Method of stabilizing fluorine-containing acid amplifier

Patent metadata

Field	Value
Publication number	US-9274420-B2
Application number	US-201314012188-A
Country	US
Kind code	B2
Filing date	Aug 28, 2013
Priority date	Aug 31, 2012
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

A method of stabilizing a fluorine-containing acid amplifier. The method is provided to include the step of dissolving a fluorine-containing acid amplifier in an organic solvent thereby producing a solution of the fluorine-containing acid amplifier, the fluorine-containing acid amplifier being represented by general formula (1):

First claim

What is claimed is:

1. A method of stabilizing a fluorine-containing acid amplifier, comprising the steps of:
dissolving a fluorine-containing acid amplifier in an organic solvent thereby producing a solution of the fluorine-containing acid amplifier,
wherein the solution consists of the fluorine-containing acid and the organic solvent, and
wherein the fluorine-containing acid amplifier is represented by general formula (1):

where
W represents a C 1 -C 20 straight-chain or branched saturated or unsaturated hydrocarbon group or a C 3 -C 20 cyclic saturated or unsaturated hydrocarbon group, both of which may have a substituent,
X represents a direct bond, —(CR A R A ) m (O) n (C═O) p — or —R B (O) q (C═O) r — where: R A mutually independently represents a hydrogen atom, a C 1 -C 6 alkyl group or a phenyl group; R B represents a phenylene group or cyclohexylene group in which any number of hydrogen atoms may be substituted with fluorine atoms, C 1 -C 4 alkyl groups or C 1 -C 4 fluorinated alkyl groups any number of hydrogen atoms of which are substituted with fluorine atoms; m is an integer of 0 to 4; n is an integer of 0 or 1; p is an integer of 0 or 1; q is an integer of 0 or 1; r is an integer of 0 or 1, and
Y is selected from formulas (a) and (b) and (c):
(a) —C(═CH 2 )Z, where Z represents a hydrogen atom, fluorine atom, CH 3 group or CF 3 group;
(b) —C d H e F f ,where d is an integer of 1 to 15, e is an integer of 0 to 30, f is an integer of 1 to 31, and the total of e and f is 2d+1; and
(c) a C 3 -C 12 cyclic saturated or unsaturated hydrocarbon group which may have a substituent.

2. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein a moiety indicated with W in the fluorine-containing acid amplifier represented by general formula (1) has a structure represented by the following formulas:

where R represents a C 1 -C 18 straight-chain or branched saturated or unsaturated hydrocarbon group which may have a substituent, and a line segment accompanied with a wavy line represents a binding site.

3. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein a moiety indicated with X—Y in the fluorine-containing acid amplifier represented by general formula (1) has a structure represented by the following formulas:

where
AB represents —C(═O)OCH 3 group, —OC(═O)CH 3 group, —C(═O)CH 3 group, —CN group, —CH═CH 2 group, —OC(═O)CH(═CH 2 ) group or —OC(═O)CCH 3 (═CH 2 ) group,
AC represents —CF 3 group, —OH group, —OCH 3 group, —C═O(oxo) group, C 1 -C 4 alkyl group, —NO 2 group, fluorine atom or a C 1 -C 4 alkyl group any number of hydrogen atoms of which are substituted with fluorine atoms,
s which represents the number of AB is an integer of 0 or 1,
t which represents the number of AC is an integer of 0 to 5,
the total of s and t meets an integer of 0 to 5, and
a line segment accompanied with a wavy line represents a binding site.

4. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the organic solvent is at least one kind selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, alcohols, ketones, cyclic ketones, polyalcohols, polyalcohol derivatives, cyclic ethers, chain ethers, esters, sulfonyl esters, amides, aromatic solvents and fluorine-based solvents.

5. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the fluorine-containing acid amplifier contained in the solution of the fluorine-containing acid amplifier has a concentration of 0.05 to 90 mass %.

6. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein a storage temperature is −30 to +50° C.

7. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the concentration of the fluorine-containing acid amplifier in the fluorine-containing acid amplifier solution is 1 to 50 mass %.

8. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the concentration of the fluorine-containing acid amplifier in the fluorine-containing acid amplifier solution is 5 to 10 mass %.

9. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the fluorine-containing acid amplifier represented by general formula (1) has any one of the following structures:

10. A method of stabilizing a fluorine-containing acid amplifier, as claimed in claim 1 , wherein the fluorine-containing acid amplifier represented by general formula (1) has any one of the following structures:

11. A solution of a fluorine-containing acid amplifier consisting of:
a fluorine-containing acid amplifier; and
an organic solvent,
wherein the fluorine-containing acid amplifier is represented by general formula (1):

where
W represents a C 1 -C 20 straight-chain or branched saturated or unsaturated hydrocarbon group or a C 3 -C 20 cyclic saturated or unsaturated hydrocarbon group, both of which may have a substituent,
X represents a direct bond, —(CR A R A ) m (O) n (C═O) p — or —R B (O) q (C═O) r — where: R A mutually independently represents a hydrogen atom, a C 1 -C 6 alkyl group or a phenyl group; R B represents a phenylene group or a cyclohexylene group, in which any number of hydrogen atoms may be substituted with fluorine atoms, C 1 -C 4 alkyl groups or C 1 -C 4 fluorinated alkyl groups any number of hydrogen atoms of which are substituted with fluorine atoms; m is an integer of 0 to 4; n is an integer of 0 or 1; p is an integer of 0 or 1; q is an integer of 0 or 1; r is an integer of 0 or 1, and
Y is selected from formulas (a) and (b) and (c):
(a) —C(═CH 2 )Z, where Z represents a hydrogen atom, fluorine atom, CH 3 group or CF 3 group;
(b) —C d H e F f , where d is an integer of 1 to 15, e is an integer of 0 to 30, f is an integer of 1 to 31, and the total of e and f is 2d+1; and
(c) a C 3 -C 12 cyclic saturated or unsaturated hydrocarbon group which may have a substituent.

12. A solution of a fluorine-containing acid amplifier, as claimed in claim 11 , wherein the organic solvent is at least one kind selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, alcohols, ketones, cyclic ketones, polyalcohols, polyalcohol derivatives, cyclic ethers, chain ethers, esters, sulfonyl esters, amides, aromatic solvents and fluorine-based solvents.

13. A solution of a fluorine-containing acid amplifier, as claimed in claim 11 , wherein the concentration of the fluorine-containing acid amplifier in the fluorine-containing acid amplifier solution is 0.05 to 90 mass %.

Assignees

• Central Glass Co Ltd
• Res Foundation For The University Of New York

Inventors

• Akiba Shinya
• Nadano Ryo
• Brainard Robert L

Classifications

• C07D319/06

  not condensed with other rings · CPC title

• G03F7/0046 Primary

  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

• G03F7/0047

  characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing · CPC title

• C09K3/00

  Materials not provided for elsewhere · CPC title