CN109400585A - 1,4-二吡啶苯类衍生物及有机电致发光器件 - Google Patents
1,4-二吡啶苯类衍生物及有机电致发光器件 Download PDFInfo
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- CN109400585A CN109400585A CN201710714098.0A CN201710714098A CN109400585A CN 109400585 A CN109400585 A CN 109400585A CN 201710714098 A CN201710714098 A CN 201710714098A CN 109400585 A CN109400585 A CN 109400585A
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- 238000005401 electroluminescence Methods 0.000 title claims description 35
- DKYZGYHYCZDGOJ-UHFFFAOYSA-N benzene;pyridine Chemical class C1=CC=CC=C1.C1=CC=NC=C1.C1=CC=NC=C1 DKYZGYHYCZDGOJ-UHFFFAOYSA-N 0.000 title description 2
- 239000000463 material Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical class C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 68
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 33
- -1 xenyl Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 13
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 230000005540 biological transmission Effects 0.000 claims description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 150000005054 naphthyridines Chemical class 0.000 claims description 8
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 8
- GXGTZUUUEQORAH-UHFFFAOYSA-N C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 Chemical class C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 GXGTZUUUEQORAH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- OGNZZTLIIQCYCG-UHFFFAOYSA-N N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 Chemical group N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 OGNZZTLIIQCYCG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001854 cinnolines Chemical class 0.000 claims description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims 1
- BSCXJHRXVLREBO-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole;quinoline Chemical compound C1CN=CO1.N1=CC=CC2=CC=CC=C21 BSCXJHRXVLREBO-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002585 base Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
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- 239000000126 substance Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- 239000011521 glass Substances 0.000 description 5
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- 239000002994 raw material Substances 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 244000061458 Solanum melongena Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- GQRAEVALMHYTEK-UHFFFAOYSA-N 2-bromo-1,4-diiodobenzene Chemical compound BrC1=CC(I)=CC=C1I GQRAEVALMHYTEK-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZSVHUITUMSDFCK-UHFFFAOYSA-N isoquinoline;quinoline Chemical compound C1=NC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 ZSVHUITUMSDFCK-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Abstract
本发明涉及1,4‑二吡啶苯类衍生物及其应用，本发明的1,4‑二吡啶苯类衍生物具有如下通式(1)所示的结构。由于本发明的化合物具有平衡的空穴和电子载流子流，从而使得使用本发明材料的器件结构更加简化，同时器件的寿命以及发光效率都得到提升。
Description
技术领域
本发明涉及1,4-二吡啶苯类衍生物和使用了其的有机电致发光器件，特别涉及寿命长、高发光效率、色纯度高的有机电致发光器件和实现其的芳香族胺衍生物。
背景技术
有机电致发光材料的有机电致发光器件(OLED)，可以用于固体发光型的全色彩显示以及固态白光照明等领域，被誉为下一代新型显示及照明技术。通常OLED器件含有发光层和夹持该层的一对对置电极。器件在两电极间施加电场时，从阴极侧注入电子，从阳极侧注入空穴，电子在发光层中与空穴复合，形成激发状态，激发状态恢复到基态时，能量以光的形式放出。
前期阶段报道的大部分主体材料是空穴传输型主体材料或电子传输型主体材料，由于载流子传输性能的不平衡，这种单极性的主体材料容易形成不利的窄的复合区域。通常当使用空穴传输型主体材料时，在发光层和电子传输层界面会产生电荷复合区域，而当使用电子传输型主体材料时，在发光层和空穴传输层界面会产生电荷复合区域，然而弱的载流子迁移率和发光层中不平衡的电荷对有机发光器件的发光效率不利，同时有机电致磷光器件这种窄的电荷复合区域会加快三重态-三重态湮灭过程，从而导致发光效率下降，尤其是在电流密度条件下为了避免这种效应，通常采用的策略是使用两个发光层，其中一层使用空穴传输型主体材料，另一个发光层使用电子传输型主体材料，将空穴传输型和电子传输型主体材料混合置于单个发光层中，然而这两种策略使得器件的制备变得复杂，且混合的主体材料会导致相分离的问题，因此，为了达到高效的电致发光效果，需要发展具有平衡的载流子传输性能的主体材料，以拓宽电荷复合区域。
中国专利申请CN105968100A虽然公开了一种咪唑类衍生物化合物，并且具体公开了化合物C-2，但其主要作为电子传输层化合物，当其作为主体发光材料时，其寿命和发光效率都有待进一步提升。
发明内容
本发明的目的在于，提供一种具有寿命长，发光效率高的双极性主体材料，以及提供一种有效地制备这类材料的方法。
本发明人为实现上述目的进行了深入研究，结果发现，当使用具有下述通式(1)所示的化合物作为有机电致发光器件的发光主体材料时，能够获得具有寿命长，发光效率高的有机电致发光器件。
本发明提供了1,4-二吡啶苯类衍生物，其结构式如下述通式(I)所示：
式(I)中，
X1～X5独立选自N或CR1，其中两个X1相同或者不同；两个X2相同或者不同；两个X3相同或者不同；两个X4相同或者不同；两个X5相同或者不同；X1～X5中的至少一个为N；R1独立的为H、C1～C4的烷基、C6～C18的取代或未取代芳基或C4～C18的取代或未取代的杂芳基；优选的，所述芳基或杂芳基选自苯基、联苯基、三联苯基、萘基、噻吩基、呋喃基、吡啶基、哒嗪基、嘧啶基、吡嗪基；
L1和L2独立的为C1～C4亚烷基、醚基、芳基、杂芳基或为单键；L1和L2相同或者不同；
Ar1和Ar2独立的为通式(II)所示结构的取代基，所述取代基上的连接位点位于苯环上或者为X6；Ar1和Ar2相同或者不同；
