WO2012144176A1 - ピレン誘導体、有機発光媒体、及びこれらを含む有機エレクトロルミネッセンス素子 - Google Patents
ピレン誘導体、有機発光媒体、及びこれらを含む有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2012144176A1 WO2012144176A1 PCT/JP2012/002578 JP2012002578W WO2012144176A1 WO 2012144176 A1 WO2012144176 A1 WO 2012144176A1 JP 2012002578 W JP2012002578 W JP 2012002578W WO 2012144176 A1 WO2012144176 A1 WO 2012144176A1
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- 150000003220 pyrenes Chemical class 0.000 title claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 186
- 125000003118 aryl group Chemical group 0.000 claims abstract description 74
- -1 phenyl-substituted anthracene Chemical class 0.000 claims abstract description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 238000005401 electroluminescence Methods 0.000 claims description 40
- 125000006413 ring segment Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 14
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 95
- 239000000463 material Substances 0.000 description 43
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 230000032258 transport Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 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 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 0 **c1c(*)c(c(*)c2*)c3c4c2c(*(*2*)c(c(*)c5*=C)c2c(*)c5O)c(*)c(*)c4c(*)c(*)c3c1*(c(c(*)c(*)c(*)c1*)c1I)N Chemical compound **c1c(*)c(c(*)c2*)c3c4c2c(*(*2*)c(c(*)c5*=C)c2c(*)c5O)c(*)c(*)c4c(*)c(*)c3c1*(c(c(*)c(*)c(*)c1*)c1I)N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 2
- NCLGCNZJCGGRIX-UHFFFAOYSA-N 2,5-diphenylaniline Chemical compound NC1=CC(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 NCLGCNZJCGGRIX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
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- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 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
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CCNJFKWGDDTZOR-UHFFFAOYSA-N n,2,5-triphenylaniline Chemical compound C=1C(C=2C=CC=CC=2)=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 CCNJFKWGDDTZOR-UHFFFAOYSA-N 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YGLVWOUNCXBPJF-UHFFFAOYSA-N (2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene Chemical compound C1=CC=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YGLVWOUNCXBPJF-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- YFCSASDLEBELEU-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene-11,12,15,16,17,18-hexacarbonitrile Chemical group N#CC1=C(C#N)C(C#N)=C2C3=C(C#N)C(C#N)=NN=C3C3=NN=NN=C3C2=C1C#N YFCSASDLEBELEU-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- OZJYZNVZBUZORU-UHFFFAOYSA-N 4-(4-aminophenyl)aniline;1,1'-biphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 OZJYZNVZBUZORU-UHFFFAOYSA-N 0.000 description 1
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- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZPHVSXGHKIGKCI-UHFFFAOYSA-N Fc1cc(-c2ccccc2)cc(-c2ccccc2)c1N(c1ccccc1)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c(c(-c1ccccc1)cc(-c1ccccc1)c1)c1F Chemical compound Fc1cc(-c2ccccc2)cc(-c2ccccc2)c1N(c1ccccc1)c1ccc(cc2)c3c1ccc(cc1)c3c2c1N(c1ccccc1)c(c(-c1ccccc1)cc(-c1ccccc1)c1)c1F ZPHVSXGHKIGKCI-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
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- 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Definitions
- the present invention relates to a pyrene derivative, an organic light emitting medium, and an organic electroluminescence device including these.
- Organic electroluminescence (EL) devices using organic substances are promising for use as solid-state, inexpensive, large-area full-color display devices, and many developments have been made.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- Patent Documents 1 to 3 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant, but further improvement in light emission characteristics (high light emission efficiency, long life, etc.) is required.
- the present invention has been made to solve the above-described problems, and an object thereof is to provide a highly efficient and long-life organic EL element.
- the present inventors have found that an organic light-emitting medium using a pyrene derivative having a specific structure at a specific position and a phenyl-substituted anthracene derivative exhibits high luminous efficiency and has a long lifetime.
- the organic electroluminescent element which used the organic thin film which consists of the organic luminescent medium for a light emitting layer discovered that it was highly efficient and long-lived, and completed this invention.
- organic light-emitting medium comprising a pyrene derivative represented by the following formula (1) and a phenyl-substituted anthracene derivative represented by the following formula (2).
- Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms
- X 1 to X 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring formation
- Ar 11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms, m is an integer from 0 to 3, and when m is 0, Ar 11 is a single bond;
- Ar 12 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, n is an integer of 1 to 3, When m or n is 2 or more, the plurality of Ar 11 and Ar 12 may be the same or different.
- Ar 12 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted benzphenanthrenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzofura 12.
- Ar 1 to Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms
- X 1 to X 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring formation
- One or more organic thin film layers including a light emitting layer are sandwiched between the cathode and the anode, 16.
- An organic electroluminescence device, wherein the light emitting layer comprises the organic light emitting medium according to any one of 1 to 14 or the pyrene derivative according to 15.
- an organic light-emitting medium, an organic thin film, and an organic EL element with high efficiency and long life can be provided.
- the organic light-emitting medium of the present invention includes a pyrene derivative represented by the following formula (1) and a phenyl-substituted anthracene derivative represented by the following formula (2).
- the pyrene derivative represented by the formula (1) functions as a doping material (dopant)
- the phenyl-substituted anthracene derivative represented by the following formula (2) functions as a host material.
- Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms
- X 1 to X 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring formation
- An aralkyl group, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 and R 7 and R 8 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring. Or a substituted or unsubstituted heterocycle.
- Ar 11 represents a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms (aromatic hydrocarbon group) or a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms (aromatic group).
- n is an integer of 1 to 3
- the plurality of Ar 11 and Ar 12 may be the same or different.
- ring-forming carbon means a carbon atom constituting a saturated aliphatic cyclic structure, an unsaturated aliphatic cyclic structure, or an aromatic hydrocarbon cyclic structure composed of carbon and hydrogen.
- Ring-forming atom means a carbon atom and a hetero atom constituting a saturated aliphatic cyclic structure, an unsaturated aliphatic cyclic structure, and an aromatic heterocyclic structure containing a hetero atom.
- the “hydrocarbon ring” includes a saturated aliphatic cyclic structure, an unsaturated aliphatic cyclic structure, or an aromatic hydrocarbon cyclic structure composed of carbon and hydrogen, and the “heterocycle” refers to a heteroatom. Including saturated aliphatic cyclic structures, unsaturated aliphatic cyclic structures, and aromatic heterocyclic structures.
- the corresponding isotopes are included in all atoms constituting the pyrene derivative represented by the formula (1) and the phenyl-substituted anthracene derivative represented by the formula (2).
- the aryl group having 6 to 30 ring carbon atoms in Ar 1 to Ar 4 , X 1 to X 8, R 1 to R 8, and Ar 12 includes a non-condensed aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms And a condensed aromatic hydrocarbon ring group having 10 to 30 ring carbon atoms and a ring assembly aromatic hydrocarbon ring group having 9 to 30 ring carbon atoms.
- non-condensed aromatic hydrocarbon ring means a group in which a plurality of aromatic rings (single ring and / or condensed ring) are bonded by a single bond
- condensed aromatic hydrocarbon ring Means a ring in which a plurality of aromatic rings are bonded by two or more common ring-forming carbon atoms
- ring-aggregated aromatic hydrocarbon ring means that an aromatic ring and an aliphatic ring are 2 Means a ring that is joined by two or more common ring-forming carbon atoms.
- aryl group having 6 to 30 ring carbon atoms include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, chrysenyl group, fluorenyl group, benzo [c] phenanthryl group, benzo [g ] Include a chrycenyl group, a triphenylenyl group, a 9,9-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a biphenylyl group, a terphenylyl group, and a fluoranthenyl group.
- a phenyl group, a biphenylyl group, a tolyl group, a xylyl group, and a naphthyl group are particularly preferable.
- the number of ring-forming carbon atoms of the aryl group is preferably 6-18, and more preferably 6-10.
- the heteroaryl group having 5 to 20 ring atoms in Ar 1 to Ar 4 and Ar 12 is a non-condensed aromatic heterocyclic group having 5 to 20 ring atoms and a condensed aromatic group having 10 to 20 ring atoms.
- Heterocyclic groups and ring-assembled aromatic heterocyclic groups having 9 to 20 ring-forming atoms are included.
- the “non-condensed aromatic heterocycle” means a group in which two or more aromatic rings (single ring and / or condensed ring) including one or more aromatic heterocycles are bonded by a single bond.
- fused aromatic heterocycle means a ring in which two or more aromatic rings including one or more aromatic heterocycles are bonded by two or more common ring-forming atoms;
- ring-aggregated aromatic hydrocarbon ring means a ring in which one or more aromatic heterocycles and an aliphatic ring are bonded by two or more common carbon atoms.
- heteroaryl group having 5 to 20 ring atoms include pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzo Thiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthronyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, flazanyl group, thienyl group, Examples include 2-methylpyrrolyl group, triazinyl group, pyrimidinyl group and the like. A dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group
- Examples of the alkyl group having 1 to 20 carbon atoms in X 1 to X 8 and R 1 to R 8 include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t- Examples include a butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and the like.
- methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl are preferred.
- the number of carbon atoms is preferably 1 to 10, more preferably 1 to 8, and still more preferably 1 to 6.
- Examples of the cycloalkyl group having 3 to 20 ring carbon atoms in X 1 to X 8 and R 1 to R 8 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, 1 -Norbornyl group, 2-norbornyl group and the like.
- the number of ring-forming carbon atoms is preferably 3 to 10, more preferably 3 to 8, and further preferably 3 to 6.
- alkyl-substituted silyl group is represented by —SiY 3, and examples of the alkyl group having 1 to 20 carbon atoms are given as Y. Specific examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group. Group, propyldimethylsilyl group and the like.
- the aryl-substituted silyl group is represented as —SiZ 3, and examples of Z include the aryl groups having 6 to 18 ring carbon atoms in the examples of the aryl groups having 6 to 30 ring carbon atoms described above. Examples thereof include a triphenylsilyl group, a phenyldimethylsilyl group, a t-butyldiphenylsilyl group, a tolylsilylsilyl group, and a trixylsilyl group.
- the alkyl- and aryl-substituted silyl group is represented by —SiY n Z (3-n) (n is 1 or 2), and examples of the alkyl group having 1 to 20 carbon atoms are given as Y.
- Examples of the aryl group having 6 to 30 ring carbon atoms include aryl groups having 6 to 18 ring carbon atoms, and specific examples thereof are as described above.
- the alkoxy group having 1 to 20 carbon atoms in X 1 to X 8 and R 1 to R 8 is represented as —OY, and examples of Y include the above alkyl groups having 1 to 20 carbon atoms. Specifically, Methoxy group, ethoxy group, butoxy group and the like.
- the aryloxy group having 6 to 30 ring carbon atoms in X 1 to X 8 and R 1 to R 8 is represented by —OZ, and examples of the aryl group having 6 to 30 ring carbon atoms are given as Z. Specific examples include a phenoxy group.
- the aralkyl group having 6 to 30 ring carbon atoms in X 1 to X 8 and R 1 to R 8 is represented by —YZ, and Y is an alkylene corresponding to the above examples of alkyl groups having 1 to 20 carbon atoms.
- Examples of the group are given, and examples of Z include the above-mentioned aryl groups having 6 to 30 ring carbon atoms. Specific examples include benzyl group, phenylethyl group, 2-phenylpropan-2-yl group and the like.
- halogen atom in X 1 to X 8 examples include fluorine, chlorine, bromine, iodine and the like, preferably a fluorine atom.
- the halogenated alkyl group having 1 to 20 carbon atoms in X 1 to X 8 is preferably a fluorinated alkyl group having 1 to 20 carbon atoms, specifically, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, Examples include a fluoroethyl group and a trifluoromethylmethyl group.
- the arylene group having 6 to 30 ring carbon atoms in Ar 11 is represented by —Z—, and examples of Z include arylene groups corresponding to the above examples of aryl groups having 6 to 30 ring carbon atoms.
- the heteroarylene group having 5 to 20 ring atoms in Ar 11 is represented by —P—, and examples of P include heteroarylene groups corresponding to the above examples of heteroaryl groups having 5 to 20 ring atoms.
- substituents in the above-mentioned “substituted or unsubstituted” groups include alkyl groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, and / or ring-forming carbon atoms having 6 to 18 carbon atoms as described above.
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 and R 7 and R 8 are bonded to each other.
- a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring are bonded to each other.
- Specific hydrocarbon rings formed include a naphthyl group, a phenanthryl group, a pyrenyl group, a 9,9-dimethylfluorenyl group, and the like.
- Specific heterocycles formed include benzofuranyl group, dibenzofuranyl group, benzothienyl group, dibenzothienyl group, 1-arylindolyl group, 9-arylcarbazolyl group and the like.
- m represents the number of repetitions of Ar 11 and is an integer of 0 to 3, preferably an integer of 0 to 2.
- the plurality of Ar 11 may be the same as or different from each other.
- Ar 11 is a single bond.
- n represents the number of substitutions of Ar 12 with Ar 11 and is an integer of 1 to 3, preferably an integer of 1 to 2.
- the plurality of Ar 12 may be the same as or different from each other.
- n is 1 and Ar 12 is bonded to the anthracene skeleton.
- X 2 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted carbon.
- An aryl group, and X 1 and X 3 to X 8 are hydrogen atoms;
- X 2 and X 6 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring formed cycloalkyl group having 3 to 10 carbon atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and / or a substituted or unsubstituted ring forming aryl group having 6 to 18 carbon atoms or an unsubstituted silyl group, or a substituted or unsubstituted ring forming An aryl group having 6 to 30 carbon atoms, and X 1 , X 3 , X 4 , X 5 , X 7 and X 8 are hydrogen atoms;
- the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms of X 2 and X 6 is preferably an alkyl group having 1 to 6 carbon atoms.
- X 2 and X 6 substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms and / or substituted or unsubstituted aryl groups having 6 to 18 ring carbon atoms are preferably substituted or unsubstituted silyl groups.
- X 1 to X 8 are hydrogen atoms.
- X 2 and X 6 are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted.
- a substituted cycloalkyl group having 3 to 20 ring carbon atoms, and X 1 , X 3 to X 5 , X 7 and X 8 are hydrogen atoms.
- Ar 3 and Ar 4 are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms.
- R 3 and R 7 , or R 2 and R 6 are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms.
- the other R 1 to R 8 are hydrogen.
- Ar 3 and Ar 4 are substituted or unsubstituted phenyl groups.
- R 3 and R 7 , or R 2 and R 6 are substituted or unsubstituted phenyl groups.
- the other R 1 to R 8 are hydrogen.
- Ar 1 and Ar 2 , Ar 3 and Ar 4 , R 1 and R 5 , R 2 and R 6 , R 3 and R 7 , R 4 in view of ease of synthesis and the like. and at least one or more R 8, X 1 and X 5, X 2 and X 6, X 3 and X 7, X 4 and X 8 are, (a point symmetry) more preferably all the same.
- m is 1 and n is 1.
- Ar 11 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms
- Ar 12 is a substituted or unsubstituted ring.
- An aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms is preferable.
- Ar 11 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalenylene group.
- Ar 11 is a substituted or unsubstituted phenylene group
- Ar 12 is a substituted or unsubstituted naphthyl group.
- Ar 12 is preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.
- Ar 12 is substituted or unsubstituted naphthyl group, substituted or unsubstituted benzanthracenyl group, substituted or unsubstituted benzphenanthrenyl group, substituted or unsubstituted phenanthryl group, or substituted or unsubstituted More preferably, it is a dibenzofuranyl group.
- the present invention further provides a compound of the following formula (10):
- the compound of the formula (10) can be used together with the derivative of the formula (2).
- the derivative of formula (2) functions as a host material
- the compound of formula (10) functions as a dopant material.
- Ar 1 ⁇ Ar 4, X 1 ⁇ X 8 is abbreviated to a respective same description as the Ar 1 ⁇ Ar 4, X 1 ⁇ X 8 of the formula (1).
- Ar 5 and Ar 6 are the same as Ar 1 to Ar 4 in the formula (1) and will not be described.
- R 11 , R 12 , R 14 to R 16 and R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon atom having 3 to 20 carbon atoms.
- R 11 , R 12 , R 14 to R 16 and R 18 have an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkyl group having 1 to 20 carbon atoms and / or a ring forming carbon.
- the silyl group substituted or unsubstituted with an aryl group having 6 to 18 carbon atoms, the aralkyl group with 6 to 30 ring carbon atoms, and the substituents substituted on these groups include the corresponding group of formula (1) and Each of them is the same as the substituent and will not be described.
- Ar 5 and Ar 6 are preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and more preferably a substituted or unsubstituted phenyl group.
- R 11 , R 12 , R 14 to R 16 and R 18 are preferably hydrogen. Also, preferably, R 12 and R 16 are preferably a substituted or unsubstituted ring aryl group having 6 to 30, more preferably a substituted or unsubstituted phenyl group. In this case, preferably the other R 11 , R 12 , R 14 to R 16 and R 18 are hydrogen.
- the compound of the above formula (10) in which Ar 5 and Ar 6 (particularly phenyl) are bonded to the m-position is more effective against the amine moiety than the compound in which Ar 5 and Ar 6 are bonded to the p-position. Since the spread of all conjugated systems is small and the electron donating property to the amine portion is kept low, the color purity is improved because the wavelength tends to be shortened. In addition, the planarity of the molecular structure is three-dimensionally high, and energy exchange with the host atom is considered to be performed efficiently, which tends to improve efficiency.
- An organic light-emitting medium using at least one of the pyrene derivatives represented by the above formula (1) as a doping material (dopant) and using at least one of the phenyl-substituted anthracene derivatives represented by the above formula (2) as a host material It has the characteristics of high luminous efficiency and long life, and when used as a light emitting layer of an organic electroluminescence element or the like, a light emitting efficiency and long life element can be obtained.
- the organic light-emitting medium of the present invention contains various materials in addition to the pyrene derivative and the phenyl-substituted anthracene derivative in order to make the light-emitting medium having a high efficiency and a long life without impairing the effect. be able to.
- the material that can be contained will be described later in the description of the organic electroluminescence element of the present invention.
- organic electroluminescence element of the present invention In the organic electroluminescence element of the present invention (hereinafter referred to as the organic EL element of the present invention), one or more organic thin film layers including at least a light emitting layer are sandwiched between a cathode and an anode.
- the light emitting layer contains the organic light emitting medium of the present invention or the pyrene derivative of the formula (10).
- the light emitting layer contains the pyrene derivative of the formula (10)
- the light emitting layer is An organic layer having a light emitting function, and when a doping system is employed, includes a host material and a dopant material.
- the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
- the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
- an organic thin film layer As a method for forming the organic thin film layer, a known method such as a vapor deposition method, a spin coating method, or an LB method can be applied.
- An organic thin film layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution and then reducing the film by a spin coating method or the like.
- a binder such as a resin and a material compound in a solvent
- reducing the film by a spin coating method or the like.
- organic EL elements having a plurality of organic thin film layers include (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), and (anode / hole injection layer).
- / Emission layer / electron injection layer / cathode (anode / hole injection layer / hole transport layer / emission layer / electron injection layer / cathode), (anode / hole injection layer / hole transport layer / emission layer / And those laminated in a structure such as an electron transport layer / electron injection layer / cathode).
- the organic EL device of the present invention can have a tandem device configuration having at least two light emitting layers.
- An example of a specific configuration is shown below.
- Anode / first light emitting layer / intermediate layer / second light emitting layer / electron transport zone / cathode Anode / first light emitting layer / electron transport zone / intermediate layer / second light emitting layer / cathode
- Anode / first light emitting layer / electron transport zone / Intermediate layer / second light emitting layer / electron transport zone / cathode anode / first light emitting layer / intermediate layer / second light emitting layer / electron transport zone / cathode anode / first light emitting layer / electron transport zone / intermediate layer / second Light emitting layer / cathode anode / first light emitting layer / electron transport zone / intermediate layer / second Light emitting layer / cathode
- An organic EL element can prevent a decrease in luminance and lifetime due to quenching by forming a plurality of organic thin film layers.
- Each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed of two or more layers.
- the layer that injects holes from the electrode is a hole injection layer
- the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
- an electron injection layer a layer that injects electrons from an electrode is referred to as an electron injection layer
- a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
- Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
- Examples of the material that can be used in the organic light emitting medium of the present invention or the light emitting layer that does not use the pyrene derivative of the formula (10) include, for example, naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenyl Condensed polycyclic aromatic compounds such as cyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, triarylamine derivatives, styrylamine derivatives, stilbene derivatives, Coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives,
- a hole injection material a compound having the ability to transport holes, the hole injection effect from the anode, the hole injection effect excellent for the light emitting layer or the light emitting material, and the thin film forming ability Is preferred.
- phthalocyanine derivatives naphthalocyanine derivatives, porphyrin derivatives, benzidine-type triphenylamine, diamine-type triphenylamine, hexacyanohexaazatriphenylene, and derivatives thereof, and polyvinylcarbazole, polysilane, conductive polymers, etc. Examples include, but are not limited to, polymer materials.
- a more effective hole injection material is a phthalocyanine derivative.
- phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.
- carriers can be sensitized by adding an electron acceptor such as a TCNQ derivative to the hole injection material.
- a preferred hole transport material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative.
- the aromatic tertiary amine derivative include N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra Biphenyl-1,1′-biphenyl-4,4′-diamine or the like, or an oligomer or polymer having an aromatic tertiary amine skeleton is not limited thereto.
- the electron injecting material a compound having an ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable.
- more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.
- the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, and bis.
- (10-Hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, and the like are exemplified, but not limited thereto.
- these electron injection materials further contain a dopant, and more preferably, a dopant typified by an alkali metal is doped in the vicinity of the cathode interface of the second organic layer in order to facilitate the reception of electrons from the cathode.
- the dopant include a donor metal, a donor metal compound, and a donor metal complex. These reducing dopants may be used singly or in combination of two or more.
- a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. It is also possible to do.
- a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
- the conductive material used for the cathode those having a work function smaller than 4 eV are suitable, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these.
- alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.
- the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
- the substrate is also preferably transparent.
- the transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering.
- the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
- the substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
- Each layer of the organic EL device of the present invention can be formed by applying any one of dry deposition methods such as vacuum deposition, sputtering, plasma and ion plating, and wet deposition methods such as spin coating, dipping and flow coating. Can do.
- the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
- the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
- the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
- an organic EL material containing a pyrene derivative represented by the formula (1), a phenyl-substituted anthracene derivative represented by the formula (2) and a solvent as an organic EL material A solution can be used.
- an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
- Example 1 A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm. This transparent electrode serves as an anode. Subsequently, the glass substrate was cleaned by irradiating ultraviolet rays and ozone, and then the substrate was placed in a vacuum deposition apparatus. Compound HT-1 was deposited as a hole injection layer on the anode to a thickness of 50 nm, and then compound HT-2 was deposited as a hole transport layer thereon to a thickness of 45 nm.
- an anthracene derivative EM-1 as a host material and a compound D-1 as a doping material were co-evaporated at a mass ratio of 25: 5 to form a light emitting layer having a thickness of 30 nm.
- the compound ET-1 was deposited to a thickness of 25 nm as an electron injection layer.
- lithium fluoride was deposited to a thickness of 1 nm, and then aluminum was deposited to a thickness of 150 nm to produce an organic EL device.
- the aluminum / lithium fluoride serves as a cathode.
- Compound HT-1, Compound HT-2, and Compound ET-1 used in the production of the organic EL device are compounds having the following structures, respectively.
- the method for measuring the external quantum yield is as follows. A current having a current density of 10 mA / cm 2 was passed through the obtained organic EL device, the emission spectrum was measured with a spectral radiance meter (CS1000: manufactured by Minolta), and the external quantum yield was calculated according to the following formula.
- N P Number of photons
- N E Number of electrons
- ⁇ Emission intensity (W / sr ⁇ m 2 ⁇ nm)
- J Current density (mA / cm 2 )
- Examples 2 to 15 and Comparative Examples 1 to 11 An organic EL device was produced in the same manner as in Example 1 except that the doping material and the host material were changed to the compounds shown in Table 1, and the external quantum yield (%) and lifetime (time) were evaluated. The results are shown in Table 1.
- the carrier balance is improved, so that a highly efficient and long-life organic EL element can be obtained. It is thought.
- the organic light-emitting medium of the present invention is useful for producing a highly efficient and long-life organic EL device.
- the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a backlight of a liquid crystal display or a light source of an instrument, a display board, a sign, and the like.
- the organic light-emitting medium of the present invention can be used not only in organic EL elements but also in fields such as electrophotographic photoreceptors, photoelectric conversion elements, solar cells, and image sensors.
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Abstract
Description
例えば、特許文献1~3には、特定の構造のアントラセンホストとジアミノピレンドーパントとの組み合わせが開示されているが、さらなる発光特性の向上(高発光効率、長寿命等)が要求されている。
本発明者らは、特定の位置に特定の構造を有するピレン誘導体と、フェニル置換アントラセン誘導体を用いた有機発光媒体が、高い発光効率を示し、かつ長寿命であることを見出した。そして、その有機発光媒体からなる有機薄膜を発光層に用いた有機エレクトロルミネッセンス素子が、高効率かつ長寿命であることを見出し、本発明を完成させた。
1.下記式(1)で表されるピレン誘導体及び下記式(2)で表されるフェニル置換アントラセン誘導体を含む有機発光媒体。
X1~X8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の環形成炭素数6~30のアラルキル基、ハロゲン原子、又は置換若しくは無置換の炭素数1~20のハロゲン化アルキル基であり、
R1~R8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、又は置換若しくは無置換の環形成炭素数6~30のアラルキル基であり、
R1とR2、R2とR3、R3とR4、R5とR6、R6とR7及びR7とR8は、それぞれ互いに結合して置換若しくは無置換の炭化水素環、又は置換若しくは無置換の複素環を形成してもよい。]
mは、0~3の整数であり、mが0の場合はAr11は単結合であり、
Ar12は、置換若しくは無置換の環形成炭素数6~30のアリール基、又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基であり、
nは、1~3の整数であり、
m又はnが2以上の場合、複数のAr11及びAr12はそれぞれ同一でも異なっていてもよい。]
2.X1~X8が水素原子である1に記載の有機発光媒体。
3.X2及びX6が置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、又は置換若しくは無置換の環形成炭素数3~20のシクロアルキル基であり、X1、X3~X5、X7及びX8が水素原子である1に記載の有機発光媒体。
4.Ar3及びAr4が置換若しくは無置換の環形成炭素数6~30のアリール基である1~3のいずれかに記載の有機発光媒体。
5.R3及びR7、又はR2及びR6が、置換若しくは無置換の環形成炭素数6~30のアリール基である1~4のいずれかに記載の有機発光媒体。
6.Ar3及びAr4が置換若しくは無置換のフェニル基である4又は5に記載の有機発光媒体。
7.R3及びR7、又はR2及びR6が置換若しくは無置換のフェニル基である5又は6に記載の有機発光媒体。
8.mが1、かつnが1である1~7のいずれかに記載の有機発光媒体。
9.mが0、かつnが1である1~7のいずれかに記載の有機発光媒体。
10.Ar11が置換若しくは無置換の環形成炭素数6~18のアリーレン基又は置換若しくは無置換の環形成原子数5~20のヘテロアリーレン基であり、Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基である8に記載の有機発光媒体。
11.Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基である9に記載の有機発光媒体。
12.Ar11が置換若しくは無置換のフェニレン基、又は置換もしくは無置換のナフタレニレン基である10に記載の有機発光媒体。
13.Ar12が置換もしくは無置換のナフチル基、置換若しくは無置換のベンズアントラセニル基、置換若しくは無置換のベンズフェナントレニル基、置換若しくは無置換のフェナントリル基、又は置換若しくは無置換のジベンゾフラニル基である11に記載の有機発光媒体。
14.Ar11が置換若しくは無置換のフェニレン基であり、Ar12が置換若しくは無置換のナフチル基である12に記載の有機発光媒体。
15. 下記式(10)で表されるピレン誘導体。
X1~X8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の環形成炭素数6~30のアラルキル基、ハロゲン原子、又は置換若しくは無置換の炭素数1~20のハロゲン化アルキル基であり、
R11、R12、R14~R16及びR18は、それぞれ独立に水素原子、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、又は置換若しくは無置換の環形成炭素数6~30のアラルキル基である。]
16.陰極と陽極の間に、発光層を含む1以上の有機薄膜層が狭持され、
前記発光層が、1~14のいずれか記載の有機発光媒体又は15記載のピレン誘導体を含む有機エレクトロルミネッセンス素子。
I.有機発光媒体
本発明の有機発光媒体は、下記式(1)で表されるピレン誘導体及び下記式(2)で表されるフェニル置換アントラセン誘導体を含むことを特徴とする。
ここで、式(1)で表されるピレン誘導体はドーピング材料(ドーパント)として、下記式(2)で表されるフェニル置換アントラセン誘導体はホスト材料として機能する。
X1~X8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の環形成炭素数6~30のアラルキル基、ハロゲン原子、又は置換若しくは無置換の炭素数1~20のハロゲン化アルキル基であり、
R1~R8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~3018のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、又は置換若しくは無置換の環形成炭素数6~30のアラルキル基であり、
R1とR2、R2とR3、R3とR4、R5とR6、R6とR7及びR7とR8は、それぞれ互いに結合して置換若しくは無置換の炭化水素環、又は置換若しくは無置換の複素環を形成してもよい。]
mは、0~3の整数であり、mが0の場合はAr11は単結合であり、
Ar12は、置換若しくは無置換の環形成炭素数6~30のアリール基、又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基であり、
nは、1~3の整数であり、
m又はnが2以上の場合、複数のAr11及びAr12はそれぞれ同一でも異なっていてもよい。]
また、「炭化水素環」は、炭素と水素からなる、飽和脂肪族環式構造、不飽和脂肪族環式構造、又は芳香族炭化水素環式構造を含み、「複素環」は、ヘテロ原子を含む、飽和脂肪族環式構造、不飽和脂肪族環式構造、及び芳香族複素環式構造を含む。
環形成炭素数6~30のアリール基の具体例としては、フェニル基、ナフチル基、アントリル基、フェナントリル基、ナフタセニル基、ピレニル基、クリセニル基、フルオレニル基、ベンゾ[c]フェナントリル基、ベンゾ[g]クリセニル基、トリフェニレニル基、9、9-ジメチルフルオレニル基、ベンゾフルオレニル基、ジベンゾフルオレニル基、ビフェニルイル基、ターフェニルイル基、フルオランテニル基等が挙げられる。上述したアリール基の中でもフェニル基、ビフェニルイル基、トリル基、キシリル基、ナフチル基が特に好ましい。前記アリール基の環形成炭素数は、6~18が好ましく、6~10がさらに好ましい。
環形成原子数5~20のヘテロアリール基の具体例としては、ピロリル基、ピラジニル基、ピリジニル基、インドリル基、イソインドリル基、フリル基、ベンゾフラニル基、イソベンゾフラニル基、ジベンゾフラニル基、ジベンゾチオフェニル基、キノリル基、イソキノリル基、キノキサリニル基、カルバゾリル基、フェナントリジニル基、アクリジニル基、フェナントロニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、オキサゾリル基、オキサジアゾリル基、フラザニル基、チエニル基、2-メチルピロリル基、トリアジニル基、ピリミジニル基等が挙げられる。好ましくは、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基である。前記ヘテロアリール基の環形成原子数は、5~14が好ましい。
アルキル置換されたシリル基は、-SiY3と表され、Yとして前記の炭素数1~20のアルキル基の例が挙げられ、具体的には、トリメチルシリル基、トリエチルシリル基、t-ブチルジメチルシリル基、プロピルジメチルシリル基等が挙げられる。
アリール置換されたシリル基は、-SiZ3と表され、Zとして前記の環形成炭素数6~30のアリール基の例のうちの環形成炭素数6~18のアリール基が挙げられ、具体的には、トリフェニルシリル基、フェニルジメチルシリル基、t-ブチルジフェニルシリル基、トリトリルシリル基、トリキシリルシリル基等が挙げられる。
アルキル及びアリール置換されたシリル基は、-SiYnZ(3-n)(nは1又は2)と表され、Yとして前記の炭素数1~20のアルキル基の例が挙げられ、Zとして前記の環形成炭素数6~30のアリール基の例のうちの環形成炭素数6~18のアリール基が挙げられ、具体例は、上記の通りである。
このとき、Ar11が置換若しくは無置換の環形成炭素数6~18のアリーレン基又は置換若しくは無置換の環形成原子数5~20のヘテロアリーレン基であり、Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基であることが好ましい。
Ar11が置換若しくは無置換のフェニレン基、又は置換もしくは無置換のナフタレニレン基であることがより好ましい。
Ar11が置換若しくは無置換のフェニレン基であり、Ar12が置換若しくは無置換のナフチル基であることがさらに好ましい。
このとき、Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基であることが好ましい。
さらに、Ar12が置換もしくは無置換のナフチル基、置換若しくは無置換のベンズアントラセニル基、置換若しくは無置換のベンズフェナントレニル基、置換若しくは無置換のフェナントリル基、又は置換若しくは無置換のジベンゾフラニル基であることがより好ましい。
Ar5、Ar6は、式(1)のAr1~Ar4と同じであり説明を略する。
また、好ましくは、R12及びR16は、好ましくは置換若しくは無置換の環形成炭素数6~30のアリール基であり、より好ましくは置換若しくは無置換のフェニル基である。この場合、好ましくは他のR11、R12、R14~R16及びR18は水素である。
尚、本発明の有機発光媒体には、その効果を損なわず、またさらに高効率で長寿命な発光媒体とするために、上記ピレン誘導体及びフェニル置換アントラセン誘導体の他に、各種の材料を含有させることができる。含有させることができる材料については、本発明の有機エレクトロルミネッセンス素子の説明において後述する。
本発明の有機エレクトロルミネッセンス素子(以下、本発明の有機EL素子という)は、陰極と陽極の間に少なくとも発光層を含む1以上の有機薄膜層が狭持されている。
発光層が本発明の有機発光媒体又は式(10)のピレン誘導体を含む。発光層が式(10)のピレン誘導体を含むとき、ホスト材料として式(2)の誘導体を共に含むことが好ましい。
発光機能を有する有機層であって、ドーピングシステムを採用する場合、ホスト材料とドーパント材料を含んでいる。このとき、ホスト材料は、主に電子と正孔の再結合を促し、励起子を発光層内に閉じ込める機能を有し、ドーパント材料は、再結合で得られた励起子を効率的に発光させる機能を有する。
複数の有機薄膜層を形成する場合、同一の方法のみで形成してもよいし、二つ又は二つ以上の方法を用いて形成してもよい。
本発明の有機EL素子は、発光層を少なくとも2つ有するタンデム素子構成とすることができる。具体的な構成の例を以下に示す。
陽極/第1発光層/中間層/第2発光層/電子輸送帯域/陰極
陽極/第1発光層/電子輸送帯域/中間層/第2発光層/陰極
陽極/第1発光層/電子輸送帯域/中間層/第2発光層/電子輸送帯域/陰極
陽極/第1発光層/中間層/第2発光層/電子輸送帯域/陰極
陽極/第1発光層/電子輸送帯域/中間層/第2発光層/陰極
陽極/第1発光層/電荷障壁層/第2発光層/電子輸送帯域/陰極
陽極/第1発光層/電荷障壁層/第2発光層/第3発光層/電子輸送帯域/陰極
本発明の有機発光媒体又は式(10)のピレン誘導体は、これらの発光層の一つ又は2以上の発光層に用いることができる。また他の発光層は他の蛍光発光性の材料を用いた有機発光媒体や燐光発光性の材料を用いた有機発光媒体を用いることができる。
上記の化合物は、本発明の目的を損なわない範囲で、本発明の有機発光媒体又は式(10)のピレン誘導体を用いる発光層にも、加えて用いることができる。
また、正孔注入材料にTCNQ誘導体等の電子受容物質を添加することによりキャリアを増感させることもできる。
芳香族三級アミン誘導体としては、例えば、N,N’-ジフェニル-N,N’-ジナフチル-1,1’-ビフェニル-4,4’-ジアミン、N,N,N’,N’-テトラビフェニル-1,1’-ビフェニル-4,4’-ジアミン等、又はこれらの芳香族三級アミン骨格を有したオリゴマー若しくはポリマーであるが、これらに限定されるものではない。
前記金属錯体化合物としては、例えば、8-ヒドロキシキノリナートリチウム、ビス(8-ヒドロキシキノリナート)亜鉛、トリス(8-ヒドロキシキノリナート)アルミニウム、トリス(8-ヒドロキシキノリナート)ガリウム、ビス(10-ヒドロキシベンゾ[h]キノリナート)ベリリウム、ビス(10-ヒドロキシベンゾ[h]キノリナート)亜鉛等が挙げられるが、これらに限定されるものではない。
好ましい形態として、これらの電子注入材料にさらにドーパントを含有し、陰極からの電子の受け取りを容易にするため、より好ましくは第2有機層の陰極界面近傍にアルカリ金属で代表されるドーパントをドープする。
ドーパントとしては、ドナー性金属、ドナー性金属化合物及びドナー性金属錯体が挙げられ、これら還元性ドーパントは1種単独で使用してもよいし、2種以上を組み合わせて使用してもよい。
このような湿式成膜法に適した溶液として、有機EL材料として式(1)で表されるピレン誘導体、式(2)で表されるフェニル置換アントラセン誘導体及び溶媒とを含有する有機EL材料含有溶液を用いることができる。
2,5-ジブロモアニリン(150g、0.598mol)、フェニルボロン酸(160g、1.79mol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(27.6g、0.0234mol)、2M炭酸ナトリウム水溶液(900mL、1.80mol)及び1,2-ジメトキシエタン(3.5L)の混合物を、アルゴン雰囲気下、75℃にて23時間撹拌した。反応混合物を室温に冷却し、水を加え、析出した固体を濾取した。得られた固体をシリカゲルカラムクロマトグラフィーで精製し、目的とする2,5-ジフェニルアニリン119g(81%)を得た。
ブロモベンゼン(36.4g、232mmol)、(a)で合成した2,5-ジフェニルアニリン(114g、464mmol)、酢酸パラジウム(II)(1.56g、6.96mmol)、BINAP(2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル)ラセミ体、8,67g、13.9mmol)及びトルエン1.5Lの混合物を、アルゴン気流下にて90℃に加熱し、ナトリウム-tert-ブトキシド(44.6g、464mmol)を加えた後、アルゴン雰囲気下にて105℃で5時間攪拌を行った。反応混合物を室温に冷却し、水を加えて分液を行った。得られた有機層の溶媒を減圧濃縮し、得られた固体をシリカゲルカラムクロマトグラフィーで精製し、目的とするN-フェニル-2,5-ジフェニルアニリン66.6g(収率85%)を得た。
1,6-ジブロモピレン(23.2g、64.5mmol)、(b)で合成したN-フェニル-2,5-ジフェニルアニリン(45.6g、142mmol)、酢酸パラジウム(0.6g、2.67mmol)、トリ-tert-ブチルホスフィン(1.08g、5.33mmol)及びトルエン(700ml)の混合物を、アルゴン気流下にて90℃に加熱し、ナトリウム-tert-ブトキシド(15.4g、160mmol)を加えた後、アルゴン雰囲気下にて105℃で3時間攪拌を行った。反応混合物を室温に冷却し、精製した固体を濾取した。得られた固体をシリカゲルクロマトグラフィーで精製し、次いで再結晶により精製し、目的とする化合物D-1を33.7g(収率62%)得た。
得られた化合物は、マススペクトル分析の結果、化合物D-1と同定した(分子量840.35に対しm/e=840)。
25mm×75mm×1.1mmサイズのガラス基板上に、膜厚120nmのインジウムスズ酸化物からなる透明電極を設けた。この透明電極は、陽極として働く。続いて、このガラス基板に紫外線及びオゾンを照射して洗浄したのち、真空蒸着装置にこの基板を設置した。
陽極上に正孔注入層として、化合物HT-1を50nmの厚さに蒸着したのち、その上に正孔輸送層として、化合物HT-2を45nmの厚さに蒸着した。次いで、ホスト材料であるアントラセン誘導体EM-1と、ドーピング材料である化合物D-1とを、質量比25:5で同時蒸着し、厚さ30nmの発光層を形成した。この発光層上に、電子注入層として、化合物ET-1を25nmの厚さに蒸着した。次に、弗化リチウムを1nmの厚さに蒸着し、次いでアルミニウムを150nmの厚さに蒸着し、有機EL素子を作製した。尚、このアルミニウム/弗化リチウムは陰極として働く。
得られた有機EL素子に電流密度10mA/cm2の電流を通電し、分光放射輝度計(CS1000:ミノルタ製)で発光スペクトルを測定し、下記数式により外部量子収率を算出した。
NE:電子数
π:円周率=3.1416
λ:波長(nm)
φ:発光強度(W/sr・m2・nm)
h:プランク定数=6.63x10-34(J・s)
c:光速度=3x108(m/s)
J:電流密度(mA/cm2)
e:電荷=1.6x10-19(C)
ドーピング材料及びホスト材料を表1に示す化合物に変更した以外は実施例1と同様にして有機EL素子を製造し、外部量子収率(%)及び寿命(時間)を評価した。結果を表1に示す。
本発明の有機EL素子は、壁掛けテレビのフラットパネルディスプレイ等の平面発光体、複写機、プリンター、液晶ディスプレイのバックライト又は計器類の光源、表示板、標識等に利用できる。
また、本発明の有機発光媒体は、有機EL素子だけでなく、電子写真感光体、光電変換素子、太陽電池、イメージセンサー等の分野においても使用できる。
この明細書に記載の文献の内容を全てここに援用する。
Claims (16)
- 下記式(1)で表されるピレン誘導体及び下記式(2)で表されるフェニル置換アントラセン誘導体を含む有機発光媒体。
X1~X8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の環形成炭素数6~30のアラルキル基、ハロゲン原子、又は置換若しくは無置換の炭素数1~20のハロゲン化アルキル基であり、
R1~R8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、又は置換若しくは無置換の環形成炭素数6~30のアラルキル基であり、
R1とR2、R2とR3、R3とR4、R5とR6、R6とR7及びR7とR8は、それぞれ互いに結合して置換若しくは無置換の炭化水素環、又は置換若しくは無置換の複素環を形成してもよい。]
mは、0~3の整数であり、mが0の場合はAr11は単結合であり、
Ar12は、置換若しくは無置換の環形成炭素数6~30のアリール基、又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基であり、
nは、1~3の整数であり、
m又はnが2以上の場合、複数のAr11及びAr12はそれぞれ同一でも異なっていてもよい。] - X1~X8が水素原子である請求項1に記載の有機発光媒体。
- X2及びX6が置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、又は置換若しくは無置換の環形成炭素数3~20のシクロアルキル基であり、X1、X3~X5、X7及びX8が水素原子である請求項1に記載の有機発光媒体。
- Ar3及びAr4が置換若しくは無置換の環形成炭素数6~30のアリール基である請求項1~3のいずれかに記載の有機発光媒体。
- R3及びR7、又はR2及びR6が、置換若しくは無置換の環形成炭素数6~30のアリール基である請求項1~4のいずれかに記載の有機発光媒体。
- Ar3及びAr4が置換若しくは無置換のフェニル基である請求項4又は5に記載の有機発光媒体。
- R3及びR7、又はR2及びR6が置換若しくは無置換のフェニル基である請求項5又は6に記載の有機発光媒体。
- mが1、かつnが1である請求項1~7のいずれかに記載の有機発光媒体。
- mが0、かつnが1である請求項1~7のいずれかに記載の有機発光媒体。
- Ar11が置換若しくは無置換の環形成炭素数6~18のアリーレン基又は置換若しくは無置換の環形成原子数5~20のヘテロアリーレン基であり、Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基である請求項8に記載の有機発光媒体。
- Ar12が置換若しくは無置換の環形成炭素数6~18のアリール基又は置換若しくは無置換の環形成原子数5~20のヘテロアリール基である請求項9に記載の有機発光媒体。
- Ar11が置換若しくは無置換のフェニレン基、又は置換もしくは無置換のナフタレニレン基である請求項10に記載の有機発光媒体。
- Ar12が置換もしくは無置換のナフチル基、置換若しくは無置換のベンズアントラセニル基、置換若しくは無置換のベンズフェナントレニル基、置換若しくは無置換のフェナントリル基、又は置換若しくは無置換のジベンゾフラニル基である請求項11に記載の有機発光媒体。
- Ar11が置換若しくは無置換のフェニレン基であり、Ar12が置換若しくは無置換のナフチル基である請求項12に記載の有機発光媒体。
- 下記式(10)で表されるピレン誘導体。
X1~X8は、それぞれ独立に水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~20のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の環形成炭素数6~30のアラルキル基、ハロゲン原子、又は置換若しくは無置換の炭素数1~20のハロゲン化アルキル基であり、
R11、R12、R14~R16及びR18は、それぞれ独立に水素原子、置換若しくは無置換の炭素数1~20のアルキル基、置換若しくは無置換の環形成炭素数3~20のシクロアルキル基、置換若しくは無置換の炭素数1~20のアルキル基及び/又は置換若しくは無置換の環形成炭素数6~18のアリール基で置換された若しくは無置換のシリル基、又は置換若しくは無置換の環形成炭素数6~30のアラルキル基である。] - 陰極と陽極の間に、発光層を含む1以上の有機薄膜層が狭持され、
前記発光層が、請求項1~14のいずれか記載の有機発光媒体又は請求項15記載のピレン誘導体を含む有機エレクトロルミネッセンス素子。
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KR20140031213A (ko) | 2014-03-12 |
US10014476B2 (en) | 2018-07-03 |
TW201247601A (en) | 2012-12-01 |
US20180309058A1 (en) | 2018-10-25 |
US10964891B2 (en) | 2021-03-30 |
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