CN108675985A - Containing unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device - Google Patents

Containing unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device Download PDF

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CN108675985A
CN108675985A CN201810250026.XA CN201810250026A CN108675985A CN 108675985 A CN108675985 A CN 108675985A CN 201810250026 A CN201810250026 A CN 201810250026A CN 108675985 A CN108675985 A CN 108675985A
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organic electroluminescence
carbon
electroluminescence device
compound
hydrogen
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不公告发明人
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Wang Meini
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Wang Meini
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Abstract

The present invention relates to display technology fields, more particularly to one kind containing unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (I)：

Description

Containing unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and show Showing device
Technical field
The present invention relates to display technology field, more particularly to one kind containing unsaturated nitrogenous heterocyclic acridine compound, 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 functional 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, the hair of most important a variety of colors certainly in organic electroluminescence device Luminescent material will also achieve the purpose that match with adjacent functional material, therefore, the organic electroluminescence device of excellent in efficiency long lifespan 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 provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode, electron injecting layer, electronics being arranged in order from top to bottom Transport layer (Electron transport Layer, abbreviation ETL), organic luminous layer (Emitting Layer, abbreviation EML), Hole transmission layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic light emission The formation probability of exciton is improved in layer as possible, therefore the organic luminous layer of organic electroluminescence device and hole adjacent thereto pass The material of defeated layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And it is in the prior art Hole transmission layer or organic luminous layer make organic electroluminescence device have higher driving voltage and lower luminous efficiency.
Invention content
The present invention provides a kind of containing unsaturated nitrogenous heterocyclic acridine compound, includes the organic electroluminescence of the compound Luminescent device and display device with the organic electroluminescence device, to solve organic electroluminescence device in the prior art High driving voltage and the problem of low luminous efficiency.
According to an aspect of the present invention, it provides a kind of containing unsaturated nitrogenous heterocyclic acridine compound, the compound As shown in formula (I)：
Wherein Ar1,Ar3,Ar4Separately it is selected from the aromatic hydrocarbon being made of carbon and hydrogen that total carbon atom number is 6~30 Base；Ar2The undersaturated oxygen heterocycle of undersaturated nitrogen heterocyclic ring, carbon atom 12~40 selected from carbon atoms 3~60；And Ar1, Ar2, Ar3,Ar4It can be former by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon The aromatic radical of sub- 6-20 being made of carbon and hydrogen is replaced, this substitution can be monosubstituted, can also be polysubstituted.
And Ar2It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen2Directly and on acridine ring N atoms connection, can also be Ar2Pass through the N atoms on the aromatic radical being made of carbon and hydrogen and acridine ring of carbon atom 6-20 Connection, is illustrated below：
Work as Ar2Selected from pyridyl group, when the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from phenyl, Ar2Direct and a word used for translation When N atoms in phenazine ring connect, shown in obtained compound such as formula (II)：
Work as Ar2Selected from pyridyl group, when the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from phenyl, Ar2Pass through carbon original Sub- 6-20's is connected with the aromatic radical that hydrogen forms with the N atoms on acridine ring by carbon, obtained compound such as formula (III) institute Show：
Further, wherein Ar3, Ar4It is selected from：B-1：
Wherein, Ar7、Ar8、Ar9Separately it is selected from the aromatic hydrocarbon being made of carbon and hydrogen that total carbon atom number is 6~30 Base, m are selected from 0 or 1；Wherein * indicates the position that B-1 is connected with N atoms in compound shown in formula (I).
Further, the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30 is selected from：Phenyl, xenyl, three Xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzene And fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Further, Ar2It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, hexichol And furyl, benzo benzo furyl, dinaphtho furyl；And Ar2Can by methyl, ethyl, propyl, butyl, amyl, oneself Base, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, third Oxygroup, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, ring penta Oxygroup, cyclohexyloxy, two cyclohexyloxies, phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene substitution.
Optionally, according to the present invention to be selected from containing unsaturated nitrogenous heterocyclic acridine compound：
It should be noted that in concrete structure listed above, the connection type of adjacent group is unique, such as in P- In 21, the phenyl ring contraposition connected on 9 carbon atoms of acridine ring is replaced by another phenyl ring, in fact, 9 carbon atoms of acridine ring The meta position of the phenyl ring of upper connection by another phenyl ring replace and 9 carbon atoms of acridine ring on the ortho position of phenyl ring that connects it is another Outer phenyl ring substitution is formed by compound, shown in following (a), (b)：
It can achieve the effect that the present invention, belong to the content of the invention to be disclosed and be protected.Such the position of substitution Change, there is no the agent structures for changing the compounds of this invention, without influence on the application technology effect of the compounds of this invention.
Therefore, in the logical formula (I) of the present invention
In, Ar1, Ar2, Ar3,Ar4The change of connection type between representative inside configuration difference or identical group, Within the scope of belonging to disclosure of the invention and protecting.
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Including according to the present invention containing unsaturated nitrogenous heterocyclic acridine compound.
Optionally, the material of the electron transfer layer of the organic electroluminescence device, hole injection layer or hole transmission layer To contain unsaturated nitrogenous heterocyclic acridine compound according to the present invention.
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.
Meanwhile the present invention also provides a kind of electronic equipment, which contains electronic display screen.
Further, above-mentioned electronic equipment is selected from：Mobile phone, computer, tablet computer, wrist-watch, VR displays, digital camera, Bracelet, counter, electronic watch.
The present invention also provides formulas (II) to show compound：
Wherein, Ar1The aryl radical being made of carbon and hydrogen for being 6~30 selected from total carbon atom number；Ar2Selected from carbon atoms 3 ~60 undersaturated nitrogen heterocyclic ring, the undersaturated oxygen heterocycle of carbon atom 12~40；
And Ar1, Ar2Can by the aliphatic alkyl of carbon atoms 1-30, carbon atoms 1-30 aliphatic alkoxy, The aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is replaced.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used for the hole transmission layer or hole injection layer of organic electroluminescence device, is improved The luminous efficiency of organic electroluminescence device, the driving voltage for reducing 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.
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 compound P-1
(1) synthesis of intermediate M-1：
In 1000 milliliters of there-necked flasks, under nitrogen protection, 500 milliliters of toluene, 19.5 grams of (0.1mol) acridines -9 are added (10H) -one, 15.8 grams of (0.1mol) 2- bromopyridines, 11.52 grams of (0.12mol) sodium tert-butoxides, 0.575 gram of (0.001mol) Pd (dba)2(bis- (dibenzalacetone) palladiums), 10% toluene solution of 2.02 grams of (0.001mol) tri-tert-butylphosphines is heated to Back flow reaction 4 hours, cooling add moisture liquid, organic layer washing, anhydrous magnesium sulfate drying, silica gel column chromatography separation, petroleum ether: Ethyl acetate=1:2 (volume ratios) elution separation, obtains 22.3 grams of compound shown in formula M-1, yield 81.98%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-1, has obtained the m/e of product：272.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-1, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 8.05 (m, 1H), δ 7.65 (m, 2H), δ 7.55 (m, 1H), δ 7.48 (m, 2H), δ 7.26 (m, 2H), δ 7.21 (m, 1H), δ 7.08 (m, 2H), δ 6.70 (m, 1H).
(2) synthesis of intermediate M-2：
In 1000 milliliters of there-necked flasks, 400 milliliters of tetrahydrofurans, 15.7 grams of (0.1mol) bromobenzenes, drop is added in nitrogen protection The hexane solution of the butyl lithium of 59.4 milliliters of (0.095mol) 1.6M is slowly added dropwise to -78 DEG C in temperature, finishes in -78 DEG C of heat preservations 30 minutes, -78 to -70 DEG C are controlled, 200 milliliters of tetrahydrochysene furans of compound shown in 21.76 grams of (0.08mol) formula M-1 are slowly added to It mutters solution, finishes, be slowly increased to room temperature, 100 milliliter 36% of hydrochloric acid is then added, 5 milliliter 95% of sulfuric acid is stirred at room temperature 8 Hour, it is adjusted to neutrality with sodium hydroxide solution, adds water and dichloromethane liquid separation, organic layer washing, anhydrous magnesium sulfate is dried, dense Be reduced to it is solvent-free after, silica gel column chromatography separation, petroleum ether:Ethyl acetate=5:2 (volume ratios) elution separation, obtains formula M-2 institutes Show 11.2 grams of compound, yield 30.35%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-2, has obtained the m/e of product：368.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-2, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 8.04 (m, 1H), δ 7.55 (m, 1H), δ 7.37~7.18 (m, 12H), δ 7.00 (m, 2H), δ 7.71 (m, 1H).
