WO2010084852A1 - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- WO2010084852A1 WO2010084852A1 PCT/JP2010/050541 JP2010050541W WO2010084852A1 WO 2010084852 A1 WO2010084852 A1 WO 2010084852A1 JP 2010050541 W JP2010050541 W JP 2010050541W WO 2010084852 A1 WO2010084852 A1 WO 2010084852A1
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- Prior art keywords
- group
- light emitting
- light
- emitting device
- aryl
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- 239000000463 material Substances 0.000 title claims description 115
- -1 naphthacene compound Chemical class 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 64
- 239000010410 layer Substances 0.000 claims description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005013 aryl ether group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000000843 powder Substances 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 230000032258 transport Effects 0.000 description 30
- 238000000746 purification Methods 0.000 description 27
- 238000000859 sublimation Methods 0.000 description 27
- 230000008022 sublimation Effects 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 239000007788 liquid Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
- SSYBGLWXGRWEFE-UHFFFAOYSA-N 3-phenyl-1-benzofuran Chemical compound C=1OC2=CC=CC=C2C=1C1=CC=CC=C1 SSYBGLWXGRWEFE-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 description 5
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003518 tetracenes Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 150000004832 aryl thioethers Chemical class 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- BBJKOMQWPCRXGD-UHFFFAOYSA-N 1-phenyl-2-(4-phenylphenoxy)ethanone Chemical compound C=1C=CC=CC=1C(=O)COC(C=C1)=CC=C1C1=CC=CC=C1 BBJKOMQWPCRXGD-UHFFFAOYSA-N 0.000 description 2
- VTIPWSSYQWOADI-UHFFFAOYSA-N 1-phenylbenzo[e][1]benzofuran Chemical compound C=1OC2=CC=C3C=CC=CC3=C2C=1C1=CC=CC=C1 VTIPWSSYQWOADI-UHFFFAOYSA-N 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- OKBSDYLCRUOJQK-UHFFFAOYSA-N 2,4-bis(4-tert-butylphenyl)-1h-pyrrole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CNC(C=2C=CC(=CC=2)C(C)(C)C)=C1 OKBSDYLCRUOJQK-UHFFFAOYSA-N 0.000 description 2
- ASSYOZGBQVKGEL-UHFFFAOYSA-N 2-naphthalen-2-yloxy-1-phenylethanone Chemical compound C=1C=C2C=CC=CC2=CC=1OCC(=O)C1=CC=CC=C1 ASSYOZGBQVKGEL-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KRSXGTAVHIDVPM-UHFFFAOYSA-N 2-phenoxyacetophenone Chemical compound C=1C=CC=CC=1C(=O)COC1=CC=CC=C1 KRSXGTAVHIDVPM-UHFFFAOYSA-N 0.000 description 2
- JWIBCOLVPJOKSD-UHFFFAOYSA-N 3,5-diphenyl-1-benzofuran Chemical compound C=1OC2=CC=C(C=3C=CC=CC=3)C=C2C=1C1=CC=CC=C1 JWIBCOLVPJOKSD-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
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- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
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- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
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- 239000005361 soda-lime glass Substances 0.000 description 1
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- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical compound C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Abstract
Description
アプライド フィジクス レターズ(Applied Physics Letters)(米国)1987年,51巻,12号,p.913-915
これらの置換基のうち、アルキル基とは、例えば、メチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。置換されている場合の置換基には特に制限は無く、例えば、アルキル基、アリール基、ヘテロアリール基等を挙げることができ、この点は、以下の記載にも共通する。また、アルキル基の炭素数は特に限定されないが、入手の容易性やコストの点から、通常、1以上20以下の範囲である。より好ましくは、1以上8以下の範囲である。
本発明において、発光層は単一層、複数層のどちらでもよく、いずれもホスト材料および必要に応じドーパント材料を主成分とする発光材料により形成される。発光材料はホスト材料とドーパント材料との混合物であっても、ホスト材料単独であっても、いずれでもよい。すなわち、本発明の発光素子では、各発光層において、ホスト材料もしくはドーパント材料のみが発光してもよいし、ホスト材料とドーパント材料がともに発光してもよい。ホスト材料とドーパント材料は、それぞれ一種類であっても、複数の組み合わせであっても、いずれでもよい。ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれでもよい。ドーパント材料は積層されていても、分散されていても、いずれでもよい。ドーパント材料の量は、多すぎると濃度消光現象が起きるため、ホスト材料に対して20重量%以下で用いることが好ましく、さらに好ましくは10重量%以下である。ドーピング方法は、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。
化合物[7]の合成
フェナンシルブロマイド9.5g、フェノール6.8g、炭酸カリウム13.3gをアセトン192mLに溶解し、窒素気流下、加熱還流させながら3時間撹拌した。室温に冷却した後、水200mLを加え、ジクロロメタン150mLで抽出した。有機層を水100mlで2回洗浄し、硫酸マグネシウムで乾燥後、ロータリーエバポレーターで溶媒を留去した。得られた反応組成生物をシリカゲルカラムクロマトグラフィーにより精製し、真空乾燥した後、黄色液体9.7g(収率86%)を得た。得られた液体の1H-NMR分析結果は次の通りであり、上記で得られた黄色液体が2-フェノキシ-1-フェニルエタノンであることが確認された。
1H-NMR(CDCl3(d=ppm)):5.27(s, 2H), 6.87-7.01(m, 2H), 7.19-7.33(m, 2H), 7.47-7.65(m, 4H), 7.96-8.03(m, 2H)。
1H-NMR(CDCl3(d=ppm)):7.22-7.79(m, 8H), 7.82(s, 1H), 7.84-7.88(m, 1H)。
1H-NMR(CDCl3(d=ppm)):7.06-8.29(m, 26H), 8.50(s, 2H)。
化合物[1]の合成
ベンゾフラン5.0gを脱水エーテル169mLに溶解させ、窒素気流下、0℃でn-ブチルリチウム(1.6Mヘキサン溶液)31.7mLを滴下し、0℃にて1時間撹拌した。次いで、5,12-ナフタセンキノン3.9gの脱水エーテル溶液30mLを滴下し、1時間室温にて撹拌した後、さらに加熱還流させながら1時間撹拌した。室温に冷却した後、さらに加熱還流させながら1時間撹拌した。室温に冷却した後、0.1M塩酸水溶液70mLを加え、室温にて1時間撹拌し、トルエン300mLで抽出した。有機層を水100mlで2回洗浄し、硫酸マグネシウムで乾燥後、ロータリーエバポレーターで溶媒を留去した。得られた反応粗生成物を真空乾燥した後、赤橙色液体6.7g(収率90%)を得た。
1H-NMR(CDCl3(d=ppm)):6.72(s, 2H), 7.10-7.91(m, 16H), 8.31(s, 2H)。
化合物[16]の合成
フェナンシルブロマイド9.5g、4-ヒドロキシビフェニル8.1g、炭酸カリウム13.3gをアセトン192mLに溶解し、窒素気流下、加熱還流させながら3時間撹拌した。室温に冷却した後、水200mLを加え、ジクロロメタン150mLで抽出した。有機層を水100mlで2回洗浄し、硫酸マグネシウムで乾燥後、ロータリーエバポレーターで溶媒を留去した。得られた反応組成生物をシリカゲルカラムクロマトグラフィーにより精製し、真空乾燥した後、黄色液体12.4g(収率90%)を得た。得られた液体の1H-NMR分析結果は次の通りであり、上記で得られた黄色液体が2-(ビフェニル-4-イル-オキシ)-1-フェニルエタノンであることが確認された。
1H-NMR(CDCl3(d=ppm)):5.20(s, 2H), 6.83-7.02(m, 2H), 7.22-7.48(m, 10H), 7.86-8.01(m, 2H)。
1H-NMR(CDCl3(d=ppm)):7.22-7.48(m, 12H), 7.50(s, 1H), 7.71(s, 1H)。
1H-NMR(CDCl3(d=ppm)):7.22-7.91(m, 34H), 8.31(s, 2H)。
化合物[18]の合成
フェナンシルブロマイド9.5g、2-ヒドロキシナフタレン6.9g、炭酸カリウム13.3gをアセトン192mLに溶解し、窒素気流下、加熱還流させながら3時間撹拌した。室温に冷却した後、水200mLを加え、ジクロロメタン150mLで抽出した。有機層を水100mlで2回洗浄し、硫酸マグネシウムで乾燥後、ロータリーエバポレーターで溶媒を留去した。得られた反応組成生物をシリカゲルカラムクロマトグラフィーにより精製し、真空乾燥した後、黄色液体10.6g(収率85%)を得た。得られた液体の1H-NMR分析結果は次の通りであり、上記で得られた黄色液体が2-(ナフタレン-2-イル-オキシ)-1-フェニルエタノンであることが確認された。
1H-NMR(CDCl3(d=ppm)):5.30(s, 2H), 6.97-7.86(m, 12H)。
1H-NMR(CDCl3(d=ppm)):7.22-7.48(m, 9H), 7.51(s, 1H), 7.67(d, 2H)。
1H-NMR(CDCl3(d=ppm)):7.19-8.03(m, 30H), 8.36(s, 2H)。
化合物[6]の合成
5,12-ナフタセンキノンの代わりに、6,11-ジフェニル-5,12-ナフタセンキノンを用いた以外は、合成例2と同様な方法で合成し、橙色粉末5.5g(収率46%)を得た。得られた粉末の1H-NMR分析結果は次の通りであり、上記で得られた橙色粉末が化合物[6]であることが確認された。
1H-NMR(CDCl3(d=ppm)):6.72(s, 2H), 7.11-7.91(m, 26H)。
化合物[21]の合成
3-フェニルベンゾフランの代わりに、3-(2-ベンゾフラニル)ベンゾフランを用いた以外は、合成例1と同様な方法で合成し、橙色粉末4.1g(収率56%)を得た。得られた粉末の1H-NMR分析結果は次の通りであり、上記で得られた橙色粉末が化合物[21]であることが確認された。
1H-NMR(CDCl3(d=ppm)):6.85-8.25(m, 26H), 8.48(s, 2H)。
化合物[22]の合成
3-フェニルベンゾフランの代わりに、3-(2-ナフチル)-5-メチルベンゾフランを用いた以外は、合成例1と同様な方法で合成し、橙色粉末3.7g(収率48%)を得た。得られた粉末の1H-NMR分析結果は次の通りであり、上記で得られた橙色粉末が化合物[22]であることが確認された。
1H-NMR(CDCl3(d=ppm)):2.35(s, 6H), 6.98-8.25(m, 28H), 8.48(s, 2H)。
化合物[43]の合成
3-フェニルベンゾフランの代わりに、3-フェニル-5-フェニルベンゾチオフェンを用いた以外は、合成例1と同様な方法で合成し、橙色粉末4.5g(収率54%)を得た。得られた粉末の1H-NMR分析結果は次の通りであり、上記で得られた橙色粉末が化合物[43]であることが確認された。
1H-NMR(CDCl3(d=ppm)):7.32-8.01(m, 34H), 8.45(s, 2H)。
化合物[62]の合成
3-フェニルベンゾフランの代わりに、N-メチル-3-フェニルインドールを用いた以外は、合成例1と同様な方法で合成し、橙色粉末3.5g(収率52%)を得た。得られた粉末の1H-NMR分析結果は次の通りであり、上記で得られた橙色粉末が化合物[62]であることが確認された。
1H-NMR(CDCl3(d=ppm)):3.60(s, 6H), 6.81-8.05(m, 26H), 8.41(s, 2H)。
化合物[94]の合成
特開2005-53900号公報記載の方法に従い合成した。2-(2-メトキシベンゾイル)-3,5-ビス(4-t-ブチルフェニル)ピロール4.7g、2,4-ビス(4-t-ブチルフェニル)ピロール3.3gを1,2-ジクロロエタン30mLに溶解し、オキシ塩化リン1.5gを加え、加熱還流下12時間反応させた。室温に冷却後、ジイソプロピルエチルアミン5.2g、三フッ化ホウ素ジエチルエーテル錯体5.6gを加え、6時間撹拌した。50mLの水を加え、ジクロロメタンを投入後、有機層を抽出し、濃縮した。粗生成物をシリカゲルクロマトグラフィーにより精製し、化合物[94]4.5gを得た。
化合物[93]の合成
特開2005-53900号公報記載の方法に従い合成した。2-(4-メトキシベンゾイル)-3,5-ビス(4-t-ブチルフェニル)ピロール4.7g、2,4-ビス(4-t-ブチルフェニル)ピロール3.3gを1,2-ジクロロエタン30mLに溶解し、オキシ塩化リン1.5gを加え、加熱還流下12時間反応させた。室温に冷却後、ジイソプロピルエチルアミン5.2g、三フッ化ホウ素ジエチルエーテル錯体5.6gを加え、6時間撹拌した。50mLの水を加え、ジクロロメタンを投入後、有機層を抽出し、濃縮した。粗生成物をシリカゲルクロマトグラフィーにより精製し、化合物[93]5.0gを得た。
化合物[7]および化合物[94]を用いた発光素子を次のように作製した。30×40mmのガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)上にITO導電膜をガラス基板中央部分に150nmの厚さで30×13mmの大きさに形成し陽極とした。陽極が形成された基板を“セミコクリン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを10nm、正孔輸送材料として、4,4’-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニルを50nm蒸着した。次に、発光材料として、ホスト材料として化合物[7]を、ドーパント材料として化合物[94](1.0×10-6mol/Lジクロロメタン溶液状態での蛍光ピーク波長:612nm)をドープ濃度が0.5重量%になるように40nmの厚さに蒸着した。次に、電子輸送材料として、下記に示すE-1を35nmの厚さに積層した。次に、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。この発光素子からは、発光効率4.5lm/Wの高効率赤色発光が得られた。この発光素子は、40mA/cm2で直流駆動したところ、輝度半減時間は3,500時間であった。
ホスト材料として1,4-ジケト-2,5-ビス(3,5-ジメチルベンジル)-3,6-ビス(4-メチルフェニル)ピロロ[3,4-c]ピロール(以下、H-1とする)を用いた以外は、実施例1と同様にして発光素子を作製した。この素子からは、発光効率2.5lm/Wの赤色発光が得られた。この発光素子は、40mA/cm2で直流駆動したところ、輝度半減時間は600時間であった。なお、H-1は、EP公開公報0133156号の実施例に従い合成したものを用いた。
ホスト材料として下記に示すH-2を用いた以外は、実施例1と同様にして発光素子を作製した。この素子からは、発光効率2.2lm/Wの桃色発光が得られた。この発光素子は、40mA/cm2で直流駆動したところ、輝度半減時間は400時間であった。なお、H-2は、市販品(東京化成工業株式会社製)を用いた。
ホスト材料として下記に示すH-3を用いた以外は、実施例1と同様にして発光素子を作製した。この素子からは、発光効率3.0lm/Wの桃色発光が得られた。この発光素子は、40mA/cm2で直流駆動したところ、輝度半減時間は900時間であった。なお、H-3は、国際公開第2007/097178号パンフレットの製造例1に従い合成したものを用いた。
ホスト材料、ドーパント材料、電子輸送材料として表1に示す材料を用いた以外は、実施例1と同様にして発光素子を作製した。なお、実施例15の化合物[64]は、市販品(Pyrromethene546;米国Exciton社製)を用いた。
ホスト材料、ドーパント材料、電子輸送材料として表1に示す材料を用いた以外は、実施例1と同様にして発光素子を作製した。
Claims (7)
- 一般式(1)で表されるナフタセン化合物を含有することを特徴とする発光素子材料。
- 前記一般式(1)のR11およびR16が、アリール基またはヘテロアリール基であることを特徴とする請求項1記載の発光素子材料。
- 前記一般式(1)のXが酸素原子であることを特徴とする請求項1または2記載の発光素子材料。
- 陽極と陰極との間に少なくとも有機層が存在し、電気エネルギーにより発光する発光素子であって、前記陽極と陰極の間のいずれかの層に請求項1~3のいずれか記載の発光素子材料を含有することを特徴とする発光素子。
- 有機層が一般式(1)で表されるナフタセン化合物と蛍光ピーク波長が500nm以上680nm以下の有機蛍光物質を含むことを特徴とする請求項4記載の発光素子。
- 蛍光ピーク波長が500nm以上680nm以下の有機蛍光物質が一般式(2)で表されるピロメテン骨格を有する化合物であることを特徴とする請求項5記載の発光素子。
- 有機層と陰極の間にさらに少なくとも電子輸送層が存在し、電子輸送層が電子受容性窒素を有するヘテロアリール環からなる化合物を含有し、ヘテロアリール環からなる化合物が炭素、水素、窒素、酸素、ケイ素、リンから選ばれる一つ以上の元素で構成されていることを特徴とする請求項4~6のいずれか記載の発光素子。
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CN112403522B (zh) * | 2020-11-12 | 2021-11-23 | 江南大学 | 介孔槲皮素锆催化剂及其在制备α,β-不饱和醇中的应用 |
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WO2013146117A1 (ja) * | 2012-03-26 | 2013-10-03 | 東レ株式会社 | 発光素子材料および発光素子 |
JPWO2013146117A1 (ja) * | 2012-03-26 | 2015-12-10 | 東レ株式会社 | 発光素子材料および発光素子 |
WO2014010611A1 (ja) * | 2012-07-13 | 2014-01-16 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
WO2016027675A1 (ja) * | 2014-08-20 | 2016-02-25 | 東レ株式会社 | 光電変換素子ならびにそれを用いたイメージセンサ、太陽電池、単色検知センサおよびフレキシブルセンサ |
JPWO2016027675A1 (ja) * | 2014-08-20 | 2017-06-01 | 東レ株式会社 | 光電変換素子ならびにそれを用いたイメージセンサ、太陽電池、単色検知センサおよびフレキシブルセンサ |
JP2017019761A (ja) * | 2015-07-15 | 2017-01-26 | 国立大学法人山形大学 | 新規ターピリジン誘導体、それを用いた電子輸送材料及び有機el素子 |
JP2019520349A (ja) * | 2016-06-03 | 2019-07-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 電気活性化合物 |
Also Published As
Publication number | Publication date |
---|---|
EP2383813A1 (en) | 2011-11-02 |
US20110272681A1 (en) | 2011-11-10 |
TW201035285A (en) | 2010-10-01 |
JPWO2010084852A1 (ja) | 2012-07-19 |
CN102272971A (zh) | 2011-12-07 |
JP5408124B2 (ja) | 2014-02-05 |
KR20110117063A (ko) | 2011-10-26 |
CN102272971B (zh) | 2015-05-27 |
EP2383813A4 (en) | 2012-08-01 |
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