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US 10,520,809 B2Granted
Resist composition and patterning process
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsJun Hatakeyama, Masaki Ohashi, Takeshi Sasami
Life of this patent
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Abstract
A resist composition comprising a base polymer and a metal salt of an iodinated aromatic group-containing carboxylic acid, the metal being selected from among sodium, magnesium, potassium, calcium, rubidium, strontium, cesium, barium, cobalt, nickel, copper, zinc, cadmium, tin, antimony, zirconium, hafnium, cerium, aluminum, and indium, exhibits a sensitizing effect and an acid diffusion suppressing effect and forms a pattern having improved resolution, LWR and CDU.
Claims13
A resist composition comprising a base polymer and a metal salt of an iodinated aromatic group-containing carboxylic acid, the metal being selected from the group consisting of sodium, magnesium, potassium, calcium, rubidium, strontium, cesium, barium, cobalt, nickel, copper, zinc, cadmium, tin, antimony, zirconium, hafnium, cerium, aluminum, and indium,
- wherein the salt has the formula (A):
- wherein R1 is hydrogen, hydroxyl, a C1-C6 straight, branched or cyclic alkyl group, C1-C6 straight, branched or cyclic alkoxy group, C2-C6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR2—C(═O)—R3, or —NR2—C(═O)—O—R3, R2 is hydrogen or a C1-C6 straight, branched or cyclic alkyl group, R3 is a C1-C6 straight, branched or cyclic alkyl group or C2-C8 straight, branched or cyclic alkenyl group, G is a single bond or a C1-C20 (p+1)-valent linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety, p is an integer of 1 to 3, q is an integer of 1 to 5, r is an integer of 0 to 3, Mn+ is a metal ion selected from the group consisting of Na+, Mg2+, K+, Ca2+, Rb+, Sr2+, Cs+, Ba2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Sn4+, Sb3+, Zr4+, Hf4+, Ce3+, Al3+, and In3+, and n indicative of the valence number of Mn+ is an integer of 1 to 4,
- wherein the base polymer consists of recurring units having the formula (a1) or recurring units having the formula (a2), and recurring units of at least one type selected from recurring units having the formulae (f1) to (f3), and optionally at least one selected from the group consisting of
- recurring units (b) having a phenolic hydroxyl group as an adhesive group,
- recurring units (c) having an adhesive group selected from hydroxyl (other than phenolic hydroxyl), lactone ring, ether, ester and cyano groups,
- recurring units (d) selected from units of indene, benzofuran, benzothiophene, acenaphthylene, chromone, coumarin, and norbornadiene, or derivatives thereof, and
- recurring units (e) which are derived from styrene, vinylnaphthalene, vinylanthracene, vinylpyrene, methyleneindene, vinylpyridine, or vinylcarbazole:
- wherein RA is each independently hydrogen or methyl, R41 and R42 are each independently an acid labile group, X is a single bond, phenylene, naphthylene, or a C1-C12 linking group containing ester moiety or lactone ring, and Y is a single bond or ester group,
- wherein RA is each independently hydrogen or methyl,
- Z1 is a single bond, phenylene, —O—Z11—, or —C(═O)—Z12—Z11—, Z11 is a C1-C6 straight, branched or cyclic alkylene group or C2-C6 straight, branched or cyclic alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or phenylene group, Z12 is —O— or —NH—,
- R51, R52, R53, R54, R, R56, R57, and R58 are each independently a C1-C12 straight, branched or cyclic alkyl group which may contain a carbonyl, ester or ether moiety, or a C6-C12 aryl, C7-C20 aralkyl, or mercaptophenyl group,
- Z2 is a single bond, —Z21—C(═O)—O—, —Z21—O—, or —Z21—O—C(═O)—, Z21 is a C1-C12 straight, branched or cyclic alkylene group which may contain a carbonyl, ester or ether moiety,
- Z3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—Z31—, or —C(═O)—Z32—Z31—, Z31 is a C1-C6 straight, branched or cyclic alkylene group or C2-C6 straight, branched or cyclic alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or a phenylene, fluorinated phenylene or trifluoromethyl-substituted phenylene group, Z32 is —O— or —NH—,
- A1 is hydrogen or trifluoromethyl, and M− is a non-nucleophilic counter ion.
