CN113979919A - Indolo spirofluorene organic compound, organic electroluminescent device and display device - Google Patents
Indolo spirofluorene organic compound, organic electroluminescent device and display device Download PDFInfo
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- CN113979919A CN113979919A CN202111405998.XA CN202111405998A CN113979919A CN 113979919 A CN113979919 A CN 113979919A CN 202111405998 A CN202111405998 A CN 202111405998A CN 113979919 A CN113979919 A CN 113979919A
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- spirofluorene
- indolo
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 37
- -1 benzofluorenyl Chemical group 0.000 claims description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 7
- 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 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- 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 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy 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 description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 19
- 229940125904 compound 1 Drugs 0.000 description 11
- 238000001704 evaporation Methods 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 8
- 238000001308 synthesis method Methods 0.000 description 8
- 238000001514 detection method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229940125810 compound 20 Drugs 0.000 description 4
- 229940125846 compound 25 Drugs 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 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
- 238000005286 illumination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 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
- C07D405/02—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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- 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
- C07D409/02—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
- C07D409/12—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 chain containing hetero atoms as chain links
-
- 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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an indolo spirofluorene organic compound, an organic electroluminescent device and a display device.
Description
Technical Field
The invention belongs to the technical field of electroluminescence, and relates to an indolo spirofluorene organic compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
The selection of the hole layer, the light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency, the driving voltage and the lifetime of the device, and functional layer materials with higher performance are still being explored.
Therefore, in order to meet the higher requirements of people for OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the art.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an indolocairofluorene organic compound, an organic electroluminescent device and a display device. The organic compound can be used as a phosphorescent host material of an OLED (organic light emitting diode) light emitting device.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an indolo spirofluorene organic compound having a structure represented by the following formula (I):
Ar1selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C5-C40 heteroaryl or substituted or unsubstituted C1-C12 alkyl;
Ar2selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C5-C40 heteroaryl;
ar is selected from H, deuterium, F, CN, substituted or unsubstituted aryl of C6-C40, substituted or unsubstituted heteroaryl of C5-C40 or substituted or unsubstituted alkyl of C1-C12;
x is selected from O, S, C(R1R2) Or NR, wherein R, R1And R2Is selected from substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C6-C40 aryl; r1And R2Independently exist or are bridged into a ring;
when the substituted group contains a substituent, the substituent is selected from one or a combination of at least two of F, CN, deuterium, alkyl of C1-C12, alkenyl of C2-C8, alkoxy of C1-C6 and aryl of C6-C40.
In the present invention, the definition of a group defines the range of the number of carbon atoms, the number of carbon atoms of which is any integer within the defined range, for example, C6-C40 aryl, the number of carbon atoms representing the aryl group can be any integer within the range of 6-40, for example, 6, 8, 10, 15, 20, 30, 35, 38 or 40, etc., and the definition of the number of carbon atoms of other groups, in turn, has the same meaning.
Preferably, Ar1And Ar2At least one heteroaryl group selected from substituted or unsubstituted C5-C40.
Preferably, the aryl group of C6 to C40 is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenfluorenyl, dibenzoindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl, or a combination of one or more groups thereof.
Preferably, the heteroaryl group of C5-C40 is selected from dibenzofuranyl, dibenzothienyl, naphthodibenzofuranyl, naphthodibenzothienyl, benzonaphthodibenzofuranyl, or benzonaphthodibenzothienyl.
Preferably, Ar1Selected from phenyl, biphenyl, methyl, ethyl, propyl, butyl, pentyl or hexyl.
Preferably, Ar2Selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzoFluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, benzonaphthyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, or benzodibenzothiophenyl.
Preferably, Ar is selected from hydrogen, phenyl, biphenyl, terphenyl or naphthyl.
In the present invention, R1And R2Independently present or bridged into a ring. Preferably, R1And R2Selected from benzene rings and bridged to form a ring, forming the following structure:
as another example, R1Selected from ethyl, R2When selected from ethyl, R1And R2The bridge ring forms the following structure:
of course, R1And R2When selected from other alkyl groups, the following structures may be formed including, but not limited to:
preferably, the organic compound is any one of the following compounds:
wherein D represents deuterium.
In the present invention, the synthetic route of the organic compound is as follows:
in another aspect, the present invention provides a light-emitting layer comprising the indolo spirofluorene organic compound as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising the indolo spirofluorene organic compound as described above.
Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode, wherein the organic thin film layer comprises the indolo spirofluorene organic compound.
Preferably, the organic thin film layer includes a light-emitting layer including the indolo spirofluorene-based organic compound as described above.
In the invention, the indolo spirofluorene organic compound is used as a phosphorescent host material of a light-emitting layer.
In another aspect, the present invention provides a display apparatus comprising the organic electroluminescent device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the organic compound can be used as a phosphorescent main body material of a light-emitting layer of an OLED light-emitting device, so that the organic electroluminescent device has lower driving voltage (below 5.56V) and higher current efficiency (above 8.76 cd/A).
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthesis example 1 Synthesis of Compound 1
Into a 250mL three-necked flask, M-1-1(5.6g, 0.01mol) and M-1-2(3.35g, 0.01mol) were charged, 100mL of toluene was added, and sodium tert-butoxide (1.2g, 0.013mol), Pd and toluene were added under stirring2(dba)3(0.046g, 0.00005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 8 hours, and detecting by HPLC (M-1)<0.05 percent), stopping the reaction and cooling to room temperature. Washing with salt water for 2 times, adding anhydrous sodium sulfate into organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene for 3 times to obtain compound 1 of 5.0g with HPLC purity>99％。
Mass spectrum detection is carried out on the compound 1, and the molecule m/z is determined to be: 814.30.
compound 1 was subjected to nuclear magnetic detection and the data was resolved as follows:1H-NMR (Bruker, Switzerland, Avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl)3)：δ8.57(m，1H)，δ8.35(s，1H)δ8.23(s，1H)，δ8.19(d，1H)，δ8.08(m，1H)，δ8.00(m，1H)，δ7.88(m，2H)，δ7.76(m，2H)，δ7.68～7.56(m，5H)，δ7.54～7.38(m，10H)，δ7.28～7.06(m，12H)，δ6.99(m，1H)。
Synthesis example 2 Synthesis of Compound 7
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-7-2, Compound 7 was obtained.
Mass spectrometric detection of compound 7 was performed to determine the molecule m/z: 854.33.
Synthesis example 3 Synthesis of Compound 10
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-10-2, Compound 10 was obtained.
Mass spectrometric detection of compound 10 was performed to determine the molecule m/z: 864.31.
Synthesis example 4 Synthesis of Compound 17
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-17-2, Compound 17 was obtained.
Compound 17 was mass-spectrometrically detected to determine the molecule m/z: 830.28.
Synthesis example 5 Synthesis of Compound 20
(1) Synthesis of Compound M-20-2
A 250ml three-mouth bottle is added with 80 ml under the protection of nitrogenDried toluene, 1.4 g (0.015mol) of aniline, 4.91 g (0.01mol) of M-20-0, 0.0575 g (0.0001mol) of Pd (dba)2(bis-dibenzylideneacetone palladium), 0.4 g (0.0002mol) of a toluene solution containing 10% tri-tert-butylphosphine and 1.44 g (0.015mol) of sodium tert-butoxide were heated to reflux for 8 hours, cooled, and then the aqueous layer was separated, the organic layer was washed 2 times with 2% hydrochloric acid, washed with water to neutrality, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and recrystallized twice with a mixed solvent of methanol and toluene to give 2.2 g of an intermediate represented by the formula M-20-2.
Performing mass spectrum detection on the intermediate shown in the formula M-20-2, and determining that the molecular M/z is as follows: 503.17.
(2) synthesis of Compound 20
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-20-2, Compound 20 was obtained.
Compound 20 was mass-spectrometrically detected to determine the molecule m/z: 982.34.
Synthesis example 6 Synthesis of Compound 25
(1) Synthesis of Compound M-25-2
Synthesis method referring to the synthesis of the compound M-20-2 in example 5, except that the compound represented by M-20-0 was changed to the compound represented by M-25-0, the compound M-25-2 was obtained.
The compound M-25-2 is subjected to mass spectrometric detection, and the molecule M/z is determined to be 361.18.
(2) Synthesis of Compound 25
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-25-2, Compound 25 was obtained.
Compound 25 was mass-spectrometrically detected to determine the molecule m/z: 840.35.
Synthesis example 7 Synthesis of Compound 33
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-2 was changed to the compound represented by M-33-2, Compound 33 was obtained.
Compound 33 was mass-spectrometrically detected to determine the molecule m/z: 813.31.
Synthesis example 8 Synthesis of Compound 81
(1) Synthesis of Compound M-41-1:
a500-ml three-necked flask was charged with nitrogen, 200 ml of acetone, 4.84 g (0.01mol) of the compound represented by formula M-41-0, 2.18 g (0.02mol) of bromoethane and 1 g (0.025mol) of sodium hydroxide were added, the mixture was stirred at room temperature for 48 hours, water and dichloromethane were added for liquid separation, the organic layer was washed with water to neutrality, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and recrystallized from a mixed solvent of methanol and chloroform to give 4.6 g of the compound represented by formula M-41-1.
The intermediate shown as the formula M-41-1 is subjected to mass spectrum detection, and two peaks with the largest M/z are as follows: 511.09, 513.09, determining the molecular formula of the product as C33H22BrN。
(2) Synthesis of Compound 81
Synthesis method referring to the synthesis of Compound 1 in example 1, except that the compound represented by M-1-1 was changed to the compound represented by M-41-1, Compound 81 was obtained.
Compound 81 was mass-spectrometrically detected to determine the molecule m/z: 766.30.
The compound used in the device examples had the following structure, and all organic OLED materials were sublimed to HPLC purity above 99.99%.
Device example 1
In the embodiment, the compound is used as a red light main body material in an organic electroluminescent device, and in the comparative embodiment, HT-1 and CBP are used as the red light main body material in the organic electroluminescent device.
The structure of the organic electroluminescent device is as follows: ITO/HTL (80 nm)/Red host material (35 nm): d-1[ 10% ]/ETL (10nm)/Alq3(15nm)/LiF (0.5nm)/Al (150 nm). Wherein "D-1 [ 10% ]" refers to the doping ratio of the red dye, i.e. the volume ratio of the red host material to Firpic is 100: 10.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-4Pa, vacuum evaporating a hole transport layer HTL on the anode layer film, wherein the evaporation rate is 0.01nm/s, and the evaporation film thickness is 80 nm;
vacuum evaporating a red light main body material and a dye D-1 on the hole transport layer to be used as a light emitting layer of the organic electroluminescent device, wherein the evaporation rate is 0.01nm/s, and the total film thickness of the evaporation is 35 nm; (ii) a
Sequentially vacuum evaporating an electron transport layer ETL and Alq3 on the luminescent layer, wherein the evaporation rates are both 0.01nm/s, and the evaporation film thicknesses are respectively 10nm and 15 nm;
and (3) evaporating LiF with the thickness of 0.5nm and Al with the thickness of 150nm on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
All the organic electroluminescent devices are prepared by the method, and the differences only lie in the selection of red light main body materials, and the details are shown in the following table 1.
And (3) performance testing:
testing the driving voltage, the current efficiency and the service life LT90 of the OLED device provided above by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance; here, LT90 indicates the time required for the luminance to decrease to 90% of the original luminance with the current density kept unchanged at 1000nit of the original luminance.
TABLE 1
As can be seen from Table 1, when the compound of the present invention is used as a red host material, the OLED device can have a lower driving voltage (below 7.19V), and simultaneously has a high current efficiency (above 29.16 cd/A) and a long lifetime (above 33h, even as high as above 80 h).
