WO1990012051A1 - Couches de decollage en polyimide solubles dans des bases utiles en microlithographie - Google Patents

Couches de decollage en polyimide solubles dans des bases utiles en microlithographie Download PDF

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Publication number
WO1990012051A1
WO1990012051A1 PCT/US1990/001671 US9001671W WO9012051A1 WO 1990012051 A1 WO1990012051 A1 WO 1990012051A1 US 9001671 W US9001671 W US 9001671W WO 9012051 A1 WO9012051 A1 WO 9012051A1
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WIPO (PCT)
Prior art keywords
acid
composition
photoresist
release
alkaline
Prior art date
Application number
PCT/US1990/001671
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English (en)
Inventor
Terry Brewer
Tony Flaim
James E Lamb, Iii
Gregg A. Barnes
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Brewer Science, Inc.
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Filing date
Publication date
Priority claimed from US07/330,795 external-priority patent/US5281690A/en
Priority claimed from US07/331,355 external-priority patent/US5057399A/en
Application filed by Brewer Science, Inc. filed Critical Brewer Science, Inc.
Publication of WO1990012051A1 publication Critical patent/WO1990012051A1/fr

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1025—Preparatory processes from tetracarboxylic acids or derivatives and diamines polymerised by radiations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention generally relates to new and improved polyamic acid/imide microlithographic com ⁇ positions , their method of manufacture, and particularly their use in a novel concurrent wet-development and im ⁇ proved lift-off process .
  • Photoresist compositions are commonly used in microlithographic processing and generally consist of a diazoquinone photosensitizer and a novolak resin binder. Normally, such compositions are coated onto semiconductor substrates ; and, when exposed to light of the proper wavelength, they are chemically altered in their solubility to alkaline developer solutions . Positive- working photoresists are initially insoluble in the alkaline developer, but after exposure to light, the ex ⁇ posed regions will dissolve or "wet-develop" in alkaline solution forming indented, micron-size line features . Sub- sequently, for many applications, the undissolved portion of the resist must be stripped from the substrate.
  • Positive-working novolak photoresists are being increasingly used under conditions which render them insoluble in conventional strippers. Ion implanta ⁇ tion, plasma hardening, deep UV hardening and other high temperature processing conditions produce, for example, crosslinking reactions within the resist. This makes stripper penetration and resist dissolution, which are es ⁇ sential to removal of the resists, virtually impossible. Oxidative strippers such as hot sulfuric acid- hydrogen peroxide mixtures can be effective against intractable resists, but removal is often slow or incom ⁇ plete. Moreover, these treatments are restricted to use on unmetallized substrates. Alternatively, removal of intrac ⁇ table resists is sometimes possible by soaking in hot chlorinated and/or phenolic solvents. However, toxicity and disposal problems associated with these materials are critical drawbacks to their use.
  • solvent-soluble release layer material is polysulfone. This material has the advantage of enabling the liftoff of metal mask layer by conventional solvent stripping. Although the material also serves to insulate and protect the metal substrate from attack by harsh oxidative strippers, it all the same requires such harsh strippers to liftoff the photoresist layer if hardened.
  • Polysulfone can serve to liftoff the photoresist material itself as in the fifth step of Figure 3, but not without other drawbacks.
  • micron feature sizes developed by dry etching are excessively more expen ⁇ sive than wet etching.
  • the dry developable release layer material requires separate plasma etching equipment in addition to that required to etch the photoresist layer and other layers of multilayer microlithographic processing. The addition of even more equipment and more steps becomes such a serious drawback that those in the art have preferred the toxicity, disposal, and other restrictions associated with employing non-conventional strippers, to remove the photoresist layers, rather than deal with a dry-developable release layers.
  • Some otherwise acceptable release layer materials do not adhere sufficiently to semi-conductor substrates or are incompatible surfaces for applying resist layers, or other organic or inorganic layers, thereto.
  • a wet-developable release layer of material that could be co-developed concurrently with the photoresist material, without requiring separate plasma etching equipment, and which could be lifted off by immer ⁇ sion in more mild and less toxic solvents and which would not errode etalized substrates, while providing good adhesion to semiconductor substrates and a compatible sur ⁇ face for applying resist layers, or other organic or inor ⁇ ganic layers, would be a surprising advancement in the art fulfilling a long felt need in the industry.
