TWI665272B - 塗布型絕緣膜形成用組成物 - Google Patents
塗布型絕緣膜形成用組成物 Download PDFInfo
- Publication number
- TWI665272B TWI665272B TW104128941A TW104128941A TWI665272B TW I665272 B TWI665272 B TW I665272B TW 104128941 A TW104128941 A TW 104128941A TW 104128941 A TW104128941 A TW 104128941A TW I665272 B TWI665272 B TW I665272B
- Authority
- TW
- Taiwan
- Prior art keywords
- insulating film
- forming
- ring
- composition
- cyclic olefin
- Prior art date
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- 239000008199 coating composition Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims abstract description 48
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims abstract description 43
- -1 cyclic olefin Chemical class 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 36
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 150000001336 alkenes Chemical class 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 10
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 7
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- 239000004711 α-olefin Substances 0.000 claims description 6
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 5
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 claims description 5
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims description 5
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 60
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 30
- 238000009413 insulation Methods 0.000 abstract description 10
- 239000011368 organic material Substances 0.000 abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000010408 film Substances 0.000 description 109
- 239000011248 coating agent Substances 0.000 description 38
- 239000000178 monomer Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004642 Polyimide Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000003746 surface roughness Effects 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 3
- 229920000052 poly(p-xylylene) Polymers 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229940069096 dodecene Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 231100000615 substance of very high concern Toxicity 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- DBUJFULDVAZULB-UHFFFAOYSA-N 1-methoxypentane Chemical compound CCCCCOC DBUJFULDVAZULB-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- FMVOPJLFZGSYOS-UHFFFAOYSA-N 2-[2-(2-ethoxypropoxy)propoxy]propan-1-ol Chemical compound CCOC(C)COC(C)COC(C)CO FMVOPJLFZGSYOS-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical group C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- WQLASZCDZBNUMT-UHFFFAOYSA-N 3,3-dimethoxybutyl propanoate Chemical compound C(CC)(=O)OCCC(C)(OC)OC WQLASZCDZBNUMT-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- ZSCDRSWJZRRPGN-UHFFFAOYSA-N 4-oxahomoadamantan-5-one Chemical group C1C(C2)C(=O)OC3CC1CC2C3 ZSCDRSWJZRRPGN-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
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- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
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- 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
- H01B3/44—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 vinyl resins; acrylic resins
- H01B3/441—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 vinyl resins; acrylic resins from alkenes
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- C09D145/00—Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
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- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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Abstract
提供一種絕緣膜形成用組成物,其形成絕緣膜之有機材料的溶解安定性以及安全性優異,可藉由塗布法形成相對電容率低、絕緣電阻值高、可濕性高之絕緣膜,且該絕緣膜可藉由塗布法形成上位層(upper layer)。
本發明之絕緣膜形成用組成物含有下列環狀烯烴共聚合物與下列溶劑。
環狀烯烴共聚合物:環狀烯烴與鏈狀烯烴之共聚合物
溶劑:含有為下列式(1)所表示之化合物且標準沸點為100℃以上、小於300℃之化合物。式(1)中,環Z係從5~6元之飽和或不飽和環烴以及苯環中所選擇之環,R1為烴基或醯基。環Z至少具有R1O基作為取代基,當具有2個以上取代基時,2個取代基可相互鍵結而與構成環Z之碳原子共同形成環。
