CN118164942A - Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device - Google Patents
Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device Download PDFInfo
- Publication number
- CN118164942A CN118164942A CN202410434629.0A CN202410434629A CN118164942A CN 118164942 A CN118164942 A CN 118164942A CN 202410434629 A CN202410434629 A CN 202410434629A CN 118164942 A CN118164942 A CN 118164942A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- anthracene compound
- benzofuran
- organic electroluminescent
- 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.)
- Pending
Links
- -1 Anthracene compound Chemical class 0.000 title claims abstract description 34
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 28
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims description 65
- 239000000543 intermediate Substances 0.000 claims description 43
- 238000002360 preparation method Methods 0.000 claims description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 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
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 44
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000001308 synthesis method Methods 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 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
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/631—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
-
- 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
-
- 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
-
- 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
- H10K85/658—Organoboranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an anthracene compound containing a benzofuran group, an intermediate and an organic electroluminescent device. The anthracene compound containing the benzofuran group has a structure shown in a formula I. The anthracene compound containing the benzofuran group can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an anthracene compound containing a benzofuran group, an intermediate and an organic electroluminescent device.
Background
An organic electroluminescent device is a device prepared by depositing one or more layers of organic materials between two metal electrodes by spin coating or vacuum evaporation, and a classical three-layer organic electroluminescent device comprises a hole transport layer, a light emitting layer and an electron transport layer. Holes generated from the anode are combined in the light emitting layer through the hole transport layer and electrons generated from the cathode are combined in the light emitting layer through the electron transport layer to form excitons, and then light is emitted. The organic electroluminescent device can adjust the emission of various desired lights by changing the material of the light emitting layer as needed.
The organic electroluminescent device is used as a novel display technology, has the unique advantages of self-luminescence, wide visual angle, low energy consumption, high efficiency, thinness, rich color, high response speed, wide application temperature range, low driving voltage, flexible and bendable transparent display panel manufacturing, environment friendliness and the like, can be applied to flat panel displays and new-generation illumination, and can also be used as a backlight source of LCD.
Since the end of the 80 s of the 20 th century, organic electroluminescent devices have been industrially used, for example, as screens for cameras and mobile phones, but the current OLED devices are limited in their wider application, particularly for large screen displays, due to low efficiency, short service life, and the like, and thus there is a need to improve the efficiency of the devices. One of the important factors that is limiting is the performance of the organic electroluminescent material in the organic electroluminescent device. Therefore, there is a need to develop stable and efficient organic electroluminescent materials to improve the current efficiency and the service life of OLED devices.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an anthracene compound containing a benzofuran group, an intermediate and an organic electroluminescent device. The anthracene compound containing the benzofuran group can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
To achieve the purpose, the invention adopts the following technical scheme:
In a first aspect, the present invention provides a benzofuran-substituted anthracene compound having a structure according to formula I:
Wherein n1 represents an integer of 0 to 7, n2 represents an integer of 0 to 8, n3 represents an integer of 0 to 4, n4 represents an integer of 0 to 3, and n5 represents an integer of 0 to 4; and n1+n2+n3+n4+n5 is less than or equal to 1 and less than 26;
The anthracene compound containing the benzofuran group does not include the following compounds:
The anthracene compound containing the benzofuran group can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
Generally, the lifetime of the device increases after the H atoms in the host material of the light emitting layer are replaced with D atoms, but the voltage and efficiency of the device are not greatly affected. The inventors have found that this is not the case for the compounds of the structure of formula I of the present invention. Because the structure of the compound comprises naphthyl, anthryl, benzofuranyl and dibenzofuranyl groups, the polarities of the groups are greatly different, and therefore, when H in different groups is replaced by D, the performances of the compounds are greatly different. The reason is that when the compound of the structure of formula I is used as a host material of the light emitting layer and the doping material together constitute the light emitting layer, all H in the doping material is not replaced by D. The specific part of the main body material is tightly combined with the doping material, and after the H of the specific part of the main body material is replaced by D, the transmission of the main body material energy to the doping material is affected, so that the efficiency and the voltage are affected. Meanwhile, after all H in the compound with the structure of the formula I is replaced by D, the energy transfer of a main material to a doped material is also influenced, so that the efficiency and the voltage are influenced.
The compound of the invention can improve the service life of the device while changing the voltage and efficiency of the device.
In the present invention, D represents a deuterium atom.
In the invention, n1 represents that n 1H atoms are replaced by D atoms on the corresponding group; n2 represents that n 2H atoms are replaced by D atoms on the corresponding group; n3 represents that n 3H atoms are replaced by D atoms on the corresponding group; n4 represents that n 4H atoms are replaced by D atoms on the corresponding group; n5 represents that n 5H atoms are replaced by D atoms on the corresponding group.
The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention.
As a preferred technical scheme of the invention, the compound of the formula I has a structure shown in the following formula I-1, formula I-2, formula I-3 or formula I-4:
wherein n1, n2, n3, n4, n5 have the same definition as above.
As a preferred embodiment of the present invention, n1 is selected from 0 or 7, n2 is selected from 0 or 8, n3 is selected from 0 or 4, n4 is selected from 0 or 3, and n5 is selected from 0 or 3.
As a preferable technical scheme of the invention, n1+n2+n3+n4+n5 is more than or equal to 11.
As a preferable technical scheme of the invention, the ratio of 11 is less than or equal to n1+n2+n3+n4+n5 to 19.
As a preferable technical scheme of the invention, the ratio of 11 is less than or equal to n1+n2+n3+n4+n5 to 16.
As a preferable technical scheme of the invention, the ratio of 14 to n1+n2+n3+n4+n5 to 15 is less than or equal to 14.
As a preferred embodiment of the present invention, n1 is selected from 7.
As a preferred embodiment of the present invention, n2 is selected from 8.
As a preferred embodiment of the present invention, n3 is selected from 4.
As a preferred embodiment of the present invention, n4 is selected from 3.
As a preferred embodiment of the present invention, n5 is selected from 3.
As a preferred embodiment of the present invention, n1 is selected from 7, and n2 is selected from 8.
As a preferred embodiment of the present invention, n1 is selected from 7, n2 is selected from 8, and n3 is selected from 4.
As a preferred technical scheme of the invention, the compound shown in the formula I is selected from any one of the following compounds:
Preferably, the compound of formula I is selected from any one of the following compounds:
It should be noted that the preparation method of the compound of formula I is not limited in any way, and the preparation methods commonly used in the art are applicable, and the synthesis method of the compound of formula I includes the following steps:
Wherein n1, n2, n3, n4, n5 have the same definition as above;
X 1、X2 is each independently selected from F, cl, br, I and X 1 is less reactive than X 2, for example, when X 1 is selected from Cl, X 2 is selected from Br; or when X 1 is selected from Br, X 2 is selected from I.
Inasecondaspect,thepresentinventionprovidesanintermediatecomprisingacompoundoftheformulaM-A,formulaM-B,formulaM-BEA:
Wherein n1, n2, n3, n4, n5 have the same definition as in claim 1;
X 1 is selected from any one of F, cl, br or I;
the intermediates do not include the following compounds:
the intermediate is used for preparing the compound shown as the formula I in the first aspect.
Preferably, the intermediate comprises any one of the following compounds:
In a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising an anthracene compound containing a benzofuran group according to the first aspect.
Preferably, the organic thin film layer comprises a light emitting layer, and the material of the light emitting layer comprises an anthracene compound containing a benzofuran group according to the first aspect.
In the present invention, the light emitting layer material further includes a compound having a structure shown in formula II and/or a compound having a structure shown in formula III:
Wherein Ar 21、Ar22 is each independently selected from any of substituted or unsubstituted C6-C20 (e.g., may be C6, C8, C10, C12, C16, or C20, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., may be C3, C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;
R 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 (e.g., C1, C2, C4, C6, C8, C10, or C12, etc.) linear or branched alkyl, C6-C12 (e.g., C6, C8, C10, or C12, etc.) cycloalkyl;
The substituents described for Ar 21、Ar22 are each independently selected from C1-C5 (which may be, for example, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) straight or branched alkyl or C6-C12 (which may be, for example, phenyl, biphenyl, naphthyl, etc.) aryl;
Ar 31、Ar32、Ar33 and Ar 34 are each independently selected from any of substituted or unsubstituted C6-C22 (e.g., may be C6, C8, C10, C16, C18, or C22, etc.) aryl, substituted or unsubstituted C12-C40 (e.g., may be C12, C18, C20, C24, C30, C36, or C40, etc.) heteroaryl;
R 31 is selected from any one of phenyl, naphthyl or biphenyl;
a is selected from 0 or 1;
The substituents described for Ar 31、Ar32、Ar33、Ar34 are each independently selected from C1-C5 straight or branched chain alkyl (which may be, for example, methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, etc.) or C6-C12 (which may be, for example, C6, C8, C10 or C12, etc.) aryl.
As a preferred embodiment of the present invention, ar 21、Ar22 is each independently selected from the group consisting of Any one of the following.
Preferably, each of R 21、R22 and R 23 is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
Preferably, ar 31、Ar32、Ar33 and Ar 34 are each independently selected from Any one or a combination of at least two of these.
As a preferred embodiment of the present invention, the compound of formula II is selected from any one of the following compounds:
As a preferred embodiment of the present invention, the compound of formula III is selected from any one of the following compounds:
preferably, the organic thin film layer further includes a hole layer including a hole transport layer, a hole injection layer, and an electron blocking layer.
In a fourth aspect, the present invention provides a display device comprising an organic electroluminescent device as described in the third aspect.
Compared with the prior art, the invention has the following beneficial effects:
According to the invention, the structure of the anthracene compound containing the benzofuran group is designed, and the anthracene compound is used as a main material of a light-emitting layer of the OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Synthesis of intermediate A-1 of preparation example 1
The preparation example provides an intermediate A-1 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
80mL of toluene, 30mL of ethanol and 15mL of water were sequentially added to a 250mL three-necked flask under nitrogen protection, and 2.2g of the mixture was further added thereto 3.2g2.12G (0.02 mol) of sodium carbonate and 0.23g (0.0002 mol) of tetraphenylphosphine palladium, slowly heating to 40 ℃ for reaction for 2 hours, heating to 60 ℃ for reaction for 2 hours, refluxing for reaction for 2 hours, cooling to room temperature, adding water to water, washing an organic layer, drying with magnesium sulfate, removing a drying agent, concentrating to dryness, separating by silica gel column chromatography, eluting with petroleum ether, and obtaining 2.7g of an intermediate A-1.
Mass spectrometry was performed on the intermediate A-1 obtained, and the mass-to-charge ratio (m/z) was found to be 361.99.
Preparation example 2 Synthesis of intermediate A-2
The preparation example provides an intermediate A-2 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
reference to the synthesis of intermediate A-1 in preparation example 1, the corresponding bromo was used And boric acid compoundsAnd (3) reacting to prepare the intermediate A-2.
Mass spectrometry was performed on the intermediate A-2 obtained, and the mass-to-charge ratio (m/z) was found to be 369.04.
Preparation example 3 Synthesis of intermediate A-3
The preparation example provides an intermediate A-2 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
reference to the synthesis of intermediate A-1 in preparation example 1, the corresponding bromo was used And boric acid compoundsAnd (3) reacting to prepare the intermediate A-3.
Mass spectrometry was performed on the intermediate A-1 obtained, and the mass-to-charge ratio (m/z) was found to be 361.99.
Preparation example 4 Synthesis of intermediate BA-1
The preparation example provides an intermediate BA-1 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
under the protection of nitrogen, 80mL of tetrahydrofuran and 3.8g of 9-bromo-10- (2-naphthyl) anthracene are added into a three-necked flask, the temperature is reduced to minus 78 ℃, 0.01mol of n-hexane solution of butyl lithium (with the concentration of 1.6M and 6.3 mL) is slowly added, then the temperature is kept between minus 78 ℃ and minus 60 ℃ for 30min, 1.5g of trimethyl borate is added, the temperature is slowly increased to room temperature for reaction for 2 hours, water and ethyl acetate are added for separating, the organic layer is washed with water and then concentrated to dryness, petroleum ether is added for stirring, and the obtained solid is filtered to obtain an intermediate BA-1.
Preparation example 5 Synthesis of intermediate BA-2
The preparation example provides an intermediate BA-2 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
Referring to the synthesis of intermediate BA-1 in preparation example 4, intermediate BA-2 was prepared.
Preparation example 6 Synthesis of intermediate BA-3
Referring to the synthesis of intermediate BA-1 in preparation example 4, intermediate BA-3 was prepared.
Preparation example 7 Synthesis of intermediate BA-4
Referring to the synthesis of intermediate BA-1 in preparation example 4, intermediate BA-4 was prepared.
Synthesis example 1 Synthesis of Compound P1
This synthetic example provides compound P1 and a method of synthesizing the same, as follows:
100mL of toluene, 40mL of ethanol and 15mL of water are sequentially added into a 250mL three-necked flask under the protection of nitrogen, 3.5g of intermediate BA-1, 3.7g of intermediate A-2, 2.12g (0.02 mol) of sodium carbonate and 0.23g (0.0002 mol) of tetraphenylphosphine palladium are added into the flask, the mixture is slowly heated to reflux reaction for 8 hours, the temperature is reduced to room temperature, water is added into the mixture, the organic layer is washed with water, then the organic layer is dried with magnesium sulfate, the drying agent is removed, the mixture is concentrated to dryness, and silica gel column chromatography separation and petroleum ether are carried out: ethyl acetate = 10:0.5 (volume ratio) elution gave 4.7g of Compound P1.
Mass spectrometry was performed on the obtained compound P1, and the mass-to-charge ratio (m/z) was found to be 593.24.
Synthesis examples 2 to 6
Referring to synthesis example 1, the following compounds were synthesized by reacting the corresponding bromo-and boronic acid-based compounds, and mass spectra of the prepared compounds were tested. The structural formulas of corresponding bromo-compounds and boric acid compounds, and the structural formulas and mass spectrum data of the prepared compounds are shown in the following table 1.
TABLE 1
Synthesis example 7 Synthesis of Compound P2
This synthesis example provides another synthesis of compound P2, which is as follows:
(1) Synthesis of intermediate BA-2EA
Adding 0.3g of intermediate BA-2, 0.15g of pinacol and 10mL of petroleum ether into a three-necked flask, refluxing for 4 hours, cooling to room temperature, and filtering to obtain a solid, namely intermediate BA-2EA;
Mass spectrometry was performed on the intermediate BA-2EA obtained, and the mass-to-charge ratio (m/z) was found to be 445.30.
(2) Synthesis of Compound P2
In accordance with synthesis example 1, compound P1 was synthesized, and intermediate A-2 and BA-2EA were reacted to synthesize compound P2.
Mass spectrometry was performed on the obtained compound P2, and mass-to-charge ratio (m/z) was found to be 608.33.
Other compounds not specifically identified as synthetic steps may be prepared by combining the above synthetic examples, as is known in the art.
The specific structures of the compounds used in the following application examples and comparative application examples are shown below:
wherein, the compound D1 is prepared by adopting the following synthesis method:
referring to synthesis example 1, the following compound D1 was synthesized by reacting the corresponding bromo-compound with a boric acid-based compound, and mass spectrometry was performed on the obtained compound D1, whereby a mass-to-charge ratio (m/z) was found to be 601.29.
The compound D3 is prepared by adopting the following synthesis method: :
5g of compound D2, 200mL of deuterated benzene (C 6D6) and 10g of trifluoromethanesulfonic acid are added into 500mL of three-port under the protection of nitrogen, the mixture is reacted for 48 hours at 60 ℃, the temperature is reduced, water is added, the organic layer is washed with water, then the organic layer is dried by magnesium sulfate, the drying agent is removed, the mixture is concentrated to dryness, and 3 times of toluene crystallization is carried out, thus obtaining 3.1g of compound D3.
Mass spectrometry was performed on the obtained compound D3, and the mass-to-charge ratio (m/z) was found to be 612.36.
Application example 1
The application example provides an organic electroluminescent device, which has the structure that: ITO/HTL HI-2 (5%) (20 nm)/HTL (50 nm)/BH: BD-3 (5%) (30 nm)/TPBI (30 nm)/Al (150 nm);
The preparation method of the organic electroluminescent device comprises the following steps:
And placing the materials of each layer into a vacuum cavity, vacuumizing to 1X 10 -5～1×10-6 Pa, and sequentially carrying out vacuum evaporation on the cleaned ITO substrate. Wherein HTL: HI-2 (5%) (20 nm) means that in the device, HTL and HI-2 co-evaporate in a volume ratio of 95:5 to form a hole injection layer, which has a thickness of 20nm. BH: BD-3 (5%) (30 nm) refers to BH and BD-3 at 95: the volume ratio of 5 was co-evaporated to form a light emitting layer with a thickness of 30nm.
BH is a host material of a blue light emitting layer, and in this application example, BH is a compound P1, and BD-3 is a doping material of the blue light emitting layer.
In the device provided in this application example, HTL: HI-2 (5%) (20 nm) is a hole injection layer and HTL (50 nm) is a hole transport layer.
Application examples 2 to 9
Application examples 2 to 9 each provide an organic electroluminescent device differing from application example 1 only in that the host material of the light-emitting layer is different, the doping material of the light-emitting layer is changed according to circumstances, (specific composition is as described in the following table 2), and other preparation steps are the same as application example 1.
Comparative application examples 1 to 3
Comparative examples 1 to 3 each provided an organic electroluminescent device differing from example 1 only in the light-emitting layer host material, the light-emitting layer doping material was changed according to circumstances (specifically, as described in table 2 below), and other preparation steps were the same as example 1.
Performance testing
Test items include luminance, driving voltage, current efficiency, LT80 of the organic electroluminescent device; the LT80 is the time required to maintain the current density of the initial luminance 1000cd/m 2 of the device unchanged and the device efficiency is reduced to 80% of the efficiency corresponding to the initial luminance 1000cd/m 2. Wherein the driving voltage, current efficiency, LT80 are all relative values.
The specific test results are shown in table 2 below:
TABLE 2
As is clear from comparison of application example 3 and application example 5, when a hydrogen atom in a dibenzofuran group in an anthracene compound containing a benzofuran group is deuterated, electron cloud density on the dibenzofuran ring is changed, so that the voltage of an organic electroluminescent device prepared by using the compound as a main material of a light-emitting layer is increased, the efficiency is reduced, but the service life is prolonged.
As can be seen from comparison of application example 3 and application example 7, the service life of the organic electroluminescent device prepared by using the compound as the main material of the luminescent layer is obviously prolonged by changing the connection position of the dibenzofuran group in the anthracene compound containing the benzofuran group to make the anthracene compound conform to the structure shown in the formula I-4.
As is clear from application examples 3 and 4, the service life of the organic electroluminescent device prepared by using the compound as the main material of the luminescent layer is obviously prolonged by changing the connection position of the dibenzofuran group in the anthracene compound containing the benzofuran group to make the anthracene compound conform to the structure shown in the formula I-2.
As is clear from application examples 3 to 5 and application example 7, when 14.ltoreq.n1+n2+n3+n4+n5.ltoreq.15 in the anthracene compounds containing a benzofuran group, the device comprehensive properties were excellent.
As can be seen from the comparison of application examples 3 and 4 with application examples 8 and 9, respectively, the performance of the organic electroluminescent device can be further improved when the anthracene compound having a benzofuranyl group provided by the present invention is used as a host material of a light-emitting layer and is matched with the compound BD-4.
As is clear from comparison of comparative application example 2 and comparative application example 3, when the hydrogen atom in the anthracene compound containing a benzofuran group is completely deuterated (comparative application example 3), the driving voltage of the organic electroluminescent device prepared by using the compound as a host material of a light emitting layer is higher, and the current efficiency is lower.
As can be seen from the above, the anthracene compound containing a benzofuran group provided by the invention can be used as a main material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
The applicant states that the detailed process flow of the present invention is illustrated by the above examples, but the present invention is not limited to the above detailed process flow, i.e. it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (10)
1. The benzofuran substituted anthracene compound is characterized in that the anthracene compound containing a benzofuran group has a structure shown in the following formula I:
Wherein n1 represents an integer of 0 to 7, n2 represents an integer of 0 to 8, n3 represents an integer of 0 to 4, n4 represents an integer of 0 to 3, and n5 represents an integer of 0 to 4; and n1+n2+n3+n4+n5 is less than or equal to 1 and less than 26;
The anthracene compound containing the benzofuran group does not include the following compounds:
2. the benzofuran-substituted anthracene compound according to claim 1, wherein the compound of formula I has a structure represented by the following formula I-1, formula I-2, formula I-3 or formula I-4:
Wherein n1, n2, n3, n4, n5 have the same definition as in claim 1.
3. The benzofuran-substituted anthracene compound according to claim 1 or 2, wherein n1 is 0 or 7, n2 is 0 or 8, n3 is 0 or 4, n4 is 0 or 3, and n5 is 0 or 3;
preferably, n1+n2+n3+n4+n5 is more than or equal to 11;
preferably, the ratio of 11.ltoreq.n1+n2+n3+n4+n5 < 19;
Preferably, the ratio of 11.ltoreq.n1+n2+n3+n4+n5 < 16;
preferably, 14.ltoreq.n1+n2+n3+n4+n5.ltoreq.15.
4. A benzofuran-substituted anthracene compound according to any one of claims 1 to 3, wherein n1 is selected from 7;
preferably, said n2 is selected from 8;
preferably, said n3 is selected from 4;
preferably, said n4 is selected from 3;
preferably, said n5 is selected from 3;
Preferably, n1 is selected from 7 and n2 is selected from 8;
Preferably, n1 is selected from 7, n2 is selected from 8, and n3 is selected from 4.
5. The benzofuran-substituted anthracene compound according to any one of claims 1 to 4, wherein the compound represented by the formula I is selected from any one of the following compounds:
Preferably, the compound of formula I is selected from any one of the following compounds:
6. anintermediatecomprisingacompoundoftheformulaM-a,formulaM-b,formulaM-bea:
Wherein n1, n2, n3, n4, n5 have the same definition as in claim 1;
X 1 is selected from any one of F, cl, br or I;
the intermediates do not include the following compounds:
The intermediate for the preparation of the benzofuran group-containing anthracene compound according to any one of claims 1 to 5;
Preferably, the intermediate comprises any one of the following compounds:
7. An organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising the benzofuran group-containing anthracene compound according to any one of claims 1 to 5;
Preferably, the organic thin film layer comprises a light-emitting layer, and a host material of the light-emitting layer comprises the benzofuran group-containing anthracene compound according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, wherein the material of the light-emitting layer further comprises a compound having a structure shown in formula II and/or a compound having a structure shown in formula III:
wherein Ar 21、Ar22 is independently selected from any one of substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;
R 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 straight or branched alkyl, C6-C12 cycloalkyl;
The substituents of Ar 21、Ar22 are each independently selected from C1-C5 straight or branched alkyl or C6-C12 aryl;
Ar 31、Ar32、Ar33 and Ar 34 are each independently selected from any one of substituted or unsubstituted C6-C22 aryl, substituted or unsubstituted C12-C40 heteroaryl;
R 31 is selected from any one of phenyl, naphthyl or biphenyl;
a is selected from 0 or 1;
The substituents described for Ar 31、Ar32、Ar33、Ar34 are each independently selected from C1-C5 straight or branched chain alkyl or C6-C12 aryl.
9. The organic electroluminescent device of claim 8, wherein each Ar 21、Ar22 is independently selected from the group consisting of Any one of them;
Preferably, each of R 21、R22 and R 23 is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl;
Preferably, ar 31、Ar32、Ar33 and Ar 34 are each independently selected from Any one or a combination of at least two of these.
10. The organic electroluminescent device according to claim 8 or 9, wherein the compound of formula II is selected from any one of the following compounds:
preferably, the compound of formula III is selected from any one of the following compounds:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410434629.0A CN118164942A (en) | 2024-04-11 | 2024-04-11 | Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410434629.0A CN118164942A (en) | 2024-04-11 | 2024-04-11 | Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118164942A true CN118164942A (en) | 2024-06-11 |
Family
ID=91354801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410434629.0A Pending CN118164942A (en) | 2024-04-11 | 2024-04-11 | Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118164942A (en) |
-
2024
- 2024-04-11 CN CN202410434629.0A patent/CN118164942A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107573306B (en) | Organic electroluminescent compound | |
| CN114890970A (en) | Anthracene compound, organic electroluminescent device and display device | |
| CN114835663A (en) | Naphtho heteroaryl compound, organic electroluminescent device and display device | |
| CN114853703A (en) | Anthracene compound, organic electroluminescent device and display device | |
| CN116751177A (en) | Anthracene compound, intermediate, anthracene mixture, organic electroluminescent device and display device | |
| CN116986997A (en) | Deuterated composition, organic electroluminescent device and display device | |
| CN116987081B (en) | Indolocarbazole compound, preparation method thereof, organic electroluminescent composition and organic electroluminescent device | |
| CN117050041A (en) | Composition containing naphthobenzofuran group and organic electroluminescent device | |
| CN110003115B (en) | Blue organic luminescent material, luminescent device and preparation method | |
| CN112479901A (en) | Organic compound with indeno-anthracene derivative as core and application thereof | |
| CN114437115B (en) | Hole transport material, preparation method thereof and OLED device | |
| CN114835699A (en) | Anthracene furan compound, intermediate, organic electroluminescent device and display device | |
| CN118164942A (en) | Anthracene compound containing benzofuran group, intermediate and organic electroluminescent device | |
| CN112480002B (en) | Organic compound containing benzanthracene and application thereof | |
| CN118164936A (en) | Anthracene compound containing naphthobenzofuran group, intermediate and organic electroluminescent device | |
| CN118164941A (en) | Anthracene compound containing benzofuran group, intermediate, composition and OLED device | |
| CN116655569A (en) | Compound containing naphthyl anthracene and application thereof in organic electroluminescent device | |
| CN116143740A (en) | Deuterated benzofuran compound, organic electroluminescent device and display device | |
| CN114933578B (en) | Anthraofuran compound, intermediate, organic electroluminescent device and display device | |
| CN107286063B (en) | Organic electroluminescent compound | |
| CN118724671A (en) | Deuterated anthracene compound, intermediate, composition, compound and OLED device | |
| CN118724854A (en) | Anthracene compound containing dibenzo five-membered heterocyclic substituent, intermediate and organic electroluminescent device | |
| CN117551065A (en) | Naphthalene-substituted anthracene compound | |
| CN114702482B (en) | Triazine compound, intermediate, organic electroluminescent device and display device | |
| CN117777207B (en) | Organic metal iridium complex 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 |
Country or region after: China Address after: 236000 No.1 Tianzhushan Road, Hefei modern industrial park, Yingzhou District, Fuyang City, Anhui Province Applicant after: Fuyang Xinyihua New Material Technology Co.,Ltd. Address before: 236000 No.1 Tianzhushan Road, Hefei modern industrial park, Yingzhou District, Fuyang City, Anhui Province Applicant before: FUYANG SINEVA MATERIAL TECHNOLOGY Co.,Ltd. Country or region before: China |
|
| CB02 | Change of applicant information |