Abstract: The present invention relates to a novel antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and an organic solvent or mixture of solvents, where the novel polymer comprises a unit containing a dye that absorbs from about 180 nm to about 450 nm and does not contain a crosslinking group.
Type:
Grant
Filed:
August 5, 1999
Date of Patent:
February 13, 2001
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Shuji Ding, Dinesh N. Khanna, Mark A. Spak, Dana L. Durham, Jianhui Shan, Eleazer Gonzalez
Abstract: The present invention relates to a novel antireflecting coating composition, where the composition comprises a polymer, thermal acid generator and a solvent composition. The invention further comprises processes for the use of such a composition in photolithography. The composition strongly absorbs radiation ranging from about 130 nm (nanometer) to about 250 nm.
Type:
Grant
Filed:
November 18, 1998
Date of Patent:
September 5, 2000
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Munirathna Padmanaban, Ralph R. Dammel, Stanley A. Ficner, Joseph E. Oberlander, John P. Sagan
Abstract: A photoresist composition comprising a film forming resin obtained by condensing a phenol derivative and a substituted diphenyl ether, a photoactive compound, and a solvent. The photoresist composition may also contain an alkali-soluble, film-forming resin, such as a novolak resin. The photoresist of the instant invention improves the photospeed, resolution and thermal stability of the photoresist images.
Type:
Grant
Filed:
November 21, 1997
Date of Patent:
August 15, 2000
Assignee:
Clariant Finance Lmited
Inventors:
Stanley F. Wanat, Kathryn H. Jensen, Ping-Hung Lu, Douglas McKenzie
Abstract: A process for producing a naphthoquinone diazide ester of a phenolic compound that is useful in a photoresist composition, which process comprises providing a naphthoquinone diazide ester solution in an organic polar solvent; adding the resulting naphthoquinone diazide ester solution to a precipitation bath that is maintained at a temperature of from about 0.degree. C. to about -30.degree. C.; and filtering the resulting naphthoquinone diazide ester.
Abstract: A polymer that when used with a suitable photoacid generator (PAG) forms a positive working photoresist. The polymer comprises of a tartaric polyanhydride backbone, an acetal protected 1,2 diol group; and a fused ring acetal group pendant to the backbone. The acetal protected .alpha.-hydroxy anhydride backbone structure, undergoes an efficient photoacid catalyzed cleavage, which gives rise to small molecular weight fragments which are readily dissolved in an aqueous base developer. This high contrast in solubility allows high resolution images to be produced. The fused rings offer etch resistance and can be comprised of either an adamantone or norcamphor ring structure. With the addition of a commercially available photo acid generator, the polymer formulation forms a positive working photoresist that offers high contrast and resolution.
Type:
Grant
Filed:
June 11, 1998
Date of Patent:
May 9, 2000
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Iain McCulloch, Anthony J. East, Ming Kang, Richard Keosian, Hyun-Nam Yoon
Abstract: The present invention provides for process of preparing a photoactive ester compound of high purity using a solid base catalyst, preferably an anionic exchange resin. The invention further provides for preparing and imaging a photosensitive composition comprising such a photoactive compound, a film-forming resin and a solvent composition.
Abstract: The invention provides a process for the generation of an antireflective bottom layer with effective reduction of substrate reflectivity and swing curve effects in lithographic applications. It involves the use of a suitably selected monomeric and/or polymeric dye which brings the real part of the refractive index into a range which is optimal for the suppression of reflection-related effects. The refractive index change is effected via anomalous dispersion, i.e., by utilizing changes in the real part of the refractive index caused by the bottom layer's absorption.
Abstract: A water soluble polymer that when used with a suitable photoacid generator (PAG) forms a negative working water soluble photoresist. The polymer comprises of a backbone, such as polyvinyl ether, coupled by a linkage group to an acetal protected .beta.-keto acid group. With the addition of a number of commercially available photo acid generators, the polymer formulation forms a negative working photoresist that is water soluble. Exposure to radiation will cause a photoacid catalyzed deprotection of the acetal group, yielding a .beta.-keto acid which, upon heating, will undergo decarboxylation, which results in a water insoluble photoproduct and evolution of CO.sub.2 as a byproduct. This photochemically induced reaction results in a significant change in the polymer solubility parameter, and the product is no longer soluble in water.
Type:
Grant
Filed:
May 27, 1998
Date of Patent:
December 7, 1999
Assignee:
Clariant International, Ltd.
Inventors:
Iain McCulloch, Anthony J. East, Ming Kang, Richard Keosian, Hyun-Nam Yoon
Abstract: The present invention relates to an antireflective coating composition comprising a novel polymer in a solvent composition. The invention further comprises processes for using the antireflective coating composition in photolithography. The antireflective coating composition comprises a novel polymer and a solvent composition, where the novel polymer of the antireflective coating comprises at least one unit containing a dye that absorbs from about 180 nm to about 450 nm and at least one unit that contains no aromatic funtionality. The solvent may be organic, preferrably, a solvent of low toxicity, or it may be water, which may additionally contain other water miscible organic solvents.
Type:
Grant
Filed:
April 30, 1997
Date of Patent:
November 30, 1999
Assignee:
Clariant Finance BVI) Limited
Inventors:
Shuji Ding, Ping-Hung Lu, Dinesh N. Khanna, Jianhui Shan, Dana L. Durham, Ralph R. Dammel, M. Dalil Rahman
Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin having consistent molecular weight and superior performance in photoresist composition, by isolating such novolak resin fractions without high temperature distillation. A method is also provided for producing photoresist composition from such a fractionated novolak resin and for producing semiconductor devices using such a photoresist composition.
