US5344742A
Expired / Lapsed
US
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Benzyl-substituted photoactive compounds and photoresist compositions comprising same
Assignee: Shipley Co Inc
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Filing: 1993-04-21
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Granted: 1994-09-06
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Expires: 2013-04-21
Abstract
Abstract The present invention comprises certain benzyl-substituted photoactive compounds and photoresist compositions comprising such photoactive compounds. The benzyl-substituted photoactive compounds of the invention are particularly suitable as the photoactive component in chemically amplified positive-acting and negative-acting compositions.
Inventors
- 👤 Roger F. Sinta
- 👤 George Barclay
- 👤 Martha M. Rajaratnam
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 09:49
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/039; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/122
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
159 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR5## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, halo, hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl, wherein at least one of R 4 , R 5 , R 6 , R 7 and R 8 is other than hydrogen.
Claim 2
Dependent Claim
159 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR5## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, halo, hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl, wherein at least one of R 4 , R 5 , R 6 , R 7 and R 8 is other than hydrogen.
Claim 3
Dependent Claim
12 words
The photoresist of claim 1 wherein the composition is a positive-acting photoresist.
Claim 4
Dependent Claim
15 words
The photoresist composition of claim 1 where the composition is a chemically amplified positive-acting composition.
Claim 5
Dependent Claim
17 words
The photoresist composition of claim 3 where the resin binder comprises a polymer having acid labile groups.
Claim 6
Dependent Claim
22 words
The photoresist composition of claim 4 where the polymer has pendant acid labile groups and contains phenolic and nonaromatic cyclic alcohol units.
Claim 7
Dependent Claim
13 words
The photoresist composition of claim 1 where the composition is a negative-acting composition.
Claim 8
Dependent Claim
23 words
The photoresist composition of claim 1 where the composition is a negative acting acid-hardening composition comprising an amine-based crosslinker and a phenolic resin.
Claim 9
Dependent Claim
18 words
The photoresist composition of claim 1 where at least one of R 1 and R 2 is hydrogen.
Claim 10
Dependent Claim
32 words
The photoresist composition of claim 1 where one or more of the groups R 4 , R 5 , R 6 , R 7 , and R 8 is an electron-withdrawing group.
Claim 11
Dependent Claim
30 words
The photoresist composition of claim 1 where one or more of the groups R 4 , R 5 , R 6 , R 7 , and R 8 is fluoro.
Claim 12
Dependent Claim
30 words
The photoresist composition of claim 1 where the photoactive compound is selected from the group consisting of pentaflurobenzyl-4-methylbenzene sulfonate, pentaflurobenzyl-4-fluorobenzene sulfonate, pentafluorobenzyl-4,5-dimethozybenzene sulfonate, pentafluorobenzyl-2,4,6-trimethylbenzene sulfonate, pentafluorobenzyl-2,3,6-trimethyl-4-methoxybenzene sulfonate and pentafluorobenzyl-ethane sulfonate.
Claim 13
Dependent Claim
11 words
The photoresist composition of claim 1 further comprising a sensitizer compound.
Claim 14
Dependent Claim
14 words
The photoresist composition of claim 12 where the sensitizer compound is a phenyl-based compound.
Claim 15
Dependent Claim
18 words
The photoresist compositions of claim 13 where the phenyl-based compound is substituted with one or more electron-donating groups.
Claim 16
Dependent Claim
22 words
An article of manufacture comprising a substrate having on at least one surface a coating layer of the photoresist of claim 1.
Claim 17
Dependent Claim
53 words
The photoresist composition of claim 1 where the substituents R 4 , R 5 , R 6 , R 7 and R 8 are each hydrogen or an electron-withdrawing group, and at least one of R 4 , R 5 , R 6 , R 7 and R 8 is an electron-withdrawing group.
Claim 18
Dependent Claim
29 words
The photoresist composition of claim 16 where the one or more electron-withdrawing R 4 , R 5 , R 6 , R 7 or R 8 groups are halo.
Claim 19
Dependent Claim
29 words
The photoresist composition of claim 16 where the one or more electron-withdrawing R 4 , R 5 , R 6 , R 7 or R 8 groups are fluoro.
