Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions and a substantially consistent molecular weight. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
Type:
Grant
Filed:
December 29, 1992
Date of Patent:
December 19, 1995
Assignee:
Hoechst Celanese Corporation
Inventors:
M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
Abstract: Poly(hydroxystyrene) resins in which a portion of the hydroxyl groups are functionalized with t-butyloxycarbonyl groups ("t-Boc") tend to decompose during drying of the wet solid and on storage in the solid state. Solutions that are more stable than the solid material can be made from the wet freshly synthesized solid by dissolving the wet solid in a solvent that forms an azeotrope with water and then distilling the azeotrope of water and solvent from the solution until the solution contains less than about 1% by weight of water.
Abstract: The present invention relates to a water insoluble. aqueous alkali soluble novolak resin blend, wherein the resin blend comprises two novolaks having dissimilar relative molecular weights and similar dissolution rates, a process for producing such a resin blend, a photoresist containing such a resin blend and a method for producing a semi-conductor device utilizing such a photoresist.
Type:
Grant
Filed:
December 29, 1992
Date of Patent:
December 20, 1994
Assignee:
Hoechst Celanese Corporation
Inventors:
Thomas J. Lynch, Chester J. Sobodacha, Dana L. Durham
Abstract: The present invention provides mixture of at least two novolak resins with a molecular weight distribution overlap of at least 50% and having dissolution rates which differ by a factor of at least 2.0. A method is also provided for producing such novolak resin mixtures.
Type:
Grant
Filed:
September 28, 1992
Date of Patent:
December 6, 1994
Assignee:
Hoechst Celanese Corporation
Inventors:
Ping H. Lu, Anthony Canize, Dinesh N. Khanna, M. Dalil Rahman
Abstract: A photosensitizer comprising a diazo ester of benzolactone ring compound, such as phenolphthalein or cresolphthalein as the backbone, where at least one of the hydroxy groups on benzolactone ring has been esterified with diazo-sulfonyl chloride consisting of 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride or a mixture thereof, and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition and a suitable solvent.
Type:
Grant
Filed:
April 2, 1993
Date of Patent:
September 20, 1994
Assignee:
Hoechst Celanese Corporation
Inventors:
Dinesh N. Khanna, Douglas McKenzie, Chester J. Sobodacha, Ralph R. Dammel
Abstract: A method of preparing a photosensitizer condensate comprising: condensing a phenolic compound with a diazo sulfonyl chloride, wherein from about 50 to 100 mole percent of the diazo moiety is 2,1,4-diazo and from 0 to about 50 mole percent of the diazo moiety is 2,1,5 diazo; the phenolic compound having, on average, from about 60 mole percent to about 100 mole percent of its hydroxy groups esterified by the diazo sulfonyl chloride; wherein the condensing is conducted in a lactone solvent in the presence of an acid scavenger; and then subsequently isolating the photosensitizer condensate.
Abstract: The present invention provides a process for producing a developer containing a surfactant which contains a very low level of metal ions and a process for developing light sensitive photoresist compositions, using such a developer, to produce semiconductor devices.
Abstract: A photoimaged article having a protected image composed of a colored image on a support; and a thin, transparent, flexible, nonself supporting, protective layer on the surface of the image. The layer is substantially nontacky at room temperature, and has at least a major amount based on the weight of the layer of one or more thermoplastic resins of a vinyl acetal, vinyl chloride, or acrylic polymer or copolymer having a Tg of from about 35.degree. C. to about 110.degree. C. The layer is capable of being adhesively transferred directly to the image when the layer is first applied on the release surface of a temporary support, and the image and protective layer are laminated together under pressure at temperatures of between about 60.degree. C. to about 180.degree. C. with subsequent removal of the temporary support. The side of said layer opposite to the image is free from additional layers. The adhesive layer is one which does not cohesively block at temperatures of about 50.degree. C. or less.
Abstract: A process for converting a normally positive working photosensitive composition to a negative working composition is disclosed. One forms a composition containing an alkali soluble resin, a 1,2 quinone diazide-4-sulfonyl compound and an acid catalyzed crosslinker in a solvent mixture. After drying and imagewise exposing, the composition is baked and developed to produce a negative image. The image-reversal negative-working photoresists of this invention have superior storage stability and shelf life.
Type:
Grant
Filed:
December 30, 1991
Date of Patent:
October 26, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Mark A. Spak, Donald Mammato, Dana Durham, Sangya Jain
Abstract: This invention relates to novel radiation sensitive compositions. More particularly the invention relates to photoresists containing phosphorus and nitrogen linked polymers; i.e., polyphosphazenes, useful in the preparation of a relief pattern on a substrate; e.g., a silicon wafer or aluminum plate. The polyphosphazenes of in this invention can be synthesized by the condensation of N-trimethylsilylalkoxyphosphorimides. Radiation sensitive positive photoresist compositions of the invention can be developed in aqueous base developer or organic solvent developer The base developer dissolution properties of the composition can be controlled by incorporating carboxylate groups into the polyphosphazene. The polyphosphazenes utilized in this invention have good solubility properties in various organic solvents and also have good mechanical, electrical, adhesion and thermal properties.
Type:
Grant
Filed:
December 18, 1991
Date of Patent:
September 28, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Thomas J. Lynch, Dana L. Durham, Chester Sobodacha
Abstract: A white, partially translucent, metallized film article which having a flexible, heat resistant, polymeric film material with opposite sides. The film material has deposited on a first side a metal coating which is spectrally reflective and partially light transmissive in the visible region of the spectrum, is capable of transmitting from about 1% to about 70% of incident visible light cast thereon; the second side having a white outermost surface, and has a visible light opacity of from about 0.5 to about 0.98.
Type:
Grant
Filed:
March 22, 1990
Date of Patent:
September 21, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Robert J. von Trebra, Gerald A. Smith, Roy E. Hensel, Oliver A. Barton, deceased
Abstract: A developer composition for positive color proofing films containinga) sodium, potassium or ammonium octyl sulfate; sodium, potassium or ammonium lauryl sulfate; sodium decyl sulfate; or sodium tetradecyl sulfate; andb) sodium or potassium borate; andc) boric acid; andd) monobasic sodium or potassium phosphate; ande) sodium or potassium citrate; andf) sodium or potassium salicylate; andg) sodium, potassium or lithium benzoate; andh) sufficient water to formulate an effective developer.
Abstract: This invention relates to positive working photopolymerizable sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to accurately predict the image quality from a lithographic printing process.
Abstract: A photosensitizer comprising a diazo ester of benzolactone ring compound, such as phenolphthalein or cresolphthalein as the backbone, where at least one of the hydroxy groups on the benzolactone ring compound has been esterified with diazo-sulfonyl chloride consisting of 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride or a mixture thereof, and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition and a suitable solvent.
Type:
Grant
Filed:
March 6, 1992
Date of Patent:
June 22, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Dinesh N. Khanna, Douglas McKenzie, Chester J. Sobodacha, Ralph R. Dammel
Abstract: A new monomer is used to prepare homo or copolymers containing blocked imide groups which are characterized by deblocking in two stages, first when acid catalyzed and thereafter in aqueous alkaline solutions. Such polymers are, therefore, especially useful in formulating positive photoresist compositions. The polymers are combined with a latent photoacid, which when exposed to actinic radiation removes the acid sensitive blocking moiety, preferably an acetal or ketal group, leaving a methylol group or substituted methylol group remaining attached to the nitrogen atom, which groups are subsequently removed by exposure to aqueous alkaline developing solutions, leaving only imide groups. ##STR1## The new monomer is a derivative of maleimide in which the imide hydrogen has been replaced with a methylol group, which is subsequently reacted to form an acetal or ketal. Preferred monomers include N-(2,4-dioxa-3,3-dimethylpentyl)-2H,5H-2,5-dioxopyrrole and related compounds.
Type:
Grant
Filed:
October 25, 1991
Date of Patent:
April 6, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Christopher E. Osuch, Michael J. McFarland
Abstract: A process for producing a color image on color proofing film which comprises:(i) providing digital data representative of the shape and color of an original image;(ii) inputting the digital data into a computer;(iii) providing a color printer which is in communication with and controlled by the computer;(iv) providing the printer with a precoated photosensitive color proofing film, a thermal wax and means for transferring the wax to the color proofing film;(v) melting the thermal wax, in response to the digital data, in a manner which provides a pattern corresponding to the shape of the original image, the pattern providing a temporary wax optical mask;(vi) exposing the photosensitive layer of the color proofing film, through the thermal wax optical mask, to actinic radiation, the wax on the color proofing film absorbing the actinic radiation, whereby a photoreaction occurs in the exposed areas of the photosensitive layer of the color proofing film; and(vii) developing the color proofing film to provide a col
Abstract: Photosensitizers containing saturated and unsaturated polycyclic compounds containing the cyclopentane-2-diazo-1,3-dione structural unit.These compounds have their maximum u.v. absorption at around 248 nm, decompose into polar products upon irradiation, and can be used as photosensitizers in positive deep u.v. or excimer laser (248 nm) lithography. They are most preferably useful with deep u.v. transparent resins for forming photoresists.
Type:
Grant
Filed:
April 30, 1991
Date of Patent:
January 26, 1993
Assignee:
Hoechst Celanese Corporation
Inventors:
Chengjiu Wu, Anne Mooring, James T. Yardley
Abstract: The method for forming an image which comprisesI). providing a mesh fabric substrate, andII). coating said substrate with a light sensitive screen printing composition which comprises in admixtureA). at least one substantially water soluble binder resin component comprising an admixture of polyvinyl alcohol and polyvinyl acetate in an amount of from about 33% to about 90% polyvinyl alcohol and from about 10% to about 67% polyvinyl acetate based on the weight of the resin component, in sufficient amount to bind the composition components in a substantially uniform film when the composition is coated on a substrate and dried; andB). a photosensitive component in sufficient amount to substantially, uniformly photosensitize the composition,C).
Abstract: The present invention relates to dyestuffs soluble in organic solvents having the structure: ##STR1## wherein R is CF.sub.3 or phenyl, R.sub.1 and R.sub.2 are the same or different substituent groups selected from the group consisting of hydrogen, hydroxy, halogen, C.sub.1 to C.sub.3 alkyl and C.sub.1 to C.sub.4 alkoxy, R.sub.3 is selected from the groups consisting of hydrogen, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy, COOH, and COOR.sub.5 wherein R.sub.5 is C.sub.1 to C.sub.4 alkyl, R.sub.6 is selected from the group consisting of hydrogen, sulfonyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy and halogen, and n is zero or a whole number ranging from 1 to 3. The dyestuffs of the invention are useful as light absorbers or antihalation agents in photosensitive compositions. They may also be used as dyeing agents for paper, fibers or films and as components in printing ink formulations.