WO2013018530A1 - AMINOINDOLO[3,2,1-jk]CARBAZOLE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME - Google Patents
AMINOINDOLO[3,2,1-jk]CARBAZOLE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME Download PDFInfo
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- WO2013018530A1 WO2013018530A1 PCT/JP2012/068045 JP2012068045W WO2013018530A1 WO 2013018530 A1 WO2013018530 A1 WO 2013018530A1 JP 2012068045 W JP2012068045 W JP 2012068045W WO 2013018530 A1 WO2013018530 A1 WO 2013018530A1
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- organic light
- emitting device
- layer
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- aminoindolo
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- -1 AMINOINDOLO[3,2,1-jk]CARBAZOLE COMPOUND Chemical class 0.000 title claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 abstract description 61
- 239000010410 layer Substances 0.000 description 88
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- GWOAJJWBCSUGHH-UHFFFAOYSA-N 1-bromo-4-(4-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(I)C=C1 GWOAJJWBCSUGHH-UHFFFAOYSA-N 0.000 description 3
- JMDDBKIVEXIIDP-UHFFFAOYSA-N C12=CC=CC=C2N2C3=CC=CC=C3C3=C2C1=CC=C3N Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3C3=C2C1=CC=C3N JMDDBKIVEXIIDP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
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- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [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 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- CUAPXNXBWGCQBG-UHFFFAOYSA-N 2-carbazol-9-ylaniline Chemical compound NC1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 CUAPXNXBWGCQBG-UHFFFAOYSA-N 0.000 description 2
- PKJSBKDIIGBJLF-UHFFFAOYSA-N 9-(2-nitrophenyl)carbazole Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 PKJSBKDIIGBJLF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LJTPQWLUDJAUQM-UHFFFAOYSA-N N-bromo-1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2,4,6,8,10,12(19),13,15,17-nonaen-10-amine Chemical compound C12=CC=CC=C2C2=CC(NBr)=CC3=C2N1C1=CC=CC=C13 LJTPQWLUDJAUQM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 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 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
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- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
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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 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- BLJGLNCGHUVKQQ-UHFFFAOYSA-N 3-diphenylphosphanylpropyl(diphenyl)phosphane;nickel Chemical compound [Ni].C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BLJGLNCGHUVKQQ-UHFFFAOYSA-N 0.000 description 1
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- FUSNVWBEHAYGEZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1c2ccccc22)cc3c1[n]2c1ccccc31 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1c2ccccc22)cc3c1[n]2c1ccccc31 FUSNVWBEHAYGEZ-UHFFFAOYSA-N 0.000 description 1
- BVLXJPWXNPQMTL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cc(c2c3cccc2)c2[n]3c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cc(c2c3cccc2)c2[n]3c(cccc3)c3c2c1 BVLXJPWXNPQMTL-UHFFFAOYSA-N 0.000 description 1
- ZTJIHNNGNVMJBI-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c1cc(c2c3cccc2)c2[n]3c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c1cc(c2c3cccc2)c2[n]3c(cccc3)c3c2c1 ZTJIHNNGNVMJBI-UHFFFAOYSA-N 0.000 description 1
- ABUDKAILYSPMQZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 ABUDKAILYSPMQZ-UHFFFAOYSA-N 0.000 description 1
- AOCDHMFHELUYGL-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1c2cccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1c2cccc1 AOCDHMFHELUYGL-UHFFFAOYSA-N 0.000 description 1
- SZVBSBPGWMJDGV-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 SZVBSBPGWMJDGV-UHFFFAOYSA-N 0.000 description 1
- GHJIYCVTXMRRTB-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1c2c3cccc2)cc2c1[n]3c1ccccc21 GHJIYCVTXMRRTB-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005286 illumination Methods 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
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 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
- 238000005191 phase separation Methods 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 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 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004043 responsiveness Effects 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
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 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
- 125000005259 triarylamine group Chemical group 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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- 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
-
- 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
Definitions
- the present invention relates to an
- aminoindolo [ 3 , 2 , 1-j k] carbazole compound and an organic light-emitting device including the compound.
- An organic light-emitting device includes an anode, a cathode, and an organic compound layer disposed between the electrodes.
- holes and electrons injected from the electrodes are recombined in the organic compound layer to generate excitons, and the excitons emit light when they return to their ground state.
- PTL 1 discloses SH-01 represented by the following formula as an aromatic amine compound that can be used in, for example, a hole-transporting layer of an organic light- emitting device.
- PTL 2 describes FH-01 represented by the following formula as a compound for an organic light-emitting device.
- PTLs 1 and 2 describe compounds that can be used in organic light-emitting devices.
- the present invention provides a novel
- the present invention provides an aminoindolo [ 3 , 2 , 1-j k] carbazole compound represented by the following Formula [1] :
- 1 represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2; and R 1 to R 32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl groups may contain fluorine atoms.
- the present invention can provide a novel
- aminoindolo [ 3 , 2 , 1- k] carbazole compound having high heat stability and an organic light-emitting device having a low driving voltage and high driving durability by using the compound .
- Figure 1 is a schematic cross-sectional view illustrating organic light-emitting devices and switching devices connected to the organic light-emitting devices. Description of Embodiment
- the present invention relates to an
- 1 represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2 ; and R 1 to R 32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl groups may contain fluorine atoms.
- R 1 to R 32 can be hydrogen atom, alkyl groups having 1 to 6 carbon atoms or fluorine atoms.
- the alkyl group may contain a fluorine atom, i.e., may be methyl fluoride or tetrafluoromethane .
- the compound according to the present invention is composed of three moieties: an aromatic amino group, an aromatic group, and an indolo [ 3 , 2 , 1-j k] carbazolyl group.
- the presence of the aromatic amino group and the aromatic group allows the compound to have a HOMO level suitable for a hole-injecting layer, a hole-transporting layer, or an electron-blocking layer.
- the aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention includes an indolo [ 3 , 2 , 1- j k] carbazolyl group having higher heat stability compared with that of a carbazolyl group, which is generally used in a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or another layer. Consequently, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound exhibits high heat stability.
- aminoindolo [3, 2, 1-j k] carbazole compound according to the present invention increases by having an alkyl group. [0024] Consequently, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound having an alkyl group can easily form a film by coating .
- aminoindolo [ 3 , 2 , 1- k] carbazole compound according to the present invention can be at least one of R 18 to R 20 and R 27 to R 29 .
- aminoindolo [ 3 , 2 , 1-j k] carbazole compound having a substituent containing fluorine can easily form a film by deposition.
- aminoindolo [ 3 , 2 , 1-j k] carbazole compound of the present invention has high heat stability and can be applied to film formation by any of coating and deposition.
- it can be expected that an organic light-emitting device
- the compounds belonging to group A do not contain alkyl groups and fluorine atoms.
- these compounds in group A have hi chemical stability, and an organic light-emitting device including such a compound as a hole-injecting, a hole- transporting, or an electron-blocking material can be expected to have a long lifetime.
- the compounds belonging to group B contain alkyl groups and thereby have high solubility and can easily form films by coating.
- These compounds have shallow HOMO levels, and an organic light-emitting device including such a compound can be expected to be driven by a lower voltage.
- the shallow HOMO level means that the HOMO level is near the vacuum energy level.
- the compounds belonging to group C contain fluorine atoms, and, thereby, the intermolecular interaction between the compounds is low. As a result, the compounds have high sublimability and can further easily form films by deposition.
- a desired aminoindolo [ 3 , 2 , 1- jk] carbazole compound of the present invention can be synthesized by appropriately selecting n, m, and 1 and the alkyl group and the fluorine atom.
- the organic light-emitting device includes at least a pair of electrodes facing each other, i.e., an anode and a cathode, and an organic compound layer disposed therebetween.
- the organic compound layer includes the
- the organic compound layer of the organic light- emitting device may be a monolayer or a multilayer.
- the multilayer includes those appropriately selected from, for example, a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, a light-emitting layer, a hole-blocking layer, an electron- transporting layer, an electron-injecting layer, and an exciton-diffusion-blocking layer .
- the organic light-emitting device includes a pair of
- electrodes a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, and an electron-injecting layer.
- the organic light-emitting device may have a
- devices may emit different colors of light.
- the light-emitting device having a plurality of light-emitting layers may include the light-emitting layers between a pair of electrodes. For example, in one
- light-emitting layers respectively emitting red, green, and blue light are layered between the anode and the cathode.
- the configuration of the organic light-emitting device according to the present embodiment is not limited thereto, and various layer configurations can be employed.
- an insulating layer may be disposed at the interface between an electrode and an organic compound layer; an adhesive layer or an interference layer may be provided; or an electron-transporting layer or a hole- transporting layer may be composed of two layers having ionization potentials different from each other.
- the configuration of the device may be a top emission type extracting light from the opposite side of the substrate, or a bottom emission type extracting light from the substrate side.
- a configuration in which light is extracted from both sides can also be employed.
- the aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention can be used in any layer as an organic compound layer of the organic light-emitting device and can be used, in particular, in the hole-injecting layer, the hole-transporting layer, or the electron-blocking layer .
- the hole-injecting layer, the hole-transporting layer, and the electron- blocking layer are organic compound layers disposed between the anode and the light-emitting layer.
- the hole-transporting layer is a layer for
- the material used for the hole-transporting layer can be a material having the HOMO level at an
- aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention is an appropriate compound satisfying this requirement.
- aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention can be used in the hole-transporting layer.
- a known low-molecular or high-molecular compound may be optionally used. More specifically, for example, a hole-injecting compound, a hole-transporting compound, a host material, a light-emitting compound, an electron- injecting compound, or an electron-transporting compound can be used together. Examples of these compounds will now be described.
- the hole-injecting/transporting compound can be a material possessing high hole mobility so that injection of holes from an anode is easy and that the injected holes can be transported to an light-emitting layer.
- Examples of the low-molecular or high-molecular material having hole- injecting/transporting ability include triarylamine
- Examples of the light-emitting material mainly related to the emission function include, in addition to phosphorescent guest materials and derivatives thereof, condensation compounds (e.g., fluorene derivatives,
- naphthalene derivatives naphthalene derivatives, pyrene derivatives, perylene
- the electron-injecting/transporting compound can be appropriately selected from those that allows easy injection of electrons from a cathode and can transport the injected electrons to a light-emitting layer, with consideration for, for example, the balance with the hole mobility of the hole- injecting/transporting compound.
- oxadiazole derivatives include oxadiazole derivatives, oxazole derivatives,
- the material of the anode can have a work function as high as possible.
- Examples of such a material include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten; alloys of these simple metals; and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide. Electrically conductive polymers such as polyaniline, polypyrrole, and polythiophene also can be used.
- Electrode materials may be used alone or in combination of two or more thereof.
- the anode may have either a monolayer structure or a multilayer structure.
- the material of the cathode can have a low work function.
- examples of such a material include alkali metals such as lithium; alkaline earth metals such as calcium;
- simple metals such as aluminum, titanium, manganese, silver, lead, and chromium; alloys of these simple metals such as magnesium-silver, aluminum-lithium, and aluminum-magnesium; and metal oxides such as indium tin oxide (ITO).
- ITO indium tin oxide
- the cathode may have either a monolayer structure or a multilayer structure.
- solvent e.g., spin coating, dipping, casting, an LB method, or an ink jet method.
- a layer formed by vacuum deposition or coating of a solution hardly causes, for example, crystallization and is stable for a long time.
- the solution may additionally contain an
- binder resin examples include, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenol resins, epoxy resins, silicone resins, and urea resins.
- binder resins may be singly used as a
- the solution for forming a film may further
- additives such as known plasticizer, antioxidant, and ultraviolet absorber.
- the organic light-emitting device according to the present embodiment can be applied to a display apparatus or a lighting system.
- the device can be used, for example, in an exposing light source of an
- the display apparatus has the organic light- emitting device according to the present embodiment in a display section.
- the display section has a plurality of pixels.
- Each pixel has the organic light-emitting device according to the present embodiment and a thin-film
- TFT transistor
- transistor is connected to the anode or the cathode of the organic light-emitting device.
- the display apparatus can be used as an image display apparatus of, for example, a PC, a head mount display, or a mobile phone.
- the image displayed may be a two-dimensional image or a three-dimensional image.
- the display apparatus may be an image output apparatus that includes an image input section for inputting image information from, for example, an area CCD, a linear CCD, or a memory card and outputs the input image to a display section.
- the image output apparatus may be a digital camera having an image pickup optical system with an image pickup device, such as a CCD sensor, as the image input section.
- an image pickup device such as a CCD sensor
- the display apparatus may have an input function for inputting information by touching an image on the display, such as a touch panel function.
- the display apparatus may be used in the display section of a multi-functional printer.
- the organic light-emitting device according to the present embodiment may be used in a lighting system.
- This lighting system includes the organic light-emitting device according to the present embodiment and a converter circuit connected to the organic light-emitting device.
- the color of illumination light of the lighting system according to the present embodiment may be white or neutral white or another color.
- Figure 1 is a schematic cross-sectional view illustrating organic light-emitting devices according to the present embodiment and TFTs as an example of switching devices connected to the organic light-emitting devices. This drawing shows two pairs of the organic light-emitting devices and the TFTs. The structure will now be described in detail.
- the display apparatus shown in Figure 1 includes a substrate 1 such as a glass substrate and a moisture-proof film 2 disposed on the substrate 1 for protecting TFTs or an organic compound layer.
- Reference numeral 3 denotes a metal gate electrode
- reference numeral 4 denotes a gate
- reference numeral 5 denotes a
- a thin-film transistor 8 includes a semiconductor layer 5, a drain electrode 6, and a source electrode 7.
- An insulating film 9 is disposed on the thin-film transistor 8.
- the source electrode 7 is connected to the anode 11 of the organic light-emitting device via a contact hole 10.
