WO2013125599A1 - 新規なカルコゲン含有有機化合物およびその用途 - Google Patents
新規なカルコゲン含有有機化合物およびその用途 Download PDFInfo
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- WO2013125599A1 WO2013125599A1 PCT/JP2013/054223 JP2013054223W WO2013125599A1 WO 2013125599 A1 WO2013125599 A1 WO 2013125599A1 JP 2013054223 W JP2013054223 W JP 2013054223W WO 2013125599 A1 WO2013125599 A1 WO 2013125599A1
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- formula
- compound represented
- compound
- alkyl
- arh
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 27
- 229910052798 chalcogen Inorganic materials 0.000 title description 17
- 150000001787 chalcogens Chemical class 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 275
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000002541 furyl group Chemical group 0.000 claims abstract description 35
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 229910052711 selenium Chemical group 0.000 claims abstract description 32
- 239000011669 selenium Chemical group 0.000 claims abstract description 32
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 32
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 239000011737 fluorine Substances 0.000 claims abstract description 25
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 239000011593 sulfur Chemical group 0.000 claims abstract description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003748 selenium group Chemical group *[Se]* 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 9
- 239000004065 semiconductor Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 61
- 239000000758 substrate Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 26
- -1 boronic acid ester Chemical class 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 16
- 238000006880 cross-coupling reaction Methods 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 9
- 230000005669 field effect Effects 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910021536 Zeolite Inorganic materials 0.000 claims description 6
- 229910000085 borane Inorganic materials 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000010457 zeolite Substances 0.000 claims description 6
- 230000031709 bromination Effects 0.000 claims description 5
- 238000005893 bromination reaction Methods 0.000 claims description 5
- VIEXQFHKRAHTQS-UHFFFAOYSA-N chloroselanyl selenohypochlorite Chemical compound Cl[Se][Se]Cl VIEXQFHKRAHTQS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 claims description 5
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 4
- 238000006138 lithiation reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 53
- 239000000126 substance Substances 0.000 abstract description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
- 239000000243 solution Substances 0.000 description 106
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- 230000015572 biosynthetic process Effects 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 43
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- 239000010410 layer Substances 0.000 description 24
- 239000012043 crude product Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000012046 mixed solvent Substances 0.000 description 16
- 239000002274 desiccant Substances 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000007639 printing Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 230000000704 physical effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 238000005266 casting Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 7
- BCOOFVJRQGJVID-UHFFFAOYSA-N C12=CC=CC=C2C(Br)=CC2=C1C1=C3C=CC=CC3=C(Br)C=C1O2 Chemical compound C12=CC=CC=C2C(Br)=CC2=C1C1=C3C=CC=CC3=C(Br)C=C1O2 BCOOFVJRQGJVID-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- BAAAEEDPKUHLID-UHFFFAOYSA-N decyl(triethoxy)silane Chemical compound CCCCCCCCCC[Si](OCC)(OCC)OCC BAAAEEDPKUHLID-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 4
- MSBVBOUOMVTWKE-UHFFFAOYSA-N 2-naphthalen-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C3=CC4=CC=CC=C4C=C3)=CC=C21 MSBVBOUOMVTWKE-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- SWAKCLHCWHYEOW-UHFFFAOYSA-N chloro selenohypochlorite Chemical compound Cl[Se]Cl SWAKCLHCWHYEOW-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000013545 self-assembled monolayer Substances 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 3
- GFAJNLWNSYFCKC-UHFFFAOYSA-N 6-decyl-3-(7-decyl-3-hydroxynaphthalen-2-yl)naphthalen-2-ol Chemical compound CCCCCCCCCCC1=CC=C2C=C(O)C(C=3C(O)=CC4=CC=C(C=C4C=3)CCCCCCCCCC)=CC2=C1 GFAJNLWNSYFCKC-UHFFFAOYSA-N 0.000 description 3
- 229920003026 Acene Polymers 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 3
- 239000012351 deprotecting agent Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 3
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical compound C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000005297 pyrex Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 3
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- 150000000094 1,4-dioxanes Chemical class 0.000 description 2
- ZQUVDVTYZAXUAL-UHFFFAOYSA-N 2-bromo-3-(3-bromonaphthalen-2-yl)naphthalene Chemical compound C1=CC=C2C=C(Br)C(C3=CC4=CC=CC=C4C=C3Br)=CC2=C1 ZQUVDVTYZAXUAL-UHFFFAOYSA-N 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
- H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
- H01L29/76—Unipolar devices, e.g. field effect transistors
- H01L29/772—Field effect transistors
- H01L29/78—Field effect transistors with field effect produced by an insulated gate
- H01L29/786—Thin film transistors, i.e. transistors with a channel being at least partly a thin film
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- 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]
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- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- 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
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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- 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
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- 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]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
Definitions
- the present invention relates to a novel chalcogen-containing organic compound and its use. More specifically, the present invention relates to a novel chalcogen-containing organic compound and a method for producing the same, an organic semiconductor material comprising the organic compound, an organic semiconductor film containing the organic semiconductor material, and an organic field effect transistor (FET) having the organic semiconductor film.
- FET organic field effect transistor
- organic compounds having semiconductor characteristics have attracted attention.
- polyacene compounds such as pentacene and tetracene have long been known as organic semiconductor materials because of their high carrier mobility.
- carrier mobility is used in a broad sense including electron mobility and hole mobility.
- Patent Document 1 compounds in which various substituents are introduced into the acene skeleton have been studied (see, for example, Patent Document 1 and Non-Patent Document 1). Furthermore, compounds in which chalcogens such as sulfur and selenium are introduced into a part of the acene skeleton, such as dibenzothienothiophene (BTBT) and dinaphthothienothiophene (DNTT) have already been studied (for example, Patent Documents 2 to 3). reference).
- BTBT dibenzothienothiophene
- DNTT dinaphthothienothiophene
- the above compound has been successfully improved in chemical stability while maintaining high carrier mobility.
- these have a linear and highly symmetric molecular structure, they have a problem that the solubility is not always sufficient even when a substituent such as an alkyl group is introduced.
- the said compound can be finally synthesize
- organic compounds having semiconductor characteristics have been developed so far.
- an organic compound having excellent chemical stability, high solubility in a solvent, and high carrier mobility for example, it can be applied or printed in the state of a solution, and can be widely used for transistor production, etc.
- Development of materials that can be used in applications is not yet fully developed.
- an organic semiconductor material having a non-linear molecule having a lower symmetry than a linear type as a basic skeleton has been attracting attention.
- Specific examples include compounds having a V-shaped or U-shaped structure such as dinaphthofuran, dinaphthothiophene, dianthrafuran, and dianthrathiophene.
- These basic skeletons (unsubstituted products) are already known (see, for example, Patent Documents 4 to 5 and Non-Patent Documents 2 to 6).
- Patent Documents 4 to 5 and Non-Patent Documents 2 to 6 are already known (see, for example, Patent Documents 4 to 5 and Non-Patent Documents 2 to 6).
- these compounds are excellent in chemical and thermal stability, they have a problem of poor solubility in solvents.
- Patent Document 6 mentions a dinaphthothiophene derivative into which 4 to 12 alkyl groups or phenyl groups are introduced, and an organic film containing this derivative.
- synthesis examples of the derivatives are not disclosed at all, and there is no description to the extent that a so-called person skilled in the art can understand the production method of the derivatives, so that the derivatives are substantially disclosed in Patent Document 6. I can't say that.
- Non-Patent Document 7 discloses a dianthrathiophene derivative represented by the following formula, but similarly, no semiconductor characteristics have been verified.
- An organic compound that is easy to synthesize, has excellent chemical stability, has semiconductor characteristics (high carrier mobility), and has high solubility in a solvent can be applied by using a solution containing the organic compound.
- the film can be formed by a method such as a printing method, its utility value is very large.
- an object of the present invention is an organic compound that is easy to synthesize, has excellent chemical stability, has semiconductor characteristics (high carrier mobility), and has high solubility in a solvent, a method for producing the organic compound,
- An object of the present invention is to provide an organic semiconductor material comprising the organic compound, an organic semiconductor film containing the organic semiconductor material, and an organic field effect transistor (FET) having the organic semiconductor film.
- FET organic field effect transistor
- the present inventors have intensively studied to solve the above problems. As a result, it has been found that the above problems can be solved by a novel chalcogen-containing organic compound having the following constitution, and the present invention has been completed.
- the present invention relates to the following [1] to [15].
- a compound represented by formula (1) [In the formula (1), X is oxygen, sulfur or selenium; two n's are each independently 0 or 1; R 1 to R 3 are each independently hydrogen, fluorine, carbon number 1; ⁇ 20 alkyl, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in said alkyl may be replaced by fluorine, and at least one on said aryl, pyridyl, furyl, thienyl and thiazolyl ring Two hydrogens may be replaced with at least one selected from halogen and alkyl having 1 to 10 carbon atoms; provided that, except when X is selenium, all R 1 to R 3 are simultaneously hydrogen. And X is sulfur and not all R 1 are butyl at the same time. ]
- R 3 are each independently fluorine, carbon atoms 1 ⁇ 20 alkyl, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in said alkyl may be replaced by fluorine, and at least one on said aryl, pyridyl, furyl, thienyl and thiazolyl ring Two hydrogens may be replaced with at least one selected from halogen and alkyl having 1 to 10 carbons.
- R 3 in formula (1-1) and formula (1-2) is the same group selected from alkyl having 4 to 15 carbon atoms, phenyl, furyl and thienyl. The described compound.
- a compound represented by formula (2) [In the formula (2), X is oxygen, sulfur or selenium; two n's are each independently 0 or 1; R 1 to R 2 are each independently hydrogen, carbon number 1 to 20 Alkyl, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in said alkyl may be replaced by fluorine, and at least one hydrogen on said aryl, pyridyl, furyl, thienyl and thiazolyl ring May be replaced by at least one selected from halogen and alkyl having 1 to 10 carbons; provided that not all R 1 to R 2 are hydrogen at the same time. ]
- R 1 in formula (2-1) is the same group selected from alkyl having 6 to 15 carbon atoms, phenyl, furyl, thienyl and thiazolyl.
- a step of coupling a compound represented by the formula (11) to obtain a compound represented by the formula (12); deprotecting methoxy of the compound represented by the formula (12) 13) a step of obtaining a compound represented by formula (13); reacting a compound represented by formula (13) with N, N-dialkylthiocarbamoyl chloride or N, N-dialkylselenocarbamoyl chloride to produce a compound represented by formula (14) And the step of obtaining the compound represented by the formula (15) by heating the compound represented by the formula (14): Sulfur or selenium).
- X is sulfur or selenium
- n and R 1 to R 3 are respectively synonymous with the same symbols in the formula (1)
- Me is methyl
- Each R is independently an alkyl having 1 to 3 carbon atoms.
- a step of coupling a compound represented by the formula (16) with boranes to obtain a boronic acid ester represented by the formula (17); A step of obtaining a compound represented by the formula (18) by bromination with: and lithiation of the compound represented by the formula (18), followed by a reaction with selenium chloride, thereby the compound represented by the formula (15) Get compound A step, compound according to [1] (wherein, X selenium) manufacturing method.
- X selenium
- n and R 1 to R 3 are respectively synonymous with the same symbols in the formula (1)
- Me is In formula (17), each R is independently alkyl having 1 to 3 carbon atoms.
- X oxygen
- X oxygen
- n and R 1 to R 3 are respectively synonymous with the same symbols in the formula (1), and Me is methyl.
- An organic semiconductor material comprising the compound according to any one of [1] to [8].
- An organic semiconductor film containing the organic semiconductor material according to [13].
- An organic field effect transistor having a substrate, a gate electrode, a gate insulating film, a source electrode, a drain electrode, and an organic semiconductor layer, wherein the organic semiconductor layer is composed of the organic semiconductor film described in [14] Organic field effect transistor.
- FET organic field effect transistor
- FIG. 1 shows (a) bottom gate-top contact type, (b) bottom gate-bottom contact type, (c) top gate-top contact type, and (d) top gate-bottom contact type organic field effect transistor (FET).
- FIG. FIG. 2 is a diagram showing an outline of film formation by the edge casting method.
- FIG. 3 is a diagram showing an outline of film formation by the gap casting method.
- FIG. 4 is a graph showing FET characteristics of the compound synthesized in Example 7.
- FIG. 5 is a UV-Vis absorption spectrum of the synthetic compound (solution).
- FIG. 6 is a UV-Vis absorption spectrum of the synthetic compound (film).
- the chalcogen-containing organic compound of the present invention is a compound represented by formula (1) or formula (2), and has a V-shaped structure in which a benzene ring is connected to both wings with a cross-linked portion (-X-) of chalcogen as a bending point. It has a structure of (formula (1)) or U-shape (formula (2)) and has a substituent at any position on the benzene ring.
- the “substituent” means an atom or group other than hydrogen.
- the compound represented by formula (1) is also referred to as “compound (1)”
- the compound represented by formula (2) is also referred to as “compound (2)”
- compound (1) and compound (2) are referred to as “compound (1)”. It is also collectively referred to as “the compound of the present invention”.
- other compounds represented by the formula (i) are also referred to as “compound (i)” (i is a formula number).
- X is oxygen, sulfur or selenium, and since the compound of the present invention exhibits high carrier mobility, oxygen or sulfur is preferable, and sulfur is particularly preferable.
- Two n's are each independently 0 or 1, preferably 0.
- R 1 , R 2 and R 3 are each independently hydrogen, fluorine, alkyl having 1 to 20 carbon atoms, aryl, pyridyl, furyl (furan ring), thienyl (thiophene ring) or thiazolyl (thiazole ring). At least one hydrogen in the alkyl may be replaced with fluorine. At least one hydrogen on the aryl, pyridyl, furyl, thienyl and thiazolyl ring is at least one selected from halogen and alkyl having 1 to 10 (preferably 1 to 6, more preferably 1 to 3) carbon atoms. May be replaced.
- R 2 and R 3 are not R 1, R 2 and R 3 only may be the same or different from each other, the plurality of R 1 are mutually However, they may be different, a plurality of R 2 may be the same or different from each other, and a plurality of R 3 may be the same or different from each other.
- the atoms or groups bonded to the 12th and 13th carbons are preferably the same, and the 1st and 11th positions, the 2nd and 10th positions, 3 Similarly, the atoms or groups bonded to the carbons at the 9th, 4th, 8th, 5th and 7th positions are preferably the same.
- the atoms or groups bonded to the 15th and 16th carbons are preferably the same, and the 14th and 17th positions, the 1st and 13th positions, Similarly, the atoms or groups bonded to the carbons at the 12th, 12th, 3rd and 11th, 4th and 10th, 5th and 9th, 6th and 8th positions are preferably the same.
- R 1 to R 3 are not hydrogen at the same time except when X is selenium. Also, X is sulfur and all R 1 are not simultaneously butyl.
- X is oxygen, sulfur or selenium.
- n's are each independently 0 or 1, preferably 0.
- R 1 and R 2 are each independently hydrogen, alkyl having 1 to 20 carbon atoms, aryl, pyridyl, furyl (furan ring), thienyl (thiophene ring) or thiazolyl (thiazole ring). At least one hydrogen in the alkyl may be replaced with fluorine. At least one hydrogen on the aryl, pyridyl, furyl, thienyl and thiazolyl ring is at least one selected from halogen and alkyl having 1 to 10 (preferably 1 to 6, more preferably 1 to 3) carbon atoms. May be replaced.
- each independently in defining R 1 and R 2, as well as R 1 and R 2 may be the same or different from each other, a plurality of R 1 are may be the same or different from each other, A plurality of R 2 may be the same or different from each other. However, not all R 1 and R 2 are hydrogen at the same time.
- the atoms or groups bonded to the 1st and 13th carbons are preferably the same, and the 2nd and 12th positions, the 3rd and 11th positions, Similarly, the atoms or groups bonded to the carbons at the 10th position, the 10th position, the 5th position and the 9th position, and the 6th position and the 8th position are also preferably the same.
- the atoms or groups bonded to the 1st and 15th carbon atoms are preferably the same, and the 2nd and 14th positions, the 3rd and 13th positions, Similarly, the atoms or groups bonded to the carbon at the 12th position, the 5th position and the 11th position, the 6th position and the 10th position, the 7th position and the 9th position, and the 16th position and the 17th position are also preferably the same.
- the alkyl having 1 to 20 carbon atoms listed as R 1 to R 3 includes, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, Examples include decyl, dodecyl, undecyl and octadecyl.
- the number of carbon atoms of the alkyl is preferably 4 to 15 and more preferably 4 to 12 from the viewpoint of both high solubility of the compound of the present invention in a solvent and ease of overlapping of electron clouds between molecules. Particularly preferred is 6-12.
- Alkyl may be either linear or branched, and is preferably linear from the viewpoint of molecular arrangement in the crystal.
- the group formed by replacing at least one hydrogen in the alkyl with fluorine a group in which all hydrogens in the alkyl such as trifluoromethyl, perfluorohexyl, perfluorooctyl and perfluorodecyl are replaced with fluorine; Only hydrogen bonded to carbon directly bonded to an aromatic ring such as fluoroethyl, 1H, 1H-perfluorohexyl, 1H, 1H-perfluorooctyl and 1H, 1H-perfluorodecyl is not replaced by fluorine. Examples include groups in which all hydrogens are replaced by fluorine.
- aryls listed as R 1 to R 3 include, for example, phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), fluorenyl (eg, 2-fluorenyl) and biphenyl Is mentioned.
- the number of carbon atoms of aryl is preferably 6 to 14, and more preferably 6 to 10. Of these, phenyl is particularly preferred.
- examples of pyridyl listed as R 1 to R 3 include 2-pyridyl, 3-pyridyl and 4-pyridyl.
- Examples of the group formed by replacing at least one hydrogen on the aryl ring with an alkyl having 1 to 10 carbon atoms include tolyl and xylyl.
- Examples of the group formed by replacing at least one hydrogen on the aryl ring with a halogen include p-fluorophenyl, pentafluorophenyl, p-chlorophenyl, and pentachlorophenyl.
- furyl listed as R 1 to R 3 is, for example, 2-furyl, 3-furyl; thienyl is, for example, 2-thienyl and 3-thienyl; thiazolyl Is, for example, 2-thiazolyl.
- At least one hydrogen on the aryl, pyridyl, furyl, thienyl and thiazolyl rings may be replaced by a halogen.
- the halogen include chlorine, bromine and fluorine, preferably fluorine.
- disubstituted derivatives that is, compounds represented by formula (1-1) or formula (1-2) are preferable.
- the compound represented by the formula (1-1) is particularly preferable because it exhibits high carrier mobility.
- R 3 s are each independently fluorine, alkyl having 1 to 20 carbons, aryl, pyridyl, furyl, thienyl or thiazolyl. At least one hydrogen in the alkyl may be replaced with fluorine. At least one hydrogen on the aryl, pyridyl, furyl, thienyl and thiazolyl ring may be replaced with at least one selected from halogen and alkyl having 1 to 10 carbons. Specific examples and preferred examples of these substituents are as described above in the description of the formulas (1) and (2).
- two R 3 s may be the same or different from each other, and are preferably the same substituent.
- Two R 3 s are preferably the same group selected from alkyl having 1 to 20 carbon atoms, phenyl, furyl and thienyl, more preferably alkyl having 1 to 20 carbon atoms. More preferably has 4 to 15 carbon atoms, particularly preferably alkyl having 4 to 12 carbon atoms, and most preferably alkyl having 6 to 12 carbon atoms.
- compounds represented by the following formula are also preferable.
- n is synonymous with the same symbol in Formula (1).
- disubstituted derivatives that is, compounds represented by the formula (2-1) are preferable from the viewpoint of high-density assembly of organic semiconductor molecules.
- R 1 s are each independently alkyl, aryl, pyridyl, furyl, thienyl or thiazolyl having 1 to 20 carbon atoms. At least one hydrogen in the alkyl may be replaced by fluorine, and at least one hydrogen on the aryl, pyridyl, furyl, thienyl and thiazolyl ring is selected from halogen and alkyl having 1 to 10 carbons. It may be replaced with at least one kind. Specific examples and preferred examples of these substituents are as described above in the description of the formulas (1) and (2).
- two R 1 s may be the same or different from each other, and are preferably the same substituent.
- the two R 1 are more preferably the same group selected from alkyl having 6 to 15 carbon atoms, phenyl, furyl, thienyl and thiazolyl.
- Formula (1-1), Formula (1-2), and Formula (2-1) are, for example, the following formulas.
- the compound of the present invention exhibits high solubility in a solvent due to its structure (non-linear and chalcogen cross-linked structure) and preferably the effect of introduction of substituents. That is, a solution can be prepared with the concentration of the compound described later. Therefore, it becomes possible to apply
- the interaction between molecules is improved by chalcogen present at the bent part of the molecule, and the ⁇ electron orbital overlap is sufficient between the molecules. Therefore, the compound of the present invention and the organic semiconductor film containing this compound are Shows a sufficiently high carrier mobility.
- the carrier mobility when used as an organic semiconductor element is preferably 0.5 cm 2 / V ⁇ s or more, more preferably 1.0 cm 2 / V ⁇ s or more, Particularly preferably, it is 5.0 cm 2 / V ⁇ s or more.
- the upper limit value of the carrier mobility is not particularly limited, but is, for example, about 50.0 cm 2 / V ⁇ s.
- the carrier mobility is, for example, a 0.2% by mass concentration o-xylene solution, a 0.2% by mass concentration 1,2-dichloroethane solution, or a 0.2% by mass concentration o-dichlorobenzene solution of the compound of the present invention.
- the details of the film forming method and the measuring method eg, edge casting method, gap casting method are as described in the examples.
- the compound of the present invention has an excellent property as an organic semiconductor material, in addition to a property of high carrier mobility, a high on / off ratio of drain current due to a gate voltage of a transistor.
- the compound of the present invention is excellent in chemical stability such as oxidation resistance. Moreover, since the compound of this invention can be synthesize
- Examples of the compound of the present invention are shown below.
- Step 3A ′ for obtaining a compound represented by Formula (15) or Formula (26) by heat dehydration is included.
- R 1 to R 3 and n have the same meanings as the same symbols in formula (1), respectively; in formulas (21) to (26), R 1 to R 2 and n Each has the same meaning as the same symbol in formula (2); each R is independently alkyl having 1 to 3 carbon atoms.
- Me is methyl
- n-Bu is normal butyl
- Et is ethyl
- Py is pyridine.
- the reaction is preferably performed in a solution state.
- the solvent include at least selected from the group consisting of nitrile solvents such as acetonitrile; halogenated solvents such as dichloromethane, chloroform, chlorobenzene, and dichlorobenzene; ether solvents such as tetrahydrofuran; aromatic hydrocarbon solvents such as toluene;
- nitrile solvents such as acetonitrile
- halogenated solvents such as dichloromethane, chloroform, chlorobenzene, and dichlorobenzene
- ether solvents such as tetrahydrofuran
- aromatic hydrocarbon solvents such as toluene
- One organic solvent is preferably used.
- organic solvents such as hexane.
- the obtained compound (crude product) may be appropriately purified between the respective steps.
- the purification method include column chromatography and recrystallization.
- Step 1A compound (11) is homocoupled in the presence of an organometallic compound, or compound (21) is homocoupled.
- the reaction temperature in Step 1A eg, the temperature of the solution
- the reaction time is usually 2 to 14 hours; the reaction is usually performed under normal pressure.
- the room temperature means a temperature environment of about 23 ° C.
- organometallic compound examples include n-butyllithium and s-butyllithium, which may be used alone or in combination of two or more.
- the amount of the organometallic compound used is usually 1.05 to 2.10 mol per 1 mol of compound (11) or (21).
- Step 2A methoxy of compound (12) or (22) is deprotected in the presence of a deprotecting agent.
- the reaction temperature in Step 2A eg, the temperature of the solution
- the reaction time is usually 1 to 2 hours
- the reaction is usually performed under normal pressure. Is called.
- Examples of the deprotecting agent include boron tribromide and aluminum chloride, which may be used alone or in combination of two or more.
- the amount of the deprotecting agent to be used is generally 2.0 to 2.4 mol with respect to 1 mol of compound (12) or (22).
- Step 3A compound (13) or (23) is reacted with N, N-dialkylthiocarbamoyl chloride or N, N-dialkylselenocarbamoyl chloride in the presence of a base.
- the reaction temperature in Step 3A eg, heating temperature of the solution
- the reaction time is usually 10 to 48 hours
- the reaction is usually performed under normal pressure.
- the number of carbon atoms of two alkyls in N, N-dialkylthiocarbamoyl chloride and N, N-dialkylselenocarbamoyl chloride is each independently 1 to 3, preferably 1 to 2.
- N, N-dialkylthiocarbamoyl chloride examples include N, N-dimethylthiocarbamoyl chloride and N, N-diethylthiocarbamoyl chloride.
- Examples of N, N-dialkylselenocarbamoyl chloride include N, N-dimethylselenocarbamoyl chloride and N, N-diethylselenocarbamoyl chloride.
- the amount of N, N-dialkylthiocarbamoyl chloride or N, N-dialkylselenocarbamoyl chloride to be used is generally 3.0 to 4.0 mol with respect to 1 mol of compound (13) or (23).
- Examples of the base include triethylamine, pyridine, and sodium hydride, and these may be used alone or in combination of two or more.
- the amount of the base used is usually 1.1 to 5.0 mol, preferably 1.5 to 2.5 mol, and usually 5 to 30 mol, preferably 10 mol, of triethylamine with respect to 1 mol of compound (13) or (23). ⁇ 20 mol.
- step 4A compound (14) or (24) is heated and cyclized to obtain compound (15) or (25) which is a compound of the present invention.
- the heating temperature in step 4A is usually 300-310 ° C .; the reaction time is usually 4-6 hours.
- Step 3A ′ zeolite is added to the solution of compound (13) or (23), followed by dehydration and cyclization to obtain compound (15) or (26) which is the compound of the present invention.
- the heating temperature in Step 3A ′ eg, the heating temperature of the solution
- the reaction time is usually 8 to 20 hours, preferably 10 to 16 hours
- the reaction is usually performed under normal pressure Done.
- the compound (2-1) of the present invention is obtained by brominating an unsubstituted compound represented by the formula (27) synthesized by a known method, followed by a known cross-coupling reaction.
- the method of introducing a desired substituent by a cross-coupling reaction is particularly useful for the synthesis of a disubstituted product.
- the compound represented by the formula (27) is brominated to obtain a compound represented by the formula (28) 1B; 28) Step 2B of obtaining a compound represented by the formula (29) by reacting the compound represented by 28) with a cross-coupling reagent (by performing a cross-coupling reaction).
- Step 1B (bromination)
- the amount of bromine used is usually 2.0 to 2.2 mol per 1 mol of compound (27).
- the heating temperature in Step 1B (eg, the heating temperature of the solution or suspension) is usually room temperature to 100 ° C., preferably 80 to 100 ° C .; the reaction time is usually 4 to 10 hours, preferably 4 to 8 hours. The reaction is usually carried out under normal pressure.
- bromination of compound (27) is preferably performed in the state of a solution or suspension.
- at least one organic solvent selected from the group consisting of acetic acid and chloroform is preferably used as the solvent.
- the obtained compound (crude product) may be appropriately purified between Step 1B and Step 2B.
- Examples of the purification method include column chromatography and recrystallization.
- the compound (28), that is, the compound represented by the formula (2-1 ') is suitable as a raw material compound used for the synthesis of the compound (29), that is, the compound represented by the formula (2-1).
- X is oxygen, sulfur or selenium; two n's are each independently 0 or 1.
- Step 2B the bromine moiety of compound (28) is substituted with substituent R 1 by a known cross-coupling reaction such as Suzuki coupling, Stille coupling, Negishi coupling, Tamao coupling, and reactions derived therefrom. Convert to R 1 has the same meaning as the same symbol in formula (2-1).
- step 2B it is preferable to perform cross coupling of compound (28) in the state of a solution or suspension.
- the solvent for example, it is preferable to use at least one organic solvent selected from the group consisting of N, N-dimethylformamide, tetrahydrofuran, toluene and diethyl ether, although it varies depending on the cross-coupling reaction form.
- cross-coupling reaction agent compound for introducing substituent R 1
- reaction conditions eg, temperature, time
- Examples of the cross-coupling reagent include R 1 -SnR 3 such as tributyl (2-thienyl) tin, tributyl (2-furyl) tin and tributyl (2-thiazolyl) tin (wherein R 1 is thienyl, furyl) Or R 1 -MgX (wherein R 1 is alkyl having 1 to 20 carbons, aryl having 6 to 14 carbons, or pyridyl, and X is thiazolyl and R is alkyl such as butyl) R 1 —B (OH) 2 (wherein R 1 is aryl having 6 to 14 carbon atoms or pyridyl); R 1 —ZnX (wherein R 1 is a halogen such as bromine); And aryl having 6 to 14 carbon atoms or pyridyl).
- the amount of the cross-coupling reagent to be used is generally 1.1-4.0 mol, preferably 2.0-3
- the catalyst examples include tetrakis (triphenylphosphine) palladium (0), 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride-dichloromethane complex and tris (dibenzylideneacetone) dipalladium (0) chloroform.
- Palladium catalysts such as complexes, and nickel catalysts such as [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride can be mentioned.
- the reaction temperature in Step 2B (eg, the temperature of the solution or suspension) is usually 0 to 140 ° C., preferably room temperature to 140 ° C .; the reaction time is usually 10 minutes to 24 hours, preferably 1 to 24 hours.
- the reaction is usually carried out under normal pressure.
- the reaction temperature varies depending on the type of coupling, for example, 80 to 140 ° C. for Still coupling, 0 ° C. to room temperature for Tamao coupling, and 80 to 110 ° C. for Suzuki coupling.
- Step 5A for obtaining a compound represented by formula (16) Step 6A for obtaining a boronic acid ester represented by formula (17) by coupling a compound represented by formula (16) with a borane; Step 7A to obtain a compound represented by the formula (18) by bromination of a boronic acid ester with copper bromide; and lithiation of the compound represented by the formula (18), followed by reaction with selenium chloride. And Step 8A for obtaining a compound represented by the formula (15).
- each R is independently alkyl having 1 to 3 carbon atoms.
- the reaction is preferably performed in a solution state.
- the solvent include pyrrolidone solvents such as N-methyl-2-pyrrolidone; halogenated solvents such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene; ether solvents such as tetrahydrofuran and 1,4-dioxane; alcohols such as methanol. It is preferable to use at least one organic solvent selected from the group consisting of: a system solvent.
- Step 5A compound (13) is reacted with trifluoromethanesulfonyl chloride or trifluoromethanesulfonic anhydride to obtain compound (16).
- the reaction temperature in Step 5A eg, the temperature of the solution
- the reaction time is usually from 2 to 24 hours.
- the amount of trifluoromethanesulfonyl chloride or trifluoromethanesulfonic anhydride used is usually 2.0 to 5.0 mol per 1 mol of compound (13).
- Step 5A can be performed in the presence of a base.
- the base include pyridine, triethylamine, and N, N-dimethyl-4-aminopyridine, which may be used alone or in combination of two or more.
- the amount of the base to be used is generally 0.1 to 10.0 mol with respect to 1 mol of compound (13).
- Step 6A the boronic ester (17) is obtained by coupling the compound (16) with boranes.
- the reaction temperature in Step 6A eg, the temperature of the solution
- the reaction time is usually 3 to 24 hours.
- boranes examples include compounds represented by the following formula, specifically 4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
- the amount of borane to be used is generally 2.0 to 5.0 mol with respect to 1 mol of compound (16).
- each R is independently alkyl having 1 to 3 carbon atoms.
- a catalyst can be used.
- palladium such as tetrakis (triphenylphosphine) palladium (0), 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride-dichloromethane complex and tris (dibenzylideneacetone) dipalladium (0) chloroform complex
- nickel catalysts such as [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride.
- Step 6A can be performed in the presence of a base.
- a base is triethylamine.
- the amount of the base to be used is generally 2.0 to 10.0 mol with respect to 1 mol of compound (16).
- Step 7A the boronate ester (17) is brominated with copper bromide to obtain the compound (18).
- the reaction temperature of Step 7A eg, the temperature of the solution
- the reaction time is usually 6 to 30 hours.
- the amount of copper bromide to be used is usually 2.0 to 10.0 mol with respect to 1 mol of boronic ester (17).
- Step 8A In Step 8A, compound (18) is lithiated and then reacted with selenium chloride to give compound (15).
- the reaction temperature in Step 8A eg, the temperature of the solution
- the reaction time is usually 1 to 5 hours.
- Examples of the lithiating agent include t-butyllithium.
- the amount of the lithiating agent to be used is generally 2.0-5.0 mol with respect to 1 mol of compound (18).
- the amount of selenium chloride to be used is generally 1.0-1.5 mol with respect to 1 mol of compound (18).
- the compound of the present invention exhibits high solubility in a solvent, so that a crude compound is synthesized by a simple method such as column chromatography or recrystallization.
- the product can be easily purified.
- the film of the present invention contains at least one compound selected from the compounds of the present invention, that is, the compound (1) and the compound (2). Since the compound of the present invention exhibits high solubility in a solvent, a solution in which these compounds are dissolved in a solvent (hereinafter also referred to as “organic semiconductor solution”) is coated or printed on a substrate to obtain a uniform surface. A film having excellent properties (eg, an organic semiconductor film) can be formed.
- Examples of the solvent used for preparing the organic semiconductor solution include pentane, hexane, heptane, diethyl ether, t-butyl methyl ether, tetrahydrofuran, methanol, ethanol, isopropanol, ethyl acetate, ethyl lactate, dioxane, benzene, toluene, Xylene, dichloromethane, chloroform, 1,2-dichloroethane, dichlorobenzene, acetonitrile, acetone, cyclohexane, cyclopentanone, cyclohexanone, ⁇ -butyrolactone, butyl cellosolve, N-methyl-2-pyrrolidone, N, N-dimethylformamide (DMF) And organic solvents such as dimethyl sulfoxide; water; or a mixture of two or more thereof.
- organic solvents such as dimethyl sulfoxide; water
- the concentration of the compound of the present invention in the organic semiconductor solution is preferably 0.05 to 10% by mass, more preferably 0.1 to 5% by mass. Since the compound of the present invention exhibits high solubility in a solvent, a high concentration solution can be prepared.
- the high concentration solution of the compound of the present invention refers to a solution in which the concentration of the compound in the organic semiconductor solution is 0.1% by mass or more.
- the organic semiconductor solution having various concentrations can be prepared by the excellent solubility of the compound of the present invention in the solvent, the crystallinity of the obtained film can be changed.
- the carrier mobility affected by the crystallinity also changes. Therefore, in the present invention, crystallinity in a wide range from crystal to amorphous can be easily adjusted, and necessary element characteristics such as the thickness of the organic semiconductor film and carrier mobility can be stably reproduced.
- a film may be formed using a resin composition containing the compound of the present invention and a polymer compound.
- the content of the polymer compound in the resin composition is usually 1 to 99% by mass, preferably 5 to 90% by mass, more preferably 5 to 80% by mass.
- the content of the solvent in the resin composition is appropriately set so that the content of the compound of the present invention and the polymer compound is in the above range, and the resin composition has a viscosity suitable for film formation. .
- the polymer compound examples include a thermoplastic polymer and a thermosetting polymer. Specifically, polyester, polyamide, polystyrene, polymethacrylic acid, polyacrylic acid, polyethylene, polypropylene, polycycloolefin, polyvinyl chloride, polyvinylidene chloride, polyvinyl acetate, polycarbonate, phenol resin, polyurethane resin, epoxy resin, Mention may be made of melamine resins, polytetrafluoroethylene, polyacetylene, polypyrrole and polyarylene vinylene. Further, a conductive polymer may be used as the polymer compound. Examples of the conductive polymer include polythiophene, polypyrrole, and polyaniline.
