JP2001509184A - アリール−置換ポリ（ｐ−アリーレン−ビニレン）類、その製造法及びエレクトロルミネセンス部品におけるその使用 - Google Patents
アリール−置換ポリ（ｐ−アリーレン−ビニレン）類、その製造法及びエレクトロルミネセンス部品におけるその使用Info
- Publication number
- JP2001509184A JP2001509184A JP52727598A JP52727598A JP2001509184A JP 2001509184 A JP2001509184 A JP 2001509184A JP 52727598 A JP52727598 A JP 52727598A JP 52727598 A JP52727598 A JP 52727598A JP 2001509184 A JP2001509184 A JP 2001509184A
- Authority
- JP
- Japan
- Prior art keywords
- vinylene
- poly
- mmol
- bis
- arylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 58
- 238000002360 preparation method Methods 0.000 title description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- -1 9-anthracenyl Chemical group 0.000 claims description 131
- 239000000203 mixture Substances 0.000 claims description 111
- 229920000642 polymer Polymers 0.000 claims description 111
- 238000006243 chemical reaction Methods 0.000 claims description 93
- 239000002904 solvent Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 150000005347 biaryls Chemical class 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
- 150000004291 polyenes Chemical class 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
- 239000000243 solution Substances 0.000 description 112
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 108
- 238000003756 stirring Methods 0.000 description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 80
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 70
- 230000015572 biosynthetic process Effects 0.000 description 66
- 238000003786 synthesis reaction Methods 0.000 description 65
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000010410 layer Substances 0.000 description 49
- 229910052763 palladium Inorganic materials 0.000 description 49
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 48
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- 238000001035 drying Methods 0.000 description 42
- 239000000047 product Substances 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- 239000012074 organic phase Substances 0.000 description 35
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 32
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 31
- 238000010992 reflux Methods 0.000 description 28
- 239000007789 gas Substances 0.000 description 27
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 239000004305 biphenyl Substances 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000004793 Polystyrene Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 16
- 239000011572 manganese Substances 0.000 description 16
- 235000006408 oxalic acid Nutrition 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 16
- 230000001681 protective effect Effects 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 238000000825 ultraviolet detection Methods 0.000 description 16
- 239000003446 ligand Substances 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- 150000003003 phosphines Chemical class 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 9
- 239000004809 Teflon Substances 0.000 description 9
- 229920006362 Teflon® Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 239000012258 stirred mixture Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- NLOCNKYNECKGNC-UHFFFAOYSA-N 1,4-bis(chloromethyl)-2-(3,7-dimethyloctoxy)-5-methoxybenzene Chemical compound COC1=CC(CCl)=C(OCCC(C)CCCC(C)C)C=C1CCl NLOCNKYNECKGNC-UHFFFAOYSA-N 0.000 description 8
- SRWLAIVZCGWRIW-UHFFFAOYSA-N 1,4-bis(chloromethyl)-2-[4-(3,7-dimethyloctoxy)phenyl]benzene Chemical group C1=CC(OCCC(C)CCCC(C)C)=CC=C1C1=CC(CCl)=CC=C1CCl SRWLAIVZCGWRIW-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- QPUMAVSVFVPLTD-UHFFFAOYSA-N 1,4-bis(chloromethyl)-2-(2,5-dimethylphenyl)benzene Chemical group CC1=CC=C(C)C(C=2C(=CC=C(CCl)C=2)CCl)=C1 QPUMAVSVFVPLTD-UHFFFAOYSA-N 0.000 description 7
- ZJGZYMYWBCQKFI-UHFFFAOYSA-N 1,4-bis(chloromethyl)-2-[3-(3,7-dimethyloctoxy)phenyl]benzene Chemical group CC(C)CCCC(C)CCOC1=CC=CC(C=2C(=CC=C(CCl)C=2)CCl)=C1 ZJGZYMYWBCQKFI-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- 238000005191 phase separation Methods 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 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 6
- IFTYHSVPPGZJQG-UHFFFAOYSA-N 1-chloro-3,7-dimethyloctane Chemical compound CC(C)CCCC(C)CCCl IFTYHSVPPGZJQG-UHFFFAOYSA-N 0.000 description 5
- QXISTPDUYKNPLU-UHFFFAOYSA-N 2-bromo-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Br)=C1 QXISTPDUYKNPLU-UHFFFAOYSA-N 0.000 description 5
- QPBGNSFASPVGTP-UHFFFAOYSA-N 2-bromoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Br)=C1 QPBGNSFASPVGTP-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- NJVLRKTULNWMSQ-UHFFFAOYSA-N diethyl 2-bromobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C(Br)=C1 NJVLRKTULNWMSQ-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000005273 aeration Methods 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
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- 238000002207 thermal evaporation Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/105—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a methine or polymethine dye
