Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Abstract

The characteristics of Noria analogs with 12 ethoxy groups and 12 hydroxy groups (Noria-OEt), which were synthesized by the condensation reaction of 3-ethoxyphenol with 1,5-pentanedial, were examined in detail. The solubility of the synthesized Noria-OEt in common organic solvents was better than that of Noria. In addition, Noria-OEt was soluble in 2.38 wt% tetrametyl ammonium hydroxide (TMAH) aqueous as a developer. The thermal stability and mechanical properties were similar to those of Noria because of the ladder structure and amorphous characteristics, which means that the film-forming properties were confirmed. These characteristics are advantageous for use as a molecular glass photoresist. The patterning properties of the negative-type, alkaline developable, multicomponent photoresist based on Noria-OEt, with polyfunctional benzyl alcohols as a crosslinker and a photoacid generator, were evaluated with an extreme ultraviolet lithography system. This negative-type photoresist with 2,4-dihydroxymethyl-6-methylphenol as a crosslinker gave a resolution pattern of 35 nm half-pitch with 10.0 mJ cm À2 .

Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids

“…However, it has low solubility in all solvents investigated and we therefore turned attention to the known semi-ethylated derivative Noria-OEt. 19 …”

“…We have also investigated the more soluble derivative, Noria-OEt, in which 12 ethyl substituents are scrambled over the 24 external O sites, for the synthesis of PLs. 19 Experimental gas uptake measurements and detailed molecular dynamics (MD) modelling suggest that Noria-OEt dissolved in 15-crown-5 is indeed a new chemically and thermally robust Type II PL.…”

Study on resist performance of chemically amplified molecular resists based on cyclic oligomers

“…Resists 3 and 4 were prepared from noria-OEt 17 with AD (DP = 49%) and noria-OMe 18 with AD (DP = 44%), respectively. Figure 2 shows Resists 5-8, which were based on calixarene dimer, 19,20 triple-ringed [14]arene, 21 β-cyclodextrin, 22 and pillar [5]arene, 23 respectively.…”

Synthesis and characteristics of multi-aryl substituted molecular glasses bearing biphenyl core

“…Molecular glasses have been explored to improve line edge roughness (LER) comparing to the conventional polymeric resists, whose performance issues was originating from chain entanglement, molecular size and composition distribution as well as acid diffusion control that hinders optimal lithographic performance [6,7]. Molecular glass resists such as polyphenol [8][9][10][11], calyx[n] arene [12][13][14][15], fullerene [16][17][18][19] and ladder cyclic molecule (noria) [20,21] are of great interest for its potential application for EUV resists. A series of tert-butyloxycarbonyl (t-Boc) protected C-4-hydroxyphenyl-calix [4]resorcinarene derivatives that produces 30 nm line space patterns under EUV conditions was developed by Chang and co-workers [22], and the first report on sub-50 nm features was obtained by a molecular glass resist using standard processing conditions.…”