  • Figures 1 thru 4 illustrates four alternative prior art processes which employ dry-developable release layer concepts.
  • the photoresist layer is wet- developed, while the release layer is dry-developed with separate plasma etching equipment. Additionally, the photoresist layer, if hardened, must be lifted with harsh strippers which are either toxic and have disposal problems, or would be deleterious to the substrate if the photoresist were removed simultaneously with the release layer.
  • Figure 1 illustrates the six principle steps of the IBM Metal Liftoff Process using dry-processable release layers.
  • Figure 2 illustrates the six principle steps of a tri-level process using dry-developable planarizing layers (or very thick release layers).
  • Figure 3 illustrates the five principle steps of the IBM ion Milling Process for metal inter layers using dry- developable release layer systems.
  • Figure 4 illustrates the seven principle steps of the metal-over-release layer ion planarization mask process.
  • Figure 5 illustrates the four principle steps of the imaging process for concurrently wet-developing the release layer and its adjacent positive-working photoresist.
  • Figure 6 illustrates a prior art process for applica ⁇ tion of prior art polyimide coatings starting with a polyamic acid solution, but which polyimide coatings can not be used as release layers for the photoresist.
  • Figure 7 illustrates a diagram of the polyamic acid chemistry involved in the general manufacturer of such materials.
  • Figure 8 illustrates the process of the present in ⁇ vention using wet-developable release layers to assist the removal of high-temperature baked photoresist.
  • Figure 9 illustrates ion implantation processes using the wet-developable release layer process of the present invention.
  • Figure 10 illustrates metal liftoff processes using the wet-developable release layer compositions of the present invention.
  • Figure 11 illustrates processes using the wet- developable release layers of the present invention as a planarizing film.
  • Figure 12 illustrates processes using the wet- developable film of the present invention to remove an epoxy encapsulant.
  • Figure 13 illustrates the formulas of two polyimide resins useful as release layers in the present invention.
  • the release layer compositions of the present inven ⁇ tion are generally derived from the polyamic acid chemistry depicted at Figure 7 but with critical dif ⁇ ferences from past polyamic acid/imides .
  • n represents the number of repeat units in the polymer and is usually greater than 10.
  • These compositions are not normally spin-coated directly from solution in the polyimide form. Instead they are ap ⁇ plied by spin-coating in the precursor polyamic acid form.
  • the polyamic acid precursor then is heated to ap ⁇ proximately 170 degrees C to remove the solvents and to partially imidize the film. This allows a controllable etch rate in alkaline developers as the composition is then patterned along with a photoresist layer. After pat ⁇ terning and stripping the resist, the polyamic acid film is heated to above 200 degrees C to complete the imidiza- tion and remains on the substrate.
  • the acidic functionalized groups may include, for ex ⁇ ample, carboxylic acids (-C00H), aromatic hydroxyls (aryl-OH), and sulfonic acids (-S0 3 H).
  • Typical acid func ⁇ tionalized polymers may be seen at Figure 13A and Figure 13B. It is particularly preferred that the acidic func ⁇ tional moieties be attached to the diamine side of the polyamic acid/imide because it is synthetically more con ⁇ venient to prepare the functionalized diamines than to prepare functionalized dyanhydrides. It is dLn ⁇ ortant to know that the polyamic acid/imides of the present invention remain sufficiently soluble in spite of the high thermal imidization which would otherwise render prior art polyamic acid/imides unsuitable as release layers.
  • Diamines with acidic functionalities suitable in con ⁇ densation reactions for preparing compositions of the present invention are commercially available.
  • the preferred group of such diamines is as follows:
  • Suitable dianhydrides include the following:
  • BPDA 3,3',4,4' - biphenyl tetracarboxylic dianhydride
  • Two especially preferred release layer compositions are copolymers of 3,5- diaminobenzoic acid and BTDA and 3,3'-dihydroxy-4,4'- diaminobiphenyl and PMDA.
  • Preferred solvent systems for polyamic acid prepara ⁇ tion and spincoating include alkyl amides such as N-methylpyrrolidone and dimethylacetamide, methyl sul- foxide, cyclic ketones such as cyclohexanone, and glymes such as 2-methoxyethyl ether.
