TWI644971B - 複分解聚合物成為介電質 - Google Patents
複分解聚合物成為介電質 Download PDFInfo
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- TWI644971B TWI644971B TW103122165A TW103122165A TWI644971B TW I644971 B TWI644971 B TW I644971B TW 103122165 A TW103122165 A TW 103122165A TW 103122165 A TW103122165 A TW 103122165A TW I644971 B TWI644971 B TW I644971B
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- Prior art keywords
- polymer
- oxoheteroolefin
- alkyl
- layer
- electronic device
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- 239000003989 dielectric material Substances 0.000 title claims abstract description 17
- 238000005649 metathesis reaction Methods 0.000 title abstract description 4
- 230000005669 field effect Effects 0.000 claims abstract description 20
- 239000003990 capacitor Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000004065 semiconductor Substances 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000009477 glass transition Effects 0.000 claims description 4
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012212 insulator Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000006116 polymerization reaction Methods 0.000 abstract description 4
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- -1 cyclic olefins Chemical class 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000013461 design Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010129 solution processing Methods 0.000 description 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QQYNRBAAQFZCLF-FBXFSONDSA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-epoxyisobenzofuran-1,3-dione Chemical compound O1[C@@H]2[C@@H]3C(=O)OC(=O)[C@@H]3[C@H]1C=C2 QQYNRBAAQFZCLF-FBXFSONDSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CHXZRHMQQRUVHF-UHFFFAOYSA-N 2-hex-5-en-1,3-diynyl-5-prop-1-ynylthiophene Chemical compound CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- QOTQFLOTGBBMEX-UHFFFAOYSA-N alpha-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 1