- the thickness of the film of the present invention can be appropriately selected according to the desired application.
- the thickness of the organic semiconductor film used in the organic semiconductor element is preferably 10 to 1,000 nm, more preferably 10 to 200 nm.
- the method for producing the film of the present invention can be used as the method for producing the film of the present invention.
- the coating method include a spin coating method, a dip coating method, and a blade method.
- the edge cast method and the gap cast method which will be described later in Examples, which are classified into coating methods developed by the present inventors, are also effective.
- Examples of the printing method include screen printing, inkjet printing, planographic printing, intaglio printing, and letterpress printing.
- inkjet printing performed by a printer using the compound solution of the present invention as an ink as it is is preferable because it is a simple method. There is no problem even if the film is formed by using a film forming method other than the above method, for example, vapor deposition.
- the temperature at the time of film formation is not particularly limited, and is usually room temperature to 200 ° C., preferably 50 to 150 ° C.
- the temperature here is, for example, the heating temperature of the organic semiconductor solution in the coating method or the printing method, the temperature of the atmosphere, and the heating temperature of the substrate used for film formation. Further, the solution temperature, the ambient temperature, and the substrate temperature may be different from each other. In the film forming method not using the above solution, for example, the vapor deposition method, it means the heating temperature of the substrate used for film formation.
- patterning is preferably performed by a printing method, and it is preferable to use a high concentration solution of the compound of the present invention in the printing method. If a high concentration solution is used, inkjet printing, mask printing, screen printing, offset printing, and the like can be utilized.
- the production of the organic semiconductor film by the printing method can be produced by a flow operation without the need for heating or a vacuum process, which contributes to cost reduction and increased responsiveness to process changes.
- the production of an organic semiconductor film by a printing method contributes to simplification of the circuit of the element, improvement of production efficiency, and reduction in the cost and weight of the element. From the above viewpoint, the compound of the present invention showing high solubility in a solvent is excellent.
- Organic semiconductor element of this invention has the said organic-semiconductor film and electrode.
- an organic semiconductor element can be obtained by combining the organic semiconductor film and an element having other semiconductor characteristics. Examples of the element having other semiconductor characteristics include a rectifying element, a thyristor that performs a switching operation, a triac, and a diac.
- the organic semiconductor element of the present invention can also be used as a display element, and a display element in which all members are composed of organic compounds is particularly useful.
- Examples of the display element include a flexible sheet-like display device (eg, electronic paper, IC card tag), a liquid crystal display element, and an electroluminescence (EL) element.
- These display elements are formed by forming the organic semiconductor film of the present invention and one or more layers including components that function the film on an insulating substrate formed of a flexible polymer. Can be produced. Since the display element manufactured by such a method has flexibility, it can be carried in a pocket or a wallet of clothes.
- Examples of the display element include a unique identification code response device.
- the unique identification code response device is a device that responds to an electromagnetic wave having a specific frequency or a specific code and returns an electromagnetic wave including the unique identification code.
- the unique ID code response device identifies a document or individual in a reusable ticket or membership card, payment method, package or product identification sticker, tag or stamp role, and company or administrative service. Used as a means.
- the unique identification code response device is a book that operates on a glass substrate or an insulating substrate made of a polymer exhibiting flexibility and receives an antenna in synchronization with a signal, and receives an identification signal. And an organic semiconductor element of the invention.
- Examples of the organic semiconductor element of the present invention include an organic field effect transistor (FET).
- the organic FET of the present invention can also be used in combination with a liquid crystal display element and an electroluminescence (EL) element.
- the organic FET of the present invention has a substrate, a gate electrode, a gate insulating film, a source electrode, a drain electrode, and an organic semiconductor layer, and the organic semiconductor layer is composed of the organic semiconductor film of the present invention.
- the organic FET of the present invention may have a carrier injection layer in order to increase the carrier injection efficiency.
- the organic FET by controlling the voltage applied to the gate electrode, carriers are induced at the interface of the organic semiconductor layer on the gate insulating film, the current flowing through the source electrode and the drain electrode is controlled, and the switching operation is performed.
- carrier mobility can be obtained from a drain current / gate voltage curve obtained by measuring a current between a source and a drain electrode while changing a drain voltage and a gate voltage. Furthermore, it is possible to observe the on / off operation of the drain current due to the gate voltage.
- the structure of the organic FET is roughly divided into a bottom gate type structure and a top gate type structure, and these are further classified into a top contact structure and a bottom contact structure.
- a mode in which a gate electrode is formed on a substrate and a gate insulating film and an organic semiconductor layer are formed in this order is called a bottom gate type; the organic semiconductor layer, the gate insulating film, and the gate electrode are formed on the substrate.
- the structure formed in this order is called a top gate type.
- a mode in which the source electrode and the drain electrode are disposed below the organic semiconductor layer (substrate side) is called a bottom contact type FET; the source electrode and the drain electrode are above the organic semiconductor layer (the organic semiconductor layer)
- a mode of being arranged on the opposite side of the substrate across the substrate is called a top contact type FET.
- the top contact structure often has better organic FET characteristics than the bottom contact structure.
- FIGS. 1A and 1B show cross sections of (a) bottom gate-top contact type, (b) bottom gate-bottom contact type, (c) top gate-top contact type, and (d) top gate-bottom contact type organic FET, respectively.
- the figure is shown.
- the organic FET of the present invention is not limited to the organic FET structure exemplified above, and may have a known organic FET structure. Further, a vertical organic FET structure may be adopted.
- substrates various substrates can be mentioned. Specifically, glass substrates, metal substrates such as gold, copper and silver, crystalline silicon substrates, amorphous silicon substrates, triacetyl cellulose substrates, norbornene substrates, polyester substrates such as polyethylene terephthalate substrates, polyvinyl substrates, polypropylene substrates, polyethylene A substrate is mentioned.
- the material of the gate electrode examples include Al, Ta, Mo, Nb, Cu, Ag, Au, Pt, In, Ni, Nd, Cr, polysilicon, amorphous silicon, highly doped silicon, tin oxide, indium oxide, and the like.
- inorganic materials such as indium tin oxide (ITO); organic materials such as conductive polymers.
- the conductive polymer may be processed to improve conductivity by adding impurities.
- Examples of the material for the gate insulating film include inorganic materials such as SiO 2 , SiN, Al 2 O 3, and Ta 2 O 5 ; and polymer materials such as polyimide and polycarbonate.
- the surface of the gate insulating film and the substrate is a known silane coupling agent such as hexamethyldisilazane (HMDS), octadecyltrichlorosilane (OTS), decyltriethoxysilane (DTS), octadecyltriethoxysilane (ODSE), etc.
- HMDS hexamethyldisilazane
- OTS octadecyltrichlorosilane
- DTS decyltriethoxysilane
- ODSE octadecyltriethoxysilane
- Surface treatment can be performed using a silane coupling agent having an alkyl group or a silane coupling agent having a fluoroalkyl group such as triethoxytridecafluorooctylsilane (F-SAM).
- F-SAM triethoxytridecafluorooctyls
- the same material as that for the gate electrode can be used, and it may be the same as or different from the material for the gate electrode, or different materials may be laminated.
- the carrier injection layer is provided in contact with both the source and drain electrodes and the organic semiconductor layer as necessary in order to increase the carrier injection efficiency.
- the carrier injection layer is formed using, for example, tetrafluorotetracyanoquinodimethane (F4TCNQ), hexaazatriphenylenehexacarbonitrile (HAT-CN), molybdenum oxide, or the like.
- the measuring method of the physical property value of a synthetic compound is as follows.
- the melting point was measured using a Toledo MP70 automatic melting point measurement system manufactured by METTLER. 1 H-NMR spectrum and 13 C-NMR spectrum were measured using ECA-600 manufactured by JEOL Ltd. and ECS400 spectrometer. For elemental analysis, JM10 MICRO CORDER manufactured by J Science Lab Co., Ltd. was used. For mass spectrometry, a JMS-T100LC APCI / ESI mass spectrometer manufactured by JEOL Ltd. and an ultraflex III TOF / TOF manufactured by Bruker Daltonics were used. In the title compounds of the following examples, all alkyls are linear groups.
- the organic layer was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and after removing the desiccant, the solution was concentrated under reduced pressure using a rotary evaporator.
- Example 1 According to Example 1, except that the starting material was changed to 6,6′-didecyl-3,3′-dimethoxy-2,2′-binaphthalene in Example 1, the title compound (yield) : 94%). Physical property values are shown below.
- Example 1 According to Example 1, except that the starting material was changed to 6,6′-dibutyl-3,3′-dimethoxy-2,2′-binaphthalene in Example 1, the title compound (yield) : 97%). Physical property values are shown below.
- Example 1 According to Example 1, except that the starting material was changed to 6,6′-dihexyl-3,3′-dimethoxy-2,2′-binaphthalene in Example 1, the title compound (yield) : 88%). Physical property values are shown below.
