JP5649242B2 - 絶縁膜 - Google Patents
絶縁膜 Download PDFInfo
- Publication number
- JP5649242B2 JP5649242B2 JP2012556967A JP2012556967A JP5649242B2 JP 5649242 B2 JP5649242 B2 JP 5649242B2 JP 2012556967 A JP2012556967 A JP 2012556967A JP 2012556967 A JP2012556967 A JP 2012556967A JP 5649242 B2 JP5649242 B2 JP 5649242B2
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- JP
- Japan
- Prior art keywords
- general formula
- propylene glycol
- ether
- insulating film
- group
- 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.)
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- 238000009413 insulation Methods 0.000 title description 2
- 229920001721 polyimide Polymers 0.000 claims description 49
- 239000004642 Polyimide Substances 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 44
- 239000011810 insulating material Substances 0.000 claims description 34
- 125000000962 organic group Chemical group 0.000 claims description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- -1 diamine compound Chemical class 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical group 0.000 claims description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 8
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 claims description 4
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims description 4
- PVMMVWNXKOSPRB-UHFFFAOYSA-N 1,2-dipropoxypropane Chemical compound CCCOCC(C)OCCC PVMMVWNXKOSPRB-UHFFFAOYSA-N 0.000 claims description 4
- QMGJMGFZLXYHCR-UHFFFAOYSA-N 1-(2-butoxypropoxy)butane Chemical compound CCCCOCC(C)OCCCC QMGJMGFZLXYHCR-UHFFFAOYSA-N 0.000 claims description 4
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims description 4
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 claims description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 4
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 claims description 4
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 4
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 claims description 4
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000002318 adhesion promoter Substances 0.000 claims description 4
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 239000002243 precursor Substances 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 6
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 230000036211 photosensitivity Effects 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000013035 low temperature curing Methods 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000005353 silylalkyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- DHDFGUSJYSYXGN-UHFFFAOYSA-N 2-amino-4-[1-(3-amino-4-hydroxyphenyl)-1,1,2,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(F)(F)C(F)(C=2C=C(N)C(O)=CC=2)C(F)(F)F)=C1 DHDFGUSJYSYXGN-UHFFFAOYSA-N 0.000 description 1
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N C1C=CC=CC1 Chemical compound C1C=CC=CC1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- FYEMSWJCLOXELN-UHFFFAOYSA-N CC1=C(C)C=CC(C(C(F)(F)F)C(F)(F)F)C=C1 Chemical compound CC1=C(C)C=CC(C(C(F)(F)F)C(F)(F)F)C=C1 FYEMSWJCLOXELN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B17/00—Insulators or insulating bodies characterised by their form