  • alkyl amides such as N-methylpyrrolidone and dimethylacetamide
  • methyl sul- foxide methyl sul- foxide
  • cyclic ketones such as cyclohexanone
  • glymes such as 2-methoxyethyl ether
  • Some monomer combinations yield polyimides which develop too fast at desired bake tempera ⁇ tures and can not be patterned to small feature sizes, for example, 3,5 diaminobenzoic acid and PMDA rather than BTDA baked for 30 minutes at 200 C rather than BTDA. In such instance it is preferred that the development rate be reduced by including other diamine components which do not bear acidic functional groups into the polymer structure.
  • High molecular weight aromatic diamines are particularly useful in this regard since they have a large dilution ef ⁇ fect on the polymer repeat unit.
  • a large number of such diamine materials have been described in the literature, for example, see the general reference "Polyimides: Syn ⁇ thesis, Characterization, and Applications," Vols. I & II; K.L. Mittal, Ed.; Plenum Press, New York (1984).
  • a few preferred diamines are , 4 ' -oxydianiline, or ODA, (particularly when copolymerized with PMDA) ,
  • BAPP 2,2-bis [4-(4-a_ ⁇ )_inophenoxy)phenyl]propane, or BAPP, bis[4-(4-aminophenoxy)phenyl]sulfone, or BAPPS.
  • this inven ⁇ tion comprises terpolymers of 3,5-diaminobenzoic acid/BTDA/BAPPS wherein the mole ratio of 3,5- diaminobenzoic acid to BAPPS is 2:1 to 4:1.
  • Another way to slow the development rate of the release layer films, but without resorting to structural modifications, is through the use of additives.
  • These in ⁇ clude compatible polymers with low developer solubility and reactive-low-molecular weight (MW) compounds which are capable of crosslinking the release layer polymer.
  • Multifunctional epoxides compounds are especially ef ⁇ fective, low MW additives.
  • a related benefit of additive use is that the curing temperature of the film can be reduced.
  • Traditional bisphenol A-type epoxy resins and cycloaliphatic diepoxides are effective additives when used at 1-20 wt. % based on polyamic acid solids.
  • An alternative means for reducing the imidization re ⁇ quirements is to modify the polymer by esterifying acid positions of the amic acid group with either an aromatic or aliphatic alcohol. This causes essentially the same change in solubility as imidization. If esterification is employed, the bake requirements may be reduced to as low as 100 C. Other release layer properties such as high tem ⁇ perature stability and solubility in alkaline media are unaffected.
  • the polyamic acids are prepared as follows: The diamine (s) is (are) charged into a sealable reactor fitted with a heavy stirrer and nitrogen purge. It is dis ⁇ solved in a portion of the solvent.
  • the dianhydride is then washed into the stirring diamine solution with the balance of the solvent to give a dianhydride/diamine mole ratio in the range 0.700 - 1.100. Ratios in the range 0.85 - 1.00 are preferred.
  • the solution is allowed to stir at ambient temperature for 24 hours to complete the polymerization.
  • the polymer solids level is usually ad ⁇ justed to 10-25 wt.%.
  • the polyamic acid solution is diluted to any con ⁇ venient level needed to obtain a desired film thickness when spincoated.
  • the products are preferably stored under refrigerated conditions to preserve physical and chemical properties. Thereafter, they may be dis ⁇ tributed and employed as release layers in microlithographic imaging processes.
  • the basic imaging process for the polyimide release layer compositions is described in Fig. 5.
  • the processes described in Figs. 8-11 are standard schemes which may use release layer composition of the present invention.
  • the unique properties of base-soluble polyimides also makes them applicable to these, device-related processes where intractable layers must be removed. These processes may or may not entail photoimaging.
  • failure analysis of IC devices often involves stripping an intractable epoxy layer (encapsulant) from the surface of a device before electrical tests can be made.
  • Using a high temperature stable polyimide release layer beneath the epoxy coating would greatly simplify this process (See Figure 12).
  • the life of the device would not be jeopardized by the polyimide release film since it has the requisite thermal and electrical properties to remain within the device.
  • base-soluble polyimides can also be envi ⁇ sioned in allied industries such as the manufacture of printed circuit boards, electronic displays, sensors, etc. , where patternable films with good chemical and tem ⁇ perature resistance are required as an integral part of a device or are needed to simplify the fabrications of a device.
  • release film thicknesses in the range 500-10,000A give the desired lithographic performance (that is, they can be imaged to feature sizes as small as one micron) and provide rapid release of positive resists.
  • Various combinations of solution solids content, spincoat- ing speeds, and spinning times will give films in this thickness range. Preferred ranges for these parameters are shown below. spinning speed: 1000-7000 RPM spinning time: 10-180 seconds polymer solids level: 2-30 wt.%
  • the release layer materials are useful on all semi ⁇ conductor substrates including silicon, silicon dioxide, silicon nitride, silicon carbide, glasses, gallium ar ⁇ senide, aluminum and other metals.
  • an adhesion promoter such as hexamethyldisilazane or an or- ganotrialkoxysilane
  • the release film is preferably baked to cause more than 80% imidization of the film un ⁇ less esterilled polymers or low MW additives are used.
  • Preferred bake temperatures lie in the range 140 - 250 C. The most preferred temperatures (which provides the best lithographic control) is obtained by correlating the structure of the release polymer and the type of solvents used for spincoating. For example, higher bake tempera ⁇ tures are required for thick films spun from heavy sol ⁇ vents such as N-methyl-pyrrolidone.
  • Convection oven baking, infrared track, and hotplate baking give acceptable results.
  • Oven bake times range from 5-120 minutes; hotplate bake times range from 15-300 seconds.
  • imidization can also be achieved by chemical techniques including exposure to gaseous reagents and high energy beams.
  • the positive photoresist, softbaking, exposure and development may follow the procedures recom ⁇ mended by the manufacturer of the photoresist.
  • the preferred developers are aqueous solutions of sodium or potassium hydroxides, tetramethylammonium hydroxide, choline hydroxide, and other aqueous alkalies.
  • the photoresist is etched away first, exposing the release layer film, which is developed concurrently although second in sequence.
  • the time required to develop the release layer film will depend on its thickness, its thermal history and its structure. Preferably 5 to 120 seconds is sufficient.
  • Overdevelopment is preferably avoided because it will con ⁇ tinue to undercut beneath the resist (Fig. 5). In liftoff processes (Fig. 10), however, a certain degree of undercut is preferred.
  • a variety of processing steps may occur before the photoresist is lifted (by dissolving the release layer) . These include substrate etching by wet or dry methods, metal deposition, glass deposition, ion implantation and various high temperature processes. The good chemical resistance and excellent high temperature stability of polyimide release films means that they will pass through these steps largely unaffected.
  • Release of the resist is accomplished by immersing or spraying the specimen with an alkaline solution that dis ⁇ solves the release layer component.
  • a room temperature photoresist developer or heated developer comprising aqueous alkali can often serve as the release bath. Some ⁇ times, at higher processing temperatures, flowed resist may cover the exposed edges of the release layer pattern and impede the penetration of the aqueous alkali release bath into the release layer.
  • a nonaqueous alkaline media comprising organics such as glycol ethers or N-methylpyrrolidone with the nonaqueous alkali ethanolamine.
  • This nonaqueous alkaline component such as ethanolamine, can be particularly effective to cause dis ⁇ solution of the .polyimide release films where simple or ⁇ ganic solvent mixtures axe not effective alone.
  • the immer ⁇ sion or spray time required to lift the resist varies with the processing conditions. Complete resist removal generally occurs within 1-60 minutes under immersion con ⁇ ditions.
  • the processes of the invention have been described with the use of positive photoresists because of their preferred use in the microelectronics industry and the codevelopment objective.
  • the polyimide release layer materials of this invention can be equally applicable to processes involving electron beam, x-ray, negative and deep UV resists.
  • positive photoresist Usually a mixture of an alkali-soluble phenolic resin (novolac) and a photosensi ⁇ tive dissolution inhibitor. In this form, the mixture can not be dissolved in aqueous alkali to produce an image. Exposure of the resist to UV light causes the photoinhibitor to chemically rearrange forming a car- boxylic acid compound. This compound and the phenolic resin can then be etched away by aqueous base (or developer) to create a positive image. Hence, the term "positive-working" resist.
