Photosensitive resin composition

1. A photosensitive resin composition comprising:

(A) a resin which decomposes by an action of acid to increase the solubility in alkali developer, in which the resin contains: a repeat unit having a group represented by the following general formula (Z); and a repeat unit having a group which decomposes by an action of acid to become an alkali soluble group;

(B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, in which the compound includes at least two kinds of compounds selected from the group consisting of compounds (B1), (B2), (B3) and (B4):

(B1) a compound capable of generating aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B2) a compound capable of generating aliphatic or aromatic sulfonic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B3) a compound capable of generating aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation; and

(B4) a compound capable of generating aliphatic or aromatic carboxylic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

(C) a solvent; and

(D) a surfactant:

wherein R 50 to R 55 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent, and at least one of R 50 to R 55 represents a fluorine atom, or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom.

2. The photosensitive resin composition according to claim 1 , wherein the repeat unit having the group represented by the general formula (Z) is represented by the following general formula (1) or (2):

wherein Q 1 represents an alicyclic hydrocarbon group; L 1 and L 2 each independently represent a linking group; Z represents a group represented by the general formula (Z); R x1 and R y1 each independently represent a hydrogen atom, a halogen atom, a cyano group or an alkyl group which may have a substituent.

3. The photosensitive resin composition according to claim 1 , wherein the repeat unit having the group which decomposes by the action of acid to become the alkali soluble group is represented by the following formula (3) or (4):

wherein Q 2 represents an alicyclic hydrocarbon group; L 3 and L 4 each independently represent a linking group; V represents a group which decomposes by an action of acid to become an alkali soluble group; R x2 and R y2 each independently represent a hydrogen atom, a halogen atom, a cyano group or an alkyl group which may have a substituent.

4. The photosensitive resin composition according to claim 1 , wherein the resin (A) is a resin having: at least one of repeat units represented by the following formula (I); at least one of repeat units represented by the following formula (II); and at least one of repeat units represented by the following formula (VI):

wherein R 1 , R 5 , R 17a and R 17 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group and an alkyl group which may have a substituent; R 2 , R 3 , R 6 and R 7 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent; R 50 to R 55 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent, and at least one of R 50 to R 55 represents a fluorine atom, or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom; R 4 represents a group represented by the following general formula (IV) or (V); R 18 represents —C(R 18d )(R 18e )(R 18f ) or —C(R 18d )(R 18e )(OR 18g ); R 18d to R 18g are the same or different, and represent a hydrogen atom, or an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent; two of R 18d , R 18e and R 18f , or two of R 18d , R 18e and R 18g may combine to form a ring:

wherein R 11 , R 12 and R 13 are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent;

R 14 and R 15 are the same or different, and represent a hydrogen atom, or an alkyl group which may have a substituent; R 16 represents an alkyl, cycloalkyl, aralkyl or aryl group which may have a substituent; two of R 14 to R 16 may combine to form a ring.

5. The photosensitive resin composition according to claim 4 , wherein R 18 in the general formula (VI) is represented by the following general formula (VI-A):

wherein R 18a and R 18b are the same or different, and represent an alkyl group which may have a substituent; R 18c represents a cycloalkyl group which may have a substituent.

6. The photosensitive resin composition according to claim 4 , wherein R 18 in the general formula (VI) is represented by the following general formula (VI-B):

wherein R 18h represents an alkyl, alkenyl, alkynyl, aralkyl or aryl group which may have a substituent; Z represents an atomic group which composes a monocyclic or polycyclic alicyclic group with the carbon atom in the general formula (VI-B).

7. The photosensitive resin composition according to claim 4 , wherein R 18 in the general formula (VI) is represented by the following general formula (VI-C):

wherein R 18′ represents an alkyl, alkenyl, alkynyl, aralkyl or aryl group which may have a substituent.

8. The photosensitive resin composition according to claim 4 , wherein at least one of R 1 in the general formula (I), R 5 in the general formula (II) and R 17 in the general formula (IV) is a trifluoromethyl group.

9. The photosensitive resin composition according to claim 4 , wherein the resin (A) further contains at least one repeat unit represented by the following general formula (III) or (VII):

wherein R 8 represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 9 and R 10 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent;

R 19 and R 20 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 21 represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, or —D—CN group; D represents a single bond or a bivalent linking group.

10. The photosensitive resin composition according to claim 4 , wherein the resin (A) further contains at least one repeating unit represented by the following general formulae (VIII) to (XVII):

wherein R 25 , R 26 and R 27 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl, cycloalkyl or aryl group which may have a substituent; R 28 , R 29 and R 30 are the same or different, and represent an alkyl, cycloalkyl or aryl group which may have a substituent; R 25 and R 26 , R 27 and R 28 , and, R 29 and R 30 may combine each other to form a ring; R 31 , R 35 , R 37 , R 40 and R 44 are the same or different, and represent a hydrogen atom, or an alkyl, cycloalkyl, acyl or alkoxycarbonyl group which may have a substituent; R 32 , R 33 , R 34 , R 41 , R 42 and R 43 are the same or different, and represent a hydrogen atom, a halogen atom, or an alkyl or alkoxy group which may have a substituent; R 36 and R 39 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 38 represents an alkyl, cycloalkyl, aralkyl or aryl group which may have a substituent; B 1 and B 2 each represents a single bond or bivalent linking group; B 3 represents a bivalent linking group; and n represents 0 or 1.

11. A photosensitive resin composition comprising:

(A) a resin which decomposes by an action of an acid to increase the solubility in an alkali developer, in which the resin contains a repeat unit having a group represented by the following general formula (Y); and

(B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, in which the compound includes at least two kinds of compounds selected from the group consisting of compounds (B1), (B2), (B3) and (B4):

(B1) a compound capable of generating aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B2) a compound capable of generating aliphatic or aromatic sulfonic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B3) a compound capable of generating aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation; and

(B4) a compound capable of generating aliphatic or aromatic carboxylic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

wherein R 50 to R 55 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent; at least one of R 50 to R 55 represents a fluorine atom, or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom; R 60 to R 62 are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent.

12. The photosensitive resin composition according to claim 11 , wherein the repeat unit having the group represented by the general formula (Y) is represented by the following general formula (1′) or (2′):

Q 1 represents an alicyclic hydrocarbon group; L 1 and L 2 each independently represent a linking group; Y represents a group represented by the general formula (Y); R x1 and R y1 each independently represent a hydrogen atom, a halogen atom, a cyano group or an alkyl group which may have a substituent.

13. The photosensitive resin composition according to claim 11 , wherein the resin (A) is a resin having: at least one of repeat units represented by the following formula (II); and at least one of repeat units represented by the following formula (II′):

wherein R 5 are the same or different, and represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 6 and R 7 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent;

R 50 to R 55 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent, and at least one of R 50 to R 55 represents a fluorine atom, or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom;

R 60 to R 62 are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent.

14. The photosensitive resin composition according to claim 11 , wherein the resin (A) is a resin having: at least one of repeat units represented by the following formula (I); at least one of repeat units represented by the following formula (II); and at least one of repeat units represented by the following formula (II′):

wherein R 2 , R 3 , R 6 and R 7 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent;

R 4 represents a group of the following general formula (IV) or (V);

R 5 are the same or different, and represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent;

R 50 to R 55 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent, and at least one of R 50 to R 55 represents a fluorine atom or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom;

R 60 to R 62 are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent;

R 11 , R 12 and R 13 are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent;

R 14 and R 15 are the same or different, and represent a hydrogen atom or an alkyl group which may have a substituent;

R 16 represents an alkyl, cycloalkyl, aralkyl or aryl group which may have a substituent, and two of R 14 to R 16 may combine to form a ring.

15. The photosensitive resin composition according to claim 14 , wherein at least one of R 5 in the general formula (I), R 5 in the general formula (II) and R 5 in the general formula (II′) is a trifluoromethyl group.

16. The photosensitive resin composition according to claim 14 , wherein the resin (A) further has at least one repeat unit represented by the following general formula (III) or (VII):

wherein R 8 represents a hydrogen atom, a halogen atom a cyano group, or an alkyl group which may have a substituent; R 9 and R 10 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl , aryl or aralkyl group which may have a substituent;

R 19 and R 20 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 21 represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, or —D—CN group; D represents a single bond or a bivalent linking group.

17. The photosensitive resin composition according to claim 14 , wherein the resin (A) further has at least one repeat unit represented by the following general formulae (VIII) to (XVII):

wherein R 25 , R 26 and R 27 are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl, cycloalkyl or aryl group which may have a substituent; R 28 , R 29 and R 30 are the same or different, and represent an alkyl, cycloalkyl or aryl group which may have a substituent; R 25 and R 26 , R 27 and R 28 , and, R 29 and R 30 may combine each other to form a ring; R 31 , R 35 , R 37 , R 40 and R 44 are the same or different, and represent a hydrogen atom, or an alkyl, cycloalkyl, acyl or alkoxycarbonyl group which may have a substituent; R 32 , R 33 , R 34 , R 41 , R 42 and R 43 are the same or different, and represent a hydrogen atom, a halogen atom, or an alkyl or alkoxy group which may have a substituent; R 36 and R 39 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 38 represents an alkyl, cycloalkyl, aralkyl or aryl group which may have a substituent; B 1 and B 2 each represents a single bond or a bivalent linking group; B 3 represents a bivalent linking group; and n represents 0 or 1.

18. A photosensitive resin composition comprising:

(A) a resin which decomposes by an action of acid to increase the solubility in alkali developer, in which the resin has a repeat unit represented by the following general formula (IA) and a repeat unit represented by the following general formula (IIA); and

(B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, in which the compound includes at least two kinds of compounds selected from the group consisting of compounds (B1), (B2), (B3) and (B4):

(B1) a compound capable of generating aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B2) a compound capable of generating aliphatic or aromatic sulfonic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B3) a compound capable of generating aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation; and

(B4) a compound capable of generating aliphatic or aromatic carboxylic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation:

wherein R 1a and R 5a are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 2a , R 3a , R 6a and R 7a are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent; R 50a to R 55a are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent; at least one of R 50a to R 55a represents a fluorine atom or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom; R 56a represents a hydrogen atom, or an alkyl, cycloalkyl, acyl or alkoxycarbonyl group which may have a substituent; R 4a represents a group of the following general formula (IVA) or (VA):

wherein R 11a , R 12a and R 13a are the same or different, and represent an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent;

R 14a and R 15a are the same or different, and represent a hydrogen atom or an alkyl group which may have a substituent; R 6a represents an alkyl, cycloalkyl, aralkyl or aryl group which may have a substituent; two of R 14a to R 16a may combine to form a ring.

19. A photosensitive resin composition comprising:

(A) a resin which decomposes by an action of acid to increase the solubility in alkali developer, in which the resin has a repeat unit represented by the following general formula (IIA) and a repeat unit represented by the following general formula (VIA); and

(B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, in which the compound includes at least two kinds of compounds selected from the group consisting of compounds (B1), (B2), (B3) and (B4):

(B1) a compound capable of generating aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B2) a compound capable of generating aliphatic or aromatic sulfonic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation;

(B3) a compound capable of generating aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with one of an actinic ray and a radiation; and

(B4) a compound capable of generating aliphatic or aromatic carboxylic acid containing no fluorine atom upon irradiation with one of an actinic ray and a radiation:

wherein R 5a represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 6a and R 7a are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent; R 50a to R 55a are the same or different, and represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a substituent, and at least one of R 50a to R 55a represents a fluorine atom or an alkyl group wherein at least one hydrogen atom is substituted with a fluorine atom; R 56a represents a hydrogen atom, or an alkyl, cycloalkyl, acyl or alkoxycarbonyl group which may have a substituent; R 17a1 and R 17a2 are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group and an alkyl group which may have a substituent; R 18a represents —C(R 18a1 )(R 18a2 )(R 18a3 ) or —C(R 18a1 )(R 18a2 )(OR 18a4 ); R 18a1 to R 18a4 are the same or different, and represent a hydrogen atom or an alkyl, cycloalkyl, alkenyl, aralkyl or aryl group which may have a substituent, and two of R 18a1 , R 18a2 and R 18a3 or two of R 18a1 , R 18a2 and R 18a4 may combine to form a ring; A 0 represents a single bond or a bivalent linking group which may have a substituent.

20. The photosensitive resin composition according to claim 19 , wherein R 18a in the general formula (VIA) is represented by the following general formula (VIA-A):

wherein R 18a5 and R 18a6 are the same or different, and represent an alkyl group which may have a substituent; R 18a7 represents a cycloalkyl group which may have a substituent.

21. The photosensitive resin composition according to claim 19 , wherein R 18a in the general formula (VIA) is represented by the following general formula (VIA-B):

wherein R 18a8 represents an alkyl, alkenyl, alkynyl, aralkyl or aryl group which may have a substituent.

22. The photosensitive resin composition according to claim 18 or 19 , wherein at least one of R 1a in the general formula (IA), R 5a in the general formula (IIA) and R 17a2 in the general formula (VIA) is a trifluoromethyl group.

23. The photosensitive resin composition according to claim 18 or 19 , wherein the resin (A) further has at least one repeat unit represented by the following general formula (IIIA) or (VIIA):

wherein R 8a represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 9a and R 10a are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkenyl, aryl or aralkyl group which may have a substituent;

R 19a and R 20a are the same or different, and represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group which may have a substituent; R 21a represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, or —B 1 —CN group; B 1 represents a single bond or a bivalent linking group.