Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Finishing or perfecting composition or product
Reexamination Certificate
1999-12-29
2002-08-13
Le, Hoa Van (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Finishing or perfecting composition or product
Reexamination Certificate
active
06432621
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a resist developer, and more particularly to a resist developer which can be suitably used for forming an image (patterns) from a positive or negative resist such as an azide compound resist or a chemical amplification resist.
2. Discussion of the Related Art
Conventionally, it has been required in the field of the art relating to lithography employed in the production of semiconductor devices and liquid crystal display devices that the dissolution selectivity of a photoresist and uniformity of fine patterns formed from the photoresist are improved. In order to satisfy the above requirement, as a positive or negative resist, there has been developed a high resolution resist such as an azide compound resist or a chemical amplification resist, the base resin of which is an alkali-soluble polymer. Also, as a developer for the resist, an aqueous solution of a quaternary ammonium hydroxide and the like has been proposed.
When the aqueous solution of a quaternary ammonium hydroxide, however, alone is used as a developer, it cannot be satisfactory in the field of the art requiring high resolution, because the dissolution selectivity of a resist is lowered as the resist patterns become fine.
In order to improve the dissolution selectivity of a resist, there has been proposed a developer prepared by mixing an aqueous solution of a quaternary ammonium hydroxide and the like with an alkylene oxide compound (Japanese Examined Patent Publication Nos. Hei 6-38159 and Hei 5-73228). The proposed developer, however, does not satisfy the required dissolution selectivity to a resist.
An object of the present invention is to provide a resist developer showing excellent dissolution selectivity, which promotes the solubility of a resist in a soluble portion and inhibits the solubility of a resist in a non-soluble portion to form uniform fine resist patterns, and capable of developing a resist in a short period of time.
These and other objects of the present invention will be apparent from the following description.
SUMMARY OF THE INVENTION
In sum, the present invention pertains to the followings:
[1] a resist developer obtained by a process comprising mixing:
(1) at least one compound selected from the group consisting of a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group in a molecule, with
(2) a salt C formed between the basic compound A and the organic compound B;
[2] a resist developer obtained by a process comprising mixing a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group in a molecule;
[3] a resist developer comprising a salt C formed between a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group in a molecule;
[4] the resist developer according to item [3] above, further comprising at least one of the basic compound A and the organic compound B;
[5] the resist developer according to any one of items [1] to [4] above, further comprising an alkylene oxide compound; and
[6] a method for developing a resist, comprising applying the resist developer according to any one of items [1] to [4] above.
DETAILED DESCRIPTION OF THE INVENTION
In one embodiment, a resist developer is obtained by a process comprising mixing:
(1) at least one compound selected from the group consisting of a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group in a molecule, with
(2) a salt C formed between the basic compound A and the organic compound B.
In another embodiment, a resist developer is obtained by a process comprising mixing a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group in a molecule.
In the present specification, the phrase “a salt C formed between a basic compound A and an organic compound B having phenolic hydroxyl group and carboxyl group (hereinafter merely referred to as “organic compound B”) is intended to mean that the salt C is composed of a salt formed between the basic compound A and the organic compound B, and/or a dissociated substance generated from the salt C.
The raw material used for the developer of the present invention includes, for instance, a combination of the basic compound A and the organic compound B; the salt C; a combination of the basic compound A, the organic compound B and the salt C; and a combination of the basic compound A and the salt C. The developer can be prepared, for instance, by dissolving the raw material in water.
In still another embodiment, the resist developer comprises a salt C, and may further comprise a basic compound A and/or an organic compound B.
Examples of the basic compound A include basic inorganic compounds such as sodium hydroxide, potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, sodium silicate, sodium metasilicate, trisodium phosphate, disodium hydrogenphosphate, and ammonia; primary amines such as ethylamine, n-propylamine, n-butylamine and 1,3-diaminopropane; secondary amines such as diethylamine, di-n-propylamine, di-n-butylamine and 4,4′-diaminodiphenylamine; tertiary amines such as n,n-dimethylethylamine, n,n-diethylmethylamine and triethylamine; imines such as bis(dialkylamino)imines; alkanolamines such as monoethanolamine, diethanolamine, triethanolamine, diethylethanolamine and propanolamine; amides such as formamide and acetamide; basic heterocyclic compounds having one or more hetero-atoms selected from nitrogen atom, oxygen atom and sulfur atom in its ring structure having 3 to 5 carbon atoms, such as pyrrole, pyrrolidine, pyrrolidone, pyridine, morpholine, pyrazine, piperidine, oxazole and thiazole; a quaternary ammonium hydroxide represented by the formula (II):
wherein each of R
4
, R
5
, R
6
and R
7
is independently an alkyl group having 1 to 6 carbon atoms, an aralkyl group having 7 or 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 8 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, and the like. Those basic compounds A can be used alone or in admixture of two or more kinds thereof.
Concrete examples of the quaternary ammonium hydroxide represented by the formula (II) include tetramethylammonium hydroxide (hereinafter referred to as “TMAH”), tetraethylammonium hydroxide, tetrabutylammonium hydroxide, tributylmethylammonium hydroxide, trimethylhydroxyethylammonium hydroxide (hereinafter referred to as “choline”), tetraethanolammonium hydroxide, methyltriethanolammonium hydroxide, and the like.
Among the basic compound A, from the viewpoint of inhibiting corrosion of a circuit pattern of a wiring plate, the basic organic compound is preferable. Further, among the basic compounds, from the viewpoint of the dissolution selectivity, the quaternary ammonium hydroxide is preferable. Also, it is desirable that each of R
4
, R
5
, R
6
and R
7
in the formula (II) has 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms, respectively. Concretely, TMAH and choline are particularly preferable.
The term “dissolution selectivity” of the resist developer described in the present specification is intended to mean a nature which promotes the solubility of a soluble region of a resist, and which inhibits the solubility of a non-soluble region of a resist. For instance, when a positive resist is developed with the resist developer, a region of the resist to which ultraviolet rays, far ultraviolet rays, excimer lasers, X-rays or electron beams are irradiated, corresponds to the soluble region of a resist, and a region of the resist to which no rays are exposed, corresponds to the non-soluble region of a resist.
Also, the term “phenolic hydroxyl group of the organic compound B” described in the present specification refers to one in which —OH group or —SH group is bonded directly to carbon atom of benzene nucleus, a conden
Kitazawa Kozo
Nomoto Shougo
Sakai Akimitsu
Birch & Stewart Kolasch & Birch, LLP
Kao Corporation
Le Hoa Van
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