  • planarization The ability of a polymer coating to create a level surface when spincoated over irregular topography.
  • strippers Liquid chemical media used to remove photoresists after processing is finished. Strippers are normally of two types: 1) mixtures of strong aqueous acids or bases with hydrogen peroxide, and 2) organic solvent mixtures which may contain organic bases to speed attack on positive photoresist. 4. developers - For positive resists, generally 1-10% aqueous solution of an alkali metal hydroxide or a tetra- alkylammonium hydroxide. The solutions may also contain buffers and surfactants.
  • wet-developed or wet-processed refers to an etching process wherein an aqueous developer is used to pattern a photoresist or release layer film.
  • dry-developed or dry-processed refers to an etching process wherein an aqueous developer is used to pattern a photoresist or release layer film or other layer within a masking structure.
  • ion implantation The use of a high energy ion beam to introduce dopant atoms into semiconductor substrates.
  • glasses and dielectrics Electrically insulating in ⁇ organic coatings such as silicone dioxide, silicone car ⁇ bide, and silicone nitride.
  • glasses and dielectrics are sometimes used as a mask for dry-processing of underlying organic films by oxygen plasma or oxygen RIE.
  • Glasses may be grown at high tem ⁇ perature, e.g., silicon dioxide coatings at about 1000 C in the presence of water vapor. They may also be produced by chemical vapor deposition (CVD) which involves the in ⁇ troduction of reactive gases over a substrate at high tem ⁇ peratures.
  • CVD chemical vapor deposition
  • SOG's spin-on-glass coatings
  • SOG's are solutions of or- ganosilicon compounds which form loosely structured glasses when heated to high temperatures.
  • a variety of wet-developable polyimide release layers were prepared and demonstrated using the following procedures: The materials shown in Table 1 were applied in their polyamic acid form onto these three inch silicon or silicon dioxide wafer substrates by spincoating. Solution solids were adjusted to approximately 6 wt.% to give a 2000-2500A film when spun at 4000 RPM for 60 seconds. The films were then imidized by baking. Bake temperatures were correlated to provide the best lithography at 1-2 micron feature sizes. Positive photoresists (SHIPLEY MICROPOSIT 1470) were spun over the release films at 5000 RPM for 30 seconds and then softbaked at 110 C for 15 minutes on an infrared track. Final resist thicknesses were about 1 micron.
  • the wafers were developed in a room temperature solution of 1:1 (v/v) SHIPLEY Microposit MF-312 and deionized water.
  • MF-312 is a concentrated aqueous solu ⁇ tion of tetramethylammonium hydroxide and buffers.
  • Development time ranged between 5 and 15 seconds to give good quality 2.0 micron geometries concurrently in both the resist and the release layers.
  • the ability to lift the resist after high temperature baking of the release layer-resist composite was used to test release capability.
  • the test specimens were baked at 200 C for 30 minutes in a convection oven after development. This treatment rendered the resist virtually insoluble in con ⁇ ventional commercial organic strippers, organic solvents TABLE 1
  • Example 7 Same criteria and results as Example 7, but polymer prepared in 72/25 diglyme/cyclohexanone. Imidization conditions were 190 °C/s min. on hotplate.
  • Control wafers with photoresist coated directly over the substrate showed less than 5% pattern removal within 15 minutes when placed in the release baths.
  • control test are not shown in Table 1 each control used unidentical release bath to its respective release sample. With the release film present, however, more than 90% of the pattern could be lifted within 15 minutes. Two release baths were treated.
  • the first [BATH 1] was warm developer (60 C); the second
  • [BATH 2] was a 60/20/20 (v/v/v) mixture of dipropylene glycol methyl ether, N-methylpyrrolidone and ethanolamine heated to 65 C.
  • Table 1 gives the composition of the release materials and other pertinent conditions which provided the lithographic quality and release results indicated.
  • a polyamic acid imide polymer composition useful as a new and improved wet-developable release-layer in multilayer microlithography, said polymer composi ⁇ tion comprising; effective amounts of acidic func ⁇ tional moieties abnormal to the amic acid structure regular positions along the polymer backbone, to effectively impart solubility in alkaline media despite high imidization.

