CN106220638B - 一种基于氧杂蒽酮的化合物及其应用 - Google Patents
一种基于氧杂蒽酮的化合物及其应用 Download PDFInfo
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- CN106220638B CN106220638B CN201610259297.2A CN201610259297A CN106220638B CN 106220638 B CN106220638 B CN 106220638B CN 201610259297 A CN201610259297 A CN 201610259297A CN 106220638 B CN106220638 B CN 106220638B
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- xanthone
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 34
- BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 239000000741 silica gel Substances 0.000 claims description 13
- 229910002027 silica gel Inorganic materials 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 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 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 60
- 238000000921 elemental analysis Methods 0.000 description 25
- 150000002500 ions Chemical class 0.000 description 24
- 238000001819 mass spectrum Methods 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- -1 xanthone compound Chemical class 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000007772 electrode material Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C)(c1ccccc1)c(cc(c(cccc1)c1[o]1)c1c1)c1NC(C=CC1*C=CC=CC=C2)=CC1C2=O Chemical compound CC(C)(c1ccccc1)c(cc(c(cccc1)c1[o]1)c1c1)c1NC(C=CC1*C=CC=CC=C2)=CC1C2=O 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- DYQUGFRRGGOYCA-UHFFFAOYSA-N 2-bromoxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3OC2=C1 DYQUGFRRGGOYCA-UHFFFAOYSA-N 0.000 description 2
- UEKROUJUENOVKW-UHFFFAOYSA-N 3-bromoxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(Br)C=C3OC2=C1 UEKROUJUENOVKW-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000001748 luminescence spectrum Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- FRMXXDGDAAGAOR-UHFFFAOYSA-N 2-(3-bromophenyl)xanthen-9-one Chemical compound BrC=1C=C(C=CC=1)C1=CC=2C(C3=CC=CC=C3OC=2C=C1)=O FRMXXDGDAAGAOR-UHFFFAOYSA-N 0.000 description 1
- RUXFNNYVHMKVRX-UHFFFAOYSA-N 2-(4-bromophenyl)xanthen-9-one Chemical compound BrC1=CC=C(C=C1)C1=CC=2C(C3=CC=CC=C3OC=2C=C1)=O RUXFNNYVHMKVRX-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
- NQANJUNTWDNHFF-UHFFFAOYSA-N 3-(3-bromophenyl)xanthen-9-one Chemical compound BrC=1C=C(C=CC=1)C=1C=CC=2C(C3=CC=CC=C3OC=2C=1)=O NQANJUNTWDNHFF-UHFFFAOYSA-N 0.000 description 1
- BUTHNTUPAXURTN-UHFFFAOYSA-N 3-(4-bromophenyl)xanthen-9-one Chemical compound BrC1=CC=C(C=C1)C=1C=CC=2C(C3=CC=CC=C3OC=2C=1)=O BUTHNTUPAXURTN-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- IBNWVUISLDIASI-UHFFFAOYSA-N C=CC(C(C=C)OC1=CCCC=C11)C1O Chemical compound C=CC(C(C=C)OC1=CCCC=C11)C1O IBNWVUISLDIASI-UHFFFAOYSA-N 0.000 description 1
- GZBCBSYOZQFQSE-RZICPAAYSA-N CC(C)(/C=C/CC1c(cccc2)c2OC1=C)/C(/C=C\C=C)=C\NC1=CC(C(C(C)=CC23)=CC2OC2=CCCC=C2C3O)=CC=[I]1 Chemical compound CC(C)(/C=C/CC1c(cccc2)c2OC1=C)/C(/C=C\C=C)=C\NC1=CC(C(C(C)=CC23)=CC2OC2=CCCC=C2C3O)=CC=[I]1 GZBCBSYOZQFQSE-RZICPAAYSA-N 0.000 description 1
- NNIJOLWBCYEYFG-UHFFFAOYSA-N CC(C)(C1C=CC=CC1N(C(C1C=CC=CC11)=C(C=CC=C2)C2=C1C1=CC=CC(C2O)C1Oc1c2cccc1)c1c2)c1cc1c2[o]c2c1cccc2 Chemical compound CC(C)(C1C=CC=CC1N(C(C1C=CC=CC11)=C(C=CC=C2)C2=C1C1=CC=CC(C2O)C1Oc1c2cccc1)c1c2)c1cc1c2[o]c2c1cccc2 NNIJOLWBCYEYFG-UHFFFAOYSA-N 0.000 description 1
- TZHLWHQKPXEJAD-UHFFFAOYSA-N CC(C)(C=C1CCC=C)C(C2Nc3ccccc3C2C=C)=CN1c(cc1)c(CCCC2)c2c1-c1cc(Oc2ccccc2C2O)c2cc1 Chemical compound CC(C)(C=C1CCC=C)C(C2Nc3ccccc3C2C=C)=CN1c(cc1)c(CCCC2)c2c1-c1cc(Oc2ccccc2C2O)c2cc1 TZHLWHQKPXEJAD-UHFFFAOYSA-N 0.000 description 1
- MYTBCFNESSOEFZ-KMSUXSLWSA-N CC(C)(c(cccc1)c1N(c(cc1)ccc1/C(/C=C\C1)=C/COC2=CCCC=C2C1O)c1c2)c1cc1c2[o]c2c1cccc2 Chemical compound CC(C)(c(cccc1)c1N(c(cc1)ccc1/C(/C=C\C1)=C/COC2=CCCC=C2C1O)c1c2)c1cc1c2[o]c2c1cccc2 MYTBCFNESSOEFZ-KMSUXSLWSA-N 0.000 description 1
- ZGBKBWZJIMSOCC-UHFFFAOYSA-N CC(C)(c(cccc1)c1N(c1cccc(-c2ccc(C(c3ccccc3O3)O)c3c2)c1)c1c2)c1cc1c2[o]c2ccccc12 Chemical compound CC(C)(c(cccc1)c1N(c1cccc(-c2ccc(C(c3ccccc3O3)O)c3c2)c1)c1c2)c1cc1c2[o]c2ccccc12 ZGBKBWZJIMSOCC-UHFFFAOYSA-N 0.000 description 1
- ZEKZACKZEHCCOU-GUPZHTLSSA-N CC(C)c1ccc(c(cccc2)c2[o]2)c2c1N(c1ccccc1)C(C=CC1)=CC1/C=C/C(O/C(/C(/C1O)=C\C)=C/C)=C1C=C Chemical compound CC(C)c1ccc(c(cccc2)c2[o]2)c2c1N(c1ccccc1)C(C=CC1)=CC1/C=C/C(O/C(/C(/C1O)=C\C)=C/C)=C1C=C ZEKZACKZEHCCOU-GUPZHTLSSA-N 0.000 description 1
- ILNPVLXWTMJIEN-UHFFFAOYSA-N CC(C=C1)(C=CC(Oc2ccccc22)=C1C2=O)Br Chemical compound CC(C=C1)(C=CC(Oc2ccccc22)=C1C2=O)Br ILNPVLXWTMJIEN-UHFFFAOYSA-N 0.000 description 1
- CFYAMZGPAYCDRX-UHFFFAOYSA-N O=C1c(ccc(Br)c2)c2Nc2ccccc12 Chemical compound O=C1c(ccc(Br)c2)c2Nc2ccccc12 CFYAMZGPAYCDRX-UHFFFAOYSA-N 0.000 description 1
- YUSHFLBKQQILNV-UHFFFAOYSA-N O=C1c2ccccc2OCc2c1cccc2 Chemical compound O=C1c2ccccc2OCc2c1cccc2 YUSHFLBKQQILNV-UHFFFAOYSA-N 0.000 description 1
- WNKRTSKKTLXOMW-UHFFFAOYSA-N OC(C=CC12)=CC1Oc1ccccc1C2=O Chemical compound OC(C=CC12)=CC1Oc1ccccc1C2=O WNKRTSKKTLXOMW-UHFFFAOYSA-N 0.000 description 1
- HABFLXGFNIQKGT-UHFFFAOYSA-N OC1C2=CCC=C=C2Oc2c1ccc(N1c(cc3[o]c4ccccc4c3c3)c3C=Cc3c1cccc3)c2 Chemical compound OC1C2=CCC=C=C2Oc2c1ccc(N1c(cc3[o]c4ccccc4c3c3)c3C=Cc3c1cccc3)c2 HABFLXGFNIQKGT-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- CEGQRCQPQHGRBV-UHFFFAOYSA-N c(cc1)cc(c2c3)c1[o]c2cc1c3C=Cc2ccccc2N1 Chemical compound c(cc1)cc(c2c3)c1[o]c2cc1c3C=Cc2ccccc2N1 CEGQRCQPQHGRBV-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
化合物 | Tg(℃) | Td(℃) | λPL(nm) | Φf | 循环伏安稳定性 |
化合物C18 | 132 | 379 | 476 | 78.5 | 优 |
材料CBP | 113 | 353 | 369 | 26.1 | 差 |
化合物C84 | 135 | 385 | 461 | 76.3 | 优 |
材料BD1 | - | 334 | 486 | 28.3 | 差 |
器件代号 | 电流效率 | 色彩 | LT95寿命 |
实施例46 | 1.3 | 蓝光 | 7.9 |
实施例47 | 1.2 | 蓝光 | 6.1 |
实施例48 | 1.4 | 蓝光 | 6.7 |
实施例49 | 1.5 | 蓝光 | 5.7 |
实施例50 | 1.3 | 蓝光 | 6.5 |
实施例51 | 1.4 | 蓝光 | 8.1 |
比较例2 | 1.0 | 蓝光 | 1.0 |
Claims (6)
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CN110372691B (zh) * | 2018-04-13 | 2021-10-22 | 江苏三月科技股份有限公司 | 一种以氧杂蒽酮为核心的化合物、其制备方法及其在oled上的应用 |
CN110372679A (zh) * | 2018-04-13 | 2019-10-25 | 江苏三月光电科技有限公司 | 一种以芳基酮为核心的化合物、其制备方法及其在oled上的应用 |
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CN111848589B (zh) * | 2019-04-30 | 2022-04-05 | 江苏三月科技股份有限公司 | 氧杂蒽酮衍生物、其制法、用途及包含其的发光器件 |
CN113004259B (zh) * | 2019-12-20 | 2023-12-26 | 江苏三月科技股份有限公司 | 一种以蒽酮骨架为核心的化合物及其应用 |
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