Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Reexamination Certificate
2002-05-14
2004-05-11
Ashton, Rosemary (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
C430S921000, C430S922000
Reexamination Certificate
active
06733951
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a positive radiation-sensitive composition for use in the manufacturing processes of lithographic printing plates and semiconductors such as IC, the manufacture of circuit boards for liquid crystals and thermal heads, and other photofabrication processes.
BACKGROUND OF THE INVENTION
A variety of kinds of compositions are used as the photosensitive compositions for use in the manufacturing processes of lithographic printing plates and semiconductors such as IC, the manufacture of circuit boards for liquid crystals and thermal heads, and other photofabrication processes, and photoresist photosensitive compositions are generally used. The photoresist photosensitive compositions are roughly classified into two kinds of a positive type and a negative type.
As one of positive photoresist photosensitive compositions, chemically amplified resist compositions are disclosed in U.S. Pat. No. 4,491,628 and EP 249139.
Chemically amplified positive resist compositions are pattern-forming materials for forming patterns on a substrate by generating an acid on the exposed area by irradiation with radiations such as far ultraviolet rays and, by the reaction with the acid as a catalyst, transforming the solubilities in a developing solution of the irradiated area and the non-irradiated area with radiation.
As such examples, the combinations of compounds which generate an acid by photodecomposition with acetal or O,N-acetal compounds (e.g., JP-A-48-89003 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”)), with ortho esters or an amide acetal compounds (e.g., JP-A-51-120714), with polymers having an acetal or ketal group at the main chain (e.g., JP-A-53-133429), with enol ether compounds (e.g., JP-A-55-12995), with N-acyliminocarbonic acid compounds (e.g., JP-A-55-126236), with polymers having an ortho ester group at the main chain (e.g., JP-A-56-17345), with tertiary alkyl ester compounds (e.g., JP-A-60-3625), with silyl ester compounds (e.g., JP-A-60-10247), and with silyl ether compounds (e.g., JP-A-60-37549 and JP-A-60-121446) can be exemplified. These combinations show high photosensitivity as quantum yields thereof exceed 1 in principle.
Similarly, as systems which are decomposed by heating in the presence of an acid and alkali-solubilized although stable during aging under room temperature, e.g., the combinations of compounds which generate an acid by exposure (e.g., those disclosed in JP-A-59-45439, JP-A-60-3625, JP-A-62-229242, JP-A-63-27829, JP-A-63-36240, JP-A-63-250642
, Polym. Eng. Sce.,
Vol. 23, p. 1012 (1983),
ACS. Sym.,
Vol. 242, p. 11 (1984),
Semiconductor World,
p. 91 (November, 1987),
Macromolecules,
Vol. 21, p. 1475 (1988), and
SPIE,
Vol. 920, p. 42 (1988)), with esters or carbonic ester compounds of tertiary or secondary carbons (e.g., t-butyl, 2-cyclohexenyl) can be exemplified. These systems also show high sensitivity and small absorption in far ultraviolet region, therefore, they are effective for shifting the wavelength of light sources to shortwave where it is possible to perform ultra-fine process.
These chemically amplified positive resists can be roughly classified into three-component series comprising an alkali-soluble resin, a compound generating an acid upon irradiation with radiation (a light-acid generating agent (i.e., a photo-acid generating agent)), and a dissolution-inhibiting compound of an alkali- soluble compound having an acid-decomposable group, and two-component series comprising a resin having a group decomposable upon reaction with an acid and becoming alkali-soluble, and a light-acid generating agent. In these two-component or three-component series chemically amplified positive resists, a resist pattern is obtained by development after heating process via an acid from a light-acid generating agent by exposure.
As described above, these chemically amplified positive resists are effective for shifting the wavelength of light sources to shortwave where it is possible to perform ultra-fine process, and further improvement of resolution has been required.
As the light-acid generating agents, a triarylsulfonium salt, a phenacylsulfonium salt and an iodonium salt are well known.
A resist composition containing an acid-decomposable polymer and a mixed acid-generating agent comprising a triphenyl-sulfonium salt and a phenacylsulfonium salt is disclosed in JP-A-2000-292917. A triarylsulfonium salt is an excellent light-acid generating agent but it is large in absorption, and so when a large amount is added for improving sensitivity, the light transmittance of the resist film lowers, and results in profile called taper. On the other hand, a phenacylsulfonium salt is relatively small in absorption but light-acid generating performance is low, therefore, when a phenacylsulfonium salt is used, the sensitivity of the resist lowers.
SUMMARY OF THE INVENTION
Accordingly, an object of the present invention is to provide a positive radiation-sensitive composition which shows high sensitivity and high resolution in pattern formation by irradiation with an actinic ray.
As a result of eager investigation, the present inventors found that the above object could be achieved by the use of a compound having a specific structure as the compound capable of generating an acid upon irradiation with an actinic ray, which led to the present invention.
(1) A positive radiation-sensitive composition comprising:
(A) at least one compound capable of generating an acid upon irradiation with an actinic ray represented by the following formula (I); and
(B) a resin having a group capable of decomposing by the action of an acid to increase the solubility in an alkali developing solution:
wherein R
1
, R
2
, R
3
, R
4
and R
5
each represents a hydrogen atom, an alkyl group, an alkoxyl group, a nitro group, a halogen atom, an alkyloxycarbonyl group, or an aryl group, and at least two of R
1
, R
2
, R
3
, R
4
and R
5
may be bonded to form a cyclic structure; R
6
and R
7
each represents a hydrogen atom, an alkyl group, a cyano group or an aryl group; Y
1
and Y
2
each represents an alkyl group, an aryl group, an aralkyl group, or an aromatic group containing a heteroatom, and Y
1
and Y
2
may be bonded to form a ring; Y
3
represents a single bond or a divalent linking group; and X
−
represents a non-nucleophilic anion; provided that at least one of R
1
, R
2
, R
3
, R
4
and R
5
, and at least one of Y
1
and Y
2
are bonded to form a ring, or at least one of R
1
, R
2
, R
3
, R
4
and R
5
, and at least one of R
6
and R
7
are bonded to form a ring; and there may be present two or more structures represented by formula (I) by being bonded at any position of R
1
to R
7
or at any position of Y
1
and Y
2
via a linking group.
(2) The positive radiation-sensitive composition as described in the above item (1), wherein the compound (A) is represented by the following formula (IA) or (IB):
wherein in formula (IA), R
1
to R
4
, R
7
, Y
1
, Y
2
and X
−
have the same meaning as those in formula (I), and Y represents a single bond or a divalent linking group; and in formula (IB), R
1
to R
4
, R
6
, R
7
, Y
1
and X
−
have the same meaning as those in formula (I), and Y represents a single bond or a divalent linking group.
(3) The positive radiation-sensitive composition as described in the above item (1) or (2), which further comprises (C) a low molecular weight dissolution-inhibiting compound: having a molecular weight of 3,000 or less; containing an acid-decomposable group; and capable of increasing the solubility in an alkali developing solution by the action of an acid.
(4) A positive radiation-sensitive composition comprising:
(A) at least one compound capable of generating an acid upon irradiation with an actinic ray represented by the following formula (I);
(C) a low molecular weight dissolution-inhibiting compound: having a molecular weight of 3,000 or less; containing an acid-decomposable group; and capable of increasing the solubility in an alkali
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