Claim 20
Dependent Claim
13 words
The photoresist composition of claim 16 where the photoresist is a chemically-amplified resist.
Claim 21
Dependent Claim
136 words
A photoresist composition comprising a resin binder and one or more photoactive compounds of of the following formula I: ##STR6## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; each R 3 phenol ring substituent is independently selected from the group consisting of hydrogen, halo, hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted aryl, and substituted and unsubstituted aralkyl; and n is an integer of from 1 to 6.
Claim 22
Dependent Claim
136 words
A photoresist composition comprising a resin binder and one or more photoactive compounds of of the following formula I: ##STR6## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; each R 3 phenol ring substituent is independently selected from the group consisting of hydrogen, halo, hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted aryl, and substituted and unsubstituted aralkyl; and n is an integer of from 1 to 6.
Claim 23
Dependent Claim
144 words
The photoresist composition of claim 20 further comprising one or more photoactive compounds of the following formula II: ##STR7## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 3 phenyl ring substituent is independently selected from the group consisting of hydrogen, halo, hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted aryl, and substituted and unsubstituted aralkyl; n is an integer of from 1 to 5; and m is an integer of from 2 to 6.
Claim 24
Dependent Claim
145 words
A photoresist composition comprising a resin binder and one or more photoactive compounds of of the following formula II: ##STR8## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 3 phenyl ring substituent is independently selected from the group consisting of hydrogen, halo hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted aryl, and substituted and unsubstituted aralkyl; n is an integer of from 1 to 5; and m is an integer of from 2 to 6.
Claim 25
Dependent Claim
145 words
A photoresist composition comprising a resin binder and one or more photoactive compounds of of the following formula II: ##STR8## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 3 phenyl ring substituent is independently selected from the group consisting of hydrogen, halo hydroxy, cyano, alkanoyl, carboxyl, sulfonyl, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted aryl, and substituted and unsubstituted aralkyl; n is an integer of from 1 to 5; and m is an integer of from 2 to 6.
Claim 26
Dependent Claim
129 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR9## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, an electron-withdrawing group, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl.
Claim 27
Dependent Claim
129 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR9## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, an electron-withdrawing group, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl.
Claim 28
Dependent Claim
27 words
The photoresist composition of claim 23 where R 1 and R 2 are each independently selected from the group consisting of hydrogen and substituted and unsubstituted aryl.
Claim 29
Dependent Claim
32 words
The photoresist composition of claim 23 where one or more of the groups R 4 , R 5 , R 6 , R 7 and R 8 is an electron withdrawing group.
Claim 30
Dependent Claim
18 words
The photoresist of claim 25 where said one or more electron-withdrawing groups is halo, sulfonyl, cyano or acyl.
Claim 31
Dependent Claim
156 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR10## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, an electron-withdrawing group, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl, wherein at least one of R 4 , R 5 , R 6 , R 7 and R 8 is other than hydrogen.
Claim 32
Dependent Claim
156 words
A photoresist comprising a resin binder and at least one photoactive compound of the following formula: ##STR10## wherein R is selected from the group consisting of substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted aralkyl, and substituted and unsubstituted aryl; R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, cyano, substituted and unsubstituted alkyl, substituted and unsubstituted alkoxy, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl; each R 4 , R 5 , R 6 , R 7 and R 8 is independently selected from the group consisting of hydrogen, an electron-withdrawing group, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aralkyl and substituted and unsubstituted aryl, wherein at least one of R 4 , R 5 , R 6 , R 7 and R 8 is other than hydrogen.
Claim 33
Dependent Claim
43 words
The photoresist composition of claim 27 where one or more of the groups R 4 , R 5 , R 6 , R 7 and R 8 is an electron withdrawing group selected from the group consisting of halo, sulfonyl, cyano or acyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-09-05 | 1998-03-07 | 1998-09-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-09-05 | 2002-03-07 | 2002-09-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-09-05 | 2006-03-07 | 2006-09-06 | $7700.00 | Window Closed / Lapsed |