JP2005330219A - Substituted vinyl group-containing dipyridophenazine derivative, electron transport material and organic electroluminescence device using the same - Google Patents
Substituted vinyl group-containing dipyridophenazine derivative, electron transport material and organic electroluminescence device using the same Download PDFInfo
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- JP2005330219A JP2005330219A JP2004149480A JP2004149480A JP2005330219A JP 2005330219 A JP2005330219 A JP 2005330219A JP 2004149480 A JP2004149480 A JP 2004149480A JP 2004149480 A JP2004149480 A JP 2004149480A JP 2005330219 A JP2005330219 A JP 2005330219A
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- 239000000463 material Substances 0.000 title claims abstract description 43
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 29
- BVQAWSJMUYMNQN-UHFFFAOYSA-N dipyridophenazine Chemical class C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 BVQAWSJMUYMNQN-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 89
- 239000010410 layer Substances 0.000 description 83
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 42
- 230000032258 transport Effects 0.000 description 39
- -1 1-methylpentyl group Chemical group 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 21
- 238000001914 filtration Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 150000003008 phosphonic acid esters Chemical class 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 229910001873 dinitrogen Inorganic materials 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000007983 Tris buffer Chemical group 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 10
- 150000001728 carbonyl compounds Chemical class 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 0 C*(C1=C(C(*)=N)C(C)=C(C)C2C1C(C1)(C3CC3)C1NC2*)=C=* Chemical compound C*(C1=C(C(*)=N)C(C)=C(C)C2C1C(C1)(C3CC3)C1NC2*)=C=* 0.000 description 8
- 238000000434 field desorption mass spectrometry Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 7
- 230000001603 reducing effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 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 4
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000005041 phenanthrolines Chemical class 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- DMEPVFSJYHJGCD-UHFFFAOYSA-N 3,5-dimethylbenzene-1,2-diamine Chemical compound CC1=CC(C)=C(N)C(N)=C1 DMEPVFSJYHJGCD-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 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
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([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
- 125000004123 n-propyl group Chemical group [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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 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
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- KCALAFIVPCAXJI-UHFFFAOYSA-N 1,10-phenanthroline-5,6-dione Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CN=C3C2=N1 KCALAFIVPCAXJI-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JBLPWFLKCBTNBV-UHFFFAOYSA-N 1,7-phenanthroline-5,6-dione Chemical compound C1=CC=C2C(=O)C(=O)C3=NC=CC=C3C2=N1 JBLPWFLKCBTNBV-UHFFFAOYSA-N 0.000 description 1
- DVYFKNZERRCRCU-UHFFFAOYSA-N 1,8-phenanthroline-5,6-dione Chemical compound C1=NC=C2C(=O)C(=O)C3=CC=CN=C3C2=C1 DVYFKNZERRCRCU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- NLXDFCLCNCWKND-UHFFFAOYSA-N 10-n-(4-butylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1NC1=C(N)C2=CC=CC=C2C2=CC=CC=C12 NLXDFCLCNCWKND-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- ZARSVJHEUIEZDE-UHFFFAOYSA-N 2,9-diethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(CC)N=C3C2=NC(CC)=CC=1C1=CC=CC=C1 ZARSVJHEUIEZDE-UHFFFAOYSA-N 0.000 description 1
- LUODSNXEIGJWST-UHFFFAOYSA-N 2,9-dimethyl-4,7-bis(4-methylphenyl)-1,10-phenanthroline Chemical compound C1=CC(C)=CC=C1C1=CC(C)=NC2=C1C=CC1=C(C=3C=CC(C)=CC=3)C=C(C)N=C21 LUODSNXEIGJWST-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- QWJXOAVPPRMFCJ-UHFFFAOYSA-N 2,9-phenanthroline-5,6-dione Chemical compound O=C1C(=O)c2ccncc2-c2cnccc12 QWJXOAVPPRMFCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VLPADTBFADIFKG-UHFFFAOYSA-N phanquone Chemical compound C1=CN=C2C(=O)C(=O)C3=NC=CC=C3C2=C1 VLPADTBFADIFKG-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- SKFLCXNDKRUHTA-UHFFFAOYSA-N phenyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CC=C1 SKFLCXNDKRUHTA-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ODJOHIWKLOPSFF-UHFFFAOYSA-N pyrido[3,2-a]phenazine Chemical class C1=CC=C2C3=NC4=CC=CC=C4N=C3C=CC2=N1 ODJOHIWKLOPSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000001275 scanning Auger electron spectroscopy Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 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
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [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
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 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
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Abstract
【課題】 本発明の目的は、前記の課題を解決するためになされたもので、有機ＥＬ素子の高輝度化、高発光効率化及び電極との付着改善による長寿命化を可能とする置換ビニル基含有ジピリドフェナジン誘導体、それを用いた電子輸送材料およびそれを利用した有機ＥＬ素子の提供。
【解決手段】 下記一般式（Ａ）
【化１】
（式中、Ｑは置換基を有することもある下記式
【化２】
で示される基群から選ばれたものである。）
ことを特徴とする置換ビニル基含有ジピリドフェナジン誘導体、それを用いた電子輸送材料および有機エレクトロルミネッセンス素子。
【選択図】 なしPROBLEM TO BE SOLVED To solve the above-mentioned problems, an object of the present invention is to provide a substituted vinyl capable of increasing the luminance of an organic EL element, increasing the luminous efficiency, and extending the life by improving the adhesion to the electrode. A group-containing dipyridophenazine derivative, an electron transport material using the derivative, and an organic EL device using the electron transport material.
The following general formula (A)
[Chemical 1]
(In the formula, Q may have a substituent;
It is selected from the group represented by )
A substituted vinyl group-containing dipyridophenazine derivative, an electron transport material using the same, and an organic electroluminescence device.
[Selection figure] None
Description
本発明は、置換ビニル基含有ジピリドフェナジン誘導体およびそれを利用した有機エレクトロルミネッセンス素子（有機ＥＬ素子）に関し、特に、高輝度化、高発光効率化及び長寿命化を可能とする新規な置換ビニル基含有ジピリドフェナジン誘導体、それを用いた電子輸送材料およびそれを利用した有機ＥＬ素子に関するものである。 The present invention relates to a substituted vinyl group-containing dipyridophenazine derivative and an organic electroluminescence device (organic EL device) using the same, and in particular, a novel substitution that enables high luminance, high luminous efficiency, and long life. The present invention relates to a vinyl group-containing dipyridophenazine derivative, an electron transport material using the same, and an organic EL device using the same.
従来、有機ＥＬ素子に電子注入層や電子輸送層を設けて発光効率を高める試みがなされてきた。しかし、発光層の発光材料とのエキサイプレックスの形成が見られたり、高輝度の発光は得られるものの、発光寿命が短いという欠点があった。また、長時間の通電により金属電極と有機層が剥離したり、有機層と電極が結晶化して白濁し、発光輝度が低下するため、このような現象を防ぐ必要がある。特許文献１には、置換基を有するフェナントロリン誘導体を有機ＥＬ素子の電子輸送層として用いることにより、高輝度で発光することが開示されている。しかし、長時間の通電により、これらの置換基を有するフェナントロリン誘導体は結晶化が起こりやすいこともあり、発光輝度が低下し、素子の発光寿命が数時間程度という欠点があった。また、通電により、金属電極と電子輸送層との剥離も生じ、有機ＥＬ素子の寿命が短くなるという問題もあった。
Conventionally, attempts have been made to increase luminous efficiency by providing an electron injection layer and an electron transport layer in an organic EL element. However, the formation of an exciplex with the light emitting material of the light emitting layer can be seen, and although high luminance light emission can be obtained, there are drawbacks in that the light emission life is short. In addition, it is necessary to prevent such a phenomenon because the metal electrode and the organic layer are separated by energization for a long time, or the organic layer and the electrode are crystallized and become white turbid, resulting in a decrease in luminance.
本発明の目的は、前記の課題を解決するためになされたもので、有機ＥＬ素子の高輝度化、高発光効率化及び電極との付着改善による長寿命化を可能とする置換ビニル基含有ジピリドフェナジン誘導体、それを用いた電子輸送材料およびそれを利用した有機ＥＬ素子を提供する点にある。 An object of the present invention is to solve the above-mentioned problems, and is a substituted vinyl group-containing diene that enables an organic EL device to have a high brightness, a high luminous efficiency, and a long life by improving adhesion to the electrode. The object is to provide a pyridophenazine derivative, an electron transport material using the derivative, and an organic EL device using the same.
本発明者らは、前記課題を解決するために鋭意検討した結果、置換ビニル基含有ジピリドフェナジン誘導体を有機ＥＬ素子の有機薄膜層、とくに電子輸送層の材料として用いることにより、前記の課題を解決することを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors have used the above-mentioned problems by using a substituted vinyl group-containing dipyridophenazine derivative as a material for an organic thin film layer of an organic EL device, particularly an electron transport layer. Has been found to solve the problem, and the present invention has been completed.
本発明の第１は、下記一般式（Ａ）
ことを特徴とする置換ビニル基含有ジピリドフェナジン誘導体に関する。
本発明の第２は、請求項１記載の置換ビニル基含有ジピリドフェナジン誘導体よりなる有機エレクトロルミネッセンス素子（有機ＥＬ素子）用電子輸送材料に関する。
本発明の第３は、陰極と陽極の間に１層または複数層からなる有機薄膜層が挟持されている有機エレクトロルミネッセンス素子（有機ＥＬ素子）において、該有機薄膜層の少なくとも１層が請求項１記載の置換ビニル基含有ジピリドフェナジン誘導体を含有することを特徴とする有機エレクトロルミネッセンス素子（有機ＥＬ素子）に関する。
本発明の第４は、陰極と陽極の間に少なくとも電子輸送層、発光層および正孔輸送層が挟持されている有機エレクトロルミネッセンス素子（有機ＥＬ素子）において、電子輸送層が請求項１記載の置換ビニル基含有ジピリドフェナジン誘導体を１種類以上含有することを特徴とする有機ＥＬ素子に関する。
The first of the present invention is the following general formula (A)
And a substituted vinyl group-containing dipyridophenazine derivative.
The second of the present invention relates to an electron transport material for an organic electroluminescence device (organic EL device) comprising the substituted vinyl group-containing dipyridophenazine derivative according to
According to a third aspect of the present invention, in the organic electroluminescence device (organic EL device) in which one or more organic thin film layers are sandwiched between the cathode and the anode, at least one of the organic thin film layers is claimed. 1. An organic electroluminescence device (organic EL device) comprising the substituted vinyl group-containing dipyridophenazine derivative according to 1.
According to a fourth aspect of the present invention, in the organic electroluminescence device (organic EL device) in which at least the electron transport layer, the light emitting layer, and the hole transport layer are sandwiched between the cathode and the anode, the electron transport layer is described in
本発明の代表的な置換ビニル基含有ジピリドフェナジン誘導体としては、下記一般式（１）〜（６）で示される化合物を挙げることができる。
Ｒ０〜Ｒ６およびＡｒ１、Ａｒ２において、置換もしくは無置換の炭素数１〜２０のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ｎ−ブチル基、ｓｅｃ−ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、イソペンチル基、ネオペンチル基、ｔｅｒｔ−ペンチル基、１−メチルペンチル基、２−メチルペンチル基、３−メチルペンチル基、３，３−ジメチルペンチル基、シクロペンチル基、ｎ−ヘキシル基、イソヘキシル基、２，３，５−トリメチルヘキシル基、シクロヘキシル基、ｎ−ヘプチル基、イソヘプチル基、４−エチル−３，３−ジメチルヘプチル基、ｎ−オクチル基、４−エチル−５−メチルオクチル基、ｎ−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−ドデシル基、ｎ−トリデシル基、ｎ−テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、エイコシル基、ヘニコシル基、ドコシル基、トリコシル基、テトラコシル基、ペンタコシル基、ヘキサコシル基、ヘプタコシル基、オクタコシル基、ノナコシル基、トリアコンチル基、２，７，８−トリメチル−デシル基、５−メチル−４−プロピルノニル基、ビシクロヘキシル−４−イル基、４′−メチル−ビシクロヘキシル−４−イル基などが挙げられる。 In R 0 to R 6 and Ar 1 and Ar 2 , the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms includes a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a sec-butyl group. , Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 3,3-dimethylpentyl group , Cyclopentyl group, n-hexyl group, isohexyl group, 2,3,5-trimethylhexyl group, cyclohexyl group, n-heptyl group, isoheptyl group, 4-ethyl-3,3-dimethylheptyl group, n-octyl group, 4-ethyl-5-methyloctyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n Tridecyl group, n-tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, Nonacosyl group, triacontyl group, 2,7,8-trimethyl-decyl group, 5-methyl-4-propylnonyl group, bicyclohexyl-4-yl group, 4'-methyl-bicyclohexyl-4-yl group and the like It is done.
Ｒ０〜Ｒ６において、置換もしくは無置換の炭素数１〜２０のアルコキシ基としては、−ＯＹで表される基であり、Ｙの例としては、メチル基、エチル基、プロピル基、イソプロピル基、ｎ−ブチル基、ｓ−ブチル基、イソブチル基、ｔ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基などが挙げられる。 In R 0 to R 6 , the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms is a group represented by —OY, and examples of Y include a methyl group, an ethyl group, a propyl group, and an isopropyl group. , N-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and the like.
Ｒ０〜Ｒ６およびＡｒ１、Ａｒ２において、置換もしくは無置換の炭素数６〜３０のアリール基としては、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、フルオレニル基、ビフェニル基、ターフェニル基、スチルベン基などが挙げられる。 In R 0 to R 6 and Ar 1 and Ar 2 , the substituted or unsubstituted aryl group having 6 to 30 carbon atoms includes phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, fluorenyl group, A biphenyl group, a terphenyl group, a stilbene group, etc. are mentioned.
Ｒ０〜Ｒ６において、置換もしくは無置換の炭素数７〜３０のアリールアルキル基としては、ベンジル基、α−メチルベンジル基、シンナミル基、α−エチルベンジル基、α，α−ジメチルベンジル基、４−メチルベンジル基、４−エチルベンジル基、２−ｔｅｒｔ−ブチルベンジル基、４−ｎ−オクチルベンジル基、ナフチルメチル基、ジフェニルメチル基などが挙げられる。 In R 0 to R 6 , the substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms includes benzyl group, α-methylbenzyl group, cinnamyl group, α-ethylbenzyl group, α, α-dimethylbenzyl group, Examples include 4-methylbenzyl group, 4-ethylbenzyl group, 2-tert-butylbenzyl group, 4-n-octylbenzyl group, naphthylmethyl group, diphenylmethyl group and the like.
Ｒ０〜Ｒ６において、置換もしくは無置換の炭素数６〜４０のアリールオキシ基としては、フェノキシ基、ナフチルオキシ基、アントリルオキシ基、ピレニルオキシ基、ビフェニルオキシ基、フルオランテニルオキシ基、クリセニルオキシ基、ピレニルオキシ基などが挙げられる。 In R 0 to R 6 , the substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms includes phenoxy group, naphthyloxy group, anthryloxy group, pyrenyloxy group, biphenyloxy group, fluoranthenyloxy group, chrysenyloxy Group, pyrenyloxy group and the like.
Ｒ０〜Ｒ６およびＡｒ１、Ａｒ２において、置換もしくは無置換の炭素数４〜３０のヘテロ環基としては、例えば、酸素原子を含むフリル基、イソベンゾフラニル基、硫黄原子を含むチエニル基、ベンゾチエニル基、窒素原子を含むピリジル基、ピラジニル基、ピリミジル基、ピリダジニル基、インドジニル基、イソインドリル基、イソキノリル基、キノリル基、キノキサリニル基、キナゾリニル基、フェナントリジニル基、フェナントロリニル基などが挙げられる。 In R 0 to R 6 and Ar 1 and Ar 2 , examples of the substituted or unsubstituted heterocyclic group having 4 to 30 carbon atoms include a furyl group containing an oxygen atom, an isobenzofuranyl group, and a thienyl containing a sulfur atom. Group, benzothienyl group, pyridyl group containing nitrogen atom, pyrazinyl group, pyrimidyl group, pyridazinyl group, indodinyl group, isoindolyl group, isoquinolyl group, quinolyl group, quinoxalinyl group, quinazolinyl group, phenanthridinyl group, phenanthrolinyl Groups and the like.
前記アルキル基、アルコキシ基、アリール基、アリールアルキル基、アリールオキシ基、ヘテロ環基の置換基の例としては、ハロゲン原子、アルキル基、シクロアルキル基、アルコキシ基、アリール基、アリールアルキル基、アリールオキシ基などが挙げられる。 Examples of the substituent of the alkyl group, alkoxy group, aryl group, arylalkyl group, aryloxy group, and heterocyclic group include halogen atom, alkyl group, cycloalkyl group, alkoxy group, aryl group, arylalkyl group, aryl An oxy group etc. are mentioned.
以下に、前記一般式（１）〜（６）で示される本発明の化合物の具体例を示すが、本発明の化合物はこれにより限定されるものではない。なお、式中、Ｍｅはメチル基、Ｅｔはエチル基、ｔ−Ｂｕはｔ−ブチル基、ｎ−Ｂｕはｎ−ブチル基、ｉ−Ｐｒはイソプロピル基、ｎ−Ｐｒはｎ−プロピル基、ＯＭｅはメトキシ基を示す。 Specific examples of the compound of the present invention represented by the general formulas (1) to (6) are shown below, but the compound of the present invention is not limited thereto. In the formula, Me is a methyl group, Et is an ethyl group, t-Bu is a t-butyl group, n-Bu is an n-butyl group, i-Pr is an isopropyl group, n-Pr is an n-propyl group, OMe Represents a methoxy group.
一般式（１）〜（６）で示される化合物は、下記の方法によりそれぞれ合成することができる。なお、以下の反応式中のｍ、Ｒ０〜Ｒ６およびＡｒ１、Ａｒ２は請求項において規定したとおりのものである。 The compounds represented by the general formulas (1) to (6) can be synthesized by the following methods, respectively. In the following reaction formula, m, R 0 to R 6 and Ar 1 and Ar 2 are as defined in the claims.
上記一般式（１）〜（６）で表される置換ビニル基含有ジピリドフェナジン誘導体は、一般式（１−ｂ）〜（６−ｂ）で表されるホスホン酸エステルをカルボニル化合物とカップリング反応させることにより合成できる。この反応は、塩基存在下、溶媒中で、通常、室温から溶媒の沸点までの温度範囲で行なわれる。具体的には、一般式（１−ｂ）〜（６−ｂ）のホスホン酸エステル基と当量のカルボニル化合物を極性溶媒に溶解した後、当量以上の塩基を添加し、所定の温度で反応させる。反応液を大量の水中もしくは塩の飽和水溶液に加えて得られる固体を濾別分取するか、又は反応液を大量の水中もしくは塩の飽和水溶液に加えてさらに任意の有機溶媒を加え、抽出して目的の置換ビニル基含有ジピリドフェナジン誘導体を得ることができる。このようにして得られる置換ビニル基含有ジピリドフェナジン誘導体は、再結晶又はカラムクロマトグラフィーにより精製することができる。ここで、一般式（１−ｂ）〜（６−ｂ）のホスホン酸エステル基のエチル基は、低級アルキル基として炭素数１〜５のアルキル基およびフェニル基であってもよいが、メチル基、エチル基であることが好ましい。また、置換ビニル基含有ジピリドフェナジン誘導体の合成で用いる塩基としては、カリウム−ｔ−ブトキサイド（ｔ−ＢｕＯＫ）のほかに、水酸化ナトリウム、水酸化カリウム、ナトリウムメチラート、ナトリウムエチラート、ナトリウムアミド、水素化ナトリウム、水素化リチウム、リチウムジイソプロピルアミドなどが挙げられる。反応溶媒としては、炭化水素、ハロゲン化炭化水素、エーテル類などが好ましい。具体的には、ベンゼン、トルエン、キシレンなどの芳香族炭化水素類、クロロホルム、クロロベンゼン、ｏ−ジクロロベンゼンなどのハロゲン化炭化水素類、エチレングリコール、ジエチレングリコール、ビス（２−メトキシエチル）エーテル、ジオキサン、テトラヒドロフランなどのエーテル類、ジメチルスルホキサイド、Ｎ，Ｎ′−ジメチルホルムアミド、Ｎ−メチルピロリドン、１，３−ジメチル−２−イミダゾリジノンなどが挙げられる。特に、テトラヒドロフラン、ｏ−ジクロロベンゼン、ジメチルスルホキサイドなどが好適である。 The substituted vinyl group-containing dipyridophenazine derivatives represented by the general formulas (1) to (6) are prepared by cupping a phosphonic acid ester represented by the general formulas (1-b) to (6-b) with a carbonyl compound. It can be synthesized by ring reaction. This reaction is usually performed in a solvent in the presence of a base in a temperature range from room temperature to the boiling point of the solvent. Specifically, the phosphonate ester group of the general formulas (1-b) to (6-b) and an equivalent carbonyl compound are dissolved in a polar solvent, and then an equivalent or more base is added and reacted at a predetermined temperature. . The reaction solution is added to a large amount of water or a saturated aqueous solution of salt, and a solid obtained by filtration is separated by filtration, or the reaction solution is added to a large amount of water or a saturated aqueous solution of salt and an arbitrary organic solvent is added for extraction. Thus, the desired substituted vinyl group-containing dipyridophenazine derivative can be obtained. The substituted vinyl group-containing dipyridophenazine derivative thus obtained can be purified by recrystallization or column chromatography. Here, the ethyl group of the phosphonic acid ester group of the general formulas (1-b) to (6-b) may be a C 1-5 alkyl group or a phenyl group as a lower alkyl group, but a methyl group An ethyl group is preferred. In addition to potassium-t-butoxide (t-BuOK), bases used in the synthesis of substituted vinyl group-containing dipyridophenazine derivatives include sodium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, sodium. Examples include amide, sodium hydride, lithium hydride, lithium diisopropylamide and the like. As the reaction solvent, hydrocarbons, halogenated hydrocarbons, ethers and the like are preferable. Specifically, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, chlorobenzene and o-dichlorobenzene, ethylene glycol, diethylene glycol, bis (2-methoxyethyl) ether, dioxane, Ethers such as tetrahydrofuran, dimethyl sulfoxide, N, N′-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like can be mentioned. In particular, tetrahydrofuran, o-dichlorobenzene, dimethyl sulfoxide and the like are suitable.
本発明の置換ビニル基含有ジピリドフェナジン誘導体は、有機ＥＬ素子用の有機化合物として使用することが好ましい。本発明の有機ＥＬ素子は、陰極と陽極の間に一層又は複数層からなる有機薄膜層が挟持されている有機ＥＬ素子において、電子輸送層が請求項１記載の置換ビニル基含有ジピリドフェナジン誘導体、とくに上記一般式（１）〜（６）の１種類または複数の種類の置換ビニル基含有ジピリドフェナジン誘導体であることを特徴とするものである。
The substituted vinyl group-containing dipyridophenazine derivative of the present invention is preferably used as an organic compound for an organic EL device. The organic EL device of the present invention is an organic EL device in which one or more organic thin film layers are sandwiched between a cathode and an anode, and the electron transport layer is the substituted vinyl group-containing dipyridophenazine according to
本発明の有機ＥＬ素子における正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層は、それぞれ二層以上の層構成により形成されてもよい。その際、正孔注入層の場合、陽極から正孔を注入する層を正孔注入層、正孔注入層から正孔を受け取り、発光層まで正孔を輸送する層を正孔輸送層と呼ぶ。同様に電子注入層の場合、陰極から電子を注入する層を電子注入層、電子注入層から電子を受け取り、発光層まで電子を輸送する層を電子輸送層と呼ぶ。これらの各層は、材料のエネルギー準位、耐熱性、有機薄膜層もしくは金属電極との密着性等の各要因により選択されて使用される。
また、本発明の有機ＥＬ素子は、前記一般式（１）〜（６）で表される置換ビニル基含有ジピリドフェナジン誘導体に、還元ドーパントを添加、含有した電子注入層を設けることが好ましい。
Each of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer in the organic EL device of the present invention may be formed of two or more layers. At that time, in the case of a hole injection layer, the layer that injects holes from the anode is called a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is called a hole transport layer. . Similarly, in the case of an electron injection layer, a layer that injects electrons from the cathode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to the 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, adhesion with the organic thin film layer or the metal electrode.
In the organic EL device of the present invention, it is preferable to provide an electron injection layer containing a reduced dopant added to the substituted vinyl group-containing dipyridophenazine derivative represented by the general formulas (1) to (6). .
本発明の有機ＥＬ素子は、前記したように陽極と陰極間に一層もしくは多層の有機薄膜層を形成した素子である。一層型の場合、陽極と陰極との間に発光層を設けている。この場合、発光層は発光材料を含有し、それに加えて陽極から注入した正孔、もしくは陰極から注入した電子を発光材料まで輸送させるために、正孔注入材料もしくは電子注入材料を含有してもよい。また、発光材料は、きわめて高い蛍光量子効率、高い正孔輸送能力及び電子輸送能力を併せ持ち、均一な薄膜を形成することが好ましい。多層型の有機ＥＬ素子としては、（陽極／発光層／電子輸送層／陰極）、（陽極／正孔輸送層／発光層／陰極）、（陽極／正孔輸送層／発光層／電子輸送層／陰極）、（陽極／正孔注入層／正孔輸送層／発光層／電子輸送層／陰極）、（陽極／正孔輸送層／発光層／電子輸送層／電子輸注入層／陰極）、（陽極／正孔注入層／正孔輸送層／発光層／電子輸送層／電子注入層／陰極）などの多層構成で積層したものなどが挙げられる。 The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. In this case, the light emitting layer contains a light emitting material, and in addition, in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material, the light emitting layer may contain a hole injecting material or an electron injecting material. Good. In addition, the light emitting material preferably has a very high fluorescence quantum efficiency, a high hole transport capability and an electron transport capability, and forms a uniform thin film. As the multilayer organic EL device, (anode / light-emitting layer / electron transport layer / cathode), (anode / hole transport layer / light-emitting layer / cathode), (anode / hole transport layer / light-emitting layer / electron transport layer) / Anode), (anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode), (anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode), Examples thereof include those laminated in a multilayer structure such as (anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode).
本発明の有機ＥＬ素子における発光層には、発光媒体および発光材料として公知の化合物を用いることができる。発光媒体としては、特に制限されることはなく、公知の化合物の中から選ぶことができるが、１，１，４，４−テトラフェニル−１，３−ブタジェン又は４，４′−（２，２−ジフェニルビニル）ビフェニルなどの多環縮合芳香族化合物、ベンゾオキサゾール系、ベンゾチアゾール系、ベンゾイミダゾール系などのヘテロ原子を含有する芳香族化合物、トリス（８−キノリノラート）アルミニウム、トリス（２−メチル−８−キノリノラート）アルミニウム、トリス（４−メチル−８−キノリノラート）アルミニウムなどのアルミニウム錯体を用いることができる。発光材料としては、ＤＣＭなどのスチリル誘導体、アントラセン系化合物、ナフタセン系化合物、フルオランテン系化合物などの多環縮合芳香族化合物などを用いることができる。 For the light emitting layer in the organic EL device of the present invention, known compounds can be used as the light emitting medium and the light emitting material. The luminescent medium is not particularly limited and can be selected from known compounds, but 1,1,4,4-tetraphenyl-1,3-butadiene or 4,4 ′-(2, Polycyclic condensed aromatic compounds such as 2-diphenylvinyl) biphenyl, aromatic compounds containing heteroatoms such as benzoxazole, benzothiazole, and benzimidazole, tris (8-quinolinolato) aluminum, tris (2-methyl) Aluminum complexes such as -8-quinolinolato) aluminum and tris (4-methyl-8-quinolinolato) aluminum can be used. As the light emitting material, a styryl derivative such as DCM, an anthracene compound, a naphthacene compound, a polycyclic condensed aromatic compound such as a fluoranthene compound, or the like can be used.
正孔注入材料または正孔輸送材料としては、正孔を輸送する能力を持ち、陽極からの正孔注入効果、発光層または発光材料に対して優れた正孔輸送効果を有し、発光層で生じた励起子の電子輸送層又は電子輸送材料への移動を防止し、かつ薄膜形成能力の優れた化合物が好ましい。具体的には、フタロシアニン誘導体、ナフタロシアニン誘導体、ポルフィリン誘導体、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、及びポリビニルカルバゾール、ポリシラン、導電性高分子等の高分子材料が挙げられるが、これらに限定されるものではない。 As a hole injection material or a hole transport material, it has the ability to transport holes, has a hole injection effect from the anode, and has an excellent hole transport effect for the light emitting layer or light emitting material. A compound that prevents the generated excitons from moving to the electron transport layer or the electron transport material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, benzidine type Examples include triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinyl carbazole, polysilane, and conductive polymer, but are not limited thereto. Absent.
これらの正孔注入材料または正孔輸送材料の中で、さらに効果的な正孔注入材料または正孔輸送材料は、芳香族三級アミン誘導体又はフタロシアニン誘導体である。芳香族三級アミン誘導体の具体例としては、トリフェニルアミン、トリトリルアミン、トリジフェニルアミン、Ｎ，Ｎ′−ジフェニル−Ｎ，Ｎ′−（３−メチルフェニル）−１，１′−ビフェニル−４，４′−ジアミン、Ｎ，Ｎ，Ｎ′，Ｎ′−（４−メチルフェニル）−１，１′−フェニル−４，４′−ジアミン、Ｎ，Ｎ，Ｎ′，Ｎ′−（４−メチルフェニル）−１，１′−ビフェニル−４，４′−ジアミン、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′−（メチルフェニル）−Ｎ，Ｎ′−（４−ｎ−ブチルフェニル）−フェナントレン−９，１０−ジアミン、Ｎ，Ｎ−ビス（４−ジ−４−トリルアミノフェニル）−４−フェニル−シクロヘキサン等、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も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。フタロシアニン（Ｐｃ）誘導体の具体例は、Ｈ２ＰＣ、ＣｕＰｃ、ＣｏＰｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、ＭｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、ＣｌＳｎＰｃ、Ｃｌ２ＳｉＰｃ、（ＨＯ）ＡｌＰｃ、（ＨＯ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰｃ等のフタロシアニン誘導体及びナフタロシアニン誘導体である。また、導電性高分子としては、ポリアニリン誘導体やポリチオフェン誘導体などが挙げられるが、これらに限定されるものではない。 Among these hole injection materials or hole transport materials, more effective hole injection materials or hole transport materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, tridiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4, 4'-diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N ', N'-(4-methyl Phenyl) -1,1'-biphenyl-4,4'-diamine, N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, N'- (Methylphenyl) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, etc. Or these aromatic tertiary amino acids An oligomer or polymer having a backbone, but not limited thereto. Specific examples of phthalocyanine (Pc) derivatives are H 2 PC, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, and MoOPc. Examples of the conductive polymer include, but are not limited to, polyaniline derivatives and polythiophene derivatives.
電子輸送材料として用いる化合物は、電子を輸送する能力を持ち、陰極からの電子注入効果、発光層または発光材料に対して、優れた電子輸送効果を有し、発光層で生成した励起子の正孔注入層への移動を防止し、かつ薄膜形成性に優れた化合物が好ましい。電子輸送材料としては金属錯体化合物、含窒素化合物などが知られている。金属錯体化合物としてはトリス（８−キノリナート）リチウム、トリス（８−キノリナート）亜鉛、トリス（８−キノリナート）銅、トリス（８−キノリナート）マンガン、トリス（８−キノリナート）アルミニウム、トリス（２−メチル−８−キノリナート）アルミニウム、トリス（４−メチル−８−キノリナート）アルミニウム、トリス（４−プロピル−８−キノリナート）アルミニウムなどが挙げられる。含窒素化合物としては、オキサゾール誘導体、チアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体及びフェナントロリン誘導体などが知られている。特に、フェナントロリン誘導体としては、４，７−ジフェニル−１，１０−フェナントロリン、４，７−ジ−ｍ−トリル−１，１０−フェナントロリン、４，７−ジ−ｐ−トリル−１，１０−フェナントロリン、２，９−ジメチル−４，７−ジフェニル−１，１０−フェナントロリン、２，９−ジメチル−４，７−ジ−ｐ−トリル−１，１０−フェナントロリン、２，９−ジメチル−４，７−ジ−ｍ−トリル−１，１０−フェナントロリン、２，９−ジエチル−４，７−ジフェニル−１，１０−フェナントロリンなどが挙げられる。 The compound used as an electron transport material has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron transport effect with respect to the light emitting layer or the light emitting material. A compound that prevents movement to the hole injection layer and is excellent in thin film formation is preferable. As electron transport materials, metal complex compounds, nitrogen-containing compounds and the like are known. Examples of metal complex compounds include tris (8-quinolinato) lithium, tris (8-quinolinato) zinc, tris (8-quinolinato) copper, tris (8-quinolinato) manganese, tris (8-quinolinato) aluminum, tris (2-methyl). -8-quinolinato) aluminum, tris (4-methyl-8-quinolinato) aluminum, tris (4-propyl-8-quinolinato) aluminum and the like. Known nitrogen-containing compounds include oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and phenanthroline derivatives. In particular, phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 4,7-di-m-tolyl-1,10-phenanthroline, 4,7-di-p-tolyl-1,10-phenanthroline. 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-di-p-tolyl-1,10-phenanthroline, 2,9-dimethyl-4,7 -Di-m-tolyl-1,10-phenanthroline, 2,9-diethyl-4,7-diphenyl-1,10-phenanthroline and the like.
本発明においては、電子輸送材料として、本発明の一般式（１）〜（６）で表される置換ビニル基含有ジピリドフェナジン誘導体を用いることが好ましい。また、本発明の有機ＥＬ素子は、前記一般式（１）〜（６）で表される置換ビニル基含有ジピリドフェナジン誘導体に、還元性ドーパントを添加、含有することが好ましい。還元性ドーパントとは、電子輸送性化合物を還元できる物質であり、一定の還元性を有するものであれば用いることができる。例えば、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属酸化物、希土類金属酸化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体などから選ばれる物質であると好ましい。 In this invention, it is preferable to use the substituted vinyl group containing dipyridophenazine derivative represented by General formula (1)-(6) of this invention as an electron transport material. Moreover, it is preferable that the organic EL element of this invention adds and contains a reducing dopant to the substituted vinyl group containing dipyridophenazine derivative represented by the said General Formula (1)-(6). A reducing dopant is a substance that can reduce an electron transporting compound and can be used as long as it has a certain reducing property. For example, alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, rare earth metal oxide, alkali metal organic complex, alkaline earth metal organic complex, etc. It is preferable that it is a substance chosen from.
これらの物質の中で、好ましい還元性ドーパントとしては、例えば、アルカリ金属としてＮａ、Ｋ、Ｒｂ、及びＣｓなどから選ばれるもの、アルカリ土類金属としてＣａ、Ｓｒ及びＢａから選ばれるものが好ましい。さらに好ましい還元性ドーパントは、Ｒｂ、Ｃｓであるが、有機ＥＬ素子に用いる電子輸送材料の特性に対応して、これらの還元性ドーパントを選ぶことが好ましい。 Among these substances, preferable reducing dopants include, for example, those selected from Na, K, Rb, and Cs as alkali metals, and those selected from Ca, Sr, and Ba as alkaline earth metals. More preferable reducing dopants are Rb and Cs, but it is preferable to select these reducing dopants according to the characteristics of the electron transport material used in the organic EL device.
有機エレクトロルミネッセンス素子の陽極に使用される導電性材料としては、４ｅＶより大きな仕事関数を持つものが適しており、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウムなど、およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板に使用される酸化錫、酸化インジウムなどの酸化金属、さらにはポリチオフェンやポリピロールなどの有機導電性樹脂が用いられる。陰極に用いられる導電性材料としては、４ｅＶより小さな仕事関数を持つものが適しており、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガンなどおよびこれらの合金が用いられるが、これらに限定されるものではない。合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウムなどが代表例として挙げられるが、これらに限定されるものではない。合金の比率は、蒸着源の温度、雰囲気、真空度などにより、適切に制御することができる。陽極、陰極は必要に応じて二層以上の層に構成されてもよい。 As a conductive material used for an anode of an organic electroluminescence element, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium And alloys thereof, 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. As the conductive material used for the cathode, a material having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and alloys thereof are used. It is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy can be appropriately controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, and the like. The anode and the cathode may be composed of two or more layers as necessary.
本発明の有機ＥＬ素子で用いる透明電極の支持基板は、効率よく発光させるために、十分透明であることが望ましい。透明電極は、上記の導電性材料を用いて、蒸着やスパッタリング等の方法で所定の透光性が確保できるように設定する。発光面の電極は、光透過率を１０％以上にすることが望ましい。基板は、機械的、熱的強度を有し、透明性を有するものであれば限定されるものではないが、ガラス基板や透明性樹脂のフィルムおよびシートが挙げられる。フィルムやシートに用いる透明性樹脂としては、ポリエチレン、ポリエチレン共重合体、ポリプロピレン、ポリプロピレン共重合体、ポリスチレン、ポリスチレン共重合体、シンジオタクチックポリスチレン、ポリメチルメタアクリレート、ナイロン、ポリエーテルサルホン、ポリサルホン、ポリカーボネート、ポリカーボネート共重合体、ポリアリレート、ポリエーテルイミド、テトラフルオロエチレン−エチレン共重合体、ポリビニリデンフルオライド、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレートなどが挙げられる。 The transparent electrode support substrate used in the organic EL device of the present invention is desirably sufficiently transparent in order to efficiently emit light. The transparent electrode is set using the above-described conductive material so that predetermined translucency can be 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 is transparent, and examples thereof include a glass substrate and a transparent resin film and sheet. Transparent resins used for films and sheets include polyethylene, polyethylene copolymer, polypropylene, polypropylene copolymer, polystyrene, polystyrene copolymer, syndiotactic polystyrene, polymethyl methacrylate, nylon, polyethersulfone, and polysulfone. , Polycarbonate, polycarbonate copolymer, polyarylate, polyetherimide, tetrafluoroethylene-ethylene copolymer, polyvinylidene fluoride, polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and the like.
本発明における有機エレクトロルミネッセンス素子の各層の形成は、真空蒸着、スパッタリング、プラズマ、イオンプレーティングなどの乾式成膜法や、スピンコーティング、ディッピング、フローコーティングなどの湿式成膜法、いずれの方法も用いることができる。陽極、陰極間に挟持される有機薄膜層の各層の膜厚は特に限定されるものではないが、適切な膜厚に設定する必要がある。通常の膜厚は０．２ｎｍから５００ｎｍの範囲で適宜選ぶのが好ましい。 The formation of each layer of the organic electroluminescent element in the present invention uses any 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. be able to. The thickness of each layer of the organic thin film layer sandwiched between the anode and the cathode is not particularly limited, but must be set to an appropriate thickness. The normal film thickness is preferably selected as appropriate in the range of 0.2 nm to 500 nm.
本発明の化合物を成膜する場合は、乾式成膜法、湿式成膜法のいずれも用いることができるが、特に、本発明の置換ビニル基含有ジピリドフェナジン誘導体を電子輸送層として用いる場合は、真空蒸着、スパッタリングなどの乾式成膜法を用いることが好ましい。 When the compound of the present invention is formed, either a dry film formation method or a wet film formation method can be used. In particular, when the substituted vinyl group-containing dipyridophenazine derivative of the present invention is used as an electron transport layer. It is preferable to use a dry film forming method such as vacuum evaporation or sputtering.
本発明の有機エレクトロルミネッセンス素子においては、本発明の請求項１の化合物、例えば一般式（１）〜（６）の化合物のほかに、発光材料、ドーピング材料、正孔注入材料、正孔輸送材料、電子注入材料、および電子輸送材料の少なくとも１種が同一層に含有されてもよい。また、本発明により得られた有機ＥＬ素子の、温度、湿度、雰囲気などに対する安定性の向上のために、素子の表面に保護層を設けたり、樹脂などにより素子全体を保護することも可能である。
In the organic electroluminescence device of the present invention, in addition to the compound of
本発明により、新規な置換ビニル基含有ジピリドフェナジン誘導体を提供することができる。そして本発明の置換ビニル基含有ジピリドフェナジン誘導体を有機ＥＬ素子の電子輸送材料として用いると、発光輝度、発光効率が高く、発光寿命が長い有機エレクトロルミネッセンス素子が得られる。このため、本発明の有機ＥＬ素子は、薄型テレビジョンやフラットパネルディスプレイの平面発光体、複写機やプリンターなどの光源、液晶ディスプレイや計器類、照明器具、表示板、標識灯などの光源として有用である。 According to the present invention, a novel substituted vinyl group-containing dipyridophenazine derivative can be provided. When the substituted vinyl group-containing dipyridophenazine derivative of the present invention is used as an electron transport material for an organic EL device, an organic electroluminescence device having high emission luminance and emission efficiency and a long emission lifetime can be obtained. For this reason, the organic EL device of the present invention is useful as a light source for flat light emitters of thin televisions and flat panel displays, light sources for copiers and printers, liquid crystal displays and instruments, lighting fixtures, display boards, and indicator lights. It is.
以下に実施例及び応用例を挙げて本発明を説明するが、本発明はこれにより何ら限定されるものではない。 Hereinafter, the present invention will be described with reference to examples and application examples, but the present invention is not limited thereto.
実施例１ 化合物（１−１）の合成
実施例２ 化合物（２−１）の合成
実施例３ 化合物（７−１）の合成
実施例４ 化合物（７−４）の合成
実施例５ 化合物（１０−１）の合成
実施例６ 化合物（１２−４）の合成
実施例７ 化合物（１４−４）の合成
実施例８ 化合物（１５−３）の合成
応用例１
厚さ１５０ｎｍのＩＴＯ透明電極を有する２５ｍｍ×２５ｍｍサイズのガラス基板をアセトン、洗浄剤（商品名：セミコクリーン５６）、イソプロパノールを用いて超音波洗浄をした。さらに、イソプロパノール中で煮沸したあと、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。このガラス基板を真空蒸着装置内に設置し、先ず、正孔注入層として下記式で示されるＤＮＴＰＤを６０ｎｍの厚さに蒸着した後、その上に正孔輸送層として下記式で示されるα−ＮＰＤを２０ｎｍの厚さに蒸着した。さらに、発光媒体としてトリス（８−キノリナート）アルミニウム（Ａｌｑ３）と発光材料である下記ルブレン（Ａｌｑ３に対して４．０ｍｏｌ％）を共蒸着し、膜厚５０ｎｍの発光層を形成した。この上に、電子輸送層として化合物（１−１）を膜厚４０ｎｍに蒸着した。次に、ＬｉＦを０．２ｎｍの厚さに蒸着し、この上にアルミニウムを膜厚１５０ｎｍに蒸着して有機ＥＬ素子を作製した。この素子に６．０Ｖの直流電圧を印加すると、電流密度４．５ｍＡ／ｃｍ２、発光輝度７４ｃｄ／ｍ２、発光効率１．６ｃｄ／Ａの下記式で示されるルブレンからの黄色発光が得られた。初期輝度３００ｃｄ／ｍ２で一定電流駆動を行なったところ、輝度が半減する時間（半減寿命）は５３０時間であった。
Application example 1
A glass substrate having a size of 25 mm × 25 mm having an ITO transparent electrode having a thickness of 150 nm was subjected to ultrasonic cleaning using acetone, a cleaning agent (trade name: Semicoclean 56), and isopropanol. Furthermore, after boiling in isopropanol, what was UV / ozone cleaned was used as a transparent conductive support substrate. This glass substrate was placed in a vacuum deposition apparatus, and first, DNTPD represented by the following formula was deposited as a hole injection layer to a thickness of 60 nm, and then a positive transport layer α- NPD was deposited to a thickness of 20 nm. Further, the tris-emitting medium (8 quinolinato) aluminum (Alq 3) as follows rubrene which is a light-emitting material (4.0 mol% with respect to Alq 3) was co-evaporated to form the light-emitting layer having a thickness of 50nm. On this, the compound (1-1) was vapor-deposited with a film thickness of 40 nm as an electron carrying layer. Next, LiF was vapor-deposited to a thickness of 0.2 nm, and aluminum was vapor-deposited thereon to a thickness of 150 nm to produce an organic EL element. When a DC voltage of 6.0 V is applied to the device, yellow light emission from rubrene represented by the following formula having a current density of 4.5 mA / cm 2 , an emission luminance of 74 cd / m 2 , and an emission efficiency of 1.6 cd / A is obtained. It was. When constant current driving was performed at an initial luminance of 300 cd / m 2 , the time during which the luminance was reduced by half (half life) was 530 hours.
応用例２
応用例１において、電子輸送層として用いた化合物（１−１）を、還元性ドーパントであるＬｉ（Ｌｉ源：サエス・ゲッター社製、Ｌｉディスペンサー）を膜厚２０ｎｍに共蒸着［化合物（１−１）：Ｌｉの重量比 １０：１］した以外は、応用例１と同様にして有機ＥＬ素子を作製した。この素子の直流印加電圧６．０Ｖで電流密度３．０ｍＡ／ｃｍ２、発光輝度１２６ｃｄ／ｍ２、発光効率４．２ｃｄ／Ａのルブレンからの黄色発光が得られた。初期輝度３００ｃｄ／ｍ２での半減寿命は１９５０時間であった。
Application example 2
In Application Example 1, the compound (1-1) used as the electron transport layer was co-deposited with Li (Li source: manufactured by SAES Getter Co., Ltd., Li dispenser) as a reducing dopant into a film thickness of 20 nm [compound (1- 1): The weight ratio of Li was 10: 1], and an organic EL device was produced in the same manner as in Application Example 1. Yellow light emission from rubrene with a current density of 3.0 mA / cm 2 , emission luminance of 126 cd / m 2 , and emission efficiency of 4.2 cd / A was obtained at a DC applied voltage of 6.0 V of this device. The half life at an initial luminance of 300 cd / m 2 was 1950 hours.
応用例３〜９
応用例２において、電子輸送層に化合物（１−１）の代わりに、表１に示した化合物を用いた以外は、応用例２と同様にして有機ＥＬ素子を作製した。これらの素子は、直流印加電圧６．０Ｖでいずれもルブレンからの黄色発光を示した。電流密度、発光輝度、発光効率、半減寿命を表１に示した。
Application examples 3-9
In Application Example 2, an organic EL device was produced in the same manner as in Application Example 2, except that the compound shown in Table 1 was used instead of the compound (1-1) in the electron transport layer. All of these devices exhibited yellow light emission from rubrene at a DC applied voltage of 6.0V. Table 1 shows the current density, light emission luminance, light emission efficiency, and half life.
比較例１
応用例１において、電子輸送材料として化合物（１−１）の代わりに、下記化合物を用いた以外は、応用例１と同様にして有機ＥＬ素子を作製した。この素子は直流印加電圧９．０Ｖでも発光しなかった。
In Application Example 1, an organic EL device was produced in the same manner as Application Example 1 except that the following compound was used instead of the compound (1-1) as the electron transport material. This device did not emit light even at a DC applied voltage of 9.0V.
比較例２
応用例９において、電子輸送材料として化合物（１５−３）の代わりに、下記化合物を用いた以外は、応用例２と同様にして有機ＥＬ素子を作製した。この素子は直流印加電圧９．０Ｖで発光しなかった。
In Application Example 9, an organic EL device was produced in the same manner as Application Example 2 except that the following compound was used instead of the compound (15-3) as the electron transport material. This device did not emit light at a DC applied voltage of 9.0V.
１ 陰極
２ 電子輸送層
３ 発光層
４ 正孔輸送層
５ 正孔注入層
６ 陽極
７ 基板
DESCRIPTION OF
Claims (4)
ことを特徴とする置換ビニル基含有ジピリドフェナジン誘導体。 The following general formula (A)
A substituted vinyl group-containing dipyridophenazine derivative characterized by the above.
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| JP2004149480A JP2005330219A (en) | 2004-05-19 | 2004-05-19 | Substituted vinyl group-containing dipyridophenazine derivative, electron transport material and organic electroluminescence device using the same |
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| JP2004149480A JP2005330219A (en) | 2004-05-19 | 2004-05-19 | Substituted vinyl group-containing dipyridophenazine derivative, electron transport material and organic electroluminescence device using the same |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007013478A1 (en) * | 2005-07-25 | 2007-02-01 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and electronic appliance |
| WO2015159541A1 (en) * | 2014-04-18 | 2015-10-22 | 保土谷化学工業株式会社 | Compound having tetraazatriphenylene ring structure, light-emitting material, and organic electroluminescent element |
| CN106749243A (en) * | 2017-01-06 | 2017-05-31 | 上海天马有机发光显示技术有限公司 | Quadripole compound, the luminescent layer material of main part comprising it, OLED display panel and electronic equipment |
| KR20210012800A (en) * | 2019-07-26 | 2021-02-03 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising same |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0688072A (en) * | 1992-09-07 | 1994-03-29 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
| JP2000150164A (en) * | 1999-12-10 | 2000-05-30 | Canon Inc | Electroluminescence element |
| WO2004006355A2 (en) * | 2002-07-10 | 2004-01-15 | E.I. Du Pont De Nemours And Company | Charge transport compositions which are quinazoline derivatives and electronic devices made with such compositions |
-
2004
- 2004-05-19 JP JP2004149480A patent/JP2005330219A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0688072A (en) * | 1992-09-07 | 1994-03-29 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
| JP2000150164A (en) * | 1999-12-10 | 2000-05-30 | Canon Inc | Electroluminescence element |
| WO2004006355A2 (en) * | 2002-07-10 | 2004-01-15 | E.I. Du Pont De Nemours And Company | Charge transport compositions which are quinazoline derivatives and electronic devices made with such compositions |
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