KR101577468B1 - Ｏｌｅｄ에서의 매트릭스 물질 및/또는 전자 차단체로서의 아크리딘 유도체의 용도 - Google Patents
Ｏｌｅｄ에서의 매트릭스 물질 및/또는 전자 차단체로서의 아크리딘 유도체의 용도 Download PDFInfo
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- KR101577468B1 KR101577468B1 KR1020107009710A KR20107009710A KR101577468B1 KR 101577468 B1 KR101577468 B1 KR 101577468B1 KR 1020107009710 A KR1020107009710 A KR 1020107009710A KR 20107009710 A KR20107009710 A KR 20107009710A KR 101577468 B1 KR101577468 B1 KR 101577468B1
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- substituted
- unsubstituted
- radical
- radicals
- light emitting
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- 239000011159 matrix material Substances 0.000 title claims abstract description 60
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title claims abstract description 18
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 title abstract description 40
- 239000000463 material Substances 0.000 claims abstract description 57
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 29
- 230000000903 blocking effect Effects 0.000 claims abstract description 17
- -1 heteroaryl radical Chemical class 0.000 claims description 213
- 150000003254 radicals Chemical class 0.000 claims description 63
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 49
- 230000004888 barrier function Effects 0.000 abstract description 2
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- 150000001251 acridines Chemical class 0.000 description 78
- 229910052741 iridium Inorganic materials 0.000 description 51
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 229910052751 metal Inorganic materials 0.000 description 28
- 239000002184 metal Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000001072 heteroaryl group Chemical group 0.000 description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000003446 ligand Substances 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 150000005840 aryl radicals Chemical class 0.000 description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 125000003107 substituted aryl group Chemical group 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 150000003413 spiro compounds Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108091006149 Electron carriers Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-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
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- JBOIAZWJIACNJF-UHFFFAOYSA-N 1h-imidazole;hydroiodide Chemical compound [I-].[NH2+]1C=CN=C1 JBOIAZWJIACNJF-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RAQZGRQLHSTDCB-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=C(C=C1)C1=CC=CC=2N(C3=CC=CC=C3CC1=2)C1=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=C(C=C1)C1=CC=CC=2N(C3=CC=CC=C3CC1=2)C1=CC=CC=C1 RAQZGRQLHSTDCB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001649081 Dina Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 241001061127 Thione Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- TVRHDFJMHSSQCP-UHFFFAOYSA-M [Ir]Cl.C1CC=CCCC=C1 Chemical class [Ir]Cl.C1CC=CCCC=C1 TVRHDFJMHSSQCP-UHFFFAOYSA-M 0.000 description 2
- 125000005595 acetylacetonate group Chemical group 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 150000001413 amino acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000000429 assembly Methods 0.000 description 2
- 230000000712 assembly Effects 0.000 description 2
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RRXYBJYIUHTJTO-UHFFFAOYSA-N europium;1,10-phenanthroline Chemical compound [Eu].C1=CN=C2C3=NC=CC=C3C=CC2=C1 RRXYBJYIUHTJTO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
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- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- KISMZLDUXRTQHO-UHFFFAOYSA-M methyl 4-(3-methylimidazol-3-ium-1-yl)benzoate;iodide Chemical compound [I-].C1=CC(C(=O)OC)=CC=C1[N+]1=CN(C)C=C1 KISMZLDUXRTQHO-UHFFFAOYSA-M 0.000 description 2
- KUBBZTZQWIGHFH-UHFFFAOYSA-N methyl 4-imidazol-1-ylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1C=NC=C1 KUBBZTZQWIGHFH-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 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 2
- 238000007740 vapor deposition Methods 0.000 description 2
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Classifications
-
- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- 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
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| Application Number | Priority Date | Filing Date | Title |
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| EP07117770 | 2007-10-02 | ||
| EP07117770.3 | 2007-10-02 |
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| EP (1) | EP2195868B1 (enExample) |
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| US10538538B2 (en) | 2017-01-13 | 2020-01-21 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
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| DE102010009903A1 (de) * | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
| KR101759481B1 (ko) * | 2010-03-25 | 2017-07-20 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
| KR101792175B1 (ko) * | 2010-04-05 | 2017-11-01 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
| KR101759482B1 (ko) * | 2010-04-09 | 2017-07-20 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
| US20120273766A1 (en) * | 2010-10-12 | 2012-11-01 | Idemitsu Kosan Co., Ltd. | Aromatic heterocyclic derivative and organic electroluminescence device using the same |
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| EP3029037A1 (en) | 2014-12-05 | 2016-06-08 | Solvay SA | Acridine derivatives and their use in organic electronic devices |
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| US10329483B2 (en) | 2014-12-30 | 2019-06-25 | Dow Global Technologies Llc | Fluorene derivatives as light emitting elements for electroluminescent devices |
| CN107851729B (zh) | 2015-08-07 | 2020-07-28 | 株式会社半导体能源研究所 | 发光元件、显示装置、电子设备及照明装置 |
| US10457864B2 (en) | 2016-02-09 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
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| WO2019018741A1 (en) * | 2017-07-20 | 2019-01-24 | Board Of Trustees Of Michigan State University | REDOX FLOW BATTERY |
| KR102428159B1 (ko) | 2017-10-24 | 2022-08-03 | 삼성디스플레이 주식회사 | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| CN109232419B (zh) * | 2018-09-17 | 2021-01-05 | 宁波卢米蓝新材料有限公司 | 一种9,10-二氢吖啶衍生物及其制备方法和用途 |
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| KR101243918B1 (ko) * | 2006-01-03 | 2013-03-14 | 삼성디스플레이 주식회사 | 청색 발광 고분자, 그 제조방법 및 이를 채용한 유기 전계발광 소자 |
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- 2008-09-26 US US12/681,023 patent/US8384068B2/en active Active
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- 2008-09-26 WO PCT/EP2008/062976 patent/WO2009047147A1/de not_active Ceased
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007110228A1 (de) | 2006-03-27 | 2007-10-04 | Novaled Ag | N-heterozyklische verbindungen und deren verwendung in elektronischen, optoelektronischen und elektroluminiszenten bauelementen. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10538538B2 (en) | 2017-01-13 | 2020-01-21 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
Also Published As
| Publication number | Publication date |
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| JP5553758B2 (ja) | 2014-07-16 |
| WO2009047147A1 (de) | 2009-04-16 |
| US8384068B2 (en) | 2013-02-26 |
| US20100219406A1 (en) | 2010-09-02 |
| EP2195868B1 (de) | 2013-01-02 |
| KR20100084168A (ko) | 2010-07-23 |
| JP2011501878A (ja) | 2011-01-13 |
| EP2195868A1 (de) | 2010-06-16 |
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