Radiation-sensitive compounds, radiation-sensitive mixture prepared therewith and copying material

Claim 2

A radiation-sensitive compound which is an ester or amide of a 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid of the general formula: ##STR9## in which R 1 and R 2 are identical or different and denote hydrogen, an alkyl group containing 1 to 6 carbon atoms, an alkyl ether group or an alkyl thioether group whose carbon chains may be interrupted by ether oxygen atoms, containing a total of 1 to 6 carbon atoms, or an acylamino group containing 2 to 6 carbon atoms, R 1 and R 2 not being hydrogen at the same time.

Claim 3

A compound as claimed in claim 1, in which R 1 denotes hydrogen and R 2 denotes alkyl ether groups or alkyl thioether groups whose carbon chain may be interrupted by ether oxygen atoms, containing 1 to 6 carbon atoms.

Claim 4

A compound as claimed in claim 1, in which R 1 denotes hydrogen or methyl and R 2 denotes methyl or an alkyl ether group containing 1-4 carbon atoms.

Claim 5

A compound as claimed in claim 1, in which R 1 denotes, in position 6, hydrogen or methyl and R 2 denotes, in position 7, methyl or the methyl ether group.

Claim 6

A compound as claimed in claim 1, in which R 1 denotes, in position 6, hydrogen and R 2 denotes, in position 7, the methyl ether group.

Claim 7

A radiation-sensitive compound as claimed in claim 1, which is an ester and is formed from the 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid of the formula I and a mono- or polyhydroxyaryl compound of the formula II: ##STR10## R b =H, an OH group, halogen or a lower alkyl group, at least one and not more than six R b groups being OH groups, X=a carbon bond, --O--, --S--, --SO 2 --, ##STR11## it being possible in each case for individual CH 2 groups to be replaced by ether functions or the hydrogen by substituents, n=1 or 2, p=1 to 3, Y=H or an optionally substituted alkoxy group, carboxy group, carboxyalkyl group, carboxyalkoxyalkyl group or aryl group, and R c =H or an optionally substituted alkyl group or aryl group, or of the formula III ##STR12## R d =H or an OH group, at least one of the R d groups being an OH group, or of the formula IV ##STR13## in which R e =H or an optionally substituted alkyl group, alkoxy group or aryl group, or of the formula V R.sub.f --OH (V) in which R f =a straight-chain or branched alkyl group, cycloalkyl group or aralkyl group, optionally substituted by halogen or an acylamino radical and containing 1 to 14 carbon atoms, whose carbon chain may be interrupted by ether oxygen atoms, or of the group --Z--OH in which Z=an alkylene radical containing 2 to 12 carbon atoms or a cycloalkylene radical containing 8 to 18 carbon atoms, whose carbon chains may be interrupted by ether oxygen atoms, or an aralkylene radical containing 8 to 16 carbon atoms, it being possible for the cycloaliphatic and aromatic members to be joined by a single bond, by --O--, --S--, --SO 2 --, --CO--, ##STR14##

Claim 8

A radiation-sensitive compound as claimed in claim 1, which is an amide formed from the 1,2-naphthoquinone (2)-diazide-4-sulfonic acid of the formula I and a primary or secondary amine of the formula VI: H--NR.sub.g R.sub.h (VI) in which R g =hydrogen, an optionally substituted alkyl, cycloalkyl, aryl or aralkyl radical containing 1 to 14 carbon atoms, whose carbon chain may be interrupted by ether oxygen atoms, R h =--E--NR g H in which E=an alkylene radical containing 2 to 12 carbon atoms, whose carbon chain may be interrupted by ether oxygen atoms, a cycloalkylene, arylene or aralkylene radical containing 8 to 18 carbon atoms, it being possible, in the case of polynuclear compounds, for the cycloaliphatic and aromatic members to be joined by a single bond, by --O--, --S--, --SO 2 --, --CO-- or --R g --.

Claim 9

A radiation-sensitive mixture which comprises in admixture: a) a water-insoluble resinous binder which is soluble or at leastswellable in aqueous alkaline or organic solvents, and b) a radiation-sensitive compound or mixure of radiation-sensitive compounds, wherein at least one of said radiation-sensitive compounds is an ester as claimed in claim 6.

Claim 10

A mixture as claimed in claim 8, further comprising a crosslinking agent.

Claim 11

A mixture as claimed in claim 8, wherein said binder is a novolak, a polyvinylphenol or a polyvinylalkylphenol.

Claim 12

A mixture as claimed in claim 8, further comprising a solvent or a solvent mixture.

Claim 13

A mixture as claimed in claim 8, further comprising a dyestuff, a leveling agent, a plasticizer, an adhesion promoter, a development accelerator or a surfactant.

Claim 14

A mixture as claimed in claim 8, wherein said binder is present in a concentration of about 15 to 99 percent by weight, based on the solid constituents of the mixture.

Claim 15

A mixture as claimed in claim 8, wherein said radiation-sensitive compound is present in a concentration of about 1 to 85 percent by weight, based on the solid constituents of the mixture.

Claim 16

A radiation-sensitive mixture which comprises in admixture: a) a water-insoluble resinous binder which is soluble or at least swellable in aqueous alkaline or organic solvents, and b) a radiation-sensitive compound or mixture of radiation-sensitive compounds, wherein at least one of said radiation-sensitive compounds is an amide as claimed in claim 7.

Claim 17

A mixture as claimed in claim 15, further comprising a crosslinking agent.

Claim 18

A mixture as claimed in claim 15, wherein said binder is a novolak, a polyvinylphenol or a polyvinylalkylphenol.

Claim 19

A mixture as claimed in claim 15, further comprising a solvent or solvent mixture.

Claim 20

A mixture as claimed in claim 15, further comprising a dyestuff, a leveling agent, a plasticizer, an adhesion promoter, a development accelerator or a surfactant.

Claim 21

A mixture as claimed in claim 15, wherein said binder is present in a concentration of about 15 to 99 percent by weight, based on the solid constituents of the mixture.

Claim 22

A mixture as claimed in claim 15, wherein said radiation-sensitive compound is present in a concentration of about 1 to 85 percent by weight, based on the solid constituents of the mixture.

Claim 23

A radiation-sensitive copying material, which comprises a coating base and a radiation-sensitive coating, wherein said radiation-sensitive coating comprises a radiation-sensitive mixture as claimed in claim 8 essentially freed of solvent.

Claim 24

A copying material as claimed in claim 22, wherein said coating base is a silicon wafer or a gallium arsenide wafer on which at least one further coating is additionally deposited between the semiconducting material and the radiation-sensitive coating.

Claim 25

A radiation-sensitive copying material which comprises a coating base and a radiation-sensitive coating, wherein said radiation-sensitive coating comprises a radiation-sensitive mixture as claimed in claim 15 essentially freed of solvent.

Claim 26

A copying material as claimed in claim 24, wherein said coating base is a silicon wafer or a gallium arsenide wafer on which at least one further coating is additionally deposited between the semiconducting material and said radiation-sensitive coating.