TWI423945B - 軸烯化合物及其使用 - Google Patents
軸烯化合物及其使用 Download PDFInfo
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- TWI423945B TWI423945B TW098134521A TW98134521A TWI423945B TW I423945 B TWI423945 B TW I423945B TW 098134521 A TW098134521 A TW 098134521A TW 98134521 A TW98134521 A TW 98134521A TW I423945 B TWI423945 B TW I423945B
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- Taiwan
- Prior art keywords
- phenyl
- group
- organic
- compound
- dopant
- Prior art date
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- PXLYGWXKAVCTPX-UHFFFAOYSA-N 1,2,3,4,5,6-hexamethylidenecyclohexane Chemical class C=C1C(=C)C(=C)C(=C)C(=C)C1=C PXLYGWXKAVCTPX-UHFFFAOYSA-N 0.000 title 1
- 239000002019 doping agent Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000463 material Substances 0.000 claims description 44
- -1 monoolefin compound Chemical class 0.000 claims description 41
- 239000007983 Tris buffer Substances 0.000 claims description 25
- 239000011159 matrix material Substances 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 23
- 239000004065 semiconductor Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- UUZLADCDKJUECN-UHFFFAOYSA-N 4-(cyanomethyl)-2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1CC#N UUZLADCDKJUECN-UHFFFAOYSA-N 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- YMMPLJAAWKZWBD-UHFFFAOYSA-N 2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1CC#N YMMPLJAAWKZWBD-UHFFFAOYSA-N 0.000 claims description 5
- UTRVZPGFBIRJKU-UHFFFAOYSA-N 2-[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC1=C(Cl)C(CC#N)=C(Cl)C(F)=C1C(F)(F)F UTRVZPGFBIRJKU-UHFFFAOYSA-N 0.000 claims description 5
- 239000004020 conductor Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 3
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 claims description 2
- FCSYGWPGJCGOAV-UHFFFAOYSA-N 4-(2-phenylphenyl)-n,n-bis[4-(2-phenylphenyl)phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1 FCSYGWPGJCGOAV-UHFFFAOYSA-N 0.000 claims description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].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 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930004069 diterpene Natural products 0.000 claims description 2
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910000906 Bronze Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000010974 bronze Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
- 230000005294 ferromagnetic effect Effects 0.000 claims 1
- 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 claims 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 24
- 239000007858 starting material Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- LSHNAQFMHASWOC-UHFFFAOYSA-N 1,1,2,2-tetrachlorocyclopropane Chemical compound ClC1(Cl)CC1(Cl)Cl LSHNAQFMHASWOC-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 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 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CFURZOACFPKEOF-UHFFFAOYSA-N 2-(2,3,5,6-tetrafluoropyridin-4-yl)acetonitrile Chemical compound FC1=NC(F)=C(F)C(CC#N)=C1F CFURZOACFPKEOF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- YDNOJUAQBFXZCR-UHFFFAOYSA-N 2-(2,3,4,5,6-pentafluorophenyl)acetonitrile Chemical compound FC1=C(F)C(F)=C(CC#N)C(F)=C1F YDNOJUAQBFXZCR-UHFFFAOYSA-N 0.000 description 3
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 3