11 more elements
A resist composition comprising a base polymer, an acid generator capable of generating sulfonic acid, sulfonimide or sulfonmethide, and a metal salt of an iodinated aromatic group-containing carboxylic acid, the metal being selected from the group consisting of sodium, magnesium, potassium, calcium, rubidium, strontium, cesium, barium, cobalt, nickel, copper, zinc, cadmium, tin, antimony, zirconium, hafnium, cerium, aluminum, and indium,
- wherein the salt has the formula (A):
- wherein R1 is hydrogen, hydroxyl, a C1-C6 straight, branched or cyclic alkyl group, C1-C6 straight, branched or cyclic alkoxy group, C2-C6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR2—C(═O)—R3, or —NR2—C(═O)—O—R3, R2 is hydrogen or a C1-C6 straight, branched or cyclic alkyl group, R3 is a C1-C6 straight, branched or cyclic alkyl group or C2-C8 straight, branched or cyclic alkenyl group, G is a single bond or a C1-C20 (p+1)-valent linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety, p is an integer of 1 to 3, q is an integer of 1 to 5, r is an integer of 0 to 3, Mn+ is a metal ion selected from the group consisting of Na+, Mg2+, K+, Ca2+, Rb+, Sr2+, Cs+, Ba2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Sn4+, Sb3+, Zr4+, Hf4+, Ce3+, Al3+, and In3+, and n indicative of the valence number of Mn+ is an integer of 1 to 4,
- wherein the base polymer consists of recurring units having the formula (a1) or recurring units having the formula (a2), and optionally at least one selected from the group consisting of
- recurring units (b) having a phenolic hydroxyl group as an adhesive group,
- recurring units (c) having an adhesive group selected from hydroxyl (other than phenolic hydroxyl), lactone ring, ether, ester and cyano groups,
- recurring units (d) selected from units of indene, benzofuran, benzothiophene, acenaphthylene, chromone, coumarin, and norbornadiene, or derivatives thereof, and
- recurring units (e) which are derived from styrene, vinylnaphthalene, vinylanthracene, vinylpyrene, methyleneindene, vinylpyridine, or vinylcarbazole:
- wherein RA is each independently hydrogen or methyl, R41 and R42 are each independently an acid labile group, X is a single bond, phenylene, naphthylene, or a C1-C12 linking group containing ester moiety or lactone ring, and Y is a single bond or ester group.
5 more elements
A resist composition comprising a base polymer, an acid generator capable of generating sulfonic acid, sulfonimide or sulfonmethide, and a metal salt of an iodinated aromatic group-containing carboxylic acid, the metal being selected from the group consisting of sodium, magnesium, potassium, calcium, rubidium, strontium, cesium, barium, cobalt, nickel, copper, zinc, cadmium, tin, antimony, zirconium, hafnium, cerium, aluminum, and indium,
- wherein the base polymer is an acid labile group-free polymer,
- wherein the salt has the formula (A):
- wherein R1 is hydrogen, hydroxyl, a C1-C6 straight, branched or cyclic alkyl group, C1-C6 straight, branched or cyclic alkoxy group, C2-C6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR2—C(═O)—R3, or —NR2—C(═O)—O—R3, R2 is hydrogen or a C1-C6 straight, branched or cyclic alkyl group, R3 is a C1-C6 straight, branched or cyclic alkyl group or C2-C8 straight, branched or cyclic alkenyl group, G is a single bond or a C1-C20 (p+1)-valent linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety, p is an integer of 1 to 3, q is an integer of 1 to 5, r is an integer of 0 to 3, Mn+ is a metal ion selected from the group consisting of Na+, Mg2+, K+, Ca2+, Rb+, Sr2+, Cs+, Ba2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Sn4+, Sb3+, Zr4+, Hf4+, Ce3+, Al3+, and In3, and n indicative of the valence number of Mn+ is an integer of 1 to 4,
- wherein the base polymer consists of at least one selected from the group consisting of:
- recurring units (b) having a phenolic hydroxyl group as an adhesive group,
- recurring units (c) having an adhesive group selected from hydroxyl (other than phenolic hydroxyl), lactone ring, ether, ester and cyano groups,
- recurring units (d) selected from units of indene, benzofuran, benzothiophene, acenaphthylene, chromone, coumarin, and norbornadiene, or derivatives thereof, and
- recurring units (e) which are derived from styrene, vinylnaphthalene, vinylanthracene, vinylpyrene, methyleneindene, vinylpyridine, or vinylcarbazole.
