JP5726734B2 - 電子デバイス用化合物 - Google Patents
電子デバイス用化合物 Download PDFInfo
- Publication number
- JP5726734B2 JP5726734B2 JP2011520335A JP2011520335A JP5726734B2 JP 5726734 B2 JP5726734 B2 JP 5726734B2 JP 2011520335 A JP2011520335 A JP 2011520335A JP 2011520335 A JP2011520335 A JP 2011520335A JP 5726734 B2 JP5726734 B2 JP 5726734B2
- Authority
- JP
- Japan
- Prior art keywords
- groups
- organic
- compound
- group
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 93
- 239000010410 layer Substances 0.000 claims description 53
- 239000000463 material Substances 0.000 claims description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 30
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 29
- -1 dibenzoanthracene Chemical compound 0.000 claims description 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000000412 dendrimer Substances 0.000 claims description 14
- 229920000736 dendritic polymer Polymers 0.000 claims description 14
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 6
- 150000007942 carboxylates Chemical group 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 6
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical compound C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 4
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims 2
- 230000000171 quenching effect Effects 0.000 claims 2
- 150000004696 coordination complex Chemical class 0.000 claims 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 0 *C1(*)c(cc(c(cccc2)c2c2c3cccc2)c3c2)c2-c(cc2C(*)(*)c3c4)c1cc2-c3cc1c4c(cccc2)c2c2ccccc12 Chemical compound *C1(*)c(cc(c(cccc2)c2c2c3cccc2)c3c2)c2-c(cc2C(*)(*)c3c4)c1cc2-c3cc1c4c(cccc2)c2c2ccccc12 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000004986 diarylamino group Chemical group 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- ULWORHXYSIFJLN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)-2-naphthalen-1-yl-5-pyren-1-ylphenyl]propan-2-ol Chemical compound C1=CC=C2C(C3=CC(=C(C=4C5=CC=C6C=CC=C7C=CC(C5=C76)=CC=4)C=C3C(C)(O)C)C(C)(C)O)=CC=CC2=C1 ULWORHXYSIFJLN-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- LHRCREOYAASXPZ-UHFFFAOYSA-N c(cc1cc2)ccc1c1c2cc2c3ccccc3ccc2c1 Chemical compound c(cc1cc2)ccc1c1c2cc2c3ccccc3ccc2c1 LHRCREOYAASXPZ-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- WHFLYJCKDUDLBK-UHFFFAOYSA-N diethyl 2-naphthalen-1-yl-5-pyren-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C2C(C=3C=C(C(=CC=3C(=O)OCC)C=3C4=CC=CC=C4C=CC=3)C(=O)OCC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WHFLYJCKDUDLBK-UHFFFAOYSA-N 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- AYIJSROMAHHOKG-UHFFFAOYSA-N 2-[5-fluoranthen-3-yl-4-(2-hydroxypropan-2-yl)-2-naphthalen-1-ylphenyl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3C1=CC(C(C)(C)O)=C(C=2C3=CC=CC=C3C=CC=2)C=C1C(C)(O)C AYIJSROMAHHOKG-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- WHJFOWHDLUVUMM-UHFFFAOYSA-N diethyl 2-bromo-3-chlorobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C(Br)=C1Cl WHJFOWHDLUVUMM-UHFFFAOYSA-N 0.000 description 2
- AUWAVTOWGKXNNK-UHFFFAOYSA-N diethyl 2-chloro-5-pyren-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C1C(=O)OCC AUWAVTOWGKXNNK-UHFFFAOYSA-N 0.000 description 2
- ZLCKIDHRJDWDOW-UHFFFAOYSA-N diethyl 2-fluoranthen-3-yl-5-naphthalen-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=CC=C2C(C=3C=C(C(=CC=3C(=O)OCC)C=3C=4C=CC=C5C6=CC=CC=C6C(C=45)=CC=3)C(=O)OCC)=CC=CC2=C1 ZLCKIDHRJDWDOW-UHFFFAOYSA-N 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 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 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 1
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- PLJDGKPRGUMSAA-UHFFFAOYSA-N 2,2',7,7'-tetraphenyl-1,1'-spirobi[fluorene] Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C=C(C23C(=CC=C4C5=CC=C(C=C5C=C43)C=3C=CC=CC=3)C=3C=CC=CC=3)C1=CC=C2C1=CC=CC=C1 PLJDGKPRGUMSAA-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- VNDFYDZORAPFSA-UHFFFAOYSA-N 2-(2-phenylethenoxy)ethenylbenzene Chemical compound C=1C=CC=CC=1C=COC=CC1=CC=CC=C1 VNDFYDZORAPFSA-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical group C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- AWZBZYRFTSPJSH-UHFFFAOYSA-N CC1(C=CC=CC1)N Chemical compound CC1(C=CC=CC1)N AWZBZYRFTSPJSH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ABMXTYASRSTZMS-UHFFFAOYSA-N OC(=O)C1=C(Cl)C=CC(Br)=C1C(O)=O Chemical compound OC(=O)C1=C(Cl)C=CC(Br)=C1C(O)=O ABMXTYASRSTZMS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- KGXCHACLIFYNOP-VOTSOKGWSA-N [(e)-2-phenylethenyl]phosphane Chemical compound P\C=C\C1=CC=CC=C1 KGXCHACLIFYNOP-VOTSOKGWSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- DWDHOTUTUOTLFA-UHFFFAOYSA-M cesium;quinoline-2-carboxylate Chemical compound [Cs+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 DWDHOTUTUOTLFA-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 1
