JP4435690B2 - 有機エレクトロルミネセンスデバイスにおける使用のためのアリール置換されたポリインデノフルオレン - Google Patents
有機エレクトロルミネセンスデバイスにおける使用のためのアリール置換されたポリインデノフルオレン Download PDFInfo
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- JP4435690B2 JP4435690B2 JP2004549129A JP2004549129A JP4435690B2 JP 4435690 B2 JP4435690 B2 JP 4435690B2 JP 2004549129 A JP2004549129 A JP 2004549129A JP 2004549129 A JP2004549129 A JP 2004549129A JP 4435690 B2 JP4435690 B2 JP 4435690B2
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- 229920000642 polymer Polymers 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 53
- -1 4-octylphenyl group Chemical group 0.000 claims description 41
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000004820 halides Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005620 boronic acid group Chemical group 0.000 claims description 6
- 239000012212 insulator Substances 0.000 claims description 6
- 125000005259 triarylamine group Chemical group 0.000 claims description 6
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical group 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 30
- 239000010410 layer Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 15
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000002800 charge carrier Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 0 CCCCCCCCC1(C)c(cc(*(*)*)cc2)c2-c2c1cc1-c3ccc(C(C)(*)*)cc3C3(c4ccccc4-c4ccccc34)c1c2 Chemical compound CCCCCCCCC1(C)c(cc(*(*)*)cc2)c2-c2c1cc1-c3ccc(C(C)(*)*)cc3C3(c4ccccc4-c4ccccc34)c1c2 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 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
- 150000002148 esters Chemical class 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical class CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 2
- KKLCYBZPQDOFQK-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1 KKLCYBZPQDOFQK-UHFFFAOYSA-N 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- RDLVNTIPWHWPDA-UHFFFAOYSA-N diethyl 2,5-diphenylbenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C=1C=C(C=2C=CC=CC=2)C(C(=O)OCC)=CC=1C1=CC=CC=C1 RDLVNTIPWHWPDA-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 1
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 1
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- ZKOZLOAYMNNGBY-UHFFFAOYSA-N 1,2,3,4-tetraoctylindeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=C(CCCCCCCC)C(CCCCCCCC)=C(CCCCCCCC)C(CCCCCCCC)=C5C4=CC=C3C2=C1 ZKOZLOAYMNNGBY-UHFFFAOYSA-N 0.000 description 1
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical group C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-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
- OOZQSVXPBCINJF-UHFFFAOYSA-N 1-bromo-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(Br)C=C1 OOZQSVXPBCINJF-UHFFFAOYSA-N 0.000 description 1
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 1
- KTQHNKGSFJUMBH-UHFFFAOYSA-N 12,12-dioctyl-6,6-bis(4-octylphenyl)indeno[1,2-b]fluorene 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane Chemical compound C(CCCCCCC)C1(C2=CC=CC=C2C2=CC=3C(C=4C=CC=CC4C3C=C21)(C2=CC=C(C=C2)CCCCCCCC)C2=CC=C(C=C2)CCCCCCCC)CCCCCCCC.C2(=CC=CC=C2)B2OC(C)(C)C(C)(C)O2 KTQHNKGSFJUMBH-UHFFFAOYSA-N 0.000 description 1
- ZBALYQKHSQLEJI-UHFFFAOYSA-N 2,8-dibromo-12,12-dioctyl-6,6-bis(4-octylphenyl)indeno[1,2-b]fluorene Chemical compound C1=CC(CCCCCCCC)=CC=C1C1(C=2C=CC(CCCCCCCC)=CC=2)C2=CC(Br)=CC=C2C2=CC(C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C33)=C3C=C21 ZBALYQKHSQLEJI-UHFFFAOYSA-N 0.000 description 1
- YUILNUQGQCXRJI-UHFFFAOYSA-N 2,8-dibromo-6,6,12,12-tetrakis(4-octylphenyl)indeno[1,2-b]fluorene Chemical compound C1=CC(CCCCCCCC)=CC=C1C1(C=2C=CC(CCCCCCCC)=CC=2)C2=CC(Br)=CC=C2C2=CC(C(C3=CC(Br)=CC=C33)(C=4C=CC(CCCCCCCC)=CC=4)C=4C=CC(CCCCCCCC)=CC=4)=C3C=C21 YUILNUQGQCXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
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- FLLOVYUUNCVOQA-UHFFFAOYSA-N indeno[1,2-b]fluorene Chemical compound C1=C2C=CC=CC2=C2C1=CC1=C3C=CC=CC3=CC1=C2 FLLOVYUUNCVOQA-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 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 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 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 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/70—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a condensed ring system consisting of at least two, mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic ring, e.g. cyclophanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- 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
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- 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
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
Description
本発明は、アリール置換されたトランス−インデノフルオレンの繰り返し単位を含む有機半導体ポリマー、このようなポリマーを調製するモノマー、このようなポリマーの調製方法、及び有機光電子工学デバイスにおけるこのようなポリマーの使用に関する。
半導体有機ポリマーは、数十年間に渡り知られている。過去10年の間、これらは、トランジスタとしての、並びに有機光起電性デバイス(特に太陽電池)、有機光検出器、及びエレクトロルミネセンスデバイスを含む光電子工学デバイスの分野における増加する用途を見出し、また、高分子発光デバイスとしても知られており、例えば、WO 90/13148を参照されたい。
