CN114249713B - 一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物及其应用 - Google Patents
一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物及其应用 Download PDFInfo
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- CN114249713B CN114249713B CN202011002504.9A CN202011002504A CN114249713B CN 114249713 B CN114249713 B CN 114249713B CN 202011002504 A CN202011002504 A CN 202011002504A CN 114249713 B CN114249713 B CN 114249713B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 16
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 title claims abstract description 14
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims description 38
- 239000002346 layers by function Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 238000005457 optimization Methods 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
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- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- -1 thioxanthone organic compound Chemical class 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052805 deuterium Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000005549 heteroarylene group Chemical group 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
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- 238000000034 method Methods 0.000 description 5
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- 229910052717 sulfur Inorganic materials 0.000 description 5
- 229910052722 tritium Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
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- 239000007772 electrode material Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 238000005286 illumination Methods 0.000 description 3
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
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- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229940125936 compound 42 Drugs 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 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 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- BUVUECNWADRNKX-UHFFFAOYSA-N NC(C=C1)=CC=C1C(C=CC(N)=C1C#N)=C1NC1=CC=CC=C1 Chemical compound NC(C=C1)=CC=C1C(C=CC(N)=C1C#N)=C1NC1=CC=CC=C1 BUVUECNWADRNKX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 239000012459 cleaning agent Substances 0.000 description 1
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000003996 delayed luminescence Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D405/14—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 three or more hetero rings
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- 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
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
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- 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
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- 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
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- 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
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
本发明涉及一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物,属于半导体技术领域;所述有机化合物的结构如通式(1),本发明化合物具有空间CT效应,通过器件结构优化,可有效提升OLED器件的光电性能以及OLED器件的寿命。
Description
技术领域
本发明属于有机光电材料领域,涉及新的氧杂蒽酮或硫杂蒽酮类有机化合物及其用作有机发光功能材料的用途,以及一种具有包含该类结构材料的发光层的有机电致发光器件。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。OLED发光器件犹如三明治的结构,包括电极材料膜层,以及夹在不同电极膜层之间的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件,当对OLED发光器件的两端电极施加电压,并通过电场作用有机层功能材料膜层中的正负电荷,正负电荷进一步在发光层中复合,即产生OLED电致发光。
OLED的发光层材料的开发及使用前后共经历了三个主要阶段,第一阶段以荧光发光机制为主,第二阶段以磷光发光机制为主,第三阶段运用TADF材料作为发光层材料,有效的利用三线态激子从而提升器件的发光效率。TADF材料发展至今,在发光层中有丰富的应用,且其结构可控,性质稳定,价格便宜无需贵重金属,在OLEDs领域的应用前景广阔。
理论上,TADF材料可以通过三线态到单线态的反系间窜跃,实现100%的激子利用率,但在实际应用充当主体或者掺杂的过程中,器件效果不佳,其主要仍然存在如下问题:(1)由于TADF材料设计要求较小的S1-T1带隙,快速的反系间窜跃速率(较短的延迟发光寿命)与高荧光量子产率难以兼得;(2)由于较强的CT效应,TADF材料存在随比例不同而导致的光谱不稳定现象。
就目前OLED显示照明产业的实际需求而言,TADF材料的发展远远不够,仍需投入大量人力物力,以解决该类材料商业化过程中遇到的效率和寿命发展滞后的难题。
发明内容
针对现有技术存在的上述问题,本发明申请人提供了一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物及其应用。本发明化合物具有空间CT效应,通过器件结构优化,可有效提升OLED器件的光电性能以及OLED器件的寿命。
一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物,所述有机化合物的结构如通式(1)所示
其中,Z每次出现相同或不同地表示为CR或者氮原子;X1表示为氧原子或者硫原子;
L1、L2分别表示为单键、取代或未取代的C6-C30亚芳基、取代或者未取代的C3-C30亚杂芳基中的一种;
R1表示为通式(2)所示结构:
通式(2)中,Z2每次出现相同或不同地表示为氮原子或者CR,同一芳环上相邻的两个R还可以键接成环;X2每次出现相同或不同地表示为单键、氧原子、硫原子或NR;
R0表示为通式(3)-通式(7)所示结构中的任一种,通过通式(3)-(7)中*所示位置与L1或者L2相连;
通式(3)中,Z3每次出现相同或不同地表示为氮原子或者CR;
通式(6)、通式(7)中,X3、X4分别独立的表示为单键、氧原子、硫原子或
R每次出现相同或不同地表示为氢原子、卤素原子、氘原子、羟基、苯胺基、联苯胺基、氰基、C1-C10的烷基、取代或者未取代的C6-C30的芳基、取代或者未取代的C3-C30的杂芳基中的任一种;
用于取代基团的取代基选自任选自氘、氚、羟基、氰基、苯胺基、联苯胺基、C1~C10烷基、氘或氚取代的C1~C10烷基、环原子数为6~30的芳基、氘或氚取代的环原子数为6~30的芳基、环原子数为5~30的杂芳基、氘或氚取代的环原子数为5~30的杂芳基中的任意一种。
优选方案,通式(1)中L1、L2分别独立的表示为单键、取代或者未取代的亚苯基、取代或者未取代的亚吡啶基中的一种;用于取代基团的取代基选自任选自氘、氚、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、苯基、二联苯基、三联苯基、萘基、菲基、苯并菲基、吡啶基、嘧啶基、喹啉基、咪唑基、噻唑基、呋喃基、苯并咪唑基、苯并呋喃基、苯并噻唑基、咔唑基、苯基咔唑基、二苯并呋喃基中的任意一种。
进一步优选,通式(1)具体的表示为通式(1-1)~通式(1-10)所示结构中的任一种:
进一步优选,通式(2)表示为通式(2-1)~通式(2-8)所示结构中的任一种:
R每次出现相同或者不同地表示为氢原子、氟原子、甲基、乙基、正丙基、异丙基、丁基、苯基、羟基、氰基、吡啶基、苯胺基、联苯胺基中的任一种;同一芳环上相邻的两个R还可以键接成取代或未取代的环原子数为5~30的杂芳基、取代或未取代的环原子数为6~30的芳基中的任一种。
优选方案,所述化合物的具体结构为以下结构中的任一种:
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一种有机电致发光器件,包括阳极与阴极,以及它们之间的一层有机发光功能层,所述有机发光功能层含有所述的有机化合物。
优选方案,有机发光功能层的主体材料含有所述的有机化合物。
优选方案,有机发光功能层的客体材料含有所述的有机化合物。
与现有技术相比,本发明有益的技术效果在于:
(1)具有较高的热稳定性,以及膜相态稳定性,从而使得材料作为器件是具有较强的稳定性,从而有效的提升器件的寿命
(2)具有高效的TADF特性,使得本发明材料作为主体材料时能充分的利用三线态能量提升器件的发光效率,减小主体材料的三线态激子猝灭延长器件的寿命;
(3)具有较高的PLQY,本发明材料作为TADF客体材料时,可有效的提升器件的发光效率
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图;
其中,1为透明基板层,2为阳极层,3为空穴注入层,4为空穴传输层,5为电子阻挡层,6为发光层,7为空穴阻挡,8为电子传输层,9为电子注入层,10为阴极层。
具体实施方式
定义
本文中使用的C6-C30芳基、环原子数为6~30的芳基是指包括具有6至30个作为成环原子的碳原子的碳环芳族体系的单价基团,本文使用的C6-C30亚芳基指包括具有6至30个作为成环原子的碳原子的碳环芳族体系的二价基团。C6-C30芳基的非限制性示例可以包括苯基、联苯基、菲基、联三苯基、萘基等。C6-C30亚芳基的非限制性示例可以包括亚苯基、亚联苯基、亚菲基、亚联三苯基、亚萘基等。当C6-20芳基和/或C6-20亚芳基包括两个或更多个环时,这些环可以彼此稠合。
本文中所使用的C3-C30杂芳基、C3-C30亚杂芳基、环原子数为5~30的杂芳基是指包括具有作为成环原子的从N、O、P和S中选择的至少一个杂原子和3至30个碳原子的碳环芳族体系的单价基团。本文使用的5-3元亚杂芳基指包括具有作为成环原子的从N、O、P和S中选择的至少一个杂原子和3至30个碳原子的碳环芳族体系的二价基团。5-30元杂芳基的非限制性实例可以包括吡啶基、二苯并呋喃基、苯并噁唑基、双苯并噁唑基、咔唑基、N-苯基咔唑基等。5-30元亚杂芳基的非限制性实例可以包括上述基团的二价基团。当5-30元杂芳基和5-30元亚杂芳基包括两个或更多个环时,这些环可以彼此稠合。
本文中使用的C1-10烷基是指包括具有1至10个碳原子的直链或支链烷基的单价基团。C1-10烷基的非限制性实例可以包括甲基、乙基、正丙基、异丙基、叔丁基、戊基。
I合成实施例
本发明合成实施例中涉及到的原料均采购于中节能万润有限公司。
合成实施例1化合物2的合成
在三口瓶中,在氮气的保护下,加入中间体A1,0.01mol与联硼酸频那醇0.012mol,加入150mL的1,4二氧六环搅拌均匀后,加入醋酸钾0.012mol,5×10-5mol的Pd(dppf)2Cl2(1,1'-双(二苯基膦)二茂铁]二氯化钯二氯甲烷络合物)在100℃下反应24h;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到中间体A1-硼酸酯;紧接着在三口瓶中,在氮气的保护下加入0.012中间体A1-硼酸酯,0.01mol 3-溴-9H-呫吨-9-酮,150mL的甲苯,搅拌均匀后加入0.02mol的K2CO3水溶液,最后加入5×10-5mol的Pd(PPh3)4,加热至120℃反应24h,反应结束后,自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到化合物2。元素分析结构(分子式C56H33NO3):理论值C,87.59;H,4.33;N,1.82;测试值:C,87.58;H,4.32;N,1.84;。LC-MS:理论值为767.25,实测值为767.56。1H NMR(400MHz,Chloroform-d)δ7.96–7.89(m,2H),7.84(dd,1H),7.81(s,2H),7.70(dd,1H),7.66(s,1H),7.57(s,1H),7.51(d,1H),7.50–7.41(m,8H),7.38–7.29(m,9H),7.28–7.23(m,3H),7.19(t,1H),7.14(s,1H),7.08–7.03(m,2H)。
合成实施例3化合物42的合成路线
在三口瓶中,在氮气的保护下加入0.012中间体B1,0.01mol 3-溴-9H-呫吨-9-酮,150mL的甲苯,搅拌均匀后加入0.02mol的K2CO3水溶液,最后加入5×10-5mol的Pd(PPh3)4,加热至120℃反应24h,反应结束后,自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到化合物42,元素分析结构(分子式C52H36N2O2):理论值C,86.64;H,5.03;N,3.89;测试值:C,86.63;H,5.05;N,3.86。LC-MS:理论值为720.28,实测值为720.36。1HNMR(400MHz,Chloroform-d)δ7.93(d,1H),7.84(dd,1H),7.80(s,1H),7.76–7.72(m,2H),7.55–7.38(m,9H),7.35–7.26(m,8H),7.23–7.09(m,5H),7.08–6.99(m,3H),1.71(s,6H)。
实施例14化合物273的合成路线
在三口瓶中,在氮气的保护下,加入0.01mol的中间体D2,0.012mol的9H-占吨-9-酮,3-(4-溴苯基),150mL的甲苯搅拌混合,加入0.03mol的叔丁醇钠,5×10-5mol的醋酸钯,加热至120℃,反应24小时;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到化合物273,元素分析结构(分子式C49H30N2O2):理论值C,86.71;H,4.46;N,4.13;测试值:C,86.70;H,4.45;N,4.14。LC-MS:理论值为678.23,实测值为678.47。1H NMR(400MHz,Chloroform-d)δ7.96–7.90(m,5H),7.85–7.79(m,1H),7.78–7.72(m,2H),7.66(s,1H),7.65–7.59(m,2H),7.55(dd,1H),7.50(s,1H),7.44(ddd,2H),7.41–7.33(m,9H),7.28(s,1H),7.13(d,3H),7.09–7.04(m,2H).
上述反应中合成实施例1的反应过程为反应条件I;实施例3的反应过程为反应条件II;实施例14的反应过程为反应条件III。
具体的合成实施例以及结构测试结果如下表1所示。
表1合成实施例
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合成实施例表格中已合成材料的核磁如下表2所示:
表2合成材料测试数据
表1中所涉及中间件体的合成具体步骤如下:
中间体A1的合成
在三口瓶中,在氮气的保护下,加入0.01mol的原料A1,0.012mol的原料B1,150mL的甲苯搅拌混合,加入0.03mol的叔丁醇钠,5×10-5mol的醋酸钯,加热至120℃,反应24小时;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到目标产物中间体A1;
中间体B1的合成
在三口瓶中,在氮气的保护下,加入0.01mol的原料A12,0.012mol的原料C1,150mL的甲苯搅拌混合,0.03mol的碳酸钾,5×10-5mol的碘化亚铜,加热至120℃,反应24小时;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到中间体E1;
在三口瓶中,在氮气的保护下,加入0.01mol的中间产物E1,0.012mol的原料A4,150mL的甲苯搅拌混合,加入0.03mol的叔丁醇钠,5×10-5mol的醋酸钯,加热至120℃,反应24小时;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到目标产物中间体B1;
中间体C1的合成
在三口瓶中,在氮气的保护下,加入0.01mol的原料A1,0.012mol的原料C1,150mL的甲苯搅拌混合,0.03mol的碳酸钾,5×10-5mol的碘化亚铜,加热至120℃,反应24小时;自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到中间体E2;
在三口瓶中,在氮气的保护下加入0.012中间体E2,0.01mol原料B2,150mL的甲苯,搅拌均匀后加入0.02mol的碳酸钾水溶液,最后加入5×10-5mol的Pd(PPh3)4,加热至120℃反应24h,反应结束后,自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到化合物中间体C1;
中间体D1的合成
在三口瓶中,在氮气的保护下加入0.012原料C3,0.01mol原料A11,150mL的甲苯,搅拌均匀后加入0.02mol的K2CO3水溶液,最后加入5*10-5mol的Pd(PPh3)4,加热至120℃反应24h,反应结束后,自然冷却至室温,过滤,滤液进行减压旋蒸(-0.09MPa,85℃),过中性硅胶柱,得到化合物中间体D1;
具体的中间体的A2-A7的合成方法与A1相同;不同之处在于使用不同的原料进行合成;中间体C2-C5的合成与C1的合成方法相同,不同之处在于使用不同的原料进行合成;中间体D2-D5的合成与D1的合成相同,不同之处在于使用的原料不同。
具体的中间体以及使用的原料如下表3所示。
表3合成所需原料表格
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II基础物性测试
本发明化合物在发光器件中使用,可以作为发光层材料使用。对本发明上述实施例制备的化合物分别进行能级、热稳定性、光谱的测试,检测结果如表4所示:
表4材料基础物性表格
化合物 | HOMO | Eg | T1 | △Est | τ(μs) | PLQY% | 光谱变化(nm) |
2 | 6.17 | 3.02 | 2.71 | 0.08 | 6.00 | 52.1 | 31 |
26 | 6.02 | 2.89 | 2.74 | 0.058 | 2.98 | 80.5 | 35 |
42 | 5.90 | 2.72 | 2.64 | 0.177 | 2.43 | 65.9 | 34 |
63 | 6.07 | 2.67 | 2.42 | 0.113 | 5.13 | 44.4 | 34 |
84 | 6.07 | 3.01 | 2.52 | 0.149 | 6.41 | 81.3 | 36 |
96 | 6.02 | 2.55 | 2.51 | 0.05 | 1.34 | 47.3 | 32 |
121 | 5.84 | 2.59 | 2.72 | 0.067 | 1.69 | 56.7 | 28 |
147 | 6.03 | 3.10 | 2.56 | 0.107 | 0.68 | 82.0 | 36 |
208 | 5.90 | 2.91 | 2.60 | 0.11 | 4.96 | 80.2 | 39 |
228 | 5.98 | 2.93 | 2.67 | 0.136 | 4.99 | 57.5 | 40 |
245 | 5.72 | 2.80 | 2.79 | 0.153 | 2.00 | 43.5 | 31 |
257 | 5.96 | 2.61 | 2.72 | 0.178 | 2.35 | 74.4 | 26 |
270 | 6.10 | 2.98 | 2.37 | 0.132 | 4.68 | 53.2 | 27 |
273 | 5.80 | 2.73 | 2.60 | 0.142 | 1.60 | 70.3 | 28 |
300 | 5.75 | 3.01 | 2.47 | 0.056 | 5.00 | 54.3 | 30 |
309 | 6.16 | 2.87 | 2.60 | 0.072 | 0.77 | 46.5 | 40 |
310 | 5.70 | 2.75 | 2.72 | 0.159 | 3.08 | 58.5 | 33 |
312 | 5.75 | 2.78 | 2.79 | 0.065 | 2.24 | 88.0 | 39 |
314 | 5.93 | 2.95 | 2.38 | 0.141 | 4.54 | 75.2 | 40 |
ref-1 | 6.14 | 2.49 | 2.64 | 0.07 | 2.21 | 43.3 | 52 |
ref-2 | 5.90 | 2.90 | 2.79 | 0.03 | 5.78 | 15.8 | 25 |
注:三线态能级T1是由Horiba的Fluorolog-3系列荧光光谱仪测试,材料的测试条件为2*10-5mol/L的甲苯溶液;最高占据分子轨道HOMO能级是由电离能量测试系统(IPS-3)测试,测试为大气环境;Eg通过双光束紫外可见分光光度计(型号:TU-1901)进行测试;S1由Horiba的Fluorolog-3系列荧光光谱仪测试,材料的测试条件为2*10-5mol/L的甲苯溶液,△Est=S1-T1;PLQY和τ由Horiba的Fluorolog-3系列荧光光谱仪测试;光谱变化由纯膜发光峰减去3%掺杂于CBP的共混膜发光峰所得,测试由Horiba的Fluorolog-3系列荧光光谱仪测试。
由上表数据可知,本发明的有机化合物具有合适的能级,以及合适的三线态能量,可应用于OLED器件的发光层作为主体或者掺杂,本发明的有机化合物具有较高的热稳定性,较快的延迟荧光寿命,使得其作为发光层材料使用时具有较高效率和较长的寿命。
III器件制备实施例
以下通过器件实施例1-30和器件比较例1-3,详细说明本发明合成的OLED材料在器件中的应用效果。本发明器件实施例2-30以及器件比较例1与器件实施例1相比制作工艺完全相同,且所采用了相同的基板材料和电极材料,电极材料的膜厚也保持一致,所不同的是对器件中的发光层材料做了更换。
器件实施例1
如图1所示,透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行清洗剂(Semiclean M-L20)洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HT-1和HI-1作为空穴注入层3,HT-1和HI-1的质量比为97:3。接着蒸镀60nm厚度的HT-1作为空穴传输层4。随后蒸镀30nm厚度的EB-1作为电子阻挡层5。上述电子阻挡材料蒸镀结束后,制作OLED发光器件的发光层6,使用CBP作为第一主体,化合物2作为第二主体,GD-1作为绿光掺杂,CBP和化合物2、GD-1质量比为67:30:3,发光层膜厚为30nm。在上述发光层6之后,继续真空蒸镀HB-1,膜厚为5nm,此层为空穴阻挡层7。在上述空穴阻挡层7之后,继续真空蒸镀ET-1和Liq,ET-1和Liq质量比为1:1,膜厚为30nm,此层为电子传输层8。在电子传输层8上,通过真空蒸镀装置,制作膜厚为1nm的LiF层,此层为电子注入层9。在电子注入层9上,通过真空蒸镀装置,制作膜厚为80nm的Mg:Ag电极层,Mg、Ag质量比为1:9,此层为阴极层10使用。
如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率、外量子效率和器件的寿命。用同样的方法制备的器件实施例和比较实施例,具体发光层的组成以及器件数据如表5所示。
表5发光层组成以及器件数据
/>
从表5数据可以看出本发明材料制备器件时,与对比材料相比从电压,效率,寿命均有不同程度的提升,具有显著的优势。
为了比较不同器件在不同电流密度的效率衰减的情况,定义效率衰减系数进行表示,它表示驱动电流为10mA/cm2时器件的效率μ10与器件的最大效率μm之差与最大效率之间的比值,/>值越大,说明器件的效率滚降越严重,反之,说明器件在高电流密度下快速衰降的问题得到了控制。对器件实施例1-30和器件比较例1-3分别进行效率衰减系数/>的测定,检测结果如表6所示:
表6
从表6的数据来看,通过实施例和比较例的效率衰减系数对比我们可以看出,本发明的有机发光器件能够有效地降低效率滚降。
综上,以上仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (4)
1.一种含有氧杂蒽酮结构的有机化合物,其特征在于,所述化合物的具体结构为以下结构中的任一种:
。
2.一种有机电致发光器件,包括阳极与阴极,以及它们之间的一层有机发光功能层,其特征在于,所述有机发光功能层含有权利要求1所述的有机化合物。
3.根据权利要求2所述的有机电致发光器件,其特征在于,有机发光功能层的主体材料含有权利要求1所述的有机化合物。
4.根据权利要求2所述的有机电致发光器件,其特征在于,有机发光功能层的客体材料含有权利要求1所述的有机化合物。
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