- HUOFGNUAVGKVDA-UHFFFAOYSA-N diethyl 2-chloro-5-naphthalen-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2C3=CC=CC=C3C=CC=2)=C1C(=O)OCC HUOFGNUAVGKVDA-UHFFFAOYSA-N 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical group CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- LDPCTBXVSGTSNJ-UHFFFAOYSA-N fluoranthen-3-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3B(O)O LDPCTBXVSGTSNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MWEKPLLMFXIZOC-UHFFFAOYSA-N pyren-1-ylboronic acid Chemical compound C1=C2C(B(O)O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MWEKPLLMFXIZOC-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- XSPDXZISEYDDMJ-UHFFFAOYSA-N triazine;1,2,4-triazine Chemical compound C1=CN=NN=C1.C1=CN=NC=N1 XSPDXZISEYDDMJ-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- 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
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/82—Cathodes
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photoreceptors In Electrophotography (AREA)
- Photovoltaic Devices (AREA)
Description
1.効率の改善の必要性が、特に蛍光OLEDの場合に、なお存在する。このことは、特に暗青色発光OLEDに当てはまる。
3.動作電圧が、特に蛍光発光OLEDの場合に、非常に高い。従って、パワー効率を改善するためにここでの改善の必要性がなお存在する。このことは、モバイル用途について非常に重要である。
Ar1、Ar2、Ar3は、出現毎に同一であるか、異なり、1つまたはそれ以上の基R1により置換されていてもよい、5〜30個の芳香族環原子を有するアリールもしくはヘテロアリール基であるが、ただし、Ar2は、アントラセン、ナフタセンまたはペンタセンを表すことがなく、
Xは、出現毎に同一であるか、異なり、BR2、C(R2)2、Si(R2)2、C=O、C=NR2、C=C(R2)2、O、S、S=O、SO2、NR2、PR2、P(=O)R2およびP(=S)R2から選ばれる基であり、
R1、R2は、出現毎に同一であるか、異なり、H、D、F、Cl、Br、I、N(Ar4)2、C(=O)Ar4、P(=O)(Ar4)2、S(=O)Ar4、S(=O)2Ar4、CR2=CR2Ar4、CHO、CR3=C(R3)2、CN、NO2、Si(R3)3、B(OR3)2、B(R3)2、B(N(R3)2)2、OSO2R3、1〜40個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルコキシ基もしくは2〜40個のC原子を有する直鎖のアルケニルもしくはアルキニル基もしくは3〜40個のC原子を有する分枝もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基であって、それぞれは、1つまたはそれ以上の基R3により置換されていてもよいものであり(ここで、各場合において、1つまたはそれ以上の非隣接CH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)R3、SO、SO2、NR3、O、SまたはCONR3により置き換えられてもよく、そして1つまたはそれ以上のH原子は、F、Cl、Br、I、CNもしくはNO2により置き換えられてもよい)、または各場合において1つまたはそれ以上の基R3により置換されていてもよい、5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系、またはこれら系の組合せであり、ここで、2つまたはそれ以上の置換基R1またはR2は、互いに単環もしくは多環の脂肪族もしくは芳香族環を形成していてもよく、
R3は、出現毎に同一であるか、異なり、H、Dまたは1〜20個のC原子を有する脂肪族もしくは芳香族炭化水素基であり、
Ar4は、出現毎に同一であるか、異なり、1つまたはそれ以上の非芳香族基R1によって置換されていてもよい、5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系であり、同じ窒素もしくはリン原子上の2つの基Arは、単結合もしくはブリッジXにより互いに連結していてもよく、
m、nは、0または1であるが、ただし、m+n=1であり、
pは、1、2、3、4、5または6であり、
ここで、Ar1、Ar2およびXは、一緒に、五員環または六員環を形成し、Ar2、Ar3およびXは、一緒に、五員環または六員環を形成するが、ただし、式(1)の化合物におけるすべての記号Xは、五員環中に結合されているか、または式(1)の化合物におけるすべての記号Xは、六員環中に結合されている)の化合物であって、基Ar1、Ar2およびAr3中のすべてのπ電子の合計は、p=1であるとき少なくとも28であり、p=2であるとき少なくとも34であり、p=3であるとき少なくとも40であり、p=4であるとき少なくとも46であり、p=5であるとき少なくとも52であり、p=6であるとき少なくとも58であることを特徴とし、以下の化合物が本発明から除かれ、
a)適切な置換基が例えばカルボキシレート基であり得る適切に置換したAr1、Ar2およびAr3のカップリング、および
b)ブリッジXの導入のための上記置換基の環化
を包含する本発明による化合物の製造方法に関する。
a)ボロン酸もしくはAr1のボロン酸誘導体の、Ar2のブロモクロロビス(カルボキシレート)誘導体へのカップリング、
b)a)からの反応生成物の、ボロン酸もしくはAr3のボロン酸誘導体へのカップリング、
c)カルボキシレート基のアルコール基への変換、および
d)酸性条件下での環化
を包含する式(1)の化合物の製造方法が好ましい。
(ここで、Ar4、Ar5、Ar6は出現毎に同一であるか、異なり、1つまたはそれ以上の基R1により置換されていてもよい、5〜30個の芳香族環原子を有するアリールもしくはヘテロアリール基であり、R1およびpは、上記と同じ意味を有し、Ar4、Ar5およびAr6中のπ電子の合計は、p=1であるとき少なくとも30であり、p=2であるとき少なくとも36であり、p=3であるとき少なくとも42である)。
以下の合成は、別段の指摘がない限り、保護ガス雰囲気下で行った。出発物質は、アルドリッチ(ALDRICH)またはABCRから購入した。
WO04/058911に一般的に記載されている方法で、それぞれの場合に個々の状況に適合(例えば、最適な効率または色を達成するための層厚の変更)させてOLEDを製造する。
Claims (13)
- 式(1)
Ar1、Ar3は、出現毎に同一であるか、異なり、1つまたはそれ以上の基R1により置換されていてもよいベンゼン、ナフタレン、アントラセン、フェナントレン、フルオランテン、ナフタセン、ベンゾアントラセン、クリセン、ピレン、ベンゾフルオランテン、トリフェニレン、ペリレン、ジベンゾアントラセン、ベンゾピレン、ピセン、ペンタセン、ペンタフェン、ピリジン、ピラジン、ピリミジン、ピリダジン、キノリン、イソキノリン、フェナントロリン、アクリジンからなる群の中から選ばれる5〜22個の芳香族環原子を有するアリールもしくはヘテロアリール基を表し、
Ar2は、1つまたはそれ以上の基R1により置換されていてもよいベンゼンであり、
Xは、C(R2)2であり、
R1は、出現毎に同一であるか、異なり、H、D、F、Si(R3)3、1〜10個のC原子を有する直鎖のアルキルもしくはアルコキシ基または3〜10個のC原子を有する分枝もしくは環式のアルキルもしくはアルコキシ基であって、それぞれは、1つまたはそれ以上の基R3により置換されていてもよく、そして各場合において1つまたはそれ以上の非隣接CH2基はR3C=CR3またはOにより置き換えられてもよく、そして1つまたはそれ以上のH原子はFにより置き換えられていてもよいもの、もしくは5〜40個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系、またはこれらの系の組合せから選ばれ、ここで、2つまたはそれ以上の置換基R1はまた、互いに単環もしくは多環の脂肪族もしくは芳香族環系を形成してもよく、
R2は、出現毎に同一であるか、異なり、H、1〜10個のC原子を有する直鎖アルキル基もしくは3〜10個のC原子を有する分枝もしくは環式アルキル基であって、各場合において1つまたはそれ以上の非隣接CH2基は−R 3 C=CR 3 −または−O−により置き換えられてもよく、そして1つまたはそれ以上のH原子はFにより置き換えられていてもよいもの、もしくは1つまたはそれ以上の置換基R 3 により置換されていてもよい、5〜16個の芳香族環原子を有する一価のアリールもしくはヘテロアリール基から選ばれ、同じ基X中に結合した2つの基R 3 は、また、互いに環構造を形成してもよく、
Ar4は、出現毎に同一であるか、異なり、1つまたはそれ以上の非芳香族基R1によって置換されていてもよい、5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系であり、同じ窒素もしくはリン原子上の2つの基Arは、単結合もしくはブリッジXにより互いに連結していてもよく、
R3は、出現毎に同一であるか、異なり、H、または1〜20個のC原子を有する脂肪族もしくは芳香族炭化水素基であり、
m、nは、0または1であるが、ただし、m+n=1であり、
pは、1であり、
ここで、Ar1、Ar2およびXは、一緒に、五員環または六員環を形成し、Ar2、Ar3およびXは、一緒に、五員環または六員環を形成するが、ただし、式(1)の化合物
におけるすべての記号Xは、五員環中に結合されているか、または式(1)の化合物におけるすべての記号Xは、六員環中に結合されている)の化合物であって、基Ar1、Ar2
およびAr3中のすべてのπ電子の合計は、少なくとも28であることを特徴とする化合物(ただし、以下の化合物を除く)。
- p=1であり、基Ar1、Ar2およびAr3中のすべてのπ電子の合計は、p=1であるとき、28〜50であることを特徴とする請求項1に記載の化合物。
- 基Ar1、Ar2およびAr3のうちの少なくとも1つが少なくとも4つの縮合環、すなわち少なくとも16個のπ電子を有することを特徴とする請求項1〜4何れか一項に記載の化合物。
- 請求項1〜6何れか一項に記載の1種またはそれ以上の化合物を含むオリゴマー、ポリマーまたはデンドリマーであって、基R1および/またはR2の少なくとも1つが、前記オリゴマー、ポリマーまたはデンドリマーへの結合を表すオリゴマー、ポリマーまたはデンドリマー。
- 請求項1〜6何れか一項に記載の化合物の製造方法であって、以下の反応工程:
a)カルボキシレート基で置換されたAr1、Ar2およびAr3のカップリング、および
b)ブリッジXの導入のための前記置換基の環化
を含む方法。 - 有機エレクトロルミネッセンスデバイス(OLED、PLED)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機集積回路(O−IC)、有機太陽電池(O−SC)、有機電場消光デバイス(O−FQD)、発光電気化学電池(LEC)、有機感光体もしくは有機レーザーダイオード(O−レーザー)から選ばれる電子デバイスにおける請求項1〜6何れか一項1に記載の化合物の使用
- 有機エレクトロルミネッセンスデバイス(OLED、PLED)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機集積回路(O−IC)、有機太陽電池(O−SC)、有機電場消光デバイス(O−FQD)、発光電気化学電池(LEC)、有機感光体もしくは有機レーザーダイオード(O−レーザー)から選ばれる有機電子デバイスであって、少なくとも1つの有機層が、請求項1〜6何れか一項に記載の化合物を含むことを特徴とする有機電子デバイス。
- 請求項1〜6何れか一項に記載の化合物が、発光層における発光物質としてもしくはホスト物質として、もしくはホール輸送層もしくはホール注入層におけるホール輸送物質もしくはホール注入物質として、または電子輸送層における電子輸送物質として使用されていることを特徴とする請求項10に記載の有機エレクトロルミネッセンスデバイス。
- 請求項1〜6何れか一項に記載の化合物が、ホスト物質と組み合わせて発光層における発光物質として使用され、前記ホスト物質が、オリゴアリーレン、縮合芳香族基を含有するオリゴアリーレン、アントラセン、オリゴアリーレンビニレン、多脚金属錯体、ホール伝導性化合物、電子伝導性化合物、ケトン、ホスフィンオキシド、スルホキシド、ボロン酸誘導体、ベンゾアントラセンまたは式(138)の化合物から選ばれることを特徴とする請求項10または11に記載の有機エレクトロルミネッセンスデバイス。
Ar4−(Ar5)p−Ar6 式(138)
(ここで、Ar4、Ar5、Ar6は、出現毎に同一であるか、異なり、1つまたはそれ以
上の基R1により置換されていてもよい、5〜30個の芳香族環原子を有するアリールも
しくはヘテロアリール基であり、R1およびpは、請求項1において記述したものと同じ
意味を有し、ここで、Ar4、Ar5およびAr6中のπ電子の合計は少なくとも30であ
る)。 - 請求項1〜6何れか一項に記載の少なくとも1種の化合物および少なくとも1種の溶媒を含む溶液または組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008035413A DE102008035413A1 (de) | 2008-07-29 | 2008-07-29 | Verbindungen für organische elektronische Vorrichtungen |
DE102008035413.9 | 2008-07-29 | ||
PCT/EP2009/003602 WO2010012328A1 (de) | 2008-07-29 | 2009-05-20 | Verbindungen für elektronische vorrichtungen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011529455A JP2011529455A (ja) | 2011-12-08 |
JP5726734B2 true JP5726734B2 (ja) | 2015-06-03 |
Family
ID=41226942
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011520335A Active JP5726734B2 (ja) | 2008-07-29 | 2009-05-20 | 電子デバイス用化合物 |
JP2011520337A Active JP5710479B2 (ja) | 2008-07-29 | 2009-05-22 | 有機エレクトロルミネセンス素子 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011520337A Active JP5710479B2 (ja) | 2008-07-29 | 2009-05-22 | 有機エレクトロルミネセンス素子 |
Country Status (8)
Country | Link |
---|---|
US (3) | US9051233B2 (ja) |
EP (2) | EP2303814B1 (ja) |
JP (2) | JP5726734B2 (ja) |
KR (3) | KR20100012781A (ja) |
CN (2) | CN102076640B (ja) |
DE (1) | DE102008035413A1 (ja) |
TW (2) | TWI478896B (ja) |
WO (2) | WO2010012328A1 (ja) |
Families Citing this family (241)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9805476D0 (en) * | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
DE102008035413A1 (de) * | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
KR101551207B1 (ko) * | 2008-09-04 | 2015-09-08 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008063490B4 (de) | 2008-12-17 | 2023-06-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
CN102421858A (zh) | 2009-06-22 | 2012-04-18 | 默克专利有限公司 | 导电制剂 |
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 |
KR20110013881A (ko) * | 2009-08-04 | 2011-02-10 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
DE102009053644B4 (de) | 2009-11-17 | 2019-07-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US9666806B2 (en) | 2009-09-16 | 2017-05-30 | Merck Patent Gmbh | Formulations for the production of electronic devices |
DE102009041289A1 (de) | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009042693A1 (de) | 2009-09-23 | 2011-03-24 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009051172A1 (de) | 2009-10-29 | 2011-05-05 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
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 |
WO2011076325A1 (en) | 2009-12-23 | 2011-06-30 | Merck Patent Gmbh | Compositions comprising polymeric binders |
KR20170093267A (ko) | 2009-12-23 | 2017-08-14 | 메르크 파텐트 게엠베하 | 유기 반도성 화합물을 포함하는 조성물 |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
DE102010006377A1 (de) | 2010-01-29 | 2011-08-04 | Merck Patent GmbH, 64293 | Styrolbasierte Copolymere, insbesondere für die Anwendung in optoelektronischen Bauteilen |
EP2366753B1 (en) * | 2010-03-02 | 2015-06-17 | Semiconductor Energy Laboratory Co., Ltd. | Light-Emitting Element and Lighting Device |
DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102010010481A1 (de) | 2010-03-06 | 2011-09-08 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102010010631A1 (de) | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010013068A1 (de) | 2010-03-26 | 2011-09-29 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
KR101896723B1 (ko) | 2010-04-12 | 2018-09-07 | 메르크 파텐트 게엠베하 | 유기 전자 소자 제조용 조성물 및 방법 |
WO2011128034A1 (en) | 2010-04-12 | 2011-10-20 | Merck Patent Gmbh | Composition having improved performance |
DE102010014933A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
KR101778825B1 (ko) | 2010-05-03 | 2017-09-14 | 메르크 파텐트 게엠베하 | 제형물 및 전자 소자 |
JP5645465B2 (ja) * | 2010-05-06 | 2014-12-24 | キヤノン株式会社 | 新規有機化合物 |
DE102010020044A1 (de) | 2010-05-11 | 2011-11-17 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
