Siemens Aktiengesellschaft

Eberhard Kuhn

Roland Rubner

Hellmut Ahne

Wolfgang Kleeberg

Erwin Schmidt

Recai Sezi

Rainer Leuschner

Siegfried Birkle

Michael Sebald

Albert Hammerschmidt

Horst Borndorfer

Eva-Maria Rissel

Dry-developable positive resist

Cost-effective, negative resists having high thermal stability based on oligomeric and/or polymeric polybenzoxazole precursors are disclosed. Also disclosed are resist solutions having a high level of storage stability when they contain a photoactive component in the form of a bisazide and when the polybenzoxazole precursors are hydroxypolyamides having the following structure: ##STR1## where R, R*, R.sub.1, R.sub.1 * and R.sub.2 are aromatic groups, R.sub.3 is an aromatic group or a norbornene residue, and wherein n.sub.1, n.sub.2 and n.sub.3, are defined as follows:

Negative resists with high thermal stability comprising end capped

Oligomeric and/or polymeric radiation-sensitive polyimide and polyisoindoloquinazoline dione precursors which are soluble in organic solvents, and are of high purity, i.e. in particular chloride-free, are produced simply by first reacting an aromatic and/or heterocyclic tetracarboxylic acid dianhydride with an olefinically unsaturated alcohol to an olefinically unsaturated tetracarboxylic acid diester, and then reacting the latter, in the presence of a carbodiimide, with a diamino compound or a diamino compound having at least one ortho-positioned amino group. The radiation-sensitive precursors thus produced are suitable, for instance, for the production of highly heat-resistant relief structures.

Method for the preparation of polyimide and polyisoindoloquinazoline

The present invention relates to oligomeric and/or polymeric precursor stages of polyimidazoles and polyimidazopyrrolones, as well as to a method for preparing these new precursor stages. The invention provides addition products of olefinically unsaturated monoepoxides on amino group-containing polycondensation products of aromatic and/or heterocyclic tetraamino compounds with dicarboxylic-acid chlorides or esters or on amino group-containing polyaddition products of the tetraamino compounds and tetracarboxylic-acid dianhydrides. The radiation-reactive precursor stages according to the invention are suited, for example, for the preparation of highly heat-resistant relief structures.

Polyimidazole and polyimidazopyrrolone precursor stages and the

The invention relates to oligomeric and/or polymeric precursor stages of polyoxazoles, as well as to a method for the preparation of these precursor stages. New radiation-reactive polymer precursor stages are provided comprised of addition products of olefinically unsaturated monoepoxides on hydroxyl group-containing polycondensation products of aromatic and/or heterocyclic dihydroxy diamino compounds with dicarboxylic-acid chlorides or esters. The radiation-reactive precursor stages according to the invention are suitable, for example, for the preparation of highly heat-resistant relief structures and as coatings for the optical fibers of light waveguides.

Polyoxazole precursor and the preparation thereof

The invention relates to heat-resistant positive resists based upon precursor stages of highly heat-resistant polymers and light-sensitive diazoquinones, as well as to a method for preparing heat-resistant relief structures of such positive resists. The positive resists of the type mentioned are developed in such a manner that they are heat-resistant as well as have a long storage life and are easily processed. The invention provides for the use of oligomer and/or polymer precursor stages of polyoxazoles in the form of polycondensation products of aromatic and/or heterocyclic dihydroxydiamino compounds and dicarboxylic acid chlorides or esters. The positive resists according to the invention are suitable especially for applications in microelectronics.

Method for the preparation of heat-resistant relief structures using

The present invention relates to oligomeric and/or polymeric radiation-reactive precursor stages of polyimides, polyisoindoloquinazoline diones, polyoxazine diones and polyquinazoline diones as well as to a method for the preparation of these radiation-reactive precursor stages. The invention provides addition products of olefinically unsaturated monoepoxides on carboxyl group-containing polyaddition products of aromatic and/or heterocyclic tetracarboxylic-acid dianhydrides and diamino compounds or diamino compounds with at least one ortho-position amido group, or on carboxyl group-containing polyaddition products of aromatic and/or heterocyclic dihdyroxy dicarboxylic acids or corresponding diaminodicarboxylic acids and diisocyanates. The radiation-reactive precursor stages according to the invention are suitable, for example, for the manufacture of highly heat-resistant relief structures.

Polyimide, polyisoindoloquinazoline dione, polyoxazine dione and

The invention relates to oligomeric and/or polymeric radiation-reactive precursor stages of polymers on the basis of heterocycles and has the objective to make available radiation-reactive precursor stages of this kind in which the problems arising due to the need of using organic solvents are eliminated. For this purpose, the invention provides addition products of cyclic carboxylic-acid anhydrides with hydroxyl group-containing compounds, where the hydroxyl group-containing compounds represent addition products of olefinically unsaturated monoepoxides on carboxyl group-containing prepolymers of polyimides, polyisoindoloquinazoline diones, polyoxazine diones and polyquinazoline diones or on amino group-containing prepolymers of polyimidazoles and polyimidazopyrrolones or on hydroxyl group-containing prepolymers of polyoxazoles. The radiation-reactive precursor stages according to the invention are suited, for example, for the manufacture of highly heat-resistant relief structues.

Radiation-reactive precursor stages of highly heat-resistant polymers

The invention relates to a method for the preparation of highly heat-resistant relief structures with a base of polymers of heterocyclic structure by applying radiation-sensitive soluble polymer precursor stages in the form of a film or foil to a substrate, irradiating the film or foil through negative patterns with actinic light or by deflecting a light, electron or ion beam, removing the non-irradiated film or foil portions and, optionally, by subsequent annealing, as well as to the use of relief structures prepared in this manner. It is provided to use as polymer precursor stages addition products of cyclic carboxylic-acid anhydrides with hydroxyl group-containing compounds, where the hydroxyl group-containing compounds represent addition products of olefinically unsaturated mono-epoxides on carboxyl group-containing prepolymers of polyimides, polyisoindoloquinazoline diones, polyoxazine diones and polyquinazoline diones or on amino group-containing prepolymers of polyimidazoles and polyimidazopyrrolones or on hydroxyl group-containing prepolymers of polyoxazoles. The relief structures prepared by the method according to the invention are suitable especially for use as resists, surface coating materials and insulating materials.

Method for the preparation of highly heat-resistant relief structures

Heat resistant positive resists containing polyoxazoles

Disclosed herein is a method for the preparation of highly heat-resistant relief structures by applying radiation-sensitive soluble polymer precursor stages in the form of a layer or a foil to a substrate; irradiating the layer or foil through negative patterns with actinic light or by deflecting a light, electron or ion beam; removing the non-irradiated layer or foil portions and, optionally, subsequently annealing, as well as to the use of the relief structures made in this manner. An object of the invention is to broaden the supply of highly heat-resistant relief structures, and for this purpose it is provided to use precursor stages of polyoxazoles in the form of addition products of olefinically unsaturated monoepoxides on hydroxyl group-containing polycondensation products of aromatic and/or heterocyclic dihydroxy diamino compounds with dicarboxylic-acid chlorides or esters. The relief structures prepared by the method according to the invention are suitable particularly for use as resists, surface coating material and insulation material.

Method for the manufacture of highly heat-resistant relief structures

The present invention relates to a method for the preparation of highly heat-resistant relief structures by applying radiation-sensitive soluble polymer precursor stages in the form of a film or a foil to a substrate; irradiating the film or the foil through negative patterns with actinic light or by deflecting a light, electron or ion beam; removing the non-irradiated film or foil portions; and optionally, by subsequent annealing; as well as to the use of the relief structures made in this manner. It is provided for this purpose to use precursor stages of polyimidazoles and polyimidazopyrrolones in the form of addition products of olefinically unsaturated monoepoxides on amino group-containing polycondensation products of aromatic and/or heterocyclic tetraamino compounds with dicarboxylic-acid chlorides or esters, or on amino group-containing polyaddition products of the tetraamino compounds and tetracarboxylic-acid dianhydrides. The relief structures prepared by the method according to the invention are suited particularly for use as resists, surface coating material and insulating material.

Method for the preparation of highly heat-resistant relief

The invention relates to new arylsulfonylazides as well as the use of these compounds. The new compounds are characterized by the general formula: ##STR1## where R=aryl; x=1 or 2; and R.sup.1 and R.sup.2 are selected from H, CH.sub.3 and Cl and may be the same or different, with the provision that CH.sub.3 and Cl are not present side by side. The compounds according to the invention are suitable as photoinitiators in the preparation of relief structures by phototechniques from olefinically unsaturated polymers, as well as cross-link enhancing agents in the radical-wise cross linking of thermoplastic polymers.

N-Azidosulfonylaryl-maleinimides

The invention relates to a method for the preparation of highly heat-resistant relief structures on the basis of polyimides, polyisoindoloquinazoline diones, polyoxazine diones and polyquinazoline diones by applying radiation-sensitive soluble polymer precursor stages to a substrate in the form of a film or a foil; irradiating the film or the foil through negative patterns with actinic light or by deflecting a light, electron or ion beam; removing the non-irradiated film or foil portions and optionally, by subsequent annealing; as well as the use of relief structures so prepared. It is an object of the invention to simplify the preparation of relief structures of the type mentioned. For this purpose, it is provided to use as the polymer precursor stages addition products of olefinically unsaturated monoepoxides to carboxyl group-containing polyaddition products of aromatic and/or heterocyclic tetracarboxylic acid dianhydrides and diamino compounds or diamino compounds with at least one orthoposition amido group or of aromatic and/or heterocyclic dihydroxy dicarboxylic acids or corresponding diamino dicarboxylic acids and diisocyanates. The relief structures prepared by the method according to the invention are suitable in particular for use as a resist, surface coating material and insulating material.

The invention relates to a method for making more efficient the preparation of relief structures by phototechniques from mixtures containing acrylate- and/or methacrylate-group-containing polymers and photo-initiators. For this purpose, the invention provides the use of aromatic azides free of maleinimide groups as photo-initiators. The method according to the invention is suitable particularly for the structurization by phototechniques of insulating materials as well as of semiconductor and conductor materials.

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Hemhofen, Germany

Eberhard Kuhn