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

Patent metadata

Field	Value
Publication number	US-9551928-B2
Application number	US-75444110-A
Country	US
Kind code	B2
Filing date	Apr 5, 2010
Priority date	Apr 6, 2009
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

According to one embodiment, An actinic-ray- or radiation-sensitive resin composition comprises a basic compound (C) having n basic groups and m groups that when exposed to actinic rays or radiation, generate an acid, provided that n and m satisfy the relationships n≧1, m≧2 and n<m.

First claim

What is claimed is:

1. An actinic-ray- or radiation-sensitive resin composition comprising:
a resin (B) whose dissolution rate in an alkali developer is increased by the action of an acid and a basic compound (C) which is any of those of general formula (1) below,

in which
A 1 represents either a group that when exposed to actinic rays or radiation, generates an acid or a hydrogen atom;
A 2 represents a group that when exposed to actinic rays or radiation, generates an acid;
provided that at least one of the groups that when exposed to actinic rays or radiation, generates an acid, represented by A1 and/or A2, represents any of those of general formulae (2-1) to (2-3) and (3-1) to (3-3) below;
B represents a basic group selected from an amino group and a phosphine group;
each of R 1 , R 3 , and R 4 independently represents a single bond, an alkylene group, a cycloalkylene group or an arylene group;
R 5 represents an unsubstituted alkylene group;
R 2 when m1=0 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and when m1≧1 represents a 2- to 4-valent connecting group;
each of L 1 and L 3 independently represents either a bivalent connecting group having a heteroatom or a single bond;
L 2 represents a connecting group;
and m1 is an integer of 0 to 3, m2 is an integer of 0 to 2 and n is an integer of 1 to 3,
provided that m which is the sum of groups that when exposed to actinic rays or radiation, generate an acid, represented by A 1 and A 2 is 2 or greater and n<m in which n is the number of basic groups represented by B, and provided that when each of A 1 , A 2 , B, R 1 , R 3 and R 4 is present in plurality, the plurality of groups may be identical to or different from each other

in which M + represents a sulfonium cation, each of R 5 to R 9 independently represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group; and * represents a site of bonding with a residue of the basic compound (C).

2. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , further comprising a compound (A) that when exposed to actinic rays or radiation, generates an acid.

3. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein at least one of the basic groups is an amino group.

4. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein at least one of the groups that when exposed to actinic rays or radiation, generate an acid is a group with an onium salt structure.

5. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein at least one of the groups that when exposed to actinic rays or radiation, generate an acid is any of those of general formulae (2-1) to (2-3) below,

in which M + represents an organic counter-cation; each of R 5 and R 6 independently represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group; and * represents a site of bonding with a residue of the basic compound (C).

6. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein at least one of the groups that when exposed to actinic rays or radiation, generate an acid is any of those of general formulae (3-1) to (3-3) below,

in which M + represents an organic counter-cation; each of R 7 to R 9 independently represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group; and * represents a site of bonding with a residue of the basic compound (C).

7. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein resin (B) whose dissolution rate in an alkali developer is increased by the action of an acid that contains repeating units of general formula (III) below,

in which
A represents an ester bond (—COO—) or an amido bond (—CONH—);
R 0 , each independently in the instance of R 0 s, represents an optionally substituted alkylene group, an optionally substituted cycloalkylene group or a combination thereof;
Z, each independently in the instance of Zs, represents an ether bond, an ester bond, a carbonyl group, an amido bond, a urethane bond or a urea bond;
R 8 represents a monovalent organic group with a lactone structure;
n is the number of repetitions of the structure of formula R 0 —Z—, being an integer of 1 to 5; and
R 7 represents a hydrogen atom, a halogen atom or an optionally substituted alkyl group.

8. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , further comprising a hydrophobic resin (D).

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

10. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) contains a repeating unit expressed by the below-specified general formula (I),

wherein in general formula (I),
R 1 represents a hydrogen atom, an optionally substituted methyl group or any of the groups of formula —CH 2 —R 9 R 9 represents a monovalent organic group,
R 2 represents an alkyl group or a cycloalkyl group,
R represents an atomic group required for forming an alicyclic structure in cooperation with a carbon atom.

11. The actinic-ray- or radiation-sensitive resin composition according to claim 10 , wherein in the general formula (I), the alicyclic structure formed by R is an alicyclic structure of a single ring.

12. The actinic-ray- or radiation-sensitive resin composition according to claim 10 , wherein the resin (B) contains at least two repeating units expressed by the general formula (I).

13. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein the resin (B) contains a repeating unit expressed by the below-specified general formula (IV)

wherein in general formula (IV), R 5 represents a hydrocarbon group having at least one cyclic structure in which neither a hydroxyl group nor a cyano group is contained,
Ra represents a hydrogen atom, an alkyl group or a group of the formula —CH 2 —O—Ra 2 in which Ra 2 represents a hydrogen atom, an alkyl group or an acyl group.

14. The actinic-ray- or radiation-sensitive resin composition according to claim 1 , wherein basic compound (C) is contained in the composition in an amount of 0.1 to 10 mass %, based on the total solid of the composition.

Assignees

• Yamaguchi Shuhei
• Tomeba Hisamitsu
• Fujita Mitsuhiro
• Fujifilm Corp

Inventors

• Yamaguchi Shuhei
• Tomeba Hisamitsu
• Fujita Mitsuhiro

Classifications

• C07C303/32

  of salts of sulfonic acids · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/0046

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

• C07C309/42

  having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C07C2101/14

  Chemistry & Metallurgy · mapped topic