WO2011147523A1 (en) | 2010-05-27 | 2011-12-01 | 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 |
JP2010226145A (ja) * | 2010-06-30 | 2010-10-07 | Fujifilm Corp | 有機発光素子 |
DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
JP5561022B2 (ja) * | 2010-08-24 | 2014-07-30 | 東レ株式会社 | 発光素子 |
DE102010048074A1 (de) | 2010-10-09 | 2012-04-12 | 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 |
DE102010054316A1 (de) | 2010-12-13 | 2012-06-14 | Merck Patent Gmbh | Substituierte Tetraarylbenzole |
DE102010055902A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
KR101866851B1 (ko) * | 2010-12-24 | 2018-06-14 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
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 |
US9653689B2 (en) | 2011-01-17 | 2017-05-16 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting diode including the same |
CN102617626B (zh) | 2011-01-17 | 2016-12-14 | 三星显示有限公司 | 缩合环化合物和包括该缩合环化合物的有机发光二极管 |
DE102011011104A1 (de) | 2011-02-12 | 2012-08-16 | Merck Patent Gmbh | Substituierte Dibenzonaphtacene |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
KR102004385B1 (ko) * | 2011-04-01 | 2019-07-26 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
JP6132470B2 (ja) | 2011-04-12 | 2017-05-24 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子に用いる化合物および有機電界発光素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5979947B2 (ja) | 2011-04-12 | 2016-08-31 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子に用いる化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
KR101957902B1 (ko) * | 2011-04-13 | 2019-03-14 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
CN103459391A (zh) | 2011-04-13 | 2013-12-18 | 默克专利有限公司 | 用于电子器件的化合物 |
US9876171B2 (en) | 2011-04-13 | 2018-01-23 | Merck Patent Gmbh | Materials for electronic devices |
JP6022541B2 (ja) | 2011-04-18 | 2016-11-09 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
KR101996647B1 (ko) * | 2011-04-29 | 2019-07-04 | 에스에프씨 주식회사 | 신규한 축합아릴화합물 및 이를 포함하는 유기전계발광소자 |
WO2012149992A1 (de) | 2011-05-04 | 2012-11-08 | Merck Patent Gmbh | Vorrichtung zur aufbewahrung von frischwaren |
US10177312B2 (en) | 2011-05-05 | 2019-01-08 | Merck Patent Gmbh | Compounds for electronic devices |
DE102011104745A1 (de) | 2011-06-17 | 2012-12-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP6100258B2 (ja) | 2011-07-29 | 2017-03-22 | メルク パテント ゲーエムベーハー | 電子素子のための化合物 |
EP3439065B1 (de) | 2011-08-03 | 2022-01-12 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
JP6046884B2 (ja) | 2011-08-11 | 2016-12-21 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5814044B2 (ja) | 2011-08-16 | 2015-11-17 | 富士フイルム株式会社 | 光電変換素子およびその使用方法、撮像素子、光センサ |
JP5890980B2 (ja) | 2011-08-18 | 2016-03-22 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用の化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP6063114B2 (ja) * | 2011-08-18 | 2017-01-18 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5952543B2 (ja) * | 2011-08-18 | 2016-07-13 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用の化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
DE102012016192A1 (de) | 2011-08-19 | 2013-02-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
KR102051790B1 (ko) | 2011-08-22 | 2019-12-04 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스 |
JP5753027B2 (ja) * | 2011-08-22 | 2015-07-22 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP6347909B2 (ja) * | 2011-08-22 | 2018-06-27 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP6012148B2 (ja) | 2011-08-22 | 2016-10-25 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP2013093541A (ja) | 2011-10-06 | 2013-05-16 | Udc Ireland Ltd | 有機電界発光素子とそれに用いることができる化合物および有機電界発光素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
CN103858249B (zh) | 2011-10-06 | 2017-10-17 | 默克专利有限公司 | 有机电致发光器件 |
JP6223984B2 (ja) | 2011-10-27 | 2017-11-01 | 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 |
DE102011117422A1 (de) | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen |
TWI425076B (zh) | 2011-11-01 | 2014-02-01 | Ind Tech Res Inst | 咔唑衍生物及包含此衍生物之有機發光二極體 |
DE102011121022A1 (de) | 2011-12-13 | 2013-06-13 | Merck Patent Gmbh | Organische Sensibilisatoren für Up- Conversion |
JP5321700B2 (ja) * | 2012-01-17 | 2013-10-23 | 三菱化学株式会社 | 有機電界発光素子、有機el照明および有機el表示装置 |
EP3101088B1 (en) | 2012-02-14 | 2017-11-29 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR101390587B1 (ko) * | 2012-03-28 | 2014-04-30 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP6034604B2 (ja) | 2012-07-09 | 2016-11-30 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
CN104684886B (zh) * | 2012-09-04 | 2017-07-18 | 默克专利有限公司 | 用于电子器件的化合物 |
EP3806176A1 (de) | 2012-10-31 | 2021-04-14 | Merck Patent GmbH | Elektronische vorrichtung |
EP2917198B1 (de) | 2012-11-12 | 2018-05-16 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
US9203045B2 (en) * | 2012-11-29 | 2015-12-01 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
KR102173856B1 (ko) | 2012-11-30 | 2020-11-04 | 메르크 파텐트 게엠베하 | 전자 소자 |
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 |
