Patent DE-10015255-A1 (DE)
Title: New and known oxime derivatives used as photosensitive acid donors in chemically amplified photoresist compositions comprising a compound which is acid curable or which increases in solubility in acid
Inventor: ASAKURA TOSHIKAGE
IPC: G03F7/038
Filed: 2000-03-28
Abstract: A chemically amplified photoresist composition comprises an acid curable compound or a compound whose solubility increases upon the action of an acid; and a (new) oxime as photosensitive acid donor. A chemically amplified photoresist composition comprises: (a) an acid curable compound or a compound whose solubility increases upon the action of an acid; and (b) compound(s) of formula (I)-(III) as photosensitive acid donor. R1  = H or optionally substituted 1-12C alkyl, phenyl, naphthyl, anthracyl, phenanthryl or heteroaryl and can be additionally substituted by a group having a -O-C bond or an -O-Si-bond which cleaves upon the action of an acid; R'1  = optionally substituted phenylene, naphthylene, -Ph-CH2-Ph-, diphenylene or oxydiphenylene or is 1-12C alkylene or -Ph-A-A1-A-Ph-; A  = O, S, NR4, O(CO), S(CO), NR4(CO), SO, SO2 or OSO2; A1  = 1-12C alkylene or 2-12C alkylene interrupted by one or more -O-; R2  = halogen or 1-10C haloalkyl; R3  = 1-18C alkylsulfonyl, 1-10C haloalkylsulfonyl, camphorylsulfonyl, phenyl-1-3C-alkylsulfonyl, 3-12C cycloalkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, or is 2-6C haloalkanoyl, halobenzoyl, -P(R9)(=Y1)-R8, -P(=Y1)(Y2-R9)-R8 or -P(=Y1)(Y2-R9)-Y3-R10; Y1-Y3  = O or S; R'3  = optionally substituted phenylenedisulfonyl, naphthylenedisulfonyl, -S(O)2-Ph-CH2-Ph-S(O)2-, diphenylenedisulfonyl or oxydiphenylenedisulfonyl, or is 2-12C alkylenedisulfonyl; X  = halogen; R4  = H or optionally substituted phenyl, 1-18C alkyl, alkyl interrupted by one or more O, 2-18C alkanoyl or 1-18C alkylsulfonyl or is phenylsulfonyl or (4-methylphenyl)sulfonyl; R5, R6  = H or optionally substituted 1-18C alkyl, 2-18C alkyl interrupted by one or more O, 2-18C alkanoyl or 1-18C alkylsulfonyl or is phenyl, benzoyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl; R7  = H, phenyl, optionally substituted 1-18C alkyl, 2-18C alkyl interrupted by one or more O, 2-18C alkanoyl or 1-18C alkylsulfonyl or is phenylsulfonyl or (4-methylphenyl)sulfonyl; and R8-R10  = optionally substituted 1-6C alkyl or phenyl or R9 and R10 together are 1,2-phenylene or 2-6C alkylene optionally substituted by 1-4C alkyl or halogen. Also claimed are: (A) preparation of the photoresist comprising applying the above composition to a substrate, baking at 60-160  deg C, image-wise irradiating with light at 150-1500 nm, optionally further baking at 60-160  deg C and developing with a solvent or an aqueous alkaline developer; (B) new oxime compounds (I)-(III) is which the -C(X)2R2 group is CF3; (C) preparation of the thermally stable isomer of the oxime ester compounds of formula (I)-(III) comprising treating the isomeric mixture of compounds of formula (X) or (XI) with an acid and then reacting with the acid halides of formula R3Cl, R''3Cl or Cl-R'3-Cl. R''3  = 1-16C alkylsulfonyl, phenyl-1-3C-alkylsulfonyl, camphorylsulfonyl, naphthylsulfonyl, trimethylphenylsulfonyl or phenylsulfonyl substituted by one or more 2-16C alkyl, 1-4C alkoxy, 1-4C haloalkyl and/or halogen.