WO2013151128A1 - フタロシアニンナノサイズ構造物、及び該ナノサイズ構造物を用いた電子素子 - Google Patents
フタロシアニンナノサイズ構造物、及び該ナノサイズ構造物を用いた電子素子 Download PDFInfo
- Publication number
- WO2013151128A1 WO2013151128A1 PCT/JP2013/060319 JP2013060319W WO2013151128A1 WO 2013151128 A1 WO2013151128 A1 WO 2013151128A1 JP 2013060319 W JP2013060319 W JP 2013060319W WO 2013151128 A1 WO2013151128 A1 WO 2013151128A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- phthalocyanine
- atom
- nanosize
- substituent
- Prior art date
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims abstract description 215
- 238000004519 manufacturing process Methods 0.000 claims abstract description 31
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 238000006243 chemical reaction Methods 0.000 claims description 46
- -1 n -Hexyl Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000003960 organic solvent Substances 0.000 claims description 30
- 239000002105 nanoparticle Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052749 magnesium Inorganic materials 0.000 claims description 12
- 125000002015 acyclic group Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052745 lead Inorganic materials 0.000 claims description 6
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical group [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 claims description 6
- 150000002815 nickel Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003136 n-heptyl 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])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 214
- 239000000463 material Substances 0.000 abstract description 60
- 239000004065 semiconductor Substances 0.000 abstract description 54
- 230000008569 process Effects 0.000 abstract description 32
- 239000006185 dispersion Substances 0.000 description 71
- 239000010410 layer Substances 0.000 description 64
- 239000010408 film Substances 0.000 description 44
- 239000002904 solvent Substances 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 31
- 239000002131 composite material Substances 0.000 description 30
- 239000000976 ink Substances 0.000 description 28
- 238000007639 printing Methods 0.000 description 26
- 238000011282 treatment Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 239000013078 crystal Substances 0.000 description 20
- 238000011156 evaluation Methods 0.000 description 20
- 150000002430 hydrocarbons Chemical group 0.000 description 20
- 239000007788 liquid Substances 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 19
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 18
- 238000001035 drying Methods 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 150000003863 ammonium salts Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000004020 conductor Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000010419 fine particle Substances 0.000 description 11
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 241000894007 species Species 0.000 description 10
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229940117389 dichlorobenzene Drugs 0.000 description 9
- 238000007645 offset printing Methods 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229910052809 inorganic oxide Inorganic materials 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 7
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- 238000000813 microcontact printing Methods 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
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- 229910021389 graphene Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
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- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 4
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- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 235000019000 fluorine Nutrition 0.000 description 4
- 238000007646 gravure printing Methods 0.000 description 4
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- 238000005470 impregnation Methods 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 4
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- 238000002834 transmittance Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
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- 125000005309 thioalkoxy group Chemical group 0.000 description 3
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
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- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/20—Obtaining compounds having sulfur atoms directly bound to the phthalocyanine skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/065—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having -COOH or -SO3H radicals or derivatives thereof, directly linked to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0678—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
- C09B67/0019—Influencing the physical properties by treatment with an acid, H2SO4 of phthalocyanines
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- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0022—Wet grinding of pigments
- C09B67/0023—Wet grinding of pigments of phthalocyanines
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- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
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- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- 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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Definitions
- the present invention relates to a phthalocyanine nanosize structure, an ink composition containing the phthalocyanine nanosize structure, an electronic device containing the phthalocyanine nanosize structure, a transistor containing the phthalocyanine nanosize structure in a channel portion, and
- the present invention relates to a photoelectric conversion element containing the phthalocyanine nanosize structure between a positive electrode and a negative electrode.
- an “organic transistor (OFET)” using an organic compound (organic semiconductor) having semiconductor characteristics in the active part (semiconductor layer) of the transistor has attracted attention (see Non-Patent Document 1).
- organic semiconductor is soft and can be processed at a low temperature, and generally has high affinity with a solvent. For this reason, there is an advantage that a semiconductor layer can be manufactured (film formation) on a flexible plastic substrate using a wet process such as coating or printing at low cost. Is expected as an indispensable material for next-generation electronic devices.
- Phthalocyanines are one of typical organic semiconductors, and are known to exhibit good transistor characteristics by controlling higher-order structures, that is, molecular arrangement and assembly state (see Non-Patent Document 2). .
- phthalocyanines have low solvent solubility, it is difficult to produce an element by a wet process, and when used for an electronic element, a dry process such as vacuum deposition or sputtering is generally used. Since such a dry process is a complicated and expensive process, it is difficult to provide a low-cost electronic device that is one of the characteristics of an organic semiconductor.
- the one-dimensional crystalline structure is a one-dimensional crystalline structure having a minor axis of 500 nm or less (hereinafter referred to as a nano-sized one-dimensional structure). (Notation) is preferable.
- Phthalocyanines are widely used as paint colorants for printing inks, and many techniques for controlling their crystal size and shape are also known.
- a solvent salt milling method for example, see Patent Document 2 in which an inorganic salt and an organic solvent are mixed with metal phthalocyanine and the pigment is finely pulverized by a grinding apparatus, or a large amount of the metal phthalocyanine is dissolved in sulfuric acid.
- a crystallization method of precipitating in water for example, see Patent Document 3).
- the present inventors have already produced a phthalocyanine nanowire using an unsubstituted phthalocyanine and a phthalocyanine having a substituent, and disclosed a device manufacturing technique by a wet process using the phthalocyanine nanowire (Patent Document 4). 5 and 6).
- Patent Document 4 a phthalocyanine nanowire having a substituent
- Patent Document 6 a device manufacturing technique by a wet process using the phthalocyanine nanowire.
- the phthalocyanine nanowire is completely optimized in terms of performance.
- the present invention has been made in view of the above problems, and aims to provide an organic semiconductor material capable of producing an electronic element by a low-cost wet process. Furthermore, the present invention aims to provide an organic semiconductor electronic device that is hard to break, lightweight, inexpensive, and has high characteristics.
- the present inventor can provide an organic semiconductor material suitable for a wet process with improved performance by optimizing a phthalocyanine derivative constituting a phthalocyanine nanosize structure.
- the headline and the present invention were completed.
- the organic semiconductor material for an electronic device active part (semiconductor layer), it is found that an electronic device having high durability, light resistance, low cost, and high characteristics can be provided, and the present invention is completed. It came to.
- the present invention A nano-sized structure containing unsubstituted phthalocyanine and substituted phthalocyanine,
- the shape of the structure has a major axis and a minor axis, and the minor axis is 500 nm or less
- the unsubstituted phthalocyanine is represented by the general formula (1) or (2),
- X is selected from the group consisting of copper atom, zinc atom, cobalt atom, nickel atom, tin atom, lead atom, magnesium atom, iron atom, palladium atom, calcium atom, GeO, TiO, VO and AlCl. Any one selected.
- a phthalocyanine nanosize structure in which the phthalocyanine having a substituent is represented by the general formula (3) or (4).
- X is selected from the group consisting of copper atom, zinc atom, cobalt atom, nickel atom, tin atom, lead atom, magnesium atom, iron atom, palladium atom, calcium atom, GeO, TiO, VO and AlCl.
- X is selected from the group consisting of copper atom, zinc atom, cobalt atom, nickel atom, tin atom, lead atom, magnesium atom, iron atom, palladium atom, calcium atom, GeO, TiO, VO and AlCl.
- Each hydrogen atom in the benzene ring of the phthalocyanine skeleton may be substituted with fluorine, chlorine or bromine
- Z 1 to Z 8 are each independently a hydrogen atom or a C 1 to C carbon atom which may have a substituent.
- acyclic hydrocarbon group an optionally substituted cyclic hydrocarbon group having 1 to 30 carbon atoms, an optionally substituted heteroaryl group, and a, b, c, and d are Each independently represents an integer of 0 to 4, but at least one is not 0, and Z 1 to Z 8 are represented by the general formula (5) or (6), and the case where both are hydrogen atoms is excluded.
- Q is each independently a hydrogen atom or a methyl group, and Q 'is an acyclic hydrocarbon group having 1 to 30 carbon atoms.
- m is an integer of 1 to 20, and R and R ′ are each independently an alkyl group having 1 to 20 carbon atoms.) Is to provide.
- the phthalocyanine nanosize structure according to the present invention is composed of phthalocyanines having excellent durability, an electronic device having a long life can be provided.
- the phthalocyanine nanosize structure according to the present invention is superior in solvent dispersibility than known phthalocyanine pigment fine particles, it is easy to form an ink composition, and thus a semiconductor layer is formed on a flexible plastic substrate by a printing method.
- the phthalocyanine nanosize structure according to the present invention has higher controllability of arrangement of phthalocyanine molecules throughout the structure than known phthalocyanine pigment fine particles, the semiconductor characteristics can be improved.
- the phthalocyanine nanosize structure according to the present invention comprises a nanosize structure from the phthalocyanine nanosize structures (nanowires) described in [Patent Document 4], [Patent Document 5] and [Patent Document 6]. Since the phthalocyanine derivative is optimized, the semiconductor characteristics are improved, and as a result, an electronic element with improved charge mobility (hereinafter simply referred to as mobility) can be provided.
- FIG. 1 is a schematic cross-sectional view of a transistor according to the present invention.
- 1 is a schematic planar equivalent circuit diagram of a transistor array including transistors according to the present invention. It is a transmission electron microscope image of solid content in a phthalocyanine nanosize structure dispersion liquid (1). It is a transmission electron microscope image of solid content in a phthalocyanine nanosize structure dispersion liquid (2). It is a transmission electron microscope image of solid content in a phthalocyanine nanosize structure dispersion liquid (3). It is a transmission electron microscope image of solid content in a phthalocyanine nanosize structure dispersion liquid (4).
- the phthalocyanine nanosize structure of the present invention is a one-dimensional (wire shape, fiber shape, thread shape, needle shape, rod shape, etc.) structure having a major axis (major axis) and a minor axis (minor axis).
