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HK80091A - Photosensitive positive composition and photoresist material prepared therewith - Google Patents

Photosensitive positive composition and photoresist material prepared therewith Download PDF

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Publication number
HK80091A
HK80091A HK800/91A HK80091A HK80091A HK 80091 A HK80091 A HK 80091A HK 800/91 A HK800/91 A HK 800/91A HK 80091 A HK80091 A HK 80091A HK 80091 A HK80091 A HK 80091A
Authority
HK
Hong Kong
Prior art keywords
propylene glycol
alkyl ether
mixture
ether acetate
radiation
Prior art date
Application number
HK800/91A
Other languages
German (de)
French (fr)
Inventor
Dana Durham
Original Assignee
Az电子材料日本株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Az电子材料日本株式会社 filed Critical Az电子材料日本株式会社
Publication of HK80091A publication Critical patent/HK80091A/en

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/022Quinonediazides
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/0048Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/022Quinonediazides
    • G03F7/0226Quinonediazides characterised by the non-macromolecular additives

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Manufacturing Of Printed Circuit Boards (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

1. Claims for the contracting states : DE, FR, GB, IT, NL, AT Radiation-sensitive positive-working mixture which is composed essentially of at least one waterin-soluble novolak resin or polyvinylphenol resin which is soluble in aqueous alkaline solutions, as binder, at least one o-quinone diazide as photosensitive compound and a solvent containing propylene glycol alkyl ether acetate, characterized in that the solvent contains a mixture of propylene glycol (C1 -C4 )alkyl ether acetate and propylene glycol (C1 -C4 )alkyl ether in a mixing ratio of between 10:1 and 1:10 or is composed thereof. 1. Claims for the contracting states : CH, LI Radiation-sensitive positive-working mixture which is composed essentially of at least one waterin-soluble novolak resin or polyvinylphenol resin which is soluble in aqueous alkaline solutions, as binder, at least one o-quinone diazide as photosensitive compound and a solvent containing propylene glycol alkyl ether acetate, characterized in that the solvent contains a mixture of propylene glycol (C1 -C4 )alkyl ether acetate and propylene glycol (C1 -C4 )alkyl ether or is composed thereof.

