CN108863896A - Biindolyl class material, organic electroluminescence device and display device - Google Patents
Biindolyl class material, organic electroluminescence device and display device Download PDFInfo
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- 0 CN(C1C=CC=C*11)C(c([n](C)c2ccccc22)c2-c(cc2)ccc2N2C(C=CCC3)=C3N(c(cc3)ccc3Nc3ccccc3)c3c2cccc3)=C1c(cc1)ccc1N1c(cccc2)c2N(c(cc2)ccc2N(CC=CC=C)c2ccccc2)c2c1cccc2 Chemical compound CN(C1C=CC=C*11)C(c([n](C)c2ccccc22)c2-c(cc2)ccc2N2C(C=CCC3)=C3N(c(cc3)ccc3Nc3ccccc3)c3c2cccc3)=C1c(cc1)ccc1N1c(cccc2)c2N(c(cc2)ccc2N(CC=CC=C)c2ccccc2)c2c1cccc2 0.000 description 3
- GQFBHWGPSXLOFG-UHFFFAOYSA-N CC(C)c(cc1)cc2c1N(c(cc1)ccc1C1=C(c([n](C)c3c4cccc3)c4-c(cc3)ccc3N3c(ccc(C(C)C)c4)c4Sc4c3ccc(C(C)C)c4)N(C)C3C=CC=CC13)c1ccc(C(C)C)cc1S2 Chemical compound CC(C)c(cc1)cc2c1N(c(cc1)ccc1C1=C(c([n](C)c3c4cccc3)c4-c(cc3)ccc3N3c(ccc(C(C)C)c4)c4Sc4c3ccc(C(C)C)c4)N(C)C3C=CC=CC13)c1ccc(C(C)C)cc1S2 GQFBHWGPSXLOFG-UHFFFAOYSA-N 0.000 description 1
- HNDRAADDGKQDAJ-UHFFFAOYSA-N CN(C1C=CC=CC11)C(c([n](C)c2ccccc22)c2-c(cc2)ccc2-[n]2c3ccc(-c4ccccc4)c4c3c3c2ccc(-c2ccccc2)c3cc4)=C1c(cc1)ccc1N1c2ccc(C3=CC=CCC3)c3ccc4C(c5ccccc5)=CCC1c4c23 Chemical compound CN(C1C=CC=CC11)C(c([n](C)c2ccccc22)c2-c(cc2)ccc2-[n]2c3ccc(-c4ccccc4)c4c3c3c2ccc(-c2ccccc2)c3cc4)=C1c(cc1)ccc1N1c2ccc(C3=CC=CCC3)c3ccc4C(c5ccccc5)=CCC1c4c23 HNDRAADDGKQDAJ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- 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
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- 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
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- 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
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- 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
- H10K50/15—Hole transporting layers
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- 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]
- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
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 following advantages 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 B is selected from carbazyl, benzo carbazole base, dibenzo-carbazole base, indeno carbazyl, indolocarbazole base, indoles
And Spirofluorene-based, acridan base, dihydrophenazine base, 10H- phenothiazinyl, 10H- phenoxazine base;B can be by the alkane of C1~C20
Base, the alkoxy of C1~C20, replaced the aryl being made of carbon and hydrogen of C6~C40, B-1;The substitution, which can be, singly to be taken
It is generation, disubstituted, it is polysubstituted:
In B-1, Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, * indicates B-1 and formula in B-1
(1) position of B connection in;Ar1, Ar2Can be by the alkyl of C1~C20, the alkoxy of C1~C20, C6~C40 by carbon and hydrogen
Replaced the aryl of composition;It is described substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted.
Further, the aryl of C6~C40 is selected from:Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene
Base, fluorenyl, fluoranthene base, indeno fluorenyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, phenyl substituted naphthyl, benzo anthryl;C1~
The alkyl of C20 is selected from methyl, ethyl, propyl, butyl, amyl, hexyl, cyclohexyl, heptyl, octyl;The alkoxy of C1~C20 selects
From methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, cyclohexyloxy, oxygroup in heptan, octyloxy.
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 hole mobile material of the organic electroluminescence device is biindolyl class material according to the present invention.
Optionally, the hole-injecting 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.
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:
By compound provided by the invention be used as organic electroluminescence device hole-injecting material or/and hole transport
Material or luminescent layer material of main part improve the luminous efficiency of organic electroluminescence device, reduce organic electroluminescent
The driving voltage of 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 intermediate 1
In 2000 milliliters of there-necked flasks, 28.6 grams of (0.1mol) 3- (4- bromophenyl) -1- Methyl-1H-indoles, 800 millis are added
Anhydrous acetonitrile is risen, 0~3 DEG C of temperature of control is slowly added dropwise 10 grams of nitric acid of 65%, is added dropwise, and controls 0~3 DEG C of temperature reaction 3
Hour, then control 0~3 DEG C of temperature and be slowly added dropwise 10 grams of nitric acid of 65%, it controls 0~3 DEG C of temperature and reacts 3 hours, then control temperature
10 grams of nitric acid of 65% are slowly added dropwise in 0~3 DEG C of degree, control 0~3 DEG C of temperature and react 8 hours, add water and methylene chloride liquid separation, water
It is washed till neutrality, the separation of organic layer silica gel column chromatography, ethyl acetate:Petroleum ether=1:9 (volume ratios) elution, eluent are 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 compound P-1
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene are added, in 28.5 grams (0.05mol)
Compound shown in mesosome 1,20.04 grams of (0.12mol) carbazoles, 14.4 grams of (0.15mol) sodium tert-butoxides, 0.58 gram (0.001mol)
Bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene solution, be heated to back flow reaction 8
It is down to room temperature after hour, dilute hydrochloric acid, liquid separation is added, neutrality is washed with water in organic layer, after anhydrous magnesium sulfate drying, crosses silica gel
Post separation, ethyl acetate:Petroleum ether=1:5 (volume ratios) elution, eluent is concentrated to dryness, with ethanol/toluene mixed solvent weight
Crystallization, obtains 26.6 grams of compound shown in formula P-1, yield 71.6%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product:742.
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 8.51 (m, 2H), δ 8.12 (m, 2H), δ 7.90 (m, 8H), δ 7.76 (m, 2H), δ
7.51 (m, 4H), δ 7.40 (m, 2H), δ 7.28 (m, 2H), δ 7.23~7.03 (m, 10H), δ 3.78 (s, 6H).
The synthesis of 2 other parts compound of embodiment
The synthetic method of reference compound P-1 only changes carbazole therein into corresponding nitrogenous aromatic series as needed
Compound.Specific reaction nitrogen-containing aromatic compound used and obtained the compound of the present invention mass spectrometric data list are such as
Under:
The synthesis of 3 compound P-33 of embodiment
1000 milliliters of there-necked flasks, nitrogen protection are added 200 milliliters of toluene, 200 milliliters of ethyl alcohol, 100 milliliters of water, and 2.85 grams
Compound shown in (0.005mol) intermediate 1,3.34 grams of (0.012mol) N- phenyl carbazole -3- boric acid, 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, organic layer magnesium sulfate is dry, silica gel column chromatography separation, ethyl acetate:Petroleum ether=1:5 (volume ratios) elution, eluent
It is concentrated to dryness, obtains 3.06 grams of product shown in formula P-33, yield 68.37%,
Mass Spectrometer Method has been carried out to product shown in obtained formula P-33, has obtained the m/e of product:894.
Nuclear-magnetism detection is carried out to product shown in obtained formula P-33, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3):δ 8.52 (m, 1H), δ 8.22 (m, 3H), δ 7.87 (m, 1H), δ 7.76 (m, 2H), δ
7.70 (d, 1H), δ 7.66~7.56 (m, 7H), δ 7.51 (m, 8H), δ 7.38 (m, 1H), δ 7.34~7.22 (m, 10H), δ 7.20
~7.13 (m, 4H), δ 7.02 (m, 2H), δ 3.79 (s, 6H).
The synthesis of 4 other parts compound of embodiment
The synthetic method of reference compound P-33 only changes N- phenyl carbazole -3- boric acid therein into phase as needed
The boric acid compound answered.Specific reaction boric acid compound used and obtained the compound of the present invention mass spectrometric data column
Table is as follows:
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Hole-injecting material/hole mobile material/luminescent layer material of main part be biindolyl class material according to the present invention.
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 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: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, 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.
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 5
Hole mobile material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole mobile material select NPB.
Organic electroluminescence device structure is:ITO/HIL02(100nm)/HTL(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Glass substrate is selected in organic electroluminescence device production in the present embodiment, ITO makees anode material, and HIL02 makees
Hole injection layer, EM1 make the material of main part of organic luminous layer, and TAZ makees electron injection as electron transport layer materials, LiF/Al
Layer/cathode material.
Organic electroluminescence device preparation process in the present embodiment 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 passed with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
The binding ability of defeated 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.
The vacuum evaporation hole transmission layer on hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 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.
Electron transfer layer of the vacuum evaporation TAZ as organic electroluminescence device on organic luminous layer;Speed is deposited in it
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 on electron transfer layer (ETL);
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 1:
Table 1
It can see by upper table, organic electroluminescence can be improved using the compound of the present invention as hole transmission layer
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 6
Hole-injecting material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole-injecting material select HIL02.
Organic electroluminescence device structure is:ITO/HIL(100nm)/HTL(40nm)/EM1(30nm)/ETL(20nm)/
LiF(0.5nm)/Al(150nm)。
Glass substrate is selected in organic electroluminescence device production in the present embodiment, ITO makees anode material, and NPB makees empty
Cave transport layer, EM1 make the material of main part of organic luminous layer, TAZ as electron transport layer materials, LiF/Al make electron injecting layer/
Cathode material.
Organic electroluminescence device preparation process in the present embodiment 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 passed with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
The binding ability of defeated layer.
Above-mentioned glass substrate is placed in vacuum chamber, the vacuum evaporation hole injection layer on anode, evaporation rate 0.1nm/
S, vapor deposition film thickness are 100nm.
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.
Electron transfer layer of the vacuum evaporation TAZ as organic electroluminescence device on organic luminous layer;Speed is deposited in it
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 on electron transfer layer (ETL);
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 2:
Table 2
It can see by upper table, organic electroluminescence can be improved using the compound of the present invention as hole injection layer
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 7
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence device:
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, other 7 organic electroluminescences hairs
Optical device selects material of the invention.
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
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 is shown in Table 3:
Table 3
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 8:
The compound of the present invention is as the material of main part in green phosphorescent OLED organic electroluminescence device:
9 organic electroluminescence devices are prepared altogether, and 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, other 8 organic electroluminescences hairs
Optical device selects material of the invention.
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
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 is shown in Table 4:
Table 4
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 (5)
1. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes biindolyl shown in formula (1)
Class material:
Wherein B is selected from carbazyl, benzo carbazole base, dibenzo-carbazole base, indeno carbazyl, indolocarbazole base, indoles and spiral shell
Fluorenyl, acridan base, dihydrophenazine base, 10H- phenothiazinyl, 10H- phenoxazine base;
B can be by the alkyl of C1~C20, the alkoxy of C1~C20, and the aryl being made of carbon and hydrogen, the B-1 of C6~C40 is taken
Generation;It is described substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted:
Ar1, Ar2The independent aryl being made of carbon and hydrogen selected from C6~C40, * indicates what B-1 was connected with B in formula (1) in B-1
Position;
Ar1, Ar2It can be taken by the alkyl of C1~C20, the aryl of the alkoxy of C1~C20, C6~C40 being made of carbon and hydrogen
Generation;It is described substitution can be it is monosubstituted, it is disubstituted, it is polysubstituted.
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.
3. organic electroluminescence device according to claim 1, biindolyl class material shown in formula (1) is selected from:
4. organic electroluminescence device as described in claim 1, which is characterized in that the hole of the organic electroluminescence device
Injection material is biindolyl class material shown in formula (1).
5. a kind of display device, which is characterized in that including organic electroluminescence device as described in claim 1.
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Cited By (2)
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WO2021000455A1 (en) * | 2019-07-04 | 2021-01-07 | 武汉华星光电半导体显示技术有限公司 | Hole transport material, preparation method therefor and electroluminescent device |
US20220213124A1 (en) * | 2019-11-05 | 2022-07-07 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Nitrogen-containing compound, electronic element, and electronic device |
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2018
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Cited By (4)
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WO2021000455A1 (en) * | 2019-07-04 | 2021-01-07 | 武汉华星光电半导体显示技术有限公司 | Hole transport material, preparation method therefor and electroluminescent device |
US11527724B2 (en) * | 2019-07-04 | 2022-12-13 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Hole transporting material, method for preparing same, and electroluminescent device |
US20220213124A1 (en) * | 2019-11-05 | 2022-07-07 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Nitrogen-containing compound, electronic element, and electronic device |
US11524970B2 (en) * | 2019-11-05 | 2022-12-13 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Nitrogen-containing compound, electronic element, and electronic device |
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