CN1271167C - 有机电致发光器件 - Google Patents
有机电致发光器件 Download PDFInfo
- Publication number
- CN1271167C CN1271167C CNB008021244A CN00802124A CN1271167C CN 1271167 C CN1271167 C CN 1271167C CN B008021244 A CNB008021244 A CN B008021244A CN 00802124 A CN00802124 A CN 00802124A CN 1271167 C CN1271167 C CN 1271167C
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- methoxy
- expression
- methyl
- ethyl
- 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 239000012044 organic layer Substances 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims abstract description 15
- 239000010410 layer Substances 0.000 claims description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000005401 electroluminescence Methods 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 26
- 238000010276 construction Methods 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 abstract description 7
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 153
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 78
- 239000000463 material Substances 0.000 description 57
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- -1 methylene dicyanoethyl Chemical group 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000470 constituent Substances 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 238000007740 vapor deposition Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 11
- 230000002194 synthesizing effect Effects 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
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- 230000004044 response Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000005135 aceanthrylenes Chemical class 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000004411 aluminium Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- JDPAVWAQGBGGHD-UHFFFAOYSA-N aceanthrylene Chemical group C1=CC=C2C(C=CC3=CC=C4)=C3C4=CC2=C1 JDPAVWAQGBGGHD-UHFFFAOYSA-N 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 5
- 150000002240 furans Chemical class 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 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 5
- 238000010992 reflux Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical class [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 3
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000004880 oxines Chemical class 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 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
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
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- 229920000728 polyester Polymers 0.000 description 2
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- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum 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
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- AKQIJUCZWUAMNJ-UHFFFAOYSA-N 1,3-benzoxazole;quinoline Chemical compound C1=CC=C2OC=NC2=C1.N1=CC=CC2=CC=CC=C21 AKQIJUCZWUAMNJ-UHFFFAOYSA-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
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- MJQNQKYYOCSNKD-UHFFFAOYSA-N 2-naphthalen-1-yl-1,3,4-oxadiazole Chemical compound O1C=NN=C1C1=CC=CC2=CC=CC=C12 MJQNQKYYOCSNKD-UHFFFAOYSA-N 0.000 description 1