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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
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19652261.7 | 1996-12-16 | ||
| DE19652261A DE19652261A1 (de) | 1996-12-16 | 1996-12-16 | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
| PCT/EP1997/006916 WO1998027136A1 (de) | 1996-12-16 | 1997-12-11 | ARYLSUBSTITUIERTE POLY(p-ARYLENVINYLENE), VERFAHREN ZUR HERSTELLUNG UND DEREN VERWENDUNG IN ELEKTROLUMINESZENZBAUELEMENTEN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001509184A true JP2001509184A (ja) | 2001-07-10 |
| JP2001509184A5 JP2001509184A5 (enExample) | 2009-07-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52727598A Pending JP2001509184A (ja) | 1996-12-16 | 1997-12-11 | アリール−置換ポリ（ｐ−アリーレン−ビニレン）類、その製造法及びエレクトロルミネセンス部品におけるその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6458909B1 (enExample) |
| EP (1) | EP0944663B1 (enExample) |
| JP (1) | JP2001509184A (enExample) |
| KR (1) | KR100541782B1 (enExample) |
| CN (2) | CN100339413C (enExample) |
| AT (1) | ATE215104T1 (enExample) |
| CA (1) | CA2275612C (enExample) |
| DE (2) | DE19652261A1 (enExample) |
| WO (1) | WO1998027136A1 (enExample) |
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| JP2001522926A (ja) * | 1997-11-05 | 2001-11-20 | アクシーバ・ゲーエムベーハー | 置換ポリ（アリーレンビニレン）、それらの製造方法、およびエレクトロルミネセント素子におけるそれらの使用 |
| JP2003524035A (ja) * | 2000-02-23 | 2003-08-12 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | アリール置換ポリ−ｐ−アリーレンビニレン |
| JP2008518078A (ja) * | 2004-11-01 | 2008-05-29 | エージェンシー フォー サイエンス、テクノロジー アンド リサーチ | ポリ（アリーレンビニレン）およびポリ（ヘテロアリーレンビニレン）発光ポリマーならびにポリマー発光デバイス |
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| JP2010515779A (ja) * | 2006-10-11 | 2010-05-13 | ユニバーシティ オブ フロリダ リサーチ ファンデーション、インク． | ペンダントパイ相互作用性／結合性置換基を含有する電気活性ポリマー、そのカーボンナノチューブ複合体、およびその形成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| IT1236509B (it) * | 1989-10-06 | 1993-03-11 | Francesco Masi | Procedimento per la preparazione di copolimeri etilene-butene-1 con densita' ultra-bassa. |
| DE69110922T2 (de) * | 1990-02-23 | 1995-12-07 | Sumitomo Chemical Co | Organisch elektrolumineszente Vorrichtung. |
| US5679757A (en) * | 1990-12-12 | 1997-10-21 | The Regents Of The University Of California | Highly organic solvent soluble, water insoluble electroluminescent polyphenylene vinylenes having pendant steroid groups and products and uses thereof |
| US5723873A (en) * | 1994-03-03 | 1998-03-03 | Yang; Yang | Bilayer composite electrodes for diodes |
| US5558904A (en) * | 1994-07-08 | 1996-09-24 | Xerox Corporation | Electroluminescent devices containing a conjugated polymer obtained via halogen precursor route chemistry |
-
1996
- 1996-12-16 DE DE19652261A patent/DE19652261A1/de not_active Withdrawn
-
1997
- 1997-12-11 CA CA002275612A patent/CA2275612C/en not_active Expired - Fee Related
- 1997-12-11 CN CNB2004100862052A patent/CN100339413C/zh not_active Expired - Fee Related
- 1997-12-11 EP EP97953781A patent/EP0944663B1/de not_active Expired - Lifetime
- 1997-12-11 JP JP52727598A patent/JP2001509184A/ja active Pending
- 1997-12-11 KR KR1019997005403A patent/KR100541782B1/ko not_active Expired - Lifetime
- 1997-12-11 WO PCT/EP1997/006916 patent/WO1998027136A1/de not_active Ceased
- 1997-12-11 AT AT97953781T patent/ATE215104T1/de not_active IP Right Cessation
- 1997-12-11 CN CNB971806438A patent/CN1267469C/zh not_active Expired - Fee Related
- 1997-12-11 DE DE59706803T patent/DE59706803D1/de not_active Expired - Lifetime
- 1997-12-16 US US08/991,559 patent/US6458909B1/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001522926A (ja) * | 1997-11-05 | 2001-11-20 | アクシーバ・ゲーエムベーハー | 置換ポリ（アリーレンビニレン）、それらの製造方法、およびエレクトロルミネセント素子におけるそれらの使用 |
| JP2003524035A (ja) * | 2000-02-23 | 2003-08-12 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | アリール置換ポリ−ｐ−アリーレンビニレン |
| JP2008518078A (ja) * | 2004-11-01 | 2008-05-29 | エージェンシー フォー サイエンス、テクノロジー アンド リサーチ | ポリ（アリーレンビニレン）およびポリ（ヘテロアリーレンビニレン）発光ポリマーならびにポリマー発光デバイス |
| JP2010515779A (ja) * | 2006-10-11 | 2010-05-13 | ユニバーシティ オブ フロリダ リサーチ ファンデーション、インク． | ペンダントパイ相互作用性／結合性置換基を含有する電気活性ポリマー、そのカーボンナノチューブ複合体、およびその形成方法 |
| US8961830B2 (en) | 2006-10-11 | 2015-02-24 | University Of Florida Research Foundation, Inc. | Electroactive polymers containing pendant pi-interacting/binding substituents, their carbon nanotube composites, and processes to form the same |
| WO2009063757A1 (ja) * | 2007-11-14 | 2009-05-22 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2275612C (en) | 2006-12-05 |
| CN1267469C (zh) | 2006-08-02 |
| ATE215104T1 (de) | 2002-04-15 |
| CA2275612A1 (en) | 1998-06-25 |
| DE19652261A1 (de) | 1998-06-18 |
| WO1998027136A1 (de) | 1998-06-25 |
| EP0944663B1 (de) | 2002-03-27 |
| CN1654505A (zh) | 2005-08-17 |
| KR20000057614A (ko) | 2000-09-25 |
| CN100339413C (zh) | 2007-09-26 |
| US6458909B1 (en) | 2002-10-01 |
| KR100541782B1 (ko) | 2006-01-10 |
| CN1244206A (zh) | 2000-02-09 |
| EP0944663A1 (de) | 1999-09-29 |
| DE59706803D1 (de) | 2002-05-02 |
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