CN117820304A - Organic material composition and application thereof - Google Patents
Organic material composition and application thereof Download PDFInfo
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- CN117820304A CN117820304A CN202211215223.0A CN202211215223A CN117820304A CN 117820304 A CN117820304 A CN 117820304A CN 202211215223 A CN202211215223 A CN 202211215223A CN 117820304 A CN117820304 A CN 117820304A
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000011368 organic material Substances 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- -1 phenylnaphthyl Chemical group 0.000 claims description 48
- 239000010410 layer Substances 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 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 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 4
- 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 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- ZAHFNCCKZJRSNY-UHFFFAOYSA-N 12-bromo-10,10-dimethyl-10h-indeno[1,2-b]triphenylene Chemical group C1=CC=C2C3=CC4=C5C(C)(C)C=C(Br)C=C5C=C4C=C3C3=CC=CC=C3C2=C1 ZAHFNCCKZJRSNY-UHFFFAOYSA-N 0.000 description 1
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ICMMJWDNKMITSS-UHFFFAOYSA-N dibenzothiophen-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3SC2=C1 ICMMJWDNKMITSS-UHFFFAOYSA-N 0.000 description 1
- LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MTYGHSICPWZTQY-UHFFFAOYSA-N n-(4-phenylphenyl)-9,9'-spirobi[fluorene]-2-amine Chemical compound C=1C=C2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C2=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 MTYGHSICPWZTQY-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- NUFPFZMBNCKWPV-UHFFFAOYSA-N spiro[fluorene-9,1'-indene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C11C=CC2=CC=CC=C21 NUFPFZMBNCKWPV-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic material composition and application thereof, wherein the organic material composition comprises at least one compound with a structure shown in a formula 1 and at least one compound with a structure shown in a formula 2, and the two materials are synergistic, so that the carrier transmission capacity is balanced, the luminous efficiency of an organic electroluminescent element is further improved, the service life of the device is prolonged, and the organic material composition has lower driving voltage.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and relates to an organic material composition and application thereof.
Background
An electroluminescent device (EL device) is a self-luminous display device, which has advantages in that it provides a wider viewing angle, a larger contrast ratio, and a faster response time.
The most important factor determining the luminous efficiency in an organic EL device is a light emitting material, which is required to have the following characteristics: high quantum efficiency, high mobility of electrons and holes, and uniformity and stability of the formed light emitting material layer.
Recently, an urgent task is to develop an organic EL device having high efficiency and long lifetime. In particular, in view of EL characteristics required for medium-and large-sized OLED panels, development of highly excellent light emitting materials superior to conventional materials is eagerly demanded. For this reason, the host material is required to have a high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability, to achieve long life, formability of an amorphous film, good adhesion to adjacent layers, and no mobility between layers.
The light emitting material may be used as a combination of host and dopant to improve color purity, light emitting efficiency, and stability. Generally, an EL device having excellent characteristics has a structure including a light emitting layer formed by doping a dopant into a host. When such a dopant/host material system is used as a light emitting material, the host material greatly affects the efficiency and lifetime of the EL device, and thus is critical in the art for the development of the host material.
CN105884623a discloses the use of indenotriphenyl-based amine derivatives as charge transport materials and electron blocking materials in organic electroluminescent devices, where indenotriphenyl-based amine derivatives are used as electron blocking layer materials in organic EL devices, with higher device voltages and lower efficiencies.
Accordingly, there is a desire in the art to further develop materials capable of giving more excellent performance to the organic electroluminescent device.
Disclosure of Invention
In view of the shortcomings of the prior art, the present invention aims to provide an organic material composition and application thereof.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic material composition comprising at least one compound of the structure represented by formula 1 and at least one compound of the structure represented by formula 2,
Z 1 selected from N and CL Y1 Ar Y1 ，Z 2 Selected from N and CL Y2 Ar Y2 ，Z 3 Selected from N and CL Y3 Ar Y3 ，Z 4 Selected from N and CL Y4 Ar Y4 ，Z 5 Selected from N and CL Y5 Ar Y5 ，Z 6 Selected from N and CL Y6 Ar Y6 ，
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 Independently selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30, a heteroarylene group,
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl,
L Y1 Ar Y1 、L Y2 Ar Y2 、L Y3 Ar Y3 、L Y4 Ar Y4 、L Y5 Ar Y5 l and L Y6 Ar Y6 Each independently, or adjacent two are linked to form a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring;
wherein n represents an integer of 0 to 3; r is R 1 ' to R 4 ' is independently selected from the group consisting of: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; ar (Ar) 5 ' and Ar 6 ' is selected from: substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 50 carbon atoms.
Preferably, the compound of the structure shown in formula 1 is a compound of the structure shown in formula 1-1,
wherein Z is 1 Selected from N and CL Y1 Ar Y1 ，Z 3 Selected from N and CL Y3 Ar Y3 ，Z 5 Selected from N and CL Y5 Ar Y5 And Z is 1 、Z 3 Z is as follows 5 At least two of which are N;
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 ar, ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 The definition of (2) is the same as that of formula 1.
Preferably, at said Z 1 、Z 3 Z is as follows 5 Wherein Z is 1 、Z 3 Is N, Z 5 For CL Y5 Ar Y5 Wherein L is Y5 Ar Y5 、L Y6 Ar Y6 Each independently or linked to form a substituted or unsubstituted benzene ring; or Z is 1 、Z 5 Is N, Z 3 For CL Y3 Ar Y3 The method comprises the steps of carrying out a first treatment on the surface of the Or Z is 3 、Z 5 Is N, Z 1 For CL Y1 Ar Y1 The method comprises the steps of carrying out a first treatment on the surface of the Or Z is 1 、Z 3 、Z 5 Is N;
preferably Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, triphenylene, anthracenyl, phenanthryl,A group or a group represented by formula 3; />
Y is selected from O, S and CR W1 R W2 ，
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 When at least one of the compounds is represented by the formula 3,
r in 3 Y1 -R Y8 、R W1 R is R W2 Any one of the compounds and L in the formula 2-1 Y2 、L Y4 Or L Y6 Is connected through chemical bonds;
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 each of which may be the same or different,
R Y1 -R Y8 each independently selectFrom hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are each substituted by-O-and/or-S-in a manner not adjacent to the O atom and/or S atom, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy,
R Y1 -R Y8 each independently or adjacent two are linked to form a ring A, which is a substituted or unsubstituted C6-C30 aromatic ring,
R W1 r is R W2 Each independently selected from a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group.
Preferably, the group represented by formula 3 is selected from any one of the following groups:
y is selected from O, S and CR W1 R W2 ，R W1 And R is W2 Each independently selected from methyl or phenyl, or R W1 And R is W2 Connecting to form a spiro ring;
R Y1 -R Y8 each independently selected from hydrogen, deuterium, substituted or unsubstituted, such groups as: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenanthryl, benzophenanthryl, pyridyl, dibenzofuranyl, dibenzothienyl, dibenzofuranylphenyl, dibenzothienyl phenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzonaphthofuranyl or benzonaphthothienyl; r is R Y1 -R Y8 Each independently or adjacent two are connected to form a ring A, and the ring A is a substituted or unsubstituted benzene ring;
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 each independently selected from the group consisting of a linkage, phenylene, biphenylene, or naphthylene;
r in the formulae 3-1 to 3-6 Y1 -R Y8 、R W1 R is R W2 Any one of the compounds and L in the formula 2-1 Y2 、L Y4 Or L Y6 Through chemical bond connection.
Preferably Ar 5 ' and Ar 6 ' is selected from the group consisting of substituted or unsubstituted:
wavy lines represent the attachment sites of the groups.
In the present invention, when the groups as described above bear substituents, each of the substituents is independently selected from deuterium, halogen, cyano, nitro, unsubstituted or R 'substituted C1-C4 straight-chain or straight-chain alkyl, unsubstituted or R' substituted C6-C20 aryl, unsubstituted or R 'substituted C3-C20 heteroaryl, or unsubstituted or R' substituted C6-C20 arylamine; r' is selected from deuterium, halogen, cyano or nitro.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl or spirobifluorenyl.
