JP7061804B2 - 含フッ素多環芳香族化合物とその製造方法、並びに前記含フッ素芳香族化合物を用いる有機薄膜トランジスタ及び太陽電池の製造方法 - Google Patents
含フッ素多環芳香族化合物とその製造方法、並びに前記含フッ素芳香族化合物を用いる有機薄膜トランジスタ及び太陽電池の製造方法 Download PDFInfo
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- JP7061804B2 JP7061804B2 JP2019169266A JP2019169266A JP7061804B2 JP 7061804 B2 JP7061804 B2 JP 7061804B2 JP 2019169266 A JP2019169266 A JP 2019169266A JP 2019169266 A JP2019169266 A JP 2019169266A JP 7061804 B2 JP7061804 B2 JP 7061804B2
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- 229910052731 fluorine Inorganic materials 0.000 title claims description 314
- 239000011737 fluorine Substances 0.000 title claims description 259
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 255
- -1 polycyclic aromatic compound Chemical class 0.000 title claims description 237
- 238000004519 manufacturing process Methods 0.000 title claims description 63
- 239000010409 thin film Substances 0.000 title claims description 41
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 5
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- 239000000463 material Substances 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000001153 fluoro group Chemical group F* 0.000 claims description 70
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 49
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- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 239000004065 semiconductor Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 18
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- 230000002194 synthesizing effect Effects 0.000 claims description 14
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- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- LSOTZYUVGZKSHR-UHFFFAOYSA-N anthracene-1,4-dione Chemical compound C1=CC=C2C=C3C(=O)C=CC(=O)C3=CC2=C1 LSOTZYUVGZKSHR-UHFFFAOYSA-N 0.000 claims description 5
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- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 13
- 239000004342 Benzoyl peroxide Substances 0.000 description 12
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 10
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- KNBYJRSSFXTESR-UHFFFAOYSA-N naphthalene-2,3-dicarbonitrile Chemical class C1=CC=C2C=C(C#N)C(C#N)=CC2=C1 KNBYJRSSFXTESR-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
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- 238000004440 column chromatography Methods 0.000 description 7
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 7
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- DUYSWCGNUMDWND-UHFFFAOYSA-N 1,2-bis(dibromomethyl)-4,5-bis(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)benzene Chemical compound FC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(C1=CC(=C(C=C1C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C(Br)Br)C(Br)Br)F DUYSWCGNUMDWND-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 6