Abstract: The present invention provides for process of preparing a photoactive ester compound of high purity using a solid base catalyst, preferably an anionic exchange resin. The invention further provides for preparing and imaging a photosensitive composition comprising such a photoactive compound, a film-forming resin and a solvent composition.
Abstract: A process for obtaining a lift-off imaging profile which comprises the steps of:a) providing a first layer of plasma etchable material wherein said material has a film thickness less than about 0.5 .mu.m (micrometer);b) providing a second layer comprising a photoimageable material on top of the first layer;c) forming a pattern in said second layer which comprises the steps of selectively exposing and developing the second layer;d) reacting the second layer with an organosilicon material; ande) etching the first layer isotropically in an oxygen atmosphere.
Type:
Grant
Filed:
February 18, 1997
Date of Patent:
July 13, 1999
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Mark A. Spak, Ralph R. Dammel, Michael Deprado
Abstract: A light sensitive positive composition comprising an alkali soluble resin, a novel photoactive compound represented by the structure ##STR1## where, X is O, S or N--R', where R' is H, alkyl, substituted alkyl, aryl or aralkyl,Y is a connecting group such as SO.sub.2, CO, O or NR',Z is a carbon containing organic ballast moiety having a molecular weight greater than about 75 and can form a bond with the connecting group,R is independently H, alkyl, alkoxy, aryl, aralkyl, halo or fluoroalkyl,m=1-3, and n.gtoreq.1;and a solvent or mixture of solvents. The invention further comprises a process for imaging the composition of this invention to give positive image. The light sensitive composition is especially useful as a positive deep-uv photoresist.
Type:
Grant
Filed:
March 7, 1997
Date of Patent:
March 2, 1999
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Dana L. Durham, Ping-Hung Lu, Joseph E. Oberlander, Dinesh N. Khanna
Abstract: The present invention relates to novel photosensitive quinolone compounds, specifically novel 3-diazo 2,4-quinolinedione compounds, that may be used in a variety of applications, such as, photosensitive coating compositions, pharmaceuticals, agricultural, amongst others. The invention further relates to a process for making the novel photosensitive 3-diazo 2,4-quinolinedione compounds. These compounds are particularity useful as a photoactive component in a positive working photoresist composition, particularity for use as a deep ultraviolet (UV) photoresist.
Type:
Grant
Filed:
March 7, 1997
Date of Patent:
February 2, 1999
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
Abstract: The invention provides a process for removing unwanted photoresist material from the periphery of a photoresist-coated substrate using a solvent composition of ethyl lactate and N-methyl pyrollidone, where the amount of N-methyl pyrollidone ranges from about 3% to about 20% by weight of the total composition, and where the solvent composition has a flash point of greater than 100.degree. F. (38.degree. C.), has an odor threshold value greater than 5000, is effective as both a backside and topside edge bead remover and can effectively remove the edge bead from an unbaked or baked photoresist film.
Abstract: A light-sensitive positive photoresist composition containing a film forming resin, a photoactive compound, a solvent, and an arylhydrazo dye. The dyed photoresist reduces the linewidth variation of the resist pattern on a reflective substrate while giving good lithographic performance.
Type:
Grant
Filed:
September 30, 1996
Date of Patent:
June 9, 1998
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Shuji Ding, Ping-Hung Lu, Dinesh N. Khanna, Anthony J. Corso
Abstract: The present invention relates to a novel antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and an organic solvent or a mixture of organic solvents, where the novel polymer comprises a unit containing a dye that absorbs from about 180 nm to about 450 nm and a unit containing a crosslinking group.
Type:
Grant
Filed:
September 30, 1996
Date of Patent:
March 31, 1998
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Iain McCulloch, Ralph R. Dammel, Anthony J. Corso, Shuji Ding, Dana L. Durham, Ping-Hung Lu, Ming Kang, Dinesh N. Khanna
Abstract: A light-sensitive positive photoresist composition containing a film forming novolak resin, a quinone-diazide photoactive compound, a solvent, and a 2,4-dinitro-1-naphthol dye, where the dye is present at a level greater than 0.5 weight percent of the total photoresist composition. The dye reduces the linewidth variation of the resist pattern on a reflective substrate without significantly reducing the lithographic performance of the light-sensitive composition.
Type:
Grant
Filed:
August 7, 1996
Date of Patent:
February 17, 1998
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Ping-Hung Lu, Ralph R. Dammel, Elaine G. Kokinda, Sunit S. Dixit
Abstract: The present invention relates to a novel aqueous antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and water, where the novel polymer of the antireflective coating comprises at least one unit containing a dye that absorbs from about 180 nm to about 450 nm, at least one unit containing a crosslinking group and at least one unit derived from a hydrophilic vinyl monomer or a vinyl monomer capable of becoming hydrophilic.
Type:
Grant
Filed:
August 16, 1996
Date of Patent:
July 29, 1997
Assignee:
Hoechst Celanese Corporation
Inventors:
Iain McCulloch, Ralph R. Dammel, Dana L. Durham, Ping-Hung Lu, Ming Kang, Dinesh N. Khanna, Shuji Ding
Abstract: The present invention relates to a novel antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and an organic solvent or a mixture of organic solvents, where the novel polymer comprises a unit containing a dye that absorbs from about 180 nm to about 450 nm and a unit containing a crosslinking group.
Type:
Grant
Filed:
August 16, 1996
Date of Patent:
July 29, 1997
Assignee:
Hoechst Celanese Corporation
Inventors:
Iain McCulloch, Ralph R. Dammel, Dana L. Durham, Ping-Hung Lu