US5258257A
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US
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Radiation sensitive compositions comprising polymer having acid labile groups
Assignee: Shipley Co Inc
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Filing: 1991-09-23
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Granted: 1993-11-02
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Expires: 2011-09-23
Abstract
Abstract The invention provides a radiation sensitive composition having a polymer binder of phenolic and cyclic alcohol units. At least a portion of the phenolic units and/or cyclic alcohol units of the polymer are bonded to acid labile groups. High solubility differentials between exposed and unexposed regions are realized with only moderate substitution of the binder with the acid labile groups.
Inventors
- 👤 Roger Sinta
- 👤 Richard C. Hemond
- 👤 David R. Medeiros
- 👤 Martha M. Rajaratnam
- 👤 James W. Thackeray
- 👤 Dianne Canistro
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:57
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233; G03F7/0045; G03F7/039; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106; Y10S430/11
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
84 words
A radiation sensitive composition comprising an admixture of a resin binder and a radiation sensitive component which generates acid upon-exposure to activating radiation, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups, and the radiation sensitive component being present in an amount capable of generating a latent image by exposure of a coating of the composition to activating radiation.
Claim 2
Dependent Claim
84 words
A radiation sensitive composition comprising an admixture of a resin binder and a radiation sensitive component which generates acid upon-exposure to activating radiation, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups, and the radiation sensitive component being present in an amount capable of generating a latent image by exposure of a coating of the composition to activating radiation.
Claim 3
Dependent Claim
25 words
The composition of claim 1 where the polymer is a selected from the group consisting of a partially hydrogenated novolak and a partially hydrogenated poly(vinylphenol).
Claim 4
Dependent Claim
23 words
The composition of claim 1 where the polymer has a major portion of phenolic units and a minor portion of cyclic alcohol units.
Claim 5
Dependent Claim
25 words
The composition of claim 1 where the concentration of cyclic alcohol units is about 50 mole percent or greater of the total of the polymer.
Claim 6
Dependent Claim
25 words
The composition of claim 1 where the concentration of cyclic alcohol units is about 60 mole percent or greater of the total of the polymer.
Claim 7
Dependent Claim
25 words
The composition of claim 1 where the concentration of cyclic alcohol units is about 70 mole percent or greater of the total of the polymer.
Claim 8
Dependent Claim
13 words
The composition of claim 1 where the acid labile groups are acetate groups.
Claim 9
Dependent Claim
127 words
The composition of claim 7 where the acid labile groups have the formula --CR 1 R 2 C(═O)--O--R 3 wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, an electron withdrawing group, halo, lower alkyl having from 1 to about 10 carbon atoms, and substituted lower alkyl having from 1 to about 10 carbon atoms; R 3 is selected from the group consisting of lower alkyl having from 1 to about 10 carbon atoms, substituted lower alkyl having from 1 to about 10 carbon atoms, aryl having from 6 to about 10 carbon atoms, substituted aryl having from 6 to 10 carbon atoms, benzyl having from 7 to 11 carbon atoms and substituted benzyl having from 7 to 11 carbon atoms.
Claim 10
Dependent Claim
18 words
The composition of claim 8 where one or both of R 1 and R 2 are a halogen.
Claim 11
Dependent Claim
13 words
The composition of claim 1 where the acid labile groups are oxycarbonyl groups.
Claim 12
Dependent Claim
21 words
The composition of claim 10 where the oxycarbonyl groups are selected from the group consisting of tert-butoxy carbonyl and benzyloxy carbonyl.
Claim 13
Dependent Claim
31 words
The composition of claim 1 where the acid labile groups are bonded to the phenolic units of the polymer, and the cyclic alcohol units are substantially free of acid labile groups.
Claim 14
Dependent Claim
23 words
The composition of claim 1 where the acid labile groups are bonded to both phenolic units and cyclic alcohol units of the polymer.
Claim 15
Dependent Claim
22 words
The composition of claim 1 where a mixture of two or more different acid labile groups are bonded to the polymer binder.
Claim 16
Dependent Claim
25 words
The composition of claim 1 where about one percent of the total hydroxyl units of the polymer binder are bonded to the acid labile groups.
Claim 17
Dependent Claim
28 words
The composition of claim 1 where between about 5 and 35 percent of the total hydroxyl units of the polymer binder are bonded to the acid labile groups.