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- VRAYTNFBRROPJU-UHFFFAOYSA-N 2-methoxy-1,3-dioxolane Chemical compound COC1OCCO1 VRAYTNFBRROPJU-UHFFFAOYSA-N 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- BTZVKSVLFLRBRE-UHFFFAOYSA-N 2-methoxypropyl acetate Chemical compound COC(C)COC(C)=O BTZVKSVLFLRBRE-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000006549 C4-C10 aryl group Chemical group 0.000 description 1
- 125000000172 C5-C10 aryl group Chemical group 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- HGLGMFSKXPGZGM-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)N2CCN(C2C(=NN(Cl)Cl)C3=CC=CC=C3OC(C)C)C4=C(C=C(C=C4C)C)C)C Chemical compound CC1=CC(=C(C(=C1)C)N2CCN(C2C(=NN(Cl)Cl)C3=CC=CC=C3OC(C)C)C4=C(C=C(C=C4C)C)C)C HGLGMFSKXPGZGM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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Abstract
本發明係關於如通常藉由使用Ru-觸媒之複分解聚合獲得之氧雜環烯烴聚合物,其顯示良好溶解性且非常適合作為諸如電容器及有機場效應電晶體等電子裝置中之介電材料。
Description
本發明係關於用於製備有機電子裝置、例如基板上之電容器或電晶體之製程,係關於可藉由該製程獲得之裝置,係關於某些氧雜環烯烴聚合物及其作為介電質、尤其作為諸如電容器及有機場效應電晶體(OFET)等印刷電子裝置中之介電層之用途。
電晶體及具體而言OFET用作(例如)諸如有機發光顯示器、電子紙(e-paper)、液晶顯示器及射頻識別標籤等印刷電子裝置之組件。
有機場效應電晶體(OFET)包括包含有機半導體材料之半導體層、包含介電材料之介電層、閘極電極及源極/汲極電極。
尤其期望者係其中介電材料可藉由溶液處理技術來施加之OFET。就可處理性角度而言,溶液處理技術較為便捷,且亦可施加至塑膠基板。因此,與溶液處理技術相容之有機介電材料容許在撓性基板上產生低成本有機場效應電晶體。
氧雜降莰烯二甲醯亞胺已藉由開環複分解聚合(ROMP)來聚合以獲得非晶質聚合物(Cetinkaya等人,Heteroatom Chemistry(2010),21,36-43)或具有可調磁性之共聚物(Zha等人,J.Am.Chem.Soc.(2012),134,14534)。
WO 12/028278及US 2008/194740揭示某些包含藉由Ni催化製備之環烯烴聚合物之層。WO 12/028279揭示相同類型之聚合物,其用作與半導體層接觸之閘極介電層。
本發明之目標係提供介電材料,其容許易於進行溶液處理,同
時產生良好介電性質及黏著性。
現已發現,如通常藉由二環氧雜烯烴之Ru-碳烯催化之開環複分解聚合獲得之氧雜環烯烴聚合物作為介電材料顯示該等有利性質。
因此,本發明主要係關於含有至少一種包含氧雜環烯烴聚合物之介電材料之電子裝置。
圖1顯示包含聚合物1閘極介電質之TGBC場效應電晶體在-20V源極電壓Vsd(上部曲線)下與閘極電壓Vgs相關之汲極電流Ids(轉移曲線)。
圖2顯示包含聚合物1之TGBC場效應電晶體在0V(正方形)、-5V(星形)、-10V(菱形)、-15V(三角形)及-20V(圓形)之閘極電壓Vgs下之輸出曲線。
本發明之包含氧雜環烯烴聚合物之介電質之另一優點在於其在強極性溶劑中之溶解性,該性質容許對在該等介質中顯示較低溶解趨勢之先前材料(例如有機半導體)之層進行溶劑處理。
Ru-碳烯及其在複分解聚合反應中作為觸媒之用途已廣泛闡述於文獻中,參見(例如)US-6407190、US-6465554及其中引用之出版物(例如US-6465554之第1欄,第9-37列);US-7037993(例如第11欄,第34列至第13欄第10列);及上文引用之參考文獻;實例係雙(三環己基膦)亞苄基二氯化釕(IV)、
複分解聚合之析出物一般闡述為應變環烯烴,通常係二環烯
