Pattern forming method, actinic ray-sensitive or radiation-sensitive composition used therein, resist film, manufacturing method of electronic device using the same, and electronic device

1. A pattern forming method comprising:

(i) a step of forming a film by using an actinic ray-sensitive or radiation-sensitive composition containing (A) a non-polymeric acid-decomposable compound having an aromatic ring and a molecular weight of 500 to 5,000 and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, wherein the compound (A) is a compound represented by the following formula (1):

wherein each R independently represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a carboxyl group, an alkylsilyl group, and a group having a structure capable of decomposing by the action of an acid to produce a polar group, and each R in the compound (A) may be the same as or different from every other R;

OR 1 represents a hydroxyl group or a group having a structure capable of decomposing by the action of an acid to produce a polar group, and each OR 1 in the compound (A) may be same as or different from every other OR 1 , with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

T represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a halogen atom, a carboxyl group, and an alkylsilyl group, and when a plurality of Ts are present, each T may be the same as or different from every other T;

p represents an integer of 1 to 4;

q represents an integer represented by (4-p);

n1 represents an integer of 3 or more;

n1 ps may be the same value or different values; and

n1 qs may be the same value or different values,

(ii) a step of exposing the film, and

(iii) a step of performing development by using an organic solvent-containing developer to form a negative pattern, wherein the developer comprises at least one kind of an organic solvent selected from the group consisting of a ketone-based solvent, an ester-based solvent, an alcohol-based solvent and an amide-based solvent.

2. The pattern forming method as claimed in claim 1 ,

wherein the compound (A) is a compound represented by the following formula (2):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (1), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

n2 represents an integer of 3 to 8;

n2 ps may be the same value or different values; and

n2 qs may be the same value or different values.

3. The pattern forming method as claimed in claim 2 ,

wherein the compound (A) is a compound represented by the following formula (3):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (2), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

four ps may be the same value or different values; and

four qs may be the same value or different values.

4. The pattern forming method as claimed in claim 3 ,

wherein the compound (A) is a compound represented by the following formula (4):

wherein OR 1 , R and T have the same meanings as OR 1 , R and T in formula (3), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group.

5. The pattern forming method as claimed in claim 1 ,

wherein at least one R in formula (1) is an aryl group represented by the following formula (5):

wherein each R 4 independently represents a hydrogen atom or a substituent,

with the proviso that at least one of the plurality of OR 1 s and the plurality of R 4 s in the compound (A) is a group having a structure capable of decomposing by the action of an acid to produce a polar group.

6. The pattern forming method as claimed in claim 1 ,

wherein the exposure in the step (ii) is exposure to an electron beam or an extreme-ultraviolet ray (EUV light).

7. The pattern forming method as claimed in claim 1 , further comprising:

(iv) a step of performing rinsing by using an organic solvent-containing rinsing solution.

8. The pattern forming method as claimed in claim 1 ,

wherein the developer comprises at least one kind of an organic solvent selected from a ketone-based solvent, an ester-based solvent and an amide-based solvent.

9. The pattern forming method as claimed in claim 1 ,

wherein the developer comprises an ester-based solvent.

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

wherein the ester-based solvent is butyl acetate, pentyl acetate or isopentyl acetate.

11. An actinic ray-sensitive or radiation-sensitive composition containing:

(A) a non-polymeric acid-decomposable compound having an aromatic ring and a molecular weight of 500 to 5,000 and

(B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation,

wherein the compound (A) is a compound represented by the following formula (1):

wherein each R independently represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a carboxyl group, an alkylsilyl group, and a group having a structure capable of decomposing by the action of an acid to produce a polar group, and each R in the compound (A) may be the same as or different from every other R;

the aryl group represented by R in formula (1) is represented by the following formula (5), wherein each R 4 independently represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxy group, a cyano group, a nitro group, a heterocyclic group, a halogen atom, a carboxyl group, and an alkylsilyl group:

OR 1 represents a hydroxyl group or a group having a structure capable of decomposing by the action of an acid to produce a polar group, and each OR 1 in the compound (A) may be same as or different from every other OR 1 , with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

T represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a halogen atom, a carboxyl group, and an alkylsilyl group, and when a plurality of Ts are present, each T may be the same as or different from every other T;

p represents an integer of 1 to 4;

q represents an integer represented by (4-p);

n1 represents an integer of 3 or more;

n1 ps may be the same value or different values; and

n1 qs may be the same value or different values.

12. The actinic ray-sensitive or radiation-sensitive composition according to claim 11 , wherein the compound (A) is a compound represented by the following formula (2):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (1), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 s and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

n2 represents an integer of 3 to 8;

n2 ps may be the same value or different values; and

n2 qs may be the same value or different values.

13. The actinic ray-sensitive or radiation-sensitive composition according to claim 12 , wherein the compound (A) is a compound represented by the following formula (3):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (2), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 S and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group;

four ps may be the same value or different values; and

four qs may be the same value or different values.

14. The actinic ray-sensitive or radiation-sensitive composition according to claim 13 , wherein the compound (A) is a compound represented by the following formula (4):

wherein OR 1 , R and T have the same meanings as OR 1 , R and T in formula (3), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T, with the proviso that at least one of the plurality of OR 1 S and the plurality of Rs is a group having a structure capable of decomposing by the action of an acid to produce a polar group.

15. The actinic ray-sensitive or radiation-sensitive composition according to claim 11 , wherein at least one R in formula (1) is an aryl group represented by formula (5),

with the proviso that at least one of the plurality of OR 1 s and the plurality of R 4 s in the compound (A) is a group having a structure capable of decomposing by the action of an acid to produce a polar group.

16. A resist formed of the actinic ray-sensitive or radiation-sensitive composition claimed in claim 11 .

17. An actinic ray-sensitive or radiation-sensitive composition containing:

(A) a non-polymeric acid-decomposable compound having an aromatic ring and a molecular weight of 500 to 5,000 and

(B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation,

wherein the compound (A) is a compound represented by the following formula (1):

wherein each R independently represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a carboxyl group, an alkylsilyl group, and a group having a structure capable of decomposing by the action of an acid to produce a polar group, and each R in the compound (A) may be the same as or different from every other R;

OR 1 represents a group having a structure capable of decomposing by the action of an acid to produce a polar group, R 1 in OR 1 represents a substituted methyl group, a 1-substituted ethyl group, a 1-substituted-n-propyl group, a 1-branched alkyl group, a silyl group, a 1-substituted alkoxymethyl group, a cyclic ether group, or an alkoxycarbonylalkyl group, and each OR 1 in the compound (A) may be same as or different from every other OR 1 ;

T represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxyl group, a cyano group, a nitro group, a hydroxyl group, a heterocyclic group, a halogen atom, a carboxyl group, and an alkylsilyl group, and when a plurality of Ts are present, each T may be the same as or different from every other T;

p represents an integer of 1 to 4;

q represents an integer represented by (4-p);

n1 represents an integer of 3 or more;

n1 ps may be the same value or different values; and

n1 qs may be the same value or different values.

18. The actinic ray-sensitive or radiation-sensitive composition according to claim 17 , wherein R 1 in formula (1) represents an alkoxycarbonylalkyl group.

19. The actinic ray-sensitive or radiation-sensitive composition according to claim 17 , wherein the compound (A) is a compound represented by the following formula (2):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (1), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T;

n2 represents an integer of 3 to 8;

n2 ps may be the same value or different values; and

n2 qs may be the same value or different values.

20. The actinic ray-sensitive or radiation-sensitive composition according to claim 19 , wherein the compound (A) is a compound represented by the following formula (3):

wherein OR 1 , R, T, p and q have the same meanings as OR 1 , R, T, p and q in formula (2), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T four ps may be the same value or different values; and

four qs may be the same value or different values.

21. The actinic ray-sensitive or radiation-sensitive composition according to claim 20 , wherein the compound (A) is a compound represented by the following formula (4):

wherein OR 1 , R and T have the same meanings as OR 1 , R and T in formula (3), respectively, and each OR 1 , R or T in the compound (A) may be the same as or different from every other OR 1 , R or T.

22. The actinic ray-sensitive or radiation-sensitive composition according to claim 17 , wherein at least one R in formula (1) is an aryl group represented by the following formula (5):

wherein each R 4 independently represents a hydrogen atom or a substituent.