- Example 6 the title compound (yield: 72%) was obtained as a pale yellow solid according to Example 6 except that the starting material decyl was changed to hexyl. Physical property values are shown below.
- Example 6 The title compound (yield: 73%) was obtained as a pale yellow solid according to Example 6 except that the starting material decyl was changed to octyl. Physical property values are shown below.
- Example 6 the title compound (yield: 81%) was obtained as a pale yellow solid according to Example 6 except that the starting material decyl was changed to butyl. Physical property values are shown below.
- Example 6 the title compound (yield: 73%) was obtained as a pale yellow solid according to Example 6 except that the starting material decyl was changed to pentyl. Physical property values are shown below.
- Example 6 the title compound (yield: 75%) was obtained as a pale yellow solid according to Example 6, except that the starting material decyl was changed to heptyl. Physical property values are shown below.
- Example 6 the title compound (yield: 83%) was obtained as a pale yellow solid according to Example 6 except that the starting material decyl was changed to dodecyl. Physical property values are shown below.
- Triethylamine (30.9 mL, 222 mmol) was added to a dehydrated dichloromethane solution (148 mL) of 6,6′-dihexyl- [2,2′-binaphthalene] -3,3′-diol (16.8 g, 37.0 mmol) at 0 ° C. ) And N, N-dimethyl-4-aminopyridine (DMAP; 633 mg, 5.18 mmol), and at 0 ° C., a dehydrated dichloromethane solution (50 mL) of trifluoromethanesulfonic anhydride (18.6 mL, 111 mmol) was added. It was dripped.
- DMAP N, N-dimethyl-4-aminopyridine
- the filtrate was washed with water and the organic layer was extracted three times with toluene.
- the combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, removed the desiccant, and concentrated under reduced pressure using a rotary evaporator.
- the obtained crude product was dissolved in chloroform, passed through silica gel, and further subjected to gel filtration chromatography using chloroform as a developing solvent to obtain the title compound (355 mg, 82%) as a yellow solid.
- a silicon substrate (made by Fujimi Fine Technology Co., Ltd.) is subjected to surface treatment with decyltriethoxysilane (DTS), and a silicon substrate (hereinafter also referred to as “substrate”) with a thermally oxidized silicon insulating film (film thickness 500 nm) is provided. Obtained.
- a piece of silicon substrate for holding a solution (hereinafter also referred to as “solution holding structure”) was placed on the substrate. While tilting the substrate, the o-xylene solution or 1,2-dichloroethane solution of the chalcogen-containing organic compound synthesized in the example (concentration of the chalcogen-containing organic compound: 0.2% by mass) (organic semiconductor solution) at 120 ° C.
- the crystal was attached to the substrate while the crystal was growing as the solvent evaporated, and the crystal growth was completed in a few minutes. In this state, the crystal film was completely dried (film thickness: 30 to 150 nm) by being left overnight (11 hours) in an argon atmosphere at 60 to 100 ° C.
- a carrier injection layer film thickness: 1 nm
- a gold source electrode and a drain electrode (30 nm) are vacuum-deposited on the obtained crystal film through a stainless steel metal mask.
- a bottom gate-top contact type organic FET having a length of 100 ⁇ m and a channel width of 1 mm was produced.
- the fabricated devices were measured for carrier mobility and on / off ratio using a semiconductor parameter analyzer (model number “keithley 4200”, Keithley Instruments Co., Ltd.).
- a spacer was placed on the surface-treated substrate used in the ⁇ edge casting method>, and a silicon substrate surface-treated with F-SAM was stacked on the substrate as a solution holding plate to form a wedge-shaped gap. .
- This was heated to 120 ° C. on a hot plate, and after stabilizing the temperature, an o-dichlorobenzene solution of the chalcogen-containing organic compound synthesized in the example (concentration of chalcogen-containing organic compound: 0.2% by mass) (organic semiconductor solution) was injected into the wedge-shaped gap. The solution is held in a wedge-shaped gap, and crystals grow as the solvent evaporates.
- the crystal film was completely dried (film thickness: 150 to 250 nm) by being left overnight (11 hours) in an argon atmosphere at 60 to 100 ° C. in this state. Thereafter, an element was produced in the same manner as in the above ⁇ edge casting method>, and FET characteristics were evaluated.
- FIG. 4 shows the FET characteristics of the compound synthesized in Example 7. According to FIG. 4, it was confirmed that the compound synthesized in Example 7 exhibited a high carrier mobility of 10 to 11 cm 2 / vs.
- the above silicon substrate with a thermally oxidized silicon insulating film (film thickness 500 nm) was subjected to ultrasonic cleaning with acetone and 2-propanol for 5 minutes each, followed by UV ozone treatment for 30 minutes. After a DTS self-assembled monolayer is formed on the cleaned substrate surface by a vapor method, a chalcogen-containing organic compound is vacuum-deposited at a deposition rate of 0.4 to 0.6 ⁇ / s. A semiconductor layer was formed.
- a carrier injection layer (film thickness: 1 nm) of tetrafluorotetracyanoquinodimethane, followed by a gold source electrode and a drain electrode (30 nm) are vacuum-deposited through a stainless steel metal mask to obtain a channel length of 100 ⁇ m and a channel width.
- a bottom gate-top contact type organic FET was produced by forming 1 mm.
- the fabricated devices were measured for carrier mobility and on / off ratio using a semiconductor parameter analyzer (model number “keithley 4200”, manufactured by Keithley Instruments Co., Ltd.).
- a semiconductor parameter analyzer model number “keithley 4200”, manufactured by Keithley Instruments Co., Ltd.
- the carrier mobility was 5.5 cm 2 / V ⁇ s
- the on / off ratio was 10 7
- the carrier mobility was 0.4 cm 2 / V ⁇ s
- the on / off ratio was 10 6 .
