WO2013108894A1 - Composé de fulvalène et son procédé de production, polymère de fulvalène et matériau de photopile et matériau de transistor organique - Google Patents
Composé de fulvalène et son procédé de production, polymère de fulvalène et matériau de photopile et matériau de transistor organique Download PDFInfo
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- WO2013108894A1 WO2013108894A1 PCT/JP2013/050985 JP2013050985W WO2013108894A1 WO 2013108894 A1 WO2013108894 A1 WO 2013108894A1 JP 2013050985 W JP2013050985 W JP 2013050985W WO 2013108894 A1 WO2013108894 A1 WO 2013108894A1
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- WIPO (PCT)
- Prior art keywords
- group
- fulvalene
- ring
- ring structure
- bonded
- Prior art date
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- -1 Fulvalene compound Chemical class 0.000 title claims abstract description 235
- XEOSBIMHSUFHQH-UHFFFAOYSA-N fulvalene Chemical compound C1=CC=CC1=C1C=CC=C1 XEOSBIMHSUFHQH-UHFFFAOYSA-N 0.000 title claims abstract description 163
- 229920000642 polymer Polymers 0.000 title claims abstract description 130
- 239000000463 material Substances 0.000 title claims abstract description 74
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 59
- 125000001424 substituent group Chemical group 0.000 claims abstract description 327
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 111
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 17
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 47
- 125000004434 sulfur atom Chemical group 0.000 claims description 37
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 24
- 238000006243 chemical reaction Methods 0.000 description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000006068 polycondensation reaction Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000000707 boryl group Chemical group B* 0.000 description 21
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- 229910052763 palladium Inorganic materials 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- NVMYRXGXUBZAIU-UHFFFAOYSA-N 9-fluoren-9-ylidenefluorene Chemical group C12=CC=CC=C2C2=CC=CC=C2C1=C1C2=CC=CC=C2C2=CC=CC=C21 NVMYRXGXUBZAIU-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000000732 arylene group Chemical group 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000004696 coordination complex Chemical group 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 229920000578 graft copolymer Polymers 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 4
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- NAWUZMMAZOQEEA-UHFFFAOYSA-N 1-ethynyl-2-phenylbenzene Chemical group C#CC1=CC=CC=C1C1=CC=CC=C1 NAWUZMMAZOQEEA-UHFFFAOYSA-N 0.000 description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000012827 research and development Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000005490 tosylate group Chemical group 0.000 description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- JPXBIAWPJOGFCF-UHFFFAOYSA-N 4-bromo-1-(4-bromo-2-iodophenyl)-2-iodobenzene Chemical group IC1=CC(Br)=CC=C1C1=CC=C(Br)C=C1I JPXBIAWPJOGFCF-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 0 CCCC1C(CC)(C(C)C*)C(CC(C)(C)C)CC1CCCIC(C)C Chemical compound CCCC1C(CC)(C(C)C*)C(CC(C)(C)C)CC1CCCIC(C)C 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
L'invention porte sur un nouveau composé ayant un squelette de fulvalène qui peut être utilisé de façon appropriée comme matériau pour un semi-conducteur organique de type n, un élément électroluminescent (EL) organique, ou similaire, et sur un procédé de production qui permet de synthétiser des composés de structures diverses ayant un squelette de fulvalène. L'invention porte sur un polymère ayant un squelette de fulvalène qui peut être utilisé de façon appropriée comme matériau pour un semi-conducteur organique de type n, un élément EL organique ou similaire. Plus précisément, l'invention porte sur un composé de fulvalène conçu pour avoir un squelette issu de fulvalène, pour avoir quatre structures cycliques particulières formées conjointement avec une partie de la fraction squelette du noyau à cinq chaînons qui forme le squelette de fulvalène et pour avoir un substituant monovalent particulier qui sert de substituant des atomes d'hydrogène ou structures cycliques respectives dans ces quatre structures cycliques ; sur un procédé pour la production du composé ; et sur un polymère de fulvalène obtenu par polymérisation d'un constituant monomère contenant ce composé de fulvalène.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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JP2012008459 | 2012-01-18 | ||
JP2012008458 | 2012-01-18 | ||
JP2012-008458 | 2012-01-18 | ||
JP2012-008459 | 2012-01-18 | ||
JP2012184569A JP6400268B2 (ja) | 2012-01-18 | 2012-08-23 | フルバレン化合物及びその製造方法、並びに、太陽電池用材料及び有機トランジスタ用材料 |
JP2012-184569 | 2012-08-23 |
Publications (1)
Publication Number | Publication Date |
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WO2013108894A1 true WO2013108894A1 (fr) | 2013-07-25 |
Family
ID=48799315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2013/050985 WO2013108894A1 (fr) | 2012-01-18 | 2013-01-18 | Composé de fulvalène et son procédé de production, polymère de fulvalène et matériau de photopile et matériau de transistor organique |
Country Status (1)
Country | Link |
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WO (1) | WO2013108894A1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103435782A (zh) * | 2013-08-17 | 2013-12-11 | 华南理工大学 | 含9,9’-联亚芴基及其衍生物的有机半导体材料及其制备方法与应用 |
CN103468245A (zh) * | 2013-08-16 | 2013-12-25 | 石家庄诚志永华显示材料有限公司 | 一种具有载流子传输能力的oled材料及其制备方法和应用 |
JP2015151450A (ja) * | 2014-02-13 | 2015-08-24 | 国立大学法人山形大学 | 9,9’−ビフルオレニリデンを骨格に含む重合体及びこれを用いた有機薄膜太陽電池 |
CN111116586A (zh) * | 2019-04-17 | 2020-05-08 | 友达光电股份有限公司 | 化合物、具有吡啶环的化合物的合成方法以及发光元件 |
US10825991B2 (en) * | 2014-04-23 | 2020-11-03 | Sumitomo Chemical Company, Limited | Composition and light emitting device using the same |
Citations (2)
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WO2010038251A1 (fr) * | 2008-10-02 | 2010-04-08 | Università Degli Studi Di Roma La Sapienza | Dérivés de bifluorénylidène, leur préparation et leurs utilisations |
JP2010155791A (ja) * | 2008-12-26 | 2010-07-15 | Nagoya Univ | 縮合多環式芳香族化合物、その製法、及び縮合多環式芳香族化合物の共重合体 |
-
2013
- 2013-01-18 WO PCT/JP2013/050985 patent/WO2013108894A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010038251A1 (fr) * | 2008-10-02 | 2010-04-08 | Università Degli Studi Di Roma La Sapienza | Dérivés de bifluorénylidène, leur préparation et leurs utilisations |
JP2010155791A (ja) * | 2008-12-26 | 2010-07-15 | Nagoya Univ | 縮合多環式芳香族化合物、その製法、及び縮合多環式芳香族化合物の共重合体 |
Non-Patent Citations (3)
Title |
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F G BRUNETTI ET AL., ANGEW CHEM INT ED, vol. 49, 2010, pages 532 - 536 * |
J LUO ET AL., ORGANIC LETTERS, vol. 12, no. 24, 2010, pages 5660 - 5663 * |
N ASSADI ET AL., EUR J ORG CHEM, 2011, pages 6773 - 6780 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103468245A (zh) * | 2013-08-16 | 2013-12-25 | 石家庄诚志永华显示材料有限公司 | 一种具有载流子传输能力的oled材料及其制备方法和应用 |
CN103435782A (zh) * | 2013-08-17 | 2013-12-11 | 华南理工大学 | 含9,9’-联亚芴基及其衍生物的有机半导体材料及其制备方法与应用 |
JP2015151450A (ja) * | 2014-02-13 | 2015-08-24 | 国立大学法人山形大学 | 9,9’−ビフルオレニリデンを骨格に含む重合体及びこれを用いた有機薄膜太陽電池 |
US10825991B2 (en) * | 2014-04-23 | 2020-11-03 | Sumitomo Chemical Company, Limited | Composition and light emitting device using the same |
CN111116586A (zh) * | 2019-04-17 | 2020-05-08 | 友达光电股份有限公司 | 化合物、具有吡啶环的化合物的合成方法以及发光元件 |
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