- the minor axis is 500 nm or less, more preferably 300 nm or less, and most preferably 100 nm or less, and includes unsubstituted phthalocyanine and a substituted phthalocyanine (phthalocyanine derivative) as a structural constituent material.
- the major axis is not particularly limited as long as (major axis / minor axis)> 1 (if the major axis / minor axis is greater than 1).
- the mixing ratio of unsubstituted phthalocyanine and substituted phthalocyanine is the mixing ratio of substituted phthalocyanine to unsubstituted phthalocyanine ([mass of substituted phthalocyanine ⁇ 100] / [mass of unsubstituted phthalocyanine]).
- the range of 1 to 200% by mass is preferable, and 1 to 120% by mass is more preferable (described later).
- phthalocyanine represented by General formula (1) As an unsubstituted phthalocyanine which comprises the phthalocyanine nanosize structure of this invention, the phthalocyanine represented by General formula (1) and the metal-free phthalocyanine represented by Formula (2) can be mentioned.
- X is not limited as long as it constitutes phthalocyanine.
- copper atom, zinc atom, cobalt atom, nickel atom, tin atom, lead atom, magnesium atom, iron atom, palladium atom Metal atoms such as calcium atoms, and metal oxides and metal halides such as GeO, TiO (titanyl), VO (vanadyl), AlCl (aluminum chloride), among others, copper atoms, zinc atoms, iron Atoms are particularly preferred.
- a feature of the phthalocyanine nanosize structure of the present invention is that a hydrogen atom of a phthalocyanine skeleton represented by the following general formula (3) or (4) is a sulfamoyl group (—SO 2 NZZ ′) in a phthalocyanine having a substituent.
- the purpose is to use a substituted phthalocyanine derivative (sulfamoyl group-substituted phthalocyanine).
- X is a copper atom, zinc atom, cobalt atom, nickel atom, tin atom, lead atom, magnesium atom, iron atom, palladium atom, calcium atom, GeO Any one selected from the group consisting of TiO, VO and AlCl,
- Each hydrogen atom in the benzene ring of the phthalocyanine skeleton may be substituted with fluorine, chlorine or bromine, and
- Z 1 to Z 8 are each independently a hydrogen atom or a C 1 to C carbon atom which may have a substituent.
- acyclic hydrocarbon group an optionally substituted cyclic hydrocarbon group having 1 to 30 carbon atoms, an optionally substituted heteroaryl group, and a, b, c, and d are Each independently represents an integer of 0 to 4, but at least one is not 0, and Z 1 to Z 8 are represented by the general formula (5) or (6), and the case where both are hydrogen atoms is excluded.
- q is an integer of 4 to 100
- Q is each independently a hydrogen atom or a methyl group
- Q ' is an acyclic hydrocarbon group having 1 to 30 carbon atoms.
- n is an integer of 1 to 20, and R and R ′ are each independently an alkyl group having 1 to 20 carbon atoms.
- the acyclic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent may be either a linear hydrocarbon group or a branched hydrocarbon group, and the hydrocarbon group may be a saturated hydrocarbon group. Either an unsaturated hydrocarbon group may be used.
- Examples of such acyclic hydrocarbon group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 1-pentyl group, 2 -Pentyl group, 3-pentyl group, 1- (2-methyl) -butyl group, 2- (2-methyl) -butyl group, 1- (3-methyl) -butyl group, 2- (3-methyl)-butyl group, (2,2-dimethyl) -propyl (also known as neopentyl), hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, 2-ethyl-hexyl , Nonyl group, decyl group, n-decyl group, undecyl group, dodecyl group, n-
- a linear or branched saturated hydrocarbon group can be mentioned, and an arbitrary hydrogen atom in the hydrocarbon group may be substituted with a known substituent (described later) that can substitute the hydrocarbon group.
- a known substituent described later
- those having 25 or less carbon atoms are preferable, and those having 22 or less carbon atoms are more preferable.
- a linear or branched unsaturated hydrocarbon group such as any one of the hydrocarbon groups, and any hydrogen atom in the hydrocarbon group is substituted with a known substituent capable of substituting the hydrocarbon group (described later) Also good.
- those having 25 or less carbon atoms are preferable, and those having 22 or less carbon atoms are more preferable.
- substituents that can be substituted on the acyclic hydrocarbon group having 1 to 30 carbon atoms include —F, —Cl, —Br, alkoxy groups, thioalkoxy groups, amino groups, —SO 2 NHY.
- Y 1 represents an alkyl group which may have a substituent
- —COOY 2 represents an alkyl group which may have a substituent
- —N 3 —CN, —NC, —NO 2
- a ⁇ represents hydrogen or an optionally substituted alkyl group
- a ⁇ represents a monovalent anion species
- —OH, —O ⁇ L + (L + represents a monovalent cationic species such as Li + , Na + , K + , ammonium salt, etc.), —SH, —S ⁇ L + (L + is Li + , Na + , K + , ammonium represents a monovalent cation species, such as salts)
- - SO 2 H, -SO 2 - L + (L + is, Li , Na +, K +, a monovalent cation species, such as ammonium salts)
- Examples of the C1-C30 cyclic hydrocarbon group which may have a substituent include a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, and the like, and any hydrogen atom in the cyclic hydrocarbon group is represented by
- the cyclic hydrocarbon group may be substituted with a known substituent that can be substituted (described later).
- —CHO, —COOH, —COO ⁇ L + (L + represents a monovalent cationic species such as Li + , Na + , K + , ammonium salt), —B (OY 4 ) 3 (Y 4 Represents hydrogen or an alkyl group which may have a substituent), —SiY 5 3 (Y 5 represents hydrogen or an alkyl group which may have a substituent), —Si (OY 6 ) 3 (Y 6 represents hydrogen or an alkyl group which may have a substituent), —P ( ⁇ O) (OY 7 ) 2 (Y 7 represents hydrogen or an alkyl group which may have a substituent), — CONY 9 Y 10 (Y 9 and Y 10 may each independently have hydrogen or a substituent.
- Y 8 represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
- —F represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
- —F represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
- —F represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
- —F represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
- —F represents an alkyl group which may have a substituent or an aryl group which may have a substituent
- the phthalocyanine having a substituent represented by the general formula (3) or (4) is a compound in which at least one hydrogen of a phthalocyanine skeleton is substituted with a sulfamoyl group (—SO 2 NZZ ′) (sulfamoyl group substitution). Phthalocyanine).
- a, b, c and d represent the number of introduced substituents of the sulfamoyl group, each independently represents an integer of 0 to 4, but at least one is not 0. That is, the sulfamoyl group to be introduced may be at least one, preferably 4 or less, more preferably 2 or less, and most preferably 1. In addition, there is no limitation in particular in the position substituted.
- substituent of the phthalocyanine having a substituent represented by the general formula (3) or (4) are shown below, but are used for the phthalocyanine nanosize structure of the present invention.
- substituents of phthalocyanine having the above-described substituents are not limited thereto.
- the phthalocyanine having a substituent represented by the general formula (3) or (4) can be obtained by combining known and commonly used methods.
- copper phthalocyanine sulfonyl chloride may be reacted with an amine represented by the following formula [Chemical Formula 10].
- Copper phthalocyanine sulfonyl chloride as a raw material can be obtained by reaction of copper phthalocyanine with chlorosulfonic acid or thionyl chloride.
- the amine represented by [Chemical Formula 10] which is the other raw material can be obtained by a known and usual method.
- the hydroxyl group of alcohol can be obtained by reductive amination using a nickel / copper / chromium catalyst, and the hydroxyl group can be obtained by Mitsunobu reaction (reference: Synthesis 1981, P. 1). It can be obtained by imidization and then amination by hydrazine reduction (Reference: Chemical Communications, 2003, P.2062). Many amines are also available as commercial products.
- ⁇ Method for producing phthalocyanine nano-sized structure for example, the methods described in WO2010 / 122921, JP2009-280531A, and WO2011 / 065133 can be used.
- a method for adjusting the major axis / minor axis ratio (aspect ratio) of the nano-sized structures obtained by the methods described in these publications and reducing the aspect ratio of the nano-sized structures is also the phthalocyanine of the present invention. It can be used for the manufacturing method of a nanosize structure. Specific examples are shown below.
- An example of a method for producing the phthalocyanine nanosize structure of the present invention is: (A) Step (a) of obtaining a composite by dissolving the unsubstituted phthalocyanine and the phthalocyanine having the substituent in a good solvent and then precipitating it in a poor solvent; (B) micronizing the complex to obtain a micronized complex (b); (C) one-dimensional crystal growth (crystal growth in one direction) in an organic solvent to form a nano-sized one-dimensional structure (nanowire or nanorod) (c) It is.
- phthalocyanines are soluble in an acid solvent such as sulfuric acid.
- an acid solvent such as sulfuric acid, chlorosulfuric acid, methanesulfonic acid, trifluoroacetic acid or the like.
- an acid solvent such as sulfuric acid, chlorosulfuric acid, methanesulfonic acid, trifluoroacetic acid or the like.
- the mixing ratio of the substituted phthalocyanine (sulfamoyl group-substituted phthalocyanine) to the unsubstituted phthalocyanine is preferably in the range of 1 to 200% by mass, more preferably 1 to 120% by mass.
- the mixing ratio is 1% by mass or more, by the action of the substituent of the phthalocyanine having the substituent, the crystal grows in one direction through the steps described later to form a favorable one-dimensional structure, while 200% by mass
- the functional group is not so large as to inhibit crystal growth, and therefore, it does not become an amorphous state or an isotropic structure through good unidirectional crystal growth to form a one-dimensional structure.
- the amount of the unsubstituted phthalocyanine and the phthalocyanine having a substituent added to the acid solvent is not particularly limited as long as there is no undissolved content and the concentration can be completely dissolved, but the solution has sufficient fluidity. As a range which maintains the viscosity of a certain level, 20 mass% or less is preferable.
