Azo dyes based on benzidine and aromatic amine classified. Liquid priming is the process of spinning hmds, diluted in solvent, onto a dehydrated wafer. Lithographic, and dissolution properties brennen k. Diazonaphthoquinone dnq novolak resists have not been used for duv integrated circuit ic applications mainly due to the low sensitivity and the strong absorbance of the dnq photoactive compound pac at 248 nm. The basic chemistry of both dnq sensitizers and novolak resins are explored. Upon exposure to light, dnq converts to a derivative that is susceptible to etching. Diazonaphthoquinonebased resists tutorial texts in.
The basic structure of dnq is shown in figure 8, along with the resonance structures that are commonly written for this compound. Highperformance liquid chromatographic method of photoactive compounds based on diazonaphthoquinone for positive photoresists byounghyounkim1, yon heekim1 and dong cheulmoon2 1analytical science, lg chem research park, lg chem ltd. Grant willson1 1department of chemical engineering, the university of texas at austin, austin, tx 78712 2etec systems inc. Other jurisdictions such as the european union eu and the united states have taken or proposed actions to manage the risks posed by some of these substances. When exposed, diazonaphthoquinone dnq novolakbased thickfilm positive resist hereafter thickfilm resist decomposes into indene ketene, producing. Patterning without chemical amplification article in chemistry of materials 1915 june 2007 with 160 reads how we measure reads. This book elucidates the reasons underlying the lasting success of dnqn resist systems by examining the correlation between the chemical structure of the.
However, a 2,1,4 dnq based resist has been characterized that. Viscosity affects the flow characteristics and film thickness, and depends on the. In spite of this, until quite recently, not even an outline of the functional mechanism of novolak resists was known. Diazonaphthoquinone based resists tutorial text series volume 11 of tutorial texts in optical engineering.
The international context on aromatic azo and benzidinebased substances is summarized in this section. In a typical synthesis, a diazonaphthoquinone dnq sulfonyl chloride is added to a phenolic compound with an amine catalyst. Performing organization name and address sra international, inc. The condensation of 2,3,4trihydroxybenzophenone with diazonaphthoquinone sulfonyl chloride in dimethylacetamide or nmethyl2pyrrolidone resulted in a diester isomer distribution that was different than that observed in acetone, 1,4dioxane, methyl ethyl ketone, tetrahydrofuran and gammabutyrolactone. Diazonaphthoquinone what does diazonaphthoquinone stand. Diazonaphthoquinone based resists by ralph dammel, 9780819410191, available at book depository with free delivery worldwide. However, over the years one specific class of photosensitive materials has been. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. There is information of nmethyl2pyrroridone in the material safety data sheet of supplier.
When exposed, diazonaphthoquinone dnq novolak based thickfilm positive resist hereafter thickfilm resist decomposes into indene ketene, producing. Dammel, diazonaphthoquinonebased resists, spie press, 1993, p. Highperformance liquid chromatographic method of photoactive. Functional group deprotection talkyl deprotection high ton requires superstrong acids requires nonnucleophilic anions requires higher bake temp. Kohl1 1school of chemical and biomolecular engineering, georgia institute of technology, atlanta, georgia 303320100 2promerus llc, brecksville, ohio 44141 correspondence to. Diazonaphthoquinone dnq is a diazo derivative of naphthoquinone. Molecular modeling of the thermal decomposition of polymers. Characterization of a nonchemically amplified resist for. Definition of diazonaphthoquinone in the dictionary. Oclcs webjunction has pulled together information and resources to assist library staff as they consider how to handle coronavirus.
Numerous and frequentlyupdated resource results are available from this search. Dnq stands for diazonaphthoquinone, a lightsensitive compound that in its unexposed form interacts with a cresolformaldehyde resin, the novolak, to make a product that is insoluble in aqueous alkaline developer solution. The above three imaging systems were subsequently refined. The pac used in conventional positive photoresists is a diazonaphthoquinone dnq, an.
Dnq compounds, 1naphthalenesulfonic acid, 6diazo5,6dihydro5oxo, sodium salt, 1naphthalenesulfonyl chloride, 6diazo5,6dihydro5oxo, 1naphthalensulfonic acid, 6diazo5,6dihydro5oxo, ester with phenyl2,3,4trihydroxyphenyl methanone, 1naphthalenesulfonic acid, 6diazo5,6. Photoresist key properties photospeed is determined by the quantum efficiency of the resist, i. The resulting curve is plotted in the conventional format as a function of the. However, a 2,1,4 dnq based resist has been characterized that bleaches at 257 nm and inhibits novolak. Novolakdiazonaphthoquinone dnq resists are photosensitive varnishes that are used in the fabrication of more than 80% of todays integrated circuits. Download fullsize image films of novolak dissolve quite rapidly in aqueous alkali, but if they contain small concentrations of a diazonaphthoquinone dnq derivative, such as the dnq5sulfonic acid ester below, the rate of dissolution. Novolak resists have accompanied the evolution of the semiconductor industry almost from its beginning. Abstract there is a continuing need to prepare pacs with less ionic impurities. Diazonaphthoquinone sulfonic acid esters are components of common photoresist materials.
Diazonaphthoquinone based resists tutorial texts in optical engineering ralph dammel on. Simulation based formulation of a nonchemically amplified resist for 257 nm laser mask fabrication benjamen m. Novolak is a phenolformaldehyde condensation polymer of moderate molecular weight. Nomination summary for diazonaphthoquinone compounds. This book elucidates the reasons underlying the lasting success of dnqn resist systems by examining the correlation between the chemical structure of the components and the photoresist. Benzoquinonehydroquinone couple for flow battery saraf nawar,1 brian huskinson,2 and michael aziz2 1harvard college, cambridge, ma 028, usa 2harvard school of engineering and applied sciences, 29 oxford street, cambridge, ma 028, usa abstract at present, there is an ongoing search for approaches toward the storage of energy from. Diazonaphthoquinonebased resists spie digital library.
Click download or read online button to get diazonaphthoquinone based resists book now. Mar 19, 2019 chemistry a diazo derivative of naphthoquinone. Electron beam exposure of diazoquinone based resists wolfgang a. Pdf download diazonaphthoquinone based resists free.
The diagram below shows adhesion of resist to a surface silylated with hmds. Acknowledgement the authors are grateful for the financial support given by ministry of information and technology and csir, india and to the director, iict and head of the. Dammel, diazonaphthoquinone based resists, spie press, 1993, p. They are currently involved in the fabrication of more than 80% of the worlds integrated circuits. Pdf the demand for ultra thick photoresist formulations is steadily increasing. The most common class of dissolution inhibitors used in nonchemically amplified novolac based resists belong the to the diazonaphthoquinone dnq family of compounds. Mack, finle technologies, austin, texas there are a large number of materials, both organic and inorganic, which are sensitive to light see, for example, ref. Diazonaphthoquinone derivatives used in photoresists. Electron beam exposure of diazoquinone based resists. Diazonaphthoquinone based resists tutorial texts in optical engineering.
For example, hanabata and coworkers 610 have used fractionation to optimize the performance of highresolution resists based on diazonaphthoquinone dnq pacs. Diazonaphthoquinonebased resists tutorial texts in optical. This book elucidates the reasons underlying the lasting success of dnqn resist systems by examining the correlation between the chemical structure of the components and the photoresist performance. The exposed regions of the photoresist film become soluble in aqueous base. Dnq compounds, 1naphthalenesulfonic acid, 6diazo5,6dihydro5oxo, sodium salt, 1naphthalenesulfonyl chloride, 6diazo5,6dihydro5oxo, 1naphthalensulfonic acid, 6diazo5,6dihydro5oxo, ester with phenyl2,3,4trihydroxyphenyl methanone, 1naphthalenesulfonic acid, 6diazo5,6dihydro5oxo,4. Acetal deprotection lower ton works with any mineral acid. Improved resolution of thick film resist effect of pre. Diazonaphthoquinone is listed in the worlds largest and most authoritative dictionary database of abbreviations and acronyms. Synthesis of diazonaphthoquinone dnq photoactive compounds. After the synthesis, the pac is washed well with water or mixture of solvents. Toxcenter includes toxicology data from the following files. In the unexposed regions of the resist film, the dnq acts as a dissolution inhibitor and. Positivetone, aqueousdevelopable, polynorbornene dielectric.
The condensation of 2,3,4trihydroxybenzophenone with diazonaphthoquinone sulfonyl chloride in dimethylacetamide or nmethyl2pyrrolidone resulted in a diester isomer distribution that was different than that observed in acetone, 1,4dioxane, methyl ethyl. Diazonaphthoquinonebased resists by ralph dammel, 9780819410191, available at book depository with free delivery worldwide. Diazonaphthoquinone based resists download ebook pdf. Because of the push in recent years toward graphic arts materials that are not only durable but also environmentally friendly and nontoxic, testing has become even more important. Diazonaphthoquinone 289 words case mismatch in snippet view article find links to article ralph dammel 1993. Improved resolution of thick film resist effect of prebake. Evidence for adverse reproductive outcomes has been inconsistent at best, with evidence for birth defects caused by chlorination dbps. Diazonaphthoquinone what does diazonaphthoquinone stand for. The text incorrectly identifies them as for 100 wafers. Information and translations of diazonaphthoquinone in the most comprehensive dictionary definitions resource on the web. Kohl1 1school of chemical and biomolecular engineering, georgia institute of technology, atlanta, georgia 303320100. Business unit electronic materials basic chemistry.
Novolak by itself is moderately soluble in the aqueous base developer. In this way, dnq has become an important reagent in photoresist technology in the semiconductor industry. Pdf resist rehydration during thick film processing researchgate. This is often effective, but is not as good as vapor priming. Nomination summary for diazonaphthoquinone compounds n20220 nominated substances. Better recovery at lower concentrations was achieved successfully. Reliable information about the coronavirus covid19 is available from the world health organization current situation, international travel.
Nomination summary for diazonaphthoquinone compounds n20220. The photoactive compound pac and an amine salt are formed. Today, all commercial resists use at least one of two approaches. Simulation based formulation of a nonchemically amplified. This site is like a library, use search box in the widget to get ebook that you want. Dammel, diazonaphthoquinonebased resists, spie optical.
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