JP5523351B2 - ペリレン半導体並びにその製造方法及び使用 - Google Patents
ペリレン半導体並びにその製造方法及び使用 Download PDFInfo
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- JP5523351B2 JP5523351B2 JP2010545463A JP2010545463A JP5523351B2 JP 5523351 B2 JP5523351 B2 JP 5523351B2 JP 2010545463 A JP2010545463 A JP 2010545463A JP 2010545463 A JP2010545463 A JP 2010545463A JP 5523351 B2 JP5523351 B2 JP 5523351B2
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- 239000004065 semiconductor Substances 0.000 title claims description 58
- 238000004519 manufacturing process Methods 0.000 title description 11
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title description 7
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000010409 thin film Substances 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 16
- 230000005669 field effect Effects 0.000 claims description 13
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 11
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 6
- 230000005693 optoelectronics Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 57
- 125000004093 cyano group Chemical group *C#N 0.000 description 52
- -1 copper perfluorinated phthalocyanine Chemical class 0.000 description 48
- 239000000203 mixture Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 41
- 239000007787 solid Substances 0.000 description 30
- 125000001246 bromo group Chemical group Br* 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 238000007639 printing Methods 0.000 description 18
- 239000010408 film Substances 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- 125000006575 electron-withdrawing group Chemical group 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 10
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 0 C*c(c1c(cc2*)I)cc(*)c(-c(c3c45)ccc4I)c1c2-c3ccc5I Chemical compound C*c(c1c(cc2*)I)cc(*)c(-c(c3c45)ccc4I)c1c2-c3ccc5I 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 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
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000002508 contact lithography Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000007646 gravure printing Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000000813 microcontact printing Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 238000007645 offset printing Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 239000003989 dielectric material Substances 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
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000013086 organic photovoltaic Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000007649 pad printing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000003837 (C1-C20) alkyl 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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical class 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 description 2
- UNBMPKNTYKDYCG-UHFFFAOYSA-N 4-methylpentan-2-amine Chemical compound CC(C)CC(C)N UNBMPKNTYKDYCG-UHFFFAOYSA-N 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 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
- 239000000654 additive Substances 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 239000000022 bacteriostatic agent Substances 0.000 description 2
- 125000005841 biaryl group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 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
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002484 cyclic voltammetry 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
- 239000003599 detergent Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000524 functional group Chemical group 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
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- WGBBUURBHXLGFM-UHFFFAOYSA-N hexan-2-amine Chemical compound CCCCC(C)N WGBBUURBHXLGFM-UHFFFAOYSA-N 0.000 description 2
- HQLZFBUAULNEGP-UHFFFAOYSA-N hexan-3-amine Chemical compound CCCC(N)CC HQLZFBUAULNEGP-UHFFFAOYSA-N 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 2
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- 238000007738 vacuum evaporation 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
- 238000004832 voltammetry Methods 0.000 description 1
- 238000001075 voltammogram Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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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
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
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- Y02E10/549—Organic PV cells
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Description
R1及びR2は、それぞれ存在する場合に、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、及び3〜22員環状部分から独立して選択され、ここで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、及び3〜22員環状部分のそれぞれは、ハロゲン、−CN、−NO2、−C(O)H、−C(O)OH、−CONH2、−OH、−NH2、−CO(C1-10アルキル)、−C(O)OC1-10アルキル、−CONH(C1-10アルキル)、−CON(C1-10アルキル)2、−S−C1-10アルキル、−O−(CH2CH2O)n(C1-10アルキル)、−NH(C1-10アルキル)、−N(C1-10アルキル)2、C1-10アルキル基、C2-10アルケニル基、C2-10アルキニル基、C1-10ハロアルキル基、C1-10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員環シクロヘテロアルキル基及び5〜14員環ヘテロアリール基から独立して選択される1〜4個の基で場合により置換され;
それらの両方が共通の炭素原子に結合する少なくともR1の1つ及びR2の1つは、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、及び3〜22員環状部分から独立して選択され、それぞれ、本明細書に記載されるように場合により置換され;
R3、R4、R5及びR6は、独立してH又は電子求引性基であり;及び
nは、1、2、3又は4である]を有する化合物を提供するものである。
R1及びR2は、それぞれ存在する場合に、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、及び3〜22員環状部分から独立して選択され、ここで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、及び3〜22員環状部分のそれぞれは、ハロゲン、−CN、−NO2、−C(O)H、−C(O)OH、−CONH2、−OH、−NH2、−CO(C1-10アルキル)、−C(O)OC1-10アルキル、−CONH(C1-10アルキル)、−CON(C1-10アルキル)2、−S−C1-10アルキル、−O−(CH2CH2O)n(C1-10アルキル)、−NH(C1-10アルキル)、−N(C1-10アルキル)2、C1-10アルキル基、C2-10アルケニル基、C2-10アルキニル基、C1-10ハロアルキル基、C1-10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員環シクロヘテロアルキル基及び5〜14員環ヘテロアリール基から独立して選択される1〜4個の基で場合により置換され;
Xは、それぞれ存在する場合に、H又は脱離基であり;
nは、1、2、3又は4である]の化合物をシアニドと反応させる段階を含んでよい。
