CN108440313A - Dihydroanthracene compound, organic electroluminescence device and display device - Google Patents

Dihydroanthracene compound, organic electroluminescence device and display device Download PDF

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CN108440313A
CN108440313A CN201810155024.2A CN201810155024A CN108440313A CN 108440313 A CN108440313 A CN 108440313A CN 201810155024 A CN201810155024 A CN 201810155024A CN 108440313 A CN108440313 A CN 108440313A
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organic electroluminescence
electroluminescence device
carbon
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 a kind of dihydroanthracene compound, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (I)：

Description

Dihydroanthracene compound, organic electroluminescence device and display device
Technical field
The present invention relates to display technology fields, more particularly to a kind of dihydroanthracene 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 dihydroanthracene compound, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence device, to solve the high driving voltage of organic electroluminescence device in the prior art and low The problem of luminous efficiency.
According to an aspect of the present invention, a kind of dihydroanthracene compound is provided, shown in the compound such as formula (I)：
Wherein Ar1,Ar2,Ar3,Ar4Separately it is selected from the fragrance being made of carbon and hydrogen that total carbon atom number is 6~30 Alkyl；And Ar1, Ar2, Ar3,Ar4It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkane of carbon atoms 1-30 Oxygroup, carbon atom 6-20 the aromatic radical being made of carbon and hydrogen replaced, this substitution can be monosubstituted, can also be take more Generation.
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.
Optionally, dihydroanthracene compound according to the present invention is selected from：
It should be noted that in concrete structure listed above, the connection type of adjacent group is unique, such as in P- In 2, the two phenyl ring contraposition connected on dihydro anthracene nucleus is replaced by another phenyl ring respectively, in fact, institute on dihydro anthracene nucleus The meta position of the phenyl ring of connection by another phenyl ring replace and dihydro anthracene nucleus on the ortho position of phenyl ring that is connected by another benzene 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 dihydroanthracene compound according to the present invention.
Optionally, the material of the hole injection layer of the organic electroluminescence device or hole transmission layer is according to the present invention Dihydroanthracene compound.
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, Ar1,Ar2Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30；And And Ar1, Ar2It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon atom 6-20 The aromatic radical being made of carbon and hydrogen 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, 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, 8.32 grams of (0.04mol) anthraquinones is slowly added to, finishes, then room temperature of slowly appreciating is added 100 milliliter 36% of hydrochloric acid, 5 milliliter 95% of sulfuric acid are stirred at room temperature 8 hours, add moisture liquid, organic layer washing, anhydrous slufuric acid Magnesium is dried, silica gel column chromatography separation, petroleum ether:Ethyl acetate=5:1 (volume ratio) elution separation, obtains chemical combination shown in formula M-1 10.1 grams of object, yield 62.97%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-1, has obtained the m/e of product：400.
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 7.61 (m, 4H), δ 7.36~7.26 (m, 10H), δ 7.15 (m, 4H).
(2) synthesis of compound P-1
In 250 milliliters of there-necked flask, under nitrogen protection, 100 milliliters of dry toluene of addition, 4.01 grams Compound shown in (0.01mol) formula M-1,4.05 grams of (0.024mol) diphenylamines, 2.5 grams of (0.026mol) sodium tert-butoxides, 0.22 Gram (0.0004mol) bis- (dibenzalacetone) palladiums, the toluene solution of the tri-tert-butylphosphine of 0.78 gram of (0.0004mol) 10%, 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 10：1) it is eluted, is obtained as eluant, eluent To 3.3 grams of product shown in formula P-1, yield 49.8%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：666.
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 7.88 (m, 4H), δ 7.43~7.22 (m, 26H), δ 7.11 (m, 4H), δ 7.00 (m, 4H).
The synthesis of other parts compound of the present invention
Synthetic method changes bromobenzene therein into only as needed in the synthesis of M-1 with reference to the synthetic method of P-1 Corresponding bromo-derivative 1 changes diphenylamines therein into corresponding aromatic amine compounds, to institute in the synthesis of compound P-1 Obtained compound has carried out Mass Spectrometer Method, and the raw material and product Mass Spectrometer Method result used in building-up process 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 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
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.
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. a kind of dihydroanthracene compound, as shown in formula (I)：
Wherein Ar1,Ar2,Ar3,Ar4Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30；
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.
2. dihydroanthracene compound according to claim 1,
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. dihydroanthracene compound according to claim 1, the fragrance being made of carbon and hydrogen that total carbon atom number is 6~30 Alkyl is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indenofluorene Base, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
4. dihydroanthracene compound according to claim 2, wherein total carbon atom number are 6~30 to be made of carbon and hydrogen Aryl radical is selected from：
Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring Penta and phenanthryl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Dihydroanthracene compound below 5.：
6. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes claim 1-5 any The dihydroanthracene compound.
7. organic electroluminescence device according to claim 6, which is characterized in that the hole of the organic electroluminescence device The material of transport layer or hole injection layer is any dihydroanthracene compounds of claim 1-5.
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. compound shown in formula (II)：
Wherein, Ar1,Ar2Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30；
The 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.
CN201810155024.2A 2018-02-23 2018-02-23 Dihydroanthracene compound, organic electroluminescence device and display device Withdrawn CN108440313A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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