WO2014106523A1 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Elektronische vorrichtung |
KR102029696B1 (ko) * | 2013-03-07 | 2019-10-08 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
JP6470495B2 (ja) * | 2013-03-07 | 2019-02-13 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を有する電子写真装置およびプロセスカートリッジ |
KR101682844B1 (ko) * | 2013-06-04 | 2016-12-05 | 이데미쓰 고산 가부시키가이샤 | 함질소 헤테로환 유도체, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기 |
JP5569630B2 (ja) * | 2013-07-16 | 2014-08-13 | 三菱化学株式会社 | 有機電界発光素子、有機el照明および有機el表示装置 |
JP6961345B2 (ja) | 2013-07-30 | 2021-11-05 | 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 |
EP3027708B1 (de) | 2013-07-30 | 2020-05-13 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN105636944B (zh) * | 2013-10-14 | 2019-03-01 | 默克专利有限公司 | 用于电子器件的材料 |
US10374170B2 (en) | 2013-12-06 | 2019-08-06 | Merck Patent Gmbh | Substituted oxepines |
US20160301003A1 (en) | 2013-12-06 | 2016-10-13 | Merck Patent Gmbh | Compositions containing a polymeric binder which comprises acrylic and/or methacrylic acid ester units |
KR101993129B1 (ko) | 2013-12-12 | 2019-06-26 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
KR102375992B1 (ko) | 2014-04-16 | 2022-03-17 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
JP6567856B2 (ja) * | 2014-04-18 | 2019-08-28 | 株式会社半導体エネルギー研究所 | 発光装置 |
EP3137458B1 (de) | 2014-04-30 | 2019-04-24 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN104017586B (zh) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | 液晶化合物、液晶组合物及其制备方法、液晶显示面板 |
TWI777568B (zh) * | 2014-05-30 | 2022-09-11 | 日商半導體能源研究所股份有限公司 | 發光元件,發光裝置,電子裝置以及照明裝置 |
CN106687563B (zh) | 2014-09-05 | 2023-03-14 | 默克专利有限公司 | 制剂和电子器件 |
JP6433207B2 (ja) * | 2014-09-05 | 2018-12-05 | キヤノン株式会社 | 電子写真感光体、電子写真装置およびプロセスカートリッジ |
KR101817836B1 (ko) * | 2014-09-23 | 2018-01-11 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
CN107532013A (zh) | 2015-01-30 | 2018-01-02 | 默克专利有限公司 | 具有低粒子含量的制剂 |
US20180006237A1 (en) | 2015-01-30 | 2018-01-04 | Merck Patent Gmbh | Materials for electronic devices |
US10686150B2 (en) | 2015-03-16 | 2020-06-16 | Lg Chem, Ltd. | Organic light emitting device |
WO2016150544A1 (en) | 2015-03-25 | 2016-09-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN107431139B (zh) | 2015-03-30 | 2020-12-01 | 默克专利有限公司 | 包含硅氧烷溶剂的有机功能材料的制剂 |
KR102610370B1 (ko) | 2015-05-18 | 2023-12-05 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 물질 |
WO2016188609A1 (en) * | 2015-05-22 | 2016-12-01 | Merck Patent Gmbh | Formulation containing an organic semiconductor and a metal complex |
EP3581633B1 (en) | 2015-06-12 | 2021-01-27 | Merck Patent GmbH | Esters containing non-aromatic cycles as solvents for oled formulations |
KR102643183B1 (ko) | 2015-07-15 | 2024-03-04 | 메르크 파텐트 게엠베하 | 유기 반도전성 화합물들을 포함하는 조성물 |
JP6946269B2 (ja) * | 2015-08-25 | 2021-10-06 | 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 GmbH | 金属錯体 |
EP3341448B1 (en) | 2015-08-28 | 2020-02-12 | Merck Patent GmbH | Compounds for electronic devices |
EP3341349B1 (de) * | 2015-08-28 | 2020-01-29 | Merck Patent GmbH | 6,9,15,18-tetrahydro-s-indaceno[1,2-b:5,6-b']difluoren- derivate und ihre verwendung in elektronischen vorrichtungen |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
KR102487494B1 (ko) * | 2015-10-20 | 2023-01-12 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP7106451B2 (ja) | 2015-12-10 | 2022-07-26 | メルク パテント ゲーエムベーハー | 非芳香族環を含むケトンを含む調合物 |
US11171294B2 (en) | 2015-12-15 | 2021-11-09 | 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 |
CN108431143A (zh) | 2015-12-16 | 2018-08-21 | 默克专利有限公司 | 含固体溶剂的制剂 |
WO2017133829A1 (de) | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
JP6371320B2 (ja) * | 2016-02-12 | 2018-08-08 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
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 |
JP2019523997A (ja) | 2016-06-16 | 2019-08-29 | 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 |
EP3472249B1 (en) | 2016-06-17 | 2022-02-02 | 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 |
US11365167B2 (en) | 2016-07-08 | 2022-06-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018024719A1 (en) | 2016-08-04 | 2018-02-08 | Merck Patent Gmbh | Formulation of an organic functional material |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
US11538992B2 (en) | 2016-10-31 | 2022-12-27 | Merck Patent Gmbh | Formulation of an organic functional material |
CN109890939B (zh) | 2016-10-31 | 2023-07-11 | 默克专利有限公司 | 有机功能材料的制剂 |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR102564613B1 (ko) | 2016-11-08 | 2023-08-07 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
US11618722B2 (en) * | 2016-11-09 | 2023-04-04 | Idemitsu Kosan Co., Ltd. | Compound, composition, organic electroluminescent element, and electronic appliance |
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 |
EP3544984B1 (en) | 2016-11-25 | 2020-12-23 | Merck Patent GmbH | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
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) |