5 more elements
A resist composition comprising a base polymer and a metal salt of an iodinated aromatic group-containing carboxylic acid, the metal being selected from the group consisting of sodium, magnesium, potassium, calcium, rubidium, strontium, cesium, barium, cobalt, nickel, copper, zinc, cadmium, tin, antimony, zirconium, hafnium, cerium, aluminum, and indium,
- wherein the salt has the formula (A):
- wherein R1 is hydrogen, hydroxyl, a C1-C6 straight, branched or cyclic alkyl group, C1-C6 straight, branched or cyclic alkoxy group, C2-C6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR2—C(═O)—R3, or —NR2—C(═O)—O—R3, R2 is hydrogen or a C1-C6 straight, branched or cyclic alkyl group, R3 is a C1-C6 straight, branched or cyclic alkyl group or C2-C8 straight, branched or cyclic alkenyl group, G is a single bond or a C1-C20 (p+1)-valent linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety, p is an integer of 1 to 3, q is an integer of 1 to 5, r is an integer of 0 to 3, Mn+ is a metal ion selected from the group consisting of Na+, Mg2+, K+, Ca2+, Rb+, Sr2+, Cs+, Ba2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Sn4+, Sb3+, Zr4+, Hf4+, Ce3+, Al3+, and In3+, and n indicative of the valence number of Mn+ is an integer of 1 to 4,
- wherein the base polymer is an acid labile group-free polymer,
- wherein the base polymer consists of recurring units of at least one type selected from recurring units having the formulae (f1) to (f3), and at least one selected from the group consisting of:
- recurring units (b) having a phenolic hydroxyl group as an adhesive group,
- recurring units (c) having an adhesive group selected from hydroxyl (other than phenolic hydroxyl), lactone ring, ether, ester and cyano groups,
- recurring units (d) selected from units of indene, benzofuran, benzothiophene, acenaphthylene, chromone, coumarin, and norbornadiene, or derivatives thereof,
- recurring units (e) which are derived from styrene, vinylnaphthalene, vinvlanthracene, and vinylpyrene, methyleneindene, vinylpyridine, or vinvlcarbazol,
- wherein RA is each independently hydrogen or methyl,
- Z1 is a single bond, phenylene, —O—Z11—, or —C(═O)—Z12—Z11—, Z11 is a C1-C6 straight, branched or cyclic alkylene group or C2-C6 straight, branched or cyclic alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or phenylene group, Z12 is —O— or —NH—,
- R51, R52, R53, R54, R, R56, R57, and R58 are each independently a C1-C12 straight, branched or cyclic alkyl group which may contain a carbonyl, ester or ether moiety, or a C6-C12 aryl, C7-C20 aralkyl, or mercaptophenyl group,
- Z2 is a single bond, —Z21—C(═O)—O—, —Z21—O—, or —Z21—O—C(═O)—, Z21 is a C1-C12 straight, branched or cyclic alkylene group which may contain a carbonyl, ester or ether moiety,
- Z3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—Z31—, or —C(═O)—Z32—Z31—, Z31 is a C1-C6 straight, branched or cyclic alkylene group or C2-C6 straight, branched or cyclic alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or a phenylene, fluorinated phenylene or trifluoromethyl-substituted phenylene group, Z32 is —O— or —NH—,
- A1 is hydrogen or trifluoromethyl, and M− is a non-nucleophilic counter ion.
11 more elements
Dependencies are inferred from the claim text.