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Abstract

Des compositions pour couches de décollage solubles dans des bases utiles en microlithographie comprennent des résines d'imide/acide polyamique fonctionnalisé d'acide nonamique. Ces matériaux permettent de développer lithographiquement des couches de décollage et d'agents photorésistants en même temps. Ils permettent également d'obtenir un décollage efficace avec des milieux alcalins même après une forte imidation.
PCT/US1990/001671 1989-03-30 1990-03-30 Couches de decollage en polyimide solubles dans des bases utiles en microlithographie WO1990012051A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US33195489A 1989-03-30 1989-03-30
US07/330,795 US5281690A (en) 1989-03-30 1989-03-30 Base-soluble polyimide release layers for use in microlithographic processing
US330,795 1989-03-30
US331,954 1989-03-30
US331,355 1989-03-31
US07/331,355 US5057399A (en) 1989-03-31 1989-03-31 Method for making polyimide microlithographic compositions soluble in alkaline media

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6335418B1 (en) 1999-02-26 2002-01-01 Osaka Prefectural Government Functional polyamic acid microfine particles, functional polyimide microfine particles, and processes for their production
EP1182229A1 (fr) * 2000-08-21 2002-02-27 Osaka Prefectural Government Particules microfines d'acide polyamique fonctionalisées et particules microfines de polyimide et procédés pour leur de production

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US4378400A (en) * 1980-07-01 1983-03-29 Ube Industries, Ltd. Gas separating material
US4451551A (en) * 1980-12-17 1984-05-29 Hitachi, Ltd. Radiation-sensitive poly(amic acid) polymer composition
US4548891A (en) * 1983-02-11 1985-10-22 Ciba Geigy Corporation Photopolymerizable compositions containing prepolymers with olefin double bonds and titanium metallocene photoinitiators
EP0159428A1 (fr) * 1982-09-30 1985-10-30 Brewer Science, Inc. Couche antiréfléchissante
US4659650A (en) * 1985-03-22 1987-04-21 International Business Machines Corporation Production of a lift-off mask and its application
US4778739A (en) * 1986-08-25 1988-10-18 International Business Machines Corporation Photoresist process for reactive ion etching of metal patterns for semiconductor devices
EP0300326A1 (fr) * 1987-07-21 1989-01-25 Hoechst Celanese Corporation Hydroxypolyimides et photorésists positifs résistant à la température préparés à partir de ceux-ci
US4880722A (en) * 1985-12-05 1989-11-14 International Business Machines Corporation Diazoquinone sensitized polyamic acid based photoresist compositions having reduced dissolution rates in alkaline developers

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4378400A (en) * 1980-07-01 1983-03-29 Ube Industries, Ltd. Gas separating material
US4451551A (en) * 1980-12-17 1984-05-29 Hitachi, Ltd. Radiation-sensitive poly(amic acid) polymer composition
EP0159428A1 (fr) * 1982-09-30 1985-10-30 Brewer Science, Inc. Couche antiréfléchissante
US4548891A (en) * 1983-02-11 1985-10-22 Ciba Geigy Corporation Photopolymerizable compositions containing prepolymers with olefin double bonds and titanium metallocene photoinitiators
US4659650A (en) * 1985-03-22 1987-04-21 International Business Machines Corporation Production of a lift-off mask and its application
US4880722A (en) * 1985-12-05 1989-11-14 International Business Machines Corporation Diazoquinone sensitized polyamic acid based photoresist compositions having reduced dissolution rates in alkaline developers
US4778739A (en) * 1986-08-25 1988-10-18 International Business Machines Corporation Photoresist process for reactive ion etching of metal patterns for semiconductor devices
EP0300326A1 (fr) * 1987-07-21 1989-01-25 Hoechst Celanese Corporation Hydroxypolyimides et photorésists positifs résistant à la température préparés à partir de ceux-ci

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6335418B1 (en) 1999-02-26 2002-01-01 Osaka Prefectural Government Functional polyamic acid microfine particles, functional polyimide microfine particles, and processes for their production
EP1182229A1 (fr) * 2000-08-21 2002-02-27 Osaka Prefectural Government Particules microfines d'acide polyamique fonctionalisées et particules microfines de polyimide et procédés pour leur de production

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