CA1165932A - Polymeric amide-ester resin heat-resistant photopolymerizable semiconductor and capacitor relief coatings - Google Patents
Polymeric amide-ester resin heat-resistant photopolymerizable semiconductor and capacitor relief coatingsInfo
- Publication number
- CA1165932A CA1165932A CA000384952A CA384952A CA1165932A CA 1165932 A CA1165932 A CA 1165932A CA 000384952 A CA000384952 A CA 000384952A CA 384952 A CA384952 A CA 384952A CA 1165932 A CA1165932 A CA 1165932A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- composition
- resin
- trimethylol propane
- aromatic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000011347 resin Substances 0.000 title claims abstract description 43
- 229920005989 resin Polymers 0.000 title claims abstract description 43
- 239000003990 capacitor Substances 0.000 title claims abstract description 5
- 239000004065 semiconductor Substances 0.000 title claims abstract description 4
- 238000000576 coating method Methods 0.000 title description 10
- 239000000203 mixture Substances 0.000 claims abstract description 73
- -1 acrylate compound Chemical class 0.000 claims abstract description 30
- 239000004952 Polyamide Substances 0.000 claims abstract description 20
- 229920002647 polyamide Polymers 0.000 claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 230000005855 radiation Effects 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 229920001721 polyimide Polymers 0.000 claims abstract description 8
- 239000004642 Polyimide Substances 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 18
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 claims description 11
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 11
- 239000003504 photosensitizing agent Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 6
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- PAMNGTABBVLRFN-UHFFFAOYSA-N 2-[bis[2-(diethylamino)-6-methylphenyl]methyl]-n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1C(C=1C(=CC=CC=1C)N(CC)CC)C1=C(C)C=CC=C1N(CC)CC PAMNGTABBVLRFN-UHFFFAOYSA-N 0.000 claims description 5
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 4
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 4
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 claims description 4
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- MTPIZGPBYCHTGQ-UHFFFAOYSA-N 2-[2,2-bis(2-prop-2-enoyloxyethoxymethyl)butoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCC(CC)(COCCOC(=O)C=C)COCCOC(=O)C=C MTPIZGPBYCHTGQ-UHFFFAOYSA-N 0.000 claims 2
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 claims 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 2
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000009719 polyimide resin Substances 0.000 claims 1
- 239000011342 resin composition Substances 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052710 silicon Inorganic materials 0.000 abstract description 9
- 239000010703 silicon Substances 0.000 abstract description 9
- 239000000470 constituent Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 235000012431 wafers Nutrition 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 8
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 4
- 235000000126 Styrax benzoin Nutrition 0.000 description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010073306 Exposure to radiation Diseases 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000010960 commercial process Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- LMGYOBQJBQAZKC-UHFFFAOYSA-N 1-(2-ethylphenyl)-2-hydroxy-2-phenylethanone Chemical compound CCC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 LMGYOBQJBQAZKC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- SONODMXIYNGWQY-UHFFFAOYSA-N 2-[bis[2-(dipropylamino)-6-methylphenyl]methyl]-3-methyl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=CC(C)=C1C(C=1C(=CC=CC=1C)N(CCC)CCC)C1=C(C)C=CC=C1N(CCC)CCC SONODMXIYNGWQY-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- VZMLJEYQUZKERO-UHFFFAOYSA-N 2-hydroxy-1-(2-methylphenyl)-2-phenylethanone Chemical compound CC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 VZMLJEYQUZKERO-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- ABKOZPAFVLROEM-UHFFFAOYSA-N [4-[4-(diethylamino)benzoyl]phenyl] prop-2-enoate Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(OC(=O)C=C)C=C1 ABKOZPAFVLROEM-UHFFFAOYSA-N 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/145—Polyamides; Polyesteramides; Polyimides
