JP2006517595A - 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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- JP2006517595A JP2006517595A JP2004549129A JP2004549129A JP2006517595A JP 2006517595 A JP2006517595 A JP 2006517595A JP 2004549129 A JP2004549129 A JP 2004549129A JP 2004549129 A JP2004549129 A JP 2004549129A JP 2006517595 A JP2006517595 A JP 2006517595A
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- 229920000642 polymer Polymers 0.000 claims abstract description 88
- 239000000178 monomer Substances 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims description 59
- -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 20
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 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
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 6
- 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
- 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
- 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
- 239000000203 mixture Substances 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
- 125000000547 substituted alkyl group Chemical group 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
- 125000004185 ester group Chemical group 0.000 claims 4
- 150000001642 boronic acid derivatives Chemical group 0.000 claims 3
- 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
- 230000003287 optical effect Effects 0.000 abstract description 4
- 230000005693 optoelectronics Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 30
- 239000010410 layer Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 16
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 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
- 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
- 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 238000006243 chemical reaction Methods 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
- 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
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- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
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- 125000004001 thioalkyl group Chemical group 0.000 description 2
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- 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
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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
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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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- 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
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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
-
- 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
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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
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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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- 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
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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
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Abstract
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 (24)
- 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。
- 前記各Pが、独立して、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反応性ボロン誘導体基、反応性ハライド基、または式−O−SO2−Z(ここで、Zは任意に置換されたアルキル及びアリールから成る群から選択される)の基から選択される請求項10に記載のモノマー。
- 請求項10または11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11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11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11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11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11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12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15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15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11において定義された通りである請求項15または16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15〜17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18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17において定義された通りである請求項15〜19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11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11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15〜19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22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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DE102008018670A1 (de) | 2008-04-14 | 2009-10-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8343381B1 (en) | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
