Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Patent
1991-09-13
1993-11-02
McCamish, Marion E.
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
430280, 430296, 430325, 430327, 430935, 430942, 428333, 428421, 4274301, 4274343, G03C 176, G03C 1492, G03F 7095, G03F 716
Patent
active
052582620
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The invention relates to a radiation-curable film composed of at least one monomolecular layer of organic polymers having long-chain side chains containing fluorine and oxiranes on a solid layer support (=so-called sandwiches), to a process for producing the sandwiches and curing them, optionally with structuring.
To produce ordered layers of organic polymers containing long-chain side groups, use is predominantly made of the Langmuir-Blodgett (LB) process. In this process, molecules are spread on a water surface and the long alkyl side groups are arranged in parallel by reducing the area per molecule. At constant shear, the molecules are drawn onto a substrate by immersion and emersion. In this process, a monomolecular layer is transferred in each immersion operation with its order being retained.
To build up LB films, use is made of amphiphilic molecules, i.e. molecules which have a hydrophilic end (a "head") and a hydrophobic end (a "tail"). There are also amphiphilic molecules in which perfluorinated alkyl chains act as hydrophobic units. In order to achieve a higher stability of the LB films, polymeric LB films, including also those having long-chain fluorine-containing side chains on a polymethacrylate or polyacrylate base have also already been prepared. Such films are described in the non-prior-published German Patent Application P 3,731,606.0. They exhibit a good order and low critical surface tension resulting therefrom, and these make them interesting, for example, for friction reduction applications. However, they can still be stripped, for example, by solvents and consequently lose their protective action. An application in microlithography is also not possible with the polymers described therein. The microstructuring of LB films with electron beams has already been described in various examples, including also even with oxirane-containing films, such as, for example, by B. Boothroyd, P. A. Delaney, R. A. Hann, R. W. Johnstone and A. Ledwith in Brit. Polym. J. 17, 360-363 (1985). There the electron-beam-induced polymerization of monomeric oxirane-containing amphiphiles in LB films is described. Structuring by crosslinking polymeric oxiranes has hitherto not yet been described in LB films.
The object was therefore to prepare synthetically easily accessible polymers which can be crosslinked by oxirane units and have nonpolar side chains and which can be satisfactorily transferred to a layer support.
The present invention achieves this object. It is based on the discovery that the products which can be obtained by copolymerization of vinyl monomers containing long-chain fluoroalkyl groups with vinyl monomers containing oxirane groups are good film formers. Owing to the fluorine-containing alkyl chains, a high etching resistance and a particularly low critical surface tension are obtained. The oxirane units are reactive and ensure the structurability. As polar units in the polymer, they should, in addition, take over the function of hydrophilic spacers which, as described, for example, by A. Laschewsky, H. Ringsdorf, G. Schmidt and J. Schneider in J. Am. Chem. Soc. 109, 788-796 (1987), make possible the different ordering tendencies of the polymer main chain (polymer coiling tendency) and the alkyl side chain (crystallization tendency) and consequently the achievement of ordered layers.
The copolymerization according to the invention proceeds particularly beneficially in solution under free-radical conditions, for example in tetrahydrofuran as solvent at 64.degree. C. with 1% azobisisobutyronitrile as free-radical initiator and with monomer ratios of 1 mol of fluoroalkyl-containing monomer to 0.05 to 10 mol of oxirane-containing monomer.
The film according to the invention is composed of at least one monomolecular layer which contains an organic polymer having long-chain fluorinated alkyl side groups and oxirane units or is composed thereof. Suitable alkyl side groups are those of the formula I: Compounds in which n=5 to 11 and m=13 to 23 are particularly readily accessible. Compounds
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T. Kitayama, Journal of Electronic Engineering, vol. 22, No. 225, 32-36 (Sep. 1985) "Lithographic Reproduction Technology Focuses on Submicron Chip Patterns".
M. Sugi, Journal of Molecular Electronics, vol. 1, 3-17 (Jul./Sep. 1985) "Langmuir-Blodgett Films-A Course Towards Molecular Electronics: A Review".
Boothroyd et al., British Polymer Journal, vol. 17, No. 4, 360-363 (1985), "Electron Irradiation of Polymerisable Langmuir-Blodgett Multilayers as Model Resists for Electron-beam Lithography".
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Erdelen Christian
Prass Werner
Ringsdorf Helmut
Scheunemann Ude
Dote Janis L.
Hoechst Aktiengesellschaft
McCamish Marion E.
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