式(II)中，
X6选自N、NR2、CRa、CRbRc；
X7选自O、S、NR3、CRdRe、或者X7不存在；当X7不存在时，式(II)中与X7相连的两个碳原子单键相连或者断开；
其中R2、R3、Ra、Rb、Rc、Rd、Re独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、噻吩基、呋喃基、吡啶基、哒嗪基、嘧啶基、吡嗪基；
式(II)中的两个苯环任选独立的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、三亚苯基、芴基、吡啶基、哒嗪基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、萘啶基、三嗪基、吡啶并吡嗪基、呋喃基、苯并呋喃基、二苯并呋喃基、氮杂-二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、氮杂-二苯并噻吩基的基团及其所组成的组中的基团取代；
任选的，式(II)中的一个苯环与其它芳基或杂芳基形成稠合芳香环，所述稠合芳香环选自萘、芴、喹啉、异喹啉、喹唑啉、喹喔啉、噌啉、萘啶、三嗪、吡啶并吡嗪、苯并呋喃、二苯并呋喃、氮杂-二苯并呋喃、苯并噻吩、二苯并噻吩、氮杂-二苯并噻吩；所述稠合芳香环任选的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基的基团所取代。
需要说明的是，本发明中，Ca～Cb的表达方式代表该基团具有的碳原子数为a～b，除非特殊说明，一般而言该碳原子数不包括取代基的碳原子数。
本发明中，对于化学元素的表述包含化学性质相同的同位素的概念，例如“氢”的表述，也包括化学性质相同的“氘”、“氚”的概念。
本发明中的杂原子，通常指选自B、N、O、S、P、P(＝O)、Si和Se中的原子或原子团。
本发明涉及一种有机电致发光器件，包括基板，以及依次形成在所述基板上的阳极层、至少含有一层发光层的有机功能层和阴极层，其特征在于：所述有机功能层中的至少一层单独或作为混合成分含有具有如下通式(I)所示结构的化合物，
式(I)中，
X1～X5独立选自N或CR1，其中两个X1相同或者不同；两个X2相同或者不同；两个X3相同或者不同；两个X4相同或者不同；两个X5相同或者不同；X1～X5中的至少一个为N；R1独立的为H、C1～C4的烷基、C6～C18的取代或未取代芳基或C4～C18的取代或未取代的杂芳基；优选的，所述芳基或杂芳基选自苯基、联苯基、三联苯基、萘基、噻吩基、呋喃基、吡啶基、哒嗪基、嘧啶基、吡嗪基；；
L1和L2独立的为亚烷基、醚基、芳基、杂芳基或为单键；L1和L2相同或者不同；
Ar1和Ar2独立的为通式(II)所示结构的取代基，所述取代基上的连接位点位于苯环上或者为X6；Ar1和Ar2相同或者不同；
式(II)中，
X6选自N、NR2、CRa、CRbRc；
X7选自O、S、NR3、CRdRe、或者X7不存在；当X7不存在时，式(II)中与X7相连的两个碳原子单键相连或者断开；
其中R2、R3、Ra、Rb、Rc、Rd、Re独立的选自H、C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、吡啶基、哒嗪基、嘧啶基、吡嗪基；
式(II)中的两个苯环任选独立的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、三亚苯基、芴基、吡啶基、哒嗪基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、萘啶基、三嗪基、吡啶并吡嗪基、呋喃基、苯并呋喃基、二苯并呋喃基、氮杂-二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、氮杂-二苯并噻吩基的基团及其所组成的组中的基团取代；
任选的，式(II)中的一个苯环与其它芳基或杂芳基形成稠合芳香环，所述稠合芳香环选自萘、芴、喹啉、异喹啉、喹唑啉、喹喔啉、噌啉、萘啶、三嗪、吡啶并吡嗪、苯并呋喃、二苯并呋喃、氮杂-二苯并呋喃、苯并噻吩、二苯并噻吩、氮杂-二苯并噻吩；所述稠合芳香环任选的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基的基团所取代。
在本发明的一个优选实施方式中，所述的Ar1和Ar2独立地选自下式基团：
其中，X8和X9独立的为O、S、NR4、CRfRg；
其中R4、Rf、Rg独立的选自H、C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、吡啶基、哒嗪基、嘧啶基、吡嗪基。
