Acceptor-substituted euv pags with high electron affinity

A positive chemically amplified EUV or e-beam photoresist composition comprising,

• 1) a compound selected from the group consisting of 1-1), 1-2), 1-3), and 1-4):
• 1-1) a compound of structure (I), wherein
• R1, R2, R1a and R2a are independently selected from the group consisting of H, nitro, cyano, and an alkylsulfonyl, wherein at least two of R1, R2, R1a and R2a are independently selected from nitro, cyano, and an alkylsulfonyl, and X− and is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonates, naphthalenesulfonate, and/or camphorsulfonate,
• 1-2) a compound of structure (Ia) wherein,
• R1 and R1a, are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-3) a compound of structure (Ib) wherein,
• R2, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-4) a compound of structure (Ic) wherein,
• R1, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate.
• 2) a photoresist resin which undergoes chemically amplified deprotection catalyzed by photogenerated acid, releasing a resin which is soluble in aqueous base,
• 3) an optional acid quencher component,
• 4) an organic spin coating solvent.

A negative chemically amplified EUV or e-beam photoresist composition comprising,

• 1c) a compound selected from the group consisting of 1-1), 1-2), 1-3), and 1-4):
• 1-1) a compound of structure (I), wherein
• R1, R2, R1a and R2a are independently selected from the group consisting of H, nitro, cyano, and an alkylsulfonyl, wherein at least two of R1, R2, R1a and R2a are independently selected from nitro, cyano, and an alkylsulfonyl, and X− and is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonates, naphthalenesulfonate, and/or camphorsulfonate,
• 1-2) a compound of structure (Ia) wherein,
• R1 and R1a, are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-3) a compound of structure (Ib) wherein,
• R2, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-4) a compound of structure (Ic) wherein,
• R1, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate.
• 2c) a photoresist resin soluble in aqueous base which undergoes chemically amplified crosslinking in the presence of a photogenerated acid,
• 3c) an optional crosslinking component,
• 4c) an optional acid quencher component,
• 5c) an organic spin coating solvent.

A negative chemically amplified EUV or e-beam photoresist composition comprising,

• 1g) a compound selected from the group consisting of 1-1), 1-2), 1-3), and 1-4);
• 1-1) a compound of structure (I), wherein
• R1, R2, R1a and R2a are independently selected from the group consisting of H, nitro, cyano, and an alkylsulfonyl, wherein at least two of R1, R2, R1a and R2a are independently selected from nitro, cyano, and an alkylsulfonyl, and X− and is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonates, naphthalenesulfonate, and/or camphorsulfonate,
• 1-2) a compound of structure (Ia) wherein,
• R1 and R1a, are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-3) a compound of structure (Ib) wherein,
• R2, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate,
• 1-4) a compound of structure (Ic) wherein,
• R1, and R2a are independently selected from the group consisting of nitro, cyano, and an alkylsulfonyl, and X− is an anion of an acid with a pKa lower than 0, and is not a halide, tosylate, trifluoromethylsulfonate, tetrafluoroborate, an aryl-substituted borate, hexafluorophosphate, hexafluoroarsenate, acetate, trifluoroacetate, methane sulfonate, C-2 to C-20 linear unsubstituted alkyl sulfonate, naphthalenesulfonate, and/or camphorsulfonate.
• 2g) a molecular glass compound comprising from 3 to 5 crosslinking moieties selected from oxiranes, oxetanes or mixtures thereof which undergo crosslinking under the influence of acid formed by irradiation of component 1a),
• 3g) an optional acid quencher component,
• 4g) an organic spin coating solvent.