The applicant states that the present invention is illustrated by the above examples of the organic compound, the organic electroluminescent device and the display device of the present invention, but the present invention is not limited to the above examples, that is, it does not mean that the present invention must be implemented by the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An indolo spirofluorene organic compound having a structure represented by the following formula (I):
Ar1selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C5-C40 heteroaryl or substituted or unsubstituted C1-C12 alkyl;
Ar2selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C5-C40 heteroaryl;
ar is selected from H, deuterium, F, CN, substituted or unsubstituted aryl of C6-C40, substituted or unsubstituted heteroaryl of C5-C40 or substituted or unsubstituted alkyl of C1-C12;
x is selected from O, S, C (R)1R2) Or NR, wherein R, R1And R2Is selected from substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C6-C40 aryl; r1And R2Independently exist or are bridged into a ring;
when the substituted group contains a substituent, the substituent is selected from one or a combination of at least two of F, CN, deuterium, alkyl of C1-C12, alkenyl of C2-C8, alkoxy of C1-C6 and aryl of C6-C40.
2. The indolo spirofluorene organic compound according to claim 1, wherein Ar is Ar1And Ar2At least one heteroaryl group selected from substituted or unsubstituted C5-C40.
3. The indoorospirofluorene organic compound according to claim 1 or 2, wherein the aryl group having 6-C40 is selected from one or a combination of two or more of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenofluorenyl, naphthofluorenyl, or benzonaphthofluorenyl;
preferably, the heteroaryl group of C5-C40 is selected from dibenzofuranyl, dibenzothienyl, naphthodibenzofuranyl, naphthodibenzothienyl, benzonaphthodibenzofuranyl, or benzonaphthodibenzothienyl.
4. The indolo spirofluorene organic compound according to any one of claims 1 to 3, wherein Ar is Ar1Selected from phenyl, biphenyl, methyl, ethyl, propyl, butyl, pentyl or hexyl;
preferably, Ar2Selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenenyl, dibenzoindenofluorenyl, naphthofluorenyl, benzonaphthyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranyl, or dibenzothiophenyl;
preferably, Ar is selected from hydrogen, phenyl, biphenyl, terphenyl or naphthyl.
5. The indolo spirofluorene organic compound according to any one of claims 1 to 4, wherein R is1And R2Selected from benzene rings and bridged to form a ring, forming the following structure:
preferably, R1Selected from ethyl, R2When selected from ethyl, R1And R2The bridge ring forms the following structure:
preferably, the indolo spirofluorene organic compound is a compound having any one of the following structures:
6. the indolo spirofluorene organic compound according to any one of claims 1 to 5, wherein the indolo spirofluorene organic compound is any one of the following compounds:
wherein D represents deuterium.
7. A light-emitting layer comprising the indolo spirofluorene organic compound according to any one of claims 1 to 6.
8. An organic electroluminescent device comprising the indolo spirofluorene organic compound according to any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising the indolo spirofluorene-based organic compound according to any one of claims 1 to 6;
preferably, the organic thin film layer comprises a hole transport layer comprising the indolo spirofluorene-based organic compound according to any one of claims 1 to 6;
preferably, the organic thin film layer includes a light-emitting layer including the indolo spirofluorene-based organic compound according to any one of claims 1 to 6;
preferably, the indolo spirofluorene organic compound is used as a phosphorescent host material of a light-emitting layer.
10. A display device characterized by comprising the organic electroluminescent device according to claim 8 or 9.
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| CN113620860A (en) * | 2020-12-14 | 2021-11-09 | 阜阳欣奕华材料科技有限公司 | Organic electroluminescent compound and preparation method and application thereof |
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| KR20100003624A (en) * | 2008-07-01 | 2010-01-11 | 덕산하이메탈(주) | Novel condensed carbazole derivatives and organic electroluminescent device comprising same |
| CN106207000A (en) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | Organic luminescent device |
| CN108922987A (en) * | 2018-06-21 | 2018-11-30 | 赵东敏 | Biindolyl class material, organic electroluminescence device and display device |
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