EP3552252B1 (en) | 2016-12-06 | 2023-05-17 | Merck Patent GmbH | Preparation process for an electronic device |
WO2018108760A1 (en) | 2016-12-13 | 2018-06-21 | Merck Patent Gmbh | Formulation of an organic functional material |
US11261291B2 (en) | 2016-12-22 | 2022-03-01 | Merck Patent Gmbh | Materials for electronic devices |
KR102504432B1 (ko) | 2016-12-22 | 2023-02-27 | 메르크 파텐트 게엠베하 | 적어도 2종의 유기-기능성 화합물을 포함하는 혼합물 |
CN110177855A (zh) | 2017-01-23 | 2019-08-27 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
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 |
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 |
CN110291064B (zh) | 2017-02-02 | 2023-04-28 | 默克专利有限公司 | 用于电子器件的材料 |
CN110268544A (zh) | 2017-03-01 | 2019-09-20 | 默克专利有限公司 | 有机电致发光器件 |
US20200055822A1 (en) | 2017-03-02 | 2020-02-20 | Merck Patent Gmbh | Materials for organic electronic devices |
KR20190131554A (ko) | 2017-03-31 | 2019-11-26 | 메르크 파텐트 게엠베하 | 유기 발광 다이오드 (oled) 를 위한 인쇄 방법 |
WO2018189050A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Formulation of an organic functional material |
KR102608491B1 (ko) | 2017-04-13 | 2023-11-30 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
KR102585423B1 (ko) | 2017-04-25 | 2023-10-05 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
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 |
KR102174388B1 (ko) * | 2017-05-12 | 2020-11-04 | 주식회사 엘지화학 | 고리 화합물 및 이를 포함하는 유기 발광 소자 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
KR20200020841A (ko) | 2017-06-23 | 2020-02-26 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
WO2019002198A1 (en) | 2017-06-26 | 2019-01-03 | Merck Patent Gmbh | HOMOGENEOUS MIXTURES |
KR102661058B1 (ko) | 2017-06-28 | 2024-04-25 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
JP2019016788A (ja) * | 2017-07-03 | 2019-01-31 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機発光素子 |
TWI813576B (zh) | 2017-07-03 | 2023-09-01 | 德商麥克專利有限公司 | 具有低含量苯酚類雜質的調配物 |
WO2019007867A1 (de) | 2017-07-05 | 2019-01-10 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
JP7135012B2 (ja) | 2017-07-05 | 2022-09-12 | メルク パテント ゲーエムベーハー | 有機電子デバイスのための組成物 |
WO2019016184A1 (en) | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL |
CN110914244A (zh) | 2017-07-28 | 2020-03-24 | 默克专利有限公司 | 用于电子器件中的螺二芴衍生物 |
EP3679024B1 (de) | 2017-09-08 | 2022-11-02 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN108675975A (zh) | 2017-10-17 | 2018-10-19 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
TWI815831B (zh) | 2017-11-23 | 2023-09-21 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
TWI820057B (zh) | 2017-11-24 | 2023-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI838352B (zh) | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
JP7293229B2 (ja) | 2017-12-15 | 2023-06-19 | 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 |
US20200308129A1 (en) | 2017-12-15 | 2020-10-01 | Merck Patent Gmbh | Substituted aromatic amines for use in organic electroluminescent devices |
US20210036245A1 (en) | 2017-12-20 | 2021-02-04 | Merck Patent Gmbh | Heteroaromatic compounds |
KR20200125660A (ko) | 2018-02-26 | 2020-11-04 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 포뮬레이션 |
TWI802656B (zh) | 2018-03-06 | 2023-05-21 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TW201938761A (zh) | 2018-03-06 | 2019-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
KR20200132912A (ko) | 2018-03-16 | 2020-11-25 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
US11603479B2 (en) | 2018-06-15 | 2023-03-14 | Merck Kgaa | Formulation of an organic functional material |
TWI837167B (zh) | 2018-08-28 | 2024-04-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TWI823993B (zh) | 2018-08-28 | 2023-12-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
CN112585242A (zh) | 2018-08-28 | 2021-03-30 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
KR20210057092A (ko) | 2018-09-12 | 2021-05-20 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
KR20210056432A (ko) | 2018-09-24 | 2021-05-18 | 메르크 파텐트 게엠베하 | 과립형 재료의 제조 방법 |
JP2022509407A (ja) | 2018-10-31 | 2022-01-20 | 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のための材料 |
CN112930606A (zh) | 2018-11-06 | 2021-06-08 | 默克专利有限公司 | 用于形成电子器件的有机元件的方法 |
KR20210132673A (ko) | 2019-02-18 | 2021-11-04 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
CN113646315A (zh) | 2019-04-11 | 2021-11-12 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
US20230006143A1 (en) | 2019-09-19 | 2023-01-05 | Merck Patent Gmbh | Mixture of two host materials, and organic electroluminescent device comprising same |
TW202130783A (zh) | 2019-11-04 | 2021-08-16 | 德商麥克專利有限公司 | 有機電致發光裝置 |
WO2021089450A1 (en) | 2019-11-04 | 2021-05-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
JP2023518173A (ja) | 2020-03-11 | 2023-04-28 | 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装置 |
KR20220151193A (ko) | 2020-03-11 | 2022-11-14 | 메르크 파텐트 게엠베하 | 유기 전계 발광 장치 |
TW202200529A (zh) | 2020-03-13 | 2022-01-01 | 德商麥克專利有限公司 | 有機電致發光裝置 |
