Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, manufacturing method of electronic device using the same, and electronic device

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:

(A) a resin having a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (4), and a group capable of decomposing by an action of an acid to produce a polar group, and

an ionic compound represented by the following formula (2):

wherein in formula (1),

each of R 11 , R 12 and R 13 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, R 13 may combine with Ar 1 to form a ring and in this case, R 13 represents an alkylene group,

X 1 represents a single bond or a divalent linking group,

Ar 1 represents an (n+1)-valent aromatic ring group and in the case of combining with R 13 to form a ring, represents an (n+2)-valent aromatic ring group, and

n represents an integer of 1 to 4;

in formula (2),

each of R 21 , R 22 , R 23 and R 24 independently represents a methyl group, an ethyl group or a propyl group,

A − represents COO − or O − ,

Ar 2 represents an (m+1)-valent aromatic ring group having no substituent other than A − and R 25 ,

R 25 represents an alkyl group, a cycloalkyl group, a thioalkyl group, an aryl group, a halogen atom, a cyano group, a nitro group, an alkoxy group, a thioalkoxy group, a carbonyloxy group, a carbonylamino group, an alkoxycarbonyl group or an alkylaminocarbonyl group, and when m is 2 or more, each R 25 of a plurality of R 25 may be the same as or different from every other R 25 or may combine with another R 25 to form a ring, and

m represents an integer of 0 or more;

and in 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 combine with L 4 to form a ring and in this case, R 42 represents an alkylene group,

L 4 represents a single bond or a divalent linking group and in the case of forming a ring together with R 42 , represents a trivalent linking 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 linking group,

Q 4 represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and

at least two members of Q 4 , M 4 and R 44 may combine to form a ring.

2. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,

wherein the resin (A) has a repeating unit represented by the following formula (3):

wherein 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 linking group,

Q 3 represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and

at least two members of Q 3 , M 3 and R 3 may combine to form a ring.

3. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,

wherein in formula (2), A − is COO − .

4. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,

wherein in formula (2), Ar 2 represents an (m+1)-valent benzene ring.

5. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , further comprising a compound capable of generating an acid having a volume of 240 Å 3 or more upon irradiation with an actinic ray or radiation.

6. A resist film comprising the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1 .

7. A pattern forming method comprising:

(i)a step of forming the resist film claimed in claim 6 ,

(ii) a step of exposing the film, and

(iii) a step of developing the exposed film by using a developer to form a pattern.

8. The pattern forming method as claimed in claim 7 ,

wherein the step (iii) is (iii′) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern.

9. The pattern forming method as claimed in claim 7 ,

wherein the exposure is performed using an X-ray, an electron beam or EUV light.

10. A method for manufacturing an electronic device, comprising the pattern forming method claimed in claim 7 .

11. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein m represents an integer of 1 or more.

12. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein m represents an integer of 2 or more.

13. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein A − represents O − .

14. An actinic ray-sensitive or radiation-sensitive resin composition comprising:

(A) a resin having a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (4), and a group capable of decomposing by an action of an acid to produce a polar group, and

an ionic compound represented by the following formula (2):

wherein in formula (1),

each of R 11 , R 12 and R 13 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, R 13 may combine with Ar 1 to form a ring and in this case, R 13 represents an alkylene group,

X 1 represents a single bond or a divalent linking group,

Ar 1 represents an (n+1)-valent aromatic ring group and in the case of combining with R 13 to form a ring, represents an (n+2)-valent aromatic ring group, and

n represents an integer of 1 to 4;

in formula (2),

each of R 21 , R 22 , R 23 and R 24 independently represents a primary or secondary alkyl group or an aryl group,

A − represents COO − or O − ,

Ar 2 represents an (m+1)-valent aromatic ring group having no substituent other than A − and R 25 ,

R 25 represents an alkyl group, a cycloalkyl group, a thioalkyl group, an aryl group, a halogen atom, a cyano group, a nitro group, an alkoxy group, a thioalkoxy group, a carbonyloxy group, a carbonylamino group, an alkoxycarbonyl group or an alkylaminocarbonyl group, and when m is 2 or more, each R 25 of a plurality of R 25 may be the same as or different from every other R 25 or may combine with another R 25 to form a ring, and

m represents an integer of 1 or more;

and in 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 combine with L 4 to form a ring and in this case, R 42 represents an alkylene group,

L 4 represents a single bond or a divalent linking group and in the case of forming a ring together with R 42 , represents a trivalent linking 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 linking group,

Q 4 represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and

at least two members of Q 4 M 4 and R 44 may combine to form a ring.

15. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 , wherein m represents an integer of 2 or more.

16. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 , wherein A − represents O − .

17. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 ,

wherein the resin (A) has a repeating unit represented by the following formula (3):

wherein 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 linking group,

Q 3 represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and

at least two members of Q 3 , M 3 and R 3 may combine to form a ring.

18. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 ,

wherein in formula (2), A − is COO − .

19. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 ,

wherein in formula (2), Ar 2 represents an (m+1)-valent benzene ring.

20. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 14 , further comprising a compound capable of generating an acid having a volume of 240 Å 3 or more upon irradiation with an actinic ray or radiation.

21. A resist film comprising the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 14 .

22. A pattern forming method comprising:

(i) a step of forming the resist film claimed in claim 21 ,

(ii) a step of exposing the film, and

(iii) a step of developing the exposed film by using a developer to form a pattern.

23. The pattern forming method as claimed in claim 22 ,

wherein the step (iii) is (iii′) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern.

24. The pattern forming method as claimed in claim 22 ,

wherein the exposure is performed using an X-ray, an electron beam or EUV light.

25. A method for manufacturing an electronic device, comprising the pattern forming method claimed in claim 22 .