DE102008024182A1 (de) * | 2008-05-19 | 2009-11-26 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtung |
DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008050841B4 (de) | 2008-10-08 | 2019-08-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
KR20110097612A (ko) | 2008-11-11 | 2011-08-31 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 |
DE102009022858A1 (de) | 2009-05-27 | 2011-12-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057050B4 (de) | 2008-11-13 | 2021-06-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057051B4 (de) | 2008-11-13 | 2021-06-17 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
EP2352801B1 (en) | 2008-12-01 | 2017-06-21 | E. I. du Pont de Nemours and Company | Electroactive materials |
JP2012510540A (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 |
KR20140116526A (ko) * | 2008-12-04 | 2014-10-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기활성 재료 |
DE102009005289B4 (de) | 2009-01-20 | 2023-06-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung und elektronische Vorrichtungen, enthaltend diese |
KR101004406B1 (ko) * | 2009-01-20 | 2010-12-28 | 경희대학교 산학협력단 | 인데노플루오렌아민 화합물의 제조방법 |
DE102009005288A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
DE102009010714A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Vernetzbare und vernetzte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung |
DE102009011223A1 (de) | 2009-03-02 | 2010-09-23 | Merck Patent Gmbh | Metallkomplexe |
DE102009013041A1 (de) | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101477613B1 (ko) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
KR101582707B1 (ko) | 2009-04-03 | 2016-01-05 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기활성 재료 |
CN102421858A (zh) | 2009-06-22 | 2012-04-18 | 默克专利有限公司 | 导电制剂 |
DE102009031021A1 (de) | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009033371A1 (de) | 2009-07-16 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009034625A1 (de) | 2009-07-27 | 2011-02-03 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8581262B2 (en) | 2009-08-04 | 2013-11-12 | Merck Patent Gmbh | Electronic devices comprising multi cyclic hydrocarbons |
DE102009053644B4 (de) | 2009-11-17 | 2019-07-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009042693A1 (de) | 2009-09-23 | 2011-03-24 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
CN102510889B (zh) | 2009-09-29 | 2015-11-25 | E.I.内穆尔杜邦公司 | 用于发光应用的氘代化合物 |
GB0917087D0 (en) | 2009-09-30 | 2009-11-11 | Lomox Ltd | Electroluminescent materials |
DE102009048791A1 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
DE102009053191A1 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009052428A1 (de) | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
DE102009053382A1 (de) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009053836A1 (de) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP5897472B2 (ja) | 2009-12-22 | 2016-03-30 | 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機能性界面活性剤 |
EP2517278B1 (en) | 2009-12-22 | 2019-07-17 | Merck Patent GmbH | Electroluminescent formulations |
WO2011076323A1 (en) | 2009-12-22 | 2011-06-30 | Merck Patent Gmbh | Formulations comprising phase-separated functional materials |
US9368761B2 (en) | 2009-12-23 | 2016-06-14 | Merck Patent Gmbh | Compositions comprising organic semiconducting compounds |
DE102010004803A1 (de) | 2010-01-16 | 2011-07-21 | Merck Patent GmbH, 64293 | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
DE102010007938A1 (de) | 2010-02-12 | 2011-10-06 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102010009193B4 (de) | 2010-02-24 | 2022-05-19 | MERCK Patent Gesellschaft mit beschränkter Haftung | Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend |
DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
JP6246468B2 (ja) | 2010-03-11 | 2017-12-13 | メルク パテント ゲーエムベーハー | 治療および化粧品におけるファイバー |
EP2545600A2 (en) | 2010-03-11 | 2013-01-16 | Merck Patent GmbH | Radiative fibers |
US9627632B2 (en) | 2010-03-23 | 2017-04-18 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
DE102010012738A1 (de) | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US20130026421A1 (en) | 2010-04-12 | 2013-01-31 | Merck Patent Gmbh | Composition and method for preparation of organic electronic devices |
DE102010014933A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010019306B4 (de) | 2010-05-04 | 2021-05-20 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
WO2011147521A1 (en) | 2010-05-27 | 2011-12-01 | Merck Patent Gmbh | Down conversion |
EP3309236B1 (en) | 2010-05-27 | 2019-11-27 | Merck Patent GmbH | Electroluminescent device comprising quantum dots and use of a formulation comprising quantum dots |
US9206352B2 (en) | 2010-05-27 | 2015-12-08 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
DE102010024335A1 (de) | 2010-06-18 | 2011-12-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102010024542A1 (de) | 2010-06-22 | 2011-12-22 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010024897A1 (de) | 2010-06-24 | 2011-12-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010033080A1 (de) * | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010048607A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102010048608A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP6022478B2 (ja) | 2011-01-13 | 2016-11-09 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
DE102012000064A1 (de) | 2011-01-21 | 2012-07-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8751777B2 (en) | 2011-01-28 | 2014-06-10 | Honeywell International Inc. | Methods and reconfigurable systems to optimize the performance of a condition based health maintenance system |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
EP2687304B1 (en) * | 2011-03-17 | 2019-01-23 | Sumitomo Chemical Company Limited | Metal complex compositions and mixture thereof |
EP2697226B1 (de) | 2011-04-13 | 2017-01-18 | Merck Patent GmbH | Verbindungen für elektronische vorrichtungen |
CN103476774B (zh) | 2011-04-13 | 2017-02-15 | 默克专利有限公司 | 用于电子器件的材料 |
WO2012143079A1 (de) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
KR101970940B1 (ko) | 2011-05-05 | 2019-04-22 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
EP2705550B1 (de) | 2011-05-05 | 2017-07-05 | Merck Patent GmbH | Verbindungen für elektronische vorrichtungen |
WO2013013754A1 (en) | 2011-07-25 | 2013-01-31 | Merck Patent Gmbh | Copolymers with functionalized side chains |
EP2737555A2 (en) | 2011-07-25 | 2014-06-04 | Merck Patent GmbH | Polymers and oligomers with functionalized side groups |
DE102011079847A1 (de) | 2011-07-26 | 2013-01-31 | Eberhard-Karls-Universität Tübingen | Komplexverbindungen mit anionischen Liganden mit zwei P-Donoren und ihre Verwendung im opto-elektronischen Bereich |
DE102011079857B4 (de) | 2011-07-26 | 2013-03-21 | Eberhard-Karls-Universität Tübingen | Komplexverbindungen mit vierzähnigen Liganden und ihre Verwendung im opto-elektronischen Bereich |
DE102011079856A1 (de) | 2011-07-26 | 2013-01-31 | Eberhard-Karls-Universität Tübingen | Komplexverbindungen mit einem Liganden mit einem N- und einem P-Donor und ihre Verwendung im opto-elektronischen Bereich |
KR102088637B1 (ko) | 2011-07-29 | 2020-03-13 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
EP3439065B1 (de) | 2011-08-03 | 2022-01-12 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
CN104105777B (zh) | 2011-10-27 | 2016-08-24 | 默克专利有限公司 | 用于电子器件的材料 |
WO2013083216A1 (de) | 2011-11-17 | 2013-06-13 | Merck Patent Gmbh | Spiro -dihydroacridinderivate und ihre verwendung als materialien für organische elektrolumineszenzvorrichtungen |
CN103137870A (zh) * | 2011-11-29 | 2013-06-05 | 海洋王照明科技股份有限公司 | 聚合物太阳能电池及其制备方法 |
KR101961613B1 (ko) | 2011-12-12 | 2019-03-25 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
DE102011121022A1 (de) | 2011-12-13 | 2013-06-13 | Merck Patent Gmbh | Organische Sensibilisatoren für Up- Conversion |