Description

The present invention relates to a radiation sensitive, positively acting mixture consisting essentially of at least one water-insoluble, aqueous-alkali-soluble novolac or polyvinyl phenol resin as a binder, at least one o-quinondiazide as a photosensitive compound and a solvent containing a propylene glycol alkyl etheracetate.
The production of positively acting photoresistants is known and is described, for example, in US-A 3.666.473, US-A 4.115.128 and US-A 4.173.470. These are alkaline soluble phenol formaldehyde novacoal resins in combination with photosensitive substances, usually substituted naphthoquinondiazide compounds.
The novola resin component of these photoresist kits is soluble in aqueous alkaline solutions, but the light-sensitive naphthoquinone compound acts as an inhibitor on the resin. However, when certain areas of the coated medium are exposed to actinic radiation, the light-sensitive medium undergoes an irradiation-induced structural transformation and the exposed areas of the coating become more soluble than the unexposed ones.
In most cases the developed layer carrier is treated with an etching solution or gas plasma. The photoresist layer protects the coated areas of the carrier from the etcher so that it can only etch the exposed areas. These are the areas exposed to actinic radiation in a positively working resist.
The photoresist relief on the layered support produced by the above process is suitable for various applications, for example as a mask or image, for example in the manufacture of semiconductor components in microelectronics.
The following are important characteristics for the production use of a photoresist: light sensitivity, development contrast, image resolution and adhesion of the resist to the layer carrier.
An increased light sensitivity is important for a photoresist, particularly when used in applications where multiple exposures are required, e.g. when producing multiple images by a repeating process or in cases where light with attenuated intensity is used, e.g. in projection exposure technology, where the light passes through a series of lenses and monochromatic filters. An increased light sensitivity is therefore particularly important for a resistive used in processes where multiple exposures are required to produce a mask or series of shots on a medium. Optimal conditions are achieved by a constant development temperature and thickness - at certain ranges - and by a developer who selects a system that is fully resistive and achieves a maximum initial resistance thickness of 10 per cent at the same time.
The developmental contrast is the difference between the percentage of layer loss in exposed areas after development and the percentage of layer loss in unexposed areas. Normally, a resistance coated carrier develops after exposure until the layer has essentially completely displaced itself in the exposed areas.
Resist image resolution is the ability of a resist system to reproduce the smallest pairs of lines and the corresponding spaces of a mask used for exposure, at the same distance from each other, with a high degree of image flank partition in the developed exposed spaces.
For many technical applications, particularly for the manufacture of semiconductor components in microelectronics, a photoresist must have a high resolution if it is to reflect very small line and spacing spaces (on the order of 1 μm).
The ability of a resistor to reproduce very small dimensions on the order of 1 J.1m and below is of paramount importance in the manufacture of VLSI circuits on silicon chips and similar components. The circuit density on such a chip can only be increased by increasing the resolution of the resistor - provided it is worked with photolithographic methods. Although negative working photoresists, in which the exposed areas of the resistor layer are insoluble in the developer and the unexposed areas are replaced by developer, in which semiconductors are used on a large scale in industry for this purpose, the positively working photoresists are by their nature a higher image resolution and are used as a replacement for the negative working resistors.
The difficulty in using conventional positive-working photoresist for the manufacture of semiconductor components in microelectronics is that the positive-working resists generally have a lower light sensitivity than the negative-working resists.
Various attempts have been made in the past to improve the photosensitivity of photoresist mixtures, for example in US-A 3.666.473 a mixture of two phenol formaldehyde novalakes is used together with a common photosensitive compound, these novalakes being defined by their solubility rate in alkaline solutions of a certain pH and by their turbidity point.
In US-A 4.115.128, a third component, a cyclic anhydride of an organic acid, is added to the phenolic resin and the naphthoquinondiazide used as a photosensitive compound to increase photosensitivity.
It is also known to be used in photoresist mixtures containing propylene glycol alkyl ethers (US-A- 4,550,069) and in mono- ((C1-C4) alkyl glycol ethers of 1,2-propandiol (DE-A-3 421 160) in the corresponding mixtures. These components act as solvents for the binder and the photosensitive compound and thus facilitate the application of the resist to the layer carrier. The known compounds are of low toxicity compared to those commonly used. However, the compounds known to be used as solvents have been shown to cause special odor irritations.
Document EP-A 0 195 315 is part of the state of the art referred to in Article 54 (3) EPC.
The present invention was designed to produce a radiation sensitive, positively acting mixture which would be less odor-inducing to operators than conventional mixtures and would have unchanged or even improved properties in terms of light sensitivity, resistance erosion rate, plasma rate and development contrast.
The solution to this problem is based on a radiation-sensitive positive-acting mixture of the type mentioned at the outset, which is characterized by the presence or absence of a mixture of propylene glycol-C4a-kyetheracetate and propylene glycol-C4 alkyl ether.
Surprisingly, it was found that such an improved resist can be produced by mixing the novolac or polyvinyl phenol resin as a binder and the o-quinondiazide as a photosensitive compound with a solvent mixture of a propylene glycol etheracetate and a propylene glycol glycol ethers component.
Sensitive mixtures containing only one of the two components of the invention, propylene glycol-alkyl ethers, have the following disadvantages: the use of propylene glycol-methyl ethers (PGMEA) causes extremely unpleasant odour disturbances for about half of the persons in contact with this substance, with the majority of women complaining of discomfort. Therefore, the use of propylene glycol-methyl ethers (PGME) also causes a strong odour disturbance for about half of the persons handling this substance, but in this case complaining of discomfort.
The preparation of the mixture and material shall be carried out by first forming a mixture of at least one resin from the group of novolaks and polyvinyl phenols and at least one photosensitive o-quinondioside compound in a solvent mixture containing propylene glycol-alkyl ether and propylene glycol-alkyl ether acetate, applying the mixture to a suitable layer carrier and drying to obtain a substantially non-stick layer with a residual solvent content of 1 to 30% by weight of the dry layer, and exposing and developing the resulting layer by means of appropriate actin radiation to remove the areas with an alkaline detergent.
The photoresist mixes of the invention not only have an excellent light sensitivity compared with known positive-working photoresist, but also have a high image resolution, good development contrast and good adhesion properties. These characteristics distinguish them clearly from some known resists, which have a moderately increased light sensitivity, but this improvement is achieved at the expense of resolution and contrast.
Err1:Expecting ',' delimiter: line 1 column 225 (char 224)
