Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
2000-08-10
2002-11-05
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...
C430S191000, C430S192000, C430S193000, C430S326000
Reexamination Certificate
active
06475693
ABSTRACT:
TECHNICAL FIELD
This invention relates to a novel positive-working radiation-sensitive resin composition and, more particularly, to a positive-working radiation-sensitive resin composition containing a radiation-sensitive novolak resin, suited for manufacture of semiconductors, production of a display surface of liquid crystal display panel, manufacture of a circuit substrate for thermal head etc., and like use.
BACKGROUND ART
In the wide field of manufacturing semiconductor integrated circuits such as LSI, preparing a display surface of liquid crystal display panel, manufacturing a circuit substrate for thermal head etc., and like use, photolithography has so far been employed for forming microelements or conducting fine processing. In the photolithography, a positive- or negative-working radiation-sensitive resin composition is used for forming a resist pattern. Of these radiation-sensitive resin compositions, those compositions containing an alkali-soluble resin and a photosensitizer of quinonediazide compound are most popularly used as the positive-working radiation-sensitive resin compositions. As such compositions, there are described compositions having different formulations as, for example, ‘novolak resin/quinonediazide compound’ in many documents such as Japanese Examined Patent Publication No. S54-23570 (U.S. Pat. No. 3,666,473), Japanese Examined Patent Publication No.56-30850 (U.S. Pat. No. 4,115,128), Japanese Unexamined Patent Publication Nos. S55-73045, S61-205933 and S62-51459, etc.
These compositions containing a novolak resin and a quinonediazide compound have so far been studied with respect to both novolak resins and photosensitizers. In respect of novolak resins, there have been developed novel resins. In addition, radiation-sensitive resin compositions having excellent properties have also been obtained by improving properties of conventionally known resins. For example, there are disclosed techniques providing a radiation-sensitive resin composition having excellent properties by using a novolak resin with a particular molecular weight distribution in Japanese Unexamined Patent Publication Nos. S60-140235 and H1-105243 and by using a novolak resin from which low-molecular-weight components of the resin has been removed in Japanese Unexamined Patent Publication Nos. S60-97347, S60-189739 and Japanese Patent Publication No.2590342.
A number of positive-working radiation-sensitive resin compositions containing quinonediazide compounds have been put into practice as a result of various technical developments having so far been made, and the aspect ratio of thickness of radiation-sensitive resin coating to resolved line width has been improved to about 5:1.
On the other hand, degree of integration of integrated circuits of semiconductor elements have been increased year by year and, in the manufacture of semiconductor elements or the like, processing of patterns with a line width of less than sub-micron order has become required. In the uses requiring such super-fine processing, good pattern reproducibility is required as well as high resolution and, from the standpoint of production cost, it is also required to improve throughput (yield per unit time) upon production. Therefore, increasing sensitivity of radiation-sensitive resin composition and reducing dependence of dimensional accuracy upon process are also important factors. However, conventionally known radiation-sensitive resin compositions can not satisfy these requirements at the same time, thus being insufficient.
An object of the present invention is to provide a radiation-sensitive resin composition capable of satisfying all of these conventionally desired properties at the same time, i.e., a radiation-sensitive resin composition which has a high sensitivity and a high resolution, which can form a good pattern with a high aspect ratio, and which provides an excellent throughput upon production and has a small dependence of dimensional accuracy upon process.
DISCLOSURE OF THE INVENTION
As a result of intensive investigations, the inventors have found that the above-described object can be attained by using a positive-working radiation-sensitive resin composition containing a specific radiation-sensitive novolak resin and a specific dissolution inhibitor, thus having achieved the present invention based on the finding.
That is, the present invention is a radiation-sensitive resin composition which contains (i) a radiation-sensitive novolak resin comprising a reaction product between an alkali-soluble novolak resin from which low-molecular-weight components have been removed by a fractional treatment and an o-naphthoquinonediazide compound, or a product obtained by removing low-molecular-weight components by fractional treatment from a reaction product between an alkali-soluble novolak resin and an o-naphthoquinonediazide compound and (ii) a dissolution inhibitor comprising a low-molecular compound represented by the following general formula (I) and having phenolic hydroxyl group or groups:
wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
each represents independently H, a C
1
to C
4
alkyl group, a C
1
to C
4
alkoxyl group, a cyclohexyl group or a group represented by the formula:
wherein R
8
represents H, a C
1
to C
4
alkyl group, a C
1
to C
4
alkoxyl group or a cyclohexyl group; each of m and n is 0, 1 or 2; each of a, b, c, d, e, f, g and h is 0 or an integer of 1 to 5 satisfying a+b≦5, c+d≦5, e+f≦5, and g+h≦5; and i is 0, 1 or 2.
The present invention will now be described more specifically below.
An alkali-soluble novolak resin from which low-molecular-weight components have been removed by fractional treatment to be used as a starting material for preparing the radiation-sensitive novolak resin of the present invention may be manufactured by removing low-molecular-weight components by fractional treatment from the novolak-type phenol resin obtained by polycondensation between at least one of phenols and an aldehyde such as formalin.
As the phenols to be used for manufacturing this alkali-soluble novolak resin, there may be illustrated cresols such as o-cresol, p-cresol and m-cresol; xylenols such as 3,5-xylenol, 2,5-xylenol, 2,3-xylenol and 3,4-xylenol; trimethylphenols such as 2,3,4-trimethylphenol, 2,3,5-trimethylphenol, 2,4,5-trimethylphenol and 3,4,5-trimethylphenol; t-butylphenols such as 2-t-butylphenol, 3-t-butylphenol and 4-t-butylphenol; methoxyphenols such as 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 2,3-dimethoxyphenol, 2,5-dimethoxyphenol and 3,5-dimethoxyphenol; ethylphenols such as 2-ethylphenol, 3-ethylphenol, 4-ethylphenol, 2,3-diethylphenol, 3,5-diethylphenol, 2,3,5-triethylphenol and 3,4,5-triethylphenol; chlorophenols such as o-chlorophenol, m-chlorophenol, p-chlorophenol and 2,3-dichlorophenol; resorcinols such as resorcinol, 2-methylresorcinol, 4-methylresorcinol and 5-methylresorcinol; catechols such as 5-methylcatechol; pyrogallols such as 5-methylpyrogallol; bisphenols such as bisphenol A, B, C, D, E or F; methylol-cresols such as 2,6-dimethylol-p-cresol; naphthols such as &agr;-naphthol, &bgr;-naphthol, etc.; and the like. These are used independently or as a mixture of two or more thereof.
As the aldehydes, there may be used salicylaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, chloroacetaldehyde, etc. independently or as a mixture of two or more thereof as well as formalin.
The polycondensation between at least one of phenols and an aldehyde such as formalin may be conducted by any conventionally known or well-known processes such as using, for example, oxalic acid as a catalyst. As a method of fractional treatment for removing low-molecular-weight components from the novolak resin obtained, any conventionally known processes may be adapted. The method of fractional treatment include e.g. liquid-liquid fractionation of novolak resin using two different solvents having different dissolution abilities to the component of the resin, a method of removing low-molecular-weight components
Arano Akio
Nishikawa Masato
Susukida Kenji
Banerjee Krishna
Chu John S.
Clariant Finance (BVI) Limited
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