DE102012022880A1 (de) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend organische Schichten |
EP3235892B1 (en) | 2012-02-14 | 2019-02-27 | Merck Patent GmbH | Materials for organic electroluminescent devices |
EP2817350A2 (de) | 2012-02-22 | 2014-12-31 | Merck Patent GmbH | Polymere enthaltend dibenzocycloheptan-struktureinheiten |
KR102139456B1 (ko) | 2012-03-23 | 2020-07-30 | 메르크 파텐트 게엠베하 | 전계발광 소자용 9,9'-스피로바이잔텐 유도체 |
DE102012011335A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Verbindungen für Organische Elekronische Vorrichtungen |
EP2867329A1 (de) | 2012-06-29 | 2015-05-06 | Merck Patent GmbH | Polymere enthaltend 2,7-pyren-struktureinheiten |
EP2872590B1 (de) | 2012-07-13 | 2018-11-14 | Merck Patent GmbH | Metallkomplexe |
US9882142B2 (en) | 2012-07-23 | 2018-01-30 | Merck Patent Gmbh | Compounds and organic electronic devices |
KR102196432B1 (ko) | 2012-07-23 | 2020-12-29 | 메르크 파텐트 게엠베하 | 화합물 및 유기 전계 발광 디바이스 |
KR20150038193A (ko) | 2012-07-23 | 2015-04-08 | 메르크 파텐트 게엠베하 | 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물 |
KR101401639B1 (ko) | 2012-07-27 | 2014-06-02 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
US11917901B2 (en) | 2012-08-07 | 2024-02-27 | Udc Ireland Limited | Metal complexes |
CN104619810B (zh) | 2012-09-10 | 2017-02-15 | 沙特基础工业公司 | 用于太阳能电池和挠性电子装置应用的共轭聚合物组合物 |
CN104619809B (zh) * | 2012-09-10 | 2016-11-09 | 沙特基础工业公司 | 制造用于太阳能电池应用的共轭聚合物组合物的方法 |
DE112013004610A5 (de) | 2012-09-20 | 2015-06-03 | Merck Patent Gmbh | Metallkomplexe |
KR101894713B1 (ko) * | 2012-10-12 | 2018-09-04 | 메르크 파텐트 게엠베하 | 방향족 단위들을 갖는 방출체들 및 호스트들 |
WO2014072017A1 (de) | 2012-11-12 | 2014-05-15 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP2926385B1 (de) | 2012-11-30 | 2020-08-05 | Merck Patent GmbH | Elektronische vorrichtung |
KR102197749B1 (ko) | 2013-01-03 | 2021-01-04 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
JP2016506414A (ja) | 2013-01-03 | 2016-03-03 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN105409022B (zh) | 2013-07-29 | 2018-06-19 | 默克专利有限公司 | 电光器件及其用途 |
US20160181537A1 (en) | 2013-07-29 | 2016-06-23 | Merck Patent Gmbh | Electroluminescence Device |
CN105612164A (zh) | 2013-10-02 | 2016-05-25 | 默克专利有限公司 | 用于oled中的含硼化合物 |
CN103525406B (zh) | 2013-10-21 | 2015-08-26 | 京东方科技集团股份有限公司 | 一种复合薄膜及其制作方法、光电元件和光电设备 |
CN103500803B (zh) * | 2013-10-21 | 2016-06-08 | 京东方科技集团股份有限公司 | 一种复合发光层及其制作方法、白光有机电致发光器件 |
EP3345984B1 (de) | 2013-12-06 | 2020-03-04 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
CN105814170B (zh) | 2013-12-12 | 2019-11-05 | 默克专利有限公司 | 电子器件的材料 |
JP6542228B2 (ja) | 2013-12-19 | 2019-07-10 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 複素環式スピロ化合物 |
CN103937292B (zh) * | 2014-03-27 | 2015-11-25 | 中南大学 | 聚(三苯胺-吩噻嗪)染料及其应用 |
JP6695863B2 (ja) | 2014-09-05 | 2020-05-20 | メルク パテント ゲーエムベーハー | 調合物と電子素子 |
JP2017537085A (ja) | 2014-11-11 | 2017-12-14 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
CN107406384B (zh) | 2014-12-04 | 2021-07-23 | 广州华睿光电材料有限公司 | 氘化的有机化合物、包含该化合物的混合物、组合物及有机电子器件 |
US10573827B2 (en) | 2014-12-11 | 2020-02-25 | Guangzhou Chinaray Optoelectronics Materials Ltd. | Organic metal complex, and polymer, mixture, composition and organic electronic device containing same and use thereof |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
CN107108862B (zh) | 2015-01-13 | 2019-08-02 | 广州华睿光电材料有限公司 | 含乙炔基交联基团的共轭聚合物、包含其的混合物、组合物、有机电子器件及其应用 |
EP3250658B1 (en) | 2015-01-30 | 2019-06-19 | Merck Patent GmbH | Materials for electronic devices |
EP3254317B1 (de) | 2015-02-03 | 2019-07-31 | Merck Patent GmbH | Metallkomplexe |
JP6800879B2 (ja) | 2015-03-30 | 2020-12-16 | メルク パテント ゲーエムベーハー | シロキサン溶媒を含む有機機能性材料の調合物 |
CN107683281A (zh) | 2015-06-10 | 2018-02-09 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
US10808170B2 (en) | 2015-06-12 | 2020-10-20 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for OLED formulations |
JP6625934B2 (ja) | 2015-07-14 | 2019-12-25 | 信越化学工業株式会社 | レジスト下層膜材料、パターン形成方法、及び化合物 |
KR102660538B1 (ko) | 2015-07-22 | 2024-04-24 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
GB201513037D0 (en) | 2015-07-23 | 2015-09-09 | Merck Patent Gmbh | Phenyl-derived compound for use in organic electronic devices |
JP6983754B2 (ja) | 2015-07-29 | 2021-12-17 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
JP6839697B2 (ja) | 2015-07-30 | 2021-03-10 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 電子素子のための材料 |
KR102599157B1 (ko) | 2015-08-14 | 2023-11-06 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 페녹사진 유도체 |
CN107849444A (zh) | 2015-08-28 | 2018-03-27 | 默克专利有限公司 | 用于电子器件的化合物 |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
CN108291103B (zh) | 2015-11-12 | 2021-12-07 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
KR20180090362A (ko) | 2015-12-10 | 2018-08-10 | 메르크 파텐트 게엠베하 | 비-방향족 사이클을 함유하는 케톤을 포함하는 제형 |
EP3391428B1 (en) | 2015-12-15 | 2022-06-29 | Merck Patent GmbH | Esters containing aromatic groups as solvents for organic electronic formulations |
KR20180095028A (ko) | 2015-12-16 | 2018-08-24 | 메르크 파텐트 게엠베하 | 둘 이상의 상이한 용매의 혼합물을 함유하는 제형 |
KR20180096676A (ko) | 2015-12-16 | 2018-08-29 | 메르크 파텐트 게엠베하 | 고체 용매를 함유하는 제형 |
CN105482813B (zh) * | 2015-12-21 | 2018-05-18 | 南京邮电大学 | 基于蒽醌基团的新型芴类双极性荧光材料及其在有机发光二极管中的应用 |
CN105552243A (zh) * | 2016-01-29 | 2016-05-04 | 桂林电子科技大学 | 一种紫外有机发光器件及其制备方法 |
CN108603107B (zh) | 2016-02-05 | 2022-08-26 | 默克专利有限公司 | 用于电子器件的材料 |
EP3417033B1 (en) | 2016-02-17 | 2021-02-24 | Merck Patent GmbH | Formulation of an organic functional material |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
TWI745361B (zh) | 2016-03-17 | 2021-11-11 | 德商麥克專利有限公司 | 具有螺聯茀結構之化合物 |
TW202340153A (zh) | 2016-04-11 | 2023-10-16 | 德商麥克專利有限公司 | 具有二苯并呋喃及/或二苯并噻吩結構之雜環化合物 |
JP7486921B2 (ja) | 2016-06-03 | 2024-05-20 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセントデバイス材料 |
KR20190019138A (ko) | 2016-06-16 | 2019-02-26 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
US11041083B2 (en) | 2016-06-17 | 2021-06-22 | Merck Patent Gmbh | Formulation of an organic functional material |
TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
EP3478698B1 (de) | 2016-06-30 | 2021-01-13 | Merck Patent GmbH | Verfahren zur auftrennung von enantiomerenmischungen von metallkomplexen |
TWI745395B (zh) | 2016-07-08 | 2021-11-11 | 德商麥克專利有限公司 | 有機電致發光裝置用之材料 |
CN109415344B (zh) | 2016-07-14 | 2022-06-03 | 默克专利有限公司 | 金属络合物 |
KR102427363B1 (ko) | 2016-08-04 | 2022-07-29 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
EP3512841B1 (de) | 2016-09-14 | 2023-04-26 | Merck Patent GmbH | Verbindungen mit spirobifluoren-strukturen |
KR102459000B1 (ko) | 2016-09-14 | 2022-10-26 | 메르크 파텐트 게엠베하 | 카르바졸 구조를 갖는 화합물 |
TWI766884B (zh) | 2016-09-30 | 2022-06-11 | 德商麥克專利有限公司 | 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途 |
WO2018060218A1 (de) | 2016-09-30 | 2018-04-05 | Merck Patent Gmbh | Carbazole mit diazadibenzofuran- oder diazadibenzothiophen-strukturen |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
CN109863223B (zh) | 2016-10-31 | 2023-06-20 | 默克专利有限公司 | 有机功能材料的制剂 |
JP7013459B2 (ja) | 2016-10-31 | 2022-01-31 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
CN109890787A (zh) | 2016-11-02 | 2019-06-14 | 默克专利有限公司 | 用于电子器件的材料 |
KR20230121632A (ko) | 2016-11-08 | 2023-08-18 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
TWI756292B (zh) | 2016-11-14 | 2022-03-01 | 德商麥克專利有限公司 | 具有受體基團與供體基團之化合物 |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
US11248138B2 (en) | 2016-11-23 | 2022-02-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink formulations, preparation methods and uses thereof |
JP7101670B2 (ja) | 2016-11-25 | 2022-07-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネッセンス素子(oled)の材料としてのビスベンゾフラン縮合2,8-ジアミノインデノ[1,2-b]フルオレン誘導体およびその関連化合物 |
EP3544985B1 (en) | 2016-11-25 | 2021-05-12 | Merck Patent GmbH | Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
US11713319B2 (en) | 2016-11-30 | 2023-08-01 | Merck Patent Gmbh | Compounds having valerolactam structures |
TW201831468A (zh) | 2016-12-05 | 2018-09-01 | 德商麥克專利有限公司 | 含氮的雜環化合物 |
KR102472751B1 (ko) | 2016-12-06 | 2022-11-30 | 메르크 파텐트 게엠베하 | 전자 디바이스의 제조 방법 |
KR102486614B1 (ko) | 2016-12-13 | 2023-01-09 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
KR102594781B1 (ko) | 2017-01-23 | 2023-10-26 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
KR102625926B1 (ko) | 2017-01-25 | 2024-01-17 | 메르크 파텐트 게엠베하 | 카르바졸 유도체 |
TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光(el)元件之方法 |
JP7069184B2 (ja) | 2017-02-02 | 2022-05-17 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
US20200055822A1 (en) | 2017-03-02 | 2020-02-20 | Merck Patent Gmbh | Materials for organic electronic devices |
TW201843143A (zh) | 2017-03-13 | 2018-12-16 | 德商麥克專利有限公司 | 含有芳基胺結構之化合物 |
CN110446611B (zh) | 2017-03-31 | 2021-05-25 | 默克专利有限公司 | 用于有机发光二极管(oled)的印刷方法 |
CN110494514A (zh) | 2017-04-10 | 2019-11-22 | 默克专利有限公司 | 有机功能材料的制剂 |
CN110573515B (zh) | 2017-04-25 | 2023-07-25 | 默克专利有限公司 | 用于电子器件的化合物 |
CN110546236A (zh) | 2017-05-03 | 2019-12-06 | 默克专利有限公司 | 有机功能材料的制剂 |
JP2020520970A (ja) | 2017-05-22 | 2020-07-16 | メルク パテント ゲーエムベーハー | 電子デバイス用六環性ヘテロ芳香族化合物 |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
CN110799484B (zh) | 2017-06-28 | 2023-09-26 | 默克专利有限公司 | 用于电子器件的材料 |
KR20200030573A (ko) | 2017-07-18 | 2020-03-20 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
TWI779067B (zh) | 2017-07-28 | 2022-10-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
TW201923028A (zh) | 2017-09-08 | 2019-06-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
KR20200090817A (ko) | 2017-11-23 | 2020-07-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
WO2019115577A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Substituted aromatic amines for use in organic electroluminescent devices |
WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
TW201938562A (zh) | 2017-12-19 | 2019-10-01 | 德商麥克專利有限公司 | 雜環化合物 |
CN111479815A (zh) | 2017-12-20 | 2020-07-31 | 默克专利有限公司 | 杂芳族化合物 |
JP7247231B2 (ja) | 2018-02-26 | 2023-03-28 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
CN111819167A (zh) | 2018-03-16 | 2020-10-23 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
JP7379389B2 (ja) | 2018-06-15 | 2023-11-14 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
EP3856868B1 (de) | 2018-09-27 | 2023-01-25 | Merck Patent GmbH | Verbindungen, die in einer organischen elektronischen vorrichtung als aktive verbindungen einsetzbar sind |
JP2022501400A (ja) | 2018-09-27 | 2022-01-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 立体障害窒素含有ヘテロ芳香族化合物を製造する方法 |
WO2020094539A1 (de) | 2018-11-05 | 2020-05-14 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
TW202034551A (zh) | 2018-11-06 | 2020-09-16 | 德商麥克專利有限公司 | 用於形成電子裝置的有機元件之方法 |
KR20210091769A (ko) | 2018-11-14 | 2021-07-22 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스의 제조에 사용될 수 있는 화합물 |
US11370879B2 (en) * | 2018-12-14 | 2022-06-28 | International Business Machines Corporation | Solution-processable indenofluorenes and methods to generate solution-processable indenofluorenes |
WO2021078710A1 (en) | 2019-10-22 | 2021-04-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021078831A1 (de) | 2019-10-25 | 2021-04-29 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
US20230069061A1 (en) | 2019-12-18 | 2023-03-02 | Merck Patent Gmbh | Aromatic compounds for organic electroluminescent devices |
KR20220116008A (ko) | 2019-12-19 | 2022-08-19 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 다환 화합물 |
CN115052865A (zh) | 2020-01-29 | 2022-09-13 | 默克专利有限公司 | 苯并咪唑衍生物 |
EP4110884A1 (de) | 2020-02-25 | 2023-01-04 | Merck Patent GmbH | Verwendung von heterocyclischen verbindungen in einer organischen elektronischen vorrichtung |
CN115244728A (zh) | 2020-03-02 | 2022-10-25 | 默克专利有限公司 | 砜化合物在有机电子器件中的用途 |
WO2021185712A1 (de) | 2020-03-17 | 2021-09-23 | Merck Patent Gmbh | Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen |
KR20220154751A (ko) | 2020-03-17 | 2022-11-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
KR20220158771A (ko) | 2020-03-26 | 2022-12-01 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 환형 화합물 |
US20230183269A1 (en) | 2020-04-06 | 2023-06-15 | Merck Patent Gmbh | Polycyclic compounds for organic electroluminescent devices |
CN115700058A (zh) | 2020-04-21 | 2023-02-03 | 默克专利有限公司 | 包含有机功能材料的乳液 |
WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2021254984A1 (de) | 2020-06-18 | 2021-12-23 | Merck Patent Gmbh | Indenoazanaphthaline |
CN115916795A (zh) | 2020-06-29 | 2023-04-04 | 默克专利有限公司 | 用于有机电致发光器件的杂芳族化合物 |
CN115916794A (zh) | 2020-06-29 | 2023-04-04 | 默克专利有限公司 | 用于有机电致发光器件的杂环化合物 |
TW202229215A (zh) | 2020-09-30 | 2022-08-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置功能層之結構化的化合物 |
TW202222748A (zh) | 2020-09-30 | 2022-06-16 | 德商麥克專利有限公司 | 用於結構化有機電致發光裝置的功能層之化合物 |
US20230389423A1 (en) | 2020-10-16 | 2023-11-30 | Merck Patent Gmbh | Heterocyclic compounds for organic electroluminescent devices |
CN116406414A (zh) | 2020-10-16 | 2023-07-07 | 默克专利有限公司 | 用于有机电致发光器件的包含杂原子的化合物 |
WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
CN116724040A (zh) | 2020-12-18 | 2023-09-08 | 默克专利有限公司 | 用于有机电致发光器件的含氮化合物 |
US20240114782A1 (en) | 2020-12-18 | 2024-04-04 | Merck Patent Gmbh | Indolo[3.2.1-jk]carbazole-6-carbonitrile derivatives as blue fluorescent emitters for use in oleds |
WO2022129113A1 (de) | 2020-12-18 | 2022-06-23 | Merck Patent Gmbh | Stickstoffhaltige heteroaromaten für organische elektrolumineszenzvorrichtungen |
KR20240000559A (ko) | 2021-04-23 | 2024-01-02 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 포뮬레이션 |
CN117425655A (zh) | 2021-04-30 | 2024-01-19 | 默克专利有限公司 | 用于有机电致发光器件的含氮杂环化合物 |
CN117730638A (zh) | 2021-08-02 | 2024-03-19 | 默克专利有限公司 | 通过组合油墨进行的印刷方法 |
CN117980439A (zh) | 2021-09-14 | 2024-05-03 | 默克专利有限公司 | 用于有机电致发光器件的含硼杂环化合物 |
TW202349760A (zh) | 2021-10-05 | 2023-12-16 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
WO2023072799A1 (de) | 2021-10-27 | 2023-05-04 | Merck Patent Gmbh | Bor- und stickstoffhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023099543A1 (en) | 2021-11-30 | 2023-06-08 | Merck Patent Gmbh | Compounds having fluorene structures |
WO2023161167A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2023161168A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Aromatische heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2023213837A1 (de) | 2022-05-06 | 2023-11-09 | Merck Patent Gmbh | Cyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023237458A1 (en) | 2022-06-07 | 2023-12-14 | Merck Patent Gmbh | Method of printing a functional layer of an electronic device by combining inks |
WO2023247338A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Organische heterocyclen für photoelektrische vorrichtungen |
WO2023247345A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Heterocyclen für photoelektrische vorrichtungen |
WO2024061942A1 (de) | 2022-09-22 | 2024-03-28 | Merck Patent Gmbh | Stickstoffenthaltende verbindungen für organische elektrolumineszenzvorrichtungen |
WO2024061948A1 (de) | 2022-09-22 | 2024-03-28 | Merck Patent Gmbh | Stickstoffenthaltende heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024094592A2 (de) | 2022-11-01 | 2024-05-10 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
DE4331401A1 (de) * | 1993-09-15 | 1995-03-16 | Hoechst Ag | Verwendung von Polymeren mit isolierten Chromophoren als Elektrolumineszenzmaterialen |
DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
EP0842208B2 (en) | 1995-07-28 | 2009-08-19 | Sumitomo Chemical Company, Limited | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
GB9609282D0 (en) | 1996-05-03 | 1996-07-10 | Cambridge Display Tech Ltd | Protective thin oxide layer |
JP3724589B2 (ja) | 1996-07-29 | 2005-12-07 | ケンブリッジ ディスプレイ テクノロジー リミテッド | エレクトロルミネセンス素子 |
US5728801A (en) | 1996-08-13 | 1998-03-17 | The Dow Chemical Company | Poly (arylamines) and films thereof |
US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
GB2335884A (en) | 1998-04-02 | 1999-10-06 | Cambridge Display Tech Ltd | Flexible substrates for electronic or optoelectronic devices |
DE19846767A1 (de) | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend Fluorbausteine mit verbesserten Eigenschaften |
DE19846766A1 (de) | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
DE19901296A1 (de) * | 1999-01-15 | 2000-07-27 | Voith Turbo Kg | Hydrodynamische Kupplung |
CA2360644A1 (en) * | 1999-02-04 | 2000-08-10 | The Dow Chemical Company | Fluorene copolymers and devices made therefrom |
CN1165563C (zh) | 1999-03-05 | 2004-09-08 | 剑桥显示技术有限公司 | 聚合物制备 |
GB9905203D0 (en) * | 1999-03-05 | 1999-04-28 | Cambridge Display Tech Ltd | Polymer preparation |
WO2000079617A1 (en) * | 1999-06-21 | 2000-12-28 | Cambridge University Technical Services Limited | Aligned polymers for an organic tft |
JP3886381B2 (ja) | 2000-01-05 | 2007-02-28 | ケンブリッジ ディスプレイ テクノロジー リミテッド | 高分子及びその製造方法と使用 |
