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US 7,022,458 B2Granted
Photoresist polymer and photoresist composition containing the same
AssigneesHynix Semiconductor Inc., Dongjin Semichem Co., Ltd.
InventorsGeun Su Lee, Cheol Kyu Bok, Seung Chan Moon, Ki Soo Shin, Jae Hyun Kim, Jung Woo Kim, Sang Hyang Lee, Jae Hyun Kang
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Abstract
Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer represented by Formula 1 and a photoresist composition containing the same have excellent etching resistance, thermal resistance and adhesive property, and high affinity to an developing solution, thereby improving LER (line edge roughness). wherein X1, X2, X3, R1, R2, R3, R4, R5, m, n, o, a, b, c, d and e are as defined in the description.
Claims20
A photoresist polymer comprising a repeating unit selected from the group consisting of Formulas 1b to 1h:
- wherein
- the relative ratio of a:b:c:d is in the range of 1˜20 mol %:1˜20 mol %:10˜60 mol %:1˜40 mol %;
- and
- the relative ratio of a:b:c:d:e is in the range of 1˜20 mol %:1˜20 mol %:10˜60 mol %:1˜40 mol %:0˜30 mol %.
1 more element
A photoresist composition comprising:
- a photoresist polymer comprising a repeating unit represented by Formula 1, a photoacid generator and an organic solvent,
- wherein
- X1, X2, X3 and X4 individually are selected from the group consisting of CH2, CH2CH2, O and S;
- R1 and R2 individually are selected from the group consisting of H, CH3 and CF3;
- R3 is selected from the group consisting of an acid labile protecting group, C1–C20 alkyl and C1–C20 cycloalkyl;
- R4 is selected from the group consisting of C1–C20 hydroxyalkyl, C1–C20 hydroxyalkyl having halogen substituent, C5–C10 alkyl including an ether group, C5–C10 alkyl including an ester group, C5–C10 cycloalkyl including an ether group, and a C5–C10 cycloalkyl including an ester group;
- R5 is selected from the group consisting of H, C1–C20 alkyl, C1–C20 alkyl carboxylate, and —O—R7, wherein R7 is C1–C20 cycloalkyl;
- m is an integer ranging from 0 to 2;
- n is an integer of 0 or 1;
- and
- the relative ratio of a:b:c:d:
- e is in the range of 1˜20 mol %:1˜20 mol %:10˜60 mol %:1˜40 mol %:0˜30 mol %;
- and
- wherein the photoacid generator selected from the group consisting of phthalimidotrifluoromethane sulfonate, dinitrobeuzyltosylate, n-decyl disulfone and naphthylimido trifluoromethane sulfonate.
11 more elements
A photoresist composition comprising:
- a photoresist polymer comprising a repeating unit represented by Formula 1, a photoacid generator and an organic solvent,
- wherein
- X1, X2, X3 and X4 individually are selected from the group consisting of CH2, CH2CH2, O and S;
- R1 and R2 individually are selected from the group consisting of H, CH3 and CF3;
- R3 is selected from the group consisting of an acid labile protecting group, C1–C20 alkyl and C1–C20 cycloalkyl;
- R4 is selected from the group consisting of C1–C20 hydroxyalkyl, C1–C20 hydroxyalkyl having halogen substituent, C5–C10 alkyl including an ether group, C5–C10 alkyl including an ester group, C5–C10 cycloalkyl including an ether group, and a C5–C10 cycloalkyl including an ester group;
- R5 is selected from the group consisting of H, C1–C20 alkyl, C1–C20 alkyl carboxylate, and —O—R7, wherein R7 is C1–C20 cycloalkyl;
- m is an integer ranging from 0 to 2;
- n is an integer of 0 or 1;
- and
- the relative ratio of a:b:c:d:e is in the range of 1˜20 mol %:1˜20 mol %:10˜60 mol %:1˜40 mol %:0˜30 mol %;
- and
- wherein the photoacid generator comprises
- (i) a first photoacid generator is selected from the group consisting of phthalimidotrifluoromethane sulfonate, dinitrobenzyltosylate, n-decyl disulfone and naphthylimido trifluoromethane sulfonate;
- and
- (ii) a second photoacid generator is selected from the group consisting of diphenyl iodide hexafluorophosphate, diphenyl iodide hexafluoroarsenate, diphenyl iodide hexafluoroantimonate, diphenyl p-methoxyphenylsulfonium triflate, diphenyl p-toluenylsulfonium triflate, diphenyl p-isobutylphenylsulfonium triflate, triphenylsulfonium hexafluororarsenate, triphenylsulfonium hexafluoro-antimonate, triphenylsulfonium triflate, and dibutyl-naphthylsulfonium triflate.
13 more elements
A method for forming a photoresist pattern, comprising:
- (a) coating a photoresist composition on a wafer to form a photoresist film, the photoresist composition comprising a photoresist polymer, a photoacid generator and an organic solvent, the photoresist polymer comprising a repeating unit of the following
- wherein
- X1, X2, X3 and X4 individually are selected from the group consisting of CH2, CH2CH2, O and S;
- R1 and R2 individually are selected from the group consisting of H, CH3 and CF3;
- R3 is selected from the group consisting of an acid labile protecting group, C1–C20 alkyl and C1–C20 cycloalkyl;
- R4 is selected from the group consisting of C1–C20 hydroxyalkyl, C1–C20 hydroxyalkyl having halogen substituent, C5–C10 alkyl including an ether group, C5–C10 alkyl including an ester group, C5–C10 cycloalkyl including an ether group, and a C5–C10 cycloalkyl including an ester group;
- R5 is selected from the group consisting of H, C1–C20 alkyl, C1–C20 alkyl carboxylate, and —O—R7, wherein R7 is C1–C20 cycloalkyl;
- m is an integer ranging from 0 to 2;
- n is an integer of 0 or 1;
- and
- the relative ratio of a:b:c:d:e is in the range of 1˜20 mol %:1˜20 mol %:10˜60 mol %:1˜40 mol %:0˜30 mol %;
- (b) exposing the photoresist film to light with an exposure energy ranging from 0.1 to 100 mJ/cm2;
- (c) baking the exposed photoresist film;
- and
- (d) developing the photoresist film to obtain a photoresist pattern.
12 more elements
Dependencies are inferred from the claim text.