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WO2011049105A1 - Précurseur de polyimide et solution précurseur de polyimide - Google Patents

Précurseur de polyimide et solution précurseur de polyimide Download PDF

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Publication number
WO2011049105A1
WO2011049105A1 PCT/JP2010/068436 JP2010068436W WO2011049105A1 WO 2011049105 A1 WO2011049105 A1 WO 2011049105A1 JP 2010068436 W JP2010068436 W JP 2010068436W WO 2011049105 A1 WO2011049105 A1 WO 2011049105A1
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Prior art keywords
formula
polyimide precursor
group
polyimide
carbon atoms
Prior art date
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Ceased
Application number
PCT/JP2010/068436
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English (en)
Japanese (ja)
Inventor
洋行 涌井
豪 松岡
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Toyobo Co Ltd
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Toyobo Co Ltd
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Filing date
Publication date
Application filed by Toyobo Co Ltd filed Critical Toyobo Co Ltd
Priority to JP2011513813A priority Critical patent/JPWO2011049105A1/ja
Publication of WO2011049105A1 publication Critical patent/WO2011049105A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • 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
    • C08G73/22—Polybenzoxazoles

Definitions

  • the present invention relates to a polyimide precursor and a polyimide precursor solution used for forming a surface protective film and an interlayer insulating film for improving the reliability of a semiconductor element.
  • polyimide resin is often used to form a surface protective film and an interlayer insulating film of a semiconductor element (see, for example, Non-Patent Document 1).
  • polyimide resin is required to have a significant performance improvement.
  • the main objective is to reduce the overall device warpage by reducing the thermal expansion difference with low thermal expansion substrates such as silicon wafers. Recently, however, this effect is conspicuous due to the extreme thinning of silicon wafers. Because it has started to appear.
  • the most effective method for reducing the thermal expansion of the polyimide resin is to make the polyimide chemical structure rigid.
  • polyimide resin obtained from p-phenylenediamine and 3,3 ′, 4,4′biphenyltetracarboxylic dianhydride (see, for example, Non-Patent Document 1) or benzoxazole in the main chain A polyimide resin having a structure (see, for example, Patent Document 1) has been proposed.
  • the polyimide resin obtained by such a method generally has poor adhesion to an inorganic substrate such as a silicon wafer. If the adhesion is poor, the polyimide resin is peeled off and swollen in the semiconductor manufacturing process, resulting in poor yield. That is, it is important to impart both low thermal expansion and high adhesion to the polyimide resin.
  • a technique of introducing a siloxane structure into a rigid polyimide structure is effective.
  • polyimide resin obtained by copolymerizing diaminobenzanilide and diamine having a siloxane structure for example, see Patent Document 2
  • acid dianhydride having a siloxane structure and fluorine in the side chain for example, see Patent Document 2
  • a polyimide resin obtained from a benzidine-type diamine having a system substituent for example, see Patent Document 3
  • the former has an amide bond and the latter has a fluorine atom, which is not necessarily a preferable method from the viewpoint of heat resistance, processability, and environmental adaptability.
  • An object of the present invention is to provide a polyimide precursor and a resin composition thereof suitably used as a material constituting a semiconductor device or the like, particularly in a site where dimensional stability, adhesion, and heat resistance are required. To do.
  • the present invention has the following configuration. 1.
  • the following general formula (Formula 1) (wherein R 1 is a tetravalent aromatic ring or aromatic heterocyclic group having 6 to 30 carbon atoms, X is a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms) , R 2 represents a divalent aromatic ring group having a benzoxazole structure) and the following general formula (Formula 2) (wherein R 1 is a tetravalent having 6 to 30 carbon atoms)
  • the precursor is 0.10 ⁇ ⁇ B / (A + B) ⁇ ⁇ 0.30 and 0.2 g / d in N-methyl-2-pyrrolidone Polyimide precursor reduced viscosity when measured at 25 ° C. and dissolved such that the concentration of the resin is characterized in that it is a 0.1 ⁇ 5.0dl / g.
  • R 2 in the formula (Chemical Formula 1) is a divalent aromatic group having a benzoxazole structure, and the following general formulas (Chemical Formula 3) to (Chemical Formula 6) (wherein R 4 , R 5 , R 6 , R 7 is at least one selected from the group consisting of an aromatic ring group or a heterocyclic group each independently consisting of a single ring or a plurality of rings.
  • R 3 in the formula (Formula 2) is a divalent organic group having a siloxane structure, and is a structure represented by the following general formula (Formula 7) (wherein m represents an integer of 1 to 30). It is characterized by 1. ⁇ 2.
  • a polyimide precursor solution wherein the polyimide precursor according to any one of the above is dissolved in an organic solvent.
  • the polyimide precursor and its precursor solution of the present invention can reduce the difference in thermal expansion coefficient between the polyimide obtained after coating and thermal cyclization on a low thermal expansion substrate such as a silicon wafer and the substrate, and is good Since high adhesion and high heat resistance are manifested, it is possible to meet demands for improving the performance of semiconductor devices such as heat cycle resistance and heat shock resistance.
  • the present invention has the following general formula (Formula 1) (wherein R 1 is a tetravalent aromatic ring or aromatic heterocyclic group having 6 to 30 carbon atoms, X is a hydrogen atom or 1 to 30 carbon atoms.
  • a repeating unit represented by a valent organic group R 2 represents a divalent aromatic ring group having a benzoxazole structure, and the following general formula (Formula 2) (wherein R 1 has 6 to 30 carbon atoms)
  • a tetravalent aromatic ring or aromatic heterocyclic group, X is a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms, and R 3 is a divalent organic group having a siloxane structure.
  • the R 1 component in the general formulas (Chemical Formula 1) and (Chemical Formula 2) is an aromatic ring or aromatic heterocyclic group having 6 to 30 carbon atoms in order to impart heat resistance to the polyimide.
  • Preferred specific examples of R 1 include pyromellitic acid, naphthalenetetracarboxylic acid, 3,3 ′, 4,4′-biphenyltetratetracarboxylic acid, 2,3 ′, 3,4′-biphenyltetratetracarboxylic acid, 2,2 ′, 3,3′-biphenyltetratetracarboxylic acid, 3,3 ′, 4,4′-oxydiphenyltetracarboxylic acid, benzophenone-3,3 ′, 4,4′-tetracarboxylic acid, diphenylsulfone -3,3 ', 4,4'-tetracarboxylic acid, 4,4'-(2,2-hexafluoroisopropylidene)
  • More preferred specific examples for lowering the linear thermal expansion coefficient of polyimide include pyromellitic acid, naphthalenetetracarboxylic acid, 3,3 ′, 4,4′-biphenyltetratetracarboxylic acid, 2,2 ′.
  • Examples include structures derived from -diphenyl-3,3 ', 4,4'-biphenyltetracarboxylic acid and 2,2'-diphenoxy-3,3', 4,4'-biphenyltetracarboxylic acid.
  • the R 2 component in the general formula (Formula 1) is not particularly limited as long as it is a divalent aromatic ring group having a benzoxazole structure, but in order to reduce the linear thermal expansion coefficient of polyimide, Formula (Chemical Formula 3) to (Chemical Formula 6) (wherein R 4 , R 5 , R 6 and R 7 each independently represents an aromatic ring group or a heterocyclic group composed of a single ring or a plurality of rings.
  • R 2 component It is preferably a divalent aromatic group having a benzoxazole structure represented by any one of Particularly preferable specific examples of the R 2 component include the following general formula (Chemical Formula 8) among the above general formula (Chemical Formula 3), particularly the following general formula (Chemical Formula 9) among the above general formula (Chemical Formula 4), Of the general formula (Chemical formula 5), the following general formulas (Chemical formula 10) to (Chemical formula 13) are particularly preferable, and among the general formula (Chemical formula 6), the following general formulas (Chemical formula 14) to (Chemical formula 16) are particularly preferable.