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BLZOHTXDDOAASQ-UHFFFAOYSA-N 1,2,3,3-tetrachlorocyclopropene Chemical compound ClC1=C(Cl)C1(Cl)Cl BLZOHTXDDOAASQ-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- XTGOWLIKIQLYRG-UHFFFAOYSA-N 2,3,4,5,6-pentafluoropyridine Chemical compound FC1=NC(F)=C(F)C(F)=C1F XTGOWLIKIQLYRG-UHFFFAOYSA-N 0.000 description 2
- LJVCZZGRMOTMIB-UHFFFAOYSA-N 2-cyano-2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]butanoic acid Chemical compound CCC(C#N)(C(O)=O)C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F LJVCZZGRMOTMIB-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical compound [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- KLZHUQDVWUXWEZ-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.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 KLZHUQDVWUXWEZ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- UPUDVKWQBVIKBG-UHFFFAOYSA-N 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxyisoquinolin-2-ium;chloride Chemical compound [Cl-].C1=C(OCC)C(OCC)=CC=C1CC1=[NH+]C=CC2=CC(OCC)=C(OCC)C=C12 UPUDVKWQBVIKBG-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- CQAYPONNLVVJEF-UHFFFAOYSA-N 2-cyano-2-(2,3,4,5,6-pentafluorophenyl)butanoic acid Chemical compound CCC(C#N)(C(O)=O)C1=C(F)C(F)=C(F)C(F)=C1F CQAYPONNLVVJEF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NXVNUSIHWZLMGF-UHFFFAOYSA-N 4-phenyl-N-(4-phenylphenyl)-N-[4-[9-[4-(4-phenyl-N-(4-phenylphenyl)anilino)phenyl]fluoren-9-yl]phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 NXVNUSIHWZLMGF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DRFFLHJFCPYGMM-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C=2C3=CC=CC=C3C=3C=CC=CC3C2)C2=CC=CC=C2)C=C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1.C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C=2C3=CC=CC=C3C=3C=CC=CC3C2)C2=CC=CC=C2)C=C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1 Chemical compound C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C=2C3=CC=CC=C3C=3C=CC=CC3C2)C2=CC=CC=C2)C=C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1.C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C=2C3=CC=CC=C3C=3C=CC=CC3C2)C2=CC=CC=C2)C=C1)C=1C2=CC=CC=C2C=2C=CC=CC2C1 DRFFLHJFCPYGMM-UHFFFAOYSA-N 0.000 description 1
- ZBODOQNBZHWZCV-UHFFFAOYSA-N COC1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1)C1=CC=C(C=C1)OC Chemical compound COC1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=C(N(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1)C1=CC=C(C=C1)OC ZBODOQNBZHWZCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- AWSPUMRSVYVNSI-UHFFFAOYSA-N N-[4-[3,5-bis[4-[bis(9,9-dimethylfluoren-2-yl)amino]phenyl]phenyl]phenyl]-N-(9,9-dimethylfluoren-2-yl)-9,9-dimethylfluoren-2-amine Chemical compound C1=CC=C2C(C)(C)C3=CC(N(C=4C=CC(=CC=4)C=4C=C(C=C(C=4)C=4C=CC(=CC=4)N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=CC(=CC=4)N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 AWSPUMRSVYVNSI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JOMZCODXKBUPAT-UHFFFAOYSA-N ethyl 2-cyano-2-(2,3,4,5,6-pentafluorophenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=C(F)C(F)=C(F)C(F)=C1F JOMZCODXKBUPAT-UHFFFAOYSA-N 0.000 description 1
- VPXWUQZBTNIGKF-UHFFFAOYSA-N ethyl 2-cyano-2-(2,3,5,6-tetrafluoropyridin-4-yl)acetate Chemical compound CCOC(=O)C(C#N)C1=C(F)C(F)=NC(F)=C1F VPXWUQZBTNIGKF-UHFFFAOYSA-N 0.000 description 1
- OFETVCKKZRYPCM-UHFFFAOYSA-N ethyl 2-cyano-2-(4-cyano-2,3,5,6-tetrafluorophenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=C(F)C(F)=C(C#N)C(F)=C1F OFETVCKKZRYPCM-UHFFFAOYSA-N 0.000 description 1
- BEHZAAUZNUYAIK-UHFFFAOYSA-N ethyl 2-cyano-2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetate Chemical compound CCOC(=O)C(C#N)C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F BEHZAAUZNUYAIK-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- WOTCTOFEBNHWND-UHFFFAOYSA-M potassium;oxaldehydate Chemical compound [K+].[O-]C(=O)C=O WOTCTOFEBNHWND-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UMHSKYSHOIGDPE-UHFFFAOYSA-N pyridine;quinoline Chemical compound C1=CC=NC=C1.N1=CC=CC2=CC=CC=C21 UMHSKYSHOIGDPE-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/02—Semiconductor bodies ; Multistep manufacturing processes therefor
- H01L29/12—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by the materials of which they are formed
- H01L29/16—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by the materials of which they are formed including, apart from doping materials or other impurities, only elements of Group IV of the Periodic Table
- H01L29/167—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by the materials of which they are formed including, apart from doping materials or other impurities, only elements of Group IV of the Periodic Table further characterised by the doping material
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/26—Light sources with substantially two-dimensional radiating surfaces characterised by the composition or arrangement of the conductive material used as an electrode
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K50/15—Hole transporting layers
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Description
本發明是相關於軸烯化合物(radialene compounds)以及其使用,以作為用於摻雜一有機半導體基質材料(semiconductive matrix material)進而改變其電特性的有機摻雜劑,以作為阻擋材料(blocker material)以及電荷注入層(charge injection layer),以及作為電極材料,另外,本發明亦相關於有機半導體材料以及使用軸烯化合物的電子組件。
在現今的應用中,所有環中的原子皆為sp2雜交(sp2-hybrized)、且會儘可能攜帶環外C-C雙鍵的脂環(alicyclics),即被命名為軸烯(radialenes),請參閱H.Hopf and G.Maas,Angew.Chem.(1992),8,955,軸烯的結構基礎是氧碳(oxocarbon)以及偽氧碳(pseudooxocarbon)化合物,而氧碳以及偽氧碳化合物則是足以被視為非苯型芳香族(non-benzoid aromatics),請參閱,例如,G.Seitz,Nachr.Chem.Tech.Lab.28(1980),pages 804-807,其中,第一個氧碳化合物,克酮酸鉀(potassium croconate),是L.Gmelin在1825年利用碳酸甲以及煤所製成,並且,會有至少一氧原子子被另一個雜原所取代的該些化合物,則是被稱之為偽氧碳,正如此領域中具通常知識者所熟知的一樣。
多年來已知,利用摻雜的方式,可以對有機半導體的導電性產生重大的影響,而如此的有機半導體基質材料的建構則是可以由具有良好電子供體(electron donor)特性的化合物、或是由具有良好電子受體(electron acceptor)特性的化合物來達成,其中,強力的電子受體(例如,四氰基醌二甲烷(TCNQ,tetracyano-quinonedimethane),或是四氟化四氰基醌二甲烷(F4TCNQ,2,3,5,6-tetrafluoro-tetracyno-
benzoquinonedimethane))已經因為用於電子供體材料的摻雜(HT)而變成為大家所熟知(M.Pfeiffer,A.Beyer,T.Fritz,K.Leo,Appl.Phys.Lett.,73(22),3202-3204(1998),以及J.Blochwitz,M.Pfeiffer,T.Fritz,K.Leo,Appl.Phys.Lett.,73(6),729-731(1998)),並且,透過在類電子供體的基礎材料(base materials)(電洞傳輸材料)中的電子傳送程序,受體分子會產生所謂的電洞(holes),並且,取決於該等電洞的數量以及移動性,該基礎材料的傳導性會顯著地變得多、或更少,舉例而言,N,N’-過芳化聯苯胺(N,N’-perarylated benzidines)(例如,TPD)、或者N,N’,N”-過芳化星狀化合物(N,N’,N”-perarylated starburst compound)(例如,TDATA)、或者亦有某些金屬酞花青(phthalocyanines)(例如,特別地是,鋅酞花青(zinc phthalocyanine)ZnPc)亦已知為具有電洞傳輸特性的基質材料。
然而,先前所述的化合物的缺點是,當其用於生產已摻雜的半導體有機層、或生產具有如此已摻雜層的相對應電子組件時,會因為在大規模生產工廠中的製造程序、或是用於技術規模的該些製造程序總是無法有足夠的精確度,因此為了達成一所需生產量,常常會導致高控制與調整支出、或是導致生產所不需要的容受度(tolerances),再者,既然在掌控摻雜劑時所遇到的生產難題可能會在電子組件中造成不需要的不規則(irregularities)、或是在該等電子組件中造成不需要的老化效應,因此,當前述所熟知的有機受體被用於電子組件(例如,發光二極體(OLEDs),場效電晶體(FET),或太陽能電池)時,仍然有其不足之處,然而,由於,例如,該等摻雜劑在特定的情況下亦共同決定了傳導性、或該有機半導體層的其他電特性,因此,同時間仍應考慮的是,所使用的摻雜劑所具有的高度電子親合性(affinities)(還原電位(reduction potential))以及其他適合於應用情形的特性,此外,該基質材料的HOMO(highest occupied molecular orbital,最高電子佔有軌域)以及該摻雜劑的LUMO(lowest unoccupied molecular orbital,最低電子未佔用軌域)二者的能量位置對該摻雜效應亦具有決定力。
本發明的任務在於克服所陳述的習知技術的缺點,特別地
是,製造出新的有機內消旋化合物,其可被使用作為用於摻雜有機半導體的摻雜劑,可在生產程序中更容易受到掌控,並且,可得到所具有的有機半導體材料為可再製的電子組件,另外,尤其是,具有一深HOMO的電洞傳輸材料也可以藉由該等新的有機內消旋化合物而進行摻雜。
此任務可通過本申請案的獨立申請專利範圍而獲得解決,而較佳實施例則是敘述於附屬申請專利範圍之中。
在依據本發明的化合物之中,因為該LUMO的位置非常的低,因此,在工業上相當感興趣的電洞傳輸材料現在首次變得可以有效率地被摻雜,另外,由於該LUMO極低的位置以及與該化合物相關聯的高還原電位,因此,即使是太陽能電池的執行效率都可以獲得大幅的改善,並且,在未改變條件的狀況下,相較於習知處的摻質,一特定程度的摻雜效應(例如,一特性傳導性的一已摻雜層)則是可以利用一大體上較低量的待摻質材料而達成,此外,由於這些化合物的高極性,因此,其在有機層中有極端的擴散穩定性,再者,藉由將可獲得的軸烯作為摻雜劑,使得該有機半導體基質能夠有一足夠電傳導性,以在具低擴散係數的特殊組件中提供該等摻雜劑較具優勢的電子親合性,進而確保在時間上穩定的一組件結構,更進一步地,會接觸進入該已摻雜層的電荷載體注入可以利用該等摻雜劑而獲得改進,而且,該已摻雜有機半導體材料以及該結果電子組件也可以因為根據本發明中所使用的化合物而具有一獲改善的長時間穩定性,而此則是關係到,例如,傳導性隨著時間的降低、或損失,另外,此亦關係到相鄰於一電光組件的非已摻雜層的該已摻雜層的穩定性,因此,電光組件的電光特性可以具有增加的長時間穩定性,例如,光發射量子產率(quantum yield)、或一太陽能電池的效率、或類似的結果。
在申請專利範圍中所揭示的[3]-軸烯化合物已經被發現對執行本發明特別的有用,且這些化合物能夠摻雜所有常見的OLED電洞傳輸材料,尤其是,可以摻雜具有一深HOMO的電洞傳輸材料。
在申請專利範圍中所揭示的[3]-軸烯化合物是強力的電子受體,並且很容易形成自由基離子鹽(此時,該[3]-軸烯化合物可以攜帶,舉例而言,一、或二、多個負電荷)、或與電子供體化合物的電荷傳輸複合
物,而如此的自由基離子鹽、或電荷傳輸複合物則是會具有各種不同且有用的應用,例如,用於改變注入層,改變傳輸層,有機導體,鐵磁體,或是電化學、或光化學體。
藉由執行摻雜實驗可發現,在接下來的實例中所使用的該等化合物提供了良好的摻雜特性,並且,尤其重要的是,該些化合物所定義的取代模式提供了具有一介於0V vs Fc/Fc+以及0.4V vs.Fc/Fc+之間的還原電位的強力接收化合物,在此,如一般所認知,Fc/Fc+代表了二茂鐵(Ferrocene)/二茂鐵鹽(Ferrocenium)氧化還原對,而還原電位則是可以被視為對一分子的該LUMO的測量,再者,較好的取代模式所牽涉到的是,六元(雜)環完全被受體單元所取代,例如,氰基(cyano),氟(fluoro),氯(chloro),溴(bromo),以及類似者,正如在環丙烷(cyclopropane)化合物中的功能單元一樣,此外,該六元(雜)環則可以是,舉例而言,全氟吡啶-4-基(perfluoropyridin-4-yl),四氟-4-(三氟甲基)苯基(tetrafluoro-4-(trifluoromethyl)phenyl),4-氰全氟苯基(4-cyanoperfluorophenyl),二氯-3,5-二氟-4-(三氟甲基)苯基(dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl),以及全氟苯基(perfluorophenyl)。
通常,對p摻雜的OLED、或有機太陽能電池而言,電洞注入材料,例如,酞花青銅複合物(phthalocyanine copper complex)(CuPc)、4,4’,4”-三(N-3-甲基苯基-N-苯基-氨基)三苯胺(4,4’,4”-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine)(m-MTDATA)、4,4’,4”-三(N-(2-萘基)-N-苯基-氨基)三苯胺(4,4’,4”-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamino)(2-TNATA)、MeO-TPD(N,N,N’,N’-四(4-甲氧基-苯基)聯苯胺(N,N,N’,N’-tetrakis(4-methoxy-phenyl)benzidine)),或是螺旋TDB(2,2’,7,7’-四-(N,N-二苯胺)-9,9’-螺旋二芴(2,2’,7,7’-tetrakis-(N,N-diphenylamino)-9,9”-spirobifluoren),亦稱之為螺旋TTP),接著,該層順序可以是,舉例而言,陽極/p摻雜HIL/EBL/EML/ETL/LiF/陰極,在此,HIL代表一電洞注入層(hole injection layer),EBL代表一電子阻擋層(electron blocking layer),LiF代表氟化鋰層(Lithium fluoride),通常,如
此的HIL材料會具有一相對而言較低的氧化電位,介於0V至0.1V vs.Fc/Fc+之間,而氧化電位則是可以被視為對於一分子的HOMO的測量,然而,同樣也需要在傳統使用作為HTL、或EBL的主要材料中達成良好的摻雜結果,它們通常會具有一介於0.2V至0.4V vs.Fc/Fc+之間的較高氧化電位,因此,需要注意的是,該等所選擇的摻質會在一HIL型態的主要材料以及一HTL型態的主要材料中提供相同的高傳導性,其中,HTL型態的材料可為,舉例而言,N,N’-二(萘-1-基)-N,N’-二(苯基)-聯苯胺(N,N’-bis(naphthalene-1-yl)-N,N’-bis(phenyl)-benzidine)、N,N’-二(萘-1-基)-N,N’-二(苯基)-9,9-螺旋-二芴(N,N’-bis(naphthalene-1-yl)-N,N’-bis(phenyl)-9,9-spiro-bifluorene)、9,9-二[4-(N,N’-二-二苯基-4-基-氨)苯基]-9H-芴(9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene)、N,N’-二(菲-9-基)-N,N’-二(苯基)-聯苯胺(N,N’-bis(phenanthren-9-yl)-N,N’-bis(phenyl)-benzidine)、2,2’-二[N,N-二(苯基-4-基)氨]9,9-螺旋-二芴(2,2’-bis[N,N’-bis(phenyl-4-yl)amino]9,9-spiro-bifluorene)、1,3,5-三{4-[二(9,9-二甲基-芴-2-基)氨基]苯基}苯(1,3,5-tri{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene),以及三(三聯苯-4-基)胺(tri(terphenyl-4-yl)amine)。
利用根據本發明所使用的化合物在一基板上的沈積率的決定可以,例如,(正如習慣上所使用的)利用一石英厚度監視器(例如,在生產OLEDs時),特別地是,基質材料以及摻雜劑的沈積率的比例的測量可以利用二個分開的石英厚度監測器而分別執行,以調整摻雜的比例。
需要瞭解的是,較佳地是,根據本發明所使用的化合物它們多少要會蒸發、或特別地是,不會分解,然而,若有需要,即使是有目的的前驅物也可以被使用作為摻雜源,以釋放根據本發明所使用的該等化合物,例如,一揮發、或非揮發無機、或有機酸的,例如,酸加成鹽(acid addition salts)、或是它們的電荷傳輸複合物,其中,酸、及/或電子供體會較佳地為非揮發性、或僅輕微揮發性,或者該電荷傳輸複合物本身可作用為摻雜劑。
較佳地是,該摻雜劑的選擇方式是,在相同的條件下(例如,特別地是,在一既定的基質材料(例如,鋅酞花青、或接下來更進一步列
舉的另一基質材料)處的摻雜濃度(莫耳比,摻雜劑:基質,層厚度,電流強度),其會產生的一傳導性會剛好等高於、或(較佳地)高於F4TCNQ,例如,大於/等於F4TCNQ的1.1倍、1.2倍,或大於/等於F4TCNQ的1.5倍、或2倍的一傳導性。
另外,較佳地是,根據本發明所使用的該摻雜劑的選擇方式亦可以是,在溫度自100℃改變至RT(20℃)之後,利用其而進行摻雜的半導體有機材料仍然具有在100℃時之傳導性(s/cm)數值的≧20%,較佳地是,≧30%,尤其較佳地是≧50%、或≧60%。
製備氧碳(oxocarbon),偽氧碳(pseudooxocarbon),以及軸烯(radialenes)結構
第一個氧碳化合物,克酮酸鉀,是L.Gmelin在1925年由碳酸鉀以及煤所製成,較佳地是,氧碳以及其酯類(esters)和鹵化物(halogenides)會與多電子化合物(electron-rich compound)進行反應,例如,脂肪族(aliphatic)與芳香胺(aromatic amines),芳族化合物(aromatics),以及雜芳族化合物(heteroaromatics)(A.H.Schmidt,Synthesis(1980)961),其中,在路易斯酸(Lewis acid)或CH酸性(CH-acidic)化合物的存在下,利用強鹼(例如,芳基乙腈(arylacetonitriles),1,3-二酮(1,3-diketone),環戊二烯(cyclopentadienes),丙二腈(malonodinitriles),受體取代二芳基甲烷(acceptor-substituted diarylmethanes),少電子二雜芳基甲烷(electron-poor diheteroarylmethanes)),四氯環丙烷(tetrachlorocyclopropene)以及酚(phenol)的反應產物特別適合於根據本發明的應用,而在執行氧化後就可以獲得[3]-軸烯(R.West et al.J.Org.Chem.(1975)40 2295;T.Kazuka,T.Shinji J.Chem.Soc.Chem.Commun.(1994)519;T.Fukunaga et al.JACS(1976)98 610)。
基質材料
本發明敘述有機半導體材料所適合的摻雜劑,例如,通常被用於OLEDs、或有機太陽能電池的電洞傳輸材料HT,較佳地是,該等半導
體材料在本質上具有電洞傳導能力(hole-conducting),而接下來所提出的是對於材料的一實例,其可關聯於依據本發明的軸烯型態摻雜劑而進行應用。
該基質材料的組成可以部分地(>10、或重量>25%)、或大體上(重量>50%、或重量>75%)、完全地包括,一金屬酞花青(metal phthalocyanines)複合物,紫菜鹼(porphyrine)(特別是金屬紫菜鹼複合物),寡噻吩(oligothiophene-),寡合苯基(oligophenyl-),寡合亞苯1,2-亞乙烯基(oligophenlene vinylene-),或寡合芴化合物(oligofluorene compound),其中,該寡合物較佳地是包括2-500、或更多個單體單元,且較佳地是,2-100、或2-50、或2-10、或更多個單體單元,另外,該寡合物亦可以包括>4、>6、或>10、或更多的單體單元,且特別地是,亦可為上述的範圍,因此,例如,4、或6-10個單體單元,6、或10-100個單體單元,或10-500個單體單元,此外,也可以使用聚合基質材料,其中,該等單體以及寡合體可以被取代、或不被取代,甚至,可以出現所列舉的寡合物的嵌段(block-)、或混合聚合物,以及一具有一三芳胺單元(triarylamine unit)的化合物、或一螺旋雙芴(spiro-biflurorene)化合物,再者,所列舉的該等基質材料亦能夠以彼此結合的方式呈現,且可選擇地是,也可以與其他的基質材料相結合,並且,該等基質材料可以包括會具有一已降低的游離能(ionizing energy)、或會降低該基質材料的游離能的電子供給取代基(electron donating substitutents),例如,烷基、或烷氧基團。
被使用作為基質材料的該等金屬酞花青複合物、或紫菜鹼複合物可以具有一主基團金屬原子、或次基團金屬原子,其中,該金屬原子Me可以為4、5、或6重配位,例如,其形式可為酮基-(Me=O)(oxo-(Me=O))、二酮基-(O=Me=O)亞胺(dioxo-(O=Me=O)imine-)、二亞胺(diimine-)、羥基(hydroxo-)、二羥基(dihydroxo-)、胺基(amino-)、或二胺(diamino-)的複合物,但並無限制,另外,該酞花青複合物、或紫菜鹼複合物的每一個都可以部分地被氫化,然而,最好不要妨礙內消旋環系統(mesomeric ring system),其中,該酞花青可以包含,例如,鎂,鋅,鐵,鎳,鈷,鎂,銅,或氧釩基(vanadyl)(=VO),以作為中心原子,此
外,相同的、或其他的金屬原子、或氧金屬(oxometal)原子也可以出現在紫菜鹼複合物之中。
特別地是,如此的可摻雜電洞傳輸材料HT可以是芳化的聯苯胺(arylated benzidines),例如,如型態TPD(其中的一個、數個、或全部的芳基基團可以具有芳香族雜原子)的N,N’-過芳化聯苯胺(N,N’-perarylated benzidines)、或其他二胺,以及適合的芳化星狀化合物(arylated starburst compounds),如N,N’,N”-過芳化星狀化合物(N,N’,N”-perarylated starburst compound)(例如,TDATA(其中的一個、數個、或全部的芳基基團可以具有芳香族雜原子)),其中,該等芳基基團可以包括苯基(phenyl),萘基(naphthyl),吡啶(pyridine)喹啉(quinoline),異喹啉(isoquinoline),噠嗪(peridazine),嘧啶(pyrimidine),吡嗪(pyrazine),吡唑(pyrazole),咪唑(imidazole),呋喃(furan),吡咯(pyrrole),吲哚(indole),或類似者,尤其是可用於上述所列舉的化合物的每一個,該等特別的化合物的苯基基團可以部分地、或完全地被噻吩基團(thiophene groups)所取代。
摻雜
該摻雜的實行方式可以是,基質分子對摻雜劑的莫耳比、或是在寡合物基質材料的情形中,基質單體數對摻雜劑的比值為,1:100000,較佳地是,1:10000,尤其較佳地是,1:5至1:1000,例如,1:10至1:100,
例如,大約1:50至1:100、或也可以為1:25至1:50。
摻雜劑的蒸散
利用根據本發明而被使用的該等摻雜劑來對該特別的基質材料所進行的摻雜,將可以利用下列程序的其中之一、或其結合而產生:在真空中一起混合蒸發一HT來源以及該摻雜劑的其中之一。
b)緊接著沈積HT以及摻雜劑,是利用藉由熱處理而使該摻雜劑接著向內擴散的方式。
c)接著藉由一摻雜劑的溶液而摻雜一HT層,是利用藉由熱處理而產生溶劑蒸發的方式。
d)藉由一摻雜劑層而進行一HT層的表面摻雜,此可施加於該HT層的任一、或二表面之上。
e)製造主材料與摻質的一溶液,並從該溶液形成一膜,舉例而言,可藉由塗覆,澆鑄,或印刷技術,或是對本領域中具通常知識者而言為已知的其他膜製造技術。
該摻雜的實行方式可以是,使該摻雜劑自一會於加熱、及/或輻射照射時釋放該摻雜劑的前驅化合物中發散出來,其中,該輻射的實行可以利用電磁輻射,尤其是可見光、UV光、或IR光,例如,利用雷射光、或可其他輻射型態,接著,蒸散所需要的熱則是藉由該輻射而獲得,並且,亦能夠有目的地輻射進入該等化合物、或前驅物、或化合物複合物(例如,要進行蒸散的電荷傳輸複合物)的某些鍵結,以藉由將該等複合物分解轉換為激態(excited state)的方式而幫助蒸散該等化合物,在此,需要瞭解的是,在接下來所敘述的蒸散條件是指沒有輻射的情況,而該些一致的蒸發條件則是為了比較的目的而使用。
舉例而言,接下來所列者可以被使用作為前驅物化合物:
a)該摻雜劑以及一惰性、非揮發性物質(例如,聚合物,分子篩(molecular sieve),氧化鋁,矽膠,以及寡合物、或另一具有高蒸散溫度的有機、或無機物質)的混合物、或是定比(stoichiometric)、或混合的結晶化合物,其中,該摻雜劑主要是藉由凡得瓦力(van der Waals
forces)、及/或氫鍵(hydrogen bridge bonding)而與此物質產生鍵結。
b)該摻雜劑以及該電子供體型態的一大體上非揮發性化合物V的混合物、或是定比、或混合的結晶化合物,其中,一大體上完全的電荷傳輸會發生在該摻雜劑以及該化合物V之間,正如在與大體上多電子芳基聚合物、或雜芳基、或是另一具有高蒸散溫度的有機、或無機物質的電荷傳輸複合物中一樣。
c)該摻雜劑以及一物質的混合物、或是定比、或混合的結晶化合物,其中,該物質是會與該摻雜劑一起蒸散、並具有與該待摻雜物質HT相同、或更高的游離能者,因此,該物質就不會在該有機基質材料中形成電洞的陷阱,根據本發明,該物質亦可以與在此的該基質材料相同,例如,可以是一金屬酞花青或聯苯胺(benzidines)衍生物,更進一步地,也可以是適合的揮發性共同物質(co-substances),例如,對苯二酚(hydroquinones)、1,4-苯二胺(1,4-phenylene diamines)、或1-胺基-4-羥基苯(1-amino-4-hydroxybenzene),或是其他形成苯醌合苯二酚(quinhydrones)、或其他電荷傳輸複合物的化合物。
電子組件(component)
包含它們的複數個電子組件、或設備的產生可以利用根據本發明之用於產生可以排列為,尤其是,層、或電性線路徑(electrical line paths)形式的已摻雜有機半導體材料的該等有機化合物而達成,特別地是,根據本發明的該等摻雜劑可以被用以產生有機發光二極體(OLEDs)、或有機太陽能電池、有機二極體,尤其是該些具有一高正流比(rectification ratio)(例如,103-107,較佳地是,104-107、或105-107)者、或是有機場效電晶體,因此,該等已摻雜層的傳導性、及/或會接觸進入該已摻雜層的電荷載體注入的改進可以藉由根據本發明的該等摻雜劑而獲得改進,特別地是,在OLEDs、或太陽能電池的例子中,該組件可以具有一接腳結構(pin structure)(該裝置具有一、或多個p摻雜電洞層、及/或一、或多個n摻雜電子傳輸層)、或是一顛倒的結構(該頂部電極以及電洞傳輸層位在光發散、或光捕捉層同側,且同時間基底位在相反側),但並不受限,另外,一注入層的製備則是可以,舉例而言,藉由在一電極以及一電荷傳輸層之間形成一包
含、或組成為根據本發明的該等有機化合物的層而達成,然而,根據本發明的該等摻雜劑的使用並不受限於上述所列舉的具有優勢的示範性實施例。
示範性實施例
現在,根據本發明的該等化合物將在接下來的敘述中被使用作為不同電洞導體(hole conductor)的摻雜劑,以被用於建構某些微電子、或光電子組件(例如,一OLED),而藉由熱蒸散,該等摻雜劑則是可以與該基質的該等電洞傳輸材料一起在高真空(大約2 x10-4Pa)下蒸散,通常,該基質材料的一沈積率會是0.2nm/s(密度大約1.5g/cm3),而該等摻雜劑的蒸散率則是可以根據所需的摻雜率而在0.001至0.5nm/s(假設相同的密度)之間變化。
在接下來的實例中,電流測量的實行方式是,測量長1mm以及寬大約0.5mm的該已摻雜HT材料在1V下的一電流路徑,而在這些情況下,ZnPc則是於實際上不會傳導電流。
合成的實例:
1.乙基2-氰基-2-芳基醋酸(ethyl 2-cyano-2-aryl acetates)a),b),c),d)以及e)
一般程序:在含207mmol任一起始材料A、B、C、D、或E以及250mmol碳酸鉀的370mL二甲基甲醯胺(dimethylformamide)溶液中快速地加入含207mmol的氰乙酸酯(cyano acetic ester)的50mL二甲基甲醯胺,使混合物在室溫下攪拌48小時,接著,將反應懸浮液與1L的冰水一起倒入一3L的破碎機之中,在攪拌的同時,利用100mL的濃縮醋酸對溶液進行酸化,之後,水溶液利用氯仿(chloroform)依序(250mL,150mL,100mL,100mL)萃取四次,而在利用硫酸鎂乾燥結合的有機層之後,在真空中移除溶劑,剩下的油不需要更近一步的純化即可於下一步驟中使用。
a)乙基2-氰基-2-(全氟苯基)醋酸(ethyl 2-cyano-2(perfluorophenyl)acetate):六氟苯(Hexafluorobenzene)(A)被使用作為起始材料。
根據上述的程序可以獲得51.9克的酯。
b)乙基2-氰基-2(全氟吡啶-4-基)醋酸(ethyl 2-cyano-2(perfluoropyridin-4-yl)acetate):五氟吡啶(Pentafluoropyridin)(B)被使用作為起始材料。根據上述的程序可以獲得47.7克的酯。
c)乙基2-氰基-2-(4-氰全氟苯基)醋酸(ethyl 2-cyano-2-(4-cyanoperfluorophenyl)acetate):五氟苯腈(Pentafluorobenzonitril)(C)被使用作為起始材料。根據上述的程序可以獲得54.3克的酯。
d)乙基2-氰基-2-(4-三氟甲基全氟苯基)醋酸(ethyl 2-cyano-2-(4-trifluoromethylperfluorophenyl)acetate):八氟甲苯(Octafluorotoluol)(D)被使用作為起始材料。根據上述的程序可以獲得66.8克的酯。
e)乙基2-氰基-2-(4-三氟甲基-2,6-二氯-3,5-二氟苯基)醋酸(ethyl 2-cyano-2-(4-trifluoromethyl-2,6-dichloro-3,5-difluorophenyl)acetate):4-三氟甲基-2,6-二氯-1,3,5-三氟苯(4-trifluoromethyl-2,6-dichloro-1,3,5-trifluorobenzene)(E)被使用作為起始材料。根據上述的程序可以獲得64.8克的酯。
2.芳基乙腈(aryl acetonitriles)f),g),h),i),以及k)
一般程序:在一250mL圓底燒瓶中,將上述所合成的所有量的乙基2-氰基-2-芳基醋酸a),b),c),d)以及e)溶解在84mL的醋酸(50%)以及4.15mL的硫酸(濃縮液)之中,混合液加熱回流16小時,在冷卻到室溫後,將混合液與120mL的冰水一起倒入一500mL的破碎機之中,攪拌超過30分鐘,之後,將有機層分開,水溶液層利用100mL的氯仿進行萃取,然後,結合的有機層利用100mL的水以及100mL的飽和碳酸氫鈉(sodium bicarbonate)溶液分別進行清洗,而在利用硫酸鎂乾燥結合的有機層之後,在真空中移除溶劑,得到棕色的油,最後,在真空中蒸餾,得到
無色緩慢固化液體(slow solidifying liquid)。
f)五氟苯基乙腈(pentafluorophenyl acetonitrile):乙基-2-氰基-2-(全氟苯基)醋酸(a)被使用作為起始材料。根據上述的程序可獲得36.4克(176mmol;以起始材料A為基礎的85%)的該芳基乙腈。
g)4-氰甲基-2,3,5,6-四氟吡啶(4-(cyanomethyl)-2,3,5,6-tetrafluoropyridine):乙基2-氰基-2(全氟吡啶-4-基)醋酸(b)被使用作為起始材料。根據上述的程序可獲得33.1克(174mmol;以起始材料B為基礎的84%)的該芳基乙腈。
h)4-氰甲基-2,3,5,6-四氟苯腈(4-(cyanomethyl)-2,3,5,6-tetrafluorobenzonitrile):乙基2-氰基-2-(4-氰全氟苯基)醋酸(c)被使用作為起始材料。根據上述的程序可獲得39.0克(182mmol;以起始材料C為基礎的88%)的該芳基乙腈。
i)2-(2,3,5,6-四氟-4-(三氟甲基)苯基)乙腈(2-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)acetonitrile):乙基2-氰基-2-(4-三氟甲基全氟苯基)醋酸(d)被使用作為起始材料。根據上述的程序可獲得48.8克(190mmol;以起始材料D為基礎的92%)的該芳基乙腈。
k)(4-三氟甲基-2,6-二氯-3,5-二氟苯基)乙腈((4-trifluoromethyl-2,6-dichloro-3,5-difluorophenyl)acetoneitrile):乙基2-氰基-2-(4-三氟甲基-2,6-二氯-3,5-二氟苯基)醋酸(e)被使用作為起始材料。根據上述的程序可獲得53.4克(184mmol;以起始材料E為基礎的89%)的該芳基乙腈。
3.[3]軸烯([3]-radialenes)l),m),n),o),以及p)
一般程序:將氫化鋰(lithium hydride)(98%)懸浮在600mL的1,2-二甲氧基乙烷(1,2-dimethoxyethane)之中,並冷卻至0℃,然後,將152mmol
的芳基乙腈f)、g)、h)、i)、或k)溶解在60mL的1,2-二甲氧基乙烷之中,並添加持續10至15分鐘的期間,將冰浴移除後,讓反應回溫45分鐘,於室溫下攪拌15分鐘之後,混合液再次冷卻至0℃,然後,逐滴地加入含有7.12克(40.0mmol)全氯環丙-1-烯(perchlorocycloprop-1-ene)的1,2-二甲氧基乙烷40mL,此時,溶液的顏色轉為深紅色,之後,持續攪拌深色溶液44小時,並同時間回溫至室溫,接著,將該反應懸浮液與1.2L的冰水一起倒入一2L的破碎機之中,再利用濃縮氯化氫將攪拌溶液酸化至pH=1(240mL HCl),並利用乙酸乙酯進行萃取(3x500mL),之後,該結合的有機溶液層以接下來的順序進行清洗:鹵水,水,以及重碳酸鹽溶液,然後,再次利用水進行清洗,而在利用硫酸鎂乾燥結合的有機層之後,在真空中小心地移除溶劑,得到一深色的物質,其可不需要進行純化即直接於接下來的轉換程序中使用。
接著,將該深色物質溶解於1400mL的醋酸(100%)之中,並利用於10分鐘前準備的360mL氫溴酸(hydrobromic acid)(48%)以及120mL硝酸(65%)的一混合液對其進行處理,所產生的混合物攪拌1.5小時,之後,將混合物過濾,所得到的橘色沈澱利用水清洗,並於真空中乾燥,可得到粗製品,此粗製品再利用梯度昇華(gradient sublimation)的方式進行純化。
1)(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶基)-乙腈((2E,2’E,2”E)-2,2’,2”-(cyclopropane-1,2,3-triylidene)tris(2-(perfluoropyridinyl)-acetonitrile))
五氟苯基乙腈(f)被使用作為起始材料。在進行根據前述程序的梯度昇華之後,可獲得9.37克(14.4mmol;以四氯環丙烷為基礎的36%)的[3]軸烯。
Mp.211℃
m)(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶-4基)-乙腈((2E,2’E,2”E)-2,2’,2”-(cyclopropane-1,2,3-triylidene)tris(2-(perfluoropyridin-4-yl)-acetonitrile)
4-氰甲基-2,3,5,6-四氟吡啶(g)被使用作為起始材料。在進
行根據前述程序的梯度昇華之後,可獲得8.40克(14.0mmol;以四氯環丙烷為基礎的35%)的[3]軸烯。
Mp.140℃
n)(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(4-氰全氟苯基)-乙腈)((2E,2’E,2”E)-2,2’,2”-(cyclopropane-1,2,3-triylidene)tris(2-(4-cyanoperfluorophenyl)-acetonitrile))
4-氰甲基-2,3,5,6-四氟苯腈(h)被使用作為起始材料。在進行根據前述程序的梯度昇華之後,可獲得10.2克(15.2mmol;以四氯環丙烷為基礎的38%)的[3]軸烯。
Mp.316℃
o)(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,3,5,6-四氟-4-(三氟甲基)苯基)-乙腈)((2E,2’E,2”E)-2,2’,2”-(cyclopropane-1,2,3-triylidene)tris(2-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-acetonitrile))
2-(2,3,5,6-四氟-4-(三氟甲基)苯基)乙腈(i)被使用作為起始材料。在進行根據前述程序的梯度昇華之後,可獲得12.8克(16.0mmol;以四氯環丙烷為基礎的40%)的[3]軸烯。
Mp.197℃
p)(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,6-二氯-3,5-二氟(三氟甲基)苯基)-乙腈)((2E,2’E,2”E)-2,2’,2”-(cyclopropane-1,2,3-triylidene)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl)-acetonitrile))
(4-三氟甲基-2,6-二氯-3,5-二氟苯基)乙腈(k)被使用作為起始材料。在進行根據前述程序的梯度昇華之後,可獲得7.92克(8.80mmol;以四氯環丙烷為基礎的22%)的[3]軸烯。
Mp.220℃
摻雜實例:
實例1:
作為一主材料的螺旋TTB以及作為一摻質材料的
(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶基)-乙腈(1)的一混合層,會利用混合的熱蒸散而在一高真空腔室中被形成在一玻璃基板之上,其中,摻雜濃度5mol%,膜厚度50nm,該玻璃基板有相距1mm的二個ITO條紋,以作為該膜的電極,然後,根據該膜的電流-電壓特徵以及樣品的幾何學,該混合層的傳導性被決定為1.7‧10-6S/cm。
實例2:
在此實例中會形成另一個類似實例1的膜,但所使用的摻質是(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶-4基)-乙腈(m),所得的膜的傳導性為4.3‧10-5S/cm。
實例3:
在此實例中會形成另一個類似實例1的膜,但所使用的摻質是(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶-4-基)-乙腈(m),且使用作為主要材料的是N,N’-二(萘-1-基)-N,N’-二(苯基)-聯苯胺)(N,N’-Bis(naphthalen-1-yl)-N,N’-bis(phenyl)-benzidine),所得的膜的傳導性為1.3‧10-5S/cm。
實例4:
在此實例中會形成另一個類似實例3的膜,但所使用的摻質是(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(4-氰全氟苯基)-乙腈)(n),其中,摻雜濃度為10mol%,所得的膜的傳導性為6.8‧10-5S/cm。
實例5:
在此實例中會形成另一個類似實例3的膜,但所使用的摻質是(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,3,5,6-四氟-4-(三氟甲基)苯基)-乙腈)(o),其中,摻雜濃度為10mol%,所得的膜的傳導性為4‧10-5S/cm。
實例8:
在此實例中會形成另一個類似實例3的膜,但所使用的摻質是(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,6-二氯-3,5-二氟(三氟甲基)苯基)-乙腈)(p),其中,摻雜濃度為10mol%,所得的膜的傳導性為1.3‧10-5S/cm。
實例9:
在此實例中會形成另一個類似實例8的膜,但所使用的摻質是9,9-二[4-(N,N’-二-二苯基-4-基-胺)苯基]9H-芴(9,9-Bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]9H-fluorene),所得的膜的傳導性為1.2‧10-5S/cm。
對本發明的各種實施例有所瞭解後,本發明在先前的敘述中以及在申請專利範圍中所揭示的特徵可以在本質上為獨立的,也可以為任意的組合。
Claims (14)
- 一種有機內消旋化合物在一有機半導體基質材料的摻雜中作為一有機摻雜劑、作為阻擋層、作為電荷注入層、或作為有機半導體本身的用途,其特徵在於,該內消旋化合物是具有下列分子式的一軸烯化合物:
- 如申請專利範圍第1項所述的用途,其中,該芳基與雜芳基是完全地以電子受體基團取代。
- 如申請專利範圍第1項所述的用途,其特徵在於,該電子受體基團選自氰基、氟、三氟甲基、氯、以及溴。
- 如申請專利範圍第1或3項所述的用途,其特徵在於,R1選自全氟吡啶-4-基、四氟-4-(三氟甲基)苯基、4-氰全氟苯基、二氯-3,5-二氟-4-(三氟甲基)苯基、以及全氟苯基。
- 一種具有下列分子式的軸烯化合物,
- 如申請專利範圍第5項所述的軸烯化合物,其中,該芳基與雜芳基是完全地以電子受體基團取代。
- 如申請專利範圍第5項所述的軸烯化合物,其選自(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟苯基)-乙腈、(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-全氟吡啶-4基)-乙腈、(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(4-氰全氟苯基)-乙腈),(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,3,5,6-四氟-4-(三氟甲基)苯基)-乙腈),以及(2E,2’E,2”E)-2,2’,2”-(環丙烷-1,2,3-三乙二烯)三(2-(2,6-二氯-3,5-二氟-4-(三氟甲基)苯基)-乙腈)。
- 一種如申請專利範圍第5項所述的軸烯化合物、或其自由基負離子鹽、二價負離子鹽、或其與供體的電荷傳輸複合物作為有機導體、鐵磁體、或電、或光化學材料的用途。
- 一種有機半導體材料,包含至少一有機基質化合物以及一摻雜劑,其特徵在於,該摻雜劑是一或多個如申請專利範圍第4項所述的軸烯化合物。
- 如申請專利範圍第9項所述的有機半導體材料,其特徵在於,該基質化合物選自酞花青銅複合物(CuPc)、4,4’,4”-三(N-3-甲基苯基-N-苯基-氨基)三苯胺(m-MTDATA)、4,4’,4”-三(N-(2-萘基)-N-苯基-氨基)三苯胺(2-TNATA)、MeO-TPD(N,N,N’,N’-四(4-甲氧基-苯基)聯苯胺)、2,2’,7,7’-四-(N,N-二苯胺)-9,9’-螺旋二芴(螺旋-TTB)、N,N’-二(萘-1-基)-N,N’-二(苯基)-聯苯胺、N,N’-二(萘-1-基)-N,N’-二(苯基)-9,9-螺旋-二芴、9,9-二[4-(N,N’-二-二苯基-4-基-氨基)苯基]-9H-芴、N,N’-二(菲-9-基)-N,N’-二(苯基)-聯苯胺、2,2’-二[N,N-二(二 苯基-4-基)氨基]9,9-螺旋-二芴、1,3,5-三{4-[二(9,9-二甲基-芴-2-基)胺]苯基}苯、以及三(三聯苯-4-基)胺。
- 如申請專利範圍第9或10項所述的有機半導體材料,其特徵在於,該摻雜劑對基質分子的一莫耳摻雜比、及/或摻雜劑對一聚合基質分子的單體單元的一莫耳摻雜比介於1:1以及1:100,000之間。
- 一種具有一電子功能活性區域的電子組件,其特徵在於,該電子功能活性區域是利用至少一或多個如申請專利範圍第4項所述的軸烯化合物而產生。
- 如申請專利範圍第12項所述的電子組件,其特徵在於,該電子功能活性區域包括一有機半導體基質材料,該有機半導體基質材料是利用用於改變該半導體基質材料的電子特性的至少一摻雜劑並利用至少一或多個如申請專利範圍第4項所述的軸烯化合物進行摻雜。
- 如申請專利範圍第12或13項所述的電子組件,其形式為一有機發光二極體、一光揮發電池、一有機太陽能電池、一有機二極體、或一有機場效電晶體。
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JPS51117039A (en) * | 1975-03-07 | 1976-10-14 | Minnesota Mining & Mfg | Semiconductor composition |
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- 2008-11-04 EP EP08019300A patent/EP2180029B1/en active Active
- 2008-11-04 ES ES08019300T patent/ES2370120T3/es active Active
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2009
- 2009-10-12 TW TW098134521A patent/TWI423945B/zh active
- 2009-10-22 JP JP2009243516A patent/JP5199978B2/ja active Active
- 2009-10-23 CN CN2009102072751A patent/CN101728485B/zh active Active
- 2009-10-23 KR KR1020090101408A patent/KR101188391B1/ko active IP Right Grant
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US3963769A (en) * | 1974-12-20 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
JPS51117039A (en) * | 1975-03-07 | 1976-10-14 | Minnesota Mining & Mfg | Semiconductor composition |
JPH07168377A (ja) * | 1993-12-16 | 1995-07-04 | Konica Corp | 電子写真感光体 |
JP2004002740A (ja) * | 2002-03-22 | 2004-01-08 | Mitsubishi Chemicals Corp | 高分子化合物、1,4−フェニレンジアミン誘導体、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
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Also Published As
Publication number | Publication date |
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CN101728485B (zh) | 2013-03-06 |
ES2370120T3 (es) | 2011-12-12 |
TW201026648A (en) | 2010-07-16 |
JP2010100621A (ja) | 2010-05-06 |
KR20100045402A (ko) | 2010-05-03 |
EP2180029A1 (en) | 2010-04-28 |
JP5199978B2 (ja) | 2013-05-15 |
EP2180029B1 (en) | 2011-07-27 |
KR101188391B1 (ko) | 2012-10-05 |
CN101728485A (zh) | 2010-06-09 |
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