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Paints Or Removers (AREA)
- Graft Or Block Polymers (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Organic Insulating Materials (AREA)
- Materials For Photolithography (AREA)
- Formation Of Insulating Films (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/183,648 US4329419A (en) | 1980-09-03 | 1980-09-03 | Polymeric heat resistant photopolymerizable composition for semiconductors and capacitors |
| US183,648 | 1980-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1165932A true CA1165932A (en) | 1984-04-17 |
Family
ID=22673724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000384952A Expired CA1165932A (en) | 1980-09-03 | 1981-09-01 | Polymeric amide-ester resin heat-resistant photopolymerizable semiconductor and capacitor relief coatings |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4329419A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0047184B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JPS5776017A (cg-RX-API-DMAC7.html) |
| KR (1) | KR900006352B1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU543702B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1165932A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3168153D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES505185A0 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2083064B (cg-RX-API-DMAC7.html) |
| HK (1) | HK69085A (cg-RX-API-DMAC7.html) |
| IE (1) | IE51582B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL63717A0 (cg-RX-API-DMAC7.html) |
| MY (1) | MY8600180A (cg-RX-API-DMAC7.html) |
| SG (1) | SG70685G (cg-RX-API-DMAC7.html) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414312A (en) * | 1980-09-03 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Photopolymerizable polyamide ester resin compositions containing an oxygen scavenger |
| US4518473A (en) * | 1981-08-06 | 1985-05-21 | The Upjohn Company | Compositions and process |
| CA1195039A (en) * | 1982-01-04 | 1985-10-08 | David L. Goff | Radiation-sensitive polyimide precursor composition derived from a diaryl fluoro compound |
| JPS58223149A (ja) * | 1982-06-22 | 1983-12-24 | Toray Ind Inc | 感光性ポリイミド用現像液 |
| DE3227584A1 (de) * | 1982-07-23 | 1984-01-26 | Merck Patent Gmbh, 6100 Darmstadt | Fotolacke |
| DE3233912A1 (de) * | 1982-09-13 | 1984-03-15 | Merck Patent Gmbh, 6100 Darmstadt | Fotolacke zur ausbildung von reliefstrukturen aus hochwaermebestaendigen polymeren |
| GB8321379D0 (en) * | 1982-10-22 | 1983-09-07 | Ciba Geigy Ag | Positive image formation |
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| US4490774A (en) * | 1983-12-19 | 1984-12-25 | General Electric Company | Capacitors containing polyfunctional acrylate polymers as dielectrics |
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| CA1303281C (en) * | 1987-09-25 | 1992-06-09 | Masakazu Uekita | Patterned thin film and process for preparing the same |
| DE3808927A1 (de) * | 1988-03-17 | 1989-10-05 | Ciba Geigy Ag | Negativ-fotoresists von polyimid-typ mit 1,2-disulfonen |
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| US5786086A (en) * | 1996-01-02 | 1998-07-28 | Union Camp Corporation | Conductive wire coating |
| US7208260B2 (en) | 1998-12-31 | 2007-04-24 | Hynix Semiconductor Inc. | Cross-linking monomers for photoresist, and process for preparing photoresist polymers using the same |
| KR100362937B1 (ko) * | 1998-12-31 | 2003-10-04 | 주식회사 하이닉스반도체 | 신규의포토레지스트가교제,이를포함하는포토레지스트중합체및포토레지스트조성물 |