烴,例如降莰烯(二環[2.2.1]庚-2-烯),其未經取代或經取代。觸媒類型由此決定所獲得聚合物鏈之類型;Ni-觸媒一般產生聚合物鏈,其中維持單體之原始二環結構且聚合物鍵係由前烯烴雙鍵形成。本發明釕碳烯觸媒導致打開一個環且形成在其非環部分中含有烯烴雙鍵之聚合物鏈,如以下反應圖中可見:
其中n表示聚合物鏈內之重複單元數,且「Ru」代表欲根據本發明使用之Ru-碳烯觸媒。
因此,氧雜環烯烴聚合物係藉由二環氧雜烯烴之Ru-碳烯催化之聚合來獲得。其中之「氧雜」表示在二環烯烴之二環系統內,氧原子置換CH2部分。典型實例係降莰烯,其中一個CH2經氧置換,由此符合結構二環[2.2.1]-5-氧雜-庚-2-烯、二環[2.2.1]-6-氧雜-庚-2-烯或二環[2.2.1]-7-氧雜-庚-2-烯,每一結構可未經取代或經取代。此一析出物之較佳實例係式I之氧雜降莰烯
其中R1至R6中之每一者選自氫及C1-C4烷基;且R7及R8係氫或取代
基;或R7及R8與其所附接之碳原子一起形成未經取代或經取代之5至12個碳原子之飽和或不飽和碳環,或包含4至11個碳原子及1或2個氧原子或基團NR9(其中R9係氫或取代基)作為環成員之飽和或不飽和環(該環未經取代或經取代)。
因此,本發明之電子裝置通常包含式II之氧雜環烯烴聚合物
其中n介於3至100000範圍內,且R1至R8中之每一者係如上文針對I所定義。更佳地,氧雜環烯烴聚合物包含式III之聚合物鏈
其中n及R2至R5中之每一者係如上文所定義,且R係氫、C1-C25烷基、C1-C25鹵代烷基、苯基、苯基-C1-C4烷基、環戊基、環己基,其中苯基部分或環戊基或環己基部分自身未經取代或經C1-C4烷基、C1-C4烷氧基、OH、鹵素取代。
本發明之電子裝置通常選自電容器、電晶體(例如有機場效應電晶體)及包含該電容器及/或電晶體之裝置;其含有氧雜環烯烴聚合物,其較佳作為電容器層或閘極絕緣層,通常作為有機薄膜電晶體(例如OFET)之一部分,由此利用其優良介電性質。
在任何地方提及之任何取代基通常選自鹵素、C1-C25烷基、C2-C25烯基、C1-C25烷硫基、C1-C25烷氧基、C2-C25烯氧基、C4-C10芳基、C1-C9雜芳基、C3-C12環烷基、C2-C11雜環烷基,其中之每一
者未經取代或經R’取代;或係C2-C25烷基、C3-C25烯基、C2-C25烷硫基、C2-C25烷氧基、C3-C25烯氧基,其在其烷基部分中夾雜有O、CO、COO、CONR、CONRCO、S、SO、SO2、NR,且未經取代或經R’取代;或選自殘基OR、COR、CH=NR、CH=N-OH、CH=N-OR、COOR、CONHR、CONRR’、CONH-NHR、CONH-NRR’、SO2R、SO3R、SO2NHR、SO2NRR’、SO2NH-NHR、SO2NH-NRR’、S(O)R、S(O)OR、S(O)NHR、S(O)NRR’、S(O)NH-NHR、S(O)NH-NRR’、SiRR’R“、PORR’、PO(OR)R’、PO(OR)2、PO(NHR)2、PO(NRR’)2、CN、NO2、NHR、NRR’、NH-NHR、NH-NRR’、CONROH;且若鍵結至飽和碳則亦可係側氧基;且其中R、R’及R”獨立地選自C1-C25烷基、C1-C25鹵代烷基、C5-C10芳基、C6-C12芳基烷基、C3-C12環烷基,較佳選自C1-C6烷基、苯基、苄基、環戊基、環己基;且R亦可係氫;其中每一芳基或雜芳基或環烷基自身未經取代或經以下基團取代:C1-C4烷基、C2-C4烯基、C1-C4烷氧基、OH、CHO、C1-C4烷基-羰基、C1-C4烷基-羰氧基、C1-C4烷氧基-羰基、烯丙氧基、鹵素。
因此,本發明係關於電子裝置,一般係有機電子裝置,此乃因其可在基板上在印刷製程中製備。基板可係玻璃,但通常係塑膠膜或片材。典型裝置係電容器、電晶體(例如電子場效應電晶體(OFET))或包含該電容器及/或電晶體之裝置。本發明之裝置含有至少一種介電材料,通常呈介電層形式,其包含本發明之氧雜環烯烴聚合物。本發明之裝置一般含有另外至少一層主要選自導體及半導體之功能性材料,其通常與本發明之氧雜環烯烴聚合物介電材料或介電層直接接觸;實例係含有與電極及/或半導體直接接觸之本發明之介電材料層之OFET。
本發明另外提供用於製備電子裝置、例如基板上之電容器或電
晶體之製程,該製程包含以下步驟
i)提供如上文所述之氧雜環烯烴聚合物在適宜溶劑中之溶液或分散液,及ii)在基板、電極材料及/或半導體上形成層,並乾燥該層。
較佳地,該製程不包含在>=150℃之溫度下進行熱處理之步驟。更佳地,該製程不包含在>=140℃之溫度下進行熱處理之步驟。最佳地,該製程不包含在>=120℃之溫度下進行熱處理之步驟。因此,步驟(ii)中之熱處理步驟(若存在)通常需要將該層加熱至在30至150℃、較佳40至140℃、尤佳50至120℃範圍內之溫度。
