Loctite (ireland) Limited

Loctite Corporation

John G Woods

John M Rooney

Stephen J Harris

David P Melody

John Rooney

Pauline Coakley

M Anthony McKervey

John Guthrie

Paul Conway

Bernard J Bolger

Anthony Francis Jacobine

David M Glaser

Francis Richard Martin

Marueen G MacManus

Walter J Steinkraus

Bernard Ryan

David Phelan

J Eisirt Casey

Anionically polymerizable monomers containing at least one silicon or titanium atom form polymeric photoresists having good dry etch resistance for use in microlithography. The monomers are of the formula ##STR1## wherein A is --H or --CH.dbd.CH.sub.2 ; X is a strong electron withdrawing group;

Anionically polymerizable monomers, polymers thereof and use of such

A photoresist coating for use in microlithography comprises a polymer of a monomer of the formula ##STR1## wherein X and Y are strong electron withdrawing groups and R.sup.4 is H or, providing that X and Y are both --CN, R.sup.4 may be aliphatic hydrocarbyl, aryl or alkaryl. Preferred monomers are of the formula ##STR2## wherein R.sup.7 is a C.sub.1 -C.sub.5 alkyl or C.sub.2 -C.sub.5 alkenyl group, more particularly ethyl 2-cyanopenta-2,4-dienoate or allyl 2-cyanopenta-2,4-dienoate. Methods for applying a resist coating by vapor deposition of these monomers and exposure to radiation are described. A positive or negative tone image can be produced, depending upon the imaging method employed.

Photoresists formed by polymerization of di-unsaturated monomers

Polymers comprising a polymer backbone having pendant or terminal betadiketone groups which contain at least one trifluoromethyl group. The betadiketone groups may be selected from trifluorocetoacetate groups (general formula I); ##STR1## hexafluoroacetylacetone groups (general formula II); ##STR2## or trifluoro-2,4-pentanedione groups (general formula III); ##STR3## where  indicates the polymer backbone, R is an alkyl, substituted alkyl, aryl or substituted aryl group and R.sup.1 is hydrogen, alkyl or substituted alkyl. Neither the R group nor the R.sup.1 group should contain any group which is sufficiently basic to initiate cyanoacrylate polymerization or any group sufficiently acidic to interfere with chain transfer.

Polymers comprising betadiketone groups and polymerizable compositions

Thiol/ene compositions

Cationically polymerizable styryloxy resins having urethane linkages, represented by the formula III ##STR1## wherein R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 is H and the other is methyl;

Polymerizable styryloxy resins and compositions thereof

An encapsulating composition for electronic devices comprises a curable material such as a silicone resin and an ion scavenger compound selected from certain calixarene or oxacalixarene compounds in which at least half of the phenolic groups have been substituted by specific groups and certain silacrown compounds. Exemplary ion scavenger compounds include ##STR1## the tetraethyl acetate of 7, 13, 19, 25-tetra-tertbutyl-27, 28, 29, 30-tetrahydroxy-2,3-dihomo-3-oxacalix-4-arene and 1,1-dimethasila-17-crown-6.

Encapsulating compositions

A curable thiol-ene formulation comprising

Thiolene compositions on based bicyclic 'ene compounds

Polyfunctional cationically polymerizable styryloxy compound of the formula ##STR1## where R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 are H and the other is methyl; R.sup.3 and R.sup.4 are H, lower alkyl, or alkoxy if R.sup.2 is not methyl; R.sup.5 is a divalent hydrocarbon radical; G is any multivalent organic or inorganic radical free of amino, aliphatic hydroxyl, aliphatic thiol or other groups which interfere with cationic polymerization; and n is an integer of two or more.

Styryloxy resins and compositions thereof

Cyanoacrylate adhesive compositions which employ calixarene compounds as accelerators give substantially reduced fixture and cure times on de-activating substrates such as wood. The calixarene compounds are preferably employed at levels of about 0.1-1% by weight of the composition. The calixarene compounds particularly useful in this invention may be represented by the formula: ##STR1## where R.sup.1 is alkyl, alkoxy, substituted alkyl or substituted alkoxy; R.sup.2 is H or alkyl; and n=4, 6, or 8.

Bonding method utilizing cyanoacrylate adhesive having calixarene

A linear or cross-linked polymer selected from polythioethers, polyethers, styrenic polymers, polyacrylates, and polyorganosiloxanes having a plurality of calixarene groups bound thereon, the calixarene groups having the formula ##STR1## where the R.sup.1 groups are the same or different H or hydrocarbyl groups; the R.sup.2 groups are H, hydrocarbyl, --CH.sub.2 C(=O)OR.sup.3, --CH.sub.2 C(=O)R.sup.3, or --C(=O)NHR.sup.3, R.sup.3 is hydrocarbyl or substituted hydrocarbyl; n is an integer of 1-8, m is an integer of 0-7 and n+m is 4-8.

Polymer bound calixarenes

A method for imaging vapor deposited photoresists of cyanoacrylates or related anionically polymerizable monomers without the use of solvent development. This method consists of treating the substrate with a compound which releases acid when exposed to high-energy radiation. In certain cases when the surface of the substrate is slightly acidic or neutral, it is necessary to activate the surface with a basic liquid or vapor which must be chosen so as not to react with the radiation-sensitive acid precursor. The substrate is exposed to actinic or ionizing radiation through a mask or to steered high-energy beams. Finally, the substrate is exposed to a vapor of cyanoacrylate monomer which condenses and polymerizes on the unirradiated regions forming a relief image.

Imaging method for vapor deposited photoresists of anionically

A method for applying a polymeric resist coating of very high molecular weight to a suitable substrate without the necessity of elaborate purification steps and for ensuring adequate coverage of raised regions in three-dimensionally patterned substrates. The method comprises exposing the substrate to be coated to the vapor of an anionically polymerizable monomer of the formula:

Resists formed by vapor deposition of anionically polymerizable monomer

Compositions useful as UV curable conformal coatings are mixtures, substantially free of isocyanate condensation catalyst, of the following constituents:

Conformal coating systems

A linear or cross-linked polymer selected from polythioethers, polyethers, styrenic polymers, polyacrylates, and polyorganosiloxanes having a plurality of calixarene groups bound thereon, the calixarene groups having the formula ##STR1## where the R.sup.1 groups are the same or different H or hydrocarbyl groups; the R.sup.2 groups are H, hydrocarbyl, --CH.sub.2 C(.dbd.O)OR.sup.3, --CH.sub.2 C(.dbd.O)R.sup.3, or --C(.dbd.O)NHR.sup.3, R.sup.3 is hydrocarbyl or substituted hydrocarbyl; n is an integer of 1-8, m is an integer of 0-7 and n+m is 4-8.

Polyfunctional cationically polymerizable styryloxy compounds of the formula ##STR1## where R.sup.1 is H or methyl; R.sup.2 is hydrocarbyl, hydrocarbyl interrupted by ether oxygen atoms, or halo substituted hydrocarbyl; R.sup.3 is H, lower alkyl, or alkoxy; G is any multivalent organic or inorganic radical free of amino or aliphatic thiol groups; and n is an integer of two or more.

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Dublin, Ireland

John G Woods