JP5155263B2 - ジベンゾシロールポリマー及びその製造方法 - Google Patents
ジベンゾシロールポリマー及びその製造方法 Download PDFInfo
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- JP5155263B2 JP5155263B2 JP2009185810A JP2009185810A JP5155263B2 JP 5155263 B2 JP5155263 B2 JP 5155263B2 JP 2009185810 A JP2009185810 A JP 2009185810A JP 2009185810 A JP2009185810 A JP 2009185810A JP 5155263 B2 JP5155263 B2 JP 5155263B2
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- polymer
- general formula
- group
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- dibenzosilol
- Prior art date
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- 229920000642 polymer Polymers 0.000 title abstract description 97
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 16
- 239000000463 material Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 17
- -1 poly (p-phenylene vinylene) Polymers 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 238000006116 polymerization reaction Methods 0.000 description 12
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000002347 injection Methods 0.000 description 10
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- 125000000524 functional group Chemical group 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 125000001475 halogen functional group Chemical group 0.000 description 7
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000010555 transalkylation reaction Methods 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 125000005619 boric acid group Chemical group 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 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 3
- 239000011521 glass Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 230000005258 radioactive decay Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
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- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OHWIQIVPGPMWHV-UHFFFAOYSA-N 1,2-dihexyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCC)C(CCCCCC)=C3CC2=C1 OHWIQIVPGPMWHV-UHFFFAOYSA-N 0.000 description 1
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
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- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- WLDODCCINAIYNV-UHFFFAOYSA-N 5,5-dibromo-1-nitro-2-(2-nitrophenyl)cyclohexa-1,3-diene Chemical group BrC1(CC(=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])[N+](=O)[O-])Br WLDODCCINAIYNV-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical class C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LFRVGFJVRIUAKL-UHFFFAOYSA-N BrC1=CC(=C(C=C1)C1=C(C=C(C=C1)Br)[N+](=O)[O-])[N+](=O)[O-].C(C)O Chemical group BrC1=CC(=C(C=C1)C1=C(C=C(C=C1)Br)[N+](=O)[O-])[N+](=O)[O-].C(C)O LFRVGFJVRIUAKL-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
