Three-Component Negative-Type Photoresist Based on C-Tetraoctyl-calix(4)resocinarene, a Cross-linker, and a Photo-acid Generator.

Abstract

Calix[4]resocinarenes(C4-RAs), "C-tertaheptyl-calix[4]resorcinarene [C(7)C4-RA], Ctertaoctyl-calix[4]resorcinarene [C(8)C4-RA], C-tertanonyl-calix[4]resorcinarene [C(9)C4-RA], and C-tertaundecyl-calix[4]resorcinarene [C(11)C4-RA]", were synthesized by the acidcatalyzed condensation of resorcinol and alkylaldehyde. The obtained C4-RAs were welldissolved in common organic solvents and their films were transparent above 300 nm. Therefore, negative working photoresists based on C4-RAs, 4,4'-methylenebis[2,6bis(hydroxymethyl)]phenol (MBHP) as a cross-linker, and a photo-acid generator diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS) has been developed. Particularly, the resist containing C(8)C4-RA had the dissolution property well-controlled by a conventional aqueous base developer [2.38 wt% aqueous tetramethylammonium hydroxide(TMAH) solution]. Thus, the photoresist consisting of C(8)C4-RA (70 wt%), MBHP (20 wt%), and DIAS (10 wt%) showed a sensitivity of 7 mJ cm2 and a contrast of 6.1 when it was exposed to 365 nm light and postbaked at 130 °C for 3 min, followed by developing with the TMAFI developer at room temperature.

A Green and Highly Efficient Solvent-free Synthesis of Novel Calicx[4]resorcinarene Derivatives Using Tungstate Sulfuric Acid

“…1 calix [4]resorcinarenes, a subclass of calixarenes, are large cyclic tetramers which have found applications, as macrocyclic receptors, 2 dendrimers in biological systems, 3 nanoparticles, 4 nano-capsule, 5 supramolecular tectons, 6 optical chemosensors, 7 host molecules or host-guest complexes, 8,9 components in liquid crystals, 10 photoresists, 11 selective membranes, 12 HPLC stationary phases, 13 surface reforming agents, 14 ion channel mimics, 15 and metal ion extraction agents. 16 For example, in a valuable study by Sanchez-Cortes, Leyton, and co-workers entitled "selective molecular recognition of polycyclic aromatic hydrocarbons (PAHs) on calix [4]arene-functionalized Ag nanoparticles by surface-enhanced raman scattering" the 25,27-dicarboethoxy-26,28-dihydroxy-p-tert-butylcalix [4]arene host molecule (DCEC) displays analytical selectivity to the polycyclic aromatic hydrocarbon guest systems bearing four benzene rings, mainly pyrene (Scheme 1).…”

Synthesis and characterization of supramolecule grafted on modified magnetic nanoparticles: new hybrid organic–inorganic phase transfer catalyst

“…These compounds are large cyclic tetramers with diverse application as macrocyclic receptors, such as dendrimers in biological systems, nanocapsules, nanoparticles, optical chemosensors, and supramolecular tectons as components in liquid crystals, molecular switches, selective membranes, HPLC stationary phase as ion channel mimics [14][15][16][17].…”

A straightforward route for covalently anchored pyridinium salt onto upper rim of c-methylcalix[4]resorcinarene with selective antibacterial activity against Gram-positive bacteria

“…The synergetic effect of functional groups and three-dimensional cavity of scaffold would result in novel, improved and fascinating properties. In this regard, synthesis of functionalized supramolecular structures via covalently anchored functional groups onto c-methylcalix [4]resorcinarene and its derivatives have received considerable attention [12][13][14][15][16][17][18][19][20][21][22][23].…”