# US 5,346,804 A · Acid-cleavable radiation-sensitive compounds, positive working radiation-sensitive mixture containing theses compounds, and radiation-sensitive recording material produced with this mixture

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- Number: US 5,346,804 A
- Document ID: US5346804A
- Status: Granted
- Kind: A
- Application number: 07/871,008
- Filed: 1992-04-20
- Granted: 1994-09-13
- Earliest claimed: 1991-04-20
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Geog Pawlowski; Ralph Dammel; Horst Roeschert; Walter Spiess; Charlotte Eckes
- Web page: https://patentgrep.com/patent/US5346804A

## CPC

- C07D 207/404: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07C 309/65: of a saturated carbon skeleton
- C07C 309/66: Methanesulfonates
- C07C 309/73: to carbon atoms of non-condensed six-membered aromatic rings
- C07C 309/74: to carbon atoms of six-membered aromatic rings being part of condensed ring systems
- C07C 309/75: containing singly-bound oxygen atoms bound to the carbon skeleton
- C07C 309/77: containing carboxyl groups bound to the carbon skeleton
- C07D 207/452: with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
- C07D 317/24: esterified
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07C 2601/14: The ring being saturated
- C07C 2602/28: Hydrogenated naphthalenes
- Y10S 430/115: Cationic or anionic
- Y10S 430/12: Nitrogen compound containing
- Y10S 430/126: Halogen compound containing
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A radiation-sensitive mixture which contains compounds of the formula I which generate under irradiation sulfonic acids and are cleavable by the latter ##STR1## in which R.sup.1 is an unsubstituted or substituted alkyl, fluorinated alkyl, perfluoroalkyl or aryl radical, R.sup.2 is a hydrogen atom, an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical, (R.sup.1 --SO.sub.2 --O--).sub.n X--, or R.sub.3 O--, R.sup.3 and R.sup.4 are identical or different and are unsubstituted or substituted alkyl, cycloalkylalkyl, cycloalkenylalkyl or aralkyl radicals, in which 1 to 3 aliphatic CH.sub.2 or CH groups are optionally replaced by one or more of NR.sup.5, O, S, CO, CO--O, CO--NH, O--CO--NH, CO--NH--CO, NH--CO--NH, SO.sub.2, SO.sub.2 --O or SO.sub.2 --NH, or unsubstituted or substituted alkenyl, alkynyl, cycloalkyl or cycloalkenyl radicals, or R.sup.3 and R.sup.4 are mutually linked to form an unsubstituted or substituted heterocyclic ring, R.sup.5 is an acyl radical, n is an integer from 1 to 3, and X is an alkylene, cyloalkylene, or arylene group. and which, in combination with alkali-soluble binders, give positive-working mixtures which are used especially in recording materials for UV radiation and high-energy radiation. The materials are distinguished by a high resolution in conjunction with high image contrast and excellent storage stability.

## Claims

### Claim 1

A positive-working radiation-sensitive mixture which comprises
a. a polymeric binder which is insoluble in water and soluble or at least swellable in aqueous alkaline solutions, and
b. a compound, which generates a strong acid under the action of actinic radiation and which has at least one acid-cleavable C--O--C bond wherein the compound is of the formula ##STR4## in which R.sup.1 is an unsubstituted or substituted alkyl, fluorinated alkyl, perfluoralkyl or aryl radical,
R.sup.2 is a hydrogen atom, an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical, (R.sup.1 --SO.sub.2 --O--).sub.n X--, or R.sup.3 O--,
R.sup.3 and R.sup.4 are identical or different and are unsubstituted or substituted alkyl, cycloalkylalkyl, cycloalkenylalkyl or aralkyl radicals, in which 1 to 3 aliphatic CH.sub.2 or CH groups are optionally replaced by one or more of NR.sup.5, O, S, CO, CO--O, CO--NH, O--CO--NH, CO--NH--CO, NH--CO--NH, SO.sub.2, SO.sub.2 --O or SO.sub.2 --NH, or unsubstituted or substituted alkenyl, alkynl, cycloalkyl or mutually linked to form an unsubstituted or substituted heterocyclic ring,
R.sup.5 is an acyl radical,
n is an integer from 1 to 3, and
X is an alkylene, cyloalkylene, or arylene group if n is 1 or X is a(n+1)-valent radical of an alkane, cycloalkane, or arena if n is 2 or 3.

### Claim 2 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein R.sup.1 is selected from the group consisting of a fluorinated alkyl group and a perfluoroalkyl group.

### Claim 3 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein R.sup.1 is an alkyl radical having 1 to 6 carbon atoms, or an aryl radical having 6 to 12 carbon atoms, optionally substituted with one or more substituents selected from the group consisting of halogen, alkyl, fluorinated alkyl, alkoxy, nitro, and cyano, and R.sup.2 is a hydrogen atom or an R.sup.3 O radical.

### Claim 4 (depends on 2)

A radiation-sensitive mixture as claimed in claim 2, wherein R.sup.1 has 1 to 6 carbon atoms and R.sup.2 is a hydrogen atom or an R.sup.3 O radical.

### Claim 5 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein R.sup.3 and R.sup.4 are identical or different and are alkyl or arylkyl groups, each having up to 15 carbon atoms.

### Claim 6 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein R.sup.2 is a hydrogen atom, and X is an aromatic six-membered ring.

### Claim 7 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein R.sup.3 and R.sup.4 form a heterocyclic ring selected from a 1, 3-dioxolane or 1, 3-dioxane ring.

### Claim 8 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein X is an alkylene group having 2 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 12 carbon atoms.

### Claim 9 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein (b) is sensitive to light of a wavelength from 190 to 350 nm.

### Claim 10 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, which contains (b) in a concentration from 2 to 60% by weight, based on the total weight of solids in the mixture.

### Claim 11 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein (a) has an extinction of less than 0.5 .mu.m.sup.-1 in the wavelength region of the sensitivity of (b).

### Claim 12 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein the binder comprises a polymer having at least one phenolic hydroxy group.

### Claim 13 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, which contains (a) in a concentration from 40 to 98% by weight, based on the total weight of solids in the mixture.

### Claim 14 (depends on 1)

A radiation-sensitive recording material comprising a support and a radiation-sensitive layer, wherein said radiation-sensitive layer is comprised of a radiation-sensitive mixture as claimed in claim 1.

### Claim 15 (depends on 14)

A method for producing a radiation-sensitive recording material as claimed in claim 14 which comprises applying said radiation-sensitive layer to said support.

### Claim 16 (depends on 15)

A method as claimed in claim 15, comprising dissolving said mixture in a solvent to form a solution, applying the resulting solution to said support, and removing said solvent.

### Claim 17 (depends on 15)

A method as claimed in claim 15, which comprises first applying said radiation-sensitive layer to a temporary support, and then applying said support to said radiation-sensitive layer, and then optionally removing said temporary support.

### Claim 18 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein the polymeric binder contains at most 30% by weight of novolak resins.

### Claim 19 (depends on 1)

A radiation-sensitive mixture as claimed in claim 1, wherein the polymeric binder contains a polymer of at least one monomer selected from the group consisting of p-hydroxystyrene and 3-methyl-4-hydroxystyrene.