JPH0625659A - Phosphamine derivative, its preparation, and electroluminescent element made using the same - Google Patents
Phosphamine derivative, its preparation, and electroluminescent element made using the sameInfo
- Publication number
- JPH0625659A JPH0625659A JP4179890A JP17989092A JPH0625659A JP H0625659 A JPH0625659 A JP H0625659A JP 4179890 A JP4179890 A JP 4179890A JP 17989092 A JP17989092 A JP 17989092A JP H0625659 A JPH0625659 A JP H0625659A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- layer
- general formula
- phosphamine
- 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- Withdrawn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
- 239000010410 layer Substances 0.000 claims abstract description 185
- 239000002356 single layer Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 230000005525 hole transport Effects 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000005266 diarylamine group Chemical group 0.000 claims description 7
- 150000003003 phosphines Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 5
- 125000005649 substituted arylene group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 54
- 150000001412 amines Chemical class 0.000 abstract description 10
- -1 aromatic tertiary amine Chemical class 0.000 description 67
- 238000000034 method Methods 0.000 description 31
- 239000010408 film Substances 0.000 description 21
- 239000010409 thin film Substances 0.000 description 20
- 238000010586 diagram Methods 0.000 description 19
- 238000007740 vapor deposition Methods 0.000 description 19
- 101100083253 Caenorhabditis elegans pho-1 gene Proteins 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052750 molybdenum Inorganic materials 0.000 description 8
- 239000011733 molybdenum Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 6
- 238000004528 spin coating Methods 0.000 description 6
- 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 5
- 239000010406 cathode material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000005427 anthranyl group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 125000004802 cyanophenyl group Chemical group 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000006303 iodophenyl group Chemical group 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical group C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- CSPVGJWCKNBRRB-UHFFFAOYSA-N indium;quinolin-8-ol Chemical compound [In].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 CSPVGJWCKNBRRB-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000004957 naphthylene group Chemical group 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000005562 phenanthrylene group Chemical group 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
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- 239000004417 polycarbonate Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
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- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000005548 pyrenylene group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
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- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 2
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- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 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
- QKLPIYTUUFFRLV-YTEMWHBBSA-N 1,4-bis[(e)-2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=CC=C1C QKLPIYTUUFFRLV-YTEMWHBBSA-N 0.000 description 1
- BCASZEAAHJEDAL-PHEQNACWSA-N 1,4-bis[(e)-2-(4-methylphenyl)ethenyl]benzene Chemical compound C1=CC(C)=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=C(C)C=C1 BCASZEAAHJEDAL-PHEQNACWSA-N 0.000 description 1
- LWGPQZLNJIVUIC-UHFFFAOYSA-N 1,4-bis[2-(2-ethylphenyl)ethenyl]benzene Chemical compound CCC1=CC=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=CC=C1CC LWGPQZLNJIVUIC-UHFFFAOYSA-N 0.000 description 1
- SWYYRSGBEBXIRE-UHFFFAOYSA-N 1,4-bis[2-(3-ethylphenyl)ethenyl]benzene Chemical compound CCC1=CC=CC(C=CC=2C=CC(C=CC=3C=C(CC)C=CC=3)=CC=2)=C1 SWYYRSGBEBXIRE-UHFFFAOYSA-N 0.000 description 1
- XBDQJALUKGQTAV-UHFFFAOYSA-N 1,4-bis[2-(3-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC(C=CC=2C=CC(C=CC=3C=C(C)C=CC=3)=CC=2)=C1 XBDQJALUKGQTAV-UHFFFAOYSA-N 0.000 description 1
- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-UHFFFAOYSA-N 0.000 description 1
- DLQSDMLDSHSVKH-UHFFFAOYSA-N 1-[2-(6,6-ditert-butylcyclohexa-2,4-dien-1-yl)ethenyl]-4-phenylbenzene Chemical group C(C)(C)(C)C1(C(C=CC=C1)C=CC1=CC=C(C=C1)C1=CC=CC=C1)C(C)(C)C DLQSDMLDSHSVKH-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- AOGDNNLIBAUIIX-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-1-ylbenzene-1,4-diamine Chemical compound C1=CC=C2C(NC=3C=CC(NC=4C5=CC=CC=C5C=CC=4)=CC=3)=CC=CC2=C1 AOGDNNLIBAUIIX-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- YTDHEFNWWHSXSU-UHFFFAOYSA-N 2,3,5,6-tetrachloroaniline Chemical compound NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl YTDHEFNWWHSXSU-UHFFFAOYSA-N 0.000 description 1
- WLLVDIMVCJQRLX-UHFFFAOYSA-N 2,3-bis(2-pyren-1-ylethenyl)pyrazine Chemical compound C1(=CC=C2C=CC3=CC=CC4=CC=C1C2=C34)C=CC=1C(=NC=CN=1)C=CC1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34 WLLVDIMVCJQRLX-UHFFFAOYSA-N 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical class C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- FZORBZJJXZJZDC-UHFFFAOYSA-N 2,5-bis(2-naphthalen-1-ylethenyl)pyrazine Chemical compound C1=CC=C2C(C=CC3=NC=C(N=C3)C=CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 FZORBZJJXZJZDC-UHFFFAOYSA-N 0.000 description 1
- ZGXQLVRLPJXTIK-LQIBPGRFSA-N 2,5-bis[(e)-2-(4-methoxyphenyl)ethenyl]pyrazine Chemical compound C1=CC(OC)=CC=C1\C=C\C(N=C1)=CN=C1\C=C\C1=CC=C(OC)C=C1 ZGXQLVRLPJXTIK-LQIBPGRFSA-N 0.000 description 1
- PAJSTGVSGZWCGO-UHFFFAOYSA-N 2,5-bis[2-(4-ethylphenyl)ethenyl]pyrazine Chemical compound C1=CC(CC)=CC=C1C=CC(N=C1)=CN=C1C=CC1=CC=C(CC)C=C1 PAJSTGVSGZWCGO-UHFFFAOYSA-N 0.000 description 1
- BFQSAUNFPAHVRZ-UHFFFAOYSA-N 2,5-bis[2-(4-methylphenyl)ethenyl]pyrazine Chemical compound C1=CC(C)=CC=C1C=CC(N=C1)=CN=C1C=CC1=CC=C(C)C=C1 BFQSAUNFPAHVRZ-UHFFFAOYSA-N 0.000 description 1
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 1
- LUHPFRGVJFNUOR-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethenyl]-1,3-benzoxazole Chemical class C1=CC(Cl)=CC=C1C=CC1=NC2=CC=CC=C2O1 LUHPFRGVJFNUOR-UHFFFAOYSA-N 0.000 description 1
- PORKWWLSRFDCLR-UHFFFAOYSA-N 2-[2-[4-[2-(1,3-benzothiazol-2-yl)ethenyl]phenyl]ethenyl]-1,3-benzothiazole Chemical compound C1=CC=C2SC(C=CC=3C=CC(C=CC=4SC5=CC=CC=C5N=4)=CC=3)=NC2=C1 PORKWWLSRFDCLR-UHFFFAOYSA-N 0.000 description 1
- XFPKINQJEVMALK-UHFFFAOYSA-N 2-[4-[4-(1,3-benzoxazol-2-yl)phenyl]phenyl]-1,3-benzoxazole Chemical group C1=CC=C2OC(C3=CC=C(C=C3)C3=CC=C(C=C3)C=3OC4=CC=CC=C4N=3)=NC2=C1 XFPKINQJEVMALK-UHFFFAOYSA-N 0.000 description 1
- HNPLZFFFNHWZPM-UHFFFAOYSA-N 2-[5-[5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazol-2-yl]-3,4-diphenylthiophen-2-yl]-5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazole Chemical compound N=1C2=CC(C(C)(C)CC)=CC(C(C)(C)CC)=C2OC=1C=1SC(C=2OC3=C(C=C(C=C3N=2)C(C)(C)CC)C(C)(C)CC)=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 HNPLZFFFNHWZPM-UHFFFAOYSA-N 0.000 description 1
- MUMFNDFRZDYMNG-UHFFFAOYSA-N 2-[5-[5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazol-2-yl]thiophen-2-yl]-5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazole Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=C2OC(C3=CC=C(S3)C=3OC4=C(C=C(C=C4N=3)C(C)(C)CC)C(C)(C)CC)=NC2=C1 MUMFNDFRZDYMNG-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- SVNTXZRQFPYYHV-UHFFFAOYSA-N 2-methyl-1,4-bis[2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1C=CC(C=C1C)=CC=C1C=CC1=CC=CC=C1C SVNTXZRQFPYYHV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KUJYDIFFRDAYDH-UHFFFAOYSA-N 2-thiophen-2-yl-5-[5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC=CC=2)=C1 KUJYDIFFRDAYDH-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- HQPIRXQACTZROS-UHFFFAOYSA-N 4-[2-(1h-benzimidazol-2-yl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C=CC1=NC2=CC=CC=C2N1 HQPIRXQACTZROS-UHFFFAOYSA-N 0.000 description 1
- UYEBVQUTQHTYOU-UHFFFAOYSA-N 5-methyl-2-[4-[2-(5-methyl-1,3-benzoxazol-2-yl)ethenyl]phenyl]-1,3-benzoxazole Chemical compound CC1=CC=C2OC(C3=CC=C(C=C3)C=CC=3OC4=CC=C(C=C4N=3)C)=NC2=C1 UYEBVQUTQHTYOU-UHFFFAOYSA-N 0.000 description 1
- XPLXHDHGYSONMX-UHFFFAOYSA-N 5-methyl-2-[5-(5-methyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound CC1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C)=NC2=C1 XPLXHDHGYSONMX-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 241000511976 Hoya Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 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
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 238000005282 brightening Methods 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
- SBAUTRQODRAAMY-UHFFFAOYSA-N calcium;5-chloroquinolin-8-ol Chemical compound [Ca].C1=CN=C2C(O)=CC=C(Cl)C2=C1.C1=CN=C2C(O)=CC=C(Cl)C2=C1 SBAUTRQODRAAMY-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- HQQKMOJOCZFMSV-UHFFFAOYSA-N dilithium phthalocyanine Chemical compound [Li+].[Li+].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HQQKMOJOCZFMSV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 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
- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
- MOOHXQFFIPDLNX-UHFFFAOYSA-N magnesium;quinolin-8-ol Chemical compound [Mg].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 MOOHXQFFIPDLNX-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 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
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、エレクトロルミネッセ
ンス素子に関し、さらに該素子に使用しうるホスファミ
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 an electroluminescence device, a phosphamine derivative which can be used in the device, and a method for producing the same.
【０００２】[0002]
【従来の技術】エレクトロルミネッセンス素子（以下，
ＥＬ素子という）の構成については種々のものが知られ
ている。そしてＩＴＯ／正孔輸送層／発光層／陰極の素
子構成における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（特開昭６３−２９
５６９５号公報を参照）。この素子構成により２０Ｖ以
上の印加電圧で数百ｃｄ／ｍ2 の高輝度を可能としてい
る。2. Description of the Related Art Electroluminescent devices (hereinafter referred to as
Various configurations are known for the configuration of an EL element). It is disclosed that an aromatic tertiary amine is used as a material for the hole transport layer in the device structure of ITO / hole transport layer / light emitting layer / cathode (JP-A-63-29).
(See Japanese Patent No. 5695). With this element structure, a high brightness of several hundred cd / m 2 is possible with an applied voltage of 20 V or more.
【０００３】[0003]
【発明が解決しようとする課題】しかしながらこのアミ
ン系の正孔輸送層は酸化に弱く、また薄膜にした時に再
結晶化を起こすことが知られている。また、従来のアミ
ン系材料を用いたＥＬ素子のイオン化ポテンシャルは、
ジアリールアミンを用いたものでも５．５ｅＶ程度であ
り、そのためＥＬ発光に必要な印加電圧が高いという欠
点があった。However, it is known that this amine-based hole transport layer is weak against oxidation and causes recrystallization when formed into a thin film. Further, the ionization potential of an EL element using a conventional amine-based material is
Even when the diarylamine is used, it is about 5.5 eV, so that there is a drawback that the applied voltage required for EL light emission is high.
【０００４】ところでアミン系材料の製造方法としては
ウルマン反応が主に用いられているが、高い反応温度を
必要とし、重金属を触媒として用いるため、廃液の処理
が困難であるという問題点がある。The Ullmann reaction is mainly used as a method for producing an amine-based material, but it requires a high reaction temperature and uses a heavy metal as a catalyst, so that it is difficult to treat the waste liquid.
【０００５】従って本発明の第１の目的は従来のアミン
系材料以外の有機化合物をＥＬ素子に用いることによ
り、膜性に優れ、印加電圧の低いＥＬ素子を提供するこ
とにある。また本発明の第２の目的は上記特性を有する
ＥＬ素子に好適な新規有機化合物およびその製造方法を
提供することにある。Therefore, a first object of the present invention is to provide an EL element having excellent film properties and a low applied voltage by using an organic compound other than the conventional amine-based material for the EL element. A second object of the present invention is to provide a novel organic compound suitable for an EL device having the above characteristics and a method for producing the same.
【０００６】[0006]
【課題を解決するための手段】上記第１の目的を達成す
る本発明の有機ＥＬ素子は、有機発光層を少なくとも含
む単層構造又は多層構造の化合物層と、この化合物層を
挟持する一対の電極とを備え、かつ前記化合物層の少な
くとも一層が、ホスファミン誘導体を含むことを特徴と
するものである。An organic EL device of the present invention that achieves the first object is a compound layer having a single-layer structure or a multilayer structure including at least an organic light-emitting layer, and a pair of compound layers sandwiching the compound layer. And an electrode, and at least one of the compound layers contains a phosphamine derivative.
【０００７】本発明の有機ＥＬ素子において用いられる
ホスファミン誘導体は、アミノ基で置換されたリン原子
を少なくとも１個有する化合物であり、例えば一般式
（Ｉ）または一般式（ＩＩ）で表される化合物が挙げら
れる。The phosphamine derivative used in the organic EL device of the present invention is a compound having at least one phosphorus atom substituted with an amino group, for example, a compound represented by the general formula (I) or the general formula (II). Is mentioned.
【０００８】[0008]
【化８】 [Chemical 8]
【化９】 先ず一般式（Ｉ）で表されるホスファミン誘導体を説明
する。一般式（Ｉ）において、Ｒ1 ，Ｒ2 ，Ｒ3 ，Ｒ4
は、炭素数１〜６のアルキル基（例えば、メチル、エチ
ル、ｎ−プロピル、ｉ−プロピル，ｎ−ブチル、ｓ−ブ
チル、ｔ−ブチル、ペンチル、シクロペンチル、ヘキシ
ル、シクロヘキシル等）、アルケニル基（例えばエテニ
ル、１ープロペニル、２ープロペニル、１ーブテニル、
２ーブテニル、３ーブテニル、ペンテニル、ヘキセニル
等）アルキニル基（例えば、アセチレニル等）、炭素数
６〜２０のアリール基（例えばフェニル、ナフチル、ビ
フェニル、アセナフチル、アントラニル、フェナンスリ
ル、ピレニル等）、置換アリール基（例えば、トリル、
エチルフェニル，ｎ−プロピルフェニル，ｉ−プロピル
フェニル、ｎーブチルフェニル、ｓ−ブチルフェニル、
ｔ−ブチルフェニル、ペンチルフェニル、ヘキシルフェ
ニル、キシレニル、メシチレニル、アニシル、フェノキ
シフェニル、アミノフェニル、ニトロフェニル、シアノ
フェニル、ホルミルフェニル、エトキシカルボニルフェ
ニル、フルオロフェニル、クロロフェニル、ブロモフェ
ニル、ヨードフェニル、スチリル等）、炭素数５〜１０
の複素芳香環（例えばピローリル、チオフェニル、フラ
ニル、ピリジニル、イミダゾリル、インドーリル、ベン
ゾチオフェニル、ベンゾフラニル等）、ベンジル基、ま
たはシンナミル基であり、Ｒ1 ，Ｒ2 ，Ｒ3 ，Ｒ4 はそ
れぞれ同一でも異なっていても良い。一般式（Ｉ）の化
合物の具体例を、図１〜図４に示す。[Chemical 9] First, the phosphamine derivative represented by the general formula (I) will be described. In the general formula (I), R 1 , R 2 , R 3 , R 4
Is an alkyl group having 1 to 6 carbon atoms (for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, etc.), an alkenyl group ( For example, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl,
2-butenyl, 3-butenyl, pentenyl, hexenyl, etc.) alkynyl group (eg, acetylenyl, etc.), aryl group having 6 to 20 carbon atoms (eg, phenyl, naphthyl, biphenyl, acenaphthyl, anthranyl, phenanthryl, pyrenyl, etc.), substituted aryl group ( For example, trill,
Ethylphenyl, n-propylphenyl, i-propylphenyl, n-butylphenyl, s-butylphenyl,
(t-butylphenyl, pentylphenyl, hexylphenyl, xylenyl, mesityrenyl, anisyl, phenoxyphenyl, aminophenyl, nitrophenyl, cyanophenyl, formylphenyl, ethoxycarbonylphenyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, styryl, etc.) , Carbon number 5-10
A heteroaromatic ring (for example, pyrrolyl, thiophenyl, furanyl, pyridinyl, imidazolyl, indolyl, benzothiophenyl, benzofuranyl, etc.), a benzyl group or a cinnamyl group, and R 1 , R 2 , R 3 and R 4 may be the same as each other. It can be different. Specific examples of the compound of the general formula (I) are shown in FIGS.
【０００９】次に一般式（ＩＩ）で表されるホスファミ
ン誘導体を説明する。Next, the phosphamine derivative represented by the general formula (II) will be described.
【００１０】一般式（ＩＩ）において、Ａｒ1 は、炭素
数６〜２０のアリール基（例えばフェニル、ナフチル、
ビフェニル、アセナフチル、アントラニル、フェナンス
リル、ピレニル等）、置換アリール基（例えば、トリ
ル、エチルフェニル，ｎ−プロピルフェニル，ｉ−プロ
ピルフェニル、ｎーブチルフェニル、ｓ−ブチルフェニ
ル、ｔ−ブチルフェニル、ペンチルフェニル、ヘキシル
フェニル、キシレニル、メシチレニル、アニシル、フェ
ノキシフェニル、アミノフェニル、ニトロフェニル、シ
アノフェニル、ホルミルフェニル、エトキシカルボニル
フェニル、フルオロフェニル、クロロフェニル、ブロモ
フェニル、ヨードフェニル、スチリル等）、炭素数５〜
１０の複素芳香環（例えばピローリル、チオフェニル、
フラニル、ピリジニル、イミダゾリル、インドーリル、
ベンゾチオフェニル、ベンゾフラニル等）である。In the general formula (II), Ar 1 is an aryl group having 6 to 20 carbon atoms (eg phenyl, naphthyl,
Biphenyl, acenaphthyl, anthranyl, phenanthryl, pyrenyl, etc.), substituted aryl groups (eg, tolyl, ethylphenyl, n-propylphenyl, i-propylphenyl, n-butylphenyl, s-butylphenyl, t-butylphenyl, pentylphenyl, hexyl) Phenyl, xylenyl, mesityrenyl, anisyl, phenoxyphenyl, aminophenyl, nitrophenyl, cyanophenyl, formylphenyl, ethoxycarbonylphenyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, styryl, etc.), carbon number 5
10 heteroaromatic rings (eg pyrrolyl, thiophenyl,
Furanyl, pyridinyl, imidazolyl, indolyl,
Benzothiophenyl, benzofuranyl, etc.).
【００１１】Ａｒ2 は炭素数６〜２０のアリーレン基
（例えばフェニレン、ナフチレン、ビフェニレン、アン
トラニレン、アセナフチレン、フェナンスリレン、ピレ
ニレン等）、置換アリーレン基（例えば、メチル、エチ
ル，ｎ−プロピル，ｉ−プロピル，ｎ−ブチル，ｓ−ブ
チル、ｔ−ブチル、ペンチル、ヘキシル、メトキシ、フ
ェノキシ、アミノ、ニトロ、シアノ、ホルミル、エステ
ル、フルオロ、クロロ、ブロモ、ヨード、ベンジル、シ
ンナミル基等で置換されたフェニレンまたはビフェニレ
ン）、または炭素数５〜１０の複素芳香環（例えばピロ
ーリレン、チオフェニレン、フラニレン、ピリジニレン
等）である。Ar 2 is an arylene group having 6 to 20 carbon atoms (eg, phenylene, naphthylene, biphenylene, anthranylene, acenaphthylene, phenanthrylene, pyrenylene, etc.), a substituted arylene group (eg, methyl, ethyl, n-propyl, i-propyl, Phenylene or biphenylene substituted with n-butyl, s-butyl, t-butyl, pentyl, hexyl, methoxy, phenoxy, amino, nitro, cyano, formyl, ester, fluoro, chloro, bromo, iodo, benzyl, cinnamyl groups, etc. ), Or a heteroaromatic ring having 5 to 10 carbon atoms (eg, pyrrolylene, thiophenylene, furanylene, pyridinylene, etc.).
【００１２】Ａｒ3 は、炭素数６〜２０のアリール基
（例えばフェニル、ナフチル、ビフェニル、アセナフチ
ル、アントラニル、フェナンスリル、ピレニル等）、置
換アリール基（例えば、トリル、エチルフェニル，ｎ−
プロピルフェニル，ｉ−プロピルフェニル、ｎーブチル
フェニル、ｓ−ブチルフェニル、ｔ−ブチルフェニル、
ペンチルフェニル、ヘキシルフェニル、キシレニル、メ
シチレニル、アニシル、フェノキシフェニル、アミノフ
ェニル、ニトロフェニル、シアノフェニル、ホルミルフ
ェニル、エトキシカルボニルフェニル、フルオロフェニ
ル、クロロフェニル、ブロモフェニル、ヨードフェニ
ル、スチリル等）、炭素数５〜１０の複素芳香環（例え
ばピローリル、チオフェニル、フラニル、ピリジニル、
イミダゾリル、インドーリル、ベンゾチオフェニル、ベ
ンゾフラニル等）、ベンジル基、またはシンナミル基で
ある。一般式（ＩＩ）の化合物の具体例を図５〜図１６
に示す。Ar 3 is an aryl group having 6 to 20 carbon atoms (eg, phenyl, naphthyl, biphenyl, acenaphthyl, anthranyl, phenanthryl, pyrenyl, etc.) and a substituted aryl group (eg, tolyl, ethylphenyl, n-).
Propylphenyl, i-propylphenyl, n-butylphenyl, s-butylphenyl, t-butylphenyl,
(Pentylphenyl, hexylphenyl, xylenyl, mesitylenyl, anisyl, phenoxyphenyl, aminophenyl, nitrophenyl, cyanophenyl, formylphenyl, ethoxycarbonylphenyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, styryl, etc.), carbon number 5 10 heteroaromatic rings (eg pyrrolyl, thiophenyl, furanyl, pyridinyl,
Imidazolyl, indolyl, benzothiophenyl, benzofuranyl, etc.), benzyl group, or cinnamyl group. Specific examples of the compound of the general formula (II) are shown in FIGS.
Shown in.
【００１３】上記一般式（ＩＩ）の化合物の中でも、そ
の下位概念である下記一般式（ＩＩＩ）で示される化合
物が特に好ましい。Among the compounds of the general formula (II), compounds represented by the following general formula (III), which is a subordinate concept thereof, are particularly preferable.
【００１４】[0014]
【化１０】 一般式（ＩＩＩ）において、Ａｒ4 は、一般式（ＩＩ）
におけるＡｒ1 の下位概念に相当し、炭素数６〜２０の
アリール基（例えばフェニル、ナフチル、ビフェニル、
アセナフチル、アントラニル、フェナンスリル、ピレニ
ル等）に限定される。またＡｒ5 は、一般式（ＩＩ）に
おけるＡｒ2 の下位概念に相当し、炭素数６〜２０のア
リーレン基（例えばフェニレン、ナフチレン、ビフェニ
レン、アセナフチレン、アントラニレン、フェナンスリ
レン、ピレニレン等）に限定される。一般式（ＩＩＩ）
の化合物の具体例を図１７〜図１８に示す。[Chemical 10] In the general formula (III), Ar 4 is the general formula (II).
Corresponding to a subordinate concept of Ar 1 and having 6 to 20 carbon atoms (eg, phenyl, naphthyl, biphenyl,
Acenaphthyl, anthranil, phenanthryl, pyrenyl, etc.). Ar 5 corresponds to a subordinate concept of Ar 2 in the general formula (II) and is limited to an arylene group having 6 to 20 carbon atoms (for example, phenylene, naphthylene, biphenylene, acenaphthylene, anthranylene, phenanthrylene, pyrenylene, etc.). General formula (III)
17 to 18 show specific examples of the compound.
【００１５】有機ＥＬ素子の構成の例としては、陽極
／有機発光層／陰極、陽極／正孔輸送層／有機発光層
／陰極、陽極／有機発光層／電子注入層／陰極、陽
極／正孔輸送層／有機発光層／電子注入層／陰極、等が
あるが、本発明の有機ＥＬ素子は、一対の電極（陽極と
陰極）により挟持された化合物層（前記の構成の素子
においては有機発光層、前記の構成の素子においては
正孔輸送層および有機発光層、前記の構成の素子にお
いては有機発光層および電子注入層、前記の構成の素
子においては正孔輸送層、有機発光層および電子注入
層）の少なくとも１層が前述した本発明のホスファミン
誘導体を含んでいれば、〜のいずれの構成であって
も良い。なお、これらの構成の有機ＥＬ素子は、いずれ
も基板により支持されることが好ましい。この基板につ
いて特別な制限はなく、従来の有機ＥＬ素子に慣用され
ているもの、例えば、ガラス、透明プラスチック、石英
等からなるものを用いることができる。Examples of the constitution of the organic EL device include anode / organic light emitting layer / cathode, anode / hole transport layer / organic light emitting layer / cathode, anode / organic light emitting layer / electron injection layer / cathode, anode / hole. There are a transport layer / organic light emitting layer / electron injection layer / cathode, etc., but the organic EL element of the present invention is a compound layer sandwiched by a pair of electrodes (anode and cathode) Layer, a hole transport layer and an organic light emitting layer in the device having the above configuration, an organic light emitting layer and an electron injection layer in the device having the above configuration, a hole transport layer, an organic light emitting layer and an electron in the device having the above configuration As long as at least one layer of the injection layer) contains the phosphamine derivative of the present invention described above, any of the following configurations can be used. In addition, it is preferable that the organic EL elements having these configurations are all supported by the substrate. There is no particular limitation on this substrate, and those commonly used in conventional organic EL devices, for example, those made of glass, transparent plastic, quartz or the like can be used.
【００１６】本発明の有機ＥＬ素子の特徴部分であるホ
スファミン誘導体を含む層は、正孔輸送層または有機発
光層であることが好ましく、正孔輸送層であることが特
に好ましい。The layer containing the phosphamine derivative, which is a characteristic part of the organic EL device of the present invention, is preferably a hole transport layer or an organic light emitting layer, and particularly preferably a hole transport layer.
【００１７】ホスファミン誘導体を含む正孔輸送層は、
ホスファミン誘導体のみからなる単層構造でも良いし、
ホスファミン誘導体の層と有機ＥＬ素子の正孔輸送層材
料として従来から使用されている物質の層との複層構造
であっても良い。さらには、ホスファミン誘導体と有機
ＥＬ素子の正孔輸送層材料として従来から使用されてい
る物質との混合物からなる層を含む単層構造または複層
構造であっても良い。ホスファミン誘導体を含む正孔輸
送層は、ホスファミン誘導体と、必要に応じて他の正孔
輸送層材料とを用いて、真空蒸着法、キャスト法、塗布
法、スピンコート法等により形成することができる。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、ポリエステル等の透明ポリマーに
ホスファミン誘導体を分散させた溶液を用いたキャスト
法、塗布法あるいはスピンコート法等や、透明ポリマー
との同時蒸着等によっても形成することができる。The hole transport layer containing a phosphamine derivative is
A single layer structure composed of only a phosphamine derivative may be used,
It may have a multilayer structure of a layer of a phosphamine derivative and a layer of a substance conventionally used as a hole transport layer material of an organic EL device. Further, it may have a single-layer structure or a multi-layer structure including a layer composed of a mixture of a phosphamine derivative and a substance conventionally used as a hole transport layer material of an organic EL device. The hole transport layer containing a phosphamine derivative can be formed by a vacuum deposition method, a casting method, a coating method, a spin coating method or the like using a phosphamine derivative and, if necessary, another hole transport layer material. . Further, it is also formed by a casting method using a solution in which a phosphamine derivative is dispersed in a transparent polymer such as polycarbonate, polyurethane, polystyrene, polyarylate, or polyester, a coating method, a spin coating method, or simultaneous vapor deposition with a transparent polymer. can do.
【００１８】ホスファミン誘導体を含む有機発光層は、
ホスファミン誘導体のみからなる単層構造でも良いし、
ホスファミン誘導体の層と有機ＥＬ素子の有機発光層材
料として従来から使用されている物質の層との複層構造
であっても良い。さらには、ホスファミン誘導体と有機
ＥＬ素子の有機発光層材料として従来から使用されてい
る物質との混合物からなる層を含む単層構造または複層
構造であっても良い。ホスファミン誘導体を含む有機発
光層は、ホスファミン誘導体と、必要に応じて他の有機
発光層材料とを用いて、真空蒸着法、キャスト法、塗布
法、スピンコート法等により形成することができる。The organic light emitting layer containing the phosphamine derivative is
A single layer structure composed of only a phosphamine derivative may be used,
It may have a multilayer structure of a layer of a phosphamine derivative and a layer of a substance conventionally used as an organic light emitting layer material of an organic EL device. Further, it may have a single-layer structure or a multi-layer structure including a layer made of a mixture of a phosphamine derivative and a substance conventionally used as a material for an organic light emitting layer of an organic EL device. The organic light emitting layer containing a phosphamine derivative can be formed by using a phosphamine derivative and, if necessary, another organic light emitting layer material by a vacuum deposition method, a casting method, a coating method, a spin coating method, or the like.
【００１９】本発明の有機ＥＬ素子においてホスファミ
ン誘導体を含む層以外の層は、従来の有機ＥＬ素子と同
様の材料を用いて形成することができる。例えば、陽極
の材料としては、仕事関数の大きい（４ｅＶ以上の）金
属、合金、電気伝導性化合物またはこれらの混合物が好
ましく用いられる。具体例としては、Ａｕ等の金属、Ｃ
ｕＩ，ＩＴＯ，ＳｎＯ2 ，ＺｎＯ等の誘電性透明材料を
挙げることができる。陽極は、蒸着法やスパッタ法等の
方法で上記材料の薄膜を形成することにより作製するこ
とができる。有機発光層からの発光を陽極より取り出す
場合、陽極の透過率は１０％より大きいことが望まし
い。また陽極のシート抵抗は数百オーム／□以下が好ま
しい。陽極の膜厚は材料にもよるが、通常１０ｎｍ〜１
μｍ、好ましくは１０〜２００ｎｍの範囲で選択され
る。In the organic EL device of the present invention, the layers other than the layer containing the phosphamine derivative can be formed by using the same material as the conventional organic EL device. For example, as the material of the anode, a metal, an alloy, an electrically conductive compound having a large work function (4 eV or more), or a mixture thereof is preferably used. As a specific example, a metal such as Au, C
Dielectric transparent materials such as uI, ITO, SnO 2 and ZnO may be mentioned. The anode can be manufactured by forming a thin film of the above material by a method such as a vapor deposition method or a sputtering method. When the light emitted from the organic light emitting layer is taken out from the anode, the transmittance of the anode is preferably higher than 10%. The sheet resistance of the anode is preferably several hundreds ohm / square or less. The thickness of the anode depends on the material, but is usually 10 nm to 1
μm, preferably in the range of 10 to 200 nm.
【００２０】また、陰極の材料としては、仕事関数の小
さい（４ｅＶ以下の）金属、合金、電気伝導性化合物ま
たはこれらの混合物が好ましく用いられる。具体例とし
ては、ナトリウム、リチウム、マグネシウム／銅混合
物、Ａｌ／Ａｌ2 Ｏ3 ，インジウム等を挙げることがで
きる。陰極は、蒸着法やスパッタ法等の方法で上記材料
の薄膜を形成することにより作製することができる。有
機発光層からの発光を陰極より取り出す場合、陽極の透
過率は１０％より大きいことが望ましい。また陰極のシ
ート抵抗は数百オーム／□以下が好ましい。陰極の膜厚
は材料にもよるが、通常１０ｎｍ〜１μｍ、好ましくは
５０〜２００ｎｍの範囲で選択される。As the material for the cathode, a metal, an alloy, an electrically conductive compound having a small work function (4 eV or less), or a mixture thereof is preferably used. Specific examples include sodium, lithium, a magnesium / copper mixture, Al / Al 2 O 3 , indium and the like. The cathode can be manufactured by forming a thin film of the above material by a method such as a vapor deposition method or a sputtering method. When the light emitted from the organic light emitting layer is taken out from the cathode, the transmittance of the anode is preferably higher than 10%. The sheet resistance of the cathode is preferably several hundred ohms / square or less. Although the thickness of the cathode depends on the material, it is usually selected in the range of 10 nm to 1 μm, preferably 50 to 200 nm.
【００２１】なお、有機発光層からの発光を効率良く取
り出すうえからは、前述した陽極と上述した陰極との少
なくとも一方を透明または半透明物質により形成するこ
とが好ましい。In order to efficiently take out the light emitted from the organic light emitting layer, it is preferable that at least one of the above-mentioned anode and the above-mentioned cathode is formed of a transparent or semitransparent material.
【００２２】また、本発明の有機ＥＬ素子における有機
発光層をホスファミン誘導体と他の物質とにより形成す
る場合、ホスファミン誘導体以外の他の有機発光層材料
としては、例えば、多環縮合芳香族化合物や、ベンゾオ
キサゾール系、ベンソチアゾール系、ベンゾイミダゾー
ル系等の蛍光増白剤、金属キレート化オキサノイド化合
物、ジスチリルベンゼン系化合物等の、薄膜形成性の良
い化合物を用いることができる。When the organic light emitting layer in the organic EL device of the present invention is formed of a phosphamine derivative and another substance, examples of the organic light emitting layer material other than the phosphamine derivative include polycyclic condensed aromatic compounds and Compounds having good thin film-forming properties such as fluorescent brightening agents such as benzoxazole-based, benzthiazole-based, and benzimidazole-based compounds, metal chelated oxanoide compounds, and distyrylbenzene-based compounds can be used.
【００２３】ここで、上記多環縮合芳香族の具体例とし
ては、アントラセン、ナフタレン、フェナントレン、ピ
レン、クリセン、ペリレン骨格等を含む縮合環発光物質
や、８〜２０個、好ましくは８個の縮合環を含む他の縮
合環発光物質等を挙げることができる。Specific examples of the above polycyclic condensed aromatic compounds include condensed ring light-emitting substances containing anthracene, naphthalene, phenanthrene, pyrene, chrysene, perylene skeleton, etc., and 8 to 20, preferably 8 condensed rings. Other condensed ring light emitting substances containing a ring can be cited.
【００２４】また、上記ベンゾオキサゾール系、ベンソ
チアゾール系、ベンゾイミダゾール系等の蛍光増白剤と
しては、例えば、特開昭５９−１９４３９３号公報に開
示されているものを挙げることができる。その代表例と
しては、２，５−ビス（５，７−ジーｔ−ペンチル−２
−ベンゾオキサゾリル）−１，３，４−チアジアゾー
ル、４，４’−ビス（５，７−ｔ−ペンチル−２−ベン
ゾオキサゾリル）スチルベン、４，４’−ビス（５，７
−ジー（２−メチル−２−ブチル）−２−ベンゾオキサ
ゾリル）スチルベン、２，５−ビス（５、７−ジーｔ−
ペンチル−２−ベンゾオキサゾリル）チオフェン、２，
５−ビス（５−（α、α−ジメチルベンジル）−２−ベ
ンゾオキサゾリル）チオフェン、２，５−ビス（５，７
−ジー（２−メチル−２−ブチル）ー２ーベンゾオキサ
ゾリル）−３，４−ジフェニルチオフェン、２，５−ビ
ス（５−メチル−２−ベンゾオキサゾリル）チオフェ
ン、４，４’−ビス（２−ベンゾオキサゾリル）ビフェ
ニル、５−メチル−２−（２−（４−（５−メチル−２
−ベンゾオキサゾリル）フェニル）ビニル）ベンゾオキ
サゾール、２−（２−（４−クロロフェニル）ビニル）
ナフト（１，２−ｄ）オキサゾール等のベンゾオキサゾ
ール系、２，２’−（ｐ−フェニレンジビニレン）ービ
スベンゾチアゾール等のベンゾチアゾール系、２，２’
−（ｐ−フェニレンジビニレン）−ビスベンゾチアゾー
ル等のベンゾチアゾール系、２−（２−（４−カルボキ
シフェニル）ビニル）ベンゾイミダゾール等のベンゾイ
ミダゾール系等の蛍光増白剤を挙げることができる。Examples of the above-mentioned benzoxazole-based, benzthiazole-based, benzimidazole-based fluorescent whitening agents include those disclosed in JP-A-59-194393. A typical example is 2,5-bis (5,7-di-t-pentyl-2.
-Benzoxazolyl) -1,3,4-thiadiazole, 4,4'-bis (5,7-t-pentyl-2-benzoxazolyl) stilbene, 4,4'-bis (5,7)
-Di (2-methyl-2-butyl) -2-benzoxazolyl) stilbene, 2,5-bis (5,7-di-t-
Pentyl-2-benzoxazolyl) thiophene, 2,
5-bis (5- (α, α-dimethylbenzyl) -2-benzoxazolyl) thiophene, 2,5-bis (5,7
-Di (2-methyl-2-butyl) -2-benzoxazolyl) -3,4-diphenylthiophene, 2,5-bis (5-methyl-2-benzoxazolyl) thiophene, 4,4 ' -Bis (2-benzoxazolyl) biphenyl, 5-methyl-2- (2- (4- (5-methyl-2
-Benzoxazolyl) phenyl) vinyl) benzoxazole, 2- (2- (4-chlorophenyl) vinyl)
Benzoxazoles such as naphtho (1,2-d) oxazole, benzothiazoles such as 2,2 ′-(p-phenylenedivinylene) -bisbenzothiazole, 2,2 ′
Fluorescent brighteners such as benzothiazoles such as-(p-phenylenedivinylene) -bisbenzothiazole and benzimidazoles such as 2- (2- (4-carboxyphenyl) vinyl) benzimidazole can be mentioned.
【００２５】前記金属キレート化オキサノイド化合物と
しては、例えば、特開昭６３−２９５６９５号公報に開
示されているものを用いることができる。その代表例と
しては、トリス（８−キノリノール）アルミニウム、ビ
ス（８−キノリノール）マグネシウム、ビス（ベンゾ
（ｆ）−８−キノリノール）亜鉛、ビス（２−メチル−
８−キノリノラート）アルミニウムオキシド、トリス
（８−キノリノール）インジウム、トリス（５−メチル
−８−キノリノール）アルミニウム、８−キノリノール
リチウム、トリス（５−クロロ−８−キノリノール）ガ
リウム、ビス（５−クロロ−８−キノリノール）カルシ
ウム、ポリ（亜鉛（ＩＩ）−ビス（８−ヒドロキシ−５
−キノリノニル）メタン）等の８−ヒドロキシキノリン
系金属錯体やジリチウムエピンドリジオン等をあげるこ
とができる。As the metal chelated oxanoide compound, for example, those disclosed in JP-A-63-295695 can be used. Typical examples thereof are tris (8-quinolinol) aluminum, bis (8-quinolinol) magnesium, bis (benzo (f) -8-quinolinol) zinc, bis (2-methyl-).
8-quinolinolate) aluminum oxide, tris (8-quinolinol) indium, tris (5-methyl-8-quinolinol) aluminum, 8-quinolinol lithium, tris (5-chloro-8-quinolinol) gallium, bis (5-chloro- 8-quinolinol) calcium, poly (zinc (II) -bis (8-hydroxy-5)
Examples thereof include 8-hydroxyquinoline-based metal complexes such as -quinolinonyl) methane) and dilithium epindridione.
【００２６】また、前記ジスチリルベンゼン系化合物と
しては、例えば、欧州特許第０３７３５８２号の明細書
に開示されているものを用いることができる。その代表
例としては、１，４−ビス（２−メチルスチリル）ベン
ゼン、１，４−ビス（３−メチルスチリル）ベンゼン、
１，４−ビス（４−メチルスチリル）ベンゼン、ジスチ
リル）ベンゼン、１，４−ビス（２−エチルスチリル）
ベンゼン、１，４−ビス（３−エチルスチリル）ベンゼ
ン、１，４−ビス（２−メチルスチリル）−２−メチル
ベンゼン、１，４−ビス（２−メチルスチリル）−２−
エチルベンゼン等を挙げることができる。As the distyrylbenzene compound, for example, those disclosed in the specification of European Patent No. 0373582 can be used. As typical examples thereof, 1,4-bis (2-methylstyryl) benzene, 1,4-bis (3-methylstyryl) benzene,
1,4-bis (4-methylstyryl) benzene, distyryl) benzene, 1,4-bis (2-ethylstyryl)
Benzene, 1,4-bis (3-ethylstyryl) benzene, 1,4-bis (2-methylstyryl) -2-methylbenzene, 1,4-bis (2-methylstyryl) -2-
Examples thereof include ethylbenzene.
【００２７】また、特開平２−２５２７９３号公報に開
示されているジスチリルピラジン誘導体も有機発光層の
材料として用いることができる。その代表例としては、
２，５−ビス（４−メチルスチリル）ピラジン、２，５
−ビス（４−エチルスチリル）ピラジン、２，５−ビス
［２−（１−ナフチル）ビニル］ピラジン、２，５−ビ
ス（４−メトキシスチリル）ピラジン、２，５−ビス
［２−（４−ビフェニル）ビニル］ピラジン、２，５−
ビス［２−（１−ピレニル）ビニル］ピラジン等を挙げ
ることができる。The distyrylpyrazine derivative disclosed in JP-A-2-252793 can also be used as a material for the organic light emitting layer. As a typical example,
2,5-bis (4-methylstyryl) pyrazine, 2,5
-Bis (4-ethylstyryl) pyrazine, 2,5-bis [2- (1-naphthyl) vinyl] pyrazine, 2,5-bis (4-methoxystyryl) pyrazine, 2,5-bis [2- (4 -Biphenyl) vinyl] pyrazine, 2,5-
Examples thereof include bis [2- (1-pyrenyl) vinyl] pyrazine.
【００２８】その他、欧州特許第０３８８７６８号明細
書や特開平３−２３１９７０号公報に開示されているジ
メチリデン誘導体を有機発光層の材料として用いること
もできる。その代表例としては、１，４−フェニレンジ
メチリディン、４，４’−ビフェニレンジメチリディ
ン、２，５−キシリレンジメチリディン、２，６−ナフ
チレンジメチリディン、１，４−ビフェニレンジメチリ
ディン、１，４−ｐ−テレフェニレンジメチリディン、
９，１０−アントラセンジイルジメチリディン、４，
４’−（２、２−ジーｔ−ブチルフェニルビニル）ビフ
ェニル、４，４’−（２，２−ジフェニルビニル）ビフ
ェニル等、およびこれらの誘導体を挙げることができ
る。In addition, the dimethylidene derivative disclosed in European Patent No. 0388768 or JP-A-3-231970 can be used as a material for the organic light emitting layer. Typical examples thereof are 1,4-phenylene dimethylidene, 4,4′-biphenylene dimethylidene, 2,5-xylylene dimethylidene, 2,6-naphthylene dimethylidene, 1,4-biphenylene. Dimethyridin, 1,4-p-telephenylenedimethyridin,
9,10-anthracene diyl dimethylidin, 4,
Examples thereof include 4 '-(2,2-di-t-butylphenylvinyl) biphenyl, 4,4'-(2,2-diphenylvinyl) biphenyl, and derivatives thereof.
【００２９】さらには、特開平２−１９１６９４号公報
に開示されているクマリン誘導体、特開平２−１９６８
８５号公報に開示されているペリレン誘導体、特開平２
−２５５７８９号公報に開示されているナフタレン誘導
体、特開平２−２８９６７６号公報および特開平２−８
８６８９号公報に開示されているフタロペリノン誘導
体、特開平２−２５０２９２号公報に開示されているス
チリルアミン誘導体も、有機発光層の材料として用いる
ことができる。上述した有機発光層材料は、目的とする
発光色、性能等に応じて適宜選択可能である。Furthermore, the coumarin derivative disclosed in Japanese Patent Application Laid-Open No. 2-191694, Japanese Patent Application Laid-Open No. 2-1968.
No. 85, a perylene derivative disclosed in Japanese Patent Application Laid-Open No. Hei 2
Naphthalene derivatives disclosed in JP-A-255789, JP-A-2-289676 and JP-A-2-8
The phthaloperinone derivative disclosed in 8689 and the styrylamine derivative disclosed in JP-A-2-250292 can also be used as the material of the organic light emitting layer. The above-mentioned organic light emitting layer material can be appropriately selected according to the desired emission color, performance, and the like.
【００３０】なお、本発明の有機ＥＬ素子における有機
発光層は、米国特許第４７６９２９２号明細書に開示さ
れているように、蛍光物質を加えて形成しても良い。こ
の時のベースとなる物質は、ホスファミン誘導体であっ
ても良いし、ホスファミン誘導体以外の有機発光層材料
であっても良い。さらには、ホスファミン誘導体と有機
発光層材料との混合物であっても良い。蛍光物質を加え
て有機発光層を形成する場合、蛍光物質の添加量は数モ
ル％以下が好ましい。蛍光物質は電子と正孔との再結合
に応答して発光するため、発光機能の一部を担うことに
なる。The organic light emitting layer in the organic EL device of the present invention may be formed by adding a fluorescent substance as disclosed in US Pat. No. 4,769,292. The base substance at this time may be a phosphamine derivative or an organic light emitting layer material other than the phosphamine derivative. Further, it may be a mixture of a phosphamine derivative and an organic light emitting layer material. When the organic light emitting layer is formed by adding the fluorescent substance, the addition amount of the fluorescent substance is preferably several mol% or less. Since the fluorescent substance emits light in response to the recombination of electrons and holes, it plays a part of the light emitting function.
【００３１】また、有機発光層材料としては、薄膜性を
有していない化合物を用いることもできる。具体例とし
ては、１，４−ジフェニル−１，３−ブタジエン、１，
１，４，４−テトラフェニル−１，３−ブタジエン、テ
トラフェニルシクロペンタジエン等を挙げることができ
る。しかし、薄膜性を有しないこれらの材料を用いた有
機ＥＬ素子は、素子の寿命が短いという欠点を有する場
合がある。Further, as the organic light emitting layer material, a compound having no thin film property can be used. Specific examples include 1,4-diphenyl-1,3-butadiene, 1,
Examples include 1,4,4-tetraphenyl-1,3-butadiene and tetraphenylcyclopentadiene. However, the organic EL device using these materials having no thin film property may have a short life of the device.
【００３２】本発明の有機ＥＬ素子において必要に応じ
て設けられる正孔輸送層は、有機発光層がホスファミン
誘導体を含んでいれば、ホスファミン誘導体を含む層で
あっても良いし、ホスファミン誘導体を含まない層であ
っても良い。ホスファミン誘導体以外の正孔輸送層材料
としては、有機ＥＬ素子の正孔輸送層材料として従来か
ら使用されている種々の物質を用いることができる。In the organic EL device of the present invention, the hole transport layer provided as necessary may be a layer containing a phosphamine derivative or a phosphamine derivative as long as the organic light emitting layer contains the phosphamine derivative. There may be no layer. As the hole transport layer material other than the phosphamine derivative, various substances conventionally used as the hole transport layer material of the organic EL element can be used.
【００３３】また、本発明の有機ＥＬ素子において必要
に応じて設けられる正孔輸送層として、ホスファミン誘
導体を含む層を設ける場合、この正孔輸送層は、前述し
たように、ホスファミン誘導体のみからなる単層構造、
ホスファミン誘導体の層と有機ＥＬ素子の正孔輸送層材
料として従来から使用されている物質の層との複層構
造、あるいはホスファミン誘導体と有機ＥＬ素子の正孔
輸送層材料として従来から使用されている物質との混合
物からなる層を含む単層構造または複層構造のいずれで
あっても良い。この場合の好ましい層構造は、ホスファ
ミン誘導体のみからなる単層構造、またはホスファミン
誘導体層と、ポルフィリン化合物（特開昭６３−２９５
６９５号公報等に開示されているもの）の層または有機
半導体性オリゴマーの層との複層構造である。When a layer containing a phosphamine derivative is provided as a hole transporting layer provided as necessary in the organic EL device of the present invention, this hole transporting layer is made of only the phosphamine derivative as described above. Single layer structure,
A multilayer structure of a phosphamine derivative layer and a layer of a substance conventionally used as a hole transport layer material for an organic EL element, or a phosphamine derivative and a hole transport layer material conventionally used as an organic EL element. It may have either a single-layer structure or a multi-layer structure including a layer composed of a mixture with a substance. In this case, a preferable layer structure is a single layer structure consisting of a phosphamine derivative alone, or a phosphamine derivative layer and a porphyrin compound (JP-A-63-295)
695) or a layer of an organic semiconducting oligomer.
【００３４】上記ポルフィリン化合物の代表例として
は、ポルフィリン、５，１０，１５，２０−テトラフェ
ニル−２１Ｈ−，２３Ｈ−ポルフィリン銅（ＩＩ）、
５，１０，１５，２０−テトラフェニル−２１Ｈ−，２
３Ｈ−ポルフィリン亜鉛（ＩＩ）、５，１０，１５，２
０−テトラキス（ペンタフルオロフェニル）−２１Ｈ
−，２３Ｈ−ポルフィリン、シリコンフタロシアニンオ
キシド、アルミニウムフタロシアニンクロリド、フタロ
シアニン（無金属）、ジリチウムフタロシアニン、銅テ
トラメチルフタロシアニン、銅フタロシアニン、クロム
フタロシアニン、亜鉛フタロシアニン、鉛フタロシアニ
ン、チタニウムフタロシアニンオキシド、マグネシウム
フタロシアニン、銅オクタメチルフタロシアニン等を挙
げることができる。 また、上記有機半導体性オリゴマ
ーとしては、特に下式Typical examples of the porphyrin compound include porphyrin, 5,10,15,20-tetraphenyl-21H-, 23H-porphyrin copper (II),
5,10,15,20-tetraphenyl-21H-, 2
3H-porphyrin zinc (II), 5,10,15,2
0-Tetrakis (pentafluorophenyl) -21H
-, 23H-porphyrin, silicon phthalocyanine oxide, aluminum phthalocyanine chloride, phthalocyanine (metal free), dilithium phthalocyanine, copper tetramethyl phthalocyanine, copper phthalocyanine, chromium phthalocyanine, zinc phthalocyanine, lead phthalocyanine, titanium phthalocyanine oxide, magnesium phthalocyanine, copper octa. Methyl phthalocyanine etc. can be mentioned. In addition, as the organic semiconductor oligomer, the following formula
【化１１】 （式中、ｋ＝１，２または３、ｍ＝１，２または３，ｎ
＝１，２または３であり、かつｋ＋ｍ＋ｎ≧５であり、
Ｒ5 ，Ｒ6 およびＲ7 はそれぞれ独立に炭素数１〜１０
のアルキル基、炭素数１〜１０のアルコキシ基またはシ
クロヘキシル基である。）で表わされる有機半導体性オ
リゴマーが好適である。[Chemical 11] (In the formula, k = 1, 2 or 3, m = 1, 2 or 3, n
= 1, 2 or 3, and k + m + n ≧ 5,
R 5 , R 6 and R 7 each independently have 1 to 10 carbon atoms.
Is an alkyl group, an alkoxy group having 1 to 10 carbon atoms, or a cyclohexyl group. The organic semiconducting oligomer represented by) is suitable.
【００３５】本発明の有機ＥＬ素子において必要に応じ
て設けられる電子注入層は、陰極から注入された電子を
有機発光層に伝達する機能を有していれば良く、その材
料としては従来公知の電子伝達化合物の中から任意のも
のを選択して用いることができる。In the organic EL device of the present invention, the electron injection layer provided as necessary may have a function of transmitting the electrons injected from the cathode to the organic light emitting layer, and its material is conventionally known. Any one of the electron transfer compounds can be selected and used.
【００３６】電子伝達化合物の好ましい具体例として
は、下式（１）〜（５）Preferable specific examples of the electron transfer compound include the following formulas (1) to (5).
【化１２】 [Chemical 12]
【化１３】 [Chemical 13]
【化１４】 [Chemical 14]
【化１５】 [Chemical 15]
【化１６】 で表わされる化合物を挙げることができる。[Chemical 16] The compound represented by
【００３７】なお、電子注入層は電子の注入性、輸送
性、障害性のいずれかを有する層であり、上記式（１）
〜（５）の化合物の他に、Ｓｉ系，ＳｉＣ系、ＣｄＳ系
等の結晶性ないし非結晶性材料を用いることもできる。The electron injecting layer is a layer having any of the electron injecting property, the electron transporting property and the obstacle property, and is represented by the above formula (1).
In addition to the compounds (5) to (5), a crystalline or non-crystalline material such as Si-based, SiC-based, CdS-based can be used.
【００３８】本発明の有機ＥＬ素子は、上述した陽極、
陰極、有機発光層、必要に応じて設けられる正孔輸送
層、および必要に応じて設けられる正孔輸送層、および
必要に応じて設けられる電子注入層以外に、層間の付着
性を改善するための層を有していても良い。このような
層（例えば有機発光層と陰極との付着性を改善するため
の層）の材料の具体例としては、トリス（８−キノリノ
ール）アルミニウム、トリス（８−キノリノール）イン
ジウム等のキノリノール金属錯体系を挙げることができ
る。The organic EL device of the present invention comprises the above-mentioned anode,
In addition to the cathode, the organic light-emitting layer, the hole transport layer provided as necessary, the hole transport layer provided as necessary, and the electron injection layer provided as necessary, for improving the adhesion between layers. It may have a layer of. Specific examples of the material of such a layer (for example, a layer for improving the adhesion between the organic light emitting layer and the cathode) include quinolinol metal complexes such as tris (8-quinolinol) aluminum and tris (8-quinolinol) indium. I can list the system.
【００３９】以上説明した本発明の有機ＥＬ素子は、そ
の構成に応じて、例えば以下のようにして製造すること
ができる。The organic EL device of the present invention described above can be manufactured, for example, as follows, depending on the structure thereof.
【００４０】（ａ）陽極／有機発光層（ホスファミン誘
導体を含む）／陰極の構成の有機ＥＬ素子の製造例
（１） まず適当な基板上に、所望の電極物質、例えば陽極物質
からなる薄膜を、１μｍ以下、好ましくは１０〜２００
ｎｍの範囲の膜厚になるように、蒸着やスパッタリング
等の方法により形成して、陽極を作製する。次に、この
陽極上にホスファミン誘導体の薄膜を形成することによ
り、有機発光層を設ける。ホスファミン誘導体の薄膜化
は、真空蒸着法、スピンコート法、キャスト法等の方法
により行うことができるが、均質な膜が得られやすく、
かつピンホールが生成しにくい等の点から、真空蒸着法
が好ましい。(A) Anode / organic light emitting layer (phosphamine
Manufacturing example of organic EL device with structure including conductor) / cathode
(1) First, a thin film made of a desired electrode material, for example, an anode material, is formed on a suitable substrate and has a thickness of 1 μm or less, preferably 10 to 200.
The anode is formed by a method such as vapor deposition or sputtering so as to have a film thickness in the range of nm. Next, an organic light emitting layer is provided by forming a thin film of a phosphamine derivative on this anode. The thinning of the phosphamine derivative can be performed by a method such as a vacuum vapor deposition method, a spin coating method, and a casting method, but a uniform film is easily obtained,
In addition, the vacuum deposition method is preferable because it is difficult to generate pinholes.
【００４１】ホスファミン誘導体を薄膜化するにあたっ
て、真空蒸着法を適用する場合、その蒸着条件は、使用
するホスファミン誘導体の種類、目的とする有機発光層
の結晶構造や会合構造等により異なるが、一般にボート
加熱温度５０〜４００℃、真空度１０-5〜１０-3Ｐａ、
蒸着速度０．０１〜５０ｎｍ／ｓｅｃ、基板温度−５０
〜＋３００℃，膜厚５ｎｍ〜５μｍの範囲で適宜選択す
ることが好ましい。When a vacuum vapor deposition method is applied to form a thin film of a phosphamine derivative, the vapor deposition conditions vary depending on the kind of the phosphamine derivative used, the crystal structure or association structure of the target organic light emitting layer, etc. Heating temperature 50 to 400 ° C., vacuum degree 10 −5 to 10 −3 Pa,
Deposition rate 0.01 to 50 nm / sec, substrate temperature -50
It is preferable to select appropriately within a range of from + 300 ° C. and a film thickness of 5 nm to 5 μm.
【００４２】有機発光層の形成後、この有機発光層上に
陰極物質からなる薄膜を、１μｍ以下、好ましくは１０
〜２００ｎｍの範囲の膜厚になるように、蒸着やスパッ
タリング等の方法により形成して、陰極を作製する。こ
れにより目的とする有機ＥＬ素子を得ることができる。
なお、この有機ＥＬ素子の製造においては、製造順を逆
にして、基板上に陰極／有機発光層／陽極の順に作製す
ることも可能である。After forming the organic light emitting layer, a thin film made of a cathode material is formed on the organic light emitting layer in a thickness of 1 μm or less, preferably 10 μm or less.
A cathode is formed by forming the film so as to have a film thickness in the range of up to 200 nm by a method such as vapor deposition or sputtering. As a result, the target organic EL device can be obtained.
In the production of this organic EL element, it is also possible to reverse the production order and produce it on the substrate in the order of cathode / organic light emitting layer / anode.
【００４３】（ｂ）陽極／有機発光層（ホスファミン誘
導体を含む）／陰極の構成の有機ＥＬ素子の製造例
（２） まず適当な基板上に、前記（ａ）の場合と同様にして、
陽極を作製する。次に、この陽極上に、正孔輸送層材
料、有機発光層材料、電子注入層材料、結着剤（ポリビ
ニルカルバゾール等）を含む溶液を塗布することによ
り、有機発光層を設ける。(B) Anode / organic light-emitting layer (phosphamine-induced )
Manufacturing example of organic EL device with structure including conductor) / cathode
(2) First, on an appropriate substrate, in the same manner as in the case of (a) above,
Make an anode. Next, a solution containing a hole transport layer material, an organic light emitting layer material, an electron injection layer material, and a binder (polyvinylcarbazole or the like) is applied onto this anode to form an organic light emitting layer.
【００４４】その後、陰極物質からなる薄膜を前記
（ａ）の場合と同様にして有機発光層上に形成して、陰
極を作製する。これにより目的とする有機ＥＬ素子が得
られる。なお有機発光層は、上述のようにして形成した
層の上に、所望の有機発光層材料の薄膜を真空蒸着法等
により形成して、複層構造としても良い。あるいは、正
孔輸送層材料や電子注入層材料とともに有機発光層材料
を同時蒸着させることにより、有機発光層を形成しても
良い。After that, a thin film made of a cathode material is formed on the organic light emitting layer in the same manner as in the case (a) to prepare a cathode. As a result, the target organic EL device is obtained. The organic light emitting layer may have a multilayer structure by forming a thin film of a desired organic light emitting layer material on the layer formed as described above by a vacuum deposition method or the like. Alternatively, the organic light emitting layer may be formed by co-evaporating the organic light emitting layer material together with the hole transport layer material and the electron injection layer material.
【００４５】（ｃ）陽極／正孔輸送層（ホスファミン誘
導体を含む）／有機発光層／陰極の構成の有機ＥＬ素子
の製造 まず適当な基板上に、前記（ａ）の場合と同様にして、
陽極を作製する。次に、この陽極上にホスファミン誘導
体の薄膜を形成することにより、正孔輸送層を設ける。
この正孔輸送層の形成は、前記（ａ）における有機発光
層（ホスファミン誘導体を含む）の形成と同様にして行
うことができる。(C) Anode / hole transport layer (phosphamine-induced )
(Including conductor) / organic light-emitting layer / cathode organic EL device
On manufacturing first suitable substrate, as in the case of the (a),
Make an anode. Next, a hole transport layer is provided by forming a thin film of a phosphamine derivative on this anode.
The formation of the hole transport layer can be performed in the same manner as the formation of the organic light emitting layer (including the phosphamine derivative) in the above (a).
【００４６】次に、正孔輸送層上に、所望の有機発光層
材料を用いて有機発光層を設ける。有機発光層は、真空
蒸着法、スピンコート法、キャスト法等の方法により有
機発光層材料を薄膜化することにより形成することがで
きるが、均質な膜が得られやすく、かつピンホールが生
成しにくい等の点から、真空蒸着法が好ましい。その
後、陰極物質からなる薄膜を前記（ａ）の場合と同様に
して有機発光層上に形成して、陰極を作製する。これに
より目的とする有機ＥＬ素子が得られる。なお、この有
機ＥＬ素子の製造においても、製造順を逆にして、基板
上に陰極／有機発光層／正孔輸送層／陽極の順に作製す
ることも可能である。Next, an organic light emitting layer is provided on the hole transport layer by using a desired organic light emitting layer material. The organic light emitting layer can be formed by thinning the organic light emitting layer material by a method such as a vacuum vapor deposition method, a spin coating method, or a casting method, but a uniform film is easily obtained and pinholes are generated. The vacuum vapor deposition method is preferable in terms of difficulty and the like. After that, a thin film made of a cathode material is formed on the organic light emitting layer in the same manner as in the case of (a) to prepare a cathode. As a result, the target organic EL device is obtained. Also in the production of this organic EL element, it is possible to reverse the production order and fabricate on the substrate in the order of cathode / organic light emitting layer / hole transport layer / anode.
【００４７】（ｄ）陽極／正孔輸送層（ホスファミン誘
導体を含む）／有機発光層／電子注入層／陰極の構成の
有機ＥＬ素子の製造例 まず、適当な基板上に、前記（ｃ）の場合と同様にし
て、陽極、正孔輸送層（ホスファミン誘導体を含む）お
よび有機発光層を形成する。(D) Anode / hole transport layer (phosphamine-induced )
(Including conductor) / organic light emitting layer / electron injection layer / cathode
Manufacturing Example of Organic EL Element First, an anode, a hole transport layer (including a phosphamine derivative) and an organic light emitting layer are formed on a suitable substrate in the same manner as in the case (c).
【００４８】有機発光層の形成後、この有機発光層上に
陰極物質からなる薄膜を、１μｍ以下、好ましくは５〜
１００ｎｍの範囲の膜厚になるように、蒸着やスパッタ
リング等の方法により形成して、電子注入層を形成す
る。この後、陰極物質からなる薄膜を前記（ｃ）の場合
と同様にして電子注入層上に形成して、陰極を作製す
る。これにより目的とする有機ＥＬ素子を得ることがで
きる。なお、この有機ＥＬ素子の製造においては、製造
順を逆にして、基板上に陰極／電子注入層／有機発光層
／正孔輸送層／陽極の順に作製することも可能である。After the organic light emitting layer is formed, a thin film of a cathode material is formed on the organic light emitting layer with a thickness of 1 μm or less, preferably 5 to 5.
The electron injection layer is formed by a method such as vapor deposition or sputtering so as to have a film thickness in the range of 100 nm. After that, a thin film made of a cathode material is formed on the electron injection layer in the same manner as in the case of (c) to prepare a cathode. As a result, the target organic EL device can be obtained. In the production of this organic EL element, it is possible to reverse the production order and produce on the substrate in the order of cathode / electron injection layer / organic light emitting layer / hole transport layer / anode.
【００４９】上述のようにして製造することができる本
発明の有機ＥＬ素子は、陽極を＋、陰極を−の極性にし
て５〜４０Ｖの直流電圧を印加することにより、発光を
生じる。逆の極性で電圧を印加しても電流は流れず、発
光は全く生じない。また、交流電圧を印加した場合に
は、陽極が＋、陰極が−の極性になった時にのみ発光を
生じる。なお、交流電圧を印加する場合、交流の波形は
任意で良い。The organic EL device of the present invention which can be manufactured as described above emits light by applying a DC voltage of 5 to 40 V with the anode having a positive polarity and the cathode having a negative polarity. Even if a voltage is applied with the opposite polarity, no current flows and no light emission occurs. When an alternating voltage is applied, light emission occurs only when the anode has a positive polarity and the cathode has a negative polarity. When an AC voltage is applied, the AC waveform may be arbitrary.
【００５０】これまで詳述してきたように本発明の有機
ＥＬ素子は、有機発光層を少なくとも含む単層構造また
は複層構造の化合物層の少なくとも一層がホスファミン
誘導体を含む。そして、このホスファミン誘導体のイオ
ン化ポテンシャルは例えば５．３〜５．５ｅＶと低いた
め、本発明の有機ＥＬ素子は低電圧で駆動させることが
できる。As described in detail above, in the organic EL device of the present invention, at least one of the compound layers having a single-layer structure or a multi-layer structure containing at least an organic light-emitting layer contains a phosphamine derivative. Since the ionization potential of this phosphamine derivative is as low as 5.3 to 5.5 eV, the organic EL device of the present invention can be driven at a low voltage.
【００５１】さらに、ホスファミン誘導体の薄膜は、経
時的な再結晶化速度が従来のアミン系材料［（例えばＴ
ＰＤと略称される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）］の薄膜よりも遅い。このため、本発明
によれば、アミン系材料を用いた場合よりも素子寿命の
長い有機ＥＬ素子を得ることが容易になる。Furthermore, the thin film of the phosphamine derivative has a recrystallization rate with time which is different from that of a conventional amine-based material [(eg T
N, N′-bis- (m-tolyl) -abbreviated as PD
N, N'-diphenyl-4,4'-diamino-1,1 '
-Biphenyl)] thin film. Therefore, according to the present invention, it becomes easier to obtain an organic EL device having a longer device life than when an amine-based material is used.
【００５２】また、本発明のホスファミン誘導体は、公
知の真空蒸着法により容易に薄膜化することができると
いう利点がある。さらに、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ホスファミン誘導体を分散させた
溶液を用いたキャスト法、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。これらの薄
膜は正孔を輸送するという電子機能を保有している。The phosphamine derivative of the present invention has an advantage that it can be easily formed into a thin film by a known vacuum deposition method. Further, a thin film can be easily formed by a casting method, a coating method, a spin coating method or the like using a solution in which the phosphamine derivative of the present invention is dispersed in a polymer such as polycarbonate, polyurethane, polystyrene, polyarylate, or polyester. . These thin films have an electronic function of transporting holes.
【００５３】このような特徴を有する本発明のホスファ
ミン誘導体は、有機ＥＬ素子の正孔輸送層、正孔輸送性
結着剤、あるいは発光層に応用することができる他、電
子写真感光体の正孔輸送層等にも応用することができ
る。有機ＥＬ素子に応用した場合には、上述のようにイ
オン化ポテンシャルが例えば５．３〜５．５ｅＶと低い
ことから、印加電圧の低減をもたらす。また、電子写真
感光体に応用した場合には電荷生成層からの良好な正孔
注入をもたらす。その他、有機非線形材料、蛍光材料、
セラミックス焼成用結着剤等として用いることもでき
る。The phosphamine derivative of the present invention having the above characteristics can be applied to a hole transport layer, a hole transport binder, or a light emitting layer of an organic EL device, and can also be applied to a positive electrode of an electrophotographic photoreceptor. It can also be applied to a hole transport layer and the like. When applied to an organic EL device, the applied voltage is reduced because the ionization potential is as low as 5.3 to 5.5 eV as described above. In addition, when applied to an electrophotographic photoreceptor, it brings about good hole injection from the charge generation layer. Others, organic nonlinear materials, fluorescent materials,
It can also be used as a binder for firing ceramics.
【００５４】一般式（ＩＩＩ）で表されるのホスファミ
ン誘導体は、一般式（ＩＶ）The phosphamine derivative represented by the general formula (III) is represented by the general formula (IV)
【化１７】 （式中、Ａｒ1 は炭素数６〜２０のアリール基、置換ア
リール基、または炭素数５〜１０の複素芳香環であり、
Ａｒ2 は、炭素数６〜２０のアリーレン基、置換アリー
レン基、または炭素数５〜１０の複素芳香環である）で
表わされるジアリールアミンと、一般式（Ｖ）[Chemical 17] (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, or a heteroaromatic ring having 5 to 10 carbon atoms,
Ar 2 is an arylene group having 6 to 20 carbon atoms, a substituted arylene group, or a heteroaromatic ring having 5 to 10 carbon atoms) and a general formula (V).
【化１８】 （式中、Ａｒ3 は炭素数６〜２０のアリール基、置換ア
リール基、炭素数５〜１０の複素芳香環、ベンジル基、
またはシンナミル基であり、Ｘは、ハロゲン原子であ
る）で表わされるハロゲン化ホスフィンとを反応させる
ことにより効率良く得ることができる。なお、一般式
（ＩＶ）、（Ｖ）におけるＡｒ1 ，Ａｒ2 ，Ａｒ3 の具
体例については、既に説明済みであるので、その説明を
省略する。またＸはハロゲンで、フッ素、塩素、臭素、
またはヨウ素である。[Chemical 18] (In the formula, Ar 3 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, a heteroaromatic ring having 5 to 10 carbon atoms, a benzyl group,
Alternatively, it is a cinnamyl group, and X is a halogen atom), and can be efficiently obtained by reacting with a halogenated phosphine represented by Since specific examples of Ar 1 , Ar 2 and Ar 3 in the general formulas (IV) and (V) have already been described, the description thereof will be omitted. X is halogen, such as fluorine, chlorine, bromine,
Or iodine.
【００５５】上述した一般式（ＩＶ）で表わされるジア
リールアミンの具体例を、図１９〜図２０に示す。また
上述した一般式（Ｖ）で表わされるハロゲン化ホスフィ
ンの具体例を図２１に示す。Specific examples of the diarylamine represented by the above general formula (IV) are shown in FIGS. A specific example of the halogenated phosphine represented by the above general formula (V) is shown in FIG.
【００５６】一般式（ＩＶ）で表されるジアリールアミ
ンと、一般式（Ｖ）で表されるハロゲン化ホスフィンと
の反応は、例えば以下のようにして行うことができる。The reaction between the diarylamine represented by the general formula (IV) and the halogenated phosphine represented by the general formula (V) can be carried out, for example, as follows.
【００５７】まず、アルゴンガス等の不活性ガスで置換
した反応容器に一般式（ＩＶ）で表わされるジアリール
アミンを入れ、溶媒を加えて溶解させる。この時の溶媒
としては、ジエチルエーテル、ＴＨＦ（テトラヒドロフ
ラン）、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。好ましい溶媒としてはＴＨＦ，特
にアルゴン気流下でナトリウム線から蒸留したＴＨＦを
挙げることができる。次いで、この溶液に２〜４等量の
塩基を加える。塩基としては、ナトリウムアルコキシ
ド、水素化ナトリウム、カリウムｔ−ブトキシド、ｎ−
ブチルリチウム、ＤＢＵ（１，８−ジアザビシクロ
［５，４，０］ウンデカー７ーエン）等の強塩基が好ま
しい。特に好ましい塩基としては、ｎ−ブチルリチウム
を挙げることができる。塩基の好ましい添加量は、２．
５当量程度である。First, the diarylamine represented by the general formula (IV) is placed in a reaction vessel which has been replaced with an inert gas such as argon gas, and a solvent is added and dissolved. As the solvent at this time, diethyl ether, THF (tetrahydrofuran), dioxane, toluene, dimethoxyethane or the like can be used. As a preferable solvent, THF, particularly THF distilled from a sodium line under a stream of argon, can be mentioned. Then 2 to 4 equivalents of base are added to this solution. As the base, sodium alkoxide, sodium hydride, potassium t-butoxide, n-
Strong bases such as butyllithium, DBU (1,8-diazabicyclo [5,4,0] undec-7-ene) are preferred. A particularly preferred base is n-butyllithium. The preferable addition amount of the base is 2.
It is about 5 equivalents.
【００５８】次に、一般式（Ｖ）で表わされるハロゲン
化ホスフィンの２〜４当量を溶媒に溶解させて、反応溶
液に滴下する。この時の溶媒としては、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、ジアリールアミンを溶解さ
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。滴下するハロゲン化ホスフィンの量は、２．５当量
程度が好ましい。また、反応温度は−７８℃〜＋１２０
℃の範囲内で適宜選択可能であるが、室温でも十分良好
な結果を得ることができる。Next, 2 to 4 equivalents of the halogenated phosphine represented by the general formula (V) is dissolved in a solvent and added dropwise to the reaction solution. As the solvent at this time, diethyl ether, THF, dioxane, toluene, dimethoxyethane or the like can be used, but it is preferable to use the same solvent as that used for dissolving the diarylamine. The amount of phosphine halide to be dropped is preferably about 2.5 equivalents. The reaction temperature is -78 ° C to +120.
The temperature can be appropriately selected within the range of ° C, but sufficiently good results can be obtained even at room temperature.
【００５９】上述のようにして、一般式（ＩＶ）で表わ
されるジアリールアミンと一般式（Ｖ）で表わされるハ
ロゲン化ホスフィンとを反応させることにより、一般式
（ＩＩＩ）で表される本発明のホスファミン誘導体を製
造することができる。As described above, the diarylamine represented by the general formula (IV) is reacted with the halogenated phosphine represented by the general formula (V) to give the compound of the present invention represented by the general formula (III). Phosphamine derivatives can be prepared.
【００６０】このようにして製造した本発明のホスファ
ミン誘導体の精製は、例えば以下のようにして、容易に
実施することができる。まず、反応溶液に水を加えて反
応を終了させ、次いで、溶媒で抽出する。この時の抽出
溶媒としては、トルエン、塩化メチレン、酢酸エチル等
を用いることができ、特に塩化メチレンが好ましい。抽
出後、抽出物を乾燥し、さらに溶媒を留去する。この
後、カラムクロマトグラフィーに付することにより、目
的とする精製物を得ることができる。カラムクロマトグ
ラフィーの担体としてはシリカゲル、アルミナ等を用い
ることができる。The phosphamine derivative of the present invention thus produced can be easily purified as follows, for example. First, water is added to the reaction solution to terminate the reaction, and then extraction is performed with a solvent. As the extraction solvent at this time, toluene, methylene chloride, ethyl acetate or the like can be used, and methylene chloride is particularly preferable. After extraction, the extract is dried and the solvent is distilled off. After that, the desired purified product can be obtained by subjecting it to column chromatography. As a carrier for column chromatography, silica gel, alumina or the like can be used.
【００６１】[0061]
【実施例】以下、本発明の実施例について説明する。 実施例１（ホスファミン誘導体の合成例） アルゴン置換した三つ口フラスコに、２．００ｇ（５．
９５ｍｍｏｌ）のＮ，Ｎ’ージフェニルーベンジジン
（東京化成社製）を入れ、ここにアルゴン気流下でナト
リウム線から蒸留した２００ｍｌのＴＨＦを加えて溶解
し、さらにこの溶液にｎ−ブチルリチウムのヘキサン溶
液１０ｍｌ（約１６ｍｍｏｌ）を加えた。これに、３ｍ
ｌ（１６ｍｍｏｌ）のジフェニルクロロホスフィン（東
京化成社製）を５０ｍｌのＴＨＦに溶解した溶液を、滴
下ロートを用いてゆっくり滴下した。これを室温で反応
させ、１８時間後に１００ｍｌの水を加えて反応を終了
させた。EXAMPLES Examples of the present invention will be described below. Example 1 (Synthesis Example of Phosphamine Derivative) 2.00 g (5.
95 mmol) of N, N'-diphenyl-benzidine (manufactured by Tokyo Kasei Co., Ltd.) was added, and 200 ml of THF distilled from a sodium wire under an argon stream was added and dissolved therein, and then hexane of n-butyllithium was added to this solution. 10 ml of solution (about 16 mmol) was added. 3m to this
A solution of 1 (16 mmol) of diphenylchlorophosphine (manufactured by Tokyo Chemical Industry Co., Ltd.) in 50 ml of THF was slowly added dropwise using a dropping funnel. This was reacted at room temperature, and after 18 hours, 100 ml of water was added to terminate the reaction.
【００６２】反応終了後、２００ｍｌの塩化メチレンに
よる抽出を２回行い、抽出物を無水硫酸ナトリウムによ
り乾燥させた後、エバポレーターで溶媒を留去し、白色
粉末を得た。この粉末を、担体として、ワコーゲルＣ−
２００（商品名、広島和光純薬社製のシリカゲル系担
体）を用い、展開液としてトルエンを用いたカラムクロ
マトグラフィーにより精製し、エバポレーターで溶媒を
留去し、２．６８ｇの白色粉末を得た（収率６４％）。After completion of the reaction, extraction with 200 ml of methylene chloride was performed twice, the extract was dried over anhydrous sodium sulfate, and the solvent was distilled off with an evaporator to obtain a white powder. Using this powder as a carrier, Wako Gel C-
200 (trade name, a silica gel carrier manufactured by Hiroshima Wako Pure Chemical Industries, Ltd.) was used for purification by column chromatography using toluene as a developing solution, and the solvent was distilled off with an evaporator to obtain 2.68 g of a white powder. (Yield 64%).
【００６３】このようにして得られた白色粉末の融点は
２２０℃であり、ＮＭＲ測定（Ｈ：４００ＭＨｚ，ＣＤ
2 Ｃｌ2 ）の結果は、δ７．４６−７．４０ｐｐｍ
（ｍ，８Ｈ），７．３４−７．２６ｐｐｍ（ｄｄ，ｄ
ｄ，１６Ｈ），７．１７−７．１０ｐｐｍ（ｔ，４
Ｈ），７．０４−６．９４ｐｐｍ（ｔ，２Ｈ＋ｄｄ，８
Ｈ）であった。The melting point of the white powder thus obtained was 220 ° C., and the NMR measurement (H: 400 MHz, CD
2 Cl 2 ) results in δ7.46-7.40 ppm
(M, 8H), 7.34-7.26 ppm (dd, d
d, 16H), 7.17-7.10 ppm (t, 4
H), 7.04-6.94 ppm (t, 2H + dd, 8
H).
【００６４】また、ＦＤ−ＭＳ（フィールドデソープシ
ョンマススペクトロスコピー）を測定した結果、Ｃ48Ｈ
38Ｎ2 Ｐ2 ＝７０４に対して、７０４のマススペクトル
の親ピークを得た。さらに、ＩＲ（赤外線吸収スペクト
ル）を測定したところ、１６００，１５００，１２８
０，９４０，７５０，７００ｃｍ-1に吸収が観測され
た。これらの測定結果から、得られた白色粉末は、図１
７の（１）に示すホスファミン誘導体（以下Ｐｈｏ−１
という）であることが確認された。Further, as a result of measuring FD-MS (field desorption mass spectroscopy), C 48 H
The parent peak of the mass spectrum of 704 was obtained for 38 N 2 P 2 = 704. Furthermore, when IR (infrared absorption spectrum) was measured, 1600, 1500, 128
Absorption was observed at 0,940,750,700 cm-1. From these measurement results, the obtained white powder is shown in FIG.
The phosphamine derivative shown in (1) of 7 (hereinafter referred to as Pho-1
It was confirmed to be).
【００６５】実施例２（ホスファミン誘導体の合成例） ２．００ｇ（６．９２ｍｍｏｌ）のＮ，Ｎ’−ジフェニ
ル−１，４−ベンゼンジアミン（関東化学社製）と、ｎ
−ブチルリチウムのヘキサン溶液１０ｍｌ（ｎ−ＢｕＬ
ｉ約１６ｍｍｏｌ）と、３ｍｌ（１６ｍｍｏｌ）のジフ
ェニルクロロホスフィンとを、実施例１と同様にして反
応させ、実施例１と同様に精製し、０．４６ｇの白色粉
末を得た（収率１１％）。Example 2 (Synthesis example of phosphamine derivative) 2.00 g (6.92 mmol) of N, N'-diphenyl-1,4-benzenediamine (manufactured by Kanto Chemical Co., Inc.) and n
-Butyllithium hexane solution 10 ml (n-BuL
i (about 16 mmol) and 3 ml (16 mmol) of diphenylchlorophosphine were reacted in the same manner as in Example 1 and purified in the same manner as in Example 1 to obtain 0.46 g of white powder (yield 11% ).
【００６６】このようにして得られた白色粉末の融点は
１７０℃であり、ＦＤ−ＭＳを測定した結果、Ｃ42Ｈ34
Ｎ2 Ｐ2 ＝６２８に対して、６２８のマススペクトルの
親ピークを得た。さらに、ＩＲを測定したところ、１６
２０，１５２０，１２８０，９７０，７６０，７１０ｃ
ｍ-1に吸収が観測された。これらの測定結果から、得ら
れた白色粉末は、図１７の（２）に示すホスファミン誘
導体（以下Ｐｈｏ−２という）であることが確認され
た。The white powder thus obtained has a melting point of 170 ° C., and FD-MS measurement results show that C 42 H 34
The parent peak of the mass spectrum of 628 was obtained for N 2 P 2 = 628. Furthermore, when IR was measured, it was 16
20, 1520, 1280, 970, 760, 710c
Absorption was observed at m-1. From these measurement results, it was confirmed that the obtained white powder was the phosphamine derivative (hereinafter referred to as Pho-2) shown in (2) of FIG.
【００６７】実施例３（ホスファミン誘導体の合成例） ２．０２ｇ（５．５６ｍｍｏｌ）のＮ，Ｎ’−ジナフチ
ル−１，４−ベンゼンジアミン（関東化学社製）と、ｎ
−ブチルリチウムのヘキサン溶液１０ｍｌ（ｎ−ＢｕＬ
ｉ約１６ｍｍｏｌ）と、２．５ｍｌ（１４ｍｍｏｌ）の
ジフェニルクロロホスフィンとを、実施例１と同様にし
て反応させ、実施例１と同様に精製し、０．６３ｇの白
色粉末を得た（収率１６％）。Example 3 (Synthesis example of phosphamine derivative) 2.02 g (5.56 mmol) of N, N'-dinaphthyl-1,4-benzenediamine (manufactured by Kanto Chemical Co., Inc.) and n
-Butyllithium hexane solution 10 ml (n-BuL
i (about 16 mmol) and 2.5 ml (14 mmol) of diphenylchlorophosphine were reacted in the same manner as in Example 1 and purified in the same manner as in Example 1 to obtain 0.63 g of white powder (yield 16%).
【００６８】このようにして得られた白色粉末の融点は
１８７℃であり、ＦＤ−ＭＳを測定した結果、Ｃ50Ｈ38
Ｎ2 Ｐ2 ＝７２８に対して、７２８のマススペクトルの
親ピークを得た。さらに、ＩＲを測定したところ、１６
４０，１６１０、１５１０，１２５０，１１８０，９８
０，９６０，７５０，７１０ｃｍ-1に吸収が観測され
た。これらの測定結果から、得られた白色粉末は、図１
７の（３）に示すホスファミン誘導体（以下Ｐｈｏ−３
という）であることが確認された。The melting point of the white powder thus obtained was 187 ° C., and the result of FD-MS measurement was C 50 H 38
The parent peak of the mass spectrum of 728 was obtained for N 2 P 2 = 728. Furthermore, when IR was measured, it was 16
40, 1610, 1510, 1250, 1180, 98
Absorption was observed at 0,960,750,710 cm-1. From these measurement results, the obtained white powder is shown in FIG.
The phosphamine derivative shown in (3) of 7 (hereinafter referred to as Pho-3
It was confirmed to be).
【００６９】（イオン化ポテンシャルの測定）実施例
１、２および３で得られたホスファミン誘導体（Ｐｈｏ
−１，Ｐｈｏ−２及びＰｈｏ−３）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ＡＣ−１（商品
名）により測定した。また、比較として、代表的な公知
アミン系材料のひとつであるＴＰＤ（Ｎ，Ｎ’−ビスー
（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。(Measurement of Ionization Potential) The phosphamine derivative (Pho) obtained in Examples 1, 2 and 3 was used.
The ionization potentials of -1, Pho-2 and Pho-3) were measured by a surface analyzer AC-1 (trade name) manufactured by Riken Keiki Co., Ltd. For comparison, TPD (N, N′-bis- (m-tolyl) -N, N′-diphenyl-4,4′-diamino-1,1′-biphenyl, which is one of typical known amine-based materials, is used. ) Was measured in the same manner.
【００７０】これらの結果を表１に示す。The results are shown in Table 1.
【表１】 表１から明らかなように、実施例１〜３で得られたホス
ファミン誘導体Ｐｈｏ−１〜３のイオン化ポテンシャル
は、５．３〜５．５ｅＶであり、この値は、ＴＰＤのイ
オン化ポテンシャルと同等、もしくはそれ以下である。
このことから、実施例１〜３で得られたホスファミン誘
導体Ｐｈｏ−１〜３は、正孔が注入されやすいという特
徴を有していることがわかる。[Table 1] As is clear from Table 1, the ionization potentials of the phosphamine derivatives Pho-1 to 3 obtained in Examples 1 to 3 are 5.3 to 5.5 eV, which is equivalent to that of TPD. Or less.
From this, it is understood that the phosphamine derivatives Pho-1 to 3 obtained in Examples 1 to 3 have a feature that holes are easily injected.
【００７１】比較例１（従来の正孔輸送層の材料である
トリフェニルアミン系化合物の合成例） ２２．５ｇ（０．０８ｍｏｌ）のＮ，Ｎ’−ジーｔ−ブ
チルジフェニルアミン、３２．６ｇ（０．１６ｍｏｌ）
のヨードベンゼン、１６．６ｇ（０．１２ｍｏｌ）の無
水炭酸カリウム、および０．５ｇ（８ｍｍｏｌ）の銅粉
を混合し、ＤＭＳＯを溶媒にして２００〜２３０℃で５
時間反応させた。反応終了後、２００ｍｌのトルエンを
加えたところ、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１〜３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 (Synthesis Example of Triphenylamine Compound as Conventional Material for Hole Transport Layer) 22.5 g (0.08 mol) of N, N′-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 DMSO was used as a solvent at 200 to 230 ° C. for 5 minutes.
Reacted for hours. After completion of the reaction, when 200 ml of toluene was added, the product was dissolved, but the inorganic salt remained as a solid substance, and thus purification was difficult unlike in the cases of Examples 1 to 3. It also required treatment of the copper salt effluent.
【００７２】実施例４（有機ＥＬ素子の製造例） ＮＡ４０材であるガラス基板（ＨＯＹＡ（株）製、２５
ｍｍ×７５ｍｍ×１ｍｍ）上に、ＩＴＯ膜（陽極に相
当）を１００ｎｍの厚さで製膜したものを透明支持基板
とした。この透明支持基板をイソプロピルアルコール中
で５分間超音波洗浄した後、乾燥窒素によりブロー、乾
燥し、さらにＵＶオゾン洗浄装置（商品名：ＵＶ３０
０、サムコインターナショナル社製）により１０分間洗
浄した。Example 4 (Production Example of Organic EL Element) 25 glass substrate made of NA40 material (manufactured by HOYA Corporation, 25)
An ITO film (corresponding to an anode) having a thickness of 100 nm formed on a (mm × 75 mm × 1 mm) film was used as a transparent supporting substrate. After ultrasonically cleaning this transparent supporting substrate for 5 minutes in isopropyl alcohol, it is blown with dry nitrogen and dried, and a UV ozone cleaning device (trade name: UV30
0, manufactured by Samco International Co., Ltd.) for 10 minutes.
【００７３】洗浄後の透明支持基板を真空蒸着装置（日
本真空技術（株）製）の基板ホルダーに取付け、真空槽
内を１×１０-4Ｐａまで排気した。なお、排気に先立っ
て、実施例１で得られたホスファミン誘導体（Ｐｈｏ−
１）２００ｍｇを入れたモリブデン製抵抗加熱ボート
と、ジメチリデン系発光材料である４、４’−ビス−
（２、２−ジフェニルビニル）−１、１’−ビフェニル
（以下、ＤＰＶＢｉという）を入れたモリブデン製抵抗
加熱ボートと、電子輸送性の付着改善物質であるトリス
（８−キノリノール）アルミニウム（以下，Ａｌｑとい
う）２００ｍｇを入れたモリブデン製抵抗加熱ボートと
を、それぞれ通電用端子台につけた。The transparent supporting substrate after cleaning was attached to a substrate holder of a vacuum vapor deposition apparatus (manufactured by Nippon Vacuum Technology Co., Ltd.), and the inside of the vacuum chamber was evacuated to 1 × 10 −4 Pa. Prior to exhaust, the phosphamine derivative obtained in Example 1 (Pho-
1) A resistance heating boat made of molybdenum containing 200 mg, and 4,4'-bis- which is a dimethylidene-based luminescent material.
A resistance heating boat made of molybdenum containing (2,2-diphenylvinyl) -1,1'-biphenyl (hereinafter, referred to as DPVBi) and tris (8-quinolinol) aluminum (hereinafter, A molybdenum resistance heating boat containing 200 mg of Alq) was attached to each of the energizing terminal blocks.
【００７４】排気後、Ｐｈｏ−１を入れたボートを２６
０℃にまで加熱し、蒸着レート０．４〜０．６ｎｍ／ｓ
ｅｃでＩＴＯ膜上にＰｈｏ−１を蒸着させて、膜厚４０
ｎｍのＰｈｏ−１層（正孔輸送層に相当）を設けた。After evacuation, the boat containing Pho-1 was
Heating up to 0 ° C., vapor deposition rate 0.4-0.6 nm / s
Pho-1 is vapor-deposited on the ITO film by ec to obtain a film thickness of 40
A Pho-1 layer (corresponding to a hole transport layer) of nm was provided.
【００７５】次いで、ＤＰＶＢｉを入れたボートを加熱
し、蒸着レート０．４〜０．６ｎｍ／ｓｅｃでＰｈｏ−
１層上にＤＰＶＢｉを蒸着させて、膜厚４０ｎｍのＤＰ
ＶＢｉ層（有機発光層に相当）を設けた。Next, the boat containing DPVBi was heated and Pho-was applied at an evaporation rate of 0.4 to 0.6 nm / sec.
DPVBi is vapor-deposited on one layer to form a DP film with a thickness of 40 nm.
A VBi layer (corresponding to an organic light emitting layer) was provided.
【００７６】次に、Ａｌｑを入れたボートを加熱し、蒸
着レート０．１〜０．３ｎｍ／ｓｅｃでＤＰＶＢｉ層上
にＡｌｑを蒸着させて、膜厚２０ｎｍのＡｌｑ層（付着
改善層に相当）を設けた。Next, the boat containing Alq was heated, and Alq was vapor-deposited on the DPVBi layer at a vapor deposition rate of 0.1 to 0.3 nm / sec to form a 20-nm-thick Alq layer (corresponding to an adhesion improving layer). Was set up.
【００７７】この後、真空槽を開け、新たに、マグネシ
ウム入りのモリブデン製ボートと銀入りのタングステン
製フィラメントボートとを通電用端子台につけた。ま
た、先に作製したガラス基板／ＩＴＯ膜／Ｐｈｏ−１層
／ＤＰＶＢｉ層／Ａｌｑ層の上に蒸着用マスクを取り付
けた。After this, the vacuum chamber was opened, and a molybdenum-containing boat containing magnesium and a tungsten-containing filament boat containing silver were newly attached to the energizing terminal block. In addition, a vapor deposition mask was attached on the glass substrate / ITO film / Pho-1 layer / DPVBi layer / Alq layer prepared above.
【００７８】そして、再び真空槽を１×１０-4Ｐａにま
で排気した後、先ず銀入りのフィラメントボートに通電
して蒸着レート０．０９〜０．１ｎｍ／ｓｅｃで銀を蒸
着させると同時に、マグネシウム入りのボートに通電し
て蒸着レート１．４〜１．７ｎｍ／ｓｅｃでマグネシウ
ムを蒸着させた。この二元同時蒸着により、Ａｌｑ層上
に膜厚１５０ｎｍのマグネシウムー銀層（陰極に相当）
が形成された。以上のようにしてガラス基板上に陰極ま
で設けたことにより、有機ＥＬ素子が得られた。Then, after the vacuum chamber was evacuated to 1 × 10 −4 Pa again, first, a filament boat containing silver was energized to deposit silver at a deposition rate of 0.09 to 0.1 nm / sec, and at the same time, A boat containing magnesium was energized to deposit magnesium at a deposition rate of 1.4 to 1.7 nm / sec. By this dual-source simultaneous vapor deposition, a 150 nm thick magnesium-silver layer (corresponding to the cathode) is formed on the Alq layer.
Was formed. An organic EL device was obtained by providing the cathode on the glass substrate as described above.
【００７９】このようにして得られた有機ＥＬ素子のマ
グネシウムー銀層を陰極とし、ＩＴＯ膜を陽極として１
３Ｖの電圧を印加したところ、１５７ｃｄ／ｍ2 の緑味
青色発光が観測された。このときの電流密度、輝度、発
光効率、および発光色を表２に示す。The magnesium-silver layer of the organic EL device thus obtained was used as a cathode, and the ITO film was used as an anode.
When a voltage of 3 V was applied, a greenish blue light emission of 157 cd / m 2 was observed. Table 2 shows the current density, luminance, luminous efficiency, and luminous color at this time.
【００８０】実施例５（有機ＥＬ素子の製造例） 正孔輸送層の材料として銅フタロシアニン（以下、Ｃｕ
Ｐｃという）とＰｈｏ−１とを用いた以外は実施例４と
同様にして、有機ＥＬ素子を得た。なお、正孔輸送層
は、ＣｕＰｃを入れたモリブデン製ボートを加熱し、蒸
着レート０．２〜０．４ｎｍ／ｓｅｃでＩＴＯ膜上にＣ
ｕＰｃを蒸着させて膜厚２０ｎｍのＣｕＰｃ層を設けた
後、Ｐｈｏ−１をいれたモリブデン製ボートを２７０℃
にまで加熱し、蒸着レート０．４〜０．６ｎｍ／ｓｅｃ
でＣｕＰｃ層上にＰｈｏ−１を蒸着させて膜厚４０ｎｍ
のＰｈｏ−１層を設けて、２層構造とすることにより形
成した。Example 5 (Production Example of Organic EL Element) Copper phthalocyanine (hereinafter Cu
An organic EL device was obtained in the same manner as in Example 4 except that Pc) and Pho-1 were used. The hole transport layer is formed by heating a molybdenum boat containing CuPc and depositing C on the ITO film at a vapor deposition rate of 0.2 to 0.4 nm / sec.
After depositing uPc to form a CuPc layer with a thickness of 20 nm, a molybdenum boat containing Pho-1 was placed at 270 ° C.
And vapor deposition rate 0.4-0.6 nm / sec
And deposit Pho-1 on the CuPc layer with a film thickness of 40 nm.
Pho-1 layer is provided to form a two-layer structure.
【００８１】このようにして得られた有機ＥＬ素子に実
施例４と同様にして１２Ｖの電圧を印加したところ、２
００ｃｄ／ｍ2 の緑味青色発光が観察された。このとき
の電流密度、輝度、発光効率、および発光色を表２に示
す。When a voltage of 12 V was applied to the organic EL device thus obtained in the same manner as in Example 4, 2
A greenish blue luminescence of 00 cd / m 2 was observed. Table 2 shows the current density, luminance, luminous efficiency, and luminous color at this time.
【００８２】実施例６（有機ＥＬ素子の製造例） Ｐｈｏ−１に代えて、実施例３で得られたホスファミン
誘導体（Ｐｈｏ−３）を用いた他は、実施例４と同様に
して、有機ＥＬ素子を得た。このようにして得られた有
機ＥＬ素子に実施例４と同様にして１５Ｖの電圧を印加
したところ、１００ｃｄ／ｍ2 の緑色発光が観測され
た。このときの電流密度、輝度、発光効率、および発光
色を表２に示す。Example 6 (Production Example of Organic EL Element) The same procedure as in Example 4 was repeated except that the phosphamine derivative (Pho-3) obtained in Example 3 was used instead of Pho-1. An EL device was obtained. When a voltage of 15 V was applied to the thus-obtained organic EL device in the same manner as in Example 4, green light emission of 100 cd / m 2 was observed. Table 2 shows the current density, luminance, luminous efficiency, and luminous color at this time.
【００８３】実施例７（有機ＥＬ素子の製造例） 正孔輸送層の材料として有機半導体性オリゴマーの１つ
であるαーセキシチオフェン（以下、Ｔ6 という）と、
Ｐｈｏ−１とを用いた以外は実施例４と同様にして、有
機ＥＬ素子を得た。Example 7 (Production Example of Organic EL Device) As a material for the hole transport layer, α-sexithiophene (hereinafter referred to as T6), which is one of the organic semiconductor oligomers,
An organic EL device was obtained in the same manner as in Example 4 except that Pho-1 was used.
【００８４】なお、正孔輸送層は、Ｔ6 を入れたモリブ
デン製ボートを加熱し、蒸着レート０．１〜０．３ｎｍ
／ｓｅｃでＩＴＯ膜上にＴ6 を蒸着させて膜厚２０ｎｍ
のＴ6 層を設けた後、Ｐｈｏ−１を入れたモリブデン製
ボートを２７０℃にまで加熱し、蒸着レート０．４〜
０．６ｎｍ／ｓｅｃでＴ6 層上にＰｈｏ−１を蒸着させ
て膜厚４０ｎｍのＰｈｏ−１層を設けて、２層構造とす
ることにより形成した。このようにして得られた有機Ｅ
Ｌ素子に実施例４と同様にして１０Ｖの電圧を印加した
ところ、２２０ｃｄ／ｍ2 の緑味青色発光が観測され
た。このときの電流密度、輝度、発光効率、および発光
色を表２に示す。The hole-transporting layer was formed by heating a molybdenum boat containing T6 to obtain a vapor deposition rate of 0.1 to 0.3 nm.
/ Sec of T6 deposited on the ITO film at a film thickness of 20 nm
After the T6 layer of No. 1 was provided, the molybdenum boat containing Pho-1 was heated to 270 ° C., and the deposition rate was 0.4 to
Pho-1 was vapor-deposited on the T6 layer at 0.6 nm / sec to form a Pho-1 layer having a film thickness of 40 nm to form a two-layer structure. Organic E obtained in this way
When a voltage of 10 V was applied to the L element in the same manner as in Example 4, 220 cd / m 2 of greenish blue light emission was observed. Table 2 shows the current density, luminance, luminous efficiency, and luminous color at this time.
【００８５】実施例８（有機ＥＬ素子の製造例） Ｔ6 に代えて、有機半導体性オリゴマーの１つである
４，４’−ビス−ジチオフェニル−１、１’−ビフェニ
ル（以下、ＢＴＢＩＢＴという）を用いた以外は実施例
７と同様にして、有機ＥＬ素子を得た。Example 8 (Production Example of Organic EL Device) Instead of T6, 4,4'-bis-dithiophenyl-1,1'-biphenyl (hereinafter referred to as BTBIBT) which is one of the organic semiconductor oligomers. An organic EL device was obtained in the same manner as in Example 7 except that was used.
【００８６】このようにして得られた有機ＥＬ素子に実
施例７と同様にして９Ｖの電圧を印加したところ、２５
０ｃｄ／ｍ2 の緑味青色発光が観測された。このときの
電流密度、輝度、発光効率、および発光色を表２に示
す。When a voltage of 9 V was applied to the thus obtained organic EL device in the same manner as in Example 7, 25
A greenish blue emission of 0 cd / m 2 was observed. Table 2 shows the current density, luminance, luminous efficiency, and luminous color at this time.
【００８７】[0087]
【表２】 表２より明らかなように、実施例４〜８で得られた各有
機ＥＬ素子は９〜１５Ｖの低電圧印加で実用上必要な輝
度である１００ｃｄ／ｍ2 以上を達成した。[Table 2] As is clear from Table 2, each of the organic EL devices obtained in Examples 4 to 8 achieved a practically required luminance of 100 cd / m 2 or more when a low voltage of 9 to 15 V was applied.
【００８８】[0088]
【発明の効果】本発明により、室温という穏和な反応条
件で、かつ廃棄問題等の原因となりやすい重金属を使用
することなくホスファミン誘導体を合成することが可能
となった。また該ホスファミン誘導体を用いた有機ＥＬ
素子のイオン化ポテンシャルは従来のアミン系材料を用
いたものよりも低く、ＥＬ素子の印加電圧を下げる効果
を示した。さらに、その素子の膜性はアミン系材料より
も優れて安定であった。Industrial Applicability According to the present invention, it is possible to synthesize a phosphamine derivative under mild reaction conditions such as room temperature and without using a heavy metal that tends to cause disposal problems. Further, an organic EL using the phosphamine derivative
The ionization potential of the device was lower than that using the conventional amine-based material, which showed the effect of lowering the applied voltage of the EL device. Further, the film property of the device was superior to that of the amine-based material and was stable.
【図面の簡単な説明】[Brief description of drawings]
【図１】は、一般式（Ｉ）の化合物の具体例を示す図、FIG. 1 is a diagram showing specific examples of compounds of general formula (I),
【図２】は、一般式（Ｉ）の化合物の具体例を示す図、FIG. 2 is a diagram showing specific examples of compounds of the general formula (I),
【図３】は、一般式（Ｉ）の化合物の具体例を示す図、FIG. 3 is a diagram showing specific examples of compounds of general formula (I),
【図４】は、一般式（Ｉ）の化合物の具体例を示す図、FIG. 4 is a diagram showing specific examples of the compound of the general formula (I),
【図５】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 5 is a diagram showing specific examples of compounds of general formula (II),
【図６】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 6 is a diagram showing specific examples of compounds of general formula (II),
【図７】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 7 is a diagram showing specific examples of compounds of general formula (II),
【図８】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 8 is a diagram showing specific examples of compounds of general formula (II),
【図９】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 9 is a diagram showing specific examples of compounds of general formula (II),
【図１０】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 10 is a diagram showing specific examples of the compound of the general formula (II),
【図１１】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 11 is a view showing specific examples of the compound of the general formula (II),
【図１２】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 12 is a view showing specific examples of the compound of the general formula (II),
【図１３】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 13 is a diagram showing specific examples of the compound of the general formula (II),
【図１４】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 14 is a diagram showing specific examples of the compound of the general formula (II),
【図１５】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 15 is a diagram showing specific examples of compounds of general formula (II),
【図１６】は、一般式（ＩＩ）の化合物の具体例を示す
図、FIG. 16 is a diagram showing specific examples of the compound of the general formula (II),
【図１７】は、一般式（ＩＩＩ）の化合物の具体例を示
す図、FIG. 17 is a diagram showing specific examples of compounds of the general formula (III),
【図１８】は、一般式（ＩＩＩ）の化合物の具体例を示
す図、FIG. 18 is a diagram showing specific examples of compounds of general formula (III),
【図１９】は、一般式（ＩＶ）の化合物の具体例を示す
図、FIG. 19 is a diagram showing specific examples of compounds of general formula (IV),
【図２０】は、一般式（ＩＶ）の化合物の具体例を示す
図、FIG. 20 is a diagram showing specific examples of compounds of general formula (IV),
【図２１】は、一般式（Ｖ）の化合物の具体例を示す図
である。FIG. 21 is a diagram showing specific examples of the compound of the general formula (V).
Claims (7)
は多層構造の化合物層と、この化合物層を挟持する一対
の電極とを備えた有機エレクトロルミネッセンス素子に
おいて、前記化合物層の少なくとも一層が、ホスファミ
ン誘導体を含むことを特徴とするエレクトロルミネッセ
ンス素子。1. In an organic electroluminescence device comprising a compound layer having a single-layer structure or a multilayer structure containing at least an organic light-emitting layer and a pair of electrodes sandwiching the compound layer, at least one of the compound layers is phosphamine. An electroluminescent device comprising a derivative.
（Ｉ）または（ＩＩ） 【化１】 【化２】 （式（Ｉ）中、Ｒ1 ，Ｒ2 ，Ｒ3 およびＲ4 は、炭素数
１〜６のアルキル基、アルケニル基、アルキニル基、炭
素数６〜２０のアリール基、置換アリール基、炭素数５
〜１０の複素芳香環、ベンジル基、またはシンナミル基
であり、Ｒ1 ，Ｒ2 ，Ｒ3 ，Ｒ4 は同一または異なって
いても良い。また式（ＩＩ）中、Ａｒ1 は、炭素数６〜
２０のアリール基、置換アリール基、または炭素数５〜
１０の複素芳香環であり、Ａｒ2 は、炭素数６〜２０の
アリーレン基、置換アリーレン基、または炭素数５〜１
０の複素芳香環であり、Ａｒ3 は、炭素数６〜２０のア
リール基、置換アリール基、炭素数５〜１０の複素芳香
環、ベンジル基、またはシンナミル基である）で表され
る化合物である、請求項１に記載の有機エレクトロルミ
ネッセンス素子。2. A phosphamine derivative is represented by the following general formula (I) or (II): [Chemical 2] (In the formula (I), R 1 , R 2 , R 3 and R 4 are an alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkynyl group, an aryl group having 6 to 20 carbon atoms, a substituted aryl group, and a carbon number. 5
10 is a heteroaromatic ring, a benzyl group, or a cinnamyl group, and R 1 , R 2 , R 3 , and R 4 may be the same or different. In the formula (II), Ar 1 has 6 to 6 carbon atoms.
20 aryl groups, substituted aryl groups, or 5 to 5 carbon atoms
10 is a heteroaromatic ring, and Ar 2 is an arylene group having 6 to 20 carbon atoms, a substituted arylene group, or 5 to 1 carbon atoms.
A heteroaromatic ring of 0, and Ar 3 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, a heteroaromatic ring having 5 to 10 carbon atoms, a benzyl group, or a cinnamyl group). The organic electroluminescence device according to claim 1, which is present.
が、その下位概念である一般式（ＩＩＩ） 【化３】 （式中、Ａｒ4 は、炭素数６〜２０のアリール基であ
り、Ａｒ5 は炭素数６〜２０のアリーレン基である）で
表される化合物である、請求項２に記載の有機エレクト
ロルミネッセンス素子。3. A phosphamine derivative represented by the general formula (II) is a subordinate concept of the general formula (III): The organic electroluminescence according to claim 2, which is a compound represented by the formula (wherein Ar 4 is an aryl group having 6 to 20 carbon atoms and Ar 5 is an arylene group having 6 to 20 carbon atoms). element.
送層である、請求項１に記載の有機エレクトロルミネッ
センス素子。4. The organic electroluminescence device according to claim 1, wherein the layer containing a phosphamine derivative is a hole transport layer.
アリール基、または炭素数５〜１０の複素芳香環であ
り、Ａｒ2 は、炭素数６〜２０のアリーレン基、置換ア
リーレン基、または炭素数５〜１０の複素芳香環であ
り、Ａｒ3 は、炭素数６〜２０のアリール基、置換アリ
ール基、炭素数５〜１０の複素芳香環、ベンジル基、ま
たはシンナミル基である）で表される化合物からなるこ
とを特徴とするホスファミン誘導体。5. The following general formula (II): (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, or a heteroaromatic ring having 5 to 10 carbon atoms, and Ar 2 is an arylene group having 6 to 20 carbon atoms or a substituted arylene group. Or a heteroaromatic ring having 5 to 10 carbon atoms, and Ar 3 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, a heteroaromatic ring having 5 to 10 carbon atoms, a benzyl group, or a cinnamyl group) A phosphamine derivative comprising a compound represented by:
の下位概念である一般式（ＩＩＩ） 【化５】 （式中、Ａｒ4 は、炭素数６〜２０のアリール基であ
り、Ａｒ5 は炭素数６〜２０のアリーレン基である）で
表される化合物である、請求項５に記載のホスファミン
誘導体。6. A compound represented by the general formula (II) is a subordinate concept of the general formula (III): The phosphamine derivative according to claim 5, which is a compound represented by the formula (wherein Ar 4 is an aryl group having 6 to 20 carbon atoms and Ar 5 is an arylene group having 6 to 20 carbon atoms).
アリール基、または炭素数５〜１０の複素芳香環であ
り、Ａｒ2 は、炭素数６〜２０のアリーレン基、置換ア
リーレン基、または炭素数５〜１０複素芳香環である）
で表されるジアリールアミンと、一般式（Ｖ） 【化７】 （式中、Ａｒ3 は、炭素数６〜２０のアリール基、置換
アリール基、炭素数５〜１０の複素芳香環、ベンジル
基、またはシンナミル基であり、Ｘはハロゲン原子であ
る）で表されるハロゲン化ホスフィンと反応させること
を特徴とする請求項５に記載の一般式（ＩＩＩ）のホス
ファミン誘導体の製造方法。7. A compound represented by the general formula (IV): (In the formula, Ar 1 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, or a heteroaromatic ring having 5 to 10 carbon atoms, and Ar 2 is an arylene group having 6 to 20 carbon atoms or a substituted arylene group. , Or a heteroaromatic ring having 5 to 10 carbon atoms)
A diarylamine represented by the following general formula (V): (In the formula, Ar 3 is an aryl group having 6 to 20 carbon atoms, a substituted aryl group, a heteroaromatic ring having 5 to 10 carbon atoms, a benzyl group, or a cinnamyl group, and X is a halogen atom). The method for producing a phosphamine derivative represented by the general formula (III) according to claim 5, wherein the phosphine derivative is reacted with a halogenated phosphine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4179890A JPH0625659A (en) | 1992-07-07 | 1992-07-07 | Phosphamine derivative, its preparation, and electroluminescent element made using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4179890A JPH0625659A (en) | 1992-07-07 | 1992-07-07 | Phosphamine derivative, its preparation, and electroluminescent element made using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0625659A true JPH0625659A (en) | 1994-02-01 |
Family
ID=16073693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4179890A Withdrawn JPH0625659A (en) | 1992-07-07 | 1992-07-07 | Phosphamine derivative, its preparation, and electroluminescent element made using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0625659A (en) |
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