Organic compounds -- part of the class 532-570 series – Organic compounds – Cyano single bonded and nitrogen or phosphorus double bonded...
Reexamination Certificate
1999-05-24
2001-06-12
Baxter, Janet (Department: 1752)
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyano single bonded and nitrogen or phosphorus double bonded...
C549S075000, C549S491000
Reexamination Certificate
active
06245930
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a novel chemical-sensitization resist composition or, more particularly, to a chemical-sensitization resist composition, which may be positive-working or negative-working, capable of giving a patterned resist layer having an excellently orthogonal cross sectional profile with high sensitivity and high pattern resolution.
It is a trend in recent years that the photolithographic patterning works in the manufacture of semiconductor devices, liquid crystal display panels and the like are conducted by using a chemical-sensitization resist composition. The working principle of the chemical-sensitization resist composition is that the solubility behavior of the resist layer in an alkaline developer solution is changed in the pattern-wise exposed areas by the catalytic activity of an acid generated from an acid-generating agent contained in the resist composition by the exposure to light. Chemical-sensitization resist compositions in general have an advantage of high sensitivity because good latent images can be formed even with a low exposure dose when the acid-generating agent has a high efficiency for radiation-induced generation of an acid.
Chemical-sensitization resist compositions are classified into positive-working and negative-working compositions, each of which comprises an acid-generating agent capable of releasing an acid by irradiation with actinic rays and a film-forming resinous ingredient which is subject to a change in the solubility in an aqueous alkaline solution by the interaction with an acid.
In the positive-working chemical-sensitization resist compositions, the film-forming resinous ingredient most widely under current use is a polyhydroxystyrene substituted for a part of the hydroxyl groups by acid-dissociable solubility-reducing groups such as tert-butoxycarbonyl groups, tetra-hydropyranyl groups and the like so as to be rendered insoluble in an aqueous alkaline solution. On the other hand, the negative-working chemical-sensitization resist compositions are formulated, as the film-forming resinous ingredient, with a combination of an alkali-soluble resin such as a novolak resin and polyhydroxystyrene resin optionally substituted for a part of the hydroxyl groups by the above mentioned solubility-reducing groups and an acid-crosslinkable compound such-as melamine resins, urea resins and the like.
It is known to employ an oximesulfonate compound as the acid-generating agent in a chemical-sensitization resist composition as is disclosed in Japanese Patent Kokai 1-124848, 2-154266, 2-161444 and 6-17433. The oximesulfonate compounds disclosed there include those having a cyano group in the molecule such as
&agr;-(p-toluenesulfonyloxyimino)phenyl acetonitrile,
&agr;-(p-chlorobenzenesulfonyloxyimino)phenyl acetonitrile,
&agr;-(4-nitrobenzenesulfonyloxyimino)phenyl acetonitrile,
&agr;-(4-nitro-2-trifluoromethylbenzenesulfonyloxyimino)phenyl acetonitrile,
&agr;-(benzenesulfonyloxyimino)-4-chlorophenyl acetonitrile,
&agr;-(benzenesulfonyloxyimino)-2,4-dichlorophenyl acetonitrile,
&agr;-(benzenesulfonyloxyimino)-2,6-dichlorophenyl acetonitrile,
&agr;-(benzenesulfonyloxyimino)-4-methoxyphenyl acetonitrile,
&agr;-(2-chlorobenzenesulfonyloxyimino)-4-methoxyphenyl acetonitrile,
&agr;-(benzenesulfonyloxyimino)-2-thienyl acetonitrile,
&agr;-(4-dodecylbenzenesulfonyloxyimino)phenyl acetonitrile,
&agr;-(4-toluenesulfonyloxyimino)-4-methoxyphenyl acetonitrile,
&agr;-(4-dodecylbenzenesulfonyloxyimino)-4-methoxyphenyl acetonitrile,
&agr;-(4-toluenesulfonyloxyimino)-3-thienyl acetonitrile, and the like.
As is taught in Japanese Patent Kokai 2-154266, these oximesulfonate compounds having a cyano group in the molecule can release an acid by the energy of various kinds of actinic rays such as deep ultraviolet light, electron beams, ion beams, X-rays and the like and, when a positive-working chemical-sensitization resist composition comprising such an oximesulfonate compound and a film-forming resinous ingredient in combination is subjected to patterning by electron beam scanning, a patterned resist layer of about 0.35 &mgr;m diameter in a hole pattern can be obtained. Also, a photocured patterned resist layer can be obtained from a negative-working chemical-sensitization resist composition comprising the oximesulfonate compound and a combination of a resin and an acid-crosslinkable compound by patterning with deep ultraviolet light.
In the manufacturing process of semiconductor devices in recent years with a rapidly proceeding trend toward a higher and higher degree of integration requiring ultrafine photolithographic patterning works, the above mentioned resist compositions are no longer quite satisfactory in several respects. Accordingly, a further improved chemical-sensitization resist composition capable of giving a patterned resist layer of an excellent cross sectional profile with a further improved pattern resolution and still with a high sensitivity is eagerly desired.
SUMMARY OF THE INVENTION
The present invention accordingly has an object, in view of the above mentioned problems and disadvantages in the prior art resist compositions, to provide a novel and improved chemical-sensitization resist composition, which may be positive-working or negative-working, capable of giving a patterned resist layer of high pattern resolution having an excellently orthogonal cross sectional profile with high sensitivity.
Thus, the chemical-sensitization resist composition provided by the present invention comprises, as a uniform solution in an organic solvent:
(A) 100 parts by weight of a film-forming resinous ingredient subject to changes in the solubility in an aqueous alkaline solution by interacting with an acid; and
(B1) from 0.5 to 20 parts by weight of an acid-generating agent capable of releasing an acid by exposure to actinic rays, which is an oximesulfonate compound having a cyano group in the molecule represented by the general formula
R
1
—C(CN)═N—O—SO
2
—R
2
, (I)
in which R
1
is an inert organic group and R
2
is an unsubstituted or substituted polycyclic monovalent hydrocarbon group including polycyclic aromatic hydrocarbon groups and polycyclic non-aromatic hydrocarbon groups, as an acid-generating agent.
In a second aspect of the invention, the acid-generating agent as the component (B2) in the chemical-sensitization resist composition is a combination of the oximesulfonate compound of the general formula (I) defined above and an onium salt compound.
In a third aspect of the invention, the acid-generating agent as the component (B3) in the chemical-sensitization resist composition is a combination of the oximesulfonate compound of the general formula (I) above and a second oximesulfonate compound having a cyano group in the molecule represented by the general formula
R
3
—C(CN)═N—O—SO
2
—R
4
, (II)
in which R
3
is an unsubstituted or substituted monovalent hydrocarbon group selected from unsaturated or saturated non-aromatic hydrocarbon groups and aromatic cyclic hydrocarbon groups and R
4
is an unsubstituted or substituted, unsaturated or saturated monovalent non-aromatic hydrocarbon group, or a third oximesulfonate compound having two or three cyano groups in the molecule represented by the general formula
A—[C(CN)═N—O—SO
2
—R
5
]
n
, (III)
in which n is 2 or 3, R
5
is an unsubstituted or substituted monovalent hydrocarbon group and A is a divalent or tervalent, when n is 2 or 3, respectively, organic group.
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Hada Hideo
Kaneko Fumitake
Nakayama Toshimasa
Oomori Katsumi
Sato Kazufumi
Ashton Rosemary
Baxter Janet
Tokyo Ohka Kogyo Co. Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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