JP6025748B2 - チオシアネート又はイソチオシアネートで置換したナフタレンジイミド及びリレンジイミド化合物、並びにn−タイプ半導体としてのそれらの使用 - Google Patents
チオシアネート又はイソチオシアネートで置換したナフタレンジイミド及びリレンジイミド化合物、並びにn−タイプ半導体としてのそれらの使用 Download PDFInfo
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- JP6025748B2 JP6025748B2 JP2013548917A JP2013548917A JP6025748B2 JP 6025748 B2 JP6025748 B2 JP 6025748B2 JP 2013548917 A JP2013548917 A JP 2013548917A JP 2013548917 A JP2013548917 A JP 2013548917A JP 6025748 B2 JP6025748 B2 JP 6025748B2
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- 239000004065 semiconductor Substances 0.000 title claims description 50
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 title description 12
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 title description 10
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical compound C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 title description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical group N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title description 2
- 150000002540 isothiocyanates Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- -1 alkyl sulfone Chemical class 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000010409 thin film Substances 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 230000005669 field effect Effects 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000007860 aryl ester derivatives Chemical group 0.000 claims description 3
- 125000005362 aryl sulfone group Chemical group 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- 239000000463 material Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 239000000758 substrate Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 238000007639 printing Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910052710 silicon Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000006413 ring segment Chemical group 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003570 air Substances 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000002094 self assembled monolayer Substances 0.000 description 7
- 239000013545 self-assembled monolayer Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000005693 optoelectronics Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 235000012431 wafers Nutrition 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 229910001867 inorganic solvent Inorganic materials 0.000 description 5
- 239000003049 inorganic solvent Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000002508 contact lithography Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 238000007646 gravure printing Methods 0.000 description 4
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000000813 microcontact printing Methods 0.000 description 4
- 238000007645 offset printing Methods 0.000 description 4
- 238000007649 pad printing Methods 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- HHBCEKAWSILOOP-UHFFFAOYSA-N 1,3-dibromo-1,3,5-triazinane-2,4,6-trione Chemical compound BrN1C(=O)NC(=O)N(Br)C1=O HHBCEKAWSILOOP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
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- 150000003141 primary amines Chemical class 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QXYVHCOWRGMSOO-UHFFFAOYSA-N N#CS.N#CS.C1=CC=C(C=CC=C2)C2=C1 Chemical compound N#CS.N#CS.C1=CC=C(C=CC=C2)C2=C1 QXYVHCOWRGMSOO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
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- 125000005841 biaryl group Chemical group 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000005137 deposition process Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- RHUVFRWZKMEWNS-UHFFFAOYSA-M silver thiocyanate Chemical compound [Ag+].[S-]C#N RHUVFRWZKMEWNS-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
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Description
有機発光ダイオード(OLED)、有機光電装置(OPV)、及び有機電界効果トランジスタ(OFET)における近年の開発は、有機エレクトロニクスの分野において多くの機会が開かれている。この分野における1つの挑戦は、高い移動度を有する環境的に安定な電子輸送(n−タイプ)有機半導体を有する薄膜デバイスを開発することである。有機n−タイプ材料の性能及び安定性は、それらのp−タイプの片方より著しく遅れる。有機n−タイプ材料の技術を高めるためのいくつかの挑戦は、周囲条件(例えば空気)に対するそれらのバルネラビリティ及び溶液加工性を含む。例えば、それは、通常の溶媒中で溶解されるべきこれらの材料のために望ましく、安価な印刷方法のためのインク中に形成されうる。
前記を考慮して、本発明の目的は、それらの概説された前記を含む、技術水準の種々の不足及び欠点を扱うことができる、有機半導体として使用されてよい化合物、及び関連した材料、組成物、複合材、及び/又はデバイスを提供することである。
R1及びR2は、それぞれ、独立して、H、C1-30アルキル基、C2-30アルケニル基、C2-30アルキニル基、C1-30ハロアルキル基、並びに、それぞれ場合により、独立して、ハロゲン、−CN、−NO2、−C(O)H、−C(O)OH、−CONH2、−OH、−NH2、−CO(C1-10アルキル)、−C(O)OC1-14アルキル、−CONH(C1-14アルキル)、−CON(C1-14アルキル)2、−S−C1-14アルキル、−O−(CH2CH2O)n(C1-14アルキル)、−NH(C1-14アルキル)、−N(C1-14アルキル)2、C1-14アルキル基、C2-14アルケニル基、C2-14アルキニル基、C1-14ハロアルキル基、C1-14アルコキシ基、C6-14アリール基、C3-14シクロアルキル基、3〜14員環のシクロへテロアルキル基、及び5〜14員環のヘテロアリール基から選択される1〜4個の基で置換された3〜22員環の環状部分から選択され、
R3は、独立して、ハロゲン、−CN、−NO2、−C(O)O(C1-14アルキル)、−C(O)O(C6-14アリール)、−CHO、C1-14アルキルスルホン、C6-14アリールスルホン、スルホン酸C1-14アルキルエステル又はC6-14アリールエステル基、−CONH2、−CONH(C1-14アルキル)、−CONH(C6-14アリール)、−CON(C1-14アルキル)2、−CON(C1-14アルキル)(C6-14アリール)、−CON(C6-14アリール)2、−C(O)H、C1-14アルコキシ基、C1-14アルキルチオ基、C6-14アリールオキシ基、C6-14アリールチオ基、C1-14アルキル基、3〜14員環のシクロへテロアルキル基、C6-20アリール基、及び5〜20員環のヘテロアリール基から選択され、かつ
nは0、1、2又は3であり、
xは、nが>0である場合に、0、1、2、3又は4であり、
yは、zが0である場合に、1、2、3又は4であり、かつzが>0である場合に、0、1、2、3又は4であり、
zは、yが0である場合に、1、2、3又は4であり、かつyが>0である場合に、0、1、2、3又は4である]の化合物によって解決される。
図1は、電界効果トランジスタの種々の配置を説明する。
本明細書にわたって、組成物が、特定の成分を有する、含む、又は含有するとして記載され、又は方法が、特定の方法工程を有する、含む、又は含有するとして記載されており、本発明の組成物は、実質的に列挙された成分からなり、又は列挙された成分からなり、かつ本発明の方法は、実質的に列挙された方法工程からなり、又は列挙された方法工程からなることが企図される。
2,6−(7)−ジクロロ−N,N’−ビス(1H,1H−ペルフルオロブチル)−ナフタレン[1,8:4,5]−ビス(ジカルボキシイミド)と2,6,7−トリクロロ−N,N’−ビス(1H,1H−ペルフルオロブチル)−ナフタレン[1,8:4,5]−ビス(ジカルボキシイミド)との混合物の製造
蒸着したOFETの製造
a)トップコンタクト配置における蒸着下OFETの製造のための一般手法
高ドープp−タイプケイ素(100)ウェハ(0.01〜0.02Ω・cm)を基材Aとして使用した。主にSiO2層で成長させた厚さ100nmを有する高ドープp−タイプケイ素(100)ウェハ(0.005〜0.02Ω・cm)(電気容量34nF/cm2)を、基材Bとして使用した。
ボトムゲートボトムコンタクト配置における標準基材上での実施例3の化合物で溶液加工したOFETについての方法
50℃まで暖めたクロロホルム中で実施例3の化合物の0.5%溶液を、5000rpmで未処理の標準ケイ素基材上でスピンコート(スピンコータ−:Primus STT15)した。標準ケイ素基材は、230nmの厚さの二酸化ケイ素層(εr=3.9)を有するケイ素ウェハ、並びに金(30nm)及び接着剤としてITOを有するD/Sコンタクトからなった。
Claims (9)
- 式I:
R1及びR2は、それぞれ、独立して、C1-30ハロアルキル基から選択され、
R3は、独立して、ハロゲン、−CN、−NO2、−C(O)O(C1-14アルキル)、−C(O)O(C6-14アリール)、−CHO、C1-14アルキルスルホン、C6-14アリールスルホン、スルホン酸C1-14アルキルエステル又はC6-14アリールエステル基、−CONH2、−CONH(C1-14アルキル)、−CONH(C6-14アリール)、−CON(C1-14アルキル)2、−CON(C1-14アルキル)(C6-14アリール)、−CON(C6-14アリール)2、−C(O)H、C1-14アルコキシ基、C1-14アルキルチオ基、C6-14アリールオキシ基、C6-14アリールチオ基、C1-14アルキル基、3〜14員環のシクロへテロアルキル基、C6-20アリール基、及び5〜20員環のヘテロアリール基から選択され、かつ
nは、0であり、
xは、0であり、
yは、0であり、
zは、2である]
の化合物。 - 前記R1及びR2が、それぞれ、C1-12ハロアルキル基から選択される、請求項1に記載の化合物。
- 前記R1及びR2が、C1-12フルオロアルキル基から選択される、請求項1又は2に記載の化合物。
- 請求項1から4までのいずれか1項に記載の1つ以上の化合物を含む薄膜半導体。
- 請求項5に記載の薄膜半導体を含む、電界効果トランジスタデバイス。
- 請求項5に記載の薄膜半導体を含む、光起電力デバイス。
- 請求項5に記載の薄膜半導体を含む、有機発光ダイオードデバイス。
- 請求項5に記載の薄膜半導体を含む、ユニポーラデバイス又は相補型回路デバイス。
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