JP4771412B2 - 感光性樹脂及びその製造方法 - Google Patents
感光性樹脂及びその製造方法 Download PDFInfo
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- JP4771412B2 JP4771412B2 JP2006031084A JP2006031084A JP4771412B2 JP 4771412 B2 JP4771412 B2 JP 4771412B2 JP 2006031084 A JP2006031084 A JP 2006031084A JP 2006031084 A JP2006031084 A JP 2006031084A JP 4771412 B2 JP4771412 B2 JP 4771412B2
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- polyimide
- polyimide resin
- resin
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- 238000000034 method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
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- 239000006087 Silane Coupling Agent Substances 0.000 description 2
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical group CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CPOUUWYFNYIYLQ-UHFFFAOYSA-M tetra(propan-2-yl)azanium;hydroxide Chemical compound [OH-].CC(C)[N+](C(C)C)(C(C)C)C(C)C CPOUUWYFNYIYLQ-UHFFFAOYSA-M 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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- 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
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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
- 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
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- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
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- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
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- 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
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- 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
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- 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
- G03F7/022—Quinonediazides
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
(2)前記ポリアミック酸を脱水閉環反応に付して、下記式(6)で表される3種の繰り返し単位からなる、フェノール性水酸基を有するポリイミドを調製する工程、
(3)前記ポリイミドを、1,2−ナフトキノンジアジドスルホニル化合物と反応させて、前記ポリイミドのフェノール性水酸基の水素原子の少なくとも一部を、1,2−ナフトキノンジアジドスルホニル基に置換する工程、
を含む、上記ポリイミド樹脂の製造方法である。
(1)フェノール性水酸基を有するジアミンとテトラカルボン酸二無水物を反応させてポリアミック酸を調製する工程、
(2)前記ポリアミック酸を脱水閉環反応に付して、下記式(6)で表される3種の繰り返し単位からなる、フェノール性水酸基を有するポリイミドを調製する工程、
(3)前記ポリイミドを、1,2−ナフトキノンジアジドスルホニル化合物と反応させて、前記ポリイミドのフェノール性水酸基の水素原子の少なくとも一部を、1,2−ナフトキノンジアジドスルホニル基に置換する工程。
(i)本発明の感光性樹脂組成物の層を基板上に形成する工程、
(ii)前記層を、所定のパターンが形成されたフォトマスクを通して波長240〜500nmの光に露光する工程、
(iii)前記層のうち露光された部分をアルカリ性溶液で溶解して、パターン化された層を得る工程。
撹拌機、温度計及び窒素置換装置を備えたフラスコ内に、4,4’−オキシジフタル酸二無水物31.0g(0.1モル)およびn−メチル−2−ピロリドン150gを仕込んだ。ついで、2,2−ビス(4−アミノー3−ヒドロキシフェニル)プロパン25.8g(0.1モル)をn−メチル−2−ピロリドン100gに溶解した溶液を反応系の温度が50℃を越えないように調節しながら、上記フラスコ内に滴下した。滴下終了後、さらに室温で10時間撹拌した。つぎに、該フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン70gを加え、150℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。
撹拌機、温度計及び窒素置換装置を備えたフラスコ内に、4,4’−オキシジフタル酸二無水物54.3g(0.175モル)、4,4’−ヘキサフルオロプロピリデンビスフタル酸二無水物33.3g(0.075モル)およびn−メチル−2−ピロリドン400gを仕込んだ。ついで、2,2−ビス(4−アミノー3−ヒドロキシフェニル)プロパン64.6g(0.25モル)をn−メチル−2−ピロリドン200gに溶解した溶液を反応系の温度が50℃を越えないように調節しながら、上記フラスコ内に滴下した。滴下終了後、さらに室温で10時間撹拌した。つぎに、該フラスコに水分受容器付き還流冷却器を取り付けた後、トルエン150gを加え、150℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。
