Salt, acid generator, resist composition, and method for producing resist patterns

Abstract

To provide a salt which allows a resist pattern having good CD uniformity to be produced, and a resist composition containing the same.SOLUTION: There are provided a salt represented by formula (I), an acid generator, and a resist composition. [In the formula, R1 and R2 each represent *-O-L10-CO-O-R10 or the like; L10 represents an alkanediyl group; R10 represents a group having a cyclic carbonate ester structure; R4, R5, R7 and R8 each represent a halogen atom, a haloalkyl group or the like; A1 and A2 each represent a hydrocarbon group; m1 represents an integer of 1-5, m2 and m8 represent integers of 0-5, and m4, m5 and m7 represent integers of 0-4, provided that 1≤m1+m7≤5 and 0≤m2+m8≤5; and AI- represents an organic anion.]SELECTED DRAWING: None

Claims

1. An acid generator containing a salt represented by formula (I). [In formula (I), R １ and R ２ These are, independently, *-O-R １０ , *-O-CO-R １０ , *-O-CO-OR １０ Or *-O-L １０ -CO-O-R １０ This represents the bond site with the benzene ring, and * indicates the bond site with the benzene ring. L １０ This represents an alkanediyl group with 1 to 6 carbon atoms. R １０ represents a group having a cyclic carbonate structure. R ４ , R ５ , R ７ and R ８ Each of these independently represents a halogen atom, a C1-C12 haloalkyl group, or a C1-C18 hydrocarbon group, and the hydrocarbon group may have substituents, and the haloalkyl group and the hydrocarbon group contain -CH 2 - stands for -O-, -CO-, -S-, or -SO ２ It may be replaced with -. A １ and A ２ Each of these independently represents a hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - stands for -O-, -CO-, -S-, or -SO ２ It may be replaced with -. m1 represents an integer from 1 to 5, and when m1 is 2 or greater, the bases within the parentheses may be the same or different. m² represents an integer between 0 and 5, and when m² is 2 or greater, the bases within the parentheses may be the same or different. m4 represents an integer from 0 to 4, and when m4 is 2 or greater, multiple R ４ They may be identical or different from one another. m5 represents an integer from 0 to 4, and when m5 is 2 or greater, multiple R ５ They may be identical or different from one another. m7 represents an integer from 0 to 4, and when m7 is 2 or greater, multiple R ７ They may be identical or different from one another. m8 represents an integer from 0 to 5, and when m8 is 2 or greater, multiple R ８ They may be identical or different from one another. However, 1 ≤ m1 + m7 ≤ 5 and 0 ≤ m2 + m8 ≤ 5. AI － This represents an organic anion.

2. A １ However, *-X ０１ -L ０１ - or * - L ０１ -X ０１ - and A ２ However, *-X ０２ -L ０２ - or * - L ０２ -X ０２ - is (X ０１ and X ０２ These are, independently, -O-, -CO-, -S-, or -SO-, respectively. ２ Represents -. L ０１ and L ０２ Each of these independently represents a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - stands for -O-, -CO-, -S-, or -SO ２ It may be replaced with -. * is R １ or R ２ This indicates the bonding site with the benzene ring to which it is bonded. ) The acid generator according to claim 1.

3. X ０１ and X ０２ The acid generator according to claim 2, wherein each is independently -O- or -S-.

4. L ０１ and L ０２ However, each independently, an alkanediyl group having 1 to 6 carbon atoms (the alkanediyl group contains -CH 2 The acid generator according to claim 2, wherein - may be replaced by -O- or -CO-.

5. R １０ The acid generator according to claim 1, wherein the group having a cyclic carbonate ester structure is a group represented by formula (Ix). [In formula (Ix), Ring W ｘ This represents a ring in a cyclic carbonate ester structure, which may have substituents. L １２ This represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - stands for -O-, -S-, -CO-, or -SO ２ It may be replaced with -. * indicates a bonding site.

6. AI － The acid generating agent according to claim 1, wherein the anion is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion.

7. AI － The acid generator according to claim 1, wherein is a sulfonate anion, and the sulfonate anion is an anion represented by formula (I-A). [In formula (IA), Q １ and Q ２ Each of these independently represents a hydrogen atom, a fluorine atom, a C1-C6 alkyl group, or a C1-C6 perfluoroalkyl group. L １ This represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and the saturated hydrocarbon group contains -CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxyl group. Y １ This represents a methyl group which may have substituents or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -SO ２ It may be replaced with - or -CO-.

8. A resist composition comprising an acid generator according to any one of claims 1 to 7 and a resin having an acid-unstable group.