適宜作為溶劑(下文亦稱為有機溶劑A)者係任何溶劑(或溶劑混合物),其能溶解至少2重量%、較佳至少5重量%、更佳至少8重量%之氧雜環烯烴聚合物。
作為有機溶劑A,一般可選擇沸點(在環境壓力下)在約80至250℃範圍內之任何溶劑。溶劑A可係該等溶劑之混合物。在較佳製程中,溶劑A之任一組份之沸點在100-220℃、尤其100-200℃範圍內。亦重要者係使用具有約150℃(例如120至180℃)沸點之主要溶劑(例如70% b.w.或更多,例如95%)及具有超過200℃、例如在200-250℃範圍內之高沸點之次要組份(30% b.w.或更少,例如5%)之摻合物。
較佳地,有機溶劑A選自由以下組成之群:N-甲基吡咯啶酮、C4-8-環烷酮、C1-4-烷基-C(O)-C1-4-烷基、C1-4-鏈烷酸C1-4-烷基酯(其中C1-4-烷基或C1-4-鏈烷酸可經羥基或O-C1-4-烷基取代)及C1-4-烷基-O-C1-4-伸烷基-O-C1-4-伸烷基-O-C1-4-烷基以及其混合物。
C1-4-烷基-C(O)-C1-4-烷基之實例係乙基異丙基酮、甲基乙基酮及甲基異丁基酮。
C1-4-鏈烷酸C1-4-烷基酯(其中C1-4-烷基或C1-4-鏈烷酸可經羥基或O-C1-4-烷基取代)之實例係乙酸乙酯、乙酸丁酯、乙酸異丁酯、乙酸
(2-甲氧基)乙基酯、乙酸(2-甲氧基)丙基酯及乳酸乙酯。
C1-4-烷基-O-C1-4-伸烷基-O-C1-4-伸烷基-O-C1-4-烷基之實例係二乙二醇二甲醚。
更佳地,有機溶劑A選自由以下組成之群:C4-8-環烷酮、C1-4-烷基-C(O)-C1-4-烷基、C1-4-鏈烷酸C1-4-烷基酯(其中C1-4-烷基或C1-4-鏈烷酸可經羥基或O-C1-4-烷基取代)及C1-4-烷基-O-C1-4-伸烷基-O-C1-4-伸烷基-O-C1-4-烷基以及其混合物。實例係甲基乙基酮(沸點80℃)、1,4-二噁烷、甲基-異丁基酮、乙酸丁酯、2-己酮、3-己酮、2-甲氧基-1,3-二氧戊環、丙二醇甲基醚乙酸酯(PGMEA)、乳酸乙酯、二甘二甲醚(DiGlyme)、5-甲基-3H-呋喃-2-酮(沸點169℃[「α-當歸內酯」])、二丙二醇二甲醚(沸點175℃[ProGlyde DMM])、N-甲基吡咯啶酮(NMP)、γ-丁內酯、苯乙酮、異佛爾酮、γ-己內酯、碳酸1,2-丙烯酯(沸點241℃);丙二醇甲基醚乙酸酯(PGMEA,沸點145℃,例如95%)與碳酸丙烯酯(例如5%)之摻合物。
最佳地,有機溶劑A選自由以下組成之群:C5-6-環烷酮、C1-4-鏈烷酸C1-4-烷基酯以及其混合物。甚至最佳地,有機溶劑A係環戊酮或PGMEA或其混合物。尤佳有機溶劑A係PGMEA或PGMEA與戊酮之混合物,其中PGMEA/環戊酮之重量比係至少99/1至20/80,更佳地99/1至30/70。
若氧雜環烯烴聚合物係作為在有機溶劑A中之溶液在電晶體層上或在基板上施加,則氧雜環烯烴聚合物可藉由任何可能的溶液製程來施加,例如旋塗、滴注或印刷。
在電晶體層上或在基板上施加作為在有機溶劑A中之溶液之氧雜環烯烴聚合物後,可實施在低於140℃之溫度(例如在60至120℃範圍內之溫度)、較佳在低於120℃之溫度(例如在60至110℃範圍內之溫度)下進行之熱處理。
包含氧雜環烯烴聚合物之層之厚度可在100至1000nm範圍內,較佳在300至1000nm範圍內,更佳在300至700nm範圍內。
包含氧雜環烯烴聚合物之層可基於該包含氧雜環烯烴聚合物之層之重量包含50至100重量%、較佳80至100%、較佳90至100重量%之氧雜環烯烴聚合物。較佳地,包含氧雜環烯烴聚合物之層基本上由氧雜環烯烴聚合物組成。
芳香族環之實例係苯基及萘基。苯基較佳。
鹵素之實例係氟、氯及溴。
C1-10-烷基之實例係甲基、乙基、丙基、異丙基、丁基、第二丁基、異丁基、第三丁基、戊基、2-乙基丁基、己基、庚基、辛基、壬基及癸基。丙基及丁基之實例係正丙基、異丙基、異丁基、第二丁基、異丁基及第三丁基。
C4-8-環烷基之實例係環丁基、環戊基、環己基、環庚基及環辛基。
C1-10-鹵代烷基之實例係三氟甲基及五氟乙基。
C2-10-烯基之實例係乙烯基、CH2-CH=CH2、CH2-CH2-CH=CH2。
C4-10-環烯基之實例係環戊基、環己基及降莰烯基。
C1-10-伸烷基之實例係亞甲基、伸乙基、伸丙基、伸丁基、伸戊基、伸己基及伸庚基。C1-4-伸烷基之實例係亞甲基、伸乙基、伸丙基及伸丁基。
C4-8-環伸烷基之實例係伸環丁基、伸環戊基、伸環己基及伸環庚基。
C1-4-鏈烷酸之實例係乙酸、丙酸及丁酸。
如藉由差示掃描量熱法所測定,本發明之氧雜環烯烴聚合物之玻璃轉變溫度較佳高於90℃,更佳高於130℃,且更佳介於150℃與300℃之間。
氧雜環烯烴聚合物之分子量可在5000至2000000g/mol、較佳10000至1000000g/mol範圍內(如藉由凝膠滲透層析法所測定)。
基板上之電晶體較佳係基板上之場效應電晶體(FET)且更佳係基板上之有機場效應電晶體(OFET)。
通常,有機場效應電晶體包含介電層及半導體層。另外,在有機場效應電晶體上通常包含閘極電極及源極/汲極電極。
有機場效應電晶體之典型設計係底部閘極設計及頂部閘極設計:在底部閘極底部接觸(BGBC)設計之情形中,閘極在基板頂部及介電層底部,半導體層在介電層頂部且源極/汲極電極在半導體層頂部。
基板上之場效應電晶體之另一設計係頂部閘極底部接觸(TGBC)設計:源極/汲極電極在基板頂部及半導體層底部,介電層在半導體層頂部且閘極電極在介電層頂部。在藉由溶液處理製備時,此處用於介電質之溶劑必須相對於半導體完全正交(即顯示介電質之良好溶解性及半導體之絕對不溶性),且另外與光阻劑處理相容。
半導體層包含半導體材料。半導體材料之實例係具有p-型傳導性(載流子:電洞)之半導體材料及具有n-型傳導性(載流子:電子)之半導體材料。
具有n-型傳導性之半導體之實例係苝二醯亞胺、萘二醯亞胺及富勒烯(fullerene)。
具有p-型傳導性之半導體材料較佳。具有p-型傳導性之半導體材料之實例係諸如以下等分子:紅螢烯(rubrene)、稠四苯、稠五苯、6,13-雙(三異丙基乙炔基)稠五苯、二茚並苝、苝二醯亞胺及四氰醌二甲烷;及諸如以下等聚合物:聚噻吩(具體而言聚3-己基噻吩(P3HT))、聚茀、聚聯乙炔、聚2,5-伸噻吩基伸乙烯基、聚對-伸苯基
伸乙烯基(PPV)及包含具有二酮基吡咯並吡咯基團之重複單元之聚合物(DPP聚合物)。
較佳地,半導體材料係包含具有二酮基吡咯並吡咯基團之單元之聚合物(DPP聚合物)。
DPP聚合物及其合成之實例闡述於(例如)以下文獻中:US 6,451,459 B1、WO 2005/049695、WO 2008/000664、WO 2010/049321、WO 2010/049323、WO 2010/108873、WO 2010/115767、WO 2010/136353及WO 2010/136352。
較佳地,DPP聚合物包含選自由以下組成之群之單元,較佳基本上由該單元組成:下式之聚合物單元
下式之共聚物單元
下式之共聚物單元
下式之共聚物單元
其中n’係4至1000、較佳4至200、更佳5至100,x’係0.995至0.005,較佳x’係0.2至0.8,y’係0.005至0.995,較佳y’係0.8至0.2,且x’+y’=1;
r’係0.985至0.005,s’係0.005至0.985,t’係0.005至0.985,u’係0.005至0.985,且r’+s’+t’+u’=1;A係下式之基團
其中a”係1、2或3,a’’’係0、1、2或3,b’係0、1、2或3,b”係0、1、2或3,c’係0、1、2或3,c”係0、1、2或3,d’係0、1、2或3,d”係0、1、2或3,前提係若a’’’為0,則b”不為0;R40及R41相同或不同且選自由以下組成之群:氫、C1-C100烷基、-COOR106”、經一或多個鹵素、羥基、硝基、-CN或C6-C18芳基取代及/或夾雜有-O-、-COO-、-OCO-或-S-之C1-C100烷基;C7-C100芳基烷基、胺基甲醯基、可經C1-C8烷基及/或C1-C8烷氧基取代1至3次之C5-C12環烷基、可經C1-C8烷基、C1-C25硫烷氧基及/或C1-C25烷氧基取代1至3次之C6-C24芳基(具體而言苯基或1-或2-萘基)或五氟苯基,其中
R106”係C1-C50烷基、較佳C4-C25烷基,
Ar1、Ar1’、Ar2、Ar2’、Ar3、Ar3’、Ar4及Ar4’彼此獨立地係可視情況縮合及/或取代之雜芳香族或芳香族環,較佳係
其中X3及X4中之一者係N且另一者係CR99,其中R99係氫、鹵素,較佳係F或C1-C25烷基,較佳可視情況夾雜有一或多個氧或硫原子之C4-C25烷基、C7-C25芳基烷基或C1-C25烷氧基,R104、R104’、R123及R123’彼此獨立地係氫、鹵素,較佳係F或C1-C25烷基,較佳係可視情況夾雜有一或多個氧或硫原子之C4-C25烷基、C7-C25芳基烷基或C1-C25烷氧基,R105、R105’、R106及R106’彼此獨立地係氫、鹵素、可視情況夾雜有一或多個氧或硫原子之C1-C25烷基;C7-C25芳基烷基或C1-C18烷氧基;R107係C7-C25芳基烷基、C6-C18芳基;經C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代之C6-C18芳基;C1-C18烷基;夾雜有-O-或-S-之C1-C18烷基;或-COOR124;R124係C1-C25烷基,較佳係可視情況夾雜有一或多個氧或硫原子
之C4-C25烷基、C7-C25芳基烷基,R108及R109彼此獨立地係H、C1-C25烷基、經E’取代及/或夾雜有D'之C1-C25烷基、C7-C25芳基烷基、C6-C24芳基、經G取代之C6-C24芳基、C2-C20雜芳基、經G取代之C2-C20雜芳基、C2-C18烯基、C2-C18炔基、C1-C18烷氧基、經E’取代及/或夾雜有D'之C1-C18烷氧基或C7-C25芳烷基,或R108與R109一起形成式=CR110R111之基團,其中R110及R111彼此獨立地係H、C1-C18烷基、經E’取代及/或夾雜有D'之C1-C18烷基、C6-C24芳基、經G取代之C6-C24芳基或C2-C20雜芳基或經G取代之C2-C20雜芳基,或R108與R109一起形成5或6員環,其可視情況經以下基團取代:C1-C18烷基、經E’取代及/或夾雜有D'之C1-C18烷基、C6-C24芳基、經G取代之C6-C24芳基、C2-C20雜芳基、經G取代之C2-C20雜芳基、C2-C18烯基、C2-C18炔基、C1-C18烷氧基、經E’取代及/或夾雜有D'之C1-C18烷氧基或C7-C25芳烷基,其中D’係-CO-、-COO-、-S-、-O-或-NR112-,E’係C1-C8硫烷氧基、C1-C8烷氧基、CN、-NR112R113、-CONR112R113或鹵素,G係E’或C1-C18烷基,且R112及R113彼此獨立地係H;C6-C18芳基;經C1-C18烷基或C1-C18烷氧基取代之C6-C18芳基;C1-C18烷基;或夾雜有-O-之C1-C18烷基,且B、D及E彼此獨立地係下式之基團
或式(24)之基團,前提係若B、D及E係式(24)之基團,則其不同於A,其中k’係1,l’係0或1,r’係0或1,z’係0或1,且Ar5、Ar6、Ar7及Ar8彼此獨立地係下式之基團
其中X5及X6中之一者係N且另一者係CR140,R140、R140’、R170及R170’彼此獨立地係H或C1-C25烷基,較佳係可視情況夾雜有一或多個氧原子之C6-C25烷基。
較佳聚合物闡述於WO2010/049321中。
Ar1及Ar1’較佳係
極佳係或
且最佳係
Ar2、Ar2’、Ar3、Ar3’、Ar4及Ar4’較佳係
更佳係
下式之基團
較佳係或
更佳係或
最佳係或
R40及R41相同或不同且較佳選自氫、C1-C100烷基,更佳係C8-C36烷基。
A較佳選自由以下組成之群:
及
包含式(20)之聚合物單元、較佳基本上由該單元組成之較佳DPP聚合物之實例顯示如下:
其中R40及R41係C1-C36烷基,較佳係C8-C36烷基,且n’係4至1000,較佳係4至200,更佳係5至100。
包含式(21)之共聚物單元、較佳基本上由該單元組成之較佳DPP聚合物之實例顯示如下:
其中R40及R41係C1-C36烷基,較佳係C8-C36烷基,且n’係4至1000,較佳係4至200,更佳係5至100。
包含式(22)之共聚物單元、較佳基本上由該單元組成之較佳DPP聚合物之實例顯示如下:
及
其中R40及R41係C1-C36烷基,較佳係C8-C36烷基,
R42係C1-C18烷基,R150係C4-C18烷基,X’=0.995至0.005,較佳x’=0.4至0.9,y’=0.005至0.995,較佳y’=0.6至0.1,且x+y=1。
包含式(22-1)之共聚物單元、較佳基本上由該單元組成之DPP聚合物較包含式(22-2)之共聚物單元、較佳基本上由該單元組成之DPP聚合物更佳。
DPP聚合物之重量平均分子量較佳為4,000道爾頓(Dalton)或更高,尤其4,000至2,000,000道爾頓,更佳10,000至1,000,000,且最佳10,000-100,000道爾頓。
包含下式之共聚物單元
(其中R40、R41係烷基,例如2-己基癸基)
或式(21-1)之共聚物單元、較佳基本上由該單元組成之DPP聚合物尤佳。例如,參見WO2010/049321之實例1:
介電層包含介電材料。介電材料可係矽/二氧化矽,或較佳係有機聚合物,例如聚(甲基丙烯酸甲酯)(PMMA)、聚(4-乙烯苯酚)(PVP)、聚(乙烯醇)(PVA)、苯并環丁烯(BCB)、聚醯亞胺(PI)。
較佳地,介電層包含本發明之氧雜環烯烴聚合物。
基板可為任一適宜基板,例如玻璃或塑膠基板。較佳地,基板係塑膠基板,例如聚醚碸、聚碳酸酯、聚碸、聚對苯二甲酸乙二酯(PET)及聚萘二甲酸乙二酯(PEN)。更佳地,塑膠基板係塑膠箔。
可藉由上文製程獲得之電晶體亦係本發明之一部分。
本發明製程之優點在於,本發明之氧雜環烯烴聚合物可抵抗收縮。
本發明製程之另一優點在於,本發明之氧雜環烯烴聚合物顯示高化學穩定性及高熱穩定性。因此,本發明製程可用於製備(例如)有機場效應電晶體,其中包含本發明之氧雜環烯烴聚合物之層係介電層,其中在介電層頂部上之電極可藉由經陰影遮罩蒸發來施加。
本發明製程之另一優點在於,本發明之氧雜環烯烴聚合物可溶於有機溶劑(溶劑A)中。較佳地,可能製備本發明之氧雜環烯烴聚合物於有機溶劑中之2重量%、更佳5重量%且最佳8重量%之溶液。因此,可能藉由溶液處理技術來施加本發明之氧雜環烯烴聚合物。
本發明製程之另一優點在於,用於溶解本發明之氧雜環烯烴聚合物之有機溶劑
(i)之沸點(在環境壓力下)較佳低於160℃,較佳低於150℃,更加低於120℃,且因此可藉由在低於120℃之溫度下、較佳在60至110℃範圍內之溫度下熱處理來移除,且(ii)較佳不溶解適宜半導體材料諸如二酮基吡咯並吡咯(DPP)噻吩,且因此容許在包含二酮基吡咯並吡咯(DPP)噻吩之半導體層上施加本發明之氧雜環烯烴聚合物時形成平滑邊界。
本發明製程之另一優點在於,製程中之所有步驟皆可在環境氣氛下實施,此意指不需要特別預防例如氮氣氛。
本發明電晶體(較佳地,其中電晶體係有機場效應電晶體且其中包含本發明之氧雜環烯烴聚合物之層係介電層,且半導體層包含半導體材料,例如二酮基吡咯並吡咯(DPP)噻吩聚合物)之優點在於,電晶體顯示高遷移率(高I開/I關比率)及低閘極漏電。
以下實例闡釋本發明。若無其他指示,則無論在何處提及,室溫(r.t.)皆表示22-25℃範圍內之溫度;過夜意指12至15小時時間段;百分比係以重量計。若無其他指示,則分子量係如藉由凝膠滲透層析法所測定。
玻璃轉變溫度係藉由差示掃描量熱法(DSC)使用Mettler-Toledo DSC 822E®及Mettler-Toledo Stare®軟體9.10、封閉標準鋁坩堝(40微升)來測定,樣品重量在4000-10000mg範圍內,氮係50ml/min,溫度梯度如下:以20℃/min自20℃第一次加熱至300℃,之後以20℃/min自300℃冷卻至20℃,且以20℃/min自20℃第二次加熱至300℃。其他縮寫:
Mw 分子量,如藉由高溫凝膠滲透層析法所獲得
NMP N-甲基吡咯啶酮
PDI 多分散性(高溫凝膠滲透層析法)
Tg 玻璃轉變溫度
b.p. 沸點(在1個大氣壓下)
a)單體1之製備
將100g對異丙基苯胺(1eq,0.74mol)添加至122.9g外-3,6-環氧基-1,2,3,6-四氫鄰苯二甲酸酐(1eq,0.74mol)於丙酮中之溶液中並攪拌2h。過濾所得沈澱物,用丙酮洗滌,乾燥並與27g乙酸鈉在550mL乙酸酐中混合。然後將混合物在回流下攪拌2h並在0℃下冷卻。過濾所得沈澱物,用水洗滌,在甲醇中重結晶並乾燥以產生呈純的白色固體之相應的1。產率=71%;1H-NMR(CDCl3):δ(ppm)1.18(d,6H),1,56(s,2H),2.79(s,2H),2.94 m,1H),3.03(s,2H),5,42(s,2H),6.59(s,2H),7.20(d,2H),7.33(d,2H)。
b)聚合物P1
在氮下將63mg(1,3-雙-(2,4,6-三甲基苯基)-2-亞咪唑啶基)二氯(鄰異丙氧基苯基亞甲基)釕(0.5% mol,100μmol)添加至於15mL無水二氯甲烷中之2g之1(1eq,18mmol)中。在回流下攪拌4h後,添加10mL無水二氯甲烷及1mL乙基乙烯基醚。將混合物傾倒於冷乙醇中。過濾沈澱物,將其溶解於最小量之二氯甲烷中並傾倒於冷庚烷中。過濾沈澱物,乾燥以產生呈白色固體之相應純聚合物P1。產率=61%
Mw=161kDa/PDI=2.1/Tg=228℃
鈉含量 14mg/kg
磷含量 24mg/kg
釕含量 117mg/kg
a)聚合物P2:
Mw=46.5kDa
PDI=1.46
Tg=238℃
b)聚合物P3:
Mw=69kDa
PDI=1.60
Tg=144℃
將金濺鍍至聚(對苯二甲酸乙二酯)(PET)箔上以形成約40nm厚的膜,然後藉由光微影製程使源極/汲極電極(通道長度:10μm;通道寬度:10mm)結構化。經由0.45μm聚四氟乙烯(PTFE)過濾器過濾二酮基吡咯並吡咯(DPP)-噻吩-聚合物於甲苯中之0.75%(重量/重量)溶液(二酮基吡咯並吡咯(DPP)-噻吩-聚合物係根據WO2010/049321之實例1之聚合物21-1:
;Mw=39,500)
,然後藉由旋塗(以1300rpm旋轉15秒,以10.000rpm/s加速)來施加。將濕有機半導體聚合物層在熱板上在100℃下乾燥30秒。經由0.45μm過濾器過濾P1於乙酸甲氧基丙基酯中之8%(重量/重量)溶液,然後藉由旋塗(1100rpm,60秒)施加。將濕層膜在熱板上在100℃下預烘烤20分鐘以獲得365nm厚的層。在P1層上蒸發經由陰影遮罩金閘極電極(厚約120nm)。整個製成之實施不使用保護性氣氛。
頂部閘極、底部接觸(TGBC)場效應電晶體之特徵的量測係用Keithley® 2612A半導體參數分析儀來量測。
包含P1閘極介電質之頂部閘極、底部接觸(TGBC)場效應電晶體
在-20V源極電壓Vsd(上部曲線)下與閘極電壓Vgs相關之汲極電流Ids(轉移曲線)顯示於圖1中。