撹拌機、温度計及び窒素置換装置を備えたフラスコ内に3,3’、4,4’−ジフェニルスルホンテトラカルボン酸二無水物89.6g(0.25モル)およびN,N−ジメチルアセトアミド500gを仕込んだ。ついで、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)プロパン32.3g(0.125モル)および9,9−ビス(4−アミノフェニル)フルオレン43.6g(0.125モル)をN,N−ジメチルアセトアミド200gに溶解した溶液を反応系の温度が50℃を越えないように調節しながら、上記フラスコ内に滴下した。滴下終了後、さらに室温で10時間撹拌した。つぎに、該フラスコに水分受容器付き還流冷却器を取り付けた後、トルエン180gを加え、150℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。
撹拌機、温度計及び窒素置換装置を備えたフラスコ内に、4,4’−オキシジフタル酸二無水物77.6g(0.25モル)およびN,N−ジメチルアセトアミド500gを仕込んだ。ついで、2,2−ビス(4−アミノー3−ヒドロキシフェニル)プロパン51.7g(0.2モル)およびジアミノシロキサン(ただし、一般式(5)のhの平均が9のもの)45.8g(0.05モル)をN,N−ジメチルアセトアミド200gに溶解した溶液を反応系の温度が50℃を越えないように調節しながら、上記フラスコ内に滴下した。滴下終了後、さらに室温で10時間撹拌した。つぎに、該フラスコに水分受容器付き還流冷却器を取り付けた後、トルエン150gを加え、150℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。
1,2−ナフトキノンジアジド−5−スルホニルクロライド7.72g、トリエチルアミン3.07gとした以外は実施例1と同様にしてポリイミド樹脂を得た。この樹脂を実施例1と同様に、1H―NMRで分析した結果、下記式で示される繰り返し単位の構造を有する樹脂(A−5)であることがわかった。また、ゲル浸透クロマトグラフィー(GPC)分析の結果、このポリマーの数平均分子量は、65400であった。
1,2−ナフトキノンジアジド−5−スルホニルクロライド20.59g、トリエチルアミン8.20gとした以外は実施例1と同様にしてポリイミド樹脂を得た。この樹脂を実施例1と同様に、1H―NMRで分析した結果、下記式で示される繰り返し単位の構造を有する樹脂(B−1)であることがわかった。また、ゲル浸透クロマトグラフィー(GPC)分析の結果、このポリマーの数平均分子量は、73000であった。
1,2−ナフトキノンジアジド−5−スルホニルクロライド0.51g、トリエチルアミン0.20gとした以外は実施例1と同様にしてポリイミド樹脂を得た。この樹脂を実施例1と同様に、1H―NMRで分析した結果、下記式で示される繰り返し単位の構造を有する樹脂(B−2)であることがわかった。また、ゲル浸透クロマトグラフィー(GPC)分析の結果、このポリマーの数平均分子量は、54000であった。
各実施例で得られた感光性ポリイミド樹脂100重量部をシクロヘキサノン400重量部に溶解し、表1に記載した量の界面活性剤、接着助剤、感光剤を添加して混合した後、テフロン製0.2ミクロンフィルターで精密ろ過を行って、各感光性樹脂組成物を得た。また、比較例として、樹脂A−1の前駆体である、式(8)で示される樹脂(C−1)を用いた。
シリコン基板の1枚につき、溶剤を除去するため100℃で2分間、ホットプレート上で加熱乾燥させた後、ライン/スペースが1ミクロンから20ミクロンまで、1ミクロン刻みに各5本ずつ設けられた石英製マスクを介して、表1中に記載の波長の光及び露光量で照射した。なお、ここで、NSR−1755i7Aは、ニコン製ステッパ型露光装置、PLA−600FAは、キャノン製コンタクトアライナ型露光装置を表す。照射後、80℃で1分間加熱しその後冷却した。
組成物がコートされた1枚のシリコンウエハと銅基板上に塗布された組成物膜についても、上記石英製マスクに代えて、幅20μmのストライプパターンの石英製マスクを使用した点を除き、現像工程まで同様にして、ストライプ状にした。該ストライプをさらに200℃のオーブンで3時間加熱した後、2気圧のプレッシャークッカー中に24時間放置したのち、剥離がないか目視で評価した。結果を表2に示す。
残りの1枚のシリコンウエハ上に塗布された組成物膜は、100℃で2分間、ホットプレート上で加熱乾燥させた後、200℃のオーブンで3時間加熱し、ASTM D149に従う絶縁破壊強さ試験に供した。結果を表2に示す。
FC−4430:界面活性剤(住友スリーエム(株)製商品名)
KBE−403:接着助剤(信越化学工業(株)製商品名)
X−70−093:界面活性剤(信越化学工業(株)製商品名)
NT−300P:感光剤(東洋合成工業(株)製商品名)
Claims (10)
- 数平均分子量が2,000〜800,000であり、下記式(3)で表される繰り返し単位からなるポリイミド樹脂。
- 1,2−ナフトキノンジアジドスルホニル基が1,2−ナフトキノンジアジド−4−スルホニル基及又は1,2−ナフトキノンジアジド−5−スルホニル基であることを特徴とする請求項1に記載のポリイミド樹脂。
- 式(3)中のnが3≦n≦400である請求項1〜5のいずれか1項に記載のポリイミド樹脂。
- (1)フェノール性水酸基を有するジアミンとテトラカルボン酸二無水物を反応させてポリアミック酸を調製する工程、
(2)前記ポリアミック酸を脱水閉環反応に付して、下記式(6)で表される3種の繰り返し単位からなる、フェノール性水酸基を有するポリイミドを調製する工程、
(3)前記ポリイミドを、1,2−ナフトキノンジアジドスルホニル化合物と反応させて、前記ポリイミドのフェノール性水酸基の水素原子の少なくとも一部を、1,2−ナフトキノンジアジドスルホニル基に置換する工程、
を含む、請求項1〜6のいずれか1項記載のポリイミド樹脂の製造方法。
- 請求項1〜6のいずれか1項記載のポリイミド樹脂を含む感光性樹脂組成物。
- (i)請求項1〜6のいずれか1項記載のポリイミド樹脂を含む層を基板上に形成する工程、
(ii)前記層を、所定のパターンが形成されたフォトマスクを通して、波長240〜500nmの光に露光する工程、
(iii)露光された層をアルカリ性溶液で溶解して、パターン化された層を得る工程、
を含むパターン化された層を形成する方法。 - 工程(ii)と(iii)の間に、40〜140℃で0.5〜10分間加熱する工程、
工程(iii)の後に、現像された層を120℃から300℃の範囲の温度で10分〜10時間加熱する工程、
をさらに含む請求項9記載のパターン化された膜を形成する方法。
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JP2006031084A JP4771412B2 (ja) | 2005-02-14 | 2006-02-08 | 感光性樹脂及びその製造方法 |
