CN117658994A - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
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- CN117658994A CN117658994A CN202310795638.8A CN202310795638A CN117658994A CN 117658994 A CN117658994 A CN 117658994A CN 202310795638 A CN202310795638 A CN 202310795638A CN 117658994 A CN117658994 A CN 117658994A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 claims description 61
- -1 cyano, phenyl Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000000872 buffer Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 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 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000001616 biphenylenes Chemical group 0.000 claims 2
- 239000000543 intermediate Substances 0.000 description 63
- 239000010410 layer Substances 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000005259 measurement Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940126540 compound 41 Drugs 0.000 description 3
- 229940125900 compound 59 Drugs 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SRKGZXIJDGWVAI-GVAVTCRGSA-M (e,3r)-7-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)C1=NC(C(C)(C)C)=CC(C=2C=CC(F)=CC=2)=C1\C=C\C(O)C[C@@H](O)CC([O-])=O SRKGZXIJDGWVAI-GVAVTCRGSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- ZARCYQBIHIVLOO-UHFFFAOYSA-N pyridine;triazine Chemical compound C1=CC=NC=C1.C1=CN=NN=C1 ZARCYQBIHIVLOO-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- 229910021595 Copper(I) iodide Inorganic materials 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
- 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
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 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
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- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 238000005265 energy consumption Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
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- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
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- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 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
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
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- 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
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
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- 239000002346 layers by function Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VMFMUJZRXZXYAH-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound C=CC(=O)NC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=1N1CCN(C)CC1 VMFMUJZRXZXYAH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 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
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 229920006395 saturated elastomer Polymers 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
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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Abstract
本发明提供一种有机化合物及其应用，本发明所述有机化合物使能够较高的稳定性并且载流子迁移率较为平衡，进而使包含该有机化合物的有机电致发光器件具有较低的驱动电压、较高的电流效率和较长的寿命。
Description
技术领域
本发明属于有机电致发光技术领域，涉及一种有机化合物及其应用。
背景技术
Pope等人于1965年首次发现了单晶蒽的电致发光性质，这是有机电致发光化合物的首例电致发光现象；1987年，美国Kodak公司的Tang等采用有机小分子半导体材料研制成功低电压、高亮度的有机发光二极管(Organic Light-Emitting Diode，OLED)。有机电致发光二极管(Organic Light-EmittingDiode，OLED)作为一种新型的显示技术，具有自发光、宽视角、低能耗、色彩丰富、响应速度快、适用温度范围广以及可实现柔性显示等诸多优点。
为了提高有机发光二极管的发光效率，各种基于荧光和磷光的发光材料体系已被开发出来，使用荧光材料的有机发光二极管具有可靠性高的特点，但其在电气激发下其内部电致发光量子效率被限制为25％，这是因为电流产生的激子的单重激发态和三重激发态的比例为1:3。与此相反，使用磷光材料的有机发光二极管已经取得了几乎100％的内部电致发光量子效率，因此磷光发光材料的开发已被广泛研究。
发光材料(客体)可与基质材料(主体)一起用作为发光材料以改善颜色纯度、发光效率和稳定性。由于当使用主体材料/客体体系作为发光器件的发光层时，主体材料对电致发光器件的效率和特性影响很大，因此主体材料的选择很重要。目前，现有有机电致发光材料的堆叠性能较差，导致有机电致发光材料的稳定性不高、载流子迁移率不平衡的问题，造成包含该有机电致发光材料的有机电致发光器件的驱动电压较高、发光效率较低、寿命较短的问题，严重限制了有机电致发光器件的应用。
发明内容
针对现有技术的不足，本发明的目的在于提供一种有机化合物及其应用。
为达到此发明目的，本发明采用以下技术方案：
一方面，本发明提供一种有机化合物，所述有机化合物具有式1所示结构
Y选自O或S，X1选自N或CLX1RX1，X2选自N或CLX2RX2，
L1-L10、LX1-LX2各自独立选自单键、取代或未取代的C6-C30的亚芳基，
R1-R9、RX1-RX2各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C30的烷氧基、取代或未取代的C7-C60的芳氧基，
R10选自取代或未取代的C1-C30的烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C30的烷氧基、取代或未取代的C7-C60的芳氧基，
所述取代的C1-C30的烷基、取代的C3-C30的环烷基、取代的C6-C60的芳基、取代的C3-C60的杂芳基、取代的C1-C30的烷氧基、取代的C7-C60的芳氧基中取代基各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合。
优选地，L1-L10、LX1-LX2各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
优选地，R1-R9、RX1-RX2各自独立选自氢、氘、卤素、取代的三嗪基；