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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- OAGUJYLHEIMULO-UHFFFAOYSA-N 1,2-dimethyl-4,5-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)benzene Chemical group CC1=C(C=C(C(=C1)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)C OAGUJYLHEIMULO-UHFFFAOYSA-N 0.000 description 4
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
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- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- DEIVNMVWRDMSMJ-UHFFFAOYSA-N hydrogen peroxide;oxotitanium Chemical compound OO.[Ti]=O DEIVNMVWRDMSMJ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000007347 radical substitution reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001552 radio frequency sputter deposition Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thin Film Transistor (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
下記(3)式で表される含フッ素多環芳香族化合物を提供する。
[2]本発明は、前記[1]に記載の含フッ素多環芳香族化合物において、前記Y1、Y2、Z1、Z2が、どれも水素原子であり、前記R1、R2、R3が、それぞれ独立に炭素数1~10のいずれかを有するアルキル基であることを特徴とする含フッ素多環芳香族化合物を提供する。
[3]本発明は、下記(6)式又は(7)式で表される化合物を用いて、臭素(Br)又はヨウ素(I)が核置換された位置にX1及びX2の置換基を導入することにより下記(8)式で表される化合物を合成する工程、及び下記(8)式で表される化合物のW1及びW2の置換基において単環芳香環と化学結合する炭素に結合する2つの水素原子を臭素化する工程、を有する合成方法によって下記(5)式で表される含フッ素単環芳香族化合物を製造し、
前記含フッ素単環芳香族化合物とパラ-ベンゾキノン又はアントラセン-1,4-ジオンとのディールス・アルダー環化付加反応によって酸素原子が含まれる含フッ素多環芳香族化合物を合成する工程、及び前記酸素原子が含まれる含フッ素多環芳香族化合物をシリルエチニル化した後、還元することによって下記(3)式で表される含フッ素シリルエチニルペンタセン化合物を製造することを特徴とする含含フッ素多環芳香族化合物の製造方法を提供する。
[4]本発明は、前記含フッ素単環芳香族化合物が、前記(6)式で表される化合物を用いて、臭素(Br)が核置換された位置に前記X1及びX2の置換基を導入することにより前記(8)式で表される化合物を合成する工程、及び前記(8)式で表される化合物のW1及びW2の置換基において単環芳香環と化学結合する炭素に結合する2つの水素原子を臭素化する工程、を有する合成方法によって製造されることを特徴する前記[3]に記載の含フッ素多環芳香族化合物の製造方法を提供する。
[5]本発明は、前記含フッ素単環芳香族化合物とアントラセン-1,4-ジオンとのディールス・アルダー環化付加反応によって、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記X3及びX4がどちらも水素原子である化合物を製造することを特徴とする前記[3]又は[4]に記載の含フッ素多環芳香族化合物の製造方法を提供する。
[6]本発明は、前記複数個の臭素を有する含フッ素単環芳香族化合物とパラ-ベンゾキノンとのディールス・アルダー環化付加反応によって、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記X3及びX4がどちらも-CF 3 、-C 4 F 9 、-C 6 F 13 、-C 8 F 17 、及び-C 10 F 21 のいずれかのパーフルオロアルキル基である化合物を製造することを特徴とする前記[3]又は[4]に記載の含フッ素多環芳香族化合物の製造方法を提供する。
[7]本発明は、前記シリルエチニル化を、前記R1、R2、R3として炭素数1~10のアルキル基のいずれかをそれぞれ独立に有するシリルアセチレン化合物を用いて行うことにより、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記R1、R2、R3が炭素数1~10のアルキル基のいずれかをそれぞれ独立に有する化合物を製造することを特徴とする前記[3]又は[6]のいずれか一項に記載の含フッ素多環芳香族化合物の製造方法を提供する。
[8]本発明は、前記(5)式で表される含フッ素単環芳香族化合物において、前記Y1、Y2、Z1、Z2が、いずれも水素原子であることを特徴とする前記[7]に記載の含フッ素多環芳香族化合物の製造方法を提供する。
[9]本発明は、前記[1]又は[2]に記載の含フッ素多環芳香族化合物を、有機半導体材料として用いることを特徴とする有機薄膜トランジスタの製造方法を提供する。
[10]本発明は、前記[1]又は[2]に記載の含フッ素多環芳香族化合物を、電子輸送層、陰極側バッファ層、又は中間電極に接するバッファ層に含まれる電子移動材料として用いることを特徴とする太陽電池の製造方法を提供する。
[発明の効果]
本発明による含フッ素多環芳香族化合物の製造方法を、次に説明する。
含フッ素ナフタロシアニン化合物は、上記(5)式で表される含フッ素単環芳香族化合物とフマロニトリル又はマレオニトリルとを用いて、基本的に下記の合成スキーム1に従って製造される。下記の合成スキーム1は、上記(1)式で表される含フッ素ナフタロシアニン化合物の中で、Mが2個の水素原子であって、環化四量化反応によって合成される含フッ素のテトラフェニルナフタロシアニン化合物、又は上記(2)式で表される含フッ素ナフタロシアニン化合物の中で、Mが金属又はホウ素(B)であって、環化三量化反応によって合成されるトリフェニルナフタロシアニン化合物、のそれぞれの合成例である。
<スキーム1>
含フッ素シリルエチルペンタセン化合物は、上記(5)式で表される含フッ素単環芳香族化合物とパラ-ベンゾキノン又はアントラセン-1,4-ジオンとを用いて、基本的に下記の合成スキーム2に従って製造される。
<スキーム2>
含フッ素ペンタセン化合物は、上記(5)式で表される含フッ素単環芳香族化合物とパラーベンゾキノン(1,4-ベンゾキノン)とを用いて、基本的に下記の合成スキーム3に従って製造される。
<スキーム3>
次に、上記(5)式で示す含フッ素単環芳香族化合物について具体例を挙げて説明する。
上記(5)式で表される含フッ素単環芳香族化合物は、上記スキーム1~3の合成工程において基本の原料として使用されるが、本発明においては市販の別の原料から合成したものを使用してもよい。例えば、市販の原料として下記(6)式又は(7)式で表される単環状芳香族化合物を使用して下記の合成スキーム4によって合成することができる。下記(6)式又は(7)式で表される単環状芳香族化合物は、オルト位で2つの臭素(Br)又は2つのヨウ素(I)が核置換した化学構造を有する化合物である。
<スキーム4>
次に、上記(5)式で表される含フッ素単環芳香族化合物を用いて製造される含フッ素多環芳香族化合物の代表例を下記に示すが、本発明はこれらの化合物に限定されるものではない。
本発明によって製造される上記の(1)式、(2)式、(3)式、及び(4)式で表される含フッ素多環芳香族化合物は、有機薄膜トランジスタを構成する有機半導体層に含まれる有機半導体材料として使用することができる。そこで、本発明による有機薄膜トランジスタの製造方法について説明する。
本発明によって製造される上記(1)式及び(2)式で表される含フッ素ナフタロシアニン化合物、及び記(3)式及び(4)式で表される含ペンタセン化合物は、太陽電池を構成する層に使用する材料として適用することができる。そこで、本発明による太陽電池の製造方法について説明する。
(1-1)下部電極/活性層(p層)/活性層(n層)/上部電極
(1-2)下部電極/バッファ層/活性層(p層)/活性層(n層)/上部電極
(1-3)下部電極/活性層(p層)/活性層(n層)/バッファ層/上部電極
(1-4)下部電極/バッファ層/活性層(p層)/活性層(n層)/バッファ層/上部電極
(1-5)下部電極/バッファ層/活性層(p層)/活性層(i層又はp材料とn材料の混合槽)/活性層(n層)/バッファ層/上部電極
(1-6)下部電極/活性層(p層)/活性層(n層)/バッファ層/中間電極/バッファ層/活性層(p層)/活性層(n層)/バッファ層/上部電極
(1-7)下部電極/バッファ層/活性層(p層)/活性層(n層)/バッファ層/中間電極/バッファ層/活性層(p層)/活性層(n層)/バッファ層/上部電極
(1-8)下部電極/バッファ層/活性層(p層)/活性層(i層、p材料とn材料の混合槽)/活性層(n層)/バッファ層/中間電極/バッファ層/活性層(p層)/活性層(i層又はp材料とn材料の混合槽)/活性層(n層)/バッファ層/上部電極
上記(1)式又は(2)式で表される含フッ素ナフタロシアニン化合物は、電子写真感光体の電荷発生層に含まれる電荷発生材料として使用することができる。そこで、本発明による電子写真感光体の製造方法を以下に説明する。
また、上記の(1)式又は(2)式で表される含フッ素ナフタロシアニン化合物は、有機発光素子の発光層に含まれる発光材料として適用することができる。そこで、本発明による有機発光素子の製造方法を以下に説明する。
(2-1)陽極/正孔輸送層/発光層/陰極
(2-2)陽極/発光層/電子輸送層/陰極
(2-3)陽極/正孔輸送層/発光層/電子輸送層/陰極
(2-4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(2-5)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(2-6)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
4,5-ビス(パーフルオロヘキシル)-o-キシレンの合成
19F NMR (376 MHz, CDCl3): δ = -81.02 (t, J = 9.68, 6F), -103.31 (s, 4F), -118.34 (s, 4F), -122.12 (s, 4F), 122.91 (s, 4F), 126.23 (s, 4F).
4 ,5-ビス(パーフルオロヘキシル)-1,2-ビス(ジブロモメチル)ベンゼンの合成
1H NMR (400 MHz, CDCl3): δ= 8.08 (s, 2H), 7.10 (s, 2H).
19F NMR (376 MHz, CDCl3): δ= -81.02 (t, J = 9.51, 6F), -103.93 (s, 4F), -118.11 (s, 4F), -122.03 (s, 4F), -122.87 (s, 4F), -126.28 (s, 4F).
1H NMR (400 MHz, CDCl3): δ= 8.31 (s, 1H), 7.70 (s, 1H), 7.03 (s, 1H), 4.60 (s, 2H)
19F NMR (376 MHz, CDCl3): δ= -81.02 (t, J = 9.51, 6F), -103.93 (s, 4F), -118.11 (s, 4F), -122.03 (s, 4F), -122.87 (s, 4F), -126.28 (s, 4F).
2,3,9,10-テトラキス(パーフルオロヘキシル)ペンタセン-6,13-ジオンの合成
19F NMR (376 MHz, CDCl3): δ= -80.78 (t, J = 9.16, 6F), -103.17 (s, 4F), -118.12 (s, 4F), -121.93 (s, 4F), -122.70 (s, 4F), -126.08 (s, 4F).
6,13-ビス(トリイソプロピルシリルエチニル)-2,3,9,10-テトラキス(パ―フルオロヘキシル)ペンタセンの合成
19F NMR (376 MHz, CDCl3): δ= -80.74 (t, J = 9.51, 6F), -103.14 (s, 4F), -118.09 (s, 4F), -121.89 (s, 4F), -122.62 (s, 4F), -126.03 (s, 4F).
6,7-ビス(トリデカフルオロヘキシル)-2,3-ジシアノナフタレンの合成
ヘキサキス(パーフルオロアルキル)ナフタロシアニンの合成
UV-vis: λmax = 762 nm (ε 9.5×103)
4 ,5-ビス(パーフルオロブチル)-o-キシレンの合成
19F NMR (376 MHz, CDCl3): δ -81.06 (t, J = 9.7 Hz, 6F), -103.36 (s, 4F), -119.20 (s, 4F), -126.16 (s, 4F).
4 ,5-ビス(パーフルオロブチル)-1,2-ビス(ジブロモメチル)ベンゼンの合成
1H NMR (400 MHz, CDCl3): δ 8.09 (s, 2H), 7.07 (s, 2H).
19F NMR (376 MHz, CDCl3): δ -80.91 (t, J = 9.9 Hz, 6F), -103.94 (s, 4F), -118.90 (s, 4F), -125.99 (s, 4F).
1H NMR (400 MHz, CDCl3): δ 8.31 (s, 1H), 7.70 (s, 1H), 7.03 (s, 1H), 4.60 (s, 2H)
19F NMR (376 MHz, CDCl3): δ -80.91 (t, J = 9.9 Hz, 6F), -103.94 (s, 4F), -118.90 (s, 4F), -125.99 (s, 4F).
6,7-ビス (パーフルオロブチル) -2,3-ジシアノナフタレンの合成
19F NMR (376 MHz, CDCl3): δ -80.91 (t, J = 9.9 Hz, 6F), -103.94 (s, 4F), -118.90 (s, 4F), -125.99 (s, 4F).
パーフルオロアルキル基(C4F9)を有するサブナフタロシアニンの合成
19F NMR (376 MHz, CDCl3): δ -80.91 (t, J = 9.9 Hz, 18F), -103.94 (s, 12F), -118.90 (s, 12F), -125.99 (s, 12F).
2,3-ビス (パーフルオロヘキシル) ペンタセン-6,13-ジオン
19F NMR (376 MHz, CDCl3): δ -80.72 (t, J = 10.2 Hz, 6F), -102.91 (s, 4F), -117.77 (s, 4F), -121.86 (s, 4F), -122.66 (s, 4F), -126.03 (s, 4F).
13C NMR and HRMS could not be recorded due to poor solubility.
6,13-ビス [ (トリイソプロピルシリル) エチニル] -2,3-ビス (パーフルオロヘキシル) ペンタセン
19F NMR (376 MHz, CDCl3): δ -80.74 (t, J = 10.2 Hz, 6F), -103.05 (s, 4F), -118.14 (s, 4F), -121.93 (s, 4F), -122.64 (s, 4F), -126.05 (s, 4F).
13C{1H} NMR (100 MHz, CDCl3): 134.2, 133.0, 131.6, 129.4, 129.3, 128.7, 126.8, 126.7, 119.6, 109.1, 103.8, 18.9, 11.6.
13C NMR signals corresponding to the C6F13 groups could not be observed.
HRMS (MALDI+) m/z calcd for C56H52F26Si2 1274.3192, found: 1274.3173 ([M]+).
Claims (10)
- 3環以上の共役系多環芳香族基を有し、前記共役系多環芳香族基の両末端に位置する芳香族基の少なくとも一つがパーフルオロアルキル基で核置換された含フッ素多環芳香族化合物であって、
下記(3)式で表される含フッ素多環芳香族化合物。
- 請求項1に記載の含フッ素多環芳香族化合物において、前記Y1、Y2、Z1、Z2が、どれも水素原子であり、前記R1、R2、R3が、それぞれ独立に炭素数1~10のいずれかを有するアルキル基であることを特徴とする含フッ素多環芳香族化合物。
- 下記(6)式又は(7)式で表される化合物を用いて、臭素(Br)又はヨウ素(I)が核置換された位置にX1及びX2の置換基を導入することにより下記(8)式で表される化合物を合成する工程、及び下記(8)式で表される化合物のW1及びW2の置換基において単環芳香環と化学結合する炭素に結合する2つの水素原子を臭素化する工程、を有する合成方法によって下記(5)式で表される含フッ素単環芳香族化合物を製造し、
前記含フッ素単環芳香族化合物とパラ-ベンゾキノン又はアントラセン-1,4-ジオンとのディールス・アルダー環化付加反応によって酸素原子が含まれる含フッ素多環芳香族化合物を合成する工程、及び前記酸素原子が含まれる含フッ素多環芳香族化合物をシリルエチニル化した後、還元することによって下記(3)式で表される含フッ素シリルエチニルペンタセン化合物を製造することを特徴とする含フッ素多環芳香族化合物の製造方法。
- 前記含フッ素単環芳香族化合物が、前記(6)式で表される化合物を用いて、臭素(Br)が核置換された位置に前記X1及びX2の置換基を導入することにより前記(8)式で表される化合物を合成する工程、及び前記(8)式で表される化合物のW1及びW2の置換基において単環芳香環と化学結合する炭素に結合する2つの水素原子を臭素化する工程、を有する合成方法によって製造されることを特徴する請求項3に記載の含フッ素多環芳香族化合物の製造方法。
- 前記含フッ素単環芳香族化合物とアントラセン-1,4-ジオンとのディールス・アルダー環化付加反応によって、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記X3及びX4がどちらも水素原子である化合物を製造することを特徴とする請求項3又は4に記載の含フッ素多環芳香族化合物の製造方法。
- 前記複数個の臭素を有する含フッ素単環芳香族化合物とパラ-ベンゾキノンとのディールス・アルダー環化付加反応によって、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記X3及びX4がどちらも-CF 3 、-C 4 F 9 、-C 6 F 13 、-C 8 F 17 、及び-C 10 F 21 のいずれかのパーフルオロアルキル基である化合物を製造することを特徴とする請求項3又は4に記載の含フッ素多環芳香族化合物の製造方法。
- 前記シリルエチニル化を、前記R1、R2、R3として炭素数1~10のアルキル基のいずれかをそれぞれ独立に有するシリルアセチレン化合物を用いて行うことにより、前記(3)式で表される含フッ素シリルエチニルペンタセン化合物において、前記R1、R2、R3が炭素数1~10のアルキル基のいずれかをそれぞれ独立に有する化合物を製造することを特徴とする請求項3~6のいずれか一項に記載の含フッ素多環芳香族化合物の製造方法。
- 前記(5)式で表される含フッ素単環芳香族化合物において、前記Y1、Y2、Z1、Z2が、いずれも水素原子であることを特徴とする請求項7に記載の含フッ素多環芳香族化合物の製造方法。
- 請求項1又は2に記載の含フッ素多環芳香族化合物を、有機半導体材料として用いることを特徴とする有機薄膜トランジスタの製造方法。
- 請求項1又は2に記載の含フッ素多環芳香族化合物を、電子輸送層、陰極側バッファ層、又は中間電極に接するバッファ層に含まれる電子移動材料として用いることを特徴とする太陽電池の製造方法。
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