  • the R 2 component include the following general formula (Chemical Formula 8) among the above general formula (Chemical Formula 3), particularly the following general formula (Chemical Formula 9) among the above general formula (Chemical Formula 4), Of the general formula (Chemical formula 5), the following general formulas (Chemical formula 10) to (Chemical formula 13) are particularly preferable, and among the general formula
  • the R 3 component in the general formula (Chemical Formula 2) is not particularly limited as long as it is a divalent organic group having a siloxane structure, but in order to impart heat resistance to the polyimide, the following general formula (Chemical Formula 7) ( In the formula, m represents an integer of 1 to 30).
  • a particularly preferred specific example is a structure represented by the following general formula (Formula 17).
  • the X component in the general formulas (Chemical Formula 1) and (Chemical Formula 2) is preferably a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms.
  • Specific examples of the monovalent organic group having 1 to 30 carbon atoms include methyl group, ethyl group, propan-1-yl group, propan-2-yl group, butan-1-yl group, butan-2-yl group, and 2-methyl. Examples include propan-1-yl group, 2-methylpropan-2-yl group, benzyl group, 2-hydroxybenzyl group, 3-hydroxybenzyl group, 4-hydroxybenzyl group and the like.
  • the total number (A + B) of the number of repeating units (A) represented by the formula (Chemical Formula 1) and the number of repeating units (B) represented by the Formula (Chemical Formula 2) in the polyimide precursor is not particularly limited, but in order to reduce the linear thermal expansion coefficient of polyimide and increase the heat resistance, it is preferably 60% or more, more preferably 70% or more, and 80% More preferably, it is the above.
  • the method for polymerizing the polyimide precursor of the present invention includes a polymerization method in which tetracarboxylic acid or a derivative thereof and a diamine are mixed in an organic solvent, but is not particularly limited to this polymerization method.
  • the monomer mixing ratio (molar ratio) when polymerizing the polyimide precursor of the present invention is expressed in terms of acid dianhydride / diamine, preferably 0.800 to 1.200 / 1.200 to 0.800. It is preferably 0.850 to 1.150 / 1.15 to 0.850, more preferably 0.900 to 1.100 / 1.100 to 0.900.
  • an end-capping agent such as dicarboxylic acid or a derivative thereof, tricarboxylic acid or a derivative thereof, aniline or a derivative thereof can be used for molecular end-capping.
  • Preferred for use in the present invention are phthalic anhydride, maleic anhydride, and ethynylaniline, and the use of maleic anhydride is more preferred.
  • the amount of the end-capping agent used is 0.001 to 1.0 mole ratio per mole of monomer component.
  • the organic solvent used for polymerizing the polyimide precursor of the present invention is not particularly limited as long as it dissolves both the raw material monomer and the polyimide precursor, and examples thereof include o-cresol, m-cresol, p. -Cresol, N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, sulfolane, halogen These solvents can be used, and these solvents can be used alone or in combination.
  • the organic solvent may be used in an amount sufficient to dissolve the charged monomer, and is usually 1 to 50% by mass, preferably 5 to 30% by mass.
  • the polymerization reaction is continuously carried out in a temperature range of 0 to 80 ° C. for 10 minutes to 50 hours with stirring and / or mixing in an organic solvent.
  • the polymerization reaction can be divided or the temperature can be increased or decreased as necessary. It doesn't matter.
  • the order of addition of monomers and the like is not particularly limited, but it is preferable to add tetracarboxylic acid or a derivative thereof to the diamine solution.
  • an additive may be added for the purpose of improving the performance of the polyimide.
  • additives vary depending on the purpose and are not particularly limited. Further, the addition method and the addition time are not particularly limited. Examples of the additive include known organic and inorganic fillers such as metal oxides such as silicon oxide, titanium oxide, and aluminum oxide, and phosphates such as calcium phosphate, calcium hydrogen phosphate, and calcium pyrophosphate.
  • the polyimide precursor resin obtained by the reaction may be reprecipitated from the reaction solution using an appropriate poor solvent.
  • the poor solvent include acetone, methanol, ethanol, 2-propanol, and water, but are not particularly limited as long as they can be efficiently reprecipitated.
  • the solvent which removes the residual reaction solvent after reprecipitation It is preferable to use the solvent used at the time of reprecipitation.
