Actinic-ray- or radiation-sensitive resin composition, resist film therefrom and method of forming pattern therewith

Patent metadata

Field	Value
Publication number	US-9568824-B2
Application number	US-201113193235-A
Country	US
Kind code	B2
Filing date	Jul 28, 2011
Priority date	Jul 29, 2010
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

Provided is 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 a repeating unit (B) with a structure that when acted on by an acid, is decomposed to thereby increase its solubility in an alkali developer, and a compound (U) structured so that when the composition is formed into a film, the compound is unevenly distributed in a surface of the film.

First claim

What is claimed is:

1. An actinic-ray- or radiation-sensitive resin composition comprising:
a resin (P) containing a repeating unit (A) that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and a repeating unit (B) with a structure that when acted on by an acid, is decomposed to thereby increase its solubility in an alkali developer, and
a compound (U) structured so that when the composition is formed into a film, the compound is unevenly distributed in a vertical direction of the film;
wherein the resin (P) further comprises a repeating unit (C) containing an alkali-soluble group represented by the general formula (C-I):

wherein,
each of R 11 , R 12 and R 13 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 13 may be bonded to Ar 1 to thereby form a ring, wherein R 13 is an alkylene group,
X 1 represents a single bond or a bivalent connecting group,
Ar 1 represents a bivalent aromatic ring group, provided that when a ring is formed by bonding to R 13 , Ar 1 represents a trivalent aromatic ring group, and
n is an integer of 1 to 4, and
wherein the repeating unit (A) is represented by any of the following general formulae (I):

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, —O—, —S—, —CO—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogenous nonaromatic heterocyclic group or a group composed of a combination of these;
each of, X 12 and X 13 independently represents a single bond, —O—, —S—, —SO 2 —, —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogenous nonaromatic heterocyclic group or a group composed of a combination of these;
L 11 represents an alkylene group, a bivalent aliphatic hydrocarbon ring group, a bivalent aromatic ring group or a group composed of a combination of two or more of these, wherein in the group composed of a combination, the two or more groups combined together may be identical to or different from each other and may be linked to each other through a connecting group selected from —O—, —S—, —SO 2 —, and —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogenous nonaromatic heterocyclic group or a group composed of a combination of these;
L 12 represents an alkylene group, an alkenylene group, a bivalent aliphatic hydrocarbon ring group, a bivalent aromatic ring group or a group composed of a combination of two or more of these, wherein the hydrogen atoms of each of these groups are partially or entirely substituted with a substituent selected from among a fluorine atom, a fluoroalkyl group, a nitro group and a cyano group wherein in the group composed of a combination, the groups combined together may be identical to or different from each other and may be linked to each other through a connecting group selected from —O—, —S—, —SO 2 , and —NR— (R represents a hydrogen atom or an alkyl group), a bivalent nitrogenous nonaromatic heterocyclic group or a group composed of a combination of these;
Ar 1 represents a bivalent aromatic ring group or a group composed of a combination of a bivalent aromatic ring group and an alkylene group;
Z 1 represents any of structural moieties represented by general formulae (ZI) to (ZIII) below,

wherein,
each of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 independently represents —CO— or —SO 2 —,
each of Rz 1 , Rz 2 and Rz 3 independently represents an alkyl group, a monovalent aliphatic hydrocarbon ring group, an aryl group or an aralkyl group, and
A + represents any of cations of general formulae (CT1) and (CT2) below, cations

wherein,
in general formula (CT1),
each of R 201 , R 202 and R 203 independently represents an organic group, and two of R 201 , R 202 and R 203 are not bonded to each other to form a ring; and
in general formula (CT2),
each of R 204 and R 205 independently represents an aryl group, an alkyl group or a cycloalkyl group.

2. The composition according to claim 1 , wherein the compound (U) contains either an acid group or a group that when acted on by an alkali developer, is decomposed to thereby produce an acid group.

3. The composition according to claim 1 , wherein the repeating unit (A) has a structure that when exposed to actinic rays or radiation, produces an acid group in a side chain of the resin (P).

4. The composition according to claim 1 , wherein the compound (U) contains at least either a fluorine atom or a silicon atom.

5. The composition according to claim 1 , wherein the compound (U) is a resin.

6. The composition according to claim 1 , wherein the compound (U) contains a polarity conversion group.

7. The composition according to claim 6 , wherein the compound (U) has at least either the partial structure of general formula (KA-1) below or the partial structure of general formula (KB-1) below:

in which
X represents the polarity conversion group, and
each of Y 1 and Y 2 independently represents an electron withdrawing group.

8. The composition according to claim 7 , wherein the above X represents a carboxylic ester, an acid anhydride, an acid imide, a carboxylic thioester, a carbonic ester, a sulfuric ester or a sulfonic ester.

9. The composition according to claim 1 , wherein the compound (U) has at least one partial structure selected from the group consisting of those of general formulae (KA-1-1) to (KA-1-17) below:

10. The composition according to claim 1 , wherein the compound (U) has at least one partial structure selected from the group consisting of those of general formulae (F2), (F3), (F4), (CS-1), (CS-2) and (CS-3) below:

in general formulae (F2) to (F4),
each of R 57 to R 68 independently represents a hydrogen atom, a fluorine atom or an alkyl group, provided that in each of R 57 -R 61 , R 62 -R 64 and R 65 -R 68 , at least one thereof is a fluorine atom or an alkyl group substituted with at least one fluorine atom, and

in general formulae (CS-1) to (CS-3),
each of R 12 to R 26 independently represents an alkyl group or a cycloalkyl group,
each of L 3 to L 5 independently represents a single bond or a bivalent connecting group, and
n is an integer of 1 to 5.

11. The composition according to claim 1 , wherein the repeating unit (B) is any of the repeating units of general

Assignees

• Takahashi Toshiya
• Tsubaki Hideaki
• Tamaoki Hiroshi
• Takahashi Hidenori
• Fujifilm Corp

Inventors

• Takahashi Toshiya
• Tsubaki Hideaki
• Tamaoki Hiroshi
• Takahashi Hidenori

Classifications

• G03F7/0392

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

• G03F7/0046

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

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/2039

  X-ray radiation · CPC title

• G03F7/0758

  with silicon- containing groups in the side chains · CPC title