CN108997317A - A kind of organic electroluminescence device and display device - Google Patents

A kind of organic electroluminescence device and display device Download PDF

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CN108997317A
CN108997317A CN201810793608.2A CN201810793608A CN108997317A CN 108997317 A CN108997317 A CN 108997317A CN 201810793608 A CN201810793608 A CN 201810793608A CN 108997317 A CN108997317 A CN 108997317A
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organic electroluminescence
electroluminescence device
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aromatic heterocyclic
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赵东敏
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    • 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
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    • C07—ORGANIC CHEMISTRY
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • 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
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Abstract

The present invention relates to field of display technology, 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 field of display technology, more particularly to a kind of biindolyl class material, organic electroluminescence device and Display device.
Background technique
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 advantage that 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 Adjust thermal stability, mechanical performance, the luminous and electric conductivity of organic material, the space so that material is significantly improved.
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 in organic semiconductor, the transmission of carrier is normal 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 The difficulty of charge injection and transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer Number, and so that different organic layers is played 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 inject 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 various colors Luminescent material will also achieve the purpose that match with adjacent functional material.Therefore, the organic electroluminescence of excellent in efficiency service life length Part be usually device architecture and various organic materials optimization collocation as a result, this is just that chemists design and develop 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 lower, generally below 10%.
In the preparation process of organic electroluminescence device, another is known as solwution method, that is, uses soluble OLED material 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.
Summary of the invention
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, the organic electroluminescence device comprising 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 Replaced the sulfur-bearing aromatic heterocyclic that oxygen-containing aromatic heterocyclic that nitrogen aromatic heterocyclic, carbon atom number are 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 by carbon atom number be 3-80 nitrogenous aromatic heterocyclic replaced, It is described substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted；N is selected from 0 or 1.
Further, wherein the 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 flowering 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 biindolyl class material according to the present invention.
Optionally, the material of main part of the luminescent layer of the organic electroluminescence device is 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 embodiment
Specific embodiment 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, the organic electroluminescence device comprising 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 compound P-1
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene, 19.2 grams of (0.05mol) 3 are added, 3'- diphenyl -1H, 1'H-2,2'- biindolyl, 18.96 grams of (0.12mol) 2- bromopyridines, 14.4 grams of (0.15mol) tert-butyl alcohols Sodium, 0.58 gram (0.001mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene Solution is down to room temperature after being heated to back flow reaction 8 hours, dilute hydrochloric acid is added, liquid separation, neutrality is washed with water in organic layer, with nothing After water magnesium sulfate is dry, cross silica gel post separation, ethyl acetate: petroleum ether=2:5 (volume ratio) elution, eluent are concentrated to dryness, It is recrystallized with methanol/toluene mixed solvent, obtains 19.1 grams of compound shown in formula P-1, yield 70.9%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e:538 of product.
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, 2H), δ 8.17 (m, 4H), δ 8.00 (m, 2H), δ 7.55~7.40 (m, 10H), δ 7.38~7.27 (m, 6H), δ 7.22 (m, 2H).
The synthesis of 2 other parts compound of embodiment
The synthetic method of reference compound P-1 can synthesize other compounds provided by the present invention, only will be therein 2- bromopyridine changes corresponding bromo-derivative into as needed.
Specific reaction bromo-derivative used and obtained a part of compound mass spectrometric data of the invention 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 biindolyl class material according to the present invention.
The typical structure of organic electroluminescence device are as follows: 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 is also possible to multi-luminescent layer.
Wherein, the substrate in conventional organic electroluminescence device can be used in substrate, 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), have lesser potential barrier with anode or hole-injecting material, vapour deposition method prepares organic electroluminescent 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 master 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 level 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 to control exciton in luminescent layer, there are 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: there is 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, is able to carry out vapor deposition 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 level 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- triazole) or TPBi (tri- (N- of 1,3,5- Phenyl -2- benzimidazole) benzene) or it is derived from any two kinds of 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 compound, 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 used as to of the invention specific 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 specific 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 are as follows: 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 Water is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface 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 layer 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 device:
Organic electroluminescence device structure are as follows:
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 in alcohol mixed solvent is toasted under clean environment To completely removing moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
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；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed Plating film thickness is respectively 10nm and 15nm；
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:
Can see by upper table, 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 device:
Organic electroluminescence device structure are as follows:
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 in alcohol mixed solvent is toasted under clean environment To completely removing moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
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；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed Plating film thickness is respectively 10nm and 15nm；
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:
Can see by upper table, 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 Mind 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 organic electroluminescence device contains biindolyl class material shown in formula (1):
Wherein Ar1The aryl being made of carbon and hydrogen selected from C6~C40, Ar2The nitrogenous heteroaromatic for being 3-80 selected from carbon atom number 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 Replaced aromatic heterocyclic, it is described substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted；
Also, work as Ar2When replaced the aryl being made of carbon and hydrogen by C6~C40, C6~C40 is made of carbon and hydrogen herein Aryl can by carbon atom number be 3-80 nitrogenous aromatic heterocyclic replaced, it is described substitution can be it is monosubstituted, it is disubstituted, it is more Replace；
N is selected from 0 or 1；
The organic electroluminescence device is red organic electroluminescence device.
2. organic electroluminescence device according to claim 1, wherein the 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, wherein biindolyl class material shown in formula (1) is selected from following knot Structure:
4. a kind of display device, which is characterized in that including the organic electroluminescence device as described in claims 1 to 3 is any.
CN201810793608.2A 2018-07-19 2018-07-19 A kind of organic electroluminescence device and display device Withdrawn CN108997317A (en)

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