包含P1作為閘極介電質之頂部閘極、底部接觸(TGBC)場效應電晶體顯示0.36cm2/Vs之遷移率(針對飽和模式計算)及5 E+5之I開/I關比率。
包含P1之頂部閘極、底部接觸(TGBC)場效應電晶體在0V(正方形)、-5V(星形)、-10V(菱形)、-15V(三角形)及-20V(圓形)之閘極電壓Vgs下與汲極電壓Vds(輸出曲線)相關之汲極電流Ids顯示於圖2中。
經由0.45μm過濾器過濾如實例1b中所獲得之聚合物P1於乙酸甲氧基丙基酯中之8%(重量/重量)溶液,且藉由旋塗(1100rpm,30秒)在具有氧化銦錫(ITO)電極之潔淨玻璃基板上施加。將濕膜在熱板上在100℃下預烘烤20分鐘以獲得490nm厚的層。然後在<1×10-6托下在P1層上經由陰影遮罩真空沈積金電極(面積=3mm2)。
按以下方式表徵由此獲得之電容器:自用LCR量計Agilent 4284A(信號振幅1V)量測之綜合電容來推斷相對電容率ε r 及損失因子tg(δ)=ε r "。用半導體參數分析儀Agilent 4155C獲得電流/電壓(I/V)曲線。崩潰電壓係電流達到1μA值時之電壓Ed。自電阻、樣品厚度及電極表面來計算體積電阻率ρ。
以相同方式使用聚合物2及3製備並研究電容器。結果彙編於下表中。
a)單體2之製備
將100g對異丙基苯胺(1eq,0.74mol)添加至122.9g外-3,6-環氧基-1,2,3,6-四氫鄰苯二甲酸酐(1eq,0.74mol)於丙酮中之溶液中。然後將混合物攪拌2h。過濾所得沈澱物,用丙酮洗滌並乾燥以產生呈白色固體之相應的純2。產率=87%。
1H-NMR(DMSO):δ(ppm)1.19(d,6H),2.67(d,1H),2.79(d,1H),2.83(m,1H),5.03(s,1H),5.14(s,1H),6.50(m,2H),7.15(d,2H),7.44(d,2H),9.60(s,1H)。
b)單體3之製備
將182.4g之2(1eq,0.63mol)添加至550mL乙酸酐及27g乙酸鈉(0.5eq,0.33mol)中。然後將混合物在回流下攪拌2h並在0℃下冷卻。過濾所得沈澱物,用水洗滌,經甲醇重結晶並乾燥以產生呈白色固體之相應的純3。產率=79%
1H-NMR(CDCl3):δ(ppm)1.18(d,6H),1,56(s,2H),2.79(s,2H),
2.94(m,1H),3.03(s,2H),5,42(s,2H),6.59(s,2H),7.20(d,2H),7.33(d,2H)。
c)聚合物P1'
在氮下將80mg雙(三環己基膦)亞苄基二氯化釕(IV)(0.5% mol,100μmol)添加至於15mL無水二氯甲烷中之5g之3(1eq,18mmol)中。在室溫下攪拌5h後,添加10mL無水二氯甲烷及1mL乙基乙烯基醚。將混合物傾倒於冷乙醇中。過濾沈澱物,將其溶解於最小量之二氯甲烷中並傾倒於冷庚烷中。過濾沈澱物,乾燥以產生呈白色固體之相應的純聚合物1’。產率=61%。
Mw=128kDa
PDI=3.4
Tg=228℃
Na含量14mg/kg
P含量24mg/kg
Ru含量117mg/kg
Claims (10)
- 一種電子裝置,其包含電容器及/或電晶體,該電容器及/或電晶體含有至少一種包含氧雜環烯烴聚合物之介電材料,其中該氧雜環烯烴聚合物包含式III之聚合物鏈
- 如請求項1之電子裝置,其中該氧雜環烯烴聚合物係藉由二環氧雜烯烴之Ru-碳烯催化之開環複分解聚合來製備。
- 如請求項1或2之電子裝置,其中該氧雜環烯烴聚合物係作為由該氧雜環烯烴聚合物組成之層而存在。
- 如請求項1或2之電子裝置,其中該氧雜環烯烴聚合物具有藉由差示掃描量熱法所測定高於90℃之玻璃轉變溫度及/或藉由凝膠滲透層析法所測定在5000至2000000g/mol範圍內之分子量。
- 如請求項1或2之電子裝置,其進一步包含基板且包含另外至少一層與該至少一種包含氧雜環烯烴聚合物之介電材料直接接觸之功能性材料。
- 如請求項5之電子裝置,其中作為介電材料之該氧雜環烯烴聚合物之層與電極層及/或半導體層直接接觸。
- 一種閘極絕緣體層,其包含氧雜環烯烴聚合物,其中該氧雜環烯烴聚合物包含如請求項1中所定義之式III聚合物鏈。
- 如請求項7之閘極絕緣層,其中該氧雜環烯烴聚合物係作為實質上由該氧雜環烯烴聚合物組成之層而存在。
- 一種用於製備基板上之電容器或電晶體之方法,該方法包含以下步驟i)提供氧雜環烯烴聚合物於適宜溶劑中之溶液或分散液,其中該氧雜環烯烴聚合物包含如請求項1中所定義之式III聚合物鏈,及ii)在基板、電極材料及/或半導體上形成層,並乾燥該層。
- 一種如請求項1中所定義之氧雜環烯烴聚合物之用途,其用作電容器或有機場效應電晶體中之介電材料。
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