds K, O and Q; (k) Compounds K, P and Q; (l) Compounds K and L; or (m) Compounds K and Q, wherein Compound G is 1,3,5-tris(phenylethynyl)benzene; Compound H is 4,4'-bis(phenylethynyl)diphenyl ether; Compound K is 3,3'-(oxydi-1,4-phenylene)bis(2,4,5-triphenylcyclopentadienone); Compound L is 2,4,4'-tris(phenylethynyl)diphenyl ether; Compound N is 4,4',4"-tris(phenylethynyl)-o-terphenyl; Compound O is 1,3-bis(phenylethynyl)benzene; Compound P is 1,4-bis(phenylethynyl)benzene and Compound Q is 1,2,4-tris(phenylethynyl)benzene.
Claim 7
Dependent Claim
38 words
An uncured or cured polymer formed by heating the oligomer or uncured polymer of claim 5 at a temperature and for a time to react a sufficient number of the pendant and terminal acetylene groups to achieve gelation.
Claim 8
Dependent Claim
21 words
The oligomer, uncured polymer or cured polymer of claim 3 formed from the reaction of 3,3'-(oxydi-1,4-phenylene)bis(2,4,5-triphenylcyclopentadienone), 1,3,5-tris(phenylethynyl)benzene and 4,4'-bis(phenylethynyl) diphenyl ether.
Claim 9
Dependent Claim
18 words
The oligomer, uncured polymer or cured polymer of claim 3 formed from the reaction of 3,3'-(oxydi-1,4-phenylene)bis(2,4,5-triphenylcyclopentadienone) and 1,3,5-tris(phenylethynyl)benzene.
Claim 10
Dependent Claim
33 words
A process comprising applying the oligomer or uncured polymer of claim 8 to a surface and heating to react additional cyclopentadienone or acetylene moieties to form an uncured polymer or a cured polymer.
Claim 11
Dependent Claim
42 words
An integrated circuit article comprising an active substrate containing transistors and an electrical interconnect structure containing patterned metal lines separated, at least partially, by layers or regions of the dielectric material comprising the oligomer, uncured polymer or cured polymer of claim 8.
Claim 12
Dependent Claim
33 words
A process comprising applying the oligomer or uncured polymer of claim 3 to a surface and heating to react additional cyclopentadienone or acetylene moieties to form an uncured polymer or a cured polymer.
Claim 13
Dependent Claim
33 words
A process comprising applying the oligomer or uncured polymer of claim 1 to a surface and heating to react additional cyclopentadienone or acetylene moieties to form an uncured polymer or a cured polymer.
Claim 14
Dependent Claim
42 words
An integrated circuit article comprising an active substrate containing transistors and an electrical interconnect structure containing patterned metal lines separated, at least partially, by layers or regions of the dielectric material comprising the oligomer, uncured polymer or cured polymer of claim 3.
Claim 15
Dependent Claim
42 words
An integrated circuit article comprising an active substrate containing transistors and an electrical interconnect structure containing patterned metal lines separated, at least partially, by layers or regions of the dielectric material comprising the oligomer, uncured polymer or cured polymer of claim 1.
Claim 16
Dependent Claim
141 words
An oligomer or uncured polymer having the formula: [A].sub.w [B].sub.z [EG].sub.v wherein A has the structure: ##STR41## and B has the structure: ##STR42## endgroups EG are independently represented by any one of the formulas: ##STR43## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and Ar 1 , Ar 2 and Ar 3 are independently an unsubstituted aromatic moiety or inertly-substituted aromatic moiety and M is a bond, y is an integer of three or more, p is the number ot unreacted acetylene groups in the given mer unit, r is one less than the number of reacted acetylene groups in the given mer unit and p+r=y-1, z is an integer from 1 to about 1000; w is an integer from 0 to about 1000 and v is an integer of two or more.
Claim 17
Dependent Claim
141 words
An oligomer or uncured polymer having the formula: [A].sub.w [B].sub.z [EG].sub.v wherein A has the structure: ##STR41## and B has the structure: ##STR42## endgroups EG are independently represented by any one of the formulas: ##STR43## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and Ar 1 , Ar 2 and Ar 3 are independently an unsubstituted aromatic moiety or inertly-substituted aromatic moiety and M is a bond, y is an integer of three or more, p is the number ot unreacted acetylene groups in the given mer unit, r is one less than the number of reacted acetylene groups in the given mer unit and p+r=y-1, z is an integer from 1 to about 1000; w is an integer from 0 to about 1000 and v is an integer of two or more.
Claim 18
Dependent Claim
38 words
An uncured or cured polymer formed by heating the oligomer or uncured polymer of claim 15 at a temperature and for a time to react a sufficient number of the pendant and terminal acetylene groups to achieve gelation.
Claim 19
Dependent Claim
33 words
A process comprising applying the oligomer or uncured polymer of claim 15 to a surface and heating to react additional cyclopentadienone or acetylene moieties to form an uncured polymer or a cured polymer.
Claim 20
Dependent Claim
42 words
An integrated circuit article comprising an active substrate containing transistors and an electrical interconnect structure containing patterned metal lines separated, at least partially, by layers or regions of the dielectric material comprising the oligomer, uncured polymer or cured polymer of claim 15.
Claim 21
Dependent Claim
34 words
A polyfunctional compound of the general formula: ##STR44## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and Ar 4 is an unsubstituted or inertly-substituted aromatic moiety.
Claim 22
Dependent Claim
34 words
A polyfunctional compound of the general formula: ##STR44## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and Ar 4 is an unsubstituted or inertly-substituted aromatic moiety.
Claim 23
Dependent Claim
17 words
Oligomers, uncured polymers or cured polymers comprising the reaction product of the polyfunctional compound of claim 19.
Claim 24
Dependent Claim
28 words
Oligomers, uncured polymers or cured polymers comprising the reaction product of at least one aromatic monomer containing at least one cyclopentadienone moiety and at least one acetylene moiety.
Claim 25
Dependent Claim
28 words
Oligomers, uncured polymers or cured polymers comprising the reaction product of at least one aromatic monomer containing at least one cyclopentadienone moiety and at least one acetylene moiety.
Claim 26
Dependent Claim
18 words
The oligomer, uncured polymer or cured polymer of claim 18 formed by the reaction of 4-(4-(phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone or 4-(4-ethynylphenyl)-2,3,5-triphenylcyclopentadieone.
Claim 27
Dependent Claim
33 words
A process comprising applying the oligomer or uncured polymer of claim 21 to a surface and heating to react additional cyclopentadienone or acetylene moieties to form an uncured polymer or a cured polymer.
Claim 28
Dependent Claim
42 words
An integrated circuit article comprising an active substrate containing transistors and an electrical interconnect structure containing patterned metal lines separated, at least partially, by layers or regions of the dielectric material comprising the oligomer, uncured polymer or cured polymer of claim 21.
Claim 29
Dependent Claim
38 words
A polyfunctional compound of the general formula: ##STR45## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and each Ar 4 is independently an unsubstituted aromatic moiety or inertly-substituted aromatic moiety.
Claim 30
Dependent Claim
38 words
A polyfunctional compound of the general formula: ##STR45## wherein R 1 and R 2 are independently H or an unsubstituted or inertly-substituted aromatic moiety and each Ar 4 is independently an unsubstituted aromatic moiety or inertly-substituted aromatic moiety.
Claim 31
Dependent Claim
17 words
An oligomer, uncured polymer or cured polymer formed by the reaction of the compound of claim 25.
Claim 32
Dependent Claim
18 words
The oligomer, uncured polymer or cured polymer of claim 26 formed by the reaction of 3,4-bis(4-(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone or 3,4-bis(3-(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone.
Claim 33
Dependent Claim
1 words
4-(4-(Phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone.
Claim 34
Dependent Claim
1 words
4-(4-(Phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone.
Claim 35
Dependent Claim
5 words
3,4-Bis( 4 -(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone or 3,4-Bis-(3-(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone.
Claim 36
Dependent Claim
5 words
3,4-Bis( 4 -(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone or 3,4-Bis-(3-(phenylethynyl)phenyl)-2,5-diphenylcyclopentadienone.
Claim 37
Dependent Claim
1 words
3,3'-(1,4-Phenylene)bis(2,5-di-(4-fluorophenyl)-4-phenylcyclopentadienone).
Claim 38
Dependent Claim
1 words
3,3'-(1,4-Phenylene)bis(2,5-di-(4-fluorophenyl)-4-phenylcyclopentadienone).
Claim 39
Dependent Claim
2 words
2,4-Cyclopentadien-1-one, 3-(4-ethynylphenyl)-2,4,5-triphenyl.
Claim 40
Dependent Claim
2 words
2,4-Cyclopentadien-1-one, 3-(4-ethynylphenyl)-2,4,5-triphenyl.
Claim 41
Dependent Claim
7 words
2,4,4'-Tris(phenylethynyl)diphenyl ether, 1,1':2',1"-terphenyl, 4,4',4"-tris(phenylethynyl) or 1,1':2',1"-terphenyl, 4,4"-bis(phenylethynyl).
Claim 42
Dependent Claim
7 words
2,4,4'-Tris(phenylethynyl)diphenyl ether, 1,1':2',1"-terphenyl, 4,4',4"-tris(phenylethynyl) or 1,1':2',1"-terphenyl, 4,4"-bis(phenylethynyl).
References Cited (Backward Citations)
US4093790A
Cited
US4011378A
Cited
JPS5213528A
Cited
US4339526A
Cited
US4380619A
Cited
US4400540A
Cited
US5227457A
Cited
US5169929A
Cited
US5338823A
Cited
US5236686A
Cited
US5334668A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2002-10-11 | 2003-04-12 | 2003-10-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-10-11 | 2007-04-12 | 2007-10-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-10-11 | 2011-04-12 | 2011-10-12 | $7700.00 | Window Closed / Lapsed |