TWI410427B - 甲矽烷基乙炔基化雜環並化合物及利用其所製之電子裝置 - Google Patents
甲矽烷基乙炔基化雜環並化合物及利用其所製之電子裝置 Download PDFInfo
- Publication number
- TWI410427B TWI410427B TW097107508A TW97107508A TWI410427B TW I410427 B TWI410427 B TW I410427B TW 097107508 A TW097107508 A TW 097107508A TW 97107508 A TW97107508 A TW 97107508A TW I410427 B TWI410427 B TW I410427B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- atoms
- isomers
- mixture
- semiconductor
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 239000004065 semiconductor Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 8
- 239000012212 insulator Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 26
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 17
- -1 ten Hydronaphthalene Chemical compound 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000005669 field effect Effects 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- JNJXAICELPDTGX-UHFFFAOYSA-N n,n'-diethylpropanimidamide Chemical compound CCNC(CC)=NCC JNJXAICELPDTGX-UHFFFAOYSA-N 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 2
- CJALNXQQXPYSRB-UHFFFAOYSA-N 5-bromothiophene-2,3-dicarbaldehyde Chemical compound BrC1=CC(C=O)=C(C=O)S1 CJALNXQQXPYSRB-UHFFFAOYSA-N 0.000 description 2
- QADZTXRADGAZAP-UHFFFAOYSA-N C#C.C(C)NC(=NCC)CC Chemical group C#C.C(C)NC(=NCC)CC QADZTXRADGAZAP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-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
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- WSEJZRIZDQWMKQ-UHFFFAOYSA-N thiophene-2,3-dicarbaldehyde Chemical compound O=CC=1C=CSC=1C=O WSEJZRIZDQWMKQ-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SWHCYTRINAKJGN-UHFFFAOYSA-N 2-[2-(1,3-dioxolan-2-yl)thiophen-3-yl]-1,3-dioxolane Chemical compound O1CCOC1C1=C(C2OCCO2)SC=C1 SWHCYTRINAKJGN-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class 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
- 241000252505 Characidae Species 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IHBGCGJSAKRORR-UHFFFAOYSA-N N-(2,2-difluoroethyl)-N-ethyl-N'-hydroxypropanimidamide thiophene Chemical class S1C=CC=C1.S1C=CC=C1.FC(CN(C(=NO)CC)CC)F IHBGCGJSAKRORR-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- ZEQICNSQVWRFGZ-UHFFFAOYSA-N S1C=CC=C1.S1C=CC=C1.NN Chemical compound S1C=CC=C1.S1C=CC=C1.NN ZEQICNSQVWRFGZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006023 eutectic alloy Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- AHIXHWRUDZFHEZ-UHFFFAOYSA-N furan-2,3-dicarbaldehyde Chemical compound O=CC=1C=COC=1C=O AHIXHWRUDZFHEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000005232 molecular self-assembly Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007790 scraping Methods 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
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 150000005082 selenophenes Chemical class 0.000 description 1
- 239000002094 self assembled monolayer Substances 0.000 description 1
- 239000013545 self-assembled monolayer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 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
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/451—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising a metal-semiconductor-metal [m-s-m] structure
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electromagnetism (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07004633 | 2007-03-07 | ||
| EP07005029 | 2007-03-12 | ||
| EP07006166 | 2007-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200904821A TW200904821A (en) | 2009-02-01 |
| TWI410427B true TWI410427B (zh) | 2013-10-01 |
Family
ID=39314905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097107508A TWI410427B (zh) | 2007-03-07 | 2008-03-04 | 甲矽烷基乙炔基化雜環並化合物及利用其所製之電子裝置 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2132213B1 (enExample) |
| JP (2) | JP5562652B2 (enExample) |
| KR (1) | KR101591101B1 (enExample) |
| CN (1) | CN101657458B (enExample) |
| GB (1) | GB2460579B (enExample) |
| TW (1) | TWI410427B (enExample) |
| WO (1) | WO2008107089A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2132213B1 (en) * | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| CN101926017B (zh) | 2007-12-17 | 2013-09-25 | 3M创新有限公司 | 基于蒽的可溶液加工的有机半导体 |
| CN102124015B (zh) * | 2008-05-30 | 2015-03-11 | 3M创新有限公司 | 甲硅烷基乙炔基并五苯化合物和组合物及其制备和使用方法 |
| CN102119164A (zh) * | 2008-06-19 | 2011-07-06 | 3M创新有限公司 | 可溶液处理的有机半导体 |
| KR101935644B1 (ko) | 2008-10-31 | 2019-01-04 | 바스프 에스이 | 유기 전계 효과 트랜지스터에 사용하기 위한 디케토피롤로피롤 중합체 |
| BRPI1011853A2 (pt) | 2009-05-27 | 2019-09-24 | Basf Se | polímero, material, camada ou componente semicondutores orgânicos, dispositivo semicondutor, processos para a preparação de um dispositivo semicondutor orgânico, e de um polímero, e, uso do polímero e/ou do material, camada ou componente semicondutores orgãnicos. |
| EP2435446B8 (en) | 2009-05-29 | 2017-02-22 | 3M Innovative Properties Company | Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same |
| KR101097313B1 (ko) * | 2009-08-10 | 2011-12-23 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
| KR101626363B1 (ko) * | 2009-12-16 | 2016-06-02 | 엘지디스플레이 주식회사 | 안트라세닐계 교호 공중합체, 그 제조 방법 및 이를 이용한 유기 박막 트랜지스터 |
| WO2011076325A1 (en) | 2009-12-23 | 2011-06-30 | Merck Patent Gmbh | Compositions comprising polymeric binders |
| WO2011076324A1 (en) | 2009-12-23 | 2011-06-30 | Merck Patent Gmbh | Compositions comprising organic semiconducting compounds |
| KR102045196B1 (ko) | 2010-04-12 | 2019-11-15 | 메르크 파텐트 게엠베하 | 개선된 성능을 갖는 조성물 |
| US20130026421A1 (en) | 2010-04-12 | 2013-01-31 | Merck Patent Gmbh | Composition and method for preparation of organic electronic devices |
| KR101839636B1 (ko) | 2010-05-19 | 2018-03-16 | 바스프 에스이 | 유기 반도체 소자에 사용하기 위한 디케토피롤로피롤 중합체 |
| WO2011147523A1 (en) | 2010-05-27 | 2011-12-01 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
| WO2012017005A2 (en) | 2010-08-05 | 2012-02-09 | Basf Se | Polymers based on benzodiones |
| US9306172B2 (en) | 2010-08-13 | 2016-04-05 | Merck Patent Gmbh | Anthra[2,3-b:7,6-b']dithiophene derivatives and their use as organic semiconductors |
| WO2012028244A1 (en) | 2010-09-02 | 2012-03-08 | Merck Patent Gmbh | Process for preparing an organic electronic device |
| US20130161568A1 (en) * | 2010-09-10 | 2013-06-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anthra[2,3-b:7,6-b']dithiophene Derivatives and their Use as Organic Semiconductors |
| CN103249739B (zh) * | 2010-12-06 | 2016-02-17 | 默克专利有限公司 | 非线性并苯衍生物及其作为有机半导体的用途 |
| GB201108864D0 (en) * | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
| GB201108865D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
| ITMI20111447A1 (it) * | 2011-07-29 | 2013-01-30 | E T C Srl | Transistor organico elettroluminescente |
| WO2013050401A2 (en) | 2011-10-04 | 2013-04-11 | Basf Se | Polymers based on benzodiones |
| WO2013083506A1 (en) | 2011-12-07 | 2013-06-13 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| GB201203159D0 (en) | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
| US9505877B2 (en) | 2012-04-02 | 2016-11-29 | Basf Se | Phenanthro[9,10-B]furan polymers and small molecules for electronic applications |
| KR102079604B1 (ko) | 2012-04-04 | 2020-04-08 | 바스프 에스이 | 디케토피롤로피롤 중합체 및 소분자 |
| JP6207606B2 (ja) | 2012-07-23 | 2017-10-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ジチエノベンゾフランポリマーおよび電子的な応用のための小分子 |
| EP2917304B1 (en) | 2012-11-07 | 2016-10-26 | Basf Se | Polymers based on naphthodiones |
| WO2014086722A1 (en) | 2012-12-04 | 2014-06-12 | Basf Se | Functionnalized benzodithiophene polymers for electronic application |
| CN105324441B (zh) | 2013-06-24 | 2018-01-02 | 巴斯夫欧洲公司 | 基于稠合二酮基吡咯并吡咯的聚合物 |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| KR102091906B1 (ko) | 2013-08-28 | 2020-03-20 | 스마트켐 리미티드 | 고분자 유기 반도체 조성물 |
| CN103554138B (zh) * | 2013-10-31 | 2016-02-17 | 兰州大学 | 一种具有有机场效应晶体管性质的材料及其制备方法 |
| JP6181318B2 (ja) | 2014-04-29 | 2017-08-16 | サビック グローバル テクノロジーズ ビー．ブイ． | 光電子工学用途のための高い導電性および吸収を有する小分子／オリゴマーの合成 |
| JP2017017216A (ja) * | 2015-07-02 | 2017-01-19 | Dic株式会社 | 半導体組成物、半導体インク |
| WO2017008883A1 (en) | 2015-07-15 | 2017-01-19 | Merck Patent Gmbh | Composition comprising organic semiconducting compounds |
| WO2017068009A1 (en) | 2015-10-21 | 2017-04-27 | Basf Se | Polymers and compounds based on dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione |
| WO2017202635A1 (en) | 2016-05-25 | 2017-11-30 | Basf Se | Semiconductors |
| WO2018114883A1 (de) * | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200529483A (en) * | 2003-11-28 | 2005-09-01 | Avecia Ltd | Improvements in and relating to organic semiconducting layers |
| TW200708515A (en) * | 2005-04-05 | 2007-03-01 | Eastman Kodak Co | Semiconductor materials for thin film transistors |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100303934B1 (ko) * | 1997-03-25 | 2001-09-29 | 포만 제프리 엘 | 낮은작동전압을필요로하는유기반도체를갖는박막전장효과트랜지스터 |
| US5936259A (en) * | 1997-10-16 | 1999-08-10 | Lucent Technologies Inc. | Thin film transistor and organic semiconductor material thereof |
| CN1237626C (zh) * | 1998-08-19 | 2006-01-18 | 普林斯顿大学理事会 | 有机光敏光电器件 |
| US7382040B2 (en) * | 2004-01-15 | 2008-06-03 | Matsushita Electric Industrial Co., Ltd. | Organic field effect transistor and display using same |
| JP2005253231A (ja) * | 2004-03-05 | 2005-09-15 | Fuji Electric Fa Components & Systems Co Ltd | 無停電電源装置、無停電電源管理システム及び無停電電源管理方法 |
| JP2006125270A (ja) * | 2004-10-28 | 2006-05-18 | Takeshi Uchida | 回転駆動装置 |
| WO2006054686A1 (ja) * | 2004-11-18 | 2006-05-26 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタの製造方法及び有機薄膜トランジスタ |
| JP2006168085A (ja) * | 2004-12-15 | 2006-06-29 | Nissan Motor Co Ltd | 情報化核酸含有木質材料及びその製造方法 |
| JP2006283536A (ja) * | 2005-03-31 | 2006-10-19 | Kagawa Setsubi Kogyosho:Kk | 配管用貫通穴埋め治具 |
| JP2007067262A (ja) * | 2005-09-01 | 2007-03-15 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| JP2006151379A (ja) * | 2005-11-21 | 2006-06-15 | Yuji Nishimura | 盗難防止兼用サドルカバー |
| JP5228907B2 (ja) * | 2006-03-10 | 2013-07-03 | コニカミノルタ株式会社 | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| US7372071B2 (en) * | 2006-04-06 | 2008-05-13 | Xerox Corporation | Functionalized heteroacenes and electronic devices generated therefrom |
| JP2007299852A (ja) * | 2006-04-28 | 2007-11-15 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| JP2007324288A (ja) * | 2006-05-31 | 2007-12-13 | Konica Minolta Holdings Inc | 有機半導体膜及びその製造方法、有機薄膜トランジスタ及びその製造方法 |
| JP2007335760A (ja) * | 2006-06-16 | 2007-12-27 | Fujifilm Corp | 光電変換膜、並びに、該光電変換膜を含む太陽電池、光電変換素子、又は撮像素子 |
| US20080042127A1 (en) * | 2006-08-17 | 2008-02-21 | Watson Mark D | Transition metal free coupling of highly fluorinated and non-fluorinated pi-electron systems |
| JP2008103464A (ja) * | 2006-10-18 | 2008-05-01 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| EP2132213B1 (en) * | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
-
2008
- 2008-02-25 EP EP08716025.5A patent/EP2132213B1/en not_active Not-in-force
- 2008-02-25 KR KR1020097020741A patent/KR101591101B1/ko not_active Expired - Fee Related
- 2008-02-25 WO PCT/EP2008/001482 patent/WO2008107089A1/en not_active Ceased
- 2008-02-25 JP JP2009552094A patent/JP5562652B2/ja not_active Expired - Fee Related
- 2008-02-25 CN CN200880007457.8A patent/CN101657458B/zh not_active Expired - Fee Related
- 2008-02-25 GB GB0917170A patent/GB2460579B/en not_active Expired - Fee Related
- 2008-03-04 TW TW097107508A patent/TWI410427B/zh not_active IP Right Cessation
-
2014
- 2014-03-14 JP JP2014051016A patent/JP2014193861A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200529483A (en) * | 2003-11-28 | 2005-09-01 | Avecia Ltd | Improvements in and relating to organic semiconducting layers |
| TW200708515A (en) * | 2005-04-05 | 2007-03-01 | Eastman Kodak Co | Semiconductor materials for thin film transistors |
Non-Patent Citations (2)
| Title |
|---|
| Marica M. Payne, et al., "Stable, Crystalline Acenedithiophenes with up to Seven Linearly Fused Rings" Org. Lett., 2004, 6, 3325-3328 * |
| Marica M. Payne, et al., "Organic Field-Effect Transistors from Solution-Deposited Functionalized Acenes with Mobilites as High as 1 cm2/V-s" J. Am. Chem. Soc., 2005, 127, 4986-4987 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2460579A (en) | 2009-12-09 |
| CN101657458A (zh) | 2010-02-24 |
| EP2132213B1 (en) | 2013-05-15 |
| GB2460579B (en) | 2011-11-02 |
| KR101591101B1 (ko) | 2016-02-03 |
| TW200904821A (en) | 2009-02-01 |
| JP2014193861A (ja) | 2014-10-09 |
| KR20100015372A (ko) | 2010-02-12 |
| JP5562652B2 (ja) | 2014-07-30 |
| HK1140768A1 (en) | 2010-10-22 |
| GB0917170D0 (en) | 2009-11-11 |
| CN101657458B (zh) | 2014-07-02 |
| JP2010520241A (ja) | 2010-06-10 |
| WO2008107089A1 (en) | 2008-09-12 |
| EP2132213A1 (en) | 2009-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI410427B (zh) | 甲矽烷基乙炔基化雜環並化合物及利用其所製之電子裝置 | |
| US7385221B1 (en) | Silylethynylated heteroacenes and electronic devices made therewith | |
| CN102549791B (zh) | 双极性聚合物半导体材料及有机电子器件 | |
| TWI477504B (zh) | 半導體材料及其製備與使用方法 | |
| EP2573833B1 (en) | Organic semiconductors, their manufacture and semiconductor devices comprising them | |
| KR101096981B1 (ko) | 신규한 축합고리 화합물 및 이를 이용한 유기전자소자 | |
| KR101844106B1 (ko) | 티오시아네이토 또는 이소티오시아네이토 치환된 나프탈렌 디이미드 및 릴렌 디이미드 화합물 및 n형 반도체로서의 그의 용도 | |
| TW201006840A (en) | Perylene semiconductors and methods of preparation and use thereof | |
| JP2008513544A (ja) | カルボニル官能化チオフェン化合物および関連する装置構造 | |
| TW201000512A (en) | Semiconductor materials prepared from rylene-(π-acceptor) copolymers | |
| JP2011519350A (ja) | Ｎ，ｎ’−ビス（フルオロフェニルアルキル）で置換されたペリレン−３，４：９，１０−テトラカルボキシイミド、ならびにその製造および使用 | |
| TW201630916A (zh) | 有機化合物及其用途 | |
| Han et al. | Solution processable low bandgap thienoisoindigo-based small molecules for organic electronic devices | |
| CN103044430B (zh) | 并吡咯二酮-噻吩醌化合物及其制备方法与应用 | |
| TW201234579A (en) | Perylene-based semiconductors and methods of preparation and use thereof | |
| TWI811309B (zh) | 基於3,7-雙(2-側氧吲哚啉-3-亞基)苯并[1,2-b:4,5-b']二呋喃-2,6-二酮二氰化物之材料及其在有機電子裝置中的用途 | |
| Lee et al. | Synthesis and characterization of fluorenone-based donor-acceptor small molecule organic semiconductors for organic field-effect transistors | |
| KR20110104218A (ko) | 용액공정용 펜타센 유도체 및 이들의 제조방법과 이를 이용한 유기박막 트렌지스터 | |
| KR100877177B1 (ko) | 아세틸렌기가 치환된 안트라센 구조의 유기반도체 화합물및 이를 이용한 유기박막트랜지스터 | |
| KR101736920B1 (ko) | 아릴기가 치환된 안트라센 화합물, 그 제조 방법 및 이를 이용한 유기 박막 트랜지스터 | |
| HK1140768B (en) | Silylethynylated heteroacenes and electronic devices made therewith | |
| KR100901856B1 (ko) | 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터 | |
| KR100901885B1 (ko) | 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터 | |
| Castrillo | Preparation and characterization of p-type organic thin film transistors based on a novel triindole derivative | |
| Yang | Development of π-Extended Heteroacene-based Materials toward Application in Organic Field-Effect Transistors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |