Synthesis of a photo‐patternable cross‐linked epoxy system containing photodegradable carbonate units for deep UV lithography

Abstract

Bis(2-(oxiran-2-ylmethyl)-1,3-dioxoisoindolin-5-yl) carbonate and polymers containing 9-anthracenylmethylmethacrylate (AMMA), p-tert-butoxy styrene (PTBS), and methacrylic acid (MAA) monomeric units were synthesized with the aim of developing a novel photo-patternable crosslinked epoxy system. The oxirane groups in bis(2-(oxiran-2-ylmethyl)-1,3-dioxoisoindolin-5-yl) carbonate were reacted with the carboxylic acid in the polymer to generate a crosslinked epoxy film, and the photo degradation of the crosslinked film was achieved through decomposition of the carbonate groups in the cross-linked film by deep UV irradiation. Because the copolymer containing anthracene groups has relatively high reflective index and absorption at 248 nm, this cross-linked system can be applied to patternable bottom antireflective coating materials for deep UV lithography applications.

Fluorescent monomers as building blocks for dye labeled polymers: synthesis and application in energy conversion, biolabeling and sensors

“…The synthesis of a series of polymerizable anthracene dyes has been described earlier. 56 Labeled An1 containing copolymers could be obtained by copolymerization with styrene, 57,58 methyl methacrylate (MMA), [59][60][61][62] 2-(dimethylamino)ethyl methacrylate (DMAEMA), 63 azacrown ether methacrylate monomers, 64 p-tert-butoxy styrene (PTBS) and methacrylic acid (MAA), 65 as well as N-(4-cyanatophenyl) maleimide (CyOPMI), 4-hydroxybutyl vinyl ether (HBuVE) and MMA. 66 An3 could be polymerized with N-vinyl-2-pyrrolidone (VP), 67 as well as with vinyl terminated poly(siloxanes).…”

“…68 Besides their good labeling properties, anthracene containing monomers are also capable of undergoing Diels-Alder reactions, e.g., in PMMA copolymers, 69 and photodimerization. [59][60][61][62][63][64][65][66][67][68][69][70][71] Moreover, polymerizable pyrenes were used to label polystyrenes, [72][73][74][75][76][77] AA in ionic liquids, 78 and MMA. 49,76,79 Due to the absence of any heteroatoms in the chromophore moieties, all monomers are suitable for advanced polymerization techniques, i.e.…”

Degradation Behavior of Biobased Epoxy Resins in Mild Acidic Media

“…The degradation of biobased epoxy resins containing appropriate functional groups has been reported in water or organic solvents at moderate temperatures, utilizing functional groups such as ester groups, 12−14 acetals, 15−17 carbonates, 18 Schiff bases, 19 and furan and maleimide linkages. 20,21 Various factors that affect degradation rates have also been discussed, 22 including solution pH, 23,24 temperature, 25,26 presence of catalyst, 27−29 solvent composition, 30 and type and concentration of monomer and curing agent.…”

Novel photolabile crosslinkers based on O-acyloxime moiety

“…Furthermore, decrosslinking technology provides an important process in the eld of polymer recycling. 1 Several stimuli such as heat, 2-6 pressure, 7 electrical voltage, 8 ultrasonic, 9 the addition of acids, [10][11][12] bases, 3,[12][13][14] and other reagents, 15,16 and light 3,7,[17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] have been applied to trigger the decrosslinking. Among them, photochemical process is appealing because of its easy remote activation and spatiotemporal control.…”

“…Although indirect methods which utilize photo-triggered release of catalysts such as strong acids have been proposed recently, 17,18,[21][22][23][24][25] the most versatile approach is to design crosslinkers bearing both polymerizing and photolabile units and to polymerize them. However, in most cases, the photolabile units used in the crosslinkers were limited to o-nitrobenzyl- [26][27][28][29][30][31][32] and coumarine-based 33,34 families.…”