JP5780664B2 - アントラセン誘導体 - Google Patents
アントラセン誘導体 Download PDFInfo
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- JP5780664B2 JP5780664B2 JP2008319547A JP2008319547A JP5780664B2 JP 5780664 B2 JP5780664 B2 JP 5780664B2 JP 2008319547 A JP2008319547 A JP 2008319547A JP 2008319547 A JP2008319547 A JP 2008319547A JP 5780664 B2 JP5780664 B2 JP 5780664B2
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- 150000001454 anthracenes Chemical class 0.000 title claims description 118
- 239000010410 layer Substances 0.000 description 245
- 239000000126 substance Substances 0.000 description 85
- 238000003786 synthesis reaction Methods 0.000 description 69
- 230000015572 biosynthetic process Effects 0.000 description 67
- 238000000034 method Methods 0.000 description 67
- 150000002894 organic compounds Chemical class 0.000 description 63
- 239000000463 material Substances 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- -1 biphenyl-4,4′-diyl group Chemical group 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 41
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
- 230000005525 hole transport Effects 0.000 description 31
- 239000000758 substrate Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000010408 film Substances 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 0 CC[n](c(cccc1)c1c1c2)c1ccc2-c(cc1)ccc1-c(cc1)ccc1-c1c(cccc2)c2c(-c(cc2)ccc2-c(cc2)ccc2-c2ccc(C(C)(C)*)cc2)c2c1cccc2 Chemical compound CC[n](c(cccc1)c1c1c2)c1ccc2-c(cc1)ccc1-c(cc1)ccc1-c1c(cccc2)c2c(-c(cc2)ccc2-c(cc2)ccc2-c2ccc(C(C)(C)*)cc2)c2c1cccc2 0.000 description 22
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000002131 composite material Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 239000002019 doping agent Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000000295 emission spectrum Methods 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 238000005859 coupling reaction Methods 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 238000006722 reduction reaction Methods 0.000 description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 239000011630 iodine Substances 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- DDCOSPFEMPUOFY-UHFFFAOYSA-N 9-phenyl-3-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 DDCOSPFEMPUOFY-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000002484 cyclic voltammetry Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 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 7
- 238000004528 spin coating Methods 0.000 description 7
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 7
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 6
- LDFCHUHQZQRSHF-UHFFFAOYSA-N 9-(4-bromophenyl)-10-phenylanthracene Chemical compound C1=CC(Br)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 LDFCHUHQZQRSHF-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 150000001543 aryl boronic acids Chemical class 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- 230000005281 excited state Effects 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- 238000010549 co-Evaporation Methods 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 4
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 4
- OGKISBUNKZIGIR-UHFFFAOYSA-N 9,10-bis(4-bromophenyl)-2-tert-butylanthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC(Br)=CC=2)C2=CC(C(C)(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 OGKISBUNKZIGIR-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 3
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 3
- QNZJXQPLZAOZLQ-UHFFFAOYSA-N 9-iodo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(I)=C2C=CC=CC2=C1C1=CC=CC=C1 QNZJXQPLZAOZLQ-UHFFFAOYSA-N 0.000 description 3
- LUBXLGUQZVKOFP-UHFFFAOYSA-N 9-phenylanthracene Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LUBXLGUQZVKOFP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- YNDGEMZBYUVHTH-UHFFFAOYSA-N [4-(10-phenylanthracen-9-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YNDGEMZBYUVHTH-UHFFFAOYSA-N 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- DHPCJDYBIIWSPN-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1c(cc(cc2)-c3ccccc3)c2c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2c3c4cccc3)ccc2[n]4-c2ccccc2)c2c1ccc(-c1ccccc1)c2 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1c(cc(cc2)-c3ccccc3)c2c(-c(cc2)ccc2-c(cc2)ccc2-c(cc2c3c4cccc3)ccc2[n]4-c2ccccc2)c2c1ccc(-c1ccccc1)c2 DHPCJDYBIIWSPN-UHFFFAOYSA-N 0.000 description 1
- KLVDTYVBWSVMMU-UHFFFAOYSA-N c(cc1)ccc1-c1cc2c(-c3ccccc3)c(ccc(-c3ccccc3)c3)c3c(-c(cc3)ccc3-c(cc3)cc4c3[nH]c3c4cccc3)c2cc1 Chemical compound c(cc1)ccc1-c1cc2c(-c3ccccc3)c(ccc(-c3ccccc3)c3)c3c(-c(cc3)ccc3-c(cc3)cc4c3[nH]c3c4cccc3)c2cc1 KLVDTYVBWSVMMU-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000009815 homocoupling reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 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
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229910000314 transition metal oxide 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-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
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
Images
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Description
本発明の大別された一は、前記したとおり下記一般式(1)で表されるアントラセン誘導体である。
本実施の形態では、本発明のアントラセン誘導体について説明する。
以下に、その合成スキームに関し具体的に説明する。
本発明のアントラセン誘導体を用いた発光素子の一態様について図1を用いて以下に説明する。
なお、本実施の形態では、第2の電極は前記したとおり陰極であり、そのような陰極材料の具体例としては、元素周期表の第1族または第2族に属する元素、すなわちリチウム(Li)やセシウム(Cs)等のアルカリ金属、およびマグネシウム(Mg)、カルシウム(Ca)、ストロンチウム(Sr)等のアルカリ土類金属、およびこれらを含む合金(MgAg、AlLi)、ユウロピウム(Eu)、イッテルビウム(Yb)等の希土類金属およびこれらを含む合金等が挙げられる。しかしながら、第2の電極103と電子輸送層との間に、電子注入を促す機能を有する層を設けることにより、仕事関数の大小に関わらず、Al、Ag、ITO、珪素若しくは酸化珪素を含有した酸化インジウム−酸化スズ等様々な導電性材料を第2の電極103として用いることができる。これら導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することが可能である。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2および実施の形態3で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2〜実施の形態4で示した構成と異なる構成の発光素子について図2を用いて説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)であり、その態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。発光ユニットとしては、実施の形態2〜実施の形態5で示した有機化合物を含む層102と同様な構成を用いることができる。つまり、実施の形態2〜実施の形態5で示した発光素子は、1つの発光ユニットを有する発光素子であり、本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
本実施の形態では、本発明のアントラセン誘導体を用いて作製された発光装置について説明する。
本実施の形態では、実施の形態7に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態1に示したアントラセン誘導体を含み、消費電力の低減された表示部を有する。
本合成例では、下記構造式(88)で表される本発明のアントラセン誘導体である9−フェニル−3−[4−(10−フェニル−9−アントリル)フェニル]−9H−カルバゾール(略称:PCzPA)の合成法を具体的に説明する。
(1)9−フェニルアントラセンの合成。
9−ブロモアントラセン5.4g(21mmol)、フェニルボロン酸2.6g(21mmol)、酢酸パラジウム(II)(略称:Pd(OAc)2)60mg(0.2mmol)、炭酸カリウム水溶液(2.0mol/L)10mL(20mmol)、トリス(オルト−トリル)ホスフィン(略称:P(o−tolyl)3)260mg(0.8mmol)、1,2−ジメトキシエタン(略称:DME)20mLを200mL三口フラスコに入れ、窒素雰囲気下にて80℃で、9時間撹拌した。反応後、析出した固体を吸引ろ過で回収してから、トルエンに溶かしフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、セライト(和光純薬工業株式会社、カタログ番号:531−16855)、アルミナを通してろ過をした。得られたろ液を水、飽和食塩水で洗浄後、硫酸マグネシウムで水分を取り除いた。この懸濁液を自然ろ過し、得られたろ液を濃縮したところ目的物である9−フェニルアントラセンの淡褐色固体を22g、収率85%で得た。(合成スキーム(a−1))
上記ステップ1(1)で得られた9−フェニルアントラセン6.0g(24mmol)を四塩化炭素80mLに溶かし、ここへ滴下ロートにて臭素3.8g(21mmol)を四塩化炭素10mLで溶かしたものを滴下撹拌した。滴下終了後、室温でさらに1時間撹拌した。反応後、ここにチオ硫酸ナトリウム水溶液を加えて撹拌してから、有機層を水酸化ナトリウム水溶液、飽和食塩水の順で洗浄し、硫酸マグネシウムを加えて水分を取り除いた。この懸濁液を自然ろ過し、ろ液を濃縮しトルエンに溶かしフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、セライト(和光純薬工業株式会社、カタログ番号:531−16855)、アルミナを通してろ過を行なった。得られたろ液を濃縮し、ジクロロメタン、ヘキサンの混合溶液により再結晶を行なったところ、目的物である9−ブロモ−10−フェニルアントラセンの淡黄色固体を7.0g、収率89%で得た。(合成スキーム(a−2))
窒素雰囲気下にて、上記ステップ1(2)で得られた9−ブロモ−10−フェニルアントラセン3.3g(10mmol)をテトラヒドロフラン(略称:THF)80mLに溶かし、−78℃にした。ここへ滴下ロートにて、n−ブチルリチウム(略称:n−BuLi)(1.6mol/L ヘキサン溶液)7.5mL(12mmol)を滴下し、1時間撹拌した。ヨウ素5.0g(20mmol)をTHF20mLに溶かした溶液を混合液に滴下し、−78℃でさらに2時間撹拌した。反応後、ここにチオ硫酸ナトリウム水溶液を加えて撹拌してから、有機層をチオ硫酸ナトリウム水溶液、飽和食塩水の順で洗浄し、硫酸マグネシウムを加えて水分を取り除いた。この懸濁液を濾過し、ろ液を濃縮し、得られた固体をエタノールにより再結晶したところ目的物である9−ヨード−10−フェニルアントラセンの淡黄色固体を3.1g、収率83%で得た。(合成スキーム(a−3))
上記ステップ1(3)で得られた9−ヨード−10−フェニルアントラセン1.0g(2.6mmol)、p−ブロモフェニルボロン酸540mg(2.7mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(略称:Pd(PPh3)4)46mg(30μmol)、2.0mol/L 炭酸カリウム水溶液3.0mL(6.0mmol)、トルエン10mLの混合物を80℃、9時間撹拌した。反応後、トルエンを加えてからフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、セライト(和光純薬工業株式会社、カタログ番号:531−16855)、アルミナを通してろ過をした。得られたろ液を水、飽和食塩水で洗浄後、硫酸マグネシウムで水分を取り除いた。この懸濁液を自然ろ過し、ろ液を濃縮し、得られた固体をクロロホルム、ヘキサンの混合溶液により再結晶したところ目的物である9−(4−ブロモフェニル)−10−フェニルアントラセン(略称;PA)の淡褐色固体を560mg、収率45%で得た。(合成スキーム(a−4))
500mL三口フラスコ中にて、上記ステップ1(1)〜(4)で得られた9−(4−ブロモフェニル)−10−フェニルアントラセン20g(49mmol)、テトラヒドロフラン(略称:THF)300mLを、窒素雰囲気下、−78℃にて撹拌した。ここに、n−ブチルリチウム(1.6mol/Lヘキサン溶液)34mL(54mmol)を滴下し、同温度で2時間攪拌した。その後、ここにホウ酸トリメチル13mL(110mmol)を加え、室温にて24時間撹拌した。反応終了後、ここに1.0mol/L塩酸200mLを加え、室温で1時間撹拌した。この混合物の有機層を水で洗浄して、有機層と水層とに分け、得られた水層を酢酸エチルでさらに抽出した。この抽出溶液を先の有機層と合わせて飽和食塩水で洗浄後、硫酸マグネシウムを加えて水分を取り除いた。これを吸引ろ過し、得られたろ液を濃縮して残渣を得た。得られた残渣をクロロホルムとヘキサンの混合溶媒により再結晶したところ、目的物である4−(10−フェニル−9−アントリル)フェニルボロン酸の白色粉末状固体を15g、収率84%で得た。(合成スキーム(a−5))
1000mL三角フラスコ中にて、9−フェニルカルバゾールを24g(100mmol)、N−ブロモこはく酸イミドを18g(100mmol)、トルエン450mL、酢酸エチル200mLを加えて、室温にて45時間撹拌した。この懸濁液を、水で洗浄した後、硫酸マグネシウムを加えて水分を取り除いた。この懸濁液をろ過し、得られたろ液を濃縮、乾燥させた。キャラメル状の目的物である3−ブロモ−9−フェニル−9H−カルバゾールを32g、収率99%で得た。(合成スキーム(a−6))
100mL三口フラスコ中にて、上記ステップ2で得られた4−(10−フェニル−9−アントリル)フェニルボロン酸を2.6g(7.0mmol)、上記ステップ3で得られた3−ブロモ−9−フェニル−9H−カルバゾールを2.3g(7.0mmol)、酢酸パラジウム(II)(略称:Pd(OAc)2)を2.0mg(10μmol)、トリス(オルト−トリル)ホスフィン(略称:P(o−tolyl)3)を6.0mg(20μmol)、炭酸カリウム水溶液(2mol/L)を5mL(10mmol)、1,2−ジメトキシエタン(略称:DME)を20mL、窒素雰囲気下で90℃にて6.5時間加熱撹拌を行った。この懸濁液を室温まで冷ました後、トルエン200mLを加えながらフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナ、セライト(和光純薬工業株式会社、カタログ番号:531−16855)を通してろ過を行った。得られたろ液を濃縮し、これにアセトンとメタノールを加えて超音波をかけた後、再結晶を行った。淡黄色粉末の目的物である9−フェニル−3−[4−(10−フェニル−9−アントリル)フェニル]−9H−カルバゾール(略称:PCzPA)を3.8g、収率95%で得た。(合成スキーム(a−7))
本合成例では、合成例1とは異なる合成法による9−フェニル−3−[4−(10−フェニル−9−アントリル)フェニル]−9H−カルバゾール(略称:PCzPA)の合成法を具体的に説明する。
500mL三口フラスコ中にて、合成例1で記載のステップ3で得られた3−ブロモ−9−フェニルカルバゾールを29g(90mmol)、テトラヒドロフラン(略称:THF)を200mL、−78℃にて撹拌し溶液とした後、ここにn−ブチルリチウムを(1.6mol/Lヘキサン溶液)110ml(69mmol)滴下し、同温度で2時間撹拌した。さらに、ここにホウ酸トリメチルを13mL(140mmoL)を加え、室温にて、24時間撹拌した。反応終了後、ここに1.0mol/L塩酸200mLを加え、室温で1時間撹拌した。これを水、水酸化ナトリウム水溶液、水の順で洗浄し、硫酸マグネシウムを加えて水分を取り除いた。この懸濁液を濾過し、得られた濾液を濃縮し、クロロホルムとヘキサンを加えて超音波をかけた後、再結晶を行った。白色粉末の目的物である9−フェニル−9H−カルバゾール−3−イルボロン酸を21g、収率80%で得た。(合成スキーム(b−1))
200mL三口フラスコ中にて、合成例1で記載のステップ1(1)〜(4)で得られた9−(4−ブロモフェニル)−10−フェニルアントラセン(略称:PA)を1.9g(4.7mmol)、合成例2で記載のステップ1で得られた9−フェニル−9H−カルバゾール−3−ボロン酸を1.4g(4.7mmol)、酢酸パラジウム(II)(略称:Pd(OAc)2)を5.6mg(25μmol)、トリス(オルト−トリル)ホスフィン(略称:P(o−tolyl)3)を52mg(170μmol)、炭酸カリウム水溶液(2.0mol/L)を7mL(15mmol)、1,2−ジメトキシエタン(略称:DME)を40mL、窒素雰囲気下で90℃にて7時間加熱撹拌を行った。この懸濁液を室温まで冷ました後、ろ過して濾物を得た。この得られたろ物を温トルエン50mLに溶かした後、トルエン400mLを加えながらフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナ、セライト(和光純薬工業株式会社、カタログ番号:531−16855)を通してろ過を行った。得られたろ液を濃縮し、これにヘキサンを加えて超音波をかけた後、再結晶を行った。淡黄色粉末の目的物である9−フェニル−3−[4−(10−フェニル−9−アントリル)フェニル]−9H−カルバゾール(略称:PCzPA)を2.0g、収率75%で得た。(合成スキーム(b−2))
本実施例では、下記構造式(98)で表される本発明のアントラセン誘導体である3,3’−(2−tert−ブチルアントラセン−9,10−ジイルジ−4,1−フェニレン)ビス(9−フェニル−9H−カルバゾール)(略称:PCzBPA)の合成法を具体的に説明する。
(1)9,10−ビス(4−ブロモフェニル)−2−tert−ブチル−9,10−ジヒドロキシ−9,10−ジヒドロアントラセンの合成。
1,4−ジブロモベンゼン(5.0g)の脱水エーテル溶液(200mL)に−78℃において1.6mol/Lのブチルリチウムヘキサン溶液(13mL)を窒素気流下にて滴下した。滴下終了後、同温度にて1時間攪拌した。ここに、−78℃にて2−tert−ブチルアントラキノン2.8g(11mmol)の脱水エーテル溶液(40mL)を滴下し、その後反応溶液をゆっくり室温まで昇温した。24時間室温で攪拌した後、水を加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄、硫酸マグネシウムで乾燥、濾過、濃縮し、残渣をシリカゲルクロマトグラフィー(展開溶媒、ヘキサン−酢酸エチル)によって精製し、9,10−ビス(4−ブロモフェニル)−2−tert−ブチル−9,10−ジヒドロキシ−9,10−ジヒドロアントラセンを5.5g、収率は90%で得た。(合成スキーム(c−1))
合成例3で記載のステップ1(1)で得られた9,10−ビス(4−ブロモフェニル)−2−tert−ブチル−9,10−ジヒドロキシ−9,10−ジヒドロアントラセン987mg(1.6mmol)、ヨウ化カリウム664mg(4.0mmol)、ホスフィン酸ナトリウム一水和物を1.48g(14mmol)を、氷酢酸12mlにて懸濁し、大気下にて2時間還流加熱撹拌した。室温まで冷ましたのち、生じた析出物を濾過し、得られた固体をメタノール約50mlで洗浄した。得られた固体を乾燥させてクリーム色粉末の9,10−ビス(4−ブロモフェニル)−2−tert−ブチルアントラセン(略称:BPA)を700mg、収率は82%で得た。(合成スキーム(c−2))
200mL三口フラスコ中にて、合成例3で記載のステップ1(1)〜(2)で得られた9,10−ジ(4−ブロモフェニル)−2−tert−ブチルアントラセン(略称:BPA)を1.6g(3.0mmol)、合成例2で記載のステップ1(1)で得られた9−フェニル−9H−カルバゾール−3−ボロン酸を1.7g(6.0mmol)、酢酸パラジウム(II)(略称:Pd(OAc)2)を13mg(60μmol)、トリス(オルト−トリル)ホスフィン(略称:P(o−tolyl)3)を36mg(120μmol)、炭酸カリウム水溶液(2.0mol/L)を5mL(10mmol)、トルエンを20mL、エタノールを5ml、窒素雰囲気下で90℃にて5.5時間加熱撹拌を行った。この懸濁液を室温まで冷ました後、トルエン200mLを加えながらフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、シリカゲル、セライト(和光純薬工業株式会社、カタログ番号:531−16855)を通して濾過を行った。得られた濾液を水で洗浄し、硫酸マグネシウムを加えて水分を取り除いた。この懸濁液を、フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、シリカゲル、アルミナ、セライト(和光純薬工業株式会社、カタログ番号:531−16855)を通して濾過し、得られたろ液を濃縮した。これをシリカゲルカラムクロマトグラフィー(トルエン:ヘキサン=1:1)にて目的物を分取した。これに酢酸エチル、メタノールを加えて超音波をかけた後、再結晶を行った。淡黄色粉末の目的物である3,3’−(2−tert−ブチルアントラセン−9,10−ジイルジ−4,1−フェニレン)ビス(9−フェニル−9H−カルバゾール)(略称:PCzBPA)を1.8g、収率67%で得た。(合成スキーム(c−3))
まず、ガラス基板2100に酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極2101を形成した。なお、その膜は110nmとし、電極面積は2mm×2mmとした。
なお、前記CIE色度座標の数値は、輝度計(トプコン社製、色彩輝度計(BM−5A)を用いて実測したものであり、これ以後の他のCIE色度座標の数値も同様である。
本発光素子2では、実施例2で説明した発光素子1の発光層2111における、PCzPAをPCzPAと4−(9H−カルバゾール−9−イル)−4’−(10−フェニル−9−アントリル)トリフェニルアミン(略称:YGAPA)との共蒸着に換え、正孔輸送層2103上に40nmの膜厚の発光層2111を形成した以外は、発光素子1と同様に作製した。なお、PCzPAとYGAPAの重量比は1:0.04(=PCzPA:YGAPA)となるように調節した。
本発光素子3では、実施例2で説明した発光素子1の発光層2111におけるPCzPAを、PCzPAとN,N’−ビス[4−(9H−カルバゾール−9−イル)フェニル]−N,N’−ジフェニルスチルベン−4,4’−ジアミン(略称:YGA2S)との共蒸着に換え、正孔輸送層2103上に30nmの膜厚の発光層2111を形成した。ここで、PCzPAとYGA2Sの重量比は1:0.05(=PCzPA:YGA2S)となるように調節した。また、電子注入層2105の膜厚を20nmとなるようにAlqとリチウムを共蒸着した。上記以外は発光素子1と同様に作製した。
まず、ガラス基板3100に酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極3101を形成した。なお、その膜は110nmとし、電極面積は2mm×2mmとした。
101 第1の電極
102 有機化合物を含む層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
121 第1の層
122 第2の層
401 駆動回路(ソース側駆動回路)
402 画素部
403 駆動回路(ゲート側駆動回路)
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極
414 絶縁物
416 有機化合物を含む層
417 第2の電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 有機化合物を含む層
956 電極
2001 筐体
2002 光源
2100 ガラス基板
2101 第1の電極
2102 複合材料を含む層
2103 正孔輸送層
2104 電子輸送層
2105 電子注入層
2106 第2の電極
2111 発光層
3001 照明装置
3002 テレビ装置
3100 ガラス基板
3101 第1の電極
3102 複合材料を含む層
3103 正孔輸送層
3104 電子輸送層
3105 電子注入層
3106 第2の電極
3111 第1の層
3112 第2の層
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015164191A (ja) * | 2007-12-21 | 2015-09-10 | 株式会社半導体エネルギー研究所 | 発光素子 |
JP2016175912A (ja) * | 2007-12-21 | 2016-10-06 | 株式会社半導体エネルギー研究所 | 化合物 |
US9972790B2 (en) | 2007-12-21 | 2018-05-15 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, and light-emitting material, light-emitting element, light-emitting device, and electronic device using the same |
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