In the preferred version, the content of solid components of the photoresist mixture, i.e. binders and diazid, is preferably about 15 to 99% by weight of binders and about 1 to 85% by weight of o-chinondiazide. In particular, the binding agent is about 50 to 90% by weight and preferably about 65 to 85% by weight, based on the weight of the solid components of the photoresist contained in the mixture. The content of diazid is in particular about 10 to 50% by weight and preferably about 15 to 35% by weight, based on the weight of the flattest components of the photoresist.The ratio of PGMEA to PGME may vary widely depending on the technical requirements of the application. For example, the ratio may be between 1:20 and 20:1. The ratio of PGMEA to PGME is preferably between 10:1 and 1:10, especially between 6:4 and 4:6.The use of the product shall be limited to the following:
Dyes which can be used as additives in the photoresist mixtures of the invention are, for example, methyl violet 2B (C.I. 42 535), crystal violet (C.I. 42 555), malachite green (C.I. 42 000), Victoria blue B (C.I. 44 045) and neutral red (C.I. 50 040), which are added in amounts of 1 to 10 per cent by weight, based on the total weight of the binder and the light-sensitive compound.
The use of intermediates may be limited to 5% by weight, based on the total weight of the binder and the light sensitive compound.
Suitable plasticizers are, for example, phosphoric acid (ji-chlorethyl) esters, stearic acid, dicampher, polypropylene, acetal resin, phenoxy resin and alkyd resin, which may be added in proportions of 1 to 10 per cent by weight, based on the total weight of the binder and the light sensitive compound.
Suitable binders are, for example, β- ((3,4-epoxycyclohexyl) -ethyltrimethoxylan, p-methyldisylan methylmethacrylate, vinyl trichlorsilan and y-aminopropyl triethoxylan up to 4% by weight, based on the total weight of the binder and the photosensitive compound.
For example, picric acid, nicotinic acid or nitrocymic acid can be added as development accelerators up to 20% by weight, relative to the total weight of the binder and the photosensitive compound. These accelerators increase the solubility of the photoresist layer in both exposed and unexposed areas and are therefore used in applications where development speed is the main concern, although this may sacrifice some degree of contrast; while the exposed areas are resolved more rapidly by the developer by adding accelerators, the development areas are also uncovered at the same time as a greater loss of photoresist from the unexposed areas.
The appropriate additional solvents are, for example, xylol, butylaceate and ethylene glycol methyl ether acetate, which may be present in up to 95% by weight of the total solvent, but preferably no additional solvents are used in the mixture.
For example, non-ionic surfactants may be used such as non-phenoxy-poly ((ethylenoxy) ethanol, octyl-noxy ((ethylenoxy) ethanol, and dinonyl-phenoxy-poly ((ethylenoxy) ethanol up to 10% by weight, based on the total weight of the binder and the photosensitive compound.
The finished photoresist solution can be applied to a support by one of the methods common to photoresist technology, such as immersion, spraying and splashing. For splashing, for example, the percentage of solids in the resist solution can be adjusted to give a coating in the desired thickness depending on the splashing speed used in the individual case and the time taken for the splashing process.
Accordingly, the present invention also concerns a radiation-sensitive, positively acting photoresist material consisting of a layered carrier and a photoresist coating on it, consisting essentially of a mixture of at least one water-insoluble, aqueous-alkaline soluble novinylphenol resin or polyvinylphenol resin as a binder, at least one o-quinondiazide as a photosensitive compound and a solvent containing a propylene glycol-alkyletheracetate, characterized by the fact that the coating was obtained by pre-drying a mixture consisting of or containing a mixture of propylene glycol-C1-C4-alkyletheracetate and propylene glycol-C1-C4-alkyletheracetate.
The photoresist solutions are particularly suitable for application on silicon wafers that carry a layer of thermally cultured silicon dioxide, such as those used in the manufacture of microprocessors and other semiconductor components used in microelectronics. Similarly, an aluminium wafer with an aluminium oxide layer can be used. The layer carrier can also be made of various polymeric resins, especially transparent polymers such as polyester.
After application of the photoresist solution to the layer carrier, the carrier is subjected to a pre-drying process at about 20 to 110 °C. This heat treatment is carried out to reduce and control the residual solvent concentration in the photoresist by evaporation without causing appreciable thermal decomposition of the photosensitive compound. The aim is generally to reduce the solvent content to a minimum and this initial heat treatment is therefore continued until the solvents are essentially evaporated and a thin layer of photoresist resin, approximately 1 J.1 m thick, remains on the layer carrier.Err1:Expecting ',' delimiter: line 1 column 446 (char 445)and their residual solvent content is adjusted during this treatment step to 1 to 30% by weight, preferably 5 to 20% by weight, and in particular to 8% to 12% by weight, in each case in relation to the dry weight of the layer.
The coated medium is then exposed to actin radiation, particularly UV radiation, in a known manner, by means of appropriate masks, negatives, stencils, etc.
The solution is preferably stirred strongly, which can be done, for example, by blowing through nitrogen. For example, aqueous alkaline, ammonium or tetramethylammonium hydroxide solutions are suitable as a developer, but any other known suitable developer can also be used. The carriers remain in the developer bath until the photoresist layer at the exposed sites is completely or at least almost completely displaced.
After removal of the coated wafers from the developer solution, heat treatment or incineration can be performed to increase the adhesion and chemical resistance of the layer to solvents and other substances. The heat treatment after development may consist of oven-hardening of layer and support below the softening point of the layer. It is performed, for example, at temperatures of 95 to 160 °C, preferably 95 to 150 °C, especially 112 to 120 °C. This heat treatment can also be performed with a heat plate, which then takes about 10 seconds and results in a longer duration of the networking of the resin layer.
For industrial applications, in particular in the manufacture of semiconductor components on silicon media with a silicon dioxide layer, the developed media can be treated with a buffered acetic solution based on fluorinated acid or with gas plasma.
The following examples explain in detail the methods of manufacture and use of the compositions of the invention, but they are not intended to limit the scope of the invention in any way and are not to be construed as indicating conditions, parameters or other values which are to be used exclusively for the practical implementation of the invention.
Example
Resistance sets were manufactured from the following components: The following are the active substances which are to be used in the preparation of the additive:
The absorption capacity of the photoresist was 1.33 ± 0.03 I/ gcm in all cases.
By adjusting the rate of slicing, the mixture was applied in such a way that after 30 minutes of air-drying in the chamber at 90 °C, a layer thickness of 2.0 μm was obtained. The layer thickness was determined by a Rudolph layer thickness meter. Light sensitivity and contrast values were determined by laser interferometry and the resulting values were subjected to linear regression, with the regression curve being run through 8 measurement points.
Err1:Expecting ',' delimiter: line 1 column 88 (char 87)
The examples show that PGME/PGMEA mixed photoresist can be produced with a significantly reduced odor disturbance, while being similar in terms of light sensitivity and contrast values to photoresist which only uses a single solvent, PGMEA.

