CN108586316A - Dihydroanthracene compound, organic electroluminescence device and display device - Google Patents

Dihydroanthracene compound, organic electroluminescence device and display device Download PDF

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CN108586316A
CN108586316A CN201810178746.XA CN201810178746A CN108586316A CN 108586316 A CN108586316 A CN 108586316A CN 201810178746 A CN201810178746 A CN 201810178746A CN 108586316 A CN108586316 A CN 108586316A
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organic electroluminescence
electroluminescence device
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carbon atoms
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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 Ar1Selected from carbon atoms 6~60, the aromatic radical being made of carbon and hydrogen；Ar1It can be by carbon atoms 1-30 Aliphatic alkyl, the aliphatic alkoxy of carbon atoms 1-30, the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen taken Generation；
A and A1It is independently selected from：
Wherein X, Y, Z are independent selected from hydrogen, the aliphatic alkyl of carbon atoms 1-30, Ar1, carbazyl, and in A-6, In A-8, A-10, X is not selected from hydrogen；Ar is selected from aliphatic alkyl, Ar1, the carbazyl of carbon atoms 1-30；
Wherein * indicates the position that A is connected with dihydroanthracene female ring；
Wherein * indicates A1The position being connected with Ar1.
Further, Ar1It is selected from：Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene Base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl； The aliphatic alkyl of carbon atoms 1-30 is selected from：Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, the last of the ten Heavenly stems Base, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl；The aliphatic alkoxy of carbon atoms 1-30 is selected from：Methoxy Base, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, ring Butoxy, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies；The aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from：Benzene Base, xenyl, naphthalene, anthryl, phenanthryl, triphenylene.
Further, Ar1It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30 Replaced, wherein the substitution, can be monosubstituted, disubstituted or polysubstituted.
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 1, the phenyl ring contraposition connected on dihydro anthracene nucleus is replaced by carbazyl, in fact, the meta position quilt of the phenyl ring connected on dihydro anthracene nucleus The ortho position of the phenyl ring connected in carbazyl substitution and dihydro anthracene nucleus is replaced by carbazyl is formed by compound, following (a), (b) It is shown：
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, A, Ar1, A1The change of connection type, belongs to this between representative inside configuration difference or identical group Within the scope of the disclosure of invention and protection.
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 main part of the organic luminous layer of the organic electroluminescence device or the material of hole transmission layer are Dihydroanthracene compound according to the present invention.
Optionally, organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green hair Photosphere, Yellow luminous layer or red light emitting 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.
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.
Beneficial effects of the present invention are as follows：
By compound provided by the invention for the hole transmission layer of organic electroluminescence device or the master of organic luminous layer Body material improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
Specific implementation mode
Specific implementation mode is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with Invention is further explained and description for specific embodiment.
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 2000 milliliters of there-necked flasks, 600 milliliters of tetrahydrofurans, 32.2 grams of (0.1mol) 9- (4- bromines are added in nitrogen protection Phenyl) carbazole, -78 DEG C are cooled to, the hexane solution of the butyl lithium of 59.4 milliliters of (0.095mol) 1.6M is slowly added dropwise, finishes 30 minutes are kept the temperature in -78 DEG C, -78 to -70 DEG C is controlled, is slowly added to 8.32 grams of (0.04mol) anthraquinones, finishes, room of slowly appreciating Then 100 milliliter 36% of hydrochloric acid is added in temperature, 5 milliliter 95% of sulfuric acid is stirred at room temperature 8 hours, adds moisture liquid, organic layer water It washes, anhydrous magnesium sulfate drying, silica gel column chromatography separation, petroleum ether:Ethyl acetate=5:1 (volume ratio) elution separation, obtains formula Compound 8.2 shown in M-1 gram, yield 27.99%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-1, has obtained the m/e of product：730.
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 8.57 (m, 2H), δ 8.20 (m, 2H), δ 7.79 (m, 4H), δ 7.56 (m, 2H), δ 7.50(m, 4H), δ 7.40 (m, 2H), δ 7.33 (m, 4H), δ 7.26~7.08 (m, 12H).
