JP6002503B2 - カルバゾール化合物 - Google Patents
カルバゾール化合物 Download PDFInfo
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- JP6002503B2 JP6002503B2 JP2012176707A JP2012176707A JP6002503B2 JP 6002503 B2 JP6002503 B2 JP 6002503B2 JP 2012176707 A JP2012176707 A JP 2012176707A JP 2012176707 A JP2012176707 A JP 2012176707A JP 6002503 B2 JP6002503 B2 JP 6002503B2
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title description 17
- -1 carbazole compound Chemical class 0.000 claims description 142
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 120
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000006267 biphenyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000010410 layer Substances 0.000 description 363
- 239000000463 material Substances 0.000 description 94
- 239000000126 substance Substances 0.000 description 89
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 150000002894 organic compounds Chemical class 0.000 description 54
- 150000001875 compounds Chemical class 0.000 description 48
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- 239000010408 film Substances 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
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- 150000002500 ions Chemical class 0.000 description 22
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- 238000000862 absorption spectrum Methods 0.000 description 20
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 20
- 238000000295 emission spectrum Methods 0.000 description 19
- 238000004770 highest occupied molecular orbital Methods 0.000 description 19
- 150000002431 hydrogen Chemical class 0.000 description 19
- 230000003287 optical effect Effects 0.000 description 19
- 238000005259 measurement Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 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 16
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000005281 excited state Effects 0.000 description 15
- 239000011159 matrix material Substances 0.000 description 15
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- 238000004458 analytical method Methods 0.000 description 13
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- VAMZXYKICWPETK-UHFFFAOYSA-N 3,6-di(carbazol-9-yl)-9-pyridin-3-ylcarbazole Chemical compound C1=CN=CC(N2C3=CC=C(C=C3C3=CC(=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=C1 VAMZXYKICWPETK-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 230000006870 function Effects 0.000 description 11
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- 238000001308 synthesis method Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 8
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- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 7
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000010549 co-Evaporation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- ZEGYQBGJQMTXKA-UHFFFAOYSA-N 3,6-di(carbazol-9-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(N3C4=CC=CC=C4C4=CC=CC=C43)C=C2C2=CC(N3C4=CC=CC=C4C4=CC=CC=C43)=CC=C21 ZEGYQBGJQMTXKA-UHFFFAOYSA-N 0.000 description 5
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 5
- UQTFIXNHFSUCBI-UHFFFAOYSA-K [Ir+3].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-] Chemical compound [Ir+3].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-] UQTFIXNHFSUCBI-UHFFFAOYSA-K 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- NSABRUJKERBGOU-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 NSABRUJKERBGOU-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 4
- 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 4
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 125000005595 acetylacetonate group Chemical group 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
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- 239000004305 biphenyl Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- ADHNFLCTOCFIFV-UHFFFAOYSA-N europium(3+) 1,10-phenanthroline Chemical compound [Eu+3].c1cnc2c(c1)ccc1cccnc21 ADHNFLCTOCFIFV-UHFFFAOYSA-N 0.000 description 4
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- 230000005283 ground state Effects 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
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- 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 3
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- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 3
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- 125000005605 benzo group Chemical group 0.000 description 3
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- 229910052792 caesium Inorganic materials 0.000 description 3
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- MWRTZEGNXOMGGC-UHFFFAOYSA-N ethyl n-benzoylethanimidate Chemical compound CCOC(C)=NC(=O)C1=CC=CC=C1 MWRTZEGNXOMGGC-UHFFFAOYSA-N 0.000 description 3
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
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- 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 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 2
- GJLCPQHEVZERAU-UHFFFAOYSA-N 2-(3-dibenzothiophen-4-ylphenyl)-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 GJLCPQHEVZERAU-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
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-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(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- LNFOMBWFZZDRKO-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(10-phenylanthracen-9-yl)phenyl]phenyl]carbazol-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=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 LNFOMBWFZZDRKO-UHFFFAOYSA-N 0.000 description 1
- NCCYEOZLSGJEDF-UHFFFAOYSA-N n,n,9-triphenyl-10h-anthracen-9-amine Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C1(C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 NCCYEOZLSGJEDF-UHFFFAOYSA-N 0.000 description 1
- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- DKQKUOFOSZLDGL-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-9,10-bis(2-phenylphenyl)anthracen-2-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(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 DKQKUOFOSZLDGL-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
- 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 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
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-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
Classifications
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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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- H10K85/60—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
本実施の形態では、本発明の一態様であるカルバゾール化合物について説明する。
下記一般式(G1)で表されるカルバゾール化合物の合成方法の一例について説明する。
本実施の形態では、本発明の一態様として実施の形態1で示したカルバゾール化合物を用いることができる発光素子について図1を用いて説明する。
本実施の形態では、本発明の一態様として、燐光性化合物と他の2種類以上の有機化合物を発光層に用いた発光素子について説明する。
本実施の形態では、本発明の一態様として、電荷発生層を挟んでEL層を複数有する構造の発光素子(以下、タンデム型発光素子という)について説明する。
本実施の形態に示す発光装置は、一対の電極間での光の共振効果を利用した微小光共振器(マイクロキャビティー)構造を有しており、図4に示す様に一対の電極(反射電極401及び半透過・半反射電極402)間に少なくともEL層405を有する構造である発光素子を複数、有している。また、EL層405は、少なくとも発光領域となる発光層404を有し、その他、正孔注入層、正孔輸送層、電子輸送層、電子注入層、電荷発生層(E)などが含まれていても良い。なお、本発明の一態様であるカルバゾール化合物は、EL層405に含まれる正孔注入層、正孔輸送層、発光層404、または電子輸送層に用いることができる。
本実施の形態では、本発明の一態様であるカルバゾール化合物を発光層に用いた発光素子を有する発光装置について説明する。
本実施の形態では、本発明の一態様であるカルバゾール化合物を含む発光素子を適用して作製された発光装置を用いて完成させた様々な電子機器の一例について、図6を用いて説明する。
本実施の形態では、本発明の一態様であるカルバゾール化合物を含む発光素子を適用して作製された発光装置を用いて完成させた照明装置の一例について、図7を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明のカルバゾール化合物の一態様である、3−[3,6−ジ(9H−カルバゾール−9−イル)−9H−カルバゾール−9−イル]ピリジン(略称:Cz2CzPy)の合成方法について説明する。なお、Cz2CzPy(略称)の構造を以下に示す。
200mL三口フラスコにて、3−(3,6−ジブロモ−9H−カルバゾール−9−イル)ピリジンを1.6g(4.0mmol)、カルバゾールを1.7g(10mmol)、よう化銅(I)を190mg(1.0mmol)、18−クラウン−6−エーテルを530mg(2.0mmol)、炭酸カリウムを2.8g(20mmol)、1,3−ジメチル−3,4,5,6−テトラヒドロ−2(1H)−ピリミジノン(略称:DMPU)を20mL含む混合物を、窒素雰囲気下、180℃で6時間撹拌し、反応させた。
まず、ガラス製の基板1100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より成膜し、陽極として機能する第1の電極1101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。
作製した発光素子1および比較発光素子1の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
まず、ガラス製の基板1100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より成膜し、陽極として機能する第1の電極1101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。
作製した発光素子2および比較発光素子2の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
上記実施例2および実施例3で用いたトリス[3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾラト]イリジウム(III)(略称:[Ir(Mptz1−mp)3])の合成方法について具体的に説明する。なお、[Ir(Mptz1−mp)3]の構造を以下に示す。
まず、アセトイミド酸エチル塩酸塩15.5g、トルエン150mL、トリエチルアミン(Et3N)31.9gを500mL三ツ口フラスコに入れ、室温で10分間撹拌した。この混合物にベンゾイルクロリド17.7gとトルエン30mLの混合溶液を50mL滴下ロートより滴下し、室温で24時間撹拌した。所定時間経過後、反応混合物を吸引ろ過し、固体をトルエンで洗浄した。得られたろ液を、濃縮してN−(1−エトキシエチリデン)ベンズアミドを得た(赤色油状物、収率82%)。ステップ1の合成スキームを下記(a−1)に示す。
次に、o−トリルヒドラジン塩酸塩8.68g、四塩化炭素100mL、トリエチルアミン(Et3N)35mLを300mLナスフラスコに入れ、室温で1時間撹拌した。所定時間経過後、この混合物に上記ステップ1で得られたN−(1−エトキシエチリデン)ベンズアミド8.72gを加えて室温で24時間撹拌した。所定時間経過後、反応混合物に水を加え、水層をクロロホルムで抽出した。この有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムを加えて乾燥させた。得られた混合物を自然濾過し、ろ液を濃縮して油状物を得た。得られた油状物をシリカゲルカラムクロマトグラフィーにより精製した。展開溶媒にはジクロロメタンを用いた。得られたフラクションを濃縮して、3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾール(略称:HMptz1−mp)を得た(橙色油状物、収率84%)。ステップ2の合成スキームを下記(a−2)に示す。
次に、上記ステップ2で得られた配位子HMptz1−mp2.71g、トリス(アセチルアセトナト)イリジウム(III)1.06gを、三方コックを付けた反応容器に入れた。この反応容器をアルゴン置換し、250℃にて48時間加熱し、反応させた。この反応混合物をジクロロメタンに溶解し、シリカゲル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、まず、ジクロロメタン用い、次いでジクロロメタン:酢酸エチル=10:1(v/v)の混合溶媒を用いた。得られたフラクションを濃縮して固体を得た。この固体を酢酸エチルで洗浄し、次いで、ジクロロメタンと酢酸エチルの混合溶媒にて再結晶し、本発明の一態様である有機金属錯体[Ir(Mptz1−mp)3]を得た(黄色粉末、収率35%)。ステップ3の合成スキームを下記(a−3)に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=1.94−2.21(m,18H),6.47−6.76(m,12H),7.29−7.52(m,12H)。
上記実施例2および実施例3で用いた3,6−ジ(9H−カルバゾール−9−イル)−9−フェニル−9H−カルバゾール(略称:PhCzGI)の合成方法について具体的に説明する。なお、PhCzGI(略称)の構造を以下に示す。
まず、200mL三口フラスコにて、3,6−ジブロモ−9−フェニル−9H−カルバゾールを2.8g(7.0mmol)、カルバゾールを2.7g(16mmol)、よう化銅(I)を1.9g(10mmol)、18−クラウン−6−エーテルを2.5g(10mmol)、炭酸カリウムを2.8g(20mmol)、1,3−ジメチル−3,4,5,6−テトラヒドロ−2(1H)−ピリミジノン(略称:DMPU)を20mL含む混合物を、窒素雰囲気下、180℃で3.5時間撹拌し、反応させた。
1H NMR(CDCl3,300MHz):δ(ppm)=7.26−7.32(m,4H),7.40(d,J=3.3Hz,8H),7.57−7.74(m,9H),8.16(d,J=7.5Hz,4H),8.28(d,J=1.5Hz,2H)。
本実施例では、実施の形態1の構造式(101)で表される本発明のカルバゾール化合物の一態様である、3−{3−[3,6−ジ−(9H−カルバゾール−9−イル)−9H−カルバゾール−9−イル]フェニル}ピリジン(略称:mCz2CzPPy)の合成方法について説明する。なお、mCz2CzPPy(略称)の構造を以下に示す。
200mlナスフラスコに3−[3−(9H−カルバゾール−9−イル−フェニル)]ピリジン1.3g(3.96mmol)、N−ブロモこはく酸イミド(略称;NBS)0.71g(4.0mmol)、酢酸エチル50mlを入れ、51時間混合物を攪拌した。所定時間攪拌後、N−ブロモこはく酸イミド(略称;NBS)0.71g(4.0mmol)を加え、45時間攪拌した。反応終了後、水を加えて混合物を撹拌した後、濾過した。得られた濾物に水を加え、超音波を照射し濾過をし、ろ物を得た。得られた固体を乾燥させ、目的物の白色固体を1.5g、収率81%で得た。
102 EL層
103 第2の電極
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
116 電荷発生層
201 陽極
202 陰極
203 EL層
204 発光層
205 燐光性化合物
206 第1の有機化合物
207 第2の有機化合物
301 第1の電極
302(1) 第1のEL層
302(2) 第2のEL層
302(n−1) 第(n−1)のEL層
302(n) 第(n)のEL層
304 第2の電極
305 電荷発生層(I)
305(1) 第1の電荷発生層(I)
305(2) 第2の電荷発生層(I)
305(n−2) 第(n−2)の電荷発生層(I)
305(n−1) 第(n−1)の電荷発生層(I)
401 反射電極
402 半透過・半反射電極
403a 第1の透明導電層
403b 第2の透明導電層
404B 第1の発光層(B)
404G 第2の発光層(G)
404R 第3の発光層(R)
405 EL層
410R 第1の発光素子(R)
410G 第2の発光素子(G)
410B 第3の発光素子(B)
501 素子基板
502 画素部
503 駆動回路部(ソース線駆動回路)
504a、504b 駆動回路部(ゲート線駆動回路)
505 シール材
506 封止基板
507 配線
508 FPC(フレキシブルプリントサーキット)
509 nチャネル型TFT
510 pチャネル型TFT
511 スイッチング用TFT
512 電流制御用TFT
513 第1の電極(陽極)
514 絶縁物
515 EL層
516 第2の電極(陰極)
517 発光素子
518 空間
1100 基板
1101 第1の電極
1102 EL層
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1114 電子輸送層
1115 電子注入層
7100 テレビジョン装置
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
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
7312 マイクロフォン
7400 携帯電話機
7401 筐体
7402 表示部
7403a、7403b 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
Claims (3)
- 式(G3)で表されるカルバゾール化合物。
(式中、R1〜R5は、それぞれ独立に、水素、置換又は無置換のフェニル基、置換又は無置換のビフェニル基のいずれかを表す。また、nは0または1である。) - 式(G4)で表されるカルバゾール化合物。
(式中、R2〜R5は、それぞれ独立に、水素、置換又は無置換のフェニル基、置換又は無置換のビフェニル基のいずれかを表す。また、nは0または1である。) - 式(100)又は式(101)で表されるカルバゾール化合物。
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US9985579B2 (en) | 2016-04-12 | 2018-05-29 | Preformed Line Products Co. | Mounting assembly for mounting a solar panel |
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Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3139321B2 (ja) | 1994-03-31 | 2001-02-26 | 東レ株式会社 | 発光素子 |
JP4140986B2 (ja) | 1997-02-14 | 2008-08-27 | 出光興産株式会社 | 有機電界発光素子 |
JP2001244077A (ja) | 2000-03-01 | 2001-09-07 | Fuji Photo Film Co Ltd | 有機発光素子 |
JP4890669B2 (ja) | 2000-03-13 | 2012-03-07 | Tdk株式会社 | 有機el素子 |
JP4560927B2 (ja) | 2000-09-22 | 2010-10-13 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子 |
FR2827518B1 (fr) | 2001-07-17 | 2005-07-08 | Sod Conseils Rech Applic | Utilisation d'extraits de ginkgo biloba pour preparer un medicament destine a traiter la sarcopenie |
JP2003133075A (ja) | 2001-07-25 | 2003-05-09 | Toray Ind Inc | 発光素子 |
JP4243328B2 (ja) | 2002-03-11 | 2009-03-25 | 財団法人神奈川科学技術アカデミー | フェニルアゾメチン系カルバゾールデンドリマーと有機el素子 |
WO2003079736A1 (en) | 2002-03-18 | 2003-09-25 | Isis Innovation Limited | Phosphorescent dendrimers for use in light-emitting devices |
GB0220092D0 (en) | 2002-08-29 | 2002-10-09 | Isis Innovation | Reactive dendrimers |
US20030205696A1 (en) | 2002-04-25 | 2003-11-06 | Canon Kabushiki Kaisha | Carbazole-based materials for guest-host electroluminescent systems |
JP2004018787A (ja) | 2002-06-19 | 2004-01-22 | Fuji Photo Film Co Ltd | カルバゾール誘導体、並びにそのポリマー、及びそれを含有する発光素子 |
TWI354011B (en) | 2003-05-16 | 2011-12-11 | Semiconductor Energy Lab | Carbazole derivative, organic semiconductor elemen |
US20040247933A1 (en) * | 2003-06-03 | 2004-12-09 | Canon Kabushiki Kaisha | Bipolar asymmetric carbazole-based host materials for electrophosphorescent guest-host OLED systems |
US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
CN104835914B (zh) | 2006-12-28 | 2018-02-09 | 通用显示公司 | 长寿命磷光有机发光器件(oled)结构 |
EP2134809B1 (en) | 2007-04-13 | 2020-09-02 | Cheil Industries Inc. | Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same |
US20080314965A1 (en) | 2007-06-23 | 2008-12-25 | Roberts Mark D | System and method for authentication of engineering notebook support information |
TWI511964B (zh) | 2007-08-08 | 2015-12-11 | Universal Display Corp | 苯并稠合噻吩/聯伸三苯混合材料 |
KR102073400B1 (ko) | 2007-08-08 | 2020-02-05 | 유니버셜 디스플레이 코포레이션 | 인광성 발광 다이오드의 단일 트리페닐렌 발색단 |
US20090153034A1 (en) | 2007-12-13 | 2009-06-18 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emittinig diodes |
US8221905B2 (en) * | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
JP2009227604A (ja) | 2008-03-21 | 2009-10-08 | Chemiprokasei Kaisha Ltd | 新規3,6−二置換カルバゾール誘導体、それよりなるホスト材料およびそれを含有する有機el素子 |
KR101432599B1 (ko) | 2010-08-04 | 2014-08-21 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
JP2012059815A (ja) * | 2010-09-07 | 2012-03-22 | Elpida Memory Inc | 半導体装置 |
KR101789162B1 (ko) * | 2010-12-01 | 2017-10-23 | 엘지디스플레이 주식회사 | 유기전계발광소자용 청색 인광 물질 및 이를 포함하는 유기전계발광소자 |
WO2012077902A2 (ko) * | 2010-12-08 | 2012-06-14 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
KR102021273B1 (ko) | 2011-05-27 | 2019-09-16 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 카바졸 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
US9051274B2 (en) | 2011-06-24 | 2015-06-09 | Semiconductor Energy Laboratory Co., Ltd. | Triarylamine compound, light-emitting element, light-emitting device, electronic device, and lighting device |
US9029558B2 (en) * | 2011-08-18 | 2015-05-12 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole compound, light-emitting element, light-emitting device, electronic device, and lighting device |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |