IP Library › Granted Patent US 9,323,153
Granted Patent B2
US 9,323,153 · App. 14/478,135 · Granted Apr 26, 2016

Actinic ray-sensitive or radiation-sensitive resin composition, and, actinic ray-sensitive or radiation-sensitive film and pattern forming method, each using the same

Inventors: Shuji Hirano (Haibara-gun, JP); Hiroo Takizawa (Haibara-gun, JP); Hideaki Tsubaki (Haibara-gun, JP)
Assignee: FUJIFILM Corporation
G03F7/0397C07D235/12C07D235/16C07D235/22C07D235/26C07D235/28G03F7/0045G03F7/0046G03F7/027G03F7/038G03F7/0392G03F7/09G03F7/11G03F7/2002G03F7/2041G03F7/30G03F7/322G03F7/325
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Quick Facts
Patent No.
US 9,323,153
App. No.
14/478,135
Granted
Apr 26, 2016
Kind
B2
Abstract

An actinic ray-sensitive or radiation-sensitive resin composition in the present invention contains a nitrogen-containing compound (N) which is represented by the following general formula (N1): wherein, in the general formula (N1), X represents a group including a hetero atom; L represents a single bond or an alkylene group; R 2 represents a substituent, in the case where a plurality of R 2 's are present, they may be the same as or different from each other and a plurality of R 2 's may be bonded to each other to form a ring; R 3 represents a hydrogen atom or a substituent; and n represents an integer of 0 to 4.

Claims (41)

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising a nitrogen-containing compound (N) which is represented by the following general formula (N1), and at least one of

a resin (Ab) of which the polarity changes by the action of an acid, containing a repeating unit (B) having a structural site which generates an acid by irradiation with actinic rays or radiation and

a compound which generates an acid by irradiation with actinic rays or radiation:

wherein, in the general formula (N1),

X represents a group including a hetero atom;

L represents a single bond or an alkylene group;

R 2 represents a substituent, and in the case where a plurality of R 2 's are present, they may be the same as or different from each other and a plurality of R 2 's may be bonded to each other to form a ring;

R 3 represents —COOR 4 and a carbon atom in R 4 which is bonded to the —COO group in —COOR 4 is a tertiary carbon atom; and

n represents an integer of 0 to 4.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein R 4 in —COOR 4 is a tertiary alkyl group having 5 or more carbon atoms.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein X is a hydroxyl group or a cyano group.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the nitrogen-containing compound (N) which is represented by the general formula (N1) is represented by any of the following general formulae:

wherein, in the general formulae, R 3 represents —COOR 4 and a carbon atom in R 4 which is bonded to the —COO group in —COOR 4 is a tertiary carbon atom.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 4 , wherein R 4 in —COOR 4 is t-amyl.

6. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (Ab) contains at least one kind of repeating unit (A) which is represented by the following general formula (A):

wherein, in the general formula (A),

R 41 , R 42 and R 43 each independently represents an hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, and, R 42 may be bonded to Ar 4 to form a ring and in this case, R 42 represents a single bond or an alkylene group;

X 4 represents a single bond, —COO— or —CONR 64 , and, R 64 represents a hydrogen atom or an alkyl group;

L 4 represents a single bond or an alkylene group;

Ar 4 represents a (n+1)-valent aromatic ring group and in a case of being bonded to R 42 to form a ring, represents a (n+2)-valent aromatic ring group; and

n represents an integer of 1 to 4.

7. An actinic ray-sensitive or radiation-sensitive film comprising the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

8. A pattern forming method comprising: forming a film including a composition according to claim 1 , irradiating the film with actinic rays or radiation, and developing the irradiated film with actinic rays or radiation.

9. The pattern forming method according to claim 8 , wherein the actinic rays or radiation is EUV light.

10. An actinic ray-sensitive or radiation-sensitive resin composition comprising a nitrogen-containing compound (N) which is represented by any of the following general formulas, and, at least one of

a resin (Ab) of which the polarity changes by the action of an acid, containing a repeating unit (B) having a structural site which generates an acid by irradiation with actinic rays or radiation and

a compound which generates an acid by irradiation with actinic rays or radiation:

wherein, in the general formulas, R 3 represents a hydrogen atom or —COOR 4 and R 4 represents an alkyl group, an aryl group, an aralkyl group, an alkenyl group or a cycloalkyl group.

11. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein R 3 is a hydrogen atom or —COOR 4 and a carbon atom in R 4 which is bonded to the —COO group in —COOR 4 is a tertiary carbon atom.

12. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein R 3 is a hydrogen atom or —COOR 4 and R 4 is a tertiary alkyl group having 5 or more carbon atoms.

13. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein R 3 is —COOR 4 and R 4 is t-amyl.

14. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein the resin (Ab) contains at least one kind of repeating unit (A) which is represented by the following general formula (A):

wherein, in the general formula (A),

R 41 , R 42 and R 43 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, and, R 42 may be bonded to Ar 4 to form a ring and in this case, R 42 represents a single bond or an alkylene group;

X 4 represents a single bond, —COO— or —CONR 64 , and, R 64 represents a hydrogen atom or an alkyl group;

L 4 represents a single bond or an alkylene group;

Ar 4 represents a (n+1)-valent aromatic ring group and in a case of being bonded to R 42 to form a ring, represents a (n+2)-valent aromatic ring group; and

n represents an integer of 1 to 4.

15. An actinic ray-sensitive or radiation-sensitive film comprising the actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 .

16. A pattern forming method comprising: forming a film including a composition according to claim 10 , irradiating the film with actinic rays or radiation, and developing the irradiated film with actinic rays or radiation.

17. The pattern forming method according to claim 16 , wherein the actinic rays or radiation is EUV light.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 5, 2014
From: HIRANO, SHUJI; TAKIZAWA, HIROO; TSUBAKI, HIDEAKI
To: FUJIFILM CORPORATION
Reel/Frame 033678/0383 →
Priority Claims (2)
JP 2012-077761 · Mar 29, 2012 · national
JP 2013-033638 · Feb 22, 2013 · national
Continuity (2)
Continuation PCTJP2013059791 · Mar 25, 2013
Related Publication 20150004533A1 · Jan 1, 2015