- JBXIOAKUBCTDES-UHFFFAOYSA-N 2h-acenaphthylen-1-one Chemical compound C1=CC(C(=O)C2)=C3C2=CC=CC3=C1 JBXIOAKUBCTDES-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- YKKGFDQJKLAEFR-UHFFFAOYSA-N 5-naphthalen-1-yl-1h-1,2,4-triazole Chemical compound N1C=NC(C=2C3=CC=CC=C3C=CC=2)=N1 YKKGFDQJKLAEFR-UHFFFAOYSA-N 0.000 description 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
- 229910001339 C alloy Inorganic materials 0.000 description 1
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Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/70—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a condensed ring system consisting of at least two, mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic ring, e.g. cyclophanes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/68—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
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- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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Abstract
提供了一种有机电致发光器件,该器件呈现很纯的颜色和高发光效率、寿命长、发红光,并提供了具有这些特点的新型化合物。有机电致发光器件包括沉积在至少一对电极之间的有机层,其中有机层包括具有荧蒽骨架结构的化合物,荧蒽骨架结构至少被一个氨基或链烯基基团取代。
Description
技术领域
本发明涉及有机电致发光器件,该器件用作光源如电视的平面发光构件和显示器的背景光,呈现很纯的颜色和高发光效率、寿命长、发红光,并涉及具有这些特点的新型化合物。
背景工艺
使用有机化合物的电致发光(以后称之为EL)器件预期可用于便宜的大屏幕固体发光型全色显示器件,其开发一直在积极进行中。一般而言,EL器件由发光层和一对处于发光层两边相互面对的电极组成。当在电极间施加电压时,电子在阴极一边注入,而空穴在阳极一边注入。电子与空穴在发光层中结合,形成激发态。当激发态返回到基态时,能量以光的形式释放出来。
虽然有机EL器件的实际应用最近已开始,但是全色显示器件仍在开发之中。特别地,希望有一种用于有机EL器件的材料,使该器件呈现很纯的颜色和高发光效率、寿命长、发红光。
为了使上述希望得到满足,发红光的器件在日本专利申请公开号Heisei 8(1996)-311442已公开,在该器件内,并四苯或并五苯的衍生物被加入至发光层中。虽然此器件呈现很纯的红光,但是此器件呈现的发光效率低至0.71m/W,且平均寿命不够,短于150小时。就实际应用而言,至少几千小时的平均寿命是必要的。一种器件在日本专利申请公开号Heisei 3(1991)-162481已公开,在该器件内,二氰亚甲基(DCM)的衍生物被加入至发光层中。但是,该器件呈现出的红光纯度不够。在日本专利申请公开号Heisei 10(1998)-340782和Heisei 11(1999)-40360中公开了使用荧蒽化合物的有机EL器件。但是,使用上述专利申请中公开的化合物的器件不发黄至红光。发光效率不够,低至4cd/A或更小。
发明内容
本发明用于克服上述问题,目标在于提供一种有机EL器件,该器件呈现很纯的颜色和高发光效率、寿命长、发红光,并提供一种具有这些特点的新型化合物。
作为本发明人大量研发具有上述优良品质的有机电致发光器件(以后称之为有机EL器件)的结果,已发现可通过使用具有以至少一个氨基或链烯基取代的荧蒽骨架结构的化合物作为发光材料达到此目标。
本发明的有机电致发光器件包括沉积在至少一对电极之间的有机层,其中有机层包含具有荧蒽骨架结构的化合物,荧蒽骨架结构至少被一个氨基或链烯基取代。
优选上述化合物选自由下列通式[1]至[18]表示的化合物:
其中X1至X20分别各自表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、取代或未取代的含6至30个碳原子的芳基、取代或未取代的含6至30个碳原子的芳氧基、取代或未取代的含6至30个碳原子的芳氨基、取代或未取代的含1至30个碳原子的烷氨基、取代或未取代的含7至30个碳原子的芳烷基氨基或取代或未取代的含8至30个碳原子的链烯基;由X1至X20表示的一对相邻基团和由X1至X20表示的基团相邻的一对取代基可结合形成环状结构;当一对相邻取代基为芳基时,此对取代基可以为单个基团;和至少一个由X1至Xi表示的取代基包括氨基或链烯基团,i表示12至20的数;
其中R1至R4分别各自表示含1至20个碳原子的烷基或取代或未取代的含6至30个碳原子的芳基;在由R1和R2表示的一对基团和由R3和R4表示的一对基团这两对基团之一或这两对基团中,形成一对的基团可通过-O-或-S-键合;R5至R16表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、取代或未取代的含6至30个碳原子的芳基、取代或未取代的含6至30个碳原子的芳氧基、取代或未取代的含6至30个碳原子的芳氨基、取代或未取代的含1至30个碳原子的烷氨基、取代或未取代的含7至30个碳原子的芳烷基氨基或取代或未取代的含8至30个碳原子的链烯基;由R5至R16表示的一对相邻基团和由R5至R16表示的基团相邻的一对取代基可结合形成环状结构;和至少一个由R5至R16表示的取代基包括氨基或链烯基团。
本发明的新型化合物为由上述通式[1]至[18]中任一通式表示的化合物。
附图的简要描述
图1表示本发明新型化合物一个例子的1H-NMR谱。
图2表示本发明新型化合物另一例子的1H-NM谱。
图3表示本发明新型化合物又一例子的1H-NMR谱。
本发明的最优选实施方案
本发明的有机电致发光器件包括沉积在至少一对电极之间的有机层,其中有机层包含具有荧蒽骨架结构的化合物,荧蒽骨架结构至少被一个氨基或链烯基取代。
此化合物为一种新型化合物,由上述通式[1]至[18]中的任一通式表示。
在通式[1]至[16]中,X1至X20分别各自表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、取代或未取代的含6至30个碳原子的芳基、取代或未取代的含6至30个碳原子的芳氧基、取代或未取代的含6至30个碳原子的芳氨基、取代或未取代的含1至30个碳原子的烷氨基、取代或未取代的含7至30个碳原子的芳烷基氨基或取代或未取代的含8至30个碳原子的链烯基;由X1至X20表示的一对相邻基团和由X1至X20表示的基团相邻的一对取代基可结合形成环状结构;当一对相邻取代基为芳基时,此对取代基可以为单个基团;和至少一个由X1至Xi表示的取代基包括氨基或链烯基团,i表示12至20的数。当一对相邻取代基为芳基时,此对取代基可以为单个基团,这意指此对取代基的相邻键与相同的单个二价芳香环基团键合。