  • the reduced viscosity is 0.1 to 5.0 dl / g when dissolved in N-methyl-2-pyrrolidone so as to have a resin concentration of 0.2 g / dl and measured at 25 ° C.
  • it is preferably 0.2 to 4.0 dl / g, 0.3 to 2 More preferably, it is 0.0 dl / g.
  • the reduced viscosity is less than 0.1 dl / g, the heat resistance of the imide film is remarkably impaired, and when the reduced viscosity is more than 5.0 dl / g, the viscosity of the polyimide precursor solution is increased and the handling property is remarkably deteriorated.
  • the reaction solution may be used as it is as a polyimide precursor solution, or the polyimide precursor reprecipitated from the reaction solution by the above method may be dissolved again in a solvent to obtain a polyimide precursor solution.
  • a solvent to obtain a polyimide precursor solution.
  • it is not particularly limited as long as it efficiently dissolves the polyimide precursor.
  • organic solvents such as -acetyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, sulfolane, and halogenated phenols.
  • the means for mixing the polyimide precursor and the organic solvent is not particularly limited.
  • a normal stirring blade a method of mixing and stirring using a stirring blade for high viscosity, a multi-screw extruder, or Examples of the method include mixing and stirring using a method using a static mixer and the like, and further using a method using a mixing and dispersing machine for high viscosity such as a roll mill.
  • the composition of the polyimide precursor in the polyimide resin precursor solution obtained in the present invention is preferably 1 to 50% by mass, more preferably 5 to 30% by mass. in this case. Since the viscosity is 0.1 to 1000 Pa ⁇ s, preferably 0.5 to 500 Pa ⁇ s, more preferably 1 to 10 Pa ⁇ s, as measured with a Brookfield viscometer, stable liquid feeding is possible. preferable.
  • polyimide precursor resin and polyimide precursor resin composition of the present invention From the polyimide precursor resin and polyimide precursor resin composition of the present invention, a polyimide resin, a polyimide coating film, and a polyimide film that have a low coefficient of linear expansion, high heat resistance, and high adhesion to a substrate such as a silicon wafer A polyimide molded body such as is obtained.
  • a method for obtaining the polyimide molded body is not particularly limited, and examples thereof include a method of applying the polyimide precursor resin composition to a substrate and then heating imidization.
  • the method for applying the polyimide precursor resin composition to the base material is not particularly limited, for example, a method of spin coating such as spin coating, a method using a squeegee such as a doctor blade, applicator, comma coater, Examples thereof include a screen printing method.
  • the substrate for applying the polyimide precursor resin composition to the substrate is not particularly limited.
  • an inorganic substrate such as a silicon wafer or a ceramic plate, or a metal substrate such as a copper foil or an SUS foil.
  • organic substrates such as polyimide films and polyethylene terephthalate films.
  • the heating conditions for heating imidization of the polyimide precursor resin composition are not particularly limited, but after preheating at a temperature of 50 ° C. to 150 ° C., preferably 60 ° C. to 130 ° C., 20 ° C. / Min or less, preferably 10 ° C / min or less.
  • a preferable example is a condition where the temperature is increased at a rate of temperature increase of 5 ° C./min or less and the final heating is performed at a temperature of 250 ° C. or higher, preferably 300 ° C. or higher, more preferably 350 ° C. or higher.
  • the glass transition temperature is 250 ° C. or higher, preferably 270 ° C. or higher, more preferably 300 ° C. or higher, while being closely adhered to a substrate such as a silicon wafer, and the thermal decomposition temperature (5% weight loss temperature).
  • a polyimide resin, a polyimide coating film and a polyimide film can be obtained which are as low as 5 to 25 ppm / ° C. or less.
  • Glass transition temperature of polyimide film The obtained polyimide film was subjected to DSC measurement under the following conditions, and the glass transition point (Tg) was determined under the following measurement conditions in accordance with JIS K7121.
  • Adhesion rate of polyimide resin coating film A 1 mm x 1 mm grid (100 squares) was created in accordance with JIS K 5600 on the obtained silicon wafer with a polyimide resin coating film, and a cello tape (registered trademark) peel test was performed. , The remaining film rate was defined as the adhesion rate.
