Pattern forming method, active light sensitive or radiation sensitive resin composition, resist film, method for manufacturing electronic device, and electronic device
The pattern forming method includes (1) forming a film using an active light sensitive or radiation sensitive resin composition, (2) exposing the film to active light or radiation, and (3) developing the exposed film using a developer including an organic solvent, in which the active light sensitive or radiation sensitive resin composition contains a resin (A) having a group which generates a polar group by being decomposed due to the action of an acid, the resin (A) has a phenolic hydroxyl group and/or a phenolic hydroxyl group protected with a group leaving due to the action of an acid, and the developer including the organic solvent contains an additive which forms at least one interaction of an ionic bond, a hydrogen bond, a chemical bond, and a dipole interaction, with the polar group.
1. A pattern forming method, comprising:
(1) forming a film using an active light sensitive or radiation sensitive resin composition;
(2) exposing the film to active light or radiation; and
(3) developing the exposed film using a developer including an organic solvent,
wherein the active light sensitive or radiation sensitive resin composition contains a resin (A) having a group which generates a polar group by being decomposed due to the action of an acid,
wherein the resin (A) has a repeating unit represented by the following General Formula (I),
wherein the developer including the organic solvent contains an additive which forms at least one interaction of an ionic bond, a hydrogen bond, a chemical bond, and a dipole interaction, with the polar group,
wherein, in General Formula (I), each of R 41 , R 42 , and R 43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group; R 42 may be bonded to Ar 4 to form a ring, and R 42 in this case represents a single bond or an alkylene group;
X 4 represents a single bond, —COO—, or —CONR 64 —, and, in the case of forming a ring with R 42 , X 4 represents a trivalent connecting group; R 64 represents a hydrogen atom or an alkyl group;
L 4 represents a single bond or an alkylene group;
Ar 4 represents an (n+1) valent aromatic ring group, and, in the case of being bonded to R 42 to form a ring, Ar 4 represents an (n+2) valent aromatic ring group;
n represents an integer of 2 or greater; and
Y 2 represents a hydrogen atom.
2. The pattern forming method according to claim 1 ,
wherein the resin (A) has a repeating unit represented by the following Formula (B-1),
wherein, in Formula (B-1), a represents 2.
3. The pattern forming method according to claim 2 ,
wherein each of X 4 and L 4 in General Formula (I) is a single bond.
4. The pattern forming method according to claim 2 ,
wherein the content of the repeating unit represented by General Formula (I) in which all of Y 2 's are hydrogen atoms is 10 mol % to 40 mol % of the entirety of repeating units in the resin (A).
5. The pattern forming method according to claim 1 ,
wherein the resin (A) further has a repeating unit having a group which is decomposed due to the action of an acid, and the repeating unit is a repeating unit represented by any one of the following General Formulas (V) and (4);
wherein, in General Formula (V), each of R 51 , R 52 , and R 53 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
R 52 may be bonded to L 5 to form a ring, and R 52 in this case represents an alkylene group;
L 5 represents a single bond or a divalent connecting group, and in the case of forming a ring with R 52 , L 5 represents a trivalent connecting group;
R 54 represents an alkyl group, and each of R 55 and R 56 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; R 55 and R 56 may be bonded to each other to form a ring; R 55 and R 56 do not represent a hydrogen atom at the same time in any case; and
wherein, in General Formula (4), each of R 41 , R 42 , and R 43 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
R 42 may be bonded to L 4 to form a ring, and R 42 in this case represents an alkylene group;
L 4 represents a single bond or a divalent connecting group, and in the case of forming a ring with R 42 , L 4 represents a trivalent connecting group;
R 44 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group;
M 4 represents a single bond or a divalent connecting group;
Q 4 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; and
at least two of Q 4 , M 4 , and R 44 may be bonded to each other to form a ring.
6. The pattern forming method according to claim 5 ,
wherein the repeating unit represented by General Formula (V) is a repeating unit represented by the following General Formula (II-1); and
wherein, in General Formula (II-1), each of R 1 and R 2 independently represents an alkyl group,
each of R 11 and R 12 independently represents an alkyl group or an alkyl group; R 13 represents a hydrogen atom; R 11 and R 12 may be connected to each other to form a ring; R 11 and R 13 may be connected to each other to form a ring;
Ra represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom; and
L 1 represents a single bond or a divalent connecting group.
7. The pattern forming method according to claim 6 ,
wherein R 11 and R 12 in General Formula (II-1) are connected to each other to form a ring.
8. The pattern forming method according to claim 7 ,
wherein each of between X 4 and L 4 in General Formula (I) is a single bond.
9. The pattern forming method according to claim 6 ,
wherein each of X 4 and L 4 in General Formula (I) is a single bond.
10. The pattern forming method according to claim 1 ,
wherein the resin (A) has a repeating unit represented by the following General Formula (I′) in addition to the repeating unit of formula (I):
wherein, in General Formula (I′), n′ represents an integer of 1 to 4;
Y 2 ′ represents a group leaving due to the action of an acid,
R 41 , R 42 , R 43 , X 4 , L 4 , and Ar 4 have the same meanings as R 41 , R 42 , R 43 , X 4 , L 4 , and Ar 4 in General Formula (I), respectively,
wherein a part of the repeating unit represented by General Formula (I′) is a repeating unit represented by the following General Formula (3); and
wherein, in General Formula (3), Ar 3 represents an aromatic ring group;
R 3 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group;
M 3 represents a single bond or a divalent connecting group;
Q 3 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; and
at least two of Q 3 , M 3 , and R 3 may be bonded to each other to form a ring.
11. The pattern forming method according to claim 10 ,
wherein R 3 in General Formula (3) is a group having 2 or more carbon atoms.
12. The pattern forming method according to claim 10 ,
wherein R 3 in General Formula (3) is a group represented by the following General Formula (3-2); and
wherein, in General Formula (3-2), each of R 61 , R 62 , and R 63 independently represents an alkyl group, an alkenyl group, a cycloalkyl group, or an aryl group;
n61 represents 0 or 1; and
at least two of R 61 to R 63 may be connected to each other to form a ring.
13. The pattern forming method according to claim 1 ,
wherein the active light sensitive or radiation sensitive resin composition further includes a compound (B) that generates an acid by active light or radiation.
14. The pattern forming method according to claim 13 ,
wherein the compound (B) that generates an acid by active light or radiation is a compound that generates an acid having a volume of 240 Å 3 or greater.
15. The pattern forming method according to claim 1 ,
wherein an electron beam or extreme ultraviolet rays are used as the active light or radiation.
16. The pattern forming method according to claim 1 ,
wherein, in General Formula (I), n represents an integer of 2 to 4.
17. A resist film which is formed of the active light sensitive or radiation sensitive resin composition according to claim 14 .
18. A pattern forming method, comprising:
(1) forming a film using an active light sensitive or radiation sensitive resin composition;
(2) exposing the film to active light or radiation; and
(3) developing the exposed film using a developer including an organic solvent,
wherein the active light sensitive or radiation sensitive resin composition contains a resin (A) having a group which generates a polar group by being decomposed due to the action of an acid,
wherein the resin (A) has a repeating unit represented by the following General Formula (VI),
wherein the developer including the organic solvent contains an additive which forms at least one interaction of an ionic bond, a hydrogen bond, a chemical bond, and a dipole interaction, with the polar group:
wherein, in General Formula (VI),
each of R 61 , R 62 , and R 63 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group,
L 6 represents a single bond or an alkylene group,
X 6 represents —COO—,
Ar 6 represents a phenylene group,
n represents an integer of 1 to 4, and
when n is 1, Y 2 is a group leaving due to the action of an acid, and when n is 2 or greater, each of Y 2 's independently represents a hydrogen atom or a group leaving due to the action of an acid, provided that at least one of Y 2 's represents a group leaving due to the action of an acid.
19. The pattern forming method according to claim 18 ,
wherein the resin (A) has a repeating unit represented by the following General Formula (I′):
wherein, in General Formula (I′),
each of R 41 , R 42 , and R 43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group,
L 4 represents a single bond or an alkylene group,
X 4 represents —COO—,
Ar 4 represents a phenylene group, and
n represents an integer of 1 to 4.
20. The pattern forming method according to claim 18 ,
wherein the resin (A) further has a repeating unit having a group which is decomposed due to the action of an acid, and the repeating unit is a repeating unit represented by any one of the following General Formulas (V) and (4):
wherein, in General Formula (V), each of R 51 , R 52 , and R 53 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
R 52 may be bonded to L 5 to form a ring, and R 52 in this case represents an alkylene group;
L 5 represents a single bond or a divalent connecting group, and in the case of forming a ring with R 52 , L 5 represents a trivalent connecting group;
R 54 represents an alkyl group, and each of R 55 and R 56 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; R 55 and R 56 may be bonded to each other to form a ring; R 55 and R 56 do not represent a hydrogen atom at the same time in any case; and
wherein, in General Formula (4), each of R 41 , R 42 , and R 43 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
R 42 may be bonded to L 4 to form a ring, and R 42 in this case represents an alkylene group;
L 4 represents a single bond or a divalent connecting group, and in the case of forming a ring with R 42 , L 4 represents a trivalent connecting group;
R 44 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group;
M 4 represents a single bond or a divalent connecting group;
Q 4 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; and
at least two of Q 4 , M 4 , and R 44 may be bonded to each other to form a ring.
21. The pattern forming method according to claim 20 ,
wherein the repeating unit represented by General Formula (V) is a repeating unit represented by the following General Formula (II-1):
wherein, in General Formula (II-1), each of R 1 and R 2 independently represents an alkyl group,
each of R 11 and R 12 independently represents an alkyl group or an alkyl group; R 13 represents a hydrogen atom; R 11 and R 12 may be connected to each other to form a ring; R 11 and R 13 may be connected to each other to form a ring;
Ra represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom; and
L 1 represents a single bond or a divalent connecting group.
22. The pattern forming method according to claim 21 ,
wherein R 11 and R 12 in General Formula (II-1) are connected to each other to form a ring.