Preferably, the heteroaryl group is selected from pyridinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, pyridylcarbazolyl, naphthylcarbazolyl, biphenylcarbazolyl, dibenzofuranylphenyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl or dibenzocarbazolyl.
Preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexenyl or adamantyl.
Preferably, the compound of the structure shown in formula 1 is selected from the following compounds:
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preferably, the compound of the structure shown in formula 2 is selected from the following compounds:
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preferably, the weight ratio of the compound of the structure shown in formula 1 to the compound of the structure shown in formula 2 in the organic material composition is 1:9-9:1, such as 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1, etc., preferably 2:8-8:2, more preferably 3:7-7:3, even more preferably 4:6-6:4.
As used in the present invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent element, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, an electron blocking material, a light emitting auxiliary material, a light emitting layer material (including a host material and a doping material), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, or hexyl.
As used herein, the term "C3-C30 cycloalkyl" refers to a mono-or polycyclic hydrocarbon derived from a hydrocarbon having from 1 to 30 ring backbone carbon atoms, which may include cyclopropyl, cyclobutyl, adamantyl, and the like.
Aryl, arylene in the present invention includes monocyclic, polycyclic or fused ring aryl groups, which may be interrupted by short non-aromatic units between the rings, and may comprise spiro structures. Aryl, arylene in the present invention include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, and the like.
Heteroaryl, heteroarylene, as used herein, includes monocyclic, polycyclic or fused ring heteroaryl groups, which rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, or sulfur. Heteroaryl, heteroarylene, in the present invention, includes, but is not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazayl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydro-acridinyl, or derivatives thereof, and the like.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl or spirobifluorenyl.
Preferably, the heteroaryl is selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridinyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthazazolyl, phenanthroimidazolyl, phenanthroxazinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, indolopyrazinyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9, 1' -indene) opyrazinyl, benzofuranocarzolyl or benzothiophenocarzolyl.
As used herein, the term "C6-C30 aryloxy" refers to a monovalent substituent represented by ZO-wherein Z represents an aryl group having 6 to 30 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
As used herein, the term "C1-C30 alkoxy" refers to a monovalent substituent represented by Z 'O-, wherein Z' represents an alkyl group having 1 to 30 carbon atoms.
As used herein, the term "substituted" refers to a compound in which a hydrogen atom is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted with a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise indicated, hydrogen atoms include protium, deuterium, or tritium.
In the present invention, "adjacent two groups are linked to form a ring" means that 2 substituents at adjacent positions in the same ring or adjacent rings can be linked to each other through chemical bonds to form a ring, and the specific way of linking to form a ring is not limited in the present invention (for example, by single bond, by benzene ring, by naphthalene ring, byCondensed, pass->Condensed, wherein->Meaning condensed positions), as hereinafter referred to in the same description, have the same meaning.
In the present invention, the definition of a group defines a range of carbon atoms, the number of carbon atoms being any integer within the defined range, for example, a C6-C60 aryl group, and the number of carbon atoms representing the aryl group may be any integer within the range of 6-60 inclusive, for example, 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, 60, or the like.
In the present invention, the each position-substituted organic compound is prepared by the following synthetic route:
the synthesis of the compounds of formulas 1 and 2 uses suzuki coupling.
In another aspect, the present invention provides an organic electroluminescent material comprising an organic material composition as described above.
In another aspect, the invention provides the use of an organic material composition or an organic electroluminescent material as described above in the preparation of an optical device.
Preferably, the optical device comprises any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quench device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the organic material composition or the organic electroluminescent material as described above.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are stacked in this order from the anode side to the cathode side.
Preferably, the material of the light emitting layer comprises a host material and a guest material, and the host material comprises the organic material composition or the organic electroluminescent material as described above.
Preferably, the guest material comprises a phosphorescent dopant comprising a transition metal-containing complex.