所述取代的三嗪基的取代基各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合。
优选地，所述取代的三嗪基的取代基各自独立选自氘、卤素、氰基、苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、二苯并呋喃基、二苯并噻吩基、9,9’-二甲基芴基、9,9’-二苯基芴基、螺二芴基、咔唑基中的任意一种或至少两种的组合。
优选地，所述有机化合物具有1-1至1-12中任意一种结构：
R11、R12各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合；
L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
X1、X2、Y、L10、R10的定义与式1中相同。
优选地，R10选自苯基；
优选地，R2-R3、R6-R9选自氢、氘；
优选地，X1选自N或CH，X2选自N或CH；
优选地，X1选自CH，X2选自CH；
优选地，X1选自N；
优选地，X2选自N；
优选地，L1-L10选自单键。
优选地，所述有机化合物选自如下化合物中的任意一种：
在本发明中，式1所示有机化合物通过如下合成路线制备得到：路线1：
路线2：
路线3：
路线4：
另一方面，本发明提供一种有机电致发光材料，所述有机电致发光材料包含如上所述的有机化合物。
另一方面，本发明提供一种有机电致发光器件，所述有机电致发光器件包括阳极、阴极和位于所述阳极和阴极之间的有机薄膜层，所述机薄膜层包括如上所述的有机化合物或如上所述的有机电致发光材料。
优选地，所述有机薄膜层包括空穴注入层、空穴传输层、发光辅助层、发光层、空穴阻挡层、电子缓冲层、电子传输层、电子缓冲层或电子注入层中的任意一种或至少两种的组合；
优选地，所述机薄膜层包括发光层，所述发光层包括如上所述的有机化合物。
优选地，所述发光层包括主体材料和客体材料，所述主体材料包括如上所述的有机化合物。
优选地，所述机薄膜层包括电子传输层，所述电子传输层包含如上所述的有机化合物。
另一方面，本发明提供一种电子设备，所述电子设备包括如上所述的有机电致发光器件。
优选地，所述电子设备包括光纤、照明设备、电子照相感光体、光电转换器、有机太阳能电池、开关元件、有机发光场效应晶体管、图像传感器或染料激光器中的任意一种。
本发明中的术语“有机电致发光材料”意指可以用于有机电致发光装置中并且可以包含至少一种化合物的材料。如有需要，有机电致发光材料可以包含在构成有机电致发光装置的任何层中。例如，有机电致发光材料可以是空穴注入材料、空穴传输材料、空穴辅助材料、发光辅助材料、电子阻挡材料、发光材料(含有主体材料和掺杂剂材料)、电子缓冲材料、空穴阻挡材料、电子传输材料、电子注入材料等。
本发明中的术语“多种有机电致发光材料”意指一种或多种包含至少两种化合物的组合的有机电致发光材料，所述材料可以包含在构成有机电致发光装置的任何层中。它可以意指包含在有机电致发光装置中之前(例如，在气相沉积之前)的材料和包含在有机电致发光装置中之后(例如，在气相沉积之后)的材料两者。例如，多种有机电致发光材料可以是至少两种化合物的组合，所述材料可以包含在以下中的至少一个中：空穴注入层、空穴传输层、空穴辅助层、发光辅助层、电子阻挡层、发光层、电子缓冲层、空穴阻挡层、电子传输层和电子注入层。至少两种化合物可以包含在同一层或不同层中，并且可以被混合-蒸发或共蒸发，或可以被单个地蒸发。
本发明中的术语“多种主体材料”意指包含至少两种主体材料的组合的有机电致发光材料。它可以意指包含在有机电致发光装置中之前(例如，在气相沉积之前)的材料和包含在有机电致发光装置中之后(例如，在气相沉积之后)的材料两者。本发明的多种主体材料可以包含在构成有机电致发光装置的任何发光层中。包含在本发明的多种主体材料中的两种或更多种化合物可以包含在一个发光层中，或者可以分别包含在不同的发光层中。例如，当一个层中包含两种或更多种主体材料时，所述层可以通过混合蒸发形成，或者可以同时通过单独的共蒸发形成。
关于取代基术语的定义
如在本发明中所用，术语“卤素”可以包括氟、氯、溴或碘。
如在本发明所用，术语“C1-C30烷基”是指衍生自具有1至30个碳原子的直链或支链饱和烃的单价取代基，其实例包括但不限于甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基和己基。
如在本发明所用，术语“C3-C30环烷基”是指衍生自具有1至30个环主链碳原子的单环烃或多环烃，所述环烷烃可包括环丙基、环丁基、环戊基、环己基、环戊甲基、环己基甲基、金刚烷基等。
本发明中芳基、亚芳基包括单环、多环或稠环芳基，所述环之间可以被短的非芳族单元间断，并且可以包含螺结构，包括但不限于苯基、联苯基、三联苯基、萘基、菲基、苯基菲基、联萘基、苯基萘基、萘基苯基、蒽基、茚基、三亚苯基、并四苯基、芘基、苝基、芴基、苯基芴基、二苯基芴基、苯并芴基、螺二芴基、基、萘并萘基、荧蒽基等。
本发明中杂芳基、亚杂芳基包括单环、多环或稠环杂芳基，所述环之间可以被短的非芳族单元间断，所述杂原子包括氮、氧、硫。包括但不限于呋喃基、苯硫基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、吩噻嗪基、菲啶基、苯并间二氧杂环戊烯基、二氢吖啶基，及其衍生物等。
如在本发明所用，术语“取代的”是指与化合物中的氢原子被另一取代基取代。该位置不限于特定位置，只要该位置上的氢能够被取代基取代即可。并且还包括氢原子被两个或更多个取代基的连接形成的基团替代。当出现两个或两个以上取代基时，两个或两个以上取代基可以相同或不同。例如，通过两个或更多个取代基的连接形成的基团可以是吡啶-三嗪。即，吡啶-三嗪可以被解释为杂芳基取代基、或其中两个杂芳基取代基相连接的取代基。
如在本发明所用，除非另有说明，氢原子包括氕、氘和氚。
在本发明中，基团的限定中限定了碳原子数的范围，其碳原子数为所限定范围内的任一整数，例如C6-C30芳基，代表芳基的碳原子数可以是6-60所包含的范围内的任意整数，例如6、8、10、13、15、17、20、22、25或30等。
相对于现有技术，本发明具有以下有益效果：
本发明提供有机电致发光化合物，所述有机电致发光化合物的HOMO、LUMO能级与相邻能级有较高的匹配度，使所述有机电致发光化合物获得较高的稳定性并且载流子迁移率较为平衡，进而使包含该有机电致发光材料的有机电致发光器件具有较低的驱动电压、较高的电流效率和较长的寿命。
附图说明
图1为本发明所述有机电致发光器件的结构示意图；
其中，1为基板、2为阳极、3为空穴注入层、4为空穴传输层、5为发光层、6为电子传输层、7为电子注入层、8为阴极。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了，所述实施例仅仅是帮助理解本发明，不应视为对本发明的具体限制。
1、中间体INT-1A的制备
中间体INT-1-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入原料SM-1-1(1mmol)，原料SM-2-1(1mmol)，甲苯(9毫升)，乙醇(3毫升)，水(3毫升)，加入四三苯基膦钯(0.05mmol)，碳酸钾(2mmol)，加热至90摄氏度，反应12小时，反应结束后，降至室温，用水与乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷＝1：50)分离，得中间体INT-1-1(0.17g，产率45％)。
中间体INT-2-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-1-1(1mmol)，(甲氧基甲基)三苯基氯化膦(1.8mmol)，THF(10毫升)，降温至-5—-10摄氏度，用恒压滴液漏斗缓慢滴加t-BuOK(27g)的四氢呋喃(150mL)溶液，温度始终维持在-5℃以下。滴加完后，在此温度下反应20min。再缓慢升至室温，待反应液到达室温后，继续反应1h，停止反应。用水与乙酸乙酯萃取反应液，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷＝1：50)分离，得中间体INT-2-1(0.33g，产率80％)。
中间体INT-3-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-2-1(1mmol)和六氟异丙醇(14mL)。在氮气保护的条件下，将温度降至-5～-10℃，到达此温度后，用恒压滴液漏斗缓慢滴加三氟甲磺酸(3mmol)，温度始终维持在-5℃以下。滴加完后，在此温度下反应20min。再缓慢升至室温，待反应液到达室温后，继续反应1h，停止反应。用水与乙酸乙酯萃取反应液，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷体积比＝1：50)分离，得中间体INT-3-1(0.29g，产率76％)。
中间体INT-1A的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，氮气保护下，依次加入中间体INT-3-1(1mmol)，双联硼酸酯(1.1mmol)，1，4-二氧六环(10mL)，加入Pd(dppf)Cl2(0.03mmol)，乙酸钾(2.5mmol)，加热至100℃，反应5小时，反应结束后，降至室温，用乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(乙酸乙酯：正己烷体积比＝1：50)分离，得中间体INT-1A(产率72％)。
中间体INT-2A至INT-24A的制备步骤如上所述，区别在于第一步用不同位置氯取代的原料替代SM-2-1，含N杂环的的原料替代SM1-1或噻吩替代SM1-1中的呋喃：
2、中间体INT-1B的制备
中间体INT-4-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-3-2(1.0mmol)，SM-3-1(1.2mmol)，Pd(dppf)Cl2(0.03mmol)，碳酸钾(2.5mmol)，1,4-二氧六环/水(10mL/2mL)，升温至90摄氏度反应5小时，反应结束后降至室温，用饱和氯化铵水溶液淬灭，乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(乙酸乙酯：正己烷＝1：50)分离，得中间体INT-4-1(产率81％)。
中间体INT-1B的合成：
取100毫升三颈圆底瓶并放入搅拌子与上接回流管，氮气保护下，依次加入原料INT-4-1(1mmol)，双联硼酸酯(1.1mmol)，1，4-二氧六环(10mL)，加入Pd(dppf)Cl2(0.03mmol)，乙酸钾(2.5mmol)，加热至100℃，反应5小时，反应结束后，降至室温，用乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(乙酸乙酯：正己烷体积比＝1：50)分离，得中间体INT-1B(产率70％)。
中间体INT-1B至INT-20B的制备步骤如上所述，区别在于第一步用不同位置氯取代的中间体替代SM-3-2：
3、中间体INT-1C的制备
中间体INT-5-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入原料SM-4-1(1mmol)，原料SM-5-1(1mmol)，DMF 10ml，加入碘化亚铜(0.05mmol)，碳酸钾(2mmol)，加热至110摄氏度，反应12小时，反应结束后，降至室温，用水与乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷体积比＝1：50)分离，得中间体INT-5-1(0.15g，产率32％)。
中间体INT-6-1的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-5-1(1mmol)，DMF 10ml，加入醋酸钯(0.05mmol)，碳酸钾(2mmol)，加热至150摄氏度，反应12小时，反应结束后，降至室温，用水与乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷体积比＝1：50)分离，得中间体INT-6-1(0.29g，产率69％)。
中间体INT-1C的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，氮气保护下，依次加入原料INT-6-1(1mmol)，双联硼酸酯(1.1mmol)，1，4-二氧六环(10mL)，加入Pd(dppf)Cl2(0.03mmol)，乙酸钾(2.5mmol)，加热至100℃，反应5小时，反应结束后，降至室温，用乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(乙酸乙酯：正己烷体积比＝1：50)分离，得中间体INT-1C(产率74％)。
中间体INT-2C至INT-20C的制备步骤如上所述，区别在于第一步用不同位置溴取代的中间体替代SM-5-1：
4、化合物3的制备
化合物3的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-1A(1mmol)，中间体INT-3D(1.1mmol)，甲苯(9毫升)，乙醇(3毫升)，水(3毫升)，加入钯132(0.05mmol)，碳酸氢钠(2mmol)，加热至90摄氏度，反应12小时，反应结束后，降至室温，用水与乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷体积比＝1：50)分离，得最终化合物3(0.61g，产率84％)。
元素分析：C53H33N3O理论值：C,87.46；H,4.57；N,5.77；O,2.20；实测值：C,87.50；H,4.58；N,5.73；HRMS(ESI)m/z[M+H]+：理论值：727.26；实测值：728.33。
化合物24的制备
化合物24的合成：同化合物3的合成，区别在于用中间体INT-3A替代中间体INT-1A，中间体INT-24D替代中间体INT-3D，得化合物24(0.58g，产率85％)。
元素分析：C47H27N3OS理论值：C,82.80；H,3.99；N,6.16；O,2.35；S,4.70；实测值：C,82.83；H,4.01；N,6.12；S,4.70；HRMS(ESI)m/z[M+H]+：理论值：681.19；实测值：682.54。
化合物41的制备
化合物41的合成：同化合物3的合成，区别在于用中间体INT-12A替代中间体INT-1A，中间体INT-41D替代中间体INT-3D，得化合物41(0.56g，产率84％)。
元素分析：C46H26N4O2理论值：C,82.87；H,3.93；N,8.40；O,4.80；实测值：C,82.93；H,3.95；N,8.32；HRMS(ESI)m/z[M+H]+：理论值：666.21；实测值：667.26。
化合物59的制备
化合物59的合成：同化合物3的合成，区别在于用中间体INT-10A替代中间体INT-1A，中间体INT-59D替代中间体INT-3D，得化合物59(0.57g，产率82％)
元素分析：C49H32N4O理论值：C,84.95；H,4.66；N,8.09；O,2.31；实测值：C,84.99；H,4.69；N,8.01；HRMS(ESI)m/z[M+H]+：理论值：692.26；实测值：693.34。
化合物67的制备
化合物67的合成：取100毫升三颈圆底瓶并放入搅拌子与上接回流管，加入中间体INT-1C(1mmol)，中间体INT-67D(1mmol)，甲苯(9毫升)，乙醇(3毫升)，水(3毫升)，加入钯132(0.05mmol)，碳酸氢钠(2mmol)，加热至90摄氏度，反应12小时，反应结束后，降至室温，用水与乙酸乙酯萃取，有机相用无水硫酸镁干燥，使用旋转蒸发仪除去溶剂，粗产物用柱层析(DCM：正己烷体积比＝1：50)分离，得最终化合物67(0.56g，产率83％)。
元素分析：C46H26N4O2理论值：C,82.87；H,3.93；N,8.40；O,4.80；实测值：C,82.90；H,3.94；N,8.36；HRMS(ESI)m/z[M+H]+：理论值：666.21；实测值：667.55。
化合物74的制备
化合物74的合成：同化合物3的合成，区别在于用中间体INT-20A替代中间体INT-1A，中间体INT-74D替代中间体INT-3D，得化合物74(0.54g，产率83％)。
元素分析：C46H28N4O理论值：C,84.64；H,4.32；N,8.58；O,2.45；实测值：C,84.71；H,4.32；N,8.52；HRMS(ESI)m/z[M+H]+：理论值：652.23；实测值：653.38。
化合物89的制备
化合物89的合成：同化合物3的合成，区别在于用中间体INT-18A替代中间体INT-1A，中间体INT-89D替代中间体INT-3D，得化合物89(0.56g，产率84％)
元素分析：C46H26N4O2理论值：C,82.87；H,3.93；N,8.40；O,4.80；实测值：C,82.93；H,3.94；N,8.33；HRMS(ESI)m/z[M+H]+：理论值：666.21；实测值：667.30。
化合物101的制备
化合物101的合成：同化合物67的合成，区别在于用中间体INT-11C替代中间体INT-1C，中间体INT-101D替代中间体INT-67D，得化合物101(0.52g，产率77％)。
元素分析：C46H26N4O2理论值：C,82.87；H,3.93；N,8.40；O,4.80；实测值：C,82.90；H,3.95；N,8.35；HRMS(ESI)m/z[M+H]+：理论值：666.21；实测值：667.38。
化合物185的制备
化合物185的合成：同化合物3的合成，区别在于用中间体INT-24A替代中间体INT-1A，中间体INT-101D替代中间体INT-3D，得化合物185(0.55g，产率81％)。
元素分析：C46H26N4OS理论值：C,80.92；H,3.84；N,8.21；O,2.34；S,4.70；实测值：C,80.94；H,3.85；N,8.18；S,4.70；HRMS(ESI)m/z[M+H]+：理论值：682.18；实测值：683.25。
器件实施例
应用例1-10和对比应用例1-2
以下应用例1-10和对比应用例1分别提供不同的OLED，结构示意图如图1所示，其均具有以下层结构：基底1(氧化铟锡(ITO)作为阳极2的涂层玻璃基板)/空穴注入层3(HIL)/空穴传输层4(HTL)/发光层5(EML)/电子传输层6(ETL)/电子注入层(EIL)7/，且最后是阴极8。
所用材料如下所示：
上述有机电致发光器件的制备包括如下步骤：
(1)基板清理：将涂布了透明ITO的玻璃基板在水性清洗剂(所述水性清洗剂的成分及浓度：乙二醇类溶剂≤10wt％，三乙醇胺≤1wt％)中超声处理，在去离子水中冲洗，在丙酮：乙醇混合溶剂(体积比1：1)中超声除油，在洁净环境下烘烤至完全除去水份，然后用紫外光和臭氧清洗。
(2)蒸镀有机发光功能层：
把上述带有阳极层的玻璃基板置于真空腔内，抽真空至1×10-6至2×10-4Pa，在上述阳极层膜上真空蒸镀HATCN与HT的混合物，其中HATCN与HT的质量比为3:97，作为空穴注入层，蒸镀厚度为10nm；
在空穴注入层上蒸镀空穴传输层(材料为HT)，蒸镀膜厚为80nm；
在空穴传输层上蒸镀发光层，具体制备方法为：以共蒸的方式真空蒸镀发光主体材料(其材料如表1所示)和客体材料(piq)2Ir(acac)，蒸镀总膜厚为30nm；
(可选)在发光层上蒸镀一层电子缓冲层，蒸镀厚度为10nm；
在电子缓冲层上蒸镀一层电子传输层，具体制备方法为：以共蒸的方式真空蒸镀ET和LiQ，蒸镀总膜厚为30nm；
在电子传输层上真空蒸镀一层电子注入层(材料为LiQ)，蒸镀总膜厚为1nm；
在电子注入层上蒸镀Al，蒸镀总膜厚为90nm。
器件中各层及其材料以及厚度等参数如下表1所示：
表1
器件性能测试：
仪器：器件的电流、电压、亮度、发光光谱等特性采用PR 650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试；
器件实施例1-10测试条件：
光电特性测试条件：电流密度为10mA/cm2。
寿命测试：电流密度为50mA/cm2，器件亮度下降至原始亮度的95％时记录时间(以小时计)。
器件性能测试结果如表2所示：
表2
| 项目 | 驱动电压(V) | 电流效率(Cd/A) | 寿命T95(hrs) |
| 实施例1 | 3.60 | 18.56 | 277.9 |
| 实施例2 | 3.58 | 19.69 | 293.5 |
| 实施例3 | 3.44 | 22.41 | 321.7 |
| 实施例4 | 3.57 | 19.14 | 275.4 |
| 实施例5 | 3.57 | 19.68 | 281.3 |
| 实施例6 | 3.52 | 20.56 | 285.5 |
| 实施例7 | 3.47 | 22.10 | 312.4 |
| 实施例8 | 3.46 | 22.24 | 306.7 |
| 实施例9 | 3.55 | 21.33 | 298.4 |
| 实施例10 | 3.51 | 20.18 | 302.4 |
| 对比例1 | 5.34 | 11.09 | 64.0 |
由表2数据可以看出，本发明有机化合物能够使得有机电致发光器件具有较低的驱动电压(3.60V以下)，较高的电流效率(高达18Cd/A以上)以及较长的寿命(270h以上)。
申请人声明，本发明通过上述实施例来说明本发明的有机化合物及其应用，但本发明并不局限于上述实施例，即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了，对本发明的任何改进，对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等，均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种有机化合物，所述有机化合物具有式1所示结构
Y选自O或S，X1选自N或CLX1RX1，X2选自N或CLX2RX2，
L1-L10、LX1-LX2各自独立选自单键、取代或未取代的C6-C30的亚芳基，
R1-R9、RX1-RX2各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C30的烷氧基、取代或未取代的C7-C60的芳氧基，
R10选自取代或未取代的C1-C30的烷基、取代或未取代的C3-C30的环烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C30的烷氧基、取代或未取代的C7-C60的芳氧基，
所述取代的C1-C30的烷基、取代的C3-C30的环烷基、取代的C6-C60的芳基、取代的C3-C60的杂芳基、取代的C1-C30的烷氧基、取代的C7-C60的芳氧基中取代基各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合。
2.根据权利要求1所述的有机化合物，其特征在于，L1-L10、LX1-LX2各自独立选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
3.根据权利要求1或2所述的有机化合物，其特征在于，R1-R9、RX1-RX2各自独立选自氢、氘、卤素、取代的三嗪基；
所述取代的三嗪基的取代基各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合。
4.根据权利要求1-3中任一项所述的有机化合物，其特征在于，所述取代的三嗪基的取代基各自独立选自氘、卤素、氰基、苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、二苯并呋喃基、二苯并噻吩基、9,9’-二甲基芴基、9,9’-二苯基芴基、螺二芴基、咔唑基中的任意一种或至少两种的组合。
5.根据权利要求1-4中任一项所述的有机化合物，其特征在于，所述有机化合物具有1-1至1-12中任意一种结构：
R11、R12各自独立选自氘、卤素、氰基、C6-C30的芳基、C3-C30的杂芳基、C1-C12的烷基、C3-C12的环烷基的一种或至少两种的组合；
L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
X1、X2、Y、L10、R10的定义与式1中相同。
优选地，R10选自苯基；
优选地，R2-R3、R6-R9选自氢、氘；
优选地，X1选自N或CH，X2选自N或CH；
优选地，X1选自CH，X2选自CH；
优选地，X1选自N；
优选地，X2选自N；
优选地，L1-L10选自单键。
6.根据权利要求1-5中任一项所述的有机化合物，其特征在于，所述有机化合物选自如下化合物中的任意一种：
7.一种有机电致发光材料，其特征在于，所述有机电致发光材料包含如权利要求1-6中任一项所述的有机化合物。
8.一种有机电致发光器件，其特征在于，所述有机电致发光器件包括阳极、阴极和位于所述阳极和阴极之间的有机薄膜层，所述机薄膜层包括如权利要求1-6中任一项所述的有机化合物或如权利要求7所述的有机电致发光材料。
9.根据权利要求8所述的有机电致发光器件，其特征在于，所述有机薄膜层包括空穴注入层、空穴传输层、发光辅助层、发光层、空穴阻挡层、电子缓冲层、电子传输层、电子缓冲层或电子注入层中的任意一种或至少两种的组合；
优选地，所述机薄膜层包括发光层，所述发光层包括如权利要求1-6中任一项所述的有机化合物；
优选地，所述发光层包括主体材料和客体材料，所述主体材料包括如权利要求1-6中任一项所述的有机化合物；
优选地，所述机薄膜层包括电子传输层，所述电子传输层包含如权利要求1-6中任一项所述的有机化合物。
10.一种电子设备，其特征在于，所述电子设备包括如权利要求8或9所述的有机电致发光器件。
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