在通式[17]和[18]中,R1至R4分别各自表示含1至20个碳原子的烷基或取代或未取代的含6至30个碳原子的芳基;在由R1和R2表示的一对基团和由R3和R4表示的一对基团这两对基团之一或这两对基团中,形成一对的基团可通过-O-或-S-键合;其中R5至R16表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、取代或未取代的含6至30个碳原子的芳基、取代或未取代的含6至30个碳原子的芳氧基、取代或未取代的含6至30个碳原子的芳氨基、取代或未取代的含1至30个碳原子的烷氨基、取代或未取代的含7至30个碳原子的芳烷基氨基或取代或未取代的含8至30个碳原子的链烯基;由R5至R16表示的一对相邻基团和由R5至R16表示的基团相邻的一对取代基可结合形成环状结构;和至少一个由R5至R16表示的取代基包括氨基或链烯基团。
在由通式[1]至[18]表示的化合物中优选的化合物在下面表示。
优选荧蒽骨架结构包括至少5个稠环和更优选至少6个稠环。通过使用具有这样结构的化合物,可发出波长更长的光如黄至红光。
优选荧蒽骨架结构以氨基基团取代。通过使用具有这样结构的化合物,可得到具有更长寿命的发光材料。
优选氨基基团为取代或未取代芳氨基基团和更优选为取代或未取代二芳氨基基团。通过使用具有这样结构的化合物,甚至当将高达2%或更高浓度的上述化合物加入发光层时,仍可得到一种器件,该器件在此化合物浓度增加时发光降低较小,且呈现高效率。
优选上述化合物具有轴对称或面对称的对称结构。通过使用具有这样结构的化合物,器件的耐久性得到改进,荧光的量子效率增强。
优选上述化合物含有至少10个六元环或五元环。由于这种结构,化合物的玻璃转化温度为100℃或更高。由此化合物组成或包括此化合物的层的热稳定性得到改进。优选上述化合物含有芳基、环烷基、芳氧基、芳硫基或芳烷基,每个基团含有4或更多个碳原子。由于这些基团具有位阻,可防止在化合物浓度增加时发光降低。
在通式[17]和[18]中,优选R15和R9分别表示含取代基的基团。当由通式[17]或[18]表示的化合物具有这一结构时,此化合物对氧化和还原的稳定性得到改进,并可延长器件的寿命。
当荧蒽骨架结构以两个氨基基团、两个链烯基团或一个氨基基团与一个链烯基团的组合取代时,具有这种荧蒽骨架结构的化合物有异构体。
在荧蒽骨架结构为7,14-二苯基二氢苊并[1,2-k]荧蒽的情况下,对异构体的例子进行了描述。
二溴取代二氢苊并[1,2-k]荧蒽有两个异构体,即3,10-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽(异构体A)和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽(异构体B)。
由作为中间体的异构体A和异构体B得到的终产品包含由异构体A衍生的氨基取代化合物和由异构体B衍生的氨基取代化合物。当制备终产品时,包含在终产品中的异构体A和异构体B的相对量因制备方法而不相同。(1)二溴取代化合物可从溶解二溴取代物的反应混合物溶液部分中得到。(2)二溴取代化合物也可从沉淀物中得到,沉淀物通过从溶液中再结晶形成,此溶液通过溶解从反应混合物溶液部分中得到的上述产品而得到。(3)二溴取代化合物也可从上述再结晶后剩下的溶液中得到。通过恰当地选择工艺和用于处理的溶剂类型,可得到含不同量的异构体A和异构体B、具体地异构体A与异构体B的摩尔比在10∶90至90∶10之间的目标化合物。
优选异构体的摩尔比误差为:(i)异构体A∶异构体B=x±10∶y±10(x+y=100)和更优选(ii)异构体A∶异构体B=x±5∶y±5(x+y=100)。在下文中,当满足关系式(i)时,异构体的比例将按约为常数进行描述和当满足关系式(ii)时,异构体的比例将按约为常数进行描述。
当本发明的上述化合物有异构体时,在有机层中可包括许多异构体。优选在异构体的比例保持在约为常数或常数的条件下制备器件。通过以此方式制备的器件,由器件发出的光谱可保持相同。换言之,发出光的颜色可保持相同。另外,通过改变异构体的比例可改变发光的颜色。当然,有机层可仅包括单个化合物,而不包括任何其它异构体。
当一个化合物包含上述的异构体时,一个异构体可比其它异构体发出更长波长的光。因此,当可发较长波长光的异构体与可发较短波长光的异构体的摩尔比优选在90∶10至60∶40的范围内和更优选在99∶1至70∶30的范围内时,可发较长波长的光如红光。
利用异构体之间1H-NMR化学位移的差别,可从每一异构体的峰面积比计算出异构体的比例。
优选有机层至少为空穴传递层和发光层中的一层。
无机化合物层可沉积在有机层和电极之间。
本发明的有机EL器件发红光。
由本发明中通式[1]至[18]表示的化合物例子包括下面表示的(A-1)至(A-18)和(B-1)至(B-17)。但是,本发明不局限于作为例子的这些化合物。在下面表示的通式中,Me意指甲基和Et意指乙基。
(φ是苯基)
由于用于本发明有机EL器件中的化合物具有以氨基基团或链烯基基团取代的荧蒽骨架结构,此化合物呈现高荧蒽收率并发红或黄光。因此,使用此化合物的有机EL器件发红至黄光,呈现高发光效率和长寿命。
本发明的有机EL器件中一层或多层有机薄膜沉积在阳极与阴极之间。当器件为单个有机层时,发光层沉积在阳极与阴极之间。发光层包含发光材料,也可包含将在阳极注入的空穴传递至发光材料的空穴注入材料或将在阴极注入的电子传递至发光材料的电子注入材料。优选发光层由具有高荧光发射量子效率和优异传递空穴和电子能力的发光材料形成,并形成均匀薄膜。含多层结构的有机EL器件具有层压结构如:(阳极/空穴注入层/发光层/阴极)、(阳极/发光层/电子注入层/阴极)和(阳极/空穴注入层/发光层/电子注入层/阴极)。
在发光层中,除了使用本发明中由通式[1]至通式[18]中任一通式表示的化合物外,如有必要,可使用传统发光材料、掺杂材料、空穴注入材料和电子注入材料。优选以1-70wt%的浓度和更优选以1-20wt%的浓度将这些化合物加入发光层、电子注入层、空穴传递层或空穴注入层的任一层中。特别地,本发明的化合物优选用作掺杂材料。
有机EL的多层结构可防止发光度受损和由猝火导致的寿命降低。如有必要,可将发光材料、其它掺杂材料、空穴注入材料和电子注入材料结合使用。通过使用其它掺杂材料,发光度和发光效率可得到改进,并可发射红光和白光。空穴注入层、发光层和电子注入层均可分别包括具有两或多层的多层结构。当空穴注入层为多层结构时,空穴从电极注入的层称之为空穴注入层和从空穴注入层接受空穴并将空穴从空穴注入层传递至发光层的层称之为空穴传递层。当电子注入层为多层结构时,电子从电极注入的层称之为电子注入层和从电子注入层接受电子并将电子从电子注入层传递至发光层的层称之为电子传递层。根据多种因素如能级、耐热性和与有机层或金属电极材料的粘合力对这些层进行选择和使用。
可在有机层中用作发光材料的材料或与由通式[1]至[18]表示的化合物相结合的主体材料的例子包括蒽、萘、菲、芘、并四苯、蔻、屈(chrysene)、荧光素、苝、酞苝、萘苝、苝酮、酞苝酮、萘苝酮、二苯基丁二烯、四苯基丁二烯、香豆素(coumarine)、噁二唑、醛连氮、二苯并噁唑啉、二苯乙烯基、吡嗪、环戊二烯、喹啉的金属配合物、氨基喹啉的金属配合物、苯并喹啉的金属配合物、亚胺、二苯基乙烯、乙烯基蒽、二氨基咔唑、吡喃、硫代吡喃、多次甲基、部花青、喔星类(oxinoid)化合物与咪唑的螯合物、喹哪啶酮(quinacridone)、红荧烯、1,2-二苯乙烯衍生物和荧光颜料。但是,上面的材料不局限于作为例子的上述化合物。
作为空穴注入材料,优选化合物具有传递空穴的能力,呈现从阳极注入空穴的优异效率和空穴注入发光层或发光材料的优异效率,防止在发光层形成的激发组分传递进入电子注入层或电子注入材料中,并具有形成薄膜的优异能力。上面化合物的例子包括酞菁衍生物、萘菁衍生物、卟啉衍生物、噁唑、噁二唑、三唑、咪唑、咪唑啉酮、咪唑硫酮、吡唑啉、吡唑啉酮、四氢咪唑、噁唑、噁二唑、腙、酰腙、多芳香基烷、1,2-二苯乙烯、丁二烯、联苯胺型三苯基胺、苯乙烯胺型三苯基胺、二胺型三苯基胺、这些化合物的衍生物和大分子化合物如聚乙烯咔唑、聚硅烷和导电大分子。但是,上面的材料不局限于作为例子的上述化合物。
在用于本发明有机EL器件的空穴注入材料中,芳香叔胺衍生物和酞菁衍生物更为有效。
芳香叔胺衍生物的例子包括三苯胺、三甲苯胺、甲苯基二苯胺、N,N’-二苯基-N,N’-(3-甲基苯基)-1,1’-联苯-4,4’-二胺、N,N,N’,N’-(4-甲基苯基)-1,1’-苯基-4,4’-二胺、N,N,N’,N’-(4-甲基苯基)-1,1’-联苯-4,4’-二胺、N,N’-二苯基-N,N’-二萘基-1,1’-联苯-4,4’-二胺、N,N’-(甲基苯基)-N,N’-(4-正丁基苯基)菲-9,10-二胺、N,N-双(4-二-4-甲苯基氨基苯基)-4-苯基环己烷和含这些芳香叔胺骨架结构的低聚物以及聚合物。但是,芳香叔胺衍生物不局限于作为例子的上述化合物。
酞菁(Pc)衍生物的例子包括H2Pc、CuPc、CoPc、NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、ClGaPc、ClInPc、ClSnPc、C12SiPc、(HO)AlPc、(HO)GaPc、VOPc、TiOPc、MoOPc、GaPc-O-GaPc和萘菁的对应衍生物。但是,酞菁和萘菁的衍生物不局限于作为例子的上述化合物。
作为电子注入材料,优选化合物具有传递电子的能力,呈现从阴极注入电子的优异效率和电子注入发光层或发光材料的优异效率,防止在发光层形成的激发组分传递进入空穴注入层或空穴注入材料中,并具有形成薄膜的优异能力。上面化合物的例子包括芴酮、蒽醌二甲烷、二苯酚合苯醌、二氧化硫代吡喃、噁唑、噁二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽醌二甲烷、蒽酮和这些化合物的衍生物。但是,上面的化合物不局限于作为例子的上述化合物。通过将受电子材料加入至空穴注入材料中或通过将给电子材料加入至电子注入材料中来改进电荷注入性质。
在本发明的有机EL器件中,更有效的电子注入材料为金属配合物和含氮的五元环衍生物。
金属配合物的例子包括8-羟基喹啉锂、二(8-羟基喹啉)锌、二(8-羟基喹啉)铜、二(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、二(10-羟基苯并[h]喹啉)铍、二(10-羟基苯并[h]喹啉)锌、二(2-甲基-8-羟基喹啉)氯镓、二(2-甲基-8-羟基喹啉)(邻甲酚)镓、二(2-甲基-8-羟基喹啉)(1-萘酚)铝和二(2-甲基-8-羟基喹啉)(2-萘酚)镓。但是,金属配合物不局限于作为例子的上述化合物。
含氮的五元环衍生物的优选例子包括噁唑、噻唑、噻二唑和三唑的衍生物。特定例子包括2,5-二(1-苯基)-1,3,4-噁唑、二甲基POPOP、2,5-二(1-苯基)-1,3,4-噻唑、2,5-二(1-苯基)-1,3,4-噁二唑、2-(4’-叔丁基苯基)-5-(4”-联苯基)-1,3,4-噁二唑、2,5-二(1-萘基)-1,3,4-噁二唑、1,4-二[2-(5-苯基噁二唑基)]苯、1,4-二[2-(5-苯基噁二唑基)-4-叔丁基苯]、2-(4’-叔丁基苯基)-5-(4”-联苯基)-1,3,4-噻二唑、2,5-二(1-萘基)-1,3,4-噻二唑、1,4-二[2-(5-苯基噻二唑基)]苯、2-(4’-叔丁基苯基)-5-(4”-联苯基)-1,3,4-三唑、2,5-二(1-萘基)-1,3,4-三唑和1,4-二[2-(5-苯基三唑基)]苯。但是,含氮的五元环衍生物不局限于作为例子的上述化合物。
在本发明的有机EL器件中,除了由通式[1]至[18]表示的化合物外,有机层还可在相同层中包含发光材料、掺杂材料、空穴注入材料和电子注入材料中至少一种材料。为了改进本发明的有机EL器件在温度、湿度和氧气方面的稳定性,可在器件表面形成保护层或整个器件以硅油或树脂进行保护。
作为用于有机EL器件阳极的导电材料,该材料的功函大于或等于4eV是合适的。这样的材料的例子包括碳、铝、钒、铁、钴、镍、钨、银、金、铂、钯、这些金属的合金、用于ITO底物和NESA底物的金属氧化物如氧化锡和氧化铟以及有机导电树脂如聚噻吩和聚吡咯。作为用于有机EL器件阴极的导电材料,该材料的功函小于4eV是合适的。这样的材料的例子包括镁、钙、锡、铅、钛、钇、锂、钌、锰、铝和这些金属的合金。但是,用于阳极和阴极的材料不局限于作为例子的上述材料。合金的典型例子包括镁银的合金、镁铟合金和锂铝合金。但是,合金不局限于作为例子的上述这些合金。合金的组成由气相淀积源的温度、气氛和真空度控制,并可进行适当的调节。如有必要,阳极和阴极可以为含两或多层的多层结构。
在本发明的有机EL器件中,优选将硫属元素化物、金属卤化物或金属氧化物层(此层有时可称之为表面层)沉积在如上所述制备的一对电极中至少一个电极的表面上。具体地,优选金属如硅和铝的硫属元素化物(包括氧化物)层沉积在发光介质层一侧的阳极表面上或金属卤化物或金属氧化物层沉积在发光介质层一侧的阴极表面上。由于上述层的原因,驱动稳定性可得到改进。
硫属元素化物的优选例子包括SiOx(1≤x≤2)、AlOx(1≤x≤1.5)、SiON和SiAlON。金属卤化物的优选例子包括LiF、MgF2、CaF2和稀土金属氟化物。金属氧化物的优选例子包括Cs2O、Li2O、MgO、SrO、BaO和CaO。
在本发明的有机EL器件中,优选电子传递化合物和还原掺杂剂的混合区域或空穴传递化合物和氧化掺杂剂的混合区域沉积在如上所述制备的一对电极中至少一个电极的表面上。由于沉积在电极对表面上混合区域的存在,电子传递化合物被还原而形成阴离子,便于电子的注入和从混合区域至发光介质的传递。空穴传递化合物被氧化而形成阳离子,便于空穴的注入和从混合区域至发光介质的传递。氧化剂掺杂剂的优选例子包括不同类型的路易斯酸和受体化合物。还原掺杂剂的优选例子包括碱金属、碱金属化合物、碱土金属、稀土金属和这些金属的化合物。
在有机EL器件中,为了得到高效发光性,优选至少器件的一面在发光波长区基本透明。优选底物也是透明的。根据气相淀积或喷镀方法,使用上面的导电材料,沉积透明电极以确保得到所规定的透明度。优选沉积在发光面上电极的透光系数大于或等于10%。只要底物有足够的机械强度和高温强度,并且为透明的,那么对底物没有特别的限制。可使用玻璃底物或透明树脂膜。透明树脂膜的例子包括聚乙烯、乙烯-乙烯基醋酸酯共聚物、乙烯-乙烯醇共聚物、聚丙烯、聚苯乙烯、聚甲基丙烯酸甲酯、聚氯乙烯、聚乙烯醇、聚乙烯缩丁醛、尼龙、聚醚醚酮、聚砜、聚醚砜、四氟乙烯-全氟烷基乙烯基醚共聚物、聚氟乙烯、四氟乙烯-乙烯共聚物、四氟乙烯-六氟丙烯共聚物、聚氯三氟乙烯、聚偏氟乙烯、聚酯、聚碳酸酯、聚氨酯、聚醚酰亚胺、聚酰亚胺和聚丙烯膜。
按照干成膜法如真空气相淀积、喷镀、等离子体电镀和离子电镀或湿成膜法如旋涂、浸渍和流涂可适当地形成有机EL器件的每一层。对膜厚度没有特别的限制,但是将厚度固定在适当值是必要的。当厚度大于适当值时,必须使用高电压以得到所规定的发光量,而效率降低。当厚度小于适当值时,会形成针孔,甚至在施用电场时也不能得到足够的发光度。一般而言,合适的厚度在5纳米至10微米之间,优选在10纳米至0.2微米之间。
当根据湿法生产器件时,将形成每一层的材料溶解或分散在合适的溶剂如乙醇、氯仿、四氢呋喃和二噁烷中,从溶液或悬浮液中形成膜。对溶剂没有特别的限制。在任何有机薄层中,可将合适的树脂和添加剂用于改进成膜性质并防止形成针孔。可用树脂的例子包括绝缘树脂如聚苯乙烯、聚碳酸酯、聚丙烯酸酯、聚酯、聚酰胺、聚氨酯、聚砜、聚甲基丙烯酸甲酯、聚丙烯酸甲酯和纤维素、由这些树脂衍生的共聚物、光导树脂如聚-N-乙烯基咔唑和聚硅烷以及导电树脂如聚噻吩和聚吡咯。添加剂的例子包括抗氧剂、紫外光吸收剂和增塑剂剂。
如上所述,当将本发明的化合物用于有机EL器件的有机层时,可得到呈现很纯颜色和高发光效率、长寿命和发红光的有机EL器件。
本发明的有机EL器件可用于平面发光构件如壁挂电视的平板显示器、复印机、打印机和液晶显示器的背景光、仪器的光源、显示面板和标记光。
通过下列的合成实施例和实施例,对本发明进行更为具体的描述:
合成实施例1(化合物A-1)
3,10-和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽通过如下所示的反应路径进行合成。
*(1)→(7)
cf.Jeff D.Debad,Allen J,Bard美国化学会志,第120卷,2476(1998)。
(A)3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽的合成
按照J.B.Allen的方法,利用二氢苊酮(1)作为原材料通过7,14-二苯基二氢苊并[1,2-k]荧蒽(6)合成3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽。3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽的结构通过FD-MS(场脱附质谱)和1H-NMR谱进行鉴定。其1H-NMR谱的化学位移与Allen的测定值一致(J.D.Debad,A.I.Bard,美国化学会志(J.Chem.Soc.),第120卷,2476页(1998))。
(B)3,10-和3,11-二苯氨基-7,14-二苯基二氢苊并荧蒽(化合物A-1)的合成
将3.56克(5.6mmole)3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽(7)、1.89克(11.2mmole)二苯胺、0.06克(0.3mmole)醋酸钯、0.22克(1.1mmole)三叔丁基膦和1.51克(14.0mmole)叔丁醇钠在室温下溶于150毫升甲苯中,在混合物加热回流的同时,使反应进行6小时。过滤所得的反应混合物,浓缩滤液,得到4.8克橙红色粉状固体。将固体溶于甲苯中后,使用硅胶充装柱的柱色谱对溶液进行分离,得到4.1克固体主组分。通过FD-MS(812)和化合物(7)的结构确认主组分为3,10-和3,11-二苯氨基-7,14-二苯基二氢苊并荧蒽(化合物A-1)。通过过滤分离的反应混合物中的沉淀物以丙酮和水进行洗涤并干燥,得到0.6克粉状固体。所得到的固体通过FD-MS(812)和1H-NMR谱确认与由滤液中得到产品的结构相同。
同样地,作为3,10-和3,11-二氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽化合物的化合物A-16(合成实施例2)、化合物B-15(合成实施例3)、化合物A-8(合成实施例4)、化合物B-18(合成实施例5)和化合物B-17(合成实施例6)按如下所示的反应路径进行合成:
合成实施例2(化合物A-16)
除了以2.31克(11.7mmole)p,p’-二甲苯胺代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。反应完成后,对反应混合物进行过滤。滤液以水洗涤,并浓缩得到红色粉状固体。使用硅胶充装柱的柱色谱对所得固体进行分离,得到2.9克高纯度主组分,主组分通过FD-MS(868)确认是化合物A-16。
合成实施例3(化合物B-15)
除了以2.27克(11.7mmole)亚氨基1,2-二苯乙烯代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。反应完成后,对沉淀在反应混合物的产品进行分离,以丙酮和水进行反复洗涤,并干燥得到3.4克橙红色粉状固体。将所得固体溶于四氢呋喃中,使用硅胶薄层的薄层色谱对其进行分离,得到2.3克高纯度主组分,主组分通过FD-MS(862)确认是化合物B-15。
合成实施例4(化合物A-8)
除了以1.0克(11.7mmole)哌啶代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。反应完成后,对反应混合物进行过滤。滤液以水洗涤,并浓缩得到红色粉状固体。将所得固体溶于甲苯中,使用硅胶充装柱的柱色谱对其进行分离,得到2.1克高纯度主组分,主组分通过FD-MS(644)确认是化合物A-8。
合成实施例5(化合物B-18)
除了以1.96克(11.7mmole)咔唑代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。反应完成后,对沉淀在反应混合物中的产品进行分离,以丙酮和水进行反复洗涤,并干燥得到3.8克橙红色粉状固体。将所得固体溶于四氢呋喃中,使用硅胶薄层的薄层色谱对其进行分离,得到2.0克高纯主组分,主组分通过FD-MS(808)确认是化合物B-18。
合成实施例6(化合物B-17)
除了以2.33克(11.7mmole)吩噻嗪代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。反应完成后,对反应混合物进行过滤。滤液以水洗涤,浓缩和并干燥得到4.2克棕色粉状固体。将所得固体溶于甲苯中,使用硅胶薄层的薄层色谱对其进行分离,得到2.6克高纯主组分,主组分通过FD-MS(872)确认是化合物B-17。
合成实施例7(化合物A-4)
化合物A-4通过如下所示的反应路径进行合成。
在合成化合物(8)的过程中,利用薄层色谱检测反应混合物,使反应继续到化合物(6)的色谱斑消失。反应完成后,反应混合物以0.1N氢氧化钠水溶液进行洗涤,浓缩,并通过硅胶充填柱的柱色谱进行分离,得到化合物(8)。
除了以3.12克(5.6mmole)化合物(8)代替化合物(7)和以0.51克(11.5mmole)哌啶代替二苯胺外,按照与合成实施例1(B)中相同的步骤进行反应。将反应所得的固体溶于甲苯中,使用硅胶充填柱的柱色谱对其进行分离,得到2.2克高纯化合物(9)。
将5.61克(10.0mmole)高纯化合物(9)溶于30ml二甲基甲酰胺中,将1.68克(11.0mmole)氧氯化磷加入所得溶液中,将混合物加热回流。反应完成后,过滤反应混合物,使用硅胶充装柱的柱色谱对其进行分离,得到4.0克高纯主组分,主组分通过FD-MS(589)确认是化合物(10)。
将4.7g(8.0mmole)化合物(10)与0.7g(10.6mmole)丙二腈进行反应。将沉淀在反应混合物中的反应产品进行分离,并溶于四氢呋喃中。使用硅胶薄层的薄层色谱对所得溶液进行分离,得到3.6克高纯橙红色晶体,该晶体通过FD-MS(637)确认是化合物A-4。
合成实施例8(化合物A-14)
化合物A-14通过如下所示的反应路径进行合成(S.H.Tucker,化学会志(J.Chem.Soc.),1462(1958)):
·(1)→(14)cf.S.H.Tucker化学会志:1462(1958)
合成实施例9(化合物A-6)
化合物A-6通过如下所示的反应路径进行合成:
合成实施例10(化合物B-5)
化合物B-5通过如下所示的反应路径进行合成(Beil.5(3)2278):
(16):cf.Beil.5(3)2278
合成实施例11(化合物A-12)
化合物A-12通过如下所示的反应路径进行合成:
合成实施例12
含3,10-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在20∶80至30∶70之间的组合物通过如下所示的反应路径进行合成:
(A)含3,10-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比为22∶78的组合物(18)的合成
将在合成实施例1(A)中所得反应混合物的溶液部分浓缩,溶解在四氢呋喃中,并再结晶,除去形成的沉淀物。浓缩溶液部分,得到二溴化合物。通过1H-NMR谱确认二溴化合物为含3,10-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比为22∶78的组合物。
(B)含3,10-和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在20∶80至30∶70之间的组合物的合成
将5.00克(7.9mmole)含3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比为22∶78的组合物(18)、2.78克(16.5mmole)二苯胺、0.09克(0.09mmole)醋酸钯、0.44克(2.2mmole)三叔丁基膦和2.12克(19.6mmole)叔丁醇钠溶于100毫升甲苯中,在混合物加热回流的同时,使反应进行6小时。反应完成后,过滤反应混合物,浓缩滤液,使用硅胶充装柱的柱色谱对其进行分离,得到6.20克橙红色粉状固体。通过FD-MS(812)和1H-NMR谱(H:400MHZ;测量溶剂:DMSO(120℃);见图1)确认此固体为含3,10-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、摩尔比在20∶80至30∶70之间的组合物。
合成实施例13
5,12-和/或5,13-双二苯基氨基-9,16-二苯基荧蒽并[8,9-a]醋蒽烯通过如下所示的反应路径进行合成:
(A)9,16-二苯基荧蒽并[8,9-a]醋蒽烯(19)的合成
按照Bandyopadhyai’s的方法,利用醋蒽烯醌作为原材料通过1,3-二苯基环戊并[a]醋蒽烯-2-酮与苊反应合成9,16-二苯基荧蒽并[8,9-a]醋蒽烯[印度化学杂志(Indian J.Chem.),第21B卷,91页(1982)]。
(B)5,12-和/或5,13-二溴-9,16-二苯基荧蒽并[8,9-a]醋蒽烯(20)的合成
将4.00克(7.6mmole)9,16-二苯基荧蒽并[8,9-a]醋蒽烯(19)溶于240毫升二氯甲烷中。在所得混合物加热回流的同时,逐滴加入18.0ml1M溴的二氯甲烷溶液,使反应进行2小时。将所得反应混合物以氢氧化钠水溶液和纯水进行洗涤并浓缩,得到5.06克黄棕色粉状固体。通过FD-MS(686)和1H-NMR谱确认此固体为5,12-二溴-9,16-二苯基荧蒽并[8,9-a]醋蒽烯和/或5,13-二溴-9,16-二苯基荧蒽并[8,9-a]醋蒽烯。
(C)5,12-和/或5,13-双二苯氨基-9,16-二苯基荧蒽并[8,9-a]醋蒽烯的合成
将5.00克(7.4mmole)5,12-和/或5,13-二溴-9,16-二苯基荧蒽并[8,9-a]醋蒽烯(20)、2.75克(16.2mmole)二苯胺、0.09克(o.4mmole)醋酸钯、0.43克(2.2mmole)三叔丁基膦和2.05克(20.6mmole)叔丁醇钠溶于200毫升甲苯中。在混合物加热回流的同时,使反应进行5小时。反应完成后,过滤反应混合物,浓缩滤液并使用含硅胶充装柱的柱色谱对其进行分离,得到4.27克黑紫色粉状固体主要组分。通过FD-MS(862)和1H-NMR谱(H:400MHZ;测量溶剂:DMSO(120℃);见图2)确认此主要组分为5,12-和/或5,13-双二苯胺基-9,16-二苯基荧蒽并[8,9-a]醋蒽烯。
合成实施例14
3,11-和/或3,12-双二苯胺基-7,16-二苯基荧蒽并[8,9-k]荧蒽通过如下所示的反应路径进行合成:
(A)2,5-二苯基荧蒽并[11’,12’-3,4]呋喃(21)的合成
按照N.Campbell’s的方法[化学杂志(J.Chem.Soc.),1555页(1949)],通过7,8-二甲基二氢苊-7,8-二醇与反-1,2-二苯甲酰乙烯反应合成2,5-二苯基荧蒽并[11’,12’-3,4]呋喃(21),7,8-二甲基二氢苊-7,8-二醇按照S.H.Tucker’s方法[化学杂志(J.Chem.Soc.),1462页(1958)]合成。
(B)7,16-二苯基荧蒽并[8,9-k]荧蒽(22)的合成
将5.00克(12.7mmole)2,5-二苯基荧蒽并[11’,12’-3,4]呋喃(21)和3.86g(19.0mmole)苊加入含500毫升二甲苯和660毫升二氯甲烷混合溶剂中。混合物在加热下回流3小时。冷却溶液,并将16.0ml1M三溴化硼的二氯甲烷溶液逐滴加入冷却溶液中。将所得溶液在60℃加热4小时。将所得反应混合物以碳酸氢钠水溶液和纯水进行洗涤、浓缩并使用硅胶充填柱的柱色谱对其进行纯化,得到3.20克黄色晶体。通过FD-MS(528)和1H-NMR谱确认此晶体为7,16-二苯基荧蒽并[8,9-k]荧蒽(22)。
(C)3,11-和/或3,12-二溴-7,16-二苯基荧蒽并[8,9-k]荧蒽(23)的合成
将2.30克(4.3mmole)7,16-二苯基荧蒽并[8,9-k]荧蒽(22)溶于230毫升二氯甲烷中。在所得溶液加热回流的同时,逐滴加入9.0ml1M溴的二氯甲烷溶液,然后使反应进行2小时。将所得反应混合物以氢氧化钠水溶液和纯水进行洗涤并浓缩,得到3.06克淡黄棕色晶体。通过FD-MS(686)和1H-NMR谱确认此晶体为3,11-和/或3,12-二溴-7,16-二苯基荧蒽并[8,9-k]荧蒽(23)。
(D)3,11-和/或3,12-双二苯氨基-7,16-二苯基荧蒽并[8,9-k]荧蒽的合成
将3.92克(5.7mmole)3,11-和/或3,12-二溴-7,16-二苯基荧蒽并[8,9-k]荧蒽(23)、2.03克(12.0mmole)二苯胺、0.07克(0.07mmole)醋酸钯、0.33克(1.7mmole)三叔丁基膦和1.56克(14.4mmole)叔丁醇钠溶于120毫升甲苯中。在混合物加热回流的同时,使反应进行6小时。反应完成后,过滤反应混合物。使用硅胶充装柱的柱色谱对滤液进行纯化,得到4.27克橙色粉状晶体。通过FD-MS(862)和1H-NMR谱(H:400MHZ;测量溶剂:DMSO(120℃);见图3)确认此晶体为3,11-和/或3,12-双二苯胺基-7,16-二苯基荧蒽并[8,9-k]荧蒽。
合成实施例15
合成含3,10-双二甲苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-双二甲苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物。
(A)含3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽的组合物(18)的合成
将在合成实施例1(A)中所得反应混合物的溶液部分浓缩,全部溶解在四氢呋喃中,并再结晶,除去形成的沉淀物。浓缩溶液部分,得到二溴化合物。通过1H-NMR谱确认二溴化合物为含3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物。
(B)含3,10-和3,11-双二甲苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物的合成
除了以二-p,p-甲苯胺代替二苯胺外,按照与合成实施例12(B)中相同的步骤合成含3,10-和3,11-双二甲苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物(A-16)。
合成实施倒16
合成含3,10-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物。
(A)含3,10-和3,11-二溴-7,14-二苯基二氢苊并[1,2-k]荧蒽的组合物(18)的合成
按照与合成实施例15(A)中相同的步骤合成含二溴化合物的组合物。
(B)含3,10-和3,11-双二甲苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物的合成
使用在上面(A)得到的组合物,按照与合成实施例12(B)中相同的步骤合成含3,10-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽和3,11-双二苯氨基-7,14-二苯基二氢苊并[1,2-k]荧蒽、其摩尔比在80∶20至90∶10之间的组合物。
实施例1
将作为空穴注入材料的下列化合物(H232)气相淀积在含ITO电极的干净玻璃板上以便形成厚度为60nm的膜。
然后,气相淀积作为空穴传递材料的下列化合物(NPD)以便形成厚度为20nm的膜。
随后,气相淀积作为发光层材料的8-羟基喹啉的铝配合物(Alq)和3,10-和3,11-二苯氨基-7,14-二苯基二氢苊并荧蒽(化合物A-1)以便形成含2.1mol%化合物A-1和厚度为50nm的膜。Alq的结构表示如下:
电子注入层单独通过Alq的气相淀积形成以便形成的膜厚度为10nm。通过LiF的气相淀积在电子注入层上形成无机化合物层以便形成的膜厚度为0.2nm。将铝气相淀积在这样形成的层上以便形成厚度为170nm的电极并得到有机EL器件。当底物保持在室温下时,形成上述层的气相淀积在10-6乇下进行。
该器件的发光性质如下:在直流5.5V电压下的发光度为103cd/m2和发光效率高达6.2cd/A。发出的光为橙色光,色度坐标为(0.56,0.44)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期长达2600小时。
此实施例表明呈现高性能的有机EL器件可通过使用化合物A-1作为掺杂材料得到。据发现所得此器件发出光的光谱与掺杂材料的荧光光谱相同。因此,这表明掺杂材料起到了发光中心的功能。
对比实施例1
除了以红荧烯代替化合物A-1进行气相淀积以便形成含4.0mol%红荧烯的膜外,按照与实施例1中相同的步骤得到有机EL器件。
此器件的发光性质如下:在直流5.5V电压下的发光度为105cd/m2和发光效率为7.6cd/A。但是发出的光为黄光,色度坐标为(0.50,0.50)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期为1000小时,比实施例1中器件的短。
对比实施例2
除了以在日本专利申请公开号Heisei 11(1999)-40360中描述的荧蒽并[8,9-k]荧蒽代替化合物A-1进行气相淀积以便形成含2mol%此种荧蒽的膜外,按照与实施例1中相同的步骤得到有机EL器件。
此器件的发光性质如下:在直流5.5V电压下的发光度为35cd/m2和发光效率为3.0cd/A。发出的光为黄绿色光。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期短至300小时。
对比实施例3
除了以在日本专利申请公开号Heisei 11(1999)-168445中描述的7,14-二苯基二氢苊并[1,2-k]荧蒽代替化合物A-1进行气相淀积以便形成含2mol%此种荧蒽的膜外,按照与实施例1中相同的步骤得到有机EL器件。
此器件的发光性质如下:在直流6V电压下的发光度为69cd/m2和发光效率为1.3cd/A。发出的光为黄绿色光。其效率比Alq单独用作发光材料的器件的效率小。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期短至400小时。所得此器件发出光的光谱与掺杂材料的荧光光谱不一致。因此,据发现上述化合物不发光,黄绿色光由Alq发出,掺杂材料不能起到发光材料的功能。
实施例2至11
除了以表1中表示的化合物代替化合物A-1进行气相淀积外,按照与实施例1中相同的步骤得到有机EL器件。
按照用于实施例1中相同的方法得到这些器件的发光性质。施用的电压、发光度、发光效率、发出光的颜色和当器件在稳定电流驱动下初始发光度为500cd/m2时的半衰期列于表1中。
实施例12
除了将在合成实施例12中得到的含规定相对量异构体的组合物(化合物A-1)以100%浓度用于发光层且不使用Alq外,在按照与实施例1中相同的步骤得到有机EL器件。
该器件的发光性质如下:在直流4.5V电压下的发光度为80cd/m2和发光效率为3.5cd/A。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期长达2100小时。此器件的寿命比实施例1中器件的更长,也可用作主要发光材料。
实施例13
除了将在合成实施例15中得到的含规定相对量异构体的组合物(化合物A-16)代替化合物A-1用于发光层外,在按照与实施例1中相同的步骤得到有机EL器件。
该器件的发光性质如下:在直流5.5V电压下的发光度为94cd/m2和发光效率为5.94cd/A。发出的光为红橙色光,色度坐标为(0.60,0.39)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期长达3200小时。
实施例14
除了将在合成实施例16中得到的含规定相对量异构体的组合物(化合物A-1)代替化合物A-1用于发光层外,在按照与实施例1中相同的步骤得到有机EL器件。
该器件的发光性质如下:在直流6V电压下的发光度为100cd/m2和发光效率为4.75cd/A。发出光的色度坐标为(0.58,0.42)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半衰期长达1800小时。通过使用上述化合物,发出光比实施例1中发出光有更多的红色。这是由于此组合物包含更多量能发出较长波长光的异构体3,11-双二苯氨基-7,14-二苯基二氢苊并[12-k]荧蒽。
表1
化合物 | 电压(V) | 发光度(cd/m2) | 发光效率(cd/A) | 发出光的颜色 | 半衰期(小时) | |
实施例2实施例3实施例4实施例5实施例6实施例7实施例8实施例9实施例10实施例11 | A-2A-8A-14A-16B-3B-15B-17B-18A-4B-5 | 5.55.85.26.06.05.55.86.17.26.0 | 140120120170160130110120110120 | 5.73.66.14.73.22.82.02.83.76.7 | 红橙色橙色红色红橙色红橙色橙色红橙色红橙色红色黄绿色 | 2800210027003100190018001700200010001800 |
工业应用
如上的详细描述,本发明的有机电致发光器件利用由通式[1]至[18]表示的化合物,发黄至红光,呈现很纯的颜色和高发光效率以及长寿命。
因此,本发明的有机电致发光器件用作光源如电视的平面发光构件和显示器的背景光是有利的。
Claims (11)
1.一种有机电致发光器件,它包括沉积在至少一对电极之间的有机层,其中有机层包含具有包含至少5个稠合环的荧蒽骨架结构的化合物,荧蒽骨架结构至少被一个氨基取代,其中所说的化合物选自由通式[2]至[18]表示的化合物:
其中,X1至X20各自独立地表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氨基、含1至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的烷氨基、含7至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳烷基氨基或含8至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的链烯基;由X1至X20表示的一对相邻基团和由X1至X20表示的基团的相邻一对取代基可结合形成环状结构;当一对相邻取代基为芳香基时,此对取代基可以为单个基团;和至少一个由X1至Xi表示的取代基包括氨基,i表示12至20的数;
其中,R1至R4各自独立表示含1至20个碳原子的烷基或含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基;在由R1和R2表示的一对基团和由R3和R4表示的一对基团中的之一或这两者中,形成一对的基团可通过-O-或-S-键合;R5至R16表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氨基、含1至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的烷氨基、含7至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳烷基氨基或含8至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的链烯基;由R5至R16表示的一对相邻基团和由R5至R16表示的基团的相邻一对取代基可结合形成环状结构;和至少一个由R5至R16表示的取代基包括氨基。
2.权利要求1的有机电致发光器件,其中有机层为空穴传递层和发光层中的至少一层。
3.权利要求1的有机电致发光器件,其中有机层包括1wt%至70wt%的所说化合物。
4.权利要求1的有机电致发光器件,其中在有机层和电极之间沉积有无机化合物层。
5.权利要求1的有机电致发光器件,它发红光。
6.权利要求1的有机电致发光器件,其中有机层包括所说的化合物及其异构体。
7.权利要求6的有机电致发光器件,其中在所说的化合物及其异构体中,可发较长波长光的异构体量与可发较短波长光的异构体量之摩尔比在90∶10至60∶40的范围内。
8.权利要求6的有机电致发光器件,其中在所说的化合物及其异构体中,由通式[17]表示的异构体量与由通式[18]表示的异构体量之摩尔比在90∶10至60∶40的范围内。
9.由下列通式[2]至[18]中任一通式表示的、具有被至少一个氨基取代的包含至少5个稠合环的荧蒽骨架结构的化合物:
其中,X1至X20各自独立地表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氨基、含1至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的烷氨基、含7至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳烷基氨基或含8至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的链烯基;由X1至X20表示的一对相邻基团和由X1至X20表示的基团的相邻一对取代基可结合形成环状结构;当一对相邻取代基为芳香基时,此对取代基可以为单个基团;和至少一个由X1至Xi表示的取代基包括氨基,i表示12至20的数;
其中,R1至R4各自独立地表示含1至20个碳原子的烷基或含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基;在由R1和R2表示的一对基团和由R3和R4表示的一对基团这两对基团之一或这两对基团中,形成一对的基团可通过-O-或-S-键合;R5至R16表示氢原子、含1至20个碳原子的线性、支链或环状烷基、含1至20个碳原子的线性、支链或环状烷氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氧基、含6至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳氨基、含1至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的烷氨基、含7至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的芳烷基氨基或含8至30个碳原子的未取代的或被甲基、乙基、甲氧基或乙氧基取代的链烯基;由R5至R16表示的一对相邻基团和由R5至R16表示的基团的相邻一对取代基可结合形成环状结构;和至少一个由R5至R16表示的取代基包括氨基。
11.权利要求9的化合物,由所述通式[3]或由所述通式[4]表示:
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- 2000-09-27 CN CNA2006100093853A patent/CN1827733A/zh active Pending
- 2000-09-27 WO PCT/JP2000/006658 patent/WO2001023497A1/ja active IP Right Grant
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Cited By (2)
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CN102790184A (zh) * | 2012-07-31 | 2012-11-21 | 昆山维信诺显示技术有限公司 | 一种琥珀色有机电致发光器件 |
CN102790184B (zh) * | 2012-07-31 | 2016-12-21 | 昆山维信诺显示技术有限公司 | 一种琥珀色有机电致发光器件 |
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US20040214043A1 (en) | 2004-10-28 |
CN1327468A (zh) | 2001-12-19 |
JP4601234B2 (ja) | 2010-12-22 |
WO2001023497A1 (fr) | 2001-04-05 |
DE60034105D1 (de) | 2007-05-10 |
US6815090B1 (en) | 2004-11-09 |
EP1138745A1 (en) | 2001-10-04 |
KR20010099809A (ko) | 2001-11-09 |
TW490990B (en) | 2002-06-11 |
EP1757670A3 (en) | 2007-03-21 |
ATE358169T1 (de) | 2007-04-15 |
EP1138745A4 (en) | 2005-04-20 |
EP1138745B1 (en) | 2007-03-28 |
US20080074045A1 (en) | 2008-03-27 |
US6818327B2 (en) | 2004-11-16 |
EP1757670A2 (en) | 2007-02-28 |
US20030054200A1 (en) | 2003-03-20 |
US20060024523A1 (en) | 2006-02-02 |
US20070003788A1 (en) | 2007-01-04 |
CN1827733A (zh) | 2006-09-06 |
KR100842989B1 (ko) | 2008-07-01 |
DE60034105T2 (de) | 2007-07-12 |
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