IP Library Granted Patent US 9,023,584
Granted Patent B2
US 9,023,584 · App. 13/901,621 · Granted May 5, 2015

Radiation-sensitive composition, and compound

Inventor: Ken Maruyama (Tokyo, JP)
Assignee: JSR Corporation
G03F7/004C07C309/27C07C381/12C07C2101/14C07C2102/42C07C2103/74G03F7/0045G03F7/0392G03F7/0397G03F7/2041Y10S430/114Y10S430/128
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Quick Facts
Patent No.
US 9,023,584
App. No.
13/901,621
Granted
May 5, 2015
Kind
B2
Abstract

A radiation-sensitive composition includes a compound represented by a formula (1), and a polymer having a structural unit that includes an acid-labile group. In the formula (1), R 1 represents a group having a polar group; n is an integer of 1 to 4, wherein, in a case where R 1 is present in a plurality of number, the plurality of R 1 s are identical or different, and optionally at least two R 1 s taken together represent a cyclic structure; A represents an alicyclic hydrocarbon group having a valency of (n+1); and M + represents a monovalent onium cation.

Claims (26)

1. A radiation-sensitive composition comprising:

a compound represented by a formula (1-A-1), a compound represented by a formula (1-B-1), or both thereof; and

a polymer comprising a structural unit that comprises an acid-labile group:

wherein, in the formulae (1-A-1) and (1-B-1),

M + is a monovalent onium cation; and

R 2 , R 3 , R 4 and R 5 each independently represent a linear or branched hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heterocyclic group having 4 to 30 carbon atoms,

wherein a part or all of hydrogen atoms included in the linear or branched hydrocarbon group having 1 to 30 carbon atoms are substituted with at least one of an aromatic hydrocarbon group or an alicyclic hydrocarbon group,

wherein the linear or branched hydrocarbon group having 1 to 30 carbon atoms does not include or includes an ester group, an amide group, a urethane group, a urea group, a carbonate group or a sulfide group between carbon atoms, and

wherein a part or all of hydrogen atoms included in the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the heterocyclic group represented by R 2 , R 3 , R 4 and R 5 are not substituted or substituted.

2. The radiation-sensitive composition according to claim 1 , wherein the polymer further comprises a structural unit represented by a formula (b-1), a structural unit represented by a formula (b-2) or a combination thereof:

wherein, in the formula (b-1), R 6 represents a hydrogen atom or a methyl group; R 7 represents a single bond, —CO—O—, or —CO—NH—; R 8 represents a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxyl group having 1 to 12 carbon atoms, or an acyloxy group having 2 to 12 carbon atoms; R represents a hydroxyl group, or a group that comprises a hydroxyl group or a hydroxyl group; p is 0 or 1; q and r are each independently an integer of 0 to 3, wherein, in a case where p is 0, a sum of q and r is no greater than 5, and in a case where R 8 is present in a plurality of number, a plurality of R 8 s are identical or different, and

in the formula (b-2), R 9 represents a hydrogen atom or a methyl group.

3. The radiation-sensitive composition according to claim 1 , wherein the radiation-sensitive composition further comprises a solvent, wherein

the solvent comprises an ethylene glycol monoalkyl ether acetate, a propylene glycol monoalkyl ether acetate or a combination thereof, and

a content of the ethylene glycol monoalkyl ether acetate, the propylene glycol monoalkyl ether acetate or the combination thereof in the solvent is no less than 70% by mass.

4. A compound represented by a formula (1-A-1) or (1-B-1):

wherein, in the formulae (1-A-1) and (1-B-1),

M + is a monovalent onium cation; and

R 2 , R 3 , R 4 and R 5 each independently represent a linear or branched hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heterocyclic group having 4 to 30 carbon atoms,

wherein a part or all of hydrogen atoms included in the linear or branched hydrocarbon group having 1 to 30 carbon atoms are substituted with at least one of an aromatic hydrocarbon group or an alicyclic hydrocarbon group,

wherein the linear or branched hydrocarbon group having 1 to 30 carbon atoms does not include or includes an ester group, an amide group, a urethane group, a urea group, a carbonate group or a sulfide group between carbon atoms, and

wherein a part or all of hydrogen atoms included in the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the heterocyclic group represented by R 2 , R 3 , R 4 and R 5 are not substituted or substituted.

5. The radiation-sensitive composition according to claim 1 , wherein the alicyclic hydrocarbon group represented by R 2 , R 3 , R 4 and R 5 is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a bornyl group, a norbornyl group, an adamantyl group, a pinanyl group, a thuiyl group, a caryle group, or a camphonyl group, a part or all of hydrogen atoms included in the alicyclic hydrocarbon group being not substituted or substituted.

6. The radiation-sensitive composition according to claim 1 , wherein the aromatic hydrocarbon group represented by R 2 , R 3 , R 4 and R 5 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, or a 1-phenanthryl group, a part or all of hydrogen atoms included in the aromatic hydrocarbon group being not substituted or substituted.

7. The compound according to claim 4 , wherein the alicyclic hydrocarbon group represented by R 2 , R 3 , R 4 and R 5 is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a bornyl group, a norbornyl group, an adamantyl group, a pinanyl group, a thuiyl group, a caryle group, or a camphonyl group, a part or all of hydrogen atoms included in the alicyclic hydrocarbon group being not substituted or substituted.

8. The compound according to claim 4 , wherein the aromatic hydrocarbon group represented by R 2 , R 3 , R 4 and R 5 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, or a 1-phenanthryl group, a part or all of hydrogen atoms included in the aromatic hydrocarbon group being not substituted or substituted.

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2013
From: MARUYAMA, KEN
To: JSR CORPORATION
Reel/Frame 030694/0580 →
Priority Claims (2)
JP 2010-264360 · Nov 26, 2010 · national
WO PCT/JP2011/074080 · Oct 19, 2011 · international
Continuity (2)
Continuation PCTJP2011076839 · Nov 21, 2011
Related Publication 20130280658A1 · Oct 24, 2013