US5338641A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Positive-working radiation-sensitive mixture and copying material produced therefrom comprising an α,α-bis(sulfonyl) diazo methane as an acid forming compound
Assignee: CLARIANT AZ (DEUTSCHLAND) AG
•
Filing: 1993-03-04
•
Granted: 1994-08-16
•
Expires: 2013-03-04
Abstract
Abstract A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents: a) an α,α-bis(sulfonyl)diazomethane, which forms a strong acid on irradiation, of the general formula ##STR1## in which R is an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical, b) a compound having at least one C--O--C or C--O--Si--bond which can be cleaved by acid, and c) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions. The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photolysis products on exposure to light.
Inventors
- 👤 Georg Pawlowski
- 👤 Hans-Joachim Merrem
- 👤 Juergen Lingnau
- 👤 Ralph Dammel
- 👤 Horst Roeschert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 20:26
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/016; G03F7/0163; G03F7/039
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
160 words
A positive-working radiation-sensitive mixture consisting essentially of, in admixture: a) a compound which forms an acid on irradiation, in an amount sufficient to cleave compound b), b) a compound having at least one C--O--C or C--O--Si bond which can be cleaved by the acid formed by compound a), said mixture comprising an amount of compound b) sufficient to render the mixture soluble or at least swellable in aqueous-alkaline solution when the acid formed from compound a) upon irradiation cleaves compound b), and c) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions, said binder being present in an amount sufficient to form a uniform film when a layer of the positive-working radiation-sensitive mixture is coated on a substrate, wherein the compound (a) is an α,α-bis(sulfonyl)diazomethane derivative of the formula I ##STR4## in which R is an alkyl, cycloalkyl, aryl or heteroaryl radical, any of which may be unsubstituted or substituted by one or more substituents.
Claim 2
Dependent Claim
160 words
A positive-working radiation-sensitive mixture consisting essentially of, in admixture: a) a compound which forms an acid on irradiation, in an amount sufficient to cleave compound b), b) a compound having at least one C--O--C or C--O--Si bond which can be cleaved by the acid formed by compound a), said mixture comprising an amount of compound b) sufficient to render the mixture soluble or at least swellable in aqueous-alkaline solution when the acid formed from compound a) upon irradiation cleaves compound b), and c) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions, said binder being present in an amount sufficient to form a uniform film when a layer of the positive-working radiation-sensitive mixture is coated on a substrate, wherein the compound (a) is an α,α-bis(sulfonyl)diazomethane derivative of the formula I ##STR4## in which R is an alkyl, cycloalkyl, aryl or heteroaryl radical, any of which may be unsubstituted or substituted by one or more substituents.
Claim 3
Dependent Claim
22 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the radical R of the compound of the formula I is substituted.
Claim 4
Dependent Claim
34 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the radical R of the compound of the formula I is an alkyl radical containing 1 to 6 carbon atoms or an aryl radical.
Claim 5
Dependent Claim
24 words
A positive-working radiation-sensitive mixture as claimed in claims 1, wherein the radical R of the compound of the formula I is an aryl radical.
Claim 6
Dependent Claim
34 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein R is an aromatic radical, the substituents of which are selected from the group consisting of alkyl, alkoxy, alkoxyalkyl, nitro, carbonyl, amido and halogen.
Claim 7
Dependent Claim
25 words
A positive-working radiation--sensitive mixture as claimed in claim 1, wherein the mixture is sensitive to UV light having a wavelength of 190 to 450 nm.
Claim 8
Dependent Claim
25 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the mixture is sensitive to UV light having a wavelength of 200 to 400 nm.
Claim 9
Dependent Claim
35 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the concentration of the acid-forming compound of the formula I is about 0.5 to 25% by weight, based on the total weight of the layer.
Claim 10
Dependent Claim
29 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the binder has an absorbance of less than about 0.5 μm -1 in the wavelength range of the irradiation.
Claim 11
Dependent Claim
23 words
A positive-working radiation-sensitive mixture as claimed in claim 1, comprising up to about 30% by weight of a novolak condensation resin as binder.
Claim 12
Dependent Claim
16 words
A positive-working radiation-sensitive mixture as claimed in claim 9, wherein the binder contains phenolic hydroxyl groups.
Claim 13
Dependent Claim
28 words
A positive-working radiation-sensitive mixture as claimed in claim 9, wherein the binder is contained in a concentration of about 60 to 96% by weight, in the radiation-sensitive mixture.
Claim 14
Dependent Claim
25 words
A positive-working radiation-sensitive mixture as claimed in claim 9, wherein the binder has an absorbance of less than about 0.3 μm -1 above 240 nm.
Claim 15
Dependent Claim
29 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the compound of the formula I has the highest molar absorption of all the resist constituents at 248 nm.
Claim 16
Dependent Claim
27 words
A positive-working radiation-sensitive copying material consisting essentially of: a support, and a radiation-sensitive layer of a radiation-sensitive mixture as claimed in claim 1 coated on the support.
Claim 17
Dependent Claim
23 words
A positive-working radiation-sensitive mixture as claimed in claim 1, comprising up to about 20% by weight of a novolak condensation resin as binder.
Claim 18
Dependent Claim
28 words
A positive-working radiation-sensitive mixture as claimed in claim 9, wherein the binder is contained in a concentration of about 70 to 94% by weight, in the radiation-sensitive mixture.
Claim 19
Dependent Claim
21 words
A positive-working radiation-sensitive mixture as recited in claim 1, wherein compound b) is a compound having at least one C--O--C bond.
Claim 20
Dependent Claim
21 words
A positive-working radiation-sensitive mixture as recited in claim 1, wherein compound b) is a compound having at least one C--O--Si bond.
Claim 21
Dependent Claim
14 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein compound (a) is bis(4-chlorophenylsulfonyl)diazomethane.
Claim 22
Dependent Claim
14 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein compound (a) is bis(4-bromophenylsulfonyl)diazomethane.
Claim 23
Dependent Claim
14 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein compound (a) is bis(phenylsulfonyl)diazomethane.
Claim 24
Dependent Claim
14 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein compound (a) is bis(t-butylphenylsulfonyl)diazomethane.
Claim 25
Dependent Claim
14 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein compound (a) is bis(4-methylphenylsulfonyl)diazomethane.
Claim 26
Dependent Claim
22 words
A positive-working radiation-sensitive mixture as claimed in claim 1, wherein the radical R of the compound of the formula I is unsubstituted.
References Cited (Backward Citations)
GB1163324A
Cited
US3515552A
Cited
US3536489A
Cited
GB1231789A
Cited
GB1234648A
Cited
US3615630A
Cited
DE1298414B
Cited
US3615455A
Cited
US3686084A
Cited
FR2071655A5
Cited
GB1388492A
Cited
US3779778A
Cited
GB1381472A
Cited
GB1381471A
Cited
US3912606A
Cited
US4101323A
Cited
US4189323A
Cited
US4247611A
Cited
US4212970A
Cited
US4232106A
Cited
US4343885A
Cited
US4248957A
Cited
US4250247A
Cited
US4279982A
Cited
US4311782A
Cited
US4371606A
Cited
US4371607A
Cited
US4506003A
Cited
US4506006A
Cited
US4491628A
Cited
EP0135348A2
Cited
US4696888A
Cited
US4619998A
Cited
US4786577A
Cited
DE3601264A1
Cited
US4806448A
Cited
US4737426A
Cited
US4603101A
Cited
EP0232972A2
Cited
US4840867A
Cited
EP0302359A2
Cited
DE3730783A1
Cited
DE3730787A1
Cited
DE3730785A1
Cited
EP0315748A2
Cited
US5250669A
Cited
US5272036A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-08-15 | 1998-02-14 | 1998-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-08-15 | 2002-02-14 | 2002-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-08-15 | 2006-02-14 | 2006-08-16 | $7700.00 | Window Closed / Lapsed |