Photoacid-generating compound, polymer derived therefrom, photoresist composition including the photoacid-generating compound or polymer, and method of forming a photoresist relief image
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example 1
Synthesis of Photoacid Generator Compound TPS NB-AdOH-DFES
[0044]FIG. 1 presents a chemical scheme for the synthesis of the photoacid generator compound referred to as TPS NB-AdOH-DFES. The synthesis process was as follows. To a suspension of 5-norbornene-2,3-dicarboxylicanhydride (20 grams, 122 millimoles) and 3-(hydroxymethyDadamantan-1-ol (22.2 grams, 121.8 millimoles) in acetonitrile (150 milliliters) was added N,N-dimethylaminopyridine (1.5 grams, 12.27 millimoles) and the reaction mixture was stirred at 65° C. for 18 hours. The mixture was cooled to room temperature and concentrated aqueous hydrochloric acid was added until the pH was reduced to 2. The crude product was filtered and dried, before being suspended in ethyl acetate (150 milliliters) and stirred for 30 minutes at room temperature. Filtration produced 28 grams (yield: 66%) of pure product (1) as a white solid. 1H NMR (acetone-d6) δ: 6.22 (m, 1H), 6.17 (m 1H), 3.69 (d, 2H), 3.53 (d, 2H), 3.40 (m, 2H), 3.14 (m, 2H), 2...
example 2
Acid Diffusion Length Evaluation
[0046]Acid diffusion length was determined as follows. An acid detector layer formulation was prepared by combining Polymer A1 (2-adamantyl-2-propyl methacrylate / alpha-(gamma-butyrolactone) methacrylate / 1-hydroxyadamantyl-3-methacrylate terpolymer, 30 / 50 / 20 molar ratio, Mw=10,000 grams / mole) shown below (5.981 weight percent of total formulation), and tent-butyl-4-hydroxypiperdine-1-carboxylate as a quencher (0.019 weight percent of total formulation) in a 50 / 50 (w / w) mixture of propylene glycol methyl ether acetate (PGMEA) and methyl 2-hydroxyisobutyrate (HBM).
Separately, an acid source layer formulation was prepared by combining a tent-butyl acrylate / methacrylic acid copolymer (70 / 30 molar ratio, respectively; 0.891% w / w solution) and photoacid generator compound PAG (inventive or comparative) (153.40 micromoles / gram based on the total formulation) in an 80 / 20 (weight / weight) mixture of 2-methyl-1-butanol and decane. The acid detector layer formulat...
example 3
Lithographic Evaluation
[0051]Lithographic evaluation of the exemplary PAG was carried out according to the following procedure. Photoresists were formulated using the components and proportions shown in Table 2. The photoresist polymer (“Polymer A2”) used in all examples was a pentapolymer incorporating monomers M1, M2, M3, M4 and M5 having the chemical structures shown below, where the mole percentage of M1 / M2 / M3 / M4 / M5 is 20 / 20 / 30 / 20 / 10 for a total of 100 mole percent of monomers. The weight average molecular weight of the polymer was 8,000 grams / mole.
The PAG (see Table 2), base (t-butyloxycarbonyl-4-hydroxypyridine (TBOC-4HP), and surface leveling agent (PF 656 surfactant, available from Omnova), are given as weight percent based on 100% solids content, with the balance of the solids being the polymer. Propylene glycol monomethyl ether acetate (51) and methyl-2-hydroxyisobutyrate (55) were used as the solvents. The weight ratio of solvent S1:S5 in the final formulation was 1:1. Th...
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