- the organic semiconductor material synthesized in each example is (1) superior in solubility in a solvent than the organic semiconductor material synthesized in the comparative example, and (2) essentially independent of the film forming method. It has become clear that it shows high carrier mobility.
- SYMBOLS 10 Source electrode, 20 ... Drain electrode, 30 ... Gate electrode, 40 ... Organic-semiconductor layer, 50 ... Gate insulating film, 60 ... Substrate, 70 ... Carrier injection layer, 80 ... Crystal film, 90 ... Organic-semiconductor solution, 100 ... Solution holding structure, 110 ... Spacer, 120 ... Solution holding plate
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Abstract
Description
[3]式(1-1)または式(1-2)で表される、前記[2]に記載の化合物。
[4]式(1-1)および式(1-2)中のR3が、炭素数4~15のアルキル、フェニル、フリルおよびチエニルから選択される同一の基である、前記[3]に記載の化合物。
[7]式(2-1)で表される、前記[6]に記載の化合物。
[14]前記[13]に記載の有機半導体材料を含む有機半導体膜。
[15]基板、ゲート電極、ゲート絶縁膜、ソース電極、ドレイン電極および有機半導体層を有する有機電界効果トランジスタであって、前記有機半導体層が前記[14]に記載の有機半導体膜で構成される有機電界効果トランジスタ。
〔カルコゲン含有有機化合物〕
本発明のカルコゲン含有有機化合物は、式(1)または式(2)で表される化合物であり、カルコゲンの架橋部分(-X-)を屈曲点としてベンゼン環が両翼に連なった、V字型(式(1))またはU字型(式(2))の構造を持ち、ベンゼン環上の任意の位置に置換基を有する。なお、本明細書において、「置換基」とは、水素以外の原子または基を意味する。
Xは、酸素、硫黄またはセレンであり、本発明の化合物が高いキャリア移動度を示すことから、酸素または硫黄が好ましく、硫黄が特に好ましい。
2つあるnは、それぞれ独立に0または1であり、好ましくは0である。
また、Xが硫黄であり、かつ全てのR1が同時にブチルであることはない。
(A)全てのR1~R2が水素であること。
(B)Xがセレンの場合を除き、全てのR3が同一の原子または基であることはないこと。
Xは、酸素、硫黄またはセレンである。
2つあるnは、それぞれ独立に0または1であり、好ましくは0である。
ただし、全てのR1~R2が同時に水素であることはない。
式(1)~(2)中、R1~R3として列挙されるピリジルとしては、例えば、2-ピリジル、3-ピリジルおよび4-ピリジルが挙げられる。
本発明の化合物(1)の中でも、以下の式で表される化合物もまた、好ましい。
また、本発明の化合物は、後述するように、有機合成化学的に実施容易な反応を用いて短工程で合成できることから、工業的に製造可能であって、実用性に富む有機半導体材料として用いることができる。
以上より、本発明の化合物は、有機半導体材料として好適に用いられる。
X=酸素の化合物(1)としては、例えば、以下の化合物が挙げられる。
本発明の化合物(1)または化合物(2)(X=硫黄またはセレン)の製造方法は、式(11)または式(21)で表される化合物をカップリングさせて、式(12)または式(22)で表される化合物を得る工程1A;式(12)または式(22)で表される化合物のメトキシを脱保護させて、式(13)または式(23)で表される化合物を得る工程2A;式(13)または式(23)で表される化合物とN,N-ジアルキルチオカルバモイルクロリドまたはN,N-ジアルキルセレノカルバモイルクロリドとを反応させて、式(14)または式(24)で表される化合物を得る工程3A;および式(14)または式(24)で表される化合物を加熱することにより、式(15)または式(25)で表される化合物を得る工程4Aを有する。
工程1Aでは、有機金属化合物の存在下、化合物(11)をホモカップリングさせ、あるいは化合物(21)をホモカップリングさせる。工程1Aの反応温度(例:溶液の温度)は、通常0~60℃、好ましくは0℃~室温であり;反応時間は、通常2~14時間であり;反応は、常圧下で通常行われる。なお、室温とは23℃程度の温度環境を意味する。
工程2Aでは、脱保護剤の存在下、化合物(12)または(22)のメトキシの脱保護を行う。工程2Aの反応温度(例:溶液の温度)は、通常-78℃~室温、好ましくは0℃~室温であり;反応時間は、通常1~2時間であり;反応は、常圧下で通常行われる。
工程3Aでは、塩基の存在下、化合物(13)または(23)と、N,N-ジアルキルチオカルバモイルクロリドまたはN,N-ジアルキルセレノカルバモイルクロリドとを反応させる。工程3Aの反応温度(例:溶液の加熱温度)は、通常60~80℃であり;反応時間は、通常10~48時間であり;反応は、常圧下で通常行われる。
工程4Aでは、化合物(14)または(24)を加熱し、環化を行うことで、本発明の化合物である化合物(15)または(25)を得る。工程4Aの加熱温度は、通常300~310℃であり;反応時間は、通常4~6時間である。
工程3A’では、化合物(13)または(23)の溶液に、ゼオライトを加え、脱水・環化を行うことで、本発明の化合物である化合物(15)または(26)を得る。工程3A’の加熱温度(例:溶液の加熱温度)は、通常160~180℃であり;反応時間は、通常8~20時間、好ましくは10~16時間であり;反応は、常圧下で通常行われる。
工程1Bでは、化合物(27)の5位および9位(n=0の場合)、6位および10位(n=1の場合)を臭素化する。臭素の使用量は、化合物(27)1molに対して、通常2.0~2.2molである。
工程2Bでは、公知のクロスカップリング反応、例えば、鈴木カップリング、スティルカップリング、根岸カップリング、玉尾カップリング、およびこれらから派生した反応によって、化合物(28)の臭素部分を置換基R1に変換する。R1は、式(2-1)中の同一記号と同義である。
クロスカップリング反応剤としては、例えば、トリブチル(2-チエニル)スズ、トリブチル(2-フリル)スズおよびトリブチル(2-チアゾリル)スズ等のR1-SnR3(式中、R1はチエニル、フリルまたはチアゾリルであり、Rはブチル等のアルキルである。);R1-MgX(式中、R1は炭素数1~20のアルキル、炭素数6~14のアリール、またはピリジルであり、Xは臭素等のハロゲンである。);R1-B(OH)2(式中、R1は炭素数6~14のアリール、またはピリジルである。);R1-ZnX(式中、R1は炭素数6~14のアリール、またはピリジルである。)が挙げられる。クロスカップリング反応剤の使用量は、化合物(28)1molに対して、通常1.1~4.0mol、好ましくは2.0~3.0molである。
工程5Aでは、化合物(13)とトリフルオロメタンスルホニルクロリドまたはトリフルオロメタンスルホン酸無水物とを反応させて、化合物(16)を得る。工程5Aの反応温度(例:溶液の温度)は、通常0~30℃であり;反応時間は、通常2~24時間である。
工程6Aでは、化合物(16)をボラン類とカップリングすることにより、ボロン酸エステル(17)を得る。工程6Aの反応温度(例:溶液の温度)は、通常20~150℃であり;反応時間は、通常3~24時間である。
工程7Aでは、ボロン酸エステル(17)を臭化銅で臭素化して、化合物(18)を得る。工程7Aの反応温度(例:溶液の温度)は、通常0~200℃であり;反応時間は、通常6~30時間である。臭化銅の使用量は、ボロン酸エステル(17)1molに対して、通常2.0~10.0molである。
工程8Aでは、化合物(18)をリチオ化した後、塩化セレンと反応させることにより、化合物(15)を得る。工程8Aの反応温度(例:溶液の温度)は、通常-80~30℃であり;反応時間は、通常1~5時間である。
本発明の膜(例:有機半導体膜)は、本発明の化合物、すなわち化合物(1)および化合物(2)から選択される少なくとも1種を含む。本発明の化合物は、溶媒に対して高い溶解性を示すため、これらを溶媒に溶解させた溶液(以下「有機半導体溶液」ともいう。)を、基板上に塗布または印刷することで、表面均一性に優れた膜(例:有機半導体膜)を形成することができる。
塗布法としては、例えば、スピンコート法、ディップコート法およびブレード法が挙げられる。また、本発明者らが開発した、塗布法に分類される、実施例にて後述するエッジキャスト法およびギャップキャスト法も有効である。
上記方法以外の製膜法、例えば蒸着法を用いて製膜を行っても差し支えはない。
本発明の有機半導体素子は、上記有機半導体膜および電極を有する。具体的には、上記有機半導体膜と、他の半導体特性を有する素子とを組み合わせることによって、有機半導体素子とすることができる。他の半導体特性を有する素子としては、例えば、整流素子、スイッチング動作を行うサイリスタ、トライアックおよびダイアックが挙げられる。
本発明の有機半導体素子の例としては、有機電界効果トランジスタ(FET)が挙げられる。本発明の有機FETは、液晶表示素子およびエレクトロルミネッセンス(EL)素子と組み合わせても用いることができる。
1H-NMRスペクトルおよび13C-NMRスペクトルは、日本電子(株)製ECA-600、およびECS400スペクトロメーターを用いて測定した。
元素分析には、(株)ジェイ・サイエンス・ラボ製JM10 MICRO CORDERを用いた。
質量分析には、日本電子(株)製JMS-T100LC APCI/ESI質量分析計、およびブルカーダルトニクス社製ultraflex III TOF/TOFを用いた。
なお、以下の実施例の表題化合物において、アルキルはいずれも直鎖状基である。
2,10-ジデシルジナフト[2,3-b:2',3'-d]フランの合成
7,7’-ジデシル-3,3’-ジメトキシ-2,2’-ビナフタレンの合成
7,7’-ジデシル-2,2’-ビナフタレン-3,3’-ジオールの合成
2,10-ジデシルジナフト[2,3-b:2',3'-d]フランの合成
2,10-ジデシルジナフト[2,3-b:2',3'-d]チオフェンの合成
O,O’-(7,7’-ジデシル-2,2’-ビナフタレン-3,3’-ジイル)ビス(ジメチルカルバモチオエート)の合成
2,10-ジデシルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジデシルジナフト[2,3-b:2',3'-d]フランの合成
3,9-ジブチルジナフト[2,3-b:2',3'-d]フランの合成
3,9-ジヘキシルジナフト[2,3-b:2',3'-d]フランの合成
3,9-ジデシルジナフト[2,3-b:2',3'-d]チオフェンの合成
O,O’-(6,6’-ジデシル-2,2’-ビナフタレン-3,3’-ジイル)ビス(ジメチルカルバモチオエート)の合成
3,9-ジデシルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジヘキシルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジオクチルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジブチルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジペンチルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジヘプチルジナフト[2,3-b:2',3'-d]チオフェンの合成
3,9-ジドデシルジナフト[2,3-b:2',3'-d]チオフェンの合成
ジナフト[2,3-b:2',3'-d]セレノフェンの合成
(第1工程)
[2,2'-ビナフタレン]-3,3'-ジイルビス(トリフルオロメタンスルホナト)の合成
1H NMR (600 MHz, CDCl3): δ 7.62-7.68 (m, 4H, ArH), 7.92 (s, 2H, ArH), 7.94-7.97 (m, 4H, ArH), 8.04 (s, 2H, ArH).
3,3'-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラニル)-2,2'-ビナフタレンの合成
1H NMR (600 MHz, CDCl3): δ 1.08 (s, 24H, CH3), 7.48 (dd, J = 8.4Hz, 8.4Hz, 2H, ArH), 7.51 (dd, J = 8.4Hz, 8.4Hz, 2H, ArH), 7.79 (s, 2H, ArH), 7.82 (d, J = 8.4Hz, ArH), 7.92 (d, J = 8.4Hz, ArH), 8.27 (s, 2H, ArH).
3,3'-ジブロモ-2,2'-ビナフタレンの合成
1H NMR (400 MHz, CDCl3): δ 7.53-7.59 (m, 4H, ArH), 7.81 (s, 2H, ArH), 7.83-7.87 (m, 4H, ArH), 8.22 (s, 2H, ArH).
ジナフト[2,3-b:2',3'-d]セレノフェンの合成
1H NMR (400 MHz, CDCl3): δ 7.51-7.57 (m, 4H, ArH), 7.86-7.90 (m, 2H, ArH), 8.02-8.06 (m, 2H, ArH), 7.81 (s, 2H, ArH), 8.28 (s, 2H, ArH), 8.71 (s, 2H, ArH).
3,9-ジヘキシルジナフト[2,3-b:2',3'-d]セレノフェンの合成
(第1工程)
6,6'-ジヘキシル-[2,2'-ビナフタレン]-3,3'-ジイルビス(トリフルオロメタンスルホナト)の合成
1H NMR (400 MHz, CDCl3): δ 0.93 (t, J = 6.8 Hz, 6H, CH3), 1.32-1.43 (m, 12H, (CH2)3), 1.75 (quin, J = 7.2 Hz, 4H, ArCH2CH2), 2.83 (t, J = 7.2 Hz, 4H, ArCH2), 7.47 (d, J = 8.4 Hz, 2H, ArH), 7.71 (s, 2H, ArH), 7.83 (s, 2H, ArH), 7.85 (d, J = 8.4 Hz, 2H, ArH), 7.97 (s, 2H, ArH).
2,2'-(6,6'-ジヘキシル-[2,2'-ビナフタレン]-3,3'-ジイル)ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン)の合成
1H NMR (400 MHz, CDCl3): δ 0.90 (t, J = 6.8 Hz, 6H, CH3), 1.08 (s, 24H, CH3), 1.31-1.43 (m, 12H, (CH2)3), 1.71 (quin, J = 7.6 Hz, 4H, ArCH2CH2), 2.79 (t, J = 7.6 Hz, 4H, ArCH2), 7.35 (d, J = 8.4 Hz, 2H, ArH), 7.67 (s, 2H, ArH), 7.72 (d, J = 8.4 Hz, 2H, ArH),7.73 (s, 2H, ArH), 8.18 (s, 2H, ArH).
3,3'-ジブロモ-6,6'-ジヘキシル-2,2'-ビナフタレンの合成
1H NMR (600 MHz, CDCl3): δ0.91 (t, J = 6.6 Hz, 6H, CH3), 1.31-1.40 (m, 12H, (CH2)3), 1.72 (quin, J = 7.2 Hz, 4H, ArCH2CH2), 2.79 (t, J = 7.2 Hz, 4H, ArCH2),7.38 (d, J = 8.4 Hz, 2H, ArH), 7.59 (s, 2H, ArH), 7.75-7.76 (m, 4H, ArH), 8.13 (s, 2H, ArH).
3,9-ジヘキシルジナフト[2,3-b:2',3'-d]セレノフェンの合成
1H NMR (600 MHz, CDCl3): δ0.90 (t, J = 6.6 Hz, 6H, CH3), 1.29-1.40 (m, 12H, (CH2)3), 1.72 (quin, J = 7.2 Hz, 4H, ArCH2CH2), 2.81 (t, J = 7.2 Hz, 4H, ArCH2),7.37 (d, J = 8.4 Hz, 2H, ArH), 7.62 (s, 2H, ArH), 7.94 (d, J = 8.4 Hz, 2H, ArH), 8.18 (s, 2H, ArH), 8.63 (s, 2H, ArH).
5,9-ジ(2-チエニル)ジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジブロモジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジ(2-チエニル)ジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジ(2-フリル)ジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジ(2-チアゾリル)ジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジオクチルジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジドデシルジナフト[2,1-b:1',2'-d]フランの合成
5,9-ジフェニルジナフト[2,1-b:1',2'-d]フランの合成
ジナフト[2,3-b:2',3'-d]チオフェンの合成
特許文献6の実施例に記載された表題化合物を、本発明の方法で合成した。
O,O’-(2,2’-ビナフタレン-3,3’-ジイル)ビス(ジメチルカルバモチオエート)の合成
ジナフト[2,3-b:2',3'-d]チオフェンの合成
実施例3で合成した化合物を0.6951mg秤量し、グローブボックス内でメスフラスコを用いて、脱気したベンゾニトリル(25ml)に溶かした(溶液濃度:4.92×10-5 M)。この調整した溶液を蓋付きのUVセルに入れ、直ちにUV-Visスペクトル(使用装置:日本分光(株)製、Jasco V-570 spectrometer)を測定した。引き続き、大気下で蓋の開け閉めを数回繰り返し、溶液と空気中の酸素とを接触させた。その後、3時間、24時間、72時間後同様に測定した結果を図5に示す。その結果、72時間放置した溶液でもスペクトルに変化は見られなかった。
以上より、実施例3で合成した化合物が化学的に安定であることが明らかとなった。
〈エッジキャスト法〉
本発明者らが開発した塗布法(エッジキャスト法;Appl. Phys. Exp. 2, 111501 (2009))に準拠し、製膜およびボトムゲート-トップコンタクト型有機FETの作製を行った。本法の概念図を、図2に示す。
本発明者らが開発した塗布法(ギャップキャスト法;Adv. Mater. 23, 1626 (2011).)に準拠し、製膜およびボトムゲート-トップコンタクト型有機FETの素子作製を行った。本法の概念図を図3に示す。
比較例1のカルコゲン含有有機化合物については、塗布法による素子作製が不可能であったため、実施例6および比較例1のカルコゲン含有有機化合物について蒸着法で素子を作製し、FET特性の比較を行った。
Claims (15)
- 式(1)で表される化合物。
Xは、酸素、硫黄またはセレンであり;
2つあるnは、それぞれ独立に0または1であり;
R1~R3は、それぞれ独立に水素、フッ素、炭素数1~20のアルキル、アリール、ピリジル、フリル、チエニルまたはチアゾリルであり、前記アルキル中の少なくとも1つの水素はフッ素で置き換えられてもよく、前記アリール、ピリジル、フリル、チエニルおよびチアゾリルの環上の少なくとも1つの水素はハロゲンおよび炭素数1~10のアルキルから選択される少なくとも1種で置き換えられてもよく;
ただし、Xがセレンの場合を除き、全てのR1~R3が同時に水素であることはなく、また、Xが硫黄であり、かつ全てのR1が同時にブチルであることはない。] - 式(1)において、要件(A)および(B)が満たされる、請求項1に記載の化合物:
(A)全てのR1~R2が水素であること。
(B)Xがセレンの場合を除き、全てのR3が同一の原子または基であることはないこと。 - 式(1-1)および式(1-2)中のR3が、炭素数4~15のアルキル、フェニル、フリルおよびチエニルから選択される同一の基である、請求項3に記載の化合物。
- 式(2)において、全てのR2が水素である、請求項5に記載の化合物。
- 式(2-1)中のR1が、炭素数6~15のアルキル、フェニル、フリル、チエニルおよびチアゾリルから選択される同一の基である、請求項7に記載の化合物。
- 式(11)で表される化合物をカップリングさせて、式(12)で表される化合物を得る工程;式(12)で表される化合物のメトキシを脱保護させて、式(13)で表される化合物を得る工程;式(13)で表される化合物とN,N-ジアルキルチオカルバモイルクロリドまたはN,N-ジアルキルセレノカルバモイルクロリドとを反応させて、式(14)で表される化合物を得る工程;および式(14)で表される化合物を加熱することにより、式(15)で表される化合物を得る工程を有する、請求項1に記載の化合物(ただし、X=硫黄またはセレン)の製造方法。
- 式(11)で表される化合物をカップリングさせて、式(12)で表される化合物を得る工程;式(12)で表される化合物のメトキシを脱保護させて、式(13)で表される化合物を得る工程;式(13)で表される化合物とトリフルオロメタンスルホニルクロリドまたはトリフルオロメタンスルホン酸無水物とを反応させて、式(16)で表される化合物を得る工程;式(16)で表される化合物をボラン類とカップリングすることにより、式(17)で表されるボロン酸エステルを得る工程;式(17)で表されるボロン酸エステルを臭化銅で臭素化して、式(18)で表される化合物を得る工程;および式(18)で表される化合物をリチオ化した後、塩化セレンと反応させることにより、式(15)で表される化合物を得る工程を有する、請求項1に記載の化合物(ただし、X=セレン)の製造方法。
- 請求項1~8のいずれか1項に記載の化合物からなる有機半導体材料。
- 請求項13に記載の有機半導体材料を含む有機半導体膜。
- 基板、ゲート電極、ゲート絶縁膜、ソース電極、ドレイン電極および有機半導体層を有する有機電界効果トランジスタであって、前記有機半導体層が請求項14に記載の有機半導体膜で構成される有機電界効果トランジスタ。
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Also Published As
Publication number | Publication date |
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US20150014673A1 (en) | 2015-01-15 |
CN104125951A (zh) | 2014-10-29 |
EP2818464A4 (en) | 2015-11-18 |
TWI583676B (zh) | 2017-05-21 |
TW201341375A (zh) | 2013-10-16 |
KR20140125407A (ko) | 2014-10-28 |
JP5867583B2 (ja) | 2016-02-24 |
US9537110B2 (en) | 2017-01-03 |
EP2818464A1 (en) | 2014-12-31 |
CN104125951B (zh) | 2017-05-24 |
KR101656763B1 (ko) | 2016-09-12 |
JPWO2013125599A1 (ja) | 2015-07-30 |
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