  • PMDA pyromellitic dianhydride
  • DAMBO 5-amino-2- (p-aminophenyl) benzoxazole (Chemical Formula 9)
  • PBABO 2,2′-p-phenylenebis (5-aminobenzoxazole) (Chemical formula 14)
  • 5,4-DAPBBO 2,6- (4,4′-diaminodiphenyl) benzo [1,2-d: 5,4-d ′] bisoxazole
  • 4,5-DAPBBO 2,6- (4,4′-diaminodiphenyl) benzo [1,2-d: 4,5-d ′] bisoxazole
  • APDS 1,3-bis (3-aminopropyl) -1,1,3,3, -tetramethyldisiloxane
  • ODA 4,4′-diaminodiphenyl ether MA: maleic anhydride
  • Example 1 The inside of the reaction vessel equipped with a nitrogen introduction tube, a thermometer, and a stirring rod was purged with nitrogen, and then 5-amino-2- (p-aminophenyl) benzoxazole 20.27 g (0.090 mol), 1, 3- (3 -Aminopropyl) -1,1,3,3-tetramethyldisiloxane 2.63 g (0.010 mol) and N-methyl-2-pyrrolidone 178.16 g were introduced and completely dissolved. When 20.07 g (0.092 mol) of anhydride and 1.57 g (0.016 mol) of maleic anhydride were introduced and stirred at a reaction temperature of 25 ° C.
  • a yellow polyimide precursor resin solution was obtained.
  • the reduced viscosity of the obtained polyimide precursor resin was 0.60 dl / g.
  • 5 g of the obtained polyimide precursor resin solution was introduced into 200 g of 2-propanol to obtain a solid polyimide precursor resin. Further, the polyimide precursor resin was washed with 2-propanol, and then at 60 ° C. for 24 hours.
  • two silicon wafers having a diameter of 8 inches were prepared, and the obtained polyimide precursor resin solution was spin-coated on each of the two sheets under a condition of 2000 rpm ⁇ 30 seconds using a spin coater, and then heated at 60 ° C. on a hot plate. By drying for 30 minutes, two silicon wafers with polyimide precursor resin were obtained.
  • the polyimide precursor resin was peeled from one of the two obtained silicon wafers with a polyimide precursor resin, and fixed to a metal frame.
  • the polyimide precursor resin coating film fixed to the metal frame and the remaining one of the two silicon wafers with the polyimide precursor resin were put into a muffle furnace under a nitrogen atmosphere, and the temperature was increased from 100 ° C.
  • the temperature was raised over a period of time, and heating was further performed at a temperature of 350 ° C. for 60 minutes to obtain a polyimide film and a silicon wafer with a polyimide resin.
  • the obtained polyimide film had a thickness of 5 ⁇ m, a linear thermal expansion coefficient of 0.5 ppm / ° C., a glass transition temperature of 380 ° C., and a thermal decomposition temperature of 550 ° C.
  • the adhesive rate was 50%. *
  • Examples 2 to 10 In the same manner as in Example 1, adjust the polyimide precursor solution at the blending ratio shown in Table 1 and Table 2, and further create a polyimide film and a polyimide resin coated silicon wafer by the same method as in Example 1. The linear thermal expansion coefficient, glass transition temperature, thermal decomposition temperature, and adhesion rate were evaluated. The results are shown in Tables 1 and 2.
  • the polyimide precursor of the present invention and the resin composition thereof can be applied to a low thermal expansion substrate such as a silicon wafer, and the difference in thermal expansion coefficient between the polyimide obtained after thermal cyclization and the substrate can be reduced, and is good. Adhesiveness and high heat resistance are manifested, so it can meet the demands for improving the performance of semiconductor devices such as heat cycle resistance and heat shock resistance, and meet the market needs for higher functionality, smaller and thinner electronic devices. I can respond. Therefore, it is important to contribute to the industry.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

L'invention concerne un précurseur de polyimide qui est approprié pour être utilisé comme matériau constitutif pour un dispositif à semi-conducteur, notamment dans les parties qui nécessitent une stabilité dimensionnelle, une adhésion et une résistance à la chaleur ; et une composition de résine du précurseur de polyimide. De façon spécifique, l'invention porte sur un précurseur de polyimide qui contient au moins une unité répétitive représentée par la formule générale (1) (dans laquelle R1 représente un groupe à noyau aromatique tétravalent ou à noyau hétérocyclique aromatique ayant 6-30 atomes de carbone ; X représente un atome d'hydrogène ou un groupe organique monovalent ayant 1-30 atomes de carbone ; et R2 représente un groupe à noyau aromatique divalent ayant une structure benzoxazole) et une unité répétitive représentée par la formule générale (2) (dans laquelle R1 représente un groupe à noyau aromatique tétravalent ou à noyau hétérocyclique aromatique ayant 6-30 atomes de carbone ; X représente un atome d'hydrogène ou un groupe organique monovalent ayant 1-30 atomes de carbone ; et R3 représente un groupe organique divalent ayant une structure siloxane). Le précurseur de polyimide est caractérisé par le fait que la relation molaire entre l'unité répétitive (A) représentée par la formule (1) et l'unité répétitive (B) représentée par la formule (2) satisfait 0,10 = {B/(A + B)} = 0,30 quand elle est obtenue à partir du rapport des aires de pics en RMN du proton, et par le fait que la viscosité réduite telle que mesurée à 25 °C par dissolution du précurseur du polyimide dans de la N-méthyl-2-pyrrolidinone de façon à avoir une concentration en résine de 0,2 g/dl est de 0,1-5,0 dl/g.
PCT/JP2010/068436 2009-10-23 2010-10-20 Précurseur de polyimide et solution précurseur de polyimide Ceased WO2011049105A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020121271A (ja) * 2019-01-30 2020-08-13 日東電工株式会社 クリーニングシートおよびクリーニング機能付搬送部材

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02251584A (ja) * 1988-11-16 1990-10-09 Asahi Chem Ind Co Ltd ヘテロ環含有ポリイミド複合体
JPH07157560A (ja) * 1993-12-02 1995-06-20 P I Zairyo Kenkyusho:Kk ポリイミドブロック共重合体の製造方法及びその溶液組成物
WO2004087793A1 (fr) * 2003-03-28 2004-10-14 Pi R & D Co. Ltd. Polyimide reticule, composition comprenant ce polyimide et procede permettant sa production
JP2004285129A (ja) * 2003-03-19 2004-10-14 Nippon Zeon Co Ltd 感光性ポリイミド前駆体、感光性ポリイミド樹脂組成物、及び該樹脂組成物を用いた半導体素子の製造方法
JP2006251478A (ja) * 2005-03-11 2006-09-21 Toyobo Co Ltd ポジ型感光性ポリイミド前駆体組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02251584A (ja) * 1988-11-16 1990-10-09 Asahi Chem Ind Co Ltd ヘテロ環含有ポリイミド複合体
JPH07157560A (ja) * 1993-12-02 1995-06-20 P I Zairyo Kenkyusho:Kk ポリイミドブロック共重合体の製造方法及びその溶液組成物
JP2004285129A (ja) * 2003-03-19 2004-10-14 Nippon Zeon Co Ltd 感光性ポリイミド前駆体、感光性ポリイミド樹脂組成物、及び該樹脂組成物を用いた半導体素子の製造方法
WO2004087793A1 (fr) * 2003-03-28 2004-10-14 Pi R & D Co. Ltd. Polyimide reticule, composition comprenant ce polyimide et procede permettant sa production
JP2006251478A (ja) * 2005-03-11 2006-09-21 Toyobo Co Ltd ポジ型感光性ポリイミド前駆体組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020121271A (ja) * 2019-01-30 2020-08-13 日東電工株式会社 クリーニングシートおよびクリーニング機能付搬送部材
JP7270397B2 (ja) 2019-01-30 2023-05-10 日東電工株式会社 クリーニングシートおよびクリーニング機能付搬送部材

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