Photosensitive composition, pattern forming method using the photosensitive composition and compound for use in the photosensitive composition
View Patent ↗A photosensitive composition comprising a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation; a pattern forming method using the photosensitive composition; a compound having a specific structure; and a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation.
1. A photosensitive composition for exposure with an ArF excimer laser comprising:
(A) a compound capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation:
A-R—X—F (I)
wherein X represents —CO— or —SO 2 —;
R represents a fluorine atom-containing divalent linking group;
A represents an acidic group; and
(C) a resin having a group capable of decomposing under the action of an acid to increase a solubility of resin (C) in alkali developer;
wherein the compound (A) capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation is a sulfonium salt compound of the compound represented by formula (I) or an iodonium salt compound of the compound represented by formula (I);
the acidic group of A in formula (I) is —SO 3 H, —CO 2 H or —X—NH—X—R 1 , wherein X represents —CO— or —SO 2 —, and a plurality of X's may be the same or different; R 1 represents a monovalent organic group and the resin (C) has no aromatic group.
2. A pattern forming method comprising:
forming a photosensitive film from a photosensitive composition according to claim 1 ; and
exposing and developing the photosensitive film.
3. The photosensitive composition according to claim 1 , which further comprises (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation.
4. The photosensitive composition according to claim 3 ,
wherein the compound as the component (B) is a sulfonium salt of fluoro-substituted alkanesulfonic acid, fluorine-substituted benzenesulfonic acid or fluorine-substituted imide acid.
5. The photosensitive composition according to claim 1 ,
wherein the resin as the component (C) has a fluorine atom in a main or side chain.
6. The photosensitive composition according to claim 5 ,
wherein the resin as the component (C) has a hexafluoroisopropanol structure.
7. The photosensitive composition according to claim 1 ,
wherein the resin as the component (C) has at least one repeating unit selected from 2-alkyl-2-adamantyl (meth)acrylate and dialkyl(1-adamantyl)methyl (meth)acrylate.
8. The photosensitive composition according to claim 1 ,
wherein the resin as the component (C) has a monocyclic or polycyclic alicyclic hydrocarbon structure.
9. The photosensitive composition according to claim 8 ,
wherein the resin as the component (C) has at least one repeating unit selected from 2-alkyl-2-adamantyl (meth)acrylate and dialkyl(1-adamantyl)methyl (meth)acrylate, at least one repeating unit having a lactone structure and at least one repeating unit having a hydroxyl group.
10. The photosensitive composition according to claim 9 ,
wherein the resin as the component (C) further has a repeating unit having a carboxyl group.
11. The photosensitive composition according to claim 1 ,
wherein the resin as the component (C) has a silicon atom in a main or side chain.
12. The photosensitive composition according to claim 1 ,
wherein the resin as the component (C) has a repeating unit having a lactone structure.
13. The photosensitive composition according to claim 1 , which further comprises at least one of (G) a basic compound and (H) at least one of a fluorine-containing surfactant and a silicon-containing surfactant.
14. The photosensitive composition according to claim 13 ,
wherein the basic compound (G) is a compound having a structure selected from an imidazole structure, a diazabicyclo structure, an onium hydroxide structure, an onium carboxylate structure, a trialkylamine structure, an aniline structure and a pyridine structure, an alkylamine derivative having at least one of a hydroxyl group and an ether bond or an aniline derivative having at least one of a hydroxyl group and an ether bond.
15. The photosensitive composition according to claim 1 , wherein the divalent linking group represented by R in formula (I) is a fluorine atom-containing divalent linking group having a carbon number of 1 to 8.
16. The photosensitive composition according to claim 1 , wherein the fluorine atom-containing divalent linking group represented by R in Formula (I) is a fluorine atom-containing alkylene group or a fluorine atom-containing phenylene group.
17. The photosensitive composition according to claim 1 , wherein R 1 represents as alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group and wherein each R 1 group optionally has a substituent.
18. A compound represented by formula (A1) or (A2):
wherein R 201 , R 202 and R 203 each independently represents an organic group;
R 204 and R 205 each independently represents an aryl group, an alkyl group or a cycloalkyl group; and
X represents an anion of the compound represented by formula (I)
A-R—X—F (I)
wherein X represents —CO— or —SO 2 —;
R represents a fluorine atom-containing divalent linking group;
A represents an acidic group;
the acidic group of A in formula (I) is —SO 3 H, —CO 2 H or —X—NH—X—R 1 , wherein X represents —CO— or —SO 2 —, and a plurality of X's may be the same or different and
R 1 represents a monovalent organic group.
19. The compound according to claim 18 , wherein the divalent linking group represented by R in formula (I) is a fluorine atom-containing divalent linking group having a carbon number of 1 to 8.
20. The photosensitive composition according to claim 18 , wherein the fluorine atom-containing divalent linking group represented by R in Formula (I) is a fluorine atom-containing alkylene group or a fluorine atom-containing phenylene group.
21. The compound according to claim 18 , wherein R 1 represents as alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group and wherein each R 1 group optionally has a substituent.
22. A compound (A) capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation:
A-R—X—F (I)
wherein X represents —CO— or —SO 2 —;
R represents a fluorine atom-containing divalent linking group;
A represents an acidic group;
wherein the compound (A) capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation is a sulfonium salt compound of the compound represented by formula (I) or an iodonium salt compound of the compound represented by formula (I);
the acidic group of A in formula (I) is —SO 3 H, —CO 2 H or —X—NH—X—R 1 , wherein X represents —CO— or —SO 2 —, and a plurality of X's may be the same or different; and
R 1 represents a monovalent organic group.
23. The compound according to claim 22 , wherein the divalent linking group represented by R in formula (I) is a fluorine atom-containing divalent linking group having a carbon number of 1 to 8.
24. The photosensitive composition according to claim 22 , wherein the fluorine atom-containing divalent linking group represented by R in Formula (I) is a fluorine atom-containing alkylene group or a fluorine atom-containing phenylene group.
25. The compound according to claim 22 , wherein R 1 represents as alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group and wherein each R 1 group optionally has a substituent.
26. A negative photosensitive composition comprising:
(A) a compound capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation:
A-R—X—F (I)
wherein X represents —CO— or —SO 2 —;
R represents a fluorine atom-containing divalent linking group;
A represents an acidic group;
(B) a resin soluble in an alkali developer; and
(F) an acid crosslinking agent capable of crosslinking with the resin soluble in an alkali developer under an action of an acid;
wherein the compound (A) capable of generating a compound represented by formula (I) upon irradiation with actinic rays or radiation is a sulfonium salt compound of the compound represented by formula (I) or an iodonium salt compound of the compound represented by formula (I);
the acidic group of A in formula (I) is —SO 3 H, —CO 2 H or —X—NH—X—R 1 , wherein X represents —CO— or —SO 2 —, and a plurality of X's may be the same or different; and
R 1 represents a monovalent organic group.
27. The photosensitive composition according to claim 26 , wherein the fluorine atom-containing divalent linking group represented by R in Formula (I) is a fluorine atom-containing alkylene group or a fluorine atom-containing phenylene group.
28. The negative photosensitive composition according to claim 26 , wherein R 1 represents as alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group and wherein each R 1 group optionally has a substituent.