CN108752321A - A kind of organic electroluminescence device and display device - Google Patents

A kind of organic electroluminescence device and display device Download PDF

Info

Publication number
CN108752321A
CN108752321A CN201810713072.9A CN201810713072A CN108752321A CN 108752321 A CN108752321 A CN 108752321A CN 201810713072 A CN201810713072 A CN 201810713072A CN 108752321 A CN108752321 A CN 108752321A
Authority
CN
China
Prior art keywords
organic electroluminescence
electroluminescence device
carbon
aromatic heterocyclic
atom number
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.)
Withdrawn
Application number
CN201810713072.9A
Other languages
Chinese (zh)
Inventor
赵东敏
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to CN201810713072.9A priority Critical patent/CN108752321A/en
Publication of CN108752321A publication Critical patent/CN108752321A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-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
    • C09K2211/1003—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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to display technology fields, more particularly to a kind of biindolyl class material, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (1)：

Description

A kind of organic electroluminescence device and display device
Technical field
The present invention relates to display technology fields, more particularly to a kind of organic electroluminescence device and display device.
Background technology
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as novel Plate display is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master It is dynamic shine, luminescent color is continuously adjustable, at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, gives birth to Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair Luminescent material, electroluminescent organic material have the following advantages：Organic material processing performance is good, can pass through vapor deposition or the side of spin coating Method forms a film on any substrate；The diversity of organic molecular structure allow to by Molecular Design and the method for modification come It adjusts the thermal stability of organic material, mechanical performance, shine and electric conductivity so that material is significantly improved space.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials Recombination.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued, the transmission of carrier normal in organic semiconductor It is described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material Charge injects and the difficulty of transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer Number, and different organic layers is made to play the part of different device layers, such as the functional material having can promote electronics from cathode Injection, some functional materials can promote hole to be injected from anode, and some materials can promote the transmission of charge, and some materials are then It can play the role of stopping electronics or hole transport.Certainly in organic electroluminescence device, most important a variety of colors Luminescent material will also achieve the purpose that match with adjacent functional material.Therefore, the organic electroluminescence of excellent in efficiency long lifespan Part is typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this, which is just chemists, designs and develops various structures Functionalization material provide great opportunities and challenges.
In organic electroluminescence device preparation process, one kind being known as vapour deposition method, i.e., each functional material passes through vacuum The mode of hot evaporation is plated on substrate and forms a film, this is also the mainstream technology of current industry.But the shortcomings that this technique it is also obvious that The characteristic of one side organic material itself determines, hot evaporation is carried out under the high temperature conditions for a long time, to the thermal stability of material It is required that very high；In addition prolonged stability contorting evaporation rate, keep thereon material distribution uniformity be also one very Important requirement；And high vacuum, high temperature deposition, energy consumption are higher；It is more main, because OLED material production technology itself compares Complexity, technology content is higher, thus price is more expensive, and prior art is used by vapor deposition mode, the utilization of OLED material Rate is relatively low, generally below 10%.
In the preparation process of organic electroluminescence device, another is known as solwution method, that is, uses soluble OLED materials Material, is dissolved in solvent, is coated on substrate by modes such as printing, ink-jet, spin coatings, such to form certain functional layers Method material is evenly distributed, and saves material, simplifies OLED device production technology, reduces OLED device production cost.
Invention content
Have the present invention provides a kind of biindolyl class material, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence devices, including the organic electroluminescence device of the compound have lower driving voltage and compared with High luminous efficiency.
According to an aspect of the present invention, a kind of biindolyl class material is provided, as shown in formula (1)：
Wherein Ar1The aryl being made of carbon and hydrogen selected from C6~C40, Ar2It is miscellaneous selected from the nitrogenous virtue that carbon atom number is 3-80 The sulfur-bearing aromatic heterocyclic that oxygen-containing aromatic heterocyclic that ring group, carbon atom number are 3-80, carbon atom number are 3-80；Ar1And Ar2It can be by The alkyl of C1~C20, the alkoxy of C1~C20, the aryl of C6~C40 being made of carbon and hydrogen, carbon atom number are containing for 3-80 Nitrogen aromatic heterocyclic, carbon atom number are replaced by the sulfur-bearing aromatic heterocyclic that the oxygen-containing aromatic heterocyclic of 3-80, carbon atom number are 3-80, institute State substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted；Also, work as Ar2It is taken by the aryl of C6~C40 being made of carbon and hydrogen Dai Shi, herein the aryl of C6~C40 being made of carbon and hydrogen can be replaced by the nitrogenous aromatic heterocyclic of 3-80 by carbon atom number, The substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted；N is selected from 0 or 1.
Further, the wherein aryl of C6~C40 is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, three Phenylene, fluorenyl, fluoranthene base, indeno fluorenyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, phenyl substituted naphthyl, benzo anthryl； The alkyl of C1~C20 is selected from methyl, ethyl, propyl, butyl, amyl, hexyl, cyclohexyl, heptyl, octyl；The alcoxyl of C1~C20 Base is selected from methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, cyclohexyloxy, oxygroup in heptan, octyloxy；Ar2Choosing From pyridyl group, quinolyl, pyrimidine radicals, benzimidazolyl, benzothiazolyl, benzoxazolyl, dibenzothiophene, dibenzo furan It mutters base, benzo dibenzofuran group, benzo dibenzothiophene, dinaphtho furyl, dinaphtho thienyl.
Further, biindolyl class material provided by the invention, selected from lower structure：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Including biindolyl class material according to the present invention.
Optionally, the electron transport material of the organic electroluminescence device is the biindolyl class material according to the present invention.
Optionally, the material of main part of the luminescent layer of the organic electroluminescence device is the biindolyl class material according to the present invention Material.
Further, the luminescent layer of the organic electroluminescence device is phosphorescence luminescent layer.
Further, the organic electroluminescence device is emitting red light device or green light emitting device.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having Organic electroluminescence devices.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used as to electron transport material or the luminescent layer master of organic electroluminescence device Body material improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
Specific implementation mode
Specific implementation mode is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with Invention is further explained and description for specific embodiment.
Have the present invention provides a kind of biindolyl class material, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence devices, including the organic electroluminescence device of the compound have lower driving voltage and compared with High luminous efficiency.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below The present invention is further described.
The synthesis of 1 compound P-1 of embodiment：
The synthesis of intermediate 1
In 2000 milliliters of there-necked flasks, 28.6 grams of (0.1mol) 3- (4- bromophenyls) -1- Methyl-1H-indoles, 800 millis are added Anhydrous acetonitrile is risen, 0~3 DEG C of temperature of control is slowly added dropwise 65% 10 grams of nitric acid, is added dropwise, 0~3 DEG C of reaction 3 of control temperature Hour, then 10 grams of the nitric acid that 0~3 DEG C of temperature is slowly added dropwise 65% is controlled, 0~3 DEG C of control temperature is reacted 3 hours, then controls temperature 65% 10 grams of nitric acid is slowly added dropwise in 0~3 DEG C of degree, and 0~3 DEG C of control temperature is reacted 8 hours, and water and dichloromethane liquid separation, water are added It is washed till neutrality, the separation of organic layer silica gel column chromatography, ethyl acetate：Petroleum ether=1：9 (volume ratios) elute, and eluent is concentrated into It is dry, it is recrystallized with methanol/toluene mixed solvent, obtains 10.1 grams of compound shown in intermediate 1, yield 35.43%.
Mass Spectrometer Method has been carried out to product shown in obtained intermediate 1, has obtained the m/e of product：570.
Nuclear-magnetism detection is carried out to product shown in obtained intermediate 1, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 7.75 (m, 2H), δ 7.58~7.48 (m, 10H), δ 7.26 (t, 2H), δ 7.02 (m, 2H), δ 3.81 (s, 6H).
The synthesis of intermediate 2
200 milliliters of dry tetrahydrofurans are added in 500 milliliters of there-necked flasks, nitrogen protection, and 5.70 grams (0.01mol) is intermediate Compound shown in body 1 after stirring and dissolving, is cooled to -78 DEG C, the butyl lithium of 15 milliliters of (0.024mol) 1.6M is being slowly added dropwise just Hexane solution finishes and keeps the temperature 30 minutes in -78 DEG C, and the trimethylborate that 3.12 grams (0.03mol) steams again is added, finishes slow liter It to room temperature, stirs 2 hours, ammonium chloride solution stirring hydrolysis, then liquid separation is added.Organic layer is concentrated to dryness, and obtains 2 institute of intermediate Show hypoboric acid, without isolation, directly carries out the next step.
The synthesis of compound P-1
100 milliliters of toluene, 100 milliliters of ethyl alcohol are added in 500 milliliters of there-necked flasks, nitrogen protection, and 100 milliliters of water add Hypoboric acid shown in the not separated intermediate 2 that step is prepared, 3.16 grams of (0.02mol) 2- bromopyridines, 0.112 gram (0.0001mol) tetra-triphenylphosphine palladium, 2.12 grams of (0.02mol) sodium carbonate, is slowly heated to back flow reaction 12 hours, cooling, Liquid separation, the drying of organic layer magnesium sulfate, silica gel column chromatography separation, ethyl acetate：Petroleum ether=3：7 (volume ratios) elute, eluent It is concentrated to dryness, obtains 4.16 grams of product shown in formula P-1, calculated since the synthesis of intermediate 2, two step total recoverys 73.5%,
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product：566.
Nuclear-magnetism detection is carried out to product shown in obtained formula P-1, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 8.66 (m, 4H), δ 8.35 (m, 2H), δ 7.78 (m, 2H), δ 7.46 (m, 2H), δ 7.38 (m, 2H), δ 7.33~7.23 (m, 6H), δ 7.12 (m, 2H), δ 7.04 (m, 2H), δ 6.90 (m, 2H), δ 3.81 (s, 6H).
The synthesis of 2 other parts compound of embodiment
The synthetic method of reference compound P-1 only changes 2- bromopyridines therein into corresponding bromo-derivative as needed. Specific reaction bromo-derivative used and obtained the compound of the present invention mass spectrometric data are listed as follows：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Electron transport material/luminescent layer material of main part be according to the present invention biindolyl class material.
The typical structure of organic electroluminescence device is：Substrate/anode/hole injection layer/hole transmission layer (HTL)/has Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light Layer can also be multi-luminescent layer.
Wherein, substrate can use the substrate in conventional organic electroluminescence device, such as：Glass or plastics.Anode can be with Using transparent high conductivity material, such as：Indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable that there is height Thermal stability (high Tg), there is smaller potential barrier, vapour deposition method to prepare organic electroluminescent with anode or hole-injecting material When device, it is desirable that material energy vacuum evaporation forms pin-hole free films.Common HIM is aromatic multi-amine class compound, mainly Derivative of tri-arylamine group.When preparing organic electroluminescence device for solwution method, it is desirable that material has suitable solubility, by solution After being coated on substrate, after solution evaporation, fine and close, uniform unformed film can be formed on substrate.Common HIM material masters There is PEDOT：PSS.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable that there is height Thermal stability (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Commonly HTM is Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated Material, material of main part need to have following characteristics：Reversible electrochemical redox current potential, with adjacent hole transmission layer and electronics The HOMO energy levels and lumo energy that transport layer matches, the good and hole to match and electron transport ability are good high Thermal stability and film forming, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also with phase Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer is needed by taking dyestuff as an example Have following characteristics：With high fluorescence or phosphorescence quantum efficiency；The absorption spectrum of dyestuff and the emission spectrum of main body have Overlapping, i.e. main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue to the greatest extent may be used Can be narrow, with the excitation purity obtained；Stability is good, can be deposited etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with Hole blocking ability；Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot The aromatic compound of the conjugate planes of structure.When vapour deposition method prepares organic electroluminescence device, electron transfer layer generally uses Alq3 (8-hydroxyquinoline aluminium) either TAZ (3- phenyl -4- (1 '-naphthalene) -5- benzene -1,2,4- triazoles) or TPBi (tri- (N- of 1,3,5- Phenyl -2- benzimidazoles) benzene) or it is derived from arbitrary two kinds of the collocation of these three materials.In some cases, in order to improve electricity The electron-transport effect of sub- transport layer, electron transfer layer may further include Li complex compounds, as LiQ or ET-02 are (as follows Formula).
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having Organic electroluminescence devices.
It can be seen that the optional factor of compound according to the present invention, organic electroluminescence device and display device is more, Claim according to the present invention can be combined into different embodiments.The embodiment of the present invention is only as to the specific of the present invention Description, is not intended as limitation of the present invention.Make below in conjunction with the organic electroluminescence device containing the compound of the present invention For embodiment, the present invention is described further.
The concrete structure of material therefor is seen below in embodiment：
Embodiment 3
Electron transport material in using the compounds of this invention as organic electroluminescence device, organic electroluminescence as a comparison There are two luminescent devices, and electron transport material selects Alq3 and ET-1 respectively.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL (20nm)/EIM(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is noted with hole Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness；
Vacuum evaporation NPB is as hole transmission layer on hole injection layer, and evaporation rate 0.1nm/s, film thickness, which is deposited, is 40nm；
Organic luminous layers of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam Plating total film thickness is 30nm；
The vacuum evaporation electron transfer layer on organic luminous layer；Its evaporation rate is 0.1nm/s, and vapor deposition total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer material (EIM) on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance see the table below：
It can thus be seen that when the electron transfer layer of organic electroluminescence device contains compound shown in the present invention, tool There are more low driving voltage and higher current efficiency.
Embodiment 4
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence devices：
Organic electroluminescence device structure is：
ITO/NPB (20nm)/feux rouges material of main part (30nm)：Ir (piq) 3 [5%]/TPBI (10nm)/Alq3 (15nm)/ LiF(0.5nm)/Al(150nm)。
One of them is comparison organic electroluminescence device, and feux rouges material of main part selects CBP.
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to, Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as cathode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 5：
The compound of the present invention is as the material of main part in green phosphorescent OLED organic electroluminescence devices：
Organic electroluminescence device structure is：
ITO/NPB (20nm)/green light material of main part (30nm)：Ir (ppy) 3 [7%]/TPBI (10nm)/Alq3 (15nm)/ LiF(0.5nm)/Al(150nm)。
One of them is comparison organic electroluminescence device, and green light material of main part selects CBP.
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to, Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art God and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies Within, then the present invention is also intended to include these modifications and variations.

Claims (4)

1. a kind of red organic electroluminescence device contains biindolyl class material shown in formula (1)：
Wherein Ar1The aryl being made of carbon and hydrogen selected from C6~C40, Ar2Selected from the nitrogenous heteroaromatic that carbon atom number is 3-80 The sulfur-bearing aromatic heterocyclic that oxygen-containing aromatic heterocyclic that base, carbon atom number are 3-80, carbon atom number are 3-80；
Ar1And Ar2It can be by the alkyl of C1~C20, the alkoxy of C1~C20, the aryl being made of carbon and hydrogen, the carbon of C6~C40 The sulfur-bearing that oxygen-containing aromatic heterocyclic that nitrogenous aromatic heterocyclic that atomicity is 3-80, carbon atom number are 3-80, carbon atom number are 3-80 Aromatic heterocyclic is replaced, the substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted；
Also, work as Ar2When being replaced by the aryl of C6~C40 being made of carbon and hydrogen, C6~C40 is made of carbon and hydrogen herein Aryl can be replaced by the nitrogenous aromatic heterocyclic of 3-80 by carbon atom number, the substitution can be it is monosubstituted, it is disubstituted, it is more Substitution；
N is selected from 0 or 1.
2. organic electroluminescence device according to claim 1, the wherein aryl of C6~C40 is selected from：Phenyl, xenyl, Terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, fluorenyl, fluoranthene base, indeno fluorenyl, Spirofluorene-based, benzo fluorenyl, dibenzo Fluorenyl, phenyl substituted naphthyl, benzo anthryl；
The alkyl of C1~C20 is selected from methyl, ethyl, propyl, butyl, amyl, hexyl, cyclohexyl, heptyl, octyl；
The alkoxy of C1~C20 is selected from methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, cyclohexyloxy, heptan Oxygroup, octyloxy；
Ar2Selected from pyridyl group, quinolyl, pyrimidine radicals, benzimidazolyl, benzothiazolyl, benzoxazolyl, dibenzothiophene, Dibenzofuran group, benzo dibenzofuran group, benzo dibenzothiophene, dinaphtho furyl, dinaphtho thienyl.
3. organic electroluminescence device according to claim 1, compound is selected from shown in formula (1)：
4. a kind of display device, including organic electroluminescence device as described in claim 1.
CN201810713072.9A 2018-06-29 2018-06-29 A kind of organic electroluminescence device and display device Withdrawn CN108752321A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810713072.9A CN108752321A (en) 2018-06-29 2018-06-29 A kind of organic electroluminescence device and display device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810713072.9A CN108752321A (en) 2018-06-29 2018-06-29 A kind of organic electroluminescence device and display device

Publications (1)

Publication Number Publication Date
CN108752321A true CN108752321A (en) 2018-11-06

Family

ID=63975590

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810713072.9A Withdrawn CN108752321A (en) 2018-06-29 2018-06-29 A kind of organic electroluminescence device and display device

Country Status (1)

Country Link
CN (1) CN108752321A (en)

Similar Documents

Publication Publication Date Title
CN107936955A (en) 7H benzos [de] anthracene class electroluminescent organic material, luminescent device and display
CN108203407A (en) Pyrene class electroluminescent organic material, luminescent device and display
CN108586430A (en) A kind of electroluminescent organic material, organic electroluminescence device and display device
CN107936952A (en) A kind of electroluminescent organic material, luminescent device and display
CN107955023A (en) A kind of electroluminescent organic material, luminescent device and display
CN107973795A (en) A kind of electroluminescent organic material, luminescent device and display
CN108456195A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN108516959A (en) Acridine compound, organic electroluminescence device and display device
CN108191744A (en) Benzfluorene class electroluminescent organic material, luminescent device and display
CN108863896A (en) Biindolyl class material, organic electroluminescence device and display device
CN108922987A (en) Biindolyl class material, organic electroluminescence device and display device
CN108623515A (en) Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device
CN109206367A (en) A kind of organic electroluminescence device and display
CN109206368A (en) A kind of dihydrobenzo indazole class electroluminescent organic material
CN109053687A (en) A kind of biindolyl class display material
CN108997318A (en) Biindolyl class electroluminescent organic material
CN108586317A (en) A kind of biindolyl class material
CN108822016A (en) A kind of synthetic method of biindolyl class material
CN109206414A (en) Dihydrobenzo indazole class electroluminescent organic material
CN108586316A (en) Dihydroanthracene compound, organic electroluminescence device and display device
CN108997191A (en) A kind of organic electroluminescence device and display device
CN108752321A (en) A kind of organic electroluminescence device and display device
CN108727357A (en) A kind of biindolyl class display material
CN109053688A (en) A kind of organic electroluminescence device and display device
CN109053686A (en) A kind of organic electroluminescence device and display device

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
WW01 Invention patent application withdrawn after publication

Application publication date: 20181106

WW01 Invention patent application withdrawn after publication