(2) synthesis of compound P-1
In 500 milliliters of there-necked flask, under nitrogen protection, 200 milliliters of dry toluene of addition, 7.32 grams Compound shown in (0.01mol) formula M-1,4 grams of (0.024mol) carbazoles, 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% add Heat is down to room temperature after 12 hours to back flow reaction, and dilute hydrochloric acid, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid After 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 3.1 grams of product shown in formula P-1, yield 31.2%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：992.
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 8.56 (m, 4H), δ 8.34 (m, 2H), δ 8.20 (m, 2H), δ 7.81 (m, 2H), δ 7.55 (m, 4H), δ 7.45~7.35 (m, 8H), δ 7.29 (m, 4H), δ 7.22~7.08 (m, 22H).
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 9- therein (4- bromobenzenes Base) carbazole changes bromo-derivative 1 into, in the synthesis of compound P-1, change carbazole therein into corresponding nitrogen heterocyclic ring class chemical combination Object has carried out Mass Spectrometer Method to obtained compound, 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 main part of organic luminous layer or the material of hole transmission layer are according to the compound of the present invention.
Organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green light emitting layer, Huang Color luminescent layer or red light emitting layer.
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 different materials concrete structure used in the present invention is seen below：
Embodiment 1
Material of main part in using the compound of the present invention as red phosphorescent OLED organic electroluminescence devices, as a comparison Organic electroluminescence device, feux rouges material of main part select CBP.
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).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer NPB on 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；Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 1：
Table 1
Feux rouges material of main part It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
CBP 1000 5.13 13.66
Compound P-1 1000 4.95 14.72
Compound P-6 1000 4.97 14.34
Compound P-9 1000 5.04 14.89
Compound P-10 1000 4.71 14.52
Compound P-16 1000 5.01 13.74
Compound P-18 1000 5.12 14.98
Compound P-27 1000 4.79 13.68
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 2
Material of main part in using the compound of the present invention as green phosphorescent OLED organic electroluminescence devices, as a comparison Organic electroluminescence device, green light material of main part selects CBP respectively.
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).
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer NPB on 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；Wherein " Ir (ppy) 3 [7%] " refers to the doping ratio of green light dyestuff The weight part ratio of example, i.e. green light material of main part and Ir (ppy) 3 are 100:7；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 2：
Table 2
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 3
Material of main part in using the compound of the present invention as blue phosphorescent OLED organic electroluminescence devices, as a comparison Organic electroluminescence device, Blue-light emitting host material selects CBP respectively.
Organic electroluminescence device structure is：ITO/NPB (20nm)/Blue-light emitting host material (30nm)：FIrpic [4%]/ TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation hole transmission layer NPB on 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；Wherein " FIrpic [4%] " refers to the doping ratio of blue light dyestuff Example, the i.e. weight part ratio of Blue-light emitting host material and FIrpic are 100:4；
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed It is respectively 10nm and 15nm to plate film thickness；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 3：
Table 3
Blue-light emitting host material It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
CBP 200 6.06 8.02
Compound P-1 200 5.69 8.04
Compound P-6 200 5.1 8.45
Compound P-9 200 5.62 8.65
Compound P-18 200 5 8.28
Compound P-27 200 5.86 9
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive Dynamic voltage.
Embodiment 4
Hole transmission layer in using the compound of the present invention as organic electroluminescence device, organic electroluminescence as a comparison Luminescent device, hole mobile material select NPB respectively.
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 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 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 4：
Table 4
Hole mobile material It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
NPB 1000 6.08 1.56
Compound P-3 1000 5.46 1.57
Compound P-9 1000 5.18 1.77
Compound P-14 1000 5.34 1.61
Compound P-15 1000 5.72 1.57
Compound P-18 1000 5.5 1.91
Compound P-20 1000 5.39 1.66
Compound P-24 1000 5.04 1.87
Compound P-26 1000 5.47 1.9
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.
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 Ar1Selected from carbon atoms 6~60, the aromatic radical being made of carbon and hydrogen；
The Ar1It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon atom 6- 20 aromatic radical being made of carbon and hydrogen is replaced；
A and A1It is independently selected from：
Wherein X, Y, Z are independent selected from hydrogen, the aliphatic alkyl of carbon atoms 1-30, Ar1, carbazyl, and in A-6, A-8, In A-10, X is not selected from hydrogen；
Ar is selected from aliphatic alkyl, Ar1, the carbazyl of carbon atoms 1-30；
Wherein * indicates the position that A is connected with dihydroanthracene female ring；
Wherein * indicates A1The position being connected with Ar1.
2. dihydroanthracene compound according to claim 1,
Wherein Ar1It is selected from：Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, Cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl；
The aliphatic alkyl of carbon atoms 1-30 is selected from：Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl Base, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl；
The aliphatic alkoxy of carbon atoms 1-30 is selected from：Methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, Heptan oxygroup, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies；
The aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from：Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene.
3. dihydroanthracene compound according to claim 1, Ar1It can be by the aliphatic alkyl of carbon atoms 1-30, carbon containing The aliphatic alkoxy of atom 1-30 is replaced, wherein the substitution, can be monosubstituted, disubstituted or polysubstituted.
4. dihydroanthracene compound according to claim 1, selected from lower structure：
5. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-4 The dihydroanthracene compound.
6. organic electroluminescence device according to claim 5, which is characterized in that the organic electroluminescence device has The material of main part of machine luminescent layer or the material of hole transmission layer are any dihydroanthracene compounds of claim 1-4.
7. organic electroluminescence device according to claim 6, which is characterized in that the organic luminous layer is blue-light-emitting Layer, green light emitting layer, Yellow luminous layer or red light emitting layer.
8. a kind of display device, which is characterized in that include the organic electroluminescence device as described in claim 5~7 is any.
9. a kind of electronic equipment, including display device described in claim 8.
10. electronic equipment according to claim 9, the electronic equipment is selected from mobile phone, computer, tablet computer, wrist-watch, VR Display, digital camera, bracelet, counter, electronic watch.
CN201810178746.XA 2018-03-05 2018-03-05 Dihydroanthracene compound, organic electroluminescence device and display device Pending CN108586316A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112321587A (en) * 2020-10-30 2021-02-05 上海天马有机发光显示技术有限公司 Organic compound, electroluminescent material and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101475433A (en) * 2009-01-22 2009-07-08 河北德隆泰化工有限公司 Anthryl derivative and preparation thereof
CN102532001A (en) * 2010-12-17 2012-07-04 清华大学 Dihydroanthracene compounds containing pyridine group and application of compounds
CN102557856A (en) * 2010-12-17 2012-07-11 清华大学 Tetraphenyl dihydro anthracenes compound containing aryl group and application thereof
CN102675128A (en) * 2011-03-07 2012-09-19 昆山维信诺显示技术有限公司 Dihydroanthracene derivative, preparation method and application thereof and luminescent device comprising dihydroanthracene derivative
CN103553936A (en) * 2013-10-30 2014-02-05 吉林奥来德光电材料股份有限公司 Anthracene containing derivative as well as preparation method and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101475433A (en) * 2009-01-22 2009-07-08 河北德隆泰化工有限公司 Anthryl derivative and preparation thereof
CN102532001A (en) * 2010-12-17 2012-07-04 清华大学 Dihydroanthracene compounds containing pyridine group and application of compounds
CN102557856A (en) * 2010-12-17 2012-07-11 清华大学 Tetraphenyl dihydro anthracenes compound containing aryl group and application thereof
CN102675128A (en) * 2011-03-07 2012-09-19 昆山维信诺显示技术有限公司 Dihydroanthracene derivative, preparation method and application thereof and luminescent device comprising dihydroanthracene derivative
CN103553936A (en) * 2013-10-30 2014-02-05 吉林奥来德光电材料股份有限公司 Anthracene containing derivative as well as preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
于军胜主编: "《显示器件技术》", 31 July 2010, 国防工业出版社 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112321587A (en) * 2020-10-30 2021-02-05 上海天马有机发光显示技术有限公司 Organic compound, electroluminescent material and application thereof

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Application publication date: 20180928