CN114560870B - 一种含硫多环芳香族化合物及其应用 - Google Patents
一种含硫多环芳香族化合物及其应用 Download PDFInfo
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- CN114560870B CN114560870B CN202210334995.XA CN202210334995A CN114560870B CN 114560870 B CN114560870 B CN 114560870B CN 202210334995 A CN202210334995 A CN 202210334995A CN 114560870 B CN114560870 B CN 114560870B
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- organic electroluminescent
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- electroluminescent device
- sulfur
- polycyclic aromatic
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- -1 polycyclic aromatic compound Chemical class 0.000 title claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000011593 sulfur Substances 0.000 title claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- PGGAYCHAGYRSPB-UHFFFAOYSA-N 1-bromo-2-(3-chlorophenoxy)benzene Chemical compound ClC1=CC=CC(OC=2C(=CC=CC=2)Br)=C1 PGGAYCHAGYRSPB-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical group 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 3
- JYGHOGAUQCUXJQ-UHFFFAOYSA-N 1-bromo-2-(3-chlorophenyl)sulfanylbenzene Chemical compound ClC1=CC=CC(SC=2C(=CC=CC=2)Br)=C1 JYGHOGAUQCUXJQ-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- RRWFUWRLNIZICP-UHFFFAOYSA-N 1-bromo-2-phenoxybenzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1 RRWFUWRLNIZICP-UHFFFAOYSA-N 0.000 description 2
- JGGSOWGJMBNDHS-UHFFFAOYSA-N 10-phenyl-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C1=CC=CC=C1 JGGSOWGJMBNDHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KHNYNFUTFKJLDD-UHFFFAOYSA-N BCR-49 Natural products C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 description 2
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- HAXBIWFMXWRORI-UHFFFAOYSA-N Benzo[k]fluoranthene Chemical compound C1=CC(C2=CC3=CC=CC=C3C=C22)=C3C2=CC=CC3=C1 HAXBIWFMXWRORI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- FTOVXSOBNPWTSH-UHFFFAOYSA-N benzo[b]fluoranthene Chemical compound C12=CC=CC=C1C1=CC3=CC=CC=C3C3=C1C2=CC=C3 FTOVXSOBNPWTSH-UHFFFAOYSA-N 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- XNHXNEXGBTXJIA-UHFFFAOYSA-N 1-bromo-4-chloro-2-phenoxybenzene Chemical compound ClC1=CC=C(Br)C(OC2=CC=CC=C2)=C1 XNHXNEXGBTXJIA-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- OQULTVCHWKEWSK-UHFFFAOYSA-N 9-phenyl-n-(4-phenylphenyl)carbazol-2-amine Chemical compound C=1C=C(C2=CC=CC=C2N2C=3C=CC=CC=3)C2=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 OQULTVCHWKEWSK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001808 coupling effect Effects 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
- 239000012153 distilled water Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MZKZCGLQGDKMBI-UHFFFAOYSA-N n-phenyldibenzothiophen-2-amine Chemical compound C=1C=C2SC3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 MZKZCGLQGDKMBI-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
本发明提供一种如通式(Ⅰ)所示的含硫多环芳香族化合物,所述化合物具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性,可作为有机电致发光器件的发光层主体材料,应用于红色磷光有机电致发光器件中,能够降低驱动电压,提高器件发光效率。
Description
技术领域
本发明涉及有机电致发光显示用材料技术领域,具体公开了一种含硫多环芳香族化合物,同时还公开了其在有机电致发光器件中的应用。
背景技术
有机电致发光(OLED)材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和美好的应用前景。随着多媒体信息技术的发展,对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件(OLEDs)。其中,OLEDs具有自身发光、低电压直流驱动、轻薄省电、全固化、视角宽、颜色丰富等一系列优点,与液晶显示器件相比,OLEDs不需要背光源,视角更宽,功耗低,其响应速度是液晶显示器件的1000倍,因此,OLEDs具有更广阔的应用前景。
自高效有机发光二极管(OLEDs)第一次被报道以来,许多学者致力于研究如何提高器件效率和稳定性。Forrest和Thompson研究组发现过渡金属配合物能应用于磷光有机电致发光器件(Phosphorescent OLEDs,Ph OLEDs)。磷光材料存在很强的自旋轨道耦合作用,能同时利用单线态和三线态激子,使磷光电致发光器件内量子效率在理论上达到了100%。然而,磷光材料激发态寿命较长,当三线态激子浓度较高时容易形成三线态-三线态湮灭和三线态-极化子间湮灭,使效率严重下降。所以,常常将磷光材料作为客体掺入到主体材料中,以此来降低自浓度淬灭过程。在磷光有机电致发光器件(PhosphorescentOLEDs,Ph OLEDs)中选择合适的主体材料十分重要。例如宽带隙的主体材料会引起磷光有机电致发光器件启亮电压的升高,相应可获取高效率。选择合适的主体材料,进而采用主客体掺杂方式来调节光色、亮度与效率,可达到改善有机电致发光显示器件性能的目的。一般来说,主体材料必备的特性包括:(1)拥有高于客体染料的三线态能级;(2)具有较好的载流子迁移率且能与相邻层能级匹配;(3)具有高的热稳定性和成膜稳定性。
目前OLED显示和照明得到了广泛的商业化应用,客户终端对OLED屏体光电及寿命要求也不断提升,为了应对这类需求,除了在OLED面板制造工艺上的精益求精,能够满足更高器件指标的OLED材料的开发就显得尤为重要。因此,开发稳定高效的主体材料,从而降低驱动电压,提高器件发光效率,延长器件寿命,将具有很重要的实际应用价值。
发明内容
本发明的目的在于提供一种有机电致发光器件的发光层主体材料,应用于红色磷光OLED器件中,能够降低驱动电压,提高器件发光效率。
第一方面,本发明提供了一种含硫多环芳香族化合物,具有如通式(Ⅰ)所示的结构:
其中,X选自O、S、Se、NRX1、CRX2RX3、PRX4和SiRX5RX6;
所述RX1~RX6各自独立地代表氢、氘、卤素、取代或未取代的具有1-20个碳原子的烷基、取代或未取代的具有1-20个碳原子的烷氧基、取代或未取代的具有1-20个碳原子的杂烷基,取代或未取代的具有3-20个碳原子的环烷基、取代或未取代的具有3-20个碳原子的烷硅基,取代或未取代的具有6-30个碳原子的芳烷基、取代或未取代的具有6-30个碳原子的芳基、取代或未取代的具有6-30个碳原子的芳氧基、取代或未取代的具有6-30个碳原子的杂芳基、取代或未取代的具有6-30个碳原子的杂芳氧基、取代或未取代的具有6-30个碳原子的芳基硅烷基、取代或未取代的具有0-20个碳原子的氨基、取代或未取代的具有1-20个碳原子的酰基、取代或未取代的具有1-20个碳原子的羰基、取代或未取代具有1-20个碳原子的羧酸基、取代或未取代具有1-20个碳原子的酯基、氰基、异氰基、取代或未取代具有1-20个碳原子的硫烷基、取代或未取代具有0-20个碳原子的亚磺酰基、取代或未取代具有0-20个碳原子的磺酰基、取代或未取代具有0-20个碳原子的膦基;
所述R1~R4各自独立地代表氢、氘、卤素、取代或未取代的具有1-20个碳原子的烷基、取代或未取代的具有1-20个碳原子的烷氧基、取代或未取代的具有3-20个碳原子的环烷基、氨基、具有1-20个碳原子的烷胺基、取代或未取代的含有苯环和/或芳杂环的芳香基团、并且R1~R4至少有一个为/>R1~R4相同或者不同;
所述Ar1、Ar2各自独立地代表取代或未取代的含有苯环和/或芳杂环的芳香基团;Ar1、Ar2相同或者不同;所述Ar1与Ar2之间成环或者不成环。
在一些实施方案中,X选自O和S。
在一些实施方案中,所述R1~R4中任意一个为
在一些实施方案中,所述R1~R4中任意两个基团为
在一些实施方案中,所述R1和R4为
在一些实施方案中,所述R2和R4为
在一些实施方案中,所述R1和R3为
在一些实施方案中,所述R2和R3为
在一些实施方案中,所述Ar1与Ar2之间相邻的苯环或芳杂环稠合成环。
在一些实施方案中,所述Ar1与Ar2之间相邻的苯环或芳杂环通过单键、双键、B、N、O、S或C原子连接成环。
在一些实施方案中,所述Ar1与Ar2之间相邻的苯环或芳杂环通过 连接成环。
在一些实施方案中,所述Ar1、Ar2各自独立地代表取代或未取代的苯环、取代或未取代的C4~C6的杂芳环、取代或未取代的多苯代脂烃、取代或未取代的稠环芳烃、取代或未取代的稠杂环芳烃、取代或未取代的联芳烃、或取代或未取代的螺二芴类;当上述基团被取代时,取代基选自:卤素、直链或支链烷基、环烷基、芳基、氨基、烷胺基、芳胺基、杂芳基、单环芳基、苯并基、吡啶并基、菲并基、萘并基、吲哚并基、苯并噻吩并基、苯并呋喃并基;所述取代基的个数选自1~7之间的整数。
在一些实施方案中,所述Ar1、Ar2各自独立地代表取代或未取代的苯环、C4~C6的杂芳环、联苯、茚、萘、苊烯、苊、芴、螺二芴、菲、蒽、荧蒽、芘、三亚苯、苯并(a)蒽、苯并(b)荧蒽、苯并(k)荧蒽、苯并(a)芘、占吨、吖啶、咔唑、二苯并呋喃或二苯并噻吩;当上述基团被取代时,取代基选自:卤素、C1~C5的直链或含支链的烷基、C3~C6的环烷基、苯基、二苯基氨基、苯并基、吡啶并基、菲并基、萘并基、吲哚并基、苯并噻吩并基、苯并呋喃并基;所述取代基的个数选自1~3之间的整数。
在一些实施方案中,所述X选自O和S;所述Ar1和Ar2各自独立地代表取代或未取代的苯环、取代或未取代的C4~C6的杂芳环、取代或未取代的多苯代脂烃、取代或未取代的稠环芳烃、取代或未取代的稠杂环芳烃、取代或未取代的联芳烃、或取代或未取代的螺二芴类;当上述基团被取代时,取代基选自:卤素、直链或支链烷基、环烷基、芳基、氨基、烷胺基、芳胺基、杂芳基、单环芳基、苯并基、吡啶并基、菲并基、萘并基、吲哚并基、苯并噻吩并基、苯并呋喃并基;所述取代基的个数选自1~7之间的整数。
在一些实施方案中,所述X选自O和S;所述Ar1和Ar2各自独立地代表取代或未取代的苯环、C4~C6的杂芳环、联苯、茚、萘、苊烯、苊、芴、螺二芴、菲、蒽、荧蒽、芘、三亚苯、苯并(a)蒽、苯并(b)荧蒽、苯并(k)荧蒽、苯并(a)芘、占吨、吖啶、咔唑、二苯并呋喃或二苯并噻吩;当上述基团被取代时,取代基选自:卤素、C1~C5的直链或含支链的烷基、C3~C6的环烷基、苯基、二苯基氨基、苯并基、吡啶并基、菲并基、萘并基、吲哚并基、苯并噻吩并基、苯并呋喃并基;所述取代基的个数选自1~3之间的整数。
在一些实施方案中,所述选自如下基团:
上述各取代基团中,“--”表示取代位。
作为本发明一种优选的实施方式,所述通式(I)所示的化合物,任意选自以下结构式所示的化合物:所述化合物选自以下结构式所示化合物:
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第二方面,本发明提供了一种所述的含硫多环芳香族化合物在制备有机电致发光器件中的应用。
优选地,所述的含硫多环芳香族化合物在有机电致发光器件中用作发光层主体材料。
第三方面,本发明提供了一种有机电致发光器件,所述有机电致发光器件包括发光层,所述发光层的主体材料中含有本发明所述的含硫多环芳香族化合物。
优选地,所述发光层的厚度为10~50nm,更优选为20~40nm。
作为一种优选的实施方案,所述有机电致发光器件中包括阳极层、阴极层、至少一个发光层和任选的其它层,其它层可以任选自空穴注入层、空穴传输层、电子注入层、电子传输层中的一个或几个。其中,发光层(EML)的主体材料包含本发明提供的所述含硫多环芳香族化合物。优选地,所述EML发光层的厚度可以为10~50nm,进一步优选为20~40nm。
更具体地,本发明提供了一种有机电致发光器件,所述有机电致发光器件由下至上依次包括透明基片、阳极层、空穴注入层、空穴传输层、电致发光层、电子传输层、电子注入层和阴极层,其中电致发光层的主体材料包括本发明提供的所述含硫多环芳香族化合物。所述EML发光层的厚度可以为10~50nm,进一步优选为20~40nm。
第四方面,本发明提供了一种显示装置,包括所述的有机电致发光器件。
第五方面,本发明提供了一种照明装置,包括所述有机电致发光器件。
本发明提供了一种新型的含硫多环芳香族化合物,具体如通式(I)所示,该系列化合物的母核结构具有良好的热稳定性,同时具有合适的HOMO和LUMO能级和Eg,通过在母核结构中的活泼位置引入具有较强给电子能力的基团,即通过在结构中引入具有较强给电子能力的芳胺结构或苯并杂环结构,获得了一类新型结构的OLED材料,这种材料具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性,可以被应用在有机电致发光领域,作为主体材料使用。
经试验,将本发明的所述化合物应用于OLED器件中,例如应用于红色磷光OLED器件中,作为主体材料使用,能够降低驱动电压,提高器件发光效率,可以有效地提升器件的光电性能,制成的OLED器件可以应用于显示或者照明领域。
具体实施方式
下面通过具体实施例对本发明的技术方案进行详细说明。以下实施例用于说明本发明,但不用来限制本发明的范围,凡其他未脱离本发明所揭示的精神下所完成的等效改变或修饰,均应包含在所属权利要求范围内。
根据本发明提供的制备方法,本领域技术人员可采用已知的常见手段来实现,如进一步选择合适的催化剂、溶剂,确定适宜的反应温度、时间、物料比等,本发明对此不作特别限定。如无特别说明,制备过程中使用的溶剂、催化剂、碱等原料均可以通过公开商业途径或者本领域已知的方法合成得到。
合成中间体
中间体M1的合成
合成路线如下:
具体操作步骤为:
(1)在2L的三口瓶中,加入2-溴苯并[b]噻吩(21.3g,0.1mol)、2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯甲酸甲酯(26.2g,0.1mol)、碳酸钠(26.5g,0.25mol)、甲苯200mL、乙醇200mL、水150mL,反应体系用氮气置换保护后加入Pd(PPh3)4(11.5g,10mmol)。加热回流反应6小时,停止反应。减蒸掉溶剂,乙酸乙酯萃取,无水硫酸镁干燥,过滤,柱层析纯化,得23.0g白色固体M1-1,收率约86%。
(2)在1L的三口瓶中,加入M1-1(26.8g,0.1mol),氢氧化钠(0.8g,0.2mol),乙醇200mL,回流反应2小时,停止反应。50%的稀盐酸调节PH为2-3,搅拌半小时,抽滤,得24.9g白色固体M1-2,收率约98%。
(3)在1L的三口瓶中,加入M1-2(25.4g,0.1mol)、25g甲磺酸、甲苯200mL开启搅拌加热,90-100℃反应2小时,降至室温,加入200mL蒸馏水,搅拌半小时,抽滤,得到21.2g白色固体M1-3,收率约90%。
(4)在2L三口瓶中加入M1-3(23.6g,0.1mol)和600mL二氯甲烷,开动搅拌,缓慢滴加(40mL,0.4mol,30%)过氧化氢水溶液,室温反应2小时,反应结束,加入100mL饱和碳酸氢钠水溶液,搅拌分液,旋干得白色固体24.1g白色固体M1-4,收率约90%。
(5)在氮气保护下,2L三口瓶中加入1-溴-2-(3-氯苯氧基)苯(28.4g,0.1mol)和THF400mL,冷却至-78℃,在搅拌下缓慢滴加正丁基锂(100mL,0.25mol),滴加时间约1小时,滴完用50mL THF冲淋滴液漏斗,滴完保温1小时。在-78℃的低温体系中,缓慢滴加M1-4(26.8g,0.1mol),然后用少量THF冲洗滴液漏斗,加完后保温1小时,然后缓慢升温至室温,在室温下搅拌反应1小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到42.6g白色固体M1-5,收率约90%。
(6)在1L三口瓶中加入M1-5(47.3g,0.1mol)、浓盐酸50mL、冰醋酸200mL,开动搅拌加热,100℃反应4小时,降至室温。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到38.59g白色固体M1,收率约85%。
产物MS[M+H]+:455;元素分析(C27H15ClO3S):理论值:C,71.29%;H,3.32%;Cl,7.79%;O,10.55%;S,7.05%;实测值:C:71.18%,H:3.29%。
中间体M3的合成
制备过程参考中间体M1的过程方法,在步骤(5)中,将反应物1-溴-2-苯氧基苯代替1-溴-2-(3-氯苯氧基)苯,其余条件不变,得35.7g白色固体M3-6,收率约85%。
在1L三口瓶中加入M3-6(45.4g,0.1mol)和二氯甲烷200mL,开动搅拌,控温0-5℃,加入溴素(1.6g,0.1mol),0-5℃反应3小时。调至中性,分离有机相,干燥,得到44.9g白色固体M3,收率约90%。
产物MS[M+H]+:500;元素分析(C27H15BrO3S):理论值:C,64.94%;H,3.03%;Br,16.00%;O,9.61%;S,6.42%;实测值:C:64.91%,H:3.10%。
中间体M4的合成
制备过程参考中间体M1的过程方法,在步骤(1)中,将反应物2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-4-氯苯甲酸甲酯代替2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯甲酸甲酯,在步骤(5)中,将反应物1-溴-2-苯氧基苯代替1-溴-2-(3-氯苯氧基)苯,其余条件不变,得36.4g白色固体,收率约80%。
产物MS[M+H]+:455;元素分析(C27H15ClO3S):理论值:C,71.29%;H,3.32%;Cl,7.79%;O,10.55%;S,7.05%;实测值:C:71.24%,H:3.28%。
中间体M5的合成
制备过程参考中间体M1的过程方法,在步骤(1)中,将反应物2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-4-氯苯甲酸甲酯代替2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯甲酸甲酯,在步骤(5)中,将反应物1-溴-4-氯-2-苯氧基苯代替1-溴-2-(3-氯苯氧基)苯,其余条件不变,得36.2g白色固体,收率约74%。
产物MS[M+H]+:490;元素分析(C27H14Cl2O3S):理论值:C,66.27%;H,2.88%;Cl,14.49%;O,9.81%;S,6.55%;实测值:C:66.13%,H:2.76%。
中间体M6的合成
合成路线如下:
在1L三口瓶中加入M1(45.4g,0.1mol)和二氯甲烷200mL,开动搅拌,控温0-5℃,加入溴素(1.6g,0.1mol),0-5℃反应3小时。调至中性,分离有机相,干燥,得到41.6g白色固体M6,收率约78%。
产物MS[M+H]+:534;元素分析(C27H14BrClO3S):理论值:C,60.75%;H,2.64%;Br,14.97%;Cl,6.64%;O,8.99%;S,6.01%;实测值:C:60.62%,H:2.59%。
中间体M7的合成
制备过程参考中间体M1的过程方法,在步骤(5)中,将反应物(2-溴苯基)(3-氯苯基)硫烷代替1-溴-2-(3-氯苯氧基)苯,其余条件不变,得35.4g白色固体,收率约75%。
产物MS[M+H]+:471;元素分析(C27H15ClO2S2):理论值:C,68.86%;H,3.21%;Cl,7.53%;O,6.79%;S,13.61%;实测值:C:68.83%,H:3.20%。
中间体M8的合成
制备过程参考中间体M1的过程方法,在步骤(1)中,将反应物2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-4-氯苯甲酸甲酯代替2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯甲酸甲酯,在步骤(5)中,将反应物(2-溴苯基)(3-氯苯基)硫烷代替1-溴-2-(3-氯苯氧基)苯,其余条件不变,得38.38g白色固体,收率约76%。
产物MS[M+H]+:506;元素分析(C27H14Cl2O2S2):理论值:C,64.16%;H,2.79%;Cl,14.03%;O,6.33%;S,12.69%;实测值:C:64.18%,H:2.75%。
中间体M9的合成
制备过程:参考中间体M1的过程方法,在步骤(5)中,将反应物(2-溴苯基)(3-氯苯基)硫烷代替1-溴-2-(3-氯苯氧基)苯得M9-6,然后参考中间体M6的合成方法,其余条件不变,得37.92g白色固体,收率约69%
产物MS[M+H]+:550;元素分析(C27H14BrClO2S2):理论值:C,58.98%;H,2.57%;Br,14.53%;Cl,6.45%;O,5.82%;S,11.66%;实测值:C:58.96%,H:2.55%。
本申请中,其他类型中间体参照以上方法进行相应替换,均可得到目标中间体。
实施例1化合物I-3的合成
合成路线如下:
制备过程为:取2L三口瓶,配磁力搅拌,氮气置换后依次加入叔丁醇钠(28.8g,0.3mol)、二苯胺(33.8g,0.2mol)和甲苯400ml。再次氮气置换后依次加入(0.8g,4mmol)三叔丁基膦和(0.5g,2mmol)乙酸钯。加完后,加热升温至85℃。开始滴加由(48.9g,0.1mol)M5和100ml甲苯组成的溶液,控温80-120℃反应4个小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到60.32g白色固体,收率约80%。
产物MS[M+H]+:755;元素分析(C51H34N2O3S):理论值:C:81.14%;H:4.54%;N:3.71%;实际值:C:81.02%,H:4.48%,N:3.72%。
实施例2化合物I-6的合成
合成路线如下:
制备过程为:取1L三口瓶,配磁力搅拌,氮气置换后依次加入叔丁醇钠(14.4g,0.15mol)、氘代二苯胺(17.9g,0.1mol)和甲苯400ml。再次氮气置换后依次加入(0.4g,2mmol)三叔丁基膦和(0.25g,1mmol)乙酸钯。加完后,加热升温至85℃。开始滴加由(48.9g,0.1mol)M1和100ml甲苯组成的溶液,控温80-120℃反应4个小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到44.78g白色固体,收率约75%。
产物MS[M+H]+:598;元素分析(C39H15D10NO3S):理论值:C:78.36%;H:5.90%;N:2.34%;实际值:C:78.29%,H:5.88%,N:2.33%。
实施例3化合物I-27的合成
合成路线如下:
制备过程参考实施例2的过程方法,将M4代替M1,N-苯基二苯并[b,d]噻吩-2-胺代替氘代二苯胺,其余条件不变,得56.13g白色固体,收率约81%。
产物MS[M+H]+:694;元素分析(C45H27NO3S2):理论值:C:77.90%;H:3.92%;N:2.02%;实际值:C:77.85%,H:3.82%,N:2.01%。
实施例4化合物I-39的合成
合成路线如下:
制备过程取2L三口瓶,配磁力搅拌,氮气置换后依次加入叔丁醇钠(14.4g,0.15mol)、N-([1,1'-联苯]-4-基)-9-苯基-9H-咔唑-2-胺(41.0g,0.1mol)和甲苯400ml。再次氮气置换后依次加入(0.4g,2mmol)三叔丁基膦和(0.23g,1mmol)乙酸钯。加完后,加热升温至85℃。开始滴加由(49.8g,0.1mol)M3和100ml甲苯组成的溶液,控温80-120℃反应4个小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得63.76g白色固体,收率约77%。
产物MS[M+H]+:829;元素分析(C57H36N2O3S):理论值:C:82.59%;H:4.38%;N:3.38%;实际值:C:82.41%,H:4.18%,N:3.37%。
实施例5化合物I-47的合成
合成路线如下:
制备过程参考实施例2的过程方法,用10H-吩噻嗪代替氘代二苯胺,其余条件不变,得51.21g白色固体,收率约83%。
产物MS[M+H]+:618;元素分析(C39H23NO3S2):理论值:C:75.83%;H:3.75%;N:2.27%;实际值:C:75.74%,H:3.70%,N:2.28%。
实施例6化合物I-112的合成
合成路线如下:
制备过程为:氮气保护下,2L三口瓶,配磁力搅拌,氮气置换后依次加入M6(53.35g,0.1mol),10H-吩噻嗪(19.9g,0.1mol),铜粉(6.3g,0.1mol)、18-冠-6(26.4g,0.1mol)、碳酸钾(20.7g,0.15mol)、邻二氯苯800ml。氮气保护下加热回流反应20小时,反应结束。降温,加水,蒸出邻二氯苯。固体产物水洗,过滤烘干,柱色谱分离,旋干得32.58g白色固体I-112-1,收率约50%。
2L三口瓶,配磁力搅拌,氮气置换后依次加入叔丁醇钠(14.4g,0.15mol)、5-苯基-5,10-二氢吩嗪(25.8g,0.1mol)和甲苯400ml。再次氮气置换后依次加入(0.4g,2mmol)三叔丁基膦和(0.23g,1mmol)乙酸钯。加完后,加热升温至85℃。开始滴加由(65.15g,0.1mol)I-112-1和100ml甲苯组成的溶液,控温80-120℃反应4个小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到68.97g白色固体I-112,收率约79%。
产物MS[M+H]+:874;元素分析(C57H35N3O3S2):理论值:C:78.33%;H:4.04%;N:4.81%;实际值:C:78.17%,H:3.99%,N:4.80%。
实施例7化合物I-108的合成
合成路线如下:
制备过程参考实施例6的过程方法,M7替代M6,二苯胺代替10H-吩噻嗪,二(4-联苯基)胺代替5-苯基-5,10-二氢吩嗪,其余条件不变,得70.07g白色固体,收率约76%。
产物MS[M+H]+:923;元素分析(C63H42N2O2S2):理论值:C:81.97%;H:4.59%;N:3.03%;实际值:C:81.88%,H:4.49%,N:2.99%。
实施例8化合物I-105的合成
合成路线如下:
制备过程参考实施例1的过程方法,M8替代M5,N-(3-(甲基-d3)苯基)萘-2-胺代替二苯胺,其余条件不变,得71.42g白色固体,收率约79%。
产物MS[M+H]+:905;元素分析(C61H36D6N2O2S2):理论值:C:80.94%;H:5.34%;N:3.09%;实际值:C:80.87%,H:5.26%,N:3.07%。
实施例9化合物I-103的合成
合成路线如下:
制备过程参考实施例2的过程方法,M7替代M1,双(3-(甲基-d3)苯基)胺代替氘代二苯胺,其余条件不变,得47.78g白色固体,收率约75%。
产物MS[M+H]+:638;元素分析(C41H23D6NO2S2):理论值:C:77.21%;H:5.53%;N:2.20%;实际值:C:77.09%,H:5.42%,N:2.17%。
依据实施例1~实施例9的技术方案,只需要简单替换对应的原料,不改变任何实质性操作,可以合成I-1~I-112的其他化合物。
实施例10
本实施例提供了一种OLED红光器件,器件的结构为:
ITO/HATCN(1nm)/HT01(40nm)/NPB(25nm)/EML(实施例1~9所提供的任一化合物)(30nm)/Bphen(40nm)/LiF(1nm)/Al。
制备过程为:
(1)将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,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分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
(2)把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀HATCN作为第一空穴注入层,蒸镀速率为0.1nm/s,蒸镀总膜厚为1nm;接着蒸镀第二空穴注入层HT01,蒸镀速率为0.1nm/s,厚度为40nm;在上述空穴注入层膜上蒸镀一层NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为25nm;其中HATCN、HT01、NPB的结构式如下:
(3)在空穴传输层上继续真空蒸镀实施例1提供的化合物I-3作为器件的EML发光层,EML发光层具体包括本发明实施例1提供的红光主体材料I-3和染料材料,利用多源共蒸的方法,调节主体材料蒸镀速率为0.1nm/s,染料材料Ir(piq)2acac作为掺杂材料掺杂浓度为5%,蒸镀总膜厚为30nm,形成器件的有机电致发光层,其中Ir(piq)2acac的结构式如下:
(4)在有机发光层上继续蒸镀一层化合物BPhen作为器件的电子传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;其中BPhen的结构式如下:
(5)在电子传输层之上依次真空蒸镀厚度为1nm的LiF作为器件的电子注入层、膜厚度为150nm的Al层作为器件的阴极,得到本发明提供的OLED器件OLED-1。
按照与上相同的步骤,仅将步骤(3)中的I-3化合物分别替换为实施例2-实施例9制得的化合物,作为红光主体材料使用,分别得到本发明提供的OLED-2~OLED-9。
按照与上相同的步骤,仅将步骤(3)中的主体材料I-3化合物替换为对比化合物C1,结构式如下所示,得到对比例OLED-10。
对比化合物C1。
按照与上相同的步骤,仅将步骤(3)中的主体材料I-3化合物替换为对比化合物C2,结构式如下所示,得到对比例OLED-11。
对比化合物C2。
所得器件的性能检测结果如表1所示。
表1
由表1数据可知,利用本发明提供的式(I)所示的有机化合物作为红光主体材料,所制备成的器件电流效率高,在亮度相同的条件下,工作电压明显比对比器件偏低,寿命比对比器件延长,是性能良好的红光主体材料。
虽然,上文中已经用一般性说明、具体实施方式及试验,对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (11)
1.一种含硫多环芳香族化合物,其特征在于,具有如通式(Ⅰ)所示的结构:
其中,X选自O或S;
所述R1~R4各自独立地代表氢、氘、卤素、具有1-20个碳原子的烷基、具有1-20个碳原子的烷氧基、具有3-20个碳原子的环烷基、氨基、具有1-20个碳原子的烷胺基、并且R1~R4至少有一个为/>R1~R4相同或者不同;
所述选自如下基团:
上述各基团中,“--”表示取代位。
2.根据权利要求1所述的化合物,其特征在于,所述R1~R4中任意一个基团为或者
所述R1~R4中任意两个基团为或者
R1和R4为或者
R2和R4为或者
R1和R3为或者
R2和R3为
3.一种含硫多环芳香族化合物,其特征在于,所述化合物选自以下结构式所示化合物:
4.权利要求1~3任一项所述的含硫多环芳香族化合物在制备有机电致发光器件中的应用。
5.根据权利要求4所述的应用,其特征在于,所述含硫多环芳香族化合物在有机电致发光器件中用作发光层主体材料。
6.一种有机电致发光器件,其特征在于,所述有机电致发光器件的发光层的主体材料中含有权利要求1~3任一项所述的含硫多环芳香族化合物。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机电致发光器件由下至上依次包括透明基片、阳极层、空穴注入层、空穴传输层、主体材料中含有权利要求1~3任一项所述的含硫多环芳香族化合物的电致发光层、电子传输层、电子注入层和阴极层。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述电致发光层的厚度为10nm~50nm。
9.根据权利要求7所述的有机电致发光器件,其特征在于,所述电致发光层的厚度为20nm~40nm。
10.一种显示装置,其特征在于,包括权利要求6~9任一项所述的有机电致发光器件。
11.一种照明装置,其特征在于,包括权利要求6~9任一项所述的有机电致发光器件。
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