Hoechst Aktiengesellschaft

Hoechst Japan Limited

Agfa-gevaert Ag

Clariant Corporation

Herberts Gmbh

Clariant Ag

Georg Pawlowski

Horst Roeschert

Ralph R Dammel

Walter Spiess

Hans-Joachim Merrem

Klaus-Juergen Przybilla

Hiroshi Okazaki

Yoshiaki Kinoshita

Munirathna Padmanaban

Seiya Masuda

Juergen Fuchs

Juergen Lingnau

Satoru Funato

Hans-Jerg Kleiner

Takanori Kudo

Gerhard Lohaus

Ivan Cabrera

Natsumi Suehiro

Heidrun Lutz

Thomas Gerdau

Gerhard Mack

Fritz Erdmann

Peter Wilharm

Charlotte Eckes

Natsumi Kawasaki

Klaus Juergen Przybilla

Juergen Theis

Hajime Endo

Winfried Meier

Dieter Mohr

Gerhard Buhr

Donald Lupo

Ude Scheunemann

Wolfgang Appel

Peter Lehmann

Werner Hickel

Willi-Kurt Gries

Uwe Falk

Yuko Nozaki

Guenter Jung

Claus-Peter Niesert

Masato Nishikawa

Akihiko Igawa

Natumi Suehiro

Andreas Mayer

Horst Wengenroth

Tetsu Yamamoto

Walter Herr

Guenter Hultsch

A negative-working radiation-sensitive mixture containing

Negative-working radiation-sensitive mixture, and radiation-sensitive

Acid-labile group protected hydroxystyrene polymers having recurrent pendant groups such as 1-(2-methanecarbonyl oxyethoxy)ethoxy group and 1-(2-N-methylcarbamatoethoxy) ethoxy group. A resist containing the polymer, a photo acid generator, a base, additives and a solvent is sensitive to UV, electron beam and X-ray. In the resist, acid is formed in the exposed area during irradiation, which deprotects acid-labile group catalytically during application of post-exposure baking. Positive patterns are formed after development using an alkaline solution.

Acid-labile group protected hydroxystyrene polymers or copolymers

A radiation-sensitive composition is disclosed which includes (a) a binder insoluble in water but soluble in or capable of being swelled in an aqueous alkali solution, (b) a dissolution inhibitor composed of (b1) a poly(N,O-acetal) having a general formula: ##STR1## wherein R.sup.3 is alkyl or substituted or unsubstituted aryl, R.sup.4 is a divalent group selected from alkylene, cycloalkylene, alkene or alkyne, R.sup.5 is alkyl, alkene, alkyne or cycloalkyl, X is --OCO--, --CO-- or --NHCO--, and p is a number not less than 1, and/or (b2) a phenol compound having a hydroxyl group which is protected by a group which can be cleaved in the presence of an acid, (c) a photosensitive compound capable of generating an acid when exposed to an active radiation, (d) a base capable of being decomposed when exposed to an active radiation to form a neutral compound derived therefrom, (e) a plasticizer, and (f) a solvent.

Radiation-sensitive composition containing plasticizer

A process for producing a solution of a basic or non-basic sulfonium compound (A) of formulae II-V: ##STR1## wherein R.sup.5, R.sup.6 and R.sup.7 each independently represent a C.sub.1 -C.sub.18 alkyl, aryl or heteroaryl group or an aryl group mono-, di- or tri-substituted with an alkyl, an alkylaryl, an aryl, a halogen, an alkoxy, a phenoxy, a thiophenol, a phenylsulfonyl or a phenylsulphenyl;

Positive-working radiation-sensitive mixture

Compounds of the general formula I: (SIL--X--).sub.m IN (I), in which SIL is a radical of the formula Si(R.sup.1)(R.sup.2)(R.sup.3), where R.sup.1 is an alkyl, haloalkyl or alkoxy radical of 1 to 8 carbon atoms, an alkenyl radical, an alkenyloxy or acyloxy radical of 2 to 8 carbon atoms, an aryl or aryloxy radical of 6 to 10 carbon atoms, or a dialkyl-, diaryl- or alkylaryl-methyleneaminooxy radical having C.sub.1 -C.sub.4 -alkyl or C.sub.6 -aryl groups; and R.sup.2 and R.sup.3 are identical or different radicals with the meaning of R.sup.1 or X--IN; X is a group C.sub.n H.sub.2n ; IN is the radical of a compound which is active as a photoinitiator or photosensitizer and which has at least one carbonyl group located on an aromatic nucleus; m is a number from 1 to 4; and n is a number from 2 to 12, or of the formula II: Si.sub.o O.sub.o-1 (--X--IN).sub.p R.sup.4.sub.2o+2-p (II), in which R.sup.4 is a radical with the meaning of R.sup.1, and two or more radicals R.sup.4 may be the same as or different from one another; o is a number from 2 to 20,000; and p is a number from 1 to o, and the symbols X and IN are as defined above, the group X being attached to an aromatic carbon atom which is positioned ortho to the carbonyl group of IN. The compounds are prepared by reacting a compound IN--H with a compound SIL--X' or a compound Si.sub.o O.sub.o-1 (--X').sub.p R.sup.4.sub.2o+2-p in the presence of a ruthenium compound. They are suitable as radical-forming photoinitiators or as photosensitizers in silicone-containing photopolymerizable mixtures, in particular for the production of waterless-printing planographic printing plates.

