Patent US1730033A successfully refreshed from Google Patents.
US5359101A
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Anionically polymerizable monomers, polymers thereof and use of such polymers in photoresists
Assignee: Henkel Loctite Ireland Ltd
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Filing: 1991-10-01
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Granted: 1994-10-25
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Expires: 2011-10-01
Abstract
Abstract Anionically polymerizable monomers containing at least one silicon or titanium atom form polymeric photoresists having good dry etch resistance for use in microlithography. The monomers are of the formula ##STR1## wherein A is --H or --CH═CH 2 ; X is a strong electron withdrawing group; Y is a strong electron withdrawing group containing at least one silicon or titanium atom. Preferably Y is ##STR2## wherein n is 1-5 and R 2 , R 3 and R 4 are C 1 -C 10 alkyl. A particularly preferred monomer is 3-trimethylsilylpropyl 2-cyanoacrylate. Methods for applying a resist coating by vapor deposition of these monomers and exposure to radiation are described. A positive or negative tone image can be produced, depending upon the imaging method employed. The imaging layer may be applied over a planarizing layer to form a multilayer photoresist.
Inventors
- 👤 John Woods
- 👤 Pauline Coakley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:49
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0757; G03F7/0758; C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0834; C07F7/0838; C07F7/18; C07F7/1804; C07F7/28; C08; C08F; C08F30/00; C08F30/04; G03F7/038; G03F7/039
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
69 words
Anionically polymerizable monomers of the formula I: ##STR27## wherein A is --H or --CH═CH 2 ; X is a strong electron withdrawing group selected from the group consisting of --CN, --COR, --COOR, --SO 2 R and --SO 3 R, wherein R is H or a hydrocarbyl group; Y is a x-valent strong electron withdrawing group containing at least one silicon or titanium atom; and x is equal to 1.
Claim 2
Dependent Claim
69 words
Anionically polymerizable monomers of the formula I: ##STR27## wherein A is --H or --CH═CH 2 ; X is a strong electron withdrawing group selected from the group consisting of --CN, --COR, --COOR, --SO 2 R and --SO 3 R, wherein R is H or a hydrocarbyl group; Y is a x-valent strong electron withdrawing group containing at least one silicon or titanium atom; and x is equal to 1.
Claim 3
Dependent Claim
36 words
Monomers according to claim 1 wherein Y is selected from --COR 1 , --COOR 1 , --SO 2 R 1 and --SO 3 R 1 , wherein R 1 is a group containing Si or Ti.
Claim 4
Dependent Claim
154 words
Monomers according to claim 2 wherein R 1 is --Si(R 2 )(R 3 )(R 4 ), wherein R 2 , R 3 and R 4 ,which may be the same or different are selected from H (provided that not more than one of R 2 , R 3 and R 4 is H), C 1 -C 1O alkyl, aryl, C 1 -C 1O alkoxy or siloxy groups of the formula: ##STR28## wherein R 5 , R 6 and R 7 , which may be the same or different, are selected from H, CH 3 or phenyl (provided that not more than one of R 5 , R 6 and R 7 is H); and wherein R 2 may also be a group selected from siloxane oligomers or polymers of the structure: ##STR29## wherein R 5 , R 6 and R 7 are defined as above and m is an integer from 2 to 100.
Claim 5
Dependent Claim
59 words
Monomers according to claim 2 wherein X is other than --CN and R is a C 1 14 C 12 hydrocarbyl group and R 1 is a C 1 -C 1O hydrocarbyl, C 6 -C 20 aryl or C 6 -C 20 hydrocarbyl aryl group, or a substituted derivative thereof, further substituted with a Si or Ti containing group.
Claim 6
Dependent Claim
153 words
Monomers according to claim 4 wherein the Si containing group is of the formula: --Si(R.sup.2)(R.sup.3)(R.sup.4) wherein R 2 , R 3 and R 4 , which may be the same or different, are selected from H (provided that not more than one of R 2 , R 3 and R 4 is H), C 1 -C 1O alkyl, aryl, C 1 -C 1O alkoxy or siloxy groups of the formula: ##STR30## wherein R 5 , R 6 and R 7 , which may be the same or different, are selected from H, CH 3 or phenyl (provided that not more than one of R 5 , R 6 and R 7 is H) wherein R 2 may also be a group selected from siloxane oligomers or polymers of the structure: ##STR31## wherein R 5 , R 6 and R 7 are defined as above and m is an integer from 2 to 100.
Claim 7
Dependent Claim
15 words
Monomers according to claim 5 wherein m is in the range from 2 to 5.
Claim 8
Dependent Claim
26 words
Monomers according to claim 5 wherein at least one of R 2 , R 3 and R 4 is C 1 -C 5 alkyl or phenyl.
Claim 9
Dependent Claim
43 words
Monomers according to claim 5 wherein Y is --COO(CH 2 ) n --O--Si(R 2 )(R 3 )(R 4 ) wherein R 2 , R 3 and R 4 are as defined in claim 5 and n is an integer from 1 to 5.
Claim 10
Dependent Claim
26 words
Monomers according to claim 8 wherein R 2 , R 3 and R 4 are C 1 -C 10 alkyl land n is at least 3.
Claim 11
Dependent Claim
37 words
Anionically polymerizable monomers of the formula: ##STR32## wherein A is --H or --CH═CH 2 , Y is an x-valent strong electron withdrawing group containing at least one silicon or titanium atom and x is equal to 1.
Claim 12
Dependent Claim
37 words
Anionically polymerizable monomers of the formula: ##STR32## wherein A is --H or --CH═CH 2 , Y is an x-valent strong electron withdrawing group containing at least one silicon or titanium atom and x is equal to 1.
Claim 13
Dependent Claim
9 words
Monomer according to claim 10 which is 3-trimethylsilylpropyl 2-cyanoacrylate.
Claim 14
Dependent Claim
35 words
Monomers according to claim 10 wherein Y is selected from --COR 1 , --COOR 1 , --SO 2 R 1 or --SO 3 R 1 wherein R 1 is a group containing Si or Ti.
Claim 15
Dependent Claim
155 words
Monomers according to claim 12 wherein R 1 is --Si(R 2 )(R 3 )(R 4 ), wherein R 2 , R 3 and R 4 , which may be the same or different, are selected from H (provided that not more than one of R 2 , R 3 and R 4 is H), C 1 -C 1O alkyl, aryl, C 1 -C 10 alkoxy or siloxy groups of the formula: ##STR33## wherein R 5 , R 6 and R 7 , which may be the same or different, are selected from H, CH 3 or phenyl (provided that not more than one of R 5 , R 6 and R 7 is H); and wherein R 2 may also be a group selected from siloxane oligomers or polymers of the structure: ##STR34## wherein R 5 , R 6 and R 7 are defined as above and m is an integer from 2 to 100.
Claim 16
Dependent Claim
42 words
Monomers according to claim 12 wherein R 1 is a C 1 -C 10 hydrocarbyl, C 6 -C 20 aryl or C 6 -C 20 hydrocarbyl aryl group, or a substituted derivative thereof, further substituted with a Si or Ti containing group.
Claim 17
Dependent Claim
154 words
Monomers according to claim 14 wherein the Si containing group is of the formula: --Si(R.sup.2)(R.sup.3)(R.sup.4) wherein R 2 , R 3 and R 4 , which may be the same or different, are selected from H (provided that not more than one of R 2 , R 3 and R 4 is H), C l -C 10 alkyl, aryl, C 1 -C 10 alkoxy or siloxy groups of the formula: ##STR35## wherein R 5 , R 6 and R 7 , which may be the same or different, are selected from H, CH 3 or phenyl (provided that not more than one of R 5 , R 6 and R 7 is H); and wherein R 2 may also be a group selected from siloxane oligomers or polymers of the structure: ##STR36## wherein R 5 , R 6 and R 7 are defined as above and m is an integer from 2 to 100.
Claim 18
Dependent Claim
15 words
Monomers according to claim 15 wherein m is in the range from 2 to 5.
Claim 19
Dependent Claim
26 words
Monomers according to claim 15 wherein at least one of R 2 , R 3 and R 4 is C 1 -C 5 alkyl or phenyl.
Claim 20
Dependent Claim
169 words
Monomers according to claim 10 wherein Y is --COO(CH 2 ) n --O--Si(R 2 )(R 3 )(R 4 ) and wherein R 2 , R 3 and R 4 , which may be the same or different, are selected from H (provided that not more than one of R 2 , R 3 and R 4 is H), C 1 C 10 alkyl, aryl, C 1 -C 10 alkoxy or siloxy groups of the formula: ##STR37## wherein R 5 , R 6 and R 7 , which may be the same or different, are selected from H, CH 3 or phenyl (provided that not more than one of R 5 , R 6 and R 7 is H); and wherein R 2 may also be a group selected from siloxane oligomers or polymers of the structure: ##STR38## wherein R 5 , R 6 and R 7 are defined as above and m is an integer from 2 to 100, and n is an integer of from 1 to 5.
Claim 21
Dependent Claim
15 words
Monomers according to claim 18 wherein m is in the range from 2 to 5.
Claim 22
Dependent Claim
26 words
Monomers according to claim 33 wherein R 2 , R 3 and R 4 are C 1 -C 5 alkyl and n is at least 3.
Claim 23
Dependent Claim
49 words
A silicon-containing α-cyanoacrylate represented by the formula: ##STR39## where R 1 is a C 1 -C 6 alkyl group having at least one group of the formula: ##STR40## thereon, and R 2 , R 3 and R 4 are the same or different C 1 -C 10 alkyl groups.
Claim 24
Dependent Claim
49 words
A silicon-containing α-cyanoacrylate represented by the formula: ##STR39## where R 1 is a C 1 -C 6 alkyl group having at least one group of the formula: ##STR40## thereon, and R 2 , R 3 and R 4 are the same or different C 1 -C 10 alkyl groups.
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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) | 1997-10-24 | 1998-04-25 | 1998-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-10-24 | 2002-04-25 | 2002-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-10-24 | 2006-04-25 | 2006-10-25 | $7700.00 | Window Closed / Lapsed |