Claims (5)

1. Radiation-sensitive positive-working mixture which is composed essentially of at least one waterin- soluble novolak resin or polyvinylphenol resin which is soluble in aqueous alkaline solutions, as binder, at least one o-quinone diazide as photosensitive compound and a solvent containing propylene glycol alkyl ether acetate, characterized in that the solvent contains a mixture of propylene glycol (G¡-C4)alkyl ether acetate and propylene glycol (G¡-C4)alkyl ether or is composed thereof.
2. Radiation-sensitive mixture according to Claim 1, characterized in that the solvent contains a mixture of propylene glycol methyl ether acetate and propylene glycol methyl ether or is composed thereof.
3. Radiation-sensitive mixture according to Claim 1, characterized in that the solvent contains a mixture of propylene glycol alkyl ether acetate and propylene glycol alkyl ether in an amount of about 5 to 100% by weight, based on the solvent.
4. Radiation-sensitive mixture according to Claim 1, characterized in that propylene glycol alkyl ether acetate and propylene glycol alkyl ether are present in a mixing ratio of about 1:1 parts by weight.
5. Radiation-sensitive positive-working photoresist material composed of a film base and a photoresist coating situated thereon which is composed essentially of a mixture of at least one water-insoluble novolak resin or polyvinylphenol resin, which is soluble in aqueous alkaline solutions, as binder, at least one o-quinone diazide as photosensitive compound and a solvent containing propylene glycol alkyl ether acetate, characterized in that the coating has been prepared by predrying a mixture, the solvent of which contains a mixture of propylene glycol (Cl-C4)alkyl ether acetate and propylene glycol (Ct-C4)alkyl ether or is composed thereof.
HK800/91A 1985-10-28 1991-10-10 Photosensitive positive composition and photoresist material prepared therewith HK80091A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US79188085A 1985-10-28 1985-10-28

