JP2013043845A - 縮合多環化合物及びこれを有する有機発光素子 - Google Patents
縮合多環化合物及びこれを有する有機発光素子 Download PDFInfo
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- JP2013043845A JP2013043845A JP2011181580A JP2011181580A JP2013043845A JP 2013043845 A JP2013043845 A JP 2013043845A JP 2011181580 A JP2011181580 A JP 2011181580A JP 2011181580 A JP2011181580 A JP 2011181580A JP 2013043845 A JP2013043845 A JP 2013043845A
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- light emitting
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- organic light
- condensed polycyclic
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- -1 polycyclic compound Chemical class 0.000 title claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 91
- 150000002894 organic compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 9
- 239000003086 colorant Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 182
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- 239000000463 material Substances 0.000 description 105
- 239000000243 solution Substances 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
- 239000002904 solvent Substances 0.000 description 37
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 235000002597 Solanum melongena Nutrition 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000003153 chemical reaction reagent Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 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 14
- 125000001424 substituent group Chemical group 0.000 description 14
- BVRDQVRQVGRNHG-UHFFFAOYSA-N 2-morpholin-4-ylpyrimido[2,1-a]isoquinolin-4-one Chemical compound N1=C2C3=CC=CC=C3C=CN2C(=O)C=C1N1CCOCC1 BVRDQVRQVGRNHG-UHFFFAOYSA-N 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
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- 230000000903 blocking effect Effects 0.000 description 12
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- 238000000859 sublimation Methods 0.000 description 12
- 230000008022 sublimation Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 125000005580 triphenylene group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- 238000002189 fluorescence spectrum Methods 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 7
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- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 5
- 125000005577 anthracene group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 5
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- 229910014265 BrCl Inorganic materials 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- TUDNMLBIHIWVJM-UHFFFAOYSA-N 2-amino-5-bromo-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=C(Br)C=C1C(O)=O TUDNMLBIHIWVJM-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- HXKTUOWCXCHYIH-UHFFFAOYSA-N cyclopenta[cd]pyrene-3,4-dione Chemical compound C=1C(C(C2=O)=O)=C3C2=CC=C(C=C2)C3=C3C2=CC=CC3=1 HXKTUOWCXCHYIH-UHFFFAOYSA-N 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000005581 pyrene group Chemical group 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CESUFNSEOLEPAN-UHFFFAOYSA-N 2-(2-bromophenyl)naphthalene Chemical compound BrC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 CESUFNSEOLEPAN-UHFFFAOYSA-N 0.000 description 2
- GXKIUSDWRQAIID-UHFFFAOYSA-N 2-(6-tert-butyl-6-chlorocyclohexa-2,4-dien-1-yl)naphthalene Chemical compound CC(C)(C)C1(Cl)C=CC=CC1C1=CC=C(C=CC=C2)C2=C1 GXKIUSDWRQAIID-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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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- 125000003277 amino group Chemical group 0.000 description 2
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
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- 239000009719 polyimide resin Substances 0.000 description 1
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class 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
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- 238000004528 spin coating Methods 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- BZFGOJWFHZOKQJ-UHFFFAOYSA-N undecacyclo[36.3.1.02,27.04,25.06,23.07,12.013,22.015,20.028,41.031,40.034,39]dotetraconta-1(42),2,4,6(23),7,9,11,13,15,17,19,21,24,26,28(41),29,31(40),32,34(39),35,37-henicosaene Chemical compound C=1C(C=2C=C3C=C4C5=CC=CC=C5C=5C(C4=CC3=CC=22)=CC3=CC=CC=C3C=5)=C3C2=CC=C(C=C2)C3=C3C2=CC=CC3=1 BZFGOJWFHZOKQJ-UHFFFAOYSA-N 0.000 description 1
- FJQSIGOOWWAUKG-UHFFFAOYSA-N undecacyclo[36.3.1.02,27.04,25.06,23.07,16.09,14.017,22.028,41.031,40.034,39]dotetraconta-1(42),2,4,6(23),7,9,11,13,15,17,19,21,24,26,28(41),29,31(40),32,34(39),35,37-henicosaene Chemical compound [CH]1C2=C(C=C3C(C=C4C5=CC=CC=C5C=5C(C4=C3)=CC3=CC=CC=C3C=5)=C3)C3=C(C=C3)C2=C2C3=CC=C3[C]2C1=CC=C3 FJQSIGOOWWAUKG-UHFFFAOYSA-N 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
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- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G15/00—Apparatus for electrographic processes using a charge pattern
- G03G15/04—Apparatus for electrographic processes using a charge pattern for exposing, i.e. imagewise exposure by optically projecting the original image on a photoconductive recording material
- G03G15/04036—Details of illuminating systems, e.g. lamps, reflectors
- G03G15/04045—Details of illuminating systems, e.g. lamps, reflectors for exposing image information provided otherwise than by directly projecting the original image onto the photoconductive recording material, e.g. digital copiers
- G03G15/04054—Details of illuminating systems, e.g. lamps, reflectors for exposing image information provided otherwise than by directly projecting the original image onto the photoconductive recording material, e.g. digital copiers by LED arrays
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Abstract
【解決手段】下記一般式[1]または[2]で示される縮合多環化合物を提供する。
〔式[1]及び[2]において、R1乃至R10は水素原子、直鎖または分枝状の炭素原子数1乃至4のアルキル基、置換あるいは無置換の炭素原子数6乃至22の芳香族炭化水素基からなる群よりそれぞれ独立に選ばれる。〕
【選択図】なし
Description
本発明に係る縮合多環化合物は下記に示すベンゾ[6’,7’]トリフェニレノ[2’,3’:5,6]インデノ[1,2,3−cd]ピレン(以下、BTIPy(a)と略記)またはベンゾ[10’,11’]トリフェニレノ[2’,3’:5,6]インデノ[1,2,3−cd]ピレン(以下、BTIPy(b)と略記)を主骨格として有する。
以下に本発明に係る縮合多環化合物の具体的な構造式を例示する。なお、例示化合物101(a)と例示化合物101(b)は互いにジアステレオマーの関係であり、他の例示化合物も同様である。
次に、本実施の形態に係る式[1]または[2]で示される縮合多環化合物の合成方法について説明する。
次に本発明に係る有機発光素子を説明する。
(1)陽極/発光層/陰極
(2)陽極/正孔輸送層/発光層/電子輸送層/陰極
(3)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(5)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(6)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
ただしこれらの素子構成例はあくまでごく基本的な素子構成であり、本発明に係る化合物を用いた有機発光素子の構成はこれらに限定されるものではない。
本実施形態に係る有機発光素子は、表示装置や照明装置に用いることができる。他にも電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライトなどに用いることができる。
(1)中間体BrCl−1の合成
シクロペンタ[cd]ピレン−3,4−ジオン:4.00g(15.6mmol)
ジイソブチルケトン:4.44g(31.2mmol)
エタノール:60mL
この反応液に、水酸化カリウム0.88g(15.6mmol)をエタノール15mLに溶解させた溶液を、室温にてゆっくり滴下して加えて、さらに10時間撹拌を続けた。
中間体PyK−1:1.97g(5.43mmol)
5−ブロモ−4−クロロアントラニル酸:1.50g(5.97mmol)
トルエン:100mL
1−ブロモ−2−ヨードベンゼン:2.00g(7.07mmol)
2−ナフタレンボロン酸:1.28g(7.42mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):245mg(0.212mmol)
トルエン:40mL
エタノール:20mL
10wt%炭酸ナトリウム水溶液:20mL
この反応溶液を、窒素下、撹拌しながら3時間半加熱還流させた。反応終了後、反応溶液を飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
BrCl−1:400mg(0.764mmol)
NpPh−1:200mg(0.802mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):26mg(23μmol)
トルエン:12mL
エタノール:6mL
30wt%炭酸セシウム水溶液:6mL
この反応溶液を、窒素下、撹拌しながら3時間加熱還流させた。反応終了後、トルエンで生成物を抽出し、飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
NpPhCl−1:365mg(0.550mmol)
酢酸パラジウム:7.4mg(33μmol)
トリシクロヘキシルホスホニウムテトラフルオロほう酸塩:24mg(66μmol)
炭酸カリウム:152mg(1.10mmol)
[MALDI−TOF−MS(マトリックス支援イオン化−飛行時間型質量分析)]
実測値:m/z=610.48 計算値:C48H34=610.27
また例示化合物104のトルエン希薄溶液について、室温下、励起波長350nmにおいて蛍光スペクトルの測定を行った。得られた蛍光スペクトルの最大発光ピークのピーク波長は488nmであった。
(1)中間体BrCl−2の合成
シクロペンタ[cd]ピレン−3,4−ジオン:3.00g(11.7mmol)
1,3−ビス(3,5−tert−ブチルフェニル)プロパン−2−オン:5.09g(11.7mmol)
エタノール:45mL
この反応液を70℃に加熱し、水酸化カリウム0.66g(11.7mmol)をエタノール12mLに溶解させた溶液を加えて、さらに4時間撹拌しながら加熱した。
中間体PyK−2:1.50g(2.29mmol)
5−ブロモ−4−クロロアントラニル酸:631mg(2.52mmol)
トルエン:75mL
BrCl−2:500mg(0.612mmol)
NpPh−1:160mg(0.643mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):21mg(18μmol)
トルエン:16mL
エタノール:8mL
30wt%炭酸セシウム水溶液:8mL
この反応溶液を、窒素下、撹拌しながら4時間加熱還流させた。反応終了後、トルエンで生成物を抽出し、飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
NpPhCl−2:407mg(0.433mmol)
酢酸パラジウム:6mg(27μmol)
トリシクロヘキシルホスホニウムテトラフルオロほう酸塩:20mg(54μmol)
炭酸カリウム:120mg(0.866mmol)
[MALDI−TOF−MS]
実測値:m/z=902.67 計算値:C70H62=902.49
また例示化合物205のトルエン希薄溶液について、室温下、励起波長350nmにおいて蛍光スペクトルの測定を行った。得られた蛍光スペクトルの最大発光ピークのピーク波長は490nmであった。
(1)中間体BrCl−3の合成
シクロペンタ[cd]ピレン−3,4−ジオン:3.00g(11.7mmol)
1,3−ジフェニルプロパン−2−オン:2.46g(11.7mmol)
エタノール:45mL
この反応液を70℃に加熱し、水酸化カリウム0.66g(11.7mmol)をエタノール12mLに溶解させた溶液を加えて、さらに3時間撹拌しながら加熱した。
中間体PyK−2:2.00g(4.65mmol)
5−ブロモ−4−クロロアントラニル酸:1.28g(5.11mmol)
トルエン:100mL
2−ブロモ−4−tert−ブチル−1−クロロベンゼン:1.00g(4.04mmol)
2−ナフタレンボロン酸:0.729g(4.24mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):140mg(0.121mmol)
トルエン:30mL
エタノール:15mL
10wt%炭酸ナトリウム水溶液:15mL
この反応溶液を、窒素下、撹拌しながら4時間加熱還流させた。反応終了後、反応溶液を飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
2−(2−tert−ブチル−2−クロロフェニル)ナフタレン:965mg(3.27mmol)
ビス(ピナコラト)ジボロン:996mg(3.92mmol)
ビス(ジベンジリデンアセトン)パラジウム(0):94mg(0.163mmol)
トリシクロヘキシルホスフィン:138mg(0.490mmol)
酢酸カリウム:642mg(6.54mmol)
1,4−ジオキサン:30mL
この反応溶液を、窒素下、95℃で7時間撹拌を行った。反応終了後、反応溶液を水で洗浄し、硫酸ナトリウム上で乾燥させた後に濃縮し粗生成物を得た。
BrCl−3:450mg(0.760mmol)
NpPh−2:308mg(0.798mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):26mg(23μmol)
トルエン:14mL
エタノール:7mL
30wt%炭酸セシウム水溶液:7mL
この反応溶液を、窒素下、撹拌しながら3時間半加熱還流させた。反応終了後、トルエンで生成物を抽出し、飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
NpPhCl−3:497mg(0.631mmol)
酢酸パラジウム:8.5mg(38μmol)
トリシクロヘキシルホスホニウムテトラフルオロほう酸塩:28mg(76μmol)
炭酸カリウム:174mg(1.26mmol)
[MALDI−TOF−MS(マトリックス支援イオン化−飛行時間型質量分析)]
実測値:m/z=734.46 計算値:C58H38=734.30
また例示化合物303のトルエン希薄溶液について、室温下、励起波長350nmにおいて蛍光スペクトルの測定を行った。得られた蛍光スペクトルの最大発光ピークのピーク波長は491nmであった。
(1)中間体NpPh−3の合成
3−ブロモ−4−クロロ−1’,1’−ビフェニル:1.30g(4.86mmol)
2−ナフタレンボロン酸:0.877g(5.10mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):168mg(0.146mmol)
トルエン:40mL
エタノール:20mL
10wt%炭酸ナトリウム水溶液:20mL
この反応溶液を、窒素下、撹拌しながら5時間加熱還流させた。反応終了後、反応溶液を飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
2−(4−クロロ−[1’,1’−ビフェニル]−3−イル)ナフタレン:1.22g(3.88mmol)
ビス(ピナコラト)ジボロン:1.18g(4.66mmol)
ビス(ジベンジリデンアセトン)パラジウム(0):112mg(0.194mmol)
トリシクロヘキシルホスフィン:163mg(0.582mmol)
酢酸カリウム:762mg(7.76mmol)
1,4−ジオキサン:40mL
この反応溶液を、窒素下、95℃で9時間撹拌を行った。反応終了後、反応溶液を水で洗浄し、硫酸ナトリウム上で乾燥させた後に濃縮し粗生成物を得た。
BrCl−2:500mg(0.612mmol)
NpPh−3:261mg(0.643mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):21mg(18μmol)
トルエン:16mL
エタノール:8mL
30wt%炭酸セシウム水溶液:8mL
この反応溶液を、窒素下、撹拌しながら4時間半加熱還流させた。反応終了後、トルエンで生成物を抽出し、飽和NaCl水溶液で洗浄した後、硫酸ナトリウム上で乾燥させてから濃縮して粗生成物を得た。
NpPhCl−4:537mg(0.520mmol)
酢酸パラジウム:7mg(31μmol)
トリシクロヘキシルホスホニウムテトラフルオロほう酸塩:23mg(62μmol)
炭酸カリウム:144mg(1.04mmol)
[MALDI−TOF−MS]
実測値:m/z=978.72 計算値:C76H66=978.52
また例示化合物401のトルエン希薄溶液について、室温下、励起波長350nmにおいて蛍光スペクトルの測定を行った。得られた蛍光スペクトルの最大発光ピークのピーク波長は500nmであった。
下記に示す比較化合物C01及びC02について、実施例1と同様の方法で蛍光スペクトルの測定を行い、最大発光ピークのピーク波長を測定した。実施例1乃至4の結果と合わせて、結果を表2に示す。
本実施例では、基板上に順次陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極が設けられた構成(6)の有機発光素子を以下に示す方法で作製した。
正孔輸送層(40nm) HT−1
電子阻止層(25nm) EB−1
発光層(30nm) ホスト材料:H9、ゲスト材料:例示化合物104(1wt%)
正孔阻止層(10nm) HB−1
電子輸送層(30nm) ET−1
金属電極層1(0.5nm) LiF
金属電極層2(100nm) Al
実施例5において、発光層ホスト材料をH9に代えてH11を、発光層ゲスト材料を例示化合物104に代えて例示化合物205を使用した他は、実施例5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5と同様に評価を行った。結果を表3に示す。
実施例5において、発光層ホスト材料をH9に代えてH14を、発光層ゲスト材料を例示化合物104に代えて例示化合物303を使用した他は、実施例5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5と同様に評価を行った。結果を表3に示す。
実施例5において、発光層ホスト材料をH9に代えてH11を、発光層ゲスト材料を例示化合物104に代えて例示化合物401を使用した他は、実施例5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5と同様に評価を行った。結果を表3に示す。
実施例5において、発光層ホスト材料をH9に代えてH14を、発光層ゲスト材料を例示化合物104に代えて比較化合物C2を使用した他は、実施例5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5と同様に評価を行った。結果を表3に示す。
本実施例では、基板上に順次陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極が設けられた構成(6)の有機発光素子において、発光層が青色発光層、緑色発光層及び赤色発光層の三層からなる、積層発光層型の白色発光素子を以下に示す方法で作製した。
正孔輸送層(30nm) HT−1
電子阻止層(10nm) EB−1
青色発光層(10nm) ホスト材料:H14、ゲスト材料:BD−1(1wt%)
緑色発光層(10nm) ホスト材料:H11、ゲスト材料:例示化合物205(1wt%)
赤色発光層(7nm) ホスト材料:H11、ゲスト材料:RD−1(0.5wt%)
正孔阻止層(10nm) HB−1
電子輸送層(30nm) ET−1
金属電極層1(0.5nm) LiF
金属電極層2(100nm) Al
5 緑色発光層
6 赤色発光層
17 TFT素子
20 陽極
21 有機化合物層
22 陰極
Claims (9)
- 下記一般式[1]または[2]で示されることを特徴とする縮合多環化合物。
〔式[1]及び[2]において、R1乃至R10は水素原子、直鎖または分枝状の炭素原子数1乃至4のアルキル基、置換あるいは無置換の炭素原子数6乃至22の芳香族炭化水素基からなる群よりそれぞれ独立に選ばれる。〕 - 前記一般式[1]または[2]で示される縮合多環化合物は、下記一般式[3]または[4]で示される化合物であることを特徴とする請求項1に記載の縮合多環化合物。
〔式[3]及び[4]において、X1乃至X10は水素原子、直鎖または分枝状の炭素原子数1乃至4のアルキル基、置換あるいは無置換のフェニル基からなる群よりそれぞれ独立に選ばれる。〕 - 一対の電極と前記一対の電極の間に配置されている有機化合物層とを有する有機発光素子において、前記有機化合物層は請求項1または2に記載の縮合多環化合物を有することを特徴とする有機発光素子。
- 前記有機化合物層は、発光層を有し、前記発光層はホストとゲストとを有し、前記ゲストが前記縮合多環化合物であることを特徴とする請求項3に記載の有機発光素子。
- 前記有機化合物層は、発光部を有し、前記発光部は複数の発光層を有し、
前記複数の発光層のうちの少なくともひとつは前記縮合多環化合物を有し、
前記複数の発光層は、それぞれの発光層がそれぞれ異なる発光色を発する発光層であり、
前記異なる発光色の混色により白色を発することを特徴とする請求項3または4に記載の有機発光素子。 - 前記有機化合物層は複数の発光層を有し、前記複数の発光層のうちの少なくともいずれかひとつは、前記縮合多環化合物を有する緑色を発する発光層であり、
前記緑色と前記緑色を発する発光層以外の発光層の発光色との混色により白色を発することを特徴とする請求項3または4に記載の有機発光素子。 - 複数の画素を有し、前記画素は請求項3乃至6の何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されてい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、前記表示部は複数の画素を有し、前記画素は請求項3乃至6の何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されてい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3乃至6に記載の有機発光素子と前記有機発光素子に接続されているインバータ回路とを有することを特徴とする照明装置。
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