A. N,N’−ビス(1−メチルペンチル)−1,7−ジシアノペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDIlMP−CN2)の調製
N,N’−ビス(1−メチルペンチル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDIlMP−Br2、R1=CH3、R2=C4H9)の調製。トリエチレングリコールジメチルエーテル(5mL)におけるPDA−Br2(550mg、1.0mmol)と2−アミノヘキサン(0.32mL、2.40mmol)との混合物をN2下でチューブ内に密封し、165℃で1時間撹拌した。室温に冷却後、溶媒を蒸留して、680mgの固体残渣を得た。溶離液としてCHCl3を用いてカラムクロマトグラフィーにより生成物を精製し、400mg(0.56mmol、収率55.8%)の明赤色の固体を得た。元素分析(計算値C,60.35;H,4.50;N,3.91):C,60.29;H,4.54;N,3.91。
N,N’−ビス(1−メチルブチル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDIlMB−Br2、R1=CH3、R2=C3H7)の調製。トリエチレングリコールジメチルエーテル(20mL)におけるPDA−Br2(2.20g、4.0mmol)と2−アミノペンタン(1.12mL、9.60mmol)との混合物を165℃で1時間撹拌した。室温に冷却後、MeOH(10mL)を添加し、沈殿物を濾過により回収し、溶離液としてCHCl3を用いてカラムクロマトグラフィーにより精製して、赤色の固体として純粋な生成物を得た(220mg、0.32mmol、収率8%)。
N,N’−ビス(1−メチルプロピル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDI1MPr−Br2(R1=CH3、R2=C2H5)の調製。トリエチレングリコールジメチルエーテル(5mL)におけるPDA−Br2(550mg、1.0mmol)とsec−ブチルアミン(0.24mL、2.40mmol)との混合物をN2下でj−youngチューブ内に密封し、165℃で1時間撹拌した。室温に冷却後、MeOH(3mL)を添加し、固体を濾過により回収した。溶離液としてCHCl3を用いてカラムクロマトグラフィーにより生成物を精製し、赤色の固体を得た(60mg、収率10%)。
N,N’−ビス(1−メチルヘキシル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDI1MH−Br2、R1=CH3、R2=C5H11)の調製。トリエチレングリコールジメチルエーテル(10mL)及びプロピオン酸(1.1mL)におけるPDA−Br2(1.10g、2.0mmol)と2−アミノヘプタン(0.72mL、4.80mmol)との混合物を165℃で1時間撹拌した。室温に冷却後、MeOH(15mL)を添加し、沈殿物が形成し、それを濾過により回収した。溶離液としてCHCl3を用いてカラムクロマトグラフィーにより固体(1.24g)を精製し、濃い茶色の固体として純粋な生成物を得た(586mg、0.79mmol、収率39%)。
N,N’−ビス(1−エチルブチル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDI1EB−Br2、R1=C2H5、R2=C3H7)の調製。トリエチレングリコールジメチルエーテル(10mL)及びプロピオン酸(1.1mL)におけるPDA−Br2(1.1g、2.0mmol)と3−アミノヘキサン(486mg、4.80mmol)との混合物を165℃で1時間撹拌した。室温に冷却後、MeOH(15mL)を添加し、得られた沈殿物を濾過により回収した。溶離液としてCHCl3を用いてカラムクロマトグラフィーにより固体を精製し、赤色の固体として純粋な生成物を得た(383mg、0.53mmol、収率26.7%)。元素分析(計算値C,60.35;H,4.50;N,3.91):C,60.57;H,4.54;N,4.05。
N,N’−ビス(1−エチルプロピル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDI1EPr−Br2、R1=C2H5、R2=C2H5)の調製。トリエチレングリコールジメチルエーテル(15mL)及びプロピオン酸(2.2mL)におけるPDA−Br2(2.20g、4.0mmol)と3−アミノペンタン(1.12mL、9.60mmol)との混合物を165℃で1時間撹拌した。室温に冷却後、MeOH(25mL)を添加し、沈殿物を濾過により回収した。溶離液としてCHCl3を用いてカラムクロマトグラフィーにより、得られた固体を精製し、赤色の固体を得た(1.11g、1.61mmol、収率40.3%)。元素分析(計算値C,59.32;H,4.10;N,4.07):C,59.04;H,4.07;N,4.06。
N,N’−ビス(1,3−ジメチルブチル)−1,7−ジブロモペリレン−3,4:9,10−ビス(ジカルボキシイミド)(PDI1M3MB−Br2、R1=CH3、R2=2−メチルプロピル)の調製。トリエチレングリコールジメチルエーテル(15mL)におけるPDA−Br2(2.20mg、41.0mmol)と1,3−ジメチルブチルアミン(1.35mL、9.60mmol)との混合物をN2下でチューブ内に密封し、165℃で1時間撹拌した。室温に冷却後、MeOH(25mL)を添加し、沈殿物を濾過により回収した。カラムクロマトグラフィー(CHCl3)により粗生成物を精製し、赤色の固体としてPDI1M3MB−Br2を得た(1.10g、1.54mmol、収率39%)。
Epsilon単一チャネルポテンシオメータとBAS C3電池スタンド(Cディスク作用電極と、裸Ag参照電極と、Ptワイヤ対向電極とを有する1区画電池)とを用いて、サイクリックボルタンメトリ実験を行った。測定中に水及び酸素を除去するために適切な予防措置をとった。60〜150mV/sの間の走査速度で0.1M THF/TBAPF6溶液に化合物(1〜3mg)を溶解することによりN2下で全ての測定を行った。ボルタンモグラムが(準)可逆である場合、前方及び逆走査のためのピーク電位の間の中間点としての見掛け電位(E1/2)を抽出することが可能である。
トップコンタクト構成を用いて本教示の化合物により薄膜トランジスタ(TFT)素子(25〜200μmのチャネル長(L)及び1.0〜4.0mmのチャネル幅(W))を製造した。ヘキサメチルジシラザンで前もって処理されたnドープSi/SiO2(300nm厚の熱酸化物)基板上に、本教示の化合物により製造した半導体膜を真空蒸着(2〜4Ås-1、P≒10-6Torr)又はスピンコートした。これらの半導体膜のXRDプロットは鋭い反射を示し、このことは高結晶化度を示唆する。オーム接点によりゲート領域をSi基板に接近させ、シャドウマスクにより半導体層上にAuソース接点及びドレイン接点を蒸着させた。全ての電気測定を、周囲雰囲気中で行った。下記で報告されるデータは、半導体膜上の異なる位置で試験した少なくとも3つの素子から測定した平均値である。
Claims (12)
- 式I:
R1 は、それぞれ存在する場合に、−CH 3 、−CF 3 、及び−C 2 H 5 から選択され;
R2は、それぞれ存在する場合に、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、及び3〜22員環状部分から選択され、それぞれ、ハロゲン、−CN、−NO2、−C(O)H、−C(O)OH、−CONH2、−OH、−NH2、−CO(C1-10アルキル)、−C(O)OC1-10アルキル、−CONH(C1-10アルキル)、−CON(C1-10アルキル)2、−S−C1-10アルキル、−O−(CH2CH2O)n(C1-10アルキル)、−NH(C1-10アルキル)、−N(C1-10アルキル)2、C1-10アルキル基、C2-10アルケニル基、C2-10アルキニル基、C1-10ハロアルキル基、C1-10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員環シクロヘテロアルキル基及び5〜14員環ヘテロアリール基から独立して選択される1〜4個の基で場合により置換され;
R3、R4、R5及びR6は、独立してH又はCNであり、ここでR3、R4、R5及びR6の内の少なくとも1つはCNであり;並びに
nは、1、2、3又は4である]の化合物。 - R 2 が、それぞれ存在する場合に、C1-12アルキル基、C1-12ハロアルキル基、及びハロゲン、C1-6アルキル基及びC1-6ハロアルキル基から独立して選択される1〜4個の基で場合により置換されるフェニル基から選択される、請求項1に記載の化合物。
- 請求項1から4のいずれか1項に記載の化合物の製造方法であって、式II:
R1 は、それぞれ存在する場合に、−CH 3 、−CF 3 、及び−C 2 H 5 から選択され;
R2は、それぞれ存在する場合に、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、及び3〜22員環状部分から選択され、それぞれ、ハロゲン、−CN、−NO2、−C(O)H、−C(O)OH、−CONH2、−OH、−NH2、−CO(C1-10アルキル)、−C(O)OC1-10アルキル、−CONH(C1-10アルキル)、−CON(C1-10アルキル)2、−S−C1-10アルキル、−O−(CH2CH2O)n(C1-10アルキル)、−NH(C1-10アルキル)、−N(C1-10アルキル)2、C1-10アルキル基、C2-10アルケニル基、C2-10アルキニル基、C1-10ハロアルキル基、C1-10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員環シクロヘテロアルキル基及び5〜14員環ヘテロアリール基から独立して選択される1〜4個の基で場合により置換され;
Xは、それぞれ存在する場合に、H又は脱離基であり;並びに
nは、1、2、3又は4である]の化合物をシアニドと反応させる段階を含む方法。 - 請求項1から4のいずれか1項に記載の1種以上の化合物を含む、電子素子、光学素子又は光電子素子である製品。
- 前記製品が、請求項1から4のいずれか1項に記載の1種以上の化合物を含む、薄膜半導体を含む電界効果トランジスタ素子である、請求項8に記載の製品。
- 前記製品が、請求項1から4のいずれか1項に記載の1種以上の化合物を含む、薄膜半導体を含む光起電力素子である、請求項8に記載の製品。
- 前記製品が、請求項1から4のいずれか1項に記載の1種以上の化合物を含む、薄膜半導体を含む有機発光ダイオード素子である、請求項8に記載の製品。
- 請求項1から4のいずれか1項に記載の1種以上の化合物を含む、薄膜半導体を含む単極回路又は相補型回路の装置である、請求項8に記載の製品。
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JP2010545463A Active JP5523351B2 (ja) | 2008-02-05 | 2009-02-05 | ペリレン半導体並びにその製造方法及び使用 |
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JP (1) | JP5523351B2 (ja) |
KR (2) | KR101638199B1 (ja) |
CN (1) | CN101952988B (ja) |
CA (1) | CA2714423A1 (ja) |
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- 2009-02-05 KR KR1020167005082A patent/KR20160029863A/ko not_active Application Discontinuation
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TW201006840A (en) | 2010-02-16 |
TWI439461B (zh) | 2014-06-01 |
CA2714423A1 (en) | 2009-08-13 |
KR20100108605A (ko) | 2010-10-07 |
WO2009098252A1 (en) | 2009-08-13 |
US20100319778A1 (en) | 2010-12-23 |
KR101638199B1 (ko) | 2016-07-08 |
EP2240970A1 (en) | 2010-10-20 |
JP2011514884A (ja) | 2011-05-12 |
US8404844B2 (en) | 2013-03-26 |
CN101952988B (zh) | 2015-12-16 |
EP2240970B1 (en) | 2018-03-14 |
CN101952988A (zh) | 2011-01-19 |
KR20160029863A (ko) | 2016-03-15 |
TWI534146B (zh) | 2016-05-21 |
TW201446764A (zh) | 2014-12-16 |
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