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

Patent metadata

Field	Value
Publication number	US-9709892-B2
Application number	US-201113637269-A
Country	US
Kind code	B2
Filing date	Mar 25, 2011
Priority date	Mar 26, 2010
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Provided is an actinic-ray- or radiation-sensitive resin composition and a method of forming a pattern using the same, ensuring excellent the etching resistivity and the stability during a post-exposure delay (PED) period. The composition contains a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, and a compound that generates an acid of pKa≧−1.5 when exposed to actinic rays or radiation.

First claim

The invention claimed is:

1. An actinic-ray- or radiation-sensitive resin composition, comprising:
a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, and
a compound that generates an acid of pKa≧−1.5 when exposed to actinic rays or radiation,
wherein
the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group is expressed by at least one selected from the group consisting of general formulae (II-1) to (II-4) below,
the resin contains no fluorine atom, and
the acid of pKa≧−1.5 generated by the compound is at least one member selected from the group consisting of a carboxylic acid, an imidic acid, and a methide acid,

in which
R 3 , or each of R 3 s independently, represents a hydrogen atom or a monovalent organic group, provided that two R 3 s may be bonded to each other to thereby form a ring;
R 4 , or each of R 4 s independently, represents a monovalent organic group, provided that at least two R 4 s may be bonded to each other to thereby form a ring and that R 3 and R 4 may be bonded to each other to thereby form a ring; and
each of R 5 s independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or an alkynyl group, provided that at least two R 5 s may be bonded to each other to thereby form a ring and that when one or two of three R 5 s are a hydrogen atom, at least one of the rest of R 5 s represents an aryl group, an alkenyl group or an alkynyl group.

2. The composition according to claim 1 , further comprising a hydrophobic resin.

3. The composition according to claim 1 , wherein the resin further contains any of the repeating units of general formulae (I) and (II) below:

in which
each of R 1 and R 3 independently represents a hydrogen atom, an optionally substituted methyl group or any of the groups of the formula —CH 2 —R 9 in which R 9 represents a monovalent organic group;
each of R 2 , R 4 , R 5 and R 6 independently represents an alkyl group or a cycloalkyl group; and
R represents an atomic group required for forming an alicyclic structure in cooperation with a carbon atom.

4. An actinic-ray- or radiation-sensitive resin composition, comprising:
a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, and
a compound that generates an acid of pKa≧−1.5 when exposed to actinic rays or radiation,
wherein
the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group is expressed by at least one selected from the group consisting of general formulae (II-1) to (II-4) below, and
the acid of pka≧−1.5 generated by the compound is expressed by any one of general formulae (B-2) and (B-3) below,

in which
R 3 , or each of R 3 s independently, represents a hydrogen atom or a monovalent organic group, provided that two R 3 s may be bonded to each other to thereby form a ring;
R 4 , or each of R 4 s independently, represents a monovalent organic group, provided that at least two R 4 s may be bonded to each other to thereby form a ring and that R 3 and R 4 may be bonded to each other to thereby form a ring; and
each of R 5 s independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or an alkynyl group, provided that at least two R 5 s may be bonded to each other to thereby form a ring and that when one or two of three R 5 s are a hydrogen atom, at least one of the rest of R 5 s represents an aryl group, an alkenyl group or an alkynyl group,

 in which
R B , or each of R B s independently, represents a monovalent organic group, provided that in general formula (B-3), two R B s may be bonded to each other to thereby form a ring;
each of X's independently represents —CO—, —SO2- or —SO—;
L, or each of L's independently, represents a bivalent connecting group; and
each of n 1 and n 2 independently is 0 or 1; and

wherein the resin contains no fluorine atom.

5. The composition according to claim 4 , wherein the resin further contains any of the repeating units of general formulae (I) and (II) below:

in which
each of R 1 and R 3 independently represents a hydrogen atom, an optionally substituted methyl group or any of the groups of the formula —CH 2 —R 9 in which R 9 represents a monovalent organic group;
each of R 2 , R 4 , R 5 and R 6 independently represents an alkyl group or a cycloalkyl group; and
R represents an atomic group required for forming an alicyclic structure in cooperation with a carbon atom.

6. An actinic-ray- or radiation-sensitive resin composition, comprising:
a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, and
a compound that generates an acid of pKa≧−1.5 when exposed to actinic rays or radiation,
wherein
the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group is expressed by at least one selected from the group consisting of general formulae (II-1), (II-2) and (II-4) below,
the acid of pka≧−1.5 generated by the compound is at least one member selected from the group consisting of a carboxylic acid, an imidic acid, and a methide acid, and
the resin contains no fluorine atom,

in which
R 3 , or each of R 3 s independently, represents a hydrogen atom or a monovalent organic group, provided that two R 3 s may be bonded to each other to thereby form a ring;
R 4 , or each of R 4 s independently, represents a monovalent organic group, provided that at least two R 4 s may be bonded to each other to thereby form a ring and that R 3 and R 4 may be bonded to each other to thereby form a ring; and
each of R 5 s independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or an alkynyl group, provided that at least two R 5 s may be bonded to each other to thereby form a ring and that when one or two of three R 5 s are a hydrogen atom, at least one of the rest of R 5 s represents an aryl group, an alkenyl group or an alkynyl group.

7. The composition according to claim 6 , wherein the acid generated by the compound is expressed by any one of general formulae (B-2) to (B-3) below:

in which R B , or each of R B s independently, represents a monovalent organic group, provided that in general formula (B-3), two R B s may be bonded to each other to thereby form a ring;
each of X's independently represents —CO—, —SO 2 — or —SO—;
L, or each of L's independently, represents a bivalent connecting group;
and each of n 1 and n 2 independently is 0 or 1.

8. The composition according to claim 6 , further comprising a hydrophob

Assignees

• Kataoka Shohei
• Iwato Kaoru
• Kamimura Sou
• Tsuchihashi Toru
• Enomoto Yuichiro
• Fujii Kana
• Mizutani Kazuyoshi
• Tarutani Shinji
• Kato Keita
• Fujifilm Corp

Inventors

• Kataoka Shohei
• Iwato Kaoru
• Kamimura Sou
• Tsuchihashi Toru
• Enomoto Yuichiro
• Fujii Kana
• Mizutani Kazuyoshi
• Tarutani Shinji
• Kato Keita

Classifications

• C08F232/08

  having condensed rings (coumarone-indene polymers C08F244/00) · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0397

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

• G03F7/0045

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

• G03F7/2041

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