- the solution contains: The range of 0.01 to 50% by mass with respect to the poor solvent is preferred. If it is 0.01% by mass or more, the concentration of the complex to be precipitated is sufficiently high, so that solids can be easily recovered. If it is 50% by mass or less, all of the unsubstituted phthalocyanines and the substituents are contained. Phthalocyanine precipitates to form a solid composite, which has no dissolved components and can be easily recovered.
- the poor solvent is not particularly limited as long as the unsubstituted phthalocyanine and the substituted phthalocyanine are insoluble or hardly soluble liquid, but the homogeneity of the precipitated complex can be kept high, and will be described later.
- Water that is suitable for the miniaturization process and has a small environmental load or an aqueous solution containing water as a main component can be cited as the most preferable poor solvent.
- the complex can be filtered using a filter paper and a Buchner funnel to remove acidic water and washed with water until the filtrate becomes neutral to recover the complex containing water.
- the recovered complex is dehydrated and dried to remove moisture, or in the next step (b), when it is microparticulated by a wet method using a dispersion solvent having affinity for water, It may be left as it is. From the observation result with a transmission electron microscope, it was confirmed that the complex of unsubstituted phthalocyanine and substituted phthalocyanine obtained in this step (a) is an isotropic structure without crystal grain boundaries. It was.
- the step (b) is not particularly limited as long as the composite obtained through the step (a) can be formed into fine particles.
- There are dry and wet methods a method of micronizing a dispersion in a dispersion solvent) as a method for micronizing a composite.
- the micronized composite is crystallized in one direction in a solvent to produce one-dimensional nano particles. In consideration of the size structure, it is preferable to make the composite into fine particles by a wet method.
- the wet method there is a method in which the composite obtained in step (a) is treated with a dispersion medium and a media disperser using fine beads such as a bead mill or a paint conditioner.
- K examples thereof include a method of processing using an emulsifying disperser typified by a film mix, a method of processing using a jet mill typified by a nanomizer manufactured by Yoshida Kikai Kogyo, and the like.
- processing by high-power ultrasonic irradiation using an ultrasonic homogenizer is also applicable, and these methods can be performed by combining one or a plurality of types.
- examples of the dispersion solvent used in the wet method include water, an organic solvent, and a water-containing organic solvent.
- the organic solvent include alcohols such as ethanol, glycols, and glycol esters in addition to the organic solvent (described later) used in the step (c) described later, and these dispersion solvents are used alone or in combination.
- water, ethanol, methanol, chlorobenzene, dichlorobenzene, N-methyl-2-pyrrolidone, and propylene glycol monomethyl ether acetate are more preferable from the viewpoint of suppressing crystal growth and crystal transition.
- the mass ratio of the composite to the dispersion solvent there is no particular limitation on the mass ratio of the composite to the dispersion solvent, but from the viewpoint of dispersion efficiency, it is preferable to treat the solid concentration in the range of 1 to 30% by mass.
- the bead diameter is preferably in the range of 0.01 to 2 mm in view of the degree of dispersion of the composite.
- the amount of the minute media used is most preferably in the range of 100 to 1000% by mass with respect to the complex dispersion from the viewpoints of the efficiency of micronization and the recovery efficiency.
- micronization When micronization is performed in water, it is preferable to remove the water by dehydrating and drying the obtained aqueous dispersion of the micronized composite.
- dehydrating and drying There is no restriction
- the degree of atomization is preferably such that the composite obtained in step (a) has a particle size of less than 1 ⁇ m.
- the micronized composite is unidirectional. From the viewpoint of promoting the growth of a one-dimensional structure with a nano size by crystal growth, it is preferably less than 500 nm, and more preferably less than 300 nm (particle size is due to dynamic light scattering).
- the step (c) is a step of forming a nano-sized one-dimensional structure by crystallizing the micronized composite obtained through the step (b) in one direction (one-dimensional crystal growth).
- the degree of nano-size one-dimensional structure is preferably such that the shape of the obtained nano-size one-dimensional structure has a width (minor axis) of 500 nm or less, more preferably 300 nm or less, and most preferably 100 nm or less. is there.
- the method for forming the nano-sized one-dimensional structure is not particularly limited as long as the fine-particle composite can be converted into a nano-sized one-dimensional structure. In the phase), a method of forming a nano-sized one-dimensional structure can be mentioned.
- the composite can be made into a nano-sized one-dimensional structure by stirring or standing the micronized composite in an organic solvent (in a liquid phase).
- stirring or standing is performed in a controlled state at a predetermined temperature.
- the solvent to be used is not particularly limited unless it has a low affinity with phthalocyanines.
- phthalocyanines Preferred are amide organic solvents, aromatic organic solvents, halogen organic solvents, glycol ester solvents, glycol ether solvents and the like having high affinity with, specifically, Examples of amide solvents include N, N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, As aromatic organic solvents, toluene, xylene, ethylbenzene, Halogen organic solvents include chlorobenzene, dichlorobenzene, chloroform, methylene chloride, dichloroethane, As glycol ester solvents, ethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, prop
- the solid content concentration of the composite with respect to the organic solvent is in the range of 0.1 to 20% from the viewpoint of appropriate fluidity and prevention of aggregation. Preferably, it is 1 to 10%.
- the temperature at the time of stirring or standing when the composite is formed into a nano-sized one-dimensional structure is preferably in the range of 5 to 300 ° C, more preferably 20 to 250 ° C. If the temperature is 5 ° C. or higher, the crystal growth of phthalocyanines can be sufficiently induced, and the target one-dimensional crystal growth enables growth to a one-dimensional structure. If present, the produced one-dimensional structure is hardly aggregated and fused, and the crystal grows in the minor axis (width) direction and does not become coarse (isotropic structure).
- stirring time or standing time for forming the one-dimensional structure, but stirring or standing for at least 10 minutes or more until the length of the nano-sized one-dimensional structure grows to 100 nm or more. preferable.
- the solvent used in this step (c) may be different from the solvent used in the wet microparticulation treatment in the step (b).
- the solvent used in the wet micronization treatment is removed, and the micronized composite thus obtained is redispersed in the solvent used in this step (c).
- Filtration, centrifugation, evaporation processing by a rotary evaporator, etc. can be mentioned. After these, further drying may be performed using a vacuum dryer or the like until the solvent is completely removed.
- the method of redispersing in the solvent used in the step (c) is not particularly limited, but known and commonly used heat treatment, stirring treatment, dispersion stirring treatment, dispersion uniform treatment, ultrasonic irradiation treatment, ultrasonic stirring treatment, One or more methods such as ultrasonic uniform treatment and ultrasonic dispersion treatment can be combined.
- a phthalocyanine nano-sized one-dimensional structure obtained by one-dimensional crystal growth of the micronized composite obtained in step (b) can be obtained.
- the major axis / minor axis ratio (aspect ratio) of the nano-sized one-dimensional structure obtained in this manner can be lowered to obtain a one-dimensional structure having an appropriate aspect ratio.
- the nano-sized one-dimensional structure obtained by the above method is stirred in an organic solvent, dispersed and stirred, dispersed and homogenized, ultrasonic irradiation, ultrasonic stirred, and uniform ultrasonic.
- the method such as ultrasonic dispersion treatment, laser irradiation treatment or the like is subjected to treatment of one kind or a combination of plural kinds.
- the aspect ratio of the nano-sized one-dimensional structure can be reduced to an appropriate size.
- the ink composition of the present invention contains the phthalocyanine nanosize structure of the present invention and an organic solvent as essential components. These ink compositions are suitable as precursor materials for forming an active part (semiconductor layer) of an electronic element by a wet process (printing or coating).
- the ink composition of the present invention is produced by dispersing the phthalocyanine nanosize one-dimensional structure in an organic solvent. Or the dispersion liquid of the phthalocyanine nanosize one-dimensional structure obtained at the said process (c) can also be used as an ink composition of this invention.
- the type of the organic solvent is not particularly limited as long as it stably disperses the phthalocyanine nanosize one-dimensional structure. Even if it is a single organic solvent, an organic solvent in which two or more types are mixed is used. However, from the viewpoint of being able to disperse well and stably, for example, amide organic solvents, aromatic organic solvents, halogen organic solvents, glycol ester solvents, glycol ethers having high affinity with phthalocyanines System solvents and the like are preferred, specifically, Examples of amide solvents include N, N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, As aromatic organic solvents, toluene, xylene, ethylbenzene, Halogen organic solvents include chlorobenzene, dichlorobenzene, chloroform, methylene chloride, dichloroethane, As glycol ester solvents, ethylene glycol monomethyl ether acetate, diethylene glycol
- the content of the phthalocyanine nanosize one-dimensional structure in the composition is set to 0.05 to 20% by mass, preferably 0.1 to 10% by mass.
- the ink composition of the present invention may contain other electron donating materials and hole transporting materials in addition to the phthalocyanine nanosize one-dimensional structure.
- examples of such materials include ⁇ -conjugated polymers that exhibit semiconducting properties, non- ⁇ conjugated polymers that exhibit semiconducting properties, and low molecular organic semiconductor compounds.
- polythiophene poly (3-hexylthiophene-2,5-diyl) (P3HT), P3HT regioregular type, polypoly-p-phenylene vinylenes, poly- p-Phenylenes, polyfluorenes, polypyrroles, polyanilines, polyacetylenes, polythienylene vinylenes, etc.
- P3HT poly(2-hexylthiophene-2,5-diyl)
- P3HT regioregular type polypoly-p-phenylene vinylenes, poly- p-Phenylenes, polyfluorenes, polypyrroles, polyanilines, polyacetylenes, polythienylene vinylenes, etc.
- non- ⁇ conjugated polymers showing semiconducting properties such as polyvinyl carbazole, and low molecular organic semiconductor compounds.
- Soluble or solvent dispersible phthalocyanine derivatives soluble or solvent dispersible porphyrin derivatives, 6,13-bis (triisopropylsilylethynyl) pentacene (TIPS-pentacene), and the like.
