Poly(4-(1-hydroxyalkyl)styrene based photoresist materials : Design, synthesis and their lithographic performance
10 Mar 2006-Vol. 6153, pp 780-787
TL;DR: In this article, the authors provide an overview on the preparation and basic lithographically important characterization of new polymers based on poly(4-(1-hydroxyalkyl)styrene -co- styrene) [Poly(4-HAS -co)-S] for negative tone imaging at DUV lithography.
Abstract: Several synthetic approaches are available to make photoresist polymers for deep UV (DUV) lithography. Two approaches were widely used in semiconductor manufacturing: i) direct polymerization of corresponding monomers by (controlled) radical, (living) ionic polymerization ii) thermal or chemical catalyzed deprotection or protection of the macromolecules. The latter approach which is also called polymer modification chemistry (PMC) or polymer analogous chemistry offers several advantageous over the direct polymerization approach. In this presentation, we will provide an overview on the preparation and basic lithographically important characterization of new polymers based on poly(4-(1-hydroxyalkyl)styrene -co- styrene) [Poly(4-HAS -co- S)]. These polymers were synthesized for the first time by PMC and this methodology is an simple alternative for the synthesis of poly(4-HAS -co- S) than conventionally used synthetically challenging free radical or low temperature anionic polymerization of the protected monomer. We have synthesized high and low molecular weight (M n ) polymers with mole fraction of functional group ranging from partial to complete functionalization. Several formulations based on poly(4-HAS -co- S) were developed and tested for negative tone imaging at DUV lithography. Lithographic performance of these polymers at DUV lithography will be compared with their molecular weight and mole fraction of functional groups.
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Patent•
05 Mar 2009TL;DR: In this paper, a pattern is formed by applying a positive resist composition comprising a polymer comprising hydroxyalkylnaphthalene-bearing recurring units and acid labile group bearing recurring units onto a substrate to form a resist film.
Abstract: A pattern is formed by applying a positive resist composition comprising a polymer comprising hydroxyalkylnaphthalene-bearing recurring units and acid labile group-bearing recurring units onto a substrate to form a resist film, heat treating and exposing the resist film to radiation, heat treating and developing the resist film with a developer to form a first pattern, and causing the resist film to crosslink and cure with the aid of heat or of acid and heat. A second pattern is then formed in the space area of the first pattern. The double patterning process reduces the pitch between patterns to one half.
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References
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TL;DR: In this article, three multidentate amines, tetramethylethylenediamine (TMEDA), N,N,NN, N',N' and N'N' were used as new ligands in the copper mediated atom transfer radical polymerization (ATRP) of styrene, methyl acrylate and methyl methacrylate.
Abstract: Three multidentate amines, tetramethylethylenediamine (TMEDA), N,N,N‘,N‘,N‘‘-pentamethyldiethylenetriamine (PMDETA) and 1,1,4,7,10,10-hexamethyltriethylenetetramine (HMTETA) have been successfully used as new ligands in the copper mediated atom transfer radical polymerization (ATRP) of styrene, methyl acrylate and methyl methacrylate. All the polymerizations were well controlled with a linear increase of molecular weights (Mn) with conversion and relatively low polydispersities throughout the reactions. Compared to the 2,2‘-bipyridine (bipy) based ligands, most multidentate amines are less expensive and the polymerization mixtures are less colored. In particular, the use of the tridentate PMDETA and the tetradentate HMTETA as the ligands resulted in faster polymerization rates for styrene and methyl acrylate than those using bipy as the ligand. This may be in part attributed to the fact that the coordination complexes between copper and the simple amines have lower redox potentials than the copper−bipy co...
428 citations
Book•
01 Jan 1980
402 citations
"Poly(4-(1-hydroxyalkyl)styrene base..." refers background in this paper
...Polymers with the desired pendant functional group can be synthesized in two ways: (1) by the incorporation of the functional group as a pendant unit of the monomer itself and polymerizing the same by any one of the chain-growth mechanisms; (2) by the chemical modification of the nonfunctionalized polymer.(1) With respect to vinyl polymers both routes are used on a regular basis....
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...literature, whereas the synthesis of functionalized polymers by performing a chemical reaction on insoluble polymers is a well-established area of research.(1) Further, the literature cites fewer examples of chemical-modification reactions that result in essentially quantitative conversion as determined by the limits of structure-determining tools such as (1)H-NMR, which is attributed to the fact that polymer crosslinking reactions compete with polymer-modification reactions, in practice....
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Journal Article•
IBM1
TL;DR: This chapter describes polymers employed in formulation of chemically amplified resists for microlithography, which have become the workhorse in device manufacturing for the last few years and are continuing to be imaging materials of choice for a few more generations.
Abstract: This chapter describes polymers employed in formulation of chemically amplified resists for microlithography, which have become the workhorse in device manufacturing for the last few years and are continuing to be imaging materials of choice for a few more generations. The primary focus is placed on chemistries that are responsible for their lithographic imaging. Furthermore, innovations in the polymer design and processing that have supported the evolution of photolithography and advancement of the microelectronics technology are described. The topics covered in this chapter include the history, rapid development in the last 20 years, the current status, and the future perspective of chemical amplification resists.
401 citations
217 citations
TL;DR: Copulation entre le (tributylvinyl) stannane and des bromoethers, Bromoaldehydes, bromocetones and des composes dibromes benzeniques as mentioned in this paper.
Abstract: Copulation entre le (tributylvinyl) stannane et des bromoethers, bromoaldehydes, bromocetones et des composes dibromes benzeniques
202 citations
"Poly(4-(1-hydroxyalkyl)styrene base..." refers background in this paper
...It is important to note that the synthesis of the polymer [PHPES] from the monomer took 8 days.(19) Based on the mechanism of photoresist functioning, given in Scheme 3, it is clear that the desired functional groups can also be introduced by the chemical modification of PS, which in turn can be achieved in a much shorter time than 8 days....
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