Radiation-sensitive resin composition, method for forming resist pattern and compound

1. A radiation-sensitive resin composition comprising:

a resin having a partial structure represented by formula (1);

a radiation-sensitive acid generator; and

a solvent;

wherein, in the formula (1),

R 1 and R 2 each independently represent a substituted or unsubstituted chain aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted or unsubstituted alicyclic hydrocarbon group having 3 to 6 carbon atoms, or R 1 and R 2 are bonded to each other to form a part of a 3- to 6-membered cyclic structure together with the carbon atom to which R 1 and R 2 are bonded;

R 3 represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms and comprising an alicyclic ring, wherein the alicyclic ring comprises —CF 2 — group, and the carbon atom of the —CF 2 — group is a ring atom of the alicyclic ring;

provided that in R 1 and R 2 , no fluorine atom is bonded to carbon atoms located at α-, β- and γ-positions of the carbon atom to which R 1 and R 2 are bonded;

in R 3 , no fluorine atom is bonded to carbon atoms located at α- and β-positions of the carbon atom to which R 3 is bonded; and

* represents a bond.

2. The radiation-sensitive resin composition according to claim 1 , wherein the partial structure represented by the formula (1) is a partial structure represented by formula (1-1-1), a partial structure represented by formula (1-1-2), a partial structure represented by formula (1-1-3), or a partial structure represented by formula (1-1-4):

wherein, in the formulae (1-1-1), (1-1-2), (1-1-3), and (1-1-4),

R 1 and R 2 have the same meanings as those in the formula (1);

R f101 and R f102 are each a fluorine atom, and R f103 to R f119 each independently represent a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms;

provided that at least one of R f103 —C—R f104 and R f105 —C—R f106 , at least one of R f107 —C—R f108 , R f109 —C—R f110 and R f111 —C—R f112 , and at least one of R f113 —C—R f114 , R f115 —C—R f116 and R f118 —C—R f119 are —CF 2 — group; and

* represents a bond.

3. The radiation-sensitive resin composition according to claim 1 , wherein the partial structure represented by the formula (1) is a partial structure represented by formula (1-2-1), a partial structure represented by formula (1-2-2), or a partial structure represented by formula (1-2-3):

wherein, in the formulae (1-2-1), (1-2-2), and (1-2-3),

R 1 and R 2 have the same meanings as those in the formula (1);

R f201 and R f202 are each a fluorine atom, and R f203 to R f217 each independently represent a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms;

provided at least one of R f204 —C—R f205 and R f207 —C—R f208 , and at least one of R f210 —C—R f211 , R f213 —C—R f214 and R f216 —C—R f217 are —CF 2 — group; and

* represents a bond.

4. The radiation-sensitive resin composition according to claim 1 , wherein a content of a structural unit having the partial structure represented by the formula (1) in the resin is 5 mol % or more and 40 mol % or less.

5. A method for forming a resist pattern, comprising:

forming a resist film from the radiation-sensitive resin composition according to claim 1 ;

exposing the resist film; and

developing the exposed resist film.

6. The method for forming a resist pattern according to claim 5 , wherein the exposure is performed with use of ArF excimer laser light or extreme ultraviolet light.

7. The method for forming a resist pattern according to claim 5 , wherein the partial structure represented by the formula (1) is a partial structure represented by formula (1-1-1), a partial structure represented by formula (1-1-2), a partial structure represented by formula (1-1-3), or a partial structure represented by formula (1-1-4):

wherein, in the formulae (1-1-1), (1-1-2), (1-1-3), and (1-1-4),

R 1 and R 2 have the same meanings as those in the formula (1);

R f101 and R f102 are each a fluorine atom, and R f103 to R f119 each independently represent a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms;

provided that at least one of R f103 —C—R f104 and R f105 —C—R f106 , at least one of R f107 —C—R f108 , R f109 —C—R f110 and R f111 —C—R f112 , and at least one of R f113 —C—R f114 , R f115 —C—R f116 and R f118 —C—R f119 are CF 2 ; and

* represents a bond.

8. The method for forming a resist pattern according to claim 5 , wherein the partial structure represented by the formula (1) is a partial structure represented by formula (1-2-1), a partial structure represented by formula (1-2-2), or a partial structure represented by formula (1-2-3):

wherein, in the formulae (1-2-1), (1-2-2), and (1-2-3),

R 1 and R 2 have the same meanings as those in the formula (1);

R f201 and R f202 are each a fluorine atom, and R f203 to R f217 each independently represent a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms;

provided at least one of R f204 —C—R f205 and R f207 —C—R f208 , and at least one of R f210 —C—R f211 , R f213 —C—R f214 and R f216 —C—R f217 are CF 2 ; and

* represents a bond.

9. The method for forming a resist pattern according to claim 5 , wherein a content of a structural unit having the partial structure represented by the formula (1) in the resin is 5 mol % or more and 40 mol % or less.

10. The method for forming a resist pattern according to claim 5 , wherein the resin comprises a first structural unit, and the partial structure represented by the formula (1) is introduced as a side chain structure of the first structural unit.

11. The method for forming a resist pattern according to claim 10 , wherein the resin further comprises a second structural unit which comprises an acid-dissociable group.

12. The method for forming a resist pattern according to claim 10 , wherein the resin further comprises a third structural unit which comprises a group comprising at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure, and a sultone structure.

13. The radiation-sensitive resin composition according to claim 1 , wherein the resin comprises a first structural unit, and the partial structure represented by the formula (1) is introduced as a side chain structure of the first structural unit.

14. The radiation-sensitive resin composition according to claim 13 , wherein the resin further comprises a second structural unit which comprises an acid-dissociable group.

15. The radiation-sensitive resin composition according to claim 14 , wherein a content of the second structural unit is 10 to 70 mol % relative to total structural units in the resin.

16. The radiation-sensitive resin composition according to claim 13 , wherein the resin further comprises a third structural unit which comprises a group comprising at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure, and a sultone structure.

17. The radiation-sensitive resin composition according to claim 16 , wherein a content of the third structural unit is 20 to 70 mol % relative to total structural units in the resin.

18. A compound represented by formula (I):

wherein, in the formula (I),

R x is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group;

R 1 and R 2 each independently represent a substituted or unsubstituted chain aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted or unsubstituted alicyclic hydrocarbon group having 3 to 6 carbon atoms, or R 1 and R 2 are bonded to each other to form a part of a 3- to 6-membered cyclic structure together with the carbon atom to which R 1 and R 2 are bonded;

R 3 represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms and comprising an alicyclic ring, wherein the alicyclic ring comprises —CF 2 — group, and the carbon atom of the —CF 2 — group is a ring atom of the alicyclic ring;

provided that in R 1 and R 2 , no fluorine atom is bonded to carbon atoms located at α-, β- and γ-positions of the carbon atom to which R 1 and R 2 are bonded; and

in R 3 , no fluorine atom is bonded to carbon atoms located at α- and β-positions of the carbon atom to which R 3 is bonded.

19. A compound represented by formula (i):

wherein, in the formula (i),

R 1 and R 2 each independently represent a substituted or unsubstituted chain aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted or unsubstituted alicyclic hydrocarbon group having 3 to 6 carbon atoms, or R 1 and R 2 are bonded to each other to form a part of a 3- to 6-membered cyclic structure together with the carbon atom to which R 1 and R 2 are bonded;

R 3 represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms and comprising an alicyclic ring, wherein the alicyclic ring comprises —CF 2 — group, and the carbon atom of the —CF 2 — group is a ring atom of the alicyclic ring;

provided that in R 1 and R 2 , no fluorine atom is bonded to carbon atoms located at α-, β- and γ-positions of the carbon atom to which R 1 and R 2 are bonded; and

in R 3 , no fluorine atom is bonded to carbon atoms located at α- and β-positions of the carbon atom to which R 3 is bonded.