JP2005060571A - エレクトロルミネスセンスポリマー、有機el素子及びディスプレイ装置 - Google Patents
エレクトロルミネスセンスポリマー、有機el素子及びディスプレイ装置 Download PDFInfo
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- JP2005060571A JP2005060571A JP2003293584A JP2003293584A JP2005060571A JP 2005060571 A JP2005060571 A JP 2005060571A JP 2003293584 A JP2003293584 A JP 2003293584A JP 2003293584 A JP2003293584 A JP 2003293584A JP 2005060571 A JP2005060571 A JP 2005060571A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- 238000005401 electroluminescence Methods 0.000 claims abstract description 83
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 17
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001454 anthracenes Chemical class 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 34
- 230000004660 morphological change Effects 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 239000000243 solution Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 239000010408 film Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- IJUDEFZBMMRSNM-UHFFFAOYSA-N 2-bromo-1-(2-bromonaphthalen-1-yl)naphthalene Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3Br)=C(Br)C=CC2=C1 IJUDEFZBMMRSNM-UHFFFAOYSA-N 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 14
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 12
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 12
- NZHXAWZPDDOMSI-UHFFFAOYSA-N 7-bromo-1-(2-bromohexyl)-9,9-diethylfluorene Chemical compound C12=CC=C(Br)C=C2C(CC)(CC)C2=C1C=CC=C2CC(Br)CCCC NZHXAWZPDDOMSI-UHFFFAOYSA-N 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 11
- 238000001514 detection method Methods 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 239000011346 highly viscous material Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- -1 poly (paraphenylene vinylene) Polymers 0.000 description 11
- 229920002223 polystyrene Polymers 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 9
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 238000001194 electroluminescence spectrum Methods 0.000 description 9
- 150000002220 fluorenes Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012156 elution solvent Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N 2,7-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C3C2=C1 CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000000950 dibromo group Chemical group Br* 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- BERXWZRVIGYECI-UHFFFAOYSA-N 4-bromo-1-[4-bromo-2-(trifluoromethyl)phenyl]-2-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1C(F)(F)F BERXWZRVIGYECI-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- CZYAFTZIQWCKOI-UHFFFAOYSA-N 1,5-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1Br CZYAFTZIQWCKOI-UHFFFAOYSA-N 0.000 description 3
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 3
- HGPVZVIPOXMTJD-UHFFFAOYSA-N 2,5-bis(4-bromophenyl)-1,3,4-oxadiazole Chemical compound C1=CC(Br)=CC=C1C1=NN=C(C=2C=CC(Br)=CC=2)O1 HGPVZVIPOXMTJD-UHFFFAOYSA-N 0.000 description 3
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 3
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 238000000944 Soxhlet extraction Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000006617 triphenylamine group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- WSBUZOZAKDVRTK-UHFFFAOYSA-N 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene Chemical compound C1=C(Br)C=C2C(CC(CC)CCCC)(CC(CC)CCCC)C3=CC(Br)=CC=C3C2=C1 WSBUZOZAKDVRTK-UHFFFAOYSA-N 0.000 description 2
- MFYGWCVLNPQWRR-UHFFFAOYSA-N 3,6-dibromo-9-octylcarbazole Chemical compound BrC1=CC=C2N(CCCCCCCC)C3=CC=C(Br)C=C3C2=C1 MFYGWCVLNPQWRR-UHFFFAOYSA-N 0.000 description 2
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 2
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 2
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 2
- IWUQQWLGRYJQQX-UHFFFAOYSA-N 9,9-diethyl-1-hexylfluorene Chemical group C12=CC=CC=C2C(CC)(CC)C2=C1C=CC=C2CCCCCC IWUQQWLGRYJQQX-UHFFFAOYSA-N 0.000 description 2
- 0 CC(CC1)**CI(C)CCC1NC Chemical compound CC(CC1)**CI(C)CCC1NC 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 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 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- OCXGTPDKNBIOTF-UHFFFAOYSA-N dibromo(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 OCXGTPDKNBIOTF-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 1
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- JTJZQRYMZSEOHP-UHFFFAOYSA-N 2,3-dibromo-1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=C(C=3Br)Br)=CC=CC2=C1 JTJZQRYMZSEOHP-UHFFFAOYSA-N 0.000 description 1
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical class C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
- LBLFZUNRAGUAFR-UHFFFAOYSA-N 3-bromo-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=C(Br)C=CC=1)C1=CC=C(C)C=C1 LBLFZUNRAGUAFR-UHFFFAOYSA-N 0.000 description 1
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical class C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 1
- YJUVFJKHTNWDNU-UHFFFAOYSA-N 9,9-bis(2-ethylhexyl)fluorene Chemical compound C1=CC=C2C(CC(CC)CCCC)(CC(CC)CCCC)C3=CC=CC=C3C2=C1 YJUVFJKHTNWDNU-UHFFFAOYSA-N 0.000 description 1
- AHCDKANCCBEQJJ-UHFFFAOYSA-N 9-bromo-9h-fluorene Chemical class C1=CC=C2C(Br)C3=CC=CC=C3C2=C1 AHCDKANCCBEQJJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- JNLMXBVXLLFQRX-UHFFFAOYSA-N CCCCCCC(C=C)N Chemical compound CCCCCCC(C=C)N JNLMXBVXLLFQRX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229920000291 Poly(9,9-dioctylfluorene) Polymers 0.000 description 1
- 229920000285 Polydioctylfluorene Polymers 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229930192419 itoside Natural products 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】 エレクトロルミネスセンスポリマーは、式(1a)のビナフチル誘導体構造単位と式(1b)のアリール構造単位
【化1】
(式中、Arは、エレクトロルミネスセンス可能なπ共役ポリマーを形成しうるアリール構造単位であり、R1、R2、R3及びR4はそれぞれ独立的に、種々の置換基を取りうる。また、ビナフチル誘導体構造単位における点線と実線とで表された二重結合は、不飽和二重結合又は飽和単結合を示している。m及びpは独立的に0〜2、n及びoは独立的に0〜8である。xはビナフチル誘導体構造単位のモル分率であり、yは該アリール構造単位のモル分率である。)
を有するポリマーである。
【選択図】 なし
Description
Y. Ohmori et al, Jpn. J. Appl. Phys., 1991, 30, L1941
を有するELポリマーを提供する。
で表されるものが挙げられる。中でも、入手容易な点でR1とR3とが共に水素原子である場合が好ましい。
(2,7−ジブロモ−9,9−ジオクチルフルオレンの合成)
13C-NMR (CDCl3, δ): 152.5, 139.1, 130.1, 126.2, 121.4, 121.1, 55.7, 40.1, 31.7, 29.6, 29.16, 29.13, 23.6, 22.6, 14.1
(2,7−ジブロモ−9,9−ジ(2−エチルヘキシル)フルオレンの合成)
13C-NMR (CDCl3, δ): 152.2, 139.0, 130.0, 127.4, 127.2, 121.0, 55.4, 44.4, 34.8, 33.6, 28.1, 27.1, 27.0, 14.1, 10.4
(2,2′−ジブロモ−1,1′−ビナフチルの合成)
13C-NMR (CDCl3, δ): 137.0, 133.2, 132.2, 130.0, 129.7, 128.1, 127.3, 126.2, 125.7, 122.6
GC-MS (m/z, %): 410(M+, 11), 252(100), 250(24), 126(36), 125(26), 113(8)
(2,2′−ジブロモ−1,1′−ビフェニルの合成)
13C-NMR (CDCl3, δ): 141.9, 132.5, 130.8, 129.3, 127.0, 123.4
GC-MS (m/z, %): 312 (M++2, 52), 310(M+, 27), 233(59), 231(59), 152(100), 141(29), 76(58), 75(23), 63(18)
(2,2′−ビス(トリフルオロメチル)−4,4′−ジブロモビフェニル[TFMB]の合成(Sandmyer反応))
13C-NMR (CDCl3, δ): 135.0, 133.7, 132.8, 130.4(q, 2J(13C-19F)=31Hz), 129.3, 122.7(q, 1J(13C-19F)=272Hz, CF3), 122.5
GC-MS (m/z, %): 448 (M++2, 74), 446(M+, 100), 348(10), 300(36), 288(52), 269(27), 268(13), 219(80), 199(19), 169(11), 99(19), 75(18), 69(18)
(2,7位にボロン構造を導入した9,9−ジオクチルフルオレンの合成)
(エンドキャップ剤であるトリフェニルアミン誘導体の合成)
13C-NMR (CDCl3, δ): 149.6, 144.5, 133.1, 130.0, 129.9, 124.9, 124.2, 123.8, 122.6, 120.1, 20.9
GC-MS (m/z, %): 353 (M++2, 52), 351(M+, 100), 272(6), 257(10), 180(10), 155(7), 136(10), 127(6), 91(7), 65(6)
(1,5−ジブロモナフタレンの合成)
13C-NMR (CDCl3, δ): 132.9, 130.8, 127.3, 127.2, 122.9
GC-MS (m/z, %): 286(M+2, 100), 284(M+, 92), 207(39), 205(40), 126(100, 74(27), 63(61)
(2,5−ビス(4−ブロモフェニル)−1,3,4−オキサジアゾールの合成)
13C-NMR (CDCl3, δ): 163.9, 132.4, 128.2, 126.5, 122.5
GC-MS (m/z, %): 380(M++2, 75), 378(M+, 40), 245(34), 253(34), 183(100), 157(39), 155(39), 102(13), 88(18), 76(35), 75(31), 50(18)
(2,2′−ジブロモ−1,1′−ビナフチルが20モル%導入された9,9−ジオクチルフルオレンポリマー[PDOF80−BiNp20]の合成)
(9,9−ジオクチルフルオレンポリマー[PDOF]の合成)
窒素気流下、還流冷却管を備えた100ml三口フラスコに、2,7−ジブロモ−9,9−ジオクチルフルオレン1.71g(3.12mmol)、2,7位にボロン構造を導入した9,9−ジオクチルフルオレン2.02g(3.14mmol)、炭酸カリウム2.2g、THF16ml、蒸留水8mlを加え、60℃に加熱した。基質の溶解を確認の後、テトラキス(トリフェニルホスフィン)パラジウム50mgを加え、約48時間加熱撹拌した。
(2,2′−ジブロモ−1,1′−ビフェニルが20モル%導入された9,9−ジオクチルフルオレンポリマー[PDOF80−BiPh20]の合成)
(2,2′−ジブロモ−1,1′−ビナフチルが20モル%導入され、トリフェニルアミン(TPA)4モル%でエンドキャップした9,9−ジオクチルフルオレンポリマーの合成)
(2,2′−ジブロモ−1,1′−ビナフチルが20モル%導入され、トリフェニルアミン(TPA)4モル%でエンドキャップした9,9−ジ(2−エチルヘキシル)フルオレンポリマーの合成)
(2,2′−ジブロモ−1,1′−ビナフチルが20モル%導入された2,2′−ビス(トリフルオロメチル)−4,4′−ジブロモビフェニル(TFMB)ポリマーの合成)
(2,2′−ジブロモ−1,1′−ビナフチルを20mol%、2,7−ジブロモ−9,9−ジエチルヘキシルフルオレンを70mol%、1,5−ジブロモナフタレンを10mol%共重合体の合成[BiNp20−EthylHexFL70−DBN10])
(2,2′−ジブロモ−1,1′−ビナフチルを20mol%、2,7−ジブロモ−9,9−ジエチルヘキシルフルオレンを70mol%、9,10−ジブロモアントラセンを10mol%共重合体の合成[BiNp20−EthylHexFL70−An10])
(2,2′−ジブロモ−1,1′−ビナフチルを20mol%、2,7−ジブロモ−9,9−ジエチルヘキシルフルオレンを70mol%、3,6−ジブロモ−N−オクチルカルバゾールを10mol%共重合体の合成[BiNp20−EthylHexFL70−Carb10])
(2,2′−ジブロモ−1,1′−ビナフチルを20mol%、2,7−ジブロモ−9,9−ジエチルヘキシルフルオレンを70mol%、2,5−ビス(4−ブロモフェニル)−1,3,4−オキサジアゾールを10mol%共重合体の合成[BiNp20−EthylHexFL70−Diazo10])
実施例1及び比較例1で得られたELポリマー自体の示差走査熱分析(DSC、昇温度速度20℃/分、対照α−アルミナ)を、窒素雰囲気下から室温から180℃まで昇温した後、ただちに液体窒素にて0℃まで急冷し、また0℃から200℃までを測定した。得られた結果を、実施例1のELポリマーについては図1(a)に、比較例1のELポリマーについては図1(b)に示す。
ITO(インジウム−酸化錫)[200nm厚、シート抵抗10Ω/sq以下、透過率80%以上]で被覆されたガラス基材を市販の洗浄剤で超音波処理し、次いで脱イオン水にてリンスし、続いてアセトン、そしてIPA(イソプロピルアルコール)で超音波処理、最後にIPAにて煮沸し脱脂処理を施した。その後、エキシマー照射装置にて数分間晒した。
比較例1のポリジオクチルフルオレンホモポリマーは、そのDSC結果を示す図1(b)からわかるように、60℃付近に変曲点(ガラス転移点)が存在し、90℃付近に結晶化に由来すると考えられるピークが存在する。一方、実施例1のオクチルフルオレン−ビナフチルコポリマーは、そのDSC結果を示す図1(a)からわかるように、ガラス転移点が約90℃に転移しており、しかもピークが観察されないことがわかる。
Claims (7)
- 式(1a)のビナフチル誘導体構造単位及び式(1b)のアリール構造単位
(式中、Arは、エレクトロルミネスセンス可能なπ共役ポリマーを形成しうるアリール構造単位であり、R1、R2、R3及びR4はそれぞれ独立的に、水素原子、アルキル基、アルケニル基、アルキニル基、アラルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基又は脂肪族ヘテロ環基である。また、ビナフチル誘導体構造単位における点線と実線とで表された二重結合は、不飽和二重結合又は飽和単結合を示している。m及びpは独立的に0、1又は2であり、n及びoは独立的に0、1、2、3、4、5、6、7又は8である。m、n、o又はpが2以上の整数である場合、2以上のR1、R2、R3又はR4は、それぞれ互いに同じでも異なっていてもよい。xはビナフチル誘導体構造単位のモル分率であり、yはアリール構造単位のモル分率である。)
を有するエレクトロルミネスセンスポリマー。 - xが0.1〜90モル%である請求項1〜3のいずれかに記載のエレクトロルミネスセンスポリマー。
- ビナフチル誘導体構造単位及びフルオレン誘導体構造単位に加えて、カルバゾール誘導体構造単位、アントラセン誘導体構造単位、ナフチル誘導体構造単位、ビフェニル誘導体構造単位、ベンゼン誘導体構造単位又は芳香族ヘテロ環誘導体構造単位の少なくとも一種を有する請求項3に記載のエレクトロルミネスセンスポリマー。
- 請求項1〜5のいずれかに記載のエレクトロルミネスセンスポリマーからなる発光層が一対の電極に挟持されている有機エレクトロルミネスセンス素子。
- 請求項6記載の有機エレクトロルミネスセンス素子を備えたディスプレイ装置。
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US10/567,124 US20070032632A1 (en) | 2003-08-14 | 2004-08-04 | Electroluminescence polymer, organic el device, and display |
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JP2005206826A (ja) * | 2003-12-25 | 2005-08-04 | Sumitomo Chemical Co Ltd | 高分子化合物の製造方法 |
JP2005232449A (ja) * | 2004-01-21 | 2005-09-02 | Sumitomo Chemical Co Ltd | 重合体およびそれを用いた高分子発光素子 |
JP2008525534A (ja) * | 2004-12-18 | 2008-07-17 | メルク パテント ゲーエムベーハー | エレクトロルミネセンスポリマーおよびその使用 |
JP2012510474A (ja) * | 2008-12-01 | 2012-05-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性材料 |
WO2012090972A1 (ja) * | 2010-12-27 | 2012-07-05 | 住友化学株式会社 | 反応性化合物及びそれを用いた高分子化合物の製造方法 |
JP2012524140A (ja) * | 2009-04-16 | 2012-10-11 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマーおよび重合方法 |
JP2012214732A (ja) * | 2011-03-25 | 2012-11-08 | Sumitomo Chemical Co Ltd | 高分子化合物及びそれを用いてなる発光素子 |
US8551624B2 (en) | 2008-12-01 | 2013-10-08 | E I Du Pont De Nemours And Company | Electroactive materials |
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JPH09272730A (ja) * | 1996-04-02 | 1997-10-21 | Polyplastics Co | 高分子重合体の製造方法 |
KR0176336B1 (ko) * | 1996-12-31 | 1999-04-01 | 박원훈 | 아세틸렌기를 함유한 플로렌계 교대 공중합체 및 이를 이용한 전계발광소자 |
JP3817957B2 (ja) * | 1998-05-12 | 2006-09-06 | 住友化学株式会社 | 有機蛍光材料および有機エレクトロルミネッセンス素子 |
DE60007080T2 (de) * | 2000-04-26 | 2004-09-23 | Sony International (Europe) Gmbh | Polyfluore mit Endgruppen, Filme und darauf beruhende Anordnungen |
JP2003327675A (ja) * | 2002-05-09 | 2003-11-19 | Daicel Chem Ind Ltd | 架橋構造を有する軸不斉化合物重合体 |
US6872475B2 (en) * | 2002-12-03 | 2005-03-29 | Canon Kabushiki Kaisha | Binaphthalene derivatives for organic electro-luminescent devices |
-
2003
- 2003-08-14 JP JP2003293584A patent/JP3915757B2/ja not_active Expired - Lifetime
-
2004
- 2004-08-04 US US10/567,124 patent/US20070032632A1/en not_active Abandoned
- 2004-08-04 WO PCT/JP2004/011175 patent/WO2005016992A1/ja active Application Filing
- 2004-08-04 CN CNB2004800300142A patent/CN100497432C/zh active Active
- 2004-08-09 TW TW093123786A patent/TW200508361A/zh unknown
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2007
- 2007-03-21 HK HK07103036.3A patent/HK1096110A1/xx unknown
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2005206826A (ja) * | 2003-12-25 | 2005-08-04 | Sumitomo Chemical Co Ltd | 高分子化合物の製造方法 |
JP2005232449A (ja) * | 2004-01-21 | 2005-09-02 | Sumitomo Chemical Co Ltd | 重合体およびそれを用いた高分子発光素子 |
JP2008525534A (ja) * | 2004-12-18 | 2008-07-17 | メルク パテント ゲーエムベーハー | エレクトロルミネセンスポリマーおよびその使用 |
JP2012510474A (ja) * | 2008-12-01 | 2012-05-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電気活性材料 |
US8551624B2 (en) | 2008-12-01 | 2013-10-08 | E I Du Pont De Nemours And Company | Electroactive materials |
JP2012524140A (ja) * | 2009-04-16 | 2012-10-11 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマーおよび重合方法 |
US8916675B2 (en) | 2009-04-16 | 2014-12-23 | Cambridge Display Technology Limited | Polymer and polymerization method |
WO2012090972A1 (ja) * | 2010-12-27 | 2012-07-05 | 住友化学株式会社 | 反応性化合物及びそれを用いた高分子化合物の製造方法 |
JP2012214732A (ja) * | 2011-03-25 | 2012-11-08 | Sumitomo Chemical Co Ltd | 高分子化合物及びそれを用いてなる発光素子 |
Also Published As
Publication number | Publication date |
---|---|
US20070032632A1 (en) | 2007-02-08 |
TWI303657B (ja) | 2008-12-01 |
CN1867603A (zh) | 2006-11-22 |
HK1096110A1 (en) | 2007-05-25 |
TW200508361A (en) | 2005-03-01 |
JP3915757B2 (ja) | 2007-05-16 |
CN100497432C (zh) | 2009-06-10 |
WO2005016992A1 (ja) | 2005-02-24 |
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