Patent CH-694663-A5 (CH)
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: BIRBAUM JEAN-LUC
IPC: C07D333/22
Filed: 2000-03-27
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. [Image] R 1H 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' 1optionally substituted phenylene, naphthylene, -Ph-CH 2-Ph-, diphenylene or oxydiphenylene or is 1-12C alkylene or -Ph-A-A 1-A-Ph-; A : O, S, NR 4, O(CO), S(CO), NR 4(CO), SO, SO 2 or OSO 2; A 11-12C alkylene or 2-12C alkylene interrupted by one or more -O-; R 2halogen or 1-10C haloalkyl; R 31-18C alkylsulfonyl, 1-10C haloalkylsulfonyl, camphorylsulfonyl, phenyl-1-3C-alkylsulfonyl, 3-12C cycloalkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, or is 2-6C haloalkanoyl, halobenzoyl, -P(R 9)(=Y 1)-R 8, -P(=Y 1)(Y 2-R 9)-R 8 or -P(=Y 1)(Y 2-R 9)-Y 3-R 1 0; Y 1-Y 3O or S; R' 3optionally substituted phenylenedisulfonyl, naphthylenedisulfonyl, -S(O) 2-Ph-CH 2-Ph-S(O) 2-, diphenylenedisulfonyl or oxydiphenylenedisulfonyl, or is 2-12C alkylenedisulfonyl; X : halogen; R 4H 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; R 5, R 6H 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; R 7H, 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 R 8-R 1 0optionally substituted 1-6C alkyl or phenyl or R 9 and R 1 0 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) 2R 2 group is CF 3; (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 R 3Cl, R'' 3Cl or Cl-R' 3-Cl. [Image] R'' 31-16C 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.