Description
本發明關於一種絕緣膜形成用組成物,其係含有作為溶質之環狀烯烴共聚合物與溶解該等之溶劑的塗布性優異之絕緣膜形成用組成物,藉由塗布法而形成「可形成上位層(upper layer)之具有可濕性的塗膜」。本案主張2014年9月3日於日本申請專利之日本特願2014-179447號之優先權,在此引用其內容。
一般來講,作為絕緣膜的材料有二氧化矽、氮化矽等無機材料、或環狀烯烴共聚合物、聚醯亞胺、聚對二甲苯、非晶質氟樹脂、聚丙烯酸樹脂等有機材料,因應用途或需求特性而被區分使用。
以往,於液晶顯示器以無機材料為主流,但近年由於顯示器之可撓化、降低成本之需求,開始取代為有機材料。
無機材料係藉由氣相沈積法形成絕緣膜,但於可藉由塗布法容易且低價地形成絕緣膜之觀點、可得到輕量且可撓之絕緣膜的觀點,有機材料較為優異。若活用前述優點,則可藉由塗布法大量、迅速且低價地形成大面積之電子裝置(非專利文獻1)。作為電子裝置,例
如有機薄膜電晶體,可藉由1)閘電極印刷、2)閘極絕緣膜印刷、3)半導體印刷、4)源‧汲電極印刷之合計4次的印刷而製造。
藉由塗布法製造電子裝置時,將前述有機材料墨水化或糊化係重要,但前述聚醯亞胺對於溶劑之低溶解性為問題所在。又,聚醯亞胺前驅物之聚醯胺酸對於溶劑之溶解性雖高,但由於為了使其聚醯亞胺化,必須以高溫加熱(專利文獻1),而有對基材或被印刷材料造成損傷之問題。
又,利用聚對二甲苯形成塗膜必須藉由加熱進行熱分解(專利文獻2)。因此,不適合藉由塗布法製造電子裝置。
再者,非晶質氟樹脂雖可藉由塗布法形成塗膜,但由於所得到塗膜之可濕性低,難以於該塗膜上藉由塗布法形成上位層,而採取藉由氣相沈積法形成電極或有機半導體等上位層之方法、將非晶質氟樹脂之塗布步驟移至前述上位層形成後之方法、或者於非晶質氟樹脂之塗膜上隔著包含無機材料之密合層而形成上位層之方法(專利文獻3)。但是,難以僅藉由塗布法製造電子裝置或發生形狀上之限制為問題所在。
另一方面,環狀烯烴共聚合物之溶劑可濕性高。又,環狀烯烴共聚合物之相對電容率低,絕緣電阻值高。但是,環狀烯烴共聚合物對於溶劑之溶解性低,即使墨水化後亦容易發生沉澱或相分離為問題所在。作為改善溶解性的方法,習知有化學修飾環狀烯烴共聚合
物之方法,但亦有化學修飾造成絕緣性能降低之問題(專利文獻4及5)。
前述有機材料墨水化時主要使用之溶劑,可使用甲苯、二甲苯、四氫呋喃、二烷、N,N-二甲基甲醯胺、N-甲基吡咯啶酮、環己酮、乙二醇系醚等,但由於揮發性過高而難以使塗膜表面平滑化,或由於被指定為高度關注物質(SVHC)之管理對象物質而難以於工業上使用,因而尋求替代品。
專利文獻1:日本特開2012-064662號公報
專利文獻2:日本特開2010-283332號公報
專利文獻3:日本特開2010-278173號公報
專利文獻4:日本特開2008-111033號公報
專利文獻5:日本特開2009-167433號公報
非專利文獻1:印刷電子學(Printed electronics)技術菅沼克昭‧棚網弘(ISBN 978-4-7693-1280-2)
因此,本發明之目的在於提供一種絕緣膜形成用組成物,形成絕緣膜之有機材料的溶解安定性以及安全性優異,可藉由塗布法形成相對電容率低、絕緣電阻值高、可濕性高之絕緣膜,且該絕緣膜可藉由塗布法形成上位層。
本發明者們為了解決前述課題而積極探討之結果,發現藉由將環狀烯烴共聚合物與特定之安全的溶劑組合,可安定地形成適合塗布法之墨水,藉由塗布該墨水,可形成相對電容率低、絕緣電阻值高之絕緣膜,且該絕緣膜具有可藉由塗布法形成上位層之可濕性。本發明係基於該等見解而完成者。
換言之,本發明提供一種含有下列環狀烯烴共聚合物與下列溶劑之絕緣膜形成用組成物。
環狀烯烴共聚合物:環狀烯烴與鏈狀烯烴之共聚合物
溶劑:含有為下列式(1)所表示之化合物且標準沸點為100℃以上、小於300℃之化合物,
(式中,環Z係從5~6元之飽和或不飽和環烴以及苯環中選擇之環,R1為烴基或醯基。環Z至少具有R1O基作為取代基,當具有2個以上取代基時,2個取代基可相互鍵結而與構成環Z之碳原子共同形成環)。
本發明亦提供一種如前述之絕緣膜形成用組成物,其中環狀烯烴共聚合物係可具有取代基之降莰烯及/或環十二烯與碳數2~8之鏈狀α-烯烴之共聚合物。
本發明亦提供一種如前述之絕緣膜形成用組
成物,其中溶劑含有選自於環己基甲醚、環己醇乙酸酯、甲氧苯、乙氧苯以及環戊基甲醚中之至少1種之化合物。
本發明亦提供一種如前述之絕緣膜形成用組成物,其黏度[25℃、剪切速度10(1/s)下]為0.1~5000mPa‧s。
換言之,本發明係與下列有關。
[1]一種含有下列環狀烯烴共聚合物與下列溶劑之絕緣膜形成用組成物。
環狀烯烴共聚合物:環狀烯烴與鏈狀烯烴之共聚合物
溶劑:含有為式(1)(式中,環Z係從5~6元之飽和或不飽和環烴以及苯環中選擇之環,R1為烴基或醯基。環Z至少具有R1O基作為取代基,當具有2個以上取代基時,2個取代基可相互鍵結而與構成環Z之碳原子共同形成環)所表示之化合物且標準沸點為100℃以上、小於300℃之化合物。
[2]如[1]之絕緣膜形成用組成物,其中環狀烯烴共聚合物含有環狀烯烴共聚合物全量之50~90重量%的來自環狀烯烴之單體單元,且含有環狀烯烴共聚合物全量之10~50重量%的來自鏈狀烯烴之單體單元。
[3]如[1]或[2]之絕緣膜形成用組成物,其中環狀烯烴共聚合物中來自環狀烯烴之單體單元與來自鏈狀烯烴之單體單元的合計含量為環狀烯烴共聚合物全量之50重量%以上。
[4]如[1]至[3]中任一項之絕緣膜形成用組成物,其中環狀烯烴共聚合物之玻璃轉移溫度(根據ISO
11375-1,-2,-3)為40~220℃。
[5]如[1]至[4]中任一項之絕緣膜形成用組成物,其中環狀烯烴共聚合物之重量平均分子量(藉由GPC之聚苯乙烯換算)為3000~200000。
[6]如[1]至[5]中任一項之絕緣膜形成用組成物,其中環狀烯烴共聚合物係可具有取代基之降莰烯及/或環十二烯與碳數2~8之鏈狀α-烯烴之共聚合物。
[7]如[1]至[6]中任一項之絕緣膜形成用組成物,其係含有作為溶質之環狀烯烴共聚合物與溶劑之絕緣膜形成用組成物,絕緣膜形成用組成物所含有之溶質全量中,環狀烯烴共聚合物所佔比率為50重量%以上。
[8]如[1]至[7]中任一項之絕緣膜形成用組成物,其中溶劑含有選自於環己基甲醚、環己醇乙酸酯、甲氧苯、乙氧苯以及環戊基甲醚中之至少1種之化合物。
[9]如[1]至[8]中任一項之絕緣膜形成用組成物,其中溶劑含有佔絕緣膜形成用組成物所含溶劑全量之50重量%以上的為式(1)所示之化合物且標準沸點為100℃以上,小於300℃之化合物。
[10]如[8]或[9]之絕緣膜形成用組成物,其中溶劑含有佔絕緣膜形成用組成物所含溶劑全量之50重量%以上的選自於環己基甲醚、環己醇乙酸酯、甲氧苯、乙氧苯以及環戊基甲醚中之至少1種之化合物。
[11]如[1]至[10]中任一項之絕緣膜形成用組成物,其中絕緣膜形成用組成物全量中,溶劑所佔比率為60重量%以上。
[12]如[1]至[11]中任一項之絕緣膜形成用組成物,其中絕緣膜形成用組成物全量中,式(1)表示之化合物所佔比率為30重量%以上。
[13]如[1]至[12]中任一項之絕緣膜形成用組成物,其中絕緣膜形成用組成物全量中,溶質所佔比率為0.05~40.00重量%。
[14]如[1]至[13]中任一項之絕緣膜形成用組成物,其中絕緣膜形成用組成物全量中,環狀烯烴共聚合物所佔比率為0.05~40.00重量%。
[15]如[1]至[14]中任一項之絕緣膜形成用組成物,其黏度[25℃、剪切速度10(1/s)下]為0.1~5000mPa‧s。
[16]一種包含[1]至[15]中任一項之絕緣膜形成用組成物之固化物的塗膜。
[17]如[16]之塗膜,其水接觸角小於90°。
[18]如[16]或[17]之塗膜,其表面粗糙度(算術平均粗糙度;Ra)為1nm以下。
[19]如[16]至[18]中任一項之塗膜,其中絕緣電阻值(根據JIS C2110)為9kV/0.1mm以上。
[20]如[16]至[19]中任一項之塗膜,其中相對電容率(IEC 60250)(1~10kHz,25℃)為2.7以下。
本發明之塗布型絕緣膜形成用組成物,安全性以及作為墨水之安定性高,藉由塗布、乾燥,可形成相較於習知產品而相對電容率低且絕緣電阻值高之絕緣膜,該絕緣膜可濕性高而可藉由塗布法形成上位層。因
此,可適用於藉由塗布法形成含絕緣膜之電子裝置(例如電晶體、電容器、電感器、熱阻器、壓電元件等)之用途。
[溶劑]
本發明之絕緣膜形成用組成物,至少含有下列式(1)所示化合物作為溶劑。
(式中,環Z係從5~6元之飽和或不飽和環烴以及苯環中選擇之環,R1為烴基或醯基。環Z至少具有R1O基作為取代基,當具有2個以上取代基時,2個取代基可相互鍵結而與構成環Z之碳原子共同形成環)
前述式中,環Z係從5~6元之飽和或不飽和環烴以及苯環中選擇之環。作為前述5~6元之飽和或不飽和環烴,可舉例如環戊烷及環己烷等環烷;環戊烯、環戊二烯、環己烯、環己二烯等環烯(包含環二烯)。
R1為烴基(-R'基)或醯基(-C(=O)R'基)。前述R'為烴基,包含脂肪族烴基、脂環型烴基、芳香族烴基以及該等鍵結之基。
作為前述脂肪族烴基,可舉例如甲基、乙基、丙基、異丙基、丁基、異丁基、s-丁基、t-丁基、戊基
、己基、癸基、十二基等碳數1~20左右(較佳為1~10,特佳為1~3)之烷基;乙烯基、烯丙基、1-丁烯基等碳數2~20左右(較佳為2~10,特佳為2~3)之烯基;乙炔基、丙炔基等碳數2~20左右(較佳為2~10,特佳為2~3)之炔基等。
作為前述脂環型烴基,可列舉環丙基、環丁基、環戊基、環己基、環辛基等3~20元左右(較佳為3~15元,特佳為5~8元)之環烷基;環戊烯基、環己烯基等3~20元左右(較佳為3~15元,特佳為5~8元)之環烯基;全氫萘-1-基、降莰基、金剛烷基、三環[5.2.1.02,6]癸烷-8-基、四環[4.4.0.12,5.17,10]十二烷-3-基等4~20元左右之橋聯環烴基等。
作為前述芳香族烴基,可列舉苯基、萘基等碳數6~14左右(較佳為6~10)之芳香族烴基。
作為R',其中較佳為碳數1~20之烷基、碳數1~20之脂肪族醯基或碳數6~14之芳香族醯基。
環Z至少具有R1O基(式(1)中所示之基)作為取代基,但除了R1O基以外亦可具有其他取代基。作為其他取代基,可舉例如鹵素原子、側氧基、羥基、取代氧基(例如C1-4烷氧基、C6-10芳氧基、C7-16芳烷氧基、C1-4醯氧基等)、羧基、取代氧羰基(例如C1-4烷氧羰基、C6-10芳氧羰基、C7-16芳烷氧羰基等)、取代或非取代胺甲醯基、氰基、硝基、取代或非取代胺基、磺酸基、雜環基(例如自以下記載之雜環構造式除去1個氫原子之基等)、烷基(例如甲基及乙基等C1-4烷基等)、烯基(例如乙烯基
、烯丙基、1-丁烯基等C2-4烯基)、炔基(例如乙炔基及丙炔基等C2-4炔基等)、C3-8環烷基、芳香基(例如苯基及萘基等C6-10芳香基)等。
作為前述2個取代基可相互鍵結而與構成環Z之碳原子共同形成之環,可列舉脂環、芳香環、雜環等。
作為前述脂環,可列舉環丙烷、環丁烷、環戊烷、環己烷、環辛烷等3~20元左右(較佳為3~15元,特佳為5~8元)之環烷;環戊烯及環己烯等3~20元左右(較佳為3~15元,特佳為5~8元)之環烯;全氫萘、降莰烷、金剛烷、三環[5.2.1.02,6]癸烷、四環[4.4.0.12,5.17,10]十二烷等4~20元左右之橋聯環烴等。
作為前述芳香環,可列舉苯、萘等碳數6~14左右(較佳為6~10)之芳香烴。
作為前述雜環,可舉例如含有氧原子作為雜原子之雜環(例如環氧乙烷(oxirane)環等3元環;氧呾(oxetane)環等4元環;呋喃環、四氫呋喃環、氧唑(oxazole)環、異氧唑環、γ-丁內酯環等5元環;4-側氧基-4H-哌喃環、四氫哌喃環、啉環等6元環;苯并呋喃環、異苯并呋喃環、4-側氧基-4H-唏環、唍環、異唍環等縮合環;3-氧雜三環[4.3.1.14,8]十一烷-2-酮環及3-氧雜三環[4.2.1.04,8]壬烷-2-酮環等橋聯環)、含有硫原子作為雜原子之雜環(例如噻吩環、噻唑環、異噻唑環、噻二唑環等5元環;4-側氧基-4H-噻喃環等6元環;苯并噻吩環等縮合環等)、含有氮原子作為雜原子之雜環(例如順丁烯二醯亞胺環、吡咯環、吡咯啶環、吡唑環、咪唑環、三
唑環等5元環;異三聚氰酸環、吡啶環、嗒環、嘧啶環、吡環、哌啶環、哌環等6元環;吲哚環、吲哚啉環、喹啉環、吖啶環、啶環、喹唑啉環、嘌呤環、咔唑環等縮合環等)等芳香族雜環型化合物以及非芳香族雜環型化合物。
式(1)所示化合物之標準沸點為100℃以上、小於300℃,較佳為100~280℃,特佳為100~250℃,最佳為100~200℃。標準沸點若小於前述範圍,則由於揮發性變得過高,塗布作業時組成物之黏度難以保持一定,而有難以形成平滑塗膜之傾向。
作為式(1)所示之化合物,其中從安全性以及環狀烯烴共聚合物之溶解性優異,且具有適度揮發性而可形成平滑性優異之塗膜的觀點來看,又以選自於環己基甲醚、環己醇乙酸酯、甲氧苯、乙氧苯以及環戊基甲醚中之至少1種之化合物為較佳。
本發明之絕緣膜形成用組成物亦可於無損本發明效果之範圍內含有式(1)所示化合物以外之化合物作為溶劑。作為式(1)所示化合物以外之化合物,可列舉乙二醇單甲醚、乙二醇單乙醚、乙二醇-n-丙醚、乙二醇-n-丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇-n-丙醚、二乙二醇-n-丁醚、三乙二醇單甲醚、三乙二醇單乙醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇-n-丙醚、丙二醇-n-丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇-n-丙醚、二丙二醇-n-丁醚、三丙二醇單甲醚、三丙二醇單乙醚等(聚)烷二醇單烷基醚類;乙二醇單甲
醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯等(聚)烷二醇單烷基醚乙酸酯類;二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲乙醚、二丙二醇二甲醚等(聚)烷二醇二烷基醚類;四氫呋喃等醚類;甲基乙基酮、環己酮、2-庚酮、3-庚酮等酮類;2-羥基丙酸甲酯、2-羥基丙酸乙酯等乳酸烷基酯類;2-羥基-2-甲基丙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、乙酸3-甲基-3-甲氧基丁酯、丙酸3-甲氧基-3-甲氧基丁酯、乙酸乙酯、乙酸n-丙酯、乙酸異丙酯、乙酸n-丁酯、乙酸異丁酯、甲酸n-戊酯、乙酸異戊酯、丙酸n-丁酯、丁酸乙酯、丁酸n-丙酯、丁酸異丙酯、丁酸n-丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸n-丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、2-側氧丁酸乙酯等酯類;甲苯、二甲苯等芳香烴類;N-甲基吡咯啶酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、四甲基尿素等醯胺類等。該等可單獨1種或組合2種以上使用。
本發明之絕緣膜形成用組成物所含溶劑全量中,式(1)表示之化合物(含有2種以上時為其總量)所佔比率例如為50重量%以上,較佳為70重量%以上,特佳為90重量%以上。溶劑中式(1)所示化合物之比率若小於前述範圍,則環狀烯烴共聚合物之溶解安定性以及安全性有降低之傾向。
[溶質]
本發明之絕緣膜形成用組成物含有為環狀烯烴與鏈狀烯烴共聚合物之環狀烯烴共聚合物作為溶質。
環狀烯烴包含多環烯烴與單環烯烴。該等可單獨1種或組合2種以上使用。
作為前述多環烯烴,較佳為碳數4~20左右之多環烯烴,可舉例如降莰烯及降莰二烯(norbornadiene)等雙環體;二環戊二烯及5,6-二氫二環戊二烯等三環體;四環十二烯等四環體等環內具有碳-碳雙鍵之多環烴[特別是橋聯環烴(含橋聯環二烯)]。
作為前述單環烯烴,較佳為碳數3~20左右之單環烯烴,可舉例如環丁烯、環戊烯、環戊二烯、環辛烯、環十二烯等環內具有碳-碳雙鍵之單環烴[特別是環烯(含環二烯)]。
前述多環或單環烯烴亦可具有各種取代基。作為前述取代基,可列舉與前述式(1)中環Z可具有之取代基同樣之例。
作為前述鏈狀烯烴,可舉例如乙烯、丙烯、1-丁烯、2-丁烯、異丁烯、1-戊烯、2-戊烯、1-己烯、2-己烯、3-己烯、1-庚烯、1-辛烯、2-辛烯、3-辛烯、4-辛烯、1-壬烯、1-癸烯、1-十二烯、1,5-己二烯、1,6-庚二烯、1,7-辛二烯等碳數2~8之烯烴(含二烯烴);苯乙烯、α-甲基苯乙烯、m-乙烯基甲苯、p-乙烯基甲苯、1-乙烯基萘等芳香族乙烯化合物。
本發明之環狀烯烴共聚合物,可藉由將至少含有前述環狀烯烴與鏈狀烯烴之單體單元混合物於複分
解聚合觸媒存在下進行共聚合(隨機共聚合、嵌段共聚合、交互共聚合或接枝共聚合)而得到。
前述來自環狀烯烴之單體單元含量為例如環狀烯烴共聚合物全量之50~90重量%,較佳為60~85重量%。
前述來自鏈狀烯烴之單體單元含量為例如環狀烯烴共聚合物全量之10~50重量%,較佳為15~40重量%。
再者,前述來自環狀烯烴之單體單元與前述來自鏈狀烯烴之單體單元的合計含量為例如環狀烯烴共聚合物全量之50重量%以上,較佳為60重量%以上,更佳為70重量%以上,再更佳為80重量%以上,最佳為90重量%以上。藉由將構成環狀烯烴共聚合物之來自環狀烯烴之單體單元與來自鏈狀烯烴之單體單元的含量調整為前述範圍,可控制玻璃轉移溫度。
環狀烯烴共聚合物之玻璃轉移溫度(根據ISO 11375-1,-2,-3),從耐熱性與加工性優異之觀點來看,較佳為例如40~220℃(特別是60~200℃)。
環狀烯烴共聚合物之重量平均分子量(藉由GPC之聚苯乙烯換算)可為例如3000~200000,較佳為5000~150000。
作為本發明之環狀烯烴共聚合物,其中較佳為環狀烯烴與鏈狀α-烯烴之共聚合物,特佳為可具有取代基之降莰烯及/或環十二烯與碳數2~8之鏈狀α-烯烴之共聚合物,尤其以可具有取代基之降莰烯與碳數2~8
之鏈狀α-烯烴之共聚合物[=具有來自下列式(2)所示可具有取代基之降莰烯單體單元與來自下列式(3)所示碳數2~8之鏈狀α-烯烴單體單元的共聚合物]為較佳。
前述式(2)中,R2、R3表示相同或相異之氫原子或前述列舉之取代基。R2與R3可相互鍵結而與構成降莰烯環之碳原子共同形成環。作為前述環,可舉例與前述式(1)中2個取代基可相互鍵結而與構成環Z之碳原子共同形成之環同樣之例。
前述式(3)中,R4表示氫原子或碳數1~6的烷基。
本發明中,可合適地使用例如商品名「TOPAS」(Polyplastics股份有限公司製)、商品名「APEL」(三井化學股份有限公司製)等市販品。
本發明之絕緣膜形成用組成物,亦可於無損本發明效果之範圍內含有前述環狀烯烴共聚合物以外之化合物(例如,環狀烯烴聚合物、聚醯亞胺、聚對二甲苯、非晶質氟樹脂、聚丙烯酸樹脂等)作為溶質,但本發明之絕緣膜形成用組成物所含溶質全量中,前述環狀烯烴共聚合物(含2種以上時為其總量)所佔比率為例如50重量%以上,較佳為70重量%以上,特佳為90重量%以上。
[絕緣膜形成用組成物]
本發明之絕緣膜形成用組成物,可藉由混合前述溶
劑與前述溶質,於例如20~120℃,攪拌0.5~48小時左右而製造。
本發明之絕緣膜形成用組成物全量中,溶劑所佔比率為例如60重量%以上(例如60.00~99.95重量%),較佳為70重量%以上(例如70.0~99.9重量%),特佳為80重量%以上(例如80.0~99.9重量%)。
又,本發明之絕緣膜形成用組成物全量中,式(1)表示之化合物(含2種以上時為其總量)所佔比率為例如30重量%以上(例如30.00~99.95重量%),較佳為35重量%以上(例如35.0~99.9重量%),更佳為40重量%以上(例如40.0~99.9重量%),特佳為50重量%以上(例如50.0~99.9重量%),最佳為60重量%以上(例如60.0~99.9重量%),再更佳為75重量%以上(例如75.0~99.9重量%)。
又,本發明之絕緣膜形成用組成物全量中,溶質所佔比率為例如0.05重量%以上(例如0.05~40.00重量%),較佳為0.1重量%以上(例如0.1~30.0重量%)。
又,本發明之絕緣膜形成用組成物全量中,環狀烯烴共聚合物所佔比率為例如0.05重量%以上(例如0.05~40.00重量%),較佳為0.1重量%以上(例如0.1~30.0重量%)。
本發明之絕緣膜形成用組成物為低黏度且塗布性優異,其黏度[25℃、剪切速度10(1/s)下]為例如0.1~5000mPa‧s,較佳為1~1000mPa‧s。另外,黏度可使用流變儀(商品名「PHYSICA UDS200」,Anton Paar公司製)測定。
本發明之絕緣膜形成用組成物可藉由塗布(可採用旋轉塗布法、浸塗法、噴霧法等慣用方法)、乾燥(例如於20~120℃加熱乾燥0.1~5分鐘左右)而形成塗膜。又,本發明之絕緣膜形成用組成物,從薄膜到厚膜之廣範圍的膜厚形成能優異,可形成具有2500nm以下(例如10~2500nm)之均勻膜厚的塗膜。
將本發明絕緣膜形成用組成物塗布、乾燥所得到之塗膜係可濕性高,水接觸角小於90°(較佳為10°以上、小於90°,特佳為30°以上、小於90°,最佳為60°以上、小於90°)。因此,可藉由塗布法形成上位層。
本發明之絕緣膜形成用組成物不易發生相分離,作為墨水之安定性高。因此,所得到塗膜之平坦性優異,表面粗糙度(算術平均粗糙度;Ra)為1nm以下(例如0.05~1nm)。
將本發明絕緣膜形成用組成物塗布、乾燥所得到之塗膜具有高絕緣電阻值(根據JIS C2110),例如為9kV/0.1mm以上,較佳為10kV/0.1mm以上。
將本發明絕緣膜形成用組成物塗布、乾燥所得到之塗膜的相對電容率(IEC 60250)(1~10kHz,25℃)低,例如為2.7以下(例如為1.5~2.7),較佳為2.5以下(例如為1.5~2.5)。
本發明之絕緣膜形成用組成物可藉由塗布法形成兼具前述特性之塗膜。又,由於得到之塗膜可濕性高,可藉由塗布法形成上位層。因此,可適用於大量、迅速且低價地形成具備大面積之絕緣膜的電子裝置之用
途。
以下,藉由實施例更具體說明本發明,但本發明不限定於該等之實施例。另外,沸點若無特別記載,則為1atm下之沸點,即標準沸點。
實施例1