AU2000275768A1 (en) | 2000-09-12 | 2002-03-26 | Ceravision Limited | Electronic device |
US6479172B2 (en) * | 2001-01-26 | 2002-11-12 | Xerox Corporation | Electroluminescent (EL) devices |
EP1388180A2 (en) * | 2001-05-18 | 2004-02-11 | Cambridge University Technical Services Limited | Electroluminescent device |
DE10143353A1 (de) | 2001-09-04 | 2003-03-20 | Covion Organic Semiconductors | Konjugierte Polymere enthaltend Spirobifluoren-Einheiten und deren Verwendung |
DE10241814A1 (de) | 2002-09-06 | 2004-03-25 | Covion Organic Semiconductors Gmbh | Prozeß zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
DE10337077A1 (de) | 2003-08-12 | 2005-03-10 | Covion Organic Semiconductors | Konjugierte Copolymere, deren Darstellung und Verwendung |
EP1627891A1 (en) * | 2004-08-11 | 2006-02-22 | Covion Organic Semiconductors GmbH | Polymers for use in organic electroluminescent devices |
-
2002
- 2002-11-08 GB GBGB0226010.7A patent/GB0226010D0/en not_active Ceased
-
2003
- 2003-11-06 KR KR1020057008006A patent/KR101077712B1/ko active IP Right Grant
- 2003-11-06 WO PCT/EP2003/012369 patent/WO2004041901A1/en active Application Filing
- 2003-11-06 EP EP03775305A patent/EP1562997B1/en not_active Expired - Lifetime
- 2003-11-06 JP JP2004549129A patent/JP4435690B2/ja not_active Expired - Lifetime
- 2003-11-06 CN CNB2003801029115A patent/CN100569827C/zh not_active Expired - Lifetime
- 2003-11-06 US US10/533,920 patent/US8860007B2/en not_active Expired - Fee Related
- 2003-11-06 DE DE60329413T patent/DE60329413D1/de not_active Expired - Lifetime
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008530254A (ja) * | 2003-06-23 | 2008-08-07 | メルク パテント ゲーエムベーハー | ポリマー |
JP2013191867A (ja) * | 2003-09-04 | 2013-09-26 | Merck Patent Gmbh | 有機導体および半導体と架橋したポリマーからなる中間バッファー層とを備えた電子デバイス |
JP2005171258A (ja) * | 2003-12-09 | 2005-06-30 | Samsung Sdi Co Ltd | 発光高分子及びそれを利用した有機電界発光ディスプレイ |
JP2010147487A (ja) * | 2003-12-12 | 2010-07-01 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP2006169265A (ja) * | 2003-12-12 | 2006-06-29 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP2009544773A (ja) * | 2006-07-25 | 2009-12-17 | メルク パテント ゲーエムベーハー | ポリマーブレンドとその有機発光素子での使用 |
JP2008074711A (ja) * | 2006-09-19 | 2008-04-03 | Okayama Univ | トリアリールエチルエテン誘導体の製造方法 |
JP2008109108A (ja) * | 2006-09-26 | 2008-05-08 | Sumitomo Chemical Co Ltd | 高分子吸着膜及びその製造方法 |
JP2012528210A (ja) * | 2009-05-29 | 2012-11-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 共役ポリマーおよび有機半導体としてのそれらの使用 |
JP2012528208A (ja) * | 2009-05-29 | 2012-11-12 | メルク パテント ゲーエムベーハー | 置換インデノフルオレン誘導体を構造単位として含むポリマー、その調製方法およびその使用 |
US9349960B2 (en) | 2009-05-29 | 2016-05-24 | Merck Patent Gmbh | Compounds and polymers which contain substituted indenofluorene derivatives as structural unit, process for the preparation thereof, and the use thereof as electronic devices and mixtures and solutions |
JP2012530820A (ja) * | 2009-06-26 | 2012-12-06 | メルク パテント ゲーエムベーハー | アルキルアルコキシ基を含む構造単位を含むポリマー、これらのポリマーを含むブレンド、これらのポリマーとブレンドを含む光電子素子 |
US9175132B2 (en) | 2009-06-26 | 2015-11-03 | Merck Patent Gmbh | Polymers comprising structural units which contain alkylalkoxy groups, blends comprising these polymers, and opto-electronic devices comprising these polymers and blends |
JP2012533661A (ja) * | 2009-07-22 | 2012-12-27 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
US10125214B2 (en) | 2009-07-22 | 2018-11-13 | Merck Patent Gmbh | Materials for electronic devices |
JP2013506647A (ja) * | 2009-09-30 | 2013-02-28 | ロモックス リミテッド | フルオレン誘導体を含む電界発光材料 |
JP2016507475A (ja) * | 2012-11-23 | 2016-03-10 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
JP2016014112A (ja) * | 2014-07-03 | 2016-01-28 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
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CN100569827C (zh) | 2009-12-16 |
JP4435690B2 (ja) | 2010-03-24 |
US20060046092A1 (en) | 2006-03-02 |
KR101077712B1 (ko) | 2011-10-27 |
KR20050084947A (ko) | 2005-08-29 |
EP1562997B1 (en) | 2009-09-23 |
CN1711301A (zh) | 2005-12-21 |
GB0226010D0 (en) | 2002-12-18 |
WO2004041901A1 (en) | 2004-05-21 |
US8860007B2 (en) | 2014-10-14 |
DE60329413D1 (de) | 2009-11-05 |
EP1562997A1 (en) | 2005-08-17 |
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