Claim 18
Dependent Claim
34 words
The composition of claim 1 where the radiation sensitive component is an acid generator compound selected from the group consisting of o-quinone diazide sulfonic acid esters, non-ionic photogenerator compounds, onium salts, and sulfonated esters.
Claim 19
Dependent Claim
28 words
The composition of claim 1 where the composition is negative acting when developed with an organic developer to remove unexposed areas of a coating layer of the composition.
Claim 20
Dependent Claim
29 words
The composition of claim 1 where the composition is positive acting when developed with an aqueous alkaline developer to remove exposed areas of a coating layer of the composition.
Claim 21
Dependent Claim
19 words
The composition of claim 1 where the phenolic units and cyclic alcohol units are randomly interspersed throughout the polymer.
Claim 22
Dependent Claim
13 words
The composition of claim 1 further comprising one or more dissolution inhibitor compounds.
Claim 23
Dependent Claim
120 words
A process for forming a relief image comprising: (a) applying a layer of a radiation sensitive composition to a substrate, the composition comprising an admixture of a resin binder and a radiation sensitive component which generates an acid upon exposure to activating radiation, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups, and the radiation sensitive component being present in an amount capable of generating a latent image by exposure of a coating of the composition to activating radiation; and (b) exposing and developing the photoresist layer on the substrate to yield a relief image.
Claim 24
Dependent Claim
120 words
A process for forming a relief image comprising: (a) applying a layer of a radiation sensitive composition to a substrate, the composition comprising an admixture of a resin binder and a radiation sensitive component which generates an acid upon exposure to activating radiation, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups, and the radiation sensitive component being present in an amount capable of generating a latent image by exposure of a coating of the composition to activating radiation; and (b) exposing and developing the photoresist layer on the substrate to yield a relief image.
Claim 25
Dependent Claim
18 words
The process of claim 22 further comprising metallizing or etching substrate areas bared of the radiation sensitive composition.
Claim 26
Dependent Claim
17 words
The process of claim 22 where the radiation sensitive composition layer is exposed with deep UV radiation.
Claim 27
Dependent Claim
25 words
The process of claim 22 where about 1 percent of the total hydroxyl units of the resin binder are bonded to the acid labile groups.
Claim 28
Dependent Claim
27 words
The process of claim 22 where between about 5 and 35 percent of the total hydroxyl units of the polymer are bonded to the acid labile groups.
Claim 29
Dependent Claim
25 words
The process of claim 22 where the concentration of cyclic alcohol units is about 50 mole percent or greater of the total of the polymer.
Claim 30
Dependent Claim
25 words
The process of claim 22 where the concentration of cyclic alcohol units is about 60 mole percent or greater of the total of the polymer.
Claim 31
Dependent Claim
25 words
The process of claim 22 where the concentration of cyclic alcohol units is about 70 mole percent or greater of the total of the polymer.
Claim 32
Dependent Claim
28 words
The process of claim 22 where the substrate comprises one or more materials selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum and aluminum oxide.
Claim 33
Dependent Claim
11 words
An article of manufacture produced by the process of claim 23.
Claim 34
Dependent Claim
68 words
An article of manufacture comprising a radiation sensitive composition coating on a substrate, the composition coating comprising a radiation sensitive component which generates an acid upon exposure to activating radiation and a resin binder, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups.
Claim 35
Dependent Claim
68 words
An article of manufacture comprising a radiation sensitive composition coating on a substrate, the composition coating comprising a radiation sensitive component which generates an acid upon exposure to activating radiation and a resin binder, the resin binder comprising a polymer having phenolic units and non-aromatic cyclic alcohol units, between about 1 and 50 percent of the total hydroxyl groups of the polymer being bonded to acid labile groups.
Claim 36
Dependent Claim
26 words
The article of claim 32 where between about 5 and 35 percent of the total hydroxyl units of the polymer are bonded to acid labile groups.
Claim 37
Dependent Claim
25 words
The article of claim 32 where the concentration of cyclic alcohol units is about 50 mole percent or greater of the total of the polymer.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1996-11-01 | 1997-05-03 | 1997-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-11-01 | 2001-05-03 | 2001-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-11-01 | 2005-05-03 | 2005-11-02 | $7700.00 | Window Closed / Lapsed |