更优选地，所述的Ar1和Ar2独立地或者同时选自下述结构式所表示基团中的一种，*表示连接位点，下述结构式所表示的基团任选的被选自C1～C4的烷基、卤素、硝基、氰基、苯基取代，在下述结构式中，当连接位点与下述结构式中的不特定原子连接时，其表示可以与结构式中的任意可连接的位点进行连接，而不仅仅限于与“*—”所在的苯环上的碳原子连接：
在本发明的一个优选实施方式中，其特征在于，L1和L2独立的为亚烷基、醚基、苯基、联苯基、三联苯基、萘基、三亚苯基、芴基、吡啶基、哒嗪基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、萘啶基、三嗪基、吡啶并吡嗪基、呋喃基、苯并呋喃基、二苯并呋喃基、氮杂-二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、氮杂-二苯并噻吩基或为单键；L1和L2相同或者不同。
在本发明的一个优选实施方式中，出于合成成本以及发光效率的考虑，式(I)中Ar1和Ar2相同；所述的相同是指Ar1和Ar2的结构相同；优选的，所述的相同进一步指连接位点相同。
在本发明的一个优选实施方式中，所述的化合物为1,4-二吡啶苯类衍生物，即式(I)中X1～X5所在的基团都为吡啶基；优选的，两个吡啶基上的N都位于对位、邻位或间位。
在本发明的一个优选实施方式中，所述的式(I)中-L1-Ar1和-L2-Ar2相同；优选的，L1和L2连接于式(I)中苯环上的对位，如下式(I-1)或(I-2)所示。
在本发明的一个优选实施方式中，所述式(I)化合物具有以下化学结构：
更进一步的，上述通式(1a)中，优选以下结构式A1至A34代表的化合物：
上述通式(1b)中，优选以下结构式B1至B34代表的化合物：
上述通式(1d)中，优选以下结构式D1至D34代表的化合物：
另一方面，本发明还涉及通式(I)所示的化合物作为发光主体材料在有机电致发光器件中的应用。
另一方面，本发明还涉及一种有机电致发光器件，其包括基板、阳极层、阴极层、以及介于阳极层与阴极层之间的至少一层有机层；其中，所述有机层中的至少一层以单独组分或以混合物组分的形式包括上述通式(I)所示的化合物。
在本发明所述的有机电致发光器件，其有机层中包括空穴注入层、空穴传输层、发光层、电子传输层和电子注入层，所述发光层包括主体材料(host)和客体材料(dopant)，其特征在于：所述式(I)化合物作为发光主体材料。
在本发明所述的有机电致发光器件，通式(I)所示结构的化合物中的一种或者两种的组合单独作为发光层材料使用，或者通式(I)所示结构的化合物中的一种或者两种以上的组合与绿色磷光染料组合作为发光层材料使用。
在本发明所述的有机电致发光器件，通式(I)所示结构的化合物中的一种或者两种以上的组合与Ir(ppy)3混合作为发光层材料使用，所采用的混合重量比例为90:10-10:90。
本公开的有机电致发光器件基于本公开化合物的优异性能，能够降低器件起亮和工作电压，提高器件效率，延长器件寿命。
本公开有机电致发光器件的基板可以使用传统有机发光器件中的基板，例如：玻璃或塑料，优选使用玻璃基板。
本公开有机电致发光器件的阳极材料可以采用透明的高导电性材料，例如铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等。本公开器件中优选使用铟锡氧(ITO)作阳极材料。
本公开有机电致发光器件的空穴注入层可以采用CuPc、TNATA和PEDT/PSS等，本公开器件制作中使用2-TNATA作空穴注入层材料。空穴传输层可以采用N,N’-二(3-甲苯基)-N,N’-二苯基-[1,1-联苯基]-4,4’-二胺(TPD)或N,N’-二苯基-N,N’-二(1-萘基)-(1,1’-联苯基)-4,4’-二胺(NPB)等三芳胺类材料。其中NPB是常用的空穴传输材料，在本公开的器件制作中的空穴传输层材料选用NPB。空穴传输层厚度一般在5nm-5μm；常见的电子传输材料有Alq3、Bphen、BCP、PBD等，本公开的器件制作中选用Alq3作电子传输层材料。
本公开有机电致发光器件的发光层可以为单发光层也可以是多发光层结构；发光颜色不限，可以为如红、黄、蓝、绿等，客体材料(也称作掺杂剂或染料)可以选用Ir(ppy)3、Ir(piq)2acac、Ir(4,6-dFppy)2(pic)(具体结构见下式)等磷光染料，优选绿色磷光染料，更优选Ir(ppy)3。
本公开有机电致发光器件的阴极可以采用金属及其混合物结构，如Mg:Ag、Ca:Ag等，也可以是电子注入层/金属层结构，如LiF/Al、Li2O/Al等常见阴极结构。其中电子注入层可以为碱金属、碱土金属以及过渡金属的单质、化合物或混合物，也可以是多层材料构成的复合阴极结构。在本公开的器件制作中优选使用的阴极材料为LiF/Al。
除以上一般说明以及实施例中所列举的内容以外，本领域技术人员已知的涉及有机电致发光器件的其它技术内容，例如制作方法及一般成分等，也适用于本公开中。本公开的化合物也可以与现有公知的发光层主体材料组合使用。
本发明化合物可以作为双极性主体材料，因具有平衡的空穴和电子载流子流，从而使得使用本发明材料的器件结构更加简化，同时器件的寿命以及发光效率都得到提升。
具体实施方式
参照下面的实施例来更具体地描述本发明，但是本发明并不局限于这些实施例。
用于有机电致发光器件的本发明通式(1)中共用的母核合成通式如下：
在氩气流下，在500mL茄型烧瓶中投入1,4-二溴-2,5-二碘苯(48.7g,0.1mol)、4-吡啶硼酸(28.7g,0.1mol)、四(三苯基膦)钯0.6g、碳酸钾(27.6g,0.2mol)、二氧六环500mL，水100ml，回流反应3小时。冷却后，加入水用二氯甲烷萃取，有机相浓缩得棕色固体，甲苯乙醇重结晶得黄色固体A028.3g,收率74.6％。1H NMR(500MHz,Chloroform)δ8.71(d,J＝15.0Hz,4H),7.90(d,J＝15.0Hz,4H),7.53(s,2H)。
同样的方法，不同在于将4-吡啶硼酸替换为等当量的3-吡啶硼酸得到B0。
同样的方法，不同在于将4-吡啶硼酸替换为等当量的3-吡啶硼酸得到D0。
主要化合物合成实施例
合成例1.A1的合成
在氩气流下，在500mL茄型烧瓶中投入A0(39g,0.1mol)、3-(N-苯基咔唑)硼酸(28.7g,0.1mol)、四(三苯基膦)钯0.6g、碳酸钾(27.6g,0.2mol)、二氧六环500mL，水100ml，回流反应3小时。冷却后，直接过滤，滤饼用二甲苯重结晶得白色固体A1＝45g,收率63.5％。
1H NMR(500MHz,Chloroform)δ8.71(d,J＝7.4Hz,4H),8.55(dd,J＝7.3,1.6Hz,2H),8.39(s,2H),8.20(d,J＝1.4Hz,2H),7.90(d,J＝7.4Hz,4H),7.66–7.55(m,8H),7.51(ddd,J＝8.9,7.4,1.5Hz,8H),7.13(dtd,J＝26.2,7.5,1.6Hz,4H)。
下表所列化合的合成方法同合成例1，不同在于将3-(N-苯基咔唑)硼酸替换为等当量的相应原料，其中所用原料均可以通过化工市场买到，具体如下所示：
合成实施例89.A5的合成
在氩气流下，在500mL茄型烧瓶中投入A0(39g,0.1mol)、咔唑(18.3g,0.1mol)、Pd2(dba)30.6g、叔丁醇钠(27.6g,0.2mol)、三叔丁基膦，二甲苯500mL，，回流反应4小时。冷却后，直接过滤，滤饼用二甲苯重结晶得白色固体A5＝42g,收率74.6％。
1H NMR(500MHz,Chloroform)δ8.71(d,J＝7.4Hz,4H),8.59–8.50(m,4H),8.23–8.15(m,2H),7.90(d,J＝7.4Hz,4H),7.52(dd,J＝7.3,1.6Hz,2H),7.45–7.35(m,2H),7.24–7.06(m,8H)。
下表1所列化合物的合成方法同合成实施例89，不同在于将母核及原料替换为等当量的相应原料，其中所用原料均可以通过化工市场买到，具体如下所示：
表1：化合物的合成方法
表2.合成实施例化合物表征数据
器件实施例
本发明器件实施例中有机电致发光器件的结构为：在基片上按照“阳极/空穴注入层(HIL)/空穴传输层(HTL)/发光层(EML)/电子传输层(ETL)/电子注入层(EIL)/阴极”的顺序层叠，各层使用材料分别为：
ITO/2-TNATA(30nm)/NPB(20nm)/通式(1)化合物：Ir(ppy)3(10％)(20nm)/BPhen(50nm)/LiF(1nm)/Al。上述材料分子结构如下：
器件实施例1.化合物A1作为发光层的主体材料
有机电致发光器件制备过程如下：
将表面涂覆了ITO透明导电薄膜的玻璃基板在清洗液中超声清洗，在去离子水中超声处理，在丙酮∶乙醇混合溶剂(体积比1∶1)混合溶液中超声除油，在洁净环境下烘烤至完全去除水分，用紫外灯进行刻蚀和臭氧处理，并用低能阳离子束轰击表面；
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上真空蒸镀2-TNATA作为空穴注入层，蒸镀速率为0.1nm/s，蒸镀总膜厚为40nm；然后蒸镀空穴传输层NPB，蒸镀速率为0.1nm/s，蒸镀膜厚为10nm；
在空穴传输层之上形成电致发光层，利用多源共蒸的方法，将作为主体的化合物A1放置在真空气相沉积设备的小室中，将作为客体的(ppy)3Ir放置在真空气相沉积设备的另一室中，调节主体材料A1蒸镀速率为0.1nm/s，Ir(ppy)3的浓度为10％，蒸镀总膜厚为20nm；
在发光层上真空蒸镀Bphen形成膜厚为50nm的电子传输层，其蒸镀速率为0.1nm/s；
在电子传输层上依次真空蒸镀厚度为1nm的LiF作为电子注入层，厚度为150nm的Al层作为器件的阴极。
器件实施例2～12.
与器件实施例1相同的方法制备得到有机电致发光器件，区别仅在于，将化合物A1置换为表3中化合物作为主体材料。
器件对比例1.CBP作为发光主体材料
采用与实施例1相同的方法制备得到有机电致发光器件，不同在于，将化合物A1替换为化合物CPB。
在同样亮度下，使用Keithley 2602数字源表亮度计(北京师范大学光电仪器厂)测定器件实施例1-6以及器件对比例1中制备得到的有机电致发光器件的驱动电压和电流效率，结果见表3。
表3.本公开化合物用作主体材料的器件性能测定结果：
| 器件例 | 主体材料 | 要求亮度cd/m<sup>2</sup> | 电压V | 效率cd/A | T90寿命h |
| 器件实施例1 | A1 | 10000 | 4.65 | 58 | 98 |
| 器件实施例2 | A3 | 10000 | 4.66 | 54 | 92 |
| 器件实施例3 | A22 | 10000 | 4.45 | 57 | 95 |
| 器件实施例4 | A24 | 10000 | 4.36 | 55 | 87 |
| 器件实施例5 | B1 | 10000 | 4.48 | 55 | 96 |
| 器件实施例6 | B3 | 10000 | 4.52 | 58 | 89 |
| 器件实施例7 | B28 | 10000 | 4.59 | 59 | 91 |
| 器件实施例8 | B24 | 10000 | 4.55 | 60 | 90 |
| 器件实施例9 | D1 | 10000 | 4.51 | 51 | 64 |
| 器件实施例10 | D3 | 10000 | 4.47 | 57 | 58 |
| 器件实施例11 | D6 | 10000 | 4.62 | 58 | 73 |
| 器件实施例12 | D24 | 10000 | 4.48 | 60 | 75 |
| 器件实施例13 | E5 | 10000 | 4.78 | 53 | 99 |
| 器件对比例1 | CBP | 10000 | 5.43 | 50 | 86 |
由表2中公开的器件实施例1-13的器件性能数据可见，在有机电致发光器件结构中其它材料相同的情况下，在器件中EML材料的调整，相比较器件对比例1，可以显著地降低器件的工作电压，并大幅度提高器件的发光效率。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于上述实施方式中的具体细节，在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，这些简单变型均属于本发明的保护范围。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合，为了避免不必要的重复，本发明对各种可能的组合方式不再另行说明。
此外，本发明的各种不同的实施方式之间也可以进行任意组合，只要其不违背本发明的思想，其同样应当视为本发明所公开的内容。
Claims (12)
1.结构如通式(I)所示的化合物：
式(I)中，
X1～X5独立选自N或CR1，其中两个X1相同或者不同；两个X2相同或者不同；两个X3相同或者不同；两个X4相同或者不同；两个X5相同或者不同；X1～X5中的至少一个为N，R1独立的为H、C1～C4的烷基、C6～C18的取代或未取代芳基或C4～C18的取代或未取代的杂芳基；优选的，所述芳基或杂芳基选自苯基、联苯基、三联苯基、萘基、噻吩基、呋喃基、吡啶基、哒嗪基、嘧啶基、吡嗪基；
L1和L2独立的为C1～C4亚烷基、醚基、芳基、杂芳基或为单键；L1和L2相同或者不同；
Ar1和Ar2独立的为通式(II)所示结构的取代基，所述取代基上的连接位点位于苯环上或者为X6；Ar1和Ar2相同或者不同；
式(II)中，
X6选自N、NR2、CRa、CRbRc；
X7选自O、S、NR3、CRdRe、或者X7不存在；当X7不存在时，式(II)中与X7相连的两个碳原子单键相连或者断开；
其中R2、R3、Ra、Rb、Rc、Rd、Re独立的选自H、C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、噻吩基、呋喃基、吡啶基、哒嗪基、嘧啶基、吡嗪基；
式(II)中的两个苯环任选独立的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、三亚苯基、芴基、吡啶基、哒嗪基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、萘啶基、三嗪基、吡啶并吡嗪基、呋喃基、苯并呋喃基、二苯并呋喃基、氮杂-二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、氮杂-二苯并噻吩基的基团及其所组成的组中的基团取代；
任选的，式(II)中的一个苯环与其它芳基或杂芳基形成稠合芳香环，所述稠合芳香环选自萘、芴、喹啉、异喹啉、喹唑啉、喹喔啉、噌啉、萘啶、三嗪、吡啶并吡嗪、苯并呋喃、二苯并呋喃、氮杂-二苯并呋喃、苯并噻吩、二苯并噻吩、氮杂-二苯并噻吩；所述稠合芳香环任选的被0、1、2、3、4个独立的选自C1～C4的烷基、卤素、硝基、氰基、取代或未取代的苯基的基团所取代。
2.根据权利要求1所述的化合物，其特征在于，Ar1和Ar2独立的选自下式基团，其中*表示连接位点，在下述结构式中，当连接位点与下述结构式中的不特定原子连接时，其表示可以与结构式中的任意可连接的位点进行连接：
其中，X8和X9独立的为O、S、NR4、CRfRg；
其中R4、Rf、Rg独立的选自H、C1～C4的烷基、卤素、硝基、氰基、苯基、联苯基、三联苯基、萘基、吡啶基、哒嗪基、嘧啶基、吡嗪基。
3.根据权利要求1所述的化合物，其特征在于，L1和L2独立的为亚烷基、醚基、苯基、联苯基、三联苯基、萘基、三亚苯基、芴基、吡啶基、哒嗪基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、萘啶基、三嗪基、吡啶并吡嗪基、呋喃基、苯并呋喃基、二苯并呋喃基、氮杂-二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、氮杂-二苯并噻吩基或为单键；L1和L2相同或者不同。
4.根据权利要求1所述的化合物，其特征在于两个Ar1和Ar2相同；所述的相同是指Ar1和Ar2的结构相同；优选的，所述的相同进一步指连接位点相同。
5.根据权利要求1所述的化合物，其特征在于，所述的化合物为1,4-二吡啶苯类衍生物，即式(I)中X1～X5所在的基团都为吡啶基；优选的，两个吡啶基上的N都位于对位、邻位或间位。
6.根据权利要求1所述的化合物，其特征在于，所述的式(I)中-L1-Ar1和-L2-Ar2相同；优选的，L1和L2连接于式(I)中苯环上的对位。
7.根据权利要求1所述的化合物，其特征在于，所述化合物为以下结构式A1至D34代表的化合物中的一种：
8.权利要求1～7中任一项所述的通式(I)所示的化合物在有机电致发光器件中的应用。
9.一种有机电致发光器件，其包括阴极、阳极以及有机层，所述有机层包含权利要求1～7中任意一项所述的通式(I)所示的化合物。
10.根据权利要求9所述的有机电致发光器件，其有机层包括空穴注入层、空穴传输层、发光层、电子传输层和电子注入层，所述发光层包括主体材料和客体材料，其特征在于：所述式(I)化合物作为发光层的主体材料。
11.根据权利要求10所述的有机电致发光器件，所述客体材料为绿色磷光染料。
12.根据权利要求9所述的有机电致发光器件，通式(I)所示结构的化合物中的一种或者两种以上的组合与Ir(ppy)3混合作为发光层材料使用，所采用的混合重量比例为90:10-85:15。
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