(3) synthesis of compound P-1
In 250 milliliters of there-necked flask, under nitrogen protection, be added 100 milliliters of dry toluene, 3.69 grams Compound shown in (0.01mol) formula M-2,2.03 grams of (0.012mol) diphenylamines, 1.25 grams of (0.013mol) sodium tert-butoxides, 0.11 Gram (0.0002mol) bis- (dibenzalacetone) palladiums, 0.39 gram of (0.0002mol) 10% tri-tert-butylphosphine toluene solution, It is down to room temperature after being heated to back flow reaction 12 hours, dilute hydrochloric acid is added, liquid separation, neutrality is washed with water in organic layer, with anhydrous sulphur After sour magnesium drying, with silica gel post separation, petroleum ether is used：Ethyl acetate (volume ratio 5：1) it is eluted, is obtained as eluant, eluent 3.29 grams of product shown in formula P-1, yield 65.67%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：501.
Nuclear-magnetism detection is carried out to obtained compound P-1, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 8.05 (m, 1H), δ 7.55 (m, 1H), δ 7.45~7.20 (m, 20H), δ 7.07 (m, 2H), δ 7.00 (m, 2H), δ 6.76 (m, 1H).
The synthesis of other parts compound of the present invention
The synthetic method of synthetic method reference P-1, only as needed in the synthesis of M-1, by 2- bromopyridines therein It changes corresponding bromo-derivative 1 into, in the synthesis of M-2, changes bromobenzene therein into bromo-derivative 2, in the synthesis of compound P-1, It changes diphenylamines therein into corresponding aromatic amine compounds, Mass Spectrometer Method has been carried out to obtained compound, had been synthesized The raw material and product Mass Spectrometer Method result of Cheng Suoyong see the table below：
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device The material of electron transfer layer, hole transmission layer or hole injection layer is according to the compound of 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 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), have a smaller potential barrier with anode, can vacuum evaporation form pin-hole free films.Commonly HIM is Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
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.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4- (1 '-naphthalene) -5- benzene -1,2,4- triazoles) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazoles) benzene) or be derived from this three Arbitrary two kinds of the collocation of kind material.
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 1
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)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, 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 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 passed with hole 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 layers 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 layers 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
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole transmission layer by upper table The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 2
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)/NPB(40nm)/EM1(30nm)/ETL(20nm)/ LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, 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 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 passed with hole 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 Hole injection layer, 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 layers 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 layers 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
Hole-injecting material It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
HIL02 1000 5.96 1.52
Compound P-45 1000 5.03 1.53
Compound P-46 1000 5.68 1.47
Compound P-47 1000 5.38 1.53
Compound P-48 1000 4.89 1.58
Compound P-52 1000 4.99 1.76
Compound P-53 1000 5.38 1.44
Compound P-56 1000 5.27 1.73
Compound P-57 1000 5.93 1.74
Compound P-60 1000 5.54 1.48
Compound P-61 1000 5.56 1.53
Compound P-62 1000 6.02 1.49
Compound P-63 1000 5.02 1.72
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole injection layer by upper table The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 3
Electron transfer layer in using the compound of the present invention as organic electroluminescence device, organic electroluminescence as a comparison Luminescent device, electron transport material select TAZ.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL (20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, HIL02 makees Hole injection layer, NPB make hole transmission layer, and EM1 makees the material of main part of organic luminous layer, and LiF/Al makees 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 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 passed with hole 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 NPB on hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 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 transport material on organic luminous layer, the electron-transport as organic electroluminescence device 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 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 3：
Table 3
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as electron transfer layer by upper table The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
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 (10)

