JP6862420B2 - ヘキサメチルインダン - Google Patents
ヘキサメチルインダン Download PDFInfo
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- JP6862420B2 JP6862420B2 JP2018507509A JP2018507509A JP6862420B2 JP 6862420 B2 JP6862420 B2 JP 6862420B2 JP 2018507509 A JP2018507509 A JP 2018507509A JP 2018507509 A JP2018507509 A JP 2018507509A JP 6862420 B2 JP6862420 B2 JP 6862420B2
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- aromatic
- aromatic ring
- organic
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- WLALVCDHIGUUDM-UHFFFAOYSA-N 1,1,2,2,3,3-hexamethylindene Chemical compound C1=CC=C2C(C)(C)C(C)(C)C(C)(C)C2=C1 WLALVCDHIGUUDM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 57
- 239000000203 mixture Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 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 claims description 35
- -1 pyrimidinyl- Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000011159 matrix material Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 238000005401 electroluminescence Methods 0.000 claims description 26
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Polymers 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000001947 vapour-phase growth Methods 0.000 claims description 4
- RVVIGDFTASPDCM-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 RVVIGDFTASPDCM-UHFFFAOYSA-N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 238000004020 luminiscence type Methods 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims 1
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 7
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- HXGCENIFQNRYNC-UHFFFAOYSA-N 1,1,2,2,3,3-hexamethyl-9H-cyclopenta[b]carbazole Chemical compound CC1(C(C(C=2C1=CC=1NC3=CC=CC=C3C=1C=2)(C)C)(C)C)C HXGCENIFQNRYNC-UHFFFAOYSA-N 0.000 description 5
- JRXUJTKEBRQYCT-UHFFFAOYSA-N 1,1,2,2,3,3-hexamethylinden-5-amine Chemical compound CC1(C)C2=CC=C(N)C=C2C(C)(C)C1(C)C JRXUJTKEBRQYCT-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- YYZSSUIMUOXEDO-UHFFFAOYSA-N 7,7-dimethyl-5-phenylindeno[2,1-b]carbazole Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 YYZSSUIMUOXEDO-UHFFFAOYSA-N 0.000 description 4
- NTKIKAGLKRUYCG-UHFFFAOYSA-N N-(2-chlorophenyl)-1,1,2,2,3,3-hexamethylinden-5-amine Chemical compound ClC1=C(C=CC=C1)NC=1C=C2C(C(C(C2=CC=1)(C)C)(C)C)(C)C NTKIKAGLKRUYCG-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QJRPRLRIJCIZEH-UHFFFAOYSA-N 8-phenyl-5,7-dihydroindeno[2,1-b]carbazole Chemical compound C1(=CC=CC=C1)C1=C2CC3=CC=4NC5=CC=CC=C5C=4C=C3C2=CC=C1 QJRPRLRIJCIZEH-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- VWUSYZMWURWIIS-UHFFFAOYSA-N tert-butyl N-(1,1,2,2,3,3-hexamethylinden-5-yl)carbamate Chemical compound C(C)(C)(C)OC(NC=1C=C2C(C(C(C2=CC=1)(C)C)(C)C)(C)C)=O VWUSYZMWURWIIS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- LHNCOOIPHAICJZ-UHFFFAOYSA-N 1,1,2,2,3,3-hexamethyl-5-(2-nitrophenyl)indene Chemical compound CC1(C(C(C2=CC(=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])(C)C)(C)C)C LHNCOOIPHAICJZ-UHFFFAOYSA-N 0.000 description 2
- BGTHOVWKFIOPET-UHFFFAOYSA-N 1,1,2,2,3,3-hexamethyl-6H-cyclopenta[c]carbazole Chemical compound CC1(C)c2ccc3[nH]c4ccccc4c3c2C(C)(C)C1(C)C BGTHOVWKFIOPET-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- FECNLRGSKHAKIM-UHFFFAOYSA-N 5-bromo-1,1,2,2,3,3-hexamethylindene Chemical compound C1=C(Br)C=C2C(C)(C)C(C)(C)C(C)(C)C2=C1 FECNLRGSKHAKIM-UHFFFAOYSA-N 0.000 description 2
- CGQWGCZNQQUZSO-UHFFFAOYSA-N 6-bromo-N-(1,1,2,2,3,3-hexamethylinden-5-yl)-1,1,2,2,3,3-hexamethylinden-5-amine Chemical compound BrC1=C(C=C2C(C(C(C2=C1)(C)C)(C)C)(C)C)NC=1C=C2C(C(C(C2=CC=1)(C)C)(C)C)(C)C CGQWGCZNQQUZSO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
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- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
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- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
Yは、出現毎に同一であるか異なりC(R1)2、N(R1)、C(=O)、C(=S)、OまたはS、好ましくは、C(R1)2またはN(R1)であり;
Xは、出現毎に同一であるか異なり、Xは、CR1またはNであり;ここで、X基の何れかがCR1であることが好ましく;
R1は、出現毎に同一であるか異なり、R1は、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々、1以上のR2により置換されてもよく、1以上の隣接しないメチレン基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはC(=O)NR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CN、NO2を含むことができる。)または、1以上の基R2により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R2により随意に置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリーオキシ基または、1以上の基R2により随意に置換されてよい5〜40個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基またはこれらの構造の組み合わせを含み;ここで、2個以上の置換基R1は、それらが結合する原子と一緒に、もしくは2個の置換基R1は、それらが結合する原子と一緒に、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R2は、出現毎に同一であるか異なり、R2は、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々、1以上の基R3により随意に置換されてもよく、1以上の隣接しないCH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、SもしくはCONR3で随意に置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で随意に置き代えられてよい。)または、1以上の基R3により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R3により随意に置換されてよい5〜40個の芳香族環原子を有するアリールオキシ、アラルコキシもしくはヘテロアリーオキシ基または、1以上の基R3により随意に置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基またはこれらの基の1以上の組み合わせを含み;ここで、2個以上の置換基R2は、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく、ここで、好ましくは、2個以上のジェミナルおよびビシナルな置換基R2は、単一のモノあるいはポリ環状の脂肪族もしくは芳香族環構造を形成してもよく;
R3は、出現毎に同一であるか異なり、R3は、H、D、F、1以上のH原子がFで置換することができる1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基を含み;ここで、1以上のH原子はFで置き代えられてよく;ここで、2個以上の置換基R3は、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく、ここで、好ましくは、ジェミナルおよびビシナルな置換基R3は、単一のモノあるいはポリ環状の脂肪族もしくは芳香族環構造を形成せず;
R4は、出現毎に同一であるか異なり、R4は、Ar1、C1−C40アルキル、C1−C40不飽和基、C3−C40環状アルキルもしくは、C3−C40不飽和環状基を含む第1の部分、さらにR2を含む部分を含み、ここで、1以上のメチレン基は、好ましくは、非ビシナルなメチレン基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、OもしくはCONR2から選ばれる置換基を含むことができ、ここで、1以上の水素原子は、D、F、Cl、Br、I、CN、NO2もしくはAr1から選ばれる置換基を含むことができ、
Ar1は、出現毎に同一であるか異なり、Ar1は、芳香族環、芳香族環構造、複素環式芳香族環、複素環式芳香族環構造もしくは芳香族複素環式芳香族環構造を含み;ここで、Ar1は、1以上の基R3を含むことができ;
mは、0、1または2であり、好ましくは、mは、1であり、非常に好ましくは、mは、0であり;
nは、0または1、好ましくは、0であり;ここで、n=0は、両方の環が、共有単結合を介して互いに結合することを意味する。
1つの態様では、上記化合物は、式(1a)、(1b)もしくは(1c)の1つから選ばれる:
R5は、出現毎に同一であるか異なり、R5は、H、D、F、Cl、Br、I、CHO、N(Ar2)2、C(=O)Ar2、P(=O)(Ar2)2、S(=O)Ar2、S(=O)2Ar2、CR6=CR6Ar2、CN、NO2、Si(R6)3、B(OR6)2、B(R6)2、B(N(R6)2)2、OSO2R6、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々、1以上のR6により置換されてもよく、1以上の隣接しないメチレン基は、R6C=CR6、C≡C、Si(R6)2、Ge(R6)2、Sn(R6)2、C=O、C=S、C=Se、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはC(=O)NR6で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CN、NO2を含むことができる。)または、1以上の基R6により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R6により随意に置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリーオキシ基または、1以上の基R6により随意に置換されてよい5〜40個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基またはこれらの構造の組み合わせを含み;ここでに、2個以上の置換基R5は、それらが結合する原子と一緒に、または2個の置換基R5は、それらが結合する原子と一緒に、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R6は、出現毎に同一であるか異なり、R6は、H、D、F、1以上のH原子がFで置換することができる1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(1以上のH原子は、Fで置換されることができる)を含み;ここで、2個以上の置換基R6は、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく、ここで、好ましくは、ジェミナルおよびビシナルな置換基R6は、単一のモノあるいはポリ環状の脂肪族もしくは芳香族環構造を形成してもよく;
Ar2は、出現毎に同一であるか異なり、Ar2は、芳香族環、芳香族環構造、複素環式芳香族環、複素環式芳香族環構造もしくは芳香族複素環式芳香族環構造を含み;ここで、Ar2は、5〜40個の環原子を含むことができ、Ar2は、1以上のR6置換基を含み;
pは、0、1、2、3、4または5である。
LUMO(eV)=(1.0658*LEh*27.212)−0.5049
HOMO(eV)=(0.8308*HEh*27.212)−1.1180
これらの値は、本願の目的のために、材料のHOMOおよびLUMOとみなすべきである。
例1
1,1,2,2,3,3-ヘキサメチル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン(4a)と、1,1,2,2,3,3-ヘキサメチル-1,2,3,6-テトラヒドロ-シクロペンタ[c]カルバゾール(5a)の合成
2Lの四ツ口フラスコ中で、51.5g(183ミリモル、1.0当量)の5-ブロモ-2,3-ジヒドロ-1,1,2,2,3,3-ヘキサメチル-1H-インデン[1562418-80-7]を、25.0g(196ミリモル、1.07当量)の2-クロロアニリンと、45.7g(476ミリモル、2.6当量)のナトリウム-tert-ブトキシドとともに、840mlの無水トルエンに溶解する。混合物を30分間脱気し、次いで411mg(1.83ミリモル、0.01当量)の酢酸パラジウム(II)と、1.01g(1.83ミリモル、0.01当量)の1,1’-ビス(ジフェニルホスフィノ)フェロセンを添加する。反応物を100℃まで4時間、加熱する。反応の完了後、300mlの水を添加し、混合物をさらに30分間撹拌する。次いで、水相を分離し、有機相を水で三回洗浄する。結合した水性層をトルエンで一度抽出する。結合した有機相を硫酸ナトリウムで脱水させ、次いで溶媒を真空で除去する。54.0g(164ミリモル、90%)の所望の二級アミン3aが、茶色がかったオイルとして得られる。
1Lの四ツ口フラスコに、54.0g(164ミリモル、1.0当量)の(2-クロロ-フェニル)-(1,1,2,2,3,3-ヘキサメチル-インダン-5-イル)-アミン3aと、56.7g(410ミリモル、2.5当量)の炭酸カリウムと、650mlの1-メチル-2-ピロリドンを入れる。混合物を30分間脱気した後、トルエン中、5.03g(49.2ミリモル、0.30当量)のピバル酸と、736mg(3.3ミリモル、0.02当量)の酢酸パラジウム(II)と、6.6ml(6.6ミリモル、0.04当量)の1モル/lのトリ-tert-ブチルホスフィン溶液とを添加する。反応物を130℃で終夜、加熱し、反応の完了後、溶媒とピバル酸を真空で除去し、残った固形物を100mlのトルエンに溶解する。溶液を150mlの水で三回洗浄し、硫酸ナトリウムで脱水する。溶媒の蒸発後、異性体混合物を、n−ヘプタンからの二回の結晶化により分離する。13.4g(45.9ミリモル、28%)の異性体4aが、薄茶色の結晶として得られ、29.1g(100ミリモル、61%)の異性体5aが、溶媒の蒸発後に得られる。
50.0g(152ミリモル、1.0当量)の2-(1,1,2,2,3,3-ヘキサメチル-インダン-5-イル)-4,4,5,5-テトラメチル-[1,3,2]ジオキサボロランと、32.3g(160ミリモル、1.05当量)の1-ブロモ-2-ニトロベンゼンとを、32.3g(305ミリモル、2.0当量)の炭酸ナトリウムととともに、400mlのトルエンと、400mlの1,4-ジオキサンと、200mlの水とに溶解する。30分間の脱気後、1.76g(1.52ミリモル、0.01当量)のテトラキス(トリフェニル-ホスフィン)パラジウム(0)を添加し、混合物を還流下で終夜、撹拌する。次いで、相を分離し、水性相をトルエンで一度抽出する。結合した有機層を飽和NaCl溶液で洗浄し、硫酸ナトリウムで脱水させる。n−ヘプタンからの結晶後、28.0g(86ミリモル、57%)の8aが僅かに茶色の結晶として得られる。より多くの生成物が沈殿するまで、残った溶液を蒸発させ、18.6g(57ミリモル、38%)の追加的生成物8aが得られる。
40.5g(124ミリモル、1.0当量)の8aを、オートクレーブ(140℃、最大7.6バール、35時間)中で2.8lの一酸化炭素の存在下で、500mlのDMFにおいて、417mg(2.5ミリモル、0.02当量)の酢酸パラジウム(II)と、2.40g(13ミリモル、0.11当量)の1,10-フェナントロリンと反応させる。反応の完了後、混合物をシリカによって、95:5ヘプタン/THFとともに濾過し、溶媒を真空で蒸発させる。異性体混合物を結晶化により分離し、14.3g(49ミリモル、40%)の異性体4aが二回の結晶後に、薄茶色がかった結晶として得られ、他方で、19.7g(67ミリモル、55%)の異性体5aが溶媒の蒸発後に得られる。
6-ブロモ-1,1,2,2,3,3-ヘキサメチル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン(9a)の合成
7-(1,1,2,2,3,3-ヘキサメチル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン-6-イル]-12,12-ジメチル-10-フェニル-10,12-ジヒドロ-10-アザ-インデノ[2,1-b]フルオレン(11a)の合成
13.0g(35.1ミリモル、1.0当量)の6-ブロモ-1,1,2,2,3,3-ヘキサメチル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン9aと、17.5g(36.2ミリモル、1.03当量)の12,12-ジメチル-10-フェニル-7-(4,4,5,5-テトラメチル-[1,3,2]ジオキサボロラン-2-イル)-10,12-ジヒドロ-10-アザ-インデノ[2,1-b]フルオリン[1379585-25-7]10aと、18.6g(70.2ミリモル、2.0当量)のリン酸カリウムとを、200mlのトルエンと、200mlの1,4-ジオキサンと、100mlの水とに溶解する。混合物を30分間脱気後、79mg(0.35ミリモル、0.01当量)の酢酸パラジウム(II)と、427mg(1.40ミリモル、0.04当量)のトリ(o-トリル)-ホスフィンを添加する。反応物を還流下で終夜、撹拌し、室温に温める。混合物をセライトによって濾過し、400mlのトルエンで希釈する。水性層を分離し、有機相をNaCl溶液で三回洗浄し、結合した有機層を硫酸ナトリウムで脱水させる。溶媒の蒸発後、残留物を60℃で200mlのn−ヘプタン中で、30分間撹拌する。濾過後、21.3g(32.8ミリモル、93%)の生成物11aが灰茶色の固形物として得られる。
7-(1,1,2,2,3,3-ヘキサメチル-9-フェニル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン-6-イル]-12,12-ジメチル-10-フェニル-10,12-ジヒドロ-10-アザ-インデノ[2,1-b]フルオレン(13a)の合成
20.0g(30.8ミリモル、1.0当量)の7-(1,1,2,2,3,3-ヘキサメチル-1,2,3,9-テトラヒドロ-9-アザ-シクロペンタ[b]フルオレン-6-イル]-12,12-ジメチル-10-フェニル-10,12-ジヒドロ-10-アザ-インデノ[2,1-b]フルオレン11aと、3.57ml(33.9ミリモル、1.10当量)のブロモベンゼンと、8.88g(92.5ミリモル、3.0当量)のナトリウム-tert-ブトキシドとを、500mlの無水トルエンに溶解する。30分間の脱気後、138mg(0.616ミリモル、0.02当量)の酢酸パラジウム(II)と、1.23ml(1.23ミリモル、0.04当量)のトリ-tert-ブチルホスフィン溶液(トルエン中1モル/l)とを添加する。反応物を還流下で二日間撹拌し、室温に冷まし、セライトによって濾過する。濾過物を約50mlに濃縮し、500mlのヘプタンを添加する。混合物を1時間撹拌し、沈殿物を濾過し、乾燥させる。18.6g(25.7ミリモル、83%)の灰色の固形物が粗生成物として得られる。生成物はヘプタン/トルエン5:1による熱抽出によって精製され、トルエン/アセトニトリルで三回、再結晶化される。二回の昇華後、2.45g(3.38ミリモル、11%)の最終生成物13aが、純度>99.9%(HPLC)で無色の固形物として得られる。
(6-ブロモ-1,1,2,2,3,3-ヘキサメチル-インダン-5-イル)-(1,1,2,2,3,3-ヘキサメチル-インダン-5-イル)-アミン(17a)の合成
50.0g(178ミリモル、1.0当量)の5-ブロモ-1,1,2,2,3,3-ヘキサメチル-インダン-5-ブロモ-1,1,2,2,3,3-ヘキサメチル-インダン1aと、31.2g(267ミリモル、1.5当量)のtert-ブチルカルバメートと、146g(356ミリモル、2.0当量)の炭酸セシウムとを750mlのtert-ブタノールに溶解し、20分間脱気する。次いで、6.52g(7.12ミリモル、0.04当量)のトリス(ジベンジリデンアセトン)ジパラジウム(0)と、4.38g(10.7ミリモル、0.04当量)のS-Phosとを添加し、混合物を終夜、還流させた。反応の完了後、溶媒を真空で除去する。52.0g(164ミリモル。92%)の茶色がかったオイルが得られる。
52.0g(164ミリモル、1.0当量)の(1,1,2,2,3,3-ヘキサメチル-インダン-5-イル)-カルバミン酸tert-ブチルエステル14aを、500mlのジクロロメタンに溶解し、63.2ml(820ミリモル、5.0当量)のトリフルオロ酢酸で処理する。反応物を室温で14時間撹拌し、反応の完了後、溶媒を蒸発させ、粗生成物を酢酸エチルに再度溶解し、炭酸ナトリウムで洗浄する。溶液を硫酸ナトリウムで脱水させ、溶媒を真空で除去した。31.7g(146ミリモル、89%)の所望の生成物15aが僅かに茶色がかったオイルとして得られる。
2Lの四ツ口フラスコ中で、30.0g(138ミリモル、1.0当量)の1,1,2,2,3,3-ヘキサメチル-インダン-5-イルアミン15aを、53.5g(148ミリモル、1.07当量)の5,6-ジブロモ-2,3-ジヒドロ-1,1,2,2,3,3-ヘキサメチル-1H-インデン[1541101-19-2]16aと、35.5g(359ミリモル、2.6当量)のナトリウム-tert-ブトキシドとともに、600mlの無水トルエンに溶解する。混合物を30分間脱気し、次いで310mg(1.38ミリモル、0.01当量)の酢酸パラジウム(II)と、765mg(1.38ミリモル、0.01当量)の1,1’-ビス(ジフェニルホスフィノ)フェロセンを添加する。反応物を100℃まで12時間、加熱する。反応の完了後、200mlの水を添加し、混合物をさらに45分間撹拌する。次いで、水性相を分離し、有機相を水で三回洗浄する。結合した水性層をトルエンで一度抽出する。結合した有機相を硫酸ナトリウムで脱水し、溶媒を真空で除去する。43.2g(86.9ミリモル、63%)の所望の第二級アミン17aが、茶色がかったオイルとして得られる。
化合物18aの合成
1Lの四ツ口フラスコに、43.0g(86.6ミリモル、1.0当量)の17aと、29.9g(217ミリモル、2.5当量)の炭酸カリウムと、500mlの1-メチル-2-ピロリドンを入れる。混合物を25分間脱気した後、トルエン中、2.65g(26.0ミリモル、0.30当量)のピバル酸と、389mg(1.73ミリモル、0.02当量)の酢酸パラジウム(II)と、3.46ml(3.46ミリモル、0.04当量)の1モル/lのトリ-tert-ブチルホスフィン溶液とを添加する。反応物を130℃で終夜、撹拌し、反応の完了後、溶媒とピバル酸を真空で除去し、残った固形物を50mlのトルエンに溶解する。溶液を75mlの水で三回洗浄し、硫酸ナトリウムで脱水する。溶媒の蒸発後、粗生成物をn−ヘプタン/トルエンからの結晶化により精製する。23.7g(56.9ミリモル、66%)の生成物18aが、薄茶色の結晶として得られる。
化合物20aの合成
25.0g(56.9ミリモル、1.00当量)の7-ブロモ-12,12-ジメチル-10-フェニル-10,12-ジヒドロ-10-アザ-インデノ[2,1-b]フルオレン19aを、23.7g(56.9ミリモル、1.00当量)の遊離体18aと、8.46g(85.3ミリモル、1.50当量)のナトリウム-t-ブトキシドとともに、500mlの無水トルエンに溶解する。反応物を30分間、脱気した後、1.30g(1.42ミリモル、0.03当量)のトリス(ジベンジリデンアセトン)ジパラジウム(0)と、2.84ml(2.84ミリモル、0.05当量)のトリ-tert-ブチルホスフィン溶液を添加する。混合物を終夜、還流させ、反応の完了後、溶液を真空で濃縮する。沈殿物を濾過し、水とエタノールとで洗浄する。生成物をヘプタン/トルエン3:1による熱抽出により精製し、トルエン/ヘプタンで三回、再結晶化させる。二回の昇華後、19.8g(25.6ミリモル、45%)の最終生成物20aが、純度>99.9%(HPLC)で無色の固形物として得られる。
化合物22aの合成:
50mlの無水DMF中、1.73g(43.3ミリモル、1.2当量)の60重量%の水素化ナトリウムの懸濁液に対して、50mlの無水DMF中、15.0g(36.1ミリモル、1.0当量)の遊離体20aをゆっくりと添加する。反応の完了後、別の50mlのトルエン中、9.66g(36.1ミリモル、1.0当量)の2-クロロ-4,6-ジフェニル-[1,3,5]トリアジンを、この混合物に添加する。終夜撹拌した後、100mlの水を滴下し、沈殿物を濾過し、水とエタノールとで洗浄し、真空で乾燥させる。生成物をヘプタン/トルエン1:1による熱抽出によって精製し、トルエン/ヘプタンで二回、再結晶化させる。二回の昇華後、7.30g(11.3ミリモル、31%)の最終生成物20aが、純度>99.9%(HPLC)で無色の固形物として得られる。
素子の調製および特性決定
以下の例V1〜E13(表1と2を参照)は、種々のOLEDのデータを示している。
ホスト材料としての、本発明の化合物の使用は、技術水準の材料と比較して、とくに素子効率に関して著しく改善されたOLED素子データを生じる。
Claims (17)
- 以下の式(2a)、(2b)または(2c)の一つから選ばれる化合物、
Xは、出現毎に同一であるか異なり、CR1またはNであり;
R1は、出現毎に同一であるか異なり、R1は、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々、1以上のR2により置換されてもよく、1以上の隣接しないメチレン基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはC(=O)NR2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CN、NO2から選ばれる置換基を含むことができる。)または、1以上の基R2により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R2により随意に置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリーオキシ基または、1以上の基R2により随意に置換されてよい5〜40個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基またはこれらの構造の組み合わせを含み;ここで、2個以上の置換基R1は、それらが結合する原子と一緒に、もしくは2個の置換基R1は、それらが結合する原子と一緒に、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R2は、出現毎に同一であるか異なり、R2は、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々、1以上の基R3により随意に置換されてもよい。)または、1以上の基R3により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R3により随意に置換されてよい5〜60個の芳香族環原子を有するアリールオキシ、アラルコキシもしくはヘテロアリーオキシ基または、10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基を含み;
R3は、出現毎に同一であるか異なり、R3は、H、D、F、1以上の水素原子がFで置換することができる1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基を含み;ここで、1以上のH原子はFで置き代えられてよく;ここで、2個以上の置換基R3は、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく、ここで、ジェミナルおよびビシナルな置換基R3は、単一のモノあるいはポリ環状の脂肪族もしくは芳香族環構造を形成せず;
R4は、出現毎に同一であるか異なり、出現毎に同一であるか異なることができる1以上のR2で置換されることができるフェニル−、ビフェニル−、テルフェニル−、クアテルフェニル−、ピリジル−、ピリミジニル−、ピラジニル−、ピリダジニル−、トリアジニル−、ジアリールアミノフェニル−もしくはジアリールアミノビフェニル基から選ばれ
Ar1は、出現毎に同一であるか異なり、Ar1は、芳香族環、芳香族環構造、複素環式芳香族環、複素環式芳香族環構造もしくは芳香族複素環式芳香族環構造を含み;ここで、Ar1は、1以上のR3置換基を含むことができる。 - R4が、以下の基の一つを含む、請求項1または2記載の化合物:
R5は、出現毎に同一であるか異なり、R5は、H、D、F、Cl、Br、I、CHO、N(Ar2)2、C(=O)Ar2、P(=O)(Ar2)2、S(=O)Ar2、S(=O)2Ar2、CR6=CR6Ar2、CN、NO2、Si(R6)3、B(OR6)2、B(R6)2、B(N(R6)2)2、OSO2R6、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々、1以上のR6により置換されてもよく、1以上の隣接しないメチレン基は、R6C=CR6、C≡C、Si(R6)2、Ge(R6)2、Sn(R6)2、C=O、C=S、C=Se、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはC(=O)NR6で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CN、NO2から選ばれる置換基を含むことができる。)または、1以上の基R6により各場合に置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R6により随意に置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリーオキシ基または、1以上の基R6により随意に置換されてよい5〜40個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基またはこれらの構造の組み合わせを含み;ここで、2個以上の置換基R5は、それらが結合する原子と一緒に、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R6は、出現毎に同一であるか異なり、R6は、H、D、F、1以上のH原子がFで置換することができる1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素(1以上のH原子は、Fで置換されることができる)を含み;ここで、2個以上の置換基R6は、モノあるいはポリ環状の脂肪族もしくは芳香族環構造を互いに形成してもよく、ここで、ジェミナルおよびビシナルな置換基R6は、単一のモノあるいはポリ環状の脂肪族もしくは芳香族環構造を形成してもよく;
Ar2は、出現毎に同一であるか異なり、Ar2は、芳香族環、芳香族環構造、複素環式芳香族環、複素環式芳香族環構造もしくは芳香族複素環式芳香族環構造を含み;ここで、Ar2は、5〜40個の環原子を含むことができ、Ar2は、1以上のR6置換基を含み;
pは、0、1、2、3、4または5である。 - 請求項1〜6何れか1項記載の少なくとも一つの化合物と、正孔注入材料(HIM)、正孔輸送材料(HTM)、正孔ブロック材料(HBM)、電子注入材料(EIM)、電子輸送材料(ETM)、電子ブロック材料(EBM)、ホスト材料、マトリックス材料、ワイドバンドギャップ材料、蛍光エミッター、燐光エミッター、n−ドーパントおよびp−ドーパントから選ばれる少なくとも一つの機能性材料を含む組成物。
- 機能性材料が、マトリックス材料から選ばれる、請求項7記載の組成物。
- 少なくとも一つの燐光エミッターをさらに含む、請求項7または8記載の組成物。
- さらに少なくとも一つのワイドバンドギャップ材料をさらに含み、ここで、ワイドバンドギャップ材料は、3.5eV以上のバンドギャップを有する、請求項7〜9何れか1項記載の組成物。
- 請求項1〜6何れか1項記載の少なくとも一つの化合物または請求項7〜10何れか1項記載の組成物と、少なくとも一つの溶媒を含む、調合物。
- 請求項1〜6何れか1項記載の少なくとも一つの化合物または請求項7〜10何れか1項記載の組成物の、電子素子での使用。
- 請求項1〜6何れか1項記載の少なくとも一つの化合物または請求項7〜10何れか1項記載の組成物を含む電子素子。
- 電子素子が、有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機エレクトロルミネッセンス素子、有機ソーラーセル(OSC)、有機光学検査器、有機光受容器から選ばれる、請求項13記載の電子素子。
- 素子が、有機発光トランジスタ(OLET)、有機電場消光素子(OFQD)、有機発光電子化学セル(OLEC)、有機レーザーダイオード(O−Laser)および有機発光ダイオード(OLED)より成る群から選ばれる有機エレクトロルミネッセンス素子であることを特徴とする、請求項13または14記載の電子素子。
- 有機発光電子化学セルまたは有機レーザーダイオードである、請求項15記載の電子素子。
- 方法は、気相堆積によりまたは溶液から、素子の少なくとも一つの有機層を堆積することを含む、請求項13〜15何れか1項記載の電子素子の製造方法。
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DE102010019306B4 (de) | 2010-05-04 | 2021-05-20 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
WO2011157339A1 (de) | 2010-06-15 | 2011-12-22 | Merck Patent Gmbh | Metallkomplexe |
DE102010027317A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
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KR102118013B1 (ko) * | 2013-02-22 | 2020-06-05 | 에스에프씨주식회사 | 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자 |
JP6502334B2 (ja) | 2013-10-08 | 2019-04-17 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN105706260B (zh) * | 2013-11-15 | 2019-08-13 | 默克专利有限公司 | 用于有机电子器件中的具有新型六元环结构的化合物 |
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2016
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- 2016-07-14 WO PCT/EP2016/001225 patent/WO2017025166A1/en active Application Filing
- 2016-07-14 US US15/751,735 patent/US10934292B2/en active Active
- 2016-07-14 KR KR1020187006762A patent/KR20180039680A/ko not_active Application Discontinuation
- 2016-07-14 CN CN201680046190.8A patent/CN107922335B/zh active Active
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JP2018530522A (ja) | 2018-10-18 |
US20200140440A1 (en) | 2020-05-07 |
CN107922335A (zh) | 2018-04-17 |
EP3334708B1 (en) | 2020-08-19 |
WO2017025166A1 (en) | 2017-02-16 |
EP3334708A1 (en) | 2018-06-20 |
US10934292B2 (en) | 2021-03-02 |
CN107922335B (zh) | 2021-06-04 |
TWI715607B (zh) | 2021-01-11 |
TW201718489A (zh) | 2017-06-01 |
KR20180039680A (ko) | 2018-04-18 |
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