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- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- OTNKFEXCDMOBHL-UHFFFAOYSA-N [3-bromo-4-(2-bromo-4-trimethylsilylphenyl)phenyl]-trimethylsilane Chemical group BrC1=CC([Si](C)(C)C)=CC=C1C1=CC=C([Si](C)(C)C)C=C1Br OTNKFEXCDMOBHL-UHFFFAOYSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 230000029936 alkylation Effects 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- ZGDJMMPBPMJJBR-UHFFFAOYSA-N bis(1H-indol-2-yl)diazene Chemical compound c1c(N=Nc2cc3ccccc3[nH]2)[nH]c2ccccc12 ZGDJMMPBPMJJBR-UHFFFAOYSA-N 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical group [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 description 1
- ICMGJLRWDJYLGU-UHFFFAOYSA-N carbamic acid;2-hydroxybenzoic acid Chemical class NC(O)=O.OC(=O)C1=CC=CC=C1O ICMGJLRWDJYLGU-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- SAWUYBUUNHDUFL-UHFFFAOYSA-N trimethyl-(1-methylbenzo[b][1]benzosilol-1-yl)silane Chemical compound C1=CC=CC2=C3C(C)([Si](C)(C)C)C=CC=C3[SiH]=C21 SAWUYBUUNHDUFL-UHFFFAOYSA-N 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
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Description
(a)各Xは同じか異なり、ホウ酸、ボロンエステル及びボランから選ばれるボロン誘導官能基である一般式(II)のモノマー、及び少なくとも2つの反応性ハロゲン官能基を有する芳香族モノマー、又は
(b)各Xは同じか異なり、反応性ハロゲン官能基である一般式(II)のモノマー、及びホウ酸、ボロンエステル及びボランから選ばれる少なくとも2つのボロン誘導官能基を有する芳香族モノマー、又は
(c)1つのXは反応性ハロゲン官能基であり、他のXはホウ酸、ボロンエステル及びボランから選択されるボロン誘導官能基である一般式(II)のモノマー、
ここで、反応混合物は、芳香族モノマーの重合の触媒に適するパラジウム触媒の触媒量、及びボロン誘導官能基をボロンアニオン基に変換するのに十分な量の塩基を含む。
M1L1 qL2 rL3 s (XI)
セリウム、サマリウム、ユーロピウム、テルビウム、ジスプロジウム、ツリウム、エルビウム及びネオジウム、及びd−ブロック金属、特に、2及び3族のもの、すなわち、元素39〜48及び72〜80、特に、ルテニウム、ロジウム、パラジウム、レニウム、オスミウム、イリジウム、プラチナ及び金。
Langeveld, Carsten Rothe, Andy Monkman, Ingrid Bach, Philipp Stossel, and Klemens Brunner, J. Am. Chem. Soc. ASAP Articles, Web Release date 28-May-2004参照。
モノマーの例
本発明の第2の側面のモノマー1及び2は次の反応スキームにより合成された。
DMF(200cm3)中の2,5−ジブロモニトロベンゼン(50.0g,179mmol)の溶液中に、銅粉末(27.0g、424mmol)が加えられ、反応混合物は125℃まで加熱された、3時間後、反応混合物は室温まで冷却され、次いでトルエン(200cm3)で処理された。不溶性無機塩がセライトによるろ過により除去され、ろ過物は乾燥するまで蒸発された。生の原材料はメタノール(500cm3)で強く洗浄され、トルエン(200cm3)に再溶解された。残りの無機塩はセライトによるろ過で再度除去され、ろ過物が蒸発されて表題の化合物(27.1g、75%)が黄色の結晶として得られた。(実測値:C,35.8;H,1.5;N,6.7.C12H6Br2N2O4の理論値はC,35.9;H,1.5;N,7.0%);νmax/cm-1(固体)730、829、1004、1103、1344、1526;δH(500MHz,CDCl3)7.18(2H,d,J8.2,ArH)、7.85(2H,dd,J8.2,2.0,ArH),8.39(2H,d,J2.0,ArH);δc(100MHz,CDCl3)1
22.9,128.1,131.9,132.0,136.6,147.4
エタノール(abs.,186cm3)中の4,4’−ジブロモ−2,2’−ジニトロ−ビフェニル(15.0g,37.3mmol)溶液に32w%のHCl水溶液(124cm3)が加えられた。錫粉末(17,6g,147mmol)が10分間以上加えられ、反応混合物は100℃で2時間還流するまで加熱された。冷却後、混合物は氷水(ca.400cm3)中に注がれ、次いで、20%のNaOH水溶液(150cm3)で塩基化された。生成物はジエチルエーテルで抽出され、有機層は塩水で洗浄され、無水MgSO4上で乾燥され、乾燥するまで蒸発された。エタノールからの再結晶化による純化により薄茶の結晶として表題の化合物(9.2g,72%)が得られた。(実測値:C,42.1;H,3.0;N,8.0.C12H10Br2N2の理論値はC,42.2;H,3.0;N,8.2%);νmax/cm-1(固体)792、994、1406、1477、1608、3210、3357、3443;δH(400MHz,CDCl3)6.92(6H,s,ArH)、3.78(4H,brs、NH2);δc(100MHz,CDCl3)118.1、121.7、122.0、122.7、132.2、145.4、m/Z(ES)340.9283(M+H)+.C12H11Br2N2の理論値340.9284)、343.1(100%)、263.1(80)、185.1(25).
で洗浄され、無水性MgSO4で乾燥され蒸発された。カラムクロマトグラフィー(ヘキサン)による純化により、表題の化合物(1.45g,15%)を非白色固体として生成した。(実測値:C,25.8;H,1.0;C12H6Br2I2の理論値はC,25.6;H,1.1%);mp89℃;νmax/cm-1(固体)710、817、993,1086,1448,1565;δH(400MHz,CDCl3)7.03(2H,d,J8.2,ArH)、7.55(2H,dd,J8.2,1.9,ArH),8.08(2H,d,J1.9,ArH);δc(100MHz,CDCl3)99.8,122.5、
130.7、131.4、141.0、146.8
ポリマーの実施例1:本発明の第1の側面のホモポリマーは、次のスキームにしたがってモノマー1及びモノマー2のスズキ重合により、続いて、ブロモベンゼン及びフェニルホウ酸の末端キャップが行われ製造された。
一般的方法:ガラス基板(Applied Films, Colorado, USAより入手可)に支持されたインジウム錫酸化物上にHC Stark of Leverkusen, GermanyからBaytron P(登録商標)として入手できるPEDT/PSS層をスピンコートにより蒸着した。電子発光ポリマー層はキシレン溶液からスピンコートによりPEDT/PSS層上に蒸着された。電子発光ポリマー層上には、カルシムの第1層及びアルミニウムの第2キャップ層からなるカソードが真空蒸着された。
bオンセット吸収(UV−Vis)によって決められる光学バンドギャップエネルギ
cEonset(OX)から決められる(フェロセンのエネルギレベルを真空下−4.8eVとする)
dEg optをHOMOエネルギレベルに加えることによって決められる
本発明の第9の側面のモノマーは、次の反応スキームにしたがって合成された。また、上記2,7結合ジベンゾシロールを有する上記の場合のように、ジメチルシリル基(ステップe)のトランスアルキル化はトリメチルシリル末端基に影響を与えず、したがってこのルートはシリコン原子に広い範囲の置換基を導入する方法を提供する。
下記の表は、コポリマーの吸収最大値及び光学的バンドギャップを示す。コポリマーの溶液UV−Vis吸収スペクトルがヘキサン中で測定された。
bポリマーのバンドギャップ、UV吸収オンセットからの測定
コポリマーの薄膜が金の実用電極上にサンプル(トルエン中の1.0重量%溶液)をスピンコートすることにより得られた。ついで、室温で50mV/sのスキャンレートで、対極電極としてプラチナ線、参照電極としてAg/AgCl電極を使用して、アセトニトリル中のBu4N+ClO4 -(0.10M)溶液中で測定された。両測定は、4.8eVのイオン化ポテンシャルを有するフェロセンに対して較正(キャリブレーション)された。
bオンセット吸収(UV−Vis)によって決められる光学バンドギャップエネルギ
cEonset(OX)から決められる(フェロセンのエネルギレベルを真空下−4.8eVとする)
dEg optをHOMOエネルギレベルに加えることによって決められる
Claims (1)
- 下記のスキームにしたがって、一般式(V)の化合物から一般式(VI)のモノマーを形成する方法であって、
ここで、Rは同じか異なり、H又は電子誘引基を表し、
各X1は同じか異なり、ハロゲンを表し、
各X3は同じか異なり、X1の電気陰性度以下の電気陰性度を有するハロゲンを表し、
Yは−CR3 2−、−SiR3 2−、−NR3−、−PR3−、−GeR3 2−、−SnR3 2−、O及びSから構成される群より選択され、ここで、R3は選択的に置換されたアルキル、アルコキシ、アリール及びヘテロアリールから構成される群より選択され、
各LGは同じか異なりハロゲンを表す前記方法。
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2004
- 2004-11-10 EP EP04798477A patent/EP1682600B1/en not_active Not-in-force
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- 2004-11-10 JP JP2006538943A patent/JP4390113B2/ja not_active Expired - Fee Related
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2006
- 2006-05-18 KR KR1020067009696A patent/KR101151967B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
---|---|
US20130334505A1 (en) | 2013-12-19 |
KR101151967B1 (ko) | 2012-06-01 |
JP2013018986A (ja) | 2013-01-31 |
WO2005047363A1 (en) | 2005-05-26 |
JP5588484B2 (ja) | 2014-09-10 |
JP2010001483A (ja) | 2010-01-07 |
KR20070012316A (ko) | 2007-01-25 |
JP2007516319A (ja) | 2007-06-21 |
US11183648B2 (en) | 2021-11-23 |
US9419233B2 (en) | 2016-08-16 |
EP1682600B1 (en) | 2013-01-23 |
EP1682600A1 (en) | 2006-07-26 |
JP4390113B2 (ja) | 2009-12-24 |
US20160343961A1 (en) | 2016-11-24 |
HK1103552A1 (en) | 2007-12-21 |
US20070248839A1 (en) | 2007-10-25 |
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