9. The resist composition according to claim 8, wherein the resin having an acid-unstable group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2). [In formulas (a1-0), (a1-1), and (a1-2), L a01 , L ａ１ and L ａ２ These are, independently, -O- or *-O- (CH ２ ) ｋ１ This represents -CO-O-, where k1 is an integer from 1 to 7, and * represents the bonding site with -CO-. R a01 , R ａ４ and R ａ５ Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a02 , R a03 and R a04 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R ａ６ and R ａ７ Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by a combination of these. m1 represents an integer between 0 and 14. n1 represents an integer between 0 and 10. n1' represents an integer between 0 and 3.

10. The resist composition according to claim 8, further comprising a resin containing a structural unit having a fluorine atom.

11. The resist composition according to claim 8, further comprising a salt that generates an acid with a lower acidity than the acid generated from the acid generator.

12. (1) A step of applying the resist composition according to claim 8 onto a substrate, (2) A step of drying the coated composition to form a composition layer, (3) Exposure step of the composition layer, (4) A step of heating the composition layer after exposure, (5) A step of developing the composition layer after heating, A method for manufacturing a resist pattern that includes [the specified element].

13. A salt represented by formula (I). [In formula (I), R １ and R ２ These are, independently, *-O-R １０ , *-O-CO-R １０ , *-O-CO-OR １０ Or *-O-L １０ -CO-O-R １０ This represents the bond site with the benzene ring, and * indicates the bond site with the benzene ring. L １０ This represents an alkanediyl group with 1 to 6 carbon atoms. R １０ This represents a group having a cyclic carbonate ester structure. R ４ , R ５ , R ７ and R ８ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and -CH 2 - in the haloalkyl group and the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO ２ -. A １ and A ２ Each of these independently represents a hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - stands for -O-, -CO-, -S-, or -SO ２ It may be replaced with -. m1 represents an integer from 1 to 5, and when m1 is 2 or greater, the bases within the parentheses may be the same or different. m² represents an integer between 0 and 5, and when m² is 2 or greater, the bases within the parentheses may be the same or different. m4 represents an integer from 0 to 4, and when m4 is 2 or greater, multiple R ４ They may be identical or different from one another. m5 represents an integer from 0 to 4, and when m5 is 2 or greater, multiple R ５ They may be identical or different from one another. m7 represents any integer from 0 to 4, and when m7 is 2 or more, the plurality of Rs ７ may be the same as or different from each other. m8 represents an integer from 0 to 5, and when m8 is 2 or greater, multiple R ８ They may be identical or different from one another. However, 1 ≤ m1 + m7 ≤ 5 and 0 ≤ m2 + m8 ≤ 5. AI － This represents an organic anion.

14. A １ However, *-X ０１ -L ０１ - or * - L ０１ -X ０１ - and A ２ However, *-X ０２ -L ０２ - or * - L ０２ -X ０２ - is (X ０１ and X ０２ These are, independently, -O-, -CO-, -S-, or -SO-, respectively. ２ Represents -. L ０１ and L ０２ Each of these independently represents a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - stands for -O-, -CO-, -S-, or -SO ２ It may be replaced with -. * is R １ or R ２ This represents the bonding site with the benzene ring to which it is bonded.) The salt according to claim 13.

15. X ０１ and X ０２ The salt according to claim 14, wherein each is independently -O- or -S-.

16. L ０１ and L ０２ However, each independently, an alkanediyl group having 1 to 6 carbon atoms (the alkanediyl group contains -CH 2 The salt according to claim 14 or 15, wherein - may be replaced by -O- or -CO-.

17. R １０ The salt according to claim 13 or 14, wherein the group having a cyclic carbonate ester structure is a group represented by formula (Ix). [In formula (Ix), Ring W ｘ This represents a ring in a cyclic carbonate ester structure, which may have substituents. L １２ This represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - stands for -O-, -S-, -CO-, or -SO ２ It may be replaced with -. * indicates a bonding site.

18. AI － The salt according to claim 13 or 14, wherein the salt is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion.

19. AI － The salt according to claim 13 or 14, wherein is a sulfonate anion, and the sulfonate anion is an anion represented by formula (I-A). [In formula (IA), Q １ and Q ２ Each of these independently represents a hydrogen atom, a fluorine atom, a C1-C6 alkyl group, or a C1-C6 perfluoroalkyl group. L １ This represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and the saturated hydrocarbon group contains -CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxyl group. Y １ This represents a methyl group which may have substituents or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -SO ２ It may be replaced with - or -CO-.

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