US11/352,267 US20060183880A1 (en) | 2005-02-14 | 2006-02-13 | Photosensitive resin and a method of preparing the same |
KR1020060014003A KR101205138B1 (ko) | 2005-02-14 | 2006-02-14 | 감광성 수지 및 그의 제조 방법 |
EP06075335A EP1705204B1 (en) | 2005-02-14 | 2006-02-14 | Photosensitive resin and a method of preparing the same |
DE602006013736T DE602006013736D1 (de) | 2005-02-14 | 2006-02-14 | Photosensitives Harz und Verfahren deren Herstellung |
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EP (1) | EP1705204B1 (ja) |
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JP2008158421A (ja) * | 2006-12-26 | 2008-07-10 | Asahi Kasei Corp | 感光性樹脂組成物及びそれを用いた感光性ドライフィルム |
JP5320639B2 (ja) * | 2008-02-13 | 2013-10-23 | 日立電線株式会社 | 絶縁電線 |
CN107356990A (zh) * | 2016-05-10 | 2017-11-17 | 住友化学株式会社 | 光学膜和使用光学膜的光学构件 |
KR102013283B1 (ko) * | 2017-12-05 | 2019-08-22 | 재단법인 오송첨단의료산업진흥재단 | 열팽창 계수를 이용한 박막전극 분리 방법 |
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DE2326314C2 (de) * | 1973-05-23 | 1983-10-27 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur Herstellung von Reliefstrukturen |
NL177718C (nl) * | 1973-02-22 | 1985-11-01 | Siemens Ag | Werkwijze ter vervaardiging van reliefstructuren uit warmte-bestendige polymeren. |
JPS5952822B2 (ja) * | 1978-04-14 | 1984-12-21 | 東レ株式会社 | 耐熱性感光材料 |
DE2931297A1 (de) * | 1979-08-01 | 1981-02-19 | Siemens Ag | Waermebestaendige positivresists und verfahren zur herstellung waermebestaendiger reliefstrukturen |
US5037720A (en) * | 1987-07-21 | 1991-08-06 | Hoechst Celanese Corporation | Hydroxylated aromatic polyamide polymer containing bound naphthoquinone diazide photosensitizer, method of making and use |
JPH0358048A (ja) * | 1989-07-27 | 1991-03-13 | Nitto Denko Corp | ポジ型感光性ポリイミド組成物 |
US5288588A (en) * | 1989-10-27 | 1994-02-22 | Nissan Chemical Industries Ltd. | Positive photosensitive polyimide resin composition comprising an o-quinone diazide as a photosensitive compound |
EP0459395B1 (en) * | 1990-05-29 | 1999-08-18 | Sumitomo Bakelite Company Limited | Positive photo-sensitive resin composition |
JP3319000B2 (ja) * | 1993-03-04 | 2002-08-26 | 東レ株式会社 | 化学線感応性組成物 |
JP3232022B2 (ja) * | 1997-03-31 | 2001-11-26 | 信越化学工業株式会社 | 感光性樹脂組成物 |
JP3426531B2 (ja) * | 1998-10-30 | 2003-07-14 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性重合体組成物、レリーフパターンの製造法及び電子部品 |
TW567198B (en) * | 1999-12-28 | 2003-12-21 | Kaneka Corp | Epoxy-modified polyimide, photosensitive composition, coverlay film, solder resist, and printed wiring board using the epoxy-modified polyimide |
JP4390028B2 (ja) * | 2000-10-04 | 2009-12-24 | 日産化学工業株式会社 | ポジ型感光性ポリイミド樹脂組成物 |
JP2002167367A (ja) * | 2000-12-01 | 2002-06-11 | Gun Ei Chem Ind Co Ltd | アミノ基含有フェノール誘導体 |
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- 2006-02-14 KR KR1020060014003A patent/KR101205138B1/ko active IP Right Grant
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KR101205138B1 (ko) | 2012-11-26 |
EP1705204A1 (en) | 2006-09-27 |
EP1705204B1 (en) | 2010-04-21 |
KR20060091256A (ko) | 2006-08-18 |
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