- the polymer material also has an effect of imparting wet process (printing or coating) suitability and film forming property (film quality after printing or coating) to the ink composition.
- the ink composition of the present invention may contain an electron-accepting material typified by fullerenes.
- an electron-accepting material typified by fullerenes.
- the electron-accepting material include naphthalene derivatives, perylene derivatives, oxazole derivatives, triazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, fullerenes, carbon nanotubes (CNT), graphene, poly-p-phenylene.
- NCDI 1,4,5,8-naphthalene tetracarboxyl diimide
- NCDI-R N′-dialkyl-1,4,5,8-naphthalene tetracarboxyl diimide
- PTCDA 3,4,9,10-perylenetetracarboxylic bisbenzimidazole
- PTCDI 3,4,9,10-perylenetetracarboxylic diimide
- PTCDI N, N′-dimethyl -3,4,9,10-perylenetetracarboxyl Kudiimide
- Triazole derivatives such as-(4-t-butylphenyl) -1,3,4-oxadiazole (PBD), 2,5-di (1-naphthyl) -1,3,4-oxadiazole (BND) As 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (TAZ), etc.
- enanthroline derivatives include bathocuproin (BCP) and bathophenanthroline (Bphen), and examples of fullerenes include unsubstituted ones such as C60, C70, C76, C78, C82, C84, C90, C94, and [6,6].
- fullerenes are preferably used because of their high charge separation rate and electron transfer rate.
- PCBM and C70 derivatives are more preferable because they are particularly excellent in charge separation speed and electron transfer speed and can provide higher photoelectric conversion efficiency.
- the electron-accepting materials include polymer-based materials (electron-accepting polymers) such as a derivative in which a cyano group is introduced into poly-p-phenylene vinylene (CN-PPV), Boramer (trade name, manufactured by TDA Research)
- the ink composition or photoelectric conversion element material
- the ink composition has wet process (printing or coating) suitability and film forming properties (film quality after printing or coating). Since there exists an effect to provide, it is preferable.
- the mixing ratio of the phthalocyanine nanosize one-dimensional structure and the electron-accepting material of the ink composition of the present invention in the photoelectric conversion element described later, it can be arbitrarily selected as long as the photoelectric conversion characteristics are obtained.
- One-dimensional structure / electron-accepting material 1/99 to 99/1 is preferable, 1/9 to 9/1 is more preferable, and 2/8 to 8/2 is more preferable. Range.
- the total content of the phthalocyanine nanosize one-dimensional structure and the electron-accepting material is 0.05 to 20% by mass with respect to the solvent.
- the content is preferably 0.1 to 10% by mass.
- a resin component may be added as a rheology adjustment or binder component. It can.
- the resin is not particularly limited as long as it is a publicly known one, and it may be a single resin or two or more resins may be used in combination. Polymethyl methacrylate, polystyrene, polycarbonate, etc. may be used. preferable.
- the content of these resins is preferably 20% by mass or less, and more preferably 10% by mass or less.
- the ink composition of the present invention may contain constitutional components and various surfactants as needed mainly for the purpose of improving wet process (printing or coating) suitability and film forming property (film quality after printing or coating). Can be added and used.
- any known and commonly used fine particle powder, or a dispersion obtained by previously dispersing these fine particle powders in a dispersant or an organic solvent in advance can be used as long as they can maintain semiconductor characteristics. You may use together and use a seed or more.
- Aerosil series (trade name, manufactured by Evonik), Cylicia, Silo Hovic, Silo Pute, Silo Page, Silo Pure, Thylosphere, Silo Mask, Silwell, Fuji Balloon (above, trade name, manufactured by Fuji Silicia),
- PMA-ST There are PMA-ST, IPA-ST (above, trade name, manufactured by Nissan Chemical Co., Ltd.), NANOBIC 3600 series, NANOBIC 3800 series (above, trade name, manufactured by BYK Chemie), etc., but there is no particular limitation. These may be used alone or in combination of two or more.
- the photoelectric conversion element transports electric charges in the film thickness direction, the surface smoothness of the film is required.
- the average particle size of the constitutional component added to the ink is preferably 1 to 150 nm, more preferably 5 to 50 nm, and PMA-ST and IPA-ST which are fine particle silica and alumina dispersion liquids (commodities) Name, manufactured by Nissan Chemical Co., Ltd.) and NANOBIC 3600 series (trade name, manufactured by Big Chemie) are preferable.
- the average particle diameter can be easily measured by, for example, a dynamic light scattering method.
- these constitutional components are electrically inactive, if the content is too high, the concentration of the phthalocyanine nanosize structure of the present invention becomes relatively thin, so that the semiconductor characteristics expressed by the phthalocyanine nanosize structure of the present invention Will be reduced. Accordingly, the content of the constitutional component in the ink composition is 90% by mass or less, preferably 70% by mass or less, based on the total solid content.
- the surfactant examples include hydrocarbons, silicons, and fluorines, and these can be used alone or in combination of two or more.
- a preferred fluorosurfactant is a nonionic fluorosurfactant having a linear perfluoroalkyl group and having a chain length of C6 or more, more preferably C8 or more.
- Specific examples include, for example, Megafuck F-482, Megafuck F-470 (R-08), Megafuck F-472SF, Megafuck R-30, Megafuck F-484, Megafuck F-486, Mega There are Facque F-172D, MegaFuck F178RM (the trade name, manufactured by DIC), etc., but there is no particular limitation. These may be used alone or in combination of two or more.
- These surfactants are contained in the ink composition in an amount of 5.0% by mass or less, preferably 1.0% by mass or less as an active ingredient, as an active ingredient.
- the materials described above are mixed and used.
- the mixing method is not particularly limited, but after adding the above-described materials to the solvent in a desired ratio, a known and commonly used method, that is, heat treatment, stirring treatment, dispersion stirring treatment, dispersion homogenization treatment, Examples thereof include a method in which one or a plurality of methods such as ultrasonic irradiation treatment, ultrasonic stirring treatment, ultrasonic homogenization, ultrasonic dispersion treatment, and laser irradiation treatment are combined and dispersed in a solvent.
- the electronic device of the present invention is an electronic device containing the phthalocyanine nanosize one-dimensional structure of the present invention in an active layer portion (semiconductor layer).
- electronic elements include photoelectric conversion elements such as solar cells and light receiving elements, transistors such as field effect transistors, electrostatic induction transistors, and bipolar transistors, electroluminescence elements, temperature sensors, gas sensors, humidity sensors, and radiation sensors. However, it is not limited to these.
- the photoelectric conversion element of the present invention has at least a pair of electrodes, that is, a positive electrode and a negative electrode, and includes the phthalocyanine nanosize structure of the present invention between these electrodes.
- FIG. 1 is a schematic view showing an example of the photoelectric conversion element of the present invention.
- reference numeral 1 is a substrate
- reference numeral 2 is an electrode a
- reference numeral 3 is a photoelectric conversion layer (organic semiconductor layer) including the phthalocyanine nanosize structure of the present invention
- reference numeral 4 is an electrode b.
- the organic semiconductor layer 3 is a film containing the phthalocyanine nanosize one-dimensional structure of the present invention.
- the organic semiconductor layer 3 is a film formed from the ink composition of the present invention.
- the phthalocyanine nanosize structure of the present invention and the electron accepting material may be mixed or laminated.
- An example in the case of being laminated is shown in FIG. It is preferable that the layer having the phthalocyanine nanosize structure of the present invention as the electron donating material is on the positive electrode side and the layer having the electron accepting material is on the negative electrode side.
- reference numeral 5 in FIG. 2 is a layer having a phthalocyanine nanosize one-dimensional structure of the present invention
- reference numeral 6 is a layer containing an electron-accepting material
- the electrode a having a reference numeral 2 is a positive electrode
- the electrode b having a reference numeral 4 is Becomes the negative electrode.
- an electron donating material other than the above-described phthalocyanine nanosize one-dimensional structure may be contained in the layer (reference numeral 5) containing the phthalocyanine nanosize structure of the present invention. Or you may contain in the layer (code
- the thickness of the organic semiconductor layer is not particularly limited as long as the thickness can sufficiently absorb light and does not cause charge deactivation.
- a thickness of ⁇ 1000 nm is preferable, more preferably 10 to 500 nm, and still more preferably 20 to 300 nm.
- the layer having the phthalocyanine nanosize structure of the present invention preferably has a thickness of 1 to 500 nm, more preferably 5 to 300 nm.
- the organic semiconductor layer can be obtained by forming the ink composition of the present invention into a film by a wet process (printing or coating) and drying it.
- a film forming method of the ink composition of the present invention a known and commonly used method can be adopted without any particular limitation, and specifically, an inkjet method, a gravure printing method, a gravure offset printing method, an offset printing method, a relief printing.
- Method letterpress reverse printing method, screen printing method, micro contact printing method, reverse coater method, air doctor coater method, blade coater method, air knife coater method, roll coater method, squeeze coater method, impregnation coater method, transfer roll coater method, Examples thereof include a kiss coater method, a cast coater method, a spray coater method, an electrostatic coater method, an ultrasonic spray coater method, a die coater method, a spin coater method, a bar coater method, a slit coater method, and a drop cast method.
- the electron-accepting material is prepared as a buffer layer described later. What is necessary is just to laminate
- silicon, glass, various resin materials, or the like can be used.
- Various resin materials include, for example, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC). , Cellulose triacetate (TAC), cellulose acetate propionate (CAP), acrylic resin, and the like.
- a material having good light transmittance is preferable, and examples of such a material include glass, PET, PC, polyimide, PES, acrylic resin, and the like.
- a conductive material having a high work function for one electrode and a conductive material having a low work function for the other electrode it is preferable to use a conductive material having a high work function for one electrode and a conductive material having a low work function for the other electrode.
- An electrode using a conductive material having a large work function is a positive electrode.
- the conductive material used for the positive electrode is preferably one that is in ohmic contact with the organic semiconductor layer 3. Furthermore, when the buffer layer 1 described later is used, it is preferable that the conductive material used for the positive electrode is in ohmic contact with the buffer layer 1.
- An electrode using a conductive material having a small work function is a negative electrode, and as the conductive material having a small work function, alkali metal or alkaline earth metal, specifically lithium, magnesium, calcium, or the like is used. . Further, tin, silver, aluminum and the like are also preferably used. Furthermore, an electrode made of an alloy made of the metal or a laminate of the metal is also preferably used.
- the conductive material used for the negative electrode is preferably one that is in ohmic contact with the organic semiconductor layer 3. Furthermore, when the buffer layer 2 described later is used, it is preferable that the conductive material used for the negative electrode is in ohmic contact with the buffer layer 2.
- the electrode a or the electrode b has a light transmittance.
- the light transmittance of the electrode is not particularly limited as long as incident light reaches the organic semiconductor layer 3 and an electromotive force is generated.
- a conductive material for example, among the conductive materials, ITO (indium oxide-tin oxide composite), FTO (fluorine-doped tin oxide), (laminated) graphene, (laminated) modified graphene, conductive by doping
- a commonly known conductive polymer conductive polyaniline, conductive polypyrrole, conductive polythiophene, polyethylenedioxythiophene (PEDOT), etc.
- these materials can be used in combination with a mesh made of a metal material having high conductivity.
- the thickness of the electrode may be in a range having light transmittance and conductivity, and varies depending on the electrode material, but is preferably 5 to 10,000 nm, preferably 10 to 5000 nm, more preferably 20 to 300 nm.
- the other electrode is not necessarily light-transmitting as long as it has conductivity, and the thickness is not particularly limited.
- the above materials are used as raw materials, such as a vacuum deposition method, a molecular beam epitaxial growth method, an ion cluster beam method, a low energy ion beam method, an ion plating method, a CVD method, a sputtering method, and an atmospheric pressure plasma method.
- Dry process inkjet method, gravure printing method, gravure offset printing method, offset printing method, relief printing method, relief printing method, screen printing method, micro contact printing method, reverse coater method, air doctor coater method, blade coater method , Air knife coater method, roll coater method, squeeze coater method, impregnation coater method, transfer roll coater method, kiss coater method, cast coater method, spray coater method, electrostatic coater method, ultrasonic spray coater method, die coater method, Pinkota method, a bar coater method, a slit coater method, include wet process drop casting, it may be appropriately used depending on the material.
- a method of forming an electrode through a pattern mask or the like using a dry process such as vapor deposition or sputtering, a conductive solid film formed by a dry process such as vapor deposition or sputtering, and a known conventional photolithographic method-etching method Electrode forming method, electrodeposition method combining dry process such as vapor deposition and sputtering and photolithographic method-lift-off method, conductive solid film formed using dry process such as vapor deposition and sputtering, resist by inkjet etc. And a method of etching using the above.
- the conductive fine particle dispersion or the conductive polymer solution or dispersion may be directly patterned by a wet process such as an ink jet method, a screen printing method, a gravure offset printing method, a letterpress reverse printing method, or a micro contact printing method. Then, after forming a solid film by coating film formation, patterning may be performed by a well-known and commonly used photolithography-etching method or laser ablation method, or a combination of a wet process and a photolithography method-lift-off method. You may do it.
- a wet process such as an ink jet method, a screen printing method, a gravure offset printing method, a letterpress reverse printing method, or a micro contact printing method.
- patterning may be performed by a well-known and commonly used photolithography-etching method or laser ablation method, or a combination of a wet process and a photolithography method-lift-off method. You may do it.
- the buffer layer 1 may be provided between the positive electrode and the organic semiconductor layer.
- the buffer layer 1 is used as necessary to enable efficient charge extraction.
- Examples of the material for forming the buffer layer 1 include graphene oxide, modified graphene, polythiophenes, polyanilines, poly-p-phenylene vinylenes, polyfluorenes, polyvinyl carbazoles, phthalocyanine derivatives (H2Pc, CuPc, ZnPc, etc.), porphyrins Derivatives and the like are preferably used. These materials may have improved conductivity (hole transportability) by doping.
- PEDOT polyethylenedioxythiophene
- PSS polystyrene sulfonate
- the thickness of the buffer layer 1 is preferably 5 to 600 nm, more preferably 10 to 200 nm.
- the buffer layer 2 between an organic-semiconductor layer and a negative electrode.
- the buffer layer 2 is used as necessary to enable efficient charge extraction.
- the above-described electron accepting materials naphthalene derivatives, perylene derivatives, oxazole derivatives, triazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, fullerenes, carbon nanotubes (CNT), modified graphenes, poly -Derivatives with a cyano group introduced into p-phenylene vinylene (CN-PPV), Boramer (trade name, manufactured by TDA Research), known low molecular organic semiconductor materials or polymeric organics with a CF 3 group or F group introduced
- perfluoro compounds such as octaazaporphyrin, perfluoropentacene and perfluorophthalocyanine, electron donating compounds such as te
- Buffer layer formation methods include vacuum deposition, molecular beam epitaxial growth, ion cluster beam method, low energy ion beam method, ion plating method, CVD method, sputtering method, atmospheric pressure plasma method and other dry processes, inkjet Method, gravure printing method, gravure offset printing method, offset printing method, relief printing method, relief printing method, screen printing method, micro contact printing method, reverse coater method, air doctor coater method, blade coater method, air knife coater method, Roll coater method, squeeze coater method, impregnation coater method, transfer roll coater method, kiss coater method, cast coater method, spray coater method, electrostatic coater method, ultrasonic spray coater method, die coater method, spin coater , A bar coater method, a slit coater method, include wet process drop casting, it may be appropriately used depending on the material.
- an inorganic oxide for the buffer layer when using an inorganic oxide for the buffer layer, as a wet process, a liquid in which fine particles of the inorganic oxide are dispersed in any organic solvent or water using a dispersion aid such as a surfactant as required is applied. Further, a drying method or a so-called sol-gel method in which a solution of an oxide precursor, for example, an alkoxide body is applied and dried can be used.
- These buffer layers may be a single layer or may be a laminate of different materials.
- the photoelectric conversion element by this invention can comprise a solar cell module by integration.
- the photoelectric conversion element of this invention can also be set as the structure which interrupts
- the photoelectric conversion element according to the present invention is integrated in series by bringing the electrode a of the photoelectric conversion element according to the present invention into contact with the electrode b of another photoelectric conversion element according to the present invention adjacent thereto.
- the solar cell module characterized by having been made into can be mentioned.
- the electrodes a of adjacent photoelectric conversion elements according to the present invention are brought into contact with each other, and the electrodes b of adjacent photoelectric conversion elements according to the present invention are brought into contact with each other, whereby the photoelectric conversion elements according to the present invention are connected in parallel and integrated.
- It may be a solar cell module characterized in that
- the transistor of the present invention is a transistor containing the phthalocyanine nanosize structure of the present invention in an active part (referred to as a channel part (semiconductor layer) in the transistor).
- a film including a phthalocyanine nanosize structure according to the present invention and a source electrode and a drain electrode connected to the film are formed on a substrate, and a gate electrode is formed thereon via a gate insulating film.
- a gate type can be mentioned.
- a bottom gate type in which a gate electrode is first formed on a substrate and a film including a phthalocyanine nanosize structure according to the present invention and a source electrode and a drain electrode connected thereto are formed via a gate insulating film can be used.
- FIG. 3 is a schematic diagram of a transistor configured as a bottom gate bottom contact type as a transistor having a film (12) containing a phthalocyanine nanosize structure according to the present invention.
- the thickness of the film (12) containing the phthalocyanine nanosize structure of the present invention can be set as appropriate, for example, 50 to 10,000 nm.
- plastic film As the substrate 7, silicon, glass, a flexible resin sheet (plastic film), or the like is used.
- plastic film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), Examples thereof include films made of cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.
- TAC cellulose triacetate
- CAP cellulose acetate propionate
- the material for forming the source electrode 10, the drain electrode 11, and the gate electrode 8 is not particularly limited as long as it is a conductive material.
- conductive polymers whose conductivity is improved by doping or the like, for example, conductive polyaniline, conductive polypyrrole, conductive polythiophene, a complex of polyethylenedioxythiophene and polystyrene sulfonic acid, and the like are also preferably used.
- gold, silver, platinum, copper, conductive polymer, and ITO, which have low electrical resistance on the contact surface with the semiconductor layer, are preferable.
- the same method as that for the electrode of the photoelectric conversion element can be used.
- Various insulating films can be used as the gate insulating layer 9.
- a polymer organic material in view of cost merit, it is preferable to use a polymer organic material, and in order to obtain high characteristics, it is preferable to use an inorganic oxide having a high relative dielectric constant.
- the polymer organic material include polyimide, polyamide, polyester, polyacrylate, photo radical polymerization system, photo cation polymerization system photo-curing resin, copolymer containing acrylonitrile component, polyvinyl phenol, polyvinyl alcohol, novolac resin, Known and conventional polymers such as epoxy resins and cyanoethyl pullulan can be used.
- inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, barium zirconate titanate, lead zirconate titanate, lead lanthanum titanate, strontium titanate, Examples include barium titanate, barium magnesium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantalate, bismuth tantalate niobate, and yttrium trioxide. Of these, silicon oxide, aluminum oxide, tantalum oxide, and titanium oxide are preferable. Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.
- a dry process such as a vacuum deposition method, a molecular beam epitaxial growth method, an ion cluster beam method, a low energy ion beam method, an ion plating method, a CVD method, a sputtering method, an atmospheric pressure plasma method, Inkjet method, gravure printing method, gravure offset printing method, offset printing method, relief printing method, relief printing method, screen printing method, micro contact printing method, reverse coater method, air doctor coater method, blade coater method, air knife coater method , Roll coater method, squeeze coater method, impregnation coater method, transfer roll coater method, kiss coater method, cast coater method, spray coater method, electrostatic coater method, ultrasonic spray coater method, die coater method, spin coater method
- Wet processes such as bar coater method, slit coater method, drop cast method, etc. are mentioned, but when precise patterning is required, wet processes such as ink jet method, letterpress reverse
- a method of applying and drying a liquid in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as necessary in the wet process of inorganic oxide, a method of applying and drying a liquid in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as necessary.
- a so-called sol-gel method in which an oxide precursor, for example, an alkoxide solution is applied and dried can be used.
- the dry film thickness of these insulating films is 0.1 to 2 ⁇ m, preferably 0.3 to 1 ⁇ m.
- the transistor as the electronic element according to the present invention can constitute an electronic component module by integration.
- the electronic component module include a transistor array (see FIG. 4) as a back substrate such as a display, an inverter or a ring oscillator as an RFID logic circuit, and the like.
- Synthesis Example 2 In Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed, except that 17.5 parts by mass of n-propylmonoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of the 40% aqueous solution of methyl monoamine. The compound represented by the formula 12] was obtained.
- Synthesis Example 3 In Synthesis Example 1, the same operation as in Synthesis Example 1 was performed except that 30 parts by mass of hexyl monoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of methyl monoamine 40% aqueous solution. The compound represented was obtained.
- Synthesis Example 4 In Synthesis Example 1, the same operation as in Synthesis Example 1 was carried out except that 55 parts by mass of dodecyl monoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of methyl monoamine 40% aqueous solution. The compound represented was obtained.
- dodecyl monoamine manufactured by Tokyo Chemical Industry Co., Ltd.
- Synthesis Example 5 In Synthesis Example 1, the same operation as in Synthesis Example 1 was performed except that 80 parts by mass of stearyl monoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of methyl monoamine 40% aqueous solution. The compound represented was obtained.
- Synthesis Example 6 In Synthesis Example 1, the same operation as in Synthesis Example 1 was performed, except that 29.4 parts by mass of cyclohexyl monoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of 40% aqueous solution of methyl monoamine. The compound represented by this was obtained.
- Synthesis Example 7 In Synthesis Example 1, the same operation as in Synthesis Example 1 was performed, except that 27.6 parts by mass of phenyl monoamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 23 parts by mass of methyl monoamine 40% aqueous solution. The compound represented by this was obtained.
- Synthesis Example 8 In Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed, except that 29.4 parts by mass of 3-thienyl monoamine was used instead of 23 parts by mass of the 40% aqueous solution of methyl monoamine. Got.
- Example 1 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> 1.6 g of copper phthalocyanine (Fastogen Blue 5380E (trade name, manufactured by DIC)) as an unsubstituted phthalocyanine and 1.2 g of a phthalocyanine derivative represented by [Chemical Formula 11] obtained in Synthesis Example 1 as a phthalocyanine having a substituent It was poured into 81 g of concentrated sulfuric acid (manufactured by Kanto Chemical Co., Ltd.) and completely dissolved to prepare a concentrated sulfuric acid solution.
- the dispersion of the pulverized complex was separated and recovered from the zirconia beads, and further dichlorobenzene was added to reduce the solid content concentration to 2% (adjustment of the dichlorobenzene 2% dispersion of the pulverized complex).
- n-type silicon substrate was prepared and used as a gate electrode, and the surface layer was thermally oxidized to form a gate insulating film made of silicon oxide.
- the phthalocyanine nanosize structure dispersion liquid (1) was spin coated to form a semiconductor film (channel portion) made of the phthalocyanine nanosize structure.
- a source / drain electrode made of a gold thin film was patterned by vapor deposition to produce a transistor (1).
- the channel length L (source electrode-drain electrode interval) was 75 ⁇ m, and the channel width W was 5.0 mm.
- the transistor characteristics of the transistor (1) were evaluated.
- the transistor characteristics were evaluated using a digital multimeter (SMU237, manufactured by Keithley), sweeping from 0 to -80V voltage (Vg) to the gate electrode, and the current (Id) between the source and drain electrodes to which -80V was applied. This was done by measuring.
- the mobility was 5 ⁇ 10 ⁇ 3 and the ON / OFF ratio was 10 4 .
- the mobility was obtained from the slope of ⁇ Id ⁇ Vg by a known method.
- the unit is cm 2 / V ⁇ s.
- the ON / OFF ratio was determined by (maximum value of absolute value of Id) / (minimum value of absolute value of Id).
- An ITO transparent conductive layer serving as a positive electrode was deposited to a thickness of 100 nm on a glass substrate by sputtering, and this was patterned into a 2 mm-wide strip by photolithography-etching.
- the obtained glass substrate with pattern ITO was subjected to ultrasonic cleaning three times for 15 minutes each in the order of neutral detergent, distilled water, acetone and ethanol, and then UV / ozone treatment for 30 minutes, and PEDOT: PSS on this.
- a buffer layer 1 made of PEDOT: PSS was formed to a thickness of 60 nm on the ITO transparent electrode layer by spin coating an aqueous dispersion (AI4083 (trade name, manufactured by HC Starck)).
- the PEDOT: PSS layer was spin-coated with the photoelectric conversion layer material (1), and the photoelectric conversion layer material (1) having a thickness of 100 nm.
- a derived organic semiconductor layer was formed.
- the “substrate on which the organic semiconductor layer is formed” and a metal mask for vapor deposition (for forming a 2 mm strip pattern) are placed in a vacuum vapor deposition apparatus, and the degree of vacuum in the apparatus is reduced to 5 ⁇ 10 ⁇ 4 Pa.
- aluminum serving as a negative electrode was deposited by vapor deposition so as to form a strip pattern having a width of 2 mm by a resistance heating method (film thickness: 80 nm).
- the photoelectric conversion element (1) having an area of 2 mm ⁇ 2 mm (a portion where the strip-like ITO layer and the aluminum layer intersect) was manufactured.
- the positive and negative electrodes of the photoelectric conversion element (1) are connected to a digital multimeter (6241A, product name (manufactured by ADC)), and the spectrum shape is AM1.5 and the irradiation intensity is 100 mW / cm 2 simulated sunlight (simple Under the irradiation (irradiation from the ITO layer side) of a type solar simulator XES151S (product name, manufactured by Mitsunaga Electric Manufacturing Co., Ltd.), the voltage was swept from ⁇ 0.1 V to +0.8 V in the atmosphere, and the current value was measured. At this time, the short-circuit current density (value of the current density when the applied voltage is 0 V.
- J sc is 4.93 mA / cm 2
- the open circuit voltage value of the applied voltage when the current density is 0. , V oc ) was 0.56 V
- the fill factor (FF) was 0.37
- the photoelectric conversion efficiency (PCE) calculated from these values was 1.01%.
- FF and PCE were calculated by the following formula.
- JV max is the value of the product of the current density and the applied voltage at the point where the product of the current density and the applied voltage is maximum between the applied voltage of 0 V and the open-circuit voltage value.
- PCE [(J sc ⁇ V oc ⁇ FF) / pseudo sunlight intensity (100 mW / cm 2 )] ⁇ 100 (%)
- Example 2 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (2) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (2) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (2) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (2) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 3 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (3) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (3) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (3) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (3) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 4 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (4) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (4) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (4) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (4) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 5 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosized structure dispersion liquid (5) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (5) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (5) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (5) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 6 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (6) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (6) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (6) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (6) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 7 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (7) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (7) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (7) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (7) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- Example 8 ⁇ Production of phthalocyanine nanosize structure and phthalocyanine nanosize structure dispersion> A phthalocyanine nanosize structure dispersion liquid (8) was obtained in the same manner as in Example (1) except that the sulfamoyl group-substituted phthalocyanine obtained in Synthesis Example (8) was used as the phthalocyanine having a substituent. ⁇ Manufacture of transistors and evaluation of transistor characteristics (mobility)> A transistor (8) was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (8) was used as the phthalocyanine nanosize structure dispersion. The evaluation results of characteristics are summarized in Table 1.
- a phthalocyanine nanosize structure dispersion liquid (1) ′ was obtained in the same manner as in Example (1) except that a sulfamoyl group-substituted phthalocyanine represented by [Chemical Formula 19] was used as the substituted phthalocyanine.
- a transistor (1) ′ was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (1) ′ was used as the phthalocyanine nanosize structure dispersion.
- the evaluation results of characteristics are summarized in Table 1.
- a phthalocyanine nanosize structure dispersion liquid (2) ′ was obtained in the same manner as in Example (1) except that a phthalocyanine derivative represented by [Chemical Formula 20] was used as the substituted phthalocyanine.
- the dispersion was adjusted according to the method described in WO2010 / 122921.
- a transistor (2) ′ was obtained as Example (1) except that the phthalocyanine nanosize structure dispersion (2) ′ was used as the phthalocyanine nanosize structure dispersion.
- the evaluation results of characteristics are summarized in Table 1.
- the phthalocyanine nanosize structure of the present invention since an phthalocyanine derivative having an optimized structure is used as the material constituting the phthalocyanine nanosize structure, an electronic device (such as a transistor) with improved characteristics can be constructed. It becomes possible.
