In order to study the influence of the nature of the moiety bearing a tetrathiafulvalenyl group in the polymers upon the microlithographic properties of resists, poly@-chloromethy1styrene)s and poly(styrene-co-p-chloromethy1styrene)s containing the 4-tetrathiafulvalenylphenoxymethyl group with a variety of controlled molecular weights and molecular weight distributions were studied. The copolymers were all prepared by reaction of poly(4-vinylbenzyl chloride) with potassium 4-tetrathiafulvalenylphenolate (3). Without exception, the resulting polylp-chloromethylstyrene-co-p-(tetrathiafulvalenylphenoxymethyl)styrene]s are highly insoluble. However, by reaction of potassium 4-tetrathiafulvalenylphenolate with poly(styrene-co-p-chloromethylstyrene) soluble copolymers could be prepared.
RESUME:Pour rCsoudre le phhomene de gonflement qui limite la resolution des resines microlithographiques classiques, nous nous sommes interessks a de nouvelles resines avec lesquelles ce phknomkne n'apparait pas. Nous avons retenu pour notre etude les resines R qui renferment en melange un polymere porteur de radicaux tktrathiafulvalknylcarbonyloxymethyles et le dibromotCtrachloroCthane. Afin de voir l'influence de la nature du radical porteur de l'unite tetrathiafulvalkne dans le polymtre sur les propriCtCs microlithographiques des resines R, nous nous sommes Cgalement interesses aux polymtres renfermant des radicaux tCtrathiafulvalCnylphCnoxymethyles. Les resines R ont Cte testees sous irradiation UV. Leurs sensibilites dependent en outre de la valeur de la masse molaire du polymke. SUMMARYIn order to solve the problem of polymer swelling which limits the resolution of negative resists, we have developed new resists where the swelling does not appear. For our study, we developed resists including polymers containing the tetrathiafulvalenylcarbonyloxymethyl radical and dibromotetrachloroethane. In order to study the influence of the nature of the radical bearing the tetrathiafulvalene unit in the polymers on the microlithographic properties of these resists, we also studied polymers containing the tetrathiafulvalenylphenoxymethyl radical. The resists have been tested under UV irradiation. The dependence of resist sensitivity on molecular weight is reported.
In order to solve the problem of polymer swelling, which limits the resolution for negative resists, new resists were developed which show no swelling. The undesirable swelling can be suppressed by converting nonpolar crosslinked polymers into polar ones, which are soluble after irradiation. This aim was attained by mixing a polystyrene bearing tetrathiafulvalenyl (TTF) groups with 1,2-dibromo-l,1,2,2-tetrachloroethane. For our study, we applied resists including poly(4-chloromethylstyrene)~ containing tetrathiafulvalenecarbonyloxymethyl groups (1 and 2). Poly(4-chloromethylstyrene)~ (4) or poly[styrene-c0-(4-~hloromethyl)styrene]s (5) with a variety of controlled molecular weights and molecular weight distributions were prepared by radical chain polymerization. The reaction of cesium tetrathiafulvalenecarboxylate (3) with 4 or 5 was carried out and the resultant substituted polymers 1 and 2 were characterized. * ) Tetrathia-2,2',5,5' bicyclopentadiCnylidene-1 : 1'.
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.
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