Silicone-compatible photoinitiators, and photosensitive mixtures

A radiation-sensitive composition is disclosed which includes:

Radiation-sensitive composition

A chemically amplified resist material comprising: a) a homopolymer or a copolymer of hydroxystyrene or hydroxystyrene partly protected by a group sensitive to an acid such as a tetrahydropyranyl or t-butoxycarbonyl group, b) a dissolution inhibitor such as poly(N,O-acetal) or phenol or bisphenol protected by a group cleavable with an acid, c) a photosensitive compound capable of generating an acid upon exposure, d) a base capable of degrading upon radiation to regulate the line width in a period between the exposure step and the processing steps after exposure, e) a low-molecular weight phenolic or polyphenolic compound having a structure represented by the following general formula or a mixture of the phenolic or polyphenolic compounds: ##STR1## where n is an integer of 1 to 5, m is an integer of 0 to 4, n+m.ltoreq.5, and p is an integer of 1 to 10, each R is a C.sub.1 -C.sub.12 alkyl group or an unsubstituted or substituted cycloalkyl group or a C.sub.1 -C.sub.5 hydroxyalkyl group, provided that hydrogen atoms may be substituted with a halogen atom and, when m is not less than 2, each R may be the same or different; A represents a hydrocarbon atomic grouping, having a valence of p, including an unsubstituted or substituted C.sub.1 -C.sub.100 alicyclic, chain aliphatic, or aromatic hydrocarbon or a combination thereof with the carbon atoms being optionally substituted with an oxygen atom, provided that when p is 1, A may represent a hydrogen atom and, when p is 2, A may represent --S--, --SO--, --SO.sub.2 --, --O--, --CO--, or a direct bond, and f) a solvent for dissolving the components a) to e).

Radiation sensitive composition

Sulfonic acid esters, radiation-sensitive mixtures prepared therewith

A radiation-curable mixture is disclosed which contains a compound which forms an acid under the action of high-energy radiation, and contains an acid-curable compound, wherein the compound which forms an acid contains aliphatically bound halogen (chlorine or bromine) and has a pK.sub.a value of less than about 12. A radiation-curable recording material and a process for recording high-energy radiation using the material are also disclosed. The mixture, and in particular the recording material produced therefrom, has relatively high sensitivity and improved resolution and, in addition, does not exhibit image fogging after development.

Radiation-curable mixture, and radiation-sensitive recording material

A chemically amplified radiation sensitive composition comprising: (a) a copolymer such as poly(4-hydroxystyrene-co-styrene), (b) a dissolution inhibitor such as polyacetal or (b') a crosslinking agent, (c) a radiation sensitive compound capable of generating an acid upon exposure to actinic radiation, (d) a radiation sensitive base capable of stabilizing the width of lines throughout steps from exposure to post-exposure bake treatment, and (e) a solvent for dissolving the components (a) to (d), can realize fine lines and spaces down to 0.22 microns, for example, using KrF laser, and possesses excellent heat and etch resistance and adhesiveness to substrates, and produces patterns with low standing waves arising due to substrate reflectiveness of exposed light.

A negative photoresist composition comprising:

Negative photoresist compositions comprising a photosensitive compound,

A novel positive-working radiation-sensitive mixture having a high sensitivity to radiation in a short-wavelength UV region is provided which can be developed in an aqueous alkaline solution, has a stable acid latent image and is used for the production of a semiconductor. The mixture comprises, as indispensable components, a) a binder insoluble in water but soluble in an aqueous alkaline solution, b) a compound having at least one bond cleavable with an acid, c) a compound capable of producing an acid upon radiation, and d.sub.1) a basic ammonium compound or d.sub.2) a basic sulfonium compound.

An optical component comprises an electromagnetic radiation-transparent polymeric medium having a second-order susceptibility of at least 10.sup.-9 electrostatic units where this polymeric medium comprises compounds having polar-aligned noncentrosymmetric molecular dipoles which have as structural element an electron acceptor which is bound to an electron donor via a conjugated .pi.-electron system, which makes possible an oscillation of the molecular dipole between a ground state having a first dipole moment and an electronically excited state having a second dipole moment different from the first, and the nonionic polymeric medium comprises an alternating arrangement of at least one Langmuir-Blodgett film each of at least two different nonionic polymers having nonlinear optical properties. Besides high mechanical and chemical stability the optical component of the invention has excellent nonlinear optical properties, for example frequency-doubling.

Optical component based on Langmuir-Blodgett layers

Positive-acting radiation-sensitive mixture and recording material

Sulfonic acid esters of 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine are disclosed. Also disclosed is a negative-working radiation-sensitive mixture containing such a compound in combination with a compound containing at least two acid-crosslinkable groups, and a water-insoluble polymeric binder which is soluble or at least swellable in aqueous alkaline solutions. The esters are esters of a sulfonic acid or sulfonic acids of the formula R--SO.sub.3 H or R'(--SO.sub.3 H).sub.2 with 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine of the formulae I and/or II ##STR1## where R is an optionally further substituted (C.sub.1 -C.sub.10)alkyl, (C.sub.5 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl-(C.sub.1 -C.sub.10)alkyl or (C.sub.3 -C.sub.9)heteroaryl radical, R' is an optionally substituted (C.sub.1 -C.sub.10)alkylene, (C.sub.6 -C.sub.10)arylene or (C.sub.3 -C.sub.9)heteroarylene radical, and n may be 1 or 2. The radiation-sensitive mixture according to the invention is remarkable for a high resolution and a high sensitivity over a wide spectral range and can be used to produce a radiation-sensitive recording material suitable for producing photoresists, electronic components, or printing plates, or for chemical milling.

Radiation-sensitive sulfonic acid esters and their use

Growing community of inventors

Wiesbaden, Germany

Georg Pawlowski