A New Photoresist Based on Calix[4]resorcinarene Dendrimer

Abstract

A new dendrimer (1), which contains phenol groups in the exterior for solubilization in aqueous alkaline solution and calix[4]resorcinarene in the interior to increase the molecular weight and number of the phenol group even in the lower generation, was designed as new negative-working, alkaline-developable photoresist material. A negative-working photoresist based on 1, 2,6-bis(hydroxymethyl)phenol as cross-linker, and diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate as a photoacid generator has been developed. This resist gave a clear negative pattern through postbaking at 110 °C after exposure to UV light, followed by developing with a 0.3% aqueous tetramethylammonium hydroxide solution at room temperature.

Synthesis of Fréchet-type poly(aryl ether) dendrimers with allyl end groups: comparative convergent and divergent approaches

“…Thus, benzyl chloride derivative 1 was prepared as described in the literature 3,6,9,10 showing spectral data in accordance with the published one. The reaction of 1 with 3,5-dihydroxybenzyl alcohol 2 in acetone at reflux in the presence of K2CO3 and catalytic amounts of Bu4NF gave 3 as an amber oil in 87 % yield.…”

The Photopolymer Science and Technology Award

“…Furthermore, he successfully extended the concept of chemical amplification to develop alkaline developable molecular resists based on calix [4]resorcinarene derivatives (8)(9)(10)(11), and various high sensitive and contrast poly(vinyl sulfonate)s and poly(vinylsulfonyl fluoride)s for 157-nm resists (12)(13)(14)(15)(16)(17). These essential contributions give the fundamental aspects of development of new resist materials.…”

Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle ) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups

“…However, there is a serious problem among the resolution of pattern, sensitivity of the photo-chemical reaction, and roughness of the pattern, i.e., these relationships are well known as "trade-off". To overcome this "trade-off", many molecular glasses such as calixarenes, 1-10 dendritic oligomers, [11][12][13][14][15][16][17][18] low-molecular-weight oligomers, 19,20 and fullerenes 21 have been reported and their resolutions showed about 50 nm regions. Recently, we could design a ladder type cyclic oligomer "noria" (noria = water wheel in Latin), 22 and examined the synthesis, physical properties, and patterning properties of noria derivatives with pendant t-butyl ester groups, 23,24 t-butyloxycarbonyl groups, 25 adamantyl ester groups, 26,27 cyclohexyl acetal moiety, 28 and oxetanyl groups 29 using electron beam (EB) or EUV exposure systems.…”