Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
2001-01-26
2002-11-26
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Diazo reproduction, process, composition, or product
Composition or product which contains radiation sensitive...
C430S270100, C430S914000, C430S921000, C430S925000
Reexamination Certificate
active
06485883
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a positive photosensitive composition for use in the production of a lithographic printing plate, a semiconductor such as IC, a circuit board for liquid crystal and thermal head and in other photofabrication processes.
BACKGROUND OF THE INVENTION
As the photosensitive composition for use in the production of a lithographic printing plate, a semiconductor such as IC, a circuit board for liquid crystal and thermal head and in other photofabrication processes, various compositions are known and photoresist photosensitive compositions are ordinarily employed. The photoresist compositions are widely divided into positive photoresist compositions and negative photoresist compositions.
One of the positive photoresist photosensitive compositions is a chemical amplification-type resist composition as described in U.S. Pat. No. 4,491,628 and European Patent No. 249,139. The chemical amplification-type positive resist composition is a pattern formation material which generates an acid in an exposed area upon irradiation with a radiation such as a far ultraviolet ray and due to a reaction using the acid as a catalyst, solubility in a developing solution differentiates in the area irradiated with the active radiation from the non-irradiated area to form a pattern on a substrate.
Examples of such a resist composition include combinations of a compound capable of generating an acid by photolysis with an acetal or O,N-acetal compound as described in JP-A-48-89003 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”), with an ortho ester or amide acetal compound as described in JP-A-51-120714, with a polymer having an acetal or ketal group on the main chain as described in JP-A-53-133429, with an enol ether compound as described in JP-A-55-12995, with an N-acyliminocarbonic acid compound as described in JP-A-55-126236, with a polymer having an ortho ester group on the main chain as described in JP-A-56-17345, with a tertiary alkyl ester compound as described in JP-A-60-3625, with a silyl ester compound as described in JP-A-60-10247 or with a silyl ether compound as described in JP-A-60-37549 and JP-A-60-121446. These combinations exhibit high photosensitivity since they have in principle a quantum yield exceeding 1.
A system which is stable at a room temperature but decomposes by heating in the presence of an acid to become alkali-soluble is also known and examples thereof include combinations of a compound capable of generating an acid on exposure with an ester or carbonic acid ester compound having a tertiary or secondary carbon (e.g., tert-butyl or 2-cyclohexenyl) as described, for example, 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, page 1012 (1983),
ACS. Sym.,
Vol. 242, page 11 (1984),
Semiconductor World,
November, 1987, page 91,
Macromolecules,
Vol. 21, page 1475 (1988), and
SPIE,
Vol. 920, page 42 (1988). Since such a system has high photosensitivity and a little absorption in a far ultraviolet region, it is suitable for ultra fine fabrication using a light source having a shorter wavelength.
In general, the chemical amplification-type positive photoresist composition is roughly divided into two types. Specifically, there are a chemical amplification positive photoresist of three-component type comprising an alkali-soluble resin, a compound capable of generating an acid upon irradiation with a radiation (hereinafter also referred to as a “photo-acid generator” sometimes) and a compound which has an acid-decomposable group and prevents the alkali-soluble resin from dissolution and a chemical amplification positive photoresist of two-component type comprising a resin having a group capable of being decomposed by a reaction with an acid to become alkali-soluble and a photo-acid generator.
The two-component or tree-component chemical amplification positive photoresist composition is subjected to exposure to generate an acid from the photo-acid generator, heat treatment and development thereby obtaining a resist pattern.
These chemical amplification-type positive photoresist compositions are suitable for ultra fine fabrication using a light source having a shorter wavelength as described above. However, further improvements in resolution and process allowance such as exposure margin and depth of focus have been desired.
A basic sulfonium compound is described as a photo-acid generator in JP-A-6-242606. A basic iodonium compound is described as a photo-acid generator in JP-A-7-333844. Also, the use of a compound generating a carboxylic acid together with a compound generating an acid other than a carboxylic acid is described as a photo-acid generator in JP-A-11-125907.
However, such a technique is still insufficient for meeting the ultra fine fabrication today and further improvements in resolution and process allowance such as exposure margin and depth of focus have been desired.
SUMMARY OF THE INVENTION
Therefore, an object of the present invention is to provide a positive photoresist composition which is improved in resolution and process allowance such as exposure margin and depth of focus in a lithographic technology using a light source having a short wavelength capable of conducting the ultra fine fabrication and a chemical amplification-type positive photoresist.
Other objects of the present invention will become apparent from the following description.
It has been found that the objects of the present invention are accomplished by the following positive photoresist compositions:
(1) a positive photoresist composition which comprises (A) a resin having a group which decomposes by the action of an acid to increase solubility in an alkaline developing solution, and (B) a compound which generates an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with an actinic ray or radiation,
(2) the positive photoresist composition as described in item (1) above, wherein the composition further comprises (D) a compound having a molecular weight of not more than 3,000 which decomposes by the action of an acid to increase solubility in an alkaline developing solution,
(3) a positive photoresist composition which comprises (B) a compound which generates an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with an actinic ray or radiation, (D) a compound having a molecular weight of not more than 3,000 which decomposes by the action of an acid to increase solubility in an alkaline developing solution, and (E) an alkali-soluble resin,
(4) the positive photoresist composition as described in any one of items (1) to (3) above, wherein the composition further comprises (C) a compound which generates a sulfonic acid upon irradiation with an actinic ray or radiation,
(5) the positive photoresist composition as described in any one of items (1) to (4) above, wherein the composition further comprises (F) a nitrogen-containing basic compound and (G) a fluorine-base or silicon-base surface active agent,
(6) the positive photoresist composition as described in any one of items (1) to (5) above, wherein (B) the compound which generates an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom upon irradiation with an actinic ray or radiation is a compound represented by the following formula (I), (II) or (III):
wherein R
1
to R
37
, which may be the same or different, each represents a hydrogen atom, a straight chain, branched chain or cyclic alkyl group, a straight chain, branched chain or cyclic alkoxy group, a hydroxy group, a halogen atom or an —S—R
38
group (wherein R
38
represents a straight chain, branched chain or cyclic alkyl group or an aryl group); and X
−
represents an anion of an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom,
(7) the positive photoresist composition as described in item (6) above, wherein X
−
represents an anion of a perfluoro
Aoai Toshiaki
Kanna Shinichi
Kodama Kunihiko
Chu John S.
Fuji Photo Film Co. , Ltd.
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