JP5677036B2 - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
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- JP5677036B2 JP5677036B2 JP2010249278A JP2010249278A JP5677036B2 JP 5677036 B2 JP5677036 B2 JP 5677036B2 JP 2010249278 A JP2010249278 A JP 2010249278A JP 2010249278 A JP2010249278 A JP 2010249278A JP 5677036 B2 JP5677036 B2 JP 5677036B2
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- light emitting
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- organic light
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- 239000000463 material Substances 0.000 claims description 93
- -1 thioxanthone compound Chemical class 0.000 claims description 75
- 150000002894 organic compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 131
- 239000010410 layer Substances 0.000 description 131
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- 239000013078 crystal Substances 0.000 description 64
- 239000000243 solution Substances 0.000 description 36
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- 239000012043 crude product Substances 0.000 description 32
- 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 32
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- 238000000034 method Methods 0.000 description 30
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 25
- 238000000859 sublimation Methods 0.000 description 21
- 230000008022 sublimation Effects 0.000 description 21
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- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
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- 235000002597 Solanum melongena Nutrition 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
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- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 5
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 0 *c1cc(-c2ccccc2)ccc1 Chemical compound *c1cc(-c2ccccc2)ccc1 0.000 description 2
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- 230000005284 excitation Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
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- 238000005215 recombination Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JGSMRGQWNLHMEI-UHFFFAOYSA-N C(C1)C=Cc(c2ccc3)c1[s]c2c3-c1cccc(-c2ccc(c(cccc3)c3c3c4cccc3)c4c2)c1 Chemical compound C(C1)C=Cc(c2ccc3)c1[s]c2c3-c1cccc(-c2ccc(c(cccc3)c3c3c4cccc3)c4c2)c1 JGSMRGQWNLHMEI-UHFFFAOYSA-N 0.000 description 1
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N C=CC(c1ccccc1)=C Chemical compound C=CC(c1ccccc1)=C IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
- PNVXPWQNWHEESV-UHFFFAOYSA-N CC1(C)c2ccccc2C(C=C2)=C1CC2c(cc1C(c2c3)=O)ccc1Sc2ccc3-c(cc1)cc2c1-c1ccccc1C2(C)C Chemical compound CC1(C)c2ccccc2C(C=C2)=C1CC2c(cc1C(c2c3)=O)ccc1Sc2ccc3-c(cc1)cc2c1-c1ccccc1C2(C)C PNVXPWQNWHEESV-UHFFFAOYSA-N 0.000 description 1
- TYKUXDUAORFCLH-LCYFTJDESA-N CCC(C(C)CC/C=C\C(c1ccc(C(C)(C)c2ccccc2-2)c-2c1)=C)=C Chemical compound CCC(C(C)CC/C=C\C(c1ccc(C(C)(C)c2ccccc2-2)c-2c1)=C)=C TYKUXDUAORFCLH-LCYFTJDESA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
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- MIGPGZSVGPGCCR-UHFFFAOYSA-N O=C(c1c2)c3cc(Br)ccc3Sc1ccc2Br Chemical compound O=C(c1c2)c3cc(Br)ccc3Sc1ccc2Br MIGPGZSVGPGCCR-UHFFFAOYSA-N 0.000 description 1
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- SQBWUIRUYJQDEI-UHFFFAOYSA-N c(cc1)ccc1-c1c(-c2ccccc2)c(-c(cc2)ccc2-[n]2c3cccc(-c4cccc5c4c(cccc4)c4[n]5-c4cc(-c5cccc(-[n]6c7ccccc7c7ccccc67)c5)ccc4)c3c3ccccc23)c(-c2ccccc2)c(-c2ccccc2)c1-c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 Chemical compound c(cc1)ccc1-c1c(-c2ccccc2)c(-c(cc2)ccc2-[n]2c3cccc(-c4cccc5c4c(cccc4)c4[n]5-c4cc(-c5cccc(-[n]6c7ccccc7c7ccccc67)c5)ccc4)c3c3ccccc23)c(-c2ccccc2)c(-c2ccccc2)c1-c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 SQBWUIRUYJQDEI-UHFFFAOYSA-N 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 238000003384 imaging method Methods 0.000 description 1
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- 229910003437 indium oxide Inorganic materials 0.000 description 1
- NJWNEWQMQCGRDO-UHFFFAOYSA-N indium zinc Chemical compound [Zn].[In] NJWNEWQMQCGRDO-UHFFFAOYSA-N 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
- 238000012905 input function Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
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- 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
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 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
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000553 poly(phenylenevinylene) 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
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 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
- 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
- 150000003918 triazines Chemical class 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
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
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Description
前記陽極と前記陰極との間に配置される有機化合物層と、を有し、
前記有機化合物層が、下記一般式[1]で示されるチオキサントン化合物を有することを特徴とする。
一般に燐光発光する有機発光素子では、ホスト材料のT1から非放射失活による発光効率の低下を防ぐために、ホスト材料のT1エネルギーはゲスト材料である燐光発光材料のT1エネルギーよりも高いことが必要とされている。
F−1:1.85g(5mmol)
F−2(フェニルボロン酸):1.5g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=364.55、計算値:C25H16OS=364.09
F−1:1.85g(5mmol)
F−3(3−ビフェニルボロン酸):2.4g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=515.98、計算値:516.15
また例示化合物A−3について、実施例1と同様の方法でT1エネルギーの測定を行ったところ、波長換算値で474nmであった。さらに例示化合物A−3について実施例1と同様の方法でエネルギーギャップの測定を行ったところ、例示化合物A−3のエネルギーギャップは3.3eVであった。
F−1:1.85g(5mmol)
F−4:4.3g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=668.22、計算値:668.84
F−1:1.85g(5mmol)
F−5:2.9g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=596.45、計算値:596.22
F−1:1.85g(5mmol)
F−6:2.9g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=596.40、計算値:596.22
F−1:1.85g(5mmol)
F−7:4.3g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=674.98、計算値:664.19
F−1:1.85g(5mmol)
F−8:5.3g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=840.77、計算値:840.25
F−1:1.9g(5mmol)
F−9:2.0g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=448.69、計算値:448.19
F−10:1.85g(5mmol)
F−6:2.9g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=596.89、計算値:596.22
F−1:1.85g(5mmol)
F−11:3.7g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=576.67、計算値:576.07
F−1:1.85g(5mmol)
F−12:3.7g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=576.46、計算値:576.07
F−1:1.85g(5mmol)
F−13:3.5g(12mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=544.87、計算値:C37H20O3S=544.11
F−14:1.45g(5mmol)
F−15:3.0g(6mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=590.84、計算値:590.17
F−14:3.5g(12mmol)
F−16:2.0g(5mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=574.79、計算値:574.11
F−14:1.45g(5mmol)
F−17:2.3g(6mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=470.54、計算値:470.08
また例示化合物C−9について、実施例1と同様の方法でT1エネルギーの測定を行ったところ、波長換算値で453nmであった。さらに例示化合物C−9について実施例1と同様の方法でエネルギーギャップの測定を行ったところ、例示化合物C−9のエネルギーギャップは3.5eVであった。
F−14:1.5g(5mmol)
F−18:3.6g(6mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):137mg(0.12mmol)
トルエン:50mL
エタノール:20mL
炭酸ナトリウム水溶液(濃度:30重量%):30mL
実測値:m/z=678.87、計算値:678.20
本実施例では、基板上に順次陽極/ホール輸送層/発光層/ホールブロッキング層/電子輸送層/陰極が順次設けられている有機発光素子を、以下に示す方法で作製した。尚、本実施例で使用した化合物の一部を下記に示す。
実施例17において、ホールブロック層(HB層)に含まれるホールブロック材料(HB材料)、並びに発光層に含まれる第一ホスト、第二ホスト及びゲストの組み合わせを下記表5に変更した他は、実施例17と同様の方法で素子を作製した。また得られた素子について実施例17と同様に評価を行った。結果を表5に示す。
実施例17において、ホールブロック層(HB層)に含まれるホールブロック材料(HB材料)、並びに発光層に含まれる第一ホスト、第二ホスト及びゲストの組み合わせを下記表6に変更した他は、実施例17と同様の方法で素子を作製した。ここで比較例1で使用した化合物H−1Aを以下に示す。
Claims (12)
- 陽極と陰極と、
前記陽極と前記陰極との間に配置される有機化合物層と、を有し、
前記有機化合物層が、下記一般式[1]で示されるチオキサントン化合物を有することを特徴とする、有機発光素子。
尚、前記アルキル基及び前記アリール基は、さらにアルキル基、芳香族炭化水素基又は芳香族複素環基を有してもよい。) - 前記一般式[1]で示されるチオキサントン化合物において、
前記R1、R4、R5及びR8が水素原子であることを特徴とする、請求項1に記載の有機発光素子。 - 前記有機化合物層が発光層を有し、
前記発光層が、前記チオキサントン化合物を有することを特徴とする、請求項1又は2に記載の有機発光素子。 - 前記有機化合物層が、発光層と、前記発光層と前記陰極との間に配置されるホールブロッキング層と、を有し、
前記ホールブロッキング層が、前記チオキサントン化合物を有することを特徴とする、請求項1乃至3のいずれか一項に記載の有機発光素子。 - 前記発光層が、ホストと、ゲストとからなり、
前記ホストが前記チオキサントン化合物であることを特徴とする、請求項1乃至4のいずれか一項に記載の有機発光素子。 - 前記ゲストが燐光発光材料であることを特徴とする、請求項5に記載の有機発光素子。
- 前記燐光発光材料がイリジウム錯体であることを特徴とする、請求項6に記載の有機発光素子。
- 複数の画素を有し、
前記画素が、請求項1乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続するスイッチング素子と、を有することを特徴とする表示装置。 - 画像を表示するための表示部と、画像情報を入力するための入力部とを有し、
前記表示部が複数の画素を有し、
前記画素が、請求項1乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続するスイッチング素子と、を有することを特徴とする画像入力装置。 - 請求項1乃至7のいずれか一項に記載の有機発光素子を有することを特徴とする、照明装置。
- 露光光源を有する電子写真方式の画像形成装置であって、
前記露光光源が、請求項1乃至7のいずれか一項に記載の有機発光素子を有することを特徴とする、画像形成装置。 - 電子写真方式の画像形成装置に設けられる露光光源であって、
前記露光光源が、請求項1乃至7のいずれか一項に記載の有機発光素子を有することを特徴とする、露光光源。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103804346B (zh) * | 2012-11-08 | 2016-06-29 | 中国科学院理化技术研究所 | 氧化硫杂蒽酮类衍生物、制备方法及其应用 |
CN104003974B (zh) * | 2013-02-27 | 2017-03-01 | 中国科学院理化技术研究所 | 氧化硫杂蒽酮类衍生物、制备方法及其应用 |
WO2014071836A1 (zh) * | 2012-11-08 | 2014-05-15 | 中国科学院理化技术研究所 | 氧化硫杂蒽酮类衍生物、制备方法及其应用 |
JP6271154B2 (ja) * | 2013-05-10 | 2018-01-31 | 住友化学株式会社 | 発光素子 |
JP6521253B2 (ja) * | 2013-07-03 | 2019-05-29 | 株式会社Kyulux | 発光材料、遅延蛍光体、有機発光素子および化合物 |
GB2522457B (en) * | 2014-01-24 | 2016-05-25 | Cambridge Display Tech Ltd | Compound, composition and organic light-emitting device |
CN104761547A (zh) * | 2015-03-26 | 2015-07-08 | 深圳市华星光电技术有限公司 | 噻吨酮-芳香胺化合物及应用该化合物的有机发光器件 |
CN107068910B (zh) * | 2016-04-25 | 2019-07-19 | 中节能万润股份有限公司 | 一种含氧杂蒽酮类化合物的有机电致发光器件及其应用 |
CN106220638B (zh) * | 2016-04-25 | 2018-06-26 | 中节能万润股份有限公司 | 一种基于氧杂蒽酮的化合物及其应用 |
CN106279137A (zh) | 2016-07-20 | 2017-01-04 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN106190107A (zh) * | 2016-07-20 | 2016-12-07 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN106188024A (zh) * | 2016-07-20 | 2016-12-07 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN106188025A (zh) | 2016-07-20 | 2016-12-07 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN106317041A (zh) * | 2016-07-20 | 2017-01-11 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN106167487A (zh) * | 2016-07-20 | 2016-11-30 | 深圳市华星光电技术有限公司 | 发光材料及其制备方法与使用该发光材料的有机发光二极管 |
CN108346756B (zh) * | 2017-01-24 | 2020-03-20 | 中节能万润股份有限公司 | 一种有机电致发光器件 |
CN106995430A (zh) * | 2017-03-15 | 2017-08-01 | 同济大学 | 新型硫杂蒽酮化合物及其应用 |
EP3618577A4 (en) * | 2017-04-27 | 2021-02-17 | Sumitomo Chemical Company Limited | COMPOSITION AND ELECTROLUMINESCENT ELEMENT INCLUDING IT |
WO2018198973A1 (ja) * | 2017-04-27 | 2018-11-01 | 住友化学株式会社 | 組成物及びそれを用いた発光素子 |
TWI776926B (zh) * | 2017-07-25 | 2022-09-11 | 德商麥克專利有限公司 | 金屬錯合物 |
CN109748916B (zh) * | 2017-11-03 | 2021-06-15 | 中节能万润股份有限公司 | 一种以氮杂螺芴和芳基酮为核心的化合物、其制备方法及其在oled上的应用 |
CN109748899B (zh) * | 2017-11-03 | 2023-04-07 | 江苏三月科技股份有限公司 | 一种含有酮的化合物及其在有机电致发光器件上的应用 |
CN108358888B (zh) * | 2018-01-23 | 2020-01-17 | 华南协同创新研究院 | 一类含硫四元稠环单元及其衍生物和制备方法与应用 |
KR102383315B1 (ko) | 2018-03-30 | 2022-04-06 | 캐논 가부시끼가이샤 | 유기발광소자, 표시장치, 촬상 장치 및 조명 장치 |
CN108218831B (zh) * | 2018-04-17 | 2020-07-07 | 吉林大学 | 具有室温磷光性质的噻吨酮化合物晶体及其制备方法和用途 |
CN112010843B (zh) * | 2019-05-30 | 2022-03-08 | 烟台显华光电材料研究院有限公司 | 一类用于制备有机光电器件的化合物及其应用 |
JP7404807B2 (ja) * | 2019-07-19 | 2023-12-26 | 東洋インキScホールディングス株式会社 | 熱電変換材料及び熱電変換素子 |
CN113004255B (zh) * | 2019-12-20 | 2023-08-01 | 江苏三月科技股份有限公司 | 一种以杂蒽酮为核心的化合物及其应用 |
CN113121515B (zh) * | 2019-12-30 | 2023-11-28 | 江苏三月科技股份有限公司 | 一种以二苯并五元杂环为核心的化合物及其应用 |
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US7700265B2 (en) * | 2004-03-24 | 2010-04-20 | Fujifilm Corporation | Image forming method, planographic printing plate precursor, and planographic printing method |
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