Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2000-12-01
2002-05-07
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S047000, C522S162000, C522S048000, C430S191000, C430S056000, C430S189000, C430S170000
Reexamination Certificate
active
06384103
ABSTRACT:
TECHNICAL FIELD
This invention relates to a novel radiation-sensitive resin composition and, more particularly, to a radiation-sensitive resin composition containing an alkali-soluble novolak resin, suited for manufacture of semiconductors, preparation 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 semiconductors 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 which contain 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 containing novolak resin and the quinonediazide compound and having different formulations 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 the novolak resin and the quinonediazide compound have so far been investigated from the viewpoint of both the novolak resin and the photosensitizer. From the viewpoint of the novolak resin, improvement of physical properties of conventionally known resins have been conducted, as well as development of novel resins, to obtain radiation-sensitive resins with excellent properties. For example, Japanese Unexamined Patent Publication Nos. S60-140235 and H1-105243 disclose techniques of imparting a particular molecular weight distribution to a novolak resin to thereby provide a radiation-sensitive resin composition having excellent properties.
However, many of conventional radiation-sensitive resin compositions still have problems such as a poor balance among various properties including sensitivity, resolution, depth of focus, pattern profile, coating-remaining ratio, heat resistance, etc., and have been required to be more improved. Particularly, in the process of manufacturing flat panel display, it has been an important subject to reduce the content of monomer and dimer in the alkali-soluble resin components as well as improvement of the above-described properties. That is, there has been a problem that, when prebaking is conducted after applying the radiation-sensitive resin composition on a substrate, monomer and dimer components in the alkali-soluble resin will vaporize during the prebaking together with a solvent and stain the inside of the prebaking furnace, resulting in contamination with impurities in the steps of manufacturing devices. For example, Japanese Unexamined Patent Publication Nos. 57-86831, S60-230136, and H3-230164 disclose the technique of fractionating a low-molecular resin component by solvent fractionation. However, this solvent fractionation technique has a problem that, since a middle-molecular component in the resin is also fractionated away as well as the monomer and dimer components, there results a reduction in sensitivity. As a technique for preventing the reduction, there may be considered a technique of subjecting an alkali-soluble resin having a previously decreased weight average molecular weight to the solvent fractionation. Such alkali-soluble resin, however, has a poor coating-remaining ratio and a poor heat resistance, though a sufficient sensitivity can be obtained, thus it having been extremely difficult to obtain a radiation-sensitive resin composition having well-balanced properties described above. In addition, most of the low-molecular component of the alkali-soluble resin fractionated by the solvent fractionation is not used as the material for radiation-sensitive resin composition and is discarded as a waste. Such manufacturing process not only provides the radiation-sensitive resin composition with an increased manufacturing cost but imposes a serious load on surrounding environment.
On the other hand, as a method for fractionating compounds, thin film distillation method has already been known. This thin film distillation method is a method of fractionating by forming a thin film of a material to be distilled on a heat transferring dish or the like by employing mechanical centrifugation force, inertia force, a dispersing apparatus, etc. to conduct distillation, thus accelerating evaporation of monomers. Heretofore, the thin film distillation method has been reported to be used in a process for manufacturing polyhydroxy compounds which are starting materials for epoxy resins (Japanese Unexamined Patent Application No. H10-87538), a process for purifying xylenol (Czechoslovakian Inventor's Certificate No. 239793) and a process for removing materials having a low melting point in waxes to be used for toner for developing statically charged image (Japanese Unexamined Patent Publication No. 7-36218). However, it has not been known to specifically apply this technique of thin film distillation to the binder resin for radiation-sensitive resin composition. Although the aforesaid Japanese Unexamined Patent Application No. H3-230164 describes that a low molecular component of novolak resin may be removed by the thin film distillation method, it merely illustrates that as an equivalent technique to the method of solvent fractionation, and nothing is disclosed as to treating conditions and the like. That is, it merely shows possibility and does not show that the thin film distillation method is more excellent than the method of solvent fractionation.
An object of the present invention is to provide a radiation-sensitive resin composition having no defects described above, having excellent sensitivity, resolution, pattern profile, heat resistance, etc. required for photoresist, and having these properties with good balance.
DISCLOSURE OF THE INVENTION
As a result of intensive investigations, the inventors have found that the above-described object can be attained by using, in the radiation-sensitive resin composition containing an alkali-soluble resin and a photosensitizer having a quinonediazide group, a novolak resin treated by the thin film distillation method to partially and selectively remove monomer and dimer so that the amounts of monomer and diner in the resin fall within a given range as the alkali-soluble resin, thus having achieved the present invention based on the finding.
That is, the present invention relates to a radiation-sensitive resin composition containing an alkali-soluble resin and a photosensitizer having a quinonediazide group, wherein the alkali-soluble resin is a novolak resin treated by a thin film distillation method.
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Arano Akio
Yamamoto Kenji
Banerjee Krishna
Clariant Finance (BVI) Limited
McClendon Sanza L
Seidleck James J.
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