JP5107237B2 - エレクトロルミネセント素子 - Google Patents
エレクトロルミネセント素子 Download PDFInfo
- Publication number
- JP5107237B2 JP5107237B2 JP2008514060A JP2008514060A JP5107237B2 JP 5107237 B2 JP5107237 B2 JP 5107237B2 JP 2008514060 A JP2008514060 A JP 2008514060A JP 2008514060 A JP2008514060 A JP 2008514060A JP 5107237 B2 JP5107237 B2 JP 5107237B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- group
- aryl
- phenyl
- 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 claims abstract description 73
- 239000000463 material Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 15
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000010410 layer Substances 0.000 abstract description 89
- 239000012044 organic layer Substances 0.000 abstract description 8
- 150000004826 dibenzofurans Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 description 140
- -1 dibenzofuran compound Chemical class 0.000 description 129
- 125000003118 aryl group Chemical group 0.000 description 79
- 125000003545 alkoxy group Chemical group 0.000 description 41
- 229910052739 hydrogen Inorganic materials 0.000 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 29
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 125000003710 aryl alkyl group Chemical group 0.000 description 24
- 230000032258 transport Effects 0.000 description 23
- 229910052736 halogen Inorganic materials 0.000 description 22
- 150000002367 halogens Chemical class 0.000 description 22
- 125000001072 heteroaryl group Chemical group 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 17
- 0 CC(*)=C(C(*)=C(*)C(*)=C1N)C1=C(C)* Chemical compound CC(*)=C(C(*)=C(*)C(*)=C1N)C1=C(C)* 0.000 description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229910052725 zinc Inorganic materials 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 229910052790 beryllium Inorganic materials 0.000 description 10
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 9
- 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 8
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 8
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 125000005561 phenanthryl group Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000005427 anthranyl group Chemical group 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 150000002484 inorganic compounds Chemical class 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LDRWNXMCWBUAHW-UHFFFAOYSA-N 2,6-di(pyren-1-yl)dibenzofuran Chemical compound C1=C2C(C3=CC=C4OC5=C(C=6C7=CC=C8C=CC=C9C=CC(C7=C98)=CC=6)C=CC=C5C4=C3)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 LDRWNXMCWBUAHW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000004185 ester group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 125000005401 siloxanyl group Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- DDDMBHCNVWBLAY-PHEQNACWSA-N 2,8-bis[(e)-2-phenylethenyl]dibenzofuran Chemical compound C=1C=CC=CC=1/C=C/C(C=C1C2=C3)=CC=C1OC2=CC=C3\C=C\C1=CC=CC=C1 DDDMBHCNVWBLAY-PHEQNACWSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 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 2
- DDPLWPWHVHFSLO-UHFFFAOYSA-N 2-phenanthren-9-yl-8-pyren-1-yldibenzofuran Chemical compound C12=CC=CC=C2C2=CC=CC=C2C=C1C1=CC=C(OC=2C3=CC(=CC=2)C=2C4=CC=C5C=CC=C6C=CC(C4=C65)=CC=2)C3=C1 DDPLWPWHVHFSLO-UHFFFAOYSA-N 0.000 description 2
- XXXACBHSLPNJIU-UHFFFAOYSA-N 4-(2,6-ditert-butyl-10-naphthalen-2-ylanthracen-9-yl)dibenzofuran Chemical compound C1=CC=CC2=CC(C3=C4C=CC(=CC4=C(C=4C5=C(C6=CC=CC=C6O5)C=CC=4)C4=CC=C(C=C43)C(C)(C)C)C(C)(C)C)=CC=C21 XXXACBHSLPNJIU-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- LFFYFVATSNGHSX-UHFFFAOYSA-N 6-bromo-2-pyren-1-yldibenzofuran Chemical compound C1=C2C(C3=CC=C4OC5=C(C4=C3)C=CC=C5Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 LFFYFVATSNGHSX-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910017109 AlON Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003828 azulenyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzoquinoline Natural products C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 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
- RCDMUNHSQCVVBJ-UHFFFAOYSA-N dibenzofuran-1-amine Chemical class O1C2=CC=CC=C2C2=C1C=CC=C2N RCDMUNHSQCVVBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- PVADDRMAFCOOPC-UHFFFAOYSA-N germanium monoxide Inorganic materials [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 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 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- TUVFNVZTFJROFS-UHFFFAOYSA-N 1,5-dibromo-3,7-ditert-butylnaphthalene Chemical compound C1=C(C(C)(C)C)C=C(Br)C2=CC(C(C)(C)C)=CC(Br)=C21 TUVFNVZTFJROFS-UHFFFAOYSA-N 0.000 description 1
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 description 1
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical class N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 1
- PQYIVUDIIIJJDM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-thiadiazole Chemical compound C1=CC=C2C(C3=NN=C(S3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 PQYIVUDIIIJJDM-UHFFFAOYSA-N 0.000 description 1
- XCAHNWGVQJYSLY-UHFFFAOYSA-N 2,5-diphenyl-1,3-thiazole Chemical compound C=1N=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 XCAHNWGVQJYSLY-UHFFFAOYSA-N 0.000 description 1
- ZNMPPGWFJMSOPK-UHFFFAOYSA-N 2,6-ditert-butylanthracene Chemical compound C1=C(C(C)(C)C)C=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 ZNMPPGWFJMSOPK-UHFFFAOYSA-N 0.000 description 1
- TZGXZNWUOXLMFL-UHFFFAOYSA-N 2,6-ditert-butylnaphthalene Chemical compound C1=C(C(C)(C)C)C=CC2=CC(C(C)(C)C)=CC=C21 TZGXZNWUOXLMFL-UHFFFAOYSA-N 0.000 description 1
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 1
- QPTWHGCUUHVOMG-UHFFFAOYSA-N 2-bromo-8-pyren-1-yldibenzofuran Chemical compound C1=C2C(C3=CC=C4OC5=CC=C(C=C5C4=C3)Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 QPTWHGCUUHVOMG-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ZFXZGNSFTILOND-UHFFFAOYSA-L 2-carboxyquinolin-8-olate;manganese(2+) Chemical compound [Mn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 ZFXZGNSFTILOND-UHFFFAOYSA-L 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 1
- LBIZVFMCGAKADX-UHFFFAOYSA-N 2-naphthalen-2-yl-8-pyren-1-yldibenzofuran Chemical compound C1=C2C(C3=CC=C4OC5=CC=C(C=C5C4=C3)C3=CC4=CC=CC=C4C=C3)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 LBIZVFMCGAKADX-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- MWKLOMOIKCPLOY-UHFFFAOYSA-N 3,5-dinaphthalen-1-yl-1h-1,2,4-triazole Chemical compound C1=CC=C2C(C3=NN=C(N3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MWKLOMOIKCPLOY-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- PCXZQANGNVBJFB-UHFFFAOYSA-N 3-methyl-9-(2-phenylphenyl)carbazole Chemical group C12=CC=CC=C2C2=CC(C)=CC=C2N1C1=CC=CC=C1C1=CC=CC=C1 PCXZQANGNVBJFB-UHFFFAOYSA-N 0.000 description 1
- UAPNUNDZDVNTDQ-UHFFFAOYSA-N 4,5-diphenyl-1,2,3-triazole Chemical compound C1=CC=CC=C1C1=NNN=C1C1=CC=CC=C1 UAPNUNDZDVNTDQ-UHFFFAOYSA-N 0.000 description 1
- YOPJQOLALJLPBS-UHFFFAOYSA-N 4,5-diphenyloxadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)ON=N1 YOPJQOLALJLPBS-UHFFFAOYSA-N 0.000 description 1
- DCSAGKFXOGNMRK-UHFFFAOYSA-N 4-(10-bromo-2,6-ditert-butylanthracen-9-yl)dibenzofuran Chemical compound C1=C(C(C)(C)C)C=CC2=C(Br)C3=CC(C(C)(C)C)=CC=C3C(C=3C=4OC5=CC=CC=C5C=4C=CC=3)=C21 DCSAGKFXOGNMRK-UHFFFAOYSA-N 0.000 description 1
- IBNIOTFLQOPTBS-UHFFFAOYSA-N 4-(2,6-ditert-butyl-10-dibenzofuran-4-ylanthracen-9-yl)dibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(C1=C3C=CC(=CC3=C(C=3C4=C(C5=CC=CC=C5O4)C=CC=3)C3=CC=C(C=C31)C(C)(C)C)C(C)(C)C)=CC=C2 IBNIOTFLQOPTBS-UHFFFAOYSA-N 0.000 description 1
- CEPDCTNETHOOEZ-UHFFFAOYSA-N 4-(2,6-ditert-butyl-10-pyren-1-ylanthracen-9-yl)dibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(C1=C3C=CC(=CC3=C(C=3C4=CC=C5C=CC=C6C=CC(C4=C65)=CC=3)C3=CC=C(C=C31)C(C)(C)C)C(C)(C)C)=CC=C2 CEPDCTNETHOOEZ-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 description 1
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZWKIJOPJWWZLDI-UHFFFAOYSA-N 4-fluoro-1h-indole Chemical compound FC1=CC=CC2=C1C=CN2 ZWKIJOPJWWZLDI-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- VBKDJWISHQGFML-UHFFFAOYSA-N 6-bromo-2-iododibenzofuran Chemical compound C12=CC(I)=CC=C2OC2=C1C=CC=C2Br VBKDJWISHQGFML-UHFFFAOYSA-N 0.000 description 1
- LBHINWRDFSXSRK-UHFFFAOYSA-N 6-phenanthren-9-yl-2-pyren-1-yldibenzofuran Chemical compound C12=CC=CC=C2C2=CC=CC=C2C=C1C1=CC=CC2=C1OC1=CC=C(C=3C4=CC=C5C=CC=C6C=CC(C4=C65)=CC=3)C=C12 LBHINWRDFSXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- BLWBMTYSBMTMAA-UHFFFAOYSA-N 9-bromo-2,6-ditert-butyl-10-iodoanthracene Chemical compound C1=C(C(C)(C)C)C=CC2=C(Br)C3=CC(C(C)(C)C)=CC=C3C(I)=C21 BLWBMTYSBMTMAA-UHFFFAOYSA-N 0.000 description 1
- TWELBQMSBSLKDQ-UHFFFAOYSA-N 9-n,10-n-bis(4-butylphenyl)-9-n,10-n-bis(2-methylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1N(C=1C=CC(CCCC)=CC=1)C=1C(=CC=CC=1)C)C1=CC=CC=C1C TWELBQMSBSLKDQ-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
- HWWJPQVZDKBEON-UHFFFAOYSA-N C(C1)C=Cc2c1c1cccc(-c(c3ccccc33)c(cccc4)c4c3-c3cc(cccc4)c4c4c3cccc4)c1[o]2 Chemical compound C(C1)C=Cc2c1c1cccc(-c(c3ccccc33)c(cccc4)c4c3-c3cc(cccc4)c4c4c3cccc4)c1[o]2 HWWJPQVZDKBEON-UHFFFAOYSA-N 0.000 description 1
- UBOZHCKXQQZRTO-CGVUKPDCSA-N C([C@H]1C=C2C3=C(C=CCC4)C4=C4C=CC=CC4C3)C1C1=C2OC2C=CC(c3c(ccc4cccc(cc5)c44)c4c5cc3)=CC12 Chemical compound C([C@H]1C=C2C3=C(C=CCC4)C4=C4C=CC=CC4C3)C1C1=C2OC2C=CC(c3c(ccc4cccc(cc5)c44)c4c5cc3)=CC12 UBOZHCKXQQZRTO-CGVUKPDCSA-N 0.000 description 1
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PFHMVNJTJDLWQA-UHFFFAOYSA-N C1=CC(c2c(ccc3c4c(cc5)ccc3)c4c5cc2)=CC2c3cc(N(c4ccccc4)c4ccccc4)ccc3OC12 Chemical compound C1=CC(c2c(ccc3c4c(cc5)ccc3)c4c5cc2)=CC2c3cc(N(c4ccccc4)c4ccccc4)ccc3OC12 PFHMVNJTJDLWQA-UHFFFAOYSA-N 0.000 description 1
- WADDUTUOTNFEKN-HMZUSVAUSA-N C1C=Cc(ccc2c(cc3)C4=C[C@H]5c(cccc6C7=C(C=C8)C9=C%10C8=CC=CC%10=CCC9C=C7)c6OC5C=C4)c4c2c3C=CC14 Chemical compound C1C=Cc(ccc2c(cc3)C4=C[C@H]5c(cccc6C7=C(C=C8)C9=C%10C8=CC=CC%10=CCC9C=C7)c6OC5C=C4)c4c2c3C=CC14 WADDUTUOTNFEKN-HMZUSVAUSA-N 0.000 description 1
- OIOGKZSNDGRGTR-UHFFFAOYSA-N C=1(C(=CC=CC1O)C(=O)O)C.CC1=NC2=C(C=CC=C2C=C1)C(=O)O.CC1=NC2=C(C=CC=C2C=C1)C(=O)O Chemical compound C=1(C(=CC=CC1O)C(=O)O)C.CC1=NC2=C(C=CC=C2C=C1)C(=O)O.CC1=NC2=C(C=CC=C2C=C1)C(=O)O OIOGKZSNDGRGTR-UHFFFAOYSA-N 0.000 description 1
- KHNBEJDCKCDOTG-UHFFFAOYSA-N CC(C=C(C)OC1)=[O]1(C)=C Chemical compound CC(C=C(C)OC1)=[O]1(C)=C KHNBEJDCKCDOTG-UHFFFAOYSA-N 0.000 description 1
- VKDIWRUULHQWJS-UHFFFAOYSA-N CC[n]1c(ccc(C)c2)c2c2c1cccc2 Chemical compound CC[n]1c(ccc(C)c2)c2c2c1cccc2 VKDIWRUULHQWJS-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IPAIJAHZKASIRX-UHFFFAOYSA-N Cc(cc1)cc2c1[n](C)c1ccccc21 Chemical compound Cc(cc1)cc2c1[n](C)c1ccccc21 IPAIJAHZKASIRX-UHFFFAOYSA-N 0.000 description 1
- FLDRLXJNISEWNZ-UHFFFAOYSA-N Cc1c(cccc2)c2nc2c1cccc2 Chemical compound Cc1c(cccc2)c2nc2c1cccc2 FLDRLXJNISEWNZ-UHFFFAOYSA-N 0.000 description 1
- XLTFRTTTZWMJJQ-UHFFFAOYSA-N Cc1c2[o]c(cccc3)c3c2ccc1 Chemical compound Cc1c2[o]c(cccc3)c3c2ccc1 XLTFRTTTZWMJJQ-UHFFFAOYSA-N 0.000 description 1
- SZQCPPRPWDXLMM-UHFFFAOYSA-N Cc1c[n](C)nc1 Chemical compound Cc1c[n](C)nc1 SZQCPPRPWDXLMM-UHFFFAOYSA-N 0.000 description 1
- GBGPVUAOTCNZPT-UHFFFAOYSA-N Cc1cc(cccc2)c2[o]1 Chemical compound Cc1cc(cccc2)c2[o]1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 1
- BLZKSRBAQDZAIX-UHFFFAOYSA-N Cc1cc2ccccc2[s]1 Chemical compound Cc1cc2ccccc2[s]1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 1
- LUYISICIYVKBTA-UHFFFAOYSA-N Cc1cc2cccnc2cc1 Chemical compound Cc1cc2cccnc2cc1 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 1
- JFMOEAUCEDWSLO-UHFFFAOYSA-N Cc1ccc(-c2ccc[s]2)[s]1 Chemical compound Cc1ccc(-c2ccc[s]2)[s]1 JFMOEAUCEDWSLO-UHFFFAOYSA-N 0.000 description 1
- VFCRTEVRAODBLT-UHFFFAOYSA-N Cc1ccc(c2ccc(C)cc2[o]2)c2c1 Chemical compound Cc1ccc(c2ccc(C)cc2[o]2)c2c1 VFCRTEVRAODBLT-UHFFFAOYSA-N 0.000 description 1
- NICUQYHIOMMFGV-UHFFFAOYSA-N Cc1cccc2c1[s]c1ccccc21 Chemical compound Cc1cccc2c1[s]c1ccccc21 NICUQYHIOMMFGV-UHFFFAOYSA-N 0.000 description 1
- MUDSDYNRBDKLGK-UHFFFAOYSA-N Cc1ccnc2c1cccc2 Chemical compound Cc1ccnc2c1cccc2 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 1
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N Cc1ccncc1 Chemical compound Cc1ccncc1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- GOZPTOHMTKTIQP-UHFFFAOYSA-N OC1=CC=CC2=CC=C3C=CC(=NC3=C21)C(=O)O Chemical compound OC1=CC=CC2=CC=C3C=CC(=NC3=C21)C(=O)O GOZPTOHMTKTIQP-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 229910003071 TaON Inorganic materials 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910010282 TiON Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
- RDIBRFFSGFBDHT-UHFFFAOYSA-L [Zn++].Oc1cccc2ccc3ccc(nc3c12)C([O-])=O.Oc1cccc2ccc3ccc(nc3c12)C([O-])=O Chemical compound [Zn++].Oc1cccc2ccc3ccc(nc3c12)C([O-])=O.Oc1cccc2ccc3ccc(nc3c12)C([O-])=O RDIBRFFSGFBDHT-UHFFFAOYSA-L 0.000 description 1
- ANCWSKHLTSPBSR-UHFFFAOYSA-L [Zn+2].OC1=C(C=CC(=C1)C)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC(=C1)C)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-] Chemical compound [Zn+2].OC1=C(C=CC(=C1)C)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC(=C1)C)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-] ANCWSKHLTSPBSR-UHFFFAOYSA-L 0.000 description 1
- OGJCHSNBNHMIPX-UHFFFAOYSA-L [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC(=CC=C1)F)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC(=CC=C1)F)C(=O)[O-] Chemical compound [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC(=CC=C1)F)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC(=CC=C1)F)C(=O)[O-] OGJCHSNBNHMIPX-UHFFFAOYSA-L 0.000 description 1