- Electrode b 5 A layer containing the phthalocyanine nanosize structure of the present invention (when electrode a is a positive electrode) or a layer containing an electron-accepting material (when electrode a is a negative electrode) 6 A layer containing an electron-accepting material (when the electrode b is a negative electrode) or a layer containing the phthalocyanine nanosize structure of the present invention (when the electrode b is a positive electrode) 7 Substrate 8 Gate electrode 9 Gate insulating film 10 Source electrode 11 Drain electrode 12 Semiconductor layer containing the phthalocyanine nanosize structure of the present invention
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Abstract
Description
一方、ウエットプロセスを想定した電子素子へより好適に展開するためには、該一次元結晶性構造物は、短径が500nm以下の一次元結晶性構造物(以下、ナノサイズ一次元構造物と表記する)であることが好ましい。
無置換フタロシアニン及び置換基を有するフタロシアニンを含有するナノサイズ構造物であって、
構造物の形状が、長径と短径を有し、その短径が500nm以下であり、
無置換フタロシアニンが、一般式(1)又は(2)で表されるものであり、
置換基を有するフタロシアニンが、一般式(3)又は(4)で表されるものであるフタロシアニンナノサイズ構造物。
フタロシアニン骨格のベンゼン環にある各水素原子はフッ素、塩素、臭素で置換されていても良く、Z1~Z8は、それぞれ独立に、水素原子、置換基を有してもよい炭素数1~30の非環状炭化水素基、置換基を有してもよい炭素数1~30の環状炭化水素基、置換基を有してもよいへテロアリール基であり、a、b、c、及びdは各々独立に0~4の整数を表すが少なくとも1つは0ではなく、Z1~Z8が一般式(5)、又は(6)である場合、及び共に水素原子である場合を除く。
を提供するものである。
以下、本発明のフタロシアニンナノサイズ構造物について説明する。
本発明のフタロシアニンナノサイズ構造物は、長径(長軸)と短径(短軸)を有する一次元性(ワイヤー状、ファイバー状、糸状、針状、ロッド状等の線状)構造物であって、その短径は500nm以下、さらに好ましくは300nm以下、最も好ましくは100nm以下であり、無置換フタロシアニンと置換基を有するフタロシアニン(フタロシアニン誘導体)を構造物構成材料として含むものである。なお、長径については、(長径/短径)>1であれば(長径/短径が1より大きければ)、特に制限は無い。又、無置換フタロシアニンと置換基を有するフタロシアニンの混合比は、置換基を有するフタロシアニンの無置換フタロシアニンに対する混合比([置換基を有するフタロシアニンの質量×100]/[無置換フタロシアニンの質量])が1~200質量%の範囲が好ましく、さらに好ましくは1~120質量%である(後記)。
フタロシアニン骨格のベンゼン環にある各水素原子はフッ素、塩素、臭素で置換されていても良く、Z1~Z8は、それぞれ独立に、水素原子、置換基を有してもよい炭素数1~30の非環状炭化水素基、置換基を有してもよい炭素数1~30の環状炭化水素基、置換基を有してもよいへテロアリール基であり、a、b、c、及びdは各々独立に0~4の整数を表すが少なくとも1つは0ではなく、Z1~Z8が一般式(5)、又は(6)である場合、及び共に水素原子である場合を除く。
-SO2NH-CH2CH3
-SO2NH-CH2CH2CH3
-SO2NH-CH(CH3)2
-SO2NH-CH2CH2CH2CH3
-SO2NH-CH(CH3)(CH2CH3)
-SO2NH-CH2-CH(CH3)2
-SO2NH-C(CH3)3
-SO2NH-(CH2)4CH3
-SO2NH-(CH2)5CH3
-SO2NH-(CH2)7CH3
-SO2NH-(CH2)11CH3
-SO2NH-(CH2)17CH3
-SO2NH-(CH2)21CH3
-SO2NH-Cy
(Cyはシクロヘキシル基を表す。)
-SO2NH-Ph
-SO2NH-Th
(Thはチエニル基を表す。)
-SO2N(CH3)2
-SO2N(CH2CH2CH3)2
本発明のフタロシアニンナノサイズ構造物の製造方法は、例えば、WO2010/122921号公報、特開2009-280531号公報、WO2011/065133号公報に記載の方法を用いることが出来る。また、これらの公報に記載されている方法で得られたナノサイズ構造物の、長径/短径比(アスペクト比)を調整し、ナノサイズ構造物のアスペクト比を下げる方法も、本発明のフタロシアニンナノサイズ構造物の製造方法に用いることができる。以下に具体例を示す。
(a)前記無置換フタロシアニンと前記置換基を有するフタロシアニンとを良溶媒に溶解させた後に、貧溶媒に析出させて複合体を得る工程(a)と、
(b)前記複合体を微粒子化して、微粒子化複合体を得る工程(b)と、
(c)前記微粒子化複合体を有機溶媒中にて一次元結晶成長(一方向に結晶成長)させ、ナノサイズの一次元構造物(ナノワイヤー又はナノロッド)化する工程(c)と
を有するものである。
一般にフタロシアニン類は硫酸などの酸溶媒に可溶であることが知られており、本発明のフタロシアニンナノサイズ構造物の製造方法においても、まず前記無置換フタロシアニンと前記置換基を有するフタロシアニン(スルファモイル基置換フタロシアニン)とを硫酸、クロロ硫酸、メタンスルホン酸、トリフルオロ酢酸等の酸溶媒に溶解させる。その後に水などの貧溶媒に投入して該無置換フタロシアニンと該置換基を有するフタロシアニンの複合体を析出させる。
本工程(a)で得られた無置換フタロシアニンと置換基を有するフタロシアニンの複合体は、透過型電子顕微鏡による観察結果から、結晶粒界がなく等方性形状の構造物であることが確認された。
工程(b)は、前記工程(a)を経て得られた複合体を微粒子化することができれば、その方法は特に限定されるものではない。複合体の微粒子化方法には乾式法と湿式法(分散溶媒中で微粒子化を行なう方法)があるが、工程(c)において溶媒中で微粒子化複合体を一方向に結晶成長させ一次元ナノサイズ構造物化を行なうことを考慮すると、湿式法で前記複合体を微粒子化することが好ましい。
工程(c)は、前記工程(b)を経て得られた微粒子化複合体を、一方向に結晶成長(一次元結晶成長)させることでナノサイズ一次元構造物化する工程である。ナノサイズ一次元構造物化の程度は、得られるナノサイズ一次元構造物の形状が、幅(短径)が500nm以下であることが好ましく、より好ましくは300nm以下であり、最も好ましくは100nm以下である。
ナノサイズ一次元構造物化の方法は、該微粒子化複合体をナノサイズ一次元構造物化することができれば、その方法は特に限定されるものではないが、該微粒子化複合体を有機溶媒中(液相中)でナノサイズ一次元構造物化する方法を挙げることができる。具体的には、該微粒子化複合体を、有機溶媒中(液相中)にて、攪拌又は静置することで、該複合体をナノサイズ一次元構造物化せしめることが出来る。なお、攪拌又は静置に際しては、所定の温度下に制御された状態で行なうことが、ナノサイズ一次元構造物の形状を制御するという観点で好ましい。
アミド系溶媒として、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、
芳香族系有機溶媒として、トルエン、キシレン、エチルベンゼン、
ハロゲン系有機溶媒として、クロロベンゼン、ジクロロベンゼン、クロロホルム、塩化メチレン、ジクロロエタン、
グリコールエステル系溶媒として、エチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、
グリコールエーテル系溶媒として、エチレングリコールメチルエーテル、エチレングリコールエチルエーテル、エチレングリコールブチルエーテル、ジエチレングリコールエチルエーテル、ジエチレングリコールブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールターシャリーブチルエーテル、ジプロピレングリコールモノメチルエーテルを最も好適な有機溶媒として挙げることができる。前記有機溶媒は単独で用いることもできるが、任意の比率で混合して使用することもでき、さらには他の有機溶媒と併用して用いることもできる。
該複合体をナノサイズ一次元構造物化する場合の攪拌又は静置時の温度は、5~300℃の範囲が好ましく、さらに好ましくは20~250℃である。温度が5℃以上であれば、十分にフタロシアニン類の結晶成長を誘発することができ、目的とする一次元結晶成長により、一次元構造物への成長が可能であり、又、250℃以下であれば生成した一次元構造物の凝集、融着がほとんど見られず、又、短径(幅)方向に結晶成長して粗大(等方性構造物)化することもない。
本発明のインキ組成物は、本発明のフタロシアニンナノサイズ構造物と有機溶媒とを必須成分として含有する。これらのインキ組成物は、ウエットプロセス(印刷又は塗布)により電子素子の活性部(半導体層)を形成する前駆体材料として好適なものである。
本発明のインキ組成物は、前記フタロシアニンナノサイズ一次元構造物を、有機溶媒に分散させることにより製造される。又は、前記工程(c)で得られたフタロシアニンナノサイズ一次元構造物の分散液を本発明のインキ組成物として用いることもできる。
アミド系溶媒として、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチルピロリドン、
芳香族系有機溶媒として、トルエン、キシレン、エチルベンゼン、
ハロゲン系有機溶媒として、クロロベンゼン、ジクロロベンゼン、クロロホルム、塩化メチレン、ジクロロエタン、
グリコールエステル系溶媒として、エチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、
グリコールエーテル系溶媒として、エチレングリコールメチルエーテル、エチレングリコールエチルエーテル、エチレングリコールブチルエーテル、ジエチレングリコールエチルエーテル、ジエチレングリコールブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールターシャリーブチルエーテル、ジプロピレングリコールモノメチルエーテルを最も好適な分散用有機溶媒として挙げることができる。
次に、本発明の電子素子について説明する。本発明の電子素子は、本発明のフタロシアニンナノサイズ一次元構造物を、活性層部(半導体層)に含有する電子素子である。電子素子の具体例として、太陽電池や受光素子などの光電変換素子、電界効果型トランジスタや静電誘導型トランジスタやバイポーラトランジスタ等のトランジスタ、電界発光素子、温度センサー、ガスセンサー、湿度センサー、放射線センサーなどが挙げられるが、これらに限定されるものではない。
次に、本発明の光電変換素子について説明する。本発明の光電変換素子は、少なくとも一対の電極、すなわち正極と負極を有し、これら電極間に本発明のフタロシアニンナノサイズ構造物を含む。図1は本発明の光電変換素子の一例を示す模式図である。図1において符号1は基板、符号2は電極a、符号3は本発明のフタロシアニンナノサイズ構造物を含む光電変換層(有機半導体層)、符号4は電極bである。
これらバッファー層は、単層であってもよく、又、異なる材料を積層したものであってもよい。
又、隣接する本発明による光電変換素子の電極a同士を接触させ、且つ、隣接する本発明による光電変換素子の電極b同士を接触させることにより、本発明による光電変換素子を並列接続させて集積化させたことを特徴とする太陽電池モジュールであってもよい。
次に、本発明のトランジスタについて説明する。本発明のトランジスタは、活性部(トランジスタではチャネル部(半導体層)言う)に本発明のフタロシアニンナノサイズ構造物を含有するトランジスタである。
このようなトランジスタとしては、基板上に本発明によるフタロシアニンナノサイズ構造物を含む膜とこれに連結するソース電極とドレイン電極を形成し、その上にゲート絶縁膜を介してゲート電極を形成したトップゲート型を挙げることができる。
銅フタロシアニンスルホン酸(DIC(株)製EXT-795 平均スルホン化度=0.95)50質量部とDMF1,000質量部の混合溶液を5℃に冷却後、塩化チオニル50質量部を滴下し、室温で1時間、70℃で5時間反応した。反応液を氷水5,000質量部に注ぎ、得られた沈殿物を回収、乾燥して銅フタロシアニンスルホン酸と銅フタロシアニンスルホニルクロリドの混合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにn-プロピルモノアミン(東京化成(株)製)17.5質量部を使用した以外は合成例1と同様の操作を行い、下記[化12]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにヘキシルモノアミン(東京化成(株)製)30質量部を使用した以外は合成例1と同様の操作を行い、下記[化13]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにドデシルモノアミン(東京化成(株)製)55質量部を使用した以外は合成例1と同様の操作を行い、下記[化14]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにステアリルモノアミン(東京化成(株)製)80質量部を使用した以外は合成例1と同様の操作を行い、下記[化15]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにシクロヘキシルモノアミン(東京化成(株)製)29.4質量部を使用した以外は合成例1と同様の操作を行い、下記[化16]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりにフェニルモノアミン(東京化成(株)製)27.6質量部を使用した以外は合成例1と同様の操作を行い、下記[化17]で表される化合物を得た。
合成例1において、メチルモノアミン40%水溶液23質量部の替わりに3-チエニルモノアミン29.4質量部を使用した以外は合成例1と同様の操作を行い、下記[化18]で表される化合物を得た。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
無置換フタロシアニンとして銅フタロシアニン(Fastogen Blue 5380E(商品名、DIC製))1.6gと、置換基を有するフタロシアニンとして合成例1で得られた[化11]で表されるフタロシアニン誘導体1.2gを濃硫酸(関東化学製)81gに投入して完全に溶解させ、濃硫酸溶液を調製した。続いて、蒸留水730gを1000mLのビーカーに投入し、これを氷水で十分冷却した後、該蒸留水を撹拌しながら、先に調製した濃硫酸溶液を投入し、無置換銅フタロシアニンと[化11]で表される銅フタロシアニン誘導体とからなる複合体を析出させた。
続いて得られた該複合体を、濾紙を用いてろ過し、蒸留水を用いて十分に洗浄し、その後、真空乾燥気で脱水処理をした。
n型のシリコン基板を用意してこれをゲート電極とし、この表面層を熱酸化処理して酸化シリコンからなるゲート絶縁膜を形成した。ここに、前記フタロシアニンナノサイズ構造物分散液(1)をスピンコートし、フタロシアニンナノサイズ構造物よりなる半導体膜(チャネル部)を形成した。次に、蒸着成膜によって、金薄膜からなるソース・ドレイン電極をパターン形成し、トランジスタ(1)を製造した。なお、チャネル長L(ソース電極-ドレイン電極間隔)を75μm、チャネル幅Wを5.0mmとした。
前記フタロシアニンナノサイズ構造物分散液(1)150mgとPCBM(フロンティアカーボン製)45mgとオルトジクロロベンゼン200mgをサンプル瓶の中に投入し、超音波洗浄機(47kHz)中で30分間超音波照射することにより光電変換素子用材料(1)を得た。
(ここで、JVmaxは、印加電圧が0Vから開放端電圧値の間で電流密度と印加電圧の積が最大となる点における電流密度と印加電圧の積の値である。)
PCE=[(Jsc×Voc×FF)/擬似太陽光強度(100mW/cm2)]×100(%)
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(2)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(2)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(2)を用いる以外は実施例(1)としてトランジスタ(2)を得た。特性の評価結果を表1にまとめた。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(3)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(3)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(3)を用いる以外は実施例(1)としてトランジスタ(3)を得た。特性の評価結果を表1にまとめた。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(4)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(4)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(4)を用いる以外は実施例(1)としてトランジスタ(4)を得た。特性の評価結果を表1にまとめた。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(5)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(5)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(5)を用いる以外は実施例(1)としてトランジスタ(5)を得た。特性の評価結果を表1にまとめた。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(6)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(6)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(6)を用いる以外は実施例(1)としてトランジスタ(6)を得た。特性の評価結果を表1にまとめた。
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(7)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(7)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(7)を用いる以外は実施例(1)としてトランジスタ(7)を得た。特性の評価結果を表1にまとめた
<フタロシアニンナノサイズ構造物とフタロシアニンナノサイズ構造物分散液の製造>
置換基を有するフタロシアニンとして合成例(8)で得たスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(8)を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(8)を用いる以外は実施例(1)としてトランジスタ(8)を得た。特性の評価結果を表1にまとめた。
WO2010/122921号公報に記載の方法で[化19]のスルファモイル基置換フタロシアニンを合成した。
置換基を有するフタロシアニンとして[化19]で表せられるスルファモイル基置換フタロシアニンを用いる以外は実施例(1)と同様にして、フタロシアニンナノサイズ構造物分散液(1)’を得た。
<トランジスタの製造とトランジスタ特性(移動度)の評価>
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(1)’を用いる以外は実施例(1)としてトランジスタ(1)’を得た。特性の評価結果を表1にまとめた。
フタロシアニンナノサイズ構造物分散液に前記フタロシアニンナノサイズ構造物分散液(2)’を用いる以外は実施例(1)としてトランジスタ(2)’を得た。特性の評価結果を表1にまとめた。
2 電極a
3 光電変換層
4 電極b
5 本発明のフタロシアニンナノサイズ構造物を含有する層(電極aが正極の場合)、又は電子受容性材料を含有する層(電極aが負極の場合)
6 電子受容性材料を含有する層(電極bが負極の場合)、又は本発明のフタロシアニンナノサイズ構造物を含有する層(電極bが正極の場合)
7 基板
8 ゲート電極
9 ゲート絶縁膜
10 ソース電極
11 ドレイン電極
12 本発明のフタロシアニンナノサイズ構造物を含有する半導体層
Claims (9)
- 無置換フタロシアニン及び置換基を有するフタロシアニンを含有するナノサイズ構造物であって、
構造物の形状が、長径と短径を有し、その短径が500nm以下であり、
無置換フタロシアニンが、一般式(1)又は(2)で表されるものであり、
(但し、式中、Xは、銅原子、亜鉛原子、コバルト原子、ニッケル原子、錫原子、鉛原子、マグネシウム原子、鉄原子、パラジウム原子、カルシウム原子、GeO、TiO、VO及びAlClからなる群から選ばれる何れかである。)
置換基を有するフタロシアニンが、一般式(3)又は(4)で表されるものであるフタロシアニンナノサイズ構造物。
フタロシアニン骨格のベンゼン環にある各水素原子はフッ素、塩素、臭素で置換されていても良く、Z1~Z8は、それぞれ独立に、水素原子、置換基を有してもよい炭素数1~30の非環状炭化水素基、置換基を有してもよい炭素数1~30の環状炭化水素基、置換基を有してもよいへテロアリール基であり、a、b、c、及びdは各々独立に0~4の整数を表すが少なくとも1つは0ではなく、Z1~Z8が一般式(5)、又は(6)である場合、及び共に水素原子である場合を除く。
- 炭素数1~22の非環状若しくは環状アルキル基が、メチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、1-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、n-ノニル基、n-デシル基、n-ウンデシル基、n-ドデシル基、n-トリデシル基、n-テトラデシル基、n-ペンタデシル基、n-ヘキサデシル基、n-ヘプタデシル基、n-オクタデシル基、n-ノナデシル基、n-ドコシル基、シクロヘキシル基である請求項2に記載のナノサイズ構造物。
- 請求項1~3の何れかに記載のフタロシアニンナノサイズ構造物と有機溶媒とを必須成分とするインキ組成物。
- 請求項1~3の何れかに記載のフタロシアニンナノサイズ構造物を含有する電子素子。
- 請求項1~3の何れかに記載のフタロシアニンナノサイズ構造物をチャネル部に含有するトランジスタ。
- 請求項6に記載のトランジスタの製造方法において、
請求項4に記載のインキ組成物を製膜することによりチャネル部を作製することを特徴とするトランジスタの製造方法。 - 少なくとも正極と負極を有する光電変換素子であって、
正極と負極の間に請求項1~3の何れかに記載のフタロシアニンナノサイズ構造物を含む膜を有することを特徴とする光電変換素子。 - 請求項8に記載の光電変換素子の製造方法において、
正極と負極の間に請求項4に記載のインキ組成物を製膜する工程を有することを特徴とする光電変換素子の製造方法。
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Also Published As
Publication number | Publication date |
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EP2837633A1 (en) | 2015-02-18 |
KR20140105540A (ko) | 2014-09-01 |
TW201400554A (zh) | 2014-01-01 |
US9324956B2 (en) | 2016-04-26 |
CN104169285B (zh) | 2016-10-26 |
US20150090975A1 (en) | 2015-04-02 |
EP2837633A4 (en) | 2016-01-06 |
TWI487751B (zh) | 2015-06-11 |
KR101715205B1 (ko) | 2017-03-10 |
CN104169285A (zh) | 2014-11-26 |
JP5338939B2 (ja) | 2013-11-13 |
JP2013216603A (ja) | 2013-10-24 |
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