- the display apparatus is not limited to this structure as long as either the anode or the cathode is connected to either the source electrode or the drain electrode of the thin-film transistor.
- the organic compound layer 12 is simplified and drawn as one layer, but is actually composed of a plurality of organic compound layers.
- protection layer 14 and a second protection layer 15 are disposed on a cathode 13 for inhibiting degradation of the organic light-emitting device.
- the switching device is not particularly limited and may be a transistor or an MIM element.
- the transistor may be a thin-film transistor employing single crystal silicon or an amorphous silicon transistor.
- the thin-film transistor is also called a TFT.
- the switching device controls the luminance.
- images can be displayed with the respective luminance.
- the luminance also can be controlled by producing an active matrix driver on a Si substrate and disposing the organic light-emitting devices thereon.
- the organic light-emitting devices can be disposed on a Si substrate.
- dehydrated toluene 550 mL were charged in a round bottom flask under light shielding.
- Example Compound A-112 with high purity (yield: -15%).
- Tg glass transition temperature
- Example Compound A- 022 with high purity.
- Tg glass transition temperature
- Tg glass transition temperature
- Tg glass transition temperatures
- each of comparative compounds SH-01 and SH-02 is increased by 16 to 20°C by replacing the carbazolyl group with an indolo [ 3 , 2 , 1-j k] carbazolyl group. It is thus recognized that the heat stability of the Example compounds is higher than that of the comparative compounds.
- a bottom emission type organic light-emitting device having a configuration composed of anode/hole-transporting layer/light-emitting layer/hole- blocking layer/electron-transporting layer/electron- injecting layer/cathode disposed in this order on a
- ITO indium tin oxide
- the glass substrate provided with the ITO film was subjected to ultrasonic washing in acetone and isopropyl alcohol (IPA) in this order, washed by boiling in IPA, and then dried. Furthermore, the substrate was subjected to UV/ozone washing.
- the thus-treated glass substrate was used as a transparent electrically conductive support substrate (ITO substrate).
- organic compound layers and electrode layers shown below were successively formed by resistance heating vacuum vapor deposition in a vacuum chamber. The layers were:
- a voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
- characteristics of the organic light-emitting device the current-voltage characteristics were measured with an ammeter 2700 manufactured by Keithley Instruments, Inc., and the
- H-l, D-l, HBM-1 , and ET -1 used in Example 4 were synthesized with reference to U.S. Patent Publication No. 2005/0236977, Japanese Patent Laid-Open No. 2010-270103, International Publication No. WO2010/107037 , and
- An organic light-emitting device was produced as in Example 4 except that the hole-transporting layer was formed using A-022 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
- An organic light-emitting device was produced as in Example 4 except that the hole-transporting layer was formed using A-113 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
- An organic light-emitting device was produced as in Example 4 except that the hole-transporting layer was formed using SH-01 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
- Table 2 shows the relative voltage at 6000 cd/m 2 (when the voltage in the organic light-emitting device of Comparative Example 2 was defined as 1) and the relative time for reducing brightness by 4% in driving at a constant current of 25 mA/m 2 (when the time in the organic light-emitting device of Comparative Example 2 was defined as 1) .
- Example compounds allowed a reduction in driving voltage and an increase in endurance time of driving compared with those by the comparative compound.
- the aminoindolo [ 3 , 2 , 1- j k] carbazole compound according to the present invention has satisfactory heat stability, and a light-emitting device in which the compound is used can have a low driving voltage and high driving durability.
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Abstract
The present invention provides a novel aminoindolo[3,2,1-jk]carbazole compound having a good film-forming property and provides an organic light-emitting device including the compound. Provided is the aminoindolo[3,2,1-jk]carbazole compound represented by Formula [1] according to Claim 1. In Formula [1], l represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2; and R1 to R32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl groups may contain fluorine atoms.
Description
DESCRIPTION
AMINOINDOLO[3, 2, 1-jk] CARBAZOLE COMPOUND AND ORGANIC
LIGHT-EMITTING DEVICE INCLUDING THE SAME
Technical Field
[0001] The present invention relates to an
aminoindolo [ 3 , 2 , 1-j k] carbazole compound and an organic light-emitting device including the compound.
Background Art
[0002] An organic light-emitting device includes an anode, a cathode, and an organic compound layer disposed between the electrodes. In the organic light-emitting device, holes and electrons injected from the electrodes are recombined in the organic compound layer to generate excitons, and the excitons emit light when they return to their ground state. Recent considerable progress in organic light-emitting devices allows a reduction in driving voltage,
diversification in emission wavelength, rapid responsiveness, and reductions in size and weight of light-emitting devices.
[0003] PTL 1 discloses SH-01 represented by the following formula as an aromatic amine compound that can be used in, for example, a hole-transporting layer of an organic light- emitting device.
[0004] PTL 2 describes FH-01 represented by the following
formula as a compound for an organic light-emitting device.
[0005]
[Chem. 1]
Citation List
Patent Literature
[0006] PTL 1 Japanese Patent Laid-Open No. 2009-298779
PTL 2 Japanese Patent Laid-Open No. 2010-087496
[0007] PTLs 1 and 2 describe compounds that can be used in organic light-emitting devices.
[0008] These compounds, however, have insufficient heat stability. In addition, organic light-emitting devices using these compounds in the hole-injecting layer, the hole- transporting layer, or the electron-blocking layer need high driving voltages.
Summary of Invention
[0009] The present invention provides a novel
aminoindolo [3, 2, 1-j k] carbazole compound having high heat stability and an organic light-emitting device having a low driving voltage and high driving durability by using the compound.
[0010] Accordingly, the present invention provides an aminoindolo [ 3 , 2 , 1-j k] carbazole compound represented by the following Formula [1] :
[0011]
[Chem. 2]
[0012] In Formula [1], 1 represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2; and R1 to R32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl groups may contain fluorine atoms.
Advantageous Effects of Invention
[0013] The present invention can provide a novel
aminoindolo [ 3 , 2 , 1- k] carbazole compound having high heat stability and an organic light-emitting device having a low driving voltage and high driving durability by using the
compound .
Brief Description of Drawings
[0014] Figure 1 is a schematic cross-sectional view illustrating organic light-emitting devices and switching devices connected to the organic light-emitting devices. Description of Embodiment
[0015] The present invention relates to an
aminoindolo [ 3 , 2 , 1-j k] carbazole compound represented by the following Formula [1] :
[0016]
[Chem. 3]
[0017] In Formula [1], 1 represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2 ; and R1 to R32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl
groups may contain fluorine atoms.
[0018] In Formula [1], R1 to R32 can be hydrogen atom, alkyl groups having 1 to 6 carbon atoms or fluorine atoms.
[0019] The alkyl group may contain a fluorine atom, i.e., may be methyl fluoride or tetrafluoromethane .
Properties of the aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention
[0020] The compound according to the present invention is composed of three moieties: an aromatic amino group, an aromatic group, and an indolo [ 3 , 2 , 1-j k] carbazolyl group.
[0021] The presence of the aromatic amino group and the aromatic group allows the compound to have a HOMO level suitable for a hole-injecting layer, a hole-transporting layer, or an electron-blocking layer.
[0022] The aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention includes an indolo [ 3 , 2 , 1- j k] carbazolyl group having higher heat stability compared with that of a carbazolyl group, which is generally used in a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or another layer. Consequently, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound exhibits high heat stability.
[0023] The solubility in organic solvents of the
aminoindolo [3, 2, 1-j k] carbazole compound according to the present invention increases by having an alkyl group.
[0024] Consequently, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound having an alkyl group can easily form a film by coating .
[0025] The position of the alkyl group in the
aminoindolo [ 3 , 2 , 1- k] carbazole compound according to the present invention can be at least one of R18 to R20 and R27 to R29.
[0026] The sublimability of the aminoindolo [ 3 , 2 , 1- jk] carbazole compound according to the present invention increases by having a substituent containing a fluorine atom.
[0027] Consequently, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound having a substituent containing fluorine can easily form a film by deposition.
[0028] By the design described above, the
aminoindolo [ 3 , 2 , 1-j k] carbazole compound of the present invention has high heat stability and can be applied to film formation by any of coating and deposition. In addition, it can be expected that an organic light-emitting device
including the compound is driven by a low voltage.
Examples of aminoindolo [ 3 , 2 , 1-j k] carbazole compound
according to the present invention
[0029] Unlimited examples of the structural formula of the aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention are specifically shown below.
[0030]
[
A-001 A-002 A-003
A-021 A-022 A-023
[0031]
[Chem.
[0032]
[Chem. 6]
[0033]
[Chem. 7]
[0034] Among the exemplified compounds, the compounds belonging to group A do not contain alkyl groups and fluorine atoms.
[0035] Accordingly, these compounds in group A have hi chemical stability, and an organic light-emitting device including such a compound as a hole-injecting, a hole- transporting, or an electron-blocking material can be
expected to have a long lifetime.
[ 0036] Among the exemplified compounds, the compounds belonging to group B contain alkyl groups and thereby have high solubility and can easily form films by coating.
[0037 ] These compounds have shallow HOMO levels, and an organic light-emitting device including such a compound can be expected to be driven by a lower voltage. The shallow HOMO level means that the HOMO level is near the vacuum energy level.
[ 0038 ] Among the exemplified compounds, the compounds belonging to group C contain fluorine atoms, and, thereby, the intermolecular interaction between the compounds is low. As a result, the compounds have high sublimability and can further easily form films by deposition.
Example of method of synthesizing aminoindolo [ 3 , 2 , 1- jk]carbazole compound according to the present invention
[0039] An example of a method of synthesizing the
aminoindolo [3, 2, 1-j k] carbazole compound represented by
Formula [1] according to the present embodiment will now be described.
[0040] The aminoindolo [3, 2, 1-j k] carbazole compound
according to the present invention can be synthesized as shown below by coupling an aromatic amine and a
bromoiodoaryl with a Pd catalyst and then coupling the coupling product and a bis (pinacol) boronic ester compound
of aminoindolo [ 3 , 2 , 1-j k] carbazole with a Pd catalyst. This synthetic method is merely an example, and any reaction route may be used for the synthesis.
[0041]
[Chem. 8]
[0042] In the reaction above, a desired aminoindolo [ 3 , 2 , 1- jk] carbazole compound of the present invention can be synthesized by appropriately selecting n, m, and 1 and the alkyl group and the fluorine atom.
Organic light-emitting device according to the present embodiment
[0043] The organic light-emitting device according to the present embodiment includes at least a pair of electrodes facing each other, i.e., an anode and a cathode, and an organic compound layer disposed therebetween. In the
organic light-emitting device according to the present invention, the organic compound layer includes the
aminoindolo [ 3 , 2 , 1-j k] carbazole compound represented by
Formula [1] .
[0044] The organic compound layer of the organic light- emitting device according to the present embodiment may be a monolayer or a multilayer. The multilayer includes those appropriately selected from, for example, a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, a light-emitting layer, a hole-blocking layer, an electron- transporting layer, an electron-injecting layer, and an exciton-diffusion-blocking layer .
[0045] A plurality of layers selected from the above- mentioned layers can be used in combination. For example, the organic light-emitting device includes a pair of
electrodes, a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, and an electron-injecting layer.
[0046] The organic light-emitting device may have a
plurality of light-emitting layers, and the respective
devices may emit different colors of light.
[0047] The light-emitting device having a plurality of light-emitting layers may include the light-emitting layers between a pair of electrodes. For example, in one
configuration, light-emitting layers respectively emitting red, green, and blue light are layered between the anode and the cathode.
[0048] The configuration of the organic light-emitting
device according to the present embodiment is not limited thereto, and various layer configurations can be employed. For example, an insulating layer may be disposed at the interface between an electrode and an organic compound layer; an adhesive layer or an interference layer may be provided; or an electron-transporting layer or a hole- transporting layer may be composed of two layers having ionization potentials different from each other.
[0049] The configuration of the device may be a top emission type extracting light from the opposite side of the substrate, or a bottom emission type extracting light from the substrate side. Alternatively, a configuration in which light is extracted from both sides can also be employed.
[0050] The aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention can be used in any layer as an organic compound layer of the organic light-emitting device and can be used, in particular, in the hole-injecting layer, the hole-transporting layer, or the electron-blocking layer .
[0051] Throughout the specification, the hole-injecting layer, the hole-transporting layer, and the electron- blocking layer are organic compound layers disposed between the anode and the light-emitting layer.
[0052] The hole-transporting layer is a layer for
conducting holes injected from an electrode to the light-
emitting layer. The material used for the hole-transporting layer can be a material having the HOMO level at an
appropriate position.
[0053] The aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention is an appropriate compound satisfying this requirement.
[0054] That is, the aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to the present invention can be used in the hole-transporting layer.
[0055] In addition to the compound of the present
invention, a known low-molecular or high-molecular compound may be optionally used. More specifically, for example, a hole-injecting compound, a hole-transporting compound, a host material, a light-emitting compound, an electron- injecting compound, or an electron-transporting compound can be used together. Examples of these compounds will now be described.
[0056] The hole-injecting/transporting compound can be a material possessing high hole mobility so that injection of holes from an anode is easy and that the injected holes can be transported to an light-emitting layer. Examples of the low-molecular or high-molecular material having hole- injecting/transporting ability include triarylamine
derivatives, phenylenediamine derivatives, stilbene
derivatives, phthalocyanine derivatives, porphyrin
derivatives, poly (vinylcarbazole ) , poly ( thiophene) , and other electrically conductive polymers.
[0057] Examples of the light-emitting material mainly related to the emission function include, in addition to phosphorescent guest materials and derivatives thereof, condensation compounds (e.g., fluorene derivatives,
naphthalene derivatives, pyrene derivatives, perylene
derivatives, tetracene derivatives, anthracene derivatives, and rubrene) , quinacridone derivatives, coumarin derivatives, stilbene derivatives, organic aluminum complexes such as tris ( 8-quinolinolato) aluminum, organic beryllium complexes, and polymer derivatives such as poly (phenylenevinylene ) derivatives, poly ( fluorene ) derivatives, and poly (phenylene) derivatives .
[0058] The electron-injecting/transporting compound can be appropriately selected from those that allows easy injection of electrons from a cathode and can transport the injected electrons to a light-emitting layer, with consideration for, for example, the balance with the hole mobility of the hole- injecting/transporting compound. Examples of the material possessing the electron-injecting/transporting ability
include oxadiazole derivatives, oxazole derivatives,
pyrazine derivatives, triazole derivatives, triazine
derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, and organic aluminum complexes.
[0059] The material of the anode can have a work function as high as possible.
[0060] Examples of such a material include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten; alloys of these simple metals; and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide. Electrically conductive polymers such as polyaniline, polypyrrole, and polythiophene also can be used.
[0061] These electrode materials may be used alone or in combination of two or more thereof. The anode may have either a monolayer structure or a multilayer structure.
[0062] The material of the cathode can have a low work function. Examples of such a material include alkali metals such as lithium; alkaline earth metals such as calcium;
simple metals such as aluminum, titanium, manganese, silver, lead, and chromium; alloys of these simple metals such as magnesium-silver, aluminum-lithium, and aluminum-magnesium; and metal oxides such as indium tin oxide (ITO).
[0063] These electrode materials may be used alone or in combination of two or more thereof. The cathode may have either a monolayer structure or a multilayer structure.
[0064] In the organic light-emitting device according to the present embodiment, a layer containing the organic
compound according to the present invention and a layer of
another organic compound are formed by the following methods.
[0065] In general, a thin film is formed by vacuum
deposition, ionic vapor deposition, sputtering, plasma CVD, or a known coating process using a solution of an
appropriate solvent (e.g., spin coating, dipping, casting, an LB method, or an ink jet method) .
[0066] A layer formed by vacuum deposition or coating of a solution hardly causes, for example, crystallization and is stable for a long time. In the case of forming a film by coating, the solution may additionally contain an
appropriate binder resin.
[0067 ] Examples of the binder resin include, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenol resins, epoxy resins, silicone resins, and urea resins.
[0068] These binder resins may be singly used as a
homopolymer or a copolymer or as a mixture of two or more of polymers. The solution for forming a film may further
optionally contain additives such as known plasticizer, antioxidant, and ultraviolet absorber.
Application of organic light-emitting device according to the present embodiment
[ 0069] The organic light-emitting device according to the present embodiment can be applied to a display apparatus or
a lighting system. In addition, the device can be used, for example, in an exposing light source of an
electrophotographic image-forming apparatus or in a
backlight of a liquid crystal display apparatus.
[0070] The display apparatus has the organic light- emitting device according to the present embodiment in a display section. The display section has a plurality of pixels. Each pixel has the organic light-emitting device according to the present embodiment and a thin-film
transistor (TFT) as an example of a switching device for controlling luminance. In the switching device, the drain electrode or the source electrode of the thin-film
transistor is connected to the anode or the cathode of the organic light-emitting device.
[0071] The display apparatus can be used as an image display apparatus of, for example, a PC, a head mount display, or a mobile phone. The image displayed may be a two-dimensional image or a three-dimensional image.
[0072] The display apparatus may be an image output apparatus that includes an image input section for inputting image information from, for example, an area CCD, a linear CCD, or a memory card and outputs the input image to a display section.
[0073] The image output apparatus may be a digital camera having an image pickup optical system with an image pickup
device, such as a CCD sensor, as the image input section.
[0074] The display apparatus may have an input function for inputting information by touching an image on the display, such as a touch panel function.
[0075] The display apparatus may be used in the display section of a multi-functional printer.
[0076] The organic light-emitting device according to the present embodiment may be used in a lighting system. This lighting system includes the organic light-emitting device according to the present embodiment and a converter circuit connected to the organic light-emitting device.
[0077] The color of illumination light of the lighting system according to the present embodiment may be white or neutral white or another color.
[0078] A display apparatus having the organic light- emitting device according to the present embodiment will now be described with reference to Figure 1.
[0079] Figure 1 is a schematic cross-sectional view illustrating organic light-emitting devices according to the present embodiment and TFTs as an example of switching devices connected to the organic light-emitting devices. This drawing shows two pairs of the organic light-emitting devices and the TFTs. The structure will now be described in detail.
[0080] The display apparatus shown in Figure 1 includes a
substrate 1 such as a glass substrate and a moisture-proof film 2 disposed on the substrate 1 for protecting TFTs or an organic compound layer. Reference numeral 3 denotes a metal gate electrode, reference numeral 4 denotes a gate
insulating film, and reference numeral 5 denotes a
semiconductor layer.
[0081] A thin-film transistor 8 includes a semiconductor layer 5, a drain electrode 6, and a source electrode 7. An insulating film 9 is disposed on the thin-film transistor 8. The source electrode 7 is connected to the anode 11 of the organic light-emitting device via a contact hole 10.
[0082] The display apparatus is not limited to this structure as long as either the anode or the cathode is connected to either the source electrode or the drain electrode of the thin-film transistor.
[0083] In this drawing, the organic compound layer 12 is simplified and drawn as one layer, but is actually composed of a plurality of organic compound layers. A first
protection layer 14 and a second protection layer 15 are disposed on a cathode 13 for inhibiting degradation of the organic light-emitting device.
[0084] In the display apparatus according to the present embodiment, the switching device is not particularly limited and may be a transistor or an MIM element. The transistor may be a thin-film transistor employing single crystal
silicon or an amorphous silicon transistor. The thin-film transistor is also called a TFT.
[0085] In the organic light-emitting device, the switching device controls the luminance. By disposing the organic light-emitting devices in a plurality of planes, images can be displayed with the respective luminance.
[0086] Alternatively, the luminance also can be controlled by producing an active matrix driver on a Si substrate and disposing the organic light-emitting devices thereon.
[0087] This is selected depending on the degree of
definition. For example, in a definition for about 1-inch QVGA, the organic light-emitting devices can be disposed on a Si substrate.
[0088] Stable display with a good image quality is
possible even in display for a long time by driving the display apparatus using the organic light-emitting devices according to the present embodiment.
Examples
Example 1
Synthesis of Example Compound A-112
[0089] (1) Synthesis of intermediate PCz-PB
[0090]
[Chem.
PCz-PB
[0091] The following reagents and solvents:
9H-carbazole: 120 g (0.718 mol) ,
2-fluoronitrobenzene : 106 g (0.754 mol),
cesium carbonate: 152 g (1.077 mol), and
dehydrated dimethylsulfoxide : 1.8 L
were charged in a round bottom flask.
[0092] This mixture was stirred under nitrogen at room temperature for 3 days. After completion of the reaction, the mixture was poured into 3 L of ice water. The
precipitated yellow solid was stirred at room temperature for 30 min and was collected by filtration. The collected solid was dissolved in 3 L of chloroform and was washed with
water, dehydrated with magnesium sulfate, and concentrated to give 229 g of 9- (2-nitrophenyl) -9H-carbazole as a yellow solid .
[0093] The following reagents and a solvent:
9- (2-nitrophenyl) -9H-carbazole: 229 g (0.794 mol) ,
SnCl2-2H20: 567 g (2.51 mol), and
ethanol: 5 L
were charged in a round bottom flask.
[0094] This mixture was stirred with heating at an
internal temperature of 70 °C under nitrogen for 8 hours.
After completion of the reaction, the mixture was allowed to cool and was concentrated. To the residue, 5 L of an
aqueous solution of 1 N sodium hydroxide was added. The resulting suspension was stirred at room temperature for 1 hour, followed by filtration. The solid collected by
filtration was dissolved in 8 L of toluene, and 7 L of an aqueous solution of 1 N sodium hydroxide was added thereto. After liquid phase separation, the aqueous layer was removed, and the organic layer was washed with water, dehydrated with magnesium sulfate, concentrated once, and heated and washed by suspension in isopropyl ether to give 124 g of 2-(9H- carbazol-9-yl) aniline as a light yellow solid (yield: 61%).
[0095] The following reagents and a solvent:
2- (9H-carbazol-9-yl) aniline: 124 g (0.480 mol),
acetic acid: 1.2 L, and
concentrated sulfuric acid: 124 mL
were charged in a round bottom flask.
[0096] This mixture was immersed in an ice water bath to cool to an internal temperature of 10°C. To the solution, a solution prepared by dissolving 33.8 g of sodium nitrite in 670 mL of distilled water was dropwise added over 15 min, followed by stirring for 10 min. Subsequently, the mixture was heated at an external temperature of 130 °C with stirring for 20 min. After completion of the reaction, the mixture was allowed to cool. One liter of distilled water was added to the mixture, and the precipitated solid was collected by filtration. This yellowish brown solid was washed by suspension in 2 L of methanol to give a brown solid. This solid was purified by column chromatography (silica gel) and then recrystallized from a solvent mixture of chloroform and ethanol to give 83.3 g of aminoindolo [ 3 , 2 , 1-j k] carbazole as a light-orange to white solid (yield: 72%) .
[0097] The following reagents and a solvent:
aminoindolo [3, 2, 1-j k] carbazole : 83.3 g (0.345 mol),
N-bromosuccinimide : 67.6 g, and
dehydrated methylene chloride: 3.3 L
were charged in a round bottom flask under light shielding.
[0098] This mixture was stirred at room temperature under light shielding for 1 hour, and 250 g of silica gel was added thereto. The mixture was stirred at room temperature
for 13 hours. After completion of the reaction, the silica gel was collected by filtration. The collected silica gel was washed three times with 1 L of chloroform in total. The chloroform was collected and was washed with water,
dehydrated with anhydrous sodium sulfate, and concentrated. The resulting solid after concentration was recrystallized from toluene and was heated and washed with acetic acid to give 62.2 g of 2-bromoaminoindolo [ 3 , 2 , 1-j k] carbazole as a white solid (yield: 57%) .
[0099] The resulting compound was identified by XH-NMR analysis .
["""H-NMR (300 MHz, CDC13) ]
6 8.12 (s,2H), 8.06-8.03 (d, 2H) , 7.87-7.84 (d, 2H) , 7.59- 7.53 (t,2H), 7.38-7.32 (t,2H).
[0100] The following reagents and solvents:
2-bromoaminoindolo [ 3, 2 , 1-j k] carbazole : 55.0 g (0.172 mol) ,
bis (pinacolato) diboron : 52.4 g (0.206 mol),
[ 1 , 1 ' -bis (diphenylphosphino) ferrocene] palladium ( II ) dichloride dichloromethane adduct : 2.11 g (2.58 mmol),
1, 1 ' -bis (diphenylphosphino) ferrocene : 1.43 g (2.58 mmol ) ,
potassium acetate: 42.2 g (0.430 mol),
dehydrated 1,4-dioxane: 550 mL, and
dehydrated toluene: 550 mL
were charged in a round bottom flask under light shielding.
[0101] This mixture was deaerated and was then heated at an external temperature of 120°C with stirring under argon for 17 hours. After completion of the reaction, the mixture was allowed to cool and was concentrated. The resulting solid after concentration was heated and washed by
suspension in toluene, followed by purification by column chromatography (silica gel) to give a white solid. This solid was washed with hexane and isopropyl ether to give 48 g of PCz-PB as a white solid (yield: 76%).
[0102] The resulting compound was identified by 1H-NMR analysis .
[ 1H-N R (300 MHz, CDC13) ]
6 8.57 (s,2H), 8.15-8.13 (d,2H), 7.93-7.90 (d,2H), 7.59- 7.53 (t,2H), 7.39-7.34 (t,2H), 1.45 (s,12H).
[0103] (2) Synthesis of Example Compound A-112
[0104]
Chem.
[0105] The following reagents and solvents:
bis ( [1, 1 ' -biphenyl] -4-yl) amine: 0.985 g (3.06 mmol), 4-bromo-4 ' -iodo-1, 1 ' -biphenyl : 1.0 g (2.79 mmol), palladium acetate: 16 mg (0.07 mmol),
xantphos: 81 mg (0.14 mmol),
sodium tertiary butoxide: 402 mg (4.18 mmol), and xylene: 10 mL
were charged in a round bottom flask.
[0106] This mixture was heated at an external temperature of 120°C with stirring under nitrogen for 2 hours. After completion of the reaction, the solution was allowed to cool, and 30 mL of methanol was added thereto. The resulting solution was washed with methanol and subjected to
purification by suction filtration and column chromatography (silica gel, toluene/heptane = 1/2) to give 1.052 g of white powder 1-1 (yield: 68%).
[0107] The following reagents and solvents:
PCz-PB: 455 mg (1.24 mmol) ,
1-1: 690 mg (1.24 mmol) ,
tetrakis (triphenylphosphine) palladium ( 0 ) : 28 mg (0.024 mmol) ,
sodium carbonate: 263 mg (2.48 mmol),
toluene: 40 mL,
ethanol: 20 mL, and
water: 20 mL
were charged in a round bottom flask.
[0108] This mixture was heated at an external temperature of 100°C with stirring for 5 hours. After completion of the reaction, the mixture was allowed to cool, washed with
methanol, and subjected to suction filtration. The
resulting product was dissolved in toluene under heating, subjected to hot filtration through silica gel, and
recrystallized to give a white powder. The resulting powder was dried in vacuum at 130°C and was purified by sublimation under conditions of lxlO"4 Pa and 380°C to give 135 mg of Example Compound A-112 with high purity (yield: -15%).
[0109] The results of identification of the resulting compound are shown below:
[MALDI-TOF-MS]
Observed value: m/z = 712.405, calculated value: C54H36N2 = 712.29,
["""H-NMR (400 MHz, CDCI3) ]
6 8.31 (s,2H), 8.20-8.18 (d,2H), 7.95-7.93 (d,2H), 7.86- 7.84 (d,2H), 7.77-7.75 (d,2H), 7.65-7.54 (m, 12H) , 7.46-7.26 (m, 14H) .
[0110] The glass transition temperature (hereinafter, referred to as Tg) of Example Compound A-112 measured with an ultra-high sensitive differential scanning calorimeter, DSC 204 Fl Phoenix (registered trademark), was 145°C.
Example 2
Synthesis of Example Compound A-022
[0111]
[Chem.
[0112] The following reagents and solvents:
PCz-PB: 3.67 g (10 mmol) ,
4-bromo-4 ' -iodo-1, 1 ' -biphenyl : 3.59 g (10 mmol), dichlorobis (triphenylphosphine) palladium: 280 mg (0.4 mmol) ,
potassium carbonate: 2.07 g (15 mmol),
dioxane: 80 mL, and
water: 5 mL
were charged in a round bottom flask.
[0113] This mixture was heated at an external temperature of 100°C with stirring under nitrogen for 9 hours. After completion of the reaction, the mixture was allowed to cool, and 200 mL of chlorobenzene was added thereto. After dissolving by heating, hot filtration through silica gel, recrystallization, and concentration were performed. The resulting product was recrystallized from 100 mL of toluene and dried in vacuum at 130°C to give 2.3 g of 1-2 (yield: 48.6%) .
[0114] The following reagents and solvents:
N-phenyl- [1, 1 ' : 4 ' , 1 * ' -terphenyl] -4-amine: 1.05 g (3.30 mmol) ,
1-2: 1.54 g (3.26 mmol) ,
bis (dibenzylideneacetone) palladium ( 0 ) : 94 mg (0.163 mmol ) ,
XPhos: 155 mg (0.325 mmol),
sodium tertiary butoxide: 626 mg (6.51 mmol), and xylene: 100 mL
were charged in a round bottom flask.
[0115] This mixture was heated at an external temperature of 120°C with stirring under nitrogen for 3 hours. After completion of the reaction, the resulting product was dissolved in toluene under heating, subjected to hot
filtration through silica gel, and recrystallized to give a white powder. The resulting powder was dried in vacuum at
130°C and was purified by sublimation under conditions of 3.3xlCT3 Pa and 380 °C to give 230 mg of Example Compound A- 022 with high purity.
[0116] The results of identification of the resulting compound are shown below:
[MALDI-TOF-MS ]
Observed value: m/z = 712.484, calculated value: C54H36N2 = 712.29
[ 1H-NMR (400 MHz , CDCI3) ]
5 8.31 (s,2H), 8.21-8.19 (d,2H), 7.96-7.94 (d,2H), 7.86- 7.84 (d,2H), 7.76-7.74 (d,2H), 7.68-7.56 (m, 12H) , 7.49-7.31
(m, 8H), 7.25-7.22 (m,5H), 7.11-7.07 (t,lH).
[0117] The glass transition temperature (hereinafter, referred to as Tg) of Example Compound A-022 measured with an ultra-high sensitive differential scanning calorimeter, DSC 204 Fl Phoenix (registered trademark), was 143°C.
Example 3
Synthesis of Example Compound A-113
[0118]
[Chem.
[0119] (1) Synthesis of intermediate 1-3
The following reagents and solvents:
PCz-PB: 5 g (13.6 mmol) ,
4-bromo-4 ' -iodo-1 , 1 ' -biphenyl : 3.85 g (12.5 mmol), dichlorobis (triphenylphosphine) palladium: 478 mg (0.68
mmol) ,
potassium carbonate: 5.64 g (40.8 mmol),
toluene: 100 mL,
ethanol: 50 mL, and
water: 50 mL
were charged in a round bottom flask.
[0120] This mixture was heated at an external temperature of 100°C with stirring under nitrogen for 3 hours. After completion of the reaction, the mixture was allowed to cool, and toluene was added thereto to extract the resulting product, followed by concentration. The resulting product was purified by column chromatography (silica gel,
chloroform/heptane = 1/2), concentrated, and dried in vacuum at 130°C to give 2 g of 1-3 (yield: 40.4%).
[0121] (2) Synthesis of intermediate 1-4
The following reagent and solvent:
1-1: 1.4 g (2.53 mmol), and
toluene: 50 mL
were charged in a round bottom flask.
[0122] This mixture was subjected to nitrogen bubbling, and the following reagents:
triethylamine : 2.65 mL (20.2 mmol),
[ 1 , 3-bis (diphenylphosphino) propane] nickel ( II )
dichloride: 274 mg (0.50 mmol), and
4, , 5, 5-tetramethyl-l, 3, 2-dioxaborolane: 1.84 mL (12.68
mmol )
were further added to the round bottom flask.
[0123] This mixture was heated at an external temperature of 100°C with stirring under nitrogen for 6 hours. After completion of the reaction, the mixture was allowed to cool, and toluene was added thereto to extract the resulting product, followed by concentration. The resulting product was purified by column chromatography (silica gel,
toluene/heptane = 1/2), concentrated, and washed with methanol. After filtration, drying in vacuum at 130°C was performed to give 1.22 g of 1-4 (yield: 80.4%).
[0124] (3) Synthesis of Example Compound A-113
The following reagents and solvents:
1-3: 792 mg (2 mmol),
1-4: 1.2 g (2 mmol) ,
bis (dibenzylideneacetone) palladium(O) : 23 mg (0.04 mmol ) ,
XPhos: 38 mg (0.08 mmol),
sodium carbonate: 636 mg (6 mmol),
toluene: 50 mL,
ethanol: 20 mL, and
water: 20 mL
were charged in a round bottom flask.
[0125] This mixture was heated at an external temperature of 90°C with stirring under nitrogen for 3 hours. After
completion of the reaction, water and ethanol were added to the mixture, followed by suction filtration. The resulting product was purified by column chromatography (silica gel, chlorobenzene/methylcyclohexane = 1/2), concentrated, and washed with ethanol, followed by suction filtration. The resulting powder was dried in vacuum at 110 °C and was then purified by sublimation under conditions of 4.1xl0~4 Pa and 395°C to give 418 mg of Example Compound A-113 with high purity (yield: 26.4%) .
[0126] The results of identification of the resulting compound are shown below:
[MALDI-TOF-MS]
Observed value: m/z = 788.734, calculated value: C6oH40N2 = 788.32
[ 1H-NMR (400 MHz, CDCI3) ]
5 8.32 (s,2H), 8.21-8.19 (d,2H), 7.96-7.94 (d,2H), 7.89- 7.87 (d,2H), 7.82-7.78 (m,4H), 7.74-7.71 (d,2H), 7.62-7.54 (m,13H) , 7.46-7.26 (m, 13H) .
[0127] The glass transition temperature (hereinafter, referred to as Tg) of Example Compound A-113 measured with an ultra-high sensitive differential scanning calorimeter, DSC 204 Fl Phoenix (registered trademark), was 157°C.
Comparative Example 1
Comparison of glass transition temperature Tg
[0128] The glass transition temperatures (hereinafter,
referred to as Tg) of comparative compound SH-01 and comparative compound SH-02 shown below were measured by DSC 204 Fl Phoenix (registered trademark) and were 141°C and 125°C, respectively. Table 1 shows comparison with Examples of the present invention.
[0129]
[Chem. 13]
[0130]
[Table 1]
[0131] The Tg of each of comparative compounds SH-01 and SH-02 is increased by 16 to 20°C by replacing the carbazolyl group with an indolo [ 3 , 2 , 1-j k] carbazolyl group. It is thus recognized that the heat stability of the Example compounds is higher than that of the comparative compounds.
Example 4
[0132] In this example, a bottom emission type organic
light-emitting device having a configuration composed of anode/hole-transporting layer/light-emitting layer/hole- blocking layer/electron-transporting layer/electron- injecting layer/cathode disposed in this order on a
substrate was produced by the following method.
[0133] A film of indium tin oxide (ITO) was formed on a glass substrate by sputtering as an anode having a thickness of 120 nm. The glass substrate provided with the ITO film was subjected to ultrasonic washing in acetone and isopropyl alcohol (IPA) in this order, washed by boiling in IPA, and then dried. Furthermore, the substrate was subjected to UV/ozone washing. The thus-treated glass substrate was used as a transparent electrically conductive support substrate (ITO substrate). On this ITO substrate, organic compound layers and electrode layers shown below were successively formed by resistance heating vacuum vapor deposition in a vacuum chamber. The layers were:
hole-transporting layer (25 nm) A-112,
light-emitting layer (20 nm) , host material: H-l, guest material: D-l (1 wt%),
hole-blocking layer (10 nm) HBM-1,
electron-transporting layer (20 nm) ETM-1,
electron-injecting layer (0.5 nm) lithium fluoride, and metal electrode layer (100 nm) aluminum.
[0134]
[Chera.
[0135] Then, in order to prevent deterioration of the organic light-emitting device due to absorption of moisture, covering with a protective glass plate and sealing with an acrylic polymer adhesive were performed in a dried air atmosphere. Thus, an organic light-emitting device was produced .
[0136] A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed. As for characteristics of the organic light-emitting device, the current-voltage
characteristics were measured with an ammeter 2700 manufactured by Keithley Instruments, Inc., and the
luminance was measured with BM7-fast manufactured by Topcon Corp .
[0137] H-l, D-l, HBM-1 , and ET -1 used in Example 4 were synthesized with reference to U.S. Patent Publication No. 2005/0236977, Japanese Patent Laid-Open No. 2010-270103, International Publication No. WO2010/107037 , and
International Publication No. WO2009/139501, respectively. Example 5
[0138] An organic light-emitting device was produced as in Example 4 except that the hole-transporting layer was formed using A-022 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
Example 6
[0139] An organic light-emitting device was produced as in Example 4 except that the hole-transporting layer was formed using A-113 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
Comparative Example 2
[0140] An organic light-emitting device was produced as in
Example 4 except that the hole-transporting layer was formed using SH-01 instead of A-112. A voltage was applied between a positive ITO electrode and a negative Al electrode of the resulting organic light-emitting device. As a result, a blue light emission was observed.
[0141] Regarding the organic light-emitting devices in Examples 4 to 6 and Comparative Example 2, Table 2 shows the relative voltage at 6000 cd/m2 (when the voltage in the organic light-emitting device of Comparative Example 2 was defined as 1) and the relative time for reducing brightness by 4% in driving at a constant current of 25 mA/m2 (when the time in the organic light-emitting device of Comparative Example 2 was defined as 1) .
[0142]
[Table 2]
[0143] The Example compounds allowed a reduction in driving voltage and an increase in endurance time of driving compared with those by the comparative compound.
[0144] As described above, the aminoindolo [ 3 , 2 , 1- j k] carbazole compound according to the present invention has satisfactory heat stability, and a light-emitting device in
which the compound is used can have a low driving voltage and high driving durability.
[0145] While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. The scope of the following claims is to be accorded the broadest interpretation so as to encompass all such modifications and equivalent structures and functions.
[0146] This application claims the benefit of Japanese Patent Application No. 2011-168335, filed August 1, 2011, which is hereby incorporated by reference herein in its entirety.
Claims
(in Formula [1], 1 represents an integer of 1 to 3; n and m each independently represent an integer of 0 to 2; and R1 to R32 represent hydrogen atom, alkyl groups having 1 to 8 carbon atoms or fluorine atoms, wherein the alkyl groups optionally contain fluorine atoms).
[2] An organic light-emitting device comprising a pair of electrodes and an organic compound layer disposed between the pair of electrodes, wherein
the organic compound layer includes the
aminoindolo [ 3 , 2 , 1-j k] carbazole compound according to Claim 1.
[3] The organic light-emitting device according to Claim 2, wherein the organic compound layer is a hole-injecting layer, a hole-transporting layer, or an electron-blocking layer.
[4] A display apparatus comprising a plurality of pixels each having an organic light-emitting device according to Claim 2 and a switching device connected to the organic light-emitting device.
[5] An image input apparatus comprising a display section for displaying an image and an input section for inputting image information, wherein the display section includes a plurality of pixels each having an organic light-emitting device according to Claim 2 and a switching device connected to the organic light-emitting device.
[6] A lighting system comprising an organic light-emitting device according to Claim 2 and a converter circuit
connected to the organic light-emitting device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/236,569 US20140167028A1 (en) | 2011-08-01 | 2012-07-10 | AMINOINDOLO[3,2,1-jk]CARBAZOLE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011168335A JP5882621B2 (en) | 2011-08-01 | 2011-08-01 | Aminoindolo [3,2,1-jk] carbazole compound and organic light-emitting device having the same |
| JP2011-168335 | 2011-08-01 |
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| Publication Number | Publication Date |
|---|---|
| WO2013018530A1 true WO2013018530A1 (en) | 2013-02-07 |
Family
ID=47629059
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| PCT/JP2012/068045 WO2013018530A1 (en) | 2011-08-01 | 2012-07-10 | AMINOINDOLO[3,2,1-jk]CARBAZOLE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME |
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| US (1) | US20140167028A1 (en) |
| JP (1) | JP5882621B2 (en) |
| WO (1) | WO2013018530A1 (en) |
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| KR102404141B1 (en) | 2015-07-17 | 2022-06-02 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| US9954187B2 (en) | 2016-04-08 | 2018-04-24 | Idemitsu Kosan Co., Ltd. | Compound, organic electroluminescence device and electronic device |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP5882621B2 (en) | 2016-03-09 |
| JP2013033804A (en) | 2013-02-14 |
| US20140167028A1 (en) | 2014-06-19 |
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