CN114507224B - Ketone-containing organic compound and application thereof - Google Patents
Ketone-containing organic compound and application thereof Download PDFInfo
- Publication number
- CN114507224B CN114507224B CN202111275938.0A CN202111275938A CN114507224B CN 114507224 B CN114507224 B CN 114507224B CN 202111275938 A CN202111275938 A CN 202111275938A CN 114507224 B CN114507224 B CN 114507224B
- Authority
- CN
- China
- Prior art keywords
- group
- organic compound
- light
- organic
- emitting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 23
- 150000002576 ketones Chemical class 0.000 title claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 47
- -1 benzopyrazinyl Chemical group 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 32
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 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 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- 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 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125851 compound 27 Drugs 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 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 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000012459 cleaning agent Substances 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
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001725 pyrenyl 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 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
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- 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
- 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
- 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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a ketone-containing organic compound and application thereof, and belongs to the technical field of semiconductors. The structure of the organic compound provided by the invention is shown as a general formula (I):the invention also discloses application of the compound. The organic compound has higher thermal stability; meanwhile, when the light-emitting layer material is used as a light-emitting layer material of an OLED light-emitting device, a TADF effect can be generated, the voltage of the device can be effectively reduced, the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.
Description
Technical Field
The invention relates to a ketone-containing organic compound and an organic electroluminescent device comprising a luminescent layer of the ketone-containing compound, belonging to the technical field of semiconductors.
Background
The organic electroluminescent device (OLED: organic Light Emission Diodes) technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect.
The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic light-emitting functional layers clamped between different electrode film layers, and materials with different functions are mutually overlapped together according to purposes to form the OLED light-emitting device. When a voltage is applied to the electrodes at the two ends of the OLED light-emitting device as a current device and positive and negative charges in the organic light-emitting functional layer act through an electric field, the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
The development and the use of the light-emitting layer material of the OLED go through three main stages, wherein the first stage is mainly based on a fluorescence light-emitting mechanism, the second stage is mainly based on a phosphorescence light-emitting mechanism, and the third stage uses a TADF material as the light-emitting layer material, so that triplet excitons are effectively utilized, and the light-emitting efficiency of the device is improved. TADF materials are developed to date, have abundant application in luminescent layers, have controllable structure, stable property and low price, do not need precious metals, and have wide application prospects in the field of OLEDs.
Theoretically, the TADF material can realize 100% exciton utilization rate through the opposite system jump from the triplet state to the singlet state, but in the process of serving as a main body or doping in practical application, the device effect is poor, and the following problems still exist mainly: (1) Because of the small S1-T1 band gap required by the TADF material design, the rapid intersystem crossing rate (shorter delayed luminescence life) and the high fluorescence quantum yield are difficult to combine; (2) Due to the strong CT effect, the TADF material has the phenomenon of spectrum instability caused by different proportions.
Disclosure of Invention
The present invention provides a ketone-containing organic compound and its application, which address the above-mentioned problems of the prior art. The ketone-containing compound material can effectively improve the photoelectric property of an OLED device and prolong the service life of the OLED device after being applied to the OLED device.
A ketone-containing organic compound having a structure represented by the general formula (1):
in the general formula (1), X represents-O-or-S-;
the Cy is represented as substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
the Z is 1 Each occurrence of which is identically or differently represented as a nitrogen atom, a carbon atom, or a C-R 1 Adjacent R 1 May also be bonded to form a ring;
the Z is 2 Each occurrence of which is identically or differently represented as a nitrogen atom, a carbon atom, or a C-R 2 Adjacent R 2 May also be bonded to form a ring;
the Z is 3 Each occurrence of which is identically or differently represented as a nitrogen atom, a carbon atom, or a C-R 3 Adjacent R 3 May also be bonded to form a ring;
R 1 -R 3 independently of each other, are represented by a hydrogen atom, a deuterium atom, a cyano group, a halogen, a C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
the substituents "substituted or unsubstituted" are optionally selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 One or more of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom and nitrogen atom.
Preferably, cy is expressed as one of the following groups:
wherein the number in the ring structure indicates the site of joinable.
Preferably, the C 6-30 Aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl, terphenyl, triphenylene, dimethylfluorenyl or diphenylfluorenyl;
the C is 2-30 Heteroaryl is represented by one of pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, pyridazinyl, thienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, quinolinyl, isoquinolinyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl, azatriphenylene, azabiphenyl, azaphenanthryl, azadimethylfluorene, azadibenzofuranyl, azadibenzothienyl;
the C is 1-10 The alkyl is one of methyl, ethyl, propyl, isopropyl and tert-butyl;
the substituent of the "substituted or unsubstituted" is one or more of protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, naphthyridinyl group, fluorenyl group, dibenzofuranyl group, N-phenylcarbazolyl group, dibenzothienyl group.
Preferably, the structure of the organic compound can be shown as any one of the general formulas (1-1) to (1-16)
Preferably, the specific structure of the organic compound is any one of the following structures:
an organic electroluminescent device comprising an anode, a cathode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer containing the organic compound.
Preferably, the organic light-emitting functional layer includes a light-emitting layer containing the organic compound; in an amount of 85 to 99 wt%, more preferably 90 to 99 wt% and most preferably 90 to 95 wt%, based on 100 wt% of the host material and the doping material of the light emitting layer.
A lighting or display element comprising said organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) The material has higher thermal stability and film phase stability, so that the material has stronger stability as a device, thereby effectively prolonging the service life of the device;
(2) The device has the characteristics of high efficiency TADF, can fully utilize triplet energy to improve the luminous efficiency of the device, reduce triplet exciton quenching of a main material and prolong the service life of the device;
(3) The material has better spectral stability, and can ensure that energy is effectively transferred to the doping material when the material is used as a sensitizer;
(4) The material has higher PLQY, and can effectively improve the efficiency of a device when being used as a sensitizer;
drawings
FIG. 1 is a schematic diagram of the structure of an OLED device using the materials of the present invention;
in the figure, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
FIG. 2 is a nuclear magnetic resonance spectrum of a compound 110 of the present invention;
FIG. 3 is a nuclear magnetic resonance spectrum of compound 14 of the present invention;
Detailed Description
The principles and features of the present invention are described below with reference to the drawings and examples, which are provided for illustration only and are not intended to limit the scope of the invention.
All raw materials in the preparation example are purchased from medium energy saving Wanchun Co., ltd.
Preparation of raw material C
The preparation process of the raw material C1 comprises the following steps:
under nitrogen atmosphere, 0.05mol of raw material M1 and 0.06mol of Mg powder are added into a three-mouth bottle, then 60ml of dry tetrahydrofuran is added for dissolving, and then 0.0004mol of simple substance I is added 2 . The reaction mixture was heated to 40 ℃ and stirred until the solution turned from yellow to colorless. And heating the mixed solution to 80 ℃, stirring and reacting for 4 hours, wherein no magnesium powder remains, and the reaction is complete, thus obtaining a raw material C1.
The preparation of the other starting material C was similar to that of the starting material C1, except that the starting material M1 was changed.
Preparation of intermediate B
The preparation process of the intermediate B1 comprises the following steps:
in a three-necked flask, 8mmol of the starting material D1 was dissolved in 50ml of anhydrous tetrahydrofuran, cooled in an ice bath and stirred for 0.5 hour; tetrahydrofuran (3 mol/L,3 mL) solution of the raw material C1 was added dropwise thereto, stirred at 0℃for 2 hours and then slowly returned to room temperature, then the reaction solution was poured into water, extracted with dichloromethane first, the organic compound was dried with magnesium sulfate, and silica gel column chromatography was performed with dichloromethane/petroleum ether (v/v=2:3) as a eluting agent, and dried after rotary evaporation, to obtain the intermediate A1.
In a three-necked flask, 100mL of methylene chloride was added, then, intermediate A1 was added thereto, and 12mmol of pyridinium chlorochromate (PCC) was further added thereto, and stirred at room temperature for 24 hours, then, the reaction solution was poured into 200mL of water, extracted with methylene chloride, the organic compound was dried with magnesium sulfate, and silica gel column chromatography was performed using methylene chloride/petroleum ether (v/v=2:3) as a eluting agent, followed by drying after rotary evaporation to obtain intermediate B1.
The synthesis of intermediate B2 to intermediate B17 is similar to the synthesis of intermediate B1, except that the starting materials and intermediates used are different, and the structural formulae of the starting materials, intermediates and products are shown in the following table.
TABLE 1
EXAMPLE 1 Synthesis of Compound 6
4.4mmol of intermediate B1 and 4.4mmolRaw material E1 was added to 50ml of toluene solution, deaerated for 10 minutes, and then 0.1mmol Pd (AcO) was added thereto 2 0.3mmol of 1,1' -bis (diphenylphosphine) ferrocene (dppf) and 6mmol of tBuona under the protection of nitrogen, the mixture is heated for 24 hours under reflux and stirring, then the reaction solution is poured into water, the dichloromethane is used for extraction, the organic compound is dried by magnesium sulfate, dichloromethane/petroleum ether (v/v=2:3) is used as a leaching agent for silica gel column chromatography separation, the mixture is dried after rotary evaporation, and the final product is dried at 280 ℃ and 4 multiplied by 10 -4 Further sublimation under Pa gave compound 6.
Example 2-example 18 was prepared similarly to example 1, except that the starting materials and intermediates used were different, and the following table shows the structural formulas of the starting materials, intermediates and products.
TABLE 2
Example 19: synthesis of Compound 27
(1) 4.4mmol of intermediate B16 and 4.4mmol of starting material E2 are added to 50ml of toluene, degassed for 10 minutes and then 0.1mmol of Pd (AcO) are added 2 0.3mmol of 1,1' -bis (diphenylphosphine) ferrocene (dppf) and 6mmol of tBuONa under nitrogen protection, the mixture was heated under reflux with stirring for 24 hoursThen pouring the reaction solution into water, extracting with dichloromethane, drying organic compound with magnesium sulfate, separating by silica gel column chromatography using dichloromethane/petroleum ether (v/v=2:3) as eluent, rotary evaporating, drying, and standing at 280 deg.C and 4×10 -4 Further sublimation under Pa gave intermediate I-1.
(2) 4.4mmol of intermediate I-1 and 4.4mmol of starting material E6 are added to 50ml of toluene, degassed for 10 minutes and then 0.1mmol of Pd (AcO) are added 2 0.3mmol of 1,1' -bis (diphenylphosphine) ferrocene (dppf) and 6mmol of tBuona under the protection of nitrogen, the mixture is heated for 24 hours under reflux and stirring, then the reaction solution is poured into water, the dichloromethane is used for extraction, the organic compound is dried by magnesium sulfate, dichloromethane/petroleum ether (v/v=2:3) is used as a leaching agent for silica gel column chromatography separation, the mixture is dried after rotary evaporation, and the final product is dried at 280 ℃ and 4 multiplied by 10 -4 Further sublimation under Pa gave compound 27.
Example 19-example 24 was prepared similarly to example 19, except that the starting materials and intermediates used were different, and the following table shows the structural formulas of the starting materials, intermediates and products.
TABLE 3 Table 3
The structural characterization of the compounds obtained in the examples is shown in table 4:
TABLE 4 Table 4
The structural characterization of compound 14, compound 110 is shown in table 5:
TABLE 5
The compound of the invention can be used as a luminescent layer material in a luminescent device. The compounds prepared in the above examples of the present invention were tested for energy level, thermal stability and spectrum, respectively, and the results are shown in table 6.
TABLE 6
| Compounds of formula (I) | HOMO(eV) | Est(eV) | τ(μs) | PLQY(％) | Spectral variation (nm) |
| 6 | -5.74 | 0.10 | 1.06 | 70.6 | 24 |
| 14 | -5.92 | 0.09 | 3.00 | 52.3 | 27 |
| 15 | -5.90 | 0.12 | 1.70 | 71.7 | 39 |
| 18 | -5.86 | 0.17 | 2.23 | 60.8 | 32 |
| 27 | -5.82 | 0.13 | 1.89 | 74.3 | 35 |
| 36 | -5.79 | 0.10 | 1.62 | 79.0 | 32 |
| 56 | -5.91 | 0.15 | 2.48 | 79.4 | 31 |
| 80 | -5.90 | 0.08 | 1.57 | 75.6 | 24 |
| 92 | -5.75 | 0.07 | 2.15 | 88.7 | 40 |
| 110 | -5.83 | 0.14 | 1.86 | 89.2 | 22 |
| 111 | -5.94 | 0.11 | 2.50 | 48.2 | 38 |
| 113 | -5.91 | 0.12 | 0.79 | 56.6 | 27 |
| 114 | -5.82 | 0.06 | 1.78 | 51.1 | 23 |
| 120 | -5.87 | 0.13 | 2.17 | 64.9 | 23 |
| 126 | -6.02 | 0.08 | 2.84 | 47.3 | 34 |
| 138 | -5.90 | 0.15 | 3.19 | 86.9 | 38 |
| 161 | -5.77 | 0.10 | 2.36 | 46.6 | 39 |
| 165 | -5.85 | 0.14 | 2.09 | 54.0 | 20 |
| 171 | -5.92 | 0.09 | 2.90 | 57.7 | 36 |
| 182 | -5.89 | 0.12 | 1.17 | 59.1 | 30 |
| 183 | -5.76 | 0.09 | 1.40 | 50.5 | 26 |
| 200 | -5.87 | 0.06 | 2.85 | 84.8 | 23 |
| 219 | -5.93 | 0.12 | 2.77 | 46.5 | 34 |
| 237 | -5.83 | 0.09 | 2.52 | 58.5 | 36 |
| ref-1 | -6.14 | 0.07 | 2.21 | 43.3 | 52 |
Note that: triplet energy level T1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test condition of the material is 2 x 10 -5 A toluene solution of mol/L; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), tested as an atmospheric environment; s1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test conditions of the material are 2 x 10 -5 mol/L toluene solution, ΔEst=S1-T1; PLQY and τ were measured by a Fluorolog-3 series fluorescence spectrometer of Horiba; spectral changes were obtained by subtracting 3% of the luminescence peak of the blend film doped with CBP from the luminescence peak of the pure film, and the test was performed by a Fluorolog-3 series fluorescence spectrometer of Horiba.
As can be seen from the above table data, the compounds of the present invention have suitable energy levels and suitable triplet energies, and can be applied to the light emitting layer of an OLED device as a host; the organic compound has higher thermal stability and shorter delayed fluorescence lifetime, and has higher efficiency and longer lifetime when being used as a luminescent layer material after being applied to an OLED device.
The effect of the compound synthesized according to the present invention on the use as a material for a light-emitting layer in a device will be described in detail below by means of device examples 1 to 24 and device comparative examples 1 to 3. Compared with the device example 1, the device examples 2-24 and the device comparative examples 1-3 of the invention have the same manufacturing process, and the same substrate material and electrode material are adopted, so that the film thickness of the electrode material is kept consistent, except that the material of the luminescent layer in the device is changed; the composition of each layer of each device is shown in Table 7, and the results of the performance test of each device are shown in Table 8.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness 150 nm) is washed, that is, washed with a cleaning agent (semiconductor M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a luminescent layer 6 of the OLED luminescent device is manufactured, CBP is used as a first main body, a compound 6 is used as a second main body, GD-1 is used as green light for doping, the mass ratio of the CBP to the compound 6 to the GD-1 is 67:30:3, and the thickness of the luminescent layer is 30nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to be carried out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 30nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 80nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10.
After completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the current efficiency, external quantum efficiency and lifetime of the device were measured. Examples of devices prepared in the same manner and comparative examples are shown in table 7; the test results of the current efficiency, external quantum efficiency and lifetime of the obtained device are shown in table 8.
TABLE 7
TABLE 8
Note that: the voltage, current efficiency and color coordinates are at a current density of 10mA/cm 2 Tested under conditions, an IVL (current-voltage-brightness) test system (fexostat scientific instruments, su); the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 means at 20mA/cm 2 The time taken for the brightness of the device to decay to 95% is now described.
As can be seen from the device data results of table 8, the organic light emitting device of the present invention achieves a greater improvement in both device efficiency and device lifetime compared to the OLED device of the known materials. Meanwhile, the organic light emitting device of the present invention has a reduced voltage compared to OLED devices of known materials.
Finally, the above embodiments are only for illustrating the technical solution of the present invention and are not limiting. Modifications and equivalents of the present invention may occur to those skilled in the art without departing from the spirit and scope of the present invention, and are intended to be encompassed by the scope of the following claims.
Claims (5)
1. The ketone-containing organic compound is characterized by having a structure represented by general formulas (1-1) to (1-3) and (1-14):
in the general formulas (1-1) to (1-3) and (1-14), X is-O-or-S-;
the Z is 1 Each occurrence is identically or differently denoted as C-R 1 Adjacent R 1 May also be bonded to form a ring;
the Z is 2 Each occurrence is identically or differently denoted as C-R 2 Adjacent R 2 May also be bonded to form a ring;
the Z is 3 Each occurrence of which is identically or differently represented as a nitrogen atom or C-R 3 ；
R 1 -R 3 Independently of each other, are represented by a hydrogen atom, a deuterium atom, a cyano group, a halogen, a C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
the C is 6-30 Aryl is phenyl, naphthyl, biphenyl, triphenylene;
the C is 2-30 Heteroaryl is represented by one of pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, pyridazinyl, thienyl, quinolinyl, isoquinolinyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl;
the C is 1-10 The alkyl is one of methyl, ethyl, propyl, isopropyl and tert-butyl;
the substituent of the "substituted or unsubstituted" is one or more of deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, phenyl group, naphthyl group, biphenyl group, and pyridyl group.
2. The organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
3. an organic electroluminescent device comprising an anode and a cathode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer contains the organic compound according to any one of claims 1 to 2.
4. The organic electroluminescent device according to claim 3, wherein the organic light-emitting functional layer comprises a light-emitting layer, wherein the light-emitting layer comprises the organic compound according to any one of claims 1 to 2.
5. A lighting or display element, characterized in that it comprises an organic electroluminescent device as claimed in claim 3 or 4.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011278700 | 2020-11-16 | ||
| CN2020112787009 | 2020-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114507224A CN114507224A (en) | 2022-05-17 |
| CN114507224B true CN114507224B (en) | 2024-02-27 |
Family
ID=81548774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111275938.0A Active CN114507224B (en) | 2020-11-16 | 2021-10-29 | Ketone-containing organic compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114507224B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015192941A1 (en) * | 2014-06-18 | 2015-12-23 | Merck Patent Gmbh | Compositions for electronic devices |
| CN109651406A (en) * | 2019-01-23 | 2019-04-19 | 苏州久显新材料有限公司 | Hot activation delayed fluorescence compound, luminescent material and organic electroluminescence device |
| CN111253382A (en) * | 2018-11-30 | 2020-06-09 | 江苏三月光电科技有限公司 | Organic compound with ketone derivative as core, preparation method and application thereof |
| CN111574508A (en) * | 2019-02-19 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound based on aza-benzene and benzo-heterocycle, preparation method and application thereof |
| KR20200108162A (en) * | 2019-03-07 | 2020-09-17 | 난징고광반도체재료유한회사 | Novel organic compound and materials for organic electroluminescent devices comprising the same and organic electroluminescent devices comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831796B (en) * | 2016-12-30 | 2019-06-11 | 上海天马有机发光显示技术有限公司 | A kind of electroluminescent organic material and organic photoelectric device |
-
2021
- 2021-10-29 CN CN202111275938.0A patent/CN114507224B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015192941A1 (en) * | 2014-06-18 | 2015-12-23 | Merck Patent Gmbh | Compositions for electronic devices |
| CN111253382A (en) * | 2018-11-30 | 2020-06-09 | 江苏三月光电科技有限公司 | Organic compound with ketone derivative as core, preparation method and application thereof |
| CN109651406A (en) * | 2019-01-23 | 2019-04-19 | 苏州久显新材料有限公司 | Hot activation delayed fluorescence compound, luminescent material and organic electroluminescence device |
| CN111574508A (en) * | 2019-02-19 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound based on aza-benzene and benzo-heterocycle, preparation method and application thereof |
| KR20200108162A (en) * | 2019-03-07 | 2020-09-17 | 난징고광반도체재료유한회사 | Novel organic compound and materials for organic electroluminescent devices comprising the same and organic electroluminescent devices comprising the same |
Non-Patent Citations (1)
| Title |
|---|
| Berenis Domantas et al..《Dyes and Pigments》.2020,第182卷第108579页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114507224A (en) | 2022-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114105956B (en) | Compound taking triazine derivative as core and organic electroluminescent device comprising compound | |
| CN113929709B (en) | Organic compound containing boron and nitrogen and organic electroluminescent device containing same | |
| CN113004259B (en) | Compound with anthrone skeleton as core and application thereof | |
| CN114105868B (en) | Organic compound with 4-cyanopyridine as core and organic electroluminescent device comprising same | |
| CN114276372B (en) | Boron-containing condensed ring compound for OLED luminescent layer and application thereof | |
| CN113929708A (en) | Boron-containing compound and application thereof in organic electroluminescent device | |
| CN115894491A (en) | Electron transport material, preparation method thereof, light-emitting device and light-emitting device | |
| CN114276337A (en) | TADF material and organic electroluminescent device comprising same | |
| CN113527112A (en) | Pyrene derivative modified by deuterated group and application thereof | |
| JP2022513608A (en) | Organic electroluminescence material and its preparation method and organic electroluminescence device | |
| CN113072568B (en) | Organic electroluminescent material containing diboron and application thereof | |
| CN115368370A (en) | Condensed nitrogen heterocyclic compound, application thereof and organic electroluminescent device containing compound | |
| CN112479904B (en) | Organic compound with indeno-anthracene derivative as core and application thereof | |
| CN114621241A (en) | Compound with triazine benzofuran structure as core framework and application thereof | |
| CN116396311A (en) | Boron-containing organic compound and organic electroluminescent device prepared from same | |
| CN114507224B (en) | Ketone-containing organic compound and application thereof | |
| CN112480133B (en) | Compound with benzospiroanthracene as core and application thereof | |
| CN114685465B (en) | Ketone-containing organic compound and organic electroluminescent device comprising same | |
| CN114249734A (en) | Compound with anthrone derivative as core and application of compound in OLED device | |
| CN114075229A (en) | Boron-containing organic compound and application thereof in organic electroluminescent device | |
| CN114621171A (en) | Organic compound with naphthalene anthracene derivative as core and application thereof | |
| CN114605449A (en) | Boron-containing organic compound and application thereof in organic electroluminescent device | |
| CN112661746A (en) | Organic electroluminescent naphthofurans compound and preparation method and application thereof | |
| CN114621203B (en) | Ketone-containing TADF organic compound and its application | |
| CN114805319B (en) | Compound taking triazine derivative as core and organic electroluminescent device comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214101 Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province Applicant before: Jiangsu March Technology Co.,Ltd. |
|
| CB02 | Change of applicant information | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |