IP Library Granted Patent US 8,617,785
Granted Patent B2
US 8,617,785 · App. 12/688,183 · Granted Dec 31, 2013

Actinic ray-sensitive or radiation-sensitive resin composition and pattern forming method using the same

Inventor: Shuhei Yamaguchi (Shizuoka, JP)
Assignee: FUJIFILM Corporation
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Quick Facts
Patent No.
US 8,617,785
App. No.
12/688,183
Granted
Dec 31, 2013
Kind
B2
Abstract

An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure; and (D) a low molecular compound having a group capable of leaving by an action of an acid, and a pattern forming method uses the composition.

Claims (63)

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

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

(B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a repeating unit represented by formula (3); and

(D) a low molecular compound having a group capable of leaving by an action of an acid:

wherein A represents an ester bond or a group represented by —CONH—;

each R 0 independently represents an alkylene group, a cycloalkylene group or a combination thereof, and when a plurality of R 0 's are present, the plurality of R 0 's are the same or different;

each Z independently represents an ether bond, an ester bond, an amide bond, a urethane bond or a urea bond, and when a plurality of Z's are present, the plurality of Z's are the same or different;

R 8 represents a monovalent organic group having a lactone structure;

n is a repetition number of the structure represented by —R 0 —Z— in the repeating unit represented by formula (3) and represents an integer of 1 to 5; and

R 7 represents a hydrogen atom, a halogen atom or an alkyl group;

and further wherein the component (D) is an amine derivative having a group capable of decomposing by the action of an acid on the nitrogen atom.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein (D) the low molecular compound having a group capable of leaving by an action of an acid is a structure represented by formula (A):

wherein each Ra independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group, and when n=2, two Ra's are the same or different and two Ra's may combine with each other to form a divalent heterocyclic hydrocarbon group or a derivative thereof;

each Rb independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group, provided that in —C(Rb)(Rb)(Rb), when one or more Rb is a hydrogen atom, at least one of the remaining Rb's is a cyclopropyl group or a 1-alkoxyalkyl group;

a plurality of Rb's may combine with each other to form an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic hydrocarbon group or a derivative thereof;

n represents an integer of 0 to 2;

m represents an integer of 1 to 3; and

n+m=3.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , which further comprises:

(C) a hydrophobic resin.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 3 ,

wherein an amount of the hydrophobic resin (C) is from 0.1 to 10 mass % based on the entire solid content of the actinic ray-sensitive or radiation-sensitive resin composition.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein (A) the compound capable of generating an acid upon irradiation with an actinic ray or radiation is a compound capable of generating an acid represented by formula (I-A), (I-B), (I-C) or (I-D):

wherein

in formulae (I-A) and (I-B), each of R 1 to R 8 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom or a hydroxyl group; each of A 1 and A 2 represents a divalent linking group or a single bond; R represents a substituent; k represents an integer of 0 to 5; n represents an integer of 0 to 5; each of m1 to m4 independently represents an integer of 0 to 12; and when a plurality of R's are present, two or more R's may combine with each other to form a ring;

in formula (I-C), each R 9 independently represents an at least partially fluorinated alkyl group or cycloalkyl group, or two R 9 's may combine with each other to form a fluorinated alkylene group; and

in formula (I-D), each R 10 independently represents an at least partially fluorinated alkyl group or cycloalkyl group, or at least two R 10 's may combine with each other to form a fluorinated alkylene group.

6. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein the repeating unit represented by formula (3) is a repeating unit represented by formula (3-1):

wherein R 7 , A, R 0 , Z and n have the same meanings as in formula (3);

R 9 represents an alkyl group, a cycloalkyl group, an alkoxycarbonyl group, a cyano group, a hydroxyl group or an alkoxy group, and when a plurality of R 9 's are present, the plurality of R 9 's are the same or different, and two members thereof may combine with each other to form a ring;

X represents an alkylene group, an oxygen atom or a sulfur atom; and

m represents an integer of 0 to 5.

7. A pattern forming method, comprising:

forming a film by using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ; and

exposing and developing the film.

8. The pattern forming method according to claim 7 ,

wherein the exposure is an immersion exposure through an immersion liquid.

9. The pattern forming method according to claim 8 ,

wherein the film is immersion-exposed through pure water as the immersion liquid.

10. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) further contains a repeating unit having a lactone group, other than the repeating unit represented by formula (3).

11. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) further contains a repeating unit having a polar group-free alicylic hydrocarbon structure and not exhibiting acid decomposability.

12. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 3 , wherein the hydrophobic resin (C) has (z) a group capable of decomposing by an action of an acid.

13. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein in formula (3), R 0 is a methylene group, and Z is an ester bond.

14. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 13 ,

wherein in formula (3), n is 1.

15. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein in formula (3), R 8 is a monovalent organic group containing a cyanolactone structure.

16. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein (A) the compound capable of generating an acid upon irradiation with an actinic ray or radiation is a compound represented by the following formula (ZI):

in formula (ZI), each of R 201 , R 202 and R 203 independently represents an organic group, two members out of R 201 to R 203 may combine to form a ring structure, and the ring may contain an oxygen atom, a sulfur atom, an ester bond, an amide bond or a carbonyl group; and

Z − represents a non-nucleophilic anion represented by the following formula (Xa):

in formula (Xa), R represents a hydrogen atom or an organic group.

17. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein (A) the compound capable of generating an acid upon irradiation with an actinic ray or radiation is a compound represented by the following formula (ZI):

in formula (ZI), each of R 201 , R 202 and R 203 independently represents an organic group, two members out of R 201 to R 203 combine to form a ring structure, and the ring may contain an oxygen atom, a sulfur atom, an ester bond, an amide bond or a carbonyl group; and

Z − represents a non-nucleophilic anion.

18. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) comprises a pair of acid-decomposable repeating units selected from the group consisting of the following twenty-two pairs of acid-decomposable repeating units:

19. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) does not contain a fluorine atom.

20. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 18 , wherein the resin (B) does not contain a fluorine atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2010
From: YAMAGUCHI, SHUHEI
To: FUJIFILM CORPORATION
Reel/Frame 023795/0741 →
Priority Claims (1)
JP 2009-008261 · Jan 16, 2009 · national
Continuity (1)
Related Publication 20100183980A1 · Jul 22, 2010