於100mL樣本瓶秤取50.0g環戊基甲醚作為溶劑,於此投入精密秤量之環狀烯烴共聚合物[降莰烯與乙烯之共聚合物;商品名「TOPAS 5013S-04」(Tg:134℃)、「TOPAS 6013S-04」(Tg:138℃)或「TOPAS 7010XITI」,皆為Polyplastics股份有限公司製]0.050g作為溶質,其後,一邊藉由攪拌片(stirrer chip)攪拌,一邊加熱至100℃,維持該狀態持續攪拌36小時而得到絕緣膜形成用組成物。
將所得到之絕緣膜形成用組成物於室溫(25℃)環境下目視觀察,環狀烯烴共聚合物完全溶解者係評估為溶解性良好「○」,有沉澱物或混濁者係評估為溶解性不良「×」。
又,對於使用之溶劑,並非有害性相關之法律規範對象者係評估為安全性良好「○」,為規範對象者係評估為安全性不良「×」。
實施例2~5及比較例1~16
除了將溶劑從環戊基甲醚變更為下列表中記載之化合物以外,與實施例1同樣地進行。
[表1]
實施例6
於100mL樣本瓶秤取47.5g環戊基甲醚,進一步投入精密秤量之環狀烯烴共聚合物(降莰烯與乙烯之共聚合物;商品名「TOPAS 5013S-04」,Polyplastics股份有限公司製)2.5g後,一邊藉由攪拌片攪拌一邊加熱至100℃。攪拌36小時後放冷至室溫而得到絕緣膜形成用組成物。
將所得到之絕緣膜形成用組成物,通過0.5μm濾筒而滴下至玻璃基板,其後使用旋轉塗布機進行旋轉塗布[旋轉塗布條件:花費3秒將轉速從0rpm提高至3000rpm,以3000rpm旋轉30秒,其後花費3秒將轉速降低至0rpm]
。其後,於加熱至100℃之加熱板乾燥5分鐘而形成塗膜。
對於所得到之塗膜,藉由下列方法測定下列物性,結果於所有項目皆滿足規格(參照表2)。
<薄膜形成能>
將塗膜之一部分以黃銅削去,以其高低差作為膜厚,藉由高低差計(小坂研究所股份有限公司製,ET4000A)測定平均表面粗糙度。
<接觸角>
使用接觸角計(協和界面科學股份有限公司製,DM-701),於25℃、1大氣壓環境下測定純水之接觸角。
<表面平坦性>
使用掃描型探針顯微鏡(SII nanotechnology股份有限公司製,SPA400)測定平均表面粗糙度。
<絕緣電阻值>
根據JIS C2110,對於0.1mm厚之塗膜進行測定。
<相對電容率>
根據IEC 60250,於25℃環境下測定1~10kHz之頻帶。
另外,參考例1中記載非晶質氟樹脂塗膜[商品名「CYTOP」(旭硝子股份有限公司製)之塗膜]之規格值,參考例2中記載環狀烯烴聚合物塗膜[商品名「ZEOCOAT」(日本ZEON股份有限公司製)之塗膜]之規格值。
可知本發明之絕緣膜形成用組成物可藉由塗布法形成表面平滑性優異之塗膜,所得到塗膜顯示良好的電氣特性。又,可知前述塗膜由於可濕性高,因此可藉由塗布溶解或分散於有機溶劑之有機半導體化合物或電極材料等而形成上位層。
本發明之塗布型絕緣膜形成用組成物,安全性以及作為墨水之安定性高,藉由塗布、乾燥,可形成相較於習知產品而相對電容率低且絕緣電阻值高之絕緣膜,該絕緣膜可濕性高而可藉由塗布法形成上位層。因此,可適用於藉由塗布法形成含絕緣膜之電子裝置之用途。
Claims (6)
- 一種絕緣膜形成用組成物,其係含有下列環狀烯烴共聚合物與下列溶劑的絕緣膜形成用組成物,絕緣膜形成用組成物所含溶劑全量中,下列式(1)所表示之化合物所佔比率為50重量%以上;環狀烯烴共聚合物:環狀烯烴與鏈狀烯烴之共聚合物,但具有環氧基的共聚合物除外;溶劑:含有為下列式(1)所表示之化合物且標準沸點為100℃以上、小於300℃之化合物,(式中,環Z係從5~6元之飽和或不飽和環烴以及苯環中所選擇之環,R1為烴基或醯基;環Z至少具有R1O基作為取代基,當具有2個以上取代基時,2個取代基可相互鍵結而與構成環Z之碳原子共同形成環)。
- 如請求項1之絕緣膜形成用組成物,其中環狀烯烴共聚合物係可具有取代基之降莰烯及/或環十二烯與碳數2~8之鏈狀α-烯烴之共聚合物。
- 如請求項1或2之絕緣膜形成用組成物,其中溶劑含有選自於環己基甲醚、環己醇乙酸酯、甲氧苯、乙氧苯以及環戊基甲醚中之至少1種的化合物。
- 如請求項1或2之絕緣膜形成用組成物,其黏度[25℃、剪切速度10(1/s)下]為0.1~5000mPa‧s。
- 如請求項3之絕緣膜形成用組成物,其黏度[25℃、剪切速度10(1/s)下]為0.1~5000mPa‧s。
- 如請求項1或2之絕緣膜形成用組成物,其中絕緣膜形成用組成物全量中,溶劑所佔比率為60重量%以上,且絕緣膜形成用組成物全量中,環狀烯烴共聚合物所佔比率為0.05重量%以上。
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