Publications (1)

Publication Number Publication Date
HK80091A true HK80091A (en) 1991-10-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
HK800/91A HK80091A (en) 1985-10-28 1991-10-10 Photosensitive positive composition and photoresist material prepared therewith

Country Status (6)

Country Link
EP (1) EP0220645B1 (en)
JP (1) JPS62105137A (en)
KR (1) KR950001004B1 (en)
AT (1) ATE56545T1 (en)
DE (1) DE3674141D1 (en)
HK (1) HK80091A (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63303343A (en) * 1987-06-03 1988-12-09 Konica Corp Photosensitive composition and photosensitive lithographic printing plate
JP2719912B2 (en) * 1987-05-07 1998-02-25 コニカ株式会社 Photosensitive lithographic printing plate
JPS63276047A (en) * 1987-05-07 1988-11-14 Konica Corp Photosensitive composition and photosensitive planographic printing plate
JPS6477051A (en) * 1987-06-03 1989-03-23 Konishiroku Photo Ind Photosensitive composition and photosensitive planographic printing plate
JP2806474B2 (en) * 1987-07-28 1998-09-30 三菱化学株式会社 Photosensitive composition
JPH01116537A (en) * 1987-10-29 1989-05-09 Konica Corp photosensitive composition
JPH01250945A (en) * 1988-03-30 1989-10-05 Sumitomo Chem Co Ltd Positive type resist composition
JPH0229750A (en) * 1988-07-20 1990-01-31 Mitsubishi Kasei Corp Photosensitive composition and photosensitive planographic printing plate
JP2947519B2 (en) * 1988-10-03 1999-09-13 コニカ株式会社 Photosensitive lithographic printing plate
JP2584311B2 (en) * 1989-03-20 1997-02-26 富士写真フイルム株式会社 Positive photoresist composition
US5558227A (en) * 1991-07-18 1996-09-24 Hakamada; Ikuhiro Sealed container having a calendar function
JP4209297B2 (en) * 2003-10-06 2009-01-14 東京応化工業株式会社 POSITIVE PHOTORESIST COMPOSITION FOR DISCHARGE NOZZLE TYPE COATING METHOD AND METHOD FOR FORMING RESIST PATTERN
US9746749B2 (en) 2008-07-11 2017-08-29 Nkt Photonics A/S Lifetime extending and performance improvements of optical fibers via loading
JP5329999B2 (en) * 2009-01-29 2013-10-30 AzエレクトロニックマテリアルズIp株式会社 Pattern formation method

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3040156A1 (en) * 1980-10-24 1982-06-03 Hoechst Ag, 6000 Frankfurt LIGHT SENSITIVE MIXTURE AND LIGHT SENSITIVE COPY MATERIAL PRODUCED THEREOF
DK241885A (en) * 1984-06-01 1985-12-02 Rohm & Haas PHOTOSENSIBLE COATING COMPOSITIONS, THERMALLY STABLE COATINGS MADE THEREOF AND APPLICATION OF SUCH COATINGS FOR THE formation of THERMALLY STABLE POLYMER PICTURES
EP0164083B1 (en) * 1984-06-07 1991-05-02 Hoechst Aktiengesellschaft Positively acting light-sensitive coating solution
DE3421160A1 (en) * 1984-06-07 1985-12-12 Hoechst Ag, 6230 Frankfurt Positive-working radiation-sensitive coating solution
US4550069A (en) * 1984-06-11 1985-10-29 American Hoechst Corporation Positive photoresist compositions with o-quinone diazide, novolak, and propylene glycol alkyl ether acetate
DE3437687A1 (en) * 1984-10-15 1986-04-17 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING NEGATIVE COPIES BY MEANS OF A MATERIAL BASED ON 1,2-CHINONDIAZIDES
EP0195315B1 (en) * 1985-03-11 1989-10-25 Hoechst Celanese Corporation Process for the production of photoresist patterns

Also Published As

Publication number Publication date
EP0220645B1 (en) 1990-09-12
DE3674141D1 (en) 1990-10-18
KR870004334A (en) 1987-05-08
KR950001004B1 (en) 1995-02-06
JPS62105137A (en) 1987-05-15
EP0220645A2 (en) 1987-05-06
JPH0459630B2 (en) 1992-09-22
EP0220645A3 (en) 1987-08-26
ATE56545T1 (en) 1990-09-15

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Effective date: 20061019