US5021320A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyamide containing the hexafluoroisopropylidene group with O-quinone diazide in positive working photoresist
Assignee: EMD Performance Materials Corp
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Filing: 1989-07-07
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Granted: 1991-06-04
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Expires: 2009-07-07
Abstract
Abstract This invention is that of high temperature polyamides containing the hexafluoroisopropylidene group. The high temperature polyamides of the invention and photo or radiation sensitizers provide improved high temperature positive resists which can be developed in aqueous alkaline developer and thermally anneal to form heat resistant, polyoxazole relief structures suitable for use in microelectronic and printing applications. The positive photoresists of the invention have improved solubility in coating solvents and improved photospeed. The polyamides of the invention can be prepared by conventional condensation reactions; e.g. the condensation of a diamine and diacid chloride. In addition the polyamides of this invention provide high temperature protective coatings with superior adhesion properties in applications other than the photoresist area.
Inventors
- 👤 Werner H. Mueller
- 👤 Dinesh N. Khanna
- 👤 Bernd Hupfer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 17:33
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233; C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/32
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
128 words
A heat resistant positive-acting photoresist composition comprising a sensitizing amount of an o-quinone diode photosensitizer in admixture with a solvent soluble polyamide polymer, said polyamide polymer having the formula ##STR10## where: X is the divalent group: ##STR11## a=0.10 to 0.50 mole fraction b=0.25 to 0.50 mole fraction c=0.00 to 0.40 mole fraction d=0.00 to 0.25 mole fraction; a+b+c+d=1, said mole fractions being based upon the total moles of X+Y+Z in said polyamide; n is an integer from 2 to 500 R is independently selected from hydrogen and a substituted or unsubstituted aliphatic or aromatic monovalent group having up to nine carbons; and Y and Z are independently selected from a substituted or an unsubstituted aliphatic, aromatic or alicyclic divalent group having up to 60 carbons and mixtures thereof.
Claim 2
Dependent Claim
128 words
A heat resistant positive-acting photoresist composition comprising a sensitizing amount of an o-quinone diode photosensitizer in admixture with a solvent soluble polyamide polymer, said polyamide polymer having the formula ##STR10## where: X is the divalent group: ##STR11## a=0.10 to 0.50 mole fraction b=0.25 to 0.50 mole fraction c=0.00 to 0.40 mole fraction d=0.00 to 0.25 mole fraction; a+b+c+d=1, said mole fractions being based upon the total moles of X+Y+Z in said polyamide; n is an integer from 2 to 500 R is independently selected from hydrogen and a substituted or unsubstituted aliphatic or aromatic monovalent group having up to nine carbons; and Y and Z are independently selected from a substituted or an unsubstituted aliphatic, aromatic or alicyclic divalent group having up to 60 carbons and mixtures thereof.
Claim 3
Dependent Claim
18 words
The composition of claim 1 wherein the mole fraction of "a" is from about 0.25 to about 0.50.
Claim 4
Dependent Claim
9 words
The composition of claim 1 wherein R is hydrogen.
Claim 5
Dependent Claim
24 words
The composition of claim 3 wherein said aromatic divalent group Y is selected from substituted or unsubstituted meta-phenylene, para-phenylene or the divalent group; ##STR12##
Claim 6
Dependent Claim
23 words
The composition of claim 4 wherein said substituted or unsubstituted meta-phenylene comprises about 20 to 100 mole percent of the divalent group Y.
Claim 7
Dependent Claim
22 words
The composition of claim 5 wherein said meta-phenylene comprises from about 40 to about 60 mole percent of the divalent group Y.
Claim 8
Dependent Claim
16 words
The composition of claim 4 wherein and the radicals of the divalent group are each para.
Claim 9
Dependent Claim
35 words
The composition of claim 6 wherein said divalent group Y comprises from about 40 to about 60 mole percent of meta-phenylene and from about 60 to about 40 mole percent of the divalent group: ##STR13##
Claim 10
Dependent Claim
32 words
The composition of claim 6 wherein said divalent group Y comprises from about 40 to about 60 mole percent of meta-phenylene and from about 60 to about 40 mole percent of para-phenylene.
Claim 11
Dependent Claim
125 words
The composition of claim 3 wherein (c) is greater than 0 and the divalent group Z has the formula: ##STR14## wherein R and R" are independently selected from hydrogen, hydroxy, lower alkyl of 1 to 6 carbons, lower alkoxy of 1 to 6 carbons, aryloxy of 6 to 9 carbons, chloro, fluoro, nitro, carboxy and carboxylic aliphatic or aromatic ester having up to 10 carbons; with the proviso that when R'" is the hexafluoroisopropylidene group, then R' and R" are not both hydroxy; and wherein R'" is independently selected from the group consisting of a carbon to carbon bond, methylene, isopropyline, polymethylene having from 2 to 12 carbons, difluoromethylene; polydifluoromethylene having 2 to 12 carbons, sulfinyl, sulfonyl, thio, oxy, carbonyl, isopropylidene, hexafluoroisopropylidene, benzenedicarbonyl and benzenedioxycarbonyl.
Claim 12
Dependent Claim
9 words
The composition of claim 10 wherein R'" is ##STR15##
Claim 13
Dependent Claim
30 words
The composition of claim 11 wherein the divalent group Y comprises about 40 to about 60 mole percent of meta-phenylene and about 60 to about 40 mole percent of para-phenylene.
Claim 14
Dependent Claim
31 words
The composition of claim 11 wherein the divalent group Y comprises about 40 to 60 mole percent of meta-phenylene and about 60 to 40 mole percent of the divalent group: ##STR16##
Claim 15
Dependent Claim
9 words
The composition of claim 4 dissolved in organic solvent.
Claim 16
Dependent Claim
13 words
The composition of claim 14 wherein said solvent comprises propylene glycol methyl ether.
Claim 17
Dependent Claim
27 words
The composition of claim 1 wherein said polyamide polymer has the formula: ##STR17## wherein Y is: ##STR18## and n is an integer of from 2 to 500.
Claim 18
Dependent Claim
9 words
The composition of claim 16 wherein Y is: ##STR19##
Claim 19
Dependent Claim
10 words
The composition of claim 16 wherein n is about 200.
Claim 20
Dependent Claim
9 words
The composition of claim 16 dissolved in organic solvent.
Claim 21
Dependent Claim
14 words
The composition of claim 14 wherein said organic solvent comprises propylene glycol methyl ether.
Claim 22
Dependent Claim
13 words
The composition of claim 19 wherein said organic solvent comprises methyl ethyl ketone.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-06-03 | 1994-12-03 | 1995-06-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-06-03 | 1998-12-03 | 1999-06-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-06-03 | 2002-12-03 | 2003-06-04 | $7700.00 | Window Closed / Lapsed |