1. one kind is containing unsaturated nitrogenous heterocyclic acridine compound, as shown in formula (I)：
Wherein Ar1,Ar3,Ar4Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30；
Ar2The undersaturated oxygen heterocycle of undersaturated nitrogen heterocyclic ring, carbon atom 12~40 selected from carbon atoms 3~60；
The Ar1, Ar2, Ar3,Ar4It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alcoxyl of carbon atoms 1-30 Base, carbon atom 6-20 the aromatic radical being made of carbon and hydrogen replaced；
And Ar2It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen2Directly and the N on acridine ring is former Son connection, can also be Ar2It is connected with the N atoms on acridine ring with the aromatic radical that hydrogen forms by carbon by carbon atom 6-20.
2. according to claim 1 contain unsaturated nitrogenous heterocyclic acridine compound,
Wherein Ar3, Ar4It is selected from：B-1：
Wherein, Ar7、Ar8、Ar9Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30, m Selected from 0 or 1；
Wherein * indicates the position that B-1 is connected with N atoms in compound shown in formula (I).
3. according to claim 1 containing unsaturated nitrogenous heterocyclic acridine compound, total carbon atom number be 6~30 by The aryl radical of carbon and hydrogen composition is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenes Base, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl；
Ar2It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, dibenzofuran group, benzo Benzofuranyl, dinaphtho furyl；
The Ar2It can be by methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, ring fourth It is base, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, pungent Oxygroup, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies, phenyl, biphenyl Base, naphthalene, anthryl, phenanthryl, triphenylene substitution.
4. according to claim 2 containing unsaturated nitrogenous heterocyclic acridine compound, wherein total carbon atom number is 6~30 The aryl radical being made of carbon and hydrogen be selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrene Base, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzanthracene Base；
Ar2It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, dibenzofuran group, benzo Benzofuranyl, dinaphtho furyl；
The Ar2It can be by methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, ring fourth It is base, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, pungent Oxygroup, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies, phenyl, biphenyl Base, naphthalene, anthryl, phenanthryl, triphenylene substitution.
Containing unsaturated nitrogenous heterocyclic acridine compound below 5.：
6. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes claim 1-5 any Described contains unsaturated nitrogenous heterocyclic acridine compound.
7. organic electroluminescence device according to claim 6, which is characterized in that the electronics of the organic electroluminescence device The material of transport layer, hole transmission layer or hole injection layer is described in claim 1-5 is any containing unsaturated nitrogenous heterocyclic Acridine compound.
8. a kind of display device, which is characterized in that include the organic electroluminescence device as described in claim 6~7 is any.
9. a kind of electronic equipment, including display device described in claim 8, the electronic equipment is selected from mobile phone, computer, tablet electricity Brain, wrist-watch, VR displays, digital camera, bracelet, counter, electronic watch.
10. formula (II) shows compound：
Wherein, Ar1The aryl radical being made of carbon and hydrogen for being 6~30 selected from total carbon atom number；Ar2Selected from carbon atoms 3~60 Undersaturated nitrogen heterocyclic ring, carbon atom 12~40 undersaturated oxygen heterocycle；
And Ar1, Ar2It can be former by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon The aromatic radical of sub- 6-20 being made of carbon and hydrogen is replaced.
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN113227106A (en) * 2018-12-28 2021-08-06 辛诺拉有限公司 Organic molecules for optoelectronic devices

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Publication number Priority date Publication date Assignee Title
CN103503188A (en) * 2011-05-05 2014-01-08 默克专利有限公司 Compounds for electronic devices

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
CN103503188A (en) * 2011-05-05 2014-01-08 默克专利有限公司 Compounds for electronic devices

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113227106A (en) * 2018-12-28 2021-08-06 辛诺拉有限公司 Organic molecules for optoelectronic devices
JP2022514625A (en) * 2018-12-28 2022-02-14 サイノラ ゲゼルシャフト ミット ベシュレンクテル ハフツング Organic molecules for optoelectronic devices
JP7265013B2 (en) 2018-12-28 2023-04-25 三星ディスプレイ株式會社 Organic molecules, uses of organic molecules, compositions, optoelectronic devices and methods for making optoelectronic devices

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