本発明者らは、6位及び/若しくは12位において、少なくとも1つの芳香族基または複素環式芳香族基で置換されたポリ(トランス−インデノフルオレン)が、上記した不都合を示さないことを見出した。従って、これらは、青色発光デバイスにおける使用に適している。さらに、本発明者らは、これらポリ(トランス−インデノフルオレン)が、ポリフルオレンと比べて、正孔輸送に対してより安定であることを見出した。一連のポリ(トランス−インデノフルオレン)に、発光デバイスにおけるより広い利用をもたらすために、本発明者等は、トランス−インデノフルオレンユニット上に少なくとも1つのアリール、またはヘテロアリール置換基を与えることにより、より高い電子親和性、従って改善された電子注入性質及び電子輸送性質を有するトランス−インデノフルオレンユニットを提供することができることを見出した。このようなアリール置換されたトランス−インデノフルオレンユニットのさらなる利点は、これらのユニットを含むポリマーが、より高いTg(ガラス転移温度)を有し、従って、より安定であり、及びより長命の発光デバイスを提供することである。
R1及びR2が、アリール若しくはヘテロアリール基を含み、R3及びR4が、アルキル基を含む場合、R1及びR2は、4−オクチルフェニル及び4−tert−ブチル−フェニル置換基から選択され、並びにR3及びR4は、オクチル置換基を含むことが好ましい。
(a)各Pがボロン酸基、ボロン酸エステル基、及びボラン基から選択されるボロン誘導体官能基である本発明の第2の側面において記載したモノマーと、独立して、ハライド、若しくは式−O−SO2−Zの部位から選択される少なくとも2つの反応性の官能基を有する芳香族モノマー、または
(b)各Pが、独立して、反応性ハライド官能基、及び式−O−SO2−Zの基から成る群から選択される本発明の第2の側面において記載したモノマーと、ボロン酸基、ボロン酸エステル基、及びボラン基から選択される少なくとも2つのボロン誘導体官能基を有する芳香族モノマー、または
(c)1つのPが、反応性ハライド官能基、若しくは式−O−SO2−Zの基であり、他方のPが、ボロン酸基、ボロン酸エステル基、及びボラン基から選択されるボロン誘導体官能基である本発明の第2の側面において記載したモノマー
式中、Zが、任意に置換されたアルキル及びアリールから成る基から選択される反応混合物であって、芳香族モノマーの重合を触媒するに適した触媒の触媒量、及びボロン誘導体官能基をボロナートアニオン性基に、特定の理論に拘束されることを望むことなく、変換させるに十分な量の塩基を含む反応混合物を重合することを包含する。
(a)Pが、式−B(OR14)(OR15)の基である本発明の第7の側面によるモノマーと、独立して、ハライドまたは式−O−SO2−Zの基から選択される少なくとも2つの反応性の官能基を有する芳香族モノマー、または
(b)Pが、反応性ハライド官能基、または式−O−SO2−Zの基である本発明の第7の側面によるモノマー
である反応混合物であって、芳香族モノマーの重合を触媒するに適した触媒の触媒量、及びボロン誘導体官能基をボロナートアニオン性基に、特定の理論に拘束されることを望むことなく、変換させるに十分な量の塩基を含む反応混合物を重合することを包含する。
本発明によるポリマーを、上記したアリール置換されたインデノフルオレンのボロン酸ジエステルと、WO 00/53656に記載されている方法に基づくジブロモ−アリールアミンとのスズキ重合により調製した。比較の目的で、上記式(I)の置換基R1〜R4が全てn−オクチルである同一のポリマーを調製した。
Claims (23)
- R1、R2、R3、及びR4のうちの少なくとも2つが、アリール基またはヘテロアリール基を含む請求項1に記載のポリマー。
- R1、R2、R3、及びR4のうちの少なくとも3つが、アリール基またはヘテロアリール基を含む請求項1に記載のポリマー。
- R1、R2、R3、及びR4が、アリール基またはヘテロアリール基を含む請求項1に記載のポリマー。
- R1及びR2が、アリール基またはヘテロアリール基を含み、R3及びR4がアルキル基を含む請求項1に記載のポリマー。
- 前記アリール基が、任意に置換されたフェニル基を含む請求項1〜5のいずれか一項に記載のポリマー。
- 前記アリール基が、4−オクチルフェニル基、または4−tert-ブチル−フェニル基を含む請求項1〜6のいずれか一項に記載のポリマー。
- 第2の繰り返しユニットを含む請求項1〜7のいずれか一項に記載のポリマー。
- 前記第2の繰り返しユニットが、トリアリールアミン、及び複素環式芳香族化合物から選択される請求項8に記載のポリマー。
- 請求項10のいずれか一項で定義された前記第1のモノマーと、前記第1のモノマーと同一であるか異なる第2のモノマーを、モノマーが重合するための条件下で反応させる工程を含むポリマーの調製方法。
- (a)各Pが、ボロン酸基、ボロン酸エステル基、およびボラン基から選択されるボロン誘導体官能基である請求項10に記載のモノマーと、独立して、ハライドまたは式−O−SO2−Zの基から選択される少なくとも2つの反応性官能基を有する芳香族モノマー、または
(b)各Pが、独立して、反応性ハライド官能基、ハライド及びZが請求項10において定義したものである式−O−SO2−Zから独立して選択される官能基から成る群から選択される請求項10に記載のモノマーと、ボロン酸基、ボロン酸エステル基、及びボラン基から選択される少なくとも2つのボロン誘導体官能基を有する芳香族モノマー、または
(c)1つのPが、反応性ハライド官能基、またはZが請求項10において定義された通りである式−O−SO2−Zの基であり、他方のPが、ボロン酸基、ボロン酸エステル基、及びボラン基から選択されるボロン酸誘導体官能基である請求項10に記載のモノマーからなる反応混合物であって、触媒量の、芳香族モノマーの重合を触媒するに適した触媒、及びボロン酸誘導体官能基をボロナートアニオン性基に変換させるために十分な量の塩基を含有する反応混合物を重合することを包含する請求項11に記載のポリマーの調製方法。 - 請求項1〜9のいずれか一項に記載のポリマーを含む有機発光デバイス。
- 前記R8、R9、R10、及びR11が、独立して、任意に置換されたアルキル、アルコキシ、アリール、アリールオキシ、ヘテロアリール、またはヘテロアリールオキシから成る群から選択される請求項14に記載のモノマー。
- Pが、官能性ハロゲン、式−O−SO2Zの一価のユニット、または式−B(OR14)(OR15)の一価のユニットから選択され、式中、R14及びR15は同一であるか異なり、独立して、水素または請求項14において定義された置換基R12及びR13を表し、結合して環を形成してもよく、Zは請求項10において定義された通りである請求項14または15に記載のモノマー。
- 前記R12、R13、R14、及びR15が同一であるか異なり、水素及び任意に置換されたアルキルから成る群から選択される請求項14〜16のいずれか一項に記載のモノマー。
- 前記R12とR13及び/またはR14とR15が、結合して任意に置換されたエチレン基を形成してもよい請求項17に記載のモノマー。
- (a)Pが、式−B(OR14)(OR15)の基であり、R14及びR15が請求項16において定義された通りである請求項14〜18のいずれか一項に記載のモノマーと、独立して、ハライド、若しくはZが請求項10において定義された通りである式−O−SO2−Zの基から選択される、少なくとも2つの反応性の官能基を有する芳香性モノマー、または
(b)Pが、反応性ハライド官能基、若しくはZが請求項10において定義された通りである式−O−SO2−Zの基である請求項14〜18のいずれか一項に記載のモノマーからなる反応混合物であって、触媒量の、芳香族モノマーの重合を触媒するに適した触媒、及びボロン酸誘導体官能基をボロナートアニオン性基に変換させるために十分な量の塩基を含有する反応混合物を重合することを包含するポリマーの調製方法。 - 請求項1〜9のいずれか一項に記載のオリゴマー、またはポリマーを含むスイッチデバイス。
- 第1の面及び第2の面を有する絶縁体、前記絶縁体の第1の面上に配置されたゲート電極、前記絶縁体の第2の面上に配置された請求項1〜9のいずれか一項に記載のポリマー、並びに前記ポリマー上に配置されたドレイン電極及びソース電極を包含する電界効果トランジスタ。
- 請求項21に記載の電界効果トランジスタを含む集積回路。
- 請求項1〜9のいずれか一項に記載のポリマーを含む光電池。
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GBGB0226010.7A GB0226010D0 (en) | 2002-11-08 | 2002-11-08 | Polymers for use in organic electroluminescent devices |
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- 2002-11-08 GB GBGB0226010.7A patent/GB0226010D0/en not_active Ceased
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2003
- 2003-11-06 EP EP03775305A patent/EP1562997B1/en not_active Expired - Lifetime
- 2003-11-06 CN CNB2003801029115A patent/CN100569827C/zh not_active Expired - Lifetime
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- 2003-11-06 WO PCT/EP2003/012369 patent/WO2004041901A1/en active Application Filing
- 2003-11-06 DE DE60329413T patent/DE60329413D1/de not_active Expired - Lifetime
- 2003-11-06 US US10/533,920 patent/US8860007B2/en not_active Expired - Fee Related
- 2003-11-06 JP JP2004549129A patent/JP4435690B2/ja not_active Expired - Lifetime
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WO2004041901A1 (en) | 2004-05-21 |
JP2006517595A (ja) | 2006-07-27 |
EP1562997B1 (en) | 2009-09-23 |
CN100569827C (zh) | 2009-12-16 |
EP1562997A1 (en) | 2005-08-17 |
GB0226010D0 (en) | 2002-12-18 |
US20060046092A1 (en) | 2006-03-02 |
KR101077712B1 (ko) | 2011-10-27 |
DE60329413D1 (de) | 2009-11-05 |
KR20050084947A (ko) | 2005-08-29 |
US8860007B2 (en) | 2014-10-14 |
CN1711301A (zh) | 2005-12-21 |
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