- H01B17/56—Insulating bodies
- H01B17/62—Insulating-layers or insulating-films on metal bodies
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/303—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 H01B3/38 or H01B3/302
- H01B3/306—Polyimides or polyesterimides
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Description
Yは2価の有機基であり、
Zは下記一般式(3)で表されるジアミン化合物から由来したものである。
また、0≦p<1、0<q≦1、p+q=1である。
nは2〜500の整数であり、
Rは水素又はアルキル基又はシリルアルキル基(silyl alkyl)からなる群より選ばれるものである。
望ましくは、上記一般式(4)のmは2〜7の整数である。
Yは2価の有機基であり、
Zは下記一般式(3)で表されるジアミン化合物から由来したものである。
また、0≦p<1、0<q≦1、p+q=1である。
nは2〜500の整数であり、
Rは水素又はアルキル基又はシリルアルキル基(silyl alkyl)からなる群より選ばれるものである。
式中、Dは、例えば下記一般式又は水素原子(-H)から選ばれるいずれか一つである。
3,3',4,4'-ジフェニルエーテルテトラカルボン酸二無水物31.0g(0.1mole)に無水メチルアルコール300mlを添加し、80℃の温度で5時間還流および撹はんして反応させた後、残留溶媒を高温減圧下で乾燥して3,3',4,4'-ジフェニルエーテルテトラカルボン酸ジメチルエステル37.4g(収得率100%)を得た。得られた3,3',4,4'-ジフェニルエーテルテトラカルボン酸ジメチルエステル37.4g(0.1mole)に、チオニルクロライド35.4g(0.3mole)を滴下し、触媒量のN,N-ジメチルホルムアミドを添加した後、90℃の温度で3時間反応させ、室温に冷却し、残留のチオニルクロライドを減圧下で除去した後、3,3',4,4'-ジフェニルエーテルテトラカルボン酸ジクロライド41.0g(収得率100%)を得た。
上記合成例1で製造された3,3',4,4'-ジフェニルエーテルテトラカルボン酸ジクロライド24.6g(60mmole)を2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン15.4g(42mmole)と1,2-ビス(2-アミノエトキシ)エタン2.7g(18mmole)、そしてピリジン10.65gが溶けているN-メチル-2-ピロリドン150mlに窒素雰囲気下0℃でゆっくり滴下し、ゆっくり室温に上昇させた後、5時間撹はんすることにより反応させた。その後、反応物を2Lの水にゆっくり滴下して沈殿物を生成させ、得られた沈殿物は濾過して分離させ、水で3回洗浄した後、減圧乾燥してポリアミド酸メチルエステル(P-1)32.5gを得た。得られたポリマーの重さ平均分子量は28,000であった。
実施例1で2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン15.4g(42mmole)と1,2-ビス(2-アミノエトキシ)エタン2.7g(18mmole)の代わりに、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン13.2g(36mmole)と1,2-ビス(2-アミノエトキシ)エタン1.8g(12mmole)および4-オキシジアニリン2.4g(12mmole)を添加することを除いては、同様の方法を用いてポリマー(P-2)を製造した。得られたポリマー(P-2)の重さ平均分子量は25,000であった。
実施例1で2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン15.4g(42mmole)と1,2-ビス(2-アミノエトキシ)エタン2.7g(18mmole)の代わりに、全量2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン22.0g(60mmole)を用いることを除いては、同様の方法を用いてポリアミド酸メチルエステル(P-3)29.5gを得た。得られたポリマーの重さ平均分子量は29,500であった。
実施例2で2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン13.2g(36mmole)と1,2-ビス(2-アミノエトキシ)エタン1.8g(12mmole)および4-オキシジアニリン2.4g(12mmole)の代わりに、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)-ヘキサフルオロプロパン17.6g(48mmole)と4-オキシジアニリン2.4g(12mmole)を添加することを除いては、同様の方法を用いてポリイミド(P-4)を製造した。得られたポリマーの重さ平均分子量は23,000であった。
上記のように得られたポリイミド前駆体(P-1、P-3)又はポリイミド(P-2、P-4)3gと光活性化合物としてジアゾナフトキノンエステル化合物(TPPA320:OD/(OD+OH)=2/3の比率によりOHおよびODから選択的に与えられる。)1.0g、溶媒N-メチル-2-ピロリドン8gに加えた後、室温で1時間撹はんさせ、これを細孔1μmのフィルターで濾過して感光性有機絶縁材組成物を製造した。
テーパー角の測定は、パターンされたレジストの断面SEMイメージにより測定し、厚さおよび残膜測定は現像前/後のレジストに対して表面プロファイラ(surface profiler)を用いて測定した。
感度評価は、ステッパー(stepper)およびアライナ(aligner)により露光部が現像液に完全に溶けてなくなる露光量を測定した。
下記一般式(1)又は一般式(2)で表されるポリイミド又はその前駆体100重量部に対し光活性物質1〜50重量部を含む感光性有機絶縁材組成物。
[一般式1]
[一般式2]
式中、Xは4価の有機基であり、
Yは2価の有機基であり、
Zは下記一般式(3)で表されるジアミン化合物から由来したものである。
[一般式3]
式中、mは2〜21の整数であり、R'は炭素数2〜6のアルキレン基である。
また、0≦p<1、0<q≦1、p+q=1である。
nは2〜500の整数であり、
Rは水素又はアルキル基又はシリルアルキル基(silyl alkyl)からなる群より選ばれるものである。
[項目2]
上記Zは、下記一般式(4)で表されるジアミン化合物から由来したことを特徴とする項目1に記載の感光性有機絶縁材組成物。
[一般式4]
式中、mは2〜21の整数である。
[項目3]
上記一般式(3)のmは2〜7の整数であることを特徴とする項目2に記載の感光性有機絶縁材組成物。
[項目4]
上記一般式(1)又は一般式(2)の置換基Xは、下記一般式で表される有機基群から選ばれる1種以上であることを特徴とする項目1に記載の感光性有機絶縁材組成物。
[項目5]
上記一般式(1)又は一般式(2)の置換基Yは、下記一般式で表される2価の有機基群から選ばれる1種以上であることを特徴とする項目1に記載の感光性有機絶縁材組成物。
[項目6]
上記一般式(1)又は一般式(2)の置換基Yは、下記一般式で表されるジアミン化合物群から選ばれる1種以上から由来する有機基であることを特徴とする項目1に記載の感光性有機絶縁材組成物。
[項目7]
上記光活性物質は、下記一般式で表される化合物群から選ばれる1種以上であることを特徴とする項目1に記載の感光性有機絶縁材組成物。
式中、Dは、例えば下記一般式で表される有機基又は水素原子(-H)から選ばれる1種以上である。
[項目8]
溶解速度調節剤、増感剤、接着力増進剤および界面活性剤からなる群より選ばれる1種以上の添加剤をポリイミド又はその前駆体100重量部に対し0.1〜30重量部を含むことを特徴とする項目1に記載の感光性有機絶縁材組成物。
[項目9]
N-メチル-2-ピロリドン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、N,N-ジエチルアセトアミド、γ-ブチロラクトン、γ-バレロラクトン、m-クレゾール、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジプロピルエーテル、プロピレングリコールジブチルエーテル、乳酸エチル、乳酸ブチル、シクロヘキサノンおよびシクロペンタノンからなる群より選ばれる1種以上の溶媒を組成物100重量部に対し40〜97重量部を含むことを特徴とする項目1に記載の感光性有機絶縁材組成物。
[項目10]
項目1に記載の感光性樹脂組成物で製造されたポリイミドフィルムを含むOLED絶縁膜、LCD絶縁膜又は半導体絶縁膜。
Claims (6)
- 下記一般式(1)で表されるポリイミド100重量部及び下記一般式(8)で表される化合物群から選ばれる1種以上である光活性物質1〜50重量部を含む感光性有機絶縁材組成物で製造されたポリイミドフィルムを含む絶縁膜。
[一般式(1)]
Xは4価の有機基であり、
Yは下記一般式(6)で表される2価の有機基群から選ばれる1種以上であり、
Zは下記一般式(4)で表されるジアミン化合物から由来したものであり、
0<p<1、0<q<1、p+q=1であり、
nは2〜500の整数である。
[一般式(4)]
[一般式(6)]
[一般式(9)]
- 上記一般式(4)のmは2〜7の整数であることを特徴とする、
請求項1に記載の絶縁膜。 - 溶解速度調節剤、増感剤、接着力増進剤および界面活性剤からなる群より選ばれる1種以上の添加剤を、前記ポリイミド100重量部に対し0.1〜30重量部を含むことを特徴とする、
請求項1から請求項3までの何れか1項に記載の絶縁膜。 - N-メチル-2-ピロリドン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、N,N-ジエチルアセトアミド、γ-ブチロラクトン、γ-バレロラクトン、m-クレゾール、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジプロピルエーテル、プロピレングリコールジブチルエーテル、乳酸エチル、乳酸ブチル、シクロヘキサノンおよびシクロペンタノンからなる群より選ばれる1種以上の溶媒を組成物100重量部に対し40〜97重量部を含むことを特徴とする、
請求項1から請求項4までの何れか1項に記載の絶縁膜。 - 上記絶縁膜は、OLED用絶縁膜、LCD用絶縁膜又は半導体用絶縁膜であることを特徴とする、
請求項1から請求項5までの何れか1項に記載の絶縁膜。
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-
2011
- 2011-02-23 KR KR1020110015963A patent/KR101304590B1/ko active IP Right Grant
- 2011-03-07 CN CN201180023554.8A patent/CN102893214B/zh active Active
- 2011-03-07 JP JP2012556967A patent/JP5649242B2/ja active Active
- 2011-03-07 EP EP11753570.8A patent/EP2546697A4/en not_active Withdrawn
- 2011-03-07 WO PCT/KR2011/001562 patent/WO2011111965A2/ko active Application Filing
- 2011-03-11 US US13/046,319 patent/US20110223538A1/en not_active Abandoned
- 2011-03-11 TW TW100108280A patent/TWI446107B/zh active
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Also Published As
Publication number | Publication date |
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CN102893214A (zh) | 2013-01-23 |
KR20110102819A (ko) | 2011-09-19 |
JP2014225031A (ja) | 2014-12-04 |
KR101304590B1 (ko) | 2013-09-05 |
TW201135359A (en) | 2011-10-16 |
JP2013522660A (ja) | 2013-06-13 |
TWI446107B (zh) | 2014-07-21 |
WO2011111965A2 (ko) | 2011-09-15 |
US20110223538A1 (en) | 2011-09-15 |
WO2011111965A3 (ko) | 2012-01-05 |
CN102893214B (zh) | 2015-11-25 |
EP2546697A4 (en) | 2017-01-25 |
EP2546697A2 (en) | 2013-01-16 |
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