CN115626898A - 一种含喹喔啉结构的稠杂环化合物及其应用 - Google Patents
一种含喹喔啉结构的稠杂环化合物及其应用 Download PDFInfo
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- CN115626898A CN115626898A CN202110804902.0A CN202110804902A CN115626898A CN 115626898 A CN115626898 A CN 115626898A CN 202110804902 A CN202110804902 A CN 202110804902A CN 115626898 A CN115626898 A CN 115626898A
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- Prior art keywords
- substituted
- unsubstituted
- phenyl
- ring
- carbazolyl
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 title claims abstract description 31
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 28
- -1 phenyl-substituted naphthyl Chemical group 0.000 claims description 67
- 239000010410 layer Substances 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- OSOLELDZBFOFHO-UHFFFAOYSA-N 2-phenylphenanthrene Chemical class C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3C=CC2=C1 OSOLELDZBFOFHO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005509 dibenzothiophenyl group Chemical class 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004434 sulfur atom 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001555 benzenes Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical group C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 claims description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical group C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005878 benzonaphthofuranyl group Chemical class 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 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
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- NXOVZLREWXNIDP-UHFFFAOYSA-N 7h-pyrazino[2,3-c]carbazole Chemical compound N1=CC=NC2=C3C4=CC=CC=C4NC3=CC=C21 NXOVZLREWXNIDP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 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 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 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
- 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 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
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 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
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000002346 layers by function 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
- 238000000034 method Methods 0.000 description 1
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- VUYVXCJTTQJVKJ-UHFFFAOYSA-L palladium(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Pd]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 VUYVXCJTTQJVKJ-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 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
- 239000004065 semiconductor Substances 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 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
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
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Abstract
本发明提供一种含喹喔啉结构的稠杂环化合物及其应用，所述含喹喔啉结构的稠杂环化合物具有式(1)所示结构，本发明的化合物使得有机电致发光器件具有更低的驱动电压，更高的电流效率和更长的寿命。
Description
技术领域
本发明属于有机电致发光材料领域，涉及一种含喹喔啉结构的稠杂环化合物及其应用。
背景技术
有机电致发光(OLED)器件是基于有机材料的一种半导体发光器件，与传统发光技术相比，其具有较宽的视角、较大的对比率以及较快的响应时间，可在无额外背光源的条件下实现全色显示，近年来备受关注。
有机电致发光器件可以由空穴注入层、空穴传输层、发光辅助层、发光层、电子传输层、电子注入层等层组成，各层材料对应为空穴注入材料、空穴传输材料、发光辅助材料、发光材料、电子传输材料、电子注入材料，随着器件结构的优化，材料的种类不断变多，其中发光层材料是OLED的关键材料，对于整个OLED产业链至关重要，也是技术壁垒最高的领域。
CN105713016A公开了一种OLED材料，所述OLED材料的结构如下：
R1选自甲基、乙基、异丙基、叔丁基、直链或枝化的C1～C12含氧烷基、苯环取代的含氮杂环结构或C5～C60多环芳基共轭结构基团中的任一种。但是其主要作为电子传输材料降低驱动电压，提高电子效率。
CN107216330A公开了一种OLED材料，所述OLED材料具有如下结构：
R1为C5-C60多环芳基共轭结构基团中的任意一种；R2为直链或枝化的C1-C12烷基或C5-C60多环芳基共轭结构基团中的任意一种；可以作为发光层或传输层，应用在有机电致发光器件中，可以获得更加稳定的效果、优良的光电性能和更长的使用寿命。
CN107602568A公开了一种基于吲哚并喹喔啉的三芳胺类衍生物，其具有如下结构：
其中，Ar1、Ar2、L独立的选自C6～C50的取代或未取代的芳基、C10～C50的取代或未取代的稠环芳基、C6～C50的取代或未取代的杂芳基、C10～C50的取代或未取代的稠环杂芳基中的一种。可做为有机发光器件中的主体发光材料、客体发光材料、电子传输材料或空穴传输材料，尤其是作为有机发光器件中的主体材料时，具有刚性结构的吲哚并喹喔啉的三芳胺类衍生物具有较高的玻璃化转变温度，而这些都有利于延长有机发光器件寿命，且表现出高效率、低驱动电压和不易结晶的优点。
虽然如上材料可作为发光层材料应用于OLED器件，但是其器件的驱动电压仍然较高，寿命提高并不理想，在本领域中，期望进一步开发性能更加优异的发光层材料以进一步降低驱动电压，提高电流效率，延长寿命。
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。
为达此目的，本发明采用以下技术方案：
一方面，本发明提供一种含喹喔啉结构的稠杂环化合物，所述化合物具有式(1)所示结构：
R1-R6各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C2-C30烯基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C2-C30烯基、取代或未取代的C2-C30炔基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
R1-R6各自独立存在或相邻两者连接成环，所述环为取代或未取代的苯环，
L选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C5-C30的亚杂芳基，
Ar1选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60的杂芳基，取代或未取代的C6-C60芳胺基、取代或未取代的C5-C60的杂芳胺基、取代或未取代的C5-C60的芳基杂芳胺基，
n选自0-3的整数(例如可以为0、1、2或3)，
m选自0-5的整数(例如可以为0、1、2、3、4或5)，
n1选自0-1的整数，
m1选自0-1的整数。
在本发明中，所述含喹喔啉结构的稠杂环化合物中喹喔啉结构与含有七元芳香环的结构稠合，这样的母核结构使得电子和空穴结合更有效，避免因空穴与空穴传输不平衡导致电流效率下降、器件寿命缩短。
优选地，n1+m1＝1。
优选地，L-Ar1选自
其中Ar2、Ar3各自独立选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60的杂芳基。
优选地，Ar2、Ar3各自独立选自取代或未取代的如下基团：苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基、二苯并咔唑基；
优选地，L-Ar1选自
其中虚线代表L与Ar3通过化学键连接成环；
更优选地，L-Ar1选自取代或未取代的如下基团：
优选地，L-Ar1选自
其中虚线代表Ar2、Ar3通过化学键连接成环，
更优选地，L-Ar1选自取代或未取代的如下基团
优选地，Ar1选自
其中X1选自N或CRX1，X2选自N或CRX2，X3选自N或CRX3，X4选自N或CRX4，X5选自N或CRX5，
RX1、RX2、RX3、RX4、RX5各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
RX1、RX2、RX3、RX4、RX5各自独立存在，或相邻两者连接成环，所述环为取代或未取代的苯环、吡啶环、萘环、蒽环、菲环、萘并噁唑环、萘并噻唑环、苯并呋喃环或苯并噻吩环，
优选地，Ar1选自
优选地，Ar1选自
其中X1、X2、X5中任意两者选自N，
Y1选自N、CRY1，Y2选自N、CRY2，Y3选自N、CRY3，Y4选自N、CRY4，
RY1、RY2、RY3、RY4各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
RY1、RY2、RY3、RY4各自独立存在，或相邻两者连接成环，所述环为取代或未取代的苯环。
更优选，X2、X5选自N。
更优选，X1、X5选自N。
更优选，Y1选自CRY1，Y2选自CRY2，Y3选自CRY3，Y4选自CRY4，
更优选，RX1、RX2、RX3、RX4、RX5、RY1、RY2、RY3、RY4各自独立选自氢、取代或未取代的如下基团：苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基。
优选地，所述L各自独立选自亚苯基、亚联苯基、亚萘基，
优选地，R1-R6各自独立选自氢、氘、氰基、氟、甲基、乙基、叔丁基、氘取代甲基、氟取代甲基、苯基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、二甲基芴基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基，
优选地，Ar1选自苯基、联苯基、三联苯基、萘基、苯并菲基、苯基取代萘基、萘基取代苯基、二苯并呋喃基、二苯并噻吩基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、2-苯基菲[3,4-d]噁唑基、2-苯基菲[3,4-d]噻唑基。
在本发明中，所述基团含有取代基时，所述取代基各自独立选自氘、卤素、氰基、未取代或R'取代的C1-C6的烷基、未取代或R'取代的C6-C12的芳基、未取代或R'取代的C2-C20的杂芳基；R'选自氘、卤素、氰基、氘取代的甲基、卤素取代的甲基。
更优选地，所述C1-C6的烷基选自甲基、乙基、叔丁基；
所述C6-C12的芳基选自苯基、联苯基、萘基；
所述C3-C20的杂芳基选自三嗪基、吡啶基、苯基取代吡啶基、吡啶基取代苯基、二苯并呋喃基、二苯并噻吩基。
优选地，所述含喹喔啉结构的稠杂环化合物为如下化合物中的任意一种：
如在本发明中所用，术语“卤素”可以包括氟、氯、溴或碘，优选氟。
如在本发明所用，术语“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、丙基、异丁基、仲丁基、叔丁基、戊基、异戊基和己基。
如在本发明所用，除非另有说明，术语“环烷基”是指衍生自具有3至30个碳原子的单环或多环非芳族烃的单价取代基。这种环烷基的实例包括但不限于环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷等。
本发明中杂芳基、亚杂芳基包括单环、多环或稠环芳基，所述环之间可以被短的非芳族单元间断，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。
优选地，所述芳基选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、9,9'-二甲基芴基、9,9'-二苯基芴基或螺二芴基。
优选地，所述杂芳基选自二苯并呋喃基、二苯并噻吩基、咔唑基、三嗪基、吡啶基、嘧啶基、咪唑基、噁唑基、噻唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、萘并咪唑基、萘并噁唑基、萘并噻唑基、菲并咪唑基、菲并噁唑基、菲并噻唑基、喹喔啉基、喹唑啉基、吲哚并咔唑基、吲哚并芴基、苯并噻吩并吡嗪基、苯并噻吩并嘧啶基、苯并呋喃并吡嗪基、苯并呋喃并嘧啶基、吲哚并吡嗪基、吲哚并嘧啶基、茚并吡嗪基、茚并嘧啶基、螺(芴-9,1’-茚)并吡嗪基、螺(芴-9,1’-茚)并嘧啶基、苯并呋喃并咔唑基或苯并噻吩并咔唑基。
如在本发明所用，术语“芳氧基”是指由RO-表示的单价取代基，其中R表示具有6至30个碳原子的芳基。这种芳氧基的实例包括但不限于苯氧基、萘氧基、二苯氧基等。
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。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。
如在本发明所用，除非另有说明，氢原子包括氕、氘和氚。
本发明中“相邻两个基团连接成环”是指处于同一环或相邻环中相邻位置的2个取代基之间可以通过化学键相互连接成环，本发明对具体的连接成环方式不做限定(举例通过单键连接、通过苯环连接、通过萘环连接、通过
稠和、通过
稠和、通过
稠和、通过
稠和、通过
稠和；其中
表示稠和位置)，如下文涉及相同的描述时，具有相同的意义。
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-C60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、15、20、30、35、40、45、50、55或60等。
在本发明中，所述含喹喔啉结构的稠杂环化合物的制备路径如下：
其中OTf代表
另一方面，本发明提供一种有机电致发材料，所述有机电致发光材料包括如上所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
另一方面，本发明提供一种有机电致发光组合物，所述有机电致发光组合物包括如上所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
另一方面，本发明提供了如上所述的含喹喔啉结构的稠杂环化合物在制备光学器件中的应用。
优选地，所述光学器件包括有机电致发光器件、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机集成电路、有机太阳能电池、有机场淬灭器件、发光电化学电池、有机激光二极管或有机光感受器中任意一种。
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和阴极，和设置在阳极和阴极间的有机层，所述有机层包括如上所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
优选地，所述有机层至少包含空穴注入层、空穴传输层、发光层、电子传输层、电子注入层。
优选地，所述发光层的材料包含主体材料和客体材料，所述主体材料包含如上所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合；
优选地，所述客体材料为磷光掺杂剂，所述磷光掺杂剂为含过渡金属的配合物，优选为含Ir或Pt的配合物。
优选地，所述电子传输层的材料至少包含如上所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
另一方面，本发明提供一种有机电致发光设备，所述有机电致发光设备包括如上所述的有机电致发光器件。
相对于现有技术，本发明具有以下有益效果：
本发明的含喹喔啉结构的稠杂环化合物有效提高电子和空穴的结合率，提高器件的发光效率和延长器件的使用寿命，本发明的化合物使得有机电致发光器件具有更低的驱动电压(3.98V以下)，更高的电流效率(26Cd/A以上)和更长的寿命(206h以上)。
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。
合成实施例
(1)1-C的合成：取50毫升双颈圆底烧瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入化合物1-A(1mmol)、1-B(1mmol)、碳酸钾(K2CO3，1.5mmol)、乙醇(3毫升)、水(3毫升)、甲苯(15毫升)和四(三苯基膦)钯(Pd(PPh3)4，0.05mmol)，加热至60摄氏度并反应12小时，反应完成后冷却至室温，加入20毫升水淬灭，二氯甲烷(3×20毫升)萃取，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以柱层析纯化(乙酸乙酯/正己烷：体积比1/10)，得1-C(0.17克，产率54％)。
(2)1-D的合成：取50毫升双颈圆底烧瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入1-C(1mmol)，双(频哪醇合)二硼(1.2mmol)，醋酸钾(2mmol)，1,4-二氧六环(20毫升)，氮气保护，加入[1,1-双(二苯基膦基)二茂铁]二氯化钯(Ⅱ)(0.05mmol)，回流12小时，反应完成后，粗产物经柱层析纯化(乙酸乙酯/正己烷：体积比1/10)，得1-D(0.27克，产率97％)。
(3)1-F的合成：同1-C的合成，区别在于用1-D替代1-B，1-E替代1-A，得1-F(0.24克，产率61％)。
(4)1-G的合成：取50毫升双颈圆底烧瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入1-F(1mmol)、二氯二(三环己基膦)钯(PdCl2(PCy3)2，0.05mmol)、特戊酸(t-BuCO2H，2mmol)、碳酸铯(Cs2CO3，2mmol)和二甲基乙酰胺(20毫升)，120摄氏度下搅拌10小时，反应完成后冷却至室温，反应体系经浓缩，粗产物以柱层析纯化(乙酸乙酯/正己烷：体积比1/10)，得到1-G(0.17克，产率47％)。
(5)1-H的合成：在50毫升三颈瓶中，加入1-G(1mmol)，二氯甲烷(20毫升)，0摄氏度条件下滴加，三溴化硼(2mmol)的二氯甲烷溶液，反应结束后，除去溶剂，粗产物以柱层析纯化(乙酸乙酯/正己烷，1/10)，得1-H(0.29克，产率84％)。
(6)1-J的合成：取50毫升双颈圆底烧瓶并放入搅拌子与上接回流管，加入1-H(1mmol)，二氯甲烷(20毫升)，吡啶(6mmol)，反应体系降温至0摄氏度，加入Tf2O(1.5mmol)，体系在室温下搅拌30分钟，随后冷却至0摄氏度，加入30毫升二氯甲烷，40毫升水，有机相用无水硫酸镁干燥，减压蒸馏除去溶剂，粗产物用柱层析(乙酸乙酯/正己烷，1/10)分离，得1-J(0.42克，产率88％)
(7)1的合成：取50毫升双颈圆底烧瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入1-J(1mmol)、1-K(1mmol)、碳酸铯(0.012mol)、三(二亚苄基丙酮)二钯(Pd2(dba)3，0.05mmol)和2-二环己基磷-2′,4′,6′-三异丙基联苯(xphos，0.055mmol)，然后加入甲苯，混合物回流24小时，反应后冷却至室温，反应体系过滤后浓缩，粗产物以柱层析纯化(二氯甲烷/正己烷，1/10(体积比))，得化合物1(0.46克，产率70％)。
元素分析：C48H31N3理论值：C，88.72；H，4.81；N，6.47；实测值：C，88.67；H，4.83；N，6.50；HRMS(ESI)m/z(M+)：理论值：649.2518；实测值：649.2525。
(1)7-C的合成：同1-C的合成，区别在于用7-A替代1-A，7-B替代1-B，得7-C(0.16克，产率51％)。
(2)7-D的合成，同1-D的合成，区别在于用7-C替代1-C，得7-D(0.26克，产率94％)
(3)7-F的合成：同1-C的合成，区别在于用7-D替代1-B，7-E替代1-A，得7-F(0.23克，产率58％)
(4)7-G的合成：同1-G的合成，区别在于用7-F替代1-F，得7-G(0.2克，产率55％)
(5)7-H的合成：同1-H的合成，区别在于用7-G替代1-G，得7-H(0.3克，产率88％)
(6)7-J的合成：同1-J的合成，区别在于用7-H替代1-H，得7-J(0.41克，产率86％)
(7)化合物7的合成：同化合物1的合成，区别在于用7-J替代1-J，7-K替代1-K，得化合物7(0.41克，产率75％)。
元素分析：C40H23N3理论值：C，88.05；H，4.25；N，7.70；实测值：C，88.10；H，4.23；N，7.67；HRMS(ESI)m/z(M+)：理论值：545.1892；实测值：545.1897。
(1)8-C的合成：同1-C的合成，区别在于用8-B替代1-B，得8-C(0.16克，产率51％)。
(2)8-D的合成，同1-D的合成，区别在于用8-C替代1-C，得8-D(0.25克，产率90％)
(3)8-F的合成：同1-C的合成，区别在于用8-D替代1-B，8-E替代1-A，得8-F(0.21克，产率53％)
(4)8-G的合成：同1-G的合成，区别在于用8-F替代1-F，得8-G(0.18克，产率50％)
(5)8-H的合成：同1-H的合成，区别在于用8-G替代1-G，得8-H(0.31克，产率89％)
(6)8-J的合成：同1-J的合成，区别在于用8-H替代1-H，得8-J(0.41克，产率86％)
(7)化合物8的合成：同化合物1的合成，区别在于用8-J替代1-J，8-K替代1-K，得化合物8(0.53克，产率81％)。
元素分析：C46H25N3S理论值：C，84.77；H，3.87；N，6.45；S，4.92；实测值：C，84.76；H，3.86；N，6.47；S，4.91；HRMS(ESI)m/z(M+)：理论值：651.1769；实测值：651.1775。
利用与如上相同的制备方法，区别仅在于使用如下表1中的原料来制备相应产物，产物的元素分析以及HRMS测试结果如表2所示。
表1
表2
器件实施例
提供一种有机电致发光器件，其具有以下层结构：基底(氧化铟锡(ITO)涂层玻璃基板)/空穴注入层(HIL)/空穴传输层(HTL)/发光层(EML)/电子传输层(ETL)/电子注入层(EIL)，且最后是阴极。
制造OLED所需的材料如下：
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HAT(CN)6作为空穴注入层，蒸镀厚度为5nm；
在空穴注入层上蒸镀空穴传输层，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和客体材料，蒸镀总膜厚为30nm；
在发光层上真空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Bphen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，蒸镀总膜厚为1nm；
在电子注入层上蒸镀Al，蒸镀总膜厚为80nm。
器件中各层及其材料以及厚度等参数如表3所示。
表3
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；
测试条件：电流密度为20mA/cm2，室温。
寿命测试：器件亮度下降至原始亮度的98％时记录时间(以小时计)。
器件性能测试结果如表4所示：
表4
| 器件实施例序号 | 驱动电压(V) | 电流效率(Cd/A) | 寿命(h) |
| 1 | 3.98 | 27 | 206 |
| 2 | 3.92 | 26 | 209 |
| 3 | 3.84 | 28 | 252 |
| 4 | 3.83 | 27 | 233 |
| 5 | 3.86 | 29 | 248 |
| 6 | 3.92 | 28 | 221 |
| 7 | 3.97 | 29 | 228 |
| 8 | 3.82 | 28 | 243 |
| 9 | 3.97 | 30 | 236 |
| 10 | 3.87 | 32 | 210 |
| 11 | 3.86 | 33 | 226 |
| 12 | 3.89 | 32 | 262 |
| 13 | 3.80 | 33 | 271 |
| 14 | 3.83 | 29 | 257 |
| 15 | 4.42 | 21 | 112 |
由表4可以看出，本发明的化合物使得有机电致发光器件具有更低的驱动电压(3.98V以下)，更高的电流效率(26Cd/A以上)和更长的寿命(206h以上)。
申请人声明，本发明通过上述实施例来说明本发明的含喹喔啉结构的稠杂环化合物及其应用，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，对本发明产品各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)
1.一种含喹喔啉结构的稠杂环化合物，其特征在于，所述化合物具有式(1)所示结构：
R1-R6各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C2-C30烯基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C2-C30烯基、取代或未取代的C2-C30炔基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
R1-R6各自独立存在或相邻两者连接成环，所述环为取代或未取代的苯环，
L选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C5-C30的亚杂芳基，
Ar1选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60的杂芳基，取代或未取代的C6-C60芳胺基、取代或未取代的C5-C60的杂芳胺基、取代或未取代的C5-C60的芳基杂芳胺基，
n选自0-3的整数，
m选自0-5的整数，
n1选自0-1的整数，
m1选自0-1的整数。
2.根据权利要求1所述的含喹喔啉结构的稠杂环化合物，其特征在于，n1+m1＝1。
3.根据权利要求1或2所述的含喹喔啉结构的稠杂环化合物，其特征在于，-L-Ar1选自
其中Ar2、Ar3各自独立选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60的杂芳基；
优选地，Ar2、Ar3各自独立选自取代或未取代的如下基团：苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基、二苯并咔唑基；
优选地，-L-Ar1选自
其中虚线代表L与Ar3通过化学键连接成环；
更优选地，-L-Ar1选自取代或未取代的如下基团：
4.根据权利要求1-3中任一项所述的含喹喔啉结构的稠杂环化合物，其特征在于，-L-Ar1选自
其中虚线代表Ar2、Ar3通过化学键连接成环，
优选地，-L-Ar1选自取代或未取代的如下基团
优选地，Ar1选自
其中X1选自N或CRX1，X2选自N或CRX2，X3选自N或CRX3，X4选自N或CRX4，X5选自N或CRX5，
RX1、RX2、RX3、RX4、RX5各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
RX1、RX2、RX3、RX4、RX5各自独立存在，或相邻两者连接成环，所述环为取代或未取代的苯环、吡啶环、萘环、蒽环、菲环、萘并噁唑环、萘并噻唑环、苯并呋喃环或苯并噻吩环，
优选地，Ar1选自
优选地，Ar1选自
其中X1、X2、X5中任意两者选自N，
Y1选自N、CRY1，Y2选自N、CRY2，Y3选自N、CRY3，Y4选自N、CRY4，
RY1、RY2、RY3、RY4各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C3-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基，
RY1、RY2、RY3、RY4各自独立存在，或相邻两者连接成环，所述环为取代或未取代的苯环。
优选地，Y1选自CRY1，Y2选自CRY2，Y3选自CRY3，Y4选自CRY4，
优选地，RX1、RX2、RX3、RX4、RX5、RY1、RY2、RY3、RY4各自独立选自氢、取代或未取代的如下基团：苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基；
优选地，所述L各自独立选自亚苯基、亚联苯基、亚萘基，
优选地，R1-R6各自独立选自氢、氘、氰基、氟、甲基、乙基、叔丁基、氘取代甲基、氟取代甲基、苯基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、二甲基芴基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基；
优选地，Ar1选自苯基、联苯基、三联苯基、萘基、苯并菲基、苯基取代萘基、萘基取代苯基、二苯并呋喃基、二苯并噻吩基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、2-苯基菲[3,4-d]噁唑基、2-苯基菲[3,4-d]噻唑基；
优选地，所述基团含有取代基时，所述取代基各自独立选自氘、卤素、氰基、未取代或R'取代的C1-C6的烷基、未取代或R'取代的C6-C12的芳基、未取代或R'取代的C3-C20的杂芳基；R'选自氘、卤素、氰基、氘取代的甲基、卤素取代的甲基；
更优选地，所述C1-C6的烷基选自甲基、乙基、叔丁基；
所述C6-C12的芳基选自苯基、联苯基、萘基；
所述C3-C20的杂芳基选自三嗪基、吡啶基、苯基取代吡啶基、吡啶基取代苯基、二苯并呋喃基、二苯并噻吩基。
5.根据权利要求1-4中任一项所述的含喹喔啉结构的稠杂环化合物，其特征在于，所述含喹喔啉结构的稠杂环化合物为如下化合物中的任意一种：
6.一种有机电致发材料，其特征在于，所述有机电致发光材料包括如权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
7.一种有机电致发光组合物，其特征在于，所述有机电致发光组合物包括如权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
8.根据权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物在制备光学器件中的应用；
优选地，所述光学器件包括有机电致发光器件、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机集成电路、有机太阳能电池、有机场淬灭器件、发光电化学电池、有机激光二极管或有机光感受器中任意一种。
9.一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和阴极，和设置在阳极和阴极间的有机层，所述有机层包括如权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合；
优选地，所述有机层至少包含空穴注入层、空穴传输层、发光层、电子传输层、电子注入层；
优选地，所述发光层的材料包含主体材料和客体材料，所述主体材料包含如权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合；
优选地，所述客体材料为磷光掺杂剂，所述磷光掺杂剂为含过渡金属的配合物，优选为含Ir或Pt的配合物；
优选地，所述电子传输层的材料至少包含如权利要求1-5中任一项所述的含喹喔啉结构的稠杂环化合物中的任意一种或至少两种的组合。
10.一种有机电致发光设备，其特征在于，所述有机电致发光设备包括如权利要求9所述的有机电致发光器件。
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