JP2015117235A - 有機化合物、発光素子、ディスプレイモジュール、照明モジュール、発光装置、表示装置、電子機器及び照明装置 - Google Patents
有機化合物、発光素子、ディスプレイモジュール、照明モジュール、発光装置、表示装置、電子機器及び照明装置 Download PDFInfo
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 238000005286 illumination Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 65
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 36
- 239000010410 layer Substances 0.000 description 193
- 239000000758 substrate Substances 0.000 description 47
- 239000000126 substance Substances 0.000 description 44
- -1 boronic acid compound Chemical class 0.000 description 35
- 239000007787 solid Substances 0.000 description 35
- 238000005401 electroluminescence Methods 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002131 composite material Substances 0.000 description 17
- 238000007789 sealing Methods 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000007983 Tris buffer Substances 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 14
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 125000005595 acetylacetonate group Chemical group 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 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 10
- 150000001721 carbon Chemical group 0.000 description 9
- 239000011229 interlayer Substances 0.000 description 9
- 229910052741 iridium Inorganic materials 0.000 description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003566 sealing material Substances 0.000 description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 7
- 238000005192 partition Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- HEZMWWAKWCSUCB-PHDIDXHHSA-N (3R,4R)-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylic acid Chemical compound O[C@@H]1C=CC(C(O)=O)=C[C@H]1O HEZMWWAKWCSUCB-PHDIDXHHSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910008449 SnF 2 Inorganic materials 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000004544 sputter deposition Methods 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 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 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- 229910003437 indium oxide Inorganic materials 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 238000010248 power generation Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 229910001930 tungsten oxide Inorganic materials 0.000 description 4
- 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 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
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- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- YFRPJYRKCNVHGK-UHFFFAOYSA-N 2-(4-phenylpyridin-2-yl)-1H-pyrimidin-6-one Chemical compound O=c1ccnc([nH]1)-c1cc(ccn1)-c1ccccc1 YFRPJYRKCNVHGK-UHFFFAOYSA-N 0.000 description 2
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- WDJPPUNHDVUKKF-UHFFFAOYSA-N 2-chloro-4-pyridin-2-ylpyrimidine Chemical compound ClC1=NC=CC(C=2N=CC=CC=2)=N1 WDJPPUNHDVUKKF-UHFFFAOYSA-N 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- MZUBDHQXEYJYIC-UHFFFAOYSA-N 4-phenylpyridine-2-carboximidamide;hydrochloride Chemical compound Cl.C1=NC(C(=N)N)=CC(C=2C=CC=CC=2)=C1 MZUBDHQXEYJYIC-UHFFFAOYSA-N 0.000 description 2
- JYUYDXDFWLZHBI-UHFFFAOYSA-N 4-pyridin-2-yl-2-[8-(4-pyridin-2-ylpyrimidin-2-yl)dibenzofuran-2-yl]pyrimidine Chemical compound c1ccc(nc1)-c1ccnc(n1)-c1ccc2oc3ccc(cc3c2c1)-c1nccc(n1)-c1ccccn1 JYUYDXDFWLZHBI-UHFFFAOYSA-N 0.000 description 2
- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 2
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 108091006149 Electron carriers Proteins 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- VJKIQKWBXNDDDG-UHFFFAOYSA-N [Na].CCOC(=O)CCO Chemical compound [Na].CCOC(=O)CCO VJKIQKWBXNDDDG-UHFFFAOYSA-N 0.000 description 2
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
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- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
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- 238000012905 input function Methods 0.000 description 1
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- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
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- 238000010030 laminating Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 1
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
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Abstract
【解決手段】ジベンゾフランの2位と8位に二つのピリジン環を含む複素芳香族基が結合した有機化合物を提供する。当該有機化合物は、発光素子の電子輸送材料として用いることが可能な有機化合物である。
【選択図】なし
Description
続いて、本発明の一態様である発光素子の例について図1(A)を用いて以下に説明する。
本発明の一態様の発光装置について図2を用いて説明する。なお、図2(A)は、発光装置を示す上面図、図2(B)は図2(A)をA−BおよびC−Dで切断した断面図である。この発光装置は、発光素子の発光を制御するものとして、点線で示された駆動回路部(ソース線駆動回路)601、画素部602、駆動回路部(ゲート線駆動回路)603を含んでいる。また、604は封止基板、605はシール材であり、シール材605で囲まれた内側は、空間607になっている。
本発明の一態様である照明装置を図6を参照しながら説明する。図6(B)は照明装置の上面図、図6(A)は図6(B)におけるe−f断面図である。
本発明の一態様である電子機器の例について説明する。電子機器として、例えば、テレビジョン装置(テレビ、またはテレビジョン受信機ともいう)、コンピュータ用などのモニタ、デジタルカメラ、デジタルビデオカメラ等のカメラ、デジタルフォトフレーム、携帯電話機(携帯電話、携帯電話装置ともいう)、携帯型ゲーム機、携帯情報端末、音響再生装置、パチンコ機などの大型ゲーム機などが挙げられる。これらの電子機器の具体例を以下に示す。
2−ピリジンボロン酸N−フェニルジエタノールアミンエステル6.0g(22.4mmol)、2,4−ジクロロピリミジン3.3g(22.4mmol)、リン酸三カリウム9.5g(44.7mmol)、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド0.785g(1.1mmol)、ヨウ化銅2.1g(11.1mmol)を500ml三口フラスコに入れ、フラスコ内を窒素置換した。この混合物に脱水N,N−ジメチルホルムアミド200mlを加え、減圧下で攪拌することにより脱気し、窒素気流下100度で6.5時間攪拌した。攪拌後、得られた反応溶液に酢酸エチルと水を加え、析出した固体を吸引ろ過で除去した。得られたろ液を水層と有機層に分液し、水層を抽出した。得られた抽出溶液と有機層を合わせて飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄した。洗浄後の有機層に無水硫酸マグネシウムを加えて乾燥させ、得られた混合物を自然ろ過してろ液を得た。このろ液を濃縮して油状物を得た。得られた油状物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、ヘキサン:酢酸エチル=10:1の混合溶媒を用いた。得られたフラクションを濃縮し、白色固体を0.85g、収率20%で得た。ステップ1の合成スキーム(a−1)を以下に示す。
2,8−ジヨードジベンゾフラン3.0g(7.1mmol)、ビス(ピナコレート)ジボロン4.0g(15.6mmol)、酢酸カリウム4.8g(48.6mmol)をフラスコに入れ、フラスコ内を窒素置換した。この混合物に脱水ジメチルスルホキシド70mlを加え、減圧下で攪拌することにより脱気した。この混合物に、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド0.408g(0.50mmol)を加え、窒素気流下90度で19時間攪拌した。攪拌後、得られた反応混合物にジクロロメタンを加えて、吸引ろ過で固体を除去した。得られたろ液を抽出し、得られた抽出溶液と有機層を合わせ水で3回洗浄した。この有機層に無水硫酸マグネシウムを加えて乾燥させ、得られた混合物を自然ろ過してろ液を得た。このろ液を濃縮して油状物を得た。得られた油状物をシリカカラムクロマトグラフィー(中性シリカ)により精製した。展開溶媒には、ヘキサン:酢酸エチル=10:1の混合溶媒を用いた。得られたフラクションを濃縮し、白色固体を1.9g、収率64%で得た。ステップ2の合成スキーム(b−1)を以下に示す。
ステップ2で合成した2,8−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボラン−2−イル)ジベンゾフラン0.88g(2.1mmol)、2−クロロ−4−(2−ピリジル)ピリミジン0.85g(4.4mmol)、トルエン22ml、エタノール9mlを100ml丸底フラスコに入れ、フラスコ内をアルゴン置換した。この混合物にテトラキス(トリフェニルホスフィン)パラジウム(0)0.194g(0.168mmol)を加え、アルゴンバブリングを20分間し、所定時間経過後、2M炭酸カリウム水溶液9mlを加えた。この反応容器にマイクロ波(2.45GHz 150W)を1時間照射することで反応させた。反応後、反応混合物を冷却し、固体を析出後、反応混合物を吸引濾過し、得られた固体を水で洗浄した。得られた固体にエタノールを加えて超音波を照射し、吸引ろ過をして白色固体を0.72g、収率72%で得た。得られた固体0.72gをトレインサブリメーション法により昇華精製した。圧力2.1Pa、アルゴン流量5mL/min、270℃の条件で、22時間加熱して行った。昇華精製後、目的物の固体を0.62g、回収率86%で得た。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。ステップ3の合成スキーム(c−1)を以下に示す。
1H−NMR.δ(DMSO−D6):7.66(t,2H),7.93(d,2H),8.16(d,2H),8.32(d,2H),8.80−8.83(m,4H),8.92(d,2H),9.12(d,2H),9.53(s,2H)
4−フェニルピリジン−2−カルボニトリル9.2g(51.3mmol)、メタノール(脱水)100mLを300mL三口フラスコに入れた。この混合物にナトリウムメトキシド127mg(2.36mmol)を加え、窒素気流下、室温で16時間撹拌した。所定時間経過後、塩化アンモニム2.7g(51.3mmol)を加え、窒素気流下、室温で18時間撹拌した。反応後、反応混合物を濃縮し、酢酸エチルを加えて超音波を照射し、吸引ろ過をして白色固体を10.8g、収率90%で得た。ステップ1の合成スキーム(a1−2)を以下に示す。
水素化ナトリウム(60% in oil)9.0g(557mmol)、ジイソプロピルエーテル400mLを1000mL三口フラスコに入れ、窒素気流下、40℃に加熱した。反応溶液の温度を42℃に保ちながら、酢酸エチル42.8g(474mmol)を滴下した。滴下後、系内の温度を42℃に保ちながら、蟻酸エチル74.4g(1005mmol)を滴下した。滴下後、40℃で14時間撹拌した。反応後、反応混合物を吸引ろ過し、固体を得た。得られた固体をヘキサンで洗浄し、白色固体を17.9g、収率27%で得た。ステップ2の合成スキーム(a2−2)を以下に示す。
4−フェニルピリジン−2−カルボキサミジン塩酸塩10.8g(46.2mmol)、ナトリウム 2−エトキシカルボニルエタノール17.9g(129.8mmol)、エタノール(脱水)220mLを1000mLナスフラスコに入れた。この混合物にナトリウムエトキシド3.1g(46.2mmol)を加え、窒素気流下、90℃で14時間加熱した。この反応混合物を濃縮し、残渣を得た。得られた残渣に水80mlと酢酸エチルを加えて超音波を照射し、吸引ろ過をして白色固体を7.7g、収率67%で得た。ステップ3の合成スキーム(a3−2)を以下に示す。
2−(4−フェニルピリジン−2−イル)ピリミジン−4(3H)−オン7.7g(30.8mmol)、塩化ホスホリル60mlを200ml三口フラスコに加え、窒素気流下、100℃で7時間加熱した。この混合物を氷にゆっくりと注ぎ、12時間撹拌した。この混合物にクロロホルムを加えて溶解し、この混合物の水層と有機層を分液し、水層をクロロホルムで抽出した。得られた抽出溶液と有機層を合わせて飽和炭酸水素ナトリウム水溶液、次いで飽和食塩水で洗浄した。洗浄後、有機層に無水硫酸マグネシウムを加えて乾燥させ、得られた混合物を自然濾過して、ろ液を得た。得られたろ液を濃縮して固体を得た。得られた固体をトルエンで再結晶し、白色固体を5.3g、収率65%で得た。ステップ4の合成スキーム(a4−2)を以下に示す。
実施例1のステップ2と同様に合成した。
2,8−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボラン−2−イル)ジベンゾフラン2.4g(5.6mmol)、4−クロロ−2−(4−フェニルピリジン−2−イル)ピリミジン3.5g(12.9mmol)、トルエン50ml、エタノール15ml、2M炭酸カリウム水溶液13mlを200mlの三口フラスコに加えた。フラスコ内を減圧下窒素置換することで脱気した。この混合物にテトラキス(トリフェニルホスフィン)パラジウム(0)0.518g(0.448mmol)を加え、90℃で12時間撹拌した。反応後、反応混合物を冷却し、固体を析出後、反応混合物を吸引濾過し、得られた固体を水、エタノールで洗浄した。さらに、得られた固体にトルエンを300mL加えて加熱還流した。この混合物をろ過して固体を0.92g、収率26%で得た。ステップ6の合成スキーム(c−2)を以下に示す。
1H−NMR.δ(DMSO−D6):7.53(t,2H),7.59(t,4H),7.91−7.96(m,6H),8.01(d,2H),8.32(d,2H),8.65(d,2H),8.79(s,2H),8.93(d,2H),9.13(d,2H),9.32(s,2H)
実施例1のステップ2と同様に合成した。
2,8−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボラン−2−イル)ジベンゾフラン2.3g(5.5mmol)、5−クロロ−1,10−フェナントロリン2.6g(12.0mmol)、ジオキサン28ml、2Mリン酸カリウム水溶液13mlを100ml丸底フラスコに入れて、アルゴンバブリングを20分間し、所定時間経過後、トリス(ジベンジリデンアセトン)パラジウム(0)0.302g(0.33mmol)、トリシクロヘキシルホスフィン20%トルエン溶液1.3ml(0.792mmol)を加えた。この反応容器にマイクロ波(2.45GHz 150W)を2時間照射することで反応させた。反応後、反応混合物を冷却し、固体を析出後、反応混合物を吸引ろ過し、得られた固体を水で洗浄した。得られた固体にエタノールを加えて超音波を照射し、吸引ろ過をして白色固体を得た。得られた固体にジクロロメタンを加えて、不溶物を自然ろ過により除去し、得られたろ液を濃縮して固体を得た。得られた固体に酢酸エチルを加えて超音波を照射し、吸引ろ過をして白色固体を1.5g、収率54%で得た。得られた固体1.5gをトレインサブリメーション法(圧力3.4Pa、アルゴン流量5mL/min、350℃、16時間)により昇華精製した。昇華精製後、目的物の固体を0.58g、回収率39%で得た。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。ステップ2の合成スキーム(c−3)を以下に示す。
1H−NMR.δ(CDCl3):7.59−7.61(m,2H),7.67−7.70(m,4H),7.82−7.85(m,4H),8.16(s,2H),8.28(dd,2H),8.33(dd,2H),9.22−9.24(m,4H)
実施例1のステップ2と同様に合成した。
2,8−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボラン−2−イル)ジベンゾフラン2.0g(4.8mmol)、2−クロロ−1,10−フェナントロリン2.3g(10.6mmol)、ジオキサン28ml、2Mリン酸カリウム水溶液13mlを100ml丸底フラスコに入れ、アルゴンバブリングを20分間し、所定時間経過後、トリス(ジベンジリデンアセトン)パラジウム(0)0.266g(0.29mmol)、トリシクロヘキシルホスフィン20%トルエン溶液1.0ml(0.696mmol)を加えた。この反応容器にマイクロ波(2.45GHz 150W)を2時間照射することで反応させた。反応後、反応混合物にジクロロメタンを加えて水層と有機層に分液し、水層を抽出し、得られた抽出溶液と有機層を合わせ水、飽和炭酸水素ナトリウム水溶液、飽和塩化ナトリウム水溶液で洗浄した。この有機層に無水硫酸マグネシウムを加えて乾燥させ、得られた混合物をセライト(和光純薬工業株式会社、カタログ番号:531−16855、本実施例中同じ)、アルミナ、セライトの順で積層した濾過補助剤を通して濾過した。さらに酢酸エチル2Lで洗浄し、得られたろ液を濃縮し、固体を得た。得られた固体に酢酸エチルを加えて超音波を照射し、吸引ろ過をして目的物の白色固体を0.75g、収率30%で得た。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。ステップ2の合成スキーム(c−4)を以下に示す。
1H−NMR.δ(CDCl3):7.66−7.69(m,2H),7.77−7.88(m,6H),8.26−8.30(m,4H),8.40(d,2H),8.56(dd,2H),9.10(s,2H),9.29(dd,2H)
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
102 第2の電極
103 EL層
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
400 基板
401 第1の電極
403 EL層
404 第2の電極
405 シール材
406 シール材
407 封止基板
412 パッド
420 ICチップ
501 第1の電極
502 第2の電極
503 EL層
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用FET
612 電流制御用FET
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 nチャネル型FET
624 pチャネル型FET
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 第1の層間絶縁膜
1021 第2の層間絶縁膜
1022 電極
1024W 発光素子の第1の電極
1024R 発光素子の第1の電極
1024G 発光素子の第1の電極
1024B 発光素子の第1の電極
1025 隔壁
1028 EL層
1029 発光素子の第2の電極
1031 封止基板
1032 シール材
1033 透明な基材
1034R 赤色の着色層
1034G 緑色の着色層
1034B 青色の着色層
1035 黒色層(ブラックマトリックス)
1036 オーバーコート層
1037 第3の層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
2001 筐体
2002 光源
3001 照明装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7210 第2の表示部
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 ボタン
Claims (17)
- 下記一般式(G1)で表される有機化合物。
(但し、一般式(G1)中、BPyは二つのピリジン環を含む複素芳香族基を表し、R1乃至R6はそれぞれ独立に炭素数1乃至6のアルキル基又は置換又は無置換のフェニル基を表す。) - 下記一般式(G2)で表される有機化合物。
(但し、一般式(G2)中、R1乃至R6、R11乃至R14及びR21乃至R24はそれぞれ独立に炭素数1乃至6のアルキル基又は置換又は無置換のフェニル基を表す。また、X及びYはそれぞれ独立に炭素原子又は窒素原子を表す。また、A及びDはそれぞれ独立に炭素原子又は窒素原子を表し、A及びD中少なくとも一つは窒素原子である。また、A、D、X又はYが炭素原子である場合、置換基を有していても良く、これら置換基は互いに結合して環を形成していても良い。) - 下記一般式(G3)で表される有機化合物。
(但し、一般式(G3)中、R1乃至R6、R10乃至R14及びR20乃至R24はそれぞれ独立に炭素数1乃至6のアルキル基又は置換又は無置換のフェニル基を表す。また、X及びYは一方が炭素原子であり、他方が窒素原子である。) - 下記一般式(G4)で表される有機化合物。
(但し、一般式(G4)中、R1乃至R6、R10乃至R16及びR20乃至R26はそれぞれ独立に炭素数1乃至6のアルキル基又は置換又は無置換のフェニル基を表す。) - 下記一般式(G5)で表される有機化合物。
(但し、一般式(G5)中、R1乃至R6、R11乃至R14、R21乃至R24及びR30乃至R35はそれぞれ独立に炭素数1乃至6のアルキル基又は置換又は無置換のフェニル基を表す。) - 下記構造式(100)で表される有機化合物。
- 下記構造式(200)で表される有機化合物。
- 下記構造式(300)で表される有機化合物。
- 下記構造式(400)で表される有機化合物。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を含む発光素子。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を電子輸送層に含む発光素子。
- 請求項10又は請求項11に記載の発光素子を含むディスプレイモジュール。
- 請求項10又は請求項11に記載の発光素子を含む照明モジュール。
- 請求項10又は請求項11に記載の発光素子と、前記発光素子を制御する手段を備えた発光装置。
- 請求項10又は請求項11に記載の発光素子を表示部に有し、前記発光素子を制御する手段を備えた表示装置。
- 請求項10又は請求項11に記載の発光素子を照明部に有し、前記発光素子を制御する手段を備えた照明装置。
- 請求項10又は請求項11に記載の発光素子を有する電子機器。
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