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| WO2006085741A1 (en) * | 2005-02-09 | 2006-08-17 | Stichting Dutch Polymer Institute | Process for preparing a polymeric relief structure |
| WO2015141618A1 (ja) * | 2014-03-17 | 2015-09-24 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物、硬化レリーフパターンの製造方法、並びに半導体装置 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635804A (cg-RX-API-DMAC7.html) * | 1962-03-21 | |||
| US3380831A (en) * | 1964-05-26 | 1968-04-30 | Du Pont | Photopolymerizable compositions and elements |
| US3479185A (en) * | 1965-06-03 | 1969-11-18 | Du Pont | Photopolymerizable compositions and layers containing 2,4,5-triphenylimidazoyl dimers |
| US3552973A (en) * | 1967-07-20 | 1971-01-05 | Du Pont | Light sensitive hexaarylbiimidazole/p- aminophenyl ketone compositions |
| US3623870A (en) * | 1969-07-22 | 1971-11-30 | Bell Telephone Labor Inc | Technique for the preparation of thermally stable photoresist |
| 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. |
| US3897395A (en) * | 1973-05-25 | 1975-07-29 | Univ Notre Dame Du Lac | Process for chain-extending unsaturated terminated polyimides and products prepared therefrom |
| DE2437348B2 (de) * | 1974-08-02 | 1976-10-07 | Ausscheidung in: 24 62 105 | Verfahren zur herstellung von reliefstrukturen |
| CH615935A5 (cg-RX-API-DMAC7.html) * | 1975-06-19 | 1980-02-29 | Ciba Geigy Ag | |
| US4093461A (en) * | 1975-07-18 | 1978-06-06 | Gaf Corporation | Positive working thermally stable photoresist composition, article and method of using |
| US4188224A (en) * | 1976-02-23 | 1980-02-12 | Ciba-Geigy Corporation | Photopolymerizable composition containing anthrones |
| US4132812A (en) * | 1977-09-02 | 1979-01-02 | W. R. Grace & Co. | Photocurable imidizable polyene-polythiol compositions |
| US4080484A (en) * | 1976-12-23 | 1978-03-21 | W. R. Grace & Co. | Photocurable imidizable polyene-polythiol compositions, method of coating therewith and coated articles |
| JPS5545748A (en) * | 1978-09-29 | 1980-03-31 | Hitachi Ltd | Photosensitive polymer and its production |
-
1980
- 1980-09-03 US US06/183,648 patent/US4329419A/en not_active Expired - Lifetime
-
1981
- 1981-09-01 AU AU74822/81A patent/AU543702B2/en not_active Ceased
- 1981-09-01 CA CA000384952A patent/CA1165932A/en not_active Expired
- 1981-09-01 JP JP56136213A patent/JPS5776017A/ja active Granted
- 1981-09-01 IE IE2006/81A patent/IE51582B1/en not_active IP Right Cessation
- 1981-09-02 GB GB8126576A patent/GB2083064B/en not_active Expired
- 1981-09-02 KR KR1019810003267A patent/KR900006352B1/ko not_active Expired
- 1981-09-02 DE DE8181304016T patent/DE3168153D1/de not_active Expired
- 1981-09-02 EP EP81304016A patent/EP0047184B1/en not_active Expired
- 1981-09-02 IL IL63717A patent/IL63717A0/xx not_active IP Right Cessation
- 1981-09-03 ES ES505185A patent/ES505185A0/es active Granted
-
1985
- 1985-09-12 HK HK690/85A patent/HK69085A/xx not_active IP Right Cessation
- 1985-09-24 SG SG706/85A patent/SG70685G/en unknown
-
1986
- 1986-12-30 MY MY180/86A patent/MY8600180A/xx unknown
-
1989
- 1989-11-22 JP JP1302294A patent/JPH02210712A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR830007762A (ko) | 1983-11-07 |
| JPH02210712A (ja) | 1990-08-22 |
| EP0047184A2 (en) | 1982-03-10 |
| DE3168153D1 (en) | 1985-02-21 |
| EP0047184A3 (en) | 1982-07-21 |
| ES8303486A1 (es) | 1983-02-01 |
| AU543702B2 (en) | 1985-04-26 |
| IL63717A0 (en) | 1981-12-31 |
| SG70685G (en) | 1986-05-02 |
| GB2083064B (en) | 1984-08-15 |
| IE51582B1 (en) | 1987-01-21 |
| AU7482281A (en) | 1982-03-11 |
| EP0047184B1 (en) | 1985-01-09 |
| JPS5776017A (en) | 1982-05-12 |
| HK69085A (en) | 1985-09-20 |
| JPH0233723B2 (cg-RX-API-DMAC7.html) | 1990-07-30 |
| ES505185A0 (es) | 1983-02-01 |
| GB2083064A (en) | 1982-03-17 |
| US4329419A (en) | 1982-05-11 |
| MY8600180A (en) | 1986-12-31 |
| KR900006352B1 (ko) | 1990-08-28 |
| IE812006L (en) | 1982-03-03 |
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