US20230337537A1 (en) | 2020-03-23 | 2023-10-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN115427521A (zh) | 2020-04-21 | 2022-12-02 | 默克专利有限公司 | 有机功能材料的制剂 |
EP4158704A1 (de) | 2020-05-29 | 2023-04-05 | Merck Patent GmbH | Organische elektrolumineszierende vorrichtung |
WO2021259824A1 (de) | 2020-06-23 | 2021-12-30 | Merck Patent Gmbh | Verfahren zur herstellung einer mischung |
WO2022017997A1 (en) | 2020-07-22 | 2022-01-27 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP4186113A1 (en) | 2020-07-22 | 2023-05-31 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR20230078587A (ko) * | 2020-10-01 | 2023-06-02 | 호도가야 가가쿠 고교 가부시키가이샤 | 광전 변환 소자에 사용하는 유기 박막 및 그 광전 변환 소자 |
TW202237797A (zh) | 2020-11-30 | 2022-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
CN116635491A (zh) | 2020-12-08 | 2023-08-22 | 默克专利有限公司 | 油墨体系和用于喷墨印刷的方法 |
KR20220092168A (ko) | 2020-12-24 | 2022-07-01 | 엘지디스플레이 주식회사 | 발광 소자 및 이를 포함한 발광 표시 장치 |
KR20230165916A (ko) | 2021-04-09 | 2023-12-05 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
EP4320649A1 (en) | 2021-04-09 | 2024-02-14 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TW202309243A (zh) | 2021-04-09 | 2023-03-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP4079742A1 (de) | 2021-04-14 | 2022-10-26 | Merck Patent GmbH | Metallkomplexe |
JP2024515366A (ja) | 2021-04-23 | 2024-04-09 | 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 |
CN117355364A (zh) | 2021-05-21 | 2024-01-05 | 默克专利有限公司 | 用于连续纯化至少一种功能材料的方法和用于连续纯化至少一种功能材料的装置 |
WO2022200638A1 (de) | 2021-07-06 | 2022-09-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
EP4402141A1 (en) | 2021-09-13 | 2024-07-24 | Merck Patent GmbH | Materials for organic electroluminescent devices |
WO2023052314A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052313A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20240075872A (ko) | 2021-09-28 | 2024-05-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
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 |
WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
CN118354991A (zh) | 2021-12-21 | 2024-07-16 | 默克专利有限公司 | 用于制备氘化的有机化合物的方法 |
WO2023152346A1 (de) | 2022-02-14 | 2023-08-17 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023208899A1 (en) | 2022-04-28 | 2023-11-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2023222559A1 (de) | 2022-05-18 | 2023-11-23 | Merck Patent Gmbh | Verfahren zur herstellung von deuterierten organischen verbindungen |
CN118235543A (zh) | 2022-06-24 | 2024-06-21 | 默克专利有限公司 | 用于有机电子器件的组合物 |
WO2023247662A1 (de) | 2022-06-24 | 2023-12-28 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
WO2024013004A1 (de) | 2022-07-11 | 2024-01-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024033282A1 (en) | 2022-08-09 | 2024-02-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024126635A1 (en) | 2022-12-16 | 2024-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2024132993A1 (de) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024132892A1 (en) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024133048A1 (en) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Method for preparing deuterated aromatic compounds |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
JP3379020B2 (ja) * | 1992-02-25 | 2003-02-17 | コニカ株式会社 | 新規なピレン系化合物及びその製造法並びに該化合物を含む電子写真感光体 |
JPH05301786A (ja) | 1992-04-27 | 1993-11-16 | Kanegafuchi Chem Ind Co Ltd | 軽量コンクリート |
DE59510315D1 (de) | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
JP2005123205A (ja) * | 2002-10-24 | 2005-05-12 | Toyota Industries Corp | 有機el素子 |
GB0226010D0 (en) * | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
US20060063027A1 (en) | 2002-12-23 | 2006-03-23 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
DE10310887A1 (de) | 2003-03-11 | 2004-09-30 | Covion Organic Semiconductors Gmbh | Matallkomplexe |
JP3970253B2 (ja) | 2003-03-27 | 2007-09-05 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
US7037601B2 (en) | 2003-05-28 | 2006-05-02 | Eastman Kodak Company | White light-emitting device structures |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
DE102004008304A1 (de) | 2004-02-20 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Organische elektronische Vorrichtungen |
EP1655359A1 (de) | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
JP5295756B2 (ja) * | 2005-04-14 | 2013-09-18 | メルク パテント ゲーエムベーハー | 有機電子素子のための化合物 |
EP1888706B1 (de) | 2005-05-03 | 2017-03-01 | Merck Patent GmbH | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
DE102005023437A1 (de) * | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
JP4568659B2 (ja) | 2005-08-16 | 2010-10-27 | 株式会社リコー | 画像形成装置及び画像形成方法 |
JP4687368B2 (ja) | 2005-10-12 | 2011-05-25 | コニカミノルタビジネステクノロジーズ株式会社 | 画像形成方法及び画像形成装置 |
US7977862B2 (en) | 2005-12-21 | 2011-07-12 | Lg Display Co., Ltd. | Organic light emitting devices |
TWI348463B (en) * | 2006-03-06 | 2011-09-11 | Lg Chemical Ltd | Novel anthracene derivative and organic electronic device using the same |
FR2899403A1 (fr) | 2006-03-31 | 2007-10-05 | Thomson Licensing Sa | Methode d'asservissement de la vitesse d'un moteur electrique au demarrage, et appareil mettant en oeuvre le systeme. |
DE102006025846A1 (de) * | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP2008127294A (ja) | 2006-11-17 | 2008-06-05 | Konica Minolta Business Technologies Inc | ピレン系化合物、該化合物を用いた有機感光体、画像形成方法及び画像形成装置 |
JP2008153047A (ja) | 2006-12-18 | 2008-07-03 | Konica Minolta Business Technologies Inc | 光電変換素子、太陽電池及び光センサー |
DE102007024850A1 (de) | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP2009009965A (ja) | 2007-06-26 | 2009-01-15 | Mitsui Chemicals Inc | 有機トランジスタ |
TWI322141B (en) * | 2007-08-28 | 2010-03-21 | Nat Univ Tsing Hua | Host material for blue oled and white light emitting device utilizing the same |
JP2009059840A (ja) | 2007-08-31 | 2009-03-19 | Mitsui Chemicals Inc | 有機トランジスタ |
DE102007058005B4 (de) | 2007-09-25 | 2018-05-17 | Osram Oled Gmbh | Strahlungsemittierende Vorrichtung und Verfahren zu deren Herstellung |
JP5407242B2 (ja) | 2007-09-28 | 2014-02-05 | 大日本印刷株式会社 | エレクトロルミネッセンス素子 |
JP2009302466A (ja) | 2008-06-17 | 2009-12-24 | Mitsui Chemicals Inc | 有機トランジスタ |
DE102008035413A1 (de) * | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
-
2008
- 2008-07-29 DE DE102008035413A patent/DE102008035413A1/de not_active Withdrawn
- 2008-09-18 KR KR1020080091606A patent/KR20100012781A/ko not_active Application Discontinuation
-
2009
- 2009-05-20 US US13/001,818 patent/US9051233B2/en active Active
- 2009-05-20 EP EP09776634.9A patent/EP2303814B1/de active Active
- 2009-05-20 JP JP2011520335A patent/JP5726734B2/ja active Active
- 2009-05-20 CN CN200980125108.0A patent/CN102076640B/zh active Active
- 2009-05-20 WO PCT/EP2009/003602 patent/WO2010012328A1/de active Application Filing
- 2009-05-22 JP JP2011520337A patent/JP5710479B2/ja active Active
- 2009-05-22 KR KR1020107028206A patent/KR101633135B1/ko active IP Right Grant
- 2009-05-22 US US13/001,823 patent/US9090532B2/en active Active
- 2009-05-22 CN CN200980125133.9A patent/CN102076641B/zh active Active
- 2009-05-22 WO PCT/EP2009/003660 patent/WO2010012330A1/de active Application Filing
- 2009-05-22 EP EP09776642.2A patent/EP2303815B1/de active Active
- 2009-05-25 TW TW098117307A patent/TWI478896B/zh active
- 2009-06-05 TW TW098118727A patent/TW201012897A/zh unknown
- 2009-06-26 KR KR1020090057711A patent/KR101104661B1/ko active IP Right Grant
-
2015
- 2015-04-21 US US14/691,708 patent/US10074807B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
WO2010012330A1 (de) | 2010-02-04 |
JP2011529614A (ja) | 2011-12-08 |
CN102076641A (zh) | 2011-05-25 |
KR20100012808A (ko) | 2010-02-08 |
US20110108821A1 (en) | 2011-05-12 |
KR20110050588A (ko) | 2011-05-16 |
TW201012897A (en) | 2010-04-01 |
DE102008035413A1 (de) | 2010-02-04 |
EP2303815A1 (de) | 2011-04-06 |
WO2010012328A1 (de) | 2010-02-04 |
US9051233B2 (en) | 2015-06-09 |
TW201012777A (en) | 2010-04-01 |
JP5710479B2 (ja) | 2015-04-30 |
EP2303814B1 (de) | 2018-12-12 |
EP2303814A1 (de) | 2011-04-06 |
KR20100012781A (ko) | 2010-02-08 |
CN102076640A (zh) | 2011-05-25 |
US20110114889A1 (en) | 2011-05-19 |
US20150228905A1 (en) | 2015-08-13 |
US10074807B2 (en) | 2018-09-11 |
KR101104661B1 (ko) | 2012-01-13 |
CN102076641B (zh) | 2015-02-18 |
CN102076640B (zh) | 2015-06-17 |
EP2303815B1 (de) | 2013-06-26 |
KR101633135B1 (ko) | 2016-06-23 |
TWI478896B (zh) | 2015-04-01 |
US9090532B2 (en) | 2015-07-28 |
JP2011529455A (ja) | 2011-12-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5726734B2 (ja) | 電子デバイス用化合物 | |
JP6250754B2 (ja) | 有機エレクトロルミネッセンス素子のためのトリフェニレン系材料 | |
JP5694194B2 (ja) | 有機エレクトロルミネセンスデバイスのための材料 | |
JP5864263B2 (ja) | エレクトロルミネセンスデバイスのための材料 | |
EP3297978B1 (en) | Materials for organic electroluminescent devices | |
JP6141397B2 (ja) | 有機エレクトロルミネセンスデバイス用材料 | |
JP5788313B2 (ja) | 有機エレクトロルミネセント素子に使用する新規物質 | |
JP5944319B2 (ja) | 有機エレクトロルミネセンス素子のための材料 | |
JP5694159B2 (ja) | 有機エレクトロルミネセントデバイス | |
JP5726732B2 (ja) | 有機エレクトロルミネッセンスデバイス用物質 | |
JP5638960B2 (ja) | 有機エレクトロルミネセントデバイスのための新規材料 | |
JP5680551B2 (ja) | 有機エレクトロルミネッセンスデバイス用材料 | |
JP5730784B2 (ja) | 電子デバイスのための化合物 | |
JP5575754B2 (ja) | 電子デバイスのための化合物 | |
JP5826631B2 (ja) | 有機エレクトロルミネセンス素子のための新規な材料 | |
KR102626977B1 (ko) | 전자 디바이스용 재료 | |
KR20110112186A (ko) | 트리아진 유도체를 포함하는 유기 전계발광 소자 | |
KR20110134411A (ko) | 유기 전자 소자 | |
JP5922223B2 (ja) | 電子デバイス用化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120517 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131107 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131112 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140210 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140701 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140925 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150303 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150401 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5726734 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |