The study of a photoresist containing poly(p‐trimethylsiloxystyrene) (1, poly[1‐(4‐trimethyl‐siloxyphenyl)ethylene]) mixed with (C6H5)3SAsF6, which could be employed in a bilevel pattern‐transfer process, is reported. The onium salt undergoes efficient photolysis under UV radiation, to generate strong acids, responsible of the cleayage of the silicon‐containing side groups. The first results obtained show that this kind of resist could be used in microlithography, because it displays a very good sensitivity to deep UV and an excellent resistance to oxygen plasma. The syntheses of the compounds and substances used in this work are described.
Poly(ptrimethylsi1oxystyrene) (1 a), polyb-(tert-butyldimethylsiloxy)styrene] (1 b), poly[p-(tri-methylsi1oxy)-a-methylstyrene] (1 c), poly[p-(tert-butyldimethylsiloxy)-a-methylstyrene) (1 d) and polyfp-[2-(tert-butyldimethylsiloxy)ethyl]styrene] (1 e) were prepared by free-radical or cationic polymerization of the corresponding monomers. Poly([p-[2(trimethylsiloxy)ethyl]styrene]-co-[p-(2-hydroxyethyl)styrene]] (2 a) was synthetized by anionic polymerization of the corresponding trimethylsilylated monomer, followed by acid hydrolysis of the resulting polymer. Polyl[p-[2-(trimethylsiloxy)ethyl]styrene]-co-[p-(tert-butoxycarbonyloxy)styrene]] (2 b) were prepared by freeradical polymerization of the corresponding monomers.
RESUME:Pour resoudre le phenomene de gonflement qui limite la resolution des rtsines microlithographiques classiques, nous nous sommes intCressCs a de nouvelles rCsines avec lesquelles ce phCnomtne n'apparait pas. Nous avons retenu pour notre Ctude les resines R qui renferment en mClange un polymere porteur de radicaux tCtrathiafulvalCnylcarbonyloxymtthyles et le dibromotCtrachloroCthane. Afin de voir l'influence de la nature du radical porteur de l'unite tetrathiafulvalene dans le polymtre sur les propriCtCs microlithographiques des resines R, nous nous sommes Cgalement intCressCs aux polymeres renfermant des radicaux tCtrathiafulvalCnylphCnoxymCthyles. Les rtsines R ont Ct C testCes sous irradiation Clectronique. Leurs sensibilitts dCpendent en outre de la valeur de la masse molaire du polymere. Des rCsolutions comprises entre 0,l et 0,4 pm ont Ct C obtenues. Ce type de rCsines possedent un certain nombre de proprietes intbressantes telles que des sensibilitks ClevCes et de bonnes rCsolutions.
SUMMARYIn order to solve the polymer swelling which limits the resolution for negative resists, new resists (R) including polymers containing the tetrathiafulvalenylcarbonyloxymethyl radical and dibromotetrachloroethane were developed where the swelling does not appear. In order to study the influence of the nature of the radical bearing the tetrathiafulvalene unit in the polymers upon the microlithographic properties of the R resists, polymers containing the tetrathiafulvalenylphenoxymethyl radical were also studied. The resists have been tested under electron beam irradiation. The dependence of resist sensitivity on molecular weight is reported. Resolutions between 0,l and 0,4 pm were obtained. These resists are shown to have a desirable combination of properties, including high sensitivity and high resolution.
We report a study on the hydrolytic instability of the oxygen‐silicon bond of the following compounds: p‐tert‐butyldimethylsilyloxytoluène, p‐triméthylsilyloxytoluène and poly(p‐triméthylsilyloxystyrène). The instability occurs in an acidic media: HCl, H−2SO4, CF3CO0H, BF3 or in presence of a salt: KPF6, KAsF6, KSbF6, NaBF4, [CH3(CH2)3]4NF, [CH3(CH2)3]4NBF4, [CH3(CH2)3]4NPF6, [CH3(CH2)3]4N AsF6, [CH3(CH2)3]4NSbF6. A mixture containing both an acid and a salt from those previously discussed can also be used.
A number of representative examples is presented. The tert‐butyldimethylsilylether derivatives are much more stable than the trimethylsilylethers. It is shown that the rate of reaction is dependent on the nucleophilicity of anion used in these salts. This simple procedure undoubtedly extends the scope for a preparation of organosilicon resists.
Si on laisse vieillir les solutions d'enduction obtenues en solubilisant le poly(p‐tri‐méthylsiloxystyrene) et l'un des sels (C6H5)2(C6H5SC6H4)SSbF6 ou (C6H5)3SAsF6 dans un solvant tel que la 3‐pentanone, on constate que le pourcentage de coupure des liaisons OSi(CH3)3 obtenue après irradiation (λ = 254 nm) avec une dose donnèe et après postcuisson dèpend de la quantitè de sel introduit. I1 en est de même de la solubilité de la rèsine ainsi traitee dans le solvant basique MF 319.
Upon treatment with ultraviolet irradiation (wavelength A = 254 nm) the resist containing both poly@-trialkylsiloxystyrene) and a triarylsulfonium salt undergoes photoinduced structural modifications which convert the silylated polymer into either poly@-hydroxystyrene) or poly[@-trialkylsiloxystyrene)-co-~-hydroxystyrene)]. Aging with the use of antimonate salts rather than arsenate salts, and bulky alkyl groups favour 0-Si bond cleavage.
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