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

Patent metadata

Field	Value
Publication number	US-9005870-B2
Application number	US-201113015169-A
Country	US
Kind code	B2
Filing date	Jan 27, 2011
Priority date	Jan 27, 2010
Publication date	Apr 14, 2015
Grant date	Apr 14, 2015

Abstract

According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin (P) containing a repeating unit (A) that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and at least two types of repeating units B1), (B2) that when acted on by an acid, are decomposed to thereby generate an alkali-soluble group, wherein the alkali-soluble group generated by the repeating unit (B1) is different from the alkali-soluble group generated by the repeating unit (B2).

First claim

What is claimed is:

1. An actinic-ray- or radiation-sensitive resin composition comprising a resin (P) containing a repeating unit (A) represented by general formula (II) below that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and at least two types of repeating units (B1), (B2) that when acted on by an acid, are decomposed to thereby generate an alkali-soluble group, wherein the alkali-soluble group generated by the repeating unit (B1) is different from the alkali-soluble group generated by the repeating unit (B2),

wherein
in general formula (II),
each of R 21 , R 22 and R 23 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group, a halogen atom, a cyano group or an alkoxycarbonyl group,
X 21 represents —O—, —S—, —CO—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogen-containing nonaromatic heterocyclic group or a group composed of a combination of these,
L 21 represents an alkylene group, an alkenylene group, a bivalent aliphatic hydrocarbon ring group or a group composed of a combination of two or more of these, provided that in the group composed of a combination, two or more groups combined together may be identical to or different from each other and may be linked to each other through, as a connecting group, —O—, —S—, —CO—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogen-containing nonaromatic heterocyclic group, a bivalent aromatic ring group or a group composed of a combination of these,
each of X 22 and X 23 independently represents a single bond, —O—, —S—, —CO—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogen-containing nonaromatic heterocyclic group or a group composed of a combination of these,
Ar 2 represents a bivalent aromatic ring group or a group composed of a combination of a bivalent aromatic ring group and an alkylene group,
L 22 represents an alkylene groupprovided that the hydrogen atoms of the alkylene group are partially or entirely substituted with a substituent selected from among a fluorine atom, a fluoroalkyl group, a nitro group and a cyano group, and
Z 2 represents a moiety that when exposed to actinic rays or radiation, becomes a sulfonic acid group, an imidate group or a methide group.

2. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein the repeating unit (B1) is expressed by general formula (V) below, and the repeating unit (B2) is expressed by general formula (VI) below,

in general formula (V), each of R 51 , R 52 and R 53 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 52 may be bonded to L 5 to thereby form a ring, which R 52 represents an alkylene group;
L 5 represents a single bond or a bivalent connecting group, provided that when a ring is formed in cooperation with R 52 , L 5 represents a trivalent connecting group; and
R 54 represents an alkyl group, and each of R 55 and R 56 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group or a monovalent aromatic ring group, provided that R 55 and R 56 may be bonded to each other to thereby form a ring, and provided that R 55 and R 56 are not simultaneously hydrogen atoms, and
in general formula (VI), each of R 61 , R 62 and R 63 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 62 may be bonded to Ar 6 to thereby form a ring, which R 62 represents an alkylene group;
Ar 6 represents a bivalent aromatic ring group;
Y, or each of Y′s independently, represents a hydrogen atom or a group that when acted on by an acid, is cleaved, provided that at least one of Y′s is a group that when acted on by an acid, is cleaved; and
n is an integer of 1 to 4.

3. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein the resin (P) further comprises a repeating unit (C) containing a group that when acted on by an alkali developer, is decomposed to thereby increase its solubility in the alkali developer.

4. A resist film produced from the composition according to claim 1 .

5. A method of forming a pattern, comprising forming the actinic-ray- or radiation-sensitive resin composition according to claim 1 into a film, exposing the film and developing the exposed film.

6. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein the resin (P) further comprises a repeating unit (D) expressed by general formula (IV) below,

in the formula,
each of R 41 , R 42 and R 43 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 42 may be bonded to Ar 4 to thereby form a ring, which R 42 in this instance is an alkylene group,
Ar 4 represents a bivalent aromatic ring group, and
n is an integer of 1 to 4.

7. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein L 22 in general formula (II) is an alkylene group substituted with a fluorine atom.

8. The actinic-ray- or radiation-sensitive resin composition according to claim 3 , wherein the repeating unit (C) comprises a lactone structure.

9. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , further comprising an ammonium salt.

10. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , further comprising a compound that when acted on by an acid, increases its basicity.

11. An actinic-ray- or radiation-sensitive resin composition comprising a resin (P) containing a repeating unit (A) represented by either of general formula (I) and (II) below that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and at least two types of repeating units (B1), (B2) that when acted on by an acid, are decomposed to thereby generate an alkali-soluble group, wherein the alkali-soluble group generated by the repeating unit (B1) is different from the alkali-soluble group generated by the repeating unit (B2),

wherein
in general formula (I),
each of R 11 , R 12 and R 13 independently represents a hydrogen atom, an alkyl group, a monovalent aliphatic hydrocarbon ring group, a halogen atom, a cyano group or an alkoxycarbonyl group,
X 11 represents a single bond,
X 12 represents —O—, —SO 2 —, or a group composed of a combination of these,
X 13 represents a single bond, —O—,—S—, —CO—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogen-containing nonaromatic heterocyclic group or a group composed of a combination of these,
L 11 represents a single bond, an alkylene group, an alkenylene group, a bivalent aliphatic hydrocarbon ring group, a bivalent aromatic ring group or a group comp

Assignees

• Takahashi Hidenori
• Hirano Shuji
• Tsubaki Hideaki
• Fujifilm Corp

Inventors

• Takahashi Hidenori
• Hirano Shuji
• Tsubaki Hideaki

Classifications

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title