- OWSSKCMPBCNEOB-UHFFFAOYSA-L [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)C)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)C)C(=O)[O-] Chemical compound [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)C)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)C)C(=O)[O-] OWSSKCMPBCNEOB-UHFFFAOYSA-L 0.000 description 1
- GVVICUIYMBWHBP-UHFFFAOYSA-L [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)F)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)F)C(=O)[O-] Chemical compound [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)F)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=C(C=C1)F)C(=O)[O-] GVVICUIYMBWHBP-UHFFFAOYSA-L 0.000 description 1
- RAAFIQLSXBDKME-UHFFFAOYSA-L [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C=1SC=CC1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C=1SC=CC1)C(=O)[O-] Chemical compound [Zn+2].OC1=C(C=CC=C1)C1(OC(=NN1)C=1SC=CC1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C=1SC=CC1)C(=O)[O-] RAAFIQLSXBDKME-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- LGHMHEQXPCDYJG-UHFFFAOYSA-K aluminum;8-hydroxy-2-methyl-1h-quinoline-2-carboxylate Chemical compound [Al+3].C1=CC=C2C=CC(C)(C([O-])=O)NC2=C1O.C1=CC=C2C=CC(C)(C([O-])=O)NC2=C1O.C1=CC=C2C=CC(C)(C([O-])=O)NC2=C1O LGHMHEQXPCDYJG-UHFFFAOYSA-K 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000008366 benzophenones Chemical group 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- UKLRYFCAOYNEEW-UHFFFAOYSA-N c(cc1)cc(c2ccc3)c1[o]c2c3Nc1ccc2[o]c3ccccc3c2c1 Chemical compound c(cc1)cc(c2ccc3)c1[o]c2c3Nc1ccc2[o]c3ccccc3c2c1 UKLRYFCAOYNEEW-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 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
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([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
- 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
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- JOFBTOVNZIUWPX-UHFFFAOYSA-N dibenzofuran-1-ylboronic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2B(O)O JOFBTOVNZIUWPX-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical class S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OJWZBBBQTAENDN-UHFFFAOYSA-N n,n-diphenyl-4-(8-pyren-1-yldibenzofuran-2-yl)aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC(=CC=C3OC2=CC=1)C=1C2=CC=C3C=CC=C4C=CC(C2=C43)=CC=1)C1=CC=CC=C1 OJWZBBBQTAENDN-UHFFFAOYSA-N 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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TWLXDPFBEPBAQB-UHFFFAOYSA-N orthoperiodic acid Chemical compound OI(O)(O)(O)(O)=O TWLXDPFBEPBAQB-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000012462 polypropylene substrate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- SXKBKLGHKDARFJ-UHFFFAOYSA-L zinc;2-(1,3-benzoxazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2O1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2O1 SXKBKLGHKDARFJ-UHFFFAOYSA-L 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic 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
- H10K85/657—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
-
- 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
-
- 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
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Massaging Devices (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
−CN、環状エーテル、−B(OR65)2及び/又はハロゲン、特にフッ素であるか、あるいは
R81とR82、R82とR83、R83とR84、R85とR86、R86とR87、R87とR88、R97とR96、R96とR95、R95とR94、R97’とR96’、R96’とR95’、R95’及び/又はR94’、並びに/又は基R91、R92及びR93、もしくはR91’、R92’及びR93’の互いに隣接する2個は一緒になって基:
Mは、結合基、たとえば単結合(直接結合)、−CO−、−COO−;−S−;−SO−;−SO2−;−O−;場合により−O−、又は−S−1個以上で中断されたC1〜C12アルキレン、C2〜C12アルケニレン、又はC2〜C12アルキニレン;又は基[M1]nであり、ここで、nは、整数1〜20であり、M1は、場合によりGで置換されているアリーレン又はヘテロアリーレン、特に、場合によりC1〜C12アルキル、ハロゲン、−OR201、−SR202及び/又は−NR203R204(式中、R201は、水素、C1〜C24アルキル、Eで置換された及び/又はDで中断されたC1〜C24アルキルである)で置換されていてもよいナフチレン、ビフェニレン、スチリレン、アントリレン、又はピレニレンであり;それぞれ場合により基C1〜C6アルキル、ハロゲン、−OH及び/又はC1〜C4アルコキシ1個以上で置換されていてもよいC2〜C12アルケニル、C3〜C6アルケノイル、C3〜C8シクロアルキル、又はベンゾイル;それぞれ、場合によりハロゲン、−OH、C1〜C12アルキル、C1〜C12アルコキシ、フェノキシ、C1〜C12アルキルスルファニル、フェニルスルファニル、−N(C1〜C12アルキル)2及び/又はジフェニルアミノで置換されていてもよいC6〜C14アリール、特にフェニル、ナフチル、フェナントリル、アントラニル、又はピレニルであり;
R202は、C1〜C24アルキル、Eで置換された及び/又はDで中断されたC1〜C24アルキル;C2〜C12アルケニル、C1〜C8アルカノイル、C2〜C12アルケニル、C3〜C6アルケノイル;それぞれ、場合により基C1〜C6アルキル、ハロゲン、−OH、C1〜C4アルコキシ又はC1〜C4アルキルスルファニル1個以上で置換されていてもよい、C3〜C8シクロアルキル、又はベンゾイル;それぞれ場合によりハロゲン、C1〜C12アルキル、C1〜C12アルコキシ、フェニル−C1〜C3アルキルオキシ、フェノキシ、C1〜C12アルキルスルファニル、フェニルスルファニル、−N(C1〜C12アルキル)2、ジフェニルアミノ、−(CO)O(C1〜C8アルキル)、−(CO)−C1〜C8アルキル、又は(CO)N(C1〜C8アルキル)2で置換されていてもよい、C6〜C14アリール、特にフェニル、ナフチル、フェナントリル、アントラニル、又はピレニルであり;
R203及びR204は、互いに独立して、水素、C1〜C24アルキル、Eで置換された及び/又はDで中断されたC1〜C24アルキル;それぞれ、場合により、基C1〜C6アルキル、ハロゲン、−OH、又はC1〜C4アルコキシ1個以上で置換されていてもよいC2〜C5アルケニル、C3〜C8シクロアルキル、又はベンゾイル;それぞれ、C1〜C12アルキル、ベンゾイル又はC1〜C12アルコキシで置換されていてもよい、フェニル−C1〜C3アルキル、C1〜C8アルカノイル、C3〜C12アルケノイル、C6〜C14アリール、特にフェニルナフチル、フェナントリルアントラニル、又はピレニルであるか;あるいはR203とR204は一緒になって、場合により−O−、−S−、又は−NR205−で中断された及び/又はヒドロキシル、C1〜C4アルコキシ、C2〜C4アルカノイルオキシ又はベンゾイルオキシで置換されていてもよいC2〜C8アルキレン又は分岐状C2〜C8アルキレンであり、ここでR203及びR2044により形成された環は、場合により、C1〜C8−アルキル、C1〜C8−アルコキシ、ハロゲン、又はシアノで1〜3回置換されていることができるフェニルにより1又は2回縮合されていてもよい;
R205は、水素、C1〜C24アルキル、Eで置換された及び/又はDで中断されたC1〜C24アルキル;C2〜C5アルケニル、C3〜C8シクロアルキル、フェニル−C1〜C3アルキル、C1〜C8アルカノイル、C3〜C12アルケノイル、C6〜C14アリール、特にベンゾイル;それぞれ、場合によりC1〜C12アルキル、ベンゾイル、又はC1〜C12アルコキシで置換されている、フェニル、ナフチル、フェナントリル、アントラニル、又はピレニルであり;
Dは、−CO−、−COO−、−OCOO−、−S−、−SO−、−SO2−、−O−、−NR5−、−SiR61R62−、−POR5−、−CR63=CR64−、又は−C≡C−であり;
Eは、ハロゲン、−OR5、−SR5、−NR5R6、
で置換されていてもよいC6〜C14アリール、特にフェニル、ナフチル、フェナントリル、アントラニル、又はピレニル[式中、R62、R63及びR64は、互いに独立してC1〜C8アルキル基、C6〜C24アリール基又はC7〜C12アラルキル基、−CN、環状エーテル及び/又は−B(OR65)2(式中、R65は、水素、C1〜C24アルキル、C3〜C8シクロアルキル、C7〜C24アラルキル、C2〜C18アルケニル、C2〜C24アルキニル、ヒドロキシ、メルカプト、C1〜C24アルコキシ、C1〜C24アルキルチオ、C6〜C30アリール、C2〜C30ヘテロアリール、ハロゲン、特にフッ素、ハロアルカン、シリル、シロキサニル、及び隣接する置換基R65と一緒に形成された脂環式の環である)である];−OR5、−SR5、−NR5R6、−COR8、−COOR7、−CONR5R6、−CN、ハロゲン、シリル、C1〜C18アルキル、又はヘテロアリールであり、
Gは、E、又はC1〜C18アルキル(式中、R5及びR6は、互いに独立してH、C6〜C18アリールである);C1〜C18アルキル、C1〜C18アルコキシ、又はシリルで置換されたC6〜C18アリール;C1〜C18アルキル、又は−O−で中断されたC1〜C18アルキルであるか;あるいは
R5とR6は一緒になって5又は6員環、特に
R7は、H、C6〜C18アリール、C7〜C12アルキルアリール(C1〜C18アルキル、もしくはC1〜C18アルコキシで置換されている);C1〜C18アルキル;又は−O−で中断されたC1〜C18アルキルであり;
R8は、C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル、C7〜C12アルキルアリール、又は−O−で中断されたC1〜C18アルキルであり;
R61及びR62は、互いに独立して、C6〜C18アリール;C1〜C18アルキル、C1〜C18アルコキシで置換されたC6〜C18アリール;又は−O−で中断されたC1〜C18アルキルであり、そして
R63及びR64は、互いに独立して、H、C6〜C18アリール;C1〜C18アルキル、C1〜C18アルコキシで置換されたC6〜C18アリール;又は−O−で中断されたC1〜C18アルキルであり;
ただしR81、R82、R83、R84、R85、R86、R87及びR88の少なくとも1個は、H、−OR201、−SR202及びC1〜C24アルキルとは異なり;さらに次の化合物:
Mが、単結合、−CO−、−COO−、−S−、−SO−、−SO2−、−O−、
A6及びA7は、互いに独立して、H、C1〜C18アルキル、E’で置換された及び/又はD’で中断されたC1〜C18アルキル、C6〜C24アリール、G’で置換されたC6〜C24アリール、C2〜C20ヘテロアリール、G’で置換されたC2〜C20ヘテロアリール、C2〜C18アルケニル、C2〜C18アルキニル、C1〜C18アルコキシ、E’で置換された及び/又はD’で中断されたC1〜C18アルコキシ、C7〜C25アラルキル、又は−CO−A28であり、
A8は、C1〜C18アルキル、E’で置換された及び/又はD’で中断されたC1〜C18アルキル、C6〜C24アリール、又はC7〜C25アラルキルであり、
A9及びA10は、互いに独立して、C1〜C18アルキル、E’で置換された及び/又はD’で中断されたC1〜C18アルキル、C6〜C24アリール、G’で置換されたC6〜C24アリール、C2〜C20ヘテロアリール、G’で置換されたC2〜C20ヘテロアリール、C2〜C18アルケニル、C2〜C18アルキニル、C1〜C18アルコキシ、E’で置換された及び/又はD’で中断されたC1〜C18アルコキシ、又はC7〜C25アラルキルであるか、あるいは
A9及びA10は、場合によりC1〜C18アルキル基1個以上で置換されていることができる環、特に5−又は6−員環を形成し;
A14及びA15は、互いに独立して、H、C1〜C18アルキル、E’で置換された及び/又はD’で中断されたC1〜C18アルキル、C6〜C24アリール、G’で置換されたC6〜C24アリール、C2〜C20ヘテロアリール、又はG’で置換されたC2〜C20ヘテロアリールであり、
D’は、−CO−;−COO−;−S−;−SO−;−SO2−;−O−;−NA25−;−SiA30A31−;−POA32−;−CA23=CA24−;又は−C≡C−であり;そして
E’は、−OA29;−SA29;−NA25A26;−COA28;−COOA27;−CONA25A26;−CN;−OCOOA27;又はハロゲンであり;G’は、E’、又はC1〜C18アルキルであり;ここで、A23、A24、A25及びA26は、互いに独立して、H;C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル、又は−O−で中断されたC1〜C18アルキルであるか;あるいはA25とA26は一緒になって5又は6員環、特に
A27及びA28は、互いに独立して、H;C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル、又は−O−で中断されたC1〜C18アルキルであり、
A29は、H;C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル;又は−O−で中断されたC1〜C18アルキルであり、
A30及びA31は、互いに独立して、C1〜C18アルキル、C6〜C18アリール、又はC1〜C18アルキルで置換されたC6〜C18アリールであり、そして
A32は、C1〜C18アルキル、C6〜C18アリール、又はC1〜C18アルキルで置換されたC6〜C18アリールである)である、化合物が好ましい。
R18及びR19は、互いに独立して、C1〜C8アルキル、又はシクロヘキサンである)である。
ここで、a及びbは、0又は1であり、
W1及びW2が、互いに独立して、式:
W3が、式:
R14は、H、シリル、たとえばトリ(C1〜C8アルキル)シリル、C1〜C18アルキル;又はEで置換された及び/又はDで中断されたC1〜C18アルキル;C1〜C18アルコキシ;又はEで置換された及び/又はDで中断されたC1〜C18アルコキシ;
R18及びR19は、互いに独立して、C1〜C18アルキル;C1〜C18アルコキシ、C6〜C18アリール;C7〜C18アラルキルであるか;又はR18とR19は一緒になって、場合によりC1〜C8アルキルで置換されていることができる環、特に5−又は6−員環を形成し、
R21、R22、R23、R24、R25、R26及びR27は、互いに独立して、H、E、C1〜C18アルキル;Eで置換された及び/又はDで中断されたC1〜C18アルキル;C7〜C18アラルキル;Gで置換されたC7〜C18アラルキルである)の基であるか;あるいは
W3が、式:
R317は、水素原子、−O−で中断されていてもよいC1〜C25アルキル基、シクロアルキル基、C7〜C18アラルキル基、C6〜C18アリール基、又はGで置換されていてもよい複素環
基を表す)の基であり;ここで
Dは、−CO−、−COO−、−OCOO−、−S−、−SO−、−SO2−、−O−、−NR5−、SiR61R62−、−POR5−、−CR63=CR64−、又は−C≡C−であり;
Eは、−OR5、−SR5、−NR5R6、−COR8、−COOR7、−OCOOR7、−CONR5R6、−CN、又はハロゲンであり;
Gは、E、又はC1〜C18アルキルであり、ここで、R5及びR6は、互いに独立して、C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル、又は−O−で中断されたC1〜C18アルキルであるか;あるいは
R5とR6は、一緒になって5又は6員環、特に
R7は、C7〜C12アルキルアリール;C1〜C18アルキル;又は−O−で中断されたC1〜C18アルキルであり;
R8は、C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;C1〜C18アルキル;C7〜C12アルキルアリール、又は−O−で中断されたC1〜C18アルキルであり;
R61及びR62は、互いに独立して、C6〜C18アリール;C1〜C18アルキルもしくはC1〜C18アルコキシで置換されたC6〜C18アリール;又は−O−で中断されたC1〜C18アルキルであり、そして
R63及びR64は、互いに独立して、H、C6〜C18アリール;C1〜C18アルキル、C1〜C18アルコキシで置換されたC6〜C18アリール;又は−O−で中断されたC1〜C18アルキルである)である]の基である。
W2は、基:
W3は、基:
bが、0又は1であり、W1及びW2が、前記定義の通りであり、好ましくは、互いに独立して、式:
W3が、式:−NR70R71の基であり、ここで、R70及びR71は、互いに独立して、式:
X1は、水素、又はC1〜C8アルキルを表し;
R75、R76、R77及びR78は、互いに独立して、H、E、C6〜C18アリール;Eで置換されたC6〜C18アリール;C1〜C18アルキル;Gで置換された及び/又はDで中断されたC1〜C18アルキル;C7〜C18アラルキル;又はEで置換されたC7〜C18アラルキルであり;
ここで、D、E、G、R11、R11’、R12’、R16、R16’、R17、R17’、R18、R19、R30、R31、R32及びR33は、前記定義の通りであり、そしてR30’、R31’、R32’及びR33’は、互いに独立して、R30の意味を有する)を形成する。
W3は、式:
E−W3と反応させるか、R100がハロゲンでない場合には、
−Hal−W3
(式中、Halはハロゲン、好ましくはブロモを表す)と反応させる工程を含む方法により製造することができる。
(a)陽極、
(b)正孔注入層及び/又は正孔輸送層、
(c)発光層、
(d)場合により電子輸送層及び
(e)陰極
をこの順序で含む。
(a)陽極、たとえばITO、
(b1)正孔注入層、たとえばCuPc、
(b2)正孔輸送層、たとえばN,N’−ジ(ナフタレン−1−イル)−N,N’−ジフェニル−ベンジジン(NPD)又はTCTA、
(c)リン光化合物と、本発明のジベンゾフラン化合物、特に化合物A−1〜A−66、B−1〜B−18、C−1及びC−2とを含む発光層、
正孔抑制層、たとえばBCP又はBAlq、
(d)電子輸送層、たとえばAlq3、及び
無機化合物層、たとえばLiF、
(e)陰極、たとえばAl
をこの順序で含むことができる。
(a)陽極、たとえばITO、
(b1)正孔注入層、たとえばCuPc、
(b2)正孔輸送層、たとえば、NPD又はTCTA、
(c)蛍光ゲスト化合物と、本発明のジベンゾフランホスト化合物、特に化合物A−1〜A−66、B−1〜B−18、C−1及びC−2とを含む発光層、
場合により正孔抑制層、たとえばBCP、
(d)電子輸送層、たとえばAlq3又はTPBI、及び
無機化合物層、たとえばLiF、
(e)陰極、たとえばAl
をこの順序で含んでいてもよい。
実施例1
2,8−ビス−((E)−スチリル)−ジベンゾフランの合成
酢酸(54g)中の臭素(92.6g、0.58mol)を、酢酸(232g)中のジベンゾフラン(23.2g、0.14mol)の溶液に、75℃で加えた。次いで、混合物を75℃で3時間攪拌した。反応混合物を室温に冷まし、H2Oに注いだ。橙色固体をNa2S2O3水溶液及びH2Oで洗浄した。次いで、n−ヘキサンからの再結晶により粗生成物を精製し、純粋な生成物を白色固体(収率38%;融点:226℃)として得た。
テトラエチルアミンヒドロキシド(13.6g、18.4mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(142mg)及びtrans−2−フェニルビニルボロン酸(2.3g、15.3mmol)を、N,N’−ジメチルアセトアミド(DMA)(30ml)中の実施例1a)からの生成物(2.00g、6.14mmol)の溶液に加えた。次いで、混合物を110℃で24時間攪拌した。反応混合物を室温に冷まし、H2Oに注いだ。ろ過及びn−ヘキサンでの洗浄後、灰色の粗生成物を得た。CH2Cl2を用いるシリカゲルカラムクロマトグラフィーにより粗生成物を精製し、白色固体(収率71%、融点:226℃)をもたらした。
1,5−ジベンゾフラニル−3,7−ジ−t−ブチルナフタレンの合成
四塩化炭素(75ml)中のFe(212mg)及び臭素(18.3g、0.11mol)を、四塩化炭素(300ml)中の2,6−ジ−t−ブチルナフタレン(25g、0.1mol)の溶液に、0℃で加えた。次いで、混合物を0℃で3.5時間攪拌した。反応混合物をH2Oに注ぎ、次いで有機層をNa2S2O3水溶液及びH2Oで洗浄した。有機層をMgSO4で乾燥し、蒸発により濃縮した。次いで、n−ヘキサンを用いるシリカゲルカラムクロマトグラフィーにより粗生成物を精製し、白色固体(収率31%;融点:226℃)をもたらした。
テトラエチルアミンヒドロキシド(3.5g、14.2mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(100mg)及び4−ジベンゾフランボロン酸(3g、14.0mmol)を、DMA(30ml)中の実施例2a)からの生成物(1.88g、4.72mmol)の溶液に加えた。混合物を110℃で1時間攪拌し、次いで室温に冷まし、これにより黄色固体の生成物を得た。これをろ過により単離し、H2Oで洗浄した。次いで、黄色固体を、CH2Cl2に溶解し、MgSO4で乾燥した。蒸発による濃縮、及び酢酸エチル/ヘキサン=1/30を溶離剤として用いるシリカゲルカラムクロマトグラフィーにより純粋な黄色固体の生成物(収率65%;融点:226℃)を得た。
11a)2−ブロモジベンゾフラン
酢酸(5g)中の臭素(23.8g、0.156mol)を、50℃で酢酸(230g)中のジベンゾフラン(25g、0.149mol)の溶液に加えた。次いで、混合物を50℃で4時間攪拌した。反応混合物を室温に冷まし、H2Oに注いだ。橙色固体をNa2S2O3水溶液及びH2Oで洗浄した。次いで、粗生成物をトルエン/CH2Cl2からの再結晶により精製し、白色固体(収率13%)として純粋な生成物を得た。
2−ブロモジベンゾフラン(2.5g、10.1mmol)、オルト過ヨウ素酸(0.49g、2.15mmol)、ヨウ素(1.02g、4.02mmol)、硫酸、H2O(2ml)及び酢酸(10ml)を、反応容器に入れ、混合物を70℃で3時間攪拌した。室温に冷ました後、反応混合物を水に注ぎ、ろ過した。白色固体をメタノールで洗浄し、目的の生成物を得た(1.92g、51%)。
ジフェニル−[4−(8−ピレン-1−イル−ジベンゾフラン−2−イル)−フェニル]−アミン
2−ナフタレン−2−イル−8−ピレン−1−イル−ジベンゾフラン
9,10−ビス−ジベンゾフラン−4−イル−2,6−ジ−t−ブチル−アントラセン
4−(2,6−ジ−t−ブチル−10−ナフタレン−2−イル−アントラセン−9−イル)−ジベンゾフランの合成
15a)9−ブロモ−2,6−ジ−t−ブチル−アントラセン
臭素(3.02g、18.9mmol)を、四塩化炭素(200ml)中の2,6−ジ−t−ブチルアントラセン(5.0g、17.2mol)の溶液に、0℃で加えた。次いで、混合物を0℃で15時間攪拌した。室温まで温めさせておいた後、溶剤の半分の量を蒸発させ、得られた混合物をメタノールに注いだ。沈殿をろ過により集め、n−ヘキサン/メタノールから再結晶し、目的の生成物を白色固体(1.13g)として得た。
実施例15a)で得た化合物を出発材料として用いて、実施例11b)で述べたのと同じ方法でヨウ素化を行った。
4−(2,6−ジ−t−ブチル−10−ピレン−1−イル−アントラセン−9−イル)−ジベンゾフラン
2,6-ジ−ピレン−1−イル−ジベンゾフラン
4−ブロモジベンゾフランを出発材料として用いたほかは、実施例11b)で述べたのと同じ方法で、6−ブロモ−2−ヨード−ジベンゾフランを製造した。
6−フェナントレン−9−イル−2−ピレン−1−イル−ジベンゾフラン
応用例1
化合物A−1、B−1、C−1、C−2、A−9、A−10及びA−7をそれぞれ、ガラス板に、厚さ60nmで真空下で蒸着した。蒸着フィルムの蛍光スペクトルを蛍光分光光度計(F-4500、HITACHI)で測定した。発光λmaxを次に示す。
次の素子構造:ITO/CuPC/TCTA/化合物B−1/TPBI/LiF/Al[ここで、ITOは酸化インジウムスズであり、CuPCは銅フタロシアニンであり、TCTAは4,4’,4”−トリ−(N−カルバゾイル)トリフェニルアミンであり、そしてTPBIは1,3,5−トリス−(N−フェニル−ベンズイミダゾール−2−イル)ベンゼンである]を製造した。この素子構造を用いて、100mA/cm2で輝度50cd/m2を確認した。
次の素子構造:ITO/CuPC/TCTA/化合物B−1+化合物G−1(1.1重量%)/TPBI/LiF/Alを製造した。この素子構造を用いて、100mA/cm2で輝度500cd/m2を確認した。
次の素子構造:ITO/CuPC/TCTA/化合物C−2/TPBI/LiF/Alを製造した。この素子構造を用いて、100mA/cm2で輝度120cd/m2を確認した。
次の素子構造:ITO/CuPC/TCTA/化合物C−2+化合物G−1(1.9重量%)/TPBI/LiF/Alを製造した。この素子構造を用いて、100mA/cm2で輝度70cd/m2を確認した。
次の素子構造:ITO/CuPC/NPD/化合物B−1/TPBI/LiF/Al[ここで、NPDはN,N’−ジ(ナフタレン−1−イル)−N,N’−ジフェニル−ベンジジンである]を製造した。この素子構造を用いて、100mA/cm2で輝度370cd/m2を確認した。
次の素子構造:ITO/CuPC/NPD/化合物B−1+TBPe(1.4%)/TPBI/LiF/Al(ここで、TPBeは2,5,8,11−テトラ−t−ブチルペリレンである)を製造した。この素子構造を用いて、88mA/cm2で輝度680cd/m2を確認した。
次の素子構造:ITO/CuPC/NPD/化合物A−10/TPBI/LiF/Alを製造した。この素子構造を用いて、111mA/cm2で輝度3,800cd/m2を確認した。
次の素子構造:ITO/CuPC/NPD/化合物A−10+TBPe(1.5%)/TPBI/LiF/Alを製造した。この素子構造を用いて、90mA/cm2で輝度2,030cd/m2を確認した。
次の素子構造:ITO/CuPC/NPD/発光層(ホストとして本発明のジベンゾフラン+ゲストとしてTBPe)/TPBI/LiF/Alを製造した。この素子構造を用いて、明るい青色EL発光を確認した。素子のEL特性を表1にまとめた。
次の素子構造:ITO/CuPC/NPD/発光層(ホストとして本発明のジベンゾフラン+ゲストとして本発明のジベンゾフラン)/TPBI/LiF/Alを製造した。この素子構造を用いて、明るい青色EL発光を確認した。素子のEL特性を表2にまとめた。
Claims (4)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05104599 | 2005-05-30 | ||
EP05104599.5 | 2005-05-30 | ||
EP05107908 | 2005-08-30 | ||
EP05107908.5 | 2005-08-30 | ||
PCT/EP2006/062483 WO2006128800A1 (en) | 2005-05-30 | 2006-05-22 | Electroluminescent device |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008545729A JP2008545729A (ja) | 2008-12-18 |
JP2008545729A5 JP2008545729A5 (ja) | 2009-07-09 |
JP5107237B2 true JP5107237B2 (ja) | 2012-12-26 |
Family
ID=36791677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008514060A Active JP5107237B2 (ja) | 2005-05-30 | 2006-05-22 | エレクトロルミネセント素子 |
Country Status (9)
Country | Link |
---|---|
US (3) | US7989644B2 (ja) |
EP (1) | EP1885818B2 (ja) |
JP (1) | JP5107237B2 (ja) |
KR (2) | KR101425423B1 (ja) |
CN (2) | CN101184822B (ja) |
AT (1) | ATE455162T1 (ja) |
DE (1) | DE602006011734D1 (ja) |
TW (1) | TW200712171A (ja) |
WO (1) | WO2006128800A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9997715B2 (en) | 2014-11-18 | 2018-06-12 | Samsung Display Co., Ltd. | Material for organic electroluminescent device and organic electroluminescent device using the same |
Families Citing this family (186)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103193697B (zh) * | 2005-09-08 | 2015-11-18 | 东丽株式会社 | 发光元件材料和发光元件 |
TWI420963B (zh) * | 2005-12-15 | 2013-12-21 | Idemitsu Kosan Co | Organic electroluminescent element materials and organic electroluminescent devices using the same |
US7651791B2 (en) | 2005-12-15 | 2010-01-26 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
EP2463930B1 (en) * | 2006-01-05 | 2017-04-12 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
EP1998387B1 (en) | 2006-03-17 | 2015-04-22 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
US8920942B2 (en) | 2006-03-23 | 2014-12-30 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and illuminating device |
JP5055818B2 (ja) * | 2006-04-19 | 2012-10-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US8623522B2 (en) | 2006-04-26 | 2014-01-07 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and electroluminescence device using the same |
WO2007125714A1 (ja) * | 2006-04-26 | 2007-11-08 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
KR20090016684A (ko) * | 2006-06-02 | 2009-02-17 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
JP4829722B2 (ja) * | 2006-08-31 | 2011-12-07 | 三井化学株式会社 | 有機電界発光素子および芳香族化合物 |
US8541112B2 (en) * | 2006-12-13 | 2013-09-24 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
CN101627102B (zh) * | 2007-03-07 | 2013-08-28 | 东丽株式会社 | 发光元件材料和发光元件 |
JP2008282610A (ja) * | 2007-05-09 | 2008-11-20 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子の製造方法 |
WO2008156105A1 (ja) * | 2007-06-21 | 2008-12-24 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2009021107A1 (en) | 2007-08-08 | 2009-02-12 | Universal Display Corporation | Single triphenylene chromophores in phosphorescent light emitting diodes |
KR101453128B1 (ko) * | 2007-07-10 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
WO2009021126A2 (en) | 2007-08-08 | 2009-02-12 | Universal Display Corporation | Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group |
JP2009046408A (ja) * | 2007-08-17 | 2009-03-05 | Konica Minolta Holdings Inc | ジハロ多環芳香族化合物、ピロリル多環芳香族化合物、及びそれらの製造方法 |
WO2009085344A2 (en) * | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
KR20090098585A (ko) * | 2008-03-14 | 2009-09-17 | (주)그라쎌 | 유기발광화합물을 발광재료로서 채용하고 있는유기전기발광소자 |
JP5491383B2 (ja) * | 2008-03-19 | 2014-05-14 | 出光興産株式会社 | アントラセン誘導体、発光材料および有機エレクトロルミネッセンス素子 |
KR100910150B1 (ko) * | 2008-04-02 | 2009-08-03 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
JP5193295B2 (ja) | 2008-05-29 | 2013-05-08 | 出光興産株式会社 | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
KR20100000772A (ko) * | 2008-06-25 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
JP5299288B2 (ja) * | 2008-07-01 | 2013-09-25 | 東レ株式会社 | 発光素子 |
KR20110043625A (ko) * | 2008-07-28 | 2011-04-27 | 이데미쓰 고산 가부시키가이샤 | 유기 발광 매체 및 유기 el 소자 |
CN102224148B (zh) * | 2008-09-23 | 2015-07-15 | 株式会社Lg化学 | 化合物、及其制备方法和使用该化合物的有机电子元件 |
CN102224150B (zh) | 2008-11-25 | 2015-08-12 | 出光兴产株式会社 | 芳香族胺衍生物以及有机电致发光元件 |
US9067947B2 (en) * | 2009-01-16 | 2015-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP5201054B2 (ja) * | 2009-03-31 | 2013-06-05 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス材料、有機エレクトロルミネッセンス素子、青色燐光発光素子、表示装置及び照明装置 |
US8206842B2 (en) * | 2009-04-06 | 2012-06-26 | Global Oled Technology Llc | Organic element for electroluminescent devices |
KR101217979B1 (ko) | 2009-04-24 | 2013-01-02 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체를 이용한 유기 전계 발광 소자 |
JP5280526B2 (ja) * | 2009-05-29 | 2013-09-04 | 出光興産株式会社 | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
KR20100130059A (ko) * | 2009-06-02 | 2010-12-10 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
JP5742092B2 (ja) * | 2009-09-02 | 2015-07-01 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
JP2013012505A (ja) * | 2009-09-17 | 2013-01-17 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP5715142B2 (ja) * | 2009-09-29 | 2015-05-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | ルミネセンス用途用の重水素化合物 |
JP5659478B2 (ja) * | 2009-10-05 | 2015-01-28 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US20120205645A1 (en) | 2009-10-28 | 2012-08-16 | Basf Se | Heteroleptic carbene complexes and the use thereof in organic electronics |
KR101838199B1 (ko) | 2009-12-14 | 2018-04-26 | 유디씨 아일랜드 리미티드 | 디아자벤즈이미다졸로카르벤 리간드를 포함하는 금속 착물 및 oled에서의 그의 용도 |
KR101358494B1 (ko) | 2009-12-16 | 2014-02-05 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전계 발광 소자 |
US20120319091A1 (en) | 2010-01-21 | 2012-12-20 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescent element comprising same |
KR101736987B1 (ko) | 2010-04-06 | 2017-05-18 | 삼성디스플레이 주식회사 | 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR101758328B1 (ko) * | 2010-04-06 | 2017-07-17 | 삼성디스플레이 주식회사 | 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자 |
US8691401B2 (en) | 2010-04-16 | 2014-04-08 | Basf Se | Bridged benzimidazole-carbene complexes and use thereof in OLEDS |
KR20110122051A (ko) | 2010-05-03 | 2011-11-09 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101877580B1 (ko) * | 2010-06-18 | 2018-08-09 | 유디씨 아일랜드 리미티드 | 디벤조푸란 화합물 및 8-히드록시퀴놀리노레이토 알칼리 토금속 또는 알칼리 금속 착물의 층을 포함하는 유기 전자 소자 |
US9142792B2 (en) | 2010-06-18 | 2015-09-22 | Basf Se | Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide |
EP2582768B1 (en) | 2010-06-18 | 2014-06-25 | Basf Se | Organic electronic devices comprising a layer of a pyridine compound and a 8-hydroxyquinolinolato earth alkaline metal, or alkali metal complex |
US20110309344A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising a layer of a pyridine compound and a 8-hydroxypquinolinolato earth alkaline metal, or alkali metal complex |
WO2011158592A1 (ja) * | 2010-06-18 | 2011-12-22 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び有機エレクトロルミネッセンス素子の製造方法 |
US9203037B2 (en) | 2010-06-18 | 2015-12-01 | Basf Se | Organic electronic devices comprising a layer of a dibenzofurane compound and a 8-hydroxypquinolinolato earth alkaline metal, or alkali metal complex |
CN103080105B (zh) * | 2010-07-08 | 2017-08-18 | Udc 爱尔兰有限责任公司 | 被氮键合5元杂环取代的二苯并呋喃和二苯并噻吩及其在有机电子中的用途 |
US9067919B2 (en) | 2010-07-08 | 2015-06-30 | Basf Se | Use of dibenzofurans and dibenzothiophenes substituted by nitrogen-bonded five-membered heterocyclic rings in organic electronics |
JP6007467B2 (ja) * | 2010-07-27 | 2016-10-12 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、 |
JP5763309B2 (ja) * | 2010-07-30 | 2015-08-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
JP5507381B2 (ja) | 2010-07-30 | 2014-05-28 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
JP5847420B2 (ja) * | 2010-09-08 | 2016-01-20 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
KR102132588B1 (ko) | 2010-09-10 | 2020-07-10 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자 및 전자기기 |
JP5623996B2 (ja) | 2010-09-21 | 2014-11-12 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体 |
EP2625171B1 (en) | 2010-10-07 | 2014-07-30 | Basf Se | Phenanthro[9,10-b]furans for electronic applications |
US9079872B2 (en) | 2010-10-07 | 2015-07-14 | Basf Se | Phenanthro[9, 10-B]furans for electronic applications |
US8932734B2 (en) | 2010-10-08 | 2015-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN103283308B (zh) * | 2010-10-11 | 2016-06-22 | 索尔维公司 | 用于发光装置的螺二芴化合物 |
US9133173B2 (en) | 2010-10-15 | 2015-09-15 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole compound, material for light-emitting element, organic semiconductor material, light-emitting element |
JP5699524B2 (ja) * | 2010-10-21 | 2015-04-15 | コニカミノルタ株式会社 | 有機光電変換素子および太陽電池 |
US8455867B2 (en) | 2010-10-26 | 2013-06-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
KR101950363B1 (ko) * | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
JP5872861B2 (ja) | 2010-11-30 | 2016-03-01 | 株式会社半導体エネルギー研究所 | カルバゾール化合物 |
CN103261171B (zh) | 2010-12-13 | 2016-03-30 | 巴斯夫欧洲公司 | 用于电子应用的双嘧啶类 |
US8362246B2 (en) | 2010-12-13 | 2013-01-29 | Basf Se | Bispyrimidines for electronic applications |
TWI545175B (zh) * | 2010-12-17 | 2016-08-11 | 半導體能源研究所股份有限公司 | 有機化合物,發光元件,發光裝置,電子裝置,以及照明裝置 |
TWI518078B (zh) * | 2010-12-28 | 2016-01-21 | 半導體能源研究所股份有限公司 | 充當發光元件材料之苯並[b]萘並[1,2-d]呋喃化合物 |
EP2674429B1 (en) | 2011-02-07 | 2020-12-23 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative and organic electroluminescent element using same |
US9806270B2 (en) | 2011-03-25 | 2017-10-31 | Udc Ireland Limited | 4H-imidazo[1,2-a]imidazoles for electronic applications |
CN114315840A (zh) | 2011-03-25 | 2022-04-12 | Udc 爱尔兰有限责任公司 | 用于电子应用的4H-咪唑并[1,2-a]咪唑 |
JP5984450B2 (ja) * | 2011-03-31 | 2016-09-06 | 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、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物 |
KR102090916B1 (ko) | 2011-06-14 | 2020-03-19 | 유디씨 아일랜드 리미티드 | 아자벤즈이미다졸 카르벤 리간드를 포함하는 금속 착물 및 oled 에서의 이의 용도 |
US9315724B2 (en) | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
WO2013002217A1 (ja) * | 2011-06-28 | 2013-01-03 | シャープ株式会社 | 化合物、電界効果トランジスタ及びその製造方法、太陽電池、有機発光素子、組成物、表示装置用アレイ並びに表示装置 |
US9640773B2 (en) | 2011-09-16 | 2017-05-02 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescence element using same |
CN108299439B (zh) | 2011-11-10 | 2021-02-09 | Udc 爱尔兰有限责任公司 | 用于电子应用的4H-咪唑并[1,2-a]咪唑 |
JP2015051925A (ja) * | 2011-11-25 | 2015-03-19 | 出光興産株式会社 | 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子 |
JP5857724B2 (ja) * | 2011-12-20 | 2016-02-10 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子の製造方法 |
KR101340255B1 (ko) * | 2011-12-26 | 2013-12-10 | 군산대학교산학협력단 | 염료감응 태양전지를 위한 신규 염료 및 이의 제조방법 |
US9871203B2 (en) | 2012-02-10 | 2018-01-16 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, organic electroluminescent element and electronic device |
JP5867583B2 (ja) | 2012-02-22 | 2016-02-24 | Jnc株式会社 | 新規なカルコゲン含有有機化合物およびその用途 |
JP5958988B2 (ja) * | 2012-03-16 | 2016-08-02 | Jnc株式会社 | 有機半導体薄膜、有機半導体素子および有機電界効果トランジスタ |
KR101640636B1 (ko) * | 2012-05-31 | 2016-07-18 | 주식회사 엘지화학 | 신규한 헤테로환 화합물 및 이를 이용한 유기 전자 소자 |
JP6088161B2 (ja) | 2012-06-29 | 2017-03-01 | 出光興産株式会社 | 芳香族アミン誘導体及び有機エレクトロルミネッセンス素子 |
JP6231561B2 (ja) | 2012-07-10 | 2017-11-15 | ユー・ディー・シー アイルランド リミテッド | 電子用途のためのベンズイミダゾ[1,2−a]ベンズイミダゾール誘導体 |
EP3133079A1 (en) | 2012-07-19 | 2017-02-22 | UDC Ireland Limited | Dinuclear metal complexes comprising carbene ligands and the use thereof in oleds |
KR101695350B1 (ko) | 2012-08-01 | 2017-01-13 | 삼성디스플레이 주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN102850334A (zh) * | 2012-08-28 | 2013-01-02 | 李崇 | 一种以二苯并呋喃为核心骨架的衍生物化合物及其在oled上的应用 |
US9312500B2 (en) | 2012-08-31 | 2016-04-12 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
CN104603137B (zh) * | 2012-09-12 | 2019-01-04 | 出光兴产株式会社 | 新型化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
CN104662023B (zh) | 2012-09-20 | 2017-08-18 | Udc 爱尔兰有限责任公司 | 供电子应用的氮杂二苯并呋喃 |
KR102080365B1 (ko) | 2012-11-06 | 2020-02-21 | 유디씨 아일랜드 리미티드 | 전자장치 응용품을 위한 페녹사실린 기재의 화합물 |
KR102022524B1 (ko) | 2012-11-22 | 2019-09-18 | 엘지디스플레이 주식회사 | 청색 인광 화합물 및 이를 사용한 유기전계발광소자 |
KR101995191B1 (ko) | 2012-12-10 | 2019-07-02 | 코니카 미놀타 가부시키가이샤 | 유기 일렉트로루미네센스 소자 재료, 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치 |
JP5968214B2 (ja) * | 2012-12-14 | 2016-08-10 | コニカミノルタ株式会社 | ジハロ多環芳香族化合物の製造方法 |
KR102104357B1 (ko) * | 2012-12-24 | 2020-04-27 | 엘지디스플레이 주식회사 | 청색 형광 화합물 및 이를 사용한 유기전계발광소자 |
JP5847354B2 (ja) | 2013-03-15 | 2016-01-20 | 出光興産株式会社 | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
TWI734860B (zh) | 2013-03-20 | 2021-08-01 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 包含Ir金屬-碳烯錯合物之有機電子裝置及設備 |
JP6088324B2 (ja) * | 2013-03-29 | 2017-03-01 | 出光興産株式会社 | 含窒素芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子 |
KR102098340B1 (ko) | 2013-04-29 | 2020-04-13 | 유디씨 아일랜드 리미티드 | 카르벤 리간드를 갖는 전이 금속 착물 및 oled에서의 그의 용도 |
WO2014199637A1 (ja) | 2013-06-11 | 2014-12-18 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料、これを用いた有機エレクトロルミネッセンス素子及び電子機器 |
KR102188028B1 (ko) * | 2013-06-18 | 2020-12-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN105518013B (zh) | 2013-07-02 | 2018-10-26 | Udc 爱尔兰有限责任公司 | 用于有机发光二级管中的单取代的二氮杂苯并咪唑卡宾金属络合物 |
CN109021022B (zh) | 2013-07-31 | 2021-04-16 | Udc 爱尔兰有限责任公司 | 发光的二氮杂苯并咪唑碳烯金属配合物 |
EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
WO2015091716A1 (en) | 2013-12-20 | 2015-06-25 | Basf Se | Highly efficient oled devices with very short decay times |
JP6516407B2 (ja) | 2013-12-20 | 2019-05-22 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
JP6494656B2 (ja) | 2014-03-31 | 2019-04-03 | ユー・ディー・シー アイルランド リミテッド | o−置換非シクロメタル化アリール基を有するカルベン配位子を含む金属錯体及び有機発光ダイオードにおけるその使用 |
JP6890975B2 (ja) * | 2014-05-05 | 2021-06-18 | 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 |
EP3174885B1 (en) | 2014-07-28 | 2019-10-02 | Idemitsu Kosan Co., Ltd. | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
KR102472084B1 (ko) | 2014-08-08 | 2022-11-29 | 유디씨 아일랜드 리미티드 | 전계발광 이미다조-퀴녹살린 카르벤 금속 착체 |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
JP6674734B2 (ja) | 2014-10-29 | 2020-04-01 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
CN107074895B (zh) | 2014-11-18 | 2020-03-17 | Udc 爱尔兰有限责任公司 | 用于有机发光二极管中的Pt-或Pd-碳烯络合物 |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
CN104672226B (zh) * | 2015-01-23 | 2017-12-22 | 固安鼎材科技有限公司 | 一种新型化合物、其制备方法及其应用 |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
JP5900675B2 (ja) * | 2015-02-10 | 2016-04-06 | コニカミノルタ株式会社 | ピロリル多環芳香族化合物の製造方法 |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
KR102342339B1 (ko) * | 2015-03-18 | 2021-12-22 | 에스에프씨주식회사 | 유기발광소자용 화합물 및 이를 포함하는 유기 발광 소자 |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10593890B2 (en) | 2015-04-06 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10693084B2 (en) | 2015-04-23 | 2020-06-23 | Sfc Co., Ltd. | Compound for organic light-emitting device and organic light-emitting device including same |
KR101923171B1 (ko) | 2015-05-27 | 2018-11-28 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2016193243A1 (en) | 2015-06-03 | 2016-12-08 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
KR102399573B1 (ko) * | 2015-08-04 | 2022-05-19 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
WO2017056053A1 (en) | 2015-10-01 | 2017-04-06 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US20180269407A1 (en) | 2015-10-01 | 2018-09-20 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
KR102458684B1 (ko) * | 2015-10-08 | 2022-10-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
JP6974315B2 (ja) * | 2015-10-27 | 2021-12-01 | 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 |
KR101614738B1 (ko) * | 2015-11-02 | 2016-04-22 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2017078182A1 (en) | 2015-11-04 | 2017-05-11 | Idemitsu Kosan Co., Ltd. | Benzimidazole fused heteroaryls |
WO2017093958A1 (en) | 2015-12-04 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
JP6375069B2 (ja) | 2015-12-21 | 2018-08-15 | 出光興産株式会社 | ヘテロ原子で架橋されたフェニルキナゾリン |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
WO2017196081A1 (en) * | 2016-05-11 | 2017-11-16 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
CN106083845A (zh) * | 2016-06-14 | 2016-11-09 | 金陵科技学院 | 一种1,5‑萘啶类有机发光材料化合物及其合成方法与应用 |
KR20180050475A (ko) * | 2016-11-04 | 2018-05-15 | 삼성디스플레이 주식회사 | 잉크 조성물, 이를 이용한 유기 발광 소자 및 이를 이용한 유기 발광 소자의 제조 방법 |
US11261176B2 (en) | 2017-01-26 | 2022-03-01 | Lg Chem, Ltd. | Amine-based compound and organic light emitting device using the same |
CN109564972B (zh) * | 2017-03-09 | 2023-02-03 | 株式会社Lg化学 | 有机发光元件 |
WO2018199466A1 (ko) * | 2017-04-27 | 2018-11-01 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기발광 소자 |
KR102016081B1 (ko) * | 2017-04-27 | 2019-08-29 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기발광 소자 |
KR102102036B1 (ko) * | 2017-06-01 | 2020-04-17 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR102606281B1 (ko) * | 2017-07-14 | 2023-11-27 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
KR101982792B1 (ko) | 2017-07-20 | 2019-05-27 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 |
CN109755415B (zh) * | 2017-11-02 | 2020-01-10 | 广东阿格蕾雅光电材料有限公司 | 含有4,6-二苯砜二苯并呋喃的双极性材料的器件 |
CN109928961B (zh) * | 2017-12-15 | 2021-06-15 | 广东阿格蕾雅光电材料有限公司 | 含有4-硫砜芳基二苯并呋喃的光电材料及应用 |
KR102162609B1 (ko) * | 2018-06-07 | 2020-10-07 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN108586353B (zh) * | 2018-06-15 | 2020-08-18 | 华南理工大学 | 一种基于蒽及其衍生物的有机发光材料及其制备方法和应用 |
KR102233421B1 (ko) * | 2018-07-06 | 2021-03-29 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
US20220384732A1 (en) * | 2018-07-09 | 2022-12-01 | Merck Patent Gmbh | Materials for electronic devices |
CN109081820A (zh) * | 2018-07-18 | 2018-12-25 | 南京工业大学 | 一种基于蒽的半导体材料、制备方法及有机场效应晶体管 |
KR102235479B1 (ko) | 2018-07-24 | 2021-04-02 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
CN108864012A (zh) * | 2018-09-03 | 2018-11-23 | 上海道亦化工科技有限公司 | 一种基于二苯并呋喃化合物及其用途和有机电致发光器件 |
CN108864013A (zh) * | 2018-09-03 | 2018-11-23 | 上海道亦化工科技有限公司 | 一种含二苯并呋喃的芳香胺化合物及其用途和发光器件 |
KR102196430B1 (ko) * | 2018-09-14 | 2020-12-30 | 주식회사 엘지화학 | 신규한 화합물, 이를 포함하는 코팅 조성물 및 이를 이용한 유기발광 소자 |
WO2020096350A1 (ko) | 2018-11-06 | 2020-05-14 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
EP3939970B1 (en) * | 2019-03-15 | 2023-12-27 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence devices, organic electroluminescence device, and electronic device |
CN110128399B (zh) * | 2019-05-31 | 2021-11-23 | 常州大学 | 基于二苯并五元芳杂环有机分子材料及其合成方法和作为空穴传输层的应用 |
CN110372683A (zh) * | 2019-07-26 | 2019-10-25 | 北京燕化集联光电技术有限公司 | 一种有机电致发光材料及其制备方法与应用 |
CN110372676B (zh) * | 2019-07-26 | 2021-05-14 | 北京燕化集联光电技术有限公司 | 一种二苯并呋喃类主体材料及其制备方法与应用 |
KR102301612B1 (ko) * | 2020-06-22 | 2021-09-13 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
CN111961038B (zh) * | 2020-07-20 | 2021-10-08 | 陕西莱特光电材料股份有限公司 | 化合物、有机致电发光器件及电子装置 |
CN112239414B (zh) * | 2020-09-29 | 2022-03-29 | 华南理工大学 | 一类基于2,6-二叔丁基蒽的蓝色有机半导体材料及其制备方法与应用 |
WO2024166615A1 (ja) * | 2023-02-06 | 2024-08-15 | 出光興産株式会社 | 化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2024166614A1 (ja) * | 2023-02-06 | 2024-08-15 | 出光興産株式会社 | 化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4016156A (en) | 1972-06-30 | 1977-04-05 | Ciba-Geigy Corporation | Distyryl compounds |
CH574950A5 (ja) * | 1972-06-30 | 1976-04-30 | Ciba Geigy Ag | |
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
JP2501198B2 (ja) | 1986-05-30 | 1996-05-29 | キヤノン株式会社 | 電子写真感光体 |
JPH02282263A (ja) | 1988-12-09 | 1990-11-19 | Nippon Oil Co Ltd | ホール輸送材料 |
JPH03792A (ja) | 1989-02-17 | 1991-01-07 | Pioneer Electron Corp | 電界発光素子 |
JP2879370B2 (ja) | 1990-11-16 | 1999-04-05 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を備えた電子写真装置並びにファクシミリ |
US5150006A (en) | 1991-08-01 | 1992-09-22 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (II) |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
JPH05109485A (ja) | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
JP3151997B2 (ja) * | 1993-03-18 | 2001-04-03 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子 |
DE4325885A1 (de) | 1993-08-02 | 1995-02-09 | Basf Ag | Elektrolumineszierende Anordnung |
JP3114445B2 (ja) | 1993-08-10 | 2000-12-04 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
US5486406A (en) | 1994-11-07 | 1996-01-23 | Motorola | Green-emitting organometallic complexes for use in light emitting devices |
US5629389A (en) | 1995-06-06 | 1997-05-13 | Hewlett-Packard Company | Polymer-based electroluminescent device with improved stability |
JPH09151182A (ja) * | 1995-11-29 | 1997-06-10 | Mita Ind Co Ltd | ジベンゾフランジアミン誘導体およびこれを用いた電子写真感光体 |
JP3503403B2 (ja) | 1997-03-17 | 2004-03-08 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子 |
DE69804529T2 (de) | 1997-05-19 | 2002-10-02 | Canon Kk | Organisches Material und elektrolumineszente Vorrichtung dasselbe nutzend |
JP3508984B2 (ja) * | 1997-05-19 | 2004-03-22 | キヤノン株式会社 | 有機化合物及び該有機化合物を用いた発光素子 |
JP3633236B2 (ja) | 1997-10-06 | 2005-03-30 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
CA2321791A1 (en) | 1998-03-18 | 1999-09-23 | Ciba Specialty Chemicals Holding Inc. | Coupling reactions with palladium catalysts |
JP4048645B2 (ja) | 1998-04-10 | 2008-02-20 | 東レ株式会社 | 発光素子 |
JP2000012230A (ja) * | 1998-06-18 | 2000-01-14 | Matsushita Electric Ind Co Ltd | 有機電界発光素子 |
US6057048A (en) | 1998-10-01 | 2000-05-02 | Xerox Corporation | Electroluminescent (EL) devices |
US6229012B1 (en) * | 1998-10-01 | 2001-05-08 | Xerox Corporation | Triazine compositions |
JP2001043979A (ja) | 2000-01-01 | 2001-02-16 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用正孔輸送材料 |
US6225467B1 (en) | 2000-01-21 | 2001-05-01 | Xerox Corporation | Electroluminescent (EL) devices |
GB2380191A (en) * | 2001-09-28 | 2003-04-02 | Sharp Kk | Benzofuran compounds their preparation and their use in electroluminescent and photovoltaic devices |
SG128438A1 (en) | 2002-03-15 | 2007-01-30 | Sumitomo Chemical Co | Polymer compound and polymer light emitting deviceusing the same |
JP4189165B2 (ja) | 2002-03-29 | 2008-12-03 | 三井化学株式会社 | スチリル化合物、および該スチリル化合物を含有する有機電界発光素子 |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
AU2003238442A1 (en) | 2002-06-06 | 2003-12-22 | Siba Spelcialty Chemicals Holding Inc. | Electroluminescent device |
CN1703937B (zh) | 2002-10-09 | 2010-11-24 | 出光兴产株式会社 | 有机电致发光的器件 |
AU2003274050A1 (en) | 2002-10-30 | 2004-05-25 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
JP4181399B2 (ja) | 2002-12-19 | 2008-11-12 | 三井化学株式会社 | ジアミン化合物、および該ジアミン化合物を含有する有機電界発光素子 |
WO2004077885A2 (en) | 2003-02-28 | 2004-09-10 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
JP2004311404A (ja) | 2003-03-26 | 2004-11-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、照明装置および表示装置 |
JP2004311405A (ja) | 2003-03-27 | 2004-11-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JPWO2004096945A1 (ja) * | 2003-05-01 | 2006-07-13 | 富士写真フイルム株式会社 | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
JP2005011804A (ja) | 2003-05-29 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
JP5112601B2 (ja) | 2003-10-07 | 2013-01-09 | 三井化学株式会社 | 複素環化合物および該化合物を含有する有機電界発光素子 |
JP4384536B2 (ja) * | 2004-04-27 | 2009-12-16 | 三井化学株式会社 | アントラセン化合物、および該アントラセン化合物を含有する有機電界発光素子 |
TWI373506B (en) * | 2004-05-21 | 2012-10-01 | Toray Industries | Light-emitting element material and light-emitting material |
GB2439030B (en) | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
KR101453128B1 (ko) * | 2007-07-10 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
-
2006
- 2006-05-22 CN CN200680019047.6A patent/CN101184822B/zh active Active
- 2006-05-22 WO PCT/EP2006/062483 patent/WO2006128800A1/en active Application Filing
- 2006-05-22 AT AT06777232T patent/ATE455162T1/de not_active IP Right Cessation
- 2006-05-22 CN CN201210028344.4A patent/CN102603688B/zh active Active
- 2006-05-22 EP EP06777232.7A patent/EP1885818B2/en active Active
- 2006-05-22 US US11/921,050 patent/US7989644B2/en active Active
- 2006-05-22 KR KR1020137016703A patent/KR101425423B1/ko active IP Right Grant
- 2006-05-22 JP JP2008514060A patent/JP5107237B2/ja active Active
- 2006-05-22 DE DE602006011734T patent/DE602006011734D1/de active Active
- 2006-05-29 TW TW095119024A patent/TW200712171A/zh unknown
-
2007
- 2007-12-28 KR KR1020077030813A patent/KR101345104B1/ko active IP Right Grant
-
2011
- 2011-06-20 US US13/164,016 patent/US8735610B2/en active Active
-
2014
- 2014-04-15 US US14/252,870 patent/US8946984B2/en active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9997715B2 (en) | 2014-11-18 | 2018-06-12 | Samsung Display Co., Ltd. | Material for organic electroluminescent device and organic electroluminescent device using the same |
Also Published As
Publication number | Publication date |
---|---|
US8735610B2 (en) | 2014-05-27 |
JP2008545729A (ja) | 2008-12-18 |
EP1885818A1 (en) | 2008-02-13 |
US20140217335A1 (en) | 2014-08-07 |
US8946984B2 (en) | 2015-02-03 |
KR20130080872A (ko) | 2013-07-15 |
US20110248217A1 (en) | 2011-10-13 |
CN101184822A (zh) | 2008-05-21 |
KR20080018218A (ko) | 2008-02-27 |
KR101425423B1 (ko) | 2014-08-01 |
ATE455162T1 (de) | 2010-01-15 |
DE602006011734D1 (de) | 2010-03-04 |
CN101184822B (zh) | 2014-11-26 |
US7989644B2 (en) | 2011-08-02 |
TW200712171A (en) | 2007-04-01 |
EP1885818B1 (en) | 2010-01-13 |
CN102603688A (zh) | 2012-07-25 |
US20090131673A1 (en) | 2009-05-21 |
EP1885818B2 (en) | 2018-10-03 |
CN102603688B (zh) | 2015-11-25 |
KR101345104B1 (ko) | 2013-12-26 |
WO2006128800A1 (en) | 2006-12-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5107237B2 (ja) | エレクトロルミネセント素子 | |
JP5138582B2 (ja) | 電子発光装置 | |
JP4963357B2 (ja) | エレクトロルミネセントデバイス | |
JP6270735B2 (ja) | 芳香族アミン誘導体及び有機エレクトロルミネッセンス素子 | |
US20080199726A1 (en) | Electroluminescent Device | |
KR20040094866A (ko) | 유기 전자발광 소자용 재료 및 이를 이용한 유기 전자발광소자 | |
JP2007527361A (ja) | エレクトロルミネセンス素子 | |
EP2589596A1 (en) | Aromatic amine derivative, and organic electroluminescent element comprising same | |
KR20190088030A (ko) | 유기 발광 소자 | |
KR20200115272A (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
EP1687856B1 (en) | Electroluminescent devices comprising 2-(p-triphenyl)-3-phenyl-pyrazine derivatives | |
JP2007504199A (ja) | エレクトロルミネセンス素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090520 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090520 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120612 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120904 |
|
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: 20121002 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121003 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5107237 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151012 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
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 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |