CN1327469A - 有机电致发光器件 - Google Patents
有机电致发光器件 Download PDFInfo
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- CN1327469A CN1327469A CN00802125A CN00802125A CN1327469A CN 1327469 A CN1327469 A CN 1327469A CN 00802125 A CN00802125 A CN 00802125A CN 00802125 A CN00802125 A CN 00802125A CN 1327469 A CN1327469 A CN 1327469A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 239000012044 organic layer Substances 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 64
- 238000005401 electroluminescence Methods 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 47
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000004104 aryloxy group Chemical group 0.000 abstract description 2
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 34
- PLKNNIMJRPBOSW-UHFFFAOYSA-N benzo[a]pentacene Chemical compound C1=CC=C2C3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=CC2=C1 PLKNNIMJRPBOSW-UHFFFAOYSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- -1 methylene dicyanoethyl Chemical group 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 238000007740 vapor deposition Methods 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 10
- 238000000434 field desorption mass spectrometry Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 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
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000203 mixture Substances 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
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 0 CCC(C)CC(*)c1c(*)ccc2ccccc12 Chemical compound CCC(C)CC(*)c1c(*)ccc2ccccc12 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 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
- 239000000725 suspension Substances 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
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-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
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LSOTZYUVGZKSHR-UHFFFAOYSA-N anthracene-1,4-dione Chemical class C1=CC=C2C=C3C(=O)C=CC(=O)C3=CC2=C1 LSOTZYUVGZKSHR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- RTVKHFLCWLKLJB-UHFFFAOYSA-N heptacyclo[16.12.0.03,16.05,14.06,11.020,29.022,27]triaconta-1(30),3(16),4,6,8,10,12,14,18,20,22,24,26,28-tetradecaene-2,17-dione Chemical class C1=CC=C2C=C(C=C3C(=O)C=4C(=CC5=C6C=CC=CC6=CC=C5C=4)C(=O)C3=C3)C3=CC2=C1 RTVKHFLCWLKLJB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004880 oxines Chemical class 0.000 description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 229910000838 Al alloy Inorganic materials 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
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-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
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 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
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 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
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 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
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 238000012545 processing 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
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000002904 solvent 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
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- BAQTXHFYWBUHBL-UHFFFAOYSA-N tetracene-1,4-dione Chemical class C1=CC=C2C=C(C=C3C(=O)C=CC(=O)C3=C3)C3=CC2=C1 BAQTXHFYWBUHBL-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- 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
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-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
- 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
- RLIPQCDHACHPJW-UHFFFAOYSA-N 2,3,4-trimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1C RLIPQCDHACHPJW-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
- 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
- IDAZKAXEKRLEHO-UHFFFAOYSA-N 8,15-benzo[a]pentacenequinone Chemical compound C1=CC=C2C(C=C3C(=O)C4=CC5=CC=CC=C5C=C4C(C3=C3)=O)=C3C=CC2=C1 IDAZKAXEKRLEHO-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
- XSXWEFJMVHGVKB-UHFFFAOYSA-N C(C=C1)=CC=C1C(C=C1)=CC=C1C1=CC=CC2=CC=C(C=C(C=C(C=C(C=CC=C3)C3=C3)C3=C3)C3=C3)C3=C12 Chemical compound C(C=C1)=CC=C1C(C=C1)=CC=C1C1=CC=CC2=CC=C(C=C(C=C(C=C(C=CC=C3)C3=C3)C3=C3)C3=C3)C3=C12 XSXWEFJMVHGVKB-UHFFFAOYSA-N 0.000 description 1
- 229910000882 Ca alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- YERRTOUSFSZICJ-UHFFFAOYSA-N methyl 2-amino-2-(4-bromophenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(Br)C=C1 YERRTOUSFSZICJ-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000006617 triphenylamine group Chemical class 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07C211/54—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 two or three six-membered aromatic rings
-
- 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
- C07C211/54—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 two or three six-membered aromatic rings
- C07C211/56—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 two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- 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
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
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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,其中有机层包含由通式[1]代表的化合物,其中R1至R14分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可被取代或不被取代;和在R1至R14中至少一对相互邻接的R不表示氢原子,但是表示结合形成环状结构的基团。
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。
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EL器件的结果,已发现可通过使用由下列通式[1]、[2]或[2’]表示的化合物作为发光材料达到此目标。
其中R1至R14分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可被取代或不被取代;和在R1至R14中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团。
其中R15至R26分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可被取代或不被取代;在R15至R26中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团;和Ar1和Ar2表示含6至30个碳原予的取代或不取代芳基或含5至30个碳原子的取代或不取代杂环基团。
用于本发明的有机EL器件中发红光的新型有机化合物由通式[2’]表示:
其中R15至R26和Ar1和Ar2除去Ar1和Ar2均表示苯基这一情况外,其它与上述通式[2]中的定义相同。本发明的最优选实施方案
本发明的有机EL器件中,有机层沉积在至少一对电极之间和有机层包括至少一种由上述通式[1]和通式[2]表示的化合物。
上述通式[1]中的R1至R14分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可以被取代。在R1至R14中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团。
除了R对相互邻接并表示结合形成环状结构的基团外,优选R1至R14表示烷基、芳氧基、芳烷基、芳基、芳氨基、烷氨基或含6至30个碳原子的芳香烷基氨基。
上述通式[2]中的R15至R26分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳香烷基氨基,这些基团可以被取代。在R15至R26中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团。Ar1和Ar2表示含6至30个碳原子的取代或不取代芳基或含5至30个碳原子的取代或不取代杂环基团。
用于本发明的有机EL器件中发红光的新型有机化合物由上述通式[2’]表示。
在通式[2’]中R15至R26,Ar1和Ar2除去Ar1和Ar2均表示苯基这一情况外,其它与上述通式[2]中的定义相同。
上述有机层包括含至少一种由上述通式[1]和通式[2]表示的化合物的发光层。
优选发光层包括0.1-20mol%和更优选1-5mol%的至少一种由上述通式[1]和通式[2]表示的化合物。
发光层可以是具有电子传递性质的发光层。无机化合物层可以沉积在有机层和电极之间。
本发明的有机EL器件发红光。
在本发明的有机EL器件中所用的化合物中,如上所述,在R1至R14中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团。除了并五苯结构外,优选形成不饱和环结构。由于这一结构,使用此化合物的有机EL器件呈现更优异的发光效率,并具有比传统器件更长的寿命。
在本发明的有机EL器件中,一层或多层有机薄膜沉积在阳极与阴极之间。当此器件含有单一有机层时,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,并优选形成均匀薄膜。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]、通式[2]或通式[2’]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。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,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、耐热性和与有机层的粘合力或金属电极材料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]、[2]和[2’]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、、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、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。上述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、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基胺、三甲苯基胺、甲苯基二苯基胺、N,N’-二苯基-N,N’-(3-甲基苯基)-1,1’-联苯基-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’-联苯基-4,4’-二胺、N,N’-二苯基-N,N’-二萘基-1,1’-联苯基-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-苯基环己烷和低聚物以及含这些芳香叔胺骨架结构的聚合物。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、Cl2SiPc、(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。上述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]、[2]或[2’]表示的化合物外,有机层还可在相同层中包含至少一种发光材料、掺杂材料、空穴注入材料和电子注入材料。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,但是效率降低。当厚度小于适当值时,会形成针孔,甚至当施用电场时也不能得到足够的发光度。一般而言,厚度的合适范围为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的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)
(1)1,2-二(溴甲基)萘的制备
将10克(64mmole)1,2-二甲基萘和46克(260mmole)N-溴琥珀酰亚胺悬浮在300毫升四氯化碳中。将1.7克(260mmole)2,2’-偶氮二(异丁腈)加入至所得悬浮液中并将混合物在10℃下剧烈搅拌2小时。反应完成后,过滤反应混合物,并以150毫升二氯甲烷洗涤残余物。将滤液和洗涤液混合,将混合溶液以柱色谱(硅胶/二氯甲烷)进行处理,不必进行额外的处理,得到定量的白色固体1,2-二(溴甲基)萘。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:4.74(2H,s),4.98(2H,s),7.3-8.1(6H,m)(2)1-(溴甲基)-2-(二溴甲基)萘的制备
将20克(64mmole)1,2-二(溴甲基)萘和23克(130mmole)N-溴琥珀酰亚胺悬浮在150毫升四氯化碳中。将1.1克(6.7mmole)2,2’-偶氮二(异丁腈)加入至所得的悬浮液中并将混合物在100℃下剧烈搅拌2小时。反应完成后,过滤反应混合物,并以150毫升二氯甲烷洗涤残余物。将滤液和洗涤液混合,将混合溶液以柱色谱(硅胶/二氯甲烷)进行处理,不必进行额外的处理,得到16克白色固体1-(溴甲基)-2-(二溴甲基)萘(收率为64%)。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:4.98(2H,s),7.27(1H,s),7.6-8.1(6H,m)(3)1,4-蒽醌的制备
在氩气中,将60g(550mmole)1,4-苯醌、100g(240mmole)1,2-二(二溴甲基)苯和235g(1.6mole)碘化钠溶于850ml的干燥二甲基甲酰胺中。在放热反应完成后,将反应溶液加热至70℃并搅拌8小时。反应完成后,形成的晶体通过过滤进行分离,并以甲醇和水进行洗涤,得到23克黄色针状晶体1,4-蒽醌(收率为47%)。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:7.07(2H,s),7.6-8.1(6H,m),8.66(2H,s)(4)8,15-苯并[a]并五苯醌的制备
在氢气中,将6.9g(33mmole)1,4-蒽醌、9.8g(25mmole)1-(溴甲基)-2-(二溴甲基)萘和25g(660mmole)碘化钠溶于85ml的干燥二甲基甲酰胺中。在放热反应完成后,将反应溶液加热至70℃并搅拌8小时。反应完成后,形成的晶体通过过滤进行分离,并以甲醇和水进行洗涤,得到定量的黄色针状晶体8,15-苯并[a]并五苯醌。
得到了该产品的FD-MS谱(场脱附质谱),结果如下:
FD-MS:358(M+)
(5)8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯的制备
在氩气中,将8.4g(36mmole)4-溴联苯溶于100ml的干燥甲苯和50ml的干燥四氢呋喃中,将所得溶液冷却至-5℃。将24毫升1.52mole/l正丁基锂的正己烷溶液逐滴加入冷却溶液中,并将溶液搅拌1小时。将2.2g(6.0mmole)固体形式的8,15-苯并[a]并五苯醌加入所得的反应溶液中,将反应混合物在室温下搅拌7小时。反应完成后,反应完成后,将水加入反应混合物中。将有机层以水洗涤两次,以氯化钠饱和溶液洗涤一次,并以硫酸镁进行干燥。然后,除去溶剂,得到油状产品。将油状产品以柱色谱(硅胶/己烷:二氯甲烷=2∶8至0∶10)进行处理,得到2.0克淡黄色针无定形固体8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯(收率为51%)。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:6.73(8H,dd),6.9-8.1(19H,m),8.44(2H,m),8.70(1H,m),9.23(1H,s)
(6)8,15-二(对联苯基)苯并[a]并五苯(化合物A-1)的制备
将1.5克8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯悬浮在150ml异丙醚和75ml二氯甲烷中。在回流条件下将40ml57%的碘化氢水溶液加入所得的悬浮液中,将所得的混合物搅拌5分钟。在反应完成后,将反应溶液加入500ml的饱和碳酸氢钠溶液中,将所得混合物搅拌10分钟。通过过滤分离形成的沉淀,并以去离子水洗涤一次,以饱和亚硫酸氢钠水溶液洗涤一次,再以去离子水洗涤三次。将洗涤过的沉淀在减压下加热干燥,得到0.84克淡红紫色固体8,15-二(对联苯基)苯并[a]并五苯(收率为51%)。在4×10-6乇的压力和320℃的温度下通过升华2小时对所得的产品进行纯化,得到450mg深紫色无定形固体。
得到了该产品的FD-MS谱,结果如下:
FD-MS:664(MO2 +,38),634(M++1,100)
合成实施例2(化合物A-2)
(1)8,15-二苯基-8,15-二氢-8,15-二羟基苯并[a]并五苯的制备
除了以溴苯代替4-溴联苯外,按照与合成实施例1(5)中相同的步骤,得到淡黄色无定形固体8,15-二苯基-8,15-二氢-8,15-二羟基苯并[a]并五苯。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:6.7-8.1(19H,m),8.44(2H,m),8.70(1H,m),9.23(1H,s)
(2)8,15-二苯基苯并[a]并五苯(化合物A-2)的制备
除了以8,15-二苯基-8,15-二氢-8,15-二羟基苯并[a]并五苯代替8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯外,按照与合成实施例1(6)中相同的步骤,得到深紫色无定形固体8,15-二苯基苯并[a]并五苯。
得到了该产品的FD-MS谱,经鉴定,该产品为目标化合物。
合成实施例3(化合物A-3)
(1)8,15-二(间联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯的制备
除了以3-溴联苯代替4-溴联苯外,按照与合成实施例1(5)中相同的步骤,得到淡黄色无定形固体8,15-二(间联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯。
(2)8,15-二(间联苯基)苯并[a]并五苯(化合物A-3)的制备
除了以8,15-二(间联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯代替8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯外,按照与合成实施例1(6)中相同的步骤,得到深紫色无定形固体8,15-二(间联苯基)苯并[a]并五苯。
得到了该产品的FD-MS谱,经鉴定,该产品为目标化合物。
合成实施例4(化合物A-4)
(1)8,15-二(邻联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯的制备
除了以2-溴联苯代替4-溴联苯外,按照与合成实施例1(5)中相同的步骤,得到淡黄色无定形固体8,15-二(邻联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯。
(2)8,15-二(邻联苯基)苯并[a]并五苯(化合物A-4)的制备
除了以8,15-二(邻联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯代替8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯外,按照与合成实施例1(6)中相同的步骤,得到深紫色无定形固体8,15-二(邻联苯基)苯并[a]并五苯。
得到了该产品的FD-MS谱,经鉴定,该产品为目标化合物。
合成实施例5(化合物A-13)
(1)(对溴苯基)二苯胺的制备
将50克(200mmole)三苯胺溶于500ml干燥的二甲基甲酰胺中。将通过在100ml干燥的二甲基甲酰胺中溶解36克(200mmole)N-溴琥珀酰亚胺制备的溶液加入所得的溶液中,得到的溶液在室温下搅拌6小时。在反应完成后,将1升水加入至反应混合物中,形成的沉淀通过过滤进行分离。将得到的黄色固体以水洗涤,在减压下干燥,并在己烷中再结晶,得到38克白色针状晶体形状的目标化合物(收率:59%)。
得到了该产品的1H-NMR谱,结果如下:
1H-NMR(CDCl3,TMS)δ:6.9-7.4(m)
(2)8,15-二(对二苯氨基苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯的制备
除了以(对溴苯基)二苯胺代替4-溴联苯外,按照与合成实施例1(5)中相同的步骤,得到淡黄色无定形固体8,15-二(对二苯氨基苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯。
(3)8,15-二(对二苯氨基苯基)苯并[a]并五苯(化合物A-13)的制备除了以8,15-二(对二苯氨基苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯代替8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯外,按照与合成实施例1(6)中相同的步骤,得到红紫色无定形固体8,15-二(对二苯胺基苯基)苯并[a]并五苯。
得到了该产品的FD-MS谱,经鉴定,该产品为目标化合物。
合成实施例6(化合物A-14)
(1)2,3-二(溴甲基)萘的制备
除了以2,3-二甲基萘代替1,2-二甲基萘外,按照与合成实施例1(1)中相同的步骤,得到定量的白色固体2,3-二(溴甲基)萘。
(2)2-(溴甲基)-3-(二溴甲基)萘的制备
除了以2,3-二(溴甲基)萘代替1,2-二(溴甲基)萘外,按照与合成实施例1(2)中相同的步骤,得到白色固体2-(溴甲基)-3-(二溴甲基)萘。
(3)1,4-并四苯醌的制备
除了以2,3-二(溴甲基)萘代替1,2-二(二溴甲基)苯外,按照与合成实施例1(3)中相同的步骤,得到黄色固体1,4-并四苯醌。
(4)8,17-苯并[a]并六苯醌的制备
除了以2,3-二(溴甲基)萘代替1,4-蒽醌外,按照与合成实施例1(4)中相同的步骤,得到黄色固体8,17-苯并[a]并六苯醌。
(5)8,17-二苯基-8,17-二氢-8,17-二羟基苯并[a]己酮的制备
除了以溴苯代替4-溴联苯和以8,17-苯并[a]并六苯醌代替8,15-苯并[a]并五苯醌外,按照与合成实施例1(5)中相同的步骤,得到淡黄色固体8,17-二苯基-8,17-二氢-8,17-二羟基苯并[a]己酮。
(6)8,17-二苯基苯并[a]并五苯(化合物A-14)的制备
除了以8,17-二苯基-8,17-二氢-8,17-二羟基苯并[a]己酮代替8,15-二(对联苯基)-8,15-二氢-8,15-二羟基苯并[a]并五苯外,按照与合成实施例1(6)中相同的步骤,得到黑色固体8,17-二苯基苯并[a]并五苯。
得到了该产品的FD-MS谱,经鉴定,该产品为目标化合物。实施例1
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8,15-二(对联苯基)苯并[a]并五苯(化合物A-1)以便形成含1.8mol%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7V电压下的发光度为101cd/m2和发光效率为2.64cd/A。发出的光为高纯红光,色度坐标为(0.63,0.37)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半寿命长达1200小时。对比实施例1
除了以如下所示的化合物(对比实施例1的化合物)代替化合物A-1进行气相淀积以便对比实施例1的化合物浓度为2.0mol%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11V电压下的发光度为100cd/m2和发光效率为0.3cd/A。电压比实施例1中的高4V,而发光效率却比实施例1中器件的发光效率低。虽然发出的光为高纯红光,色度坐标为(0.67,0.32),但是当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半寿命却短至270小时。对比实施例2
除了以如下所示的化合物(DCJTB)代替化合物A-1进行气相淀积以便DCJTB浓度为2.0mol%外,DCJTB为DCM的衍生物,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9V电压下的发光度为91cd/m2和发光效率为1.53cd/A。电压比实施例1中的高2V,而发光效率却比实施例1中器件的发光效率低。虽然发出的光为高纯红光,色度坐标为(0.65,0.35),但是当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半寿命却短至120小时。
实施例2
除了以化合物A-3代替化合物A-1进行气相淀积以便化合物A-3浓度为2.0mol%外,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7V电压下的发光度为120cd/m2和发光效率为3.26cd/A。发出的光为高纯红光,色度坐标为(0.59,0.39)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半寿命长达1000小时。
实施例3
除了以化合物A-22代替化合物A-1进行气相淀积以便化合物A-22浓度为1.9mol%外,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7V电压下的发光度为110cd/m2和发光效率为2.5cd/A。发出的光为高纯红光,色度坐标为(0.64,0.33)。当此器件在稳定电流驱动下初始发光度为500cd/m2时,其半寿命长达1600小时。
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]、[2]或[2’]表示的化合物,发红光,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 (10)
1.一种有机电致发光器件,包括沉积在至少一对电极之间的有机层,其中有机层包含由通式[1]表示的化合物:其中R1至R14分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可被取代或不被取代;和在R1至R14中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团。
3.一种由通式[2’]表示的新型化合物:其中R15至R26分别各自表示氢原子、含1至10个碳原子的烷基、含6至20个碳原子的芳氧基、含6至20个碳原子的芳烷基、含6至30个碳原子的芳基、含6至30个碳原子的芳氨基、含2至20个碳原子的烷氨基或含6至30个碳原子的芳烷基氨基,这些基团可被取代或不被取代;在R15至R26中至少一对相互邻接的R不表示氢原子,而是表示结合形成环状结构的基团;和Ar1和Ar2表示含6至30个碳原子的取代或不取代芳基或含5至30个碳原子的取代或不取代杂环基团,Ar1和Ar2均表示苯基这一情况除外。
4.权利要求1的有机电致发光器件,其中有机层包括含由通式[1]表示的化合物的发光层。
5.权利要求2的有机电致发光器件,其中有机层包括含由通式[2]表示的化合物的发光层。
6.权利要求4的有机电致发光器件,其中发光层包含0.1-20mol%的由通式[1]表示的化合物。
7.权利要求5的有机电致发光器件,其中发光层包含0.1-20mol%的由通式[2]表示的化合物。
8.权利要求4至7中任一项的有机电致发光器件,其中发光层具有传递电子的性质。
9.权利要求1、2和4至8中任一项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。
10.权利要求1、2和4至8中任一项的有机电致发光器件,它发红光。
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JP27946399A JP2001102172A (ja) | 1999-09-30 | 1999-09-30 | 有機エレクトロルミネッセンス素子 |
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EP (1) | EP1138744A4 (zh) |
JP (1) | JP2001102172A (zh) |
KR (1) | KR20010093121A (zh) |
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- 1999-09-30 JP JP27946399A patent/JP2001102172A/ja not_active Withdrawn
-
2000
- 2000-09-27 EP EP00962881A patent/EP1138744A4/en not_active Withdrawn
- 2000-09-27 KR KR1020017006680A patent/KR20010093121A/ko not_active Application Discontinuation
- 2000-09-27 WO PCT/JP2000/006657 patent/WO2001023496A1/ja not_active Application Discontinuation
- 2000-09-27 CN CNB008021252A patent/CN1174078C/zh not_active Expired - Fee Related
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CN100425599C (zh) * | 2005-12-31 | 2008-10-15 | 清华大学 | 一种有机电致发光材料及其应用 |
CN106866348A (zh) * | 2017-01-18 | 2017-06-20 | 中国科学院上海有机化学研究所 | 一种多环芳烃化合物、合成方法及用途 |
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US6489046B1 (en) | 2002-12-03 |
CN1174078C (zh) | 2004-11-03 |
TW504942B (en) | 2002-10-01 |
KR20010093121A (ko) | 2001-10-27 |
JP2001102172A (ja) | 2001-04-13 |
EP1138744A4 (en) | 2006-06-28 |
EP1138744A1 (en) | 2001-10-04 |
WO2001023496A1 (fr) | 2001-04-05 |
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