JP7319029B2 - ヘテロ環化合物及びそれを含む有機電界発光素子 - Google Patents
ヘテロ環化合物及びそれを含む有機電界発光素子 Download PDFInfo
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- JP7319029B2 JP7319029B2 JP2018145417A JP2018145417A JP7319029B2 JP 7319029 B2 JP7319029 B2 JP 7319029B2 JP 2018145417 A JP2018145417 A JP 2018145417A JP 2018145417 A JP2018145417 A JP 2018145417A JP 7319029 B2 JP7319029 B2 JP 7319029B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 50
- 238000005401 electroluminescence Methods 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 46
- 230000005525 hole transport Effects 0.000 claims description 30
- 239000002019 doping agent Substances 0.000 claims description 9
- 230000003111 delayed effect Effects 0.000 claims description 6
- 239000010410 layer Substances 0.000 description 124
- 239000000126 substance Substances 0.000 description 115
- -1 3,3- dimethylbutyl group Chemical group 0.000 description 89
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 27
- 125000000623 heterocyclic group Chemical group 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 12
- 229910052805 deuterium Inorganic materials 0.000 description 11
- 125000004431 deuterium atom Chemical group 0.000 description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 239000002356 single layer Substances 0.000 description 10
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- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 9
- 239000007810 chemical reaction solvent Substances 0.000 description 9
- 229940125807 compound 37 Drugs 0.000 description 9
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
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- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940127573 compound 38 Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-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
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 3
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
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- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- 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
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Description
ート)、Ir(dpbic)3などであってもよい。
本発明の一実施形態によるヘテロ環化合物は、例えば、下記のように合成してもよい。但し、本発明の一実施形態によるヘテロ環化合物の合成方法はこれに限らない。
化合物37は、例えば、下記方法によって合成されてもよい。
カルバゾール(16.72g、100mmol)を1、3-ジメチル-2-イミタゾリジノン(DMI)(50mL)に完全に溶かした後、KOtBu(11.8g、105mmol)を加える。反応混合物を120℃まで上げた後、1-ブロモ-3、5-ジフルオロベンゼン(5.75mL、50mmol)を徐々に滴加した後、反応温度を140℃まで上げてから、10時間還流する。反応を終了する。反応混合物を室温に冷却した後、氷水(500mL)に反応混合物を注ぎ、30分間攪拌する。得られた固体をガラスろ過器でろ過した後、蒸留水で数回洗浄し、EtOH(500mL)で洗浄する。得られた固体を真空乾燥させて、中間化合物1(21.3g、87%)を得た。1H NMR(300MHZ、CDCl3):δppm8.13(d、4H)、7.84(s、2H)、7.77(s、1H)、7.53(d、4H)、7.44(t、4H)、7.32(t、4H)。
中間化合物1(16.4g、33.6mmol)、ビス(ピナコラート)ジボロン(17.1g、67.2mmol)と酢酸カリウム(32.97g、336mmol)を1、4-ジオキサン(200mL)に溶かした後、窒素気流下で60℃で15分間攪拌する。反応混合物にPd(dppf)CH2Cl2(0.82g、1.0mmol)を加えた後、80℃で14時間攪拌する。反応混合物を室温に冷却して、トルエンで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン(MC)=1:3(V/V))で精製して、中間化合物2(11.76g、収率:65%)を得た。1H NMR(300MHZ、CDCl3):δppm8.17-8.11(m、6H)、7.87(s、1H)、7.54-7.40(s、9H)、7.34-7.30(m、3H)、1.36(s、12H)。
中間化合物2(11.76g、22mmol)と1-ブロモ-2-ニトロベンゼン(3.68g、18.2mmol)をジオキサン/トルエン(30mL/30mL)に溶かした後、反応混合物にK2CO3(7.6g、55mmol)と蒸留水10mLを入れ、20分間窒素気流下で攪拌した後、Pd(PPh3)4(0)(0.8g、0.69mmol)を入れて、反応混合物を80℃で12時間攪拌する。反応終了後、温度を常温にした後、エチルアセテート(EA)(100mL)で抽出してから、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=10:1(V/V))で精製して、中間化合物3(8.02g、収率69%)を得た。1H NMR(300MHZ、DMSO-d6) ppm8.77(d、1H)、8.42(d、1H)、8.33(d、2H)、8.26(d、2H)、7.65(d、1H)、7.59-7.55(m、2H)、7.52-7.43(m、6H)、7.37-7.25(m、7H)。
窒素気流下で、中間化合物3(9.9g、37.8mmol)、PPh3(7.92g、30.2mmol)、及びo-ジクロロベンゼン(80mL)を混合し、185℃で12時間攪拌した後、蒸留を介して、反応溶媒を除去し、EA(100mL)で抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=10:1(V/V))で精製して、MeOHで洗浄した後、真空乾燥して中間化合物4(5.04g、収率67%)を得た。1H NMR(300MHZ、DMSO-d6) ppm11.33(s、1H)、8.65(d、1H)、8.45-8.18(m、5H)、7.69(d、1H)、7.52-7.43(m、8H)、7.36-7.23(m、7H)。
窒素気流下で、中間化合物4(3.0g、6.03mmol)、3-ヨード-9-フェニル-9H-カルバゾール(3.3g、9.04mmol)、Cu(0.038g、0.603mmol)、K2CO3(0.38g、6.03mmol)、Na2CO3(0.64g、6.03mmol)、及びニトロベンゼン(20mL)を混合した後、195℃で18時間攪拌した。蒸留を介して、反応溶媒を除去し、EA(100mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン=10:1(V/V))で精製して、最終的に化合物37(2.29g、収率51%)を得た。1H NMR(300MHZ、DMSO-d6) ppm8.88(d、1H)、8.50(d、1H)、8.29(d、2H)、7.77-7.76(m、4H)、7.61-7.41(m、10H)、7.39-7.22(m、9H)、7.20-7.05(m、4H)、6.63(dd、1H)、6.56(t、1H)、6.33(d、1H)、HRMS(El、m/z):calcd for C54H34N3 738.2783、found 738.7284.
(1)中間化合物6の合成
窒素気流下で、カルコン(15.65g、75.14mmol)、エチル-2-ニトロアセテート(10.0g、75.13mmol)、NH4OAc(34.75g、451mmol)、及びEtOH(375mL)を混合した後、100℃で20時間攪拌して、反応を終了する。ジクロロメタン(MC)(500mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=1:2(V/V))で精製して、中間化合物6(7.04g、収率38%)を得た。1H NMR(300MHZ、DMSO-d6) ppm11.69(s、1H)、7.90(dd、2H)、7.82(dd、2H)、7.50(m、6H)、7.00(s、1H)、6.66(s、1H)。
窒素気流下で、中間化合物6(7.51g、30.37mmol)とPOCl3(60mL)を混合した後、140℃で12時間攪拌する。蒸留を介して、POCl3を除去し、EA(100mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、中間化合物7(3.02g、収率37%)を得た。1H NMR(300MHZ、CDCl3) ppm7.98(dd、2H)、7.77(s、1H)、7.60(m、2H)、7.42(m、7H)。HRMS(El、m/z):calcd for C17H12ClN 256.0658、found 256.0658.
窒素気流下で、中間化合物4(2.87g、6.03mmol)、中間化合物7(2.38g、8.96mmol)、Cu(0.037g、0.582mmol)、K2CO3(0.80g、5.77mmol)、Na2CO3(0.61g、5.77mmol)、及びニトロベンゼン(13mL)を混合した後、195℃で27時間攪拌した。蒸留を介して、反応溶媒を除去し、EA(100mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、最終的に化合物38(2.62g、収率60%)を得た。1H NMR(300MHZ、DMSO-d6) ppm8.91(d、1H)、8.55(d、1H)、8.30(d、2H)、7.79(s、1H)、7.73(d、2H)、7.67(m、2H)、7.60(t、3H)、7.51(m、3H)、7.44-7.30(m、13H)、7.20(d、3H)、7.08(s、1H)、6.68(s、2H)、HRMS(El、m/z):calcd for C53H34N4 726.2783、found 726.2783.
窒素気流下で、9-フェニル-9H-カルバゾール(4.0g、16.4mmol)、Kl(3.57g、21.5mmol)、KlO3(4.6g、21.5mmol)、及びAcOH(80mL)を混合した80℃で12時間攪拌する。反応終結後、得られた固体をガラスろ過器でろ過し、水(200mL)で洗浄し、1M NaHCO3(100mL)で洗浄し、1M Na2S2O3(100mL)で洗浄する。得られた固体をEAに溶かしてから水で洗浄し、有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン)で精製して、中間化合物9(7.62g、収率94%)を得た。1H NMR(300MHZ、CDCl3) ppm8.38(s、2H)、7.59(m、4H)、7.43(m、3H)、7.17(d、2H)。
窒素気流下で、中間化合物9(5.0g、10.1mmol)をTHF(80mL)に溶かした後、反応温度を-80℃まで下げる。反応混合物にn-BuLi(2.5 inへキサン、4mL、10.0mmol)を徐々に滴加した後、同じ温度で1時間攪拌する。反応混合物にトリフェニルシリルクロライド溶液(4.5g、15.2mmol、THF(30mL))を徐々に滴加し、-80℃で30分間攪拌した後、反応混合物を室温で18時間攪拌する。反応混合物に20%NH4Cl溶液を入れて、反応を終了する。反応混合物をジクロロメタンで抽出し、有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、中間化合物10(2.82g、収率47%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.41(s、1H)、7.8.40(s、1H)、7.71-7.42(m、24H)。HRMS(El、m/z):calcd for C36H26Sil 627.0879、found 627.0880.
窒素気流下で、中間化合物4(1.32g、2.65mmol)、中間化合物10(2.50g、3.98mmol)、Cu(0.0017g、0.265mmol)、K2CO3(0.366g、2.65mmol)、Na2CO3(0.281g、2.65mmol)、及びニトロベンゼン(10mL)を混合した後、195℃で27時間攪拌した。蒸留を介して、反応溶媒を除去し、EtOAc(100mL)で抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン=10:1(V/V))で精製して、最終的に化合物40(2.14g、収率81%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.61(s、1H)、8.28(d、1H)、8.24(d、2H)、7.67(s、1H)、7.66-7.62(m、7H)、7.61-7.57(m、6H)、7.55-7.39(m、6H)、7.22(m、2H)、7.29-7.05(m、4H)、6.91(t、1H)、6.65(dd、1H)、6.49(d、1H)、6.40(t、1H)、HRMS(FAB、m/z):calcd for C72H48N4Si 966.3648、found 966.3676.
窒素気流下で、1、3-ジブロモベンゼン(5.12mL、42.39mmol)をTHF(200mL)に溶かした後、反応温度を-78℃まで下げる。反応混合物にn-BuLi(2.5M inへキサン、17mL、42.5mmol)を徐々に滴加した後、同じ温度で1時間攪拌する。反応混合物にトリフェニルシリルクロライド溶液(15g、50.87mmol、THF(50mL))を徐々に滴加し、-78℃で1分間攪拌した後、反応混合物を室温で12時間攪拌する。反応混合物に20%NH4Cl溶液を入れて、反応を終了する。反応混合物をEAで抽出し、有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン)で精製して、中間化合物12(10.57g、収率60%)を得た。1H NMR(300MHZ、CDCl3):ppm7.62(t、1H)、7.57-7.51(m、7H)、7.45-7.40(m、4H)、7.38-7.35(m、6H)、7.21(d、1H)。
窒素気流下で、中間化合物12(6.85g、16.5mmol)、ビス(ピナコラート)ジボロン(6.28g、16.5mmol)、酢酸カリウム(3.56g、36.27mmol)、及び1、4-ジオキサン(40mL)を混合し、60℃で15分間攪拌する。反応混合物にPd(dppf)CH2Cl2(0.18g、0.25mmol)を加えた後、80℃で14時間攪拌する。反応混合物を室温に冷却させて、トルエンで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=5:1(V/V))で精製して、中間化合物13(6.34g、収率:81%)を得た。1H NMR(300MHZ、CD2Cl2):δppm8.00(s、1H)、7.89(d、2H)、7.68(d、1H)、7.64-7.58(m、6H)、7.49-7.40(m、10H)、1.34(s、12H)。
窒素気流下で、1-ブロモ-2-ニトロベンゼン(2.18g、10.8mmol)、中間化合物13(6.0g、13mmol)、K2CO3(4.5g、32.6mmol)、ジオキサン(30mL)、トルエン(30mL)、及び蒸留水(10mL)を混合し、20分間攪拌した後、Pd(PPh3)4(0.47g、0.41mmol)を入れて、90℃で12時間攪拌する。反応混合物を室温に冷却して、EAで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、中間化合物14(6.34g、収率:81%)を得た。1H NMR(300MHZ、DMSO-d6):δppm7.86(d、1H)、7.84-7.59(m、8H)、7.55-7.40(m、14H)。
窒素気流下で、中間化合物14(2.6g、5.68mmol)、P(OEt)3(30mL)、及びジクロロベンゼン(15mL)を混合した後、150℃で20時間攪拌する。蒸留を介して、反応溶媒を除去し、EAで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=6:1(V/V))で精製して、中間化合物15(1.52g、収率:62%)を得た。1H NMR(300MHZ、DMSO-d6):δppm8.33(s、1H)、8.01(d、1H)、7.55-7.44(m、13H)、7.23(m、1H)。
1-ブロモ-3、5-ジフルオロベンゼン(10g、52.1mmol)をc-H2SO4(10mL)に入れて20分間攪拌した後、発煙HNO3(2.5mL)を30分間滴加する。反応混合物を2時間攪拌した後、反応混合物を氷水(500mL)に徐々に注ぎ、30分間攪拌する。得られた固体をガラスろ過器でろ過した後、蒸留水で十分に洗浄する。形成された固体をEAに溶かして抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=6:1(V/V))で精製して、中間化合物16(9.25g、収率:75%)を得た。1H NMR(300MHZ、DMSO-d6):δppm7.90(ddd、1H)、7.86(ddd、1H)。
窒素気流下で、中間化合物16(19.5g、82mmol)、フェニルボロン酸(11g、90.2mmol)、K2CO3(22.2g、161mmol)、EtOH(160mL)、及びトルエン(200mL)を混合し、20分間攪拌した後、Pd(PPh3)4(1.0g、0.64mmol)を入れて、90℃で10時間攪拌する。反応混合物をEAで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=6:1(V/V))で精製して、中間化合物17(15g、収率:78%)を得た。1H NMR(300MHZ、CD2Cl2):δppm7.52-7.42(m、3H)、7.13-7.04(m、2H)、7.13-7.04(m、2H)。
窒素気流下で、中間化合物17(15g、64mmol)、PPh3(33.59g、128mmol)、及びo-ジクロロベンゼン(130mL)を混合した後、185℃で15時間攪拌して、反応を終了する。反応混合物を室温に冷却した後、反応混合物をセライト(celite)でろ過し、減圧蒸留して反応溶媒を除去した後、EAで抽出し、MgSO4で水分を除去した後、カラムクロマトグラフィ(n-へキサン:EA=10:1(V/V))で精製して、中間化合物18(7.15g、収率:55%)を得た。1H NMR(300MHZ、CDCl3):δppm8.15(s、1H)、8.13(d、1H)、7.44-7.35(m、2H)、7.30-7.25(m、1H)、6.91(dd、1H)、6.72(m、1H)。
窒素気流下で、中間化合物18(7.0g、34.4mmol)、ヨードベンゼン(7.0g、34.4mmol)、Cu(0.22g、3.44mmol)、 K2CO3(4.75g、34.4mmol)、Na2CO3(3.65g、34.4mmol)、及びニトロベンゼン(50mL)を混合した後、195℃で12時間攪拌した。蒸留を介して、反応溶媒を除去し、EtOAc(100mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン)で精製して、中間化合物19(7.9g、収率82%)を得た。1H NMR(300MHZ、CD2Cl2) ppm7.22-7.65(m、4H)、7.63-7.58(m、2H)、7.55-7.49(m、5H)、MS(El、m/z):278.
中間化合物19(0.99g、3.52mmol)を無水DMF(10mL)に溶かした後、NaH(0.084g、3.52mmol)を入れて、反応混合物を30分間攪拌した後、中間化合物15(1.51g、3.54mmol)を無水DMF(10mL)に溶かした溶液を反応混合物に徐々に滴加してから、100℃で12時間攪拌する。反応混合物を室温に冷却した後、MCで抽出し、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、中間化合物20(1.86g、収率77%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.64(s、1H)、7.72-7.60(m、15H)、7.55-7.48(m、2H)。
中間化合物20(1.8g、2.63mmol)を無水DMF(20mL)に溶かした後、NaH(0.063g、2.63mmol)を入れて、反応混合物を30分間攪拌した後、カルバゾール(0.45g、2.70mmol)を無水DMF(10mL)に溶かした溶液を反応混合物に徐々に滴加してから、120℃で15時間攪拌する。反応混合物を室温に冷却した後、EAで抽出し、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、最終的に化合物41(1.99g、収率90%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.55(s、1H)、8.47(s、1H)、8.30-8.17(m、12H)、7.87(s、1H)、7.71(s、1H)、7.60-7.57(m、5H)、7.53-7.44(m、20H)、HRMS(FAB、m/z):calcd for C60H41N3Si 831.3070、found 831.3049.
中間化合物19(5g、17.9mmol)をCH2Cl2(50mL)に溶かした後、NBS(3.2g、18mmol)を徐々に反応混合物に入れ、室温で明かりを遮断し、12時間攪拌する。蒸留水(100mL)を加えて反応を終了させ、MCで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン)で精製して、中間化合物22(5.0g、収率85%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.00(s、1H)、7.88(dt、1H)、7.66(dt、1H)、761-7.58(m、7H)。
窒素気流下で、中間化合物22(3.5g、9.77mmol)をTHF(50mL)に溶かした後、反応温度を-78℃まで下げる。反応混合物にn-BuLi(2.5M inへキサン、4.3mL、10.7mmol)を徐々に滴加した後、同じ温度で1時間攪拌する。反応混合物にトリフェニルシリルクロライド溶液(2.89g、9.80mmol、THF(20mL))を徐々に滴加し、-78℃で30分間攪拌した後、反応混合物を室温で12時間攪拌する。反応混合物に20%NH4Cl溶液を入れて、反応を終了させる。反応混合物をMCで抽出し、有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン=15:1(V/V))で精製して、中間化合物23(3.52g、収率67%)を得た。1H NMR(300MHZ、DMSO-d6):ppm8.61(s、1H)、8.49(s、1H)、7.73-7.62(m、6H)、7.51-7.42(m、14H)、7.36-7.32(m、2H)、7.22(d、1H)。
窒素気流下で、カルバゾール(0.96g、5.72mmol)、KOtBu(0.65g、5.83mmol)、及び1、3-ジメチル-2-イミダゾリジノン(DMI)(10mL)を混合した後、反応温度を120℃まで上げ、中間化合物23(1.5g、2,79mmol)をDMI(7mL)に溶かした溶液を徐々に反応混合物に滴加し、反応混合物を180℃で10時間攪拌する。反応混合物を室温に冷却した後、氷水(50mL)を入れて、30分間攪拌する。得られた固体をガラスろ過器でろ過した後、蒸留水で数回洗浄する。得られた固体化合物をEAに溶かして抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:MC=10:1(V/V))で精製して、最終的に化合物21(1.51g、収率65%)を得た。1H NMR(300MHZ、CD2Cl2) ppm8.56(s、1H)、8.25-8.20(m、3H)、8.02(d、1H)、7.77(dd、1H)、7.72(d、1H)、7.58(d、2H)、7.53-7.26(m、24H)、7.18(dd、1H)、7.10-6.98(m、4H)、6.88-6.78(m、2H)、6.49(t、1H)。
5H-ピロロ[3、2-c:4、5-c’]ジピリジン(16.92g、100mmol)を1、3-ジメチル-2-イミタゾリジノン(DMI)(50mL)に完全に溶かした後、KOtBu(11.8g、105mmol)を加える。反応混合物を120℃まで上げた後、1-ブロモ-3、5-ジフルオロベンゼン(5.75mL、50mmol)を徐々に滴加した後、反応温度を140℃まで上げてから、10時間還流させる。反応終了後、反応混合物を室温に冷却した後、氷水(500mL)に反応混合物を注ぎ、30分間攪拌する。得られた固体をガラスろ過器でろ過した後、蒸留水で数回洗浄し、EtOH(500mL)で洗浄する。得られた固体を真空乾燥し、中間化合物24(39.3g、収率80%)を得た。1H NMR(300MHZ、CDCl3):δppm9.32(d、4H)、8.35(d、4H)、7.53(d、4H)、7.50(s、3H)
中間化合物24(30.0g、61.1mmol)、ビス(ピナコラート)ジボロン(18,62g、73.3mmol)と酢酸カリウム(23.99g、244.4mmol)を1、4-ジオキサン(200mL)に溶かした後、窒素気流下で60℃で15分間攪拌する。反応混合物にPd(dppf)CH2Cl2(0.82g、1.0mmol)を加えた後、80℃で14時間攪拌する。反応混合物を室温に冷却して、トルエンで抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン(MC)=1:3(V/V))で精製して、中間化合物25(19.74g、収率:60%)を得た。1H NMR(300MHZ、CDCl3):δppm9.32(d、4H)、8.35(d、4H)、7.57-7.53(m、5H)、7.41(s、2H)、1.21(s、12H)
中間化合物25(15.0g、27.9mmol)と1-ブロモ-2-ニトロベンゼン(5.64g、27.9mmol)をジオキサン/トルエン(30mL/30mL)に溶かした後、反応混合物にK2CO3(7.7g、55.8mmol)と蒸留水(10mL)を入れ、20分間窒素気流下で攪拌した後、Pd(PPh3)4(0)(0.8g、0.69mmol)を入れて、反応混合物を80℃で12時間攪拌する。反応終了後、温度を常温にした後、エチルアセテート(EA)(100mL)で抽出してから、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=10:1(V/V))で精製して、中間化合物26(10.42g、収率70%)を得た。1H NMR(300MHZ、CDCl3):δppm9.34(d、4H)、8.35(d、4H)、8.17(s、2H)、8.03-8.01(m、2H)、7.87-7.80(m、2H)、7.61(s、1H)、7.51(d、4H)
窒素気流下で、中間化合物26(10.0g、18.7mmol)、PPh3(7.92g、30.2mmol)、及びo-ジクロロベンゼン(80mL)を混合し、185℃で12時間攪拌した後、蒸留を介して、反応溶媒を除去し、EA(100mL)で抽出した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:EA=10:1(V/V))で精製し、MeOHで洗浄してから真空乾燥して、中間化合物27(6.11g、収率65%)を得た。1H NMR(300MHZ、DMSO-d6) ppm11.33(s、1H)、9.34(d、4H)、8.35(d、4H)、8.17(m、1H)、7.63(m、2H)、7.55-7.50(m、5H)、7.32(s、1H)、7.18(m、1H)
窒素気流下で、中間化合物27(5.0g、9.97mmol)、ブロモベンゼン(1.72g、10.98mmol)、Cu(0.038g、0.603mmol)、K2CO3(1.38g、9.97mmol)、Na2CO3(1.06g、9.97mmol)、及びニトロベンゼン(20mL)を混合した後、195℃で18時間攪拌した。蒸留を介して、反応溶媒を除去し、EA(100mL)で有機層を分離した後、MgSO4で水分を除去し、カラムクロマトグラフィ(n-へキサン:ジクロロメタン=10:1(V/V))で精製して、最終的に化合物28(3.46g、収率60%)を得た。1H NMR(300MHZ、DMSO-d6) ppm9.34(d、4H)、8.55(d、1H)、8.35(d、4H)、7.94(d、1H)、7.63-7.51(m、10H)、7.32(m、2H)、7.16(m、1H)
上述した化合物37を発光層のホスト材料として使用し、実施例1のボトムエミッション型有機電界発光素子を製作した。
[実施例1化合物]
[実施例2化合物]
[比較例1化合物]
図5は、化合物1のねじれ角によるHOMOエネルギー準位及び三重項エネルギー準位の変化を測定したグラフである。図5を参照すると、化学式1のXが単結合である場合、化学式1で表わされる骨格と化学式2または化学式3で表わされる置換基とをの結合のねじれ角が50度以上であれば、比較的高い三重項エネルギー準位を有することが分かる。
HTR:正孔輸送領域 HIL:正孔注入層
HTL:電子輸送層 EML:発光層
ETR:電子輸送領域 ETL:電子輸送層
EIL:電子注入層 EL2:第2電極
Claims (4)
- 下記化合物群1に表された化合物のうちから選択されるいずれか一つのヘテロ環化合物。
[化合物群1]
- 第1電極と、
第1電極の上に設けられた正孔輸送領域と、
前記正孔輸送領域の上に設けられた発光層と、
前記発光層の上に設けられた電子輸送領域と、
前記電子輸送領域の上に設けられた第2電極と、を含み、
前記発光層は、請求項1によるヘテロ環化合物を含む、有機電界発光素子。 - 前記発光層はホスト及びドーパントを含み、
前記ホストは、請求項1によるヘテロ環化合物を含むものである、請求項2に記載の有機電界発光素子。 - 前記ホストは、りん光ホスト、または熱活性遅延蛍光ホストである、請求項3に記載の有機電界発光素子。
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