JPH06293778A - Silanamine derivative and its production - Google Patents
Silanamine derivative and its productionInfo
- Publication number
- JPH06293778A JPH06293778A JP5078344A JP7834493A JPH06293778A JP H06293778 A JPH06293778 A JP H06293778A JP 5078344 A JP5078344 A JP 5078344A JP 7834493 A JP7834493 A JP 7834493A JP H06293778 A JPH06293778 A JP H06293778A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- substituted
- derivative
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 150000004756 silanes Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- 238000005401 electroluminescence Methods 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000010409 thin film Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- -1 aromatic tertiary amine Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- MSFZMZDSTSIPFX-UHFFFAOYSA-N n-phenylpyren-1-amine Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1NC1=CC=CC=C1 MSFZMZDSTSIPFX-UHFFFAOYSA-N 0.000 description 2
- GJNGMQYHOZFQNX-UHFFFAOYSA-N n-pyren-1-ylacetamide Chemical compound C1=C2C(NC(=O)C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 GJNGMQYHOZFQNX-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical group [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 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
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HMMPCBAWTWYFLR-UHFFFAOYSA-N n-pyridin-2-ylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=N1 HMMPCBAWTWYFLR-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】Detailed Description of the Invention
【０００１】[0001]
【産業上の利用分野】本発明は、有機エレクトロルミネ
ッセンス素子（以下、有機ＥＬ素子という）や電子写真
感光体等で用いられる正孔輸送材料として好適なシラナ
ミン誘導体およびその製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silanamine derivative suitable as a hole transporting material used in organic electroluminescent elements (hereinafter referred to as organic EL elements), electrophotographic photoreceptors and the like, and a method for producing the same.
【０００２】[0002]
【従来の技術】有機ＥＬ素子としては種々の構成のもの
があるが、ＩＴＯ（陽極）／正孔輸送層／発光層／陰極
の素子構成のものは高輝度発光が可能なものとして知ら
れている（特開昭６３−２９５６９５号公報参照）。こ
の構成の有機ＥＬ素子では２０Ｖ以上の印加電圧で数百
ｃｄ／ｍ2 の高輝度発光が可能であり、前記公報には正
孔輸送層の材料として芳香族第三級アミンを用いること
が開示されている。2. Description of the Related Art There are various types of organic EL devices, and the device structure of ITO (anode) / hole transport layer / light emitting layer / cathode is known to be capable of high-luminance light emission. (See JP-A-63-295695). The organic EL device having this structure is capable of high-luminance light emission of several hundred cd / m 2 at an applied voltage of 20 V or higher, and the publication discloses that an aromatic tertiary amine is used as the material of the hole transport layer. Has been done.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、アミン
系の材料には、酸化に弱いという難点や、薄膜としたと
きに経時的に再結晶化を起こすという難点がある。ま
た、アミン系の材料は主としてウルマン反応を利用して
製造されるが、この反応は高い反応温度を必要とし、ま
た、重金属を触媒として用いるために廃液の処理が困難
である。However, amine-based materials have the drawback that they are weak against oxidation and that they recrystallize over time when formed into a thin film. Further, the amine-based material is mainly produced by utilizing the Ullmann reaction, but this reaction requires a high reaction temperature, and the treatment of the waste liquid is difficult because a heavy metal is used as a catalyst.
【０００４】本発明の目的は、酸化に強いとともに再結
晶化を起こしにくい正孔輸送層等を得るのに好適なシラ
ナミン誘導体およびその製造方法を提供することにあ
る。An object of the present invention is to provide a silanamin derivative suitable for obtaining a hole transport layer which is strong against oxidation and hardly recrystallized, and a method for producing the same.
【０００５】[0005]
【課題を解決するための手段】上目的を達成する本発明
のシラナミン誘導体は、一般式（Ｉ）The silanamin derivative of the present invention which achieves the above object has the general formula (I):
【化４】 （式中、Ａｒ1 は炭素数６〜２０のアリール基または炭
素数３〜１０の複素芳香環基であり、これらの基にはア
ルキル基またはフェニル基が核置換されていてもよい。
Ａｒ2 は炭素数７〜２０のアリール基または炭素数３〜
１０の複素芳香環基であり、これらの基にはアルキル基
またはフェニル基が核置換されていてもよい。Ａｒ3 は
炭素数６〜２０のアリール基であり、この基にはアルキ
ル基が核置換されていてもよい。）で表されるものであ
る。[Chemical 4] (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 10 carbon atoms, and these groups may be substituted with an alkyl group or a phenyl group as a nucleus.
Ar 2 is an aryl group having 7 to 20 carbon atoms or 3 to 3 carbon atoms.
10 heteroaromatic ring groups, which may be nucleus-substituted with an alkyl group or a phenyl group. Ar 3 is an aryl group having 6 to 20 carbon atoms, and an alkyl group may be nucleus-substituted in this group. ) Is represented.
【０００６】また、本発明のシラナミン誘導体の製造方
法は、一般式（II）Further, the method for producing the silanamin derivative of the present invention has the general formula (II)
【化５】 （式中、Ａｒ1 は炭素数６〜２０のアリール基または炭
素数３〜１０の複素芳香環基であり、これらの基にはア
ルキル基またはフェニル基が核置換されていてもよい。
Ａｒ2 は炭素数７〜２０のアリール基または炭素数３〜
１０の複素芳香環基であり、これらの基にはアルキル基
またはフェニル基が核置換されていてもよい。）で表さ
れるアミンと、一般式(III)[Chemical 5] (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 10 carbon atoms, and these groups may be substituted with an alkyl group or a phenyl group as a nucleus.
Ar 2 is an aryl group having 7 to 20 carbon atoms or 3 to 3 carbon atoms.
10 heteroaromatic ring groups, which may be nucleus-substituted with an alkyl group or a phenyl group. ) And the general formula (III)
【化６】 （式中、Ａｒ3 は炭素数６〜２０のアリール基であり、
この基にはアルキル基が核置換されていてもよい。）で
表されるハロゲン化シランとを縮合反応させることを特
徴とするものである。[Chemical 6] (In the formula, Ar 3 is an aryl group having 6 to 20 carbon atoms,
An alkyl group may be nucleus-substituted in this group. ) And a halogenated silane represented by the formula (6) are subjected to a condensation reaction.
【０００７】以下、本発明を詳細に説明する。まず本発
明のシラナミン誘導体について説明すると、このシラナ
ミン誘導体は前述のように一般式（Ｉ）The present invention will be described in detail below. First, the silanamin derivative of the present invention will be described. This silanamin derivative has the general formula (I) as described above.
【化７】 で表されるものである。[Chemical 7] It is represented by.
【０００８】ここで、Ａｒ1 は炭素数６〜２０のアリー
ル基または炭素数３〜１０の複素芳香環基であり、これ
らの基にはアルキル基またはフェニル基が核置換されて
いてもよい。炭素数６〜２０のアリール基の具体例とし
ては、フェニル基、ナフチル基、ビフェニル基、アント
ラニル基、アセナフチル基、フェナンスリル基、ピレニ
ル基等が挙げられる。また、炭素数３〜１０の複素芳香
環基の具体例としては、ピローリル基、チオフェニル
基、フラニル基、ピリジニル基、イミダゾリル基、イン
ドーリル基、ベンゾチオフェニル基、ベンゾフラニル基
等が挙げられる。そして、これらの基に核置換し得るア
ルキル基の具体例としてはメチル基、エチル基などが挙
げられる。Here, Ar 1 is an aryl group having 6 to 20 carbon atoms or a heteroaromatic ring group having 3 to 10 carbon atoms, and these groups may be nucleus-substituted with an alkyl group or a phenyl group. Specific examples of the aryl group having 6 to 20 carbon atoms include phenyl group, naphthyl group, biphenyl group, anthranyl group, acenaphthyl group, phenanthryl group and pyrenyl group. Further, specific examples of the heteroaromatic ring group having 3 to 10 carbon atoms include a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, an imidazolyl group, an indolyl group, a benzothiophenyl group, a benzofuranyl group and the like. Specific examples of the alkyl group which can be nuclear-substituted with these groups include a methyl group and an ethyl group.
【０００９】上記一般式（Ｉ）中のＡｒ2 は、炭素数７
〜２０のアリール基または炭素数３〜１０の複素芳香環
基であり、これらの基にはアルキル基またはフェニル基
が核置換されていてもよい。炭素数７〜２０のアリール
基の具体例としては、ナフチル基、ビフェニル基、アン
トラニル基、アセナフチル基、フェナンスリル基、ピレ
ニル基等が挙げられる。また、炭素数３〜１０の複素芳
香環基の具体例としては、Ａｒ1 の説明の中で挙げたも
のと同じものが例示される。そして、これらの基に核置
換し得るアルキル基の具体例としては、Ａｒ1 の説明の
中で挙げたものと同じものが例示される。Ar 2 in the general formula (I) has 7 carbon atoms.
To an aryl group having 20 to 20 carbon atoms or a heteroaromatic ring group having 3 to 10 carbon atoms, and these groups may be substituted with an alkyl group or a phenyl group as a nucleus. Specific examples of the aryl group having 7 to 20 carbon atoms include naphthyl group, biphenyl group, anthranyl group, acenaphthyl group, phenanthryl group and pyrenyl group. Further, specific examples of the heteroaromatic ring group having 3 to 10 carbon atoms include the same ones as mentioned in the description of Ar 1 . Specific examples of the alkyl group which can be nuclear-substituted with these groups are the same as those mentioned in the description of Ar 1 .
【００１０】上記一般式（Ｉ）中のＡｒ3 は炭素数６〜
２０のアリール基であり、この基にはアルキル基が核置
換されていてもよい。このアリール基の具体例として
は、Ａｒ1 の説明の中で挙げたものと同じものが例示さ
れる。また、この基に核置換し得るアルキル基の具体例
としても、Ａｒ1 の説明の中で挙げたものと同じものが
例示される。Ar 3 in the general formula (I) has 6 to 6 carbon atoms.
20 aryl groups, which may be nucleus-substituted with alkyl groups. Specific examples of the aryl group are the same as those mentioned in the description of Ar 1 . Further, specific examples of the alkyl group which can be nuclear-substituted with this group are also the same as those mentioned in the description of Ar 1 .
【００１１】本発明のシラナミン誘導体の具体例を、図
１および図２に示す。本発明のシラナミン誘導体は、公
知の真空蒸着法等により容易に薄膜化することができ
る。さらには、ポリカーボネート、ポリウレタン、ポリ
スチレン、ポリアリレート、ポリエステル等のポリマー
に本発明のシラナミン誘導体を分散させた溶液を用いキ
ャスト法、塗布法、スピンコート法等によっても、容易
に薄膜化することができる。Specific examples of the silanamine derivative of the present invention are shown in FIGS. 1 and 2. The silanamin derivative of the present invention can be easily formed into a thin film by a known vacuum deposition method or the like. Further, it is possible to easily form a thin film by a casting method, a coating method, a spin coating method or the like using a solution in which the silanamin derivative of the present invention is dispersed in a polymer such as polycarbonate, polyurethane, polystyrene, polyarylate or polyester. .
【００１２】上述のようにして薄膜化することができる
本発明のシラナミン誘導体は、正孔を輸送するという電
子機能を保有している一方で、アミン系材料に比べて耐
酸化性に優れ、かつ、薄膜とした場合でも再結晶化を起
こしにくいという特性を有している。したがって、本発
明のシラナミン誘導体は有機ＥＬ素子の正孔輸送層の材
料や正孔輸送性結着剤の材料あるいは電子写真感光体の
電荷輸送層（正孔輸送層）の材料等の正孔輸送材料とし
て好適である。The silanamin derivative of the present invention, which can be formed into a thin film as described above, has an electronic function of transporting holes, but is more excellent in oxidation resistance than amine-based materials, and Also, it has a characteristic that recrystallization is difficult to occur even when formed into a thin film. Therefore, the silanamine derivative of the present invention is a hole transporting material such as a material for a hole transporting layer of an organic EL device, a material for a hole transporting binder or a material for a charge transporting layer (hole transporting layer) of an electrophotographic photoreceptor. It is suitable as a material.
【００１３】このような特性を有する本発明のシラナミ
ン誘導体は、例えば以下に述べる本発明の方法により合
成することができる。本発明の方法は、前述したよう
に、一般式（II）The silanamin derivative of the present invention having such characteristics can be synthesized, for example, by the method of the present invention described below. As described above, the method of the present invention has the general formula (II)
【化８】 で表されるアミンと、一般式(III)[Chemical 8] An amine represented by the general formula (III)
【化９】 で表されるハロゲン化シランとを縮合反応させることを
特徴とするものである。[Chemical 9] It is characterized in that the halogenated silane represented by
【００１４】ここで、上記一般式（II）におけるＡｒ1
とＡｒ2 、および上記一般式(III)におけるＡｒ3 は、
本発明のシラナミ誘導体を表す前述の一般式（Ｉ）にお
けるＡｒ1 、Ａｒ2 およびＡｒ3 と同じである。また、
一般式(III) におけるＸはハロゲン原子であり、具体例
としてはフッ素、塩素、臭素、ヨウ素が挙げられる。一
般式（II）で表されるアミンの具体例を図３に示す。ま
た、一般式(III) で表されるハロゲン化シランの具体例
を図４に示す。Here, Ar 1 in the above general formula (II)
And Ar 2 , and Ar 3 in the above general formula (III),
It is the same as Ar 1 , Ar 2 and Ar 3 in the above-mentioned general formula (I) representing the silanami derivative of the present invention. Also,
X in the general formula (III) is a halogen atom, and specific examples thereof include fluorine, chlorine, bromine and iodine. A specific example of the amine represented by the general formula (II) is shown in FIG. A specific example of the halogenated silane represented by the general formula (III) is shown in FIG.
【００１５】一般式（II）で表されるアミンと一般式(I
II) で表されるハロゲン化シランとの縮合は、例えば以
下のようにして行うことができる。まず、一般式（II）
で表されるアミンを、アルゴンガス等の不活性ガス雰囲
気中で、溶媒に溶解させる。溶媒としてはジエチルエー
テル、ＴＨＦ（テトラヒドロフラン）、メタノール、エ
タノール、ＤＭＳＯ（ジメチルスルホキシド）、ＤＭＦ
（ジメチルホルムアミド）、トルエン等を用いることが
できるが、特にＴＨＦが好適である。また、溶媒は市販
のものを用いてもよいが、精製したものを用いることが
好ましい。溶媒の精製は、モレキュラーシーブスやシリ
カゲルによる乾燥、ナトリウムや五塩化リンからの蒸
留、不活性ガス雰囲気中での水素化カルシウムからの蒸
留等により行うことができる。The amine represented by the general formula (II) and the general formula (I
The condensation with the halogenated silane represented by II) can be performed, for example, as follows. First, general formula (II)
The amine represented by is dissolved in a solvent in an atmosphere of an inert gas such as argon gas. As the solvent, diethyl ether, THF (tetrahydrofuran), methanol, ethanol, DMSO (dimethyl sulfoxide), DMF
(Dimethylformamide), toluene and the like can be used, but THF is particularly preferable. A commercially available solvent may be used, but a purified solvent is preferably used. Purification of the solvent can be performed by drying with molecular sieves or silica gel, distillation from sodium or phosphorus pentachloride, distillation from calcium hydride in an inert gas atmosphere, and the like.
【００１６】次いで、上述のようにして得た溶液に、一
般式（II）のアミンに対して１〜５当量の塩基および１
〜５当量の一般式(III) のハロゲン化シランを順次加え
る。塩基としては水酸化ナトリウム、炭酸カリウム、水
素化ナトリウム、ピリジン、トリエチルアミン、ｔ−ブ
トキシカリウム、ＤＢＵ（１，８−ジアザビシクロ
［５．４．０．］ウンデク−７−エン）、ｎ−ブチルリ
チウム、フェニルリチウム等を用いることができるが、
ｎ−ブチルリチウムが特に好適である。塩基の好ましい
添加量は１．０〜２．４当量である。また、ハロゲン化
シランの好ましい添加量は１．０〜１．３当量である。Then, to the solution obtained as described above, 1 to 5 equivalents of the base and 1 to the amine of the general formula (II) are added.
~ 5 equivalents of halogenated silane of general formula (III) are added sequentially. As the base, sodium hydroxide, potassium carbonate, sodium hydride, pyridine, triethylamine, potassium t-butoxy, DBU (1,8-diazabicyclo [5.4.0.] Undec-7-ene), n-butyllithium, Phenyllithium or the like can be used,
n-Butyllithium is particularly preferred. The preferred addition amount of the base is 1.0 to 2.4 equivalents. Moreover, the preferable addition amount of the halogenated silane is 1.0 to 1.3 equivalents.
【００１７】なお、塩基およびハロゲン化シランは溶媒
に溶解させて前記溶液に添加してもよい。塩基を溶解す
る溶媒としては、ＴＨＦ、トルエン、ジエチルエーテ
ル、ジオキサン、ジメトキシエタン等を用いることがで
きるが、一般式（II）のアミンを溶解させる際に用いた
溶媒と同じものを用いることが好ましい。また、ハロゲ
ン化シランを溶解する溶媒としては、ジエチルエーテ
ル、ＴＨＦ、ジオキサン、トルエン、ジメトキシエタン
等を用いることができるが、一般式（II）のアミンを溶
解させる際に用いた溶媒と同じものを用いることが好ま
しい。The base and halogenated silane may be dissolved in a solvent and added to the above solution. As the solvent for dissolving the base, THF, toluene, diethyl ether, dioxane, dimethoxyethane or the like can be used, but it is preferable to use the same solvent as used for dissolving the amine of the general formula (II). . As the solvent for dissolving the halogenated silane, diethyl ether, THF, dioxane, toluene, dimethoxyethane or the like can be used, but the same solvent as used for dissolving the amine of the general formula (II) can be used. It is preferable to use.
【００１８】この後、反応温度−８０〜１００℃で１〜
３６時間反応させることにより、アミンとハロゲン化シ
ランとを縮合反応させる。反応温度は前述の範囲内から
適宜選択可能であり、室温でも十分に良好な収率で目的
とするシラナミン誘導体が得られる。また、反応時間も
前述の範囲内から適宜選択可能であり、８時間程度でも
十分に良好な収率で目的とするシラナミン誘導体が得ら
れる。Thereafter, at a reaction temperature of -80 to 100 ° C., 1 to
By reacting for 36 hours, the amine and the halogenated silane are condensed. The reaction temperature can be appropriately selected from the above range, and the desired silanamine derivative can be obtained even at room temperature with a sufficiently good yield. Further, the reaction time can be appropriately selected from the above range, and the target silanamin derivative can be obtained in a sufficiently good yield even for about 8 hours.
【００１９】反応生成物（目的とするシラナミン誘導
体）は、反応液からトルエン、ジエチルエーテル、酢酸
エチル等の溶媒で抽出し、無水硫酸マグネシウム等の乾
燥剤で乾燥した後に溶媒を留去し、この後トルエン、Ｄ
ＭＦ、ピリジン等の溶媒により再結晶させるか、シリカ
ゲルまたは活性アルミナを担持したカラムクロマトグラ
フィーにかけることにより、精製することができる。場
合によっては、さらに昇華精製を行なってもよい。The reaction product (the desired silanamine derivative) is extracted from the reaction solution with a solvent such as toluene, diethyl ether, ethyl acetate, dried with a desiccant such as anhydrous magnesium sulfate, and then the solvent is distilled off. After toluene, D
It can be purified by recrystallization with a solvent such as MF or pyridine, or by subjecting it to column chromatography supporting silica gel or activated alumina. Depending on the case, further sublimation purification may be performed.
【００２０】本発明の方法によれば、触媒として重金属
を使用することなく比較的に低い反応温度下で本発明の
シラナミン誘導体を得ることができることから、ウルマ
ン反応を利用してアミン系材料を得る場合よりも製造が
容易である。According to the method of the present invention, the silanamine derivative of the present invention can be obtained at a relatively low reaction temperature without using a heavy metal as a catalyst. Therefore, an Ullmann reaction is used to obtain an amine material. It is easier to manufacture than in the case.
【００２１】このようにして得られる本発明のシラナミ
ン誘導体は、前述したように正孔を輸送するという電子
機能を保有している一方で、アミン系材料に比べて耐酸
化性に優れ、かつ、薄膜とした場合でも再結晶化を起こ
しにくいという特性を有していることから、正孔輸送材
料として好適である。The silanamine derivative of the present invention thus obtained possesses the electronic function of transporting holes as described above, but is more excellent in oxidation resistance than amine-based materials, and It is suitable as a hole-transporting material because it has a characteristic that it is difficult to recrystallize even when formed into a thin film.
【００２２】本発明のシラナミン誘導体を正孔輸送層と
して用いた有機ＥＬ素子は、正孔輸送層の材料として前
記一般式（Ｉ）で表されるシラナミン誘導体を用いる以
外は公知の方法により製造することができる。このとき
の素子構成は、陽極／正孔輸送層／発光層／陰極、
陽極／正孔輸送層／発光層／電子注入層／陰極等、陽極
と発光層との間に正孔輸送層が介在している構成であれ
ばよい。正孔輸送層以外の構成部材の材料としては種々
の物質を用いることができ、目的とする有機ＥＬ素子の
用途等に応じて適宜選択可能である。The organic EL device using the silanamin derivative of the present invention as the hole transport layer is manufactured by a known method except that the silanamin derivative represented by the general formula (I) is used as the material of the hole transport layer. be able to. The device structure at this time is as follows: anode / hole transport layer / light emitting layer / cathode
Any structure may be used, such as an anode / hole transport layer / light emitting layer / electron injection layer / cathode, as long as the hole transport layer is interposed between the anode and the light emitting layer. Various materials can be used as the material of the constituent members other than the hole transport layer, and can be appropriately selected depending on the intended use of the organic EL device and the like.
【００２３】有機ＥＬ素子の正孔輸送層として本発明の
シラナミン誘導体を用いた場合には、このシラナミン誘
導体がアミン系材料に比べて耐酸化性に優れ、かつ、薄
膜とした場合でも再結晶化を起こしにくいという特性を
有していることから、正孔輸送層としてアミン系材料を
用いた有機ＥＬ素子よりも素子寿命の長いものを得るこ
とができる。When the silanamin derivative of the present invention is used as the hole transport layer of the organic EL device, the silanamin derivative is more excellent in oxidation resistance than the amine-based material and recrystallized even when formed into a thin film. Since it has a characteristic of being less likely to cause the above, it is possible to obtain a device having a longer device life than the organic EL device using the amine-based material as the hole transport layer.
【００２４】[0024]
【実施例】以下、本発明の実施例について説明する。 実施例１（シラナミン誘導体の製造） まず、水素化カルシウムからアルゴンガス雰囲気下蒸留
したＴＨＦ １５０ｍｌにアルゴンガス雰囲気下で、Ｎ
−フェニル−１−ナフチルアミン［図３（１）に示すア
ミン；東京化成（株）製］３．０２ｇ（１３．８ｍ mo
l）を溶解させた。次いで、上で得られた溶液にｎ−ブ
チルリチウムのヘキサン溶液（アルドリッチ社製）１２
ｍｌ（約２０ｍ mol）とトリフェニルクロロシラン［図
４（１）に示すハロゲン化シラン；信越化学（株）製］
４．２８ｇ（１４．５ｍ mol）とを加えて、室温で８時
間反応させた。反応終了後、反応生成物を酢酸エチルで
抽出し、無水硫酸マグネシウムで乾燥した後にロータリ
ーエバポレーターで溶媒を留去し、得られた化合物をピ
リジンで洗浄したところ、２．０２ｇの白色粉末が得ら
れた。EXAMPLES Examples of the present invention will be described below. Example 1 (Production of Silanamine Derivative) First, 150 ml of THF distilled from calcium hydride under an argon gas atmosphere was subjected to N 2 under an argon gas atmosphere.
-Phenyl-1-naphthylamine [amine shown in FIG. 3 (1); manufactured by Tokyo Kasei Co., Ltd.] 3.02 g (13.8 mmo)
l) was dissolved. Then, a hexane solution of n-butyllithium (manufactured by Aldrich Co.) 12 was added to the solution obtained above.
ml (about 20 mmol) and triphenylchlorosilane [halogenated silane shown in Fig. 4 (1); manufactured by Shin-Etsu Chemical Co., Ltd.]
4.28 g (14.5 mmol) was added, and the mixture was reacted at room temperature for 8 hours. After completion of the reaction, the reaction product was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, the solvent was distilled off with a rotary evaporator, and the obtained compound was washed with pyridine. 2.02 g of white powder was obtained. It was
【００２５】この白色粉末のＦＤ−Ｍａｓｓ（フィール
ドディフュージョンマススペクトロスコピー）を測定し
たところ、Ｃ34Ｈ27ＮＳｉ＝４７７に対して４７７の親
ピークが得られた。また、この白色粉末のＩＲスペクト
ルを測定したところ、１６２０，１５２０，１３００，
８８０（ｃｍ-1）に吸収が観測された。これらのことか
ら、得られた白色粉末は、目的とするＮ−トリフェニル
シリル−Ｎ−フェニル−１−ナフチルアミン［図１
（１）に示すシラナミン誘導体；融点１７６℃。以下Ｓ
Ｎ−１と略記する。］であると同定された（収率３１
％）。When the FD-Mass (field diffusion mass spectroscopy) of this white powder was measured, a parent peak of 477 was obtained for C 34 H 27 NSi = 477. The IR spectrum of this white powder was measured and found to be 1620, 1520, 1300,
Absorption was observed at 880 (cm -1 ). From these facts, the obtained white powder shows the desired N-triphenylsilyl-N-phenyl-1-naphthylamine [Fig.
Silanamine derivative shown in (1); melting point 176 ° C. Below S
It is abbreviated as N-1. ] (Yield 31
%).
【００２６】実施例２（シラナミン誘導体の製造） Ｎ−フェニル−１−ナフチルアミンに代えてＮ−フェニ
ル−２−ナフチルアミン［図３（２）に示すアミン；東
京化成（株）製］３．０６ｇ（１４．０ｍ mol）を用
い、このアミンとトリフェニルクロロシラン［図４
（１）に示すハロゲン化シラン；信越化学（株）製］
４．２８ｇ（１４．５ｍ mol）とを実施例１と同様にし
て反応させた。反応終了後、反応生成物を実施例１と同
様にして精製して、１．２６ｇの白色粉末を得た。Example 2 (Production of Silanamine Derivative) N-phenyl-2-naphthylamine [amine shown in FIG. 3 (2); manufactured by Tokyo Kasei Co., Ltd.] 3.06 g (instead of N-phenyl-1-naphthylamine) 14.0mmol) and the amine and triphenylchlorosilane [Fig.
Halogenated silane shown in (1); manufactured by Shin-Etsu Chemical Co., Ltd.]
4.28 g (14.5 mmol) was reacted in the same manner as in Example 1. After completion of the reaction, the reaction product was purified in the same manner as in Example 1 to obtain 1.26 g of white powder.
【００２７】この白色粉末のＦＤ−Ｍａｓｓを測定した
ところ、Ｃ34Ｈ27ＮＳｉ＝４７７に対して４７７の親ピ
ークが得られた。また、この白色粉末のＩＲスペクトル
を測定したところ、１６２０，１５２０，１３００，８
６０（ｃｍ-1）に吸収が観測された。これらのことか
ら、得られた白色粉末は、目的とするＮ−トリフェニル
シリル−Ｎ−フェニル−２−ナフチルアミン［図１
（２）に示すシラナミン誘導体；融点２０１℃。以下Ｓ
Ｎ−２と略記する。］であると同定された（収率１９
％）。When the FD-Mass of this white powder was measured, a parent peak of 477 was obtained for C 34 H 27 NSi = 477. The IR spectrum of this white powder was measured and found to be 1620, 1520, 1300, 8
Absorption was observed at 60 (cm -1 ). From these facts, the obtained white powder shows that the target N-triphenylsilyl-N-phenyl-2-naphthylamine [Fig.
Silanamine derivative shown in (2); melting point 201 ° C. Below S
Abbreviated as N-2. ] Was identified (yield 19
%).
【００２８】実施例３（シラナミン誘導体の製造） （１）原料のアミンの製造 まず、１−アミノピレリン４．２２ｇ（１９．４ｍ mo
l）と無水酢酸５ｍｌ（４９ｍ mol）とを１００ｍｌの
塩化メチレンに溶解させて室温で１２時間反応させた
後、反応液から４．７３ｇの１−アセチルアミノピレン
を濾別した。次いで、得られた１−アセチルアミノピレ
ンの４．０４ｇ（１５．６ｍ mol）と、８．５５ｇ（４
１．９ｍ mol）のヨードベンゼン、７．３０ｇ（５２．
９ｍmol）の無水炭酸カリウム、および０．０５ｇの銅
粉を２００ｍｌのＤＭＳＯに懸濁させ、アルゴンガス雰
囲気下、１９０℃で５時間反応させた。この後、４ｇの
水酸化カリウムを２０ｍｌの水に溶解させたものを加え
て、さらに５時間反応させた。反応終了後、反応液を濾
過し、母液中の反応性生物を酢酸エチルで抽出し、無水
硫酸マグネシウムで乾燥した後にロータリーエバポレー
ターで溶媒を留去し、残渣を、シリカゲルを担持したカ
ラムクロマトグラフィーにより精製して、２．５２ｇの
Ｎ−１−ピレニル−アニリン［図３（３）に示すアミ
ン］を得た。Example 3 (Production of Silanamine Derivative) (1) Production of Raw Material Amine First, 4.22 g (19.4 mmo) of 1-aminopyrelin.
l) and 5 ml (49 mmol) of acetic anhydride were dissolved in 100 ml of methylene chloride and reacted at room temperature for 12 hours, and then 4.73 g of 1-acetylaminopyrene was filtered off from the reaction solution. Then, 4.04 g (15.6 mmol) of the obtained 1-acetylaminopyrene and 8.55 g (4
1.9 mmol of iodobenzene, 7.30 g (52.
Anhydrous potassium carbonate (9 mmol) and 0.05 g of copper powder were suspended in 200 ml of DMSO and reacted at 190 ° C. for 5 hours under an argon gas atmosphere. After this, 4 g of potassium hydroxide dissolved in 20 ml of water was added, and the reaction was further continued for 5 hours. After completion of the reaction, the reaction solution was filtered, the reaction product in the mother liquor was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was distilled off with a rotary evaporator, and the residue was subjected to silica gel-supported column chromatography. Purification yielded 2.52 g of N-1-pyrenyl-aniline [amine shown in FIG. 3 (3)].
【００２９】（２）シラナミン誘導体の製造 まず、上記（１）で得られたＮ−１−ピレニル−アニリ
ンの１．００ｇ（３．４１ｍ mol）と、トリフェニルク
ロロシラン［図４（１）に示すハロゲン化シラン；信越
化学（株）製］１．２１ｇ（４．１０ｍ mol）とを、実
施例１と同様に反応させた。このとき、塩基としてはｎ
−ブチルリチウムのヘキサン溶液（アルドリッチ社製）
５ｍｌ（約８ｍ mol）を用いた。反応終了後、反応生成
物を実施例１と同様にして精製して、０．１２ｇの白色
粉末を得た。(2) Production of Silanamine Derivative First, 1.00 g (3.41 mmol) of N-1-pyrenyl-aniline obtained in (1) above and triphenylchlorosilane [shown in FIG. 4 (1)]. Halogenated silane; manufactured by Shin-Etsu Chemical Co., Ltd.] 1.21 g (4.10 mmol) was reacted in the same manner as in Example 1. At this time, the base is n
-Butyl lithium hexane solution (Aldrich)
5 ml (about 8 mmol) was used. After completion of the reaction, the reaction product was purified in the same manner as in Example 1 to obtain 0.12 g of white powder.
【００３０】この白色粉末のＦＤ−Ｍａｓｓを測定した
ところ、Ｃ40Ｈ29ＮＳｉ＝５５１に対して５５１の親ピ
ークが得られた。また、この白色粉末のＩＲスペクトル
を測定したところ、１６２０，１５２０，１３００，８
６０（ｃｍ-1）に吸収が観測された。これらのことか
ら、得られた白色粉末は、目的とするＮ−トリフェニル
シリル−Ｎ−１−ピレニル−アニリン［図１（３）に示
すシラナミン誘導体；融点２６３℃。以下ＳＮ−３と略
記する。］であると同定された（収率６％）。When FD-Mass of this white powder was measured, a parent peak of 551 was obtained for C 40 H 29 NSi = 551. The IR spectrum of this white powder was measured and found to be 1620, 1520, 1300, 8
Absorption was observed at 60 (cm -1 ). From these facts, the obtained white powder was the target N-triphenylsilyl-N-1-pyrenyl-aniline [silanamine derivative shown in FIG. 1 (3); melting point 263 ° C. Hereinafter referred to as SN-3. ] Was identified (yield 6%).
【００３１】実施例４（シラナミン誘導体の製造） Ｎ−フェニル−１−ナフチルアミンに代えてＮ，Ｎ−ジ
−２−ピリジルアミン［図３（４）に示すアミン；東京
化成（株）製］５．０３ｇ（２９．４ｍ mol）を用い、
このアミンとトリフェニルクロロシラン［図４（１）に
示すハロゲン化シラン；信越化学（株）製］８．９８ｇ
（３０．４ｍ mol）とを実施例１と同様にして反応させ
た。このとき、塩基としてはｎ−ブチルリチウムのヘキ
サン溶液（アルドリッチ社製）２０ｍｌ（約３２ｍ mo
l）を用いた。反応終了後、反応生成物を実施例１と同
様にして精製して、１．４３ｇの白色粉末を得た。Example 4 (Production of Silanamine Derivative) N, N-di-2-pyridylamine [amine shown in FIG. 3 (4); manufactured by Tokyo Kasei Co., Ltd.] 5 in place of N-phenyl-1-naphthylamine Using 0.03 g (29.4 mmol),
8.98 g of this amine and triphenylchlorosilane [halogenated silane shown in FIG. 4 (1); manufactured by Shin-Etsu Chemical Co., Ltd.]
(30.4 mmol) was reacted in the same manner as in Example 1. At this time, as a base, 20 ml of a hexane solution of n-butyllithium (manufactured by Aldrich) (about 32 mmo)
l) was used. After completion of the reaction, the reaction product was purified in the same manner as in Example 1 to obtain 1.43 g of white powder.
【００３２】この白色粉末のＦＤ−Ｍａｓｓを測定した
ところ、Ｃ28Ｈ23Ｎ3 Ｓｉ＝４２９に対して４２９の親
ピークが得られた。また、この白色粉末のＩＲスペクト
ルを測定したところ、１６２０，１５２０，１３００，
８６０（ｃｍ-1）に吸収が観測された。これらのことか
ら、得られた白色粉末は、目的とするＮ−トリフェニル
シリル−Ｎ，Ｎ−ジ−２−ピリジルアミン［図１（４）
に示すシラナミン誘導体；融点１４５℃。以下ＳＮ−４
と略記する。］であると同定された（収率１１％）。When the FD-Mass of this white powder was measured, a parent peak of 429 was obtained for C 28 H 23 N 3 Si = 429. The IR spectrum of this white powder was measured and found to be 1620, 1520, 1300,
Absorption was observed at 860 (cm -1 ). From these things, the obtained white powder is the target N-triphenylsilyl-N, N-di-2-pyridylamine [Figure 1 (4)
Silanamin derivative shown in the table; melting point 145 ° C. Below SN-4
Is abbreviated. ] Was identified (yield 11%).
【００３３】比較例１（アミン系材料の製造） ２２．５ｇ（０．０８ mol）の４，４′−ジ−ｔ−ブチ
ルジフェニルアミン、３２．６ｇ（０．１６ mol）のヨ
ードベンゼン、１６．６ｇ（０．１２ mol）の無水炭酸
カリウム、および０．５ｇ（８ｍ mol）の銅粉を混合
し、ＤＭＳＯを溶媒にして５時間反応させた。このと
き、反応温度としては２００〜２３０℃という高温を要
した。反応終了後、２００ｍｌのトルエンを加えたとこ
ろ、反応生成物は溶解したが無機塩が固形物として残っ
たため、実施例１〜実施例４の場合と異なり精製が困難
であった。また、銅塩の廃液の処理を必要とした。Comparative Example 1 (Production of amine material) 22.5 g (0.08 mol) of 4,4'-di-t-butyldiphenylamine, 32.6 g (0.16 mol) of iodobenzene, 16. 6 g (0.12 mol) of anhydrous potassium carbonate and 0.5 g (8 mmol) of copper powder were mixed and reacted with DMSO as a solvent for 5 hours. At this time, a high temperature of 200 to 230 ° C. was required as the reaction temperature. When 200 ml of toluene was added after the completion of the reaction, the reaction product was dissolved, but the inorganic salt remained as a solid substance, so that purification was difficult unlike in the cases of Examples 1 to 4. It also required treatment of copper salt effluent.
【００３４】イオン化ポテンシャルの測定 実施例１〜実施例４で得られた各シラナミン誘導体のイ
オン化ポテンシャルを、理研計器社製の表面分析装置Ａ
Ｃ−１（商品名）により測定した。また、比較として、
アミン系材料の一つであるＴＰＤ［Ｎ，Ｎ′−ビス−
（ｍ−トリル）−Ｎ，Ｎ′−ジフェニル−４，４′−ジ
アミノ−１，１′−ビフェニル］のイオン化ポテンシャ
ルを同様にして測定した。これらの結果を表１に示す。 Measurement of Ionization Potential The ionization potential of each of the silanamin derivatives obtained in Examples 1 to 4 was measured by the surface analyzer A manufactured by Riken Keiki Co., Ltd.
It was measured by C-1 (trade name). Also, as a comparison,
One of the amine-based materials, TPD [N, N'-bis-
The ionization potential of (m-tolyl) -N, N'-diphenyl-4,4'-diamino-1,1'-biphenyl] was similarly measured. The results are shown in Table 1.
【００３５】[0035]
【表１】 [Table 1]
【００３６】表１から明らかなように、実施例１〜実施
例４で得られた各シラナミン誘導体のイオン化ポテンシ
ャルは５．７〜５．９ｅＶであり、この値はＴＰＤのイ
オン化ポテンシャル５．４ｅＶよりも大きい。このこと
から、各シラナミン誘導体はＴＰＤよりも酸化されにく
いことがわかる。As is apparent from Table 1, the ionization potentials of the respective silanamine derivatives obtained in Examples 1 to 4 are 5.7 to 5.9 eV, and this value is based on the ionization potential of TPD of 5.4 eV. Is also big. From this, it is understood that each silanamin derivative is less likely to be oxidized than TPD.
【００３７】また、ＵＶ−ランプを用いて空気中で紫外
線を照射すると、ＴＰＤは酸化されて着色するが、実施
例１〜実施例４で得られた各シラナミン誘導体は着色せ
ずに白色のままである。このことは、各シラナミン誘導
体がＴＰＤよりも酸化されにくいことを示唆している。Further, when UV light is irradiated in the air using a UV-lamp, TPD is oxidized and colored, but the respective silanamine derivatives obtained in Examples 1 to 4 remain white without coloring. Is. This suggests that each silanamin derivative is less susceptible to oxidation than TPD.
【００３８】応用例１（有機ＥＬ素子の製造） まず、膜厚１００ｎｍのＩＴＯ透明電極を成膜してある
ガラス基板（２５ｍｍ×１．１ｍｍ：ホーヤ（株）製）
をイソプロピルアルコールで３０分間超音波洗浄し、さ
らに浸漬して洗浄した。そして、洗浄後のガラス基板を
乾燥窒素ガスで乾燥し、市販の真空蒸着装置の基板ホル
ダーに固定した。また、モリブデン製抵抗加熱ボートに
ＳＮ−１（Ｎ−トリフェニルシリル−Ｎ−フェニル−１
−ナフチルアミン；実施例１で得られたシラナミン誘導
体）２００ｍｇを入れ、別のモリブデン製抵抗加熱ボー
トに４，４−ビス［２，２−フェニルビニル］ビフェニ
ル（以下ＤＰＶＢｉと略記する）２００ｍｇを入れ、さ
らに別のモリブデン製抵抗加熱ボートにトリス（８−ヒ
ドロキシ）アルミニウム（以下Ａｌｑと略記する）２０
０ｍｇを入れ、これらの抵抗加熱ボートを上記の真空蒸
着装置に取付けた。Application Example 1 (Production of Organic EL Element) First, a glass substrate (25 mm × 1.1 mm: manufactured by Hoya Co., Ltd.) on which an ITO transparent electrode having a film thickness of 100 nm is formed.
Was ultrasonically cleaned with isopropyl alcohol for 30 minutes and further immersed for cleaning. Then, the washed glass substrate was dried with dry nitrogen gas and fixed to a substrate holder of a commercially available vacuum vapor deposition device. In addition, SN-1 (N-triphenylsilyl-N-phenyl-1) was added to the resistance heating boat made of molybdenum.
-Naphthylamine; 200 mg of the silanamine derivative obtained in Example 1), and 200 mg of 4,4-bis [2,2-phenylvinyl] biphenyl (hereinafter abbreviated as DPVBi) was placed in another molybdenum resistance heating boat. In another resistance heating boat made of molybdenum, tris (8-hydroxy) aluminum (hereinafter abbreviated as Alq) 20 was added.
0 mg was put in, and these resistance heating boats were attached to the above vacuum deposition apparatus.
【００３９】次いで、真空槽を４×１０-4Ｐａまで減圧
した後、ＳＮ−１の入った前記抵抗加熱ボートに通電し
て加熱し、蒸着速度０．１〜０．７ｎｍ／秒でＩＴＯ透
明電極上にＳＮ−１を蒸着して、膜厚６０ｎｍの正孔輸
送層を設けた。次に、ＤＰＶＢｉの入った前記抵抗加熱
ボートに通電して加熱し、蒸着速度０．１〜０．３ｎｍ
／秒で上記正孔輸送層上にＤＰＶＢｉを蒸着して、膜厚
４０ｎｍの発光層を設けた。さらに、Ａｌｑの入った前
記抵抗加熱ボートに通電して加熱し、蒸着速度０．１ｎ
ｍ／秒で上記発光層上にＡｌｑを蒸着して、膜厚２０ｎ
ｍの電子注入層（付着改善層）を設けた。なお、正孔輸
送層、発光層および電子注入層を設ける際の基板温度は
いずれも室温であった。Then, the vacuum chamber was decompressed to 4 × 10 -4 Pa, and the resistance heating boat containing SN-1 was energized to heat it, and the ITO transparent at a deposition rate of 0.1 to 0.7 nm / sec. SN-1 was vapor-deposited on the electrode to provide a hole transport layer having a film thickness of 60 nm. Next, the resistance heating boat containing DPVBi is energized and heated, and the deposition rate is 0.1 to 0.3 nm.
DPVBi was vapor-deposited on the hole-transporting layer at a rate of 1 / sec to form a light-emitting layer having a thickness of 40 nm. Further, the resistance heating boat containing Alq is energized and heated to a vapor deposition rate of 0.1 n.
Alq is vapor-deposited on the above light emitting layer at a rate of
m electron injection layer (adhesion improving layer) was provided. The substrate temperature at the time of providing the hole transport layer, the light emitting layer and the electron injection layer was room temperature.
【００４０】次に、真空槽を開けて電子注入層上にステ
ンレス鋼製のマスクを設置した。また、マグネシウム３
ｇを入れたモリブデン製抵抗加熱ボートと、銀５００ｍ
ｇを入れたタングステン製フィラメントとを、真空蒸着
装置に取付けた。この後、再度真空槽を２×１０-4Ｐａ
まで減圧してから、マグネシウムの入った前記抵抗加熱
ボートに通電して加熱し、蒸着速度２〜３ｎｍ／秒で上
記電子注入層上にマグネシウムを蒸着すると同時に、銀
を入れた前記フィラメントを加熱して蒸着速度０．１〜
０．２ｎｍ／秒で上記電子注入層上に銀を蒸着して、Ｉ
ＴＯ透明電極に対する対向電極としてマグネシウムと銀
との合金からなる電極を設けた。これにより、目的とす
る有機ＥＬ素子が得られた。Next, the vacuum chamber was opened and a mask made of stainless steel was placed on the electron injection layer. Also, magnesium 3
Molybdenum resistance heating boat containing g and silver 500m
The tungsten filament containing g was attached to a vacuum vapor deposition apparatus. After this, the vacuum chamber is again set to 2 × 10 −4 Pa.
Then, the resistance heating boat containing magnesium is energized and heated, and magnesium is vapor-deposited on the electron injection layer at a vapor deposition rate of 2 to 3 nm / sec. At the same time, the filament containing silver is heated. Vapor deposition rate 0.1
Evaporating silver on the electron injection layer at 0.2 nm / sec, I
An electrode made of an alloy of magnesium and silver was provided as a counter electrode for the TO transparent electrode. As a result, the intended organic EL device was obtained.
【００４１】この有機ＥＬ素子について、ＩＴＯ透明電
極を陽極にしマグネシウムと銀との合金からなる対向電
極を陰極として直流１９Ｖの電圧を印加したところ、電
流密度２７．５ｍＡ／ｃｍ2 で電流が流れ、輝度４００
ｃｄ／ｍ2 の青色発光が得られた。When a voltage of DC 19 V was applied to this organic EL device with the ITO transparent electrode as the anode and the counter electrode made of an alloy of magnesium and silver as the cathode, a current flowed at a current density of 27.5 mA / cm 2 . Brightness 400
A blue emission of cd / m 2 was obtained.
【００４２】薄膜維持能の評価 ＮＡ（開口数）４０材であるガラス基板上にＩＴＯ膜を
１００ｎｍの厚さで成膜したものについて応用例１と同
様にして超音波洗浄および乾燥を行った後、応用例１と
同様にして、ＩＴＯ膜上に膜厚６０ｎｍのＳＮ−１層を
設けた。このものを１ヶ月間空気中にさらした後、再結
晶化によるＳＮ−１層の破壊の有無を光学顕微鏡により
観察した。この結果、再結晶化によるＳＮ−１層の破壊
は光学顕微鏡下では認められなかった。このことから、
ＳＮ−１の薄膜は再結晶化を起こしにくく、良好な薄膜
維持能を有していることがわかる。一方、同様の試験を
ＴＰＤについて行ったところ、１ヶ月後には光学顕微鏡
下で認められる再結晶化が生じていた。このことから、
ＴＰＤの薄膜はＳＮ−１の薄膜よりも再結晶化を起こし
易く、ＴＰＤの薄膜維持能はＳＮ−１よりも劣っている
ことがわかる。 Evaluation of Thin Film Maintainability A glass substrate having a NA (numerical aperture) of 40 and an ITO film having a thickness of 100 nm was subjected to ultrasonic cleaning and drying in the same manner as in Application Example 1. A SN-1 layer having a film thickness of 60 nm was provided on the ITO film in the same manner as in Application Example 1. After exposing this to air for one month, the presence or absence of destruction of the SN-1 layer due to recrystallization was observed with an optical microscope. As a result, destruction of the SN-1 layer due to recrystallization was not observed under an optical microscope. From this,
It can be seen that the thin film of SN-1 does not easily recrystallize and has a good thin film maintaining ability. On the other hand, when a similar test was conducted on TPD, recrystallization observed under an optical microscope had occurred after one month. From this,
It can be seen that the thin film of TPD is more likely to cause recrystallization than the thin film of SN-1, and the thin film maintaining ability of TPD is inferior to that of SN-1.
【００４３】[0043]
【発明の効果】以上説明したように、本発明のシラナミ
ン誘導体は酸化されにくいとともに、薄膜とした場合で
も再結晶化を起こしにくい。したがって、本発明によれ
ば酸化に強いとともに薄膜維持能の高い正孔輸送層等を
提供することが可能になる。As described above, the silanamin derivative of the present invention is hard to be oxidized and is hard to be recrystallized even when formed into a thin film. Therefore, according to the present invention, it is possible to provide a hole transport layer or the like that is strong against oxidation and has a high ability to maintain a thin film.
【図１】本発明のシラナミン誘導体の具体例を示す構造
式である。FIG. 1 is a structural formula showing a specific example of the silanamin derivative of the present invention.
【図２】本発明のシラナミン誘導体の他の具体例を示す
構造式である。FIG. 2 is a structural formula showing another specific example of the silanamin derivative of the present invention.
【図３】本発明の方法で用いるアミンの具体例を示す構
造式である。FIG. 3 is a structural formula showing a specific example of an amine used in the method of the present invention.
【図４】本発明の方法で用いるハロゲン化シランの具体
例を示す構造式である。FIG. 4 is a structural formula showing a specific example of a halogenated silane used in the method of the present invention.
Claims (4)
素数３〜１０の複素芳香環基であり、これらの基にはア
ルキル基またはフェニル基が核置換されていてもよい。
Ａｒ2 は炭素数７〜２０のアリール基または炭素数３〜
１０の複素芳香環基であり、これらの基にはアルキル基
またはフェニル基が核置換されていてもよい。Ａｒ3 は
炭素数６〜２０のアリール基であり、この基にはアルキ
ル基が核置換されていてもよい。）で表されるシラナミ
ン誘導体。1. A compound represented by the general formula (I): (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 10 carbon atoms, and these groups may be substituted with an alkyl group or a phenyl group as a nucleus.
Ar 2 is an aryl group having 7 to 20 carbon atoms or 3 to 3 carbon atoms.
10 heteroaromatic ring groups, which may be nucleus-substituted with an alkyl group or a phenyl group. Ar 3 is an aryl group having 6 to 20 carbon atoms, and an alkyl group may be nucleus-substituted in this group. ) A silanamine derivative represented by.
素数３〜１０の複素芳香環基であり、これらの基にはア
ルキル基またはフェニル基が核置換されていてもよい。
Ａｒ2 は炭素数７〜２０のアリール基または炭素数３〜
１０の複素芳香環基であり、これらの基にはアルキル基
またはフェニル基が核置換されていてもよい。）で表さ
れるアミンと、一般式(III) 【化３】 （式中、Ａｒ3 は炭素数６〜２０のアリール基であり、
この基にはアルキル基が核置換されていてもよい。）で
表されるハロゲン化シランとを縮合反応させることを特
徴とする、請求項１に記載のシラナミン誘導体の製造方
法。2. A compound represented by the general formula (II): (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 10 carbon atoms, and these groups may be substituted with an alkyl group or a phenyl group as a nucleus.
Ar 2 is an aryl group having 7 to 20 carbon atoms or 3 to 3 carbon atoms.
10 heteroaromatic ring groups, which may be nucleus-substituted with an alkyl group or a phenyl group. ) And an amine represented by the general formula (III): (In the formula, Ar 3 is an aryl group having 6 to 20 carbon atoms,
An alkyl group may be nucleus-substituted in this group. The method for producing a silanamine derivative according to claim 1, wherein the halogenated silane represented by the formula (1) is subjected to a condensation reaction.
なることを特徴とする正孔輸送材料。3. A hole transport material comprising the silanamin derivative according to claim 1.
している有機エレクトロルミネッセンス素子において、 前記正孔輸送層が、請求項１に記載のシラナミン誘導体
からな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。4. An organic electroluminescence device having a hole transport layer interposed between an anode and a light emitting layer, wherein the hole transport layer is composed of the silanamin derivative according to claim 1. Organic electroluminescent device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5078344A JPH06293778A (en) | 1993-04-05 | 1993-04-05 | Silanamine derivative and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5078344A JPH06293778A (en) | 1993-04-05 | 1993-04-05 | Silanamine derivative and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06293778A true JPH06293778A (en) | 1994-10-21 |
Family
ID=13659376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5078344A Withdrawn JPH06293778A (en) | 1993-04-05 | 1993-04-05 | Silanamine derivative and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06293778A (en) |
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