In another aspect, the present invention provides an organic electroluminescent device comprising an organic electroluminescent device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the organic material composition of the invention ensures that the carrier transmission capacity is balanced by the cooperation of at least one compound with the structure shown in the formula 1 and at least one compound with the structure shown in the formula 2, thereby improving the luminous efficiency of the organic electroluminescent element, prolonging the service life of the device and having lower driving voltage.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention, in which 1 is an anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a cathode.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Preparation example of the Compound of formula 1
Synthesis of compound H1: a25 ml two-necked round bottom flask was taken and placed in a stirrer and a return tube connected thereto, dried and then charged with nitrogen, and H1-A (1 mmol, CAS respectively was added1198396-40-5)、H1-B(1mmol，CAS182918-13-4) Potassium carbonate (K) 2 CO 3 1.5 mmol), ethanol (3 ml), water (3 ml), toluene (10 ml) and tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.05 mmol) was heated to 60℃and reacted for 12 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, quenched with water, extracted with methylene chloride (3X 20 ml), and the obtained extract was dried over magnesium sulfate, filtered and dried by spin-drying in order to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate/n-hexane: volume ratio 1/10) to give compound H1 (0.46 g, yield 73%).
Elemental analysis: c (C) 46 H 33 N 3 Theoretical value: c,88.01; h,5.30; n,6.69; actual measurement value: c,88.06; h,5.32; n,6.62; HRMS (ESI) M/z [ M+H ]] + : theoretical value: 627.27; actual measurement value: 628.21.
synthesis of compound H4: a50 ml two-necked round bottom flask was taken and placed in a stirrer and a return tube connected thereto, dried and then charged with nitrogen, and Compound H4-A (14.1 mmol, CAS2095370-50-4) H4-B (18.3 mmol, CAS 1883265-32-4), tetrakis (triphenylphosphine) palladium (0.7 mmol), potassium carbonate (28.2 mmol), 42 ml of toluene, 10 ml of ethanol and 14 ml of distilled water, and the mixture was stirred at 140℃for 8 hours. After the completion of the reaction, the reaction mixture was added dropwise to methanol to obtain a solid, and the obtained solid was filtered. Purifying by column chromatography (ethyl acetate/n-hexane: volume ratio 1/10) to obtainCompound H4 (5.8 g, 75% yield).
Synthesis of intermediate H10-B: to a 500mL four-necked flask equipped with a mechanical stirrer, a thermometer and a reflux condenser, 20g (1.0 mol) of cyanuric chloride, 62.9g (2.1 mol) of 4-boric acid-m-terphenyl, 37.7g of potassium carbonate were charged, 140mL of toluene, 60mL of ethanol and 60mL of water were measured, and the flask was purged with nitrogen under the liquid surface for 20 minutes. Finally, 0.4g of bis (triphenylphosphine) palladium (II) dichloride is added into the flask, heating is started, the internal temperature is controlled to be 75 ℃, reflux is started, and the system is clear yellow. The reaction was heated for 8h. After the reaction was completed, it was purified by column chromatography (eluent: DCM: hexane=1:2) to give intermediate H10-B29.0 g (yield 50%).
The corresponding products H2 to H3 and H10 to H17 were prepared by using the raw materials 1 and 2 in Table 3 as raw materials according to the preparation method of H1 and the corresponding products H5 to H9 were prepared by using the preparation method of H4 as shown in Table 3, and the structural characterization data of the products are shown in Table 4.
TABLE 3 Table 3
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TABLE 4 Table 4
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Preparation example of the Compound of formula 2
Synthesis of compound C1: a150 mL two-necked round bottom flask was taken and placed in a stirrer and upper reflux tube, after drying, nitrogen was charged, and a mixture of 5g (11.8 mmol) of 12-bromo-10, 10-dimethyl-10H-indeno [1,2-b ] triphenylene, 6.8g (14.1 mmol) of N- (biphenyl-4-yl) -9,9' -spirobifluorene-2-amine, 0.03g (0.11 mmol) of palladium (II) acetate, 0.04g (0.11 mmol) of 2- (dicyclohexylphosphino) biphenyl, 1.7g (17.7 mmol) of sodium t-butoxide and 100mL of toluene was added, respectively, and refluxed overnight under nitrogen. After the reaction was completed, it was then cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, and the solvent was removed, and purified by column chromatography (hexane/dichloromethane: volume ratio 10/1) to give 5.8g of the product as a yellow solid (yield 60%).
Synthesis of intermediate C6-B: to a 1L three-necked flask equipped with magnetic stirring under nitrogen purge were added 20g (0.1 mol) of dibenzo [ B, D ] thiophen-2-amine, 27g of 2-bromodibenzothiophene, 0.87g of tris (dibenzylideneacetone) dipalladium (0), 0.78g of 2-dicyclohexylphosphine-2, 6-dimethoxybiphenyl, 14.4g of sodium t-butoxide, 200mL of anhydrous toluene, and the mixture was heated to 110℃under nitrogen atmosphere to react for 3 hours. After the completion of the reaction, 28.6g (yield: 75%) of pure product was purified by column chromatography (Hexane: ea=10:1).
The corresponding products were prepared by referring to the preparation method of C1 described above using raw material 1 and raw material 2 in Table 5 as raw materials, and the structural characterization data of the products are shown in Table 6.
TABLE 5
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TABLE 6
Device embodiment
An organic electroluminescent device (e.g., OLED) is provided, the structure of which is shown in fig. 1, having the following layer structure: a base (indium tin oxide (ITO as anode 1) coated glass substrate)/hole injection layer 2 (HIL)/hole transport layer 3 (HTL)/light emitting layer 4 (EML)/electron transport layer 5 (ETL)/electron injection layer 6 (EIL), and finally a cathode 7.
The materials required for the fabrication of an OLED are as follows:
the preparation of the organic electroluminescent device comprises the following steps:
(1) Cleaning a substrate: ultrasonic treatment is carried out on the glass substrate coated with the transparent ITO layer (anode 1) in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are that an ethylene glycol solvent is less than or equal to 10wt% and triethanolamine is less than or equal to 1wt%), washing in deionized water and washing in acetone: ultrasonic degreasing in ethanol mixed solvent (volume ratio 1:1), baking in clean environment until completely removing water, and cleaning with ultraviolet light and ozone.
(2) Evaporating an organic light-emitting functional layer:
placing the above glass substrate with anode 1 into vacuum chamber, and vacuumizing to 1×10 -6 Up to 2X 10 -4 Pa, vacuum deposition of HAT (CN) on the anode 1 6 And H isT mixtures, wherein HAT (CN) 6 The mass ratio of HT to the hole injection layer 2 is 3:97, and the vapor deposition thickness is 10nm;
evaporating a hole transport layer 3 on the hole injection layer 2, wherein the evaporating thickness is 80nm;
the light-emitting layer 4 is evaporated on the hole transport layer 3, and the specific preparation method is as follows: vacuum evaporating the luminescent host material and the guest material in a co-evaporation mode, wherein the total evaporation thickness is 30nm;
an electron transport layer 5 is vacuum evaporated on the luminescent layer 4, and the preparation method specifically comprises the following steps: vacuum evaporating BPhen and LiQ in a co-evaporation mode, wherein the total thickness of evaporation is 30nm;
vacuum evaporating an electron injection layer 6 on the electron transport layer 5, wherein the total thickness of the evaporation is 1nm;
al was vapor-deposited on the electron injection layer 6 as the cathode 7, and the total vapor-deposited thickness was 80nm.
Parameters of the layers and their materials and thicknesses in examples 1 to 14 and comparative examples 1 to 5 of the device are shown in Table 5.
TABLE 7
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Device performance test:
instrument: the characteristics of current, voltage, brightness, luminescence spectrum and the like of the device are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
photoelectric characteristic test conditions: the current density was 10mA/cm 2 Room temperature.
Life test: the current density was 20mA/cm 2 The time (in hours) was recorded at room temperature when the device brightness was reduced to 95% of the original brightness.
The device performance test results are shown in table 8:
TABLE 8
| Device embodiment number | Driving voltage (V) | Current efficiency (Cd/A) | Lifetime (h) |
| Example 1 | 3.57 | 25.71 | 546.3 |
| Example 2 | 3.60 | 24.69 | 553.0 |
| Example 3 | 3.50 | 25.76 | 549.9 |
| Example 4 | 3.44 | 25.97 | 577.8 |
| Example 5 | 3.38 | 26.00 | 581.1 |
| Example 6 | 3.58 | 25.76 | 583.9 |
| Example 7 | 3.60 | 25.06 | 540.6 |
| Example 8 | 3.62 | 24.96 | 539.7 |
| Example 9 | 3.21 | 26.03 | 657.9 |
| Example 10 | 3.64 | 24.78 | 538.2 |
| Example 11 | 3.35 | 25.69 | 587.3 |
| Example 12 | 3.67 | 25.50 | 533.9 |
| Example 13 | 3.66 | 24.79 | 541.1 |
| Example 14 | 3.28 | 26.21 | 650.7 |
| Example 15 | 3.31 | 25.11 | 556.7 |
| Example 16 | 3.57 | 24.78 | 549.8 |
| Example 17 | 3.49 | 25.09 | 559.1 |
| Example 18 | 3.37 | 25.64 | 570.9 |
| Example 19 | 3.50 | 25.00 | 563.8 |
| Example 20 | 3.44 | 25.56 | 569.7 |
| Example 21 | 3.39 | 25.61 | 569.0 |
| Example 22 | 3.27 | 26.01 | 580.6 |
| Example 23 | 3.30 | 25.87 | 577.5 |
| Example 24 | 3.34 | 26.41 | 581.6 |
| Comparative example 1 | 4.45 | 12 | 85 |
| Comparative example 2 | 5.00 | 12 | 29 |
| Comparative example 3 | 4.50 | 16 | 69 |
| Comparative example 4 | 5.02 | 11 | 38 |
| Comparative example 5 | 4.8 | 5 | 5 |
As can be seen from table 6, the organic material composition of the present invention has significantly improved lifetime characteristics. When the organic material composition is used as an organic functional layer material, the device can have lower driving voltage (below 3.7V), higher current efficiency (above 24 Cd/A) and higher service life (above 533 h).
From a comparison of comparative examples 1-5 with examples 1-14, it can be seen that the components of the compositions described herein have a synergistic effect in reducing device drive voltage, improving current efficiency, and extending lifetime.
The applicant states that the process of the invention is illustrated by the above examples, but the invention is not limited to, i.e. does not mean that the invention must be carried out in dependence on the above process steps. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (10)
1. An organic material composition, characterized in that the organic material composition comprises at least one compound with a structure shown in a formula 1 and at least one compound with a structure shown in a formula 2,
Z 1 selected from N and CL Y1 Ar Y1 ，Z 2 Selected from N and CL Y2 Ar Y2 ，Z 3 Selected from N and CL Y3 Ar Y3 ，Z 4 Selected from N and CL Y4 Ar Y4 ，Z 5 Selected from N and CL Y5 Ar Y5 ，Z 6 Selected from N and CL Y6 Ar Y6 ，
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 Independently selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl,
L Y1 Ar Y1 、L Y2 Ar Y2 、L Y3 Ar Y3 、L Y4 Ar Y4 、L Y5 Ar Y5 l and L Y6 Ar Y6 Each independently, or adjacent two are linked to form a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring;
wherein n represents an integer of 0 to 3; r1 'to R4' are independently selected from the group consisting of: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; ar5 'and Ar6' are selected from the group consisting of: substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 50 carbon atoms.
2. The organic material composition according to claim 1, wherein the compound of the structure represented by formula 1 is a compound of the structure represented by formula 1-1,
wherein Z is 1 Selected from N and CL Y1 Ar Y1 ，Z 3 Selected from N and CL Y3 Ar Y3 ，Z 5 Selected from N and CL Y5 Ar Y5 And Z is 1 、Z 3 Z is as follows 5 At least two of which are N;
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 ar, ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 Is defined as in claim 1.
3. The organic material composition according to claim 1 or 2, wherein in said Z 1 、Z 3 Z is as follows 5 Wherein Z is 1 、Z 3 Is N, Z 5 For CL Y5 Ar Y5 Wherein L is Y5 Ar Y5 、L Y6 Ar Y6 Each independently or linked to form a substituted or unsubstituted benzene ring; or Z is 1 、Z 5 Is N, Z 3 For CL Y3 Ar Y3 The method comprises the steps of carrying out a first treatment on the surface of the Or Z is 3 、Z 5 Is N, Z 1 For CL Y1 Ar Y1 The method comprises the steps of carrying out a first treatment on the surface of the Or Z is 1 、Z 3 、Z 5 Is N;
preferably Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, triphenylene, anthracenyl, phenanthryl,A group or a group represented by formula 3;
y is selected from O, S and CR W1 R W2 ，
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 When at least one of the compounds is represented by the formula 3,
r in 3 Y1 -R Y8 、R W1 R is R W2 Any one of the compounds and L in the formula 2-1 Y2 、L Y4 Or L Y6 Is connected through chemical bonds;
Ar Y1 、Ar Y2 、Ar Y3 、Ar Y4 、Ar Y5 、Ar Y6 each of which may be the same or different,
R Y1 -R Y8 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are each not adjacent to O and/or S atoms, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy,
R Y1 -R Y8 each independently or adjacent two are linked to form a ring A, which is a substituted or unsubstituted C6-C30 aromatic ring,
R W1 r is R W2 Each independently selected from substituted or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-C30 aryl;
preferably, the group represented by formula 3 is selected from any one of the following groups:
and
Y is selected from O, S and CR W1 R W2 ，R W1 And R is W2 Each independently selected from methyl or phenyl, or R W1 And R is W2 Connecting to form a spiro ring;
R Y1 -R Y8 each independently selected from hydrogen, deuterium, substituted or unsubstituted, such groups as: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl, phenanthryl, benzophenanthryl, pyridyl, dibenzofuranyl, dibenzothienyl, dibenzofuranylphenyl, dibenzothienyl phenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzonaphthofuranyl or benzonaphthothienyl; r is R Y1 -R Y8 Each independently or adjacent two are connected to form a ring A, and the ring A is a substituted or unsubstituted benzene ring;
L Y1 、L Y2 、L Y3 、L Y4 、L Y5 、L Y6 each independently selected from the group consisting of a linkage, phenylene, biphenylene, or naphthylene;
r in the formulae 3-1 to 3-6 Y1 -R Y8 、R W1 R is R W2 Any one of the compounds and L in the formula 2-1 Y2 、L Y4 Or L Y6 Through chemical bond connection.
4. The organic material composition according to any one of claims 1 to 3, wherein Ar 5 ' and Ar 6 ' is selected from the group consisting of substituted or unsubstituted:
wavy lines represent the attachment sites of the groups.
5. The organic material composition according to any one of claims 1 to 4, wherein the compound of the structure represented by formula 1 is selected from the group consisting of:
preferably, the compound of the structure shown in formula 2 is selected from the following compounds:
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6. the organic material composition according to any one of claims 1 to 5, wherein the weight ratio of the compound of the structure represented by formula 1 to the compound of the structure represented by formula 2 is 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 3:7 to 7:3, still more preferably 4:6 to 6:4.
7. An organic electroluminescent material, characterized in that it comprises an organic material composition according to any one of claims 1 to 6.
8. Use of the organic material composition according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7 for the preparation of an optical device.
9. An organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, wherein the material of the organic layer comprises the organic material composition of any one of claims 1-6 or the organic electroluminescent material of claim 7;
preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are stacked in this order from the anode side to the cathode side;
preferably, the material of the light emitting layer comprises a host material and a guest material, the host material comprising the organic material composition according to any one of claims 1 to 6 or the organic electroluminescent material according to claim 7;
preferably, the guest material comprises a phosphorescent dopant comprising a transition metal-containing complex